# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_ra5
_database_code_depnum_ccdc_archive 'CCDC 2153056'
loop_
_audit_author_name
_audit_author_address
'Sabina Yashmin'
;Indian Institute of Technology, Guwahati
India
;
_audit_update_record             
;
2022-02-18 deposited with the CCDC.	2022-04-25 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            'C27 H21 N O'
_chemical_formula_weight         375.45

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.9415(9)
_cell_length_b                   20.8156(11)
_cell_length_c                   11.0217(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.915(9)
_cell_angle_gamma                90
_cell_volume                     1928.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    957
_cell_measurement_theta_min      2.6110
_cell_measurement_theta_max      25.6050

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.963
_exptl_transmission_factor_max   0.985
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6743
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3414
_reflns_number_gt                1709
_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)+(0.0601P)²+0.0386P] 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         3414
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.4614(3) 0.38245(9) 0.45388(16) 0.0507(6) Uani 1 1 d . . . . .
N1 N 0.6167(3) 0.53386(11) 0.28325(19) 0.0397(6) Uani 1 1 d . . . . .
C23 C 0.6634(4) 0.46070(12) 0.4593(2) 0.0368(7) Uani 1 1 d . . . . .
C1 C 0.5652(3) 0.48489(13) 0.3329(2) 0.0358(7) Uani 1 1 d . . . . .
C2 C 0.4169(3) 0.45361(13) 0.2717(2) 0.0362(7) Uani 1 1 d . . . . .
C3 C 0.3196(4) 0.47409(13) 0.1485(2) 0.0410(8) Uani 1 1 d . . . . .
C17 C 0.3678(3) 0.40176(13) 0.3315(2) 0.0394(7) Uani 1 1 d . . . . .
C4 C 0.3766(4) 0.52757(14) 0.0930(2) 0.0405(8) Uani 1 1 d . . . . .
C18 C 0.6070(4) 0.41064(13) 0.5146(2) 0.0402(8) Uani 1 1 d . . . . .
C16 C 0.2273(4) 0.36821(14) 0.2739(3) 0.0424(8) Uani 1 1 d . . . . .
C13 C 0.5222(4) 0.55527(13) 0.1634(2) 0.0395(7) Uani 1 1 d . . . . .
C22 C 0.8138(4) 0.48500(14) 0.5286(2) 0.0450(8) Uani 1 1 d . . . . .
H22 H 0.8558 0.5182 0.4937 0.054 Uiso 1 1 calc R U . . .
C19 C 0.6916(4) 0.38610(14) 0.6350(2) 0.0479(8) Uani 1 1 d . . . . .
H19 H 0.6497 0.3533 0.6710 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7260(4) 0.63935(14) 0.1803(3) 0.0497(9) Uani 1 1 d . . . . .
H11 H 0.7867 0.6239 0.2613 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5811(4) 0.60952(14) 0.1116(3) 0.0435(8) Uani 1 1 d . . . . .
C15 C 0.1348(4) 0.39056(15) 0.1516(3) 0.0515(9) Uani 1 1 d . . . . .
H15 H 0.0390 0.3698 0.1092 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1770(4) 0.44121(14) 0.0907(3) 0.0485(9) Uani 1 1 d . . . . .
H14 H 0.1095 0.4539 0.0096 0.058 Uiso 1 1 calc R U . . .
C20 C 0.8392(4) 0.41134(15) 0.7002(3) 0.0527(9) Uani 1 1 d . . . . .
H20 H 0.8983 0.3950 0.7808 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4909(4) 0.63317(15) -0.0118(3) 0.0507(9) Uani 1 1 d . . . . .
C21 C 0.9012(4) 0.46052(15) 0.6482(2) 0.0519(9) Uani 1 1 d . . . . .
H21 H 1.0013 0.4771 0.6935 0.062 Uiso 1 1 calc R U . . .
C24 C 0.1776(4) 0.31041(15) 0.3381(3) 0.0519(9) Uani 1 1 d . . . . .
C5 C 0.2901(4) 0.55233(15) -0.0316(3) 0.0515(9) Uani 1 1 d . . . . .
H5 H 0.1937 0.5336 -0.0798 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3458(4) 0.60246(16) -0.0805(3) 0.0565(10) Uani 1 1 d . . . . .
H6 H 0.2868 0.6174 -0.1624 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5492(5) 0.68637(17) -0.0608(3) 0.0656(11) Uani 1 1 d . . . . .
H8 H 0.4902 0.7025 -0.1417 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7790(5) 0.69116(15) 0.1291(3) 0.0628(10) Uani 1 1 d . . . . .
H10 H 0.8750 0.7106 0.1757 0.075 Uiso 1 1 calc R U . . .
C25 C 0.3056(4) 0.25783(15) 0.3690(3) 0.0655(10) Uani 1 1 d . . . . .
H25A H 0.3271 0.2467 0.2920 0.098 Uiso 1 1 calc R U . . .
H25B H 0.2685 0.2205 0.4014 0.098 Uiso 1 1 calc R U . . .
H25C H 0.4013 0.2733 0.4329 0.098 Uiso 1 1 calc R U . . .
C9 C 0.6895(5) 0.71471(17) 0.0073(3) 0.0707(11) Uani 1 1 d . . . . .
H9 H 0.7259 0.7497 -0.0270 0.085 Uiso 1 1 calc R U . . .
C26 C 0.0234(4) 0.27979(16) 0.2490(3) 0.0704(11) Uani 1 1 d . . . . .
H26A H -0.0614 0.3106 0.2301 0.106 Uiso 1 1 calc R U . . .
H26B H -0.0024 0.2431 0.2909 0.106 Uiso 1 1 calc R U . . .
H26C H 0.0374 0.2665 0.1701 0.106 Uiso 1 1 calc R U . . .
C27 C 0.1487(5) 0.33190(17) 0.4620(3) 0.0919(15) Uani 1 1 d . . . . .
H27A H 0.2414 0.3537 0.5176 0.138 Uiso 1 1 calc R U . . .
H27B H 0.1276 0.2949 0.5057 0.138 Uiso 1 1 calc R U . . .
H27C H 0.0591 0.3605 0.4400 0.138 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 C18 1.376(3) . ?
O1 C17 1.383(3) . ?
N1 C1 1.312(3) . ?
N1 C13 1.377(3) . ?
C23 C18 1.386(4) . ?
C23 C22 1.395(4) . ?
C23 C1 1.460(3) . ?
C1 C2 1.424(4) . ?
C2 C3 1.406(3) . ?
C2 C17 1.411(4) . ?
C3 C14 1.396(4) . ?
C3 C4 1.444(4) . ?
C17 C16 1.388(4) . ?
C4 C13 1.393(4) . ?
C4 C5 1.423(3) . ?
C18 C19 1.382(4) . ?
C16 C15 1.399(4) . ?
C16 C24 1.536(4) . ?
C13 C12 1.444(4) . ?
C22 C21 1.381(3) . ?
C19 C20 1.374(4) . ?
C11 C10 1.374(4) . ?
C11 C12 1.403(4) . ?
C12 C7 1.412(4) . ?
C15 C14 1.370(4) . ?
C20 C21 1.378(4) . ?
C7 C8 1.407(4) . ?
C7 C6 1.413(4) . ?
C24 C26 1.533(4) . ?
C24 C25 1.536(4) . ?
C24 C27 1.541(4) . ?
C5 C6 1.346(4) . ?
C8 C9 1.358(5) . ?
C10 C9 1.396(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
C18 O1 C17 120.6(2) . . ?
C1 N1 C13 117.6(3) . . ?
C18 C23 C22 117.3(2) . . ?
C18 C23 C1 119.2(3) . . ?
C22 C23 C1 123.5(3) . . ?
N1 C1 C2 124.1(2) . . ?
N1 C1 C23 118.9(3) . . ?
C2 C1 C23 117.0(2) . . ?
C3 C2 C17 119.6(3) . . ?
C3 C2 C1 119.2(3) . . ?
C17 C2 C1 121.1(2) . . ?
C14 C3 C2 117.4(3) . . ?
C14 C3 C4 125.8(3) . . ?
C2 C3 C4 116.8(3) . . ?
O1 C17 C16 116.9(3) . . ?
O1 C17 C2 119.8(3) . . ?
C16 C17 C2 123.3(2) . . ?
C13 C4 C5 119.0(3) . . ?
C13 C4 C3 118.7(2) . . ?
C5 C4 C3 122.2(3) . . ?
O1 C18 C19 115.3(3) . . ?
O1 C18 C23 122.2(2) . . ?
C19 C18 C23 122.5(3) . . ?
C17 C16 C15 114.8(3) . . ?
C17 C16 C24 122.8(3) . . ?
C15 C16 C24 122.4(3) . . ?
N1 C13 C4 123.5(3) . . ?
N1 C13 C12 116.4(3) . . ?
C4 C13 C12 120.1(2) . . ?
C21 C22 C23 121.0(3) . . ?
C20 C19 C18 118.4(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 C13 121.8(3) . . ?
C7 C12 C13 119.2(3) . . ?
C14 C15 C16 123.8(3) . . ?
C15 C14 C3 121.0(3) . . ?
C19 C20 C21 121.2(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 122.9(3) . . ?
C12 C7 C6 118.5(3) . . ?
C20 C21 C22 119.6(3) . . ?
C26 C24 C25 106.6(2) . . ?
C26 C24 C16 111.6(3) . . ?
C25 C24 C16 110.5(3) . . ?
C26 C24 C27 107.6(3) . . ?
C25 C24 C27 110.3(3) . . ?
C16 C24 C27 110.1(2) . . ?
C6 C5 C4 120.9(3) . . ?
C5 C6 C7 122.2(3) . . ?
C9 C8 C7 121.5(3) . . ?
C11 C10 C9 120.4(4) . . ?
C8 C9 C10 119.9(3) . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040

