# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       mshi@mail.sioc.ac.cn
_publ_contact_author_name        'Min Shi'
_publ_author_name                'Min Shi'

data_dm11329
_database_code_depnum_ccdc_archive 'CCDC 833190'
#TrackingRef '- dm11329.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 Br O5'
_chemical_formula_weight         395.24

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5579(17)
_cell_length_b                   9.7108(19)
_cell_length_c                   11.568(3)
_cell_angle_alpha                73.985(4)
_cell_angle_beta                 68.692(3)
_cell_angle_gamma                73.448(3)
_cell_volume                     842.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    2259
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.07

_exptl_crystal_description       PRISM
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    2.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5453
_exptl_absorpt_correction_T_max  0.7906
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5945
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3585
_reflns_number_gt                2988
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0971P)^2^+1.0638P] where P=(Fo^2^+2Fc^2^)/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         3585
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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 0.31553(5) 0.40146(4) 0.34947(4) 0.02566(16) Uani 1 1 d . . .
O1 O 0.8556(4) -0.0698(3) 0.1694(3) 0.0279(7) Uani 1 1 d . . .
O2 O 0.6894(4) 0.1538(3) 0.1778(3) 0.0249(6) Uani 1 1 d . . .
O3 O 0.8462(3) -0.0839(3) 0.5447(2) 0.0164(5) Uani 1 1 d . . .
O4 O 0.5918(4) 0.0648(3) 0.8166(3) 0.0263(7) Uani 1 1 d . . .
O5 O 0.7999(4) -0.1366(3) 0.7854(3) 0.0216(6) Uani 1 1 d . . .
C1 C 0.6205(8) 0.3252(5) 0.0043(5) 0.0431(13) Uani 1 1 d . . .
H1A H 0.4968 0.3400 0.0480 0.065 Uiso 1 1 calc R . .
H1B H 0.6411 0.3454 -0.0872 0.065 Uiso 1 1 calc R . .
H1C H 0.6691 0.3917 0.0252 0.065 Uiso 1 1 calc R . .
C2 C 0.7041(6) 0.1692(5) 0.0459(4) 0.0280(9) Uani 1 1 d . . .
H2A H 0.6453 0.1004 0.0368 0.034 Uiso 1 1 calc R . .
H2B H 0.8261 0.1486 -0.0057 0.034 Uiso 1 1 calc R . .
C3 C 0.7766(5) 0.0273(4) 0.2285(4) 0.0189(8) Uani 1 1 d . . .
C4 C 0.7594(5) 0.0287(4) 0.3599(4) 0.0154(7) Uani 1 1 d . . .
C5 C 0.8601(5) -0.0752(4) 0.4203(4) 0.0156(7) Uani 1 1 d . . .
C6 C 1.0002(5) -0.1978(4) 0.3709(4) 0.0206(8) Uani 1 1 d . . .
H6A H 0.9545 -0.2869 0.3945 0.031 Uiso 1 1 calc R . .
H6B H 1.0927 -0.2152 0.4074 0.031 Uiso 1 1 calc R . .
H6C H 1.0450 -0.1716 0.2786 0.031 Uiso 1 1 calc R . .
C7 C 0.6203(5) 0.1465(4) 0.4231(4) 0.0153(7) Uani 1 1 d . . .
H7 H 0.5100 0.1462 0.4116 0.018 Uiso 1 1 calc R . .
C8 C 0.5986(5) 0.1109(4) 0.5623(4) 0.0158(7) Uani 1 1 d . . .
H8 H 0.5024 0.1644 0.6166 0.019 Uiso 1 1 calc R . .
C9 C 0.7097(5) 0.0067(4) 0.6129(3) 0.0150(7) Uani 1 1 d . . .
C10 C 0.6917(5) -0.0177(4) 0.7493(4) 0.0178(8) Uani 1 1 d . . .
C11 C 0.7976(6) -0.1609(5) 0.9163(4) 0.0266(9) Uani 1 1 d . . .
H11A H 0.6787 -0.1556 0.9740 0.032 Uiso 1 1 calc R . .
H11B H 0.8452 -0.0851 0.9272 0.032 Uiso 1 1 calc R . .
C12 C 0.9050(7) -0.3101(6) 0.9458(5) 0.0415(13) Uani 1 1 d . . .
H12A H 0.8465 -0.3850 0.9490 0.062 Uiso 1 1 calc R . .
H12B H 0.9220 -0.3231 1.0277 0.062 Uiso 1 1 calc R . .
H12C H 1.0164 -0.3195 0.8798 0.062 Uiso 1 1 calc R . .
C13 C 0.6552(5) 0.3007(4) 0.3730(3) 0.0140(7) Uani 1 1 d . . .
C14 C 0.8138(5) 0.3257(4) 0.3633(4) 0.0184(8) Uani 1 1 d . . .
H14 H 0.9001 0.2454 0.3832 0.022 Uiso 1 1 calc R . .
C15 C 0.8457(5) 0.4660(4) 0.3252(4) 0.0231(8) Uani 1 1 d . . .
H15 H 0.9525 0.4812 0.3213 0.028 Uiso 1 1 calc R . .
C16 C 0.7236(5) 0.5840(4) 0.2929(4) 0.0224(8) Uani 1 1 d . . .
H16 H 0.7477 0.6796 0.2656 0.027 Uiso 1 1 calc R . .
C17 C 0.5666(5) 0.5636(4) 0.3002(4) 0.0198(8) Uani 1 1 d . . .
H17 H 0.4824 0.6442 0.2778 0.024 Uiso 1 1 calc R . .
C18 C 0.5345(5) 0.4221(4) 0.3413(4) 0.0152(7) Uani 1 1 d . . .

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 0.0189(2) 0.0212(2) 0.0386(3) -0.00302(16) -0.01501(18) -0.00140(14)
O1 0.0415(18) 0.0194(14) 0.0227(16) -0.0086(12) -0.0129(14) 0.0019(12)
O2 0.0424(18) 0.0151(13) 0.0206(15) -0.0028(11) -0.0181(13) -0.0010(12)
O3 0.0168(13) 0.0149(12) 0.0164(14) -0.0062(10) -0.0053(11) 0.0018(10)
O4 0.0323(16) 0.0218(14) 0.0194(15) -0.0079(12) -0.0068(13) 0.0046(12)
O5 0.0253(14) 0.0201(13) 0.0172(14) -0.0053(11) -0.0084(12) 0.0022(11)
C1 0.072(4) 0.025(2) 0.032(3) 0.0004(19) -0.032(3) 0.006(2)
C2 0.039(2) 0.0215(19) 0.022(2) -0.0045(16) -0.0152(19) 0.0046(17)
C3 0.0250(19) 0.0104(15) 0.020(2) -0.0034(14) -0.0057(16) -0.0037(14)
C4 0.0194(18) 0.0116(15) 0.0148(18) -0.0014(13) -0.0046(15) -0.0043(13)
C5 0.0171(17) 0.0138(16) 0.0167(19) -0.0051(14) -0.0036(15) -0.0044(13)
C6 0.0216(19) 0.0150(17) 0.022(2) -0.0056(15) -0.0053(16) 0.0008(14)
C7 0.0154(17) 0.0104(15) 0.0198(19) -0.0030(13) -0.0048(14) -0.0030(13)
C8 0.0189(17) 0.0096(15) 0.0186(19) -0.0038(13) -0.0051(15) -0.0023(13)
C9 0.0172(17) 0.0136(16) 0.0144(18) -0.0023(13) -0.0045(14) -0.0041(13)
C10 0.0208(18) 0.0153(16) 0.0175(19) -0.0012(14) -0.0057(15) -0.0059(14)
C11 0.035(2) 0.025(2) 0.018(2) -0.0026(16) -0.0108(18) -0.0023(17)
C12 0.054(3) 0.036(3) 0.023(2) -0.002(2) -0.016(2) 0.008(2)
C13 0.0174(17) 0.0119(15) 0.0140(18) -0.0052(13) -0.0058(14) -0.0014(13)
C14 0.0186(18) 0.0144(17) 0.021(2) -0.0049(14) -0.0068(15) 0.0001(14)
C15 0.0187(19) 0.0245(19) 0.031(2) -0.0113(17) -0.0061(17) -0.0077(15)
C16 0.032(2) 0.0134(17) 0.021(2) -0.0057(14) -0.0026(17) -0.0088(15)
C17 0.0247(19) 0.0122(16) 0.021(2) -0.0034(14) -0.0099(16) 0.0018(14)
C18 0.0174(17) 0.0157(16) 0.0150(18) -0.0047(14) -0.0072(14) -0.0027(13)

_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 C18 1.907(4) . ?
O1 C3 1.212(5) . ?
O2 C3 1.345(5) . ?
O2 C2 1.453(5) . ?
O3 C9 1.374(4) . ?
O3 C5 1.380(5) . ?
O4 C10 1.204(5) . ?
O5 C10 1.331(5) . ?
O5 C11 1.460(5) . ?
C1 C2 1.506(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.477(5) . ?
C4 C5 1.342(5) . ?
C4 C7 1.521(5) . ?
C5 C6 1.499(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.503(5) . ?
C7 C13 1.523(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.342(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.485(5) . ?
C11 C12 1.502(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.390(5) . ?
C13 C14 1.406(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(5) . ?
C17 H17 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
C3 O2 C2 115.5(3) . . ?
C9 O3 C5 117.8(3) . . ?
C10 O5 C11 115.2(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C1 106.2(3) . . ?
O2 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
O2 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O1 C3 O2 122.0(4) . . ?
O1 C3 C4 127.8(4) . . ?
O2 C3 C4 110.2(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 C7 122.7(3) . . ?
C3 C4 C7 117.4(3) . . ?
C4 C5 O3 122.8(3) . . ?
C4 C5 C6 128.5(4) . . ?
O3 C5 C6 108.6(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 109.2(3) . . ?
C8 C7 C13 107.3(3) . . ?
C4 C7 C13 114.9(3) . . ?
C8 C7 H7 108.5 . . ?
C4 C7 H7 108.5 . . ?
C13 C7 H7 108.5 . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 O3 123.5(3) . . ?
C8 C9 C10 121.1(3) . . ?
O3 C9 C10 115.3(3) . . ?
O4 C10 O5 125.1(4) . . ?
O4 C10 C9 122.4(3) . . ?
O5 C10 C9 112.5(3) . . ?
O5 C11 C12 107.5(3) . . ?
O5 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O5 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.1(3) . . ?
C18 C13 C7 123.4(3) . . ?
C14 C13 C7 119.4(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C13 C18 C17 122.6(3) . . ?
C13 C18 Br1 120.8(3) . . ?
C17 C18 Br1 116.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.103