# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 2300318'
loop_
_audit_author_name
_audit_author_address
'Dr. Ruchir Kant'
;CSIR CDRI, Lucknow
India
;
_audit_update_record             
;
2023-10-10 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.34

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'
N N 0.0311 0.0180 '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'
#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.363(2)
_cell_length_b                   10.957(2)
_cell_length_c                   12.286(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.460(8)
_cell_angle_gamma                90.00
_cell_volume                     1522.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1388
_cell_measurement_theta_min      6.9
_cell_measurement_theta_max      68.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.8020
_exptl_absorpt_correction_T_max  0.9499
#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            30181
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.89
_diffrn_reflns_theta_max         68.42
_reflns_number_total             2767
_reflns_number_gt                1810
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1025P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2767
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41402(17) 1.21285(16) 0.11520(18) 0.0737(6) Uani 1 1 d . . .
H1 H 0.4498 1.2657 0.0691 0.088 Uiso 1 1 calc R . .
C2 C 0.40822(18) 1.24417(16) 0.2217(2) 0.0784(6) Uani 1 1 d . . .
H2 H 0.4399 1.3182 0.2474 0.094 Uiso 1 1 calc R . .
C3 C 0.35522(18) 1.16649(17) 0.29309(17) 0.0748(6) Uani 1 1 d . . .
H3 H 0.3504 1.1895 0.3654 0.090 Uiso 1 1 calc R . .
C4 C 0.31059(17) 1.05676(16) 0.25635(15) 0.0652(5) Uani 1 1 d . . .
H4 H 0.2765 1.0048 0.3043 0.078 Uiso 1 1 calc R . .
C5 C 0.31559(13) 1.02129(13) 0.14643(13) 0.0492(4) Uani 1 1 d . . .
C6 C 0.26952(14) 0.90924(15) 0.10390(13) 0.0502(4) Uani 1 1 d . . .
C7 C 0.27421(14) 0.88251(13) -0.00404(12) 0.0490(4) Uani 1 1 d . . .
C8 C 0.32702(16) 0.96933(16) -0.06987(14) 0.0609(5) Uani 1 1 d . . .
H8 H 0.3303 0.9505 -0.1433 0.073 Uiso 1 1 calc R . .
C9 C 0.36640(14) 1.10109(14) 0.07373(14) 0.0554(5) Uani 1 1 d . . .
C10 C 0.22847(15) 0.76546(14) -0.05322(13) 0.0560(5) Uani 1 1 d . . .
C11 C 0.16822(14) 0.67954(13) 0.01935(12) 0.0498(4) Uani 1 1 d . . .
C12 C 0.04877(15) 0.69526(14) 0.03544(13) 0.0550(5) Uani 1 1 d . . .
C13 C -0.00030(15) 0.61764(16) 0.10824(14) 0.0617(5) Uani 1 1 d . . .
H13 H -0.0794 0.6276 0.1200 0.074 Uiso 1 1 calc R . .
C14 C 0.06404(16) 0.52597(15) 0.16385(13) 0.0592(5) Uani 1 1 d . . .
C15 C 0.18090(15) 0.51111(14) 0.14360(14) 0.0580(5) Uani 1 1 d . . .
H15 H 0.2245 0.4481 0.1785 0.070 Uiso 1 1 calc R . .
C16 C 0.23527(14) 0.58695(14) 0.07305(13) 0.0540(5) Uani 1 1 d . . .
C17 C 0.36463(16) 0.5703(2) 0.05838(19) 0.0809(6) Uani 1 1 d . . .
H17A H 0.3731 0.5450 -0.0153 0.121 Uiso 1 1 calc R . .
H17B H 0.3976 0.5092 0.1083 0.121 Uiso 1 1 calc R . .
H17C H 0.4055 0.6461 0.0727 0.121 Uiso 1 1 calc R . .
C18 C -0.02589(18) 0.79222(19) -0.02465(17) 0.0792(6) Uani 1 1 d . . .
H18A H -0.1052 0.7876 -0.0042 0.119 Uiso 1 1 calc R . .
H18B H -0.0264 0.7796 -0.1020 0.119 Uiso 1 1 calc R . .
H18C H 0.0065 0.8712 -0.0059 0.119 Uiso 1 1 calc R . .
C19 C 0.0103(2) 0.4452(2) 0.24514(17) 0.0851(7) Uani 1 1 d . . .
H19A H -0.0264 0.4949 0.2967 0.128 Uiso 1 1 calc R . .
H19B H 0.0710 0.3963 0.2832 0.128 Uiso 1 1 calc R . .
H19C H -0.0479 0.3931 0.2074 0.128 Uiso 1 1 calc R . .
H6 H 0.2354(14) 0.8529(15) 0.1527(14) 0.061(5) Uiso 1 1 d . . .
N1 N 0.37147(14) 1.07392(13) -0.03495(12) 0.0666(5) Uani 1 1 d . . .
O6 O 0.24112(14) 0.74048(12) -0.14783(10) 0.0902(5) Uani 1 1 d . . .


_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 1.361(3) . ?
C1 C9 1.414(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.399(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(2) . ?
C4 H4 0.9300 . ?
C5 C9 1.412(2) . ?
C5 C6 1.415(2) . ?
C6 C7 1.364(2) . ?
C6 H6 0.968(17) . ?
C7 C8 1.418(2) . ?
C7 C10 1.490(2) . ?
C8 N1 1.308(2) . ?
C8 H8 0.9300 . ?
C9 N1 1.375(2) . ?
C10 O6 1.2159(19) . ?
C10 C11 1.505(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.389(2) . ?
C12 C18 1.508(3) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(2) . ?
C14 C19 1.506(3) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.509(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C2 C1 C9 120.86(18) . . ?
C2 C1 H1 119.6 . . ?
C9 C1 H1 119.6 . . ?
C1 C2 C3 120.84(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.83(19) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.76(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C9 119.39(15) . . ?
C4 C5 C6 123.02(15) . . ?
C9 C5 C6 117.57(15) . . ?
C7 C6 C5 119.87(14) . . ?
C7 C6 H6 121.4(9) . . ?
C5 C6 H6 118.7(9) . . ?
C6 C7 C8 117.92(14) . . ?
C6 C7 C10 122.32(14) . . ?
C8 C7 C10 119.75(14) . . ?
N1 C8 C7 124.86(15) . . ?
N1 C8 H8 117.6 . . ?
C7 C8 H8 117.6 . . ?
N1 C9 C5 122.54(14) . . ?
N1 C9 C1 119.18(15) . . ?
C5 C9 C1 118.28(16) . . ?
O6 C10 C7 120.87(14) . . ?
O6 C10 C11 121.81(14) . . ?
C7 C10 C11 117.31(13) . . ?
C16 C11 C12 121.01(14) . . ?
C16 C11 C10 118.42(14) . . ?
C12 C11 C10 120.53(14) . . ?
C13 C12 C11 118.00(15) . . ?
C13 C12 C18 120.33(16) . . ?
C11 C12 C18 121.67(16) . . ?
C14 C13 C12 122.46(16) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C15 C14 C13 117.88(15) . . ?
C15 C14 C19 120.44(18) . . ?
C13 C14 C19 121.68(18) . . ?
C14 C15 C16 122.26(16) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C11 118.36(15) . . ?
C15 C16 C17 119.92(15) . . ?
C11 C16 C17 121.69(15) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 N1 C9 117.24(13) . . ?

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
C9 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C9 -0.6(3) . . . . ?
C3 C4 C5 C6 -179.29(16) . . . . ?
C4 C5 C6 C7 178.01(15) . . . . ?
C9 C5 C6 C7 -0.7(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C5 C6 C7 C10 179.26(14) . . . . ?
C6 C7 C8 N1 -0.3(3) . . . . ?
C10 C7 C8 N1 -178.99(16) . . . . ?
C4 C5 C9 N1 -178.27(15) . . . . ?
C6 C5 C9 N1 0.5(2) . . . . ?
C4 C5 C9 C1 1.9(2) . . . . ?
C6 C5 C9 C1 -179.31(15) . . . . ?
C2 C1 C9 N1 178.49(16) . . . . ?
C2 C1 C9 C5 -1.7(3) . . . . ?
C6 C7 C10 O6 -174.90(16) . . . . ?
C8 C7 C10 O6 3.8(3) . . . . ?
C6 C7 C10 C11 4.2(2) . . . . ?
C8 C7 C10 C11 -177.19(14) . . . . ?
O6 C10 C11 C16 84.5(2) . . . . ?
C7 C10 C11 C16 -94.54(17) . . . . ?
O6 C10 C11 C12 -97.8(2) . . . . ?
C7 C10 C11 C12 83.17(19) . . . . ?
C16 C11 C12 C13 1.4(2) . . . . ?
C10 C11 C12 C13 -176.29(14) . . . . ?
C16 C11 C12 C18 -178.01(15) . . . . ?
C10 C11 C12 C18 4.3(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C18 C12 C13 C14 178.86(15) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C12 C13 C14 C19 178.04(16) . . . . ?
C13 C14 C15 C16 2.2(2) . . . . ?
C19 C14 C15 C16 -177.08(16) . . . . ?
C14 C15 C16 C11 -1.4(2) . . . . ?
C14 C15 C16 C17 176.99(17) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C10 C11 C16 C15 177.24(13) . . . . ?
C12 C11 C16 C17 -178.77(16) . . . . ?
C10 C11 C16 C17 -1.1(2) . . . . ?
C7 C8 N1 C9 0.1(3) . . . . ?
C5 C9 N1 C8 -0.2(2) . . . . ?
C1 C9 N1 C8 179.62(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        68.42
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.079



####################################################################
#                         END of data
####################################################################



