# 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 
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data_pb_25_02_373
_database_code_depnum_ccdc_archive 'CCDC 2237741'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-01-24 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_chemical_absolute_configuration unk
_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 0.0033 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8734(3)
_cell_length_b                   15.4556(7)
_cell_length_c                   17.6587(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1603.00(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.8422.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.123
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33944
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_min         2.307
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2861
_reflns_number_total             3289
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 
;
 Flack x determined using 1040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.1795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C7(H7), C15(H15), C18(H18), C4(H4), C19(H19), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.4412(3) 0.44457(9) 0.42898(8) 0.0534(4) Uani 1 1 d . . . . .
O1 O 0.6230(3) 0.23471(10) 0.36970(11) 0.0689(5) Uani 1 1 d . . . . .
N1 N 0.4672(3) 0.35043(11) 0.43951(10) 0.0506(4) Uani 1 1 d . . . . .
O3 O 0.1085(3) 0.82358(11) 0.39042(10) 0.0757(5) Uani 1 1 d . . . . .
C8 C 0.2902(4) 0.17469(15) 0.30934(12) 0.0526(5) Uani 1 1 d . . . . .
C9 C 0.2182(5) 0.26175(15) 0.28962(13) 0.0602(6) Uani 1 1 d . . . . .
H9 H 0.090673 0.269421 0.259138 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1954(4) 0.55672(14) 0.38952(12) 0.0523(5) Uani 1 1 d . . . . .
C14 C 0.3502(4) 0.61299(15) 0.35569(14) 0.0586(6) Uani 1 1 d . . . . .
H14 H 0.479018 0.590718 0.332049 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1675(5) 0.10055(15) 0.29138(13) 0.0629(6) Uani 1 1 d . . . . .
H7 H 0.035685 0.105126 0.262478 0.076 Uiso 1 1 calc R U . . .
C1 C 0.6503(5) 0.34342(17) 0.49471(14) 0.0667(7) Uani 1 1 d . . . . .
H1A H 0.784016 0.371520 0.475424 0.100 Uiso 1 1 calc R U . . .
H1B H 0.682931 0.283484 0.503950 0.100 Uiso 1 1 calc R U . . .
H1C H 0.604630 0.370638 0.541156 0.100 Uiso 1 1 calc R U . . .
C15 C 0.3154(4) 0.70126(15) 0.35670(14) 0.0612(6) Uani 1 1 d . . . . .
H15 H 0.420261 0.737889 0.333674 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3306(5) 0.33017(15) 0.31422(12) 0.0591(6) Uani 1 1 d . . . . .
C3 C 0.4877(4) 0.16484(15) 0.35183(12) 0.0537(5) Uani 1 1 d . . . . .
C12 C 0.2337(4) 0.46018(14) 0.38839(13) 0.0540(5) Uani 1 1 d . . . . .
H12 H 0.107815 0.431630 0.414911 0.065 Uiso 1 1 calc R U . . .
C18 C -0.0314(4) 0.68058(16) 0.42496(14) 0.0627(6) Uani 1 1 d . . . . .
H18 H -0.161067 0.702778 0.448093 0.075 Uiso 1 1 calc R U . . .
C2 C 0.5357(4) 0.31986(14) 0.36338(13) 0.0552(5) Uani 1 1 d . . . . .
H2 H 0.656574 0.357716 0.344223 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5610(4) 0.08505(15) 0.37630(14) 0.0621(6) Uani 1 1 d . . . . .
H4 H 0.694426 0.079985 0.404317 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1254(4) 0.73546(14) 0.39179(13) 0.0563(6) Uani 1 1 d . . . . .
C19 C 0.0070(4) 0.59180(16) 0.42337(14) 0.0623(6) Uani 1 1 d . . . . .
H19 H -0.098599 0.555131 0.445971 0.075 Uiso 1 1 calc R U . . .
C11 C 0.2541(5) 0.42241(15) 0.30901(13) 0.0687(7) Uani 1 1 d . . . . .
H11A H 0.107901 0.425338 0.283572 0.082 Uiso 1 1 calc R U . . .
H11B H 0.363116 0.455656 0.279775 0.082 Uiso 1 1 calc R U . . .
C5 C 0.4338(5) 0.01241(16) 0.35870(16) 0.0695(7) Uani 1 1 d . . . . .
H5 H 0.479998 -0.041731 0.375792 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2390(5) 0.02021(17) 0.31595(16) 0.0712(7) Uani 1 1 d . . . . .
H6 H 0.155208 -0.028833 0.303542 0.085 Uiso 1 1 calc R U . . .
C17 C -0.0759(6) 0.86205(18) 0.4298(2) 0.0938(10) Uani 1 1 d . . . . .
H17A H -0.215802 0.848809 0.404216 0.141 Uiso 1 1 calc R U . . .
H17B H -0.055196 0.923640 0.431384 0.141 Uiso 1 1 calc R U . . .
H17C H -0.081486 0.839757 0.480522 0.141 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
O2 N1 1.475(2) . ?
O2 C12 1.435(3) . ?
O1 C3 1.377(3) . ?
O1 C2 1.417(3) . ?
N1 C1 1.455(3) . ?
N1 C2 1.481(3) . ?
O3 C16 1.366(3) . ?
O3 C17 1.418(4) . ?
C8 C9 1.453(3) . ?
C8 C7 1.390(3) . ?
C8 C3 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.320(3) . ?
C13 C14 1.393(3) . ?
C13 C12 1.509(3) . ?
C13 C19 1.370(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.381(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C10 C2 1.493(3) . ?
C10 C11 1.498(3) . ?
C3 C4 1.376(3) . ?
C12 H12 0.9800 . ?
C12 C11 1.523(3) . ?
C18 H18 0.9300 . ?
C18 C16 1.382(3) . ?
C18 C19 1.391(3) . ?
C2 H2 0.9800 . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C19 H19 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C12 O2 N1 108.46(14) . . ?
C3 O1 C2 120.09(18) . . ?
O2 N1 C2 103.21(15) . . ?
C1 N1 O2 103.55(16) . . ?
C1 N1 C2 112.55(19) . . ?
C16 O3 C17 117.7(2) . . ?
C7 C8 C9 123.9(2) . . ?
C3 C8 C9 118.3(2) . . ?
C3 C8 C7 117.7(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C14 C13 C12 121.0(2) . . ?
C19 C13 C14 117.9(2) . . ?
C19 C13 C12 121.2(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C9 C10 C2 120.6(2) . . ?
C9 C10 C11 126.3(2) . . ?
C2 C10 C11 112.3(2) . . ?
O1 C3 C8 121.3(2) . . ?
C4 C3 O1 116.8(2) . . ?
C4 C3 C8 121.9(2) . . ?
O2 C12 C13 106.62(18) . . ?
O2 C12 H12 109.1 . . ?
O2 C12 C11 109.18(19) . . ?
C13 C12 H12 109.1 . . ?
C13 C12 C11 113.76(18) . . ?
C11 C12 H12 109.1 . . ?
C16 C18 H18 120.4 . . ?
C16 C18 C19 119.3(2) . . ?
C19 C18 H18 120.4 . . ?
O1 C2 N1 108.86(18) . . ?
O1 C2 C10 115.90(18) . . ?
O1 C2 H2 108.6 . . ?
N1 C2 C10 105.93(19) . . ?
N1 C2 H2 108.6 . . ?
C10 C2 H2 108.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
O3 C16 C15 115.6(2) . . ?
O3 C16 C18 124.8(2) . . ?
C15 C16 C18 119.6(2) . . ?
C13 C19 C18 122.0(2) . . ?
C13 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C10 C11 C12 109.39(18) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 N1 C2 O1 165.02(15) . . . . ?
O2 N1 C2 C10 -69.7(2) . . . . ?
O2 C12 C11 C10 51.5(3) . . . . ?
O1 C3 C4 C5 -178.8(2) . . . . ?
N1 O2 C12 C13 171.40(16) . . . . ?
N1 O2 C12 C11 -65.3(2) . . . . ?
C8 C9 C10 C2 -0.1(4) . . . . ?
C8 C9 C10 C11 -169.2(2) . . . . ?
C8 C7 C6 C5 0.0(4) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C9 C8 C7 C6 -176.0(2) . . . . ?
C9 C8 C3 O1 -5.3(3) . . . . ?
C9 C8 C3 C4 176.5(2) . . . . ?
C9 C10 C2 O1 11.1(3) . . . . ?
C9 C10 C2 N1 -109.7(3) . . . . ?
C9 C10 C11 C12 119.5(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C12 C11 C10 170.4(2) . . . . ?
C14 C13 C12 O2 62.2(3) . . . . ?
C14 C13 C12 C11 -58.2(3) . . . . ?
C14 C13 C19 C18 -0.4(4) . . . . ?
C14 C15 C16 O3 179.2(2) . . . . ?
C14 C15 C16 C18 -0.9(4) . . . . ?
C7 C8 C9 C10 173.6(2) . . . . ?
C7 C8 C3 O1 177.7(2) . . . . ?
C7 C8 C3 C4 -0.5(3) . . . . ?
C1 N1 C2 O1 54.0(2) . . . . ?
C1 N1 C2 C10 179.32(18) . . . . ?
C3 O1 C2 N1 99.8(2) . . . . ?
C3 O1 C2 C10 -19.4(3) . . . . ?
C3 C8 C9 C10 -3.1(3) . . . . ?
C3 C8 C7 C6 0.8(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C12 O2 N1 C1 -167.65(18) . . . . ?
C12 O2 N1 C2 74.85(19) . . . . ?
C12 C13 C14 C15 -180.0(2) . . . . ?
C12 C13 C19 C18 -180.0(2) . . . . ?
C2 O1 C3 C8 17.1(3) . . . . ?
C2 O1 C3 C4 -164.6(2) . . . . ?
C2 C10 C11 C12 -50.4(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C16 C18 C19 C13 -0.3(4) . . . . ?
C19 C13 C14 C15 0.4(4) . . . . ?
C19 C13 C12 O2 -118.2(2) . . . . ?
C19 C13 C12 C11 121.4(2) . . . . ?
C19 C18 C16 O3 -179.2(2) . . . . ?
C19 C18 C16 C15 0.9(4) . . . . ?
C11 C10 C2 O1 -178.4(2) . . . . ?
C11 C10 C2 N1 60.8(2) . . . . ?
C17 O3 C16 C15 -176.1(2) . . . . ?
C17 O3 C16 C18 4.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
