# Electronic Supplementary Material (ESI) for RSC Advances.
# 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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#  data retrieval see:
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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_a
_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C16 H16 O4'

_chemical_formula_weight         272.29



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           Triclinic

_symmetry_space_group_name_H-M   P-1



loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   7.326(4)

_cell_length_b                   7.814(4)

_cell_length_c                   12.700(7)

_cell_angle_alpha                75.280(6)

_cell_angle_beta                 84.078(6)

_cell_angle_gamma                88.663(6)

_cell_volume                     699.4(6)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2305

_cell_measurement_theta_min      2.69

_cell_measurement_theta_max      28.08



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.35

_exptl_crystal_size_min          0.21

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.293

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             288

_exptl_absorpt_coefficient_mu    0.093

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9595

_exptl_absorpt_correction_T_max  0.9808

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      296(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       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5306

_diffrn_reflns_av_R_equivalents  0.0128

_diffrn_reflns_av_sigmaI/netI    0.0174

_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         2.70

_diffrn_reflns_theta_max         25.49

_reflns_number_total             2579

_reflns_number_gt                2059

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_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)+(0.0650P)²+0.1034P] 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_number_reflns         2579

_refine_ls_number_parameters     184

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0502

_refine_ls_R_factor_gt           0.0410

_refine_ls_wR_factor_ref         0.1204

_refine_ls_wR_factor_gt          0.1115

_refine_ls_goodness_of_fit_ref   1.037

_refine_ls_restrained_S_all      1.037

_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




































C1 C 1.17315(19) 0.25372(18) 0.42346(11) 0.0418(3) Uani 1 1 d . . .
C2 C 1.03165(18) 0.23526(17) 0.50466(11) 0.0386(3) Uani 1 1 d . . .
C3 C 0.85896(19) 0.32840(18) 0.48191(11) 0.0411(3) Uani 1 1 d . . .
C4 C 0.85332(19) 0.43917(17) 0.36931(11) 0.0386(3) Uani 1 1 d . . .
C5 C 0.69849(19) 0.53755(18) 0.33550(11) 0.0432(3) Uani 1 1 d . . .
H5 H 0.5959 0.5343 0.3856 0.052 Uiso 1 1 calc R . .
C6 C 0.6939(2) 0.63993(19) 0.22918(12) 0.0455(4) Uani 1 1 d . . .
C7 C 0.8514(2) 0.6446(2) 0.15527(12) 0.0497(4) Uani 1 1 d . . .
H7 H 0.8512 0.7132 0.0838 0.060 Uiso 1 1 calc R . .
C8 C 1.0062(2) 0.5497(2) 0.18641(12) 0.0493(4) Uani 1 1 d . . .
H8 H 1.1094 0.5539 0.1366 0.059 Uiso 1 1 calc R . .
C9 C 1.00572(19) 0.44752(18) 0.29346(11) 0.0406(3) Uani 1 1 d . . .
C10 C 1.3566(2) 0.1671(2) 0.43212(14) 0.0558(4) Uani 1 1 d . . .
H10A H 1.4297 0.2028 0.3629 0.084 Uiso 1 1 calc R . .
H10B H 1.3413 0.0409 0.4520 0.084 Uiso 1 1 calc R . .
H10C H 1.4170 0.2019 0.4870 0.084 Uiso 1 1 calc R . .
C11 C 1.0604(2) 0.12171(18) 0.61323(11) 0.0422(3) Uani 1 1 d . . .
H11 H 1.1774 0.0742 0.6208 0.051 Uiso 1 1 calc R . .
C12 C 0.9410(2) 0.0783(2) 0.70174(12) 0.0486(4) Uani 1 1 d . . .
H12 H 0.8221 0.1220 0.6968 0.058 Uiso 1 1 calc R . .
C13 C 0.9863(2) -0.0352(2) 0.80737(12) 0.0495(4) Uani 1 1 d . . .
C14 C 1.2158(3) -0.1994(2) 0.90944(13) 0.0600(5) Uani 1 1 d . . .
H14A H 1.1337 -0.3001 0.9364 0.072 Uiso 1 1 calc R . .
H14B H 1.2101 -0.1316 0.9640 0.072 Uiso 1 1 calc R . .
C15 C 1.4079(3) -0.2610(2) 0.88825(16) 0.0711(5) Uani 1 1 d . . .
H15A H 1.4132 -0.3227 0.8316 0.107 Uiso 1 1 calc R . .
H15B H 1.4448 -0.3390 0.9540 0.107 Uiso 1 1 calc R . .
H15C H 1.4890 -0.1607 0.8656 0.107 Uiso 1 1 calc R . .
C16 C 0.5260(2) 0.7440(2) 0.19419(15) 0.0647(5) Uani 1 1 d . . .
H16A H 0.4231 0.6652 0.2058 0.097 Uiso 1 1 calc R . .
H16B H 0.5463 0.8039 0.1180 0.097 Uiso 1 1 calc R . .
H16C H 0.5012 0.8293 0.2364 0.097 Uiso 1 1 calc R . .
O1 O 1.16348(13) 0.35520(13) 0.32014(8) 0.0460(3) Uani 1 1 d . . .
O2 O 0.72438(15) 0.31781(16) 0.55049(8) 0.0608(3) Uani 1 1 d . . .
O3 O 1.16173(15) -0.08966(14) 0.80674(8) 0.0552(3) Uani 1 1 d . . .
O4 O 0.87659(18) -0.07585(18) 0.88759(9) 0.0741(4) Uani 1 1 d . . .






_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 O1 1.3577(17) . ?
C1 C2 1.367(2) . ?
C1 C10 1.492(2) . ?
C2 C3 1.463(2) . ?
C2 C11 1.4706(19) . ?
C3 O2 1.2359(18) . ?
C3 C4 1.476(2) . ?
C4 C9 1.389(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.406(2) . ?
C6 C16 1.501(2) . ?
C7 C8 1.377(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9300 . ?
C9 O1 1.3742(18) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.327(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.473(2) . ?
C12 H12 0.9300 . ?
C13 O4 1.2097(19) . ?
C13 O3 1.344(2) . ?
C14 O3 1.4543(18) . ?
C14 C15 1.497(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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






























































O1 C1 C2 123.49(13) . . ?
O1 C1 C10 109.77(12) . . ?
C2 C1 C10 126.74(13) . . ?
C1 C2 C3 119.76(12) . . ?
C1 C2 C11 118.00(13) . . ?
C3 C2 C11 122.23(12) . . ?
O2 C3 C2 123.74(13) . . ?
O2 C3 C4 120.76(13) . . ?
C2 C3 C4 115.49(12) . . ?
C9 C4 C5 118.17(13) . . ?
C9 C4 C3 119.67(13) . . ?
C5 C4 C3 122.17(13) . . ?
C6 C5 C4 121.73(13) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.10(14) . . ?
C5 C6 C16 120.98(14) . . ?
C7 C6 C16 120.92(14) . . ?
C8 C7 C6 121.44(14) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 118.97(14) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
O1 C9 C4 121.82(12) . . ?
O1 C9 C8 116.59(13) . . ?
C4 C9 C8 121.59(14) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C2 128.33(14) . . ?
C12 C11 H11 115.8 . . ?
C2 C11 H11 115.8 . . ?
C11 C12 C13 123.60(15) . . ?
C11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
O4 C13 O3 122.82(14) . . ?
O4 C13 C12 123.41(15) . . ?
O3 C13 C12 113.76(13) . . ?
O3 C14 C15 107.75(14) . . ?
O3 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O3 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O1 C9 119.76(11) . . ?
C13 O3 C14 116.32(12) . . ?



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 -0.2(2) . . . . ?
C10 C1 C2 C3 -179.21(13) . . . . ?
O1 C1 C2 C11 -179.77(12) . . . . ?
C10 C1 C2 C11 1.2(2) . . . . ?
C1 C2 C3 O2 179.52(13) . . . . ?
C11 C2 C3 O2 -0.9(2) . . . . ?
C1 C2 C3 C4 -0.46(19) . . . . ?
C11 C2 C3 C4 179.08(11) . . . . ?
O2 C3 C4 C9 -179.38(13) . . . . ?
C2 C3 C4 C9 0.60(19) . . . . ?
O2 C3 C4 C5 0.7(2) . . . . ?
C2 C3 C4 C5 -179.34(12) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 C6 -179.36(12) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C4 C5 C6 C16 179.67(13) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C16 C6 C7 C8 -179.98(14) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C5 C4 C9 O1 179.85(12) . . . . ?
C3 C4 C9 O1 -0.1(2) . . . . ?
C5 C4 C9 C8 -0.3(2) . . . . ?
C3 C4 C9 C8 179.78(13) . . . . ?
C7 C8 C9 O1 179.86(12) . . . . ?
C7 C8 C9 C4 0.0(2) . . . . ?
C1 C2 C11 C12 -176.52(14) . . . . ?
C3 C2 C11 C12 3.9(2) . . . . ?
C2 C11 C12 C13 -179.05(13) . . . . ?
C11 C12 C13 O4 -179.27(16) . . . . ?
C11 C12 C13 O3 0.9(2) . . . . ?
C2 C1 O1 C9 0.8(2) . . . . ?
C10 C1 O1 C9 179.91(11) . . . . ?
C4 C9 O1 C1 -0.6(2) . . . . ?
C8 C9 O1 C1 179.52(12) . . . . ?
O4 C13 O3 C14 -1.0(2) . . . . ?
C12 C13 O3 C14 178.79(13) . . . . ?
C15 C14 O3 C13 174.06(13) . . . . ?



_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        25.49

_diffrn_measured_fraction_theta_full 0.992

_refine_diff_density_max         0.197

_refine_diff_density_min         -0.209

_refine_diff_density_rms         0.047

_database_code_depnum_ccdc_archive 'CCDC 979580'
