# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_DMSS-AM
_database_code_depnum_ccdc_archive 'CCDC 2329895'
loop_
_audit_author_name
_audit_author_address
'Yongyang Gong'
;Guilin University of Technology
China
;
_audit_update_record             
;
2024-01-31 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_audit_creation_date             2023-12-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            DMSS-AM
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H34 N4 O6'
_chemical_formula_sum            'C22 H36 N4 O6'
_chemical_formula_weight         452.55
_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 0.0181 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   10.105(4)
_cell_length_b                   7.746(3)
_cell_length_c                   15.032(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.13(3)
_cell_angle_gamma                90
_cell_volume                     1176.5(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    323
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      33.13
_cell_measurement_theta_min      5.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5692
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0863 after correction.
The Ratio of minimum to maximum transmission is 0.7558.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             488
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.499
_diffrn_reflns_theta_min         5.227
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1504
_reflns_number_total             2158
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'cis-12 2023.11.22'
_computing_data_collection       ?
_computing_data_reduction        'cis-12 2023.11.22'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.106
_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)+(0.1368P)²+0.0191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.2109
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.33044(16) 0.1136(2) 0.56579(10) 0.0676(5) Uani 1 1 d . . . . .
O002 O 0.3751(2) 0.0722(2) 0.42328(12) 0.0765(6) Uani 1 1 d . . . . .
O003 O 0.4669(2) 1.1713(3) 0.87876(15) 0.0902(7) Uani 1 1 d . . . . .
N004 N 0.54607(19) 0.8380(2) 0.82218(13) 0.0604(5) Uani 1 1 d . . . . .
N005 N 0.5538(2) 0.6403(3) 0.66884(13) 0.0666(6) Uani 1 1 d . . . . .
C006 C 0.4421(2) 0.3366(3) 0.49304(15) 0.0537(6) Uani 1 1 d . . . . .
C007 C 0.4677(2) 0.4110(3) 0.57558(16) 0.0563(6) Uani 1 1 d . . . . .
C008 C 0.5253(2) 0.5744(3) 0.58595(15) 0.0558(6) Uani 1 1 d . . . . .
C009 C 0.3811(2) 0.1629(3) 0.48851(15) 0.0565(6) Uani 1 1 d . . . . .
C00A C 0.5759(3) 0.6536(3) 0.82808(18) 0.0694(7) Uani 1 1 d . . . . .
C00B C 0.5180(3) 0.5548(3) 0.74973(17) 0.0682(7) Uani 1 1 d . . . . .
C00C C 0.6288(3) 0.9417(4) 0.8812(2) 0.0769(8) Uani 1 1 d . . . . .
C00D C 0.2702(3) -0.0559(4) 0.5681(2) 0.0777(8) Uani 1 1 d . . . . .
C00E C 0.4085(3) 0.8786(4) 0.8394(3) 0.0834(9) Uani 1 1 d . . . . .
C00F C 0.6012(3) 1.1295(4) 0.8653(3) 0.0912(10) Uani 1 1 d . . . . .
C00G C 0.3844(4) 1.0671(5) 0.8244(3) 0.0958(11) Uani 1 1 d . . . . .
H007 H 0.449(2) 0.351(3) 0.6261(18) 0.060(7) Uiso 1 1 d . . . . .
H00E H 0.722(3) 0.910(4) 0.867(2) 0.086(9) Uiso 1 1 d . . . . .
H00C H 0.413(3) 0.541(4) 0.7526(19) 0.079(8) Uiso 1 1 d . . . . .
H00A H 0.542(3) 0.598(4) 0.884(2) 0.084(8) Uiso 1 1 d . . . . .
H00D H 0.557(3) 0.437(4) 0.7491(19) 0.077(8) Uiso 1 1 d . . . . .
H00B H 0.679(3) 0.646(3) 0.8272(16) 0.062(6) Uiso 1 1 d . . . . .
H00L H 0.616(3) 1.153(4) 0.800(3) 0.097(11) Uiso 1 1 d . . . . .
H00J H 0.386(4) 0.836(5) 0.904(3) 0.121(12) Uiso 1 1 d . . . . .
H00N H 0.290(4) 1.095(6) 0.838(3) 0.126(13) Uiso 1 1 d . . . . .
H00O H 0.408(4) 1.090(5) 0.762(3) 0.116(13) Uiso 1 1 d . . . . .
H00K H 0.352(3) 0.815(5) 0.798(3) 0.108(11) Uiso 1 1 d . . . . .
H00F H 0.611(4) 0.917(5) 0.948(3) 0.120(12) Uiso 1 1 d . . . . .
H00G H 0.184(5) -0.052(6) 0.531(3) 0.145(16) Uiso 1 1 d . . . . .
H005 H 0.570(3) 0.752(5) 0.674(2) 0.086(9) Uiso 1 1 d . . . . .
H00H H 0.225(4) -0.061(5) 0.624(3) 0.120(12) Uiso 1 1 d . . . . .
H00I H 0.325(4) -0.137(5) 0.540(3) 0.114(12) Uiso 1 1 d . . . . .
H00M H 0.651(4) 1.203(6) 0.910(3) 0.124(12) Uiso 1 1 d . . . . .


_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
O001 C009 1.334(3) . ?
O001 C00D 1.447(3) . ?
O002 C009 1.207(3) . ?
O003 C00F 1.414(4) . ?
O003 C00G 1.409(4) . ?
N004 C00A 1.462(3) . ?
N004 C00C 1.450(3) . ?
N004 C00E 1.454(4) . ?
N005 C008 1.372(3) . ?
N005 C00B 1.437(3) . ?
N005 H005 0.88(4) . ?
C006 C007 1.388(3) . ?
C006 C008 1.417(3) 3_666 ?
C006 C009 1.481(3) . ?
C007 C008 1.401(3) . ?
C007 H007 0.91(3) . ?
C00A C00B 1.513(4) . ?
C00A H00A 1.01(3) . ?
C00A H00B 1.04(3) . ?
C00B H00C 1.06(3) . ?
C00B H00D 0.99(3) . ?
C00C C00F 1.500(5) . ?
C00C H00E 1.00(3) . ?
C00C H00F 1.04(4) . ?
C00D H00G 1.03(5) . ?
C00D H00H 0.97(4) . ?
C00D H00I 0.94(4) . ?
C00E C00G 1.496(5) . ?
C00E H00J 1.06(4) . ?
C00E H00K 0.97(4) . ?
C00F H00L 1.00(4) . ?
C00F H00M 1.01(5) . ?
C00G H00N 1.00(4) . ?
C00G H00O 0.99(4) . ?

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
C009 O001 C00D 116.7(2) . . ?
C00G O003 C00F 110.1(3) . . ?
C00C N004 C00A 112.8(2) . . ?
C00C N004 C00E 108.3(2) . . ?
C00E N004 C00A 113.4(2) . . ?
C008 N005 C00B 123.1(2) . . ?
C008 N005 H005 119(2) . . ?
C00B N005 H005 115(2) . . ?
C007 C006 C008 120.3(2) . 3_666 ?
C007 C006 C009 119.25(19) . . ?
C008 C006 C009 120.44(19) 3_666 . ?
C006 C007 C008 123.0(2) . . ?
C006 C007 H007 119.6(15) . . ?
C008 C007 H007 117.4(15) . . ?
N005 C008 C006 122.2(2) . 3_666 ?
N005 C008 C007 121.1(2) . . ?
C007 C008 C006 116.7(2) . 3_666 ?
O001 C009 C006 112.74(19) . . ?
O002 C009 O001 121.8(2) . . ?
O002 C009 C006 125.5(2) . . ?
N004 C00A C00B 111.8(2) . . ?
N004 C00A H00A 113.6(17) . . ?
N004 C00A H00B 104.9(13) . . ?
C00B C00A H00A 107.3(17) . . ?
C00B C00A H00B 109.5(13) . . ?
H00A C00A H00B 110(2) . . ?
N005 C00B C00A 109.0(2) . . ?
N005 C00B H00C 110.2(16) . . ?
N005 C00B H00D 108.1(16) . . ?
C00A C00B H00C 112.8(16) . . ?
C00A C00B H00D 109.0(17) . . ?
H00C C00B H00D 108(2) . . ?
N004 C00C C00F 109.6(3) . . ?
N004 C00C H00E 105.6(18) . . ?
N004 C00C H00F 112(2) . . ?
C00F C00C H00E 112.2(19) . . ?
C00F C00C H00F 107(2) . . ?
H00E C00C H00F 110(3) . . ?
O001 C00D H00G 108(3) . . ?
O001 C00D H00H 106(2) . . ?
O001 C00D H00I 110(2) . . ?
H00G C00D H00H 94(3) . . ?
H00G C00D H00I 106(4) . . ?
H00H C00D H00I 131(3) . . ?
N004 C00E C00G 109.7(3) . . ?
N004 C00E H00J 108(2) . . ?
N004 C00E H00K 109(2) . . ?
C00G C00E H00J 114(2) . . ?
C00G C00E H00K 108(2) . . ?
H00J C00E H00K 107(3) . . ?
O003 C00F C00C 112.1(3) . . ?
O003 C00F H00L 105(2) . . ?
O003 C00F H00M 104(2) . . ?
C00C C00F H00L 107(2) . . ?
C00C C00F H00M 111(2) . . ?
H00L C00F H00M 118(3) . . ?
O003 C00G C00E 112.3(3) . . ?
O003 C00G H00N 108(2) . . ?
O003 C00G H00O 107(2) . . ?
C00E C00G H00N 110(2) . . ?
C00E C00G H00O 106(2) . . ?
H00N C00G H00O 114(3) . . ?

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
N004 C00A C00B N005 49.8(3) . . . . ?
N004 C00C C00F O003 58.6(4) . . . . ?
N004 C00E C00G O003 -58.3(4) . . . . ?
C006 C007 C008 N005 -177.3(2) . . . . ?
C006 C007 C008 C006 -0.1(3) . . . 3_666 ?
C007 C006 C009 O001 14.1(3) . . . . ?
C007 C006 C009 O002 -166.2(2) . . . . ?
C008 N005 C00B C00A 174.5(2) . . . . ?
C008 C006 C007 C008 0.1(4) 3_666 . . . ?
C008 C006 C009 O001 -166.16(19) 3_666 . . . ?
C008 C006 C009 O002 13.5(3) 3_666 . . . ?
C009 C006 C007 C008 179.9(2) . . . . ?
C00A N004 C00C C00F 174.8(2) . . . . ?
C00A N004 C00E C00G -175.3(3) . . . . ?
C00B N005 C008 C006 178.0(2) . . . 3_666 ?
C00B N005 C008 C007 -4.9(4) . . . . ?
C00C N004 C00A C00B -163.9(2) . . . . ?
C00C N004 C00E C00G 58.7(4) . . . . ?
C00D O001 C009 O002 1.2(3) . . . . ?
C00D O001 C009 C006 -179.1(2) . . . . ?
C00E N004 C00A C00B 72.5(3) . . . . ?
C00E N004 C00C C00F -58.8(3) . . . . ?
C00F O003 C00G C00E 56.0(4) . . . . ?
C00G O003 C00F C00C -56.0(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 7.3 0.1 ?
2 0.500 0.500 0.000 7.3 0.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
