# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_om
_database_code_depnum_ccdc_archive 'CCDC 2141571'
loop_
_audit_author_name
_audit_author_address
'SURAJIT DUARI'
;Calcutta University
India
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_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      monoclinic
_space_group_IT_number           14
_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                   13.729(6)
_cell_length_b                   5.448(2)
_cell_length_c                   23.303(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.322(7)
_cell_angle_gamma                90
_cell_volume                     1688.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6985
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1087 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.8758.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32688
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.095
_diffrn_reflns_theta_min         1.804
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2635
_reflns_number_total             3695
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.013
_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)+(0.0464P)²+0.3747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1191
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.53989(10) -0.1276(2) 0.35889(5) 0.0815(4) Uani 1 1 d . . . . .
O2 O 0.38353(7) 0.2236(2) 0.35463(4) 0.0658(3) Uani 1 1 d . . . . .
N1 N 0.43879(9) 0.1863(3) 0.31298(5) 0.0611(3) Uani 1 1 d . . . . .
C1 C 0.51330(11) 0.0165(3) 0.31822(7) 0.0590(4) Uani 1 1 d . . . . .
C2 C 0.55888(11) 0.0573(3) 0.26550(6) 0.0532(3) Uani 1 1 d . . . . .
H2 H 0.548974 -0.090044 0.240611 0.064 Uiso 1 1 calc R U . . .
C3 C 0.49659(10) 0.2649(3) 0.23232(6) 0.0471(3) Uani 1 1 d . . . . .
C4 C 0.42803(10) 0.3369(3) 0.26301(6) 0.0510(3) Uani 1 1 d . . . . .
C5 C 0.35924(11) 0.5276(3) 0.24489(7) 0.0619(4) Uani 1 1 d . . . . .
H5 H 0.313108 0.570286 0.266455 0.074 Uiso 1 1 calc R U . . .
C6 C 0.36276(11) 0.6489(3) 0.19402(7) 0.0617(4) Uani 1 1 d . . . . .
H6 H 0.318218 0.777596 0.181101 0.074 Uiso 1 1 calc R U . . .
C7 C 0.43189(10) 0.5852(3) 0.16042(6) 0.0523(3) Uani 1 1 d . . . . .
C8 C 0.49957(10) 0.3857(3) 0.17915(5) 0.0474(3) Uani 1 1 d . . . . .
C9 C 0.56586(12) 0.3218(3) 0.14344(6) 0.0613(4) Uani 1 1 d . . . . .
H9 H 0.609508 0.189808 0.154313 0.074 Uiso 1 1 calc R U . . .
C10 C 0.56638(14) 0.4511(4) 0.09345(7) 0.0748(5) Uani 1 1 d . . . . .
H10 H 0.610334 0.406213 0.070642 0.090 Uiso 1 1 calc R U . . .
C11 C 0.50182(14) 0.6500(4) 0.07606(7) 0.0769(5) Uani 1 1 d . . . . .
H11 H 0.503901 0.738755 0.042291 0.092 Uiso 1 1 calc R U . . .
C12 C 0.43611(13) 0.7140(3) 0.10829(7) 0.0667(4) Uani 1 1 d . . . . .
H12 H 0.392787 0.845441 0.095911 0.080 Uiso 1 1 calc R U . . .
C13 C 0.67157(11) 0.1078(3) 0.28823(7) 0.0594(4) Uani 1 1 d . . . . .
H13A H 0.703350 -0.034502 0.310061 0.071 Uiso 1 1 calc R U . . .
H13B H 0.700418 0.130185 0.254563 0.071 Uiso 1 1 calc R U . . .
C14 C 0.69507(13) 0.3293(3) 0.32745(7) 0.0728(5) Uani 1 1 d . . . . .
H14A H 0.665584 0.472117 0.305852 0.109 Uiso 1 1 calc R U . . .
H14B H 0.766614 0.350107 0.340228 0.109 Uiso 1 1 calc R U . . .
H14C H 0.668043 0.307479 0.361366 0.109 Uiso 1 1 calc R U . . .
C15 C 0.44328(12) 0.3643(4) 0.40461(7) 0.0722(5) Uani 1 1 d . . . . .
H15A H 0.472694 0.507023 0.390550 0.087 Uiso 1 1 calc R U . . .
H15B H 0.497011 0.263769 0.427935 0.087 Uiso 1 1 calc R U . . .
C16 C 0.37288(11) 0.4410(3) 0.44100(6) 0.0568(4) Uani 1 1 d . . . . .
C17 C 0.36522(12) 0.3081(3) 0.48989(7) 0.0610(4) Uani 1 1 d . . . . .
H17 H 0.404704 0.168771 0.500504 0.073 Uiso 1 1 calc R U . . .
C18 C 0.30012(14) 0.3776(4) 0.52342(7) 0.0756(5) Uani 1 1 d . . . . .
H18 H 0.296038 0.286047 0.556422 0.091 Uiso 1 1 calc R U . . .
C19 C 0.24181(14) 0.5808(4) 0.50806(9) 0.0869(6) Uani 1 1 d . . . . .
H19 H 0.197330 0.627436 0.530375 0.104 Uiso 1 1 calc R U . . .
C20 C 0.24866(17) 0.7168(4) 0.45966(10) 0.0953(7) Uani 1 1 d . . . . .
H20 H 0.208876 0.855768 0.449252 0.114 Uiso 1 1 calc R U . . .
C21 C 0.31424(16) 0.6481(3) 0.42650(8) 0.0811(5) Uani 1 1 d . . . . .
H21 H 0.319055 0.742138 0.394017 0.097 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 C1 1.2152(18) . ?
O2 N1 1.3867(16) . ?
O2 C15 1.4643(18) . ?
N1 C1 1.362(2) . ?
N1 C4 1.4018(19) . ?
C1 C2 1.527(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.5102(19) . ?
C2 C13 1.531(2) . ?
C3 C4 1.3727(19) . ?
C3 C8 1.4126(19) . ?
C4 C5 1.398(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.415(2) . ?
C7 C8 1.426(2) . ?
C7 C12 1.417(2) . ?
C8 C9 1.420(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.500(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.494(2) . ?
C16 C17 1.376(2) . ?
C16 C21 1.379(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.361(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9300 . ?

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
N1 O2 C15 109.73(11) . . ?
O2 N1 C4 122.15(13) . . ?
C1 N1 O2 124.42(12) . . ?
C1 N1 C4 113.23(12) . . ?
O1 C1 N1 125.65(16) . . ?
O1 C1 C2 128.17(15) . . ?
N1 C1 C2 106.08(12) . . ?
C1 C2 H2 109.4 . . ?
C1 C2 C13 109.15(12) . . ?
C3 C2 C1 103.19(12) . . ?
C3 C2 H2 109.4 . . ?
C3 C2 C13 115.99(12) . . ?
C13 C2 H2 109.4 . . ?
C4 C3 C2 108.76(12) . . ?
C4 C3 C8 119.75(13) . . ?
C8 C3 C2 131.49(13) . . ?
C3 C4 N1 108.70(13) . . ?
C3 C4 C5 123.66(13) . . ?
C5 C4 N1 127.63(14) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 117.05(14) . . ?
C6 C5 H5 121.5 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.21(14) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 119.55(13) . . ?
C6 C7 C12 121.89(14) . . ?
C12 C7 C8 118.56(14) . . ?
C3 C8 C7 117.74(12) . . ?
C3 C8 C9 124.15(13) . . ?
C9 C8 C7 118.11(13) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.90(16) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.83(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.09(16) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.48(16) . . ?
C11 C12 H12 119.3 . . ?
C2 C13 H13A 108.8 . . ?
C2 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C2 113.71(13) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 110.4 . . ?
O2 C15 H15B 110.4 . . ?
O2 C15 C16 106.51(12) . . ?
H15A C15 H15B 108.6 . . ?
C16 C15 H15A 110.4 . . ?
C16 C15 H15B 110.4 . . ?
C17 C16 C15 121.01(15) . . ?
C17 C16 C21 118.29(16) . . ?
C21 C16 C15 120.70(16) . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.21(16) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.76(18) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.99(19) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.15(19) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.59(18) . . ?
C20 C21 H21 119.7 . . ?

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
O1 C1 C2 C3 -177.65(14) . . . . ?
O1 C1 C2 C13 -53.7(2) . . . . ?
O2 N1 C1 O1 1.7(2) . . . . ?
O2 N1 C1 C2 -174.85(12) . . . . ?
O2 N1 C4 C3 176.22(11) . . . . ?
O2 N1 C4 C5 -4.8(2) . . . . ?
O2 C15 C16 C17 96.59(17) . . . . ?
O2 C15 C16 C21 -83.74(18) . . . . ?
N1 O2 C15 C16 168.60(12) . . . . ?
N1 C1 C2 C3 -1.23(14) . . . . ?
N1 C1 C2 C13 122.67(13) . . . . ?
N1 C4 C5 C6 -179.74(14) . . . . ?
C1 N1 C4 C3 1.03(17) . . . . ?
C1 N1 C4 C5 179.99(14) . . . . ?
C1 C2 C3 C4 1.87(14) . . . . ?
C1 C2 C3 C8 -178.78(13) . . . . ?
C1 C2 C13 C14 -59.75(17) . . . . ?
C2 C3 C4 N1 -1.82(15) . . . . ?
C2 C3 C4 C5 179.17(13) . . . . ?
C2 C3 C8 C7 -177.50(13) . . . . ?
C2 C3 C8 C9 2.2(2) . . . . ?
C3 C2 C13 C14 56.23(18) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C3 C8 C9 C10 -178.20(14) . . . . ?
C4 N1 C1 O1 176.74(14) . . . . ?
C4 N1 C1 C2 0.21(16) . . . . ?
C4 C3 C8 C7 1.79(19) . . . . ?
C4 C3 C8 C9 -178.47(13) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C5 C6 C7 C12 -179.03(14) . . . . ?
C6 C7 C8 C3 -2.15(19) . . . . ?
C6 C7 C8 C9 178.10(13) . . . . ?
C6 C7 C12 C11 -179.29(15) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C8 C3 C4 N1 178.74(11) . . . . ?
C8 C3 C4 C5 -0.3(2) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C7 0.9(3) . . . . ?
C12 C7 C8 C3 177.89(12) . . . . ?
C12 C7 C8 C9 -1.86(19) . . . . ?
C13 C2 C3 C4 -117.41(14) . . . . ?
C13 C2 C3 C8 61.94(19) . . . . ?
C15 O2 N1 C1 77.57(18) . . . . ?
C15 O2 N1 C4 -97.07(16) . . . . ?
C15 C16 C17 C18 -179.73(15) . . . . ?
C15 C16 C21 C20 179.26(16) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C16 C21 C20 -1.1(2) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C16 0.7(3) . . . . ?
C21 C16 C17 C18 0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and n-Hexane'
