# 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. 
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data_cd15073
_database_code_depnum_ccdc_archive 'CCDC 1469918'
_audit_update_record             
;
2017-11-13 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Br O3'
_chemical_formula_weight         385.24

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   18.502(3)
_cell_length_b                   7.5450(13)
_cell_length_c                   14.387(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.633(3)
_cell_angle_gamma                90
_cell_volume                     1745.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1779
_cell_measurement_theta_min      5.066
_cell_measurement_theta_max      45.090

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.369
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5224
_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            5212
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             3208
_reflns_number_gt                2500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.874

_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)+(0.0620P)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       0.0045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.009(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
Br1 Br 0.63655(5) 0.73910(12) 0.59443(5) 0.0860(3) Uani 1 1 d . . . . .
O1 O 0.78931(19) 0.6664(5) 0.2551(3) 0.0477(9) Uani 1 1 d . . . . .
O2 O 0.7278(3) 1.1798(7) 0.0571(4) 0.0835(15) Uani 1 1 d . . . . .
O3 O 0.8618(2) 1.1397(5) 0.1764(3) 0.0530(10) Uani 1 1 d . . . . .
C1 C 0.6996(3) 0.7001(7) 0.2106(4) 0.0460(13) Uani 1 1 d . . . . .
C2 C 0.6857(3) 0.8764(8) 0.1535(4) 0.0415(12) Uani 1 1 d . . . . .
C3 C 0.7664(3) 0.9250(7) 0.1644(3) 0.0362(10) Uani 1 1 d . . . . .
C4 C 0.8212(3) 0.7958(6) 0.2219(3) 0.0356(11) Uani 1 1 d . . . . .
C5 C 0.9081(2) 0.7612(7) 0.2492(3) 0.0363(10) Uani 1 1 d . . . . .
C6 C 0.9629(3) 0.6916(8) 0.3474(4) 0.0547(15) Uani 1 1 d . . . . .
H6 H 0.9464 0.6737 0.3981 0.066 Uiso 1 1 calc R U . . .
C7 C 1.0435(4) 0.6475(9) 0.3712(5) 0.0676(17) Uani 1 1 d . . . . .
H7 H 1.0817 0.6072 0.4391 0.081 Uiso 1 1 calc R U . . .
C8 C 1.0658(3) 0.6634(9) 0.2957(5) 0.0611(16) Uani 1 1 d . . . . .
H8 H 1.1188 0.6296 0.3106 0.073 Uiso 1 1 calc R U . . .
C9 C 1.0106(3) 0.7292(9) 0.1968(4) 0.0529(12) Uani 1 1 d . . . . .
H9 H 1.0267 0.7405 0.1452 0.063 Uiso 1 1 calc R U . . .
C10 C 0.9322(3) 0.7786(7) 0.1728(4) 0.0437(12) Uani 1 1 d . . . . .
H10 H 0.8953 0.8237 0.1056 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6557(4) 0.5489(9) 0.1333(6) 0.0620(16) Uani 1 1 d . . . . .
H11A H 0.6738 0.5442 0.0813 0.093 Uiso 1 1 calc R U . . .
H11B H 0.5967 0.5679 0.0978 0.093 Uiso 1 1 calc R U . . .
H11C H 0.6689 0.4391 0.1720 0.093 Uiso 1 1 calc R U . . .
C12 C 0.6133(3) 0.9585(9) 0.1019(4) 0.0577(15) Uani 1 1 d . . . . .
H12A H 0.6086 1.0634 0.0655 0.069 Uiso 1 1 calc R U . . .
H12B H 0.5669 0.9112 0.1021 0.069 Uiso 1 1 calc R U . . .
C13 C 0.7811(3) 1.0915(7) 0.1258(4) 0.0430(12) Uani 1 1 d . . . . .
C14 C 0.8800(4) 1.3079(8) 0.1466(6) 0.0649(17) Uani 1 1 d . . . . .
H14A H 0.8820 1.2954 0.0815 0.097 Uiso 1 1 calc R U . . .
H14B H 0.9328 1.3496 0.2024 0.097 Uiso 1 1 calc R U . . .
H14C H 0.8374 1.3914 0.1360 0.097 Uiso 1 1 calc R U . . .
C15 C 0.6827(3) 0.7100(7) 0.3032(4) 0.0413(11) Uani 1 1 d . . . . .
C16 C 0.6115(3) 0.6413(8) 0.2973(4) 0.0487(13) Uani 1 1 d . . . . .
H16 H 0.5722 0.5876 0.2342 0.058 Uiso 1 1 calc R U . . .
C17 C 0.5970(4) 0.6504(9) 0.3837(5) 0.0568(15) Uani 1 1 d . . . . .
H17 H 0.5491 0.6016 0.3787 0.068 Uiso 1 1 calc R U . . .
C18 C 0.6539(3) 0.7315(9) 0.4749(4) 0.0496(12) Uani 1 1 d . . . . .
C19 C 0.7255(3) 0.8049(8) 0.4828(4) 0.0567(15) Uani 1 1 d . . . . .
H19 H 0.7639 0.8615 0.5454 0.068 Uiso 1 1 calc R U . . .
C20 C 0.7391(3) 0.7931(7) 0.3981(4) 0.0503(14) Uani 1 1 d . . . . .
H20 H 0.7873 0.8418 0.4039 0.060 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 C18 1.900(4) . ?
O1 C4 1.345(6) . ?
O1 C1 1.476(6) . ?
O2 C13 1.196(6) . ?
O3 C13 1.347(6) . ?
O3 C14 1.432(7) . ?
C1 C15 1.513(7) . ?
C1 C2 1.517(8) . ?
C1 C11 1.518(8) . ?
C2 C12 1.322(7) . ?
C2 C3 1.467(7) . ?
C3 C4 1.354(6) . ?
C3 C13 1.453(7) . ?
C4 C5 1.477(6) . ?
C5 C6 1.373(7) . ?
C5 C10 1.381(6) . ?
C6 C7 1.395(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.344(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.377(7) . ?
C15 C20 1.392(7) . ?
C16 C17 1.398(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(8) . ?
C19 C20 1.363(8) . ?
C19 H19 0.9300 . ?
C20 H20 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
C4 O1 C1 108.5(4) . . ?
C13 O3 C14 116.1(4) . . ?
O1 C1 C15 107.7(4) . . ?
O1 C1 C2 103.8(4) . . ?
C15 C1 C2 112.4(4) . . ?
O1 C1 C11 105.5(4) . . ?
C15 C1 C11 114.4(4) . . ?
C2 C1 C11 112.1(5) . . ?
C12 C2 C3 129.7(5) . . ?
C12 C2 C1 124.5(5) . . ?
C3 C2 C1 105.7(4) . . ?
C4 C3 C13 129.1(4) . . ?
C4 C3 C2 107.5(4) . . ?
C13 C3 C2 123.2(4) . . ?
O1 C4 C3 114.3(4) . . ?
O1 C4 C5 112.8(4) . . ?
C3 C4 C5 132.7(4) . . ?
C6 C5 C10 119.3(4) . . ?
C6 C5 C4 119.7(4) . . ?
C10 C5 C4 120.6(4) . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.9(6) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.2(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 119.6(4) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 120.0 . . ?
C2 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
O2 C13 O3 122.4(5) . . ?
O2 C13 C3 124.3(5) . . ?
O3 C13 C3 113.2(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 117.4(5) . . ?
C16 C15 C1 122.3(4) . . ?
C20 C15 C1 120.3(4) . . ?
C15 C16 C17 121.6(5) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 118.9(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.9(5) . . ?
C17 C18 Br1 119.4(4) . . ?
C19 C18 Br1 119.7(4) . . ?
C20 C19 C18 119.4(5) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C15 121.8(5) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?

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 O1 C1 C15 -123.5(4) . . . . ?
C4 O1 C1 C2 -4.2(5) . . . . ?
C4 O1 C1 C11 113.9(5) . . . . ?
O1 C1 C2 C12 -179.7(5) . . . . ?
C15 C1 C2 C12 -63.6(6) . . . . ?
C11 C1 C2 C12 66.9(6) . . . . ?
O1 C1 C2 C3 3.0(5) . . . . ?
C15 C1 C2 C3 119.1(4) . . . . ?
C11 C1 C2 C3 -110.4(5) . . . . ?
C12 C2 C3 C4 -178.0(5) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C12 C2 C3 C13 6.6(8) . . . . ?
C1 C2 C3 C13 -176.2(4) . . . . ?
C1 O1 C4 C3 4.1(5) . . . . ?
C1 O1 C4 C5 -171.8(4) . . . . ?
C13 C3 C4 O1 173.0(5) . . . . ?
C2 C3 C4 O1 -2.0(5) . . . . ?
C13 C3 C4 C5 -12.1(8) . . . . ?
C2 C3 C4 C5 172.8(5) . . . . ?
O1 C4 C5 C6 -40.9(6) . . . . ?
C3 C4 C5 C6 144.2(5) . . . . ?
O1 C4 C5 C10 131.5(5) . . . . ?
C3 C4 C5 C10 -43.4(8) . . . . ?
C10 C5 C6 C7 3.2(8) . . . . ?
C4 C5 C6 C7 175.7(5) . . . . ?
C5 C6 C7 C8 -4.0(9) . . . . ?
C6 C7 C8 C9 2.5(10) . . . . ?
C7 C8 C9 C10 -0.4(10) . . . . ?
C8 C9 C10 C5 -0.3(9) . . . . ?
C6 C5 C10 C9 -1.1(8) . . . . ?
C4 C5 C10 C9 -173.5(5) . . . . ?
C14 O3 C13 O2 2.8(8) . . . . ?
C14 O3 C13 C3 -176.4(4) . . . . ?
C4 C3 C13 O2 163.0(5) . . . . ?
C2 C3 C13 O2 -22.7(8) . . . . ?
C4 C3 C13 O3 -17.8(7) . . . . ?
C2 C3 C13 O3 156.6(4) . . . . ?
O1 C1 C15 C16 -142.0(5) . . . . ?
C2 C1 C15 C16 104.3(6) . . . . ?
C11 C1 C15 C16 -25.0(7) . . . . ?
O1 C1 C15 C20 39.1(6) . . . . ?
C2 C1 C15 C20 -74.6(6) . . . . ?
C11 C1 C15 C20 156.0(5) . . . . ?
C20 C15 C16 C17 -1.5(8) . . . . ?
C1 C15 C16 C17 179.6(5) . . . . ?
C15 C16 C17 C18 1.1(9) . . . . ?
C16 C17 C18 C19 0.1(9) . . . . ?
C16 C17 C18 Br1 -178.2(5) . . . . ?
C17 C18 C19 C20 -0.8(9) . . . . ?
Br1 C18 C19 C20 177.5(4) . . . . ?
C18 C19 C20 C15 0.4(8) . . . . ?
C16 C15 C20 C19 0.8(8) . . . . ?
C1 C15 C20 C19 179.7(5) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

