# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_tcb_hobt_gd_bhm_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2102031'
loop_
_audit_author_name
_audit_author_address
'GOBINDA DOLAI'
;CCDC
India
;
_audit_update_record             
;
2021-09-18 deposited with the CCDC.	2021-09-28 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 H6 Cl3 N3 O2'
_chemical_formula_weight         342.56

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0723(6)
_cell_length_b                   13.1809(9)
_cell_length_c                   10.5798(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.957(3)
_cell_angle_gamma                90.00
_cell_volume                     1404.40(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6307
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.63

_exptl_crystal_description       blocked
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13230
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2452
_reflns_number_gt                2112
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.2206P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2452
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.22092(5) 0.64837(5) 0.60985(6) 0.0684(2) Uani 1 1 d . . .
Cl3 Cl 0.68228(6) 0.59340(5) 0.86027(7) 0.0740(3) Uani 1 1 d . . .
Cl2 Cl 0.52087(8) 0.96830(5) 0.73531(9) 0.0881(3) Uani 1 1 d . . .
O2 O 0.48534(14) 0.48094(10) 0.62773(13) 0.0485(4) Uani 1 1 d . . .
O1 O 0.3753(2) 0.47131(12) 0.81104(17) 0.0723(5) Uani 1 1 d . . .
N1 N 0.46256(17) 0.37814(13) 0.61343(15) 0.0481(4) Uani 1 1 d . . .
N2 N 0.54883(18) 0.31076(15) 0.66302(18) 0.0580(5) Uani 1 1 d . . .
C8 C 0.35606(19) 0.33384(15) 0.55648(16) 0.0411(4) Uani 1 1 d . . .
N3 N 0.50238(19) 0.22127(15) 0.63914(18) 0.0602(5) Uani 1 1 d . . .
C1 C 0.45424(18) 0.63198(15) 0.73530(16) 0.0407(4) Uani 1 1 d . . .
C6 C 0.56744(19) 0.67332(16) 0.79086(18) 0.0453(5) Uani 1 1 d . . .
C7 C 0.43042(19) 0.52058(15) 0.73609(18) 0.0440(5) Uani 1 1 d . . .
C9 C 0.3837(2) 0.23163(15) 0.57373(18) 0.0464(5) Uani 1 1 d . . .
C2 C 0.36295(18) 0.69769(16) 0.68010(18) 0.0459(5) Uani 1 1 d . . .
C5 C 0.5904(2) 0.77671(17) 0.79095(19) 0.0520(5) Uani 1 1 d . . .
H5 H 0.6676 0.8036 0.8268 0.062 Uiso 1 1 calc R . .
C13 C 0.2441(2) 0.36907(18) 0.4920(2) 0.0540(5) Uani 1 1 d . . .
H13 H 0.2274 0.4378 0.4803 0.065 Uiso 1 1 calc R . .
C10 C 0.2944(3) 0.15793(17) 0.5275(2) 0.0567(6) Uani 1 1 d . . .
H10 H 0.3100 0.0890 0.5392 0.068 Uiso 1 1 calc R . .
C3 C 0.3818(2) 0.80099(17) 0.6803(2) 0.0537(5) Uani 1 1 d . . .
H3 H 0.3193 0.8443 0.6435 0.064 Uiso 1 1 calc R . .
C4 C 0.4957(2) 0.83854(16) 0.7365(2) 0.0528(5) Uani 1 1 d . . .
C12 C 0.1605(2) 0.2957(2) 0.4470(2) 0.0620(6) Uani 1 1 d . . .
H12 H 0.0843 0.3151 0.4024 0.074 Uiso 1 1 calc R . .
C11 C 0.1849(2) 0.19185(19) 0.4654(2) 0.0613(6) Uani 1 1 d . . .
H11 H 0.1238 0.1450 0.4339 0.074 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0451(4) 0.0819(5) 0.0776(4) 0.0020(3) -0.0166(3) -0.0075(3)
Cl3 0.0632(4) 0.0693(4) 0.0884(5) 0.0097(3) -0.0295(3) 0.0024(3)
Cl2 0.0900(5) 0.0425(4) 0.1321(7) -0.0103(3) 0.0129(5) -0.0046(3)
O2 0.0572(9) 0.0452(8) 0.0432(8) -0.0035(6) 0.0015(6) -0.0103(6)
O1 0.0971(13) 0.0561(10) 0.0647(10) 0.0032(8) 0.0290(10) -0.0176(9)
N1 0.0504(10) 0.0438(9) 0.0498(9) -0.0037(7) -0.0096(8) -0.0024(7)
N2 0.0528(10) 0.0602(12) 0.0605(11) -0.0011(9) -0.0144(9) 0.0053(8)
C8 0.0414(10) 0.0470(10) 0.0350(9) -0.0028(8) 0.0000(8) -0.0022(8)
N3 0.0629(11) 0.0522(11) 0.0651(12) -0.0012(9) -0.0146(9) 0.0083(9)
C1 0.0410(10) 0.0462(10) 0.0350(9) -0.0004(8) 0.0040(8) -0.0050(8)
C6 0.0411(10) 0.0510(11) 0.0438(10) -0.0006(8) 0.0007(8) -0.0017(8)
C7 0.0418(10) 0.0486(11) 0.0415(10) 0.0018(8) -0.0001(8) -0.0070(8)
C9 0.0523(11) 0.0462(11) 0.0409(10) -0.0010(8) 0.0011(9) 0.0005(9)
C2 0.0364(10) 0.0564(12) 0.0449(10) 0.0019(9) 0.0020(8) -0.0022(8)
C5 0.0466(11) 0.0549(13) 0.0545(12) -0.0100(10) 0.0033(9) -0.0109(9)
C13 0.0542(12) 0.0563(12) 0.0512(11) -0.0037(9) -0.0088(9) 0.0059(10)
C10 0.0707(15) 0.0487(12) 0.0508(12) -0.0032(9) 0.0030(11) -0.0091(10)
C3 0.0482(11) 0.0508(12) 0.0622(13) 0.0049(10) 0.0054(10) 0.0077(9)
C4 0.0526(12) 0.0440(11) 0.0622(13) -0.0050(9) 0.0131(10) -0.0020(9)
C12 0.0461(12) 0.0842(17) 0.0553(13) -0.0116(12) -0.0106(10) -0.0002(11)
C11 0.0598(13) 0.0697(15) 0.0544(13) -0.0132(11) 0.0027(11) -0.0229(12)

_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
Cl1 C2 1.728(2) . ?
Cl3 C6 1.720(2) . ?
Cl2 C4 1.729(2) . ?
O2 N1 1.382(2) . ?
O2 C7 1.384(2) . ?
O1 C7 1.172(2) . ?
N1 N2 1.343(2) . ?
N1 C8 1.354(2) . ?
N2 N3 1.292(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.388(3) . ?
N3 C9 1.378(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.385(3) . ?
C1 C7 1.488(3) . ?
C6 C5 1.382(3) . ?
C9 C10 1.406(3) . ?
C2 C3 1.375(3) . ?
C5 C4 1.374(3) . ?
C5 H5 0.9300 . ?
C13 C12 1.364(3) . ?
C13 H13 0.9300 . ?
C10 C11 1.350(4) . ?
C10 H10 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C12 C11 1.403(4) . ?
C12 H12 0.9300 . ?
C11 H11 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
N1 O2 C7 113.14(14) . . ?
N2 N1 C8 113.03(17) . . ?
N2 N1 O2 120.02(16) . . ?
C8 N1 O2 126.90(16) . . ?
N3 N2 N1 107.31(17) . . ?
N1 C8 C9 101.80(17) . . ?
N1 C8 C13 134.87(19) . . ?
C9 C8 C13 123.31(19) . . ?
N2 N3 C9 108.42(18) . . ?
C6 C1 C2 117.95(18) . . ?
C6 C1 C7 121.15(17) . . ?
C2 C1 C7 120.90(17) . . ?
C5 C6 C1 121.64(19) . . ?
C5 C6 Cl3 119.48(16) . . ?
C1 C6 Cl3 118.88(16) . . ?
O1 C7 O2 123.49(19) . . ?
O1 C7 C1 128.97(19) . . ?
O2 C7 C1 107.53(15) . . ?
N3 C9 C8 109.44(18) . . ?
N3 C9 C10 130.6(2) . . ?
C8 C9 C10 120.0(2) . . ?
C3 C2 C1 121.88(18) . . ?
C3 C2 Cl1 119.11(16) . . ?
C1 C2 Cl1 119.01(16) . . ?
C4 C5 C6 118.00(19) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C12 C13 C8 115.2(2) . . ?
C12 C13 H13 122.4 . . ?
C8 C13 H13 122.4 . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 122.4(2) . . ?
C5 C4 Cl2 119.26(17) . . ?
C3 C4 Cl2 118.30(18) . . ?
C13 C12 C11 122.5(2) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C10 C11 C12 122.0(2) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.050
