# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2g7pcs
_database_code_depnum_ccdc_archive 'CCDC 2271505'
loop_
_audit_author_name
_audit_author_address
'Tatiana Groutso'
;The university of Auckland
New Zealand
;
_audit_update_record             
;
2023-06-22 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          83
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Br O3'
_chemical_formula_weight         246.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6869(2)
_cell_length_b                   5.97800(10)
_cell_length_c                   10.0410(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.575(2)
_cell_angle_gamma                90
_cell_volume                     459.224(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    6675
_cell_measurement_theta_min      3.5810
_cell_measurement_theta_max      74.4790

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_F_000             246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.892
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4287
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.783
_diffrn_reflns_theta_max         68.153
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1634
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.970

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+0.3962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1634
_refine_ls_number_parameters     120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0447
_refine_ls_wR_factor_gt          0.0447
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3972(4) 0.7572(6) 0.2345(4) 0.0139(7) Uani 1 1 d . . . . .
H1 H 0.370544 0.915668 0.218049 0.017 Uiso 1 1 calc R U . . .
C2 C 0.4087(4) 0.7257(5) 0.3835(3) 0.0137(9) Uani 1 1 d . . . . .
H2 H 0.515688 0.723466 0.435459 0.016 Uiso 1 1 calc R U . . .
C3 C 0.2590(4) 0.7013(11) 0.4374(3) 0.0147(7) Uani 1 1 d . . . . .
C4 C 0.0783(3) 0.6845(13) 0.3640(3) 0.0167(6) Uani 1 1 d . . . . .
H4A H 0.005204 0.799803 0.397471 0.020 Uiso 1 1 calc R U . . .
H4B H 0.028463 0.540875 0.384221 0.020 Uiso 1 1 calc R U . . .
C5 C 0.0730(4) 0.7088(11) 0.2100(3) 0.0149(9) Uani 1 1 d . . . . .
H5A H -0.023381 0.622149 0.166995 0.018 Uiso 1 1 calc R U . . .
H5B H 0.055048 0.864374 0.184809 0.018 Uiso 1 1 calc R U . . .
C6 C 0.2448(4) 0.6259(5) 0.1642(3) 0.0125(8) Uani 1 1 d . . . . .
C8 C 0.2799(3) 0.6720(10) 0.0208(3) 0.0135(6) Uani 1 1 d . . . . .
C10 C 0.5457(4) 0.6993(10) 0.1501(3) 0.0157(7) Uani 1 1 d . . . . .
H10A H 0.635959 0.813296 0.157599 0.019 Uiso 1 1 calc R U . . .
H10B H 0.597444 0.555561 0.175333 0.019 Uiso 1 1 calc R U . . .
C12 C 0.2654(4) 0.3691(6) 0.1854(3) 0.0139(7) Uani 1 1 d . . . . .
H12A H 0.388922 0.332250 0.195759 0.017 Uiso 1 1 calc R U . . .
H12B H 0.216854 0.327829 0.267574 0.017 Uiso 1 1 calc R U . . .
Br7 Br 0.25726(3) 0.68300(8) 0.62741(3) 0.01698(12) Uani 1 1 d . . . . .
O9 O 0.4538(2) 0.6928(9) 0.0147(2) 0.0156(4) Uani 1 1 d . . . . .
O11 O 0.1801(3) 0.6923(9) -0.07914(19) 0.0177(4) Uani 1 1 d . . . . .
O13 O 0.1825(3) 0.2421(4) 0.0790(2) 0.0176(6) Uani 1 1 d . . . . .
H13 H 0.076622 0.242135 0.083753 0.026 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
C1 C2 1.501(5) . ?
C1 C6 1.526(4) . ?
C1 C10 1.526(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.327(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.511(4) . ?
C3 Br7 1.912(3) . ?
C4 C5 1.550(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.523(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.515(4) . ?
C6 C12 1.556(4) . ?
C8 O11 1.209(4) . ?
C8 O9 1.350(3) . ?
C10 O9 1.471(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 O13 1.412(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 H13 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 111.4(3) . . ?
C2 C1 C10 123.3(3) . . ?
C6 C1 C10 102.0(3) . . ?
C2 C1 H1 106.3 . . ?
C6 C1 H1 106.3 . . ?
C10 C1 H1 106.3 . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 126.9(3) . . ?
C2 C3 Br7 120.2(2) . . ?
C4 C3 Br7 112.9(2) . . ?
C3 C4 C5 114.5(2) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 109.3(3) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C8 C6 C5 117.9(3) . . ?
C8 C6 C1 98.4(3) . . ?
C5 C6 C1 110.0(3) . . ?
C8 C6 C12 106.5(3) . . ?
C5 C6 C12 111.1(3) . . ?
C1 C6 C12 112.4(3) . . ?
O11 C8 O9 120.3(3) . . ?
O11 C8 C6 130.5(3) . . ?
O9 C8 C6 109.2(2) . . ?
O9 C10 C1 101.6(2) . . ?
O9 C10 H10A 111.4 . . ?
C1 C10 H10A 111.4 . . ?
O9 C10 H10B 111.4 . . ?
C1 C10 H10B 111.4 . . ?
H10A C10 H10B 109.3 . . ?
O13 C12 C6 113.2(3) . . ?
O13 C12 H12A 108.9 . . ?
C6 C12 H12A 108.9 . . ?
O13 C12 H12B 108.9 . . ?
C6 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C8 O9 C10 110.4(2) . . ?
C12 O13 H13 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
C6 C1 C2 C3 -33.9(5) . . . . ?
C10 C1 C2 C3 -155.6(5) . . . . ?
C1 C2 C3 C4 4.9(9) . . . . ?
C1 C2 C3 Br7 -175.2(3) . . . . ?
C2 C3 C4 C5 -2.6(10) . . . . ?
Br7 C3 C4 C5 177.5(5) . . . . ?
C3 C4 C5 C6 29.0(8) . . . . ?
C4 C5 C6 C8 -169.5(5) . . . . ?
C4 C5 C6 C1 -57.8(6) . . . . ?
C4 C5 C6 C12 67.2(5) . . . . ?
C2 C1 C6 C8 -174.6(3) . . . . ?
C10 C1 C6 C8 -41.1(4) . . . . ?
C2 C1 C6 C5 61.6(4) . . . . ?
C10 C1 C6 C5 -165.0(3) . . . . ?
C2 C1 C6 C12 -62.7(4) . . . . ?
C10 C1 C6 C12 70.7(4) . . . . ?
C5 C6 C8 O11 -29.6(8) . . . . ?
C1 C6 C8 O11 -147.6(6) . . . . ?
C12 C6 C8 O11 96.0(6) . . . . ?
C5 C6 C8 O9 149.8(5) . . . . ?
C1 C6 C8 O9 31.8(5) . . . . ?
C12 C6 C8 O9 -84.6(5) . . . . ?
C2 C1 C10 O9 163.3(4) . . . . ?
C6 C1 C10 O9 37.3(5) . . . . ?
C8 C6 C12 O13 -44.9(3) . . . . ?
C5 C6 C12 O13 84.7(3) . . . . ?
C1 C6 C12 O13 -151.6(3) . . . . ?
O11 C8 O9 C10 170.5(5) . . . . ?
C6 C8 O9 C10 -8.9(7) . . . . ?
C1 C10 O9 C8 -18.1(6) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051

