# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_pa107a
_database_code_depnum_ccdc_archive 'CCDC 2124741'
loop_
_audit_author_name
_audit_author_address
'Rahman Bikas'
;Imam khomeini International University, Qazvin
Iran
;
_audit_update_record             
;
2021-11-27 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Br N3 O5 W'
_chemical_formula_sum            'C15 H14 Br N3 O5 W'
_chemical_formula_weight         580.05

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'
W W -0.8490 6.8722 '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                   7.663(2)
_cell_length_b                   10.481(3)
_cell_length_c                   10.845(3)
_cell_angle_alpha                95.43(3)
_cell_angle_beta                 93.93(3)
_cell_angle_gamma                104.74(4)
_cell_volume                     834.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7980
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.308
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    9.345
_shelx_estimated_absorpt_T_min   0.172
_shelx_estimated_absorpt_T_max   0.244
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_T_max  0.264
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
	model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_measurement_device_type  
;
Kuma KM4 kappa-geometry diffractometer with a CCD detector
;
_diffrn_measurement_method       w/
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7989
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3275
_reflns_number_gt                3105
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0893P)²+0.4292P]
 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3275
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.089
_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
W W 0.63075(3) 0.78629(2) 0.31500(2) 0.02058(15) Uani 1 1 d . . . . .
O3 O 0.4287(7) 0.8203(5) 0.2757(5) 0.0298(11) Uani 1 1 d . . . . .
O4 O 0.6431(7) 0.6594(5) 0.2036(4) 0.0267(10) Uani 1 1 d . . . . .
Br Br 0.40980(10) 0.79871(7) 0.98618(6) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.5592(7) 0.6899(5) 0.4546(4) 0.0283(11) Uani 1 1 d . . . . .
C1 C 0.5859(9) 0.8494(6) 0.6350(6) 0.0218(13) Uani 1 1 d . . . . .
C2 C 0.5172(9) 0.7226(7) 0.5709(6) 0.0230(14) Uani 1 1 d . . . . .
C3 C 0.4055(10) 0.6220(7) 0.6264(6) 0.0271(15) Uani 1 1 d . . . . .
H3 H 0.3545 0.5371 0.5808 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3688(9) 0.6468(7) 0.7501(6) 0.0246(14) Uani 1 1 d . . . . .
H4 H 0.2926 0.5789 0.7889 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4441(9) 0.7705(7) 0.8149(6) 0.0240(14) Uani 1 1 d . . . . .
C6 C 0.5515(9) 0.8729(7) 0.7613(6) 0.0231(14) Uani 1 1 d . . . . .
H6 H 0.6015 0.9574 0.8077 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7037(9) 0.9595(6) 0.5834(6) 0.0213(13) Uani 1 1 d . . . . .
H7 H 0.7592 1.0386 0.6371 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7363(7) 0.9544(5) 0.4672(5) 0.0200(11) Uani 1 1 d . . . . .
N2 N 0.8529(8) 1.0683(5) 0.4331(5) 0.0227(12) Uani 1 1 d . . . . .
C8 C 0.8668(8) 1.0533(6) 0.3113(6) 0.0213(13) Uani 1 1 d . . . . .
O1 O 0.7855(7) 0.9379(4) 0.2427(4) 0.0255(10) Uani 1 1 d . . . . .
C9 C 0.9739(9) 1.1567(7) 0.2483(6) 0.0252(14) Uani 1 1 d . . . . .
C10 C 1.0575(9) 1.2857(6) 0.3086(6) 0.0235(14) Uani 1 1 d . . . . .
H10 H 1.0412 1.3072 0.3933 0.028 Uiso 1 1 calc R U . . .
C11 C 1.1639(10) 1.3818(6) 0.2447(7) 0.0258(15) Uani 1 1 d . . . . .
H11 H 1.2187 1.4685 0.2857 0.031 Uiso 1 1 calc R U . . .
C12 C 1.1899(9) 1.3500(7) 0.1192(6) 0.0234(14) Uani 1 1 d . . . . .
C13 C 1.1026(10) 1.2224(7) 0.0581(7) 0.0270(15) Uani 1 1 d . . . . .
H13 H 1.1165 1.2012 -0.0272 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9978(10) 1.1291(7) 0.1213(6) 0.0266(14) Uani 1 1 d . . . . .
H14 H 0.9396 1.0437 0.0788 0.032 Uiso 1 1 calc R U . . .
N3 N 1.2952(9) 1.4434(6) 0.0561(6) 0.0324(14) Uani 1 1 d . . . . .
H31 H 1.3443 1.4167 -0.0129 0.050 Uiso 1 1 d R U . . .
H32 H 1.3699 1.5161 0.1030 0.05(3) Uiso 1 1 d R . . . .
O1M O 0.9147(7) 0.7685(5) 0.3847(5) 0.0265(11) Uani 1 1 d . . . . .
H1M H 0.9762 0.8172 0.4471 0.02(2) Uiso 1 1 d R . . . .
C1M C 1.0075(11) 0.6771(8) 0.3321(9) 0.040(2) Uani 1 1 d . . . . .
H1M1 H 0.9359 0.5860 0.3361 0.060 Uiso 1 1 calc R U . . .
H1M2 H 1.1262 0.6918 0.3791 0.060 Uiso 1 1 calc R U . . .
H1M3 H 1.0241 0.6910 0.2451 0.060 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
W O3 1.710(6) . ?
W O4 1.736(5) . ?
W O2 1.932(5) . ?
W O1 1.987(5) . ?
W N1 2.242(5) . ?
W O1M 2.313(5) . ?
Br C5 1.900(7) . ?
O2 C2 1.357(8) . ?
C1 C2 1.395(9) . ?
C1 C6 1.423(9) . ?
C1 C7 1.456(9) . ?
C2 C3 1.392(10) . ?
C3 C4 1.404(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(10) . ?
C6 H6 0.9500 . ?
C7 N1 1.301(9) . ?
C7 H7 0.9500 . ?
N1 N2 1.395(8) . ?
N2 C8 1.329(9) . ?
C8 O1 1.337(8) . ?
C8 C9 1.443(9) . ?
C9 C14 1.414(9) . ?
C9 C10 1.414(9) . ?
C10 C11 1.397(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(9) . ?
C11 H11 0.9500 . ?
C12 N3 1.370(9) . ?
C12 C13 1.411(9) . ?
C13 C14 1.369(10) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
N3 H31 0.9124 . ?
N3 H32 0.9125 . ?
O1M C1M 1.431(8) . ?
O1M H1M 0.8423 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?

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
O3 W O4 105.2(2) . . ?
O3 W O2 97.9(2) . . ?
O4 W O2 101.7(2) . . ?
O3 W O1 96.3(2) . . ?
O4 W O1 98.4(2) . . ?
O2 W O1 151.3(2) . . ?
O3 W N1 97.4(2) . . ?
O4 W N1 156.4(2) . . ?
O2 W N1 81.9(2) . . ?
O1 W N1 71.70(19) . . ?
O3 W O1M 172.08(19) . . ?
O4 W O1M 82.4(2) . . ?
O2 W O1M 82.6(2) . . ?
O1 W O1M 80.0(2) . . ?
N1 W O1M 74.84(19) . . ?
C2 O2 W 135.1(4) . . ?
C2 C1 C6 119.3(6) . . ?
C2 C1 C7 123.8(6) . . ?
C6 C1 C7 116.7(6) . . ?
O2 C2 C3 116.9(6) . . ?
O2 C2 C1 122.4(6) . . ?
C3 C2 C1 120.6(6) . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.4(6) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.2(6) . . ?
C4 C5 Br 119.0(5) . . ?
C6 C5 Br 118.7(5) . . ?
C5 C6 C1 118.7(6) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C1 123.0(6) . . ?
N1 C7 H7 118.5 . . ?
C1 C7 H7 118.5 . . ?
C7 N1 N2 115.7(5) . . ?
C7 N1 W 128.4(4) . . ?
N2 N1 W 115.8(4) . . ?
C8 N2 N1 109.8(5) . . ?
N2 C8 O1 120.4(6) . . ?
N2 C8 C9 122.4(6) . . ?
O1 C8 C9 117.1(6) . . ?
C8 O1 W 122.1(4) . . ?
C14 C9 C10 118.2(6) . . ?
C14 C9 C8 119.3(6) . . ?
C10 C9 C8 122.6(6) . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.9(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
N3 C12 C11 120.3(6) . . ?
N3 C12 C13 120.2(6) . . ?
C11 C12 C13 119.5(6) . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 121.6(6) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C12 N3 H31 119.5 . . ?
C12 N3 H32 116.7 . . ?
H31 N3 H32 113.1 . . ?
C1M O1M W 126.5(5) . . ?
C1M O1M H1M 111.6 . . ?
W O1M H1M 122.0 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?

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
W O2 C2 C3 155.1(5) . . . . ?
W O2 C2 C1 -26.9(11) . . . . ?
C6 C1 C2 O2 -173.5(7) . . . . ?
C7 C1 C2 O2 1.9(11) . . . . ?
C6 C1 C2 C3 4.4(10) . . . . ?
C7 C1 C2 C3 179.9(7) . . . . ?
O2 C2 C3 C4 175.0(6) . . . . ?
C1 C2 C3 C4 -3.0(11) . . . . ?
C2 C3 C4 C5 -0.1(11) . . . . ?
C3 C4 C5 C6 1.7(11) . . . . ?
C3 C4 C5 Br -174.9(5) . . . . ?
C4 C5 C6 C1 -0.3(11) . . . . ?
Br C5 C6 C1 176.4(5) . . . . ?
C2 C1 C6 C5 -2.8(10) . . . . ?
C7 C1 C6 C5 -178.5(6) . . . . ?
C2 C1 C7 N1 9.3(11) . . . . ?
C6 C1 C7 N1 -175.2(6) . . . . ?
C1 C7 N1 N2 -179.7(6) . . . . ?
C1 C7 N1 W -0.1(9) . . . . ?
C7 N1 N2 C8 -176.5(6) . . . . ?
W N1 N2 C8 3.9(6) . . . . ?
N1 N2 C8 O1 -4.5(8) . . . . ?
N1 N2 C8 C9 178.0(6) . . . . ?
N2 C8 O1 W 3.1(8) . . . . ?
C9 C8 O1 W -179.2(4) . . . . ?
N2 C8 C9 C14 173.5(6) . . . . ?
O1 C8 C9 C14 -4.2(10) . . . . ?
N2 C8 C9 C10 -6.3(11) . . . . ?
O1 C8 C9 C10 176.1(6) . . . . ?
C14 C9 C10 C11 -1.4(11) . . . . ?
C8 C9 C10 C11 178.4(7) . . . . ?
C9 C10 C11 C12 -0.6(11) . . . . ?
C10 C11 C12 N3 -179.5(7) . . . . ?
C10 C11 C12 C13 2.3(11) . . . . ?
N3 C12 C13 C14 179.9(7) . . . . ?
C11 C12 C13 C14 -1.9(11) . . . . ?
C12 C13 C14 C9 -0.1(11) . . . . ?
C10 C9 C14 C13 1.8(11) . . . . ?
C8 C9 C14 C13 -178.0(7) . . . . ?

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
N3 H31 O4 0.91 2.16 3.031(8) 158.6 2_775
N3 H32 O4 0.91 2.37 3.233(8) 158.3 1_665
O1M H1M N2 0.84 1.88 2.708(8) 169.5 2_776

_refine_diff_density_max         1.362
_refine_diff_density_min         -1.723
_refine_diff_density_rms         0.270

_shelxl_version_number           2013-2

