# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1519781'
_audit_update_record             
;
2016-11-29 deposited with the CCDC.
2017-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Br2 O6'
_chemical_formula_weight         554.22
_chemical_oxdiff_usercomment     'mark Coster sample MJC-2-049A'


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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.0088(1)
_cell_length_b                   14.48800(10)
_cell_length_c                   25.2409(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2197.36(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    12375
_cell_measurement_theta_min      3.0540
_cell_measurement_theta_max      76.6840

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5546
_exptl_crystal_size_mid          0.2710
_exptl_crystal_size_min          0.2193
_exptl_absorpt_coefficient_mu    5.007
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.31272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15254
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.502
_diffrn_reflns_theta_max         76.889
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4594
_reflns_number_gt                4580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_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)+(0.0478P)²+0.8656P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1909 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.012(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4594
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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 0.9044(5) 0.9109(2) 0.56884(11) 0.0160(5) Uani 1 1 d . . . . .
C2 C 0.8754(5) 1.0146(2) 0.57669(11) 0.0166(5) Uani 1 1 d . . . . .
H2 H 0.7630 1.0249 0.6053 0.020 Uiso 1 1 calc R U . . .
C3 C 0.7709(6) 1.0420(2) 0.52349(12) 0.0203(6) Uani 1 1 d . . . . .
H3A H 0.8867 1.0546 0.4966 0.024 Uiso 1 1 calc R U . . .
H3B H 0.6748 1.0970 0.5273 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6336(5) 0.9563(2) 0.50878(12) 0.0213(6) Uani 1 1 d . . . . .
H4A H 0.4727 0.9689 0.5131 0.026 Uiso 1 1 calc R U . . .
H4B H 0.6617 0.9385 0.4715 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9462(5) 0.8498(2) 0.61694(12) 0.0183(6) Uani 1 1 d . . . . .
H5 H 1.0649 0.8793 0.6389 0.022 Uiso 1 1 calc R U . . .
C6 C 1.0448(6) 0.7635(2) 0.59087(15) 0.0267(7) Uani 1 1 d . . . . .
H6A H 1.1450 0.7304 0.6155 0.032 Uiso 1 1 calc R U . . .
H6B H 0.9261 0.7209 0.5790 0.032 Uiso 1 1 calc R U . . .
C7 C 1.1726(5) 0.8023(2) 0.54417(13) 0.0242(6) Uani 1 1 d . . . . .
H7A H 1.3338 0.8044 0.5522 0.029 Uiso 1 1 calc R U . . .
H7B H 1.1498 0.7633 0.5124 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0829(5) 1.0679(2) 0.59040(12) 0.0203(6) Uani 1 1 d . . . . .
H8A H 1.2117 1.0437 0.5703 0.024 Uiso 1 1 calc R U . . .
H8B H 1.0637 1.1340 0.5816 0.024 Uiso 1 1 calc R U . . .
C9 C 1.3085(6) 1.0909(2) 0.66575(12) 0.0185(6) Uani 1 1 d . . . . .
C10 C 1.3261(5) 1.08160(19) 0.72453(12) 0.0178(5) Uani 1 1 d . . . . .
C11 C 1.1555(5) 1.0456(2) 0.75543(13) 0.0234(6) Uani 1 1 d . . . . .
H11 H 1.0232 1.0240 0.7390 0.028 Uiso 1 1 calc R U . . .
C12 C 1.1769(6) 1.0409(2) 0.81006(13) 0.0242(6) Uani 1 1 d . . . . .
H12 H 1.0600 1.0169 0.8314 0.029 Uiso 1 1 calc R U . . .
C13 C 1.3721(6) 1.0719(2) 0.83279(12) 0.0210(6) Uani 1 1 d . . . . .
C14 C 1.5461(6) 1.1065(2) 0.80294(14) 0.0256(7) Uani 1 1 d . . . . .
H14 H 1.6798 1.1265 0.8194 0.031 Uiso 1 1 calc R U . . .
C15 C 1.5211(6) 1.1113(2) 0.74846(14) 0.0243(6) Uani 1 1 d . . . . .
H15 H 1.6386 1.1351 0.7273 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7426(5) 0.8359(2) 0.65158(12) 0.0231(6) Uani 1 1 d . . . . .
H16A H 0.6514 0.8927 0.6527 0.028 Uiso 1 1 calc R U . . .
H16B H 0.6499 0.7846 0.6379 0.028 Uiso 1 1 calc R U . . .
C17 C 0.6982(6) 0.8360(2) 0.74510(13) 0.0203(6) Uani 1 1 d . . . . .
C18 C 0.8214(5) 0.82702(19) 0.79636(12) 0.0184(6) Uani 1 1 d . . . . .
C19 C 1.0343(6) 0.7900(2) 0.79896(12) 0.0211(6) Uani 1 1 d . . . . .
H19 H 1.1041 0.7686 0.7675 0.025 Uiso 1 1 calc R U . . .
C20 C 1.1461(5) 0.7838(2) 0.84690(13) 0.0233(6) Uani 1 1 d . . . . .
H20 H 1.2901 0.7570 0.8489 0.028 Uiso 1 1 calc R U . . .
C21 C 1.0413(5) 0.8180(2) 0.89203(12) 0.0204(6) Uani 1 1 d . . . . .
C22 C 0.8298(6) 0.8557(2) 0.89047(13) 0.0259(7) Uani 1 1 d . . . . .
H22 H 0.7614 0.8784 0.9218 0.031 Uiso 1 1 calc R U . . .
C23 C 0.7206(6) 0.8594(2) 0.84245(13) 0.0227(6) Uani 1 1 d . . . . .
H23 H 0.5746 0.8843 0.8408 0.027 Uiso 1 1 calc R U . . .
O1 O 0.7025(4) 0.88333(15) 0.54414(9) 0.0203(4) Uani 1 1 d . . . . .
O2 O 1.0882(4) 0.89448(14) 0.53491(8) 0.0192(4) Uani 1 1 d . . . . .
O3 O 0.8288(4) 0.81387(17) 0.70394(8) 0.0237(5) Uani 1 1 d . . . . .
O4 O 0.5092(4) 0.8614(2) 0.74123(10) 0.0317(6) Uani 1 1 d . . . . .
O5 O 1.1186(4) 1.05627(16) 0.64695(8) 0.0209(4) Uani 1 1 d . . . . .
O6 O 1.4498(4) 1.12550(19) 0.63825(10) 0.0288(5) Uani 1 1 d . . . . .
Br1 Br 1.40239(7) 1.06750(2) 0.90800(2) 0.02833(10) Uani 1 1 d . . . . .
Br2 Br 1.19646(6) 0.81099(2) 0.95757(2) 0.02833(10) 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
C1 O2 1.418(4) . ?
C1 O1 1.421(4) . ?
C1 C5 1.523(4) . ?
C1 C2 1.526(4) . ?
C2 C8 1.507(4) . ?
C2 C3 1.534(4) . ?
C3 C4 1.536(4) . ?
C4 O1 1.444(4) . ?
C5 C16 1.517(4) . ?
C5 C6 1.531(4) . ?
C6 C7 1.515(5) . ?
C7 O2 1.447(4) . ?
C8 O5 1.453(4) . ?
C9 O6 1.206(4) . ?
C9 O5 1.334(4) . ?
C9 C10 1.494(4) . ?
C10 C15 1.387(4) . ?
C10 C11 1.390(5) . ?
C11 C12 1.387(5) . ?
C12 C13 1.381(5) . ?
C13 C14 1.382(5) . ?
C13 Br1 1.908(3) . ?
C14 C15 1.385(5) . ?
C16 O3 1.455(4) . ?
C17 O4 1.198(4) . ?
C17 O3 1.341(4) . ?
C17 C18 1.496(4) . ?
C18 C19 1.389(4) . ?
C18 C23 1.393(4) . ?
C19 C20 1.387(5) . ?
C20 C21 1.393(4) . ?
C21 C22 1.383(5) . ?
C21 Br2 1.902(3) . ?
C22 C23 1.379(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
O2 C1 O1 110.7(2) . . ?
O2 C1 C5 104.8(2) . . ?
O1 C1 C5 109.1(2) . . ?
O2 C1 C2 109.4(2) . . ?
O1 C1 C2 103.7(2) . . ?
C5 C1 C2 119.2(2) . . ?
C8 C2 C1 116.1(3) . . ?
C8 C2 C3 114.0(2) . . ?
C1 C2 C3 100.8(2) . . ?
C2 C3 C4 102.9(2) . . ?
O1 C4 C3 106.7(2) . . ?
C16 C5 C1 113.8(3) . . ?
C16 C5 C6 116.8(3) . . ?
C1 C5 C6 101.3(2) . . ?
C7 C6 C5 103.2(2) . . ?
O2 C7 C6 106.9(2) . . ?
O5 C8 C2 106.8(2) . . ?
O6 C9 O5 123.7(3) . . ?
O6 C9 C10 124.0(3) . . ?
O5 C9 C10 112.3(3) . . ?
C15 C10 C11 119.7(3) . . ?
C15 C10 C9 117.7(3) . . ?
C11 C10 C9 122.6(3) . . ?
C12 C11 C10 120.6(3) . . ?
C13 C12 C11 118.4(3) . . ?
C12 C13 C14 122.3(3) . . ?
C12 C13 Br1 118.9(2) . . ?
C14 C13 Br1 118.8(2) . . ?
C13 C14 C15 118.5(3) . . ?
C14 C15 C10 120.6(3) . . ?
O3 C16 C5 105.4(2) . . ?
O4 C17 O3 124.4(3) . . ?
O4 C17 C18 124.5(3) . . ?
O3 C17 C18 111.1(3) . . ?
C19 C18 C23 119.4(3) . . ?
C19 C18 C17 122.0(3) . . ?
C23 C18 C17 118.5(3) . . ?
C20 C19 C18 120.8(3) . . ?
C19 C20 C21 118.1(3) . . ?
C22 C21 C20 122.2(3) . . ?
C22 C21 Br2 119.7(2) . . ?
C20 C21 Br2 118.1(2) . . ?
C23 C22 C21 118.5(3) . . ?
C22 C23 C18 120.9(3) . . ?
C1 O1 C4 108.1(2) . . ?
C1 O2 C7 109.3(2) . . ?
C17 O3 C16 116.3(2) . . ?
C9 O5 C8 115.6(2) . . ?

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 C1 C2 C8 -48.0(3) . . . . ?
O1 C1 C2 C8 -166.1(2) . . . . ?
C5 C1 C2 C8 72.4(3) . . . . ?
O2 C1 C2 C3 75.7(3) . . . . ?
O1 C1 C2 C3 -42.4(3) . . . . ?
C5 C1 C2 C3 -163.8(3) . . . . ?
C8 C2 C3 C4 157.6(3) . . . . ?
C1 C2 C3 C4 32.5(3) . . . . ?
C2 C3 C4 O1 -12.5(3) . . . . ?
O2 C1 C5 C16 -164.2(3) . . . . ?
O1 C1 C5 C16 -45.6(3) . . . . ?
C2 C1 C5 C16 73.1(4) . . . . ?
O2 C1 C5 C6 -38.0(3) . . . . ?
O1 C1 C5 C6 80.6(3) . . . . ?
C2 C1 C5 C6 -160.7(3) . . . . ?
C16 C5 C6 C7 157.6(3) . . . . ?
C1 C5 C6 C7 33.5(3) . . . . ?
C5 C6 C7 O2 -18.2(3) . . . . ?
C1 C2 C8 O5 -81.3(3) . . . . ?
C3 C2 C8 O5 162.1(2) . . . . ?
O6 C9 C10 C15 -2.8(5) . . . . ?
O5 C9 C10 C15 177.1(3) . . . . ?
O6 C9 C10 C11 176.7(3) . . . . ?
O5 C9 C10 C11 -3.5(4) . . . . ?
C15 C10 C11 C12 1.4(5) . . . . ?
C9 C10 C11 C12 -178.0(3) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C11 C12 C13 Br1 179.2(2) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
Br1 C13 C14 C15 -178.7(3) . . . . ?
C13 C14 C15 C10 -0.3(5) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
C9 C10 C15 C14 178.6(3) . . . . ?
C1 C5 C16 O3 -155.5(2) . . . . ?
C6 C5 C16 O3 87.0(3) . . . . ?
O4 C17 C18 C19 174.6(3) . . . . ?
O3 C17 C18 C19 -6.9(4) . . . . ?
O4 C17 C18 C23 -7.2(5) . . . . ?
O3 C17 C18 C23 171.3(3) . . . . ?
C23 C18 C19 C20 0.8(5) . . . . ?
C17 C18 C19 C20 179.0(3) . . . . ?
C18 C19 C20 C21 -1.7(5) . . . . ?
C19 C20 C21 C22 1.4(5) . . . . ?
C19 C20 C21 Br2 -179.2(2) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
Br2 C21 C22 C23 -179.6(3) . . . . ?
C21 C22 C23 C18 -0.8(5) . . . . ?
C19 C18 C23 C22 0.5(5) . . . . ?
C17 C18 C23 C22 -177.8(3) . . . . ?
O2 C1 O1 C4 -81.1(3) . . . . ?
C5 C1 O1 C4 164.0(2) . . . . ?
C2 C1 O1 C4 36.1(3) . . . . ?
C3 C4 O1 C1 -14.6(3) . . . . ?
O1 C1 O2 C7 -89.6(3) . . . . ?
C5 C1 O2 C7 27.9(3) . . . . ?
C2 C1 O2 C7 156.8(2) . . . . ?
C6 C7 O2 C1 -5.9(3) . . . . ?
O4 C17 O3 C16 9.4(5) . . . . ?
C18 C17 O3 C16 -169.1(3) . . . . ?
C5 C16 O3 C17 152.9(3) . . . . ?
O6 C9 O5 C8 -3.8(4) . . . . ?
C10 C9 O5 C8 176.3(2) . . . . ?
C2 C8 O5 C9 173.4(2) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.071

_shelxl_version_number           2012-9



