# Electronic Supplementary Material (ESI) for Green 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).
# 
# 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_cd15337
_audit_block_doi                 10.5517/ccdc.csd.cc1lb6dj
_database_code_depnum_ccdc_archive 'CCDC 1469567'
_audit_update_record             
;
2016-03-19 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Br O6'
_chemical_formula_weight         357.15

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'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.0731(17)
_cell_length_b                   9.3483(17)
_cell_length_c                   17.357(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1472.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2149
_cell_measurement_theta_min      4.949
_cell_measurement_theta_max      43.506

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.816
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5321
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8809
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2887
_reflns_number_gt                2170
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 782 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.018(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2887
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27016(7) 0.31068(8) 0.20758(3) 0.0860(3) Uani 1 1 d . . . . .
O1 O 0.8591(5) 0.6348(4) 0.6159(2) 0.0713(11) Uani 1 1 d . . . . .
O2 O 0.6519(4) 0.5095(3) 0.62403(18) 0.0488(8) Uani 1 1 d . . . . .
O3 O 0.4936(5) 0.1933(4) 0.5876(2) 0.0727(11) Uani 1 1 d . . . . .
O4 O 0.4332(4) 0.3437(3) 0.68038(19) 0.0633(10) Uani 1 1 d . . . . .
O5 O 0.4477(3) 0.6750(3) 0.55497(17) 0.0507(8) Uani 1 1 d . . . . .
O6 O 0.3092(3) 0.4819(3) 0.52957(18) 0.0446(8) Uani 1 1 d . . . . .
C1 C 0.7687(6) 0.5653(5) 0.5836(3) 0.0535(12) Uani 1 1 d . . . . .
C2 C 0.7575(6) 0.5242(4) 0.5006(3) 0.0542(12) Uani 1 1 d . . . . .
H2A H 0.8516 0.4907 0.4812 0.065 Uiso 1 1 calc R U . . .
H2B H 0.7247 0.6044 0.4695 0.065 Uiso 1 1 calc R U . . .
C3 C 0.6437(5) 0.4045(4) 0.5002(3) 0.0426(10) Uani 1 1 d . . . . .
H3 H 0.6959 0.3148 0.5106 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5513(5) 0.4409(4) 0.5724(2) 0.0403(10) Uani 1 1 d . . . . .
C5 C 0.4898(5) 0.3090(5) 0.6136(3) 0.0452(10) Uani 1 1 d . . . . .
C6 C 0.3732(7) 0.2286(6) 0.7260(3) 0.0772(17) Uani 1 1 d . . . . .
H6A H 0.2853 0.1929 0.7020 0.116 Uiso 1 1 calc R U . . .
H6B H 0.3500 0.2633 0.7766 0.116 Uiso 1 1 calc R U . . .
H6C H 0.4444 0.1530 0.7298 0.116 Uiso 1 1 calc R U . . .
C7 C 0.4299(5) 0.5488(5) 0.5531(2) 0.0402(10) Uani 1 1 d . . . . .
C8 C 0.1955(5) 0.5709(5) 0.4967(3) 0.0542(12) Uani 1 1 d . . . . .
H8A H 0.1410 0.6164 0.5373 0.081 Uiso 1 1 calc R U . . .
H8B H 0.1302 0.5131 0.4664 0.081 Uiso 1 1 calc R U . . .
H8C H 0.2398 0.6426 0.4646 0.081 Uiso 1 1 calc R U . . .
C9 C 0.5578(5) 0.3849(4) 0.4261(2) 0.0414(10) Uani 1 1 d . . . . .
C10 C 0.5272(5) 0.2483(4) 0.4005(3) 0.0456(12) Uani 1 1 d . . . . .
H10 H 0.5636 0.1702 0.4277 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4432(6) 0.2254(5) 0.3349(3) 0.0509(12) Uani 1 1 d . . . . .
H11 H 0.4225 0.1329 0.3184 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3912(5) 0.3405(6) 0.2949(3) 0.0567(12) Uani 1 1 d . . . . .
C13 C 0.4215(7) 0.4774(6) 0.3187(3) 0.0628(15) Uani 1 1 d . . . . .
H13 H 0.3850 0.5552 0.2913 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5064(6) 0.4986(5) 0.3838(3) 0.0555(13) Uani 1 1 d . . . . .
H14 H 0.5292 0.5913 0.3992 0.067 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 C12 1.893(5) . ?
O1 C1 1.187(6) . ?
O2 C1 1.374(6) . ?
O2 C4 1.430(5) . ?
O3 C5 1.173(5) . ?
O4 C5 1.309(6) . ?
O4 C6 1.442(6) . ?
O5 C7 1.191(5) . ?
O6 C7 1.326(5) . ?
O6 C8 1.442(5) . ?
C1 C2 1.495(7) . ?
C2 C3 1.522(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C9 1.516(6) . ?
C3 C4 1.546(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.531(6) . ?
C4 C7 1.531(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.373(6) . ?
C9 C10 1.380(6) . ?
C10 C11 1.387(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(8) . ?
C13 C14 1.381(7) . ?
C13 H13 0.9300 . ?
C14 H14 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
C1 O2 C4 110.0(3) . . ?
C5 O4 C6 116.7(4) . . ?
C7 O6 C8 116.1(3) . . ?
O1 C1 O2 119.9(5) . . ?
O1 C1 C2 130.1(5) . . ?
O2 C1 C2 110.0(4) . . ?
C1 C2 C3 103.9(4) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C9 C3 C2 116.2(4) . . ?
C9 C3 C4 115.8(4) . . ?
C2 C3 C4 101.7(3) . . ?
C9 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C4 C3 H3 107.5 . . ?
O2 C4 C5 107.5(3) . . ?
O2 C4 C7 107.5(3) . . ?
C5 C4 C7 111.7(4) . . ?
O2 C4 C3 105.1(3) . . ?
C5 C4 C3 113.5(3) . . ?
C7 C4 C3 111.0(3) . . ?
O3 C5 O4 125.5(4) . . ?
O3 C5 C4 123.6(4) . . ?
O4 C5 C4 110.9(4) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 O6 126.0(4) . . ?
O5 C7 C4 123.3(4) . . ?
O6 C7 C4 110.6(4) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.5(4) . . ?
C14 C9 C3 122.3(4) . . ?
C10 C9 C3 119.2(4) . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 Br1 119.4(4) . . ?
C13 C12 Br1 119.6(4) . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 121.0(4) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?

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
C4 O2 C1 O1 175.0(4) . . . . ?
C4 O2 C1 C2 -5.0(5) . . . . ?
O1 C1 C2 C3 165.2(5) . . . . ?
O2 C1 C2 C3 -14.9(5) . . . . ?
C1 C2 C3 C9 153.4(4) . . . . ?
C1 C2 C3 C4 26.7(4) . . . . ?
C1 O2 C4 C5 143.8(4) . . . . ?
C1 O2 C4 C7 -95.8(4) . . . . ?
C1 O2 C4 C3 22.5(4) . . . . ?
C9 C3 C4 O2 -157.1(3) . . . . ?
C2 C3 C4 O2 -30.2(4) . . . . ?
C9 C3 C4 C5 85.6(4) . . . . ?
C2 C3 C4 C5 -147.4(4) . . . . ?
C9 C3 C4 C7 -41.2(5) . . . . ?
C2 C3 C4 C7 85.8(4) . . . . ?
C6 O4 C5 O3 1.2(8) . . . . ?
C6 O4 C5 C4 -179.0(4) . . . . ?
O2 C4 C5 O3 -126.2(5) . . . . ?
C7 C4 C5 O3 116.1(5) . . . . ?
C3 C4 C5 O3 -10.4(6) . . . . ?
O2 C4 C5 O4 54.0(5) . . . . ?
C7 C4 C5 O4 -63.7(5) . . . . ?
C3 C4 C5 O4 169.9(4) . . . . ?
C8 O6 C7 O5 6.2(6) . . . . ?
C8 O6 C7 C4 -169.4(4) . . . . ?
O2 C4 C7 O5 26.6(5) . . . . ?
C5 C4 C7 O5 144.4(4) . . . . ?
C3 C4 C7 O5 -87.8(5) . . . . ?
O2 C4 C7 O6 -157.6(3) . . . . ?
C5 C4 C7 O6 -39.9(5) . . . . ?
C3 C4 C7 O6 87.9(4) . . . . ?
C2 C3 C9 C14 -40.9(6) . . . . ?
C4 C3 C9 C14 78.3(5) . . . . ?
C2 C3 C9 C10 140.3(4) . . . . ?
C4 C3 C9 C10 -100.5(5) . . . . ?
C14 C9 C10 C11 -1.8(7) . . . . ?
C3 C9 C10 C11 177.0(4) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C10 C11 C12 Br1 -177.6(4) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
Br1 C12 C13 C14 178.2(4) . . . . ?
C10 C9 C14 C13 2.4(8) . . . . ?
C3 C9 C14 C13 -176.4(5) . . . . ?
C12 C13 C14 C9 -1.7(8) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

