# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_SK14
_database_code_depnum_ccdc_archive 'CCDC 1841619'
loop_
_audit_author_name
_audit_author_address
'Rajat Saha'
;KAZI NAZRUL UNIVERSITY
India
;
_audit_update_record             
;
2018-05-06 deposited with the CCDC.	2020-09-29 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         'C8 H2 Br4 O4, C5 H4 Br N'
_chemical_formula_sum            'C13 H6 Br5 N O4'
_chemical_formula_weight         639.74

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                   8.8412(19)
_cell_length_b                   9.012(2)
_cell_length_c                   12.227(3)
_cell_angle_alpha                70.384(3)
_cell_angle_beta                 71.053(3)
_cell_angle_gamma                77.807(4)
_cell_volume                     862.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    665
_cell_measurement_theta_min      7.40
_cell_measurement_theta_max      22.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.464
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    11.668
_shelx_estimated_absorpt_T_min   0.174
_shelx_estimated_absorpt_T_max   0.292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.176
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(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            9209
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.839
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3189
_reflns_number_gt                2649
_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-2014/7 (Sheldrick, 2015)'
_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)+(0.0574P)²+0.3159P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3189
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.58513(7) 0.27146(6) 0.58763(4) 0.04496(19) Uani 1 1 d . . . . .
Br2 Br 0.41866(7) 0.10398(6) 0.23856(4) 0.0493(2) Uani 1 1 d . . . . .
Br3 Br 0.32602(7) 0.79236(7) 0.11632(6) 0.0531(2) Uani 1 1 d . . . . .
Br4 Br 0.10631(6) 0.55985(8) 0.08081(6) 0.0602(2) Uani 1 1 d . . . . .
Br5 Br 0.95756(10) 0.72948(14) 0.53736(8) 0.0967(3) Uani 1 1 d . . . . .
O1 O 0.4056(5) 0.4267(5) 0.3532(4) 0.0568(10) Uani 1 1 d . . . . .
O2 O 0.6629(5) 0.3461(4) 0.2759(3) 0.0533(10) Uani 1 1 d . . . . .
H2 H 0.6667 0.4392 0.2355 0.080 Uiso 1 1 calc R U . . .
O3 O 0.7186(4) 0.6294(4) 0.1496(3) 0.0415(8) Uani 1 1 d . . . . .
H3 H 0.7346 0.6994 0.1721 0.062 Uiso 1 1 calc R U . . .
O4 O 0.7372(5) 0.8122(4) -0.0290(3) 0.0499(10) Uani 1 1 d . . . . .
N1 N 0.8240(5) 0.8068(6) 0.2319(4) 0.0482(11) Uani 1 1 d . . . . .
C1 C 0.5086(6) 0.1557(6) 0.4254(4) 0.0345(10) Uani 1 1 d . . . . .
C2 C 0.5392(6) 0.1134(6) 0.5377(4) 0.0346(10) Uani 1 1 d . . . . .
C3 C 0.4687(6) 0.0430(6) 0.3884(4) 0.0350(11) Uani 1 1 d . . . . .
C4 C 0.5187(7) 0.3270(6) 0.3458(4) 0.0396(12) Uani 1 1 d . . . . .
C5 C 0.5917(6) 0.5930(6) 0.0202(4) 0.0327(10) Uani 1 1 d . . . . .
C6 C 0.4242(6) 0.6200(5) 0.0527(4) 0.0314(10) Uani 1 1 d . . . . .
C7 C 0.3344(6) 0.5277(6) 0.0339(4) 0.0341(10) Uani 1 1 d . . . . .
C8 C 0.6918(6) 0.6909(6) 0.0443(4) 0.0346(11) Uani 1 1 d . . . . .
C9 C 0.8523(7) 0.7416(8) 0.3400(6) 0.0531(14) Uani 1 1 d . . . . .
H9 H 0.8254 0.6402 0.3854 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9209(7) 0.8241(9) 0.3840(6) 0.0619(17) Uani 1 1 d . . . . .
C11 C 0.9601(8) 0.9714(10) 0.3175(7) 0.082(2) Uani 1 1 d . . . . .
H11 H 1.0073 1.0279 0.3464 0.098 Uiso 1 1 calc R U . . .
C12 C 0.9291(9) 1.0376(9) 0.2054(7) 0.078(2) Uani 1 1 d . . . . .
H12 H 0.9558 1.1386 0.1585 0.094 Uiso 1 1 calc R U . . .
C13 C 0.8582(7) 0.9515(8) 0.1645(6) 0.0617(17) Uani 1 1 d . . . . .
H13 H 0.8348 0.9948 0.0905 0.074 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 C2 1.886(5) . ?
Br2 C3 1.897(4) . ?
Br3 C6 1.890(5) . ?
Br4 C7 1.895(5) . ?
Br5 C10 1.885(6) . ?
O1 C4 1.197(7) . ?
O2 C4 1.293(6) . ?
O2 H2 0.8200 . ?
O3 C8 1.298(5) . ?
O3 H3 0.8200 . ?
O4 C8 1.206(6) . ?
N1 C13 1.324(8) . ?
N1 C9 1.336(7) . ?
C1 C3 1.388(6) . ?
C1 C2 1.397(6) . ?
C1 C4 1.526(7) . ?
C2 C3 1.398(6) 2_656 ?
C3 C2 1.398(6) 2_656 ?
C5 C6 1.393(7) . ?
C5 C7 1.396(7) 2_665 ?
C5 C8 1.525(6) . ?
C6 C7 1.380(6) . ?
C7 C5 1.396(7) 2_665 ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(10) . ?
C11 C12 1.391(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(9) . ?
C12 H12 0.9300 . ?
C13 H13 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
C4 O2 H2 109.5 . . ?
C8 O3 H3 109.5 . . ?
C13 N1 C9 122.3(5) . . ?
C3 C1 C2 119.9(4) . . ?
C3 C1 C4 121.2(4) . . ?
C2 C1 C4 118.9(4) . . ?
C1 C2 C3 119.7(4) . 2_656 ?
C1 C2 Br1 118.7(4) . . ?
C3 C2 Br1 121.5(3) 2_656 . ?
C1 C3 C2 120.3(4) . 2_656 ?
C1 C3 Br2 119.5(3) . . ?
C2 C3 Br2 120.1(3) 2_656 . ?
O1 C4 O2 126.9(5) . . ?
O1 C4 C1 122.2(5) . . ?
O2 C4 C1 110.9(5) . . ?
C6 C5 C7 118.2(4) . 2_665 ?
C6 C5 C8 121.0(4) . . ?
C7 C5 C8 120.7(4) 2_665 . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 Br3 121.5(4) . . ?
C5 C6 Br3 117.8(3) . . ?
C6 C7 C5 121.1(4) . 2_665 ?
C6 C7 Br4 121.2(4) . . ?
C5 C7 Br4 117.7(3) 2_665 . ?
O4 C8 O3 126.0(4) . . ?
O4 C8 C5 121.4(4) . . ?
O3 C8 C5 112.6(4) . . ?
N1 C9 C10 120.0(6) . . ?
N1 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 Br5 121.2(5) . . ?
C9 C10 Br5 119.0(5) . . ?
C10 C11 C12 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 119.2(7) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N1 C13 C12 119.3(7) . . ?
N1 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?

_refine_diff_density_max         0.706
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.141


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 1.75 2.557(5) 168 1_555
O3 H3 N1 0.82 1.81 2.598(4) 161 1_555
####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 1841620'
loop_
_audit_author_name
_audit_author_address
'Corrado Rizzoli'
;University of Parma
Italy
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2020-09-29 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         'C8 H2 Br4 O4, C8 Br4 O4, 2(C5 H7 N2), 2(H2 O)'
_chemical_formula_sum            'C26 H20 Br8 N4 O10'
_chemical_formula_weight         1187.74

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                   8.914(2)
_cell_length_b                   10.446(3)
_cell_length_c                   10.466(3)
_cell_angle_alpha                65.089(7)
_cell_angle_beta                 86.050(8)
_cell_angle_gamma                75.658(8)
_cell_volume                     855.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4877
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      32.14

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.305
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    9.433
_shelx_estimated_absorpt_T_min   0.314
_shelx_estimated_absorpt_T_max   0.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_T_max  0.389
_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                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9617
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3147
_reflns_number_gt                2507
_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, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP 3 for windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.1052P)²+20.2067P] 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     'SHELXL-2014/7 (Sheldrick 2015b)'
_refine_ls_extinction_coef       0.0071(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3147
_refine_ls_number_parameters     221
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.2164
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_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 0.62515(12) 0.60818(14) 0.02036(15) 0.0370(4) Uani 1 1 d . . . . .
Br2 Br 0.86575(14) 0.77884(12) 0.07700(13) 0.0317(4) Uani 1 1 d . . . . .
Br3 Br 1.13852(13) 0.56612(14) 0.58895(13) 0.0351(4) Uani 1 1 d . . . . .
Br4 Br 1.38660(15) 0.73891(15) 0.63363(15) 0.0411(4) Uani 1 1 d . . . . .
O1 O 1.2706(13) 0.2329(10) 0.5660(10) 0.050(3) Uani 1 1 d . . . . .
O2 O 1.2091(10) 0.3977(9) 0.3495(9) 0.0340(19) Uani 1 1 d . . . . .
H1O2 H 1.2349 0.4718 0.2957 0.051 Uiso 1 1 calc R U . . .
O3 O 1.2328(11) 0.7617(10) -0.0691(10) 0.045(2) Uani 1 1 d . . . . .
O4 O 1.2694(10) 0.6158(9) 0.1579(9) 0.0325(19) Uani 1 1 d . . . . .
O1W O 1.3669(12) 0.9895(11) -0.1871(12) 0.060(3) Uani 1 1 d . . . . .
H1W1 H 1.3257 0.9201 -0.1629 0.089 Uiso 1 1 d R U . . .
H2W1 H 1.3278 1.0512 -0.2651 0.089 Uiso 1 1 d R U . . .
N1 N 1.3325(14) 1.0183(10) 0.2558(11) 0.034(2) Uani 1 1 d . . . . .
H1N1 H 1.431(17) 1.037(15) 0.219(15) 0.041 Uiso 1 1 d . U . . .
N2 N 1.4035(14) 0.8276(13) 0.1902(13) 0.044(3) Uani 1 1 d . U . . .
H1N2 H 1.4941 0.8447 0.1730 0.053 Uiso 1 1 calc R U . . .
H2N2 H 1.3828 0.7577 0.1773 0.053 Uiso 1 1 calc R U . . .
C1 C 1.2860(14) 0.3430(13) 0.4707(12) 0.030(2) Uani 1 1 d . . . . .
C2 C 1.3969(13) 0.4277(11) 0.4817(11) 0.025(2) Uani 1 1 d . . . . .
C3 C 1.3464(13) 0.5292(12) 0.5393(11) 0.025(2) Uani 1 1 d . . . . .
C4 C 1.4520(14) 0.6010(13) 0.5565(11) 0.030(2) Uani 1 1 d . . . . .
C5 C 1.2095(12) 0.6583(12) 0.0368(12) 0.025(2) Uani 1 1 d . . . . .
C6 C 1.1021(12) 0.5734(11) 0.0201(10) 0.020(2) Uani 1 1 d . . . . .
C7 C 0.9425(12) 0.6175(11) 0.0309(11) 0.022(2) Uani 1 1 d . . . . .
C8 C 0.8431(12) 0.5444(12) 0.0105(11) 0.024(2) Uani 1 1 d . . . . .
C9 C 1.230(2) 1.1056(15) 0.3016(16) 0.050(4) Uani 1 1 d . . . . .
H9 H 1.2605 1.1789 0.3139 0.060 Uiso 1 1 calc R U . . .
C10 C 1.082(2) 1.0899(16) 0.3309(17) 0.057(4) Uani 1 1 d . . . . .
H10 H 1.0109 1.1519 0.3609 0.069 Uiso 1 1 calc R U . . .
C11 C 1.0437(18) 0.9764(17) 0.3137(17) 0.052(4) Uani 1 1 d . . . . .
H11 H 0.9451 0.9604 0.3358 0.062 Uiso 1 1 calc R U . . .
C12 C 1.1453(15) 0.8900(13) 0.2660(14) 0.037(3) Uani 1 1 d . . . . .
H12 H 1.1163 0.8170 0.2523 0.045 Uiso 1 1 calc R U . . .
C13 C 1.2946(15) 0.9102(13) 0.2372(12) 0.033(3) Uani 1 1 d . . . . .


_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 C8 1.902(11) . ?
Br2 C7 1.900(10) . ?
Br3 C3 1.880(11) . ?
Br4 C4 1.888(12) . ?
O1 C1 1.195(15) . ?
O2 C1 1.312(14) . ?
O2 H1O2 0.8200 . ?
O3 C5 1.229(14) . ?
O4 C5 1.262(14) . ?
O1W H1W1 0.8299 . ?
O1W H2W1 0.8301 . ?
N1 C9 1.338(18) . ?
N1 C13 1.346(15) . ?
N1 H1N1 0.96(15) . ?
N2 C13 1.343(17) . ?
N2 H1N2 0.8600 . ?
N2 H2N2 0.8600 . ?
C1 C2 1.519(15) . ?
C2 C4 1.374(17) 2_866 ?
C2 C3 1.399(15) . ?
C3 C4 1.403(16) . ?
C4 C2 1.374(17) 2_866 ?
C5 C6 1.519(13) . ?
C6 C8 1.366(15) 2_765 ?
C6 C7 1.395(15) . ?
C7 C8 1.383(15) . ?
C8 C6 1.366(15) 2_765 ?
C9 C10 1.37(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.40(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.34(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(18) . ?
C12 H12 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
C1 O2 H1O2 109.5 . . ?
H1W1 O1W H2W1 107.7 . . ?
C9 N1 C13 121.4(13) . . ?
C9 N1 H1N1 123(9) . . ?
C13 N1 H1N1 114(9) . . ?
C13 N2 H1N2 120.0 . . ?
C13 N2 H2N2 120.0 . . ?
H1N2 N2 H2N2 120.0 . . ?
O1 C1 O2 122.1(11) . . ?
O1 C1 C2 122.2(11) . . ?
O2 C1 C2 115.7(10) . . ?
C4 C2 C3 120.1(11) 2_866 . ?
C4 C2 C1 120.6(10) 2_866 . ?
C3 C2 C1 119.2(10) . . ?
C2 C3 C4 118.9(11) . . ?
C2 C3 Br3 118.7(8) . . ?
C4 C3 Br3 122.4(9) . . ?
C2 C4 C3 121.0(11) 2_866 . ?
C2 C4 Br4 119.3(9) 2_866 . ?
C3 C4 Br4 119.7(9) . . ?
O3 C5 O4 125.1(10) . . ?
O3 C5 C6 117.5(10) . . ?
O4 C5 C6 117.4(9) . . ?
C8 C6 C7 118.0(9) 2_765 . ?
C8 C6 C5 121.7(10) 2_765 . ?
C7 C6 C5 120.3(9) . . ?
C8 C7 C6 120.8(10) . . ?
C8 C7 Br2 120.9(8) . . ?
C6 C7 Br2 118.3(7) . . ?
C6 C8 C7 121.2(10) 2_765 . ?
C6 C8 Br1 118.1(8) 2_765 . ?
C7 C8 Br1 120.7(8) . . ?
N1 C9 C10 121.6(14) . . ?
N1 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C11 117.0(14) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
C12 C11 C10 121.4(15) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.6(12) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
N2 C13 N1 117.9(12) . . ?
N2 C13 C12 123.3(11) . . ?
N1 C13 C12 118.8(12) . . ?

_refine_diff_density_max         2.098
_refine_diff_density_min         -1.795
_refine_diff_density_rms         0.264

####################################################################### 
# 
# 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 1841622'
loop_
_audit_author_name
_audit_author_address
'Rajat Saha'
;KAZI NAZRUL UNIVERSITY
India
;
_audit_update_record             
;
2018-05-06 deposited with the CCDC.	2020-09-29 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         'C8H2Br4O4, C8Br4O4, 2(C6H7N2O), 2(H2O)'
_chemical_formula_sum            'C28 H20 Br8 N4 O12'
_chemical_formula_weight         1243.76

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                   9.0292(10)
_cell_length_b                   9.4163(11)
_cell_length_c                   12.2764(14)
_cell_angle_alpha                108.671(2)
_cell_angle_beta                 108.502(2)
_cell_angle_gamma                93.051(2)
_cell_volume                     923.69(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    10382
_cell_measurement_theta_min      1.872
_cell_measurement_theta_max      25.495

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.236
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   0.209
_exptl_transmission_factor_max   0.736
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    8.748
_shelx_estimated_absorpt_T_min   0.193
_shelx_estimated_absorpt_T_max   0.302
_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      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'ω scan'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10382
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3443
_reflns_number_gt                3062
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0241P)²+0.7208P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3443
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.88569(4) 0.60765(5) 0.62422(4) 0.05375(14) Uani 1 1 d . . . . .
Br2 Br 0.64194(5) 0.86253(4) 0.64723(4) 0.05414(14) Uani 1 1 d . . . . .
Br3 Br 0.86917(4) 0.44669(5) 0.07521(3) 0.04144(12) Uani 1 1 d . . . . .
Br4 Br 0.72590(4) 0.61937(4) -0.12697(3) 0.03867(12) Uani 1 1 d . . . . .
O1 O 1.0390(3) 0.9050(3) 0.1172(2) 0.0435(6) Uani 1 1 d . . . . .
O2 O 0.7391(4) 0.2145(4) 0.5649(3) 0.0595(8) Uani 1 1 d . . . . .
O3 O 0.7667(3) 0.2434(3) 0.4014(2) 0.0453(6) Uani 1 1 d . . . . .
H3O H 0.7390 0.2989 0.3616 0.088(19) Uiso 1 1 calc R . . . .
O4 O 0.6875(3) 0.3999(3) 0.2731(2) 0.0428(6) Uani 1 1 d . . . . .
O5 O 0.5893(3) 0.1877(3) 0.1054(2) 0.0419(6) Uani 1 1 d . . . . .
O1W O 0.3118(3) 0.7873(3) 0.2273(2) 0.0458(6) Uani 1 1 d . . . . .
H1W1 H 0.2991 0.7838 0.2943 0.055 Uiso 1 1 d R U . . .
H2W1 H 0.2248 0.8293 0.1949 0.055 Uiso 1 1 d R U . . .
N1 N 0.6156(4) 0.8423(4) 0.2490(3) 0.0442(7) Uani 1 1 d . . . . .
N2 N 0.8463(5) 1.0388(4) 0.0681(4) 0.0510(9) Uani 1 1 d . . . . .
C1 C 0.7023(6) 0.8016(6) 0.3407(4) 0.0655(13) Uani 1 1 d . . . . .
H1 H 0.6541 0.7662 0.3859 0.079 Uiso 1 1 calc R U . . .
C2 C 0.8635(6) 0.8123(7) 0.3683(5) 0.0727(15) Uani 1 1 d . . . . .
H2 H 0.9254 0.7850 0.4325 0.087 Uiso 1 1 calc R U . . .
C3 C 0.9315(5) 0.8640(5) 0.2994(4) 0.0537(11) Uani 1 1 d . . . . .
H3 H 1.0403 0.8712 0.3171 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8406(4) 0.9051(4) 0.2045(3) 0.0339(7) Uani 1 1 d . . . . .
C5 C 0.6787(4) 0.8934(4) 0.1809(3) 0.0362(8) Uani 1 1 d . . . . .
H5 H 0.6143 0.9211 0.1178 0.043 Uiso 1 1 calc R U . . .
C6 C 0.9171(4) 0.9513(4) 0.1262(3) 0.0351(7) Uani 1 1 d . . . . .
C7 C 0.7112(4) 0.2748(4) 0.4885(3) 0.0364(8) Uani 1 1 d . . . . .
C8 C 0.6016(4) 0.3926(4) 0.4936(3) 0.0306(7) Uani 1 1 d . . . . .
C9 C 0.6629(4) 0.5468(4) 0.5534(3) 0.0325(7) Uani 1 1 d . . . . .
C10 C 0.5619(4) 0.6532(4) 0.5609(3) 0.0304(7) Uani 1 1 d . . . . .
C11 C 0.6164(4) 0.3261(4) 0.1595(3) 0.0312(7) Uani 1 1 d . . . . .
C12 C 0.5577(4) 0.4227(4) 0.0807(3) 0.0285(7) Uani 1 1 d . . . . .
C13 C 0.6562(4) 0.4755(4) 0.0295(3) 0.0281(7) Uani 1 1 d . . . . .
C14 C 0.5983(4) 0.5517(4) -0.0517(3) 0.0279(7) Uani 1 1 d . . . . .
H1N H 0.515(6) 0.831(5) 0.236(4) 0.061(14) Uiso 1 1 d . . . . .
H21 H 0.768(6) 1.074(5) 0.080(4) 0.059(13) Uiso 1 1 d . . . . .
H22 H 0.883(6) 1.055(5) 0.020(4) 0.055(13) Uiso 1 1 d . . . . .


_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 C9 1.892(3) . ?
Br2 C10 1.885(3) . ?
Br3 C13 1.885(3) . ?
Br4 C14 1.887(3) . ?
O1 C6 1.229(4) . ?
O2 C7 1.213(4) . ?
O3 C7 1.280(4) . ?
O3 H3O 0.8200 . ?
O4 C11 1.267(4) . ?
O5 C11 1.228(4) . ?
O1W H1W1 0.8765 . ?
O1W H2W1 0.9313 . ?
N1 C1 1.332(5) . ?
N1 C5 1.337(5) . ?
N1 H1N 0.87(5) . ?
N2 C6 1.319(5) . ?
N2 H21 0.83(5) . ?
N2 H22 0.81(5) . ?
C1 C2 1.376(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 C6 1.498(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.524(4) . ?
C8 C9 1.388(5) . ?
C8 C10 1.391(5) 2_666 ?
C9 C10 1.391(5) . ?
C10 C8 1.391(5) 2_666 ?
C11 C12 1.527(4) . ?
C12 C13 1.393(4) . ?
C12 C14 1.394(4) 2_665 ?
C13 C14 1.396(4) . ?
C14 C12 1.394(4) 2_665 ?

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 O3 H3O 109.5 . . ?
H1W1 O1W H2W1 101.8 . . ?
C1 N1 C5 122.6(4) . . ?
C1 N1 H1N 115(3) . . ?
C5 N1 H1N 123(3) . . ?
C6 N2 H21 122(3) . . ?
C6 N2 H22 116(3) . . ?
H21 N2 H22 122(4) . . ?
N1 C1 C2 119.7(4) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 C6 119.4(3) . . ?
C5 C4 C6 122.5(3) . . ?
N1 C5 C4 119.8(3) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O1 C6 N2 123.3(4) . . ?
O1 C6 C4 119.5(3) . . ?
N2 C6 C4 117.1(3) . . ?
O2 C7 O3 123.6(3) . . ?
O2 C7 C8 119.0(3) . . ?
O3 C7 C8 117.3(3) . . ?
C9 C8 C10 118.9(3) . 2_666 ?
C9 C8 C7 120.8(3) . . ?
C10 C8 C7 120.3(3) 2_666 . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 Br1 118.4(2) . . ?
C10 C9 Br1 121.1(3) . . ?
C9 C10 C8 120.7(3) . 2_666 ?
C9 C10 Br2 121.2(3) . . ?
C8 C10 Br2 118.1(2) 2_666 . ?
O5 C11 O4 128.2(3) . . ?
O5 C11 C12 116.5(3) . . ?
O4 C11 C12 115.3(3) . . ?
C13 C12 C14 119.6(3) . 2_665 ?
C13 C12 C11 120.0(3) . . ?
C14 C12 C11 120.2(3) 2_665 . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 Br3 118.8(2) . . ?
C14 C13 Br3 121.0(2) . . ?
C12 C14 C13 120.2(3) 2_665 . ?
C12 C14 Br4 118.3(2) 2_665 . ?
C13 C14 Br4 121.5(2) . . ?

_refine_diff_density_max         0.886
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1841623'
loop_
_audit_author_name
_audit_author_address
'Rajat Saha'
;KAZI NAZRUL UNIVERSITY
India
;
_audit_update_record             
;
2018-05-06 deposited with the CCDC.	2020-09-29 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         '4(C8 H Br4 O4), 4(C5 H7 N2), 5(H2 O)'
_chemical_formula_sum            'C52 H42 Br16 N8 O21'
_chemical_formula_weight         2393.49

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           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4075(4)
_cell_length_b                   18.8184(5)
_cell_length_c                   21.0347(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3723.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3471
_cell_measurement_theta_min      2.607
_cell_measurement_theta_max      25.559

_exptl_crystal_description       Whisker
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_F_000             2276
_exptl_transmission_factor_min   0.298
_exptl_transmission_factor_max   0.420
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    8.672
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_T_max  0.420
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54589
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.607
_diffrn_reflns_theta_max         25.559
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3471
_reflns_number_gt                2562
_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 SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP 3 FOR WINDOWS'
_computing_publication_material  'PLATON99 (SPEK, 1999)'
_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)+(0.0354P)²+7.3693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3471
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
O2W O 0.064(2) 0.0458(11) 0.5934(14) 0.129(11) Uani 0.25 1 d . . P . .
H1W2 H 0.1446 0.0383 0.6101 0.155 Uiso 0.25 1 d R U P . .
H2W2 H 0.0192 0.0748 0.6171 0.155 Uiso 0.25 1 d R U P . .
O1W O 0.0969(6) 0.0665(3) 0.4918(4) 0.150(3) Uani 1 1 d . . . . .
H1W1 H 0.1709 0.0744 0.4697 0.180 Uiso 1 1 d R U . . .
H2W1 H 0.0299 0.0559 0.4664 0.180 Uiso 1 1 d R U . . .
C1 C 0.3377(4) 0.0300(2) 0.3516(2) 0.0248(9) Uani 1 1 d . . . . .
C2 C 0.4397(4) -0.0100(2) 0.3833(2) 0.0244(9) Uani 1 1 d . . . . .
C3 C 0.4340(4) -0.0827(2) 0.3825(2) 0.0219(9) Uani 1 1 d . . . . .
C4 C 0.3293(4) -0.1189(2) 0.3487(2) 0.0222(9) Uani 1 1 d . . . . .
C5 C 0.2283(4) -0.0786(2) 0.3162(2) 0.0243(9) Uani 1 1 d . . . . .
C6 C 0.2338(4) -0.0049(2) 0.3172(2) 0.0265(10) Uani 1 1 d . . . . .
C7 C 0.3431(5) 0.1108(2) 0.3504(2) 0.0272(10) Uani 1 1 d . . . . .
C8 C 0.3254(4) -0.1997(2) 0.3453(2) 0.0247(10) Uani 1 1 d . . . . .
O1 O 0.4140(3) 0.14234(16) 0.31222(16) 0.0373(8) Uani 1 1 d . . . . .
O2 O 0.2632(4) 0.13867(15) 0.39442(15) 0.0387(8) Uani 1 1 d . . . . .
H1O2 H 0.2684 0.1837 0.3920 0.046 Uiso 1 1 d R U . . .
O3 O 0.2610(4) -0.22925(15) 0.39126(15) 0.0358(8) Uani 1 1 d . . . . .
O4 O 0.3812(3) -0.22880(15) 0.29961(16) 0.0336(7) Uani 1 1 d . . . . .
Br1 Br 0.58789(5) 0.03931(2) 0.42557(3) 0.04276(16) Uani 1 1 d . . . . .
Br2 Br 0.10135(5) 0.05006(2) 0.26993(3) 0.04325(16) Uani 1 1 d . . . . .
Br3 Br 0.57436(5) -0.13820(2) 0.42445(3) 0.04092(16) Uani 1 1 d . . . . .
Br4 Br 0.08904(5) -0.12811(3) 0.26817(3) 0.04131(16) Uani 1 1 d . . . . .
C11 C 0.6233(6) 0.2492(3) 0.3807(3) 0.0505(14) Uani 1 1 d . . . . .
H11 H 0.5400 0.2758 0.3791 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6732(5) 0.2278(3) 0.4373(2) 0.0401(12) Uani 1 1 d . . . . .
H12 H 0.6255 0.2400 0.4744 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8103(7) 0.1950(3) 0.3268(3) 0.0529(15) Uani 1 1 d . . . . .
H13 H 0.8558 0.1846 0.2887 0.063 Uiso 1 1 calc R U . . .
C14 C 0.8661(6) 0.1711(3) 0.3826(3) 0.0439(13) Uani 1 1 d . . . . .
H14 H 0.9493 0.1444 0.3824 0.053 Uiso 1 1 calc R U . . .
C15 C 0.7982(5) 0.1869(2) 0.4400(2) 0.0345(11) Uani 1 1 d . . . . .
N1 N 0.6908(6) 0.2331(3) 0.3265(2) 0.0563(14) Uani 1 1 d . . . . .
N2 N 0.8496(5) 0.1631(2) 0.4953(2) 0.0525(12) Uani 1 1 d . . . . .
H1N2 H 0.9255 0.1377 0.4959 0.063 Uiso 1 1 calc R U . . .
H2N2 H 0.8066 0.1733 0.5302 0.063 Uiso 1 1 calc R U . . .
H1N1 H 0.649(6) 0.246(3) 0.288(3) 0.063 Uiso 1 1 d . 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
O2W H1W2 0.8500 . ?
O2W H2W2 0.8501 . ?
O1W H1W1 0.8500 . ?
O1W H2W1 0.8500 . ?
C1 C6 1.382(6) . ?
C1 C2 1.391(6) . ?
C1 C7 1.521(5) . ?
C2 C3 1.370(6) . ?
C2 Br1 1.896(4) . ?
C3 C4 1.392(5) . ?
C3 Br3 1.900(4) . ?
C4 C5 1.395(6) . ?
C4 C8 1.523(5) . ?
C5 C6 1.387(6) . ?
C5 Br4 1.899(4) . ?
C6 Br2 1.900(4) . ?
C7 O1 1.201(5) . ?
C7 O2 1.303(5) . ?
C8 O4 1.224(5) . ?
C8 O3 1.270(5) . ?
O2 H1O2 0.8500 . ?
C11 C12 1.340(8) . ?
C11 N1 1.341(8) . ?
C11 H11 0.9300 . ?
C12 C15 1.408(7) . ?
C12 H12 0.9300 . ?
C13 N1 1.334(8) . ?
C13 C14 1.361(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(7) . ?
C14 H14 0.9300 . ?
C15 N2 1.336(6) . ?
N1 H1N1 0.93(6) . ?
N2 H1N2 0.8600 . ?
N2 H2N2 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
H1W2 O2W H2W2 107.7 . . ?
H1W1 O1W H2W1 107.7 . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 C7 119.4(4) . . ?
C2 C1 C7 121.7(4) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 Br1 121.6(3) . . ?
C1 C2 Br1 117.9(3) . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 Br3 121.1(3) . . ?
C4 C3 Br3 117.4(3) . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 C8 121.9(4) . . ?
C5 C4 C8 120.2(4) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 Br4 121.6(3) . . ?
C4 C5 Br4 117.7(3) . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 Br2 118.6(3) . . ?
C5 C6 Br2 120.8(3) . . ?
O1 C7 O2 126.6(4) . . ?
O1 C7 C1 121.6(4) . . ?
O2 C7 C1 111.8(4) . . ?
O4 C8 O3 127.3(4) . . ?
O4 C8 C4 118.3(4) . . ?
O3 C8 C4 114.4(4) . . ?
C7 O2 H1O2 109.0 . . ?
C12 C11 N1 121.4(6) . . ?
C12 C11 H11 119.3 . . ?
N1 C11 H11 119.3 . . ?
C11 C12 C15 119.6(5) . . ?
C11 C12 H12 120.2 . . ?
C15 C12 H12 120.2 . . ?
N1 C13 C14 120.5(6) . . ?
N1 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N2 C15 C14 121.1(5) . . ?
N2 C15 C12 121.4(5) . . ?
C14 C15 C12 117.6(5) . . ?
C13 N1 C11 121.0(5) . . ?
C13 N1 H1N1 120(4) . . ?
C11 N1 H1N1 118(4) . . ?
C15 N2 H1N2 120.0 . . ?
C15 N2 H2N2 120.0 . . ?
H1N2 N2 H2N2 120.0 . . ?

_refine_diff_density_max         0.978
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.132

