# Electronic Supplementary Material (ESI) for ChemComm.
# 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_SGSS326X
_database_code_depnum_ccdc_archive 'CCDC 2034533'
loop_
_audit_author_name
_audit_author_address
'Subhash Chandra Ghosh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         312.36

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   7.0141(7)
_cell_length_b                   11.0390(11)
_cell_length_c                   22.180(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.678(3)
_cell_angle_gamma                90
_cell_volume                     1702.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2707
_cell_measurement_theta_min      2.6151
_cell_measurement_theta_max      28.6409
_cell_measurement_temperature    301.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.095
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9920

_exptl_special_details           
;
;

_diffrn_ambient_temperature      301.(2)

_diffrn_source                   'MICRO FOCUS TUBE'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            25369
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32

_refine_special_details          
;
;

_reflns_number_total             5626
_reflns_number_gt                1821
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1973
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_gt          0.2518
_refine_ls_wR_factor_ref         0.3669
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_number_reflns         5626
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1854P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.3581(4) 0.1077(3) 0.56185(10) 0.1216(9) Uani d . . . 1 . .
O O2 -0.1863(4) 0.1896(3) 0.24555(12) 0.1294(10) Uani d . . . 1 . .
O O3 0.4605(3) 0.27430(17) 0.36500(9) 0.0876(6) Uani d . . . 1 . .
N N1 0.7915(3) 0.2390(2) 0.53097(12) 0.0942(8) Uani d . . . 1 . .
N N2 0.4569(4) 0.1727(2) 0.47362(11) 0.0842(7) Uani d . . . 1 . .
C C1 0.9624(5) 0.2741(4) 0.55961(18) 0.1116(11) Uani d . . . 1 . .
H H1 1.0517 0.304946 0.536219 0.134 Uiso calc U . R 1 . .
C C2 1.0137(5) 0.2674(3) 0.62103(19) 0.1131(11) Uani d . . . 1 . .
H H2 1.135614 0.291774 0.638504 0.136 Uiso calc U . R 1 . .
C C3 0.8866(6) 0.2254(4) 0.65581(18) 0.1161(12) Uani d . . . 1 . .
H H3 0.917307 0.222224 0.697889 0.139 Uiso calc U . R 1 . .
C C4 0.7087(5) 0.1869(3) 0.62812(15) 0.1042(10) Uani d . . . 1 . .
H H4 0.617721 0.156552 0.651039 0.125 Uiso calc U . R 1 . .
C C5 0.6698(5) 0.1947(3) 0.56596(14) 0.0861(8) Uani d . . . 1 . .
C C6 0.4798(5) 0.1531(3) 0.53421(14) 0.0860(8) Uani d . . . 1 . .
C C7 0.2927(4) 0.1579(2) 0.43088(12) 0.0772(7) Uani d . . . 1 . .
C C8 0.1341(4) 0.0908(3) 0.44122(13) 0.0880(9) Uani d . . . 1 . .
H H8 0.131949 0.052264 0.478409 0.106 Uiso calc U . R 1 . .
C C9 -0.0223(4) 0.0810(3) 0.39583(13) 0.0881(9) Uani d . . . 1 . .
H H9 -0.129877 0.037178 0.403292 0.106 Uiso calc U . R 1 . .
C C10 -0.0204(4) 0.1354(3) 0.33987(13) 0.0808(8) Uani d . . . 1 . .
C C11 0.1412(4) 0.2017(2) 0.32994(13) 0.0813(8) Uani d . . . 1 . .
H H11 0.144972 0.238037 0.292289 0.098 Uiso calc U . R 1 . .
C C12 0.2953(4) 0.2145(2) 0.37467(12) 0.0753(7) Uani d . . . 1 . .
C C13 -0.1844(4) 0.1263(3) 0.29048(15) 0.0941(9) Uani d . . . 1 . .
C C14 -0.3423(4) 0.0398(4) 0.29563(16) 0.1104(11) Uani d . . . 1 . .
H H14A -0.444156 0.052935 0.262844 0.166 Uiso calc U . R 1 . .
H H14B -0.390265 0.051793 0.33375 0.166 Uiso calc U . R 1 . .
H H14C -0.294995 -0.041521 0.293647 0.166 Uiso calc U . R 1 . .
C C15 0.4649(5) 0.4074(3) 0.36728(15) 0.1030(11) Uani d . . . 1 . .
C C16 0.3698(10) 0.4504(4) 0.4198(2) 0.173(2) Uani d . . . 1 . .
H H16A 0.342732 0.535384 0.415407 0.26 Uiso calc U . R 1 . .
H H16B 0.45388 0.436592 0.457043 0.26 Uiso calc U . R 1 . .
H H16C 0.251895 0.406731 0.420804 0.26 Uiso calc U . R 1 . .
C C17 0.6768(7) 0.4329(5) 0.3768(3) 0.194(3) Uani d . . . 1 . .
H H17A 0.735504 0.396867 0.344431 0.29 Uiso calc U . R 1 . .
H H17B 0.732908 0.399398 0.414984 0.29 Uiso calc U . R 1 . .
H H17C 0.697476 0.5189 0.376952 0.29 Uiso calc U . R 1 . .
C C18 0.3663(7) 0.4595(4) 0.30924(19) 0.1449(16) Uani d . . . 1 . .
H H18A 0.416143 0.422433 0.275456 0.217 Uiso calc U . R 1 . .
H H18B 0.388685 0.545277 0.308698 0.217 Uiso calc U . R 1 . .
H H18C 0.230549 0.444385 0.306255 0.217 Uiso calc U . R 1 . .
H H1C 0.560(4) 0.208(3) 0.4537(12) 0.085(8) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.223(4) ?
O2 C13 . 1.216(4) ?
O3 C12 . 1.375(3) ?
O3 C15 . 1.470(4) ?
N1 C5 . 1.322(4) ?
N1 C1 . 1.337(4) ?
N2 C6 . 1.349(4) ?
N2 C7 . 1.400(3) ?
N2 H1C . 0.98(3) ?
C1 C2 . 1.364(5) ?
C1 H1 . 0.93 ?
C2 C3 . 1.338(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.382(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.372(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.494(4) ?
C7 C8 . 1.381(4) ?
C7 C12 . 1.397(4) ?
C8 C9 . 1.391(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.391(4) ?
C10 C13 . 1.482(4) ?
C11 C12 . 1.373(4) ?
C11 H11 . 0.93 ?
C13 C14 . 1.478(5) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 C18 . 1.493(5) ?
C15 C16 . 1.496(5) ?
C15 C17 . 1.500(6) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O3 C15 . . 119.2(2) ?
C5 N1 C1 . . 115.9(3) ?
C6 N2 C7 . . 129.3(3) ?
C6 N2 H1C . . 121.2(16) ?
C7 N2 H1C . . 109.3(16) ?
N1 C1 C2 . . 124.0(4) ?
N1 C1 H1 . . 118.0 ?
C2 C1 H1 . . 118.0 ?
C3 C2 C1 . . 119.2(3) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 118.8(3) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 118.3(3) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
N1 C5 C4 . . 123.8(3) ?
N1 C5 C6 . . 116.2(3) ?
C4 C5 C6 . . 120.0(3) ?
O1 C6 N2 . . 124.5(3) ?
O1 C6 C5 . . 121.9(3) ?
N2 C6 C5 . . 113.6(3) ?
C8 C7 C12 . . 119.7(2) ?
C8 C7 N2 . . 123.9(3) ?
C12 C7 N2 . . 116.4(2) ?
C7 C8 C9 . . 119.8(3) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
C10 C9 C8 . . 121.1(3) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 118.5(3) ?
C9 C10 C13 . . 122.4(3) ?
C11 C10 C13 . . 119.2(3) ?
C12 C11 C10 . . 121.3(3) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 O3 . . 122.3(3) ?
C11 C12 C7 . . 119.7(3) ?
O3 C12 C7 . . 117.8(2) ?
O2 C13 C14 . . 120.6(3) ?
O2 C13 C10 . . 119.3(3) ?
C14 C13 C10 . . 120.2(3) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O3 C15 C18 . . 110.5(3) ?
O3 C15 C16 . . 109.5(3) ?
C18 C15 C16 . . 110.3(4) ?
O3 C15 C17 . . 102.0(3) ?
C18 C15 C17 . . 112.6(4) ?
C16 C15 C17 . . 111.6(4) ?
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 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?



