# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2040195'
loop_
_audit_author_name
_audit_author_address
'SK SHAMIM ISLAM'
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H19 N O'
_chemical_formula_weight         409.46

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.4594(4)
_cell_length_b                   11.1120(5)
_cell_length_c                   12.7546(6)
_cell_angle_alpha                72.9290(10)
_cell_angle_beta                 85.1410(10)
_cell_angle_gamma                80.7110(10)
_cell_volume                     996.60(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      25

_exptl_crystal_description       rectengular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6745
_exptl_absorpt_correction_T_max  0.7212
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12034
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.082
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3498
_reflns_number_gt                2883
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0611P)²+0.1329P] 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_number_reflns         3498
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.27781(13) 0.52370(9) 0.61460(8) 0.0176(3) Uani 1 1 d . . . . .
N1 N 0.22129(16) 0.35605(11) 0.55058(9) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.17746(19) 0.31621(14) 0.46135(11) 0.0155(3) Uani 1 1 d . . . . .
C30 C 0.2996(2) 0.59740(14) 0.22223(12) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.19954(19) 0.39895(14) 0.35163(12) 0.0162(3) Uani 1 1 d . . . . .
C13 C 0.14368(19) 0.16044(14) 0.61876(12) 0.0162(3) Uani 1 1 d . . . . .
C12 C 0.12559(19) 0.19789(14) 0.50317(12) 0.0169(3) Uani 1 1 d . . . . .
H12 H 0.0856 0.1505 0.4630 0.020 Uiso 1 1 calc R U . . .
C7 C 0.27631(19) 0.55793(13) 0.42820(12) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.3463(2) 0.79455(14) 0.38623(13) 0.0195(4) Uani 1 1 d . . . . .
H5 H 0.3533 0.8155 0.3100 0.023 Uiso 1 1 calc R U . . .
C8 C 0.25863(19) 0.47634(14) 0.53054(12) 0.0152(3) Uani 1 1 d . . . . .
C9 C 0.25463(19) 0.51565(14) 0.33397(12) 0.0162(3) Uani 1 1 d . . . . .
C14 C 0.20676(19) 0.25933(13) 0.64741(12) 0.0161(3) Uani 1 1 d . . . . .
C18 C 0.1178(2) 0.04931(14) 0.70303(12) 0.0197(4) Uani 1 1 d . . . . .
H18 H 0.0700 -0.0160 0.6882 0.024 Uiso 1 1 calc R U . . .
C28 C 0.2636(2) 0.80016(15) 0.08420(12) 0.0219(4) Uani 1 1 d . . . . .
H28 H 0.2046 0.8832 0.0602 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3281(2) 0.73455(14) 0.61771(13) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.3216 0.7138 0.6939 0.024 Uiso 1 1 calc R U . . .
C24 C 0.1575(2) 0.34954(14) 0.26100(12) 0.0177(3) Uani 1 1 d . . . . .
C29 C 0.2131(2) 0.72169(14) 0.18476(12) 0.0189(3) Uani 1 1 d . . . . .
H29 H 0.1203 0.7525 0.2277 0.023 Uiso 1 1 calc R U . . .
C22 C -0.0221(2) 0.36701(16) 0.10724(13) 0.0262(4) Uani 1 1 d . . . . .
H22 H -0.1137 0.4116 0.0597 0.031 Uiso 1 1 calc R U . . .
C25 C 0.4363(2) 0.55305(15) 0.15525(12) 0.0204(4) Uani 1 1 d . . . . .
H25 H 0.4938 0.4695 0.1782 0.025 Uiso 1 1 calc R U . . .
C6 C 0.31427(19) 0.67342(14) 0.44882(12) 0.0161(3) Uani 1 1 d . . . . .
C16 C 0.2346(2) 0.13688(15) 0.83218(12) 0.0218(4) Uani 1 1 d . . . . .
H16 H 0.2681 0.1257 0.9034 0.026 Uiso 1 1 calc R U . . .
C23 C 0.0222(2) 0.41600(15) 0.18792(12) 0.0214(4) Uani 1 1 d . . . . .
H23 H -0.0386 0.4939 0.1936 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2035(2) 0.18580(16) 0.16819(13) 0.0259(4) Uani 1 1 d . . . . .
H20 H 0.2648 0.1084 0.1617 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3674(2) 0.88288(15) 0.43942(13) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.3893 0.9636 0.3980 0.027 Uiso 1 1 calc R U . . .
C27 C 0.4011(2) 0.75594(15) 0.01912(12) 0.0236(4) Uani 1 1 d . . . . .
H27 H 0.4352 0.8091 -0.0482 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2474(2) 0.23417(14) 0.24943(12) 0.0210(4) Uani 1 1 d . . . . .
H19 H 0.3386 0.1888 0.2971 0.025 Uiso 1 1 calc R U . . .
C21 C 0.0685(2) 0.25238(16) 0.09656(13) 0.0275(4) Uani 1 1 d . . . . .
H21 H 0.0390 0.2202 0.0417 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3566(2) 0.85423(15) 0.55334(13) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.3688 0.9164 0.5866 0.027 Uiso 1 1 calc R U . . .
C1 C 0.30988(19) 0.64792(14) 0.56308(12) 0.0169(3) Uani 1 1 d . . . . .
C15 C 0.2547(2) 0.24889(14) 0.75331(12) 0.0187(3) Uani 1 1 d . . . . .
H15 H 0.2982 0.3148 0.7698 0.022 Uiso 1 1 calc R U . . .
C17 C 0.1644(2) 0.03879(15) 0.80763(12) 0.0215(4) Uani 1 1 d . . . . .
H17 H 0.1491 -0.0349 0.8634 0.026 Uiso 1 1 calc R U . . .
C26 C 0.4873(2) 0.63214(15) 0.05495(12) 0.0228(4) Uani 1 1 d . . . . .
H26 H 0.5797 0.6018 0.0116 0.027 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 1.3522(17) . ?
O1 C1 1.3934(17) . ?
N1 C8 1.3555(19) . ?
N1 C14 1.3884(18) . ?
N1 C11 1.4155(19) . ?
C11 C12 1.371(2) . ?
C11 C10 1.444(2) . ?
C30 C29 1.389(2) . ?
C30 C25 1.397(2) . ?
C30 C9 1.492(2) . ?
C10 C9 1.373(2) . ?
C10 C24 1.492(2) . ?
C13 C18 1.407(2) . ?
C13 C14 1.412(2) . ?
C13 C12 1.421(2) . ?
C7 C8 1.363(2) . ?
C7 C9 1.442(2) . ?
C7 C6 1.458(2) . ?
C5 C4 1.381(2) . ?
C5 C6 1.395(2) . ?
C14 C15 1.394(2) . ?
C18 C17 1.374(2) . ?
C28 C29 1.384(2) . ?
C28 C27 1.384(2) . ?
C2 C1 1.372(2) . ?
C2 C3 1.381(2) . ?
C24 C19 1.390(2) . ?
C24 C23 1.395(2) . ?
C22 C21 1.380(2) . ?
C22 C23 1.382(2) . ?
C25 C26 1.385(2) . ?
C6 C1 1.399(2) . ?
C16 C15 1.372(2) . ?
C16 C17 1.404(2) . ?
C20 C19 1.383(2) . ?
C20 C21 1.384(2) . ?
C4 C3 1.391(2) . ?
C27 C26 1.382(2) . ?

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
C8 O1 C1 103.97(11) . . ?
C8 N1 C14 131.92(13) . . ?
C8 N1 C11 118.50(12) . . ?
C14 N1 C11 109.47(12) . . ?
C12 C11 N1 107.73(12) . . ?
C12 C11 C10 133.94(14) . . ?
N1 C11 C10 118.30(13) . . ?
C29 C30 C25 118.43(13) . . ?
C29 C30 C9 120.71(13) . . ?
C25 C30 C9 120.77(13) . . ?
C9 C10 C11 121.13(14) . . ?
C9 C10 C24 123.16(13) . . ?
C11 C10 C24 115.71(12) . . ?
C18 C13 C14 117.97(13) . . ?
C18 C13 C12 133.67(14) . . ?
C14 C13 C12 108.33(13) . . ?
C11 C12 C13 108.00(13) . . ?
C8 C7 C9 118.98(13) . . ?
C8 C7 C6 103.86(13) . . ?
C9 C7 C6 137.15(13) . . ?
C4 C5 C6 118.87(14) . . ?
O1 C8 N1 120.39(12) . . ?
O1 C8 C7 115.44(13) . . ?
N1 C8 C7 124.16(14) . . ?
C10 C9 C7 118.17(13) . . ?
C10 C9 C30 122.76(13) . . ?
C7 C9 C30 119.02(13) . . ?
N1 C14 C15 130.28(13) . . ?
N1 C14 C13 106.37(12) . . ?
C15 C14 C13 123.18(13) . . ?
C17 C18 C13 118.92(14) . . ?
C29 C28 C27 120.49(14) . . ?
C1 C2 C3 116.38(14) . . ?
C19 C24 C23 118.29(14) . . ?
C19 C24 C10 120.95(13) . . ?
C23 C24 C10 120.73(14) . . ?
C28 C29 C30 120.66(14) . . ?
C21 C22 C23 120.58(15) . . ?
C26 C25 C30 120.73(14) . . ?
C5 C6 C1 117.34(14) . . ?
C5 C6 C7 136.92(14) . . ?
C1 C6 C7 105.70(12) . . ?
C15 C16 C17 121.38(14) . . ?
C22 C23 C24 120.54(15) . . ?
C19 C20 C21 120.12(16) . . ?
C5 C4 C3 121.71(15) . . ?
C26 C27 C28 119.47(14) . . ?
C20 C19 C24 121.01(15) . . ?
C22 C21 C20 119.45(15) . . ?
C2 C3 C4 120.85(15) . . ?
C2 C1 O1 124.18(13) . . ?
C2 C1 C6 124.80(14) . . ?
O1 C1 C6 110.99(13) . . ?
C16 C15 C14 116.93(14) . . ?
C18 C17 C16 121.49(14) . . ?
C27 C26 C25 120.21(15) . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.085



