# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2238743'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT MADRAS
India
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.22

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.1110(7)
_cell_length_b                   7.3567(4)
_cell_length_c                   13.9127(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.039(3)
_cell_angle_gamma                90
_cell_volume                     1126.05(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9477
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      68.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.740
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21157
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.780
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2039
_reflns_number_gt                1782
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_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)+(0.0670P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2039
_refine_ls_number_parameters     149
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.38404(12) 0.67015(18) 0.39589(10) 0.0493(3) Uani 1 1 d . . . . .
C2 C 0.28770(13) 0.5927(2) 0.33456(11) 0.0560(4) Uani 1 1 d . . . . .
H2 H 0.222688 0.542646 0.360856 0.067 Uiso 1 1 calc R U . . .
C3 C 0.28748(15) 0.5892(2) 0.23549(12) 0.0647(4) Uani 1 1 d . . . . .
H3 H 0.222455 0.537068 0.195612 0.078 Uiso 1 1 calc R U . . .
C4 C 0.38336(17) 0.6628(2) 0.19500(12) 0.0701(5) Uani 1 1 d . . . . .
H4 H 0.382650 0.660824 0.128083 0.084 Uiso 1 1 calc R U . . .
C5 C 0.47940(17) 0.7388(2) 0.25393(13) 0.0721(5) Uani 1 1 d . . . . .
H5 H 0.543953 0.788408 0.226870 0.086 Uiso 1 1 calc R U . . .
C6 C 0.48075(14) 0.7420(2) 0.35346(12) 0.0622(4) Uani 1 1 d . . . . .
H6 H 0.546862 0.792561 0.392775 0.075 Uiso 1 1 calc R U . . .
C7 C 0.39249(11) 0.67946(18) 0.50178(10) 0.0491(3) Uani 1 1 d . . . . .
H7 H 0.467792 0.716791 0.533282 0.059 Uiso 1 1 calc R U . . .
C8 C 0.31031(11) 0.64341(17) 0.56097(9) 0.0446(3) Uani 1 1 d . . . . .
C9 C 0.33767(12) 0.65810(19) 0.66824(10) 0.0519(3) Uani 1 1 d . . . . .
C10 C 0.45176(16) 0.7480(2) 0.71488(12) 0.0705(5) Uani 1 1 d . . . . .
H10A H 0.452563 0.751024 0.783948 0.106 Uiso 1 1 calc R U . . .
H10B H 0.455141 0.869832 0.690717 0.106 Uiso 1 1 calc R U . . .
H10C H 0.520846 0.680777 0.699916 0.106 Uiso 1 1 calc R U . . .
C11 C 0.18140(11) 0.58350(17) 0.52760(9) 0.0433(3) Uani 1 1 d . . . . .
O1 O 0.26404(10) 0.59751(17) 0.71708(8) 0.0696(3) Uani 1 1 d . . . . .
O2 O 0.15507(9) 0.42096(12) 0.51671(7) 0.0554(3) Uani 1 1 d . . . . .
O3 O 0.20586(15) 0.06633(16) 0.57798(9) 0.0828(4) Uani 1 1 d D . . . .
H3A H 0.203(2) 0.172(3) 0.5578(19) 0.124 Uiso 1 1 d D U . . .
H3B H 0.211(3) 0.075(4) 0.6397(13) 0.124 Uiso 1 1 d D U . . .
N1 N 0.10114(11) 0.71555(17) 0.51210(9) 0.0521(3) Uani 1 1 d . . . . .
H1A H 0.1216(16) 0.827(3) 0.5215(12) 0.062 Uiso 1 1 d . U . . .
H1B H 0.0243(16) 0.688(2) 0.4994(12) 0.062 Uiso 1 1 d . 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
C1 C2 1.394(2) . ?
C1 C6 1.3999(19) . ?
C1 C7 1.4647(19) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3388(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.4848(19) . ?
C8 C11 1.5084(17) . ?
C9 O1 1.2186(17) . ?
C9 C10 1.495(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.2353(15) . ?
C11 N1 1.3159(17) . ?
O3 H3A 0.828(17) . ?
O3 H3B 0.855(17) . ?
N1 H1A 0.855(19) . ?
N1 H1B 0.871(18) . ?

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
C2 C1 C6 117.72(14) . . ?
C2 C1 C7 124.79(12) . . ?
C6 C1 C7 117.48(13) . . ?
C3 C2 C1 120.89(13) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.42(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.70(15) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.29(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.96(15) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 131.00(12) . . ?
C8 C7 H7 114.5 . . ?
C1 C7 H7 114.5 . . ?
C7 C8 C9 122.85(12) . . ?
C7 C8 C11 124.65(12) . . ?
C9 C8 C11 112.50(11) . . ?
O1 C9 C8 118.35(12) . . ?
O1 C9 C10 120.96(14) . . ?
C8 C9 C10 120.69(13) . . ?
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 . . ?
O2 C11 N1 123.44(12) . . ?
O2 C11 C8 121.26(11) . . ?
N1 C11 C8 115.29(11) . . ?
H3A O3 H3B 105(2) . . ?
C11 N1 H1A 121.5(12) . . ?
C11 N1 H1B 119.0(12) . . ?
H1A N1 H1B 119.0(16) . . ?

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
C6 C1 C2 C3 -0.8(2) . . . . ?
C7 C1 C2 C3 -179.75(13) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C7 C1 C6 C5 -179.81(14) . . . . ?
C2 C1 C7 C8 -10.1(2) . . . . ?
C6 C1 C7 C8 170.90(14) . . . . ?
C1 C7 C8 C9 178.82(13) . . . . ?
C1 C7 C8 C11 -1.0(2) . . . . ?
C7 C8 C9 O1 -169.34(13) . . . . ?
C11 C8 C9 O1 10.46(18) . . . . ?
C7 C8 C9 C10 11.7(2) . . . . ?
C11 C8 C9 C10 -168.49(12) . . . . ?
C7 C8 C11 O2 89.30(17) . . . . ?
C9 C8 C11 O2 -90.49(15) . . . . ?
C7 C8 C11 N1 -91.14(16) . . . . ?
C9 C8 C11 N1 89.06(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O2 0.828(17) 1.968(18) 2.7780(15) 166(3) . yes
O3 H3B O1 0.855(17) 1.980(17) 2.8332(17) 176(3) 2_546 yes
N1 H1A O3 0.855(19) 2.10(2) 2.9249(18) 163.3(16) 1_565 yes
N1 H1B O2 0.871(18) 2.131(18) 2.9923(16) 169.9(16) 3_566 yes

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.027

