# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         182

_publ_requested_journal          'Chemical Communications'

loop_
_publ_author_name
'Hawker, Craig J.'
'Wolffs, Martin'
'Kade, Matt'

_publ_contact_author_name        'Craig J. Hawker'
_publ_contact_author_address     
;
Santa Barbara
California
United States
93106
;

_publ_contact_author_email       hawker@mrl.ucsb.edu
# Attachment '- H080510.CIF'

data_h080510
_database_code_depnum_ccdc_archive 'CCDC 833163'
#TrackingRef '- H080510.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 O4'
_chemical_formula_weight         209.21

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)/c

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

_cell_length_a                   9.089(3)
_cell_length_b                   10.451(3)
_cell_length_c                   12.182(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.965(5)
_cell_angle_gamma                90.00
_cell_volume                     1080.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8493
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2174
_reflns_number_gt                1500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0400P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.25(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2174
_refine_ls_number_parameters     141
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   2.294
_refine_ls_restrained_S_all      2.417
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.003

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
C1 C 1.0524(3) 0.09045(19) 0.5864(2) 0.0630(7) Uani 1 1 d . . .
H1 H 1.0877 0.1530 0.6442 0.076 Uiso 1 1 calc R . .
C2 C 1.0358(3) 0.12023(19) 0.47215(19) 0.0618(7) Uani 1 1 d . . .
H2 H 1.0610 0.2021 0.4546 0.074 Uiso 1 1 calc R . .
C3 C 0.9820(2) 0.03017(19) 0.38313(18) 0.0548(6) Uani 1 1 d . . .
C4 C 0.9561(3) 0.0637(2) 0.25726(19) 0.0639(7) Uani 1 1 d . . .
H4A H 0.9881 -0.0085 0.2210 0.077 Uiso 1 1 calc R . .
H4B H 1.0238 0.1352 0.2566 0.077 Uiso 1 1 calc R . .
C5 C 0.7845(3) 0.09907(18) 0.18205(18) 0.0554(6) Uani 1 1 d . . .
C6 C 0.7389(3) 0.21321(19) 0.2381(2) 0.0637(7) Uani 1 1 d D . .
C7 C 0.5166(3) 0.09926(19) 0.2542(2) 0.0711(7) Uani 1 1 d D . .
C8 C 0.3619(4) 0.1396(3) 0.1723(3) 0.1265(14) Uani 1 1 d . . .
H8A H 0.3219 0.2072 0.2071 0.190 Uiso 1 1 calc R . .
H8B H 0.2906 0.0684 0.1552 0.190 Uiso 1 1 calc R . .
H8C H 0.3718 0.1697 0.1008 0.190 Uiso 1 1 calc R . .
C9 C 0.5150(7) 0.0627(4) 0.3694(3) 0.166(2) Uani 1 1 d . . .
H9A H 0.4514 -0.0125 0.3617 0.249 Uiso 1 1 calc R . .
H9B H 0.4720 0.1314 0.4008 0.249 Uiso 1 1 calc R . .
H9C H 0.6206 0.0452 0.4215 0.249 Uiso 1 1 calc R . .
C10 C 0.6817(3) -0.0175(2) 0.16946(19) 0.0578(6) Uani 1 1 d D . .
C11 C 0.7742(4) 0.1362(2) 0.0572(2) 0.0857(9) Uani 1 1 d . . .
H11A H 0.8182 0.0689 0.0249 0.129 Uiso 1 1 calc R . .
H11B H 0.8321 0.2138 0.0605 0.129 Uiso 1 1 calc R . .
H11C H 0.6659 0.1490 0.0084 0.129 Uiso 1 1 calc R . .
O1 O 0.8080(2) 0.31234(14) 0.25494(17) 0.0872(7) Uani 1 1 d . . .
O4 O 0.7043(2) -0.11680(14) 0.12999(14) 0.0786(6) Uani 1 1 d . . .
O2B O 0.5861(6) 0.2134(5) 0.2286(5) 0.0766(10) Uani 0.384(4) 1 d PD . .
O2A O 0.6373(4) 0.1972(3) 0.2987(4) 0.0766(10) Uani 0.616(4) 1 d PD . .
O3B O 0.5856(7) -0.0148(6) 0.2374(5) 0.0766(10) Uani 0.38 1 d PD . .
O3A O 0.5480(4) -0.0089(4) 0.1874(3) 0.0766(10) Uani 0.616(4) 1 d PD . .

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
C1 0.0709(16) 0.0503(12) 0.0560(14) -0.0028(10) 0.0082(11) 0.0041(10)
C2 0.0619(14) 0.0514(12) 0.0621(16) 0.0040(10) 0.0099(11) -0.0012(10)
C3 0.0474(12) 0.0552(12) 0.0578(14) 0.0032(10) 0.0140(10) 0.0082(9)
C4 0.0619(15) 0.0666(13) 0.0652(16) 0.0023(11) 0.0252(12) 0.0026(10)
C5 0.0622(14) 0.0526(11) 0.0470(13) 0.0046(9) 0.0140(10) -0.0041(9)
C6 0.0582(14) 0.0474(12) 0.0769(17) 0.0078(10) 0.0136(12) -0.0023(10)
C7 0.0669(16) 0.0518(12) 0.100(2) -0.0123(12) 0.0367(14) -0.0084(10)
C8 0.112(3) 0.124(3) 0.109(3) -0.039(2) -0.003(2) 0.043(2)
C9 0.293(7) 0.097(2) 0.090(3) -0.007(2) 0.046(3) -0.038(3)
C10 0.0647(15) 0.0510(12) 0.0518(13) 0.0032(9) 0.0136(11) 0.0010(10)
C11 0.108(2) 0.0887(18) 0.0527(15) 0.0095(13) 0.0198(15) -0.0255(15)
O1 0.0846(13) 0.0515(9) 0.1209(16) -0.0027(9) 0.0313(11) -0.0152(8)
O4 0.1096(14) 0.0558(10) 0.0757(12) -0.0118(8) 0.0397(11) -0.0064(8)
O2B 0.0610(16) 0.0548(9) 0.111(3) -0.0233(16) 0.0273(17) -0.0108(10)
O2A 0.0610(16) 0.0548(9) 0.111(3) -0.0233(16) 0.0273(17) -0.0108(10)
O3B 0.0610(16) 0.0548(9) 0.111(3) -0.0233(16) 0.0273(17) -0.0108(10)
O3A 0.0610(16) 0.0548(9) 0.111(3) -0.0233(16) 0.0273(17) -0.0108(10)

_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
C1 C3 1.381(3) 3_756 ?
C1 C2 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C1 1.381(3) 3_756 ?
C3 C4 1.507(3) . ?
C4 C5 1.545(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(3) . ?
C5 C10 1.510(3) . ?
C5 C11 1.540(3) . ?
C6 O1 1.190(2) . ?
C6 O2B 1.352(5) . ?
C6 O2A 1.383(4) . ?
C7 O3B 1.396(6) . ?
C7 O2B 1.436(5) . ?
C7 O2A 1.456(3) . ?
C7 C8 1.466(4) . ?
C7 C9 1.460(4) . ?
C7 O3A 1.479(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O4 1.192(2) . ?
C10 O3A 1.312(4) . ?
C10 O3B 1.402(7) . ?
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
C3 C1 C2 121.5(2) 3_756 . ?
C3 C1 H1 119.2 3_756 . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 121.1(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C1 C3 C2 117.4(2) 3_756 . ?
C1 C3 C4 121.2(2) 3_756 . ?
C2 C3 C4 121.41(19) . . ?
C3 C4 C5 114.58(18) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C10 115.18(19) . . ?
C6 C5 C11 108.65(18) . . ?
C10 C5 C11 106.64(18) . . ?
C6 C5 C4 107.69(17) . . ?
C10 C5 C4 108.90(17) . . ?
C11 C5 C4 109.7(2) . . ?
O1 C6 O2B 118.4(3) . . ?
O1 C6 O2A 115.2(2) . . ?
O2B C6 O2A 35.4(2) . . ?
O1 C6 C5 123.7(2) . . ?
O2B C6 C5 113.8(3) . . ?
O2A C6 C5 119.4(2) . . ?
O3B C7 O2B 115.0(4) . . ?
O3B C7 O2A 109.7(3) . . ?
O2B C7 O2A 33.4(2) . . ?
O3B C7 C8 121.2(3) . . ?
O2B C7 C8 90.1(3) . . ?
O2A C7 C8 117.6(3) . . ?
O3B C7 C9 94.4(4) . . ?
O2B C7 C9 125.7(3) . . ?
O2A C7 C9 95.2(3) . . ?
C8 C7 C9 113.1(3) . . ?
O3B C7 O3A 23.3(3) . . ?
O2B C7 O3A 109.2(3) . . ?
O2A C7 O3A 118.3(2) . . ?
C8 C7 O3A 99.9(2) . . ?
C9 C7 O3A 113.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O3A 115.5(2) . . ?
O4 C10 O3B 119.3(3) . . ?
O3A C10 O3B 24.6(3) . . ?
O4 C10 C5 123.6(2) . . ?
O3A C10 C5 120.2(2) . . ?
O3B C10 C5 114.7(3) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 O2B C7 119.9(4) . . ?
C6 O2A C7 116.4(3) . . ?
C7 O3B C10 120.7(5) . . ?
C10 O3A C7 121.1(3) . . ?

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
C3 C1 C2 C3 0.7(4) 3_756 . . . ?
C1 C2 C3 C1 -0.7(4) . . . 3_756 ?
C1 C2 C3 C4 177.03(19) . . . . ?
C1 C3 C4 C5 81.5(3) 3_756 . . . ?
C2 C3 C4 C5 -96.1(2) . . . . ?
C3 C4 C5 C6 59.8(2) . . . . ?
C3 C4 C5 C10 -65.7(2) . . . . ?
C3 C4 C5 C11 177.87(18) . . . . ?
C10 C5 C6 O1 179.7(2) . . . . ?
C11 C5 C6 O1 -60.8(3) . . . . ?
C4 C5 C6 O1 58.0(3) . . . . ?
C10 C5 C6 O2B -23.7(4) . . . . ?
C11 C5 C6 O2B 95.8(4) . . . . ?
C4 C5 C6 O2B -145.4(3) . . . . ?
C10 C5 C6 O2A 15.6(3) . . . . ?
C11 C5 C6 O2A 135.1(3) . . . . ?
C4 C5 C6 O2A -106.1(3) . . . . ?
C6 C5 C10 O4 -177.8(2) . . . . ?
C11 C5 C10 O4 61.6(3) . . . . ?
C4 C5 C10 O4 -56.8(3) . . . . ?
C6 C5 C10 O3A 11.5(3) . . . . ?
C11 C5 C10 O3A -109.1(3) . . . . ?
C4 C5 C10 O3A 132.6(3) . . . . ?
C6 C5 C10 O3B -15.5(4) . . . . ?
C11 C5 C10 O3B -136.2(4) . . . . ?
C4 C5 C10 O3B 105.5(3) . . . . ?
O1 C6 O2B C7 -155.6(3) . . . . ?
O2A C6 O2B C7 -61.4(5) . . . . ?
C5 C6 O2B C7 46.4(6) . . . . ?
O3B C7 O2B C6 -26.9(6) . . . . ?
O2A C7 O2B C6 61.3(5) . . . . ?
C8 C7 O2B C6 -151.8(5) . . . . ?
C9 C7 O2B C6 89.2(6) . . . . ?
O3A C7 O2B C6 -51.3(5) . . . . ?
O1 C6 O2A C7 161.2(2) . . . . ?
O2B C6 O2A C7 57.0(4) . . . . ?
C5 C6 O2A C7 -33.4(4) . . . . ?
O3B C7 O2A C6 49.7(5) . . . . ?
O2B C7 O2A C6 -56.1(5) . . . . ?
C8 C7 O2A C6 -94.1(4) . . . . ?
C9 C7 O2A C6 146.3(4) . . . . ?
O3A C7 O2A C6 26.0(4) . . . . ?
O2B C7 O3B C10 -17.5(6) . . . . ?
O2A C7 O3B C10 -53.3(5) . . . . ?
C8 C7 O3B C10 89.1(6) . . . . ?
C9 C7 O3B C10 -150.5(5) . . . . ?
O3A C7 O3B C10 63.0(9) . . . . ?
O4 C10 O3B C7 -159.9(3) . . . . ?
O3A C10 O3B C7 -72.2(9) . . . . ?
C5 C10 O3B C7 37.0(6) . . . . ?
O4 C10 O3A C7 169.5(3) . . . . ?
O3B C10 O3A C7 64.4(8) . . . . ?
C5 C10 O3A C7 -19.1(5) . . . . ?
O3B C7 O3A C10 -72.9(9) . . . . ?
O2B C7 O3A C10 36.0(4) . . . . ?
O2A C7 O3A C10 0.7(5) . . . . ?
C8 C7 O3A C10 129.6(4) . . . . ?
C9 C7 O3A C10 -109.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.038