# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_FO6598
_database_code_depnum_ccdc_archive 'CCDC 1845339'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 B Br O4'
_chemical_formula_sum            'C16 H20 B Br O4'
_chemical_formula_weight         367.04

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.2446(3)
_cell_length_b                   10.9482(5)
_cell_length_c                   21.3662(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.091(3)
_cell_angle_gamma                90
_cell_volume                     1677.80(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    19180
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.108
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4965
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19180
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3834
_reflns_number_gt                3241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0228P)²+3.2536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.22773(4) -0.03152(3) 0.379587(15) 0.03235(10) Uani 1 1 d . . .
B1 B 0.4826(4) 0.3800(3) 0.38021(15) 0.0215(6) Uani 1 1 d . . .
O1 O 0.2383(3) 0.41367(18) 0.45420(10) 0.0281(4) Uani 1 1 d . . .
O2 O 0.2106(3) 0.28615(17) 0.53546(10) 0.0273(4) Uani 1 1 d . . .
O3 O 0.3719(3) 0.35314(16) 0.32478(9) 0.0237(4) Uani 1 1 d . . .
O4 O 0.5489(3) 0.49655(17) 0.38432(9) 0.0244(4) Uani 1 1 d . . .
C1 C 0.5508(4) 0.2757(2) 0.42949(13) 0.0216(5) Uani 1 1 d . . .
C2 C 0.4594(4) 0.2541(2) 0.47885(13) 0.0242(6) Uani 1 1 d . . .
H2 H 0.495(5) 0.193(3) 0.5114(17) 0.040(10) Uiso 1 1 d . . .
C3 C 0.2942(4) 0.3280(2) 0.48734(13) 0.0242(6) Uani 1 1 d . . .
C4 C 0.0494(5) 0.3556(3) 0.54782(17) 0.0317(7) Uani 1 1 d . . .
H4C H -0.002(5) 0.310(3) 0.5815(16) 0.034(9) Uiso 1 1 d . . .
H4B H 0.088(5) 0.436(4) 0.5627(18) 0.045(11) Uiso 1 1 d . . .
H4A H -0.049(6) 0.358(4) 0.510(2) 0.055(12) Uiso 1 1 d . . .
C5 C 0.3277(4) 0.4687(2) 0.29103(13) 0.0228(5) Uani 1 1 d . . .
C6 C 0.4771(4) 0.5595(2) 0.32538(13) 0.0234(6) Uani 1 1 d . . .
C7 C 0.3983(5) 0.6817(3) 0.34287(18) 0.0340(7) Uani 1 1 d . . .
H7C H 0.496(5) 0.731(3) 0.3660(16) 0.030(9) Uiso 1 1 d . . .
H7B H 0.340(5) 0.724(4) 0.3031(19) 0.051(11) Uiso 1 1 d . . .
H7A H 0.315(5) 0.669(4) 0.3705(18) 0.045(11) Uiso 1 1 d . . .
C8 C 0.6438(5) 0.5809(3) 0.29067(17) 0.0346(7) Uani 1 1 d . . .
H8C H 0.702(5) 0.506(3) 0.2826(17) 0.034(9) Uiso 1 1 d . . .
H8B H 0.741(5) 0.626(3) 0.3179(17) 0.039(10) Uiso 1 1 d . . .
H8A H 0.608(5) 0.624(4) 0.2525(19) 0.051(11) Uiso 1 1 d . . .
C9 C 0.3402(5) 0.4483(3) 0.22173(15) 0.0309(7) Uani 1 1 d . . .
H9C H 0.457(5) 0.417(3) 0.2172(15) 0.027(8) Uiso 1 1 d . . .
H9B H 0.242(5) 0.391(3) 0.2023(17) 0.039(10) Uiso 1 1 d . . .
H9A H 0.317(5) 0.528(4) 0.1989(19) 0.047(11) Uiso 1 1 d . . .
C10 C 0.1275(4) 0.4986(3) 0.29943(17) 0.0314(7) Uani 1 1 d . . .
H10C H 0.040(6) 0.429(4) 0.2791(19) 0.055(12) Uiso 1 1 d . . .
H10B H 0.084(5) 0.574(4) 0.2776(17) 0.041(10) Uiso 1 1 d . . .
H10A H 0.116(5) 0.505(3) 0.344(2) 0.043(10) Uiso 1 1 d . . .
C11 C 0.7129(4) 0.2009(2) 0.41772(12) 0.0211(5) Uani 1 1 d . . .
C12 C 0.7363(4) 0.0802(2) 0.43928(13) 0.0227(5) Uani 1 1 d . . .
H12 H 0.645(4) 0.044(3) 0.4590(15) 0.024(8) Uiso 1 1 d . . .
C13 C 0.8879(4) 0.0114(2) 0.42850(13) 0.0239(6) Uani 1 1 d . . .
H13 H 0.902(4) -0.068(3) 0.4419(15) 0.028(8) Uiso 1 1 d . . .
C14 C 1.0202(4) 0.0639(3) 0.39595(13) 0.0240(6) Uani 1 1 d . . .
C15 C 1.0030(4) 0.1826(3) 0.37332(14) 0.0246(6) Uani 1 1 d . . .
H15 H 1.094(5) 0.216(3) 0.3526(16) 0.033(9) Uiso 1 1 d . . .
C16 C 0.8482(4) 0.2498(2) 0.38445(14) 0.0252(6) Uani 1 1 d . . .
H16 H 0.835(4) 0.330(3) 0.3687(15) 0.028(8) Uiso 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
Br1 C14 1.903(3) . ?
B1 O4 1.362(4) . ?
B1 O3 1.366(4) . ?
B1 C1 1.584(4) . ?
O1 C3 1.210(3) . ?
O2 C3 1.345(3) . ?
O2 C4 1.448(4) . ?
O3 C5 1.469(3) . ?
O4 C6 1.465(3) . ?
C1 C2 1.343(4) . ?
C1 C11 1.482(4) . ?
C2 C3 1.477(4) . ?
C2 H2 0.97(4) . ?
C4 H4C 0.99(4) . ?
C4 H4B 0.96(4) . ?
C4 H4A 1.00(4) . ?
C5 C9 1.512(4) . ?
C5 C10 1.522(4) . ?
C5 C6 1.573(4) . ?
C6 C8 1.521(4) . ?
C6 C7 1.522(4) . ?
C7 H7C 0.97(3) . ?
C7 H7B 1.01(4) . ?
C7 H7A 0.91(4) . ?
C8 H8C 0.95(4) . ?
C8 H8B 0.98(4) . ?
C8 H8A 0.95(4) . ?
C9 H9C 0.93(3) . ?
C9 H9B 0.99(4) . ?
C9 H9A 1.01(4) . ?
C10 H10C 1.05(4) . ?
C10 H10B 0.98(4) . ?
C10 H10A 0.97(4) . ?
C11 C16 1.396(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.378(4) . ?
C12 H12 0.92(3) . ?
C13 C14 1.386(4) . ?
C13 H13 0.92(3) . ?
C14 C15 1.386(4) . ?
C15 C16 1.389(4) . ?
C15 H15 0.92(3) . ?
C16 H16 0.94(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
O4 B1 O3 114.6(2) . . ?
O4 B1 C1 123.9(3) . . ?
O3 B1 C1 120.8(2) . . ?
C3 O2 C4 114.9(2) . . ?
B1 O3 C5 107.5(2) . . ?
B1 O4 C6 107.8(2) . . ?
C2 C1 C11 121.7(2) . . ?
C2 C1 B1 120.4(2) . . ?
C11 C1 B1 117.8(2) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 125(2) . . ?
C3 C2 H2 115(2) . . ?
O1 C3 O2 124.2(3) . . ?
O1 C3 C2 124.3(3) . . ?
O2 C3 C2 111.5(2) . . ?
O2 C4 H4C 105(2) . . ?
O2 C4 H4B 110(2) . . ?
H4C C4 H4B 110(3) . . ?
O2 C4 H4A 111(2) . . ?
H4C C4 H4A 108(3) . . ?
H4B C4 H4A 113(3) . . ?
O3 C5 C9 108.4(2) . . ?
O3 C5 C10 105.8(2) . . ?
C9 C5 C10 109.6(3) . . ?
O3 C5 C6 103.1(2) . . ?
C9 C5 C6 114.7(2) . . ?
C10 C5 C6 114.4(2) . . ?
O4 C6 C8 106.3(2) . . ?
O4 C6 C7 107.6(2) . . ?
C8 C6 C7 109.6(3) . . ?
O4 C6 C5 104.0(2) . . ?
C8 C6 C5 114.3(2) . . ?
C7 C6 C5 114.4(2) . . ?
C6 C7 H7C 110(2) . . ?
C6 C7 H7B 109(2) . . ?
H7C C7 H7B 112(3) . . ?
C6 C7 H7A 109(2) . . ?
H7C C7 H7A 105(3) . . ?
H7B C7 H7A 112(3) . . ?
C6 C8 H8C 111(2) . . ?
C6 C8 H8B 110(2) . . ?
H8C C8 H8B 104(3) . . ?
C6 C8 H8A 111(2) . . ?
H8C C8 H8A 111(3) . . ?
H8B C8 H8A 110(3) . . ?
C5 C9 H9C 110(2) . . ?
C5 C9 H9B 111(2) . . ?
H9C C9 H9B 109(3) . . ?
C5 C9 H9A 109(2) . . ?
H9C C9 H9A 111(3) . . ?
H9B C9 H9A 107(3) . . ?
C5 C10 H10C 109(2) . . ?
C5 C10 H10B 112(2) . . ?
H10C C10 H10B 106(3) . . ?
C5 C10 H10A 110(2) . . ?
H10C C10 H10A 109(3) . . ?
H10B C10 H10A 110(3) . . ?
C16 C11 C12 117.9(2) . . ?
C16 C11 C1 120.3(2) . . ?
C12 C11 C1 121.8(2) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119(2) . . ?
C11 C12 H12 120(2) . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 121(2) . . ?
C14 C13 H13 120(2) . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 Br1 119.0(2) . . ?
C15 C14 Br1 119.0(2) . . ?
C14 C15 C16 118.2(3) . . ?
C14 C15 H15 120(2) . . ?
C16 C15 H15 121(2) . . ?
C15 C16 C11 121.7(3) . . ?
C15 C16 H16 118(2) . . ?
C11 C16 H16 120(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.082
