# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) 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_name        'Jie Hu'
_publ_contact_author_email       hu_j2006@lzu.cn
_publ_author_name                'Yong-Ming Liang'

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 805342'
#TrackingRef 'P21n.cif'

_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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   13.741(4)
_cell_length_b                   6.0599(16)
_cell_length_c                   17.805(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.656(3)
_cell_angle_gamma                90.00
_cell_volume                     1396.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    634
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_T_max  0.9790
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4248
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2448
_reflns_number_gt                1419
_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^)+(0.0663P)^2^+0.1444P] 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         2448
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.55674(19) 0.3677(4) 0.30225(16) 0.0451(7) Uani 1 1 d . . .
H1 H 0.5647 0.2560 0.2690 0.054 Uiso 1 1 calc R . .
C2 C 0.5836(2) 0.3294(5) 0.38310(17) 0.0524(8) Uani 1 1 d . . .
H2 H 0.6096 0.1923 0.4038 0.063 Uiso 1 1 calc R . .
C3 C 0.5722(2) 0.4919(6) 0.43302(18) 0.0575(8) Uani 1 1 d . . .
H3 H 0.5912 0.4662 0.4876 0.069 Uiso 1 1 calc R . .
C4 C 0.5329(2) 0.6918(6) 0.40215(18) 0.0643(9) Uani 1 1 d . . .
H4 H 0.5237 0.8016 0.4357 0.077 Uiso 1 1 calc R . .
C5 C 0.5065(2) 0.7319(5) 0.32130(18) 0.0553(8) Uani 1 1 d . . .
H5 H 0.4807 0.8694 0.3011 0.066 Uiso 1 1 calc R . .
C6 C 0.51810(17) 0.5704(4) 0.27018(15) 0.0380(6) Uani 1 1 d . . .
C7 C 0.49291(18) 0.6168(4) 0.18113(15) 0.0408(7) Uani 1 1 d . . .
H7 H 0.4672 0.7685 0.1705 0.049 Uiso 1 1 calc R . .
C8 C 0.41023(19) 0.4625(4) 0.12972(16) 0.0441(7) Uani 1 1 d . . .
C9 C 0.4329(2) 0.2971(5) 0.08879(16) 0.0460(7) Uani 1 1 d . . .
C10 C 0.60593(19) 0.4261(4) 0.11740(15) 0.0422(7) Uani 1 1 d . . .
C11 C 0.58916(18) 0.5970(4) 0.15869(14) 0.0384(6) Uani 1 1 d . . .
C12 C 0.3030(2) 0.4964(6) 0.12648(19) 0.0621(9) Uani 1 1 d . . .
C13 C 0.1904(2) 0.7400(7) 0.1629(3) 0.0988(14) Uani 1 1 d . . .
H13A H 0.1401 0.7112 0.1115 0.148 Uiso 1 1 calc R . .
H13B H 0.1887 0.8936 0.1756 0.148 Uiso 1 1 calc R . .
H13C H 0.1749 0.6527 0.2025 0.148 Uiso 1 1 calc R . .
C14 C 0.3651(2) 0.1210(5) 0.04000(18) 0.0649(9) Uani 1 1 d . . .
H14A H 0.3147 0.0793 0.0638 0.097 Uiso 1 1 calc R . .
H14B H 0.4063 -0.0050 0.0377 0.097 Uiso 1 1 calc R . .
H14C H 0.3306 0.1752 -0.0130 0.097 Uiso 1 1 calc R . .
C15 C 0.6994(2) 0.3682(5) 0.09688(17) 0.0551(8) Uani 1 1 d . . .
H15A H 0.7532 0.4735 0.1208 0.083 Uiso 1 1 calc R . .
H15B H 0.6826 0.3707 0.0400 0.083 Uiso 1 1 calc R . .
H15C H 0.7227 0.2233 0.1167 0.083 Uiso 1 1 calc R . .
C16 C 0.6647(2) 0.7733(5) 0.18425(16) 0.0455(7) Uani 1 1 d . . .
H16 H 0.7267 0.7585 0.1745 0.055 Uiso 1 1 calc R . .
O1 O 0.23097(18) 0.3779(5) 0.0961(2) 0.1278(13) Uani 1 1 d . . .
O2 O 0.29248(14) 0.6831(4) 0.16184(14) 0.0732(7) Uani 1 1 d . . .
O3 O 0.53159(14) 0.2669(3) 0.08675(11) 0.0513(5) Uani 1 1 d . . .
O4 O 0.65093(14) 0.9392(3) 0.21773(12) 0.0586(6) 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 0.0417(15) 0.0466(17) 0.0497(17) -0.0033(14) 0.0190(13) 0.0068(13)
C2 0.0476(17) 0.0616(19) 0.0504(18) 0.0121(16) 0.0197(14) 0.0089(14)
C3 0.0527(18) 0.081(2) 0.0433(17) -0.0021(18) 0.0215(14) -0.0036(16)
C4 0.080(2) 0.067(2) 0.054(2) -0.0115(18) 0.0337(18) 0.0026(18)
C5 0.066(2) 0.0439(17) 0.063(2) -0.0018(16) 0.0300(16) 0.0051(14)
C6 0.0302(13) 0.0416(15) 0.0435(15) -0.0034(13) 0.0140(12) -0.0013(11)
C7 0.0350(14) 0.0405(15) 0.0466(16) 0.0015(13) 0.0132(12) 0.0017(11)
C8 0.0340(15) 0.0514(17) 0.0437(16) 0.0064(14) 0.0088(12) -0.0014(12)
C9 0.0419(17) 0.0495(17) 0.0411(16) 0.0049(14) 0.0067(13) -0.0092(13)
C10 0.0403(15) 0.0463(17) 0.0387(15) 0.0023(14) 0.0116(12) -0.0040(12)
C11 0.0379(14) 0.0396(15) 0.0376(14) 0.0019(13) 0.0127(12) -0.0037(11)
C12 0.0407(18) 0.077(2) 0.065(2) -0.0018(18) 0.0125(16) -0.0099(17)
C13 0.046(2) 0.129(4) 0.128(3) 0.000(3) 0.039(2) 0.020(2)
C14 0.0565(19) 0.063(2) 0.064(2) -0.0084(17) 0.0057(16) -0.0139(15)
C15 0.0525(18) 0.0606(19) 0.0575(18) -0.0064(16) 0.0252(15) 0.0013(15)
C16 0.0424(16) 0.0483(17) 0.0464(16) 0.0022(14) 0.0156(13) 0.0006(13)
O1 0.0511(15) 0.149(3) 0.186(3) -0.075(2) 0.0442(17) -0.0364(16)
O2 0.0388(12) 0.0839(17) 0.0980(18) -0.0051(14) 0.0244(12) 0.0065(11)
O3 0.0460(11) 0.0480(12) 0.0566(12) -0.0098(10) 0.0130(9) -0.0042(9)
O4 0.0610(13) 0.0452(12) 0.0701(14) -0.0101(11) 0.0227(11) -0.0076(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 C2 1.380(4) . ?
C1 C6 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.531(4) . ?
C7 C11 1.509(3) . ?
C7 C8 1.518(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.336(4) . ?
C8 C12 1.469(4) . ?
C9 O3 1.382(3) . ?
C9 C14 1.489(4) . ?
C10 C11 1.334(3) . ?
C10 O3 1.377(3) . ?
C10 C15 1.491(4) . ?
C11 C16 1.451(4) . ?
C12 O1 1.195(4) . ?
C12 O2 1.326(4) . ?
C13 O2 1.451(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.215(3) . ?
C16 H16 0.9300 . ?

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 120.7(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 121.1(2) . . ?
C1 C6 C7 120.8(2) . . ?
C11 C7 C8 109.7(2) . . ?
C11 C7 C6 110.28(19) . . ?
C8 C7 C6 112.0(2) . . ?
C11 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
C9 C8 C12 119.9(3) . . ?
C9 C8 C7 121.8(2) . . ?
C12 C8 C7 118.3(3) . . ?
C8 C9 O3 121.6(2) . . ?
C8 C9 C14 129.9(3) . . ?
O3 C9 C14 108.5(2) . . ?
C11 C10 O3 121.3(2) . . ?
C11 C10 C15 129.8(2) . . ?
O3 C10 C15 108.9(2) . . ?
C10 C11 C16 120.4(2) . . ?
C10 C11 C7 122.4(2) . . ?
C16 C11 C7 117.2(2) . . ?
O1 C12 O2 121.4(3) . . ?
O1 C12 C8 126.9(4) . . ?
O2 C12 C8 111.7(3) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C11 123.3(3) . . ?
O4 C16 H16 118.3 . . ?
C11 C16 H16 118.3 . . ?
C12 O2 C13 118.0(3) . . ?
C10 O3 C9 120.0(2) . . ?

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 0.1(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 -177.7(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 177.2(2) . . . . ?
C5 C6 C7 C11 116.4(3) . . . . ?
C1 C6 C7 C11 -61.3(3) . . . . ?
C5 C6 C7 C8 -121.2(3) . . . . ?
C1 C6 C7 C8 61.1(3) . . . . ?
C11 C7 C8 C9 16.7(3) . . . . ?
C6 C7 C8 C9 -106.0(3) . . . . ?
C11 C7 C8 C12 -164.1(2) . . . . ?
C6 C7 C8 C12 73.1(3) . . . . ?
C12 C8 C9 O3 176.4(2) . . . . ?
C7 C8 C9 O3 -4.5(4) . . . . ?
C12 C8 C9 C14 -3.7(4) . . . . ?
C7 C8 C9 C14 175.5(3) . . . . ?
O3 C10 C11 C16 -174.4(2) . . . . ?
C15 C10 C11 C16 6.4(4) . . . . ?
O3 C10 C11 C7 5.8(4) . . . . ?
C15 C10 C11 C7 -173.4(2) . . . . ?
C8 C7 C11 C10 -17.5(3) . . . . ?
C6 C7 C11 C10 106.3(3) . . . . ?
C8 C7 C11 C16 162.7(2) . . . . ?
C6 C7 C11 C16 -73.5(3) . . . . ?
C9 C8 C12 O1 7.6(5) . . . . ?
C7 C8 C12 O1 -171.6(4) . . . . ?
C9 C8 C12 O2 -171.8(3) . . . . ?
C7 C8 C12 O2 9.0(4) . . . . ?
C10 C11 C16 O4 175.4(3) . . . . ?
C7 C11 C16 O4 -4.8(4) . . . . ?
O1 C12 O2 C13 0.2(5) . . . . ?
C8 C12 O2 C13 179.6(3) . . . . ?
C11 C10 O3 C9 8.9(4) . . . . ?
C15 C10 O3 C9 -171.7(2) . . . . ?
C8 C9 O3 C10 -9.6(4) . . . . ?
C14 C9 O3 C10 170.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050