# 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_f
_database_code_depnum_ccdc_archive 'CCDC 2092531'
loop_
_audit_author_name
_audit_author_address
'Dr. Malay Dolai'
;Vidyasagar University
India
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2021-10-12 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            'C12 H16 Br N O5'
_chemical_formula_weight         334.17

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.2787(16)
_cell_length_b                   10.7136(13)
_cell_length_c                   10.6360(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.998(4)
_cell_angle_gamma                90
_cell_volume                     1330.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    432
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.12

_exptl_crystal_description       plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.105
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6225
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15131
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.744
_diffrn_reflns_theta_max         29.144
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3589
_reflns_number_gt                2701
_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 Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0267P)²+0.5203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3589
_refine_ls_number_parameters     189
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
Br Br -0.04442(2) 0.48688(2) 0.81101(3) 0.02745(9) Uani 1 1 d . . . . .
O1 O 0.29752(14) 0.59788(13) 0.52675(17) 0.0180(4) Uani 1 1 d . . . . .
O2 O 0.20014(15) 0.37663(14) 0.49456(18) 0.0223(4) Uani 1 1 d . . . . .
O3 O 0.55056(15) 0.77492(14) 0.60397(17) 0.0183(4) Uani 1 1 d D . . . .
H3A H 0.590(2) 0.7055(17) 0.634(3) 0.044(9) Uiso 1 1 d D . . . .
O4 O 0.46370(17) 1.10246(14) 0.62315(18) 0.0244(4) Uani 1 1 d D . . . .
H4A H 0.451(3) 1.148(3) 0.551(2) 0.051(10) Uiso 1 1 d D . . . .
O5 O 0.35310(14) 1.04219(13) 0.83729(17) 0.0180(4) Uani 1 1 d D . . . .
H5A H 0.324(3) 1.012(2) 0.897(3) 0.051(10) Uiso 1 1 d D . . . .
N1 N 0.35786(17) 0.79542(16) 0.6748(2) 0.0144(4) Uani 1 1 d . . . . .
H1 H 0.366(2) 0.746(2) 0.620(3) 0.021(7) Uiso 1 1 d . . . . .
C1 C 0.2299(2) 0.57295(19) 0.5950(2) 0.0151(5) Uani 1 1 d . . . . .
C2 C 0.1698(2) 0.45532(19) 0.5787(2) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.0918(2) 0.4306(2) 0.6430(3) 0.0192(5) Uani 1 1 d . . . . .
H3 H 0.051082 0.353847 0.628176 0.023 Uiso 1 1 calc R U . . .
C4 C 0.0717(2) 0.5194(2) 0.7317(3) 0.0185(5) Uani 1 1 d . . . . .
C5 C 0.1321(2) 0.6272(2) 0.7596(3) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.120579 0.683426 0.823372 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2130(2) 0.65538(19) 0.6925(2) 0.0151(5) Uani 1 1 d . . . . .
C7 C 0.1490(3) 0.2558(2) 0.4752(3) 0.0316(7) Uani 1 1 d . . . . .
H7A H 0.168433 0.211739 0.560048 0.047 Uiso 1 1 calc R U . . .
H7B H 0.177665 0.208392 0.413257 0.047 Uiso 1 1 calc R U . . .
H7C H 0.065596 0.264223 0.439131 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2810(2) 0.76458(19) 0.7292(2) 0.0165(5) Uani 1 1 d . . . . .
H8 H 0.269529 0.816903 0.796149 0.020 Uiso 1 1 calc R U . . .
C9 C 0.43686(19) 0.90236(18) 0.7072(2) 0.0127(5) Uani 1 1 d . . . . .
C10 C 0.5560(2) 0.8537(2) 0.7145(2) 0.0166(5) Uani 1 1 d . . . . .
H10A H 0.607445 0.925110 0.715507 0.020 Uiso 1 1 calc R U . . .
H10B H 0.588309 0.806099 0.797463 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3911(2) 0.99620(18) 0.5944(2) 0.0170(5) Uani 1 1 d . . . . .
H11A H 0.391170 0.958655 0.509356 0.020 Uiso 1 1 calc R U . . .
H11B H 0.311624 1.020400 0.587390 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4466(2) 0.96063(19) 0.8411(2) 0.0154(5) Uani 1 1 d . . . . .
H12A H 0.449912 0.893193 0.905831 0.019 Uiso 1 1 calc R U . . .
H12B H 0.519102 1.008263 0.872121 0.019 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
Br C4 1.900(2) . ?
O1 C1 1.288(3) . ?
O2 C2 1.363(3) . ?
O2 C7 1.426(3) . ?
O3 C10 1.431(3) . ?
O3 H3A 0.889(10) . ?
O4 C11 1.420(3) . ?
O4 H4A 0.884(10) . ?
O5 C12 1.433(3) . ?
O5 H5A 0.886(10) . ?
N1 C8 1.293(3) . ?
N1 C9 1.472(3) . ?
N1 H1 0.82(3) . ?
C1 C6 1.426(3) . ?
C1 C2 1.444(3) . ?
C2 C3 1.363(3) . ?
C3 C4 1.415(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.355(3) . ?
C5 C6 1.423(3) . ?
C5 H5 0.9500 . ?
C6 C8 1.420(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 C12 1.526(3) . ?
C9 C10 1.533(3) . ?
C9 C11 1.533(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C2 O2 C7 117.28(19) . . ?
C10 O3 H3A 108(2) . . ?
C11 O4 H4A 109(2) . . ?
C12 O5 H5A 105(2) . . ?
C8 N1 C9 127.86(19) . . ?
C8 N1 H1 115.1(18) . . ?
C9 N1 H1 116.9(18) . . ?
O1 C1 C6 123.06(19) . . ?
O1 C1 C2 120.6(2) . . ?
C6 C1 C2 116.3(2) . . ?
O2 C2 C3 125.9(2) . . ?
O2 C2 C1 112.64(19) . . ?
C3 C2 C1 121.5(2) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 Br 119.62(18) . . ?
C3 C4 Br 118.88(17) . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C8 C6 C5 118.6(2) . . ?
C8 C6 C1 120.3(2) . . ?
C5 C6 C1 120.96(19) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C6 122.4(2) . . ?
N1 C8 H8 118.8 . . ?
C6 C8 H8 118.8 . . ?
N1 C9 C12 113.14(17) . . ?
N1 C9 C10 107.27(16) . . ?
C12 C9 C10 107.10(19) . . ?
N1 C9 C11 105.77(19) . . ?
C12 C9 C11 111.50(17) . . ?
C10 C9 C11 112.08(18) . . ?
O3 C10 C9 110.94(19) . . ?
O3 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
O4 C11 C9 107.66(19) . . ?
O4 C11 H11A 110.2 . . ?
C9 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C9 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
O5 C12 C9 113.07(19) . . ?
O5 C12 H12A 109.0 . . ?
C9 C12 H12A 109.0 . . ?
O5 C12 H12B 109.0 . . ?
C9 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.090

