# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1939459'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;School of Chemistry The University of Melbourne
Australia
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Br4 Na2 O8'
_chemical_formula_weight         597.76
_chemical_oxdiff_usercomment     'KME (Kamran)'

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'
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'

_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+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   12.3021(4)
_cell_length_b                   12.3021(4)
_cell_length_c                   42.415(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6419.1(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    2780
_cell_measurement_theta_min      3.7040
_cell_measurement_theta_max      34.5800

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.474
_exptl_crystal_F_000             4512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.154
_exptl_absorpt_coefficient_mu    10.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.070
_exptl_absorpt_correction_T_max  0.361
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.688
_oxdiff_exptl_absorpt_empirical_full_max 1.997
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            7271
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.449
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2682
_reflns_number_gt                2315
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     204
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      0.984
_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
C1 C 0.000000 0.500000 0.5132(6) 0.015(2) Uani 1 2 d S TU P . .
C2 C 0.0957(10) 0.5068(6) 0.4957(3) 0.0147(19) Uani 1 1 d . U . . .
C3 C 0.0986(10) 0.5065(6) 0.4626(4) 0.0134(18) Uani 1 1 d . U . . .
C4 C 0.000000 0.500000 0.4468(5) 0.012(2) Uani 1 2 d S TU P . .
C5 C 0.000000 0.500000 0.5487(6) 0.0128(19) Uani 1 2 d S TU P . .
C6 C 0.000000 0.500000 0.4102(6) 0.0146(17) Uani 1 2 d S TU P . .
C7 C 0.500000 0.500000 0.5182(5) 0.013(2) Uani 1 2 d S TU P . .
C8 C 0.4976(5) 0.5952(10) 0.5000(4) 0.0138(19) Uani 1 1 d . U . . .
C9 C 0.4967(5) 0.5988(10) 0.4673(3) 0.0123(17) Uani 1 1 d . U . . .
C10 C 0.500000 0.500000 0.4514(5) 0.011(2) Uani 1 2 d S TU P . .
C11 C 0.500000 0.500000 0.5540(6) 0.0158(17) Uani 1 2 d S TU P . .
C12 C 0.500000 0.500000 0.4145(7) 0.0124(18) Uani 1 2 d S TU P . .
O1 O -0.0401(4) 0.5822(5) 0.56193(15) 0.0194(12) Uani 1 1 d . U . . .
O2 O 0.0022(4) 0.4083(7) 0.3971(3) 0.0171(17) Uani 1 1 d . U . . .
O3 O 0.0011(4) 0.1936(3) 0.3559(4) 0.0215(9) Uani 1 1 d . U . . .
H3A H 0.003174 0.151239 0.336567 0.026 Uiso 1 1 calc R U . . .
H3B H -0.000067 0.148047 0.374520 0.026 Uiso 1 1 calc R U . . .
O4 O 0.2327(7) 0.2397(5) 0.3198(2) 0.0252(16) Uani 1 1 d . U . . .
H4A H 0.265951 0.285318 0.303876 0.030 Uiso 1 1 calc R U . . .
H4B H 0.188313 0.184570 0.309709 0.030 Uiso 1 1 calc R U . . .
O5 O 0.5912(7) 0.4983(5) 0.5674(3) 0.0193(17) Uani 1 1 d . U . . .
O6 O 0.4178(5) 0.4609(4) 0.40118(14) 0.0182(12) Uani 1 1 d . U . . .
O7 O 0.7684(5) 0.2689(7) 0.6436(2) 0.0223(13) Uani 1 1 d . U . . .
H7A H 0.724441 0.236681 0.660147 0.027 Uiso 1 1 calc R U . . .
H7B H 0.824593 0.313739 0.653005 0.027 Uiso 1 1 calc R U . . .
O8 O 0.5024(3) 0.2488(4) 0.6077(4) 0.0174(12) Uani 1 1 d . U . . .
H8A H 0.503872 0.204592 0.626663 0.021 Uiso 1 1 calc R U . . .
H8B H 0.501226 0.201635 0.589417 0.021 Uiso 1 1 calc R U . . .
Br1 Br 0.22861(10) 0.51858(11) 0.51900(4) 0.0193(4) Uani 1 1 d . U . . .
Br2 Br 0.22881(11) 0.51030(15) 0.44040(3) 0.0190(4) Uani 1 1 d . U . . .
Br3 Br 0.48616(12) 0.72881(10) 0.44442(3) 0.0188(4) Uani 1 1 d . U . . .
Br4 Br 0.49412(18) 0.72932(11) 0.52312(3) 0.0184(4) Uani 1 1 d . U . . .
Na1 Na 0.65669(19) 0.3726(2) 0.60599(18) 0.0198(6) Uani 1 1 d . U . . .
Na2 Na 0.1278(2) 0.3466(2) 0.35784(18) 0.0196(6) Uani 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
C1 C2 1.397(18) 10_454 ?
C1 C2 1.397(18) . ?
C1 C5 1.50(3) . ?
C2 C3 1.401(16) . ?
C2 Br1 1.917(13) . ?
C3 C4 1.388(17) . ?
C3 Br2 1.859(13) . ?
C4 C6 1.55(3) . ?
C5 O1 1.257(14) . ?
C5 O1 1.257(14) 10_454 ?
C6 O2 1.259(15) 10_454 ?
C6 O2 1.259(15) . ?
C7 C8 1.403(19) 10_554 ?
C7 C8 1.403(19) . ?
C7 C11 1.52(3) . ?
C8 C9 1.389(16) . ?
C8 Br4 1.919(13) . ?
C9 C10 1.390(17) . ?
C9 Br3 1.876(13) . ?
C10 C12 1.57(3) . ?
C11 O5 1.256(15) 10_554 ?
C11 O5 1.256(15) . ?
C12 O6 1.254(14) 10_554 ?
C12 O6 1.254(14) . ?
O2 Na2 2.394(10) . ?
O2 Na1 2.493(10) 4_464 ?
O3 Na1 2.428(5) 4_464 ?
O3 Na2 2.445(5) . ?
O3 H3A 0.9700 . ?
O3 H3B 0.9700 . ?
O4 Na2 2.449(9) . ?
O4 Na1 2.522(10) 16_444 ?
O4 H4A 0.9700 . ?
O4 H4B 0.9700 . ?
O5 Na1 2.392(10) . ?
O5 Na2 2.464(11) 3_655 ?
O7 Na1 2.462(9) . ?
O7 Na2 2.499(9) 8 ?
O7 H7A 0.9700 . ?
O7 H7B 0.9700 . ?
O8 Na1 2.435(5) . ?
O8 Na2 2.445(5) 12_454 ?
O8 H8A 0.9700 . ?
O8 H8B 0.9700 . ?
Na1 Na2 3.140(3) 3_655 ?
Na1 Na2 3.813(3) 8 ?
Na1 Na2 3.815(3) 12_454 ?

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 C1 C2 115(2) 10_454 . ?
C2 C1 C5 122.3(10) 10_454 . ?
C2 C1 C5 122.3(10) . . ?
C1 C2 C3 123.7(15) . . ?
C1 C2 Br1 116.6(12) . . ?
C3 C2 Br1 119.7(11) . . ?
C4 C3 C2 117.4(15) . . ?
C4 C3 Br2 120.6(12) . . ?
C2 C3 Br2 121.9(12) . . ?
C3 C4 C3 122(2) 10_454 . ?
C3 C4 C6 118.8(10) 10_454 . ?
C3 C4 C6 118.8(10) . . ?
O1 C5 O1 127(2) . 10_454 ?
O1 C5 C1 116.5(11) . . ?
O1 C5 C1 116.5(11) 10_454 . ?
O2 C6 O2 127(2) 10_454 . ?
O2 C6 C4 116.3(12) 10_454 . ?
O2 C6 C4 116.3(12) . . ?
C8 C7 C8 113(2) 10_554 . ?
C8 C7 C11 123.4(10) 10_554 . ?
C8 C7 C11 123.4(10) . . ?
C9 C8 C7 125.2(15) . . ?
C9 C8 Br4 118.8(12) . . ?
C7 C8 Br4 116.0(12) . . ?
C8 C9 C10 117.2(15) . . ?
C8 C9 Br3 123.1(12) . . ?
C10 C9 Br3 119.8(12) . . ?
C9 C10 C9 122(2) . 10_554 ?
C9 C10 C12 119.0(10) . . ?
C9 C10 C12 119.0(10) 10_554 . ?
O5 C11 O5 127(2) 10_554 . ?
O5 C11 C7 116.7(12) 10_554 . ?
O5 C11 C7 116.7(12) . . ?
O6 C12 O6 126(2) 10_554 . ?
O6 C12 C10 116.8(12) 10_554 . ?
O6 C12 C10 116.8(12) . . ?
C6 O2 Na2 127.2(8) . . ?
C6 O2 Na1 125.7(8) . 4_464 ?
Na2 O2 Na1 79.9(4) . 4_464 ?
Na1 O3 Na2 80.24(14) 4_464 . ?
Na1 O3 H3A 115.2 4_464 . ?
Na2 O3 H3A 115.2 . . ?
Na1 O3 H3B 115.2 4_464 . ?
Na2 O3 H3B 115.2 . . ?
H3A O3 H3B 112.3 . . ?
Na2 O4 Na1 100.2(4) . 16_444 ?
Na2 O4 H4A 111.7 . . ?
Na1 O4 H4A 111.7 16_444 . ?
Na2 O4 H4B 111.7 . . ?
Na1 O4 H4B 111.7 16_444 . ?
H4A O4 H4B 109.5 . . ?
C11 O5 Na1 128.3(8) . . ?
C11 O5 Na2 125.4(8) . 3_655 ?
Na1 O5 Na2 80.6(4) . 3_655 ?
Na1 O7 Na2 100.5(4) . 8 ?
Na1 O7 H7A 111.7 . . ?
Na2 O7 H7A 111.7 8 . ?
Na1 O7 H7B 111.7 . . ?
Na2 O7 H7B 111.7 8 . ?
H7A O7 H7B 109.5 . . ?
Na1 O8 Na2 102.87(18) . 12_454 ?
Na1 O8 H8A 111.2 . . ?
Na2 O8 H8A 111.2 12_454 . ?
Na1 O8 H8B 111.2 . . ?
Na2 O8 H8B 111.2 12_454 . ?
H8A O8 H8B 109.1 . . ?
O5 Na1 O3 80.4(4) . 3_655 ?
O5 Na1 O8 99.4(4) . . ?
O3 Na1 O8 177.5(5) 3_655 . ?
O5 Na1 O7 165.2(3) . . ?
O3 Na1 O7 85.2(4) 3_655 . ?
O8 Na1 O7 95.2(4) . . ?
O5 Na1 O2 87.58(17) . 3_655 ?
O3 Na1 O2 80.1(4) 3_655 3_655 ?
O8 Na1 O2 97.4(4) . 3_655 ?
O7 Na1 O2 93.3(4) . 3_655 ?
O5 Na1 O4 99.3(4) . 8 ?
O3 Na1 O4 97.8(3) 3_655 8 ?
O8 Na1 O4 84.7(3) . 8 ?
O7 Na1 O4 79.32(19) . 8 ?
O2 Na1 O4 172.5(4) 3_655 8 ?
O5 Na1 Na2 50.7(2) . 3_655 ?
O3 Na1 Na2 50.13(13) 3_655 3_655 ?
O8 Na1 Na2 127.90(16) . 3_655 ?
O7 Na1 Na2 120.6(3) . 3_655 ?
O2 Na1 Na2 48.7(2) 3_655 3_655 ?
O4 Na1 Na2 134.7(3) 8 3_655 ?
O5 Na1 Na2 137.0(3) . 8 ?
O3 Na1 Na2 92.84(14) 3_655 8 ?
O8 Na1 Na2 89.03(13) . 8 ?
O7 Na1 Na2 40.1(2) . 8 ?
O2 Na1 Na2 133.4(3) 3_655 8 ?
O4 Na1 Na2 39.2(2) 8 8 ?
Na2 Na1 Na2 142.85(8) 3_655 8 ?
O5 Na1 Na2 71.2(2) . 12_454 ?
O3 Na1 Na2 139.42(17) 3_655 12_454 ?
O8 Na1 Na2 38.66(11) . 12_454 ?
O7 Na1 Na2 122.9(2) . 12_454 ?
O2 Na1 Na2 70.5(2) 3_655 12_454 ?
O4 Na1 Na2 114.6(2) 8 12_454 ?
Na2 Na1 Na2 89.30(10) 3_655 12_454 ?
Na2 Na1 Na2 127.68(8) 8 12_454 ?
O2 Na2 O8 98.9(4) . 11_544 ?
O2 Na2 O3 81.8(4) . . ?
O8 Na2 O3 177.6(6) 11_544 . ?
O2 Na2 O4 165.4(3) . . ?
O8 Na2 O4 95.3(4) 11_544 . ?
O3 Na2 O4 84.2(3) . . ?
O2 Na2 O5 88.20(18) . 4_464 ?
O8 Na2 O5 99.0(4) 11_544 4_464 ?
O3 Na2 O5 78.6(4) . 4_464 ?
O4 Na2 O5 92.8(4) . 4_464 ?
O2 Na2 O7 98.5(4) . 16_444 ?
O8 Na2 O7 82.6(4) 11_544 16_444 ?
O3 Na2 O7 99.6(3) . 16_444 ?
O4 Na2 O7 80.0(2) . 16_444 ?
O5 Na2 O7 172.8(4) 4_464 16_444 ?
O2 Na2 Na1 51.4(2) . 4_464 ?
O8 Na2 Na1 129.12(15) 11_544 4_464 ?
O3 Na2 Na1 49.63(13) . 4_464 ?
O4 Na2 Na1 120.2(3) . 4_464 ?
O5 Na2 Na1 48.7(2) 4_464 4_464 ?
O7 Na2 Na1 134.8(3) 16_444 4_464 ?
O2 Na2 Na1 135.9(3) . 16_444 ?
O8 Na2 Na1 89.41(13) 11_544 16_444 ?
O3 Na2 Na1 91.75(14) . 16_444 ?
O4 Na2 Na1 40.6(3) . 16_444 ?
O5 Na2 Na1 133.4(3) 4_464 16_444 ?
O7 Na2 Na1 39.4(2) 16_444 16_444 ?
Na1 Na2 Na1 141.36(8) 4_464 16_444 ?
O2 Na2 Na1 72.4(2) . 11_544 ?
O8 Na2 Na1 38.48(11) 11_544 11_544 ?
O3 Na2 Na1 140.21(18) . 11_544 ?
O4 Na2 Na1 121.6(2) . 11_544 ?
O5 Na2 Na1 71.0(2) 4_464 11_544 ?
O7 Na2 Na1 113.5(2) 16_444 11_544 ?
Na1 Na2 Na1 90.64(10) 4_464 11_544 ?
Na1 Na2 Na1 127.83(8) 16_444 11_544 ?

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
C2 C1 C2 C3 -0.3(5) 10_454 . . . ?
C5 C1 C2 C3 179.7(5) . . . . ?
C2 C1 C2 Br1 179.0(6) 10_454 . . . ?
C5 C1 C2 Br1 -1.0(6) . . . . ?
C1 C2 C3 C4 0.5(10) . . . . ?
Br1 C2 C3 C4 -178.7(4) . . . . ?
C1 C2 C3 Br2 -177.6(4) . . . . ?
Br1 C2 C3 Br2 3.2(9) . . . . ?
C2 C3 C4 C3 -0.2(5) . . . 10_454 ?
Br2 C3 C4 C3 177.9(6) . . . 10_454 ?
C2 C3 C4 C6 179.8(5) . . . . ?
Br2 C3 C4 C6 -2.1(6) . . . . ?
C2 C1 C5 O1 -68.1(5) 10_454 . . . ?
C2 C1 C5 O1 111.9(5) . . . . ?
C2 C1 C5 O1 111.9(5) 10_454 . . 10_454 ?
C2 C1 C5 O1 -68.1(5) . . . 10_454 ?
C3 C4 C6 O2 92.4(4) 10_454 . . 10_454 ?
C3 C4 C6 O2 -87.6(4) . . . 10_454 ?
C3 C4 C6 O2 -87.6(4) 10_454 . . . ?
C3 C4 C6 O2 92.4(4) . . . . ?
C8 C7 C8 C9 0.5(5) 10_554 . . . ?
C11 C7 C8 C9 -179.5(4) . . . . ?
C8 C7 C8 Br4 179.9(5) 10_554 . . . ?
C11 C7 C8 Br4 -0.1(5) . . . . ?
C7 C8 C9 C10 -1.0(9) . . . . ?
Br4 C8 C9 C10 179.6(4) . . . . ?
C7 C8 C9 Br3 176.7(4) . . . . ?
Br4 C8 C9 Br3 -2.7(7) . . . . ?
C8 C9 C10 C9 0.5(4) . . . 10_554 ?
Br3 C9 C10 C9 -177.3(5) . . . 10_554 ?
C8 C9 C10 C12 -179.5(4) . . . . ?
Br3 C9 C10 C12 2.7(5) . . . . ?
C8 C7 C11 O5 -92.5(4) 10_554 . . 10_554 ?
C8 C7 C11 O5 87.5(4) . . . 10_554 ?
C8 C7 C11 O5 87.5(4) 10_554 . . . ?
C8 C7 C11 O5 -92.5(4) . . . . ?
C9 C10 C12 O6 66.4(4) . . . 10_554 ?
C9 C10 C12 O6 -113.6(4) 10_554 . . 10_554 ?
C9 C10 C12 O6 -113.6(4) . . . . ?
C9 C10 C12 O6 66.4(4) 10_554 . . . ?
O2 C6 O2 Na2 53.2(9) 10_454 . . . ?
C4 C6 O2 Na2 -126.8(9) . . . . ?
O2 C6 O2 Na1 -52.7(8) 10_454 . . 4_464 ?
C4 C6 O2 Na1 127.3(8) . . . 4_464 ?
O5 C11 O5 Na1 54.6(9) 10_554 . . . ?
C7 C11 O5 Na1 -125.4(9) . . . . ?
O5 C11 O5 Na2 -53.2(8) 10_554 . . 3_655 ?
C7 C11 O5 Na2 126.8(8) . . . 3_655 ?

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
O3 H3A O1 0.97 1.98 2.834(13) 146.1 4_454
O3 H3A Br1 0.97 3.03 3.717(17) 128.8 11_544
O3 H3B O6 0.97 2.02 2.891(13) 147.8 13_454
O3 H3B Br3 0.97 3.13 3.785(17) 126.1 6_545
O4 H4A Br1 0.97 3.04 3.764(9) 132.4 7_654
O4 H4A Br4 0.97 3.04 3.828(7) 138.8 4_464
O4 H4B O1 0.97 2.21 3.093(9) 151.2 4_454
O4 H4B Br1 0.97 3.12 3.771(9) 125.6 11_544
O4 H4B Br4 0.97 2.88 3.523(7) 125.1 7_654
O7 H7A Br2 0.97 2.96 3.744(7) 138.6 12_454
O7 H7A Br3 0.97 3.10 3.838(9) 133.6 12_454
O7 H7B O6 0.97 2.11 3.011(10) 153.6 8
O7 H7B Br2 0.97 2.97 3.611(7) 124.6 8
O7 H7B Br3 0.97 3.09 3.704(9) 122.3 15_654
O8 H8A O6 0.97 1.91 2.803(13) 152.9 12_454
O8 H8A Br2 0.97 2.83 3.518(18) 129.0 12_454
O8 H8B O1 0.97 1.94 2.861(14) 158.9 6_545
O8 H8B Br4 0.97 2.94 3.599(18) 126.4 10_554
O3 H3A O1 0.97 1.98 2.834(13) 146.1 4_454
O3 H3A Br1 0.97 3.03 3.717(17) 128.8 11_544
O3 H3B O6 0.97 2.02 2.891(13) 147.8 13_454
O3 H3B Br3 0.97 3.13 3.785(17) 126.1 6_545
O4 H4A Br1 0.97 3.04 3.764(9) 132.4 7_654
O4 H4A Br4 0.97 3.04 3.828(7) 138.8 4_464
O4 H4B O1 0.97 2.21 3.093(9) 151.2 4_454
O4 H4B Br1 0.97 3.12 3.771(9) 125.6 11_544
O4 H4B Br4 0.97 2.88 3.523(7) 125.1 7_654
O7 H7A Br2 0.97 2.96 3.744(7) 138.6 12_454
O7 H7A Br3 0.97 3.10 3.838(9) 133.6 12_454
O7 H7B O6 0.97 2.11 3.011(10) 153.6 8
O7 H7B Br2 0.97 2.97 3.611(7) 124.6 8
O7 H7B Br3 0.97 3.09 3.704(9) 122.3 15_654
O8 H8A O6 0.97 1.91 2.803(13) 152.9 12_454
O8 H8A Br2 0.97 2.83 3.518(18) 129.0 12_454
O8 H8B O1 0.97 1.94 2.861(14) 158.9 6_545
O8 H8B Br4 0.97 2.94 3.599(18) 126.4 10_554

_refine_diff_density_max         0.674
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.181

####################################################################### 
# 
# 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 1939460'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;School of Chemistry The University of Melbourne
Australia
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Br4 K2 O8'
_chemical_formula_weight         629.98
_chemical_oxdiff_usercomment     'kamran sample NMe'

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'
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'
K K 0.2009 0.2494 '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                   11.6690(5)
_cell_length_b                   7.2589(3)
_cell_length_c                   10.7100(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.479(5)
_cell_angle_gamma                90
_cell_volume                     878.37(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    130.01(10)
_cell_measurement_reflns_used    2700
_cell_measurement_theta_min      3.9420
_cell_measurement_theta_max      36.1590

_exptl_crystal_description       'TRIANGULAR PLATE'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.382
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.632
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    9.667
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.075
_exptl_absorpt_correction_T_max  0.529
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.459
_oxdiff_exptl_absorpt_empirical_full_max 2.118
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            9857
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.336
_diffrn_reflns_theta_max         36.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4078
_reflns_number_gt                3238
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0387P)²+0.0668P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4078
_refine_ls_number_parameters     116
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.094
_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
C1 C 0.7587(2) 0.4932(3) 0.5472(2) 0.0128(4) Uani 1 1 d . . . . .
C2 C 0.6240(2) 0.4982(3) 0.5227(2) 0.0118(4) Uani 1 1 d . . . . .
C3 C 0.5548(2) 0.5954(3) 0.4192(2) 0.0131(4) Uani 1 1 d . . . . .
C4 C 0.4320(2) 0.5978(4) 0.3967(2) 0.0131(4) Uani 1 1 d . . . . .
O1 O 0.80081(16) 0.3585(3) 0.50097(17) 0.0160(3) Uani 1 1 d . . . . .
O2 O 0.81545(17) 0.6245(3) 0.61012(18) 0.0168(4) Uani 1 1 d . . . . .
O3 O 0.93909(18) 0.0174(3) 0.84164(19) 0.0199(4) Uani 1 1 d D . . . .
O4 O 0.92805(19) -0.1331(3) 0.38010(19) 0.0212(4) Uani 1 1 d D . . . .
Br1 Br 0.63143(3) 0.72439(4) 0.31006(3) 0.01867(8) Uani 1 1 d . . . . .
Br2 Br 0.33725(2) 0.72171(4) 0.25223(3) 0.01589(7) Uani 1 1 d . . . . .
K K 0.84376(5) -0.00056(8) 0.57873(5) 0.01754(11) Uani 1 1 d . . . . .
H4A H 0.931(5) -0.2479(14) 0.379(4) 0.056(16) Uiso 1 1 d D . . . .
H3B H 1.0067(16) 0.058(6) 0.871(4) 0.046(13) Uiso 1 1 d D . . . .
H4B H 0.883(3) -0.096(5) 0.312(2) 0.034(11) Uiso 1 1 d D . . . .
H3A H 0.893(3) 0.059(6) 0.881(4) 0.062(15) Uiso 1 1 d 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
C1 O1 1.251(3) . ?
C1 O2 1.256(3) . ?
C1 C2 1.528(3) . ?
C2 C3 1.389(3) . ?
C2 C4 1.393(3) 3_666 ?
C3 C4 1.393(3) . ?
C3 Br1 1.888(2) . ?
C4 Br2 1.889(2) . ?
O1 K 2.744(2) . ?
O2 K 2.772(2) 1_565 ?
O3 K 2.760(2) . ?
O3 H3B 0.829(10) . ?
O3 H3A 0.823(10) . ?
O4 K 2.732(2) . ?
O4 K 2.764(2) 3_756 ?
O4 H4A 0.834(10) . ?
O4 H4B 0.829(10) . ?
Br1 K 3.8523(7) 1_565 ?
Br2 K 3.7079(6) 3_666 ?
K K 4.3834(11) 3_756 ?
K H4B 3.08(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
O1 C1 O2 126.8(2) . . ?
O1 C1 C2 116.1(2) . . ?
O2 C1 C2 117.1(2) . . ?
C3 C2 C4 118.6(2) . 3_666 ?
C3 C2 C1 121.1(2) . . ?
C4 C2 C1 120.2(2) 3_666 . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 Br1 118.37(18) . . ?
C4 C3 Br1 120.81(18) . . ?
C3 C4 C2 120.5(2) . 3_666 ?
C3 C4 Br2 120.94(17) . . ?
C2 C4 Br2 118.47(18) 3_666 . ?
C1 O1 K 133.05(15) . . ?
C1 O2 K 137.96(16) . 1_565 ?
K O3 H3B 121(3) . . ?
K O3 H3A 113(3) . . ?
H3B O3 H3A 111(3) . . ?
K O4 K 105.80(7) . 3_756 ?
K O4 H4A 113(4) . . ?
K O4 H4A 108(4) 3_756 . ?
K O4 H4B 107(3) . . ?
K O4 H4B 114(3) 3_756 . ?
H4A O4 H4B 109(3) . . ?
C3 Br1 K 96.32(8) . 1_565 ?
C4 Br2 K 98.53(7) . 3_666 ?
O4 K O1 99.90(6) . . ?
O4 K O3 132.80(7) . . ?
O1 K O3 105.14(6) . . ?
O4 K O4 74.20(7) . 3_756 ?
O1 K O4 79.09(7) . 3_756 ?
O3 K O4 72.19(6) . 3_756 ?
O4 K O2 79.97(6) . 1_545 ?
O1 K O2 162.00(6) . 1_545 ?
O3 K O2 87.29(6) . 1_545 ?
O4 K O2 117.67(7) 3_756 1_545 ?
O4 K Br2 158.79(5) . 3_666 ?
O1 K Br2 63.04(4) . 3_666 ?
O3 K Br2 67.01(4) . 3_666 ?
O4 K Br2 111.98(5) 3_756 3_666 ?
O2 K Br2 112.15(4) 1_545 3_666 ?
O4 K Br1 61.67(5) . 1_545 ?
O1 K Br1 103.35(4) . 1_545 ?
O3 K Br1 143.76(5) . 1_545 ?
O4 K Br1 135.66(5) 3_756 1_545 ?
O2 K Br1 60.52(4) 1_545 1_545 ?
Br2 K Br1 108.006(16) 3_666 1_545 ?
O4 K K 37.35(5) . 3_756 ?
O1 K K 89.30(4) . 3_756 ?
O3 K K 103.33(5) . 3_756 ?
O4 K K 36.85(4) 3_756 3_756 ?
O2 K K 100.62(4) 1_545 3_756 ?
Br2 K K 144.79(2) 3_666 3_756 ?
Br1 K K 98.924(19) 1_545 3_756 ?
O4 K H4B 14.9(4) . . ?
O1 K H4B 89.5(6) . . ?
O3 K H4B 147.2(4) . . ?
O4 K H4B 82.4(6) 3_756 . ?
O2 K H4B 86.6(7) 1_545 . ?
Br2 K H4B 144.1(4) 3_666 . ?
Br1 K H4B 53.7(7) 1_545 . ?
K K H4B 46.7(6) 3_756 . ?

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
O1 C1 C2 C3 -94.6(3) . . . . ?
O2 C1 C2 C3 84.8(3) . . . . ?
O1 C1 C2 C4 84.4(3) . . . 3_666 ?
O2 C1 C2 C4 -96.2(3) . . . 3_666 ?
C4 C2 C3 C4 0.3(4) 3_666 . . . ?
C1 C2 C3 C4 179.3(2) . . . . ?
C4 C2 C3 Br1 -179.77(18) 3_666 . . . ?
C1 C2 C3 Br1 -0.8(3) . . . . ?
C2 C3 C4 C2 -0.3(4) . . . 3_666 ?
Br1 C3 C4 C2 179.77(18) . . . 3_666 ?
C2 C3 C4 Br2 -177.49(19) . . . . ?
Br1 C3 C4 Br2 2.6(3) . . . . ?
O2 C1 O1 K 101.5(3) . . . . ?
C2 C1 O1 K -79.2(3) . . . . ?
O1 C1 O2 K 112.4(3) . . . 1_565 ?
C2 C1 O2 K -66.9(3) . . . 1_565 ?
C2 C3 Br1 K -53.4(2) . . . 1_565 ?
C4 C3 Br1 K 126.6(2) . . . 1_565 ?
C3 C4 Br2 K -128.9(2) . . . 3_666 ?
C2 C4 Br2 K 53.84(19) 3_666 . . 3_666 ?

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
O4 H4A O3 0.834(10) 2.005(14) 2.828(3) 169(5) 4
O3 H3B O2 0.829(10) 2.090(15) 2.887(3) 161(4) 2_746
O4 H4B O2 0.829(10) 2.12(2) 2.862(3) 149(4) 4_565
O3 H3A O1 0.823(10) 1.960(12) 2.776(3) 171(5) 4_566
O3 H3A Br2 0.823(10) 3.14(4) 3.657(2) 123(4) 3_666

_refine_diff_density_max         1.056
_refine_diff_density_min         -1.654
_refine_diff_density_rms         0.210

