# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
'Patricia E. Standen'
'Mark R. J. Elsegood'
'Marc C. Kimber'
'Simon J. Teat'
_publ_contact_author_name        'Mark R.J. Elsegood'
_publ_contact_author_email       M.R.J.Elsegood@lboro.ac.uk

data_?
_database_code_depnum_ccdc_archive 'CCDC 893728'
#TrackingRef '- 19.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 O2'
_chemical_formula_sum            'C11 H16 O2'
_chemical_formula_weight         180.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.3188(14)
_cell_length_b                   7.8255(10)
_cell_length_c                   11.8409(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.7750(18)
_cell_angle_gamma                90.00
_cell_volume                     998.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6497
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      33.60

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Beam line 11.3.1 at the ALS'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14038
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         33.62
_reflns_number_total             3034
_reflns_number_gt                2659
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker APEX 2'
_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 and local programs'

_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^)+(0.0621P)^2^+0.1811P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.37404(5) 0.04096(7) 0.79369(5) 0.02265(14) Uani 1 1 d . . .
H1 H 0.3576 -0.0546 0.8175 0.034 Uiso 1 1 calc R . .
C1 C 0.49572(7) 0.03635(10) 0.78060(7) 0.02147(16) Uani 1 1 d . . .
C2 C 0.51887(8) 0.20243(11) 0.71900(7) 0.02679(18) Uani 1 1 d . . .
H2A H 0.4682 0.2167 0.6341 0.032 Uiso 1 1 calc R . .
C3 C 0.65772(9) 0.19017(14) 0.74291(9) 0.0338(2) Uani 1 1 d . . .
H3 H 0.7026 0.2277 0.6915 0.041 Uiso 1 1 calc R . .
C4 C 0.70616(8) 0.11714(12) 0.84910(8) 0.03000(19) Uani 1 1 d . . .
H4 H 0.7915 0.0938 0.8869 0.036 Uiso 1 1 calc R . .
C5 C 0.60027(7) 0.07841(10) 0.89816(7) 0.02227(16) Uani 1 1 d . . .
H5 H 0.6169 -0.0114 0.9612 0.027 Uiso 1 1 calc R . .
C6 C 0.55306(8) 0.25416(10) 0.93041(7) 0.02337(17) Uani 1 1 d . . .
H6 H 0.4835 0.2333 0.9643 0.028 Uiso 1 1 calc R . .
C7 C 0.50013(9) 0.34099(11) 0.80680(8) 0.02870(19) Uani 1 1 d . . .
H7A H 0.5464 0.4467 0.8020 0.034 Uiso 1 1 calc R . .
H7B H 0.4112 0.3692 0.7902 0.034 Uiso 1 1 calc R . .
C8 C 0.51324(8) -0.13361(11) 0.72280(8) 0.02805(19) Uani 1 1 d . . .
H8A H 0.5981 -0.1374 0.7156 0.034 Uiso 1 1 calc R . .
H8B H 0.5055 -0.2289 0.7751 0.034 Uiso 1 1 calc R . .
C9 C 0.42127(9) -0.15931(12) 0.60253(8) 0.02950(19) Uani 1 1 d . . .
H9 H 0.4232 -0.0807 0.5420 0.035 Uiso 1 1 calc R . .
C10 C 0.33824(12) -0.28210(16) 0.57436(10) 0.0449(3) Uani 1 1 d . . .
H10A H 0.3334 -0.3632 0.6324 0.054 Uiso 1 1 calc R . .
H10B H 0.2831 -0.2897 0.4959 0.054 Uiso 1 1 calc R . .
C11 C 0.65197(8) 0.36001(11) 1.01765(8) 0.02695(18) Uani 1 1 d . . .
H11A H 0.7229 0.3785 0.9866 0.032 Uiso 1 1 calc R . .
H11B H 0.6177 0.4729 1.0288 0.032 Uiso 1 1 calc R . .
O2 O 0.69274(7) 0.27124(9) 1.12852(6) 0.03243(17) Uani 1 1 d . . .
H2 H 0.7446 0.3316 1.1785 0.049 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
O1 0.0195(3) 0.0202(3) 0.0244(3) 0.0010(2) 0.0010(2) 0.00089(19)
C1 0.0197(3) 0.0198(3) 0.0212(3) -0.0006(3) 0.0008(3) 0.0006(3)
C2 0.0294(4) 0.0253(4) 0.0212(3) 0.0020(3) 0.0010(3) -0.0038(3)
C3 0.0314(4) 0.0384(5) 0.0314(4) -0.0020(4) 0.0092(4) -0.0102(4)
C4 0.0221(4) 0.0313(4) 0.0336(4) -0.0041(3) 0.0041(3) -0.0030(3)
C5 0.0202(3) 0.0194(3) 0.0225(3) 0.0006(3) -0.0005(3) 0.0005(3)
C6 0.0241(4) 0.0182(3) 0.0222(4) -0.0008(3) -0.0012(3) -0.0004(3)
C7 0.0337(4) 0.0184(4) 0.0258(4) 0.0023(3) -0.0032(3) -0.0003(3)
C8 0.0252(4) 0.0243(4) 0.0307(4) -0.0064(3) 0.0026(3) 0.0016(3)
C9 0.0337(4) 0.0288(4) 0.0258(4) -0.0057(3) 0.0088(3) -0.0061(3)
C10 0.0550(7) 0.0483(6) 0.0291(5) -0.0083(4) 0.0092(4) -0.0262(5)
C11 0.0293(4) 0.0210(4) 0.0242(4) -0.0007(3) -0.0014(3) -0.0036(3)
O2 0.0341(3) 0.0292(3) 0.0238(3) 0.0010(2) -0.0062(2) -0.0100(3)

_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
O1 C1 1.4326(10) . ?
C1 C8 1.5361(11) . ?
C1 C2 1.5513(11) . ?
C1 C5 1.5623(11) . ?
C2 C3 1.5124(13) . ?
C2 C7 1.5609(13) . ?
C3 C4 1.3369(14) . ?
C4 C5 1.5137(12) . ?
C5 C6 1.5644(11) . ?
C6 C11 1.5168(11) . ?
C6 C7 1.5581(12) . ?
C8 C9 1.4990(13) . ?
C9 C10 1.3139(14) . ?
C11 O2 1.4314(10) . ?

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
O1 C1 C8 109.22(6) . . ?
O1 C1 C2 109.62(6) . . ?
C8 C1 C2 116.91(7) . . ?
O1 C1 C5 112.96(6) . . ?
C8 C1 C5 114.44(6) . . ?
C2 C1 C5 92.96(6) . . ?
C3 C2 C1 100.01(7) . . ?
C3 C2 C7 105.32(7) . . ?
C1 C2 C7 101.07(7) . . ?
C4 C3 C2 107.91(8) . . ?
C3 C4 C5 107.52(8) . . ?
C4 C5 C1 99.98(7) . . ?
C4 C5 C6 106.69(7) . . ?
C1 C5 C6 100.39(6) . . ?
C11 C6 C7 113.19(7) . . ?
C11 C6 C5 114.22(7) . . ?
C7 C6 C5 102.49(6) . . ?
C6 C7 C2 103.37(6) . . ?
C9 C8 C1 113.13(7) . . ?
C10 C9 C8 125.08(9) . . ?
O2 C11 C6 108.90(7) . . ?

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
O1 C1 C2 C3 166.31(7) . . . . ?
C8 C1 C2 C3 -68.74(8) . . . . ?
C5 C1 C2 C3 50.65(7) . . . . ?
O1 C1 C2 C7 58.38(8) . . . . ?
C8 C1 C2 C7 -176.68(7) . . . . ?
C5 C1 C2 C7 -57.28(7) . . . . ?
C1 C2 C3 C4 -34.29(10) . . . . ?
C7 C2 C3 C4 70.22(10) . . . . ?
C2 C3 C4 C5 0.22(11) . . . . ?
C3 C4 C5 C1 33.65(9) . . . . ?
C3 C4 C5 C6 -70.48(9) . . . . ?
O1 C1 C5 C4 -163.36(7) . . . . ?
C8 C1 C5 C4 70.83(8) . . . . ?
C2 C1 C5 C4 -50.59(7) . . . . ?
O1 C1 C5 C6 -54.17(8) . . . . ?
C8 C1 C5 C6 -179.98(7) . . . . ?
C2 C1 C5 C6 58.60(7) . . . . ?
C4 C5 C6 C11 -57.29(9) . . . . ?
C1 C5 C6 C11 -161.12(7) . . . . ?
C4 C5 C6 C7 65.52(8) . . . . ?
C1 C5 C6 C7 -38.30(8) . . . . ?
C11 C6 C7 C2 125.54(8) . . . . ?
C5 C6 C7 C2 2.03(8) . . . . ?
C3 C2 C7 C6 -68.48(8) . . . . ?
C1 C2 C7 C6 35.25(8) . . . . ?
O1 C1 C8 C9 59.95(9) . . . . ?
C2 C1 C8 C9 -65.20(10) . . . . ?
C5 C1 C8 C9 -172.31(7) . . . . ?
C1 C8 C9 C10 -116.93(12) . . . . ?
C7 C6 C11 O2 178.91(7) . . . . ?
C5 C6 C11 O2 -64.30(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.96 2.7953(9) 176.0 3_657
O2 H2 O1 0.84 1.94 2.7831(9) 175.7 4_666

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        33.62
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037

#===END