# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_bm1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2174840'
loop_
_audit_author_name
_audit_author_address
'SUVAM BHATTACHARJEE'
;VISVA BHARATI
India
;
_audit_update_record             
;
2022-05-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N4 O'
_chemical_formula_weight         430.49

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.1723(4)
_cell_length_b                   10.9238(5)
_cell_length_c                   12.8796(6)
_cell_angle_alpha                65.0360(10)
_cell_angle_beta                 78.3340(10)
_cell_angle_gamma                71.5360(10)
_cell_volume                     1106.17(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37416
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3847
_reflns_number_gt                3354
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0404P)²+0.3313P] 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         3847
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
N3 N 0.50265(13) 0.35918(12) 0.30651(9) 0.0401(3) Uani 1 1 d . . . . .
N2 N 0.66324(13) 0.48985(12) 0.15592(9) 0.0389(3) Uani 1 1 d . . . . .
O1 O 0.43182(15) 0.11436(14) 0.58074(9) 0.0688(4) Uani 1 1 d . . . . .
N1 N 0.78648(14) 0.47755(12) 0.07934(10) 0.0446(3) Uani 1 1 d . . . . .
N4 N 0.54749(14) 0.25936(13) 0.41901(10) 0.0445(3) Uani 1 1 d . . . . .
C14 C 0.62465(15) 0.36724(14) 0.21920(11) 0.0366(3) Uani 1 1 d . . . . .
C13 C 0.72874(16) 0.26640(14) 0.18244(11) 0.0380(3) Uani 1 1 d . . . . .
C15 C 0.36816(16) 0.33236(14) 0.29379(12) 0.0398(3) Uani 1 1 d . . . . .
C8 C 0.82611(16) 0.34112(15) 0.09557(12) 0.0399(3) Uani 1 1 d . . . . .
C7 C 0.59029(16) 0.62609(14) 0.15834(12) 0.0400(3) Uani 1 1 d . . . . .
C20 C 0.31823(17) 0.23982(15) 0.39733(12) 0.0436(3) Uani 1 1 d . . . . .
C22 C 0.65271(16) 0.28317(16) 0.47163(11) 0.0415(3) Uani 1 1 d . . . . .
C28 C 0.65801(17) 0.41690(16) 0.44959(13) 0.0464(4) Uani 1 1 d . . . . .
H28 H 0.596179 0.493763 0.396487 0.056 Uiso 1 1 calc R U . . .
C12 C 0.75364(19) 0.12145(16) 0.21237(14) 0.0512(4) Uani 1 1 d . . . . .
H12 H 0.692193 0.070369 0.270440 0.061 Uiso 1 1 calc R U . . .
C21 C 0.43157(18) 0.19281(16) 0.47940(12) 0.0478(4) Uani 1 1 d . . . . .
C16 C 0.28922(17) 0.38694(16) 0.19644(13) 0.0485(4) Uani 1 1 d . . . . .
H16 H 0.326458 0.444299 0.125858 0.058 Uiso 1 1 calc R U . . .
C9 C 0.94817(18) 0.27349(17) 0.03598(14) 0.0522(4) Uani 1 1 d . . . . .
H9 H 1.012776 0.321985 -0.020977 0.063 Uiso 1 1 calc R U . . .
C27 C 0.75601(19) 0.43561(18) 0.50713(14) 0.0535(4) Uani 1 1 d . . . . .
H27 H 0.760026 0.525880 0.491203 0.064 Uiso 1 1 calc R U . . .
C23 C 0.74681(19) 0.16945(17) 0.54939(13) 0.0508(4) Uani 1 1 d . . . . .
H23 H 0.745901 0.079058 0.562899 0.061 Uiso 1 1 calc R U . . .
C6 C 0.67460(19) 0.69123(17) 0.18549(14) 0.0523(4) Uani 1 1 d . . . . .
H6 H 0.776019 0.646379 0.204036 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4572(2) 0.89411(16) 0.15661(13) 0.0516(4) Uani 1 1 d . . . . .
C19 C 0.17940(18) 0.20738(18) 0.40874(15) 0.0540(4) Uani 1 1 d . . . . .
H19 H 0.143628 0.147739 0.478739 0.065 Uiso 1 1 calc R U . . .
C24 C 0.84203(19) 0.19093(18) 0.60682(14) 0.0559(4) Uani 1 1 d . . . . .
H24 H 0.903880 0.114059 0.659897 0.067 Uiso 1 1 calc R U . . .
C25 C 0.84787(18) 0.32437(19) 0.58738(14) 0.0534(4) Uani 1 1 d . . . . .
C17 C 0.15274(19) 0.35234(18) 0.20891(16) 0.0565(4) Uani 1 1 d . . . . .
H17 H 0.096479 0.387951 0.145239 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6071(2) 0.82375(18) 0.18492(15) 0.0573(4) Uani 1 1 d . . . . .
H5 H 0.664140 0.866974 0.204136 0.069 Uiso 1 1 calc R U . . .
C1 C 0.44142(19) 0.69289(17) 0.12996(16) 0.0577(4) Uani 1 1 d . . . . .
H1 H 0.384631 0.649221 0.111064 0.069 Uiso 1 1 calc R U . . .
C2 C 0.3763(2) 0.82587(18) 0.12966(17) 0.0630(5) Uani 1 1 d . . . . .
H2 H 0.274959 0.870516 0.110731 0.076 Uiso 1 1 calc R U . . .
C18 C 0.09673(19) 0.26558(19) 0.31416(17) 0.0608(5) Uani 1 1 d . . . . .
H18 H 0.002465 0.247032 0.320254 0.073 Uiso 1 1 calc R U . . .
C10 C 0.9673(2) 0.13509(19) 0.06513(16) 0.0593(4) Uani 1 1 d . . . . .
H10 H 1.045936 0.088342 0.026454 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8714(2) 0.05984(18) 0.15255(16) 0.0602(4) Uani 1 1 d . . . . .
H11 H 0.889326 -0.035152 0.169889 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3862(2) 1.03903(18) 0.15634(17) 0.0688(5) Uani 1 1 d . . . . .
H4A H 0.427767 1.105317 0.089929 0.103 Uiso 1 1 calc R U . . .
H4B H 0.409117 1.042079 0.224577 0.103 Uiso 1 1 calc R U . . .
H4C H 0.276466 1.061962 0.154347 0.103 Uiso 1 1 calc R U . . .
C26 C 0.9505(2) 0.3462(2) 0.65262(18) 0.0775(6) Uani 1 1 d . . . . .
H26A H 0.944288 0.444064 0.625070 0.116 Uiso 1 1 calc R U . . .
H26B H 1.055162 0.295825 0.641258 0.116 Uiso 1 1 calc R U . . .
H26C H 0.917456 0.312520 0.733014 0.116 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
N3 C15 1.4091(17) . ?
N3 C14 1.4123(17) . ?
N3 N4 1.4425(16) . ?
N2 N1 1.3542(16) . ?
N2 C14 1.3586(17) . ?
N2 C7 1.4364(18) . ?
O1 C21 1.2222(18) . ?
N1 C8 1.3496(18) . ?
N4 C21 1.3936(18) . ?
N4 C22 1.4250(18) . ?
C14 C13 1.393(2) . ?
C13 C12 1.414(2) . ?
C13 C8 1.4152(19) . ?
C15 C16 1.384(2) . ?
C15 C20 1.385(2) . ?
C8 C9 1.413(2) . ?
C7 C1 1.370(2) . ?
C7 C6 1.377(2) . ?
C20 C19 1.391(2) . ?
C20 C21 1.453(2) . ?
C22 C28 1.381(2) . ?
C22 C23 1.383(2) . ?
C28 C27 1.383(2) . ?
C12 C11 1.362(2) . ?
C16 C17 1.379(2) . ?
C9 C10 1.355(2) . ?
C27 C25 1.378(2) . ?
C23 C24 1.379(2) . ?
C6 C5 1.380(2) . ?
C3 C2 1.379(2) . ?
C3 C5 1.383(2) . ?
C3 C4 1.508(2) . ?
C19 C18 1.370(2) . ?
C24 C25 1.388(2) . ?
C25 C26 1.510(2) . ?
C17 C18 1.394(2) . ?
C1 C2 1.383(2) . ?
C10 C11 1.412(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
C15 N3 C14 119.63(11) . . ?
C15 N3 N4 104.71(10) . . ?
C14 N3 N4 114.18(11) . . ?
N1 N2 C14 113.05(11) . . ?
N1 N2 C7 117.78(11) . . ?
C14 N2 C7 129.16(11) . . ?
C8 N1 N2 103.93(11) . . ?
C21 N4 C22 124.13(12) . . ?
C21 N4 N3 110.55(11) . . ?
C22 N4 N3 118.54(11) . . ?
N2 C14 C13 106.90(11) . . ?
N2 C14 N3 120.86(12) . . ?
C13 C14 N3 132.18(12) . . ?
C14 C13 C12 135.76(13) . . ?
C14 C13 C8 103.92(12) . . ?
C12 C13 C8 120.32(13) . . ?
C16 C15 C20 121.68(13) . . ?
C16 C15 N3 128.31(13) . . ?
C20 C15 N3 110.00(12) . . ?
N1 C8 C9 126.82(13) . . ?
N1 C8 C13 112.21(12) . . ?
C9 C8 C13 120.97(13) . . ?
C1 C7 C6 120.22(14) . . ?
C1 C7 N2 120.92(13) . . ?
C6 C7 N2 118.81(13) . . ?
C15 C20 C19 120.48(15) . . ?
C15 C20 C21 108.45(12) . . ?
C19 C20 C21 131.06(14) . . ?
C28 C22 C23 119.85(14) . . ?
C28 C22 N4 121.33(13) . . ?
C23 C22 N4 118.78(13) . . ?
C22 C28 C27 119.46(14) . . ?
C11 C12 C13 117.16(15) . . ?
O1 C21 N4 124.39(15) . . ?
O1 C21 C20 130.34(14) . . ?
N4 C21 C20 105.26(12) . . ?
C17 C16 C15 116.92(15) . . ?
C10 C9 C8 117.32(15) . . ?
C25 C27 C28 121.89(15) . . ?
C24 C23 C22 119.57(15) . . ?
C7 C6 C5 119.34(15) . . ?
C2 C3 C5 117.22(15) . . ?
C2 C3 C4 121.90(16) . . ?
C5 C3 C4 120.88(16) . . ?
C18 C19 C20 118.27(15) . . ?
C23 C24 C25 121.67(15) . . ?
C27 C25 C24 117.53(15) . . ?
C27 C25 C26 121.47(16) . . ?
C24 C25 C26 121.00(16) . . ?
C16 C17 C18 121.91(16) . . ?
C6 C5 C3 121.88(15) . . ?
C7 C1 C2 119.44(15) . . ?
C3 C2 C1 121.88(16) . . ?
C19 C18 C17 120.54(15) . . ?
C9 C10 C11 121.89(16) . . ?
C12 C11 C10 122.32(16) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.027

