# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ke049
_database_code_depnum_ccdc_archive 'CCDC 2120714'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-11
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        '5-bromo-resorcylic acid acetone solvate'
_chemical_formula_moiety         'C7 H5 Br O4, C3 H6 O'
_chemical_formula_sum            'C10 H11 Br O5'
_chemical_formula_weight         291.10
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.8141(5)
_cell_length_b                   27.892(2)
_cell_length_c                   8.7246(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.630(3)
_cell_angle_gamma                90
_cell_volume                     1133.51(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2862
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.610
_cell_measurement_theta_min      2.521
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.629
_exptl_absorpt_correction_T_max  0.8878
_exptl_absorpt_correction_T_min  0.5366
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.6044.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Crystallised from acetone solution by slow cooling'
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8599
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         2.521
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1806
_reflns_number_total             2390
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0192P)²+2.1538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0821
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4A)
2.b Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C2S(H2SA,H2SB,H2SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.21480(9) 0.56940(2) 0.46057(5) 0.02103(13) Uani 1 1 d . . . . .
O2 O 1.3632(6) 0.55104(9) 1.0328(3) 0.0175(6) Uani 1 1 d . . . . .
O1 O 1.1739(6) 0.49917(9) 0.8386(3) 0.0191(6) Uani 1 1 d . . . . .
H1 H 1.319081 0.483224 0.884567 0.029 Uiso 1 1 calc R U . . .
O4 O 0.2356(6) 0.66014(10) 0.6536(3) 0.0202(7) Uani 1 1 d . . . . .
H4 H 0.243824 0.685388 0.707082 0.030 Uiso 1 1 calc R U . . .
O3 O 1.0875(6) 0.63043(10) 1.0532(3) 0.0250(7) Uani 1 1 d . . . . .
H3 H 1.221941 0.610480 1.078726 0.037 Uiso 1 1 calc R U . . .
O1S O 0.7814(8) 0.74840(11) 0.2546(4) 0.0401(9) Uani 1 1 d . . . . .
C3S C 0.6113(11) 0.74360(17) 0.4855(5) 0.0375(12) Uani 1 1 d . . . . .
H3SA H 0.663454 0.777633 0.495338 0.056 Uiso 1 1 calc R U . . .
H3SB H 0.712023 0.726594 0.581794 0.056 Uiso 1 1 calc R U . . .
H3SC H 0.403570 0.740286 0.470909 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4601(8) 0.63189(13) 0.7197(4) 0.0159(9) Uani 1 1 d . . . . .
C6 C 0.4897(8) 0.58770(14) 0.6483(4) 0.0145(9) Uani 1 1 d . . . . .
C7 C 0.7151(8) 0.55822(13) 0.7105(4) 0.0147(9) Uani 1 1 d . . . . .
H7 H 0.730930 0.528498 0.660188 0.018 Uiso 1 1 calc R U . . .
C2 C 0.9256(8) 0.57107(14) 0.8484(4) 0.0141(8) Uani 1 1 d . . . . .
C4 C 0.6644(8) 0.64464(14) 0.8570(4) 0.0173(9) Uani 1 1 d . . . . .
H4A H 0.644520 0.674058 0.908076 0.021 Uiso 1 1 calc R U . . .
C1S C 0.6949(9) 0.72271(15) 0.3458(5) 0.0210(10) Uani 1 1 d . . . . .
C3 C 0.8954(8) 0.61526(14) 0.9203(4) 0.0170(9) Uani 1 1 d . . . . .
C1 C 1.1705(8) 0.54005(13) 0.9139(5) 0.0161(9) Uani 1 1 d . . . . .
C2S C 0.6695(10) 0.67030(14) 0.3250(5) 0.0281(11) Uani 1 1 d . . . . .
H2SA H 0.725118 0.661099 0.228509 0.042 Uiso 1 1 calc R U . . .
H2SB H 0.470439 0.660570 0.316119 0.042 Uiso 1 1 calc R U . . .
H2SC H 0.796053 0.654395 0.416587 0.042 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 C6 1.897(3) . ?
O2 C1 1.243(4) . ?
O1 H1 0.8400 . ?
O1 C1 1.318(4) . ?
O4 H4 0.8400 . ?
O4 C5 1.344(4) . ?
O3 H3 0.8400 . ?
O3 C3 1.355(4) . ?
O1S C1S 1.220(5) . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
C3S C1S 1.495(6) . ?
C5 C6 1.404(5) . ?
C5 C4 1.391(5) . ?
C6 C7 1.361(5) . ?
C7 H7 0.9500 . ?
C7 C2 1.410(5) . ?
C2 C3 1.407(5) . ?
C2 C1 1.458(5) . ?
C4 H4A 0.9500 . ?
C4 C3 1.380(5) . ?
C1S C2S 1.474(6) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
C1 O1 H1 109.5 . . ?
C5 O4 H4 109.5 . . ?
C3 O3 H3 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
C1S C3S H3SA 109.5 . . ?
C1S C3S H3SB 109.5 . . ?
C1S C3S H3SC 109.5 . . ?
O4 C5 C6 119.0(3) . . ?
O4 C5 C4 122.4(3) . . ?
C4 C5 C6 118.5(4) . . ?
C5 C6 Br1 119.5(3) . . ?
C7 C6 Br1 119.6(3) . . ?
C7 C6 C5 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C2 121.0(3) . . ?
C2 C7 H7 119.5 . . ?
C7 C2 C1 121.3(3) . . ?
C3 C2 C7 118.1(3) . . ?
C3 C2 C1 120.6(3) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4A 119.5 . . ?
O1S C1S C3S 120.6(4) . . ?
O1S C1S C2S 122.2(4) . . ?
C2S C1S C3S 117.1(4) . . ?
O3 C3 C2 122.0(3) . . ?
O3 C3 C4 117.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
O2 C1 O1 121.9(3) . . ?
O2 C1 C2 122.7(3) . . ?
O1 C1 C2 115.4(3) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
Br1 C6 C7 C2 179.0(3) . . . . ?
O4 C5 C6 Br1 0.5(5) . . . . ?
O4 C5 C6 C7 179.4(4) . . . . ?
O4 C5 C4 C3 -178.8(4) . . . . ?
C5 C6 C7 C2 0.1(6) . . . . ?
C5 C4 C3 O3 179.1(4) . . . . ?
C5 C4 C3 C2 -1.4(6) . . . . ?
C6 C5 C4 C3 1.6(6) . . . . ?
C6 C7 C2 C3 0.2(6) . . . . ?
C6 C7 C2 C1 -178.8(4) . . . . ?
C7 C2 C3 O3 179.9(4) . . . . ?
C7 C2 C3 C4 0.5(6) . . . . ?
C7 C2 C1 O2 178.0(4) . . . . ?
C7 C2 C1 O1 -2.2(6) . . . . ?
C4 C5 C6 Br1 -179.9(3) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C3 C2 C1 O2 -0.9(6) . . . . ?
C3 C2 C1 O1 178.8(4) . . . . ?
C1 C2 C3 O3 -1.1(6) . . . . ?
C1 C2 C3 C4 179.5(4) . . . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ke047
_database_code_depnum_ccdc_archive 'CCDC 2120715'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        '5-bromo-resorcylic acid DMF solvate'
_chemical_formula_moiety         'C7 H5 Br O4, C3 H7 N O'
_chemical_formula_sum            'C10 H12 Br N O5'
_chemical_formula_weight         306.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8995(4)
_cell_length_b                   17.2454(6)
_cell_length_c                   13.5191(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.328(5)
_cell_angle_gamma                90
_cell_volume                     2367.10(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.3570
_cell_measurement_theta_min      2.0030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.483
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'crystallised by slow cooling from DMF solution'
_exptl_crystal_size_max          0.2688
_exptl_crystal_size_mid          0.2063
_exptl_crystal_size_min          0.1449
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10853
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.002
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9531   19.0000  -90.0000 105

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3281 -100.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9531 -100.0000  -30.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega  -89.00  -53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3281 -178.0000    0.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0098221000
_diffrn_orient_matrix_UB_12      -0.0104763000
_diffrn_orient_matrix_UB_13      -0.0530589000
_diffrn_orient_matrix_UB_21      0.0013862000
_diffrn_orient_matrix_UB_22      -0.0398054000
_diffrn_orient_matrix_UB_23      0.0137764000
_diffrn_orient_matrix_UB_31      -0.0691130000
_diffrn_orient_matrix_UB_32      0.0006806000
_diffrn_orient_matrix_UB_33      -0.0128981000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3500
_reflns_number_total             4656
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C104(H10A), C1S(H1S), C4(H4A), C101(H10B), C107(H107), C8(H7)
2.b Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C102(H10C,H10D,H10E), C2S(H2SA,H2SB,H2SC), C10(H10F,H10G,
 H10H)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O104(H104), O103(H103), O1(H101), O3(H3), O5(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Br10 Br 0.17860(3) 0.08125(2) 0.71525(3) 0.02135(12) Uani 1 1 d . . . . .
Br1 Br 0.81384(3) -0.00576(2) 0.76041(3) 0.02018(12) Uani 1 1 d . . . . .
O4 O 0.9567(2) 0.14637(16) 0.8385(2) 0.0220(7) Uani 1 1 d . . . . .
H4 H 0.9982 0.1883 0.8557 0.033 Uiso 1 1 calc GR . . . .
O104 O 0.0434(2) 0.23335(16) 0.6265(2) 0.0217(7) Uani 1 1 d . . . . .
H104 H 0.0044 0.2757 0.6061 0.032 Uiso 1 1 calc GR . . . .
O2 O 0.3878(2) 0.25978(16) 0.53506(18) 0.0189(6) Uani 1 1 d . . . . .
O101 O 0.0853(2) 0.27731(17) 0.89713(19) 0.0274(7) Uani 1 1 d . . . . .
O103 O 0.4036(2) 0.40440(16) 0.77633(19) 0.0198(6) Uani 1 1 d . . . . .
H103 H 0.4812 0.4051 0.8205 0.030 Uiso 1 1 calc GR . . . .
O1 O 0.6363(2) 0.21458(16) 0.92598(19) 0.0203(6) Uani 1 1 d . . . . .
H101 H 0.7165 0.2243 0.9585 0.030 Uiso 1 1 calc GR . . . .
O102 O 0.6258(2) 0.34358(16) 0.90164(19) 0.0209(6) Uani 1 1 d . . . . .
N1S N 0.2944(3) 0.0270(2) 1.0204(2) 0.0174(7) Uani 1 1 d . . . . .
O1S O 0.4247(2) 0.13328(17) 1.0703(2) 0.0301(7) Uani 1 1 d . . . . .
N101 N 0.2135(3) 0.3840(2) 0.9438(2) 0.0191(8) Uani 1 1 d . . . . .
O3 O 0.6170(2) 0.32144(17) 0.6476(2) 0.0249(7) Uani 1 1 d . . . . .
H3 H 0.5386 0.3220 0.6048 0.037 Uiso 1 1 calc GR . . . .
O5 O 0.3719(2) 0.13061(16) 0.5228(2) 0.0230(7) Uani 1 1 d . . . . .
H1 H 0.2940 0.1415 0.4842 0.034 Uiso 1 1 calc GR . . . .
C6 C 0.7517(3) 0.0969(2) 0.7270(3) 0.0153(9) Uani 1 1 d . . . . .
C5 C 0.8337(3) 0.1608(2) 0.7696(3) 0.0144(9) Uani 1 1 d . . . . .
C104 C 0.2257(3) 0.3203(2) 0.7024(3) 0.0161(9) Uani 1 1 d . . . . .
H10A H 0.1733 0.3638 0.6695 0.019 Uiso 1 1 calc R . . . .
C1S C 0.3156(3) 0.1016(3) 1.0237(3) 0.0218(10) Uani 1 1 d . . . . .
H1S H 0.2428 0.1343 0.9881 0.026 Uiso 1 1 calc R . . . .
C4 C 0.7863(3) 0.2357(2) 0.7410(3) 0.0172(9) Uani 1 1 d . . . . .
H4A H 0.8423 0.2789 0.7684 0.021 Uiso 1 1 calc R . . . .
C3S C 0.1648(3) -0.0063(2) 0.9633(3) 0.0252(10) Uani 1 1 d . . . . .
H3SA H 0.1018 0.0354 0.9311 0.038 Uiso 1 1 calc GR . . . .
H3SB H 0.1356 -0.0356 1.0129 0.038 Uiso 1 1 calc GR . . . .
H3SC H 0.1699 -0.0411 0.9076 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.6567(3) 0.2473(2) 0.6720(3) 0.0151(8) Uani 1 1 d . . . . .
C101 C 0.1926(3) 0.3088(3) 0.9424(3) 0.0214(10) Uani 1 1 d . . . . .
H10B H 0.2656 0.2765 0.9789 0.026 Uiso 1 1 calc R . . . .
C107 C 0.3784(3) 0.1935(2) 0.7990(3) 0.0156(9) Uani 1 1 d . . . . .
H107 H 0.4303 0.1499 0.8323 0.019 Uiso 1 1 calc R . . . .
C106 C 0.2493(3) 0.1831(2) 0.7348(3) 0.0156(9) Uani 1 1 d . . . . .
C102 C 0.3412(3) 0.4185(3) 1.0018(3) 0.0267(10) Uani 1 1 d . . . . .
H10C H 0.3337 0.4537 1.0562 0.040 Uiso 1 1 calc GR . . . .
H10D H 0.3712 0.4476 0.9525 0.040 Uiso 1 1 calc GR . . . .
H10E H 0.4048 0.3775 1.0358 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.4372(3) 0.1948(3) 0.5595(3) 0.0187(9) Uani 1 1 d . . . . .
C2 C 0.5736(3) 0.2791(2) 0.8849(3) 0.0164(9) Uani 1 1 d . . . . .
C7 C 0.5735(3) 0.1830(2) 0.6311(3) 0.0151(9) Uani 1 1 d . . . . .
C103 C 0.3565(3) 0.3309(2) 0.7659(3) 0.0149(8) Uani 1 1 d . . . . .
C8 C 0.6235(3) 0.1093(2) 0.6590(3) 0.0155(9) Uani 1 1 d . . . . .
H7 H 0.5682 0.0659 0.6306 0.019 Uiso 1 1 calc R . . . .
C9 C 0.4349(3) 0.2675(2) 0.8163(3) 0.0146(8) Uani 1 1 d . . . . .
C105 C 0.1699(3) 0.2468(2) 0.6860(3) 0.0146(9) Uani 1 1 d . . . . .
C2S C 0.3994(3) -0.0271(2) 1.0757(3) 0.0256(10) Uani 1 1 d . . . . .
H2SA H 0.4174 -0.0604 1.0239 0.038 Uiso 1 1 calc GR . . . .
H2SB H 0.3725 -0.0591 1.1241 0.038 Uiso 1 1 calc GR . . . .
H2SC H 0.4792 0.0019 1.1164 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.1056(4) 0.4361(3) 0.8875(3) 0.0380(12) Uani 1 1 d . . . . .
H10F H 0.0285 0.4057 0.8450 0.057 Uiso 1 1 calc GR . . . .
H10G H 0.1322 0.4701 0.8408 0.057 Uiso 1 1 calc GR . . . .
H10H H 0.0833 0.4677 0.9389 0.057 Uiso 1 1 calc GR . . . .


_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
Br10 C106 1.897(4) . ?
Br1 C6 1.891(4) . ?
O4 C5 1.348(4) . ?
O104 C105 1.340(4) . ?
O2 C1 1.235(5) . ?
O101 C101 1.231(4) . ?
O103 C103 1.355(4) . ?
O1 C2 1.318(4) . ?
O102 C2 1.232(4) . ?
N1S C1S 1.306(5) . ?
N1S C3S 1.458(4) . ?
N1S C2S 1.455(5) . ?
O1S C1S 1.250(4) . ?
N101 C101 1.316(5) . ?
N101 C102 1.453(4) . ?
N101 C10 1.456(5) . ?
O3 C3 1.351(4) . ?
O5 C1 1.312(5) . ?
C6 C5 1.403(5) . ?
C6 C8 1.381(4) . ?
C5 C4 1.393(5) . ?
C104 C103 1.384(4) . ?
C104 C105 1.388(5) . ?
C4 C3 1.395(4) . ?
C3 C7 1.412(5) . ?
C107 C106 1.370(4) . ?
C107 C9 1.398(5) . ?
C106 C105 1.406(5) . ?
C1 C7 1.463(5) . ?
C2 C9 1.471(5) . ?
C7 C8 1.380(5) . ?
C103 C9 1.403(5) . ?

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
C1S N1S C3S 122.1(3) . . ?
C1S N1S C2S 121.2(3) . . ?
C2S N1S C3S 116.7(3) . . ?
C101 N101 C102 122.6(3) . . ?
C101 N101 C10 119.8(3) . . ?
C102 N101 C10 117.6(4) . . ?
C5 C6 Br1 121.1(3) . . ?
C8 C6 Br1 119.4(3) . . ?
C8 C6 C5 119.4(4) . . ?
O4 C5 C6 117.7(3) . . ?
O4 C5 C4 122.6(3) . . ?
C4 C5 C6 119.8(3) . . ?
C103 C104 C105 120.9(4) . . ?
O1S C1S N1S 124.9(4) . . ?
C5 C4 C3 120.2(4) . . ?
O3 C3 C4 117.1(3) . . ?
O3 C3 C7 123.0(3) . . ?
C4 C3 C7 119.9(4) . . ?
O101 C101 N101 124.8(4) . . ?
C106 C107 C9 120.9(3) . . ?
C107 C106 Br10 118.8(3) . . ?
C107 C106 C105 120.7(4) . . ?
C105 C106 Br10 120.5(3) . . ?
O2 C1 O5 122.7(3) . . ?
O2 C1 C7 122.9(4) . . ?
O5 C1 C7 114.4(4) . . ?
O1 C2 C9 114.0(3) . . ?
O102 C2 O1 123.4(3) . . ?
O102 C2 C9 122.6(4) . . ?
C3 C7 C1 120.2(4) . . ?
C8 C7 C3 118.9(3) . . ?
C8 C7 C1 120.9(3) . . ?
O103 C103 C104 117.0(3) . . ?
O103 C103 C9 122.6(3) . . ?
C104 C103 C9 120.4(4) . . ?
C7 C8 C6 121.8(3) . . ?
C107 C9 C2 121.2(3) . . ?
C107 C9 C103 118.5(3) . . ?
C103 C9 C2 120.3(4) . . ?
O104 C105 C104 123.3(3) . . ?
O104 C105 C106 118.1(3) . . ?
C104 C105 C106 118.6(3) . . ?

_shelx_SHELXL_version_number     2014/7

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-13 -1 -3 0.1228 -13.1638 -1.1702 -3.1968 0.3112 -0.0157 0.9502
-14 4 13 0.1344 -13.8489 3.9769 13.4073 -0.6170 0.0072 0.7869
-4 6 18 0.1296 -3.9840 5.6738 18.4433 -0.9989 0.0227 0.0413
15 0 -2 0.0886 14.8576 -0.4642 -2.1395 -0.0276 0.0096 -0.9996
7 -6 -18 0.1126 7.2504 -5.6129 -18.3890 0.9633 -0.0199 -0.2677
-15 3 2 0.0907 -14.7075 3.1367 1.9852 0.0063 -0.1179 0.9930
0 24 -4 0.0313 -0.3714 23.5476 -4.1635 -0.0221 -0.9952 0.0954
15 -1 -2 0.1098 14.9058 -0.9313 -2.4156 -0.0085 0.0245 -0.9997
-1 -24 4 0.1033 -1.4344 -23.6046 4.4866 0.0233 0.9994 0.0252

_olex2_date_sample_data_collection 2016-11-03
_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ke055
_database_code_depnum_ccdc_archive 'CCDC 2120722'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-11
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        '5-bromo-resorcylic acid ethanol solvate'
_chemical_formula_moiety         'C7 H5 Br O4, C2 H6 O'
_chemical_formula_sum            'C9 H11 Br O5'
_chemical_formula_weight         279.09
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.7541(10)
_cell_length_b                   5.1393(5)
_cell_length_c                   18.7589(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.411(3)
_cell_angle_gamma                90
_cell_volume                     1036.46(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.590
_cell_measurement_theta_min      2.847
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.965
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.8554.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'Crystallised by fast cooling of an ethanol solution'
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.044
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19118
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1584
_reflns_number_total             2042
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0122P)²+1.2504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4A)
2.c Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O1S(H1S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.11382(3) 1.05122(6) 0.72782(2) 0.01499(10) Uani 1 1 d . . . . .
O1 O -0.01974(19) 0.2741(4) 0.55850(12) 0.0166(5) Uani 1 1 d . . . . .
H1 H -0.056494 0.153755 0.536186 0.025 Uiso 1 1 calc R U . . .
O2 O 0.14291(19) 0.1154(4) 0.50037(12) 0.0161(5) Uani 1 1 d . . . . .
O3 O 0.36402(19) 0.3175(4) 0.52695(12) 0.0168(5) Uani 1 1 d . . . . .
H3 H 0.312579 0.216580 0.506931 0.025 Uiso 1 1 calc R U . . .
O4 O 0.38492(18) 1.0035(4) 0.69541(12) 0.0150(5) Uani 1 1 d . . . . .
H4 H 0.461087 0.968293 0.693926 0.022 Uiso 1 1 calc R U . . .
O1S O 0.37848(19) 0.4126(5) 0.79639(12) 0.0227(6) Uani 1 1 d . . . . .
H1S H 0.351359 0.291256 0.770341 0.034 Uiso 1 1 calc R U . . .
C1 C 0.0992(3) 0.2735(6) 0.54274(17) 0.0129(7) Uani 1 1 d . . . . .
C7 C 0.1192(3) 0.6450(6) 0.62639(17) 0.0127(7) Uani 1 1 d . . . . .
H7 H 0.031735 0.642396 0.632256 0.015 Uiso 1 1 calc R U . . .
C2 C 0.1740(3) 0.4692(6) 0.57932(16) 0.0108(7) Uani 1 1 d . . . . .
C6 C 0.1905(3) 0.8192(6) 0.66372(17) 0.0108(7) Uani 1 1 d . . . . .
C3 C 0.3035(3) 0.4808(6) 0.57080(16) 0.0127(7) Uani 1 1 d . . . . .
C4 C 0.3750(3) 0.6610(6) 0.60847(17) 0.0125(7) Uani 1 1 d . . . . .
H4A H 0.462157 0.669540 0.601679 0.015 Uiso 1 1 calc R U . . .
C5 C 0.3196(3) 0.8288(6) 0.65598(17) 0.0122(7) Uani 1 1 d . . . . .
C1S C 0.2819(3) 0.5024(6) 0.84091(18) 0.0186(8) Uani 1 1 d . . . . .
H1SA H 0.253730 0.359458 0.872017 0.022 Uiso 1 1 calc R U . . .
H1SB H 0.209943 0.562317 0.811318 0.022 Uiso 1 1 calc R U . . .
C2S C 0.3320(3) 0.7225(7) 0.88541(19) 0.0231(9) Uani 1 1 d . . . . .
H2SA H 0.401043 0.659819 0.915830 0.035 Uiso 1 1 calc R U . . .
H2SB H 0.265988 0.790665 0.915313 0.035 Uiso 1 1 calc R U . . .
H2SC H 0.361631 0.860969 0.854194 0.035 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 C6 1.896(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.319(4) . ?
O2 C1 1.237(4) . ?
O3 H3 0.8400 . ?
O3 C3 1.353(4) . ?
O4 H4 0.8400 . ?
O4 C5 1.349(4) . ?
O1S H1S 0.8400 . ?
O1S C1S 1.426(4) . ?
C1 C2 1.450(4) . ?
C7 H7 0.9500 . ?
C7 C2 1.403(4) . ?
C7 C6 1.362(4) . ?
C2 C3 1.407(4) . ?
C6 C5 1.401(4) . ?
C3 C4 1.386(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.385(4) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.498(4) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
C1 O1 H1 109.5 . . ?
C3 O3 H3 109.5 . . ?
C5 O4 H4 109.5 . . ?
C1S O1S H1S 109.5 . . ?
O1 C1 C2 114.9(3) . . ?
O2 C1 O1 122.1(3) . . ?
O2 C1 C2 123.0(3) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C2 120.5(3) . . ?
C7 C2 C1 120.5(3) . . ?
C7 C2 C3 118.4(3) . . ?
C3 C2 C1 121.0(3) . . ?
C7 C6 Br1 119.4(2) . . ?
C7 C6 C5 121.1(3) . . ?
C5 C6 Br1 119.4(2) . . ?
O3 C3 C2 122.4(3) . . ?
O3 C3 C4 117.1(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4A 119.9 . . ?
O4 C5 C6 118.1(3) . . ?
O4 C5 C4 122.7(3) . . ?
C4 C5 C6 119.2(3) . . ?
O1S C1S H1SA 110.0 . . ?
O1S C1S H1SB 110.0 . . ?
O1S C1S C2S 108.3(3) . . ?
H1SA C1S H1SB 108.4 . . ?
C2S C1S H1SA 110.0 . . ?
C2S C1S H1SB 110.0 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
Br1 C6 C5 O4 0.5(4) . . . . ?
Br1 C6 C5 C4 -179.2(2) . . . . ?
O1 C1 C2 C7 -1.2(4) . . . . ?
O1 C1 C2 C3 176.2(3) . . . . ?
O2 C1 C2 C7 179.5(3) . . . . ?
O2 C1 C2 C3 -3.2(5) . . . . ?
O3 C3 C4 C5 -178.0(3) . . . . ?
C1 C2 C3 O3 2.1(5) . . . . ?
C1 C2 C3 C4 -177.1(3) . . . . ?
C7 C2 C3 O3 179.5(3) . . . . ?
C7 C2 C3 C4 0.4(5) . . . . ?
C7 C6 C5 O4 -179.0(3) . . . . ?
C7 C6 C5 C4 1.2(5) . . . . ?
C2 C7 C6 Br1 -179.2(2) . . . . ?
C2 C7 C6 C5 0.3(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C6 C7 C2 C1 176.3(3) . . . . ?
C6 C7 C2 C3 -1.1(5) . . . . ?
C3 C4 C5 O4 178.3(3) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ke034
_database_code_depnum_ccdc_archive 'CCDC 2120721'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        '3,5-dibromo-resorcylic acid DMF solvate'
_chemical_formula_moiety         'C7 H4 Br2 O4, C3 H7 N O'
_chemical_formula_sum            'C10 H11 Br2 N O5'
_chemical_formula_weight         385.02
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.6810(12)
_cell_length_b                   3.8913(3)
_cell_length_c                   18.1986(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1252.10(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8419
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.486
_exptl_absorpt_correction_T_max  0.5412
_exptl_absorpt_correction_T_min  0.2169
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1134 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.4008.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.042
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'crystallised by slow cooling of a DMF solution'
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.152
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11495
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2251
_reflns_number_total             2315
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.031(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0176P)²+0.3192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0468
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.969(14)
 0.031(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1S(H1S)
3.b Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.29192(2) 0.27682(9) 0.56028(3) 0.01322(11) Uani 1 1 d . . . . .
Br1 Br 0.50750(2) 0.90366(10) 0.37261(3) 0.01492(12) Uani 1 1 d . . . . .
O3 O 0.60914(18) 0.7713(8) 0.50148(19) 0.0167(7) Uani 1 1 d . . . . .
H3 H 0.6393 0.7056 0.5342 0.025 Uiso 1 1 calc GR . . . .
O1 O 0.55712(19) 0.2607(8) 0.6968(2) 0.0203(8) Uani 1 1 d . . . . .
H1 H 0.5945 0.2147 0.7235 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.64640(16) 0.5157(9) 0.62866(18) 0.0176(7) Uani 1 1 d . . . . .
C2 C 0.5214(2) 0.4894(11) 0.5826(2) 0.0114(9) Uani 1 1 d . . . . .
C1 C 0.5802(2) 0.4254(11) 0.6376(3) 0.0141(9) Uani 1 1 d . . . . .
C3 C 0.5393(2) 0.6540(11) 0.5167(3) 0.0117(9) Uani 1 1 d . . . . .
C6 C 0.3919(2) 0.4311(10) 0.5423(2) 0.0112(9) Uani 1 1 d . . . . .
C7 C 0.4465(2) 0.3767(11) 0.5944(3) 0.0128(9) Uani 1 1 d . . . . .
H7 H 0.4338 0.2623 0.6389 0.015 Uiso 1 1 calc R . . . .
O1S O 0.66399(18) 0.1054(8) 0.78756(18) 0.0178(7) Uani 1 1 d . . . . .
O4 O 0.35327(17) 0.6205(8) 0.42583(18) 0.0155(7) Uani 1 1 d . . . . .
H4 H 0.3683 0.7427 0.3907 0.023 Uiso 1 1 calc GR . . . .
N1S N 0.7813(2) -0.1395(9) 0.7891(2) 0.0124(8) Uani 1 1 d . . . . .
C2S C 0.7904(2) -0.1356(13) 0.8686(3) 0.0179(9) Uani 1 1 d . . . . .
H2SA H 0.8344 0.0051 0.8816 0.027 Uiso 1 1 calc GR . . . .
H2SB H 0.7981 -0.3708 0.8864 0.027 Uiso 1 1 calc GR . . . .
H2SC H 0.7450 -0.0385 0.8914 0.027 Uiso 1 1 calc GR . . . .
C4 C 0.4829(3) 0.6990(11) 0.4634(3) 0.0116(9) Uani 1 1 d . . . . .
C1S C 0.7203(2) -0.0234(11) 0.7561(3) 0.0147(9) Uani 1 1 d . . . . .
H1S H 0.7187 -0.0385 0.7040 0.018 Uiso 1 1 calc R . . . .
C3S C 0.8435(3) -0.2813(12) 0.7465(3) 0.0178(10) Uani 1 1 d . . . . .
H3SA H 0.8885 -0.1379 0.7531 0.027 Uiso 1 1 calc GR . . . .
H3SB H 0.8296 -0.2859 0.6944 0.027 Uiso 1 1 calc GR . . . .
H3SC H 0.8542 -0.5155 0.7633 0.027 Uiso 1 1 calc GR . . . .
C5 C 0.4087(2) 0.5877(11) 0.4752(2) 0.0117(9) 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
Br2 C6 1.895(4) . ?
Br1 C4 1.886(5) . ?
O3 C3 1.345(5) . ?
O1 C1 1.318(6) . ?
O2 C1 1.233(5) . ?
C2 C1 1.465(6) . ?
C2 C3 1.395(6) . ?
C2 C7 1.413(6) . ?
C3 C4 1.401(7) . ?
C6 C7 1.370(6) . ?
C6 C5 1.398(6) . ?
O1S C1S 1.253(5) . ?
O4 C5 1.335(5) . ?
N1S C2S 1.457(7) . ?
N1S C1S 1.314(6) . ?
N1S C3S 1.454(6) . ?
C4 C5 1.399(6) . ?

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
C3 C2 C1 120.3(4) . . ?
C3 C2 C7 119.1(4) . . ?
C7 C2 C1 120.5(4) . . ?
O1 C1 C2 115.0(4) . . ?
O2 C1 O1 122.7(4) . . ?
O2 C1 C2 122.3(4) . . ?
O3 C3 C2 122.7(4) . . ?
O3 C3 C4 117.9(4) . . ?
C2 C3 C4 119.3(4) . . ?
C7 C6 Br2 119.3(3) . . ?
C7 C6 C5 121.5(4) . . ?
C5 C6 Br2 119.2(3) . . ?
C6 C7 C2 120.5(4) . . ?
C1S N1S C2S 122.8(4) . . ?
C1S N1S C3S 120.5(4) . . ?
C3S N1S C2S 116.7(4) . . ?
C3 C4 Br1 119.7(3) . . ?
C5 C4 Br1 118.7(3) . . ?
C5 C4 C3 121.6(4) . . ?
O1S C1S N1S 125.5(4) . . ?
C6 C5 C4 117.9(4) . . ?
O4 C5 C6 118.3(4) . . ?
O4 C5 C4 123.8(4) . . ?


_olex2_exptl_crystal_mounting_method 
'crystal was coated in perfluoro polyether oil and mounted on a MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.969(14)
2 0.031(14)

####################################################################### 
# 
# 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_KE050
_database_code_depnum_ccdc_archive 'CCDC 2120717'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C7 H5 Br O4, C2 H6 O S'
_chemical_formula_sum            'C9 H11 Br O5 S'
_chemical_formula_weight         311.15
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.8467(5)
_cell_length_b                   8.5738(5)
_cell_length_c                   9.3115(6)
_cell_angle_alpha                73.0626(18)
_cell_angle_beta                 68.6204(18)
_cell_angle_gamma                83.6321(19)
_cell_volume                     558.02(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7549
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.441
_exptl_absorpt_coefficient_mu    3.872
_exptl_absorpt_correction_T_max  0.7901
_exptl_absorpt_correction_T_min  0.4274
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0984 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.5409.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.8517
_exptl_crystal_description       plate
_exptl_crystal_F_000             311.8721
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'Crystallised from DMSO solution by slow evaporation'
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11487
_diffrn_reflns_theta_full        25.9999
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.44
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2005
_reflns_number_total             2195
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5482
_refine_diff_density_min         -0.3233
_refine_diff_density_rms         0.0922
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.3460
_refine_ls_goodness_of_fit_ref   1.0743
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0200
_refine_ls_restrained_S_all      1.0743
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+0.2812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0520
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4a)
2.b Idealised Me refined as rotating group:
 C2S(H2Sa,H2Sb,H2Sc), C1S(H1Sa,H1Sb,H1Sc)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.07130(3) 0.41060(2) 0.20804(2) 0.01662(8) Uani 1.000000 .
S1S S 0.77718(6) 0.99366(6) -0.75913(6) 0.01268(11) Uani 1.000000 .
O4 O 0.33029(19) 0.12879(17) 0.22176(16) 0.0172(3) Uani 1.000000 .
O2 O 0.70018(19) 0.55748(17) -0.49546(16) 0.0181(3) Uani 1.000000 .
O3 O 0.75076(19) 0.27743(17) -0.31234(17) 0.0169(3) Uani 1.000000 .
O1 O 0.45777(19) 0.71009(16) -0.40116(17) 0.0171(3) Uani 1.000000 .
C6 C 0.2871(3) 0.3745(2) 0.0431(2) 0.0116(4) Uani 1.000000 .
C5 C 0.3901(3) 0.2329(2) 0.0747(2) 0.0122(4) Uani 1.000000 .
C3 C 0.6000(3) 0.3152(2) -0.1986(2) 0.0122(4) Uani 1.000000 .
C7 C 0.3417(3) 0.4867(2) -0.1044(2) 0.0118(4) Uani 1.000000 .
C2 C 0.4992(3) 0.4594(2) -0.2281(2) 0.0118(4) Uani 1.000000 .
C1 C 0.5610(3) 0.5790(2) -0.3857(2) 0.0135(4) Uani 1.000000 .
C4 C 0.5463(3) 0.2051(2) -0.0478(2) 0.0129(4) Uani 1.000000 .
O1S O 0.57840(18) 0.93656(16) -0.67833(16) 0.0144(3) Uani 1.000000 .
C2S C 0.8646(3) 0.9750(3) -0.6032(2) 0.0182(4) Uani 1.000000 .
C1S C 0.8990(3) 0.8282(3) -0.8334(3) 0.0191(4) Uani 1.000000 .
H7 H 0.2721(3) 0.5836(2) -0.1227(2) 0.0142(5) Uiso 1.000000 R
H4a H 0.6172(3) 0.1093(2) -0.0280(2) 0.0154(5) Uiso 1.000000 R
H4 H 0.4169(9) 0.068(2) 0.2375(12) 0.0258(5) Uiso 1.000000 GR
H3 H 0.774(2) 0.3540(13) -0.3969(9) 0.0254(5) Uiso 1.000000 GR
H2Sa H 0.8029(14) 1.0539(12) -0.5427(11) 0.0272(6) Uiso 1.000000 GR
H2Sb H 0.8426(18) 0.8643(6) -0.5312(10) 0.0272(6) Uiso 1.000000 GR
H2Sc H 0.9964(5) 0.9963(17) -0.6498(3) 0.0272(6) Uiso 1.000000 GR
H1Sa H 0.8668(16) 0.7262(4) -0.7478(6) 0.0286(7) Uiso 1.000000 GR
H1Sb H 0.8662(16) 0.8212(12) -0.9232(12) 0.0286(7) Uiso 1.000000 GR
H1Sc H 1.0309(3) 0.8466(9) -0.8698(17) 0.0286(7) Uiso 1.000000 GR
H1 H 0.5044(18) 0.7739(13) -0.4927(11) 0.0256(5) Uiso 1.000000 GR


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 C6 1.8940(19) . ?
S1S O1S 1.5289(14) . ?
S1S C2S 1.781(2) . ?
S1S C1S 1.787(2) . ?
O4 C5 1.343(2) . ?
O2 C1 1.234(2) . ?
O3 C3 1.352(2) . ?
O1 C1 1.315(2) . ?
C6 C5 1.400(3) . ?
C6 C7 1.374(3) . ?
C5 C4 1.391(3) . ?
C3 C2 1.404(3) . ?
C3 C4 1.388(3) . ?
C7 C2 1.402(3) . ?
C2 C1 1.468(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
C2S S1S O1S 106.83(9) . . ?
C1S S1S O1S 104.43(9) . . ?
C1S S1S C2S 98.68(10) . . ?
C5 C6 Br1 118.92(14) . . ?
C7 C6 Br1 120.19(14) . . ?
C7 C6 C5 120.89(18) . . ?
C6 C5 O4 118.00(17) . . ?
C4 C5 O4 123.24(17) . . ?
C4 C5 C6 118.75(18) . . ?
C2 C3 O3 122.59(18) . . ?
C4 C3 O3 117.32(17) . . ?
C4 C3 C2 120.09(18) . . ?
C2 C7 C6 120.55(18) . . ?
C7 C2 C3 118.79(18) . . ?
C1 C2 C3 119.94(17) . . ?
C1 C2 C7 121.27(18) . . ?
O1 C1 O2 122.65(18) . . ?
C2 C1 O2 122.08(18) . . ?
C2 C1 O1 115.27(17) . . ?
C3 C4 C5 120.88(18) . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        '5-bromo-resorcylic acid DMSO solvate'
####################################################################### 
# 
# 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_KE062
_database_code_depnum_ccdc_archive 'CCDC 2120716'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-11
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_formula_moiety         'C7 H5 Br O4, C2 H4 O'
_chemical_formula_sum            'C9 H9 Br O5'
_chemical_formula_weight         277.072
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   4.2750(4)
_cell_length_b                   10.1068(9)
_cell_length_c                   12.6263(12)
_cell_angle_alpha                108.660(3)
_cell_angle_beta                 98.455(3)
_cell_angle_gamma                97.857(3)
_cell_volume                     501.32(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4692
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      3.22
_exptl_absorpt_coefficient_mu    4.097
_exptl_absorpt_correction_T_max  0.7134
_exptl_absorpt_correction_T_min  0.4591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1363 before and 0.0858 after correction.
The Ratio of minimum to maximum transmission is 0.7175.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_description       plate
_exptl_crystal_F_000             275.765
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'Crystallised by precipitation from dioxane with toluene'
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.9978
_diffrn_reflns_Laue_measured_fraction_max 0.9980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8977
_diffrn_reflns_point_group_measured_fraction_full 0.9978
_diffrn_reflns_point_group_measured_fraction_max 0.9980
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.22
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              11
_reflns_limit_k_min              -12
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1734
_reflns_number_total             1975
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         1.6534
_refine_diff_density_min         -0.6153
_refine_diff_density_rms         0.1295
_refine_ls_d_res_high            0.8110
_refine_ls_d_res_low             6.3318
_refine_ls_goodness_of_fit_ref   1.0591
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.0591
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+0.9221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0815
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2S(H2Sa,H2Sb), C1S(H1Sa,H1Sb)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4a)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O3(H3)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br1 Br 0.34593(9) 0.01983(3) 0.66843(3) 0.02613(14) Uani 1.000000 .
O1 O -0.3616(6) 0.3315(2) 0.4984(2) 0.0243(5) Uani 1.000000 .
H1 H -0.481(7) 0.3660(5) 0.4598(19) 0.0364(8) Uiso 1.000000 GR
O4 O 0.7009(6) 0.2849(2) 0.8823(2) 0.0263(6) Uani 1.000000 .
H4 H 0.709(8) 0.1981(10) 0.8568(18) 0.0394(8) Uiso 1.000000 GR
O1S O 0.8872(6) 0.0626(2) 0.9202(2) 0.0228(5) Uani 1.000000 .
O3 O 0.2306(6) 0.6354(2) 0.7926(2) 0.0287(6) Uani 1.000000 .
H3 H 0.095(8) 0.6479(7) 0.743(2) 0.0431(9) Uiso 1.000000 GR
C6 C 0.2954(8) 0.2122(3) 0.7077(3) 0.0198(7) Uani 1.000000 .
C2S C 1.1232(9) 0.1434(4) 1.0219(3) 0.0237(7) Uani 1.000000 .
H2Sa H 1.3424(9) 0.1400(4) 1.0059(3) 0.0284(9) Uiso 1.000000 R
H2Sb H 1.0989(9) 0.2442(4) 1.0471(3) 0.0284(9) Uiso 1.000000 R
C7 C 0.0786(8) 0.2502(3) 0.6367(3) 0.0187(7) Uani 1.000000 .
H7 H -0.0512(8) 0.1794(3) 0.5696(3) 0.0225(8) Uiso 1.000000 R
C1S C 0.9182(9) -0.0838(3) 0.8848(3) 0.0237(7) Uani 1.000000 .
H1Sa H 0.7531(9) -0.1396(3) 0.8152(3) 0.0284(9) Uiso 1.000000 R
H1Sb H 1.1334(9) -0.0917(3) 0.8661(3) 0.0284(9) Uiso 1.000000 R
C3 C 0.2421(8) 0.4954(3) 0.7626(3) 0.0206(7) Uani 1.000000 .
C1 C -0.1868(8) 0.4339(3) 0.5885(3) 0.0203(7) Uani 1.000000 .
C2 C 0.0476(8) 0.3925(3) 0.6625(3) 0.0194(7) Uani 1.000000 .
C5 C 0.4854(8) 0.3145(4) 0.8088(3) 0.0214(7) Uani 1.000000 .
C4 C 0.4562(8) 0.4555(4) 0.8350(3) 0.0224(7) Uani 1.000000 .
H4a H 0.5835(8) 0.5255(4) 0.9031(3) 0.0269(9) Uiso 1.000000 R
O2 O -0.2164(6) 0.5605(2) 0.6102(2) 0.0250(5) Uani 1.000000 .


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 C6 1.898(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.307(4) . ?
O4 H4 0.8400 . ?
O4 C5 1.342(4) . ?
O1S C2S 1.434(4) . ?
O1S C1S 1.433(4) . ?
O3 H3 0.8400 . ?
O3 C3 1.352(4) . ?
C6 C7 1.372(5) . ?
C6 C5 1.406(5) . ?
C2S H2Sa 0.9900 . ?
C2S H2Sb 0.9900 . ?
C2S C1S 1.506(5) 2_757 ?
C7 H7 0.9500 . ?
C7 C2 1.399(4) . ?
C1S H1Sa 0.9900 . ?
C1S H1Sb 0.9900 . ?
C3 C2 1.408(5) . ?
C3 C4 1.389(5) . ?
C1 C2 1.463(5) . ?
C1 O2 1.249(4) . ?
C5 C4 1.384(5) . ?
C4 H4a 0.9500 . ?

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 O1 H1 109.5 . . ?
C5 O4 H4 109.5 . . ?
C1S O1S C2S 109.7(2) . . ?
C3 O3 H3 109.5 . . ?
C7 C6 Br1 119.8(3) . . ?
C5 C6 Br1 119.3(2) . . ?
C5 C6 C7 120.9(3) . . ?
H2Sa C2S O1S 109.64(18) . . ?
H2Sb C2S O1S 109.64(16) . . ?
H2Sb C2S H2Sa 108.2 . . ?
C1S C2S O1S 110.1(3) 2_757 . ?
C1S C2S H2Sa 109.64(19) 2_757 . ?
C1S C2S H2Sb 109.64(18) 2_757 . ?
H7 C7 C6 119.80(19) . . ?
C2 C7 C6 120.4(3) . . ?
C2 C7 H7 119.80(19) . . ?
C2S C1S O1S 110.4(3) 2_757 . ?
H1Sa C1S O1S 109.57(17) . . ?
H1Sa C1S C2S 109.57(19) . 2_757 ?
H1Sb C1S O1S 109.57(17) . . ?
H1Sb C1S C2S 109.57(19) . 2_757 ?
H1Sb C1S H1Sa 108.1 . . ?
C2 C3 O3 122.4(3) . . ?
C4 C3 O3 117.2(3) . . ?
C4 C3 C2 120.4(3) . . ?
C2 C1 O1 116.5(3) . . ?
O2 C1 O1 121.9(3) . . ?
O2 C1 C2 121.6(3) . . ?
C3 C2 C7 118.8(3) . . ?
C1 C2 C7 120.9(3) . . ?
C1 C2 C3 120.4(3) . . ?
C6 C5 O4 124.1(3) . . ?
C4 C5 O4 116.8(3) . . ?
C4 C5 C6 119.1(3) . . ?
C5 C4 C3 120.4(3) . . ?
H4a C4 C3 119.79(19) . . ?
H4a C4 C5 119.8(2) . . ?


_olex2_exptl_crystal_mounting_method 
'crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        '5-bromo-resorcylic acid dioxane hemisolvate'
####################################################################### 
# 
# 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_KE061
_database_code_depnum_ccdc_archive 'CCDC 2120720'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_formula_moiety         'C7 H5 Br O4, 0.5(C4 H8 O)'
_chemical_formula_sum            'C9 H9 Br O4.5'
_chemical_formula_weight         269.07
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   4.9186(7)
_cell_length_b                   14.079(2)
_cell_length_c                   14.695(2)
_cell_angle_alpha                97.214(4)
_cell_angle_beta                 91.367(3)
_cell_angle_gamma                98.717(4)
_cell_volume                     996.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    120
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    4.114
_exptl_absorpt_correction_T_max  0.9379
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1118 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.6322.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7926
_exptl_crystal_description       prism
_exptl_crystal_F_000             535.2321
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallised from butanone solution'
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.054
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_av_unetI/netI     0.1487
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17196
_diffrn_reflns_theta_full        26.8118
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_min         2.80
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9925
_diffrn_measured_fraction_theta_max 0.9925
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2467
_reflns_number_total             4245
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.9541
_refine_diff_density_min         -1.6888
_refine_diff_density_rms         0.4464
_refine_ls_d_res_high            0.7878
_refine_ls_d_res_low             7.2824
_refine_ls_goodness_of_fit_ref   1.0368
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.0368
_refine_ls_shift/su_max          0.0035
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0076P)²+2.1741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0897
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3S(H3Sa,H3Sb)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7a), C4(H4a), C14(H14), C11(H11)
2.c Idealised Me refined as rotating group:
 C1S(H1Sa,H1Sb,H1Sc), C4S(H4Sa,H4Sb,H4Sc)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O8(H8), O1(H1), O7(H7), O5(H5)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br2 Br 0.57633(13) 0.04177(4) 0.83313(4) 0.02574(19) Uani 1.000000 .
Br1 Br -0.09538(13) -0.72962(4) 0.74112(5) 0.0299(2) Uani 1.000000 .
O3 O 0.6485(8) -0.3544(2) 0.7153(3) 0.0222(10) Uani 1.000000 .
O4 O -0.0874(9) -0.5343(3) 0.8525(3) 0.0285(10) Uani 1.000000 .
O2 O 0.8828(8) -0.4432(3) 0.5844(2) 0.0202(9) Uani 1.000000 .
O8 O 0.5768(8) -0.1712(3) 0.7830(2) 0.0190(9) Uani 1.000000 .
O1 O 0.7226(8) -0.5984(3) 0.5331(3) 0.0242(10) Uani 1.000000 .
O7 O -0.1313(8) -0.2398(3) 0.5521(3) 0.0245(10) Uani 1.000000 .
O1S O -0.0847(9) -0.3499(3) 0.9335(3) 0.0411(12) Uani 1.000000 .
O5 O -0.2252(8) 0.0519(3) 0.5862(3) 0.0205(9) Uani 1.000000 .
O6 O -0.3738(8) -0.0970(3) 0.5131(3) 0.0210(9) Uani 1.000000 .
C1 C 0.7188(12) -0.5177(4) 0.5897(4) 0.0195(14) Uani 1.000000 .
C12 C 0.3839(12) -0.1429(4) 0.7302(4) 0.0164(13) Uani 1.000000 .
C14 C 0.1617(11) -0.0121(4) 0.6916(4) 0.0172(13) Uani 1.000000 .
C8 C -0.2170(12) -0.0416(4) 0.5711(4) 0.0186(14) Uani 1.000000 .
C9 C -0.0100(11) -0.0754(4) 0.6252(4) 0.0129(13) Uani 1.000000 .
C2 C 0.5094(11) -0.5234(4) 0.6574(4) 0.0165(13) Uani 1.000000 .
C11 C 0.2204(11) -0.2057(4) 0.6644(4) 0.0159(13) Uani 1.000000 .
C3 C 0.4801(11) -0.4411(4) 0.7178(4) 0.0160(13) Uani 1.000000 .
C5 C 0.1098(12) -0.5280(4) 0.7895(4) 0.0217(14) Uani 1.000000 .
C7 C 0.3295(11) -0.6092(4) 0.6656(4) 0.0199(14) Uani 1.000000 .
C6 C 0.1348(11) -0.6113(4) 0.7303(4) 0.0184(14) Uani 1.000000 .
C2S C -0.2067(13) -0.3028(5) 0.9902(4) 0.0337(17) Uani 1.000000 .
C13 C 0.3513(11) -0.0449(4) 0.7432(4) 0.0173(13) Uani 1.000000 .
C10 C 0.0252(11) -0.1730(4) 0.6132(4) 0.0162(13) Uani 1.000000 .
C4 C 0.2828(11) -0.4424(4) 0.7828(4) 0.0189(14) Uani 1.000000 .
C3S C -0.1270(14) -0.1955(4) 1.0080(4) 0.0372(18) Uani 1.000000 .
C1S C -0.4331(12) -0.3504(5) 1.0422(4) 0.0376(18) Uani 1.000000 .
C4S C 0.0819(14) -0.1500(5) 0.9480(4) 0.0413(19) Uani 1.000000 .
H7a H 0.3435(11) -0.6666(4) 0.6256(4) 0.0239(17) Uiso 1.000000 R
H4a H 0.2657(11) -0.3851(4) 0.8225(4) 0.0227(16) Uiso 1.000000 R
H14 H 0.1448(11) 0.0547(4) 0.7005(4) 0.0206(16) Uiso 1.000000 R
H11 H 0.2426(11) -0.2720(4) 0.6544(4) 0.0191(16) Uiso 1.000000 R
H3 H 0.763(8) -0.3612(11) 0.674(3) 0.0333(15) Uiso 1.000000 GR
H4 H -0.084(9) -0.4799(11) 0.884(3) 0.0427(16) Uiso 1.000000 GR
H8 H 0.605(8) -0.2267(17) 0.761(2) 0.0285(14) Uiso 1.000000 GR
H1 H 0.836(9) -0.5875(10) 0.492(2) 0.0363(15) Uiso 1.000000 GR
H7 H -0.257(8) -0.2147(12) 0.529(3) 0.0368(15) Uiso 1.000000 GR
H5 H -0.346(8) 0.0658(7) 0.551(3) 0.0308(14) Uiso 1.000000 GR
H3Sa H -0.2957(14) -0.1658(4) 1.0023(4) 0.045(2) Uiso 1.000000 R
H3Sb H -0.0556(14) -0.1784(4) 1.0725(4) 0.045(2) Uiso 1.000000 R
H1Sa H -0.405(4) -0.4170(10) 1.047(2) 0.056(3) Uiso 1.000000 GR
H1Sb H -0.433(5) -0.3143(17) 1.1037(10) 0.056(3) Uiso 1.000000 GR
H1Sc H -0.6100(14) -0.351(3) 1.0097(14) 0.056(3) Uiso 1.000000 GR
H4Sa H 0.123(6) -0.0802(6) 0.9681(18) 0.062(3) Uiso 1.000000 GR
H4Sb H 0.251(3) -0.179(2) 0.952(2) 0.062(3) Uiso 1.000000 GR
H4Sc H 0.009(4) -0.161(3) 0.8843(6) 0.062(3) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C13 1.891(5) . ?
Br1 C6 1.893(5) . ?
O3 C3 1.372(6) . ?
O4 C5 1.358(6) . ?
O2 C1 1.235(6) . ?
O8 C12 1.348(6) . ?
O1 C1 1.324(6) . ?
O7 C10 1.349(6) . ?
O1S C2S 1.225(7) . ?
O5 C8 1.314(6) . ?
O6 C8 1.244(6) . ?
C1 C2 1.450(7) . ?
C12 C11 1.377(7) . ?
C12 C13 1.403(7) . ?
C14 C9 1.405(7) . ?
C14 C13 1.357(7) . ?
C8 C9 1.449(8) . ?
C9 C10 1.400(7) . ?
C2 C3 1.397(7) . ?
C2 C7 1.405(7) . ?
C11 C10 1.374(7) . ?
C3 C4 1.377(7) . ?
C5 C6 1.393(8) . ?
C5 C4 1.382(7) . ?
C7 C6 1.365(7) . ?
C2S C3S 1.490(8) . ?
C2S C1S 1.489(8) . ?
C3S C4S 1.493(8) . ?

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 121.8(5) . . ?
C2 C1 O2 122.8(5) . . ?
C2 C1 O1 115.3(5) . . ?
C11 C12 O8 122.8(5) . . ?
C13 C12 O8 118.0(5) . . ?
C13 C12 C11 119.2(5) . . ?
C13 C14 C9 121.1(5) . . ?
O6 C8 O5 122.1(5) . . ?
C9 C8 O5 115.5(5) . . ?
C9 C8 O6 122.4(5) . . ?
C8 C9 C14 121.5(5) . . ?
C10 C9 C14 117.5(5) . . ?
C10 C9 C8 120.9(5) . . ?
C3 C2 C1 119.9(5) . . ?
C7 C2 C1 122.9(5) . . ?
C7 C2 C3 117.3(5) . . ?
C10 C11 C12 120.3(5) . . ?
C2 C3 O3 121.3(5) . . ?
C4 C3 O3 116.6(5) . . ?
C4 C3 C2 122.1(5) . . ?
C6 C5 O4 118.0(5) . . ?
C4 C5 O4 122.1(5) . . ?
C4 C5 C6 119.9(5) . . ?
C6 C7 C2 121.0(5) . . ?
C5 C6 Br1 120.1(4) . . ?
C7 C6 Br1 119.3(4) . . ?
C7 C6 C5 120.5(5) . . ?
C3S C2S O1S 119.6(6) . . ?
C1S C2S O1S 121.4(6) . . ?
C1S C2S C3S 119.1(6) . . ?
C12 C13 Br2 119.3(4) . . ?
C14 C13 Br2 120.1(4) . . ?
C14 C13 C12 120.6(5) . . ?
C9 C10 O7 122.2(5) . . ?
C11 C10 O7 116.5(5) . . ?
C11 C10 C9 121.3(5) . . ?
C5 C4 C3 119.2(5) . . ?
C4S C3S C2S 117.1(6) . . ?


_olex2_exptl_crystal_mounting_method 
'crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
'5-bromo-resorcylic acid 2-butanone hemisolvate'
####################################################################### 
# 
# 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_ke031
_database_code_depnum_ccdc_archive 'CCDC 2120718'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        '3,5-dibromo-resorcylic acid dioxane solvate'
_chemical_formula_moiety         'C7 H4 Br2 O4, C4 H8 O2'
_chemical_formula_sum            'C11 H12 Br2 O6'
_chemical_formula_weight         400.03
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0921(3)
_cell_length_b                   9.6935(6)
_cell_length_c                   27.0491(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.041(2)
_cell_angle_gamma                90
_cell_volume                     1334.93(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6745
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.091
_exptl_absorpt_correction_T_max  0.7097
_exptl_absorpt_correction_T_min  0.4818
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.6789.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'crystallised by evaporation from dioxane'
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            13871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2290
_reflns_number_total             2628
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0118P)²+1.3001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0443
_refine_ls_wR_factor_ref         0.0462
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB), C1S(H1SA,H1SB)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.07234(5) 0.27020(3) 0.29059(2) 0.01261(7) Uani 1 1 d . . . . .
Br2 Br -0.20612(6) 0.29882(3) 0.49240(2) 0.02450(9) Uani 1 1 d . . . . .
O3 O -0.3547(4) 0.47997(19) 0.28120(6) 0.0159(4) Uani 1 1 d . . . . .
H3 H -0.475629 0.535377 0.278249 0.024 Uiso 1 1 calc R U . . .
O4 O 0.0890(3) 0.20925(18) 0.40379(6) 0.0144(4) Uani 1 1 d . . . . .
H4 H 0.178978 0.188837 0.380037 0.022 Uiso 1 1 calc R U . . .
O2S O -0.5305(3) 1.05303(18) 0.36763(6) 0.0150(4) Uani 1 1 d . . . . .
O2 O -0.8397(3) 0.63294(18) 0.39074(6) 0.0145(4) Uani 1 1 d . . . . .
H2 H -0.955022 0.685985 0.381030 0.022 Uiso 1 1 calc R U . . .
O1S O -0.2161(3) 0.81402(18) 0.37389(6) 0.0158(4) Uani 1 1 d . . . . .
O1 O -0.7397(3) 0.63503(18) 0.31060(6) 0.0154(4) Uani 1 1 d . . . . .
C5 C -0.0962(5) 0.3009(2) 0.38954(9) 0.0105(5) Uani 1 1 d . . . . .
C3 C -0.3298(5) 0.4413(2) 0.32881(9) 0.0092(5) Uani 1 1 d . . . . .
C2 C -0.4904(5) 0.4936(2) 0.36585(9) 0.0102(5) Uani 1 1 d . . . . .
C1 C -0.6985(5) 0.5928(3) 0.35290(9) 0.0107(5) Uani 1 1 d . . . . .
C7 C -0.4516(5) 0.4481(3) 0.41469(9) 0.0126(5) Uani 1 1 d . . . . .
H7 H -0.558603 0.481409 0.439509 0.015 Uiso 1 1 calc R U . . .
C4 C -0.1368(5) 0.3445(2) 0.34107(9) 0.0092(5) Uani 1 1 d . . . . .
C2S C -0.4734(5) 0.9736(3) 0.32428(9) 0.0150(6) Uani 1 1 d . . . . .
H2SA H -0.467913 1.034034 0.295722 0.018 Uiso 1 1 calc R U . . .
H2SB H -0.611201 0.906093 0.318541 0.018 Uiso 1 1 calc R U . . .
C6 C -0.2580(5) 0.3552(3) 0.42606(9) 0.0116(5) Uani 1 1 d . . . . .
C3S C -0.5327(5) 0.9659(3) 0.41048(10) 0.0164(6) Uani 1 1 d . . . . .
H3SA H -0.671582 0.897997 0.406848 0.020 Uiso 1 1 calc R U . . .
H3SB H -0.568135 1.021123 0.439522 0.020 Uiso 1 1 calc R U . . .
C4S C -0.2732(5) 0.8939(3) 0.41719(9) 0.0162(6) Uani 1 1 d . . . . .
H4SA H -0.135485 0.961514 0.422861 0.019 Uiso 1 1 calc R U . . .
H4SB H -0.278888 0.833786 0.445824 0.019 Uiso 1 1 calc R U . . .
C1S C -0.2128(5) 0.9011(3) 0.33078(10) 0.0158(6) Uani 1 1 d . . . . .
H1SA H -0.178219 0.845666 0.301756 0.019 Uiso 1 1 calc R U . . .
H1SB H -0.073513 0.968808 0.334319 0.019 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 C4 1.890(2) . ?
Br2 C6 1.890(2) . ?
O3 H3 0.8200 . ?
O3 C3 1.345(3) . ?
O4 H4 0.8200 . ?
O4 C5 1.347(3) . ?
O2S C2S 1.437(3) . ?
O2S C3S 1.434(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.320(3) . ?
O1S C4S 1.438(3) . ?
O1S C1S 1.440(3) . ?
O1 C1 1.230(3) . ?
C5 C4 1.389(3) . ?
C5 C6 1.400(3) . ?
C3 C2 1.400(3) . ?
C3 C4 1.394(3) . ?
C2 C1 1.469(3) . ?
C2 C7 1.403(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.366(3) . ?
C2S H2SA 0.9700 . ?
C2S H2SB 0.9700 . ?
C2S C1S 1.509(3) . ?
C3S H3SA 0.9700 . ?
C3S H3SB 0.9700 . ?
C3S C4S 1.503(3) . ?
C4S H4SA 0.9700 . ?
C4S H4SB 0.9700 . ?
C1S H1SA 0.9700 . ?
C1S H1SB 0.9700 . ?

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
C3 O3 H3 109.5 . . ?
C5 O4 H4 109.5 . . ?
C3S O2S C2S 110.43(19) . . ?
C1 O2 H2 109.5 . . ?
C4S O1S C1S 110.46(19) . . ?
O4 C5 C4 124.2(2) . . ?
O4 C5 C6 117.6(2) . . ?
C4 C5 C6 118.2(2) . . ?
O3 C3 C2 122.6(2) . . ?
O3 C3 C4 118.0(2) . . ?
C4 C3 C2 119.5(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 119.1(2) . . ?
C7 C2 C1 121.3(2) . . ?
O2 C1 C2 114.1(2) . . ?
O1 C1 O2 122.5(2) . . ?
O1 C1 C2 123.4(2) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C5 C4 Br1 119.31(18) . . ?
C5 C4 C3 121.4(2) . . ?
C3 C4 Br1 119.25(18) . . ?
O2S C2S H2SA 109.6 . . ?
O2S C2S H2SB 109.6 . . ?
O2S C2S C1S 110.2(2) . . ?
H2SA C2S H2SB 108.1 . . ?
C1S C2S H2SA 109.6 . . ?
C1S C2S H2SB 109.6 . . ?
C5 C6 Br2 119.16(18) . . ?
C7 C6 Br2 119.49(19) . . ?
C7 C6 C5 121.4(2) . . ?
O2S C3S H3SA 109.5 . . ?
O2S C3S H3SB 109.5 . . ?
O2S C3S C4S 110.6(2) . . ?
H3SA C3S H3SB 108.1 . . ?
C4S C3S H3SA 109.5 . . ?
C4S C3S H3SB 109.5 . . ?
O1S C4S C3S 110.0(2) . . ?
O1S C4S H4SA 109.7 . . ?
O1S C4S H4SB 109.7 . . ?
C3S C4S H4SA 109.7 . . ?
C3S C4S H4SB 109.7 . . ?
H4SA C4S H4SB 108.2 . . ?
O1S C1S C2S 110.1(2) . . ?
O1S C1S H1SA 109.6 . . ?
O1S C1S H1SB 109.6 . . ?
C2S C1S H1SA 109.6 . . ?
C2S C1S H1SB 109.6 . . ?
H1SA C1S H1SB 108.1 . . ?

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
O3 C3 C2 C1 1.1(4) . . . . ?
O3 C3 C2 C7 -179.9(2) . . . . ?
O3 C3 C4 Br1 -1.4(3) . . . . ?
O3 C3 C4 C5 179.0(2) . . . . ?
O4 C5 C4 Br1 1.3(3) . . . . ?
O4 C5 C4 C3 -179.1(2) . . . . ?
O4 C5 C6 Br2 0.5(3) . . . . ?
O4 C5 C6 C7 -179.6(2) . . . . ?
O2S C2S C1S O1S 57.7(3) . . . . ?
O2S C3S C4S O1S -58.0(3) . . . . ?
C3 C2 C1 O2 178.9(2) . . . . ?
C3 C2 C1 O1 -0.9(4) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C2 C3 C4 Br1 178.12(18) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C2 C7 C6 Br2 178.71(19) . . . . ?
C2 C7 C6 C5 -1.2(4) . . . . ?
C1 C2 C7 C6 179.7(2) . . . . ?
C7 C2 C1 O2 0.0(3) . . . . ?
C7 C2 C1 O1 -179.8(2) . . . . ?
C4 C5 C6 Br2 -179.60(18) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C4 C3 C2 C1 -178.4(2) . . . . ?
C4 C3 C2 C7 0.6(4) . . . . ?
C2S O2S C3S C4S 58.1(3) . . . . ?
C6 C5 C4 Br1 -178.53(18) . . . . ?
C6 C5 C4 C3 1.0(4) . . . . ?
C3S O2S C2S C1S -57.8(3) . . . . ?
C4S O1S C1S C2S -58.0(3) . . . . ?
C1S O1S C4S C3S 58.0(3) . . . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal coated in perfluoro polyether oil and mounted on a MiTeGen sample holder directly into the precooled cryostream'
_olex2_submission_original_sample_id 'BRA DIO'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_KE048
_database_code_depnum_ccdc_archive 'CCDC 2120723'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C7 H5 Br O4, C4 H8 O'
_chemical_formula_sum            'C11 H13 Br O5'
_chemical_formula_weight         305.13
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.8148(4)
_cell_length_b                   15.5203(12)
_cell_length_c                   15.6723(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.448(2)
_cell_angle_gamma                90
_cell_volume                     1163.74(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7743
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.149
_cell_measurement_theta_min      2.616
_exptl_absorpt_coefficient_mu    3.539
_exptl_absorpt_correction_T_max  0.8939
_exptl_absorpt_correction_T_min  0.2738
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1736 before and 0.0957 after correction.
The Ratio of minimum to maximum transmission is 0.3063.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7414
_exptl_crystal_description       prism
_exptl_crystal_F_000             615.2619
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Crystallised from THF by slow cooling'
_exptl_crystal_size_max          0.802
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.064
_diffrn_reflns_av_R_equivalents  0.1354
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25375
_diffrn_reflns_theta_full        27.2001
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         2.62
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          
'The THF solvent molecule is disordered over two sites'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1975
_reflns_number_total             2578
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.8443
_refine_diff_density_min         -1.2476
_refine_diff_density_rms         0.2599
_refine_ls_d_res_high            0.7774
_refine_ls_d_res_low             7.7866
_refine_ls_goodness_of_fit_ref   0.9714
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      0.9666
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1442
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3s) \\sim Ueq, Uanis(C2s) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5s) \\sim Ueq, Uanis(C4s) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(C14a)=Sof(C2s)=Sof(C4s)=Sof(H6sd)=Sof(H6sc)=Sof(H1sd)=Sof(H1sc)=Sof(H4sb)=
 Sof(H4sa)=Sof(H2sa)=Sof(H2sb)=1-FVAR(1)
 Sof(C3s)=Sof(C5s)=Sof(H3sa)=Sof(H3sb)=Sof(H6sa)=Sof(H6sb)=Sof(H1sb)=Sof(H1sa)=
 Sof(H5sb)=Sof(H5sa)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3s(H3sa,H3sb), C6s(H6sd,H6sc), C6s(H6sa,H6sb), C1s(H1sb,H1sa), C1s(H1sd,
 H1sc), C4s(H4sb,H4sa), C5s(H5sb,H5sa), C2s(H2sa,H2sb)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4a), C7(H7)
4.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Br1 Br -0.14176(9) 0.30258(3) 0.26201(3) 0.01707(19) Uani 1.000000 . . .
O4 O -0.2317(7) 0.4666(2) 0.1606(2) 0.0198(7) Uani 1.000000 . . .
O2 O 0.8306(6) 0.5611(2) 0.42364(19) 0.0155(7) Uani 1.000000 . . .
O3 O 0.5105(6) 0.6343(2) 0.2962(2) 0.0203(8) Uani 1.000000 . . .
O1 O 0.7269(6) 0.4269(2) 0.46261(19) 0.0158(7) Uani 1.000000 . . .
C7 C 0.2853(8) 0.4135(3) 0.3378(3) 0.0125(9) Uani 1.000000 . . .
O1s O 0.3252(9) 0.0980(2) 0.4434(2) 0.0381(10) Uani 1.000000 . . .
C5 C -0.0110(9) 0.4763(3) 0.2211(3) 0.0137(9) Uani 1.000000 . . .
C4 C 0.1407(9) 0.5512(3) 0.2305(3) 0.0154(9) Uani 1.000000 . . .
C6 C 0.0631(9) 0.4069(3) 0.2757(3) 0.0142(9) Uani 1.000000 . . .
C3 C 0.3685(9) 0.5591(3) 0.2927(3) 0.0135(9) Uani 1.000000 . . .
C1 C 0.6807(9) 0.4957(3) 0.4136(3) 0.0144(9) Uani 1.000000 . . .
C3s C 0.228(4) 0.1977(12) 0.5533(12) 0.027(4) Uani 0.431(17) . U 1
C6s C 0.4428(12) 0.1797(3) 0.4286(3) 0.0250(12) Uani 1.000000 . . .
C2 C 0.4429(9) 0.4897(3) 0.3482(3) 0.0128(9) Uani 1.000000 . . .
C1s C 0.2047(12) 0.0986(4) 0.5232(3) 0.0308(13) Uani 1.000000 . . .
C4s C 0.312(2) 0.2379(6) 0.4904(6) 0.022(3) Uani 0.569(17) . U 2
C5s C 0.493(3) 0.2213(8) 0.5181(7) 0.021(4) Uani 0.431(17) . U 1
C2s C 0.305(3) 0.1778(9) 0.5680(7) 0.025(3) Uani 0.569(17) . U 2
H4a H 0.0889(9) 0.5986(3) 0.1937(3) 0.0185(11) Uiso 1.000000 R . .
H7 H 0.3338(8) 0.3659(3) 0.3746(3) 0.0150(11) Uiso 1.000000 R . .
H4 H -0.255(7) 0.5120(13) 0.131(2) 0.0297(11) Uiso 1.000000 GR . .
H3 H 0.659(6) 0.6291(11) 0.329(3) 0.0305(11) Uiso 1.000000 GR . .
H1 H 0.869(6) 0.4351(13) 0.498(2) 0.0237(10) Uiso 1.000000 GR . .
H3sa H 0.068(4) 0.2324(12) 0.5273(12) 0.033(5) Uiso 0.431(17) R . 1
H3sb H 0.245(4) 0.2033(12) 0.6166(12) 0.033(5) Uiso 0.431(17) R . 1
H6sd H 0.6489(12) 0.1786(3) 0.4415(3) 0.0300(14) Uiso 0.569(17) R . 2
H6sc H 0.3934(12) 0.1985(3) 0.3685(3) 0.0300(14) Uiso 0.569(17) R . 2
H6sa H 0.6206(12) 0.1733(3) 0.4031(3) 0.0300(14) Uiso 0.431(17) R . 1
H6sb H 0.3122(12) 0.2149(3) 0.3897(3) 0.0300(14) Uiso 0.431(17) R . 1
H1sb H 0.0072(12) 0.0797(4) 0.5148(3) 0.0369(15) Uiso 0.431(17) R . 1
H1sa H 0.3103(12) 0.0606(4) 0.5659(3) 0.0369(15) Uiso 0.431(17) R . 1
H1sd H -0.0019(12) 0.0987(4) 0.5126(3) 0.0369(15) Uiso 0.569(17) R . 2
H1sc H 0.2650(12) 0.0473(4) 0.5579(3) 0.0369(15) Uiso 0.569(17) R . 2
H4sb H 0.428(2) 0.2896(6) 0.5052(6) 0.026(3) Uiso 0.569(17) R . 2
H4sa H 0.121(2) 0.2562(6) 0.4669(6) 0.026(3) Uiso 0.569(17) R . 2
H5sb H 0.516(3) 0.2846(8) 0.5144(7) 0.026(4) Uiso 0.431(17) R . 1
H5sa H 0.659(3) 0.1963(8) 0.5527(7) 0.026(4) Uiso 0.431(17) R . 1
H2sa H 0.174(3) 0.1985(9) 0.6077(7) 0.030(4) Uiso 0.569(17) R . 2
H2sb H 0.493(3) 0.1701(9) 0.5998(7) 0.030(4) Uiso 0.569(17) R . 2


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 C6 1.895(5) . ?
O4 C5 1.350(5) . ?
O2 C1 1.245(5) . ?
O3 C3 1.351(5) . ?
O1 C1 1.320(5) . ?
C7 C6 1.368(6) . ?
C7 C2 1.404(6) . ?
O1s C6s 1.419(6) . ?
O1s C1s 1.437(6) . ?
C5 C4 1.373(6) . ?
C5 C6 1.397(6) . ?
C4 C3 1.389(6) . ?
C3 C2 1.405(6) . ?
C1 C2 1.452(6) . ?
C3s C1s 1.609(19) . ?
C3s C5s 1.49(2) . ?
C6s C4s 1.513(10) . ?
C6s C5s 1.539(12) . ?
C1s C2s 1.470(14) . ?
C4s C2s 1.536(15) . ?

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 C7 C6 121.0(4) . . ?
C1s O1s C6s 110.1(4) . . ?
C4 C5 O4 122.4(4) . . ?
C6 C5 O4 118.1(4) . . ?
C6 C5 C4 119.4(4) . . ?
C3 C4 C5 121.3(4) . . ?
C7 C6 Br1 120.1(3) . . ?
C5 C6 Br1 119.7(3) . . ?
C5 C6 C7 120.2(4) . . ?
C4 C3 O3 117.4(4) . . ?
C2 C3 O3 123.1(4) . . ?
C2 C3 C4 119.5(4) . . ?
O1 C1 O2 121.9(4) . . ?
C2 C1 O2 122.8(4) . . ?
C2 C1 O1 115.3(4) . . ?
C3 C2 C7 118.5(4) . . ?
C1 C2 C7 120.6(4) . . ?
C1 C2 C3 120.9(4) . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted onto MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C3s 0.0100
C4s 0.0100
C5s 0.0100
C2s 0.0100

_chemical_name_systematic        '5-bromo-resorcylic acid THF solvate'
####################################################################### 
# 
# 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_ke064
_database_code_depnum_ccdc_archive 'CCDC 2120730'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        'Resorcylic acid acetic acid solvate'
_chemical_formula_moiety         'C7 H6 O4, C2 H4 O2'
_chemical_formula_sum            'C9 H10 O6'
_chemical_formula_weight         214.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.6177(5)
_cell_length_b                   17.933(2)
_cell_length_c                   11.6033(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.898(4)
_cell_angle_gamma                90
_cell_volume                     946.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4022
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0879 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.9155. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'Crystallised by slow cooling from acetic acid'
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.118
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16041
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1387
_reflns_number_total             1868
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.2996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4A), C6(H6)
2.b Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O3(H3), O1S(H1S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O1 O 0.5415(3) 0.81390(7) 0.11497(11) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.6028 0.8547 0.1402 0.030 Uiso 1 1 calc GR . . . .
O4 O -0.2374(3) 0.55612(6) -0.13546(11) 0.0197(3) Uani 1 1 d . . . . .
H4 H -0.3889 0.5637 -0.1823 0.030 Uiso 1 1 calc GR . . . .
O3 O -0.2362(3) 0.82045(7) -0.13089(11) 0.0209(3) Uani 1 1 d . . . . .
H3 H -0.1492 0.8557 -0.0955 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.1832(3) 0.88533(7) 0.01750(11) 0.0190(3) Uani 1 1 d . . . . .
O2S O 0.7574(3) 0.94224(7) 0.20189(11) 0.0181(3) Uani 1 1 d . . . . .
O1S O 0.3734(3) 1.01198(7) 0.12390(11) 0.0184(3) Uani 1 1 d . . . . .
H1S H 0.3204 0.9725 0.0911 0.028 Uiso 1 1 calc GR . . . .
C2 C 0.1526(4) 0.75409(10) -0.00590(15) 0.0143(4) Uani 1 1 d . . . . .
C7 C 0.2686(4) 0.68408(10) 0.03161(15) 0.0156(4) Uani 1 1 d . . . . .
H7 H 0.4384 0.6819 0.0877 0.019 Uiso 1 1 calc R . . . .
C4 C -0.2351(4) 0.69022(10) -0.13626(15) 0.0151(4) Uani 1 1 d . . . . .
H4A H -0.4027 0.6918 -0.1936 0.018 Uiso 1 1 calc R . . . .
C1 C 0.2918(4) 0.82264(10) 0.04231(15) 0.0146(4) Uani 1 1 d . . . . .
C3 C -0.1046(4) 0.75592(10) -0.09058(15) 0.0137(4) Uani 1 1 d . . . . .
C5 C -0.1155(4) 0.62231(10) -0.09634(15) 0.0145(4) Uani 1 1 d . . . . .
C1S C 0.6256(4) 1.00209(10) 0.19425(15) 0.0151(4) Uani 1 1 d . . . . .
C2S C 0.7376(4) 1.06823(10) 0.26551(16) 0.0192(4) Uani 1 1 d . . . . .
H2SA H 0.7032 1.0617 0.3442 0.029 Uiso 1 1 calc GR . . . .
H2SB H 0.6372 1.1121 0.2323 0.029 Uiso 1 1 calc GR . . . .
H2SC H 0.9447 1.0735 0.2660 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.1395(4) 0.61892(10) -0.01190(16) 0.0171(4) Uani 1 1 d . . . . .
H6 H 0.2200 0.5732 0.0143 0.020 Uiso 1 1 calc R . . . .


_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
O1 C1 1.316(2) . ?
O4 C5 1.358(2) . ?
O3 C3 1.353(2) . ?
O2 C1 1.244(2) . ?
O2S C1S 1.229(2) . ?
O1S C1S 1.314(2) . ?
C2 C7 1.404(2) . ?
C2 C1 1.454(2) . ?
C2 C3 1.406(2) . ?
C7 C6 1.368(2) . ?
C4 C3 1.387(2) . ?
C4 C5 1.384(2) . ?
C5 C6 1.398(2) . ?
C1S C2S 1.487(2) . ?

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 C2 C1 121.12(16) . . ?
C7 C2 C3 117.97(16) . . ?
C3 C2 C1 120.91(16) . . ?
C6 C7 C2 122.02(16) . . ?
C5 C4 C3 119.85(15) . . ?
O1 C1 C2 115.25(15) . . ?
O2 C1 O1 121.98(16) . . ?
O2 C1 C2 122.77(15) . . ?
O3 C3 C2 122.49(16) . . ?
O3 C3 C4 117.05(15) . . ?
C4 C3 C2 120.46(16) . . ?
O4 C5 C4 122.61(15) . . ?
O4 C5 C6 116.55(15) . . ?
C4 C5 C6 120.83(16) . . ?
O2S C1S O1S 122.51(16) . . ?
O2S C1S C2S 122.39(16) . . ?
O1S C1S C2S 115.09(15) . . ?
C7 C6 C5 118.86(16) . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluroo polyether oil and mounted on MiTeGen sample holders directly into the pre-cooled cryostream.'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ke037
_database_code_depnum_ccdc_archive 'CCDC 2120728'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        '3,5-dibromo-resorcylic acid pentanol solvate'
_chemical_formula_moiety         'C7 H4 Br2 O4, C5 H12 O'
_chemical_formula_sum            'C12 H16 Br2 O5'
_chemical_formula_weight         400.07
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.1238(4)
_cell_length_b                   24.7317(15)
_cell_length_c                   7.2459(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.5848(19)
_cell_angle_gamma                90
_cell_volume                     1452.96(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.591
_exptl_absorpt_correction_T_max  0.6449
_exptl_absorpt_correction_T_min  0.2455
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1163 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.3807.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_preparation       'cut from a larger crystal'
_exptl_crystal_recrystallization_method 
'crystallised by slow cooling from pentanol solution'
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.138
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21736
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.512
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2526
_reflns_number_total             2841
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0163P)²+1.8096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Sof(H1SA)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=Sof(C1SA)=Sof(H1SD)=Sof(H1SE)=
 Sof(C2SA)=Sof(H2SC)=Sof(H2SD)=Sof(C3SA)=Sof(H3SC)=Sof(H3SD)=Sof(C4SA)=
 Sof(H4SC)=Sof(H4SD)=1-FVAR(1)
 Sof(H1S)=Sof(C3SB)=Sof(H3SA)=Sof(H3SB)=Sof(H5SD)=Sof(H5SE)=Sof(H5SF)=
 Sof(C4SB)=Sof(H4SA)=Sof(H4SB)=Sof(C1SB)=Sof(H1SB)=Sof(H1SC)=Sof(C2SB)=
 Sof(H2SA)=Sof(H2SB)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C3SB(H3SA,H3SB), C4SB(H4SA,H4SB), C1SB(H1SB,H1SC), C2SB(H2SA,H2SB), C1SA(H1SD,
 H1SE), C2SA(H2SC,H2SD), C3SA(H3SC,H3SD), C4SA(H4SC,H4SD)
3.b Me refined with riding coordinates:
 C5S(H5SA,H5SB,H5SC), C5S(H5SD,H5SE,H5SF)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
3.d Tetrahedral OH refined with riding coordinates:
 O1S(H1S), O1S(H1SA)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.51487(3) 0.67632(2) 0.40530(4) 0.02177(9) Uani 1 1 d . . . . .
Br1 Br 0.81023(4) 0.88253(2) 0.52178(5) 0.02888(10) Uani 1 1 d . . . . .
O2 O 1.1318(3) 0.64717(9) 0.6771(3) 0.0304(5) Uani 1 1 d . . . . .
H2 H 1.221445 0.635218 0.724647 0.046 Uiso 1 1 calc R U . . .
O4 O 0.5496(2) 0.80241(8) 0.4084(3) 0.0219(4) Uani 1 1 d . . . . .
H4 H 0.475573 0.779964 0.376463 0.033 Uiso 1 1 calc R U . . .
O3 O 1.0935(2) 0.81481(8) 0.6654(3) 0.0251(5) Uani 1 1 d . . . . .
H3 H 1.173054 0.795783 0.706916 0.038 Uiso 1 1 calc R U . . .
O1 O 1.2479(2) 0.72684(9) 0.7553(3) 0.0251(5) Uani 1 1 d . . . . .
O1S O 1.3863(3) 0.59945(9) 0.8307(3) 0.0347(6) Uani 1 1 d . . . . .
H1S H 1.436348 0.629178 0.831698 0.052 Uiso 0.583(7) 1 calc R U P A 1
H1SA H 1.433271 0.619840 0.910338 0.052 Uiso 0.417(7) 1 calc R U P A 2
C2 C 0.9781(3) 0.72601(12) 0.6125(4) 0.0181(6) Uani 1 1 d . . . . .
C6 C 0.6986(3) 0.71956(11) 0.4847(3) 0.0155(6) Uani 1 1 d . . . . .
C4 C 0.8220(3) 0.80650(11) 0.5360(4) 0.0166(6) Uani 1 1 d . . . . .
C3 C 0.9672(3) 0.78242(12) 0.6067(4) 0.0174(6) Uani 1 1 d . . . . .
C7 C 0.8409(3) 0.69518(11) 0.5502(4) 0.0175(6) Uani 1 1 d . . . . .
H7 H 0.847184 0.656838 0.553628 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6857(3) 0.77589(11) 0.4746(3) 0.0171(6) Uani 1 1 d . . . . .
C1 C 1.1311(3) 0.69994(12) 0.6880(4) 0.0208(6) Uani 1 1 d . . . . .
C3SB C 1.1690(10) 0.5215(3) 1.2059(8) 0.0354(16) Uani 0.583(7) 1 d . . P A 1
H3SA H 1.079746 0.494442 1.186376 0.042 Uiso 0.583(7) 1 calc R U P A 1
H3SB H 1.120806 0.554021 1.260856 0.042 Uiso 0.583(7) 1 calc R U P A 1
C5S C 1.2216(5) 0.4709(2) 1.5120(6) 0.0622(13) Uani 1 1 d . . . . .
H5SA H 1.309701 0.456649 1.597056 0.093 Uiso 0.417(7) 1 calc R U P A 1
H5SB H 1.156832 0.497484 1.576655 0.093 Uiso 0.417(7) 1 calc R U P A 1
H5SC H 1.149687 0.441135 1.467872 0.093 Uiso 0.417(7) 1 calc R U P A 1
H5SD H 1.211522 0.478111 1.643810 0.093 Uiso 0.583(7) 1 calc R U P A 2
H5SE H 1.117875 0.455647 1.458584 0.093 Uiso 0.583(7) 1 calc R U P A 2
H5SF H 1.311270 0.445018 1.497300 0.093 Uiso 0.583(7) 1 calc R U P A 2
C4SB C 1.2995(8) 0.4986(3) 1.3426(12) 0.0356(17) Uani 0.583(7) 1 d . . P A 1
H4SA H 1.373693 0.528169 1.387998 0.043 Uiso 0.583(7) 1 calc R U P A 1
H4SB H 1.366545 0.471799 1.279174 0.043 Uiso 0.583(7) 1 calc R U P A 1
C1SB C 1.3532(8) 0.5829(3) 1.0328(10) 0.0288(16) Uani 0.583(7) 1 d . . P A 1
H1SB H 1.456995 0.571229 1.100106 0.035 Uiso 0.583(7) 1 calc R U P A 1
H1SC H 1.307466 0.613818 1.099565 0.035 Uiso 0.583(7) 1 calc R U P A 1
C2SB C 1.2302(7) 0.5366(2) 1.0199(8) 0.0313(16) Uani 0.583(7) 1 d . . P A 1
H2SA H 1.135002 0.546989 0.935503 0.038 Uiso 0.583(7) 1 calc R U P A 1
H2SB H 1.282990 0.504599 0.966301 0.038 Uiso 0.583(7) 1 calc R U P A 1
C1SA C 1.3353(10) 0.5540(3) 0.9134(12) 0.031(2) Uani 0.417(7) 1 d . . P A 2
H1SD H 1.415625 0.524522 0.897166 0.037 Uiso 0.417(7) 1 calc R U P A 2
H1SE H 1.227353 0.542541 0.855309 0.037 Uiso 0.417(7) 1 calc R U P A 2
C2SA C 1.3199(10) 0.5641(3) 1.1128(14) 0.027(2) Uani 0.417(7) 1 d . . P A 2
H2SC H 1.234175 0.591863 1.128245 0.033 Uiso 0.417(7) 1 calc R U P A 2
H2SD H 1.425809 0.578208 1.168102 0.033 Uiso 0.417(7) 1 calc R U P A 2
C3SA C 1.2742(13) 0.5125(3) 1.2143(12) 0.024(2) Uani 0.417(7) 1 d . . P A 2
H3SC H 1.168904 0.498581 1.156595 0.029 Uiso 0.417(7) 1 calc R U P A 2
H3SD H 1.359937 0.484907 1.195972 0.029 Uiso 0.417(7) 1 calc R U P A 2
C4SA C 1.2558(12) 0.5189(4) 1.4216(14) 0.035(2) Uani 0.417(7) 1 d . . P A 2
H4SC H 1.359070 0.534377 1.479032 0.042 Uiso 0.417(7) 1 calc R U P A 2
H4SD H 1.165945 0.544991 1.440370 0.042 Uiso 0.417(7) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C6 1.896(3) . ?
Br1 C4 1.885(3) . ?
O2 H2 0.8400 . ?
O2 C1 1.308(4) . ?
O4 H4 0.8400 . ?
O4 C5 1.348(3) . ?
O3 H3 0.8400 . ?
O3 C3 1.349(3) . ?
O1 C1 1.234(3) . ?
O1S H1S 0.8400 . ?
O1S H1SA 0.8400 . ?
O1S C1SB 1.560(7) . ?
O1S C1SA 1.352(8) . ?
C2 C3 1.399(4) . ?
C2 C7 1.402(4) . ?
C2 C1 1.475(4) . ?
C6 C7 1.362(4) . ?
C6 C5 1.399(4) . ?
C4 C3 1.390(4) . ?
C4 C5 1.392(4) . ?
C7 H7 0.9500 . ?
C3SB H3SA 0.9900 . ?
C3SB H3SB 0.9900 . ?
C3SB C4SB 1.514(9) . ?
C3SB C2SB 1.512(8) . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?
C5S H5SD 0.9800 . ?
C5S H5SE 0.9800 . ?
C5S H5SF 0.9800 . ?
C5S C4SB 1.574(8) . ?
C5S C4SA 1.393(10) . ?
C4SB H4SA 0.9900 . ?
C4SB H4SB 0.9900 . ?
C1SB H1SB 0.9900 . ?
C1SB H1SC 0.9900 . ?
C1SB C2SB 1.519(9) . ?
C2SB H2SA 0.9900 . ?
C2SB H2SB 0.9900 . ?
C1SA H1SD 0.9900 . ?
C1SA H1SE 0.9900 . ?
C1SA C2SA 1.479(13) . ?
C2SA H2SC 0.9900 . ?
C2SA H2SD 0.9900 . ?
C2SA C3SA 1.530(12) . ?
C3SA H3SC 0.9900 . ?
C3SA H3SD 0.9900 . ?
C3SA C4SA 1.527(12) . ?
C4SA H4SC 0.9900 . ?
C4SA H4SD 0.9900 . ?

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 H2 109.5 . . ?
C5 O4 H4 109.5 . . ?
C3 O3 H3 109.5 . . ?
C1SB O1S H1S 109.5 . . ?
C1SA O1S H1SA 109.5 . . ?
C3 C2 C7 119.0(2) . . ?
C3 C2 C1 119.8(2) . . ?
C7 C2 C1 121.1(3) . . ?
C7 C6 Br2 119.4(2) . . ?
C7 C6 C5 121.2(2) . . ?
C5 C6 Br2 119.39(19) . . ?
C3 C4 Br1 119.1(2) . . ?
C3 C4 C5 121.7(3) . . ?
C5 C4 Br1 119.2(2) . . ?
O3 C3 C2 122.5(2) . . ?
O3 C3 C4 118.2(3) . . ?
C4 C3 C2 119.3(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
O4 C5 C6 124.1(2) . . ?
O4 C5 C4 117.9(3) . . ?
C4 C5 C6 118.0(2) . . ?
O2 C1 C2 114.9(2) . . ?
O1 C1 O2 123.8(3) . . ?
O1 C1 C2 121.3(3) . . ?
H3SA C3SB H3SB 107.5 . . ?
C4SB C3SB H3SA 108.6 . . ?
C4SB C3SB H3SB 108.6 . . ?
C2SB C3SB H3SA 108.6 . . ?
C2SB C3SB H3SB 108.6 . . ?
C2SB C3SB C4SB 114.8(7) . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?
H5SD C5S H5SE 109.5 . . ?
H5SD C5S H5SF 109.5 . . ?
H5SE C5S H5SF 109.5 . . ?
C4SB C5S H5SA 109.5 . . ?
C4SB C5S H5SB 109.5 . . ?
C4SB C5S H5SC 109.5 . . ?
C4SA C5S H5SD 109.5 . . ?
C4SA C5S H5SE 109.5 . . ?
C4SA C5S H5SF 109.5 . . ?
C3SB C4SB C5S 112.0(5) . . ?
C3SB C4SB H4SA 109.2 . . ?
C3SB C4SB H4SB 109.2 . . ?
C5S C4SB H4SA 109.2 . . ?
C5S C4SB H4SB 109.2 . . ?
H4SA C4SB H4SB 107.9 . . ?
O1S C1SB H1SB 110.3 . . ?
O1S C1SB H1SC 110.3 . . ?
H1SB C1SB H1SC 108.6 . . ?
C2SB C1SB O1S 106.9(4) . . ?
C2SB C1SB H1SB 110.3 . . ?
C2SB C1SB H1SC 110.3 . . ?
C3SB C2SB C1SB 112.5(5) . . ?
C3SB C2SB H2SA 109.1 . . ?
C3SB C2SB H2SB 109.1 . . ?
C1SB C2SB H2SA 109.1 . . ?
C1SB C2SB H2SB 109.1 . . ?
H2SA C2SB H2SB 107.8 . . ?
O1S C1SA H1SD 109.7 . . ?
O1S C1SA H1SE 109.7 . . ?
O1S C1SA C2SA 109.9(7) . . ?
H1SD C1SA H1SE 108.2 . . ?
C2SA C1SA H1SD 109.7 . . ?
C2SA C1SA H1SE 109.7 . . ?
C1SA C2SA H2SC 109.3 . . ?
C1SA C2SA H2SD 109.3 . . ?
C1SA C2SA C3SA 111.5(7) . . ?
H2SC C2SA H2SD 108.0 . . ?
C3SA C2SA H2SC 109.3 . . ?
C3SA C2SA H2SD 109.3 . . ?
C2SA C3SA H3SC 108.4 . . ?
C2SA C3SA H3SD 108.4 . . ?
H3SC C3SA H3SD 107.5 . . ?
C4SA C3SA C2SA 115.4(7) . . ?
C4SA C3SA H3SC 108.4 . . ?
C4SA C3SA H3SD 108.4 . . ?
C5S C4SA C3SA 114.1(8) . . ?
C5S C4SA H4SC 108.7 . . ?
C5S C4SA H4SD 108.7 . . ?
C3SA C4SA H4SC 108.7 . . ?
C3SA C4SA H4SD 108.7 . . ?
H4SC C4SA H4SD 107.6 . . ?

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
_geom_hbond_publ_flag
O2 H2 O1S 0.84 1.74 2.573(3) 169.2 . yes
O4 H4 O1 0.84 2.00 2.724(3) 143.2 4_475 yes
O3 H3 O1 0.84 1.84 2.575(3) 145.8 . yes
O1S H1S O4 0.84 1.99 2.806(3) 164.3 4_676 yes

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
Br2 C6 C7 C2 -179.1(2) . . . . ?
Br2 C6 C5 O4 -1.0(4) . . . . ?
Br2 C6 C5 C4 179.23(19) . . . . ?
Br1 C4 C3 O3 1.1(3) . . . . ?
Br1 C4 C3 C2 -178.14(19) . . . . ?
Br1 C4 C5 O4 -0.5(3) . . . . ?
Br1 C4 C5 C6 179.25(19) . . . . ?
O1S C1SB C2SB C3SB -172.1(5) . . . . ?
O1S C1SA C2SA C3SA -176.0(7) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C3 C2 C1 O2 -176.2(2) . . . . ?
C3 C2 C1 O1 3.7(4) . . . . ?
C3 C4 C5 O4 179.9(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C7 C2 C3 O3 179.5(2) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C7 C2 C1 O2 5.4(4) . . . . ?
C7 C2 C1 O1 -174.7(3) . . . . ?
C7 C6 C5 O4 178.8(2) . . . . ?
C7 C6 C5 C4 -1.0(4) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C5 C4 C3 O3 -179.3(2) . . . . ?
C5 C4 C3 C2 1.5(4) . . . . ?
C1 C2 C3 O3 1.1(4) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
C1 C2 C7 C6 178.4(2) . . . . ?
C4SB C3SB C2SB C1SB -65.3(8) . . . . ?
C2SB C3SB C4SB C5S -166.0(5) . . . . ?
C1SA C2SA C3SA C4SA 179.9(8) . . . . ?
C2SA C3SA C4SA C5S -177.2(7) . . . . ?


_olex2_exptl_crystal_mounting_method 
'crystal coated in perfluoro polyether oil and mounted on a MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ke057
_database_code_depnum_ccdc_archive 'CCDC 2120725'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        '5-bromo-resorcylic acid methanol solvate'
_chemical_formula_moiety         'C7 H5 Br O4, C H4 O'
_chemical_formula_sum            'C8 H9 Br O5'
_chemical_formula_weight         265.06
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.8463(3)
_cell_length_b                   14.8609(10)
_cell_length_c                   13.0678(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.0313(19)
_cell_angle_gamma                90
_cell_volume                     937.52(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6416
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.378
_exptl_absorpt_correction_T_max  0.8154
_exptl_absorpt_correction_T_min  0.4952
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1185 before and 0.0746 after correction.
The Ratio of minimum to maximum transmission is 0.6073.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.075
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.080
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1551
_reflns_number_total             1833
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²+1.8236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4A)
2.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O4(H4), O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.12643(6) 0.30409(2) 0.79003(2) 0.01700(11) Uani 1 1 d . . . . .
O1S O 1.3521(5) 0.62382(14) 1.00985(17) 0.0196(5) Uani 1 1 d . . . . .
H1S H 1.5030 0.6094 1.0422 0.029 Uiso 1 1 calc GR . . . .
O4 O 1.2003(4) 0.47963(14) 0.90560(16) 0.0145(5) Uani 1 1 d . . . . .
H4 H 1.2309 0.5301 0.9332 0.022 Uiso 1 1 calc GR . . . .
O1 O 0.2730(4) 0.42382(14) 0.54601(16) 0.0154(5) Uani 1 1 d . . . . .
H1 H 0.1325 0.4301 0.5042 0.023 Uiso 1 1 calc GR . . . .
O3 O 0.4601(4) 0.64566(14) 0.73839(17) 0.0165(5) Uani 1 1 d . . . . .
H3 H 0.3287 0.6406 0.6923 0.025 Uiso 1 1 calc GR . . . .
O2 O 0.1595(4) 0.56424(14) 0.58882(15) 0.0134(5) Uani 1 1 d . . . . .
C6 C 0.9169(6) 0.4113(2) 0.7714(2) 0.0122(6) Uani 1 1 d . . . . .
C2 C 0.5406(6) 0.4933(2) 0.6817(2) 0.0102(6) Uani 1 1 d . . . . .
C1 C 0.3097(6) 0.4972(2) 0.6025(2) 0.0120(6) Uani 1 1 d . . . . .
C5 C 0.9843(6) 0.4860(2) 0.8339(2) 0.0111(6) Uani 1 1 d . . . . .
C7 C 0.6997(6) 0.4151(2) 0.6972(2) 0.0116(6) Uani 1 1 d . . . . .
H7 H 0.6563 0.3639 0.6554 0.014 Uiso 1 1 calc R . . . .
C4 C 0.8279(6) 0.5640(2) 0.8203(2) 0.0117(6) Uani 1 1 d . . . . .
H4A H 0.8728 0.6149 0.8624 0.014 Uiso 1 1 calc R . . . .
C3 C 0.6061(6) 0.5680(2) 0.7457(2) 0.0114(6) Uani 1 1 d . . . . .
C1S C 1.3607(7) 0.7163(2) 0.9815(3) 0.0234(8) Uani 1 1 d . . . . .
H1SA H 1.3718 0.7537 1.0435 0.035 Uiso 1 1 calc GR . . . .
H1SB H 1.1927 0.7316 0.9378 0.035 Uiso 1 1 calc GR . . . .
H1SC H 1.5237 0.7272 0.9439 0.035 Uiso 1 1 calc GR . . . .


_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 C6 1.893(3) . ?
O1S C1S 1.425(4) . ?
O4 C5 1.346(3) . ?
O1 C1 1.320(4) . ?
O3 C3 1.354(3) . ?
O2 C1 1.238(4) . ?
C6 C5 1.400(4) . ?
C6 C7 1.369(4) . ?
C2 C1 1.458(4) . ?
C2 C7 1.399(4) . ?
C2 C3 1.408(4) . ?
C5 C4 1.387(4) . ?
C4 C3 1.388(4) . ?

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
C5 C6 Br1 119.8(2) . . ?
C7 C6 Br1 119.8(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C2 C1 120.9(3) . . ?
C7 C2 C3 118.4(3) . . ?
C3 C2 C1 120.7(3) . . ?
O1 C1 C2 115.0(3) . . ?
O2 C1 O1 122.4(3) . . ?
O2 C1 C2 122.6(3) . . ?
O4 C5 C6 118.5(3) . . ?
O4 C5 C4 122.1(3) . . ?
C4 C5 C6 119.4(3) . . ?
C6 C7 C2 121.1(3) . . ?
C5 C4 C3 120.4(3) . . ?
O3 C3 C2 122.8(3) . . ?
O3 C3 C4 117.0(3) . . ?
C4 C3 C2 120.3(3) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_RA_DMF
_database_code_depnum_ccdc_archive 'CCDC 2120727'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        'resorcylic acid DMF solvate'
_chemical_formula_moiety         'C3 H7 N O, C7 H6 O4'
_chemical_formula_sum            'C10 H13 N O5'
_chemical_formula_weight         227.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.320(4)
_cell_length_b                   24.910(7)
_cell_length_c                   7.009(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.322(7)
_cell_angle_gamma                90
_cell_volume                     2137.8(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2498
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.950
_cell_measurement_theta_min      1.663
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.4234
_diffrn_reflns_av_unetI/netI     0.1886
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32606
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.950
_diffrn_reflns_theta_min         1.663
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   Synchrotron
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_source_voltage           0.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2360
_reflns_number_total             5627
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0928
_refine_ls_restrained_S_all      0.843
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2140
_refine_ls_wR_factor_ref         0.2537
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C18(H18), C29(H29), C20(H20), C24(H24), C27(H27),
 C0AA(H0AA)
2.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7), O8(H8), O6(H6), O9(H9), O10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1AA O 0.49485(17) 0.79131(8) 0.7677(2) 0.0395(5) Uani 1 1 d . . . . .
N12 N 0.5050(2) 0.88250(10) 0.7740(3) 0.0347(6) Uani 1 1 d . . . . .
C17 C 0.5399(2) 0.83438(12) 0.8242(3) 0.0341(7) Uani 1 1 d . . . . .
H17 H 0.604686 0.831925 0.910651 0.041 Uiso 1 1 calc R U . . .
C31 C 0.4052(2) 0.89020(13) 0.6440(4) 0.0404(8) Uani 1 1 d . . . . .
H31A H 0.375782 0.855169 0.600923 0.061 Uiso 1 1 calc R U . . .
H31B H 0.421714 0.911262 0.532667 0.061 Uiso 1 1 calc R U . . .
H31C H 0.351268 0.909338 0.711236 0.061 Uiso 1 1 calc R U . . .
C32 C 0.5637(3) 0.93022(12) 0.8432(4) 0.0431(8) Uani 1 1 d . . . . .
H32A H 0.519646 0.950447 0.926636 0.065 Uiso 1 1 calc R U . . .
H32B H 0.578133 0.952644 0.733907 0.065 Uiso 1 1 calc R U . . .
H32C H 0.633061 0.919880 0.915909 0.065 Uiso 1 1 calc R U . . .
O2 O 0.21728(16) 0.50953(8) 0.5093(2) 0.0359(5) Uani 1 1 d . . . . .
O4 O 0.36648(16) 0.57541(8) 0.6606(3) 0.0363(5) Uani 1 1 d . . . . .
H4 H 0.338800 0.545587 0.627166 0.055 Uiso 1 1 calc R U . . .
O7 O 0.29747(18) 0.76193(8) 0.5598(3) 0.0400(5) Uani 1 1 d . . . . .
H7 H 0.361791 0.764090 0.613156 0.060 Uiso 1 1 calc R U . . .
O8 O 0.06536(16) 0.54394(8) 0.3490(3) 0.0368(5) Uani 1 1 d . . . . .
H8 H 0.053383 0.511461 0.322185 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1951(2) 0.60394(12) 0.4889(3) 0.0312(7) Uani 1 1 d . . . . .
C15 C 0.1306(2) 0.64760(12) 0.4171(3) 0.0328(7) Uani 1 1 d . . . . .
H15 H 0.061166 0.640697 0.348368 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1622(2) 0.54877(12) 0.4519(3) 0.0313(7) Uani 1 1 d . . . . .
C18 C 0.3328(2) 0.66806(12) 0.6192(3) 0.0330(7) Uani 1 1 d . . . . .
H18 H 0.400953 0.675385 0.691684 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2680(2) 0.71010(12) 0.5429(3) 0.0327(7) Uani 1 1 d . . . . .
C25 C 0.2985(2) 0.61551(12) 0.5903(3) 0.0310(7) Uani 1 1 d . . . . .
C29 C 0.1643(2) 0.69933(12) 0.4428(3) 0.0343(7) Uani 1 1 d . . . . .
H29 H 0.118518 0.728000 0.393910 0.041 Uiso 1 1 calc R U . . .
O0AA O 0.71774(17) 0.72913(9) 1.0323(2) 0.0384(5) Uani 1 1 d . . . . .
O6 O 0.84929(18) 0.65936(9) 1.2084(3) 0.0422(6) Uani 1 1 d . . . . .
H6 H 0.823615 0.689868 1.179080 0.063 Uiso 1 1 calc R U . . .
O9 O 0.80129(17) 0.47678(8) 1.0164(3) 0.0406(5) Uani 1 1 d . . . . .
H9 H 0.858605 0.473344 1.092212 0.061 Uiso 1 1 calc R U . . .
O10 O 0.58210(16) 0.69911(8) 0.8181(3) 0.0390(5) Uani 1 1 d . . . . .
H10 H 0.570292 0.732174 0.804386 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7021(2) 0.63574(12) 0.9653(3) 0.0309(7) Uani 1 1 d . . . . .
C19 C 0.7719(2) 0.52921(12) 1.0060(3) 0.0315(7) Uani 1 1 d . . . . .
C20 C 0.6474(2) 0.59427(12) 0.8587(3) 0.0324(7) Uani 1 1 d . . . . .
H20 H 0.585196 0.602745 0.771351 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7930(2) 0.62134(12) 1.0969(3) 0.0327(7) Uani 1 1 d . . . . .
C24 C 0.8266(2) 0.56910(12) 1.1179(3) 0.0337(7) Uani 1 1 d . . . . .
H24 H 0.886966 0.560074 1.208343 0.040 Uiso 1 1 calc R U . . .
C26 C 0.6695(2) 0.69156(12) 0.9426(3) 0.0339(7) Uani 1 1 d . . . . .
C27 C 0.6806(2) 0.54256(12) 0.8767(3) 0.0370(7) Uani 1 1 d . . . . .
H27 H 0.642190 0.515342 0.802060 0.044 Uiso 1 1 calc R U . . .
N2 N 0.0248(2) 0.36053(10) 0.2256(3) 0.0333(6) Uani 1 1 d . . . . .
O3 O -0.00170(16) 0.45053(8) 0.2295(2) 0.0349(5) Uani 1 1 d . . . . .
C0AA C 0.0503(2) 0.40928(12) 0.2844(3) 0.0335(7) Uani 1 1 d . . . . .
H0AA H 0.112817 0.413585 0.375236 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0867(2) 0.31402(12) 0.3016(4) 0.0422(8) Uani 1 1 d . . . . .
H5A H 0.117102 0.295253 0.196727 0.063 Uiso 1 1 calc R U . . .
H5B H 0.038364 0.289697 0.362658 0.063 Uiso 1 1 calc R U . . .
H5C H 0.146209 0.325795 0.396706 0.063 Uiso 1 1 calc R U . . .
C6 C -0.0709(2) 0.35022(13) 0.0874(4) 0.0404(8) Uani 1 1 d . . . . .
H6A H -0.131807 0.338352 0.155909 0.061 Uiso 1 1 calc R U . . .
H6B H -0.053515 0.322186 -0.002504 0.061 Uiso 1 1 calc R U . . .
H6C H -0.091436 0.383225 0.016319 0.061 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
O1AA C17 1.252(3) . ?
N12 C17 1.308(4) . ?
N12 C31 1.460(3) . ?
N12 C32 1.447(3) . ?
C17 H17 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O2 C16 1.232(3) . ?
O4 H4 0.8400 . ?
O4 C25 1.361(3) . ?
O7 H7 0.8400 . ?
O7 C21 1.343(4) . ?
O8 H8 0.8400 . ?
O8 C16 1.330(3) . ?
C14 C15 1.407(4) . ?
C14 C16 1.448(4) . ?
C14 C25 1.418(4) . ?
C15 H15 0.9500 . ?
C15 C29 1.360(4) . ?
C18 H18 0.9500 . ?
C18 C21 1.388(4) . ?
C18 C25 1.384(4) . ?
C21 C29 1.414(4) . ?
C29 H29 0.9500 . ?
O0AA C26 1.242(3) . ?
O6 H6 0.8400 . ?
O6 C22 1.367(3) . ?
O9 H9 0.8400 . ?
O9 C19 1.355(4) . ?
O10 H10 0.8400 . ?
O10 C26 1.323(3) . ?
C11 C20 1.403(4) . ?
C11 C22 1.417(4) . ?
C11 C26 1.451(4) . ?
C19 C24 1.393(4) . ?
C19 C27 1.405(4) . ?
C20 H20 0.9500 . ?
C20 C27 1.353(4) . ?
C22 C24 1.368(4) . ?
C24 H24 0.9500 . ?
C27 H27 0.9500 . ?
N2 C0AA 1.309(4) . ?
N2 C5 1.455(3) . ?
N2 C6 1.464(3) . ?
O3 C0AA 1.249(3) . ?
C0AA H0AA 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C17 N12 C31 121.1(2) . . ?
C17 N12 C32 121.7(2) . . ?
C32 N12 C31 117.2(2) . . ?
O1AA C17 N12 125.4(3) . . ?
O1AA C17 H17 117.3 . . ?
N12 C17 H17 117.3 . . ?
N12 C31 H31A 109.5 . . ?
N12 C31 H31B 109.5 . . ?
N12 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N12 C32 H32A 109.5 . . ?
N12 C32 H32B 109.5 . . ?
N12 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 O4 H4 109.5 . . ?
C21 O7 H7 109.5 . . ?
C16 O8 H8 109.5 . . ?
C15 C14 C16 122.3(2) . . ?
C15 C14 C25 117.6(3) . . ?
C25 C14 C16 120.0(2) . . ?
C14 C15 H15 118.9 . . ?
C29 C15 C14 122.2(3) . . ?
C29 C15 H15 118.9 . . ?
O2 C16 O8 122.3(3) . . ?
O2 C16 C14 124.2(2) . . ?
O8 C16 C14 113.5(2) . . ?
C21 C18 H18 119.9 . . ?
C25 C18 H18 119.9 . . ?
C25 C18 C21 120.3(3) . . ?
O7 C21 C18 123.6(3) . . ?
O7 C21 C29 116.5(3) . . ?
C18 C21 C29 119.9(3) . . ?
O4 C25 C14 121.0(3) . . ?
O4 C25 C18 118.4(2) . . ?
C18 C25 C14 120.6(3) . . ?
C15 C29 C21 119.4(3) . . ?
C15 C29 H29 120.3 . . ?
C21 C29 H29 120.3 . . ?
C22 O6 H6 109.5 . . ?
C19 O9 H9 109.5 . . ?
C26 O10 H10 109.5 . . ?
C20 C11 C22 117.4(3) . . ?
C20 C11 C26 122.4(2) . . ?
C22 C11 C26 120.2(3) . . ?
O9 C19 C24 123.2(2) . . ?
O9 C19 C27 117.0(3) . . ?
C24 C19 C27 119.8(3) . . ?
C11 C20 H20 119.1 . . ?
C27 C20 C11 121.9(2) . . ?
C27 C20 H20 119.1 . . ?
O6 C22 C11 120.8(3) . . ?
O6 C22 C24 118.0(2) . . ?
C24 C22 C11 121.2(3) . . ?
C19 C24 H24 120.1 . . ?
C22 C24 C19 119.8(3) . . ?
C22 C24 H24 120.1 . . ?
O0AA C26 O10 122.4(3) . . ?
O0AA C26 C11 123.7(2) . . ?
O10 C26 C11 113.8(2) . . ?
C19 C27 H27 120.1 . . ?
C20 C27 C19 119.9(3) . . ?
C20 C27 H27 120.1 . . ?
C0AA N2 C5 121.7(2) . . ?
C0AA N2 C6 121.2(2) . . ?
C5 N2 C6 117.0(2) . . ?
N2 C0AA H0AA 117.7 . . ?
O3 C0AA N2 124.7(2) . . ?
O3 C0AA H0AA 117.7 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C31 N12 C17 O1AA 0.9(4) . . . . ?
C32 N12 C17 O1AA -178.6(3) . . . . ?
O7 C21 C29 C15 178.6(2) . . . . ?
C14 C15 C29 C21 0.8(4) . . . . ?
C15 C14 C16 O2 178.7(2) . . . . ?
C15 C14 C16 O8 -1.5(4) . . . . ?
C15 C14 C25 O4 -178.6(2) . . . . ?
C15 C14 C25 C18 1.0(4) . . . . ?
C16 C14 C15 C29 -176.2(2) . . . . ?
C16 C14 C25 O4 -2.5(4) . . . . ?
C16 C14 C25 C18 177.1(2) . . . . ?
C18 C21 C29 C15 -2.1(4) . . . . ?
C21 C18 C25 O4 177.2(2) . . . . ?
C21 C18 C25 C14 -2.4(4) . . . . ?
C25 C14 C15 C29 -0.2(4) . . . . ?
C25 C14 C16 O2 2.7(4) . . . . ?
C25 C14 C16 O8 -177.5(2) . . . . ?
C25 C18 C21 O7 -177.8(2) . . . . ?
C25 C18 C21 C29 3.0(4) . . . . ?
O6 C22 C24 C19 -179.6(2) . . . . ?
O9 C19 C24 C22 178.9(3) . . . . ?
O9 C19 C27 C20 -179.6(3) . . . . ?
C11 C20 C27 C19 0.4(4) . . . . ?
C11 C22 C24 C19 1.0(4) . . . . ?
C20 C11 C22 O6 -178.8(2) . . . . ?
C20 C11 C22 C24 0.6(4) . . . . ?
C20 C11 C26 O0AA -178.5(3) . . . . ?
C20 C11 C26 O10 2.1(4) . . . . ?
C22 C11 C20 C27 -1.3(4) . . . . ?
C22 C11 C26 O0AA 0.7(4) . . . . ?
C22 C11 C26 O10 -178.7(3) . . . . ?
C24 C19 C27 C20 1.2(4) . . . . ?
C26 C11 C20 C27 177.9(3) . . . . ?
C26 C11 C22 O6 2.0(4) . . . . ?
C26 C11 C22 C24 -178.7(3) . . . . ?
C27 C19 C24 C22 -2.0(4) . . . . ?
C5 N2 C0AA O3 -177.5(3) . . . . ?
C6 N2 C0AA O3 -0.7(4) . . . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream.'
_olex2_submission_special_instructions 'No special instructions were received'

_vrf_RINTA01_RA_DMF              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystal was a needle of likely twinning, which could not
be resolved satisfactorily. No better crystal could be grown.
;
_vrf_PLAT020_RA_DMF              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.423 Report
RESPONSE: The crystal was a needle of likely twinning, which could not
be resolved satisfactorily. No better crystal could be grown.
;
####################################################################### 
# 
# 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_ke056
_database_code_depnum_ccdc_archive 'CCDC 2120729'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        '5-bromo-resorcylic acid dioxane solvate'
_chemical_formula_moiety         'C7 H5 Br O4, 2(C2 H4 O)'
_chemical_formula_sum            'C11 H13 Br O6'
_chemical_formula_weight         321.12
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   22.7597(16)
_cell_length_b                   6.6011(5)
_cell_length_c                   16.7307(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2513.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.288
_exptl_absorpt_correction_T_max  0.8788
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0758 after correction.
The Ratio of minimum to maximum transmission is 0.7101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Crystallised from dioxane solution'
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1271
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            71370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.774
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2267
_reflns_number_total             2914
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.878
_refine_diff_density_min         -0.603
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+4.9669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H4A(0.5) H1B(0.5) H3A(0.5)
3.a Riding coordinates:
 O1A(H1A), O3B(H3B), O4B(H4BA)
3.b Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C2S(H2SA,H2SB), C1S(H1SA,H1SB), C4S(H4SA,H4SB)
3.c Aromatic/amide H refined with riding coordinates:
 C4B(H4B), C7A(H7A), C7B(H7B), C4A(H4AA)
3.d Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O1B(H1B), O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Br1A Br 0.40007(2) 0.2500 1.24843(3) 0.02815(15) Uani 1 2 d S T P . .
Br1B Br 0.48345(2) 0.2500 0.54430(3) 0.02915(16) Uani 1 2 d S T P . .
O1A O 0.60080(15) 0.2500 1.41164(18) 0.0233(8) Uani 1 2 d S T P . .
H1A H 0.6267 0.2500 1.4455 0.035 Uiso 1 2 d RS T P . .
O2A O 0.67788(14) 0.2500 1.3283(2) 0.0227(8) Uani 1 2 d S T P . .
C4B C 0.3593(2) 0.2500 0.7271(3) 0.0167(10) Uani 1 2 d S T P . .
H4B H 0.3177 0.2500 0.7319 0.020 Uiso 1 2 calc RS T P . .
C6A C 0.4814(2) 0.2500 1.2267(3) 0.0168(10) Uani 1 2 d S T P . .
C2A C 0.5810(2) 0.2500 1.2747(3) 0.0142(9) Uani 1 2 d S T P . .
C5B C 0.3855(2) 0.2500 0.6515(3) 0.0174(10) Uani 1 2 d S T P . .
C1A C 0.6247(2) 0.2500 1.3396(3) 0.0182(10) Uani 1 2 d S T P . .
C6B C 0.4473(2) 0.2500 0.6461(3) 0.0163(10) Uani 1 2 d S T P . .
C7A C 0.5215(2) 0.2500 1.2892(3) 0.0154(9) Uani 1 2 d S T P . .
H7A H 0.5076 0.2500 1.3427 0.018 Uiso 1 2 calc RS T P . .
O4A O 0.45977(14) 0.2500 1.08896(18) 0.0207(7) Uani 1 2 d S T P . .
H4A H 0.4750 0.2871 1.0456 0.031 Uiso 0.5 1 calc GR . . . .
O1B O 0.54902(15) 0.2500 0.8449(2) 0.0256(8) Uani 1 2 d S T P . .
H1B H 0.5677 0.2302 0.8875 0.038 Uiso 0.5 1 calc GR . . . .
O3B O 0.36642(14) 0.2500 0.86731(19) 0.0217(8) Uani 1 2 d S T P . .
H3B H 0.3909 0.2500 0.9032 0.033 Uiso 1 2 d RS T P . .
O3A O 0.65847(13) 0.2500 1.1753(2) 0.0221(8) Uani 1 2 d S T P . .
H3A H 0.6784 0.2847 1.2153 0.033 Uiso 0.5 1 calc GR . . . .
O2B O 0.47249(14) 0.2500 0.92833(18) 0.0217(8) Uani 1 2 d S T P . .
O4B O 0.35425(14) 0.2500 0.58357(19) 0.0221(8) Uani 1 2 d S T P . .
H4BA H 0.3187 0.2500 0.5941 0.033 Uiso 1 2 d RS T P . .
C7B C 0.4810(2) 0.2500 0.7134(3) 0.0137(9) Uani 1 2 d S T P . .
H7B H 0.5226 0.2500 0.7086 0.016 Uiso 1 2 calc RS T P . .
C1B C 0.4927(2) 0.2500 0.8599(3) 0.0167(10) Uani 1 2 d S T P . .
C4A C 0.56020(19) 0.2500 1.1319(3) 0.0144(9) Uani 1 2 d S T P . .
H4AA H 0.5738 0.2500 1.0782 0.017 Uiso 1 2 calc RS T P . .
C5A C 0.5009(2) 0.2500 1.1468(3) 0.0140(9) Uani 1 2 d S T P . .
C3B C 0.3942(2) 0.2500 0.7953(3) 0.0151(10) Uani 1 2 d S T P . .
C2B C 0.4556(2) 0.2500 0.7891(3) 0.0144(9) Uani 1 2 d S T P . .
C3A C 0.6010(2) 0.2500 1.1945(3) 0.0155(9) Uani 1 2 d S T P . .
O3S O 0.62557(14) 0.2500 0.9589(2) 0.0242(8) Uani 1 2 d S T P . .
O1S O 0.67687(17) 0.2500 1.5341(2) 0.0333(9) Uani 1 2 d S T P . .
O4S O 0.74061(16) 0.2500 0.9021(3) 0.0360(10) Uani 1 2 d S T P . .
O2S O 0.71071(16) 0.2500 1.6965(2) 0.0270(8) Uani 1 2 d S T P . .
C3S C 0.66109(16) 0.0705(6) 0.9620(2) 0.0318(9) Uani 1 1 d . . . . .
H3SA H 0.6357 -0.0506 0.9568 0.038 Uiso 1 1 calc R . . . .
H3SB H 0.6814 0.0632 1.0143 0.038 Uiso 1 1 calc R . . . .
C2S C 0.71637(16) 0.0738(6) 1.6482(2) 0.0273(8) Uani 1 1 d . . . . .
H2SA H 0.7118 -0.0485 1.6819 0.033 Uiso 1 1 calc R . . . .
H2SB H 0.7561 0.0703 1.6240 0.033 Uiso 1 1 calc R . . . .
C1S C 0.67079(17) 0.0725(6) 1.5832(2) 0.0317(9) Uani 1 1 d . . . . .
H1SA H 0.6755 -0.0505 1.5500 0.038 Uiso 1 1 calc R . . . .
H1SB H 0.6311 0.0696 1.6073 0.038 Uiso 1 1 calc R . . . .
C4S C 0.70548(16) 0.0724(6) 0.8963(3) 0.0357(10) Uani 1 1 d . . . . .
H4SA H 0.7307 -0.0493 0.9002 0.043 Uiso 1 1 calc R . . . .
H4SB H 0.6853 0.0695 0.8439 0.043 Uiso 1 1 calc R . . . .


_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
Br1A C6A 1.887(4) . ?
Br1B C6B 1.891(4) . ?
O1A C1A 1.323(6) . ?
O2A C1A 1.225(6) . ?
C4B C5B 1.400(6) . ?
C4B C3B 1.390(6) . ?
C6A C7A 1.386(6) . ?
C6A C5A 1.409(6) . ?
C2A C1A 1.472(6) . ?
C2A C7A 1.377(6) . ?
C2A C3A 1.417(6) . ?
C5B C6B 1.409(7) . ?
C5B O4B 1.341(5) . ?
C6B C7B 1.363(6) . ?
O4A C5A 1.347(5) . ?
O1B C1B 1.306(6) . ?
O3B C3B 1.360(5) . ?
O3A C3A 1.346(5) . ?
O2B C1B 1.234(6) . ?
C7B C2B 1.392(6) . ?
C1B C2B 1.455(6) . ?
C4A C5A 1.372(6) . ?
C4A C3A 1.400(6) . ?
C3B C2B 1.402(6) . ?
O3S C3S 1.435(4) 8_565 ?
O3S C3S 1.435(4) . ?
O1S C1S 1.438(4) . ?
O1S C1S 1.438(4) 8_565 ?
O4S C4S 1.423(4) 8_565 ?
O4S C4S 1.423(4) . ?
O2S C2S 1.422(4) 8_565 ?
O2S C2S 1.422(4) . ?
C3S C4S 1.494(5) . ?
C2S C1S 1.503(5) . ?

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
C3B C4B C5B 119.9(4) . . ?
C7A C6A Br1A 120.0(3) . . ?
C7A C6A C5A 120.5(4) . . ?
C5A C6A Br1A 119.5(3) . . ?
C7A C2A C1A 122.4(4) . . ?
C7A C2A C3A 118.9(4) . . ?
C3A C2A C1A 118.8(4) . . ?
C4B C5B C6B 118.9(4) . . ?
O4B C5B C4B 122.6(4) . . ?
O4B C5B C6B 118.4(4) . . ?
O1A C1A C2A 113.2(4) . . ?
O2A C1A O1A 123.2(4) . . ?
O2A C1A C2A 123.6(4) . . ?
C5B C6B Br1B 119.5(3) . . ?
C7B C6B Br1B 120.0(4) . . ?
C7B C6B C5B 120.6(4) . . ?
C2A C7A C6A 121.0(4) . . ?
C6B C7B C2B 121.2(4) . . ?
O1B C1B C2B 114.5(4) . . ?
O2B C1B O1B 122.9(4) . . ?
O2B C1B C2B 122.6(4) . . ?
C5A C4A C3A 121.1(4) . . ?
O4A C5A C6A 117.6(4) . . ?
O4A C5A C4A 123.6(4) . . ?
C4A C5A C6A 118.9(4) . . ?
C4B C3B C2B 120.5(4) . . ?
O3B C3B C4B 117.5(4) . . ?
O3B C3B C2B 121.9(4) . . ?
C7B C2B C1B 119.9(4) . . ?
C7B C2B C3B 118.9(4) . . ?
C3B C2B C1B 121.2(4) . . ?
O3A C3A C2A 122.5(4) . . ?
O3A C3A C4A 117.8(4) . . ?
C4A C3A C2A 119.7(4) . . ?
C3S O3S C3S 111.3(4) 8_565 . ?
C1S O1S C1S 109.1(4) . 8_565 ?
C4S O4S C4S 111.0(4) 8_565 . ?
C2S O2S C2S 109.8(4) 8_565 . ?
O3S C3S C4S 110.3(3) . . ?
O2S C2S C1S 110.7(3) . . ?
O1S C1S C2S 110.0(3) . . ?
O4S C4S C3S 109.7(3) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_exptl_crystal_mounting_method 
'Crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ke033
_database_code_depnum_ccdc_archive 'CCDC 2120719'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        '3,5-dibromo-resorcylic acid THF solvate'
_chemical_formula_moiety         'C7 H4 Br2 O4, C4 H8 O'
_chemical_formula_sum            'C11 H12 Br2 O5'
_chemical_formula_weight         384.03
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9275(3)
_cell_length_b                   16.6356(9)
_cell_length_c                   15.8268(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.1838(17)
_cell_angle_gamma                90
_cell_volume                     1287.17(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.307
_exptl_absorpt_correction_T_max  0.2997
_exptl_absorpt_correction_T_min  0.1246
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1122 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.4157.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'cut from a larger crystal'
_exptl_crystal_recrystallization_method 'crystallised from THF by fast cooling'
_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.342
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19514
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.777
_diffrn_reflns_theta_min         2.449
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2405
_reflns_number_total             2740
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0156P)²+0.5415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0491
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O6A) = Uanis(O6)
3. Others
 Sof(H11)=Sof(O6A)=Sof(H6A)=1-FVAR(1)
 Sof(O6)=Sof(H6)=Sof(H7)=FVAR(1)
 Sof(C18A)=Sof(H18C)=Sof(H18D)=1-FVAR(2)
 Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C18A(H18C,H18D)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11)
4.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O6(H6), O6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.47756(4) 0.78884(2) 0.30348(2) 0.01484(7) Uani 1 1 d . . . . .
Br2 Br 0.35832(5) 0.67444(2) 0.63405(2) 0.02016(7) Uani 1 1 d . . . . .
O3 O -0.2830(3) 0.97076(9) 0.43603(10) 0.0170(3) Uani 1 1 d . . . . .
O4 O -0.3285(3) 0.91948(9) 0.56429(10) 0.0178(3) Uani 1 1 d . . . . .
H4 H -0.448386 0.953861 0.562242 0.027 Uiso 1 1 calc R U . . .
O5 O 0.5649(3) 0.68105(9) 0.46578(9) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.633797 0.684691 0.421380 0.023 Uiso 1 1 calc R U . . .
O6 O 0.0641(3) 0.90681(10) 0.34611(10) 0.0159(4) Uani 0.921(3) 1 d . . P A 1
H6 H -0.052305 0.939108 0.357022 0.024 Uiso 0.921(3) 1 calc R U P A 1
C7 C 0.0595(4) 0.80356(12) 0.55098(14) 0.0128(4) Uani 1 1 d . . . . .
H7 H -0.025495 0.805867 0.600190 0.015 Uiso 0.921(3) 1 calc R U P A 1
O8 O 0.1193(4) 0.37437(10) 0.64151(10) 0.0276(4) Uani 1 1 d . . . . .
C9 C 0.3813(4) 0.73967(12) 0.46895(13) 0.0119(4) Uani 1 1 d . . . . .
C10 C 0.2543(4) 0.74602(12) 0.54296(13) 0.0123(4) Uani 1 1 d . . . . .
C11 C 0.1167(4) 0.85471(12) 0.41121(13) 0.0123(4) Uani 1 1 d . . . . .
H11 H 0.073775 0.891646 0.367464 0.015 Uiso 0.079(3) 1 calc R U P A 2
C12 C 0.3095(4) 0.79470(12) 0.40382(13) 0.0110(4) Uani 1 1 d . . . . .
C13 C -0.1625(5) 0.48754(16) 0.64075(17) 0.0314(6) Uani 1 1 d . . . . .
H13A H -0.344090 0.464644 0.639168 0.038 Uiso 1 1 calc R U . B 1
H13B H -0.177367 0.543223 0.622573 0.038 Uiso 1 1 calc R U . B 1
C14 C -0.0116(4) 0.85888(12) 0.48501(13) 0.0114(4) Uani 1 1 d . . . . .
C15 C 0.0111(5) 0.43993(14) 0.58806(15) 0.0222(5) Uani 1 1 d . . . . .
H15A H -0.097544 0.419813 0.537104 0.027 Uiso 1 1 calc R U . . .
H15B H 0.158074 0.472789 0.571390 0.027 Uiso 1 1 calc R U . . .
C16 C -0.2180(4) 0.92037(12) 0.49331(14) 0.0131(4) Uani 1 1 d . . . . .
C17 C 0.1007(6) 0.39390(16) 0.72867(16) 0.0322(6) Uani 1 1 d . . . . .
H17A H 0.278247 0.389353 0.762497 0.039 Uiso 1 1 calc R U . C 1
H17B H -0.026330 0.358180 0.752141 0.039 Uiso 1 1 calc R U . C 1
C18 C -0.0005(13) 0.4794(2) 0.7280(2) 0.0321(13) Uani 0.821(14) 1 d . . P D 1
H18A H 0.150847 0.517081 0.735330 0.039 Uiso 0.821(14) 1 calc R U P D 1
H18B H -0.115637 0.488181 0.772605 0.039 Uiso 0.821(14) 1 calc R U P D 1
O6A O -0.059(4) 0.8065(11) 0.6234(12) 0.0159(4) Uani 0.079(3) 1 d . . P A 2
H6A H -0.209085 0.828399 0.613813 0.024 Uiso 0.079(3) 1 calc R U P A 2
C18A C -0.155(6) 0.4476(18) 0.7225(13) 0.044(8) Uani 0.179(14) 1 d . . P D 2
H18C H -0.318759 0.415521 0.724684 0.053 Uiso 0.179(14) 1 calc R U P D 2
H18D H -0.140773 0.486454 0.768550 0.053 Uiso 0.179(14) 1 calc R U P D 2


_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 C12 1.883(2) . ?
Br2 C10 1.891(2) . ?
O3 C16 1.247(3) . ?
O4 H4 0.8200 . ?
O4 C16 1.308(3) . ?
O5 H5 0.8200 . ?
O5 C9 1.335(2) . ?
O6 H6 0.8200 . ?
O6 C11 1.346(3) . ?
C7 H7 0.9300 . ?
C7 C10 1.373(3) . ?
C7 C14 1.403(3) . ?
C7 O6A 1.352(19) . ?
O8 C15 1.441(3) . ?
O8 C17 1.431(3) . ?
C9 C10 1.399(3) . ?
C9 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(3) . ?
C11 C14 1.398(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C15 1.494(3) . ?
C13 C18 1.513(5) . ?
C13 C18A 1.451(18) . ?
C14 C16 1.460(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.507(4) . ?
C17 C18A 1.539(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O6A H6A 0.8200 . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?

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
C16 O4 H4 109.5 . . ?
C9 O5 H5 109.5 . . ?
C11 O6 H6 109.5 . . ?
C10 C7 H7 120.0 . . ?
C10 C7 C14 120.06(19) . . ?
C14 C7 H7 120.0 . . ?
O6A C7 C10 119.0(8) . . ?
O6A C7 C14 120.9(8) . . ?
C17 O8 C15 109.29(17) . . ?
O5 C9 C10 117.55(18) . . ?
O5 C9 C12 124.31(18) . . ?
C12 C9 C10 118.14(18) . . ?
C7 C10 Br2 119.65(16) . . ?
C7 C10 C9 121.41(19) . . ?
C9 C10 Br2 118.94(15) . . ?
O6 C11 C12 117.71(18) . . ?
O6 C11 C14 122.94(18) . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C14 119.34(19) . . ?
C14 C11 H11 120.3 . . ?
C9 C12 Br1 119.53(15) . . ?
C9 C12 C11 121.50(19) . . ?
C11 C12 Br1 118.97(15) . . ?
H13A C13 H13B 109.4 . . ?
C15 C13 H13A 111.6 . . ?
C15 C13 H13B 111.6 . . ?
C15 C13 C18 100.9(2) . . ?
C18 C13 H13A 111.6 . . ?
C18 C13 H13B 111.6 . . ?
C18A C13 C15 107.7(7) . . ?
C7 C14 C16 120.29(19) . . ?
C11 C14 C7 119.52(18) . . ?
C11 C14 C16 120.19(19) . . ?
O8 C15 C13 105.61(19) . . ?
O8 C15 H15A 110.6 . . ?
O8 C15 H15B 110.6 . . ?
C13 C15 H15A 110.6 . . ?
C13 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
O3 C16 O4 122.37(18) . . ?
O3 C16 C14 121.60(19) . . ?
O4 C16 C14 116.03(19) . . ?
O8 C17 H17A 110.6 . . ?
O8 C17 H17B 110.6 . . ?
O8 C17 C18 105.6(2) . . ?
O8 C17 C18A 102.8(8) . . ?
H17A C17 H17B 108.7 . . ?
C18 C17 H17A 110.6 . . ?
C18 C17 H17B 110.6 . . ?
C13 C18 H18A 111.1 . . ?
C13 C18 H18B 111.1 . . ?
C17 C18 C13 103.1(3) . . ?
C17 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
C7 O6A H6A 109.5 . . ?
C13 C18A C17 104.5(10) . . ?
C13 C18A H18C 110.9 . . ?
C13 C18A H18D 110.9 . . ?
C17 C18A H18C 110.9 . . ?
C17 C18A H18D 110.9 . . ?
H18C C18A H18D 108.9 . . ?

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
O5 C9 C10 Br2 2.1(3) . . . . ?
O5 C9 C10 C7 -178.77(19) . . . . ?
O5 C9 C12 Br1 -0.3(3) . . . . ?
O5 C9 C12 C11 -179.79(19) . . . . ?
O6 C11 C12 Br1 -1.2(3) . . . . ?
O6 C11 C12 C9 178.32(18) . . . . ?
O6 C11 C14 C7 -178.39(19) . . . . ?
O6 C11 C14 C16 1.6(3) . . . . ?
C7 C14 C16 O3 179.26(19) . . . . ?
C7 C14 C16 O4 -0.4(3) . . . . ?
O8 C17 C18 C13 27.7(4) . . . . ?
O8 C17 C18A C13 -30(2) . . . . ?
C10 C7 C14 C11 0.2(3) . . . . ?
C10 C7 C14 C16 -179.80(19) . . . . ?
C10 C9 C12 Br1 179.50(15) . . . . ?
C10 C9 C12 C11 0.0(3) . . . . ?
C11 C14 C16 O3 -0.8(3) . . . . ?
C11 C14 C16 O4 179.60(18) . . . . ?
C12 C9 C10 Br2 -177.69(15) . . . . ?
C12 C9 C10 C7 1.5(3) . . . . ?
C12 C11 C14 C7 1.2(3) . . . . ?
C12 C11 C14 C16 -178.82(18) . . . . ?
C14 C7 C10 Br2 177.59(15) . . . . ?
C14 C7 C10 C9 -1.6(3) . . . . ?
C14 C11 C12 Br1 179.20(15) . . . . ?
C14 C11 C12 C9 -1.3(3) . . . . ?
C15 O8 C17 C18 -5.4(4) . . . . ?
C15 O8 C17 C18A 30.9(14) . . . . ?
C15 C13 C18 C17 -38.2(4) . . . . ?
C15 C13 C18A C17 19(2) . . . . ?
C17 O8 C15 C13 -19.4(3) . . . . ?
C18 C13 C15 O8 35.6(3) . . . . ?
O6A C7 C10 Br2 -1.7(10) . . . . ?
O6A C7 C10 C9 179.2(10) . . . . ?
O6A C7 C14 C11 179.4(10) . . . . ?
O6A C7 C14 C16 -0.6(10) . . . . ?
C18A C13 C15 O8 -1.2(16) . . . . ?


_olex2_exptl_crystal_mounting_method 
'Crystal coated in perfluoro polyether oil and mounted on a MiTeGen sample holder directly into the cold cryostream'
_olex2_submission_original_sample_id 'BRA THF FC'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_RA_DIO
_database_code_depnum_ccdc_archive 'CCDC 2120724'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        'resorcylic acid dioxane hemisolvate'
_chemical_formula_moiety         'C7 H6 O4, C2 H4 O'
_chemical_formula_sum            'C9 H10 O5'
_chemical_formula_weight         198.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.2219(17)
_cell_length_b                   6.4624(8)
_cell_length_c                   11.2303(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.089(2)
_cell_angle_gamma                90
_cell_volume                     895.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4830
_cell_measurement_temperature    120
_cell_measurement_theta_max      0.3361
_cell_measurement_theta_min      1.651
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3361
_diffrn_reflns_av_unetI/netI     0.1471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12446
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         1.651
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   Synchrotron
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_source_voltage           0.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1838
_reflns_number_total             2269
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0816
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1277P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2186
_refine_ls_wR_factor_ref         0.2268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O1 O 0.41463(9) 1.36881(19) 0.88537(11) 0.0241(4) Uani 1 1 d . . . . .
O2 O 0.27355(9) 1.1336(2) 0.72157(12) 0.0256(4) Uani 1 1 d . . . . .
H2 H 0.314842 1.232354 0.745528 0.038 Uiso 1 1 calc R U . . .
O3 O 0.17890(10) 0.50767(19) 0.87613(12) 0.0266(4) Uani 1 1 d . . . . .
H3 H 0.139244 0.498510 0.800965 0.040 Uiso 1 1 calc R U . . .
O4 O 0.46969(9) 1.29218(19) 1.09331(10) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.506866 1.395718 1.098364 0.038 Uiso 1 1 calc R U . . .
O5 O 0.03811(10) 0.4553(2) 0.63148(12) 0.0286(4) Uani 1 1 d . . . . .
C6 C 0.35028(11) 1.0605(3) 0.94814(15) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.28371(12) 1.0101(3) 0.82163(15) 0.0211(4) Uani 1 1 d . . . . .
C8 C 0.23376(12) 0.6897(3) 0.89535(16) 0.0226(4) Uani 1 1 d . . . . .
C9 C 0.22522(12) 0.8251(3) 0.79686(15) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.180420 0.792830 0.713913 0.027 Uiso 1 1 calc R U . . .
C10 C 0.41337(12) 1.2523(3) 0.97247(15) 0.0210(4) Uani 1 1 d . . . . .
C11 C 0.35663(12) 0.9209(3) 1.04571(16) 0.0227(4) Uani 1 1 d . . . . .
H11 H 0.400091 0.953195 1.129190 0.027 Uiso 1 1 calc R U . . .
C12 C 0.30020(12) 0.7366(3) 1.02154(15) 0.0230(4) Uani 1 1 d . . . . .
H12 H 0.306013 0.645012 1.087557 0.028 Uiso 1 1 calc R U . . .
C13 C 0.02806(13) 0.2954(3) 0.53961(17) 0.0271(4) Uani 1 1 d . . . . .
H13A H -0.042394 0.229900 0.516891 0.033 Uiso 1 1 calc R U . . .
H13B H 0.083160 0.190846 0.576300 0.033 Uiso 1 1 calc R U . . .
C14 C -0.04074(13) 0.6154(3) 0.57822(18) 0.0274(4) Uani 1 1 d . . . . .
H14A H -0.031438 0.723965 0.640898 0.033 Uiso 1 1 calc R U . . .
H14B H -0.113099 0.558759 0.556535 0.033 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
O1 C10 1.239(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.345(2) . ?
O3 H3 0.8200 . ?
O3 C8 1.358(2) . ?
O4 H4 0.8200 . ?
O4 C10 1.3173(19) . ?
O5 C13 1.432(2) . ?
O5 C14 1.437(2) . ?
C6 C7 1.414(2) . ?
C6 C10 1.464(2) . ?
C6 C11 1.398(3) . ?
C7 C9 1.396(2) . ?
C8 C9 1.383(2) . ?
C8 C12 1.406(2) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.380(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.507(3) 3_566 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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 O2 H2 109.5 . . ?
C8 O3 H3 109.5 . . ?
C10 O4 H4 109.5 . . ?
C13 O5 C14 110.74(12) . . ?
C7 C6 C10 119.31(16) . . ?
C11 C6 C7 118.60(15) . . ?
C11 C6 C10 122.04(14) . . ?
O2 C7 C6 122.79(15) . . ?
O2 C7 C9 117.38(14) . . ?
C9 C7 C6 119.83(16) . . ?
O3 C8 C9 122.40(14) . . ?
O3 C8 C12 116.84(15) . . ?
C9 C8 C12 120.76(15) . . ?
C7 C9 H9 119.9 . . ?
C8 C9 C7 120.16(14) . . ?
C8 C9 H9 119.9 . . ?
O1 C10 O4 122.10(15) . . ?
O1 C10 C6 122.39(14) . . ?
O4 C10 C6 115.51(15) . . ?
C6 C11 H11 119.1 . . ?
C12 C11 C6 121.81(14) . . ?
C12 C11 H11 119.1 . . ?
C8 C12 H12 120.6 . . ?
C11 C12 C8 118.83(16) . . ?
C11 C12 H12 120.6 . . ?
O5 C13 H13A 109.6 . . ?
O5 C13 H13B 109.6 . . ?
O5 C13 C14 110.22(15) . 3_566 ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 3_566 . ?
C14 C13 H13B 109.6 3_566 . ?
O5 C14 C13 110.35(15) . 3_566 ?
O5 C14 H14A 109.6 . . ?
O5 C14 H14B 109.6 . . ?
C13 C14 H14A 109.6 3_566 . ?
C13 C14 H14B 109.6 3_566 . ?
H14A C14 H14B 108.1 . . ?

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
O2 C7 C9 C8 178.82(15) . . . . ?
O3 C8 C9 C7 -179.76(14) . . . . ?
O3 C8 C12 C11 -179.36(14) . . . . ?
C6 C7 C9 C8 -1.1(2) . . . . ?
C6 C11 C12 C8 -0.7(3) . . . . ?
C7 C6 C10 O1 -3.3(2) . . . . ?
C7 C6 C10 O4 177.27(14) . . . . ?
C7 C6 C11 C12 0.2(3) . . . . ?
C9 C8 C12 C11 0.3(3) . . . . ?
C10 C6 C7 O2 -1.5(2) . . . . ?
C10 C6 C7 C9 178.43(14) . . . . ?
C10 C6 C11 C12 -177.46(14) . . . . ?
C11 C6 C7 O2 -179.23(15) . . . . ?
C11 C6 C7 C9 0.7(2) . . . . ?
C11 C6 C10 O1 174.28(15) . . . . ?
C11 C6 C10 O4 -5.1(2) . . . . ?
C12 C8 C9 C7 0.6(3) . . . . ?
C13 O5 C14 C13 -57.7(2) . . . 3_566 ?
C14 O5 C13 C14 57.6(2) . . . 3_566 ?


_olex2_exptl_crystal_mounting_method 
'crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'

_vrf_PLAT020_RA_DIO              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.336 Report
RESPONSE: The crystal was a needle with potential twinning, which could not be
resolved satisfactorily.
;
_vrf_RINTA01_RA_DIO              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystal was a needle with potential twinning, which could not be 
resolved satisfactorily.
;
####################################################################### 
# 
# 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_ke042
_database_code_depnum_ccdc_archive 'CCDC 2120726'
loop_
_audit_author_name
_audit_author_address
'Edkins K.'
;The University of Manchester
United Kingdom
;
_audit_update_record             
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
katharina.edkins@manchester.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        
'3,5-dibromo-resorcylic acid acetic acid solvate'
_chemical_formula_moiety         'C7 H4 Br2 O4, C2 H4 O2'
_chemical_formula_sum            'C9 H8 Br2 O6'
_chemical_formula_weight         371.97
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.2749(9)
_cell_length_b                   3.9072(2)
_cell_length_c                   35.441(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.9201(16)
_cell_angle_gamma                90
_cell_volume                     2363.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9711
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.16
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.066
_exptl_absorpt_coefficient_mu    6.873
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1404 before and 0.0915 after correction. The Ratio of minimum to maximum transmission is 0.6331. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.091
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0030
0.00 -1.00 0.00 0.4310
0.00 1.00 0.00 0.3970
-1.00 0.00 -1.00 0.0330
0.00 0.00 -1.00 0.0370
0.00 0.00 1.00 0.0150

_exptl_crystal_size_max          0.862
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.069
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1977
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            48462
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.019
_diffrn_reflns_theta_min         2.327
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3364
_reflns_number_total             4111
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         1.363
_refine_diff_density_min         -1.677
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+8.8146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.b Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1S(H1S), O4(H4), O3(H3), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br -0.09891(2) 0.53810(8) 0.32771(2) 0.01483(10) Uani 1 1 d . . . . .
Br1 Br 0.14589(2) 1.17768(8) 0.42777(2) 0.01448(10) Uani 1 1 d . . . . .
O2 O 0.24812(14) 0.8952(7) 0.29287(7) 0.0190(5) Uani 1 1 d . . . . .
O2S O 0.02279(14) 1.7308(7) 0.53828(7) 0.0188(5) Uani 1 1 d . . . . .
O1S O 0.10475(15) 1.4024(7) 0.51202(8) 0.0221(5) Uani 1 1 d . . . . .
H1S H 0.063635 1.360374 0.496729 0.033 Uiso 1 1 calc R U . . .
O4 O -0.01828(14) 0.8763(6) 0.39826(7) 0.0161(5) Uani 1 1 d . . . . .
H4 H -0.002599 1.023865 0.414935 0.024 Uiso 1 1 calc R U . . .
O3 O 0.23032(15) 1.0898(7) 0.36115(8) 0.0220(5) Uani 1 1 d . . . . .
H3 H 0.255313 1.054705 0.342993 0.033 Uiso 1 1 calc R U . . .
O1 O 0.15188(15) 0.6004(7) 0.25762(7) 0.0200(5) Uani 1 1 d . . . . .
H1 H 0.184975 0.592256 0.242603 0.030 Uiso 1 1 calc R U . . .
C5 C 0.03127(18) 0.8611(8) 0.37292(9) 0.0115(6) Uani 1 1 d . . . . .
C1S C 0.0886(2) 1.6099(9) 0.53871(10) 0.0158(6) Uani 1 1 d . . . . .
C2 C 0.12948(19) 0.8042(8) 0.31718(9) 0.0123(6) Uani 1 1 d . . . . .
C7 C 0.05226(19) 0.6803(8) 0.31006(9) 0.0127(6) Uani 1 1 d . . . . .
H7 H 0.032949 0.577552 0.286150 0.015 Uiso 1 1 calc R U . . .
C4 C 0.10777(19) 0.9838(8) 0.37960(9) 0.0116(6) Uani 1 1 d . . . . .
C1 C 0.18106(19) 0.7705(8) 0.28825(10) 0.0135(6) Uani 1 1 d . . . . .
C2S C 0.1562(2) 1.6799(9) 0.56914(11) 0.0200(7) Uani 1 1 d . . . . .
H2SA H 0.197602 1.796230 0.558010 0.030 Uiso 1 1 calc R U . . .
H2SB H 0.176465 1.463467 0.580693 0.030 Uiso 1 1 calc R U . . .
H2SC H 0.139212 1.826113 0.588776 0.030 Uiso 1 1 calc R U . . .
C6 C 0.00457(18) 0.7071(8) 0.33753(9) 0.0113(6) Uani 1 1 d . . . . .
C3 C 0.15767(19) 0.9602(8) 0.35236(9) 0.0122(6) 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
Br2 C6 1.887(3) . ?
Br1 C4 1.891(3) . ?
O2 C1 1.244(4) . ?
O2S C1S 1.229(4) . ?
O1S H1S 0.8400 . ?
O1S C1S 1.309(4) . ?
O4 H4 0.8400 . ?
O4 C5 1.335(4) . ?
O3 H3 0.8400 . ?
O3 C3 1.344(4) . ?
O1 H1 0.8400 . ?
O1 C1 1.306(4) . ?
C5 C4 1.391(4) . ?
C5 C6 1.403(4) . ?
C1S C2S 1.488(5) . ?
C2 C7 1.405(5) . ?
C2 C1 1.465(5) . ?
C2 C3 1.405(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.374(4) . ?
C4 C3 1.393(5) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
C1S O1S H1S 109.5 . . ?
C5 O4 H4 109.5 . . ?
C3 O3 H3 109.5 . . ?
C1 O1 H1 109.5 . . ?
O4 C5 C4 124.2(3) . . ?
O4 C5 C6 117.7(3) . . ?
C4 C5 C6 118.2(3) . . ?
O2S C1S O1S 122.0(3) . . ?
O2S C1S C2S 124.0(3) . . ?
O1S C1S C2S 114.0(3) . . ?
C7 C2 C1 120.5(3) . . ?
C7 C2 C3 119.8(3) . . ?
C3 C2 C1 119.7(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C5 C4 Br1 118.7(2) . . ?
C5 C4 C3 122.2(3) . . ?
C3 C4 Br1 119.1(2) . . ?
O2 C1 O1 122.7(3) . . ?
O2 C1 C2 121.9(3) . . ?
O1 C1 C2 115.4(3) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C5 C6 Br2 119.1(2) . . ?
C7 C6 Br2 119.8(2) . . ?
C7 C6 C5 121.1(3) . . ?
O3 C3 C2 123.5(3) . . ?
O3 C3 C4 118.0(3) . . ?
C4 C3 C2 118.5(3) . . ?

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
Br1 C4 C3 O3 -2.6(4) . . . . ?
Br1 C4 C3 C2 177.7(2) . . . . ?
O4 C5 C4 Br1 1.2(4) . . . . ?
O4 C5 C4 C3 179.5(3) . . . . ?
O4 C5 C6 Br2 0.8(4) . . . . ?
O4 C5 C6 C7 -179.7(3) . . . . ?
C5 C4 C3 O3 179.2(3) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C2 C7 C6 Br2 -179.8(2) . . . . ?
C2 C7 C6 C5 0.7(5) . . . . ?
C7 C2 C1 O2 175.8(3) . . . . ?
C7 C2 C1 O1 -4.5(5) . . . . ?
C7 C2 C3 O3 -179.0(3) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C4 C5 C6 Br2 180.0(2) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C1 C2 C7 C6 178.8(3) . . . . ?
C1 C2 C3 O3 1.4(5) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C6 C5 C4 Br1 -177.8(2) . . . . ?
C6 C5 C4 C3 0.4(5) . . . . ?
C3 C2 C7 C6 -0.8(5) . . . . ?
C3 C2 C1 O2 -4.6(5) . . . . ?
C3 C2 C1 O1 175.2(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_vrf_RINTA01_ke042               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This crystal form shows slight disintegration upon cutting and 
no better crystal could be grown.
;
