# Electronic Supplementary Material (ESI) for ChemComm.
# 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_final
_database_code_depnum_ccdc_archive 'CCDC 2115049'
loop_
_audit_author_name
_audit_author_address
'Pravin Kumar'
;IISER Bhopal
India
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_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         'C18 H13 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2597(13)
_cell_length_b                   14.3246(16)
_cell_length_c                   8.6454(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.870(4)
_cell_angle_gamma                90
_cell_volume                     1269.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3062
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.82
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_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            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40037
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.077
_diffrn_reflns_theta_min         2.443
_diffrn_ambient_temperature      140.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                3251
_reflns_number_total             3708
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.026
_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)+(0.0580P)²+0.3893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.15389(7) 0.56622(5) 0.36768(8) 0.02324(16) Uani 1 1 d . . . . .
N1 N 0.25866(8) 0.61969(6) 0.43111(10) 0.02283(18) Uani 1 1 d . . . . .
C1 C -0.07418(10) 0.32103(8) 0.04150(13) 0.0276(2) Uani 1 1 d . . . . .
H1 H -0.134534 0.280101 -0.009327 0.033 Uiso 1 1 calc R . . . .
C2 C 0.03390(10) 0.35300(7) -0.03535(12) 0.0256(2) Uani 1 1 d . . . . .
H2 H 0.046892 0.334671 -0.139319 0.031 Uiso 1 1 calc R . . . .
C3 C 0.12304(9) 0.41183(7) 0.03996(11) 0.02212(19) Uani 1 1 d . . . . .
H3 H 0.197235 0.433291 -0.012527 0.027 Uiso 1 1 calc R . . . .
C4 C 0.10399(9) 0.43957(7) 0.19269(11) 0.01988(19) Uani 1 1 d . . . . .
C5 C 0.19937(9) 0.50099(7) 0.26958(11) 0.02004(19) Uani 1 1 d . . . . .
C6 C 0.33235(9) 0.50821(6) 0.26594(10) 0.01896(18) Uani 1 1 d . . . . .
C7 C 0.36396(9) 0.58393(6) 0.36857(10) 0.01857(18) Uani 1 1 d . . . . .
C8 C 0.49855(9) 0.61299(6) 0.39626(10) 0.01864(18) Uani 1 1 d . . . . .
C9 C 0.59369(9) 0.55874(7) 0.32173(10) 0.01959(18) Uani 1 1 d . . . . .
C10 C 0.72612(10) 0.58215(7) 0.34330(12) 0.0237(2) Uani 1 1 d . . . . .
H10 H 0.790727 0.545690 0.295258 0.028 Uiso 1 1 calc R . . . .
C11 C 0.76298(10) 0.65757(8) 0.43358(12) 0.0269(2) Uani 1 1 d . . . . .
H11 H 0.852688 0.672898 0.447452 0.032 Uiso 1 1 calc R . . . .
C12 C -0.00597(10) 0.40826(7) 0.26915(12) 0.0241(2) Uani 1 1 d . . . . .
H12 H -0.020328 0.427405 0.372419 0.029 Uiso 1 1 calc R . . . .
C13 C -0.09394(10) 0.34903(8) 0.19304(13) 0.0278(2) Uani 1 1 d . . . . .
H13 H -0.168344 0.327422 0.244965 0.033 Uiso 1 1 calc R . . . .
C14 C 0.43215(9) 0.45573(7) 0.19314(11) 0.02173(19) Uani 1 1 d . . . . .
H14 H 0.410822 0.404949 0.126331 0.026 Uiso 1 1 calc R . . . .
C15 C 0.55734(9) 0.48063(7) 0.22235(11) 0.02197(19) Uani 1 1 d . . . . .
H15 H 0.624402 0.445658 0.176042 0.026 Uiso 1 1 calc R . . . .
C16 C 0.66870(10) 0.71144(8) 0.50463(12) 0.0258(2) Uani 1 1 d . . . . .
H16 H 0.695490 0.763257 0.566435 0.031 Uiso 1 1 calc R . . . .
C17 C 0.53652(10) 0.69114(7) 0.48721(11) 0.02173(19) Uani 1 1 d . . . . .
C18 C 0.43883(11) 0.75338(8) 0.56153(13) 0.0284(2) Uani 1 1 d . . . . .
H18A H 0.375802 0.776055 0.482600 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.483958 0.806604 0.610266 0.043 Uiso 1 1 calc GR . . . .
H18C H 0.392960 0.718118 0.640223 0.043 Uiso 1 1 calc GR . . . .


_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 N1 1.4158(11) . ?
O1 C5 1.3549(11) . ?
N1 C7 1.3267(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.3889(15) . ?
C1 C13 1.3913(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3897(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3987(13) . ?
C4 C5 1.4599(13) . ?
C4 C12 1.3998(13) . ?
C5 C6 1.3696(13) . ?
C6 C7 1.4319(13) . ?
C6 C14 1.4323(13) . ?
C7 C8 1.4545(13) . ?
C8 C9 1.4188(13) . ?
C8 C17 1.4153(13) . ?
C9 C10 1.4060(13) . ?
C9 C15 1.4520(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3785(15) . ?
C11 H11 0.9500 . ?
C11 C16 1.3954(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3887(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.3489(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.3903(14) . ?
C17 C18 1.5015(14) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 N1 110.05(7) . . ?
C7 N1 O1 104.56(7) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C13 119.90(9) . . ?
C13 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.95(10) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.29(9) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.27(8) . . ?
C3 C4 C12 119.63(9) . . ?
C12 C4 C5 121.11(9) . . ?
O1 C5 C4 117.47(8) . . ?
O1 C5 C6 109.03(8) . . ?
C6 C5 C4 133.51(9) . . ?
C5 C6 C7 104.39(8) . . ?
C5 C6 C14 134.22(9) . . ?
C7 C6 C14 121.27(8) . . ?
N1 C7 C6 111.96(8) . . ?
N1 C7 C8 127.14(9) . . ?
C6 C7 C8 120.89(8) . . ?
C9 C8 C7 115.60(8) . . ?
C17 C8 C7 124.08(9) . . ?
C17 C8 C9 120.30(9) . . ?
C8 C9 C15 121.57(8) . . ?
C10 C9 C8 119.04(9) . . ?
C10 C9 C15 119.39(9) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.53(9) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C16 120.09(9) . . ?
C16 C11 H11 120.0 . . ?
C4 C12 H12 120.2 . . ?
C13 C12 C4 119.55(9) . . ?
C13 C12 H12 120.2 . . ?
C1 C13 H13 119.7 . . ?
C12 C13 C1 120.66(9) . . ?
C12 C13 H13 119.7 . . ?
C6 C14 H14 121.0 . . ?
C15 C14 C6 117.97(9) . . ?
C15 C14 H14 121.0 . . ?
C9 C15 H15 118.7 . . ?
C14 C15 C9 122.62(9) . . ?
C14 C15 H15 118.7 . . ?
C11 C16 H16 119.2 . . ?
C17 C16 C11 121.63(9) . . ?
C17 C16 H16 119.2 . . ?
C8 C17 C18 122.14(9) . . ?
C16 C17 C8 118.39(9) . . ?
C16 C17 C18 119.46(9) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 N1 C7 C6 -0.17(10) . . . . ?
O1 N1 C7 C8 -179.31(8) . . . . ?
O1 C5 C6 C7 -0.65(10) . . . . ?
O1 C5 C6 C14 175.35(10) . . . . ?
N1 O1 C5 C4 -179.70(8) . . . . ?
N1 O1 C5 C6 0.59(10) . . . . ?
N1 C7 C8 C9 176.05(9) . . . . ?
N1 C7 C8 C17 -5.59(15) . . . . ?
C1 C2 C3 C4 -0.43(15) . . . . ?
C2 C1 C13 C12 -0.50(16) . . . . ?
C2 C3 C4 C5 179.67(9) . . . . ?
C2 C3 C4 C12 -0.44(15) . . . . ?
C3 C4 C5 O1 143.59(9) . . . . ?
C3 C4 C5 C6 -36.78(16) . . . . ?
C3 C4 C12 C13 0.84(15) . . . . ?
C4 C5 C6 C7 179.70(10) . . . . ?
C4 C5 C6 C14 -4.30(19) . . . . ?
C4 C12 C13 C1 -0.37(16) . . . . ?
C5 O1 N1 C7 -0.25(10) . . . . ?
C5 C4 C12 C13 -179.28(9) . . . . ?
C5 C6 C7 N1 0.51(11) . . . . ?
C5 C6 C7 C8 179.71(8) . . . . ?
C5 C6 C14 C15 -176.41(10) . . . . ?
C6 C7 C8 C9 -3.02(12) . . . . ?
C6 C7 C8 C17 175.34(8) . . . . ?
C6 C14 C15 C9 -1.03(15) . . . . ?
C7 C6 C14 C15 -0.95(14) . . . . ?
C7 C8 C9 C10 -179.73(8) . . . . ?
C7 C8 C9 C15 1.12(13) . . . . ?
C7 C8 C17 C16 179.99(9) . . . . ?
C7 C8 C17 C18 -1.46(14) . . . . ?
C8 C9 C10 C11 -0.99(14) . . . . ?
C8 C9 C15 C14 0.93(15) . . . . ?
C9 C8 C17 C16 -1.72(13) . . . . ?
C9 C8 C17 C18 176.83(9) . . . . ?
C9 C10 C11 C16 0.04(15) . . . . ?
C10 C9 C15 C14 -178.22(9) . . . . ?
C10 C11 C16 C17 0.07(16) . . . . ?
C11 C16 C17 C8 0.76(15) . . . . ?
C11 C16 C17 C18 -177.82(9) . . . . ?
C12 C4 C5 O1 -36.29(13) . . . . ?
C12 C4 C5 C6 143.33(11) . . . . ?
C13 C1 C2 C3 0.90(16) . . . . ?
C14 C6 C7 N1 -176.14(9) . . . . ?
C14 C6 C7 C8 3.07(13) . . . . ?
C15 C9 C10 C11 178.18(9) . . . . ?
C17 C8 C9 C10 1.84(13) . . . . ?
C17 C8 C9 C15 -177.31(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
