# Electronic Supplementary Material (ESI) for Chemical Science.
# 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_cm18cas

_audit_creation_method           SHELXL-97
_audit_update_record             
; 
? 
;

_chemical_name_systematic        
; 
? 
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Br O3'
_chemical_formula_sum            'C18 H17 Br O3'
_chemical_formula_structural     ?
_chemical_formula_weight         361.23

_chemical_absolute_configuration ad
_chemical_formula_iupac          ?
_chemical_formula_analytical     ?
_chemical_compound_source        ?

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)   '
_symmetry_space_group_name_Hall  'P 2yb '

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

_cell_length_a                   8.4484(19)
_cell_length_b                   6.0156(13)
_cell_length_c                   16.494(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.755(3)
_cell_angle_gamma                90.00
_cell_volume                     810.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2117
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.87
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_id                cm18cas

_exptl_crystal_preparation       
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 1 -4) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_absorpt_coefficient_mu    2.545
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5003
_exptl_absorpt_correction_T_max  0.8350
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'

_exptl_special_details           
; 
One distinct cell was identified using APEX2 (Bruker, 2010).  Seven 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2005) then corrected for absorption by 
integration using SHELXTL/XPREP V2005/2 (Bruker, 2005) before using 
SAINT/SADABS (Bruker, 2005) to sort, merge, and scale 
the combined data.  No decay correction was applied. 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  cm18cas
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_device       'Siemens Platform/ApexII CCD'
_diffrn_measurement_method       'profile data from  ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11991

_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2923
_reflns_number_gt                2761
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 V2010.11-3 (Bruker, 2010)'



_computing_cell_refinement       'SAINT V7.68A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V7.68A, XPREP V2005/2, SADABS V2008/2, TWINABS V2008/2 
(Bruker, 2005 & 2008) 
;
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_molecular_graphics    
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'

_refine_special_details          
; 
Structure was phased by direct methods (Sheldrick, 2008).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the 
full-matrix least-squares refinement on F².  The final difference 
Fourier map had no significant features.  A final analysis of 
variance between observed and calculated structure factors showed little 
dependence on amplitude or resolution. 
;

_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)+(0.0323P)²+0.0946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack (1983),  1287 Friedels'
_refine_ls_abs_structure_Flack   -0.008(7)
_refine_ls_number_reflns         2923
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0599
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 -0.34303(3) 0.96516(6) 0.539256(16) 0.04694(10) Uani 1 1 d . . .
O1 O 0.3278(2) 0.3278(3) 0.69952(11) 0.0312(4) Uani 1 1 d . . .
O2 O 0.48825(19) 0.1423(3) 0.88299(10) 0.0282(4) Uani 1 1 d . . .
O3 O 0.4608(2) 0.6375(3) 0.67746(11) 0.0365(4) Uani 1 1 d . . .
C1 C 0.5912(2) -0.0337(5) 0.86364(12) 0.0245(4) Uani 1 1 d . . .
C2 C 0.4539(3) 0.0572(4) 0.79796(14) 0.0253(5) Uani 1 1 d . . .
H2 H 0.3555 -0.0407 0.7804 0.030 Uiso 1 1 calc R . .
C3 C 0.4816(3) 0.2127(4) 0.73283(16) 0.0305(6) Uani 1 1 d . . .
H3A H 0.5693 0.3200 0.7577 0.037 Uiso 1 1 calc R . .
H3B H 0.5141 0.1296 0.6878 0.037 Uiso 1 1 calc R . .
C4 C 0.3351(3) 0.5395(4) 0.67484(14) 0.0257(6) Uani 1 1 d . . .
C5 C 0.1689(3) 0.6369(4) 0.64393(14) 0.0259(5) Uani 1 1 d . . .
C6 C 0.0281(3) 0.5301(4) 0.65322(15) 0.0315(6) Uani 1 1 d . . .
H6 H 0.0367 0.3899 0.6805 0.038 Uiso 1 1 calc R . .
C7 C -0.1251(3) 0.6276(5) 0.62273(15) 0.0317(6) Uani 1 1 d . . .
H7 H -0.2212 0.5553 0.6291 0.038 Uiso 1 1 calc R . .
C8 C -0.1347(3) 0.8307(4) 0.58317(14) 0.0307(6) Uani 1 1 d . . .
C9 C 0.0029(3) 0.9422(5) 0.57311(13) 0.0306(5) Uani 1 1 d . . .
H9 H -0.0065 1.0827 0.5460 0.037 Uiso 1 1 calc R . .
C10 C 0.1551(3) 0.8426(4) 0.60385(14) 0.0285(5) Uani 1 1 d . . .
H10 H 0.2508 0.9158 0.5974 0.034 Uiso 1 1 calc R . .
C11 C 0.7616(3) 0.0386(4) 0.86436(13) 0.0265(5) Uani 1 1 d . . .
C12 C 0.8467(3) -0.0729(5) 0.81484(15) 0.0384(7) Uani 1 1 d . . .
H12 H 0.7977 -0.1956 0.7815 0.046 Uiso 1 1 calc R . .
C13 C 1.0033(3) -0.0048(7) 0.81409(17) 0.0490(8) Uani 1 1 d . . .
H13 H 1.0609 -0.0810 0.7800 0.059 Uiso 1 1 calc R . .
C14 C 1.0759(3) 0.1727(6) 0.86240(19) 0.0458(7) Uani 1 1 d . . .
H14 H 1.1834 0.2178 0.8618 0.055 Uiso 1 1 calc R . .
C15 C 0.9923(3) 0.2842(5) 0.91139(17) 0.0387(6) Uani 1 1 d . . .
H15 H 1.0421 0.4069 0.9445 0.046 Uiso 1 1 calc R . .
C16 C 0.8355(3) 0.2185(4) 0.91281(15) 0.0302(5) Uani 1 1 d . . .
H16 H 0.7785 0.2961 0.9468 0.036 Uiso 1 1 calc R . .
C17 C 0.5770(3) -0.2564(4) 0.90358(16) 0.0303(5) Uani 1 1 d . . .
H17A H 0.6456 -0.2529 0.9620 0.036 Uiso 1 1 calc R . .
H17B H 0.6232 -0.3713 0.8732 0.036 Uiso 1 1 calc R . .
C18 C 0.4059(3) -0.3273(5) 0.90524(16) 0.0363(6) Uani 1 1 d . . .
H18A H 0.4119 -0.4620 0.9393 0.055 Uiso 1 1 calc R . .
H18B H 0.3415 -0.3576 0.8479 0.055 Uiso 1 1 calc R . .
H18C H 0.3536 -0.2081 0.9296 0.055 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 C8 1.904(2) . ?
O1 C4 1.343(3) . ?
O1 C3 1.451(3) . ?
O2 C2 1.451(3) . ?
O2 C1 1.456(3) . ?
O3 C4 1.206(3) . ?
C1 C2 1.476(3) . ?
C1 C11 1.501(3) . ?
C1 C17 1.511(4) . ?
C2 C3 1.487(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.486(3) . ?
C5 C10 1.394(4) . ?
C5 C6 1.394(3) . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(4) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.514(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 C3 117.5(2) . . ?
C2 O2 C1 61.01(13) . . ?
O2 C1 C2 59.33(14) . . ?
O2 C1 C11 114.4(2) . . ?
C2 C1 C11 118.1(2) . . ?
O2 C1 C17 115.53(18) . . ?
C2 C1 C17 120.9(2) . . ?
C11 C1 C17 115.83(19) . . ?
O2 C2 C1 59.67(14) . . ?
O2 C2 C3 116.5(2) . . ?
C1 C2 C3 121.6(2) . . ?
O2 C2 H2 115.7 . . ?
C1 C2 H2 115.7 . . ?
C3 C2 H2 115.7 . . ?
O1 C3 C2 106.45(18) . . ?
O1 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
O1 C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O3 C4 O1 124.1(2) . . ?
O3 C4 C5 124.5(2) . . ?
O1 C4 C5 111.5(2) . . ?
C10 C5 C6 119.4(2) . . ?
C10 C5 C4 118.1(2) . . ?
C6 C5 C4 122.6(2) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 122.3(2) . . ?
C7 C8 Br1 119.61(19) . . ?
C9 C8 Br1 118.1(2) . . ?
C8 C9 C10 118.2(3) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C16 119.2(2) . . ?
C12 C11 C1 119.6(2) . . ?
C16 C11 C1 121.2(2) . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C1 C17 C18 116.1(2) . . ?
C1 C17 H17A 108.3 . . ?
C18 C17 H17A 108.3 . . ?
C1 C17 H17B 108.3 . . ?
C18 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C2 O2 C1 C11 109.4(2) . . . . ?
C2 O2 C1 C17 -112.3(2) . . . . ?
C1 O2 C2 C3 -112.8(2) . . . . ?
C11 C1 C2 O2 -103.1(3) . . . . ?
C17 C1 C2 O2 103.2(2) . . . . ?
O2 C1 C2 C3 104.3(2) . . . . ?
C11 C1 C2 C3 1.2(4) . . . . ?
C17 C1 C2 C3 -152.4(2) . . . . ?
C4 O1 C3 C2 146.8(2) . . . . ?
O2 C2 C3 O1 -90.7(2) . . . . ?
C1 C2 C3 O1 -159.9(2) . . . . ?
C3 O1 C4 O3 1.2(3) . . . . ?
C3 O1 C4 C5 -178.8(2) . . . . ?
O3 C4 C5 C10 10.0(3) . . . . ?
O1 C4 C5 C10 -170.0(2) . . . . ?
O3 C4 C5 C6 -170.4(2) . . . . ?
O1 C4 C5 C6 9.7(3) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 Br1 178.95(18) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
Br1 C8 C9 C10 -178.90(17) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C6 C5 C10 C9 0.0(4) . . . . ?
C4 C5 C10 C9 179.7(2) . . . . ?
O2 C1 C11 C12 -152.5(2) . . . . ?
C2 C1 C11 C12 -85.7(3) . . . . ?
C17 C1 C11 C12 69.3(3) . . . . ?
O2 C1 C11 C16 26.4(3) . . . . ?
C2 C1 C11 C16 93.2(3) . . . . ?
C17 C1 C11 C16 -111.8(3) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C1 C11 C12 C13 178.9(3) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
C12 C11 C16 C15 -0.1(4) . . . . ?
C1 C11 C16 C15 -179.0(2) . . . . ?
O2 C1 C17 C18 40.6(3) . . . . ?
C2 C1 C17 C18 -27.5(3) . . . . ?
C11 C1 C17 C18 178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.999
_diffrn_standards_number         ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_time  ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.042

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 -1.00 0.0610
-1.00 0.00 1.00 0.1020
0.00 1.00 0.00 0.1550
0.00 -1.00 0.00 0.1670
0.00 0.00 1.00 0.0260
0.00 0.00 -1.00 0.0490
_database_code_depnum_ccdc_archive 'CCDC 1003604'
