# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 2150459'
loop_
_audit_author_name
_audit_author_address
'Dr. Ruchir Kant'
;CSIR CDRI, Lucknow
India
;
_audit_update_record             
;
2022-02-07 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Br N3 O2'
_chemical_formula_weight         320.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.692(6)
_cell_length_b                   7.901(2)
_cell_length_c                   11.323(6)
_cell_angle_alpha                72.27(5)
_cell_angle_beta                 88.36(9)
_cell_angle_gamma                75.68(6)
_cell_volume                     634.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    665
_cell_measurement_theta_min      7.1
_cell_measurement_theta_max      68.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    4.447
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.5016
_exptl_absorpt_correction_T_max  0.6904
#===============================================================================

# 7. EXPERIMENTAL DATA


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'


_diffrn_reflns_number            12288
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_sigmaI/netI    0.0713
_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       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         7.06
_diffrn_reflns_theta_max         68.77
_reflns_number_total             2281
_reflns_number_gt                1672
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1078P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.062(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2281
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1799
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.06453(8) -0.27198(7) 1.38002(5) 0.0606(4) Uani 1 1 d . . .
C1 C 0.9753(6) -0.0261(6) 1.2784(4) 0.0416(11) Uani 1 1 d . . .
C2 C 1.0004(7) 0.1136(6) 1.3212(4) 0.0437(11) Uani 1 1 d . . .
H2 H 1.0580 0.0855 1.3983 0.052 Uiso 1 1 calc R . .
C3 C 0.9395(6) 0.2950(6) 1.2488(4) 0.0402(11) Uani 1 1 d . . .
H3 H 0.9563 0.3896 1.2764 0.048 Uiso 1 1 calc R . .
C4 C 0.8517(6) 0.3332(6) 1.1329(4) 0.0354(10) Uani 1 1 d . . .
C5 C 0.8261(6) 0.1921(6) 1.0911(4) 0.0367(10) Uani 1 1 d . . .
C6 C 0.8890(7) 0.0092(6) 1.1668(4) 0.0413(11) Uani 1 1 d . . .
H6 H 0.8719 -0.0867 1.1409 0.050 Uiso 1 1 calc R . .
C7 C 0.7883(6) 0.5186(6) 1.0532(4) 0.0351(10) Uani 1 1 d . . .
C8 C 0.6802(7) 0.4107(6) 0.8979(4) 0.0414(11) Uani 1 1 d . . .
H8 H 0.6236 0.4374 0.8206 0.050 Uiso 1 1 calc R . .
C9 C 0.7358(7) 0.2371(6) 0.9705(4) 0.0427(11) Uani 1 1 d . . .
H9 H 0.7164 0.1431 0.9433 0.051 Uiso 1 1 calc R . .
C10 C 0.6684(6) 0.7386(6) 0.8886(4) 0.0391(11) Uani 1 1 d . . .
C11 C 0.5826(7) 0.8375(6) 0.7622(4) 0.0435(11) Uani 1 1 d . . .
C12 C 0.4692(8) 1.1339(7) 0.6199(5) 0.0521(13) Uani 1 1 d . . .
H12A H 0.3668 1.0946 0.5999 0.063 Uiso 1 1 calc R . .
H12B H 0.5554 1.1273 0.5562 0.063 Uiso 1 1 calc R . .
C13 C 0.4098(8) 1.3286(8) 0.6274(6) 0.0615(15) Uani 1 1 d . . .
H13A H 0.3557 1.4103 0.5487 0.092 Uiso 1 1 calc R . .
H13B H 0.5121 1.3652 0.6479 0.092 Uiso 1 1 calc R . .
H13C H 0.3239 1.3332 0.6902 0.092 Uiso 1 1 calc R . .
N1 N 0.7079(5) 0.5511(5) 0.9392(3) 0.0342(8) Uani 1 1 d . . .
N2 N 0.7973(6) 0.6759(5) 1.0710(4) 0.0424(9) Uani 1 1 d . . .
N3 N 0.7201(6) 0.8136(5) 0.9662(4) 0.0430(10) Uani 1 1 d . . .
O1 O 0.5522(6) 0.7651(5) 0.6913(3) 0.0647(11) Uani 1 1 d . . .
O2 O 0.5512(5) 1.0175(4) 0.7417(3) 0.0497(9) Uani 1 1 d . . .


_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 C1 1.896(5) . ?
C1 C6 1.362(7) . ?
C1 C2 1.389(7) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(6) . ?
C4 C7 1.437(6) . ?
C5 C6 1.407(6) . ?
C5 C9 1.453(7) . ?
C6 H6 0.9300 . ?
C7 N2 1.336(6) . ?
C7 N1 1.371(6) . ?
C8 C9 1.336(7) . ?
C8 N1 1.390(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 N3 1.317(6) . ?
C10 N1 1.374(6) . ?
C10 C11 1.487(7) . ?
C11 O1 1.176(6) . ?
C11 O2 1.329(6) . ?
C12 O2 1.462(6) . ?
C12 C13 1.520(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N2 N3 1.371(5) . ?

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
C6 C1 C2 121.9(4) . . ?
C6 C1 Br1 119.9(4) . . ?
C2 C1 Br1 118.2(4) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 C7 118.0(4) . . ?
C3 C4 C7 121.1(4) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 C9 119.3(4) . . ?
C6 C5 C9 121.6(4) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N2 C7 N1 110.7(4) . . ?
N2 C7 C4 129.6(4) . . ?
N1 C7 C4 119.7(4) . . ?
C9 C8 N1 119.3(4) . . ?
C9 C8 H8 120.4 . . ?
N1 C8 H8 120.4 . . ?
C8 C9 C5 121.3(4) . . ?
C8 C9 H9 119.4 . . ?
C5 C9 H9 119.4 . . ?
N3 C10 N1 110.5(4) . . ?
N3 C10 C11 126.3(4) . . ?
N1 C10 C11 123.2(4) . . ?
O1 C11 O2 126.0(5) . . ?
O1 C11 C10 124.4(4) . . ?
O2 C11 C10 109.6(4) . . ?
O2 C12 C13 106.6(5) . . ?
O2 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O2 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C10 104.0(4) . . ?
C7 N1 C8 122.4(4) . . ?
C10 N1 C8 133.5(4) . . ?
C7 N2 N3 106.5(4) . . ?
C10 N3 N2 108.3(4) . . ?
C11 O2 C12 116.1(4) . . ?

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
C6 C1 C2 C3 -1.1(8) . . . . ?
Br1 C1 C2 C3 179.0(4) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C2 C3 C4 C7 -179.0(4) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C7 C4 C5 C6 179.2(4) . . . . ?
C3 C4 C5 C9 -179.6(4) . . . . ?
C7 C4 C5 C9 -0.6(7) . . . . ?
C2 C1 C6 C5 1.2(7) . . . . ?
Br1 C1 C6 C5 -178.9(3) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C9 C5 C6 C1 179.0(4) . . . . ?
C5 C4 C7 N2 -179.5(5) . . . . ?
C3 C4 C7 N2 -0.5(8) . . . . ?
C5 C4 C7 N1 -0.9(7) . . . . ?
C3 C4 C7 N1 178.1(4) . . . . ?
N1 C8 C9 C5 -0.6(7) . . . . ?
C4 C5 C9 C8 1.4(7) . . . . ?
C6 C5 C9 C8 -178.4(5) . . . . ?
N3 C10 C11 O1 173.1(5) . . . . ?
N1 C10 C11 O1 -5.4(8) . . . . ?
N3 C10 C11 O2 -5.2(7) . . . . ?
N1 C10 C11 O2 176.3(4) . . . . ?
N2 C7 N1 C10 0.0(5) . . . . ?
C4 C7 N1 C10 -178.9(4) . . . . ?
N2 C7 N1 C8 -179.4(4) . . . . ?
C4 C7 N1 C8 1.8(7) . . . . ?
N3 C10 N1 C7 -0.3(5) . . . . ?
C11 C10 N1 C7 178.5(4) . . . . ?
N3 C10 N1 C8 179.0(5) . . . . ?
C11 C10 N1 C8 -2.2(8) . . . . ?
C9 C8 N1 C7 -1.0(7) . . . . ?
C9 C8 N1 C10 179.9(5) . . . . ?
N1 C7 N2 N3 0.3(5) . . . . ?
C4 C7 N2 N3 179.0(4) . . . . ?
N1 C10 N3 N2 0.5(5) . . . . ?
C11 C10 N3 N2 -178.2(4) . . . . ?
C7 N2 N3 C10 -0.5(5) . . . . ?
O1 C11 O2 C12 0.8(8) . . . . ?
C10 C11 O2 C12 179.1(4) . . . . ?
C13 C12 O2 C11 168.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        68.77
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.039
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.288


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#                         END of data
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