# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2octc
_database_code_depnum_ccdc_archive 'CCDC 2256652'
loop_
_audit_author_name
_audit_author_address
'Anand Singh'
;IIT Kanpur
India
;
_audit_update_record             
;
2023-04-16 deposited with the CCDC.	2023-07-03 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         'C19 H22 N2 O3'
_chemical_formula_sum            'C19 H22 N2 O3'
_chemical_formula_weight         326.38

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.811(3)
_cell_length_b                   21.127(6)
_cell_length_c                   9.099(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.689(8)
_cell_angle_gamma                90
_cell_volume                     1685.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3743
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.07

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5712
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            20015
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_av_R_equivalents  0.1157
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.685
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_full        25.242
_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             3017
_reflns_number_gt                1943
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick 2008)'
_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)+(0.1107P)²+1.6931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3017
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2393
_refine_ls_wR_factor_gt          0.2036
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 O 0.3122(3) 0.78633(13) 0.3480(3) 0.0333(7) Uani 1 1 d . . . . .
O2 O 0.2178(3) 0.59039(13) 0.0657(3) 0.0383(8) Uani 1 1 d . . . . .
O3 O 0.3848(3) 0.55683(13) 0.3176(3) 0.0397(8) Uani 1 1 d . . . . .
N1 N 0.2843(4) 0.71353(14) 0.1557(4) 0.0307(8) Uani 1 1 d . . . . .
H1 H 0.242487 0.703918 0.050417 0.037 Uiso 1 1 calc R U . . .
N2 N 0.5345(4) 0.67127(15) 0.3261(4) 0.0309(8) Uani 1 1 d . . . . .
C1 C 0.1783(4) 0.81831(17) 0.0687(5) 0.0275(9) Uani 1 1 d . . . . .
C2 C 0.0769(5) 0.80052(19) -0.0889(5) 0.0308(9) Uani 1 1 d . . . . .
H2A H 0.060014 0.756905 -0.116499 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0001(5) 0.84580(19) -0.2064(5) 0.0339(10) Uani 1 1 d . . . . .
H3A H -0.070804 0.832704 -0.313645 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0239(5) 0.9105(2) -0.1717(5) 0.0366(10) Uani 1 1 d . . . . .
C5 C 0.1252(5) 0.9273(2) -0.0132(5) 0.0372(10) Uani 1 1 d . . . . .
H5A H 0.143404 0.970931 0.014302 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2009(5) 0.88248(19) 0.1064(5) 0.0343(10) Uani 1 1 d . . . . .
H6A H 0.268614 0.895496 0.214897 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0608(5) 0.9589(2) -0.3020(6) 0.0463(12) Uani 1 1 d . . . . .
H7A H -0.029493 1.001460 -0.256428 0.070 Uiso 1 1 calc R U . . .
H7B H -0.170723 0.953882 -0.339563 0.070 Uiso 1 1 calc R U . . .
H7C H -0.037386 0.952941 -0.395102 0.070 Uiso 1 1 calc R U . . .
C8 C 0.2649(4) 0.77215(17) 0.2028(5) 0.0290(9) Uani 1 1 d . . . . .
C9 C 0.3730(4) 0.66627(17) 0.2763(4) 0.0281(9) Uani 1 1 d . . . . .
H9A H 0.355933 0.672104 0.375840 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5816(5) 0.64933(19) 0.2040(5) 0.0346(10) Uani 1 1 d . . . . .
H10A H 0.678424 0.669456 0.223950 0.052 Uiso 1 1 calc R U . . .
H10B H 0.503413 0.660520 0.093642 0.052 Uiso 1 1 calc R U . . .
H10C H 0.594781 0.603273 0.212172 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6384(5) 0.66589(17) 0.4929(5) 0.0296(9) Uani 1 1 d . . . . .
C12 C 0.6034(5) 0.68998(18) 0.6157(5) 0.0342(10) Uani 1 1 d . . . . .
H12A H 0.506671 0.708858 0.585929 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7085(5) 0.68648(19) 0.7793(5) 0.0369(10) Uani 1 1 d . . . . .
H13A H 0.682463 0.702623 0.860920 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8511(5) 0.65983(19) 0.8266(5) 0.0363(10) Uani 1 1 d . . . . .
H14A H 0.923327 0.658021 0.939353 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8859(5) 0.6360(2) 0.7063(5) 0.0373(10) Uani 1 1 d . . . . .
H15A H 0.982897 0.617170 0.737079 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7825(5) 0.63888(18) 0.5425(5) 0.0340(10) Uani 1 1 d . . . . .
H16A H 0.809503 0.622328 0.462007 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3122(5) 0.60099(18) 0.2032(5) 0.0303(9) Uani 1 1 d . . . . .
C18 C 0.3527(6) 0.49066(18) 0.2640(6) 0.0473(13) Uani 1 1 d . . . . .
H18A H 0.242677 0.485654 0.188853 0.057 Uiso 1 1 calc R U . . .
H18B H 0.378017 0.463009 0.360640 0.057 Uiso 1 1 calc R U . . .
C19 C 0.4442(6) 0.4715(2) 0.1781(8) 0.0614(15) Uani 1 1 d . . . . .
H19A H 0.426686 0.426552 0.148793 0.092 Uiso 1 1 calc R U . . .
H19B H 0.552691 0.478443 0.250813 0.092 Uiso 1 1 calc R U . . .
H19C H 0.413428 0.496821 0.077953 0.092 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 C8 1.225(4) . ?
O2 C17 1.197(5) . ?
O3 C17 1.340(4) . ?
O3 C18 1.467(5) . ?
N1 C8 1.351(5) . ?
N1 C9 1.449(5) . ?
N1 H1 0.8800 . ?
N2 C11 1.402(5) . ?
N2 C9 1.443(5) . ?
N2 C10 1.458(5) . ?
C1 C2 1.380(5) . ?
C1 C6 1.391(5) . ?
C1 C8 1.493(5) . ?
C2 C3 1.379(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.399(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(6) . ?
C4 C7 1.503(6) . ?
C5 C6 1.381(6) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C17 1.531(5) . ?
C9 H9A 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.399(6) . ?
C11 C12 1.403(6) . ?
C12 C13 1.381(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.380(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.377(6) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C18 C19 1.487(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C17 O3 C18 116.4(3) . . ?
C8 N1 C9 120.9(3) . . ?
C8 N1 H1 119.5 . . ?
C9 N1 H1 119.5 . . ?
C11 N2 C9 119.7(3) . . ?
C11 N2 C10 118.3(3) . . ?
C9 N2 C10 114.6(3) . . ?
C2 C1 C6 118.8(4) . . ?
C2 C1 C8 123.4(3) . . ?
C6 C1 C8 117.8(3) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 117.2(4) . . ?
C5 C4 C7 122.2(4) . . ?
C3 C4 C7 120.7(4) . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6A 119.8 . . ?
C1 C6 H6A 119.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 121.8(3) . . ?
O1 C8 C1 121.5(3) . . ?
N1 C8 C1 116.7(3) . . ?
N2 C9 N1 112.9(3) . . ?
N2 C9 C17 111.2(3) . . ?
N1 C9 C17 107.9(3) . . ?
N2 C9 H9A 108.2 . . ?
N1 C9 H9A 108.2 . . ?
C17 C9 H9A 108.2 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 N2 121.3(4) . . ?
C16 C11 C12 117.7(4) . . ?
N2 C11 C12 120.9(4) . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 121.1(4) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C15 C16 C11 120.9(4) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?
O2 C17 O3 125.0(4) . . ?
O2 C17 C9 126.2(3) . . ?
O3 C17 C9 108.8(3) . . ?
O3 C18 C19 110.1(4) . . ?
O3 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
O3 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 0.2(6) . . . . ?
C8 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C2 C3 C4 C7 179.8(4) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C7 C4 C5 C6 179.0(4) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C2 C1 C6 C5 -1.3(6) . . . . ?
C8 C1 C6 C5 179.2(4) . . . . ?
C9 N1 C8 O1 -5.0(6) . . . . ?
C9 N1 C8 C1 177.0(3) . . . . ?
C2 C1 C8 O1 -155.3(4) . . . . ?
C6 C1 C8 O1 24.2(6) . . . . ?
C2 C1 C8 N1 22.7(6) . . . . ?
C6 C1 C8 N1 -157.8(4) . . . . ?
C11 N2 C9 N1 136.5(3) . . . . ?
C10 N2 C9 N1 -73.9(4) . . . . ?
C11 N2 C9 C17 -102.1(4) . . . . ?
C10 N2 C9 C17 47.5(4) . . . . ?
C8 N1 C9 N2 -84.5(4) . . . . ?
C8 N1 C9 C17 152.2(4) . . . . ?
C9 N2 C11 C16 147.0(4) . . . . ?
C10 N2 C11 C16 -1.5(5) . . . . ?
C9 N2 C11 C12 -35.8(5) . . . . ?
C10 N2 C11 C12 175.7(4) . . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
N2 C11 C12 C13 -177.7(4) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C11 -0.4(6) . . . . ?
N2 C11 C16 C15 177.6(4) . . . . ?
C12 C11 C16 C15 0.2(6) . . . . ?
C18 O3 C17 O2 4.7(6) . . . . ?
C18 O3 C17 C9 -173.8(3) . . . . ?
N2 C9 C17 O2 -118.0(4) . . . . ?
N1 C9 C17 O2 6.3(6) . . . . ?
N2 C9 C17 O3 60.4(4) . . . . ?
N1 C9 C17 O3 -175.3(3) . . . . ?
C17 O3 C18 C19 80.7(5) . . . . ?

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
N1 H1 O1 0.88 2.24 2.933(4) 135.0 4_575 yes
C10 H10B O1 0.98 2.45 3.411(5) 166.1 4_575 yes

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.086



