# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_CAPPRO6_3
_database_code_depnum_ccdc_archive 'CCDC 2190703'
loop_
_audit_author_name
_audit_author_address
'Kazuhiko Takatori'
;Meiji Pharmaceutical University, Synthetic Organic Chemistry
Japan
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C14 H26 N2 O6 S'
_chemical_formula_moiety         'C14 H26 N2 O6 S'
_chemical_formula_weight         350.43
_chemical_melting_point          ?
_chemical_absolute_configuration rmad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.6428(3)
_cell_length_b                   14.1206(7)
_cell_length_c                   18.2790(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1714.58(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11113
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      68.11
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752.00
_exptl_absorpt_coefficient_mu    1.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_T_max  0.872

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19789
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_theta_max         68.164
_diffrn_reflns_theta_min         3.956
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3112
_reflns_number_gt                3037
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# 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          0.0326
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0904
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     231
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0536P)²+0.5110P] 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         0.20
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
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)
;

#==============================================================================
# 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
S12 S 1.35642(11) 0.22129(4) 0.36765(4) 0.0314(2) Uani 1 1 d . . . . .
O3 O 0.8734(3) 0.76641(13) 0.33543(11) 0.0276(4) Uani 1 1 d . . . . .
O8 O 0.9897(3) 0.50614(13) 0.44065(10) 0.0287(4) Uani 1 1 d . . . . .
O13 O 0.7258(3) 0.62542(14) 0.31826(11) 0.0299(5) Uani 1 1 d . . . . .
O20 O 0.5559(3) 0.80137(13) 0.46609(10) 0.0285(4) Uani 1 1 d . . . . .
O21 O 0.5328(3) 0.84533(13) 0.34837(10) 0.0274(4) Uani 1 1 d . . . . .
O22 O 0.3316(4) 0.92262(16) 0.22005(13) 0.0434(6) Uani 1 1 d D . . . .
H22A H 0.323(7) 0.9900(6) 0.217(2) 0.065 Uiso 1 1 d D U . . .
H22B H 0.389(6) 0.900(3) 0.2645(13) 0.065 Uiso 1 1 d D U . . .
N6 N 1.0918(3) 0.53060(15) 0.32486(11) 0.0221(5) Uani 1 1 d . . . . .
N19 N 0.2042(4) 0.87394(16) 0.50624(12) 0.0220(5) Uani 1 1 d . . . . .
C1 C 0.8750(4) 0.67374(18) 0.32765(13) 0.0216(5) Uani 1 1 d . . . . .
C2 C 1.0884(4) 0.63388(18) 0.33322(15) 0.0238(6) Uani 1 1 d . . . . .
H2 H 1.1488 0.6518 0.3814 0.029 Uiso 1 1 calc R U . . .
C3 C 1.2248(4) 0.66769(19) 0.27092(15) 0.0282(6) Uani 1 1 d . . . . .
H3A H 1.1897 0.7328 0.2554 0.034 Uiso 1 1 calc R U . . .
H3B H 1.3684 0.6658 0.2853 0.034 Uiso 1 1 calc R U . . .
C4 C 1.1797(5) 0.5962(2) 0.21106(16) 0.0305(6) Uani 1 1 d . . . . .
H4A H 1.2900 0.5942 0.1747 0.037 Uiso 1 1 calc R U . . .
H4B H 1.0524 0.6119 0.1857 0.037 Uiso 1 1 calc R U . . .
C5 C 1.1621(4) 0.50174(19) 0.25131(13) 0.0256(6) Uani 1 1 d . . . . .
H5A H 1.0633 0.4595 0.2272 0.031 Uiso 1 1 calc R U . . .
H5B H 1.2938 0.4691 0.2540 0.031 Uiso 1 1 calc R U . . .
C7 C 1.0439(4) 0.47335(17) 0.38058(14) 0.0224(5) Uani 1 1 d . . . . .
C9 C 1.0687(4) 0.36675(17) 0.37051(15) 0.0226(5) Uani 1 1 d . . . . .
H9 H 1.0484 0.3507 0.3177 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9149(5) 0.3127(2) 0.41629(17) 0.0322(6) Uani 1 1 d . . . . .
H10A H 0.7788 0.3282 0.3994 0.039 Uiso 1 1 calc R U . . .
H10B H 0.9290 0.3306 0.4678 0.039 Uiso 1 1 calc R U . . .
H10C H 0.9380 0.2445 0.4111 0.039 Uiso 1 1 calc R U . . .
C11 C 1.2860(4) 0.34133(19) 0.39248(15) 0.0255(6) Uani 1 1 d . . . . .
H11A H 1.3007 0.3491 0.4460 0.031 Uiso 1 1 calc R U . . .
H11B H 1.3797 0.3862 0.3685 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4675(4) 0.83795(17) 0.41363(14) 0.0219(5) Uani 1 1 d . . . . .
C15 C 0.2570(4) 0.87828(17) 0.42652(14) 0.0214(5) Uani 1 1 d . . . . .
H15 H 0.1569 0.8404 0.3980 0.026 Uiso 1 1 calc R U . . .
C16 C 0.2274(4) 0.98343(18) 0.40950(14) 0.0252(6) Uani 1 1 d . . . . .
H16A H 0.1993 0.9931 0.3568 0.030 Uiso 1 1 calc R U . . .
H16B H 0.3485 1.0204 0.4231 0.030 Uiso 1 1 calc R U . . .
C17 C 0.0464(6) 1.0127(2) 0.45614(18) 0.0427(8) Uani 1 1 d . . . . .
H17A H 0.0686 1.0762 0.4777 0.051 Uiso 1 1 calc R U . . .
H17B H -0.0773 1.0147 0.4260 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0265(5) 0.9380(2) 0.51641(15) 0.0298(6) Uani 1 1 d . . . . .
H18A H 0.0296 0.9680 0.5654 0.036 Uiso 1 1 calc R U . . .
H18B H -0.1009 0.9024 0.5112 0.036 Uiso 1 1 calc R U . . .
H3 H 0.764(8) 0.789(4) 0.335(3) 0.078(16) Uiso 1 1 d . . . . .
H12 H 1.399(7) 0.242(3) 0.308(2) 0.070(13) Uiso 1 1 d . . . . .
H19A H 0.190(5) 0.819(3) 0.5200(18) 0.031(9) Uiso 1 1 d . . . . .
H19B H 0.312(6) 0.895(2) 0.5305(18) 0.032(9) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_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
S12 C11 1.816(3) . ?
S12 H12 1.16(4) . ?
O3 C1 1.316(3) . ?
O3 H3 0.80(6) . ?
O8 C7 1.245(3) . ?
O13 C1 1.215(3) . ?
O20 C14 1.238(3) . ?
O21 C14 1.274(3) . ?
O22 H22A 0.955(7) . ?
O22 H22B 0.954(7) . ?
N6 C7 1.339(3) . ?
N6 C2 1.467(3) . ?
N6 C5 1.480(3) . ?
N19 C18 1.499(4) . ?
N19 C15 1.500(3) . ?
N19 H19A 0.81(4) . ?
N19 H19B 0.89(4) . ?
C1 C2 1.529(4) . ?
C2 C3 1.532(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C9 1.525(3) . ?
C9 C10 1.526(4) . ?
C9 C11 1.540(4) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 C15 1.528(4) . ?
C15 C16 1.530(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.531(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.531(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C11 S12 H12 93(2) . . ?
C1 O3 H3 114(4) . . ?
H22A O22 H22B 114(4) . . ?
C7 N6 C2 121.2(2) . . ?
C7 N6 C5 126.8(2) . . ?
C2 N6 C5 111.9(2) . . ?
C18 N19 C15 106.3(2) . . ?
C18 N19 H19A 116(3) . . ?
C15 N19 H19A 111(2) . . ?
C18 N19 H19B 111(2) . . ?
C15 N19 H19B 106(2) . . ?
H19A N19 H19B 105(3) . . ?
O13 C1 O3 124.5(2) . . ?
O13 C1 C2 124.0(2) . . ?
O3 C1 C2 111.5(2) . . ?
N6 C2 C1 111.9(2) . . ?
N6 C2 C3 102.9(2) . . ?
C1 C2 C3 112.6(2) . . ?
N6 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
C4 C3 C2 102.2(2) . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C3 C4 C5 104.4(2) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
N6 C5 C4 102.8(2) . . ?
N6 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
N6 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
O8 C7 N6 121.0(2) . . ?
O8 C7 C9 120.3(2) . . ?
N6 C7 C9 118.6(2) . . ?
C7 C9 C10 110.8(2) . . ?
C7 C9 C11 107.4(2) . . ?
C10 C9 C11 111.6(2) . . ?
C7 C9 H9 109.0 . . ?
C10 C9 H9 109.0 . . ?
C11 C9 H9 109.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 S12 113.18(18) . . ?
C9 C11 H11A 108.9 . . ?
S12 C11 H11A 108.9 . . ?
C9 C11 H11B 108.9 . . ?
S12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
O20 C14 O21 126.7(3) . . ?
O20 C14 C15 118.1(2) . . ?
O21 C14 C15 115.2(2) . . ?
N19 C15 C14 110.4(2) . . ?
N19 C15 C16 102.0(2) . . ?
C14 C15 C16 116.6(2) . . ?
N19 C15 H15 109.2 . . ?
C14 C15 H15 109.2 . . ?
C16 C15 H15 109.2 . . ?
C15 C16 C17 104.5(2) . . ?
C15 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 106.4(2) . . ?
C18 C17 H17A 110.4 . . ?
C16 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
C16 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
N19 C18 C17 105.0(2) . . ?
N19 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
N19 C18 H18B 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?

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
C7 N6 C2 C1 -79.8(3) . . . . ?
C5 N6 C2 C1 103.0(3) . . . . ?
C7 N6 C2 C3 159.0(2) . . . . ?
C5 N6 C2 C3 -18.1(3) . . . . ?
O13 C1 C2 N6 0.8(4) . . . . ?
O3 C1 C2 N6 179.8(2) . . . . ?
O13 C1 C2 C3 116.2(3) . . . . ?
O3 C1 C2 C3 -64.8(3) . . . . ?
N6 C2 C3 C4 35.0(3) . . . . ?
C1 C2 C3 C4 -85.7(3) . . . . ?
C2 C3 C4 C5 -39.7(3) . . . . ?
C7 N6 C5 C4 176.8(3) . . . . ?
C2 N6 C5 C4 -6.2(3) . . . . ?
C3 C4 C5 N6 28.5(3) . . . . ?
C2 N6 C7 O8 2.0(4) . . . . ?
C5 N6 C7 O8 178.7(2) . . . . ?
C2 N6 C7 C9 -174.5(2) . . . . ?
C5 N6 C7 C9 2.2(4) . . . . ?
O8 C7 C9 C10 33.8(4) . . . . ?
N6 C7 C9 C10 -149.7(2) . . . . ?
O8 C7 C9 C11 -88.4(3) . . . . ?
N6 C7 C9 C11 88.2(3) . . . . ?
C7 C9 C11 S12 -169.06(19) . . . . ?
C10 C9 C11 S12 69.3(3) . . . . ?
C18 N19 C15 C14 164.5(2) . . . . ?
C18 N19 C15 C16 39.9(3) . . . . ?
O20 C14 C15 N19 5.9(3) . . . . ?
O21 C14 C15 N19 -174.7(2) . . . . ?
O20 C14 C15 C16 121.6(3) . . . . ?
O21 C14 C15 C16 -59.0(3) . . . . ?
N19 C15 C16 C17 -36.1(3) . . . . ?
C14 C15 C16 C17 -156.4(2) . . . . ?
C15 C16 C17 C18 19.7(3) . . . . ?
C15 N19 C18 C17 -27.8(3) . . . . ?
C16 C17 C18 N19 4.5(4) . . . . ?

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
O3 H3 O21 . . . 2.533(3) 0.80(5) 1.74(5) 170(5) no
O22 H22A O13 . . 4_655 2.973(3) 0.955(9) 2.042(17) 164(4) no
O22 H22B O21 . . . 2.912(3) 0.95(3) 1.96(3) 173(3) no
N19 H19A O20 . . 3_466 2.712(3) 0.81(4) 1.94(4) 157(3) no
N19 H19B O8 . . 3_466 2.721(3) 0.89(4) 1.90(3) 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.


