# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
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data_cu_2016003_0m
_database_code_depnum_ccdc_archive 'CCDC 1510140'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Br O7'
_chemical_formula_sum            'C16 H17 Br O7'
_chemical_formula_weight         401.19
_chemical_absolute_configuration ad
_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 0.0180 0.0090 '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 -0.6760 1.2810 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5345(9)
_cell_length_b                   10.8618(18)
_cell_length_c                   14.707(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.962(7)
_cell_angle_gamma                90
_cell_volume                     870.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      68
_cell_measurement_theta_min      3
_shelx_estimated_absorpt_T_max   68
_shelx_estimated_absorpt_T_min   3
_exptl_absorpt_coefficient_mu    3.532
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0624 after correction.
The Ratio of minimum to maximum transmission is 0.5776.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6095
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.509
_diffrn_reflns_theta_min         3.051
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                2856
_reflns_number_total             3000
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.089(12)
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.053
_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)+(0.0512P)²+0.2411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1058
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5A), C16(H16)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 1.03933(13) 0.46430(9) 1.00039(4) 0.0985(4) Uani 1 1 d . . . . .
O1 O 0.8036(17) 0.6473(6) 1.1040(3) 0.137(3) Uani 1 1 d . . . . .
O2 O 0.5653(7) 0.6463(3) 0.6665(2) 0.0589(8) Uani 1 1 d . . . . .
O3 O 0.6609(4) 0.4700(3) 0.59454(19) 0.0520(6) Uani 1 1 d . . . . .
O4 O 0.6449(5) 0.2662(3) 0.5842(3) 0.0589(8) Uani 1 1 d . . . . .
O5 O 0.1612(5) 0.2942(3) 0.6122(2) 0.0521(7) Uani 1 1 d . . . . .
H5 H 0.0132 0.2900 0.5931 0.078 Uiso 1 1 calc GR . . . .
O6 O 0.2931(7) 0.4386(3) 0.4113(2) 0.0678(10) Uani 1 1 d . . . . .
O7 O -0.0145(7) 0.3126(4) 0.4289(3) 0.0748(11) Uani 1 1 d . . . . .
C1 C 0.7843(10) 0.5758(5) 0.9537(3) 0.0626(12) Uani 1 1 d . . . . .
C3 C 0.718(4) 0.7353(10) 1.1643(5) 0.204(9) Uani 1 1 d . . . . .
H3A H 0.5424 0.7373 1.1524 0.306 Uiso 1 1 calc GR . . . .
H3B H 0.7810 0.8154 1.1535 0.306 Uiso 1 1 calc GR . . . .
H3C H 0.7750 0.7120 1.2274 0.306 Uiso 1 1 calc GR . . . .
C2 C 0.6968(16) 0.6546(6) 1.0128(4) 0.0839(19) Uani 1 1 d . . . . .
C4 C 0.5077(19) 0.7332(6) 0.9775(5) 0.101(3) Uani 1 1 d . . . . .
H4 H 0.4452 0.7872 1.0167 0.122 Uiso 1 1 calc R . . . .
C5 C 0.4094(13) 0.7325(5) 0.8834(5) 0.0763(16) Uani 1 1 d . . . . .
H5A H 0.2838 0.7867 0.8602 0.092 Uiso 1 1 calc R . . . .
C6 C 0.4978(9) 0.6520(4) 0.8252(3) 0.0538(10) Uani 1 1 d . . . . .
C7 C 0.3801(9) 0.6469(4) 0.7245(3) 0.0563(10) Uani 1 1 d . . . . .
H7 H 0.2740 0.7189 0.7095 0.068 Uiso 1 1 calc R . . . .
C8 C 0.4930(9) 0.5743(4) 0.5894(3) 0.0493(9) Uani 1 1 d . . . . .
H8 H 0.4896 0.6214 0.5323 0.059 Uiso 1 1 calc R . . . .
C9 C 0.5419(7) 0.3634(4) 0.5810(3) 0.0436(8) Uani 1 1 d . . . . .
C10 C 0.2631(7) 0.3833(3) 0.5630(3) 0.0433(8) Uani 1 1 d . . . . .
C11 C 0.1634(7) 0.3719(4) 0.4593(3) 0.0481(9) Uani 1 1 d . . . . .
C12 C 0.2134(13) 0.4400(6) 0.3112(3) 0.0784(16) Uani 1 1 d . . . . .
H12A H 0.1927 0.3566 0.2876 0.094 Uiso 1 1 calc R . . . .
H12B H 0.0581 0.4829 0.2954 0.094 Uiso 1 1 calc R . . . .
C13 C 0.402(3) 0.5031(9) 0.2717(6) 0.130(4) Uani 1 1 d . . . . .
H13A H 0.3647 0.4979 0.2056 0.195 Uiso 1 1 calc GR . . . .
H13B H 0.5582 0.4652 0.2932 0.195 Uiso 1 1 calc GR . . . .
H13C H 0.4082 0.5880 0.2901 0.195 Uiso 1 1 calc GR . . . .
C14 C 0.2421(7) 0.5171(3) 0.5941(3) 0.0444(9) Uani 1 1 d . . . . .
H14 H 0.1077 0.5611 0.5553 0.053 Uiso 1 1 calc R . . . .
C15 C 0.2331(8) 0.5307(5) 0.6970(3) 0.0545(10) Uani 1 1 d . . . . .
H15A H 0.0655 0.5397 0.7072 0.065 Uiso 1 1 calc R . . . .
H15B H 0.3070 0.4602 0.7316 0.065 Uiso 1 1 calc R . . . .
C16 C 0.6846(9) 0.5738(4) 0.8605(3) 0.0542(10) Uani 1 1 d . . . . .
H16 H 0.7454 0.5188 0.8216 0.065 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
Br1 C1 1.896(6) . ?
O1 C3 1.438(13) . ?
O1 C2 1.371(8) . ?
O2 C7 1.442(6) . ?
O2 C8 1.379(5) . ?
O3 C8 1.459(6) . ?
O3 C9 1.330(5) . ?
O4 C9 1.197(5) . ?
O5 H5 0.8200 . ?
O5 C10 1.385(5) . ?
O6 C11 1.309(6) . ?
O6 C12 1.463(6) . ?
O7 C11 1.197(5) . ?
C1 C2 1.366(8) . ?
C1 C16 1.387(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 C4 1.381(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(11) . ?
C5 H5A 0.9300 . ?
C5 C6 1.373(7) . ?
C6 C7 1.512(6) . ?
C6 C16 1.369(7) . ?
C7 H7 0.9800 . ?
C7 C15 1.517(6) . ?
C8 H8 0.9800 . ?
C8 C14 1.534(6) . ?
C9 C10 1.535(5) . ?
C10 C11 1.535(5) . ?
C10 C14 1.534(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.452(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.530(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9300 . ?

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 O1 C3 115.7(9) . . ?
C8 O2 C7 110.7(3) . . ?
C9 O3 C8 111.9(3) . . ?
C10 O5 H5 109.5 . . ?
C11 O6 C12 116.8(4) . . ?
C2 C1 Br1 119.6(4) . . ?
C2 C1 C16 121.0(6) . . ?
C16 C1 Br1 119.4(4) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C2 C4 125.1(6) . . ?
C1 C2 O1 116.4(7) . . ?
C1 C2 C4 118.5(5) . . ?
C2 C4 H4 119.7 . . ?
C2 C4 C5 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C7 119.7(5) . . ?
C16 C6 C5 119.0(5) . . ?
C16 C6 C7 121.2(4) . . ?
O2 C7 C6 110.5(4) . . ?
O2 C7 H7 109.3 . . ?
O2 C7 C15 104.0(4) . . ?
C6 C7 H7 109.3 . . ?
C6 C7 C15 114.3(4) . . ?
C15 C7 H7 109.3 . . ?
O2 C8 O3 107.8(4) . . ?
O2 C8 H8 111.6 . . ?
O2 C8 C14 109.2(4) . . ?
O3 C8 H8 111.6 . . ?
O3 C8 C14 104.9(3) . . ?
C14 C8 H8 111.6 . . ?
O3 C9 C10 111.1(3) . . ?
O4 C9 O3 122.8(4) . . ?
O4 C9 C10 126.1(4) . . ?
O5 C10 C9 107.4(3) . . ?
O5 C10 C11 110.7(3) . . ?
O5 C10 C14 116.6(3) . . ?
C11 C10 C9 109.7(3) . . ?
C14 C10 C9 102.0(3) . . ?
C14 C10 C11 109.9(3) . . ?
O6 C11 C10 110.8(3) . . ?
O7 C11 O6 126.1(4) . . ?
O7 C11 C10 123.1(4) . . ?
O6 C12 H12A 110.3 . . ?
O6 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 O6 107.2(6) . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 C10 104.7(3) . . ?
C8 C14 H14 112.2 . . ?
C10 C14 H14 112.2 . . ?
C15 C14 C8 101.0(3) . . ?
C15 C14 C10 113.8(3) . . ?
C15 C14 H14 112.2 . . ?
C7 C15 C14 103.6(4) . . ?
C7 C15 H15A 111.0 . . ?
C7 C15 H15B 111.0 . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C1 C16 H16 119.6 . . ?
C6 C16 C1 120.7(4) . . ?
C6 C16 H16 119.6 . . ?

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 C1 C2 O1 0.3(8) . . . . ?
Br1 C1 C2 C4 -178.7(5) . . . . ?
Br1 C1 C16 C6 179.0(4) . . . . ?
O1 C2 C4 C5 -179.3(7) . . . . ?
O2 C7 C15 C14 -33.0(4) . . . . ?
O2 C8 C14 C10 -137.5(4) . . . . ?
O2 C8 C14 C15 -19.0(4) . . . . ?
O3 C8 C14 C10 -22.2(4) . . . . ?
O3 C8 C14 C15 96.3(4) . . . . ?
O3 C9 C10 O5 -137.7(3) . . . . ?
O3 C9 C10 C11 101.9(4) . . . . ?
O3 C9 C10 C14 -14.6(4) . . . . ?
O4 C9 C10 O5 41.4(6) . . . . ?
O4 C9 C10 C11 -79.0(5) . . . . ?
O4 C9 C10 C14 164.5(4) . . . . ?
O5 C10 C11 O6 -167.4(4) . . . . ?
O5 C10 C11 O7 14.9(6) . . . . ?
O5 C10 C14 C8 138.4(4) . . . . ?
O5 C10 C14 C15 29.0(5) . . . . ?
C1 C2 C4 C5 -0.4(11) . . . . ?
C3 O1 C2 C1 176.8(9) . . . . ?
C3 O1 C2 C4 -4.3(13) . . . . ?
C2 C1 C16 C6 0.8(8) . . . . ?
C2 C4 C5 C6 1.0(11) . . . . ?
C4 C5 C6 C7 176.4(5) . . . . ?
C4 C5 C6 C16 -0.7(9) . . . . ?
C5 C6 C7 O2 134.0(5) . . . . ?
C5 C6 C7 C15 -109.1(5) . . . . ?
C5 C6 C16 C1 -0.2(8) . . . . ?
C6 C7 C15 C14 -153.5(4) . . . . ?
C7 O2 C8 O3 -115.0(4) . . . . ?
C7 O2 C8 C14 -1.5(5) . . . . ?
C7 C6 C16 C1 -177.3(4) . . . . ?
C8 O2 C7 C6 144.9(4) . . . . ?
C8 O2 C7 C15 21.9(5) . . . . ?
C8 O3 C9 O4 -178.5(4) . . . . ?
C8 O3 C9 C10 0.6(4) . . . . ?
C8 C14 C15 C7 31.0(4) . . . . ?
C9 O3 C8 O2 130.1(3) . . . . ?
C9 O3 C8 C14 13.8(4) . . . . ?
C9 C10 C11 O6 -49.0(5) . . . . ?
C9 C10 C11 O7 133.4(5) . . . . ?
C9 C10 C14 C8 21.7(4) . . . . ?
C9 C10 C14 C15 -87.6(4) . . . . ?
C10 C14 C15 C7 142.6(4) . . . . ?
C11 O6 C12 C13 -171.5(6) . . . . ?
C11 C10 C14 C8 -94.6(4) . . . . ?
C11 C10 C14 C15 156.0(3) . . . . ?
C12 O6 C11 O7 -0.4(8) . . . . ?
C12 O6 C11 C10 -177.9(4) . . . . ?
C14 C10 C11 O6 62.4(5) . . . . ?
C14 C10 C11 O7 -115.2(5) . . . . ?
C16 C1 C2 O1 178.5(6) . . . . ?
C16 C1 C2 C4 -0.5(9) . . . . ?
C16 C6 C7 O2 -48.9(6) . . . . ?
C16 C6 C7 C15 68.0(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
