# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_SSP41_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2251989'
loop_
_audit_author_name
_audit_author_address
'Swati Singh'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2023-03-27 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        SS-P4-3a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.08 H2.24 N0.32 O0.48'
_chemical_formula_weight         39.40

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 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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7425(15)
_cell_length_b                   8.7545(18)
_cell_length_c                   18.745(4)
_cell_angle_alpha                101.445(7)
_cell_angle_beta                 91.780(6)
_cell_angle_gamma                93.333(6)
_cell_volume                     1242.0(4)
_cell_formula_units_Z            25
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3802
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.37

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61478
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6162
_reflns_number_gt                2726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0784P)²+0.2347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6162
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1437
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.2106
_refine_ls_wR_factor_gt          0.1615
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_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
O1_1 O 1.0280(2) 0.43138(18) 0.32546(9) 0.0791(5) Uani 1 1 d . . . . .
O2_1 O 0.9187(3) 0.6653(2) 0.05231(10) 0.1066(7) Uani 1 1 d . . . . .
O3_1 O 1.0635(3) 0.2988(2) 0.21423(10) 0.0969(6) Uani 1 1 d . . . . .
N1_1 N 0.8541(2) 0.8016(2) 0.16298(10) 0.0699(5) Uani 1 1 d . . . . .
C1_1 C 0.8915(3) 0.6909(2) 0.27133(12) 0.0597(5) Uani 1 1 d . . . . .
C2_1 C 0.8398(3) 0.8133(2) 0.23833(12) 0.0615(6) Uani 1 1 d . . . . .
C3_1 C 0.7728(3) 0.9450(3) 0.27891(14) 0.0722(6) Uani 1 1 d . . . . .
H3_1 H 0.737899 1.023601 0.255866 0.087 Uiso 1 1 calc R U . . .
C4_1 C 0.7577(3) 0.9606(3) 0.35220(14) 0.0797(7) Uani 1 1 d . . . . .
H4_1 H 0.712911 1.049410 0.379039 0.096 Uiso 1 1 calc R U . . .
C5_1 C 0.8088(3) 0.8446(3) 0.38619(14) 0.0820(7) Uani 1 1 d . . . . .
H5_1 H 0.799515 0.855434 0.436261 0.098 Uiso 1 1 calc R U . . .
C6_1 C 0.8736(3) 0.7127(3) 0.34685(13) 0.0748(7) Uani 1 1 d . . . . .
H6_1 H 0.906740 0.635304 0.370998 0.090 Uiso 1 1 calc R U . . .
C7_1 C 0.9570(3) 0.5521(2) 0.22623(12) 0.0626(6) Uani 1 1 d . . . . .
C8_1 C 0.9633(3) 0.5440(3) 0.15257(13) 0.0689(6) Uani 1 1 d . . . . .
C9_1 C 0.9101(3) 0.6740(3) 0.11843(13) 0.0753(7) Uani 1 1 d . . . . .
C10_1 C 1.0196(3) 0.4173(3) 0.25339(14) 0.0695(6) Uani 1 1 d . . . . .
C11_1 C 1.0858(4) 0.2977(3) 0.35171(15) 0.0914(8) Uani 1 1 d . . . . .
H11A_1 H 1.205330 0.281715 0.339874 0.110 Uiso 1 1 calc R U . . .
H11B_1 H 1.015063 0.204339 0.329401 0.110 Uiso 1 1 calc R U . . .
C12_1 C 1.0690(5) 0.3310(4) 0.43239(17) 0.1267(12) Uani 1 1 d . . . . .
H12A_1 H 1.098665 0.241530 0.451477 0.190 Uiso 1 1 calc R U . . .
H12B_1 H 0.951834 0.353718 0.443443 0.190 Uiso 1 1 calc R U . . .
H12C_1 H 1.145698 0.419226 0.454110 0.190 Uiso 1 1 calc R U . . .
C14_1 C 0.8108(4) 0.9322(3) 0.12938(15) 0.0979(9) Uani 1 1 d . . . . .
H14A_1 H 0.834965 0.908534 0.078586 0.147 Uiso 1 1 calc R U . . .
H14B_1 H 0.878994 1.024629 0.152891 0.147 Uiso 1 1 calc R U . . .
H14C_1 H 0.690132 0.949320 0.134581 0.147 Uiso 1 1 calc R U . . .
O1_2 O 0.4276(3) 0.6572(3) 0.47150(11) 0.1157(7) Uani 1 1 d . . . . .
O2_2 O 0.5970(3) 0.2900(2) 0.24746(12) 0.1083(7) Uani 1 1 d . . . . .
O3_2 O 0.4981(3) 0.3936(2) 0.15918(11) 0.1158(7) Uani 1 1 d . . . . .
N1_2 N 0.3517(2) 0.7811(3) 0.38178(11) 0.0758(6) Uani 1 1 d . . . . .
N2_2 N 1.0175(3) 0.4256(3) 0.10281(11) 0.0948(7) Uani 1 1 d . . . . .
H2A_2 H 1.053087 0.344049 0.116284 0.114 Uiso 1 1 calc R U . . .
H2B_2 H 1.016606 0.431525 0.057550 0.114 Uiso 1 1 calc R U . . .
N3_2 N 0.5431(3) 0.4197(3) 0.38198(13) 0.1029(8) Uani 1 1 d . . . . .
H3A_2 H 0.581324 0.338461 0.355014 0.124 Uiso 1 1 calc R U . . .
H3B_2 H 0.545474 0.428808 0.428539 0.124 Uiso 1 1 calc R U . . .
C1_2 C 0.4020(3) 0.6709(3) 0.25484(13) 0.0641(6) Uani 1 1 d . . . . .
C2_2 C 0.3457(3) 0.7927(3) 0.30792(13) 0.0662(6) Uani 1 1 d . . . . .
C3_2 C 0.2851(3) 0.9248(3) 0.28876(15) 0.0803(7) Uani 1 1 d . . . . .
H3_2 H 0.249349 1.003979 0.324989 0.096 Uiso 1 1 calc R U . . .
C4_2 C 0.2762(3) 0.9422(3) 0.21840(17) 0.0870(8) Uani 1 1 d . . . . .
H4_2 H 0.234456 1.031890 0.206525 0.104 Uiso 1 1 calc R U . . .
C5_2 C 0.3299(4) 0.8253(3) 0.16483(15) 0.0890(8) Uani 1 1 d . . . . .
H5_2 H 0.324669 0.835920 0.116439 0.107 Uiso 1 1 calc R U . . .
C6_2 C 0.3917(3) 0.6916(3) 0.18284(14) 0.0776(7) Uani 1 1 d . . . . .
H6_2 H 0.427207 0.613671 0.145997 0.093 Uiso 1 1 calc R U . . .
C7_2 C 0.4677(3) 0.5342(3) 0.27783(13) 0.0682(6) Uani 1 1 d . . . . .
C8_2 C 0.4796(3) 0.5328(3) 0.35124(15) 0.0777(7) Uani 1 1 d . . . . .
C9_2 C 0.4188(3) 0.6613(3) 0.40606(15) 0.0826(7) Uani 1 1 d . . . . .
C10_2 C 0.5267(3) 0.3964(3) 0.22834(16) 0.0787(7) Uani 1 1 d . . . . .
C11_2 C 0.5512(6) 0.2582(5) 0.1084(2) 0.1553(17) Uani 1 1 d . . . . .
H11A_2 H 0.673819 0.246689 0.116249 0.186 Uiso 1 1 calc R U . . .
H11B_2 H 0.487741 0.164498 0.116261 0.186 Uiso 1 1 calc R U . . .
C12_2 C 0.5185(9) 0.2779(7) 0.0389(2) 0.241(3) Uani 1 1 d . . . . .
H12A_2 H 0.575075 0.201141 0.005383 0.361 Uiso 1 1 calc R U . . .
H12B_2 H 0.561452 0.380538 0.034427 0.361 Uiso 1 1 calc R U . . .
H12C_2 H 0.395888 0.265893 0.027935 0.361 Uiso 1 1 calc R U . . .
C14_2 C 0.2918(4) 0.9084(4) 0.43639(15) 0.1035(9) Uani 1 1 d . . . . .
H14A_2 H 0.299921 0.881646 0.483583 0.155 Uiso 1 1 calc R U . . .
H14B_2 H 0.173627 0.924750 0.424709 0.155 Uiso 1 1 calc R U . . .
H14C_2 H 0.362731 1.002202 0.436701 0.155 Uiso 1 1 calc R U . . .


_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
O1_1 C10_1 1.331(3) . ?
O1_1 C11_1 1.445(3) . ?
O2_1 C9_1 1.231(3) . ?
O3_1 C10_1 1.218(3) . ?
N1_1 C9_1 1.357(3) . ?
N1_1 C2_1 1.404(3) . ?
N1_1 C14_1 1.461(3) . ?
C1_1 C6_1 1.403(3) . ?
C1_1 C2_1 1.410(3) . ?
C1_1 C7_1 1.462(3) . ?
C2_1 C3_1 1.387(3) . ?
C3_1 C4_1 1.363(3) . ?
C4_1 C5_1 1.372(3) . ?
C5_1 C6_1 1.371(3) . ?
C7_1 C8_1 1.371(3) . ?
C7_1 C10_1 1.476(3) . ?
C8_1 N2_2 1.346(3) . ?
C8_1 C9_1 1.483(3) . ?
C11_1 C12_1 1.494(4) . ?
O1_2 C9_2 1.234(3) . ?
O2_2 C10_2 1.214(3) . ?
O3_2 C10_2 1.303(3) . ?
O3_2 C11_2 1.454(4) . ?
N1_2 C9_2 1.348(3) . ?
N1_2 C2_2 1.408(3) . ?
N1_2 C14_2 1.463(3) . ?
N3_2 C8_2 1.349(3) . ?
C1_2 C6_2 1.398(3) . ?
C1_2 C2_2 1.406(3) . ?
C1_2 C7_2 1.462(3) . ?
C2_2 C3_2 1.380(3) . ?
C3_2 C4_2 1.358(4) . ?
C4_2 C5_2 1.377(4) . ?
C5_2 C6_2 1.387(3) . ?
C7_2 C8_2 1.379(3) . ?
C7_2 C10_2 1.473(3) . ?
C8_2 C9_2 1.475(4) . ?
C11_2 C12_2 1.367(6) . ?

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
C10_1 O1_1 C11_1 115.65(19) . . ?
C9_1 N1_1 C2_1 123.2(2) . . ?
C9_1 N1_1 C14_1 116.9(2) . . ?
C2_1 N1_1 C14_1 119.84(19) . . ?
C6_1 C1_1 C2_1 115.9(2) . . ?
C6_1 C1_1 C7_1 124.7(2) . . ?
C2_1 C1_1 C7_1 119.4(2) . . ?
C3_1 C2_1 N1_1 119.1(2) . . ?
C3_1 C2_1 C1_1 121.1(2) . . ?
N1_1 C2_1 C1_1 119.74(19) . . ?
C4_1 C3_1 C2_1 120.7(2) . . ?
C3_1 C4_1 C5_1 119.7(2) . . ?
C6_1 C5_1 C4_1 120.5(2) . . ?
C5_1 C6_1 C1_1 122.1(2) . . ?
C8_1 C7_1 C1_1 118.7(2) . . ?
C8_1 C7_1 C10_1 116.0(2) . . ?
C1_1 C7_1 C10_1 125.3(2) . . ?
N2_2 C8_1 C7_1 126.9(2) . . ?
N2_2 C8_1 C9_1 111.5(2) . . ?
C7_1 C8_1 C9_1 121.5(2) . . ?
O2_1 C9_1 N1_1 122.0(2) . . ?
O2_1 C9_1 C8_1 120.6(2) . . ?
N1_1 C9_1 C8_1 117.4(2) . . ?
O3_1 C10_1 O1_1 120.1(2) . . ?
O3_1 C10_1 C7_1 124.0(2) . . ?
O1_1 C10_1 C7_1 115.9(2) . . ?
O1_1 C11_1 C12_1 107.0(2) . . ?
C10_2 O3_2 C11_2 116.9(3) . . ?
C9_2 N1_2 C2_2 123.3(2) . . ?
C9_2 N1_2 C14_2 117.3(2) . . ?
C2_2 N1_2 C14_2 119.3(2) . . ?
C6_2 C1_2 C2_2 116.3(2) . . ?
C6_2 C1_2 C7_2 124.7(2) . . ?
C2_2 C1_2 C7_2 119.0(2) . . ?
C3_2 C2_2 C1_2 120.9(2) . . ?
C3_2 C2_2 N1_2 119.2(2) . . ?
C1_2 C2_2 N1_2 119.9(2) . . ?
C4_2 C3_2 C2_2 121.7(2) . . ?
C3_2 C4_2 C5_2 119.1(3) . . ?
C4_2 C5_2 C6_2 120.2(3) . . ?
C5_2 C6_2 C1_2 121.8(2) . . ?
C8_2 C7_2 C1_2 118.6(2) . . ?
C8_2 C7_2 C10_2 116.4(2) . . ?
C1_2 C7_2 C10_2 125.0(2) . . ?
N3_2 C8_2 C7_2 126.5(3) . . ?
N3_2 C8_2 C9_2 112.0(2) . . ?
C7_2 C8_2 C9_2 121.5(2) . . ?
O1_2 C9_2 N1_2 121.7(3) . . ?
O1_2 C9_2 C8_2 120.8(3) . . ?
N1_2 C9_2 C8_2 117.5(2) . . ?
O2_2 C10_2 O3_2 119.8(3) . . ?
O2_2 C10_2 C7_2 125.1(3) . . ?
O3_2 C10_2 C7_2 115.1(2) . . ?
C12_2 C11_2 O3_2 108.9(3) . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.059

