# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_cmp_2a_m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hmynr
_database_code_depnum_ccdc_archive 'CCDC 2313085'
loop_
_audit_author_name
_audit_author_address
'Chirag Chamakiya'
;BKNMU Junagadh
India
;
_audit_update_record             
;
2023-12-09 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-12-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_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 0.0033 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.045(3)
_cell_length_b                   12.408(11)
_cell_length_c                   15.626(14)
_cell_angle_alpha                80.01(2)
_cell_angle_beta                 88.13(2)
_cell_angle_gamma                87.10(2)
_cell_volume                     771.2(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17994
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.756
_diffrn_reflns_theta_min         2.301
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3231
_reflns_number_total             3901
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.15(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.050
_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)+(0.0720P)²+0.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O23 O 0.1054(3) 0.98520(8) 0.75627(6) 0.0664(3) Uani 1 1 d . . . . .
N21 N 0.1940(2) 0.91239(7) 0.59865(6) 0.0394(2) Uani 1 1 d . . . . .
H21 H 0.071551 0.971754 0.593626 0.047 Uiso 1 1 calc R U . . .
N22 N 0.2467(2) 0.89698(7) 0.44725(6) 0.0394(2) Uani 1 1 d . . . . .
C1 C 0.3075(3) 0.86152(8) 0.53204(7) 0.0354(2) Uani 1 1 d . . . . .
C2 C 0.5009(3) 0.76558(9) 0.56670(7) 0.0368(3) Uani 1 1 d . . . . .
C3 C 0.6409(3) 0.70259(9) 0.50701(7) 0.0393(3) Uani 1 1 d . . . . .
H3 H 0.768998 0.639119 0.526070 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5845(3) 0.73678(9) 0.41895(7) 0.0369(3) Uani 1 1 d . . . . .
C5 C 0.3871(3) 0.83462(9) 0.39324(7) 0.0390(3) Uani 1 1 d . . . . .
H5 H 0.353111 0.856902 0.334105 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4991(3) 0.76205(9) 0.65852(7) 0.0404(3) Uani 1 1 d . . . . .
H6 H 0.605534 0.709117 0.699186 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3093(3) 0.85223(9) 0.67566(7) 0.0387(3) Uani 1 1 d . . . . .
C8 C 0.2354(3) 0.89355(10) 0.75745(7) 0.0445(3) Uani 1 1 d . . . . .
C9 C 0.3277(3) 0.82225(11) 0.84188(8) 0.0463(3) Uani 1 1 d . . . . .
C10 C 0.2751(4) 0.71090(11) 0.85825(8) 0.0530(3) Uani 1 1 d . . . . .
H10 H 0.186808 0.678014 0.815502 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3539(4) 0.64802(14) 0.93850(10) 0.0665(4) Uani 1 1 d . . . . .
H11 H 0.314588 0.573621 0.949328 0.080 Uiso 1 1 calc R U . . .
C12 C 0.4892(4) 0.69528(17) 1.00164(10) 0.0723(5) Uani 1 1 d . . . . .
H12 H 0.545520 0.652642 1.054597 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5413(5) 0.80573(18) 0.98653(10) 0.0766(5) Uani 1 1 d . . . . .
H13 H 0.631641 0.837653 1.029531 0.092 Uiso 1 1 calc R U . . .
C14 C 0.4594(4) 0.87017(14) 0.90699(9) 0.0624(4) Uani 1 1 d . . . . .
H14 H 0.492478 0.944974 0.897382 0.075 Uiso 1 1 calc R U . . .
C15 C 0.7278(3) 0.67498(9) 0.35156(7) 0.0383(3) Uani 1 1 d . . . . .
C16 C 0.7614(3) 0.56079(10) 0.36829(8) 0.0459(3) Uani 1 1 d . . . . .
H16 H 0.689846 0.522685 0.421687 0.055 Uiso 1 1 calc R U . . .
C17 C 0.9007(4) 0.50327(11) 0.30609(9) 0.0545(3) Uani 1 1 d . . . . .
H17 H 0.920571 0.427182 0.318200 0.065 Uiso 1 1 calc R U . . .
C18 C 1.0101(4) 0.55854(13) 0.22618(9) 0.0579(4) Uani 1 1 d . . . . .
H18 H 1.104772 0.519930 0.184893 0.069 Uiso 1 1 calc R U . . .
C19 C 0.9770(4) 0.67144(12) 0.20853(8) 0.0546(3) Uani 1 1 d . . . . .
H19 H 1.049452 0.708956 0.155004 0.065 Uiso 1 1 calc R U . . .
C20 C 0.8359(3) 0.72962(10) 0.27023(8) 0.0462(3) Uani 1 1 d . . . . .
H20 H 0.813282 0.805621 0.257261 0.055 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
O23 C8 1.2259(18) . ?
N21 H21 0.8600 . ?
N21 C1 1.3639(16) . ?
N21 C7 1.3829(17) . ?
N22 C1 1.3483(18) . ?
N22 C5 1.3358(16) . ?
C1 C2 1.4254(17) . ?
C2 C3 1.4055(17) . ?
C2 C6 1.428(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.3906(19) . ?
C4 C5 1.4234(18) . ?
C4 C15 1.4927(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.3845(18) . ?
C7 C8 1.4740(19) . ?
C8 C9 1.502(2) . ?
C9 C10 1.387(2) . ?
C9 C14 1.396(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(2) . ?
C15 C20 1.4004(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.3913(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.3929(19) . ?
C20 H20 0.9300 . ?

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
C1 N21 H21 125.8 . . ?
C1 N21 C7 108.36(11) . . ?
C7 N21 H21 125.8 . . ?
C5 N22 C1 114.82(11) . . ?
N21 C1 C2 108.95(11) . . ?
N22 C1 N21 125.22(11) . . ?
N22 C1 C2 125.83(10) . . ?
C1 C2 C6 105.93(10) . . ?
C3 C2 C1 116.96(11) . . ?
C3 C2 C6 137.11(11) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.86(11) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 118.30(10) . . ?
C3 C4 C15 122.00(11) . . ?
C5 C4 C15 119.69(11) . . ?
N22 C5 C4 125.22(11) . . ?
N22 C5 H5 117.4 . . ?
C4 C5 H5 117.4 . . ?
C2 C6 H6 126.4 . . ?
C7 C6 C2 107.14(10) . . ?
C7 C6 H6 126.4 . . ?
N21 C7 C6 109.62(11) . . ?
N21 C7 C8 119.01(11) . . ?
C6 C7 C8 131.26(11) . . ?
O23 C8 C7 120.40(11) . . ?
O23 C8 C9 120.74(11) . . ?
C7 C8 C9 118.84(12) . . ?
C10 C9 C8 121.93(12) . . ?
C10 C9 C14 118.99(13) . . ?
C14 C9 C8 119.04(14) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.30(14) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.39(17) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.97(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.36(16) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.97(17) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C4 120.82(11) . . ?
C16 C15 C20 118.03(11) . . ?
C20 C15 C4 121.14(12) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.84(13) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.50(14) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.33(12) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.54(13) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.76(13) . . ?
C19 C20 H20 119.6 . . ?

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
O23 C8 C9 C10 138.52(15) . . . . ?
O23 C8 C9 C14 -39.1(2) . . . . ?
N21 C1 C2 C3 -179.64(10) . . . . ?
N21 C1 C2 C6 -0.41(13) . . . . ?
N21 C7 C8 O23 -7.84(19) . . . . ?
N21 C7 C8 C9 173.26(11) . . . . ?
N22 C1 C2 C3 0.13(17) . . . . ?
N22 C1 C2 C6 179.36(11) . . . . ?
C1 N21 C7 C6 0.12(13) . . . . ?
C1 N21 C7 C8 176.71(10) . . . . ?
C1 N22 C5 C4 0.79(17) . . . . ?
C1 C2 C3 C4 0.10(16) . . . . ?
C1 C2 C6 C7 0.47(13) . . . . ?
C2 C3 C4 C5 0.11(16) . . . . ?
C2 C3 C4 C15 179.29(10) . . . . ?
C2 C6 C7 N21 -0.38(13) . . . . ?
C2 C6 C7 C8 -176.41(12) . . . . ?
C3 C2 C6 C7 179.47(13) . . . . ?
C3 C4 C5 N22 -0.60(18) . . . . ?
C3 C4 C15 C16 35.54(17) . . . . ?
C3 C4 C15 C20 -143.69(12) . . . . ?
C4 C15 C16 C17 -178.79(11) . . . . ?
C4 C15 C20 C19 178.37(11) . . . . ?
C5 N22 C1 N21 179.19(10) . . . . ?
C5 N22 C1 C2 -0.55(17) . . . . ?
C5 C4 C15 C16 -145.29(12) . . . . ?
C5 C4 C15 C20 35.47(16) . . . . ?
C6 C2 C3 C4 -178.82(13) . . . . ?
C6 C7 C8 O23 167.89(14) . . . . ?
C6 C7 C8 C9 -11.0(2) . . . . ?
C7 N21 C1 N22 -179.59(11) . . . . ?
C7 N21 C1 C2 0.19(13) . . . . ?
C7 C8 C9 C10 -42.58(18) . . . . ?
C7 C8 C9 C14 139.77(14) . . . . ?
C8 C9 C10 C11 -177.87(13) . . . . ?
C8 C9 C14 C13 178.85(14) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C10 C9 C14 C13 1.1(2) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
C15 C4 C5 N22 -179.80(10) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C15 C20 C19 -0.88(19) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C20 C15 C16 C17 0.47(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
