# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 2111276'
loop_
_audit_author_name
_audit_author_address
'Ashok Kumar Pandey'
;CSIR Indian Institute of Chemical Technology Hyderabad
India
;
_audit_update_record             
;
2021-09-22 deposited with the CCDC.	2023-06-19 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         'C15 H15 Br2 N O5'
_chemical_formula_sum            'C15 H15 Br2 N O5'
_chemical_formula_weight         449.10

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                   8.1671(5)
_cell_length_b                   9.9200(6)
_cell_length_c                   11.5668(6)
_cell_angle_alpha                109.881(2)
_cell_angle_beta                 98.181(2)
_cell_angle_gamma                102.053(2)
_cell_volume                     838.33(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3754
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   0.4701
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.858
_shelx_estimated_absorpt_T_min   0.365
_shelx_estimated_absorpt_T_max   0.617
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27035
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.925
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3754
_reflns_number_gt                3136
_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 2018/2 (Sheldrick, 2018)'
_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)+(0.0398P)²+0.5367P] 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       0.050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3754
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Br2 Br -0.01751(3) 0.18814(3) 0.07830(3) 0.05583(14) Uani 1 1 d . . . . .
Br1 Br 0.79175(4) 1.06878(3) 0.66549(3) 0.05552(14) Uani 1 1 d . . . . .
O1 O 0.35196(18) 0.35868(17) 0.24282(15) 0.0356(3) Uani 1 1 d . . . . .
O5 O 0.3208(2) 0.5012(2) 0.09074(16) 0.0435(4) Uani 1 1 d . . . . .
O4 O 0.1143(2) 0.5944(2) 0.16759(17) 0.0454(4) Uani 1 1 d . . . . .
O3 O 0.7684(2) 0.1395(2) 0.32550(16) 0.0473(4) Uani 1 1 d . . . . .
N1 N 0.6281(2) 0.3419(2) 0.26085(19) 0.0382(4) Uani 1 1 d . . . . .
O2 O 0.6186(2) -0.04500(19) 0.14301(18) 0.0491(4) Uani 1 1 d . . . . .
C3 C 0.4745(3) 0.6539(3) 0.42585(19) 0.0315(4) Uani 1 1 d . . . . .
C7 C 0.5258(3) 0.4218(2) 0.2858(2) 0.0310(4) Uani 1 1 d . . . . .
C4 C 0.5882(3) 0.5807(2) 0.3683(2) 0.0316(4) Uani 1 1 d . . . . .
C13 C 0.0615(3) 0.3414(3) 0.2470(2) 0.0389(5) Uani 1 1 d . . . . .
H13A H -0.023214 0.396639 0.263567 0.047 Uiso 1 1 calc R U . . .
H13B H 0.072203 0.294786 0.308016 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2339(3) 0.4488(2) 0.2637(2) 0.0313(4) Uani 1 1 d . . . . .
C11 C 0.2885(3) 0.5687(3) 0.3971(2) 0.0366(5) Uani 1 1 d . . . . .
H11A H 0.217314 0.636841 0.404709 0.044 Uiso 1 1 calc R U . . .
H11B H 0.271723 0.522501 0.457722 0.044 Uiso 1 1 calc R U . . .
C2 C 0.5361(3) 0.8004(3) 0.5114(2) 0.0374(5) Uani 1 1 d . . . . .
H2 H 0.460871 0.850668 0.548209 0.045 Uiso 1 1 calc R U . . .
C8 C 0.5573(3) 0.1842(3) 0.1846(2) 0.0418(5) Uani 1 1 d . . . . .
H8A H 0.556419 0.166959 0.096737 0.050 Uiso 1 1 calc R U . . .
H8B H 0.439471 0.151863 0.190812 0.050 Uiso 1 1 calc R U . . .
C14 C 0.2169(3) 0.5235(2) 0.1683(2) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.6625(3) 0.0946(3) 0.2281(2) 0.0344(5) Uani 1 1 d . . . . .
C15 C 0.3000(4) 0.5642(4) -0.0050(3) 0.0612(8) Uani 1 1 d . . . . .
H15A H 0.380421 0.542742 -0.057015 0.092 Uiso 1 1 calc R U . . .
H15B H 0.184861 0.521273 -0.056534 0.092 Uiso 1 1 calc R U . . .
H15C H 0.321045 0.670256 0.035135 0.092 Uiso 1 1 calc R U . . .
C5 C 0.7631(3) 0.6571(3) 0.3980(2) 0.0390(5) Uani 1 1 d . . . . .
H5 H 0.838385 0.609761 0.358267 0.047 Uiso 1 1 calc R U . . .
C1 C 0.7100(3) 0.8715(3) 0.5417(2) 0.0385(5) Uani 1 1 d . . . . .
C6 C 0.8248(3) 0.8019(3) 0.4857(2) 0.0409(5) Uani 1 1 d . . . . .
H6 H 0.941370 0.851678 0.506695 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7095(5) -0.1429(4) 0.1727(4) 0.0741(10) Uani 1 1 d . . . . .
H10A H 0.668683 -0.239961 0.105936 0.111 Uiso 1 1 calc R U . . .
H10B H 0.830440 -0.103723 0.181420 0.111 Uiso 1 1 calc R U . . .
H10C H 0.689999 -0.150308 0.250476 0.111 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
Br2 C13 1.936(2) . ?
Br1 C1 1.898(2) . ?
O1 C7 1.368(3) . ?
O1 C12 1.437(2) . ?
O5 C14 1.318(3) . ?
O5 C15 1.452(3) . ?
O4 C14 1.202(3) . ?
O3 C9 1.199(3) . ?
N1 C7 1.265(3) . ?
N1 C8 1.448(3) . ?
O2 C9 1.334(3) . ?
O2 C10 1.437(3) . ?
C3 C2 1.386(3) . ?
C3 C4 1.400(3) . ?
C3 C11 1.503(3) . ?
C7 C4 1.469(3) . ?
C4 C5 1.401(3) . ?
C13 C12 1.520(3) . ?
C12 C11 1.526(3) . ?
C12 C14 1.530(3) . ?
C2 C1 1.382(3) . ?
C8 C9 1.510(3) . ?
C5 C6 1.381(4) . ?
C1 C6 1.384(3) . ?

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 O1 C12 120.94(17) . . ?
C14 O5 C15 115.14(19) . . ?
C7 N1 C8 118.67(19) . . ?
C9 O2 C10 116.0(2) . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 C11 121.42(19) . . ?
C4 C3 C11 118.8(2) . . ?
N1 C7 O1 120.0(2) . . ?
N1 C7 C4 121.53(19) . . ?
O1 C7 C4 118.28(18) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C7 119.75(19) . . ?
C5 C4 C7 120.66(19) . . ?
C12 C13 Br2 111.94(16) . . ?
O1 C12 C13 105.26(17) . . ?
O1 C12 C11 111.18(17) . . ?
C13 C12 C11 109.81(18) . . ?
O1 C12 C14 112.26(17) . . ?
C13 C12 C14 109.29(17) . . ?
C11 C12 C14 108.96(18) . . ?
C3 C11 C12 110.61(17) . . ?
C1 C2 C3 119.6(2) . . ?
N1 C8 C9 110.69(19) . . ?
O4 C14 O5 125.3(2) . . ?
O4 C14 C12 120.5(2) . . ?
O5 C14 C12 114.28(17) . . ?
O3 C9 O2 123.9(2) . . ?
O3 C9 C8 125.9(2) . . ?
O2 C9 C8 110.2(2) . . ?
C6 C5 C4 120.7(2) . . ?
C2 C1 C6 121.8(2) . . ?
C2 C1 Br1 118.48(18) . . ?
C6 C1 Br1 119.72(18) . . ?
C5 C6 C1 118.7(2) . . ?

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.063



