# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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 2263835'
loop_
_audit_author_name
_audit_author_address
'Ranjan Patra'
;Amity Institute of Click Chemistry Research and Studies
India
;
_audit_update_record             
;
2023-05-18 deposited with the CCDC.	2023-06-20 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            'C23 H15 N O'
_chemical_formula_weight         321.36

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   22.3743(7)
_cell_length_b                   5.3342(2)
_cell_length_c                   13.0665(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1559.47(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8056
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS 2.05 (Sheldrick, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24697
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.397
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3884
_reflns_number_gt                3436
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0453P)²+0.6188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1447 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N -0.49653(10) -0.5853(4) -0.44560(16) 0.0220(5) Uani 1 1 d . . . . .
O1 O -0.37345(8) -0.1777(4) -0.52913(15) 0.0272(4) Uani 1 1 d . . . . .
C1 C -0.38430(13) 0.0142(5) -0.5983(2) 0.0251(6) Uani 1 1 d . . . . .
C2 C -0.34263(13) 0.1832(6) -0.6349(2) 0.0284(6) Uani 1 1 d . . . . .
H2 H -0.302626 0.174920 -0.615844 0.034 Uiso 1 1 calc R U . . .
C3 C -0.36350(13) 0.3654(5) -0.7012(2) 0.0284(6) Uani 1 1 d . . . . .
H3 H -0.336857 0.483501 -0.726886 0.034 Uiso 1 1 calc R U . . .
C4 C -0.42347(13) 0.3771(5) -0.7308(2) 0.0258(6) Uani 1 1 d . . . . .
H4 H -0.436019 0.500887 -0.776098 0.031 Uiso 1 1 calc R U . . .
C5 C -0.46428(12) 0.2053(5) -0.6931(2) 0.0242(6) Uani 1 1 d . . . . .
H5 H -0.504213 0.212391 -0.712660 0.029 Uiso 1 1 calc R U . . .
C6 C -0.44438(12) 0.0207(5) -0.6251(2) 0.0235(5) Uani 1 1 d . . . . .
C7 C -0.47267(12) -0.1798(5) -0.5689(2) 0.0225(5) Uani 1 1 d . . . . .
C8 C -0.42798(11) -0.2945(5) -0.5114(2) 0.0217(5) Uani 1 1 d . . . . .
C9 C -0.43985(11) -0.4979(5) -0.44815(19) 0.0206(5) Uani 1 1 d . . . . .
C10 C -0.39512(11) -0.6323(5) -0.3844(2) 0.0214(5) Uani 1 1 d . . . . .
C11 C -0.33544(12) -0.5587(5) -0.3804(2) 0.0268(6) Uani 1 1 d . . . . .
H11 H -0.323137 -0.417280 -0.416320 0.032 Uiso 1 1 calc R U . . .
C12 C -0.29411(12) -0.6933(6) -0.3236(2) 0.0294(6) Uani 1 1 d . . . . .
H12 H -0.254424 -0.641767 -0.321514 0.035 Uiso 1 1 calc R U . . .
C13 C -0.31185(12) -0.9051(6) -0.2697(2) 0.0290(6) Uani 1 1 d . . . . .
H13 H -0.284097 -0.996387 -0.232045 0.035 Uiso 1 1 calc R U . . .
C14 C -0.37113(12) -0.9793(5) -0.2724(2) 0.0273(6) Uani 1 1 d . . . . .
H14 H -0.383265 -1.120384 -0.236113 0.033 Uiso 1 1 calc R U . . .
C15 C -0.41239(12) -0.8443(5) -0.3289(2) 0.0242(6) Uani 1 1 d . . . . .
H15 H -0.452138 -0.895256 -0.329847 0.029 Uiso 1 1 calc R U . . .
C16 C -0.54014(11) -0.4816(5) -0.5029(2) 0.0212(5) Uani 1 1 d . . . . .
C17 C -0.53031(12) -0.2736(5) -0.5647(2) 0.0236(5) Uani 1 1 d . . . . .
H17 H -0.561215 -0.200311 -0.601668 0.028 Uiso 1 1 calc R U . . .
C18 C -0.59952(11) -0.6075(5) -0.4952(2) 0.0219(5) Uani 1 1 d . . . . .
C19 C -0.60686(12) -0.8156(5) -0.4323(2) 0.0267(6) Uani 1 1 d . . . . .
H19 H -0.574264 -0.876494 -0.395835 0.032 Uiso 1 1 calc R U . . .
C20 C -0.66145(13) -0.9338(5) -0.4229(2) 0.0304(6) Uani 1 1 d . . . . .
H20 H -0.665496 -1.071100 -0.379599 0.037 Uiso 1 1 calc R U . . .
C21 C -0.71013(12) -0.8479(6) -0.4779(2) 0.0296(6) Uani 1 1 d . . . . .
H21 H -0.747005 -0.926777 -0.471425 0.035 Uiso 1 1 calc R U . . .
C22 C -0.70379(12) -0.6455(6) -0.5422(2) 0.0309(7) Uani 1 1 d . . . . .
H22 H -0.736424 -0.589178 -0.579777 0.037 Uiso 1 1 calc R U . . .
C23 C -0.64918(13) -0.5244(5) -0.5514(2) 0.0288(6) Uani 1 1 d . . . . .
H23 H -0.645451 -0.387592 -0.595042 0.035 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
N1 C16 1.349(3) . ?
N1 C9 1.351(3) . ?
O1 C1 1.387(3) . ?
O1 C8 1.389(3) . ?
C1 C2 1.382(4) . ?
C1 C6 1.390(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.398(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.399(4) . ?
C6 C7 1.444(4) . ?
C7 C17 1.385(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.390(4) . ?
C9 C10 1.486(4) . ?
C10 C11 1.393(4) . ?
C10 C15 1.398(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.384(4) . ?
C16 C17 1.389(4) . ?
C16 C18 1.492(3) . ?
C18 C19 1.391(4) . ?
C18 C23 1.404(4) . ?
C19 C20 1.380(4) . ?
C20 C21 1.383(4) . ?
C21 C22 1.375(4) . ?
C22 C23 1.387(4) . ?

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
C16 N1 C9 121.6(2) . . ?
C1 O1 C8 106.6(2) . . ?
C2 C1 O1 126.1(3) . . ?
C2 C1 C6 123.3(3) . . ?
O1 C1 C6 110.6(2) . . ?
C1 C2 C3 116.6(3) . . ?
C2 C3 C4 121.9(3) . . ?
C5 C4 C3 120.3(3) . . ?
C4 C5 C6 118.8(3) . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 106.1(2) . . ?
C5 C6 C7 134.8(3) . . ?
C17 C7 C8 119.3(2) . . ?
C17 C7 C6 134.1(3) . . ?
C8 C7 C6 106.6(2) . . ?
O1 C8 C9 128.1(2) . . ?
O1 C8 C7 110.1(2) . . ?
C9 C8 C7 121.8(2) . . ?
N1 C9 C8 117.6(2) . . ?
N1 C9 C10 116.9(2) . . ?
C8 C9 C10 125.5(2) . . ?
C11 C10 C15 118.2(2) . . ?
C11 C10 C9 122.1(3) . . ?
C15 C10 C9 119.7(2) . . ?
C12 C11 C10 120.9(3) . . ?
C11 C12 C13 120.1(3) . . ?
C14 C13 C12 119.6(3) . . ?
C15 C14 C13 120.3(3) . . ?
C14 C15 C10 120.9(3) . . ?
N1 C16 C17 122.4(2) . . ?
N1 C16 C18 115.0(2) . . ?
C17 C16 C18 122.7(2) . . ?
C7 C17 C16 117.3(2) . . ?
C19 C18 C23 117.9(2) . . ?
C19 C18 C16 120.3(2) . . ?
C23 C18 C16 121.8(2) . . ?
C20 C19 C18 121.5(2) . . ?
C19 C20 C21 120.0(3) . . ?
C22 C21 C20 119.7(3) . . ?
C21 C22 C23 120.6(3) . . ?
C22 C23 C18 120.3(3) . . ?

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
C8 O1 C1 C2 178.0(3) . . . . ?
C8 O1 C1 C6 -0.3(3) . . . . ?
O1 C1 C2 C3 -178.0(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
O1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
O1 C1 C6 C7 0.1(3) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 177.8(3) . . . . ?
C1 C6 C7 C17 -177.8(3) . . . . ?
C5 C6 C7 C17 3.7(5) . . . . ?
C1 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C8 -178.4(3) . . . . ?
C1 O1 C8 C9 179.6(3) . . . . ?
C1 O1 C8 C7 0.4(3) . . . . ?
C17 C7 C8 O1 177.9(2) . . . . ?
C6 C7 C8 O1 -0.4(3) . . . . ?
C17 C7 C8 C9 -1.3(4) . . . . ?
C6 C7 C8 C9 -179.6(2) . . . . ?
C16 N1 C9 C8 0.7(4) . . . . ?
C16 N1 C9 C10 -178.0(2) . . . . ?
O1 C8 C9 N1 -177.8(2) . . . . ?
C7 C8 C9 N1 1.3(4) . . . . ?
O1 C8 C9 C10 0.7(4) . . . . ?
C7 C8 C9 C10 179.8(2) . . . . ?
N1 C9 C10 C11 -179.6(2) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
N1 C9 C10 C15 2.4(4) . . . . ?
C8 C9 C10 C15 -176.1(2) . . . . ?
C15 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C11 C12 -177.4(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C11 C10 C15 C14 -0.8(4) . . . . ?
C9 C10 C15 C14 177.2(3) . . . . ?
C9 N1 C16 C17 -2.6(4) . . . . ?
C9 N1 C16 C18 177.2(2) . . . . ?
C8 C7 C17 C16 -0.6(4) . . . . ?
C6 C7 C17 C16 177.2(3) . . . . ?
N1 C16 C17 C7 2.5(4) . . . . ?
C18 C16 C17 C7 -177.3(2) . . . . ?
N1 C16 C18 C19 0.0(3) . . . . ?
C17 C16 C18 C19 179.8(2) . . . . ?
N1 C16 C18 C23 -178.9(2) . . . . ?
C17 C16 C18 C23 0.9(4) . . . . ?
C23 C18 C19 C20 -1.7(4) . . . . ?
C16 C18 C19 C20 179.3(3) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C19 C18 C23 C22 1.2(4) . . . . ?
C16 C18 C23 C22 -179.8(3) . . . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044

