# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1841621'
loop_
_audit_author_name
_audit_author_address
'Rajat Saha'
;KAZI NAZRUL UNIVERSITY
India
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H2 Br4 O4, C8 H6 N2'
_chemical_formula_sum            'C16 H8 Br4 N2 O4'
_chemical_formula_weight         611.88

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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   9.4972(18)
_cell_length_b                   14.745(3)
_cell_length_c                   13.181(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1845.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    29997
_cell_measurement_theta_min      2.072
_cell_measurement_theta_max      27.513

_exptl_crystal_description       Rhombohedral
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.202
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   0.295
_exptl_transmission_factor_max   0.417
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    8.746
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29997
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2199
_reflns_number_gt                1576
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0227P)²+1.4697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0045(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2199
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_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 0.54707(3) 0.13559(2) 0.44468(2) 0.04276(12) Uani 1 1 d . . . . .
Br2 Br 0.96838(4) 0.13551(2) 0.74353(2) 0.04569(12) Uani 1 1 d . . . . .
O1 O 0.8549(2) 0.02272(14) 0.53156(16) 0.0478(6) Uani 1 1 d . . . . .
H1O1 H 0.865529 -0.027238 0.532508 0.072 Uiso 1 1 d R U . . .
O2 O 0.6818(2) 0.00871(14) 0.64507(16) 0.0481(6) Uani 1 1 d . . . . .
C5 C 0.7589(3) 0.05282(19) 0.5935(2) 0.0317(7) Uani 1 1 d . . . . .
C6 C 0.7582(3) 0.15550(18) 0.59328(19) 0.0262(6) Uani 1 1 d . . . . .
C7 C 0.6687(3) 0.20296(18) 0.52939(19) 0.0266(6) Uani 1 1 d . . . . .
C8 C 0.8474(3) 0.20314(18) 0.65803(19) 0.0286(6) Uani 1 1 d . . . . .
N1 N 1.1168(3) 0.15553(17) 0.4669(2) 0.0421(7) Uani 1 1 d . . . . .
C1 C 0.8520(4) 0.2028(3) 0.2760(2) 0.0585(10) Uani 1 1 d . . . . .
H1 H 0.791453 0.171757 0.232711 0.070 Uiso 1 1 calc R U . . .
C2 C 0.9388(4) 0.1552(2) 0.3382(3) 0.0484(9) Uani 1 1 d . . . . .
H3 H 0.938269 0.092088 0.337220 0.058 Uiso 1 1 calc R U . . .
C3 C 1.0292(3) 0.2021(2) 0.4037(2) 0.0341(7) Uani 1 1 d . . . . .
C4 C 1.1964(3) 0.2023(2) 0.5277(3) 0.0479(9) Uani 1 1 d . . . . .
H4 H 1.255167 0.171713 0.572592 0.057 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 C7 1.889(3) . ?
Br2 C8 1.893(3) . ?
O1 C5 1.302(3) . ?
O1 H1O1 0.7437 . ?
O2 C5 1.192(3) . ?
C5 C6 1.514(4) . ?
C6 C7 1.386(4) . ?
C6 C8 1.393(4) . ?
C7 C7 1.387(5) 8_565 ?
C8 C8 1.382(5) 8_565 ?
N1 C4 1.299(4) . ?
N1 C3 1.363(4) . ?
C1 C2 1.358(5) . ?
C1 C1 1.393(8) 8_565 ?
C1 H1 0.9300 . ?
C2 C3 1.401(4) . ?
C2 H3 0.9300 . ?
C3 C3 1.412(6) 8_565 ?
C4 C4 1.407(7) 8_565 ?
C4 H4 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
C5 O1 H1O1 115.0 . . ?
O2 C5 O1 127.0(3) . . ?
O2 C5 C6 122.9(3) . . ?
O1 C5 C6 110.0(2) . . ?
C7 C6 C8 119.4(2) . . ?
C7 C6 C5 120.6(2) . . ?
C8 C6 C5 120.0(2) . . ?
C6 C7 C7 120.33(15) . 8_565 ?
C6 C7 Br1 117.9(2) . . ?
C7 C7 Br1 121.72(8) 8_565 . ?
C8 C8 C6 120.29(15) 8_565 . ?
C8 C8 Br2 121.78(8) 8_565 . ?
C6 C8 Br2 117.9(2) . . ?
C4 N1 C3 117.7(3) . . ?
C2 C1 C1 121.1(2) . 8_565 ?
C2 C1 H1 119.4 . . ?
C1 C1 H1 119.4 8_565 . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H3 120.4 . . ?
C3 C2 H3 120.4 . . ?
N1 C3 C2 120.1(3) . . ?
N1 C3 C3 120.26(17) . 8_565 ?
C2 C3 C3 119.6(2) . 8_565 ?
N1 C4 C4 122.04(19) . 8_565 ?
N1 C4 H4 119.0 . . ?
C4 C4 H4 119.0 8_565 . ?

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
O2 C5 C6 C7 -87.4(4) . . . . ?
O1 C5 C6 C7 93.2(3) . . . . ?
O2 C5 C6 C8 92.2(4) . . . . ?
O1 C5 C6 C8 -87.1(3) . . . . ?
C8 C6 C7 C7 0.5(3) . . . 8_565 ?
C5 C6 C7 C7 -179.89(17) . . . 8_565 ?
C8 C6 C7 Br1 -178.84(19) . . . . ?
C5 C6 C7 Br1 0.8(3) . . . . ?
C7 C6 C8 C8 -0.5(3) . . . 8_565 ?
C5 C6 C8 C8 179.88(17) . . . 8_565 ?
C7 C6 C8 Br2 -179.7(2) . . . . ?
C5 C6 C8 Br2 0.6(3) . . . . ?
C1 C1 C2 C3 0.4(4) 8_565 . . . ?
C4 N1 C3 C2 -178.6(3) . . . . ?
C4 N1 C3 C3 1.5(3) . . . 8_565 ?
C1 C2 C3 N1 179.8(3) . . . . ?
C1 C2 C3 C3 -0.4(4) . . . 8_565 ?
C3 N1 C4 C4 -1.6(3) . . . 8_565 ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.087

