# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_fp54v9c
_database_code_depnum_ccdc_archive 'CCDC 1573301'
_audit_update_record             
;
2017-09-08 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Fomitopin-A
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         262.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration unk

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

_cell_length_a                   6.6564(2)
_cell_length_b                   10.3704(3)
_cell_length_c                   17.9622(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1239.92(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2350
_cell_measurement_theta_min      4.2597
_cell_measurement_theta_max      72.0511
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4664
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.92
_diffrn_reflns_theta_max         72.19
_reflns_number_total             2382
_reflns_number_gt                2235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_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)+(0.0601P)²+0.1655P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         2382
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_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
O1 O 0.6877(2) 0.78388(13) 0.69639(8) 0.0224(3) Uani 1 1 d . . .
O2 O 0.7083(2) 0.97800(14) 0.74410(8) 0.0276(3) Uani 1 1 d . . .
O3 O 1.0173(2) 0.35810(13) 0.55864(8) 0.0248(3) Uani 1 1 d . . .
H3A H 1.154(5) 0.357(3) 0.5657(16) 0.053(8) Uiso 1 1 d . . .
O4 O 0.4059(2) 0.36146(15) 0.61392(9) 0.0283(3) Uani 1 1 d . . .
H4A H 0.393(6) 0.380(3) 0.669(2) 0.079(11) Uiso 1 1 d . . .
C1 C 0.7728(3) 0.90403(18) 0.69813(11) 0.0205(4) Uani 1 1 d . . .
C2 C 0.9354(3) 0.92696(18) 0.64163(10) 0.0194(4) Uani 1 1 d . . .
C3 C 1.0704(3) 1.04424(18) 0.65252(11) 0.0230(4) Uani 1 1 d . . .
H3B H 1.0939 1.0612 0.7060 0.028 Uiso 1 1 calc R . .
H3C H 1.0108 1.1220 0.6294 0.028 Uiso 1 1 calc R . .
C4 C 1.2689(3) 1.00481(19) 0.61254(12) 0.0252(4) Uani 1 1 d . . .
H4B H 1.3860 1.0226 0.6450 0.030 Uiso 1 1 calc R . .
H4C H 1.2850 1.0541 0.5657 0.030 Uiso 1 1 calc R . .
C5 C 1.2538(3) 0.85765(18) 0.59568(11) 0.0223(4) Uani 1 1 d . . .
H5A H 1.2187 0.8422 0.5429 0.027 Uiso 1 1 calc R . .
H5B H 1.3818 0.8132 0.6071 0.027 Uiso 1 1 calc R . .
C6 C 1.0847(3) 0.81207(17) 0.64783(10) 0.0187(4) Uani 1 1 d . . .
C7 C 0.9728(3) 0.68977(17) 0.63101(10) 0.0186(4) Uani 1 1 d . . .
C8 C 0.7741(3) 0.68311(17) 0.65407(10) 0.0195(4) Uani 1 1 d . . .
C9 C 0.6543(3) 0.57694(19) 0.64150(10) 0.0205(4) Uani 1 1 d . . .
H9A H 0.5174 0.5779 0.6564 0.025 Uiso 1 1 calc R . .
C10 C 0.7345(3) 0.46815(18) 0.60693(10) 0.0201(4) Uani 1 1 d . . .
C11 C 0.9380(3) 0.46981(18) 0.58803(10) 0.0198(4) Uani 1 1 d . . .
C12 C 1.0528(3) 0.57990(18) 0.59789(10) 0.0195(4) Uani 1 1 d . . .
H12A H 1.1887 0.5804 0.5817 0.023 Uiso 1 1 calc R . .
C13 C 0.8305(3) 0.9360(2) 0.56461(11) 0.0246(4) Uani 1 1 d . . .
H13A H 0.7387 1.0098 0.5643 0.037 Uiso 1 1 calc R . .
H13B H 0.7546 0.8566 0.5553 0.037 Uiso 1 1 calc R . .
H13C H 0.9321 0.9471 0.5256 0.037 Uiso 1 1 calc R . .
C14 C 1.1700(3) 0.80135(19) 0.72772(11) 0.0223(4) Uani 1 1 d . . .
H14A H 1.2636 0.7286 0.7303 0.033 Uiso 1 1 calc R . .
H14B H 1.0595 0.7875 0.7629 0.033 Uiso 1 1 calc R . .
H14C H 1.2408 0.8812 0.7405 0.033 Uiso 1 1 calc R . .
C15 C 0.6107(3) 0.34722(19) 0.59432(12) 0.0232(4) Uani 1 1 d . . .
H15A H 0.6195 0.3228 0.5411 0.028 Uiso 1 1 calc R . .
H15B H 0.6692 0.2760 0.6239 0.028 Uiso 1 1 calc R . .

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
O1 0.0199(7) 0.0216(7) 0.0256(7) -0.0051(6) 0.0052(5) -0.0011(6)
O2 0.0262(7) 0.0254(7) 0.0313(7) -0.0083(6) 0.0067(6) -0.0003(6)
O3 0.0217(7) 0.0210(7) 0.0319(8) -0.0072(6) 0.0014(6) 0.0026(6)
O4 0.0208(7) 0.0314(8) 0.0326(8) -0.0061(6) 0.0025(6) -0.0048(6)
C1 0.0179(9) 0.0208(9) 0.0227(9) -0.0020(7) -0.0022(7) 0.0029(7)
C2 0.0203(9) 0.0182(9) 0.0198(9) -0.0004(7) 0.0000(7) 0.0028(8)
C3 0.0237(10) 0.0199(9) 0.0254(10) 0.0005(7) 0.0001(8) 0.0018(8)
C4 0.0237(10) 0.0239(10) 0.0281(10) 0.0013(8) 0.0010(8) -0.0030(8)
C5 0.0191(10) 0.0230(10) 0.0250(10) 0.0001(7) 0.0017(8) -0.0003(8)
C6 0.0170(9) 0.0201(9) 0.0190(9) 0.0003(7) 0.0016(8) 0.0018(8)
C7 0.0199(10) 0.0192(9) 0.0166(8) 0.0020(7) -0.0008(7) 0.0004(7)
C8 0.0212(10) 0.0200(9) 0.0172(8) -0.0011(7) 0.0005(7) 0.0032(8)
C9 0.0171(9) 0.0232(10) 0.0213(9) 0.0010(7) -0.0004(7) 0.0021(8)
C10 0.0222(9) 0.0202(9) 0.0180(8) 0.0011(7) -0.0021(7) -0.0005(8)
C11 0.0229(9) 0.0190(9) 0.0177(9) -0.0004(7) -0.0004(7) 0.0046(8)
C12 0.0164(9) 0.0236(9) 0.0183(9) 0.0016(7) 0.0009(7) 0.0038(8)
C13 0.0244(10) 0.0250(10) 0.0245(10) 0.0021(8) -0.0022(8) 0.0029(8)
C14 0.0214(9) 0.0200(9) 0.0254(10) 0.0005(8) -0.0020(8) 0.0004(8)
C15 0.0215(10) 0.0209(10) 0.0270(10) -0.0039(8) -0.0008(8) 0.0004(8)

_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
O1 C1 1.369(2) . ?
O1 C8 1.415(2) . ?
O2 C1 1.206(2) . ?
O3 C11 1.378(2) . ?
O3 H3A 0.92(3) . ?
O4 C15 1.416(2) . ?
O4 H4A 1.00(4) . ?
C1 C2 1.503(3) . ?
C2 C3 1.525(3) . ?
C2 C6 1.556(3) . ?
C2 C13 1.552(3) . ?
C3 C4 1.559(3) . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C4 C5 1.559(3) . ?
C4 H4B 0.9900 . ?
C4 H4C 0.9900 . ?
C5 C6 1.539(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(3) . ?
C6 C14 1.547(3) . ?
C7 C12 1.391(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.378(3) . ?
C9 C10 1.394(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(3) . ?
C10 C15 1.518(3) . ?
C11 C12 1.385(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C1 O1 C8 121.08(15) . . ?
C11 O3 H3A 109.7(18) . . ?
C15 O4 H4A 110(2) . . ?
O2 C1 O1 116.57(17) . . ?
O2 C1 C2 128.17(18) . . ?
O1 C1 C2 115.26(15) . . ?
C1 C2 C3 117.65(16) . . ?
C1 C2 C6 106.89(15) . . ?
C3 C2 C6 103.02(15) . . ?
C1 C2 C13 106.71(15) . . ?
C3 C2 C13 109.35(15) . . ?
C6 C2 C13 113.40(15) . . ?
C2 C3 C4 103.37(15) . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3C 111.1 . . ?
C4 C3 H3C 111.1 . . ?
H3B C3 H3C 109.1 . . ?
C3 C4 C5 106.95(16) . . ?
C3 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
C3 C4 H4C 110.3 . . ?
C5 C4 H4C 110.3 . . ?
H4B C4 H4C 108.6 . . ?
C6 C5 C4 103.27(16) . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 C5 120.00(16) . . ?
C7 C6 C2 108.40(15) . . ?
C5 C6 C2 100.87(14) . . ?
C7 C6 C14 107.94(15) . . ?
C5 C6 C14 108.54(15) . . ?
C2 C6 C14 110.85(15) . . ?
C12 C7 C8 116.86(17) . . ?
C12 C7 C6 126.00(17) . . ?
C8 C7 C6 117.06(16) . . ?
C9 C8 C7 122.84(17) . . ?
C9 C8 O1 116.30(17) . . ?
C7 C8 O1 120.74(16) . . ?
C8 C9 C10 119.87(17) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 118.02(17) . . ?
C11 C10 C15 120.04(17) . . ?
C9 C10 C15 121.82(17) . . ?
C12 C11 O3 122.02(17) . . ?
C12 C11 C10 120.95(17) . . ?
O3 C11 C10 117.03(17) . . ?
C11 C12 C7 121.21(17) . . ?
C11 C12 H12A 119.4 . . ?
C7 C12 H12A 119.4 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C10 113.56(16) . . ?
O4 C15 H15A 108.9 . . ?
C10 C15 H15A 108.9 . . ?
O4 C15 H15B 108.9 . . ?
C10 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        72.19
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        'Fomitopsis pinicola'
