# 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_st306_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2116278'
loop_
_audit_author_name
_audit_author_address
'Shruti Rajput'
;IIT DELHI
India
;
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2022-01-14 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         'C20 H13 Br N2 O'
_chemical_formula_sum            'C20 H13 Br N2 O'
_chemical_formula_weight         377.22

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'
Br Br -0.2901 2.4595 '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                   8.0295(5)
_cell_length_b                   8.2401(7)
_cell_length_c                   13.3944(10)
_cell_angle_alpha                99.581(2)
_cell_angle_beta                 107.210(2)
_cell_angle_gamma                100.420(2)
_cell_volume                     809.45(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.544
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             380.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.542
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            10899
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_av_R_equivalents  0.1459
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.637
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2854
_reflns_number_gt                2490
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0689P)²+3.2013P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.105(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2839
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Br1 Br 0.28411(6) 0.74555(5) 0.32838(3) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.6579(6) 1.0553(5) 0.8550(4) 0.0397(10) Uani 1 1 d . . . . .
N1 N 0.4433(7) 0.5416(6) 0.7548(4) 0.0335(11) Uani 1 1 d . . . . .
N2 N 0.5377(7) 0.7255(6) 0.6507(4) 0.0362(12) Uani 1 1 d . . . . .
C8 C 0.5837(8) 0.6097(8) 0.8547(5) 0.0334(13) Uani 1 1 d . . . . .
C2 C 0.3364(8) 0.6684(8) 0.4691(5) 0.0357(13) Uani 1 1 d . . . . .
C9 C 0.6631(9) 0.5006(8) 0.9098(5) 0.0378(14) Uani 1 1 d . . . . .
H9 H 0.618539 0.381489 0.882018 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2668(8) 0.4937(7) 0.5809(5) 0.0346(13) Uani 1 1 d . . . . .
C13 C 0.6468(8) 0.7876(8) 0.8969(5) 0.0350(13) Uani 1 1 d . . . . .
C10 C 0.8070(9) 0.5630(9) 1.0051(5) 0.0416(15) Uani 1 1 d . . . . .
H10 H 0.858082 0.486784 1.043433 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2209(8) 0.5317(8) 0.4810(5) 0.0342(13) Uani 1 1 d . . . . .
H3 H 0.115820 0.467577 0.423518 0.041 Uiso 1 1 calc R U . . .
C17 C 0.0695(9) 0.7620(8) 0.8140(5) 0.0369(14) Uani 1 1 d . . . . .
H17 H -0.003694 0.690797 0.841570 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4916(9) 0.7589(8) 0.5532(5) 0.0369(14) Uani 1 1 d . . . . .
H1 H 0.568948 0.849237 0.540721 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4235(8) 0.5965(7) 0.6612(5) 0.0324(13) Uani 1 1 d . . . . .
C16 C 0.2554(8) 0.7816(7) 0.8498(5) 0.0342(13) Uani 1 1 d . . . . .
H16 H 0.308309 0.722622 0.901188 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3016(9) 0.4023(7) 0.7331(5) 0.0387(14) Uani 1 1 d . . . . .
H6 H 0.283268 0.338766 0.783663 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3646(8) 0.8882(7) 0.8102(5) 0.0328(13) Uani 1 1 d . . . . .
C12 C 0.7964(8) 0.8468(8) 0.9899(5) 0.0367(14) Uani 1 1 d . . . . .
H12 H 0.844850 0.965658 1.016587 0.044 Uiso 1 1 calc R U . . .
C14 C 0.5623(8) 0.9183(7) 0.8508(5) 0.0336(13) Uani 1 1 d . . . . .
C11 C 0.8766(9) 0.7376(9) 1.0446(5) 0.0418(15) Uani 1 1 d . . . . .
H11 H 0.978033 0.781070 1.108442 0.050 Uiso 1 1 calc R U . . .
C18 C -0.0085(9) 0.8461(8) 0.7383(5) 0.0394(15) Uani 1 1 d . . . . .
H18 H -0.135081 0.832744 0.713755 0.047 Uiso 1 1 calc R U . . .
C19 C 0.0999(9) 0.9506(8) 0.6981(6) 0.0417(15) Uani 1 1 d . . . . .
H19 H 0.046385 1.007262 0.645463 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1931(9) 0.3697(8) 0.6296(5) 0.0388(14) Uani 1 1 d . . . . .
H5 H 0.087197 0.280700 0.595388 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2852(8) 0.9727(7) 0.7344(5) 0.0371(14) Uani 1 1 d . . . . .
H20 H 0.357897 1.045592 0.707391 0.044 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
Br1 C2 2.040(6) . ?
O1 C14 1.227(7) . ?
N1 C7 1.378(8) . ?
N1 C6 1.385(8) . ?
N1 C8 1.416(8) . ?
N2 C7 1.328(8) . ?
N2 C1 1.338(8) . ?
C8 C9 1.381(8) . ?
C8 C13 1.418(9) . ?
C2 C3 1.386(9) . ?
C2 C1 1.389(9) . ?
C9 C10 1.387(9) . ?
C9 H9 0.9500 . ?
C4 C3 1.384(9) . ?
C4 C7 1.402(8) . ?
C4 C5 1.432(9) . ?
C13 C12 1.390(9) . ?
C13 C14 1.496(8) . ?
C10 C11 1.394(10) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C17 C18 1.384(9) . ?
C17 C16 1.396(9) . ?
C17 H17 0.9500 . ?
C1 H1 0.9500 . ?
C16 C15 1.405(8) . ?
C16 H16 0.9500 . ?
C6 C5 1.353(9) . ?
C6 H6 0.9500 . ?
C15 C20 1.391(8) . ?
C15 C14 1.476(8) . ?
C12 C11 1.383(9) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C18 C19 1.396(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(9) . ?
C19 H19 0.9500 . ?
C5 H5 0.9500 . ?
C20 H20 0.9500 . ?

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
C7 N1 C6 107.3(5) . . ?
C7 N1 C8 127.3(5) . . ?
C6 N1 C8 125.4(5) . . ?
C7 N2 C1 114.5(5) . . ?
C9 C8 N1 119.1(5) . . ?
C9 C8 C13 119.9(6) . . ?
N1 C8 C13 120.9(5) . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 Br1 121.4(5) . . ?
C1 C2 Br1 117.5(5) . . ?
C8 C9 C10 120.7(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C3 C4 C7 117.8(6) . . ?
C3 C4 C5 136.3(6) . . ?
C7 C4 C5 105.9(5) . . ?
C12 C13 C8 118.0(6) . . ?
C12 C13 C14 116.8(5) . . ?
C8 C13 C14 125.2(5) . . ?
C9 C10 C11 120.0(6) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C4 C3 C2 116.4(5) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
C18 C17 C16 120.2(6) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N2 C1 C2 123.4(6) . . ?
N2 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 C7 N1 124.3(5) . . ?
N2 C7 C4 126.6(6) . . ?
N1 C7 C4 109.1(5) . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C5 C6 N1 110.2(6) . . ?
C5 C6 H6 124.9 . . ?
N1 C6 H6 124.9 . . ?
C20 C15 C16 119.3(6) . . ?
C20 C15 C14 119.3(5) . . ?
C16 C15 C14 121.4(5) . . ?
C11 C12 C13 121.9(6) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
O1 C14 C15 120.4(5) . . ?
O1 C14 C13 119.6(6) . . ?
C15 C14 C13 119.8(5) . . ?
C12 C11 C10 119.2(6) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C17 C18 C19 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.7(6) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C6 C5 C4 107.6(6) . . ?
C6 C5 H5 126.2 . . ?
C4 C5 H5 126.2 . . ?
C19 C20 C15 120.1(6) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?

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
C7 N1 C8 C9 -134.2(6) . . . . ?
C6 N1 C8 C9 44.0(9) . . . . ?
C7 N1 C8 C13 43.9(9) . . . . ?
C6 N1 C8 C13 -137.9(6) . . . . ?
N1 C8 C9 C10 176.7(6) . . . . ?
C13 C8 C9 C10 -1.4(10) . . . . ?
C9 C8 C13 C12 4.3(9) . . . . ?
N1 C8 C13 C12 -173.8(6) . . . . ?
C9 C8 C13 C14 -174.0(6) . . . . ?
N1 C8 C13 C14 7.9(9) . . . . ?
C8 C9 C10 C11 -2.0(10) . . . . ?
C7 C4 C3 C2 0.6(9) . . . . ?
C5 C4 C3 C2 -179.8(7) . . . . ?
C1 C2 C3 C4 1.3(9) . . . . ?
Br1 C2 C3 C4 -178.1(4) . . . . ?
C7 N2 C1 C2 0.6(9) . . . . ?
C3 C2 C1 N2 -2.1(10) . . . . ?
Br1 C2 C1 N2 177.3(5) . . . . ?
C1 N2 C7 N1 -179.2(6) . . . . ?
C1 N2 C7 C4 1.6(9) . . . . ?
C6 N1 C7 N2 -178.2(6) . . . . ?
C8 N1 C7 N2 0.3(10) . . . . ?
C6 N1 C7 C4 1.2(7) . . . . ?
C8 N1 C7 C4 179.7(6) . . . . ?
C3 C4 C7 N2 -2.2(10) . . . . ?
C5 C4 C7 N2 178.1(6) . . . . ?
C3 C4 C7 N1 178.4(5) . . . . ?
C5 C4 C7 N1 -1.3(7) . . . . ?
C18 C17 C16 C15 0.7(9) . . . . ?
C7 N1 C6 C5 -0.7(7) . . . . ?
C8 N1 C6 C5 -179.2(6) . . . . ?
C17 C16 C15 C20 -0.5(9) . . . . ?
C17 C16 C15 C14 176.8(6) . . . . ?
C8 C13 C12 C11 -3.9(10) . . . . ?
C14 C13 C12 C11 174.5(6) . . . . ?
C20 C15 C14 O1 29.3(9) . . . . ?
C16 C15 C14 O1 -148.1(6) . . . . ?
C20 C15 C14 C13 -156.6(6) . . . . ?
C16 C15 C14 C13 26.1(8) . . . . ?
C12 C13 C14 O1 36.4(9) . . . . ?
C8 C13 C14 O1 -145.3(6) . . . . ?
C12 C13 C14 C15 -137.8(6) . . . . ?
C8 C13 C14 C15 40.5(9) . . . . ?
C13 C12 C11 C10 0.6(10) . . . . ?
C9 C10 C11 C12 2.4(10) . . . . ?
C16 C17 C18 C19 -0.1(10) . . . . ?
C17 C18 C19 C20 -0.8(10) . . . . ?
N1 C6 C5 C4 -0.1(8) . . . . ?
C3 C4 C5 C6 -178.7(7) . . . . ?
C7 C4 C5 C6 0.9(7) . . . . ?
C18 C19 C20 C15 1.0(10) . . . . ?
C16 C15 C20 C19 -0.3(9) . . . . ?
C14 C15 C20 C19 -177.7(6) . . . . ?

_refine_diff_density_max         1.306
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.158

