# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_yuty0905
_audit_creation_date             2013-09-09
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H10 Br2 O3'
_chemical_formula_sum            'C11 H10 Br2 O3'
_chemical_formula_weight         350.01
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.6547(13)
_cell_length_b                   14.1169(10)
_cell_length_c                   16.8780(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2538.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8560
_cell_measurement_theta_min      3.6560
_exptl_absorpt_coefficient_mu    6.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2900
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2400
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7163
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.13
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9844
_diffrn_measured_fraction_theta_max 0.8948
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   91.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000  -60.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   46.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega   50.00   75.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  160.0000  132.0000 17
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0372334000
_diffrn_orient_matrix_UB_12      -0.0063691000
_diffrn_orient_matrix_UB_13      -0.0344141000
_diffrn_orient_matrix_UB_21      -0.0530258000
_diffrn_orient_matrix_UB_22      -0.0184296000
_diffrn_orient_matrix_UB_23      -0.0203797000
_diffrn_orient_matrix_UB_31      -0.0155702000
_diffrn_orient_matrix_UB_32      0.0462586000
_diffrn_orient_matrix_UB_33      -0.0128897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1274
_reflns_number_total             2479
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.6188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1486
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.18124(9) 0.53478(5) 0.30032(4) 0.0698(3) Uani 1 1 d . . .
Br2 Br 0.04988(10) 0.22256(6) 0.29778(4) 0.0843(4) Uani 1 1 d . . .
O1 O 0.0944(4) 0.4280(3) 0.0580(2) 0.0550(12) Uani 1 1 d . . .
O2 O 0.2728(5) 0.4001(4) 0.1234(2) 0.0655(14) Uani 1 1 d . . .
O3 O -0.0322(5) 0.4123(5) 0.1919(2) 0.089(2) Uani 1 1 d . . .
C1 C 0.2574(7) 0.3230(5) 0.4316(4) 0.0549(18) Uani 1 1 d . . .
H1 H 0.3080 0.3091 0.3882 0.066 Uiso 1 1 calc R . .
C2 C 0.3070(7) 0.3168(5) 0.5069(4) 0.064(2) Uani 1 1 d . . .
H2 H 0.3896 0.2975 0.5145 0.077 Uiso 1 1 calc R . .
C3 C 0.2320(8) 0.3399(5) 0.5712(4) 0.067(2) Uani 1 1 d . . .
H3 H 0.2643 0.3358 0.6223 0.081 Uiso 1 1 calc R . .
C4 C 0.1123(8) 0.3681(6) 0.5601(4) 0.068(2) Uani 1 1 d . . .
H4 H 0.0634 0.3845 0.6036 0.082 Uiso 1 1 calc R . .
C5 C 0.0608(7) 0.3731(5) 0.4843(4) 0.0573(19) Uani 1 1 d . . .
H5 H -0.0220 0.3923 0.4773 0.069 Uiso 1 1 calc R . .
C6 C 0.1339(6) 0.3493(4) 0.4193(3) 0.0461(17) Uani 1 1 d . . .
C7 C 0.0768(6) 0.3543(5) 0.3385(3) 0.0496(17) Uani 1 1 d . . .
H7 H -0.0049 0.3857 0.3427 0.060 Uiso 1 1 calc R . .
C8 C 0.1506(6) 0.4014(5) 0.2736(3) 0.0467(17) Uani 1 1 d . . .
H8 H 0.2305 0.3683 0.2656 0.056 Uiso 1 1 calc R . .
C9 C 0.0796(8) 0.4082(5) 0.1956(3) 0.0524(19) Uani 1 1 d . . .
C10 C 0.1620(7) 0.4115(5) 0.1216(3) 0.0469(17) Uani 1 1 d . . .
C11 C 0.1608(7) 0.4301(5) -0.0164(3) 0.064(2) Uani 1 1 d . . .
H11A H 0.1030 0.4441 -0.0584 0.096 Uiso 1 1 calc R . .
H11B H 0.1988 0.3695 -0.0258 0.096 Uiso 1 1 calc R . .
H11C H 0.2247 0.4779 -0.0146 0.096 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
Br1 0.1007(8) 0.0499(5) 0.0589(5) 0.0072(3) -0.0106(4) -0.0068(5)
Br2 0.1182(9) 0.0660(6) 0.0686(5) -0.0124(4) 0.0007(5) -0.0338(6)
O1 0.052(3) 0.074(3) 0.038(2) 0.002(2) -0.004(2) 0.002(3)
O2 0.045(3) 0.098(4) 0.054(3) 0.004(3) 0.004(2) 0.006(3)
O3 0.035(3) 0.179(7) 0.053(3) -0.005(3) -0.007(2) 0.006(4)
C1 0.050(5) 0.056(4) 0.059(4) 0.012(3) 0.008(3) -0.001(4)
C2 0.063(6) 0.054(4) 0.076(5) 0.016(4) -0.018(4) 0.002(4)
C3 0.082(6) 0.062(5) 0.057(4) 0.008(4) -0.021(4) -0.007(5)
C4 0.076(6) 0.089(6) 0.040(4) 0.008(4) 0.006(4) 0.000(6)
C5 0.058(5) 0.062(4) 0.052(4) 0.005(3) 0.004(3) 0.011(4)
C6 0.047(5) 0.045(4) 0.046(3) 0.006(3) -0.002(3) -0.001(4)
C7 0.040(4) 0.060(4) 0.048(3) -0.004(3) 0.007(3) 0.002(4)
C8 0.040(4) 0.055(4) 0.045(3) 0.001(3) 0.007(3) -0.002(4)
C9 0.051(5) 0.065(5) 0.041(3) 0.002(3) -0.005(3) 0.007(5)
C10 0.052(5) 0.048(4) 0.041(3) -0.007(3) 0.002(4) 0.000(4)
C11 0.086(6) 0.069(5) 0.037(3) -0.007(3) 0.008(4) 0.004(5)

_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 C8 1.964(7) . ?
Br2 C7 2.004(7) . ?
O1 C10 1.312(7) . ?
O1 C11 1.442(7) . ?
O2 C10 1.192(7) . ?
O3 C9 1.193(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(8) . ?
C1 C6 1.383(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.349(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(8) . ?
C6 C7 1.494(8) . ?
C7 H7 0.9800 . ?
C7 C8 1.504(8) . ?
C8 H8 0.9800 . ?
C8 C9 1.522(9) . ?
C9 C10 1.528(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C10 O1 C11 116.5(5) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.3(6) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(7) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(6) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(7) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(7) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.8(6) . . ?
C1 C6 C7 122.4(6) . . ?
C5 C6 C7 118.8(6) . . ?
Br2 C7 H7 108.5 . . ?
C6 C7 Br2 109.1(4) . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 118.2(6) . . ?
C8 C7 Br2 103.6(4) . . ?
C8 C7 H7 108.5 . . ?
Br1 C8 H8 110.1 . . ?
C7 C8 Br1 110.1(4) . . ?
C7 C8 H8 110.1 . . ?
C7 C8 C9 113.5(6) . . ?
C9 C8 Br1 102.7(4) . . ?
C9 C8 H8 110.1 . . ?
O3 C9 C8 123.0(6) . . ?
O3 C9 C10 121.9(6) . . ?
C8 C9 C10 115.1(7) . . ?
O1 C10 C9 111.0(6) . . ?
O2 C10 O1 126.1(6) . . ?
O2 C10 C9 122.9(6) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
Br1 C8 C9 O3 -90.8(8) . . . . ?
Br1 C8 C9 C10 88.0(6) . . . . ?
Br2 C7 C8 Br1 177.6(3) . . . . ?
Br2 C7 C8 C9 63.1(6) . . . . ?
O3 C9 C10 O1 6.0(11) . . . . ?
O3 C9 C10 O2 -173.9(8) . . . . ?
C1 C2 C3 C4 -0.2(12) . . . . ?
C1 C6 C7 Br2 72.7(7) . . . . ?
C1 C6 C7 C8 -45.3(9) . . . . ?
C2 C1 C6 C5 2.3(10) . . . . ?
C2 C1 C6 C7 -178.5(6) . . . . ?
C2 C3 C4 C5 1.2(13) . . . . ?
C3 C4 C5 C6 -0.5(12) . . . . ?
C4 C5 C6 C1 -1.3(10) . . . . ?
C4 C5 C6 C7 179.5(6) . . . . ?
C5 C6 C7 Br2 -108.2(6) . . . . ?
C5 C6 C7 C8 133.9(6) . . . . ?
C6 C1 C2 C3 -1.6(11) . . . . ?
C6 C7 C8 Br1 -61.5(7) . . . . ?
C6 C7 C8 C9 -176.0(6) . . . . ?
C7 C8 C9 O3 28.0(10) . . . . ?
C7 C8 C9 C10 -153.1(6) . . . . ?
C8 C9 C10 O1 -172.9(5) . . . . ?
C8 C9 C10 O2 7.2(10) . . . . ?
C11 O1 C10 O2 1.7(10) . . . . ?
C11 O1 C10 C9 -178.2(6) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 992325'
