# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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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# 
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#  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.
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data_03021m
#TrackingRef '16836_web_deposit_cif_file_0_ZouYong_1358088140.03021m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 O4'
_chemical_formula_sum            'C17 H18 O4'
_chemical_formula_weight         286.31

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.820(3)
_cell_length_b                   8.1262(18)
_cell_length_c                   18.945(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.565(10)
_cell_angle_gamma                90.00
_cell_volume                     1480.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2740
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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 AXS SMART 1000 CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7280
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.03
_reflns_number_total             3215
_reflns_number_gt                2220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT-PLUS (Bruker, 2003)'
_computing_data_reduction        SAINT-PLUS
_computing_structure_solution    'SHELXTL (Bruker, 2005)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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^)+(0.0506P)^2^+0.2401P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.89357(14) 0.66770(17) 0.82201(9) 0.0274(3) Uani 1 1 d . . .
C2 C 0.76300(14) 0.72742(18) 0.75765(9) 0.0285(3) Uani 1 1 d . . .
H2 H 0.7238 0.7043 0.6985 0.034 Uiso 1 1 calc R . .
C3 C 0.68921(14) 0.82119(17) 0.77947(9) 0.0274(3) Uani 1 1 d . . .
C4 C 0.74272(15) 0.85491(18) 0.86493(9) 0.0291(3) Uani 1 1 d . . .
H4 H 0.6911 0.9179 0.8793 0.035 Uiso 1 1 calc R . .
C5 C 0.87433(15) 0.79433(18) 0.92969(9) 0.0293(3) Uani 1 1 d . . .
C6 C 0.94992(15) 0.70225(18) 0.90924(10) 0.0292(3) Uani 1 1 d . . .
H6 H 1.0397 0.6625 0.9540 0.035 Uiso 1 1 calc R . .
C7 C 0.98140(14) 0.58020(19) 0.80208(9) 0.0300(3) Uani 1 1 d . . .
H7 H 1.0787 0.5936 0.8440 0.036 Uiso 1 1 calc R . .
C8 C 0.94604(15) 0.48549(19) 0.73474(10) 0.0315(4) Uani 1 1 d . . .
H8 H 1.0208 0.4554 0.7318 0.038 Uiso 1 1 calc R . .
C9 C 0.80913(14) 0.42004(18) 0.66412(9) 0.0282(3) Uani 1 1 d . . .
C10 C 0.77686(15) 0.40649(18) 0.58079(9) 0.0288(3) Uani 1 1 d . . .
H10 H 0.8406 0.4469 0.5698 0.035 Uiso 1 1 calc R . .
C11 C 0.65440(15) 0.33564(18) 0.51438(9) 0.0285(3) Uani 1 1 d . . .
C12 C 0.55896(14) 0.27671(18) 0.52934(9) 0.0287(3) Uani 1 1 d . . .
C13 C 0.59020(15) 0.28772(19) 0.61162(10) 0.0325(4) Uani 1 1 d . . .
H13 H 0.5265 0.2468 0.6226 0.039 Uiso 1 1 calc R . .
C14 C 0.71409(15) 0.35820(19) 0.67824(10) 0.0315(3) Uani 1 1 d . . .
H14 H 0.7346 0.3645 0.7347 0.038 Uiso 1 1 calc R . .
C15 C 1.05409(17) 0.7800(2) 1.08197(10) 0.0431(4) Uani 1 1 d . . .
H15A H 1.0558 0.6594 1.0826 0.065 Uiso 1 1 calc R . .
H15B H 1.0747 0.8206 1.1370 0.065 Uiso 1 1 calc R . .
H15C H 1.1241 0.8215 1.0743 0.065 Uiso 1 1 calc R . .
C16 C 0.48808(17) 0.9875(2) 0.72788(11) 0.0408(4) Uani 1 1 d . . .
H16A H 0.4691 0.9360 0.7667 0.061 Uiso 1 1 calc R . .
H16B H 0.4001 1.0179 0.6733 0.061 Uiso 1 1 calc R . .
H16C H 0.5448 1.0864 0.7555 0.061 Uiso 1 1 calc R . .
C17 C 0.33817(17) 0.1489(2) 0.46841(11) 0.0444(4) Uani 1 1 d . . .
H17A H 0.3771 0.0609 0.5119 0.067 Uiso 1 1 calc R . .
H17B H 0.2591 0.1060 0.4127 0.067 Uiso 1 1 calc R . .
H17C H 0.3069 0.2394 0.4873 0.067 Uiso 1 1 calc R . .
O1 O 0.56100(10) 0.87497(14) 0.71058(6) 0.0349(3) Uani 1 1 d . . .
O2 O 0.91995(11) 0.83582(15) 1.01224(7) 0.0401(3) Uani 1 1 d . . .
O3 O 0.62940(12) 0.32233(15) 0.43427(7) 0.0415(3) Uani 1 1 d . . .
H3 H 0.5535(19) 0.272(2) 0.4003(12) 0.050 Uiso 1 1 d . . .
O4 O 0.44214(11) 0.20745(14) 0.45865(7) 0.0380(3) 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
C1 0.0291(7) 0.0245(8) 0.0299(8) -0.0026(6) 0.0180(7) -0.0039(6)
C2 0.0305(8) 0.0287(8) 0.0260(7) -0.0024(6) 0.0162(7) -0.0016(6)
C3 0.0248(7) 0.0263(8) 0.0295(8) -0.0003(6) 0.0149(6) -0.0020(6)
C4 0.0305(8) 0.0285(8) 0.0337(8) -0.0030(6) 0.0217(7) -0.0011(6)
C5 0.0337(8) 0.0284(8) 0.0273(8) -0.0041(6) 0.0186(7) -0.0069(6)
C6 0.0261(7) 0.0278(8) 0.0279(8) 0.0005(6) 0.0125(6) -0.0018(6)
C7 0.0234(7) 0.0312(8) 0.0310(8) -0.0011(6) 0.0133(6) 0.0001(6)
C8 0.0271(7) 0.0341(9) 0.0343(8) -0.0017(7) 0.0184(7) 0.0026(6)
C9 0.0284(7) 0.0260(8) 0.0310(8) -0.0013(6) 0.0177(7) 0.0042(6)
C10 0.0297(7) 0.0285(8) 0.0334(8) 0.0005(6) 0.0214(7) 0.0005(6)
C11 0.0331(8) 0.0285(8) 0.0266(8) 0.0026(6) 0.0188(7) 0.0037(6)
C12 0.0265(7) 0.0280(8) 0.0285(8) -0.0015(6) 0.0142(7) -0.0005(6)
C13 0.0326(8) 0.0370(9) 0.0343(8) -0.0001(7) 0.0231(7) -0.0033(7)
C14 0.0350(8) 0.0350(9) 0.0275(8) -0.0013(7) 0.0200(7) 0.0000(7)
C15 0.0499(10) 0.0419(10) 0.0279(8) -0.0023(7) 0.0171(8) 0.0002(8)
C16 0.0402(9) 0.0450(10) 0.0403(10) 0.0059(8) 0.0252(8) 0.0155(8)
C17 0.0358(9) 0.0530(11) 0.0432(10) -0.0069(8) 0.0223(8) -0.0137(8)
O1 0.0299(5) 0.0397(7) 0.0317(6) -0.0034(5) 0.0159(5) 0.0072(5)
O2 0.0416(6) 0.0497(7) 0.0272(6) -0.0040(5) 0.0190(5) 0.0031(5)
O3 0.0404(6) 0.0581(8) 0.0280(6) -0.0072(5) 0.0211(5) -0.0138(6)
O4 0.0325(6) 0.0483(7) 0.0320(6) -0.0064(5) 0.0180(5) -0.0113(5)

_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 C2 1.384(2) . ?
C1 C6 1.405(2) . ?
C1 C7 1.477(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 O1 1.3749(17) . ?
C3 C4 1.380(2) . ?
C4 C5 1.395(2) . ?
C4 H4 0.9500 . ?
C5 O2 1.3673(17) . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.332(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.474(2) . ?
C8 H8 0.9500 . ?
C9 C14 1.391(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.375(2) . ?
C10 H10 0.9500 . ?
C11 O3 1.3714(17) . ?
C11 C12 1.398(2) . ?
C12 O4 1.3659(17) . ?
C12 C13 1.380(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O2 1.4242(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O1 1.4197(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O4 1.4267(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 H3 0.845(19) . ?

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
C2 C1 C6 119.28(13) . . ?
C2 C1 C7 122.21(13) . . ?
C6 C1 C7 118.30(13) . . ?
C1 C2 C3 120.09(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
O1 C3 C4 123.41(13) . . ?
O1 C3 C2 115.33(13) . . ?
C4 C3 C2 121.27(13) . . ?
C3 C4 C5 118.50(14) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
O2 C5 C6 124.39(13) . . ?
O2 C5 C4 114.52(13) . . ?
C6 C5 C4 121.08(14) . . ?
C5 C6 C1 119.77(13) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C1 130.34(13) . . ?
C8 C7 H7 114.8 . . ?
C1 C7 H7 114.8 . . ?
C7 C8 C9 130.16(14) . . ?
C7 C8 H8 114.9 . . ?
C9 C8 H8 114.9 . . ?
C14 C9 C10 117.95(13) . . ?
C14 C9 C8 122.60(13) . . ?
C10 C9 C8 119.24(13) . . ?
C11 C10 C9 121.16(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
O3 C11 C10 118.70(13) . . ?
O3 C11 C12 121.16(13) . . ?
C10 C11 C12 120.14(13) . . ?
O4 C12 C13 126.01(13) . . ?
O4 C12 C11 114.66(13) . . ?
C13 C12 C11 119.30(13) . . ?
C12 C13 C14 120.20(14) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 121.24(14) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 O1 C16 117.87(12) . . ?
C5 O2 C15 117.91(12) . . ?
C11 O3 H3 109.4(13) . . ?
C12 O4 C17 117.79(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
C6 C1 C2 C3 0.3(2) . . . . ?
C7 C1 C2 C3 -174.45(13) . . . . ?
C1 C2 C3 O1 179.68(13) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
O1 C3 C4 C5 -179.83(13) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 O2 179.01(12) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
O2 C5 C6 C1 -179.48(13) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C7 C1 C6 C5 175.31(14) . . . . ?
C2 C1 C7 C8 -30.8(3) . . . . ?
C6 C1 C7 C8 154.41(17) . . . . ?
C1 C7 C8 C9 -8.8(3) . . . . ?
C7 C8 C9 C14 -41.2(3) . . . . ?
C7 C8 C9 C10 144.17(17) . . . . ?
C14 C9 C10 C11 0.6(2) . . . . ?
C8 C9 C10 C11 175.45(14) . . . . ?
C9 C10 C11 O3 -178.61(13) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
O3 C11 C12 O4 -0.2(2) . . . . ?
C10 C11 C12 O4 -179.30(13) . . . . ?
O3 C11 C12 C13 177.91(14) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
O4 C12 C13 C14 178.63(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C9 0.4(2) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C8 C9 C14 C13 -175.71(14) . . . . ?
C4 C3 O1 C16 8.1(2) . . . . ?
C2 C3 O1 C16 -172.50(13) . . . . ?
C6 C5 O2 C15 -0.3(2) . . . . ?
C4 C5 O2 C15 -179.36(13) . . . . ?
C13 C12 O4 C17 3.8(2) . . . . ?
C11 C12 O4 C17 -178.22(14) . . . . ?

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
O3 H3 O1 0.845(19) 2.089(19) 2.8252(16) 145.4(17) 3_666

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.03
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040


_database_code_depnum_ccdc_archive 'CCDC 919496'