# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1483374'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Br O'
_chemical_formula_weight         391.29

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.005(2)
_cell_length_b                   9.977(2)
_cell_length_c                   18.125(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.34(3)
_cell_angle_gamma                90.00
_cell_volume                     1807.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5150
_cell_measurement_theta_min      2.2492
_cell_measurement_theta_max      27.4798

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5676
_exptl_absorpt_correction_T_max  0.7714

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12617
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4118
_reflns_number_gt                3677
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_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)+(0.1509P)²+4.7659P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4118
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.1883
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001

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 0.19169(5) 0.81842(5) 0.11162(3) 0.0339(2) Uani 1 1 d . . .
C14 C -0.0452(5) 0.6936(5) 0.1607(3) 0.0289(10) Uani 1 1 d . . .
H14 H -0.0860 0.7287 0.1165 0.035 Uiso 1 1 calc R . .
O1 O -0.1615(4) 0.4542(4) 0.52521(18) 0.0347(8) Uani 1 1 d . . .
C13 C 0.0896(5) 0.7166(5) 0.1779(3) 0.0282(10) Uani 1 1 d . . .
C15 C -0.1187(5) 0.6194(5) 0.2085(3) 0.0268(10) Uani 1 1 d . . .
H15 H -0.2109 0.6038 0.1971 0.032 Uiso 1 1 calc R . .
C2 C -0.0901(5) 0.3253(5) 0.4218(3) 0.0265(10) Uani 1 1 d . . .
C10 C -0.0604(5) 0.5664(5) 0.2735(2) 0.0240(9) Uani 1 1 d . . .
C17 C -0.2820(5) 0.6401(5) 0.4091(2) 0.0252(9) Uani 1 1 d . . .
C1 C -0.1389(5) 0.4450(6) 0.4596(3) 0.0307(11) Uani 1 1 d . . .
C21 C -0.5212(6) 0.6554(6) 0.4199(3) 0.0332(11) Uani 1 1 d . . .
H21 H -0.6049 0.6113 0.4233 0.040 Uiso 1 1 calc R . .
C16 C -0.1559(5) 0.5561(5) 0.4023(3) 0.0264(10) Uani 1 1 d . . .
H16 H -0.0777 0.6179 0.4094 0.032 Uiso 1 1 calc R . .
C9 C -0.1430(5) 0.4866(5) 0.3257(2) 0.0248(9) Uani 1 1 d . . .
H9 H -0.2348 0.4756 0.3026 0.030 Uiso 1 1 calc R . .
C8 C -0.0887(5) 0.3479(5) 0.3458(3) 0.0248(9) Uani 1 1 d . . .
C12 C 0.1498(5) 0.6679(5) 0.2420(3) 0.0305(11) Uani 1 1 d . . .
H12 H 0.2416 0.6854 0.2535 0.037 Uiso 1 1 calc R . .
C4 C -0.0106(6) 0.1033(5) 0.4059(3) 0.0333(11) Uani 1 1 d . . .
H4 H 0.0168 0.0192 0.4259 0.040 Uiso 1 1 calc R . .
C11 C 0.0745(5) 0.5927(5) 0.2898(3) 0.0299(10) Uani 1 1 d . . .
H11 H 0.1155 0.5588 0.3342 0.036 Uiso 1 1 calc R . .
C20 C -0.5170(6) 0.7946(6) 0.4200(3) 0.0354(12) Uani 1 1 d . . .
C7 C -0.0474(5) 0.2473(5) 0.2994(3) 0.0280(10) Uani 1 1 d . . .
H7 H -0.0448 0.2625 0.2478 0.034 Uiso 1 1 calc R . .
C5 C -0.0094(5) 0.1229(5) 0.3292(3) 0.0295(10) Uani 1 1 d . . .
C18 C -0.2760(6) 0.7790(6) 0.4098(3) 0.0352(11) Uani 1 1 d . . .
H18 H -0.1920 0.8226 0.4068 0.042 Uiso 1 1 calc R . .
C3 C -0.0502(6) 0.2021(6) 0.4526(3) 0.0340(11) Uani 1 1 d . . .
H3 H -0.0507 0.1876 0.5044 0.041 Uiso 1 1 calc R . .
C19 C -0.3915(6) 0.8549(6) 0.4149(3) 0.0397(13) Uani 1 1 d . . .
H19 H -0.3851 0.9499 0.4149 0.048 Uiso 1 1 calc R . .
C6 C 0.0297(6) 0.0072(6) 0.2813(3) 0.0387(12) Uani 1 1 d . . .
H6A H -0.0404 -0.0613 0.2811 0.058 Uiso 1 1 calc R . .
H6B H 0.1141 -0.0313 0.3008 0.058 Uiso 1 1 calc R . .
H6C H 0.0410 0.0390 0.2308 0.058 Uiso 1 1 calc R . .
C22 C -0.4056(5) 0.5794(5) 0.4150(3) 0.0301(10) Uani 1 1 d . . .
H22 H -0.4113 0.4843 0.4157 0.036 Uiso 1 1 calc R . .
C23 C -0.6463(7) 0.8740(8) 0.4243(4) 0.0565(18) Uani 1 1 d . . .
H23A H -0.7110 0.8420 0.3862 0.085 Uiso 1 1 calc R . .
H23B H -0.6281 0.9693 0.4163 0.085 Uiso 1 1 calc R . .
H23C H -0.6832 0.8617 0.4731 0.085 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 C13 1.903(5) . ?
C14 C15 1.375(7) . ?
C14 C13 1.391(7) . ?
O1 C1 1.224(6) . ?
C13 C12 1.376(7) . ?
C15 C10 1.397(6) . ?
C2 C8 1.397(6) . ?
C2 C3 1.401(7) . ?
C2 C1 1.470(7) . ?
C10 C11 1.394(7) . ?
C10 C9 1.509(6) . ?
C17 C22 1.385(7) . ?
C17 C18 1.387(7) . ?
C17 C16 1.524(7) . ?
C1 C16 1.523(7) . ?
C21 C22 1.389(7) . ?
C21 C20 1.390(8) . ?
C16 C9 1.561(6) . ?
C9 C8 1.525(7) . ?
C8 C7 1.383(7) . ?
C12 C11 1.391(7) . ?
C4 C3 1.369(8) . ?
C4 C5 1.404(7) . ?
C20 C19 1.399(9) . ?
C20 C23 1.522(8) . ?
C7 C5 1.400(7) . ?
C5 C6 1.505(7) . ?
C18 C19 1.387(8) . ?

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
C15 C14 C13 119.0(4) . . ?
C12 C13 C14 121.2(5) . . ?
C12 C13 Br1 119.6(4) . . ?
C14 C13 Br1 119.2(4) . . ?
C14 C15 C10 121.3(5) . . ?
C8 C2 C3 121.4(5) . . ?
C8 C2 C1 110.2(4) . . ?
C3 C2 C1 128.5(5) . . ?
C11 C10 C15 118.3(4) . . ?
C11 C10 C9 121.1(4) . . ?
C15 C10 C9 120.5(4) . . ?
C22 C17 C18 118.3(5) . . ?
C22 C17 C16 120.7(4) . . ?
C18 C17 C16 121.0(5) . . ?
O1 C1 C2 126.3(5) . . ?
O1 C1 C16 126.0(5) . . ?
C2 C1 C16 107.7(4) . . ?
C22 C21 C20 121.4(5) . . ?
C1 C16 C17 114.5(4) . . ?
C1 C16 C9 105.7(4) . . ?
C17 C16 C9 114.5(4) . . ?
C10 C9 C8 115.4(4) . . ?
C10 C9 C16 113.0(4) . . ?
C8 C9 C16 103.5(4) . . ?
C7 C8 C2 119.9(5) . . ?
C7 C8 C9 128.8(4) . . ?
C2 C8 C9 111.3(4) . . ?
C13 C12 C11 119.2(5) . . ?
C3 C4 C5 121.8(5) . . ?
C12 C11 C10 120.9(4) . . ?
C21 C20 C19 117.2(5) . . ?
C21 C20 C23 119.6(6) . . ?
C19 C20 C23 123.2(6) . . ?
C8 C7 C5 119.5(5) . . ?
C7 C5 C4 119.4(5) . . ?
C7 C5 C6 122.0(5) . . ?
C4 C5 C6 118.5(5) . . ?
C17 C18 C19 120.7(5) . . ?
C4 C3 C2 118.0(5) . . ?
C18 C19 C20 121.4(5) . . ?
C17 C22 C21 121.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.834
_refine_diff_density_min         -1.111
_refine_diff_density_rms         0.225
