# 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 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_d8_n_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1952336'
loop_
_audit_author_name
_audit_author_address
'Sandip Kundu'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2019-09-09 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2019-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 N2 O'
_chemical_formula_sum            'C26 H20 N2 O'
_chemical_formula_weight         376.44
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.6475(8)
_cell_length_b                   12.5986(10)
_cell_length_c                   26.1644(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3839.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.344
_cell_measurement_theta_min      3.796
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1015 before and 0.0754 after correction. The Ratio of minimum to maximum transmission is 0.8833. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26950
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.383
_diffrn_reflns_theta_max         53.383
_diffrn_reflns_theta_min         5.084
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2143
_reflns_number_total             2202
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.114
_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)+(0.0527P)²+1.5340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C17(H17), C10(H10), C14(H14), C7(H7), C9(H9), C15(H15),
 C26(H26), C25(H25), C22(H22), C16(H16), C24(H24), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.46138(11) 0.17954(10) 0.43177(5) 0.0393(4) Uani 1 1 d . . . . .
N1 N 0.27718(13) 0.44106(12) 0.47932(6) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.49248(13) 0.51411(12) 0.62340(6) 0.0343(4) Uani 1 1 d . . . . .
C5 C 0.39579(16) 0.26396(15) 0.44568(7) 0.0319(5) Uani 1 1 d . . . . .
C6 C 0.29741(16) 0.29423(15) 0.41801(7) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.43361(16) 0.31756(15) 0.48750(7) 0.0317(5) Uani 1 1 d . . . . .
C1 C 0.36908(16) 0.40591(15) 0.50530(7) 0.0309(5) Uani 1 1 d . . . . .
C11 C 0.24382(16) 0.38840(15) 0.43594(7) 0.0317(5) Uani 1 1 d . . . . .
C21 C 0.55634(16) 0.47421(15) 0.71239(7) 0.0334(5) Uani 1 1 d . . . . .
C19 C 0.49401(16) 0.44817(15) 0.58189(7) 0.0339(5) Uani 1 1 d . . . . .
H19 H 0.553960 0.399472 0.574399 0.041 Uiso 1 1 calc R . . . .
C13 C 0.32995(16) 0.54314(15) 0.57810(7) 0.0330(5) Uani 1 1 d . . . . .
C12 C 0.39710(16) 0.46166(15) 0.55236(7) 0.0317(5) Uani 1 1 d . . . . .
C18 C 0.39216(16) 0.57253(15) 0.62221(7) 0.0342(5) Uani 1 1 d . . . . .
C20 C 0.58271(17) 0.52399(17) 0.66134(7) 0.0384(5) Uani 1 1 d . . . . .
H20A H 0.598838 0.600333 0.666699 0.046 Uiso 1 1 calc R . . . .
H20B H 0.653405 0.491041 0.647575 0.046 Uiso 1 1 calc R . . . .
C8 C 0.16349(17) 0.28222(16) 0.34788(8) 0.0404(6) Uani 1 1 d . . . . .
H8 H 0.134929 0.246523 0.318537 0.048 Uiso 1 1 calc R . . . .
C17 C 0.35353(18) 0.64837(17) 0.65694(7) 0.0415(5) Uani 1 1 d . . . . .
H17 H 0.396223 0.665634 0.686741 0.050 Uiso 1 1 calc R . . . .
C10 C 0.14973(16) 0.42882(16) 0.40751(7) 0.0359(5) Uani 1 1 d . . . . .
H10 H 0.112637 0.492054 0.418408 0.043 Uiso 1 1 calc R . . . .
C14 C 0.22517(16) 0.59491(16) 0.56836(8) 0.0379(5) Uani 1 1 d . . . . .
H14 H 0.180957 0.577615 0.539011 0.045 Uiso 1 1 calc R . . . .
C7 C 0.25500(17) 0.24137(16) 0.37427(7) 0.0374(5) Uani 1 1 d . . . . .
H7 H 0.290046 0.177340 0.363122 0.045 Uiso 1 1 calc R . . . .
C9 C 0.11179(17) 0.37756(17) 0.36448(8) 0.0406(5) Uani 1 1 d . . . . .
H9 H 0.049743 0.406645 0.345526 0.049 Uiso 1 1 calc R . . . .
C3 C 0.54370(17) 0.26579(16) 0.50551(7) 0.0360(5) Uani 1 1 d . . . . .
H3A H 0.535377 0.236802 0.540480 0.043 Uiso 1 1 calc R . . . .
H3B H 0.608625 0.316485 0.504844 0.043 Uiso 1 1 calc R . . . .
C15 C 0.18784(18) 0.67148(16) 0.60239(8) 0.0435(6) Uani 1 1 d . . . . .
H15 H 0.117699 0.707473 0.595840 0.052 Uiso 1 1 calc R . . . .
C26 C 0.63141(19) 0.49167(17) 0.75287(8) 0.0427(6) Uani 1 1 d . . . . .
H26 H 0.696690 0.535738 0.747998 0.051 Uiso 1 1 calc R . . . .
C25 C 0.6123(2) 0.44584(18) 0.80001(8) 0.0488(6) Uani 1 1 d . . . . .
H25 H 0.664456 0.458008 0.827320 0.059 Uiso 1 1 calc R . . . .
C22 C 0.46188(18) 0.41025(17) 0.72036(8) 0.0424(6) Uani 1 1 d . . . . .
H22 H 0.409744 0.397499 0.693118 0.051 Uiso 1 1 calc R . . . .
C16 C 0.25049(19) 0.69720(17) 0.64604(8) 0.0461(6) Uani 1 1 d . . . . .
H16 H 0.221554 0.749523 0.668793 0.055 Uiso 1 1 calc R . . . .
C4 C 0.56018(18) 0.17709(17) 0.46623(8) 0.0458(6) Uani 1 1 d . . . . .
H4A H 0.632060 0.188437 0.446793 0.055 Uiso 1 1 calc R . . . .
H4B H 0.564885 0.107436 0.483623 0.055 Uiso 1 1 calc R . . . .
C24 C 0.5173(2) 0.38227(18) 0.80735(8) 0.0493(6) Uani 1 1 d . . . . .
H24 H 0.503640 0.350840 0.839793 0.059 Uiso 1 1 calc R . . . .
C23 C 0.4423(2) 0.36444(18) 0.76769(8) 0.0492(6) Uani 1 1 d . . . . .
H23 H 0.376918 0.320599 0.772755 0.059 Uiso 1 1 calc R . . . .


_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 C5 1.359(2) . ?
O1 C4 1.462(2) . ?
N1 C1 1.343(2) . ?
N1 C11 1.371(2) . ?
N2 C19 1.368(2) . ?
N2 C18 1.381(2) . ?
N2 C20 1.451(2) . ?
C5 C6 1.408(3) . ?
C5 C2 1.359(3) . ?
C6 C11 1.420(3) . ?
C6 C7 1.413(3) . ?
C2 C1 1.422(3) . ?
C2 C3 1.514(3) . ?
C1 C12 1.455(3) . ?
C11 C10 1.419(3) . ?
C21 C20 1.507(3) . ?
C21 C26 1.391(3) . ?
C21 C22 1.380(3) . ?
C19 C12 1.378(3) . ?
C13 C12 1.456(3) . ?
C13 C18 1.412(3) . ?
C13 C14 1.407(3) . ?
C18 C17 1.393(3) . ?
C8 C7 1.370(3) . ?
C8 C9 1.412(3) . ?
C17 C16 1.378(3) . ?
C10 C9 1.371(3) . ?
C14 C15 1.383(3) . ?
C3 C4 1.530(3) . ?
C15 C16 1.394(3) . ?
C26 C25 1.380(3) . ?
C25 C24 1.380(3) . ?
C22 C23 1.385(3) . ?
C24 C23 1.375(3) . ?

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
C5 O1 C4 107.08(14) . . ?
C1 N1 C11 119.04(16) . . ?
C19 N2 C18 108.47(15) . . ?
C19 N2 C20 125.87(16) . . ?
C18 N2 C20 125.63(16) . . ?
O1 C5 C6 122.12(17) . . ?
O1 C5 C2 114.97(16) . . ?
C2 C5 C6 122.90(17) . . ?
C5 C6 C11 114.46(17) . . ?
C5 C6 C7 124.97(18) . . ?
C7 C6 C11 120.49(17) . . ?
C5 C2 C1 118.78(17) . . ?
C5 C2 C3 108.12(16) . . ?
C1 C2 C3 133.10(17) . . ?
N1 C1 C2 120.91(17) . . ?
N1 C1 C12 116.62(16) . . ?
C2 C1 C12 122.47(17) . . ?
N1 C11 C6 123.58(17) . . ?
N1 C11 C10 118.63(17) . . ?
C10 C11 C6 117.79(17) . . ?
C26 C21 C20 118.74(17) . . ?
C22 C21 C20 122.65(17) . . ?
C22 C21 C26 118.60(18) . . ?
N2 C19 C12 111.08(17) . . ?
C18 C13 C12 106.70(17) . . ?
C14 C13 C12 135.17(18) . . ?
C14 C13 C18 118.13(18) . . ?
C1 C12 C13 127.70(17) . . ?
C19 C12 C1 126.77(17) . . ?
C19 C12 C13 105.52(16) . . ?
N2 C18 C13 108.23(16) . . ?
N2 C18 C17 128.60(18) . . ?
C17 C18 C13 123.17(18) . . ?
N2 C20 C21 115.02(16) . . ?
C7 C8 C9 119.76(19) . . ?
C16 C17 C18 116.89(19) . . ?
C9 C10 C11 120.68(19) . . ?
C15 C14 C13 118.66(19) . . ?
C8 C7 C6 120.19(19) . . ?
C10 C9 C8 121.05(19) . . ?
C2 C3 C4 102.24(15) . . ?
C14 C15 C16 121.68(19) . . ?
C25 C26 C21 120.9(2) . . ?
C26 C25 C24 119.8(2) . . ?
C21 C22 C23 120.6(2) . . ?
C17 C16 C15 121.45(19) . . ?
O1 C4 C3 107.46(15) . . ?
C23 C24 C25 120.0(2) . . ?
C24 C23 C22 120.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate-Hexane'
