# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd212166
_database_code_depnum_ccdc_archive 'CCDC 898028'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Br O3'
_chemical_formula_weight         399.27

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   10.687(8)
_cell_length_b                   12.035(9)
_cell_length_c                   14.902(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1917(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1994
_cell_measurement_theta_min      5.087
_cell_measurement_theta_max      38.258

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.160
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0895
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9193
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0833
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3560
_reflns_number_gt                2315
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0652P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3560
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.89935(9) 1.30544(5) -0.07606(5) 0.1212(4) Uani 1 1 d . . .
O1 O 1.0324(3) 1.0361(3) 0.2937(2) 0.0738(10) Uani 1 1 d . . .
O2 O 0.7610(2) 0.8884(2) 0.23881(19) 0.0496(7) Uani 1 1 d . . .
O3 O 1.0869(4) 0.7404(3) 0.0289(3) 0.0964(13) Uani 1 1 d . . .
C1 C 0.8979(3) 0.8902(3) 0.2406(3) 0.0464(10) Uani 1 1 d . . .
C2 C 0.9264(4) 1.0007(4) 0.2824(3) 0.0535(11) Uani 1 1 d . . .
C3 C 0.8100(4) 1.0506(4) 0.3063(3) 0.0566(12) Uani 1 1 d . . .
H3 H 0.7991 1.1185 0.3351 0.068 Uiso 1 1 calc R . .
C4 C 0.7201(4) 0.9818(4) 0.2798(3) 0.0507(11) Uani 1 1 d . . .
C5 C 0.5849(4) 0.9926(4) 0.2863(3) 0.0570(11) Uani 1 1 d . . .
C6 C 0.5093(4) 0.9100(6) 0.2576(4) 0.0824(18) Uani 1 1 d . . .
H6 H 0.5444 0.8462 0.2329 0.099 Uiso 1 1 calc R . .
C7 C 0.3805(5) 0.9186(8) 0.2645(5) 0.119(3) Uani 1 1 d . . .
H7 H 0.3286 0.8617 0.2446 0.143 Uiso 1 1 calc R . .
C8 C 0.3308(6) 1.0152(8) 0.3023(5) 0.107(2) Uani 1 1 d . . .
H8 H 0.2445 1.0242 0.3056 0.128 Uiso 1 1 calc R . .
C9 C 0.4060(6) 1.0950(7) 0.3337(5) 0.108(2) Uani 1 1 d . . .
H9 H 0.3720 1.1576 0.3610 0.129 Uiso 1 1 calc R . .
C10 C 0.5313(5) 1.0848(5) 0.3259(4) 0.0847(16) Uani 1 1 d . . .
H10 H 0.5827 1.1411 0.3476 0.102 Uiso 1 1 calc R . .
C11 C 0.9412(5) 0.7995(4) 0.3058(3) 0.0660(13) Uani 1 1 d . . .
H11A H 0.9057 0.8129 0.3640 0.099 Uiso 1 1 calc R . .
H11B H 1.0308 0.8004 0.3099 0.099 Uiso 1 1 calc R . .
H11C H 0.9141 0.7282 0.2842 0.099 Uiso 1 1 calc R . .
C12 C 0.9477(3) 0.8750(3) 0.1471(3) 0.0459(10) Uani 1 1 d . . .
H12 H 1.0377 0.8613 0.1531 0.055 Uiso 1 1 calc R . .
C13 C 0.8925(4) 0.7722(3) 0.1010(3) 0.0525(11) Uani 1 1 d . . .
H13A H 0.8682 0.7192 0.1469 0.063 Uiso 1 1 calc R . .
H13B H 0.8173 0.7942 0.0693 0.063 Uiso 1 1 calc R . .
C14 C 0.9776(7) 0.7152(4) 0.0364(3) 0.0741(15) Uani 1 1 d . . .
C15 C 0.9186(8) 0.6205(5) -0.0144(4) 0.112(2) Uani 1 1 d . . .
H15A H 0.8651 0.6495 -0.0605 0.168 Uiso 1 1 calc R . .
H15B H 0.8703 0.5758 0.0262 0.168 Uiso 1 1 calc R . .
H15C H 0.9830 0.5758 -0.0412 0.168 Uiso 1 1 calc R . .
C16 C 0.9343(4) 0.9776(3) 0.0891(3) 0.0482(10) Uani 1 1 d . . .
C17 C 0.8192(5) 1.0197(4) 0.0654(3) 0.0664(13) Uani 1 1 d . . .
H17 H 0.7471 0.9825 0.0832 0.080 Uiso 1 1 calc R . .
C18 C 0.8087(6) 1.1161(5) 0.0159(4) 0.0791(15) Uani 1 1 d . . .
H18 H 0.7302 1.1434 0.0007 0.095 Uiso 1 1 calc R . .
C19 C 0.9115(7) 1.1699(4) -0.0099(3) 0.0750(14) Uani 1 1 d U . .
C20 C 1.0291(6) 1.1310(4) 0.0085(3) 0.0718(13) Uani 1 1 d U . .
H20 H 1.0998 1.1678 -0.0124 0.086 Uiso 1 1 calc R . .
C21 C 1.0393(5) 1.0336(4) 0.0598(3) 0.0625(12) Uani 1 1 d . . .
H21 H 1.1182 1.0065 0.0744 0.075 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 C19 1.911(5) . ?
O1 C2 1.221(5) . ?
O2 C4 1.352(5) . ?
O2 C1 1.463(5) . ?
O3 C14 1.212(7) . ?
C1 C2 1.500(6) . ?
C1 C12 1.503(6) . ?
C1 C11 1.533(6) . ?
C2 C3 1.427(6) . ?
C3 C4 1.328(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.455(6) . ?
C5 C6 1.351(7) . ?
C5 C10 1.380(7) . ?
C6 C7 1.384(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.337(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.350(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C16 1.514(6) . ?
C12 C13 1.533(6) . ?
C12 H12 0.9800 . ?
C13 C14 1.490(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.506(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.376(6) . ?
C16 C21 1.380(6) . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.332(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(8) . ?
C20 C21 1.404(7) . ?
C20 H20 0.9300 . ?
C21 H21 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 O2 C1 107.6(3) . . ?
O2 C1 C2 102.9(3) . . ?
O2 C1 C12 109.6(3) . . ?
C2 C1 C12 114.9(3) . . ?
O2 C1 C11 107.6(3) . . ?
C2 C1 C11 107.9(3) . . ?
C12 C1 C11 113.2(3) . . ?
O1 C2 C3 128.9(4) . . ?
O1 C2 C1 123.7(4) . . ?
C3 C2 C1 107.4(3) . . ?
C4 C3 C2 107.1(4) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
C3 C4 O2 114.8(4) . . ?
C3 C4 C5 130.0(4) . . ?
O2 C4 C5 115.2(4) . . ?
C6 C5 C10 118.6(4) . . ?
C6 C5 C4 120.5(4) . . ?
C10 C5 C4 120.8(5) . . ?
C5 C6 C7 121.0(6) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 118.1(7) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C9 C8 C7 120.7(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.0(7) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 121.4(7) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
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 . . ?
C1 C12 C16 113.3(3) . . ?
C1 C12 C13 112.2(3) . . ?
C16 C12 C13 111.5(3) . . ?
C1 C12 H12 106.4 . . ?
C16 C12 H12 106.4 . . ?
C13 C12 H12 106.4 . . ?
C14 C13 C12 115.2(4) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
O3 C14 C13 122.2(5) . . ?
O3 C14 C15 123.1(6) . . ?
C13 C14 C15 114.7(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.7(4) . . ?
C17 C16 C12 122.1(4) . . ?
C21 C16 C12 120.1(4) . . ?
C16 C17 C18 121.3(5) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 122.2(5) . . ?
C18 C19 Br1 120.5(5) . . ?
C20 C19 Br1 117.3(5) . . ?
C19 C20 C21 117.8(5) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C16 C21 C20 121.1(5) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?

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 C2 -3.8(4) . . . . ?
C4 O2 C1 C12 -126.5(3) . . . . ?
C4 O2 C1 C11 110.1(4) . . . . ?
O2 C1 C2 O1 -177.9(4) . . . . ?
C12 C1 C2 O1 -58.8(6) . . . . ?
C11 C1 C2 O1 68.5(5) . . . . ?
O2 C1 C2 C3 3.5(4) . . . . ?
C12 C1 C2 C3 122.6(4) . . . . ?
C11 C1 C2 C3 -110.1(4) . . . . ?
O1 C2 C3 C4 179.4(5) . . . . ?
C1 C2 C3 C4 -2.0(5) . . . . ?
C2 C3 C4 O2 -0.5(5) . . . . ?
C2 C3 C4 C5 -178.9(4) . . . . ?
C1 O2 C4 C3 2.9(5) . . . . ?
C1 O2 C4 C5 -178.5(4) . . . . ?
C3 C4 C5 C6 -177.6(5) . . . . ?
O2 C4 C5 C6 4.0(6) . . . . ?
C3 C4 C5 C10 -0.9(8) . . . . ?
O2 C4 C5 C10 -179.3(4) . . . . ?
C10 C5 C6 C7 2.3(9) . . . . ?
C4 C5 C6 C7 179.1(6) . . . . ?
C5 C6 C7 C8 -0.2(10) . . . . ?
C6 C7 C8 C9 -2.4(11) . . . . ?
C7 C8 C9 C10 2.7(11) . . . . ?
C8 C9 C10 C5 -0.5(11) . . . . ?
C6 C5 C10 C9 -2.0(9) . . . . ?
C4 C5 C10 C9 -178.9(5) . . . . ?
O2 C1 C12 C16 74.8(4) . . . . ?
C2 C1 C12 C16 -40.5(4) . . . . ?
C11 C1 C12 C16 -165.0(3) . . . . ?
O2 C1 C12 C13 -52.5(4) . . . . ?
C2 C1 C12 C13 -167.8(3) . . . . ?
C11 C1 C12 C13 67.7(4) . . . . ?
C1 C12 C13 C14 -147.9(4) . . . . ?
C16 C12 C13 C14 83.8(4) . . . . ?
C12 C13 C14 O3 8.4(7) . . . . ?
C12 C13 C14 C15 -174.9(4) . . . . ?
C1 C12 C16 C17 -64.5(6) . . . . ?
C13 C12 C16 C17 63.2(6) . . . . ?
C1 C12 C16 C21 114.0(4) . . . . ?
C13 C12 C16 C21 -118.3(4) . . . . ?
C21 C16 C17 C18 -1.5(7) . . . . ?
C12 C16 C17 C18 177.1(4) . . . . ?
C16 C17 C18 C19 0.1(8) . . . . ?
C17 C18 C19 C20 2.2(8) . . . . ?
C17 C18 C19 Br1 -178.5(4) . . . . ?
C18 C19 C20 C21 -2.9(8) . . . . ?
Br1 C19 C20 C21 177.7(3) . . . . ?
C17 C16 C21 C20 0.7(7) . . . . ?
C12 C16 C21 C20 -177.9(4) . . . . ?
C19 C20 C21 C16 1.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.050
