# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_hyc15_0m
_database_code_depnum_ccdc_archive 'CCDC 1414938'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Penchinone D'
_chemical_name_common            'Penchinone D'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 O7'
_chemical_formula_sum            'C19 H20 O7'
_chemical_formula_weight         360.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   9.9508(3)
_cell_length_b                   19.0262(6)
_cell_length_c                   19.3662(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3666.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      69.36

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4872
_exptl_absorpt_correction_T_max  0.6740
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19511
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.57
_diffrn_reflns_theta_max         69.64
_reflns_number_total             3394
_reflns_number_gt                3385
_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 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)+(0.0446P)²+1.8427P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.00350(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     248
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_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
O3 O 0.70952(10) -0.09723(5) 0.49709(5) 0.0218(2) Uani 1 1 d . . .
O1S O 0.36971(9) 0.12442(5) 0.66946(5) 0.0179(2) Uani 1 1 d D . .
H1SB H 0.4485(10) 0.1349(9) 0.6624(8) 0.027 Uiso 1 1 d D . .
H1SA H 0.3686(17) 0.1054(8) 0.7077(6) 0.027 Uiso 1 1 d D . .
O4 O 0.78589(10) -0.01865(5) 0.38494(5) 0.0216(2) Uani 1 1 d . . .
H4 H 0.7404 -0.0558 0.3869 0.032 Uiso 1 1 calc R . .
O2 O 0.74596(10) -0.04320(5) 0.62708(5) 0.0222(2) Uani 1 1 d . . .
H2 H 0.7638 -0.0218 0.6639 0.033 Uiso 1 1 calc R . .
O7 O 0.83227(9) 0.06031(5) 0.70254(5) 0.0193(2) Uani 1 1 d . . .
O6' O 1.24087(9) 0.24763(5) 0.67987(5) 0.0230(2) Uani 1 1 d . . .
H6' H 1.2790 0.2085 0.6755 0.034 Uiso 1 1 calc R . .
O8 O 0.63127(9) 0.16294(5) 0.64250(5) 0.0212(2) Uani 1 1 d . . .
C10 C 0.56578(16) -0.09967(8) 0.50488(8) 0.0285(3) Uani 1 1 d . . .
H10A H 0.5412 -0.0830 0.5511 0.043 Uiso 1 1 calc R . .
H10B H 0.5345 -0.1481 0.4989 0.043 Uiso 1 1 calc R . .
H10C H 0.5237 -0.0695 0.4700 0.043 Uiso 1 1 calc R . .
C3 C 0.76282(13) -0.03106(7) 0.50684(7) 0.0171(3) Uani 1 1 d . . .
C2 C 0.78355(13) -0.00360(6) 0.57272(7) 0.0165(3) Uani 1 1 d . . .
C1 C 0.84066(12) 0.06392(6) 0.58071(7) 0.0159(3) Uani 1 1 d . . .
C7 C 0.85505(12) 0.09427(6) 0.64896(7) 0.0156(3) Uani 1 1 d . . .
C4' C 0.91031(13) 0.16766(6) 0.65556(6) 0.0149(3) Uani 1 1 d . . .
C3' C 0.82986(13) 0.22825(6) 0.65174(6) 0.0157(3) Uani 1 1 d . . .
C2' C 0.89161(13) 0.29388(6) 0.65816(7) 0.0165(3) Uani 1 1 d . . .
H2' H 0.8377 0.3350 0.6555 0.020 Uiso 1 1 calc R . .
C1' C 1.02926(13) 0.30103(7) 0.66828(6) 0.0164(3) Uani 1 1 d . . .
C7' C 1.09626(13) 0.37017(7) 0.67278(7) 0.0183(3) Uani 1 1 d . . .
H7' H 1.1742 0.3762 0.6451 0.022 Uiso 1 1 calc R . .
C8' C 1.05994(13) 0.42480(7) 0.71108(7) 0.0195(3) Uani 1 1 d . . .
H8' H 1.1115 0.4664 0.7050 0.023 Uiso 1 1 calc R . .
C9' C 0.94827(14) 0.42926(7) 0.76254(7) 0.0226(3) Uani 1 1 d . . .
H9'1 H 0.9003 0.3843 0.7641 0.034 Uiso 1 1 calc R . .
H9'2 H 0.8859 0.4667 0.7490 0.034 Uiso 1 1 calc R . .
H9'3 H 0.9854 0.4397 0.8083 0.034 Uiso 1 1 calc R . .
C4 C 0.80359(13) 0.00695(7) 0.44919(7) 0.0178(3) Uani 1 1 d . . .
C6 C 0.88145(13) 0.10055(7) 0.52122(7) 0.0184(3) Uani 1 1 d . . .
H6 H 0.9213 0.1457 0.5260 0.022 Uiso 1 1 calc R . .
C5 C 0.86501(14) 0.07264(7) 0.45662(7) 0.0205(3) Uani 1 1 d . . .
H5 H 0.8951 0.0977 0.4171 0.025 Uiso 1 1 calc R . .
C5' C 1.04746(13) 0.17359(7) 0.66549(7) 0.0175(3) Uani 1 1 d . . .
H5' H 1.1012 0.1324 0.6686 0.021 Uiso 1 1 calc R . .
C6' C 1.10745(13) 0.23968(7) 0.67105(6) 0.0174(3) Uani 1 1 d . . .
C8 C 0.68283(13) 0.22134(7) 0.64288(7) 0.0177(3) Uani 1 1 d . . .
C9 C 0.59896(14) 0.28649(7) 0.63551(9) 0.0289(3) Uani 1 1 d . . .
H9A H 0.6306 0.3138 0.5958 0.043 Uiso 1 1 calc R . .
H9B H 0.6067 0.3149 0.6775 0.043 Uiso 1 1 calc R . .
H9C H 0.5048 0.2733 0.6284 0.043 Uiso 1 1 calc R . .


_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
O3 C3 1.3791(15) . ?
O3 C10 1.4389(18) . ?
O1S H1SB 0.821(9) . ?
O1S H1SA 0.823(9) . ?
O4 C4 1.3477(16) . ?
O4 H4 0.8400 . ?
O2 C2 1.3475(16) . ?
O2 H2 0.8400 . ?
O7 C7 1.2432(16) . ?
O6' C6' 1.3471(16) . ?
O6' H6' 0.8400 . ?
O8 C8 1.2238(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 C4 1.3908(19) . ?
C3 C2 1.3939(18) . ?
C2 C1 1.4133(17) . ?
C1 C6 1.4065(18) . ?
C1 C7 1.4493(18) . ?
C7 C4' 1.5062(17) . ?
C4' C5' 1.3828(18) . ?
C4' C3' 1.4053(17) . ?
C3' C2' 1.3972(17) . ?
C3' C8 1.4789(18) . ?
C2' C1' 1.3904(18) . ?
C2' H2' 0.9500 . ?
C1' C6' 1.4039(18) . ?
C1' C7' 1.4773(17) . ?
C7' C8' 1.3272(19) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.4950(19) . ?
C8' H8' 0.9500 . ?
C9' H9'1 0.9800 . ?
C9' H9'2 0.9800 . ?
C9' H9'3 0.9800 . ?
C4 C5 1.3987(18) . ?
C6 C5 1.3689(19) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C5' C6' 1.3961(18) . ?
C5' H5' 0.9500 . ?
C8 C9 1.5011(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 O3 C10 113.42(10) . . ?
H1SB O1S H1SA 105.7(14) . . ?
C4 O4 H4 109.5 . . ?
C2 O2 H2 109.5 . . ?
C6' O6' H6' 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C3 C4 118.49(11) . . ?
O3 C3 C2 121.62(11) . . ?
C4 C3 C2 119.78(12) . . ?
O2 C2 C3 117.68(11) . . ?
O2 C2 C1 122.28(12) . . ?
C3 C2 C1 120.03(12) . . ?
C6 C1 C2 118.47(12) . . ?
C6 C1 C7 121.41(11) . . ?
C2 C1 C7 120.12(11) . . ?
O7 C7 C1 122.42(11) . . ?
O7 C7 C4' 118.52(11) . . ?
C1 C7 C4' 118.87(11) . . ?
C5' C4' C3' 120.17(12) . . ?
C5' C4' C7 116.59(11) . . ?
C3' C4' C7 123.23(11) . . ?
C2' C3' C4' 118.54(11) . . ?
C2' C3' C8 121.66(11) . . ?
C4' C3' C8 119.78(11) . . ?
C1' C2' C3' 122.23(12) . . ?
C1' C2' H2' 118.9 . . ?
C3' C2' H2' 118.9 . . ?
C2' C1' C6' 118.03(11) . . ?
C2' C1' C7' 122.69(12) . . ?
C6' C1' C7' 119.21(11) . . ?
C8' C7' C1' 127.40(12) . . ?
C8' C7' H7' 116.3 . . ?
C1' C7' H7' 116.3 . . ?
C7' C8' C9' 128.28(12) . . ?
C7' C8' H8' 115.9 . . ?
C9' C8' H8' 115.9 . . ?
C8' C9' H9'1 109.5 . . ?
C8' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C8' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
O4 C4 C3 121.00(12) . . ?
O4 C4 C5 118.37(12) . . ?
C3 C4 C5 120.63(12) . . ?
C5 C6 C1 121.46(12) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C6 C5 C4 119.54(12) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C4' C5' C6' 120.41(12) . . ?
C4' C5' H5' 119.8 . . ?
C6' C5' H5' 119.8 . . ?
O6' C6' C5' 122.16(12) . . ?
O6' C6' C1' 117.24(11) . . ?
C5' C6' C1' 120.59(12) . . ?
O8 C8 C3' 119.75(12) . . ?
O8 C8 C9 121.06(12) . . ?
C3' C8 C9 119.18(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C10 O3 C3 C4 -104.45(14) . . . . ?
C10 O3 C3 C2 79.30(15) . . . . ?
O3 C3 C2 O2 -1.92(18) . . . . ?
C4 C3 C2 O2 -178.11(12) . . . . ?
O3 C3 C2 C1 178.85(11) . . . . ?
C4 C3 C2 C1 2.65(19) . . . . ?
O2 C2 C1 C6 177.74(12) . . . . ?
C3 C2 C1 C6 -3.06(18) . . . . ?
O2 C2 C1 C7 -2.82(18) . . . . ?
C3 C2 C1 C7 176.38(12) . . . . ?
C6 C1 C7 O7 -172.67(12) . . . . ?
C2 C1 C7 O7 7.91(19) . . . . ?
C6 C1 C7 C4' 2.25(18) . . . . ?
C2 C1 C7 C4' -177.18(11) . . . . ?
O7 C7 C4' C5' 82.13(15) . . . . ?
C1 C7 C4' C5' -92.98(14) . . . . ?
O7 C7 C4' C3' -98.19(15) . . . . ?
C1 C7 C4' C3' 86.70(15) . . . . ?
C5' C4' C3' C2' 0.02(18) . . . . ?
C7 C4' C3' C2' -179.65(11) . . . . ?
C5' C4' C3' C8 -178.45(12) . . . . ?
C7 C4' C3' C8 1.88(18) . . . . ?
C4' C3' C2' C1' -0.13(19) . . . . ?
C8 C3' C2' C1' 178.31(12) . . . . ?
C3' C2' C1' C6' 0.90(19) . . . . ?
C3' C2' C1' C7' 177.87(12) . . . . ?
C2' C1' C7' C8' 48.7(2) . . . . ?
C6' C1' C7' C8' -134.32(15) . . . . ?
C1' C7' C8' C9' 4.3(2) . . . . ?
O3 C3 C4 O4 3.07(19) . . . . ?
C2 C3 C4 O4 179.38(12) . . . . ?
O3 C3 C4 C5 -176.47(11) . . . . ?
C2 C3 C4 C5 -0.15(19) . . . . ?
C2 C1 C6 C5 0.99(19) . . . . ?
C7 C1 C6 C5 -178.44(12) . . . . ?
C1 C6 C5 C4 1.5(2) . . . . ?
O4 C4 C5 C6 178.54(12) . . . . ?
C3 C4 C5 C6 -1.9(2) . . . . ?
C3' C4' C5' C6' -0.71(19) . . . . ?
C7 C4' C5' C6' 178.98(11) . . . . ?
C4' C5' C6' O6' -179.16(12) . . . . ?
C4' C5' C6' C1' 1.51(19) . . . . ?
C2' C1' C6' O6' 179.05(11) . . . . ?
C7' C1' C6' O6' 1.97(18) . . . . ?
C2' C1' C6' C5' -1.58(18) . . . . ?
C7' C1' C6' C5' -178.66(11) . . . . ?
C2' C3' C8 O8 -174.68(12) . . . . ?
C4' C3' C8 O8 3.74(18) . . . . ?
C2' C3' C8 C9 4.46(19) . . . . ?
C4' C3' C8 C9 -177.12(12) . . . . ?

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
O1S H1SB O8 0.821(9) 1.934(9) 2.7539(13) 177.2(17) .
O1S H1SA O7 0.823(9) 1.973(9) 2.7877(13) 170.2(16) 8_557
O4 H4 O1S 0.84 2.02 2.7490(13) 144.2 5_656
O4 H4 O3 0.84 2.30 2.7441(13) 113.7 .
O2 H2 O7 0.84 1.86 2.5984(13) 145.6 .
O6' H6' O1S 0.84 1.84 2.6794(13) 176.8 1_655

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        69.64
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051
_chemical_compound_source        'Penthorum Chinese'
