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

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#                 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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_n1246_0m
#TrackingRef 'web_deposit_cif_file_0_DanielT.Cohen_1335894966.DKR_6a-Major.cif'


_audit_update_record             
;
2012-01-09 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Br O4'
_chemical_formula_weight         339.18
_chemical_absolute_configuration ad


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   5.3717(3)
_cell_length_b                   18.0674(8)
_cell_length_c                   29.3071(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2844.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1884
_cell_measurement_theta_min      6.04
_cell_measurement_theta_max      64.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    4.043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5828
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_process_details   'SADABS (Bruker)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4779
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0946
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         65.16
_reflns_number_total             4779
_reflns_number_gt                3499
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1000P)²+0.1984P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_number_reflns         4779
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_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
Br1 Br 0.8028(2) 0.27489(4) 0.04159(2) 0.0335(2) Uani 1 1 d . . .
Br2 Br 0.3095(2) 0.50869(5) 0.20090(2) 0.0351(2) Uani 1 1 d . . .
O6 O 0.3120(13) 0.3201(3) 0.25585(15) 0.0257(11) Uani 1 1 d . . .
O5 O 0.2909(14) 0.4221(3) 0.30214(17) 0.0351(13) Uani 1 1 d . . .
O1 O -0.1652(12) 0.4633(3) -0.01395(16) 0.0279(13) Uani 1 1 d . . .
O2 O -0.1915(15) 0.3624(3) -0.06263(17) 0.0340(13) Uani 1 1 d . . .
O7 O 0.1978(14) 0.1577(3) 0.29544(18) 0.0379(14) Uani 1 1 d . . .
O3 O -0.2660(14) 0.6325(4) -0.0456(2) 0.049(2) Uani 1 1 d . . .
O8 O 0.3810(11) 0.1304(3) 0.22870(16) 0.0282(14) Uani 1 1 d . . .
O4 O -0.0519(12) 0.6504(3) 0.01945(18) 0.0330(14) Uani 1 1 d . . .
C1 C 0.184(2) 0.0762(4) 0.2190(2) 0.0317(18) Uani 1 1 d . . .
H1A H 0.0191 0.1005 0.2194 0.038 Uiso 1 1 calc R . .
H1B H 0.1850 0.0364 0.2422 0.038 Uiso 1 1 calc R . .
C2 C -0.2380(18) 0.7035(5) 0.0345(3) 0.040(2) Uani 1 1 d . . .
H2A H -0.4024 0.6792 0.0372 0.048 Uiso 1 1 calc R . .
H2B H -0.2521 0.7444 0.0122 0.048 Uiso 1 1 calc R . .
C3 C 0.7280(17) 0.2783(4) 0.1053(2) 0.029(2) Uani 1 1 d . . .
C4 C 0.1456(14) 0.4948(4) 0.0444(2) 0.0257(17) Uani 1 1 d . . .
C5 C 0.7770(17) 0.3116(4) 0.3215(2) 0.0284(19) Uani 1 1 d . . .
H5A H 0.9555 0.2990 0.3181 0.034 Uiso 1 1 calc R . .
H5B H 0.7558 0.3433 0.3488 0.034 Uiso 1 1 calc R . .
C6 C 0.6231(15) 0.2841(4) 0.1975(2) 0.0225(17) Uani 1 1 d . . .
C7 C 0.0343(17) 0.4673(5) 0.1227(3) 0.0283(19) Uani 1 1 d . . .
H7 H -0.0789 0.4465 0.1440 0.034 Uiso 1 1 calc R . .
C8 C 0.2483(14) 0.5018(4) 0.1375(2) 0.027(2) Uani 1 1 d . . .
C9 C 0.3628(16) 0.5284(5) 0.0603(3) 0.029(2) Uani 1 1 d . . .
H9 H 0.4762 0.5489 0.0389 0.035 Uiso 1 1 calc R . .
C10 C -0.0891(17) 0.6202(5) -0.0218(3) 0.0281(19) Uani 1 1 d . . .
C11 C 0.2871(19) 0.4716(4) -0.0808(2) 0.0305(18) Uani 1 1 d . . .
H11A H 0.4673 0.4828 -0.0789 0.037 Uiso 1 1 calc R . .
H11B H 0.2561 0.4411 -0.1083 0.037 Uiso 1 1 calc R . .
C12 C 0.6775(18) 0.3501(4) 0.2786(2) 0.0250(16) Uani 1 1 d . . .
H12 H 0.7941 0.3853 0.2632 0.030 Uiso 1 1 calc R . .
C13 C 0.8390(16) 0.2502(4) 0.1819(2) 0.0262(18) Uani 1 1 d . . .
H13 H 0.9520 0.2295 0.2033 0.031 Uiso 1 1 calc R . .
C14 C 0.5174(18) 0.3134(5) 0.1194(2) 0.030(2) Uani 1 1 d . . .
H14 H 0.4080 0.3353 0.0978 0.036 Uiso 1 1 calc R . .
C15 C 0.1974(19) 0.4318(4) -0.0377(2) 0.0254(16) Uani 1 1 d . . .
H15 H 0.3152 0.3957 -0.0235 0.030 Uiso 1 1 calc R . .
C16 C 0.4116(18) 0.3754(5) 0.2830(3) 0.032(2) Uani 1 1 d . . .
C17 C 0.5871(17) 0.2158(4) 0.2755(2) 0.0263(18) Uani 1 1 d . . .
H17 H 0.7411 0.1890 0.2657 0.032 Uiso 1 1 calc R . .
C18 C 0.8939(17) 0.2457(4) 0.1356(3) 0.0291(19) Uani 1 1 d . . .
H18 H 1.0395 0.2212 0.1251 0.035 Uiso 1 1 calc R . .
C19 C 0.1213(15) 0.5668(4) -0.0323(2) 0.0238(19) Uani 1 1 d . . .
H19 H 0.2831 0.5900 -0.0233 0.029 Uiso 1 1 calc R . .
C20 C 0.6189(18) 0.2419(5) 0.3251(2) 0.035(2) Uani 1 1 d . . .
H20A H 0.4555 0.2530 0.3391 0.042 Uiso 1 1 calc R . .
H20B H 0.7042 0.2037 0.3436 0.042 Uiso 1 1 calc R . .
C21 C 0.0886(15) 0.4926(4) -0.0060(2) 0.0233(17) Uani 1 1 d . . .
C22 C 0.1366(17) 0.5418(4) -0.0822(2) 0.030(2) Uani 1 1 d . . .
H22A H -0.0316 0.5324 -0.0948 0.036 Uiso 1 1 calc R . .
H22B H 0.2200 0.5798 -0.1012 0.036 Uiso 1 1 calc R . .
C23 C 0.3675(16) 0.1659(5) 0.2694(2) 0.027(2) Uani 1 1 d . . .
C24 C 0.4173(17) 0.5326(5) 0.1062(3) 0.031(2) Uani 1 1 d . . .
H24 H 0.5657 0.5558 0.1165 0.037 Uiso 1 1 calc R . .
C25 C 0.5650(16) 0.2880(5) 0.2479(3) 0.0270(19) Uani 1 1 d . . .
C26 C -0.0725(18) 0.4075(4) -0.0422(3) 0.0311(19) Uani 1 1 d . . .
C27 C 0.2359(17) 0.0449(5) 0.1729(3) 0.036(2) Uani 1 1 d . . .
H27A H 0.2264 0.0844 0.1501 0.055 Uiso 1 1 calc R . .
H27B H 0.1124 0.0067 0.1658 0.055 Uiso 1 1 calc R . .
H27C H 0.4029 0.0231 0.1726 0.055 Uiso 1 1 calc R . .
C28 C -0.157(2) 0.7333(5) 0.0805(3) 0.050(3) Uani 1 1 d . . .
H28A H -0.1645 0.6937 0.1032 0.075 Uiso 1 1 calc R . .
H28B H -0.2673 0.7738 0.0896 0.075 Uiso 1 1 calc R . .
H28C H 0.0145 0.7518 0.0783 0.075 Uiso 1 1 calc R . .
C29 C -0.0145(16) 0.4633(5) 0.0758(3) 0.0282(19) Uani 1 1 d . . .
H29 H -0.1599 0.4386 0.0654 0.034 Uiso 1 1 calc R . .
C30 C 0.4632(17) 0.3171(4) 0.1662(3) 0.0280(19) Uani 1 1 d . . .
H30 H 0.3179 0.3421 0.1765 0.034 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 C3 1.910(7) . ?
Br2 C8 1.892(7) . ?
O6 C16 1.385(10) . ?
O6 C25 1.496(11) . ?
O5 C16 1.204(11) . ?
O1 C26 1.396(9) . ?
O1 C21 1.482(10) . ?
O2 C26 1.197(10) . ?
O7 C23 1.198(10) . ?
O3 C10 1.199(10) . ?
O8 C23 1.356(9) . ?
O8 C1 1.469(11) . ?
O4 C10 1.342(10) . ?
O4 C2 1.454(11) . ?
C1 C27 1.489(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C28 1.514(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C14 1.362(13) . ?
C3 C18 1.389(12) . ?
C4 C29 1.381(11) . ?
C4 C9 1.395(12) . ?
C4 C21 1.509(10) . ?
C5 C20 1.522(12) . ?
C5 C12 1.533(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C13 1.390(12) . ?
C6 C30 1.391(11) . ?
C6 C25 1.511(11) . ?
C7 C8 1.377(12) . ?
C7 C29 1.400(11) . ?
C7 H7 0.9500 . ?
C8 C24 1.404(11) . ?
C9 C24 1.380(11) . ?
C9 H9 0.9500 . ?
C10 C19 1.517(12) . ?
C11 C22 1.504(12) . ?
C11 C15 1.531(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.505(14) . ?
C12 C25 1.560(11) . ?
C12 H12 1.0000 . ?
C13 C18 1.390(10) . ?
C13 H13 0.9500 . ?
C14 C30 1.404(10) . ?
C14 H14 0.9500 . ?
C15 C26 1.521(14) . ?
C15 C21 1.554(10) . ?
C15 H15 1.0000 . ?
C17 C23 1.496(12) . ?
C17 C25 1.538(11) . ?
C17 C20 1.538(10) . ?
C17 H17 1.0000 . ?
C18 H18 0.9500 . ?
C19 C22 1.533(10) . ?
C19 C21 1.557(10) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 H24 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?

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 O6 C25 91.0(6) . . ?
C26 O1 C21 91.4(6) . . ?
C23 O8 C1 116.6(6) . . ?
C10 O4 C2 116.1(7) . . ?
O8 C1 C27 107.1(7) . . ?
O8 C1 H1A 110.3 . . ?
C27 C1 H1A 110.3 . . ?
O8 C1 H1B 110.3 . . ?
C27 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
O4 C2 C28 107.8(8) . . ?
O4 C2 H2A 110.1 . . ?
C28 C2 H2A 110.1 . . ?
O4 C2 H2B 110.1 . . ?
C28 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
C14 C3 C18 122.4(7) . . ?
C14 C3 Br1 119.2(6) . . ?
C18 C3 Br1 118.5(6) . . ?
C29 C4 C9 118.6(7) . . ?
C29 C4 C21 121.0(7) . . ?
C9 C4 C21 120.5(7) . . ?
C20 C5 C12 103.8(7) . . ?
C20 C5 H5A 111.0 . . ?
C12 C5 H5A 111.0 . . ?
C20 C5 H5B 111.0 . . ?
C12 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C13 C6 C30 119.1(7) . . ?
C13 C6 C25 121.1(7) . . ?
C30 C6 C25 119.8(7) . . ?
C8 C7 C29 119.2(8) . . ?
C8 C7 H7 120.4 . . ?
C29 C7 H7 120.4 . . ?
C7 C8 C24 120.9(7) . . ?
C7 C8 Br2 118.9(6) . . ?
C24 C8 Br2 120.1(6) . . ?
C24 C9 C4 121.8(8) . . ?
C24 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
O3 C10 O4 124.4(8) . . ?
O3 C10 C19 126.2(7) . . ?
O4 C10 C19 109.3(7) . . ?
C22 C11 C15 104.5(7) . . ?
C22 C11 H11A 110.9 . . ?
C15 C11 H11A 110.9 . . ?
C22 C11 H11B 110.9 . . ?
C15 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C16 C12 C5 113.5(7) . . ?
C16 C12 C25 84.2(7) . . ?
C5 C12 C25 106.2(6) . . ?
C16 C12 H12 116.1 . . ?
C5 C12 H12 116.1 . . ?
C25 C12 H12 116.1 . . ?
C18 C13 C6 121.7(8) . . ?
C18 C13 H13 119.2 . . ?
C6 C13 H13 119.2 . . ?
C3 C14 C30 119.5(7) . . ?
C3 C14 H14 120.3 . . ?
C30 C14 H14 120.3 . . ?
C26 C15 C11 111.4(7) . . ?
C26 C15 C21 84.1(7) . . ?
C11 C15 C21 106.3(6) . . ?
C26 C15 H15 116.8 . . ?
C11 C15 H15 116.8 . . ?
C21 C15 H15 116.8 . . ?
O5 C16 O6 124.5(9) . . ?
O5 C16 C12 139.8(8) . . ?
O6 C16 C12 95.7(7) . . ?
C23 C17 C25 112.9(7) . . ?
C23 C17 C20 112.6(7) . . ?
C25 C17 C20 104.2(7) . . ?
C23 C17 H17 109.0 . . ?
C25 C17 H17 109.0 . . ?
C20 C17 H17 109.0 . . ?
C3 C18 C13 117.6(8) . . ?
C3 C18 H18 121.2 . . ?
C13 C18 H18 121.2 . . ?
C10 C19 C22 114.9(7) . . ?
C10 C19 C21 111.2(6) . . ?
C22 C19 C21 103.0(6) . . ?
C10 C19 H19 109.2 . . ?
C22 C19 H19 109.2 . . ?
C21 C19 H19 109.2 . . ?
C5 C20 C17 104.5(6) . . ?
C5 C20 H20A 110.9 . . ?
C17 C20 H20A 110.9 . . ?
C5 C20 H20B 110.9 . . ?
C17 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
O1 C21 C4 110.5(6) . . ?
O1 C21 C15 89.9(6) . . ?
C4 C21 C15 121.9(6) . . ?
O1 C21 C19 109.5(6) . . ?
C4 C21 C19 116.1(6) . . ?
C15 C21 C19 105.6(6) . . ?
C11 C22 C19 104.5(6) . . ?
C11 C22 H22A 110.8 . . ?
C19 C22 H22A 110.8 . . ?
C11 C22 H22B 110.8 . . ?
C19 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
O7 C23 O8 122.9(8) . . ?
O7 C23 C17 126.8(7) . . ?
O8 C23 C17 110.3(7) . . ?
C9 C24 C8 118.5(8) . . ?
C9 C24 H24 120.8 . . ?
C8 C24 H24 120.8 . . ?
O6 C25 C6 110.9(6) . . ?
O6 C25 C17 108.5(6) . . ?
C6 C25 C17 117.2(7) . . ?
O6 C25 C12 89.1(6) . . ?
C6 C25 C12 121.1(7) . . ?
C17 C25 C12 106.2(6) . . ?
O2 C26 O1 126.7(9) . . ?
O2 C26 C15 138.6(8) . . ?
O1 C26 C15 94.6(6) . . ?
C1 C27 H27A 109.5 . . ?
C1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C28 H28A 109.5 . . ?
C2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C29 C7 121.0(8) . . ?
C4 C29 H29 119.5 . . ?
C7 C29 H29 119.5 . . ?
C6 C30 C14 119.7(8) . . ?
C6 C30 H30 120.1 . . ?
C14 C30 H30 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        65.16
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.120
_database_code_depnum_ccdc_archive 'CCDC 879780'
#######################################################################
#
#                 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_n1209_0m
#TrackingRef 'web_deposit_cif_file_1_DanielT.Cohen_1335894966.DKR_6b-Minor.cif'


_audit_update_record             
;
2012-01-09 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Br O4'
_chemical_formula_weight         339.18
_chemical_absolute_configuration ad


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                   5.4193(3)
_cell_length_b                   9.4004(5)
_cell_length_c                   28.0840(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1430.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4940
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      28.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Bruker)'

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12801
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         30.21
_reflns_number_total             4174
_reflns_number_gt                3204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1000P)²+0.7641P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_number_reflns         4174
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   0.584
_refine_ls_restrained_S_all      0.584
_refine_ls_shift/su_max          0.002
_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 0.22310(6) 1.06970(3) -0.037858(9) 0.03024(10) Uani 1 1 d . . .
O4 O 0.3064(4) 1.0619(2) 0.18121(6) 0.0192(4) Uani 1 1 d . . .
O1 O 0.6576(3) 0.6455(2) 0.14317(6) 0.0162(4) Uani 1 1 d . . .
O2 O 0.6370(4) 0.4088(2) 0.16079(7) 0.0263(5) Uani 1 1 d . . .
O3 O -0.0001(4) 0.9029(2) 0.18276(9) 0.0309(5) Uani 1 1 d . . .
C1 C 0.2159(5) 0.9299(3) 0.18422(8) 0.0160(5) Uani 1 1 d . . .
C2 C 0.2856(5) 0.5855(2) 0.15878(8) 0.0155(5) Uani 1 1 d . . .
H2 H 0.1605 0.5486 0.1357 0.019 Uiso 1 1 calc R . .
C3 C 0.2874(6) 0.9579(3) 0.01672(8) 0.0180(5) Uani 1 1 d . . .
C4 C 0.1302(6) 1.1757(3) 0.17178(10) 0.0230(6) Uani 1 1 d . . .
H4A H 0.1851 1.2641 0.1878 0.028 Uiso 1 1 calc R . .
H4B H -0.0335 1.1494 0.1848 0.028 Uiso 1 1 calc R . .
C5 C 0.1976(6) 0.6044(3) 0.21011(9) 0.0188(5) Uani 1 1 d . . .
H5A H 0.2117 0.5143 0.2281 0.023 Uiso 1 1 calc R . .
H5B H 0.0241 0.6372 0.2111 0.023 Uiso 1 1 calc R . .
C6 C 0.4177(5) 0.7256(3) 0.14450(8) 0.0130(5) Uani 1 1 d . . .
C7 C 0.3744(5) 0.8005(3) 0.09816(8) 0.0132(5) Uani 1 1 d . . .
C8 C 0.5435(5) 0.9027(3) 0.08368(9) 0.0161(5) Uani 1 1 d . . .
H8 H 0.6889 0.9182 0.1019 0.019 Uiso 1 1 calc R . .
C9 C 0.5016(5) 0.9827(3) 0.04275(9) 0.0190(5) Uani 1 1 d . . .
H9 H 0.6169 1.0527 0.0328 0.023 Uiso 1 1 calc R . .
C10 C 0.5408(6) 0.5224(3) 0.15499(9) 0.0181(5) Uani 1 1 d . . .
C11 C 0.1102(7) 1.2007(4) 0.11909(10) 0.0292(7) Uani 1 1 d . . .
H11A H 0.2717 1.2285 0.1065 0.044 Uiso 1 1 calc R . .
H11B H -0.0093 1.2768 0.1130 0.044 Uiso 1 1 calc R . .
H11C H 0.0550 1.1132 0.1034 0.044 Uiso 1 1 calc R . .
C12 C 0.4194(5) 0.8218(3) 0.18888(8) 0.0139(5) Uani 1 1 d . . .
H12 H 0.5830 0.8697 0.1926 0.017 Uiso 1 1 calc R . .
C13 C 0.3718(6) 0.7179(3) 0.23034(9) 0.0197(6) Uani 1 1 d . . .
H13A H 0.5281 0.6743 0.2413 0.024 Uiso 1 1 calc R . .
H13B H 0.2940 0.7679 0.2575 0.024 Uiso 1 1 calc R . .
C14 C 0.1643(5) 0.7761(3) 0.07091(9) 0.0157(5) Uani 1 1 d . . .
H14 H 0.0491 0.7056 0.0806 0.019 Uiso 1 1 calc R . .
C15 C 0.1213(5) 0.8543(3) 0.02954(9) 0.0172(5) Uani 1 1 d . . .
H15 H -0.0203 0.8363 0.0106 0.021 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 C3 1.891(2) . ?
O4 C1 1.337(3) . ?
O4 C4 1.458(3) . ?
O1 C10 1.359(3) . ?
O1 C6 1.503(3) . ?
O2 C10 1.199(3) . ?
O3 C1 1.198(4) . ?
C1 C12 1.505(4) . ?
C2 C10 1.508(4) . ?
C2 C5 1.529(3) . ?
C2 C6 1.552(3) . ?
C2 H2 1.0000 . ?
C3 C15 1.373(4) . ?
C3 C9 1.392(4) . ?
C4 C11 1.502(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C13 1.534(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.498(3) . ?
C6 C12 1.540(3) . ?
C7 C8 1.389(4) . ?
C7 C14 1.391(4) . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.541(4) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C1 O4 C4 116.9(2) . . ?
C10 O1 C6 91.01(19) . . ?
O3 C1 O4 123.5(3) . . ?
O3 C1 C12 125.1(3) . . ?
O4 C1 C12 111.3(2) . . ?
C10 C2 C5 113.5(2) . . ?
C10 C2 C6 83.8(2) . . ?
C5 C2 C6 106.77(19) . . ?
C10 C2 H2 116.1 . . ?
C5 C2 H2 116.1 . . ?
C6 C2 H2 116.1 . . ?
C15 C3 C9 121.8(2) . . ?
C15 C3 Br1 119.1(2) . . ?
C9 C3 Br1 119.1(2) . . ?
O4 C4 C11 109.9(2) . . ?
O4 C4 H4A 109.7 . . ?
C11 C4 H4A 109.7 . . ?
O4 C4 H4B 109.7 . . ?
C11 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C2 C5 C13 103.8(2) . . ?
C2 C5 H5A 111.0 . . ?
C13 C5 H5A 111.0 . . ?
C2 C5 H5B 111.0 . . ?
C13 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C7 C6 O1 110.4(2) . . ?
C7 C6 C12 115.4(2) . . ?
O1 C6 C12 108.01(19) . . ?
C7 C6 C2 123.4(2) . . ?
O1 C6 C2 88.85(18) . . ?
C12 C6 C2 106.98(19) . . ?
C8 C7 C14 119.5(2) . . ?
C8 C7 C6 118.4(2) . . ?
C14 C7 C6 121.9(2) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C3 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C3 C9 H9 120.7 . . ?
O2 C10 O1 126.0(3) . . ?
O2 C10 C2 137.6(3) . . ?
O1 C10 C2 96.3(2) . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 C6 108.8(2) . . ?
C1 C12 C13 111.8(2) . . ?
C6 C12 C13 103.8(2) . . ?
C1 C12 H12 110.8 . . ?
C6 C12 H12 110.8 . . ?
C13 C12 H12 110.8 . . ?
C5 C13 C12 105.3(2) . . ?
C5 C13 H13A 110.7 . . ?
C12 C13 H13A 110.7 . . ?
C5 C13 H13B 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C7 C14 C15 120.5(2) . . ?
C7 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C3 C15 C14 118.9(2) . . ?
C3 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        30.21
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.086


_database_code_depnum_ccdc_archive 'CCDC 879781'
