# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_13juna
_database_code_depnum_ccdc_archive 'CCDC 1035484'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Br Cl O3'
_chemical_formula_sum            'C18 H12 Br Cl O3'
_chemical_formula_weight         391.64

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'
Cl Cl 0.1484 0.1585 '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   C2/c

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

_cell_length_a                   13.884(4)
_cell_length_b                   10.515(4)
_cell_length_c                   22.936(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.166(7)
_cell_angle_gamma                90.00
_cell_volume                     3329.0(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    2.641
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_T_max  0.590
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8794
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3108
_reflns_number_gt                2058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_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)+(0.0473P)²+4.5940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.33218(4) 0.75321(5) 0.772326(18) 0.0913(2) Uani 1 1 d . . .
Cl Cl 0.01972(8) 1.02647(13) 0.32927(5) 0.0941(4) Uani 1 1 d . . .
O1 O 0.3789(2) 1.2391(2) 0.42758(12) 0.0708(7) Uani 1 1 d . . .
O3 O 0.4851(2) 1.1360(3) 0.60391(13) 0.0953(10) Uani 1 1 d . . .
C6 C 0.2293(2) 1.0249(3) 0.49197(13) 0.0510(8) Uani 1 1 d . . .
C5 C 0.2455(2) 1.1008(3) 0.44445(14) 0.0516(8) Uani 1 1 d . . .
C8 C 0.3794(2) 1.1161(3) 0.51802(14) 0.0508(8) Uani 1 1 d . . .
C9 C 0.3129(2) 1.0368(3) 0.53787(14) 0.0490(8) Uani 1 1 d . . .
C10 C 0.3175(2) 0.9664(3) 0.59389(14) 0.0502(8) Uani 1 1 d . . .
C7 C 0.3416(3) 1.1642(3) 0.45865(14) 0.0534(8) Uani 1 1 d . . .
C4 C 0.1822(3) 1.1054(4) 0.39457(15) 0.0608(9) Uani 1 1 d . . .
H4 H 0.1935 1.1573 0.3632 0.073 Uiso 1 1 calc R . .
C3 C 0.1001(3) 1.0290(4) 0.39289(16) 0.0646(10) Uani 1 1 d . . .
O2 O 0.5371(3) 1.1951(4) 0.52159(15) 0.1206(14) Uani 1 1 d . . .
C13 C 0.3243(3) 0.8397(3) 0.69909(14) 0.0575(9) Uani 1 1 d . . .
C1 C 0.1480(3) 0.9502(4) 0.49009(16) 0.0630(9) Uani 1 1 d . . .
H1 H 0.1368 0.8989 0.5217 0.076 Uiso 1 1 calc R . .
C2 C 0.0827(3) 0.9534(4) 0.43959(17) 0.0683(10) Uani 1 1 d . . .
H2 H 0.0268 0.9040 0.4374 0.082 Uiso 1 1 calc R . .
C11 C 0.2475(3) 0.9863(3) 0.63153(14) 0.0582(9) Uani 1 1 d . . .
H11 H 0.1968 1.0423 0.6209 0.070 Uiso 1 1 calc R . .
C16 C 0.4752(3) 1.1537(3) 0.54699(16) 0.0604(9) Uani 1 1 d . . .
C12 C 0.2519(3) 0.9240(4) 0.68473(14) 0.0617(9) Uani 1 1 d . . .
H12 H 0.2058 0.9398 0.7104 0.074 Uiso 1 1 calc R . .
C15 C 0.3900(3) 0.8803(4) 0.60946(16) 0.0640(10) Uani 1 1 d . . .
H15 H 0.4372 0.8654 0.5844 0.077 Uiso 1 1 calc R . .
C14 C 0.3938(3) 0.8153(4) 0.66207(16) 0.0686(10) Uani 1 1 d . . .
H14 H 0.4424 0.7561 0.6723 0.082 Uiso 1 1 calc R . .
C17 C 0.5816(4) 1.1571(6) 0.6346(2) 0.120(2) Uani 1 1 d . . .
H17A H 0.6299 1.1169 0.6131 0.144 Uiso 1 1 calc R . .
H17B H 0.5952 1.2476 0.6368 0.144 Uiso 1 1 calc R . .
C18 C 0.5862(7) 1.1075(9) 0.6897(4) 0.282(7) Uani 1 1 d . . .
H18A H 0.5224 1.0831 0.6980 0.422 Uiso 1 1 calc R . .
H18B H 0.6117 1.1702 0.7176 0.422 Uiso 1 1 calc R . .
H18C H 0.6277 1.0342 0.6923 0.422 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br 0.1033(4) 0.1097(4) 0.0605(3) 0.0318(2) 0.0067(2) 0.0107(3)
Cl 0.0836(8) 0.1111(9) 0.0795(7) 0.0010(6) -0.0289(6) -0.0001(7)
O1 0.0738(18) 0.0724(17) 0.0668(16) 0.0181(13) 0.0106(14) -0.0153(14)
O3 0.087(2) 0.112(2) 0.078(2) 0.0249(17) -0.0281(16) -0.0367(18)
C6 0.053(2) 0.0495(19) 0.0510(19) 0.0012(15) 0.0057(16) -0.0061(16)
C5 0.054(2) 0.0516(19) 0.0500(18) 0.0015(15) 0.0072(16) -0.0010(16)
C8 0.0514(19) 0.0497(19) 0.0512(18) -0.0032(15) 0.0050(15) -0.0047(16)
C9 0.0527(19) 0.0467(18) 0.0480(17) -0.0017(14) 0.0072(15) -0.0030(15)
C10 0.053(2) 0.0481(19) 0.0489(18) 0.0014(15) 0.0031(15) -0.0062(16)
C7 0.058(2) 0.0501(19) 0.0531(19) 0.0001(16) 0.0113(16) -0.0001(17)
C4 0.065(2) 0.065(2) 0.052(2) 0.0068(17) 0.0054(17) 0.0045(19)
C3 0.062(2) 0.073(2) 0.055(2) -0.0034(19) -0.0061(18) 0.005(2)
O2 0.082(2) 0.192(4) 0.087(2) 0.008(2) 0.0070(18) -0.066(3)
C13 0.066(2) 0.063(2) 0.0422(18) 0.0056(16) -0.0012(16) -0.0039(19)
C1 0.063(2) 0.066(2) 0.059(2) 0.0031(18) 0.0043(18) -0.0118(19)
C2 0.057(2) 0.078(3) 0.069(2) -0.005(2) -0.0004(19) -0.013(2)
C11 0.058(2) 0.065(2) 0.0519(19) 0.0068(17) 0.0055(16) 0.0101(18)
C16 0.062(2) 0.058(2) 0.061(2) -0.0019(17) 0.0037(19) -0.0094(19)
C12 0.063(2) 0.075(2) 0.0484(19) 0.0038(17) 0.0111(17) 0.007(2)
C15 0.066(2) 0.067(2) 0.062(2) 0.0092(18) 0.0180(18) 0.0088(19)
C14 0.073(3) 0.064(2) 0.069(2) 0.013(2) 0.008(2) 0.015(2)
C17 0.105(4) 0.133(5) 0.108(4) 0.007(4) -0.048(3) -0.040(4)
C18 0.278(11) 0.257(11) 0.260(10) 0.162(9) -0.200(9) -0.154(9)

_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
Br C13 1.903(3) . ?
Cl C3 1.740(4) . ?
O1 C7 1.215(4) . ?
O3 C16 1.311(4) . ?
O3 C17 1.462(5) . ?
C6 C1 1.372(5) . ?
C6 C5 1.388(4) . ?
C6 C9 1.486(4) . ?
C5 C4 1.367(5) . ?
C5 C7 1.496(5) . ?
C8 C9 1.359(4) . ?
C8 C16 1.475(5) . ?
C8 C7 1.494(4) . ?
C9 C10 1.478(4) . ?
C10 C15 1.373(5) . ?
C10 C11 1.383(5) . ?
C4 C3 1.391(5) . ?
C3 C2 1.376(5) . ?
O2 C16 1.173(5) . ?
C13 C12 1.354(5) . ?
C13 C14 1.375(5) . ?
C1 C2 1.393(5) . ?
C11 C12 1.380(5) . ?
C15 C14 1.383(5) . ?
C17 C18 1.363(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
C16 O3 C17 116.7(4) . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 C9 130.4(3) . . ?
C5 C6 C9 109.1(3) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 C7 130.2(3) . . ?
C6 C5 C7 107.5(3) . . ?
C9 C8 C16 128.8(3) . . ?
C9 C8 C7 109.1(3) . . ?
C16 C8 C7 122.1(3) . . ?
C8 C9 C10 129.1(3) . . ?
C8 C9 C6 108.8(3) . . ?
C10 C9 C6 122.1(3) . . ?
C15 C10 C11 118.8(3) . . ?
C15 C10 C9 121.2(3) . . ?
C11 C10 C9 119.9(3) . . ?
O1 C7 C8 128.6(3) . . ?
O1 C7 C5 126.0(3) . . ?
C8 C7 C5 105.4(3) . . ?
C5 C4 C3 117.0(3) . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 Cl 119.5(3) . . ?
C4 C3 Cl 118.8(3) . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 Br 119.9(3) . . ?
C14 C13 Br 118.6(3) . . ?
C6 C1 C2 118.2(3) . . ?
C3 C2 C1 120.5(4) . . ?
C12 C11 C10 120.8(3) . . ?
O2 C16 O3 122.9(4) . . ?
O2 C16 C8 123.3(4) . . ?
O3 C16 C8 113.8(3) . . ?
C13 C12 C11 119.1(3) . . ?
C10 C15 C14 120.7(3) . . ?
C13 C14 C15 118.9(3) . . ?
C18 C17 O3 109.7(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.061
