# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1920668'
loop_
_audit_author_name
_audit_author_address
'Bipul Sarma'
;Tezpur University
India
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2019-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C96 H56 Br12 N12 O5'
_chemical_formula_weight         2416.44

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.6559(5)
_cell_length_b                   15.6308(9)
_cell_length_c                   16.2787(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2202.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4236
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      15.42

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   0.185
_exptl_transmission_factor_max   0.315
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    5.518
_shelx_estimated_absorpt_T_min   0.271
_shelx_estimated_absorpt_T_max   0.390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50377
_diffrn_reflns_av_unetI/netI     0.1478
_diffrn_reflns_av_R_equivalents  0.2068
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         28.482
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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             5555
_reflns_number_gt                2350
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0593P)²+1.0931P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5555
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1928
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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
Br1 Br 1.0932(2) 0.73631(13) 0.49653(9) 0.1056(7) Uani 1 1 d . . . . .
Br2 Br 0.9984(2) 0.49197(10) -0.12162(10) 0.1099(7) Uani 1 1 d . . . . .
Br3 Br 0.36939(15) 0.47945(8) 0.06662(8) 0.0676(4) Uani 1 1 d . . . . .
C1 C 0.9446(13) 0.9107(8) 0.1513(7) 0.055(3) Uani 1 1 d . . . . .
H1 H 0.9119 0.9257 0.0989 0.066 Uiso 1 1 calc R U . . .
C2 C 0.8996(13) 0.8377(7) 0.1929(6) 0.045(3) Uani 1 1 d . . . . .
C3 C 0.9777(12) 0.8400(7) 0.2704(7) 0.046(3) Uani 1 1 d . . . . .
C4 C 0.9842(13) 0.7875(7) 0.3387(7) 0.053(3) Uani 1 1 d . . . . .
H4 H 0.9253 0.7378 0.3409 0.064 Uiso 1 1 calc R U . . .
C5 C 1.0792(13) 0.8095(8) 0.4036(7) 0.054(3) Uani 1 1 d . . . . .
C6 C 1.1705(13) 0.8853(9) 0.4023(8) 0.063(4) Uani 1 1 d . . . . .
H6 H 1.2320 0.8985 0.4474 0.076 Uiso 1 1 calc R U . . .
C7 C 1.1696(13) 0.9380(8) 0.3370(8) 0.059(3) Uani 1 1 d . . . . .
H7 H 1.2313 0.9867 0.3349 0.071 Uiso 1 1 calc R U . . .
C8 C 1.0686(12) 0.9152(7) 0.2712(8) 0.050(3) Uani 1 1 d . . . . .
C9 C 0.7946(11) 0.7707(7) 0.1569(6) 0.040(3) Uani 1 1 d . . . . .
C10 C 0.8829(11) 0.6833(7) 0.1498(7) 0.039(2) Uani 1 1 d . . . . .
C11 C 0.8890(11) 0.6655(6) 0.0622(6) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.9495(12) 0.5932(7) 0.0206(7) 0.050(3) Uani 1 1 d . . . . .
H12 H 1.0061 0.5517 0.0483 0.060 Uiso 1 1 calc R U . . .
C13 C 0.9212(13) 0.5871(7) -0.0623(7) 0.057(3) Uani 1 1 d . . . . .
C14 C 0.8366(13) 0.6500(8) -0.1031(7) 0.055(3) Uani 1 1 d . . . . .
H14 H 0.8205 0.6442 -0.1593 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7764(11) 0.7196(7) -0.0643(7) 0.047(3) Uani 1 1 d . . . . .
H15 H 0.7183 0.7601 -0.0926 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8062(10) 0.7277(7) 0.0209(6) 0.039(3) Uani 1 1 d . . . . .
C17 C 0.6476(11) 0.7561(7) 0.2078(6) 0.043(3) Uani 1 1 d . . . . .
C18 C 0.5387(11) 0.6886(7) 0.1946(6) 0.041(3) Uani 1 1 d . . . . .
C19 C 0.5215(12) 0.6221(7) 0.1397(7) 0.046(3) Uani 1 1 d . . . . .
H19 H 0.5966 0.6128 0.0998 0.055 Uiso 1 1 calc R U . . .
C20 C 0.3936(13) 0.5693(7) 0.1433(7) 0.051(3) Uani 1 1 d . . . . .
C21 C 0.2803(13) 0.5811(9) 0.2029(8) 0.056(3) Uani 1 1 d . . . . .
H21 H 0.1964 0.5440 0.2053 0.067 Uiso 1 1 calc R U . . .
C22 C 0.2915(14) 0.6473(10) 0.2583(8) 0.069(4) Uani 1 1 d . . . . .
H22 H 0.2149 0.6564 0.2974 0.083 Uiso 1 1 calc R U . . .
C23 C 0.4214(12) 0.7005(8) 0.2542(7) 0.048(3) Uani 1 1 d . . . . .
C24 C 0.5969(13) 0.8035(9) 0.2713(7) 0.059(3) Uani 1 1 d . . . . .
H24 H 0.6486 0.8505 0.2931 0.070 Uiso 1 1 calc R U . . .
N1 N 1.0444(11) 0.9579(6) 0.1986(6) 0.056(2) Uani 1 1 d . . . . .
H1A H 1.0850 1.0061 0.1851 0.067 Uiso 1 1 calc R U . . .
N2 N 0.7560(9) 0.7900(6) 0.0718(5) 0.049(2) Uani 1 1 d . . . . .
H2 H 0.7075 0.8352 0.0561 0.059 Uiso 1 1 calc R U . . .
N3 N 0.4590(10) 0.7729(7) 0.2993(6) 0.067(3) Uani 1 1 d . . . . .
H3 H 0.4046 0.7948 0.3382 0.080 Uiso 1 1 calc R U . . .
O1 O 0.9294(8) 0.6421(5) 0.2078(4) 0.0482(19) Uani 1 1 d . . . . .
O2 O 0.200(5) 0.107(3) 0.141(3) 0.116(16) Uani 0.25 1 d . . P . .


_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 C5 1.900(11) . ?
Br2 C13 1.895(11) . ?
Br3 C20 1.890(12) . ?
C1 N1 1.372(14) . ?
C1 C2 1.383(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.433(15) . ?
C2 C9 1.505(14) . ?
C3 C4 1.383(15) . ?
C3 C8 1.414(14) . ?
C4 C5 1.383(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(17) . ?
C6 C7 1.344(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.429(15) . ?
C7 H7 0.9300 . ?
C8 N1 1.373(14) . ?
C9 N2 1.456(12) . ?
C9 C17 1.535(14) . ?
C9 C10 1.569(14) . ?
C10 O1 1.212(11) . ?
C10 C11 1.455(14) . ?
C11 C16 1.383(13) . ?
C11 C12 1.417(14) . ?
C12 C13 1.375(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(16) . ?
C14 C15 1.361(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.416(14) . ?
C15 H15 0.9300 . ?
C16 N2 1.352(12) . ?
C17 C24 1.346(14) . ?
C17 C18 1.431(14) . ?
C18 C19 1.379(15) . ?
C18 C23 1.416(14) . ?
C19 C20 1.383(15) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(15) . ?
C21 C22 1.376(17) . ?
C21 H21 0.9300 . ?
C22 C23 1.401(17) . ?
C22 H22 0.9300 . ?
C23 N3 1.388(15) . ?
C24 N3 1.364(14) . ?
C24 H24 0.9300 . ?
N1 H1A 0.8600 . ?
N2 H2 0.8600 . ?
N3 H3 0.8600 . ?

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 C1 C2 110.3(10) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C1 C2 C3 106.1(10) . . ?
C1 C2 C9 123.6(10) . . ?
C3 C2 C9 130.2(10) . . ?
C4 C3 C8 117.6(11) . . ?
C4 C3 C2 135.5(10) . . ?
C8 C3 C2 106.9(10) . . ?
C3 C4 C5 119.4(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.7(11) . . ?
C4 C5 Br1 119.8(9) . . ?
C6 C5 Br1 118.5(9) . . ?
C7 C6 C5 121.3(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 116.3(12) . . ?
C6 C7 H7 121.8 . . ?
C8 C7 H7 121.8 . . ?
N1 C8 C3 108.2(10) . . ?
N1 C8 C7 128.1(11) . . ?
C3 C8 C7 123.7(12) . . ?
N2 C9 C2 111.4(9) . . ?
N2 C9 C17 110.7(8) . . ?
C2 C9 C17 113.2(8) . . ?
N2 C9 C10 102.8(8) . . ?
C2 C9 C10 109.9(8) . . ?
C17 C9 C10 108.3(8) . . ?
O1 C10 C11 130.6(10) . . ?
O1 C10 C9 124.5(9) . . ?
C11 C10 C9 104.9(8) . . ?
C16 C11 C12 121.3(9) . . ?
C16 C11 C10 108.9(9) . . ?
C12 C11 C10 129.4(10) . . ?
C13 C12 C11 117.3(10) . . ?
C13 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
C12 C13 C14 120.8(10) . . ?
C12 C13 Br2 119.5(10) . . ?
C14 C13 Br2 119.7(9) . . ?
C15 C14 C13 122.9(11) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 C16 117.1(11) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
N2 C16 C11 112.0(9) . . ?
N2 C16 C15 127.4(10) . . ?
C11 C16 C15 120.6(10) . . ?
C24 C17 C18 107.8(10) . . ?
C24 C17 C9 127.1(10) . . ?
C18 C17 C9 125.1(8) . . ?
C19 C18 C23 117.7(10) . . ?
C19 C18 C17 136.4(10) . . ?
C23 C18 C17 105.9(9) . . ?
C18 C19 C20 120.6(10) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 121.0(11) . . ?
C19 C20 Br3 120.3(8) . . ?
C21 C20 Br3 118.7(10) . . ?
C22 C21 C20 120.5(12) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 118.1(11) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
N3 C23 C22 130.3(11) . . ?
N3 C23 C18 107.5(10) . . ?
C22 C23 C18 122.1(12) . . ?
C17 C24 N3 110.4(11) . . ?
C17 C24 H24 124.8 . . ?
N3 C24 H24 124.8 . . ?
C1 N1 C8 108.4(9) . . ?
C1 N1 H1A 125.8 . . ?
C8 N1 H1A 125.8 . . ?
C16 N2 C9 111.1(8) . . ?
C16 N2 H2 124.4 . . ?
C9 N2 H2 124.4 . . ?
C24 N3 C23 108.3(9) . . ?
C24 N3 H3 125.8 . . ?
C23 N3 H3 125.8 . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.088

