# Electronic Supplementary Material (ESI) for ChemComm.
# 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_bm_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2313021'
loop_
_audit_author_name
_audit_author_address
'SUVAM BHATTACHARJEE'
;VISVA BHARATI
India
;
_audit_update_record             
;
2023-12-09 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;
_audit_creation_date             2023-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N3 O2'
_chemical_formula_sum            'C14 H11 N3 O2'
_chemical_formula_weight         253.26
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   8.1213(7)
_cell_length_b                   11.1938(9)
_cell_length_c                   13.6325(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1239.31(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28821
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.441
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2071
_reflns_number_total             2164
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.093
_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)+(0.0388P)²+0.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0781
_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:
 C7(H7), C13(H13), C5(H5), C3(H3), C9(H9), C4(H4), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
N1 N 0.25952(19) 0.35148(14) 0.39072(11) 0.0463(4) Uani 1 1 d . . . . .
N2 N 0.42146(19) 0.32144(13) 0.37959(12) 0.0449(4) Uani 1 1 d . . . . .
O1 O -0.0621(2) 0.4274(2) 0.40767(15) 0.0966(7) Uani 1 1 d . . . . .
N3 N -0.0428(2) 0.45594(17) 0.49264(15) 0.0611(5) Uani 1 1 d . . . . .
O2 O -0.1568(2) 0.4882(2) 0.54427(16) 0.1026(7) Uani 1 1 d . . . . .
C7 C 0.5156(2) 0.34883(17) 0.45743(14) 0.0472(5) Uani 1 1 d . . . . .
H7 H 0.628050 0.335439 0.463867 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4733(2) 0.26855(16) 0.28963(14) 0.0468(4) Uani 1 1 d . . . . .
C13 C 0.6345(3) 0.28231(17) 0.25944(15) 0.0522(5) Uani 1 1 d . . . . .
H13 H 0.707879 0.325639 0.297900 0.063 Uiso 1 1 calc R U . . .
C1 C 0.2551(2) 0.40089(15) 0.48047(13) 0.0428(4) Uani 1 1 d . . . . .
C6 C 0.4128(2) 0.40078(16) 0.52614(13) 0.0447(4) Uani 1 1 d . . . . .
C2 C 0.1218(2) 0.45169(17) 0.53356(15) 0.0486(5) Uani 1 1 d . . . . .
C5 C 0.4367(3) 0.44980(18) 0.62007(14) 0.0542(5) Uani 1 1 d . . . . .
H5 H 0.540238 0.448802 0.649181 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1482(3) 0.49900(19) 0.62431(15) 0.0569(5) Uani 1 1 d . . . . .
H3 H 0.060334 0.532255 0.658497 0.068 Uiso 1 1 calc R U . . .
C9 C 0.3618(3) 0.20517(19) 0.23406(16) 0.0599(6) Uani 1 1 d . . . . .
H9 H 0.253467 0.195786 0.254858 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3062(3) 0.4985(2) 0.66744(15) 0.0601(5) Uani 1 1 d . . . . .
H4 H 0.320933 0.532145 0.729204 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6879(3) 0.23160(18) 0.17165(16) 0.0584(6) Uani 1 1 d . . . . .
C14 C 0.8648(3) 0.2444(3) 0.1400(2) 0.0851(8) Uani 1 1 d . . . . .
H14A H 0.913722 0.166674 0.133867 0.128 Uiso 1 1 calc R U . . .
H14B H 0.924107 0.289957 0.188074 0.128 Uiso 1 1 calc R U . . .
H14C H 0.869291 0.284692 0.077897 0.128 Uiso 1 1 calc R U . . .
C11 C 0.5751(3) 0.1700(2) 0.11535(19) 0.0703(7) Uani 1 1 d . . . . .
H11 H 0.607505 0.137514 0.055592 0.084 Uiso 1 1 calc R U . . .
C10 C 0.4147(3) 0.1560(2) 0.14678(18) 0.0725(7) Uani 1 1 d . . . . .
H10 H 0.341130 0.112629 0.108493 0.087 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
N1 N2 1.366(2) . ?
N1 C1 1.343(2) . ?
N2 C7 1.343(2) . ?
N2 C8 1.426(2) . ?
O1 N3 1.212(2) . ?
N3 O2 1.218(2) . ?
N3 C2 1.450(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(3) . ?
C8 C13 1.381(3) . ?
C8 C9 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.394(3) . ?
C1 C6 1.424(3) . ?
C1 C2 1.420(3) . ?
C6 C5 1.406(3) . ?
C2 C3 1.363(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.356(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C4 H4 0.9300 . ?
C12 C14 1.507(3) . ?
C12 C11 1.380(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.380(4) . ?
C10 H10 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 N1 N2 103.21(15) . . ?
N1 N2 C8 118.84(15) . . ?
C7 N2 N1 113.82(16) . . ?
C7 N2 C8 127.32(17) . . ?
O1 N3 O2 122.2(2) . . ?
O1 N3 C2 118.59(19) . . ?
O2 N3 C2 119.25(19) . . ?
N2 C7 H7 126.6 . . ?
N2 C7 C6 106.73(17) . . ?
C6 C7 H7 126.6 . . ?
C13 C8 N2 119.36(18) . . ?
C9 C8 N2 119.50(18) . . ?
C9 C8 C13 121.14(19) . . ?
C8 C13 H13 119.8 . . ?
C8 C13 C12 120.35(19) . . ?
C12 C13 H13 119.8 . . ?
N1 C1 C6 111.93(16) . . ?
N1 C1 C2 130.50(17) . . ?
C2 C1 C6 117.56(16) . . ?
C7 C6 C1 104.30(16) . . ?
C7 C6 C5 134.23(19) . . ?
C5 C6 C1 121.45(18) . . ?
C1 C2 N3 121.31(18) . . ?
C3 C2 N3 118.78(18) . . ?
C3 C2 C1 119.90(18) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.6 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.31(19) . . ?
C4 C3 H3 119.3 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.3(2) . . ?
C10 C9 H9 120.8 . . ?
C5 C4 C3 120.91(19) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C13 C12 C14 120.2(2) . . ?
C11 C12 C13 118.3(2) . . ?
C11 C12 C14 121.4(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?

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
N1 N2 C7 C6 0.0(2) . . . . ?
N1 N2 C8 C13 153.28(17) . . . . ?
N1 N2 C8 C9 -26.4(3) . . . . ?
N1 C1 C6 C7 0.7(2) . . . . ?
N1 C1 C6 C5 179.13(17) . . . . ?
N1 C1 C2 N3 0.4(3) . . . . ?
N1 C1 C2 C3 -178.81(19) . . . . ?
N2 N1 C1 C6 -0.67(19) . . . . ?
N2 N1 C1 C2 178.81(17) . . . . ?
N2 C7 C6 C1 -0.4(2) . . . . ?
N2 C7 C6 C5 -178.5(2) . . . . ?
N2 C8 C13 C12 -179.86(17) . . . . ?
N2 C8 C9 C10 179.32(19) . . . . ?
O1 N3 C2 C1 -8.1(3) . . . . ?
O1 N3 C2 C3 171.1(2) . . . . ?
N3 C2 C3 C4 -179.3(2) . . . . ?
O2 N3 C2 C1 172.1(2) . . . . ?
O2 N3 C2 C3 -8.8(3) . . . . ?
C7 N2 C8 C13 -25.3(3) . . . . ?
C7 N2 C8 C9 155.05(19) . . . . ?
C7 C6 C5 C4 177.6(2) . . . . ?
C8 N2 C7 C6 178.59(16) . . . . ?
C8 C13 C12 C14 -178.6(2) . . . . ?
C8 C13 C12 C11 1.3(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C13 C12 C11 C10 -1.9(4) . . . . ?
C1 N1 N2 C7 0.4(2) . . . . ?
C1 N1 N2 C8 -178.31(15) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C6 C1 C2 N3 179.82(17) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C5 C4 C3 0.8(3) . . . . ?
C2 C1 C6 C7 -178.89(15) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C12 C11 C10 C9 1.4(4) . . . . ?
C14 C12 C11 C10 178.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
