# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ic16451
_database_code_depnum_ccdc_archive 'CCDC 1036447'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

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           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                   9.8399(6)
_cell_length_b                   5.2999(3)
_cell_length_c                   28.5110(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.305(6)
_cell_angle_gamma                90.00
_cell_volume                     1471.27(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1802
_cell_measurement_theta_min      4.5690
_cell_measurement_theta_max      74.5300

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4894
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         67.96
_reflns_number_total             2684
_reflns_number_gt                1946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.1000P)²+0.0000P] 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_number_reflns         2684
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.101
_refine_ls_shift/su_mean         0.010

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 0.49681(17) 0.9650(3) 0.07880(6) 0.0721(5) Uani 1 1 d . . .
H1A H 0.4687 0.9847 0.0505 0.108 Uiso 1 1 calc R . .
O2 O 0.63652(17) 0.8151(4) 0.01016(6) 0.0813(6) Uani 1 1 d . . .
O3 O 0.85785(14) 0.4964(3) 0.02290(5) 0.0626(4) Uani 1 1 d . . .
O4 O 0.89665(15) 0.2317(3) 0.11192(6) 0.0671(5) Uani 1 1 d . . .
C1 C 0.5684(2) 0.7338(4) 0.08544(7) 0.0496(5) Uani 1 1 d . . .
H1B H 0.5014 0.5959 0.0831 0.059 Uiso 1 1 calc R . .
C2 C 0.6595(2) 0.6976(4) 0.04746(7) 0.0536(5) Uani 1 1 d . . .
C3 C 0.7720(2) 0.5225(4) 0.05711(7) 0.0498(5) Uani 1 1 d . . .
C4 C 0.80007(19) 0.4099(4) 0.09937(7) 0.0487(5) Uani 1 1 d . . .
C5 C 0.7272(2) 0.4738(4) 0.14132(7) 0.0522(5) Uani 1 1 d . . .
H5A H 0.6576 0.3436 0.1434 0.063 Uiso 1 1 calc R . .
C6 C 0.65319(19) 0.7276(4) 0.13444(7) 0.0476(5) Uani 1 1 d . . .
H6A H 0.7243 0.8574 0.1348 0.057 Uiso 1 1 calc R . .
C7 C 0.5664(2) 0.7985(4) 0.17337(7) 0.0562(5) Uani 1 1 d . . .
H7A H 0.6271 0.8079 0.2033 0.067 Uiso 1 1 calc R . .
H7B H 0.5288 0.9658 0.1665 0.067 Uiso 1 1 calc R . .
C8 C 0.4496(2) 0.6229(4) 0.17947(7) 0.0516(5) Uani 1 1 d . . .
C9 C 0.4631(3) 0.4387(5) 0.21407(9) 0.0678(6) Uani 1 1 d . . .
H9A H 0.5459 0.4219 0.2342 0.081 Uiso 1 1 calc R . .
C10 C 0.3541(3) 0.2770(5) 0.21934(10) 0.0812(8) Uani 1 1 d . . .
H10A H 0.3647 0.1527 0.2426 0.097 Uiso 1 1 calc R . .
C11 C 0.2321(3) 0.3023(5) 0.19017(11) 0.0812(8) Uani 1 1 d . . .
H11A H 0.1597 0.1941 0.1934 0.097 Uiso 1 1 calc R . .
C12 C 0.2159(3) 0.4864(6) 0.15609(10) 0.0778(8) Uani 1 1 d . . .
H12A H 0.1323 0.5039 0.1365 0.093 Uiso 1 1 calc R . .
C13 C 0.3237(2) 0.6460(5) 0.15085(8) 0.0631(6) Uani 1 1 d . . .
H13A H 0.3116 0.7711 0.1277 0.076 Uiso 1 1 calc R . .
C14 C 0.7972(3) 0.3882(6) -0.02116(9) 0.0840(8) Uani 1 1 d . . .
H14A H 0.8646 0.3790 -0.0423 0.126 Uiso 1 1 calc R . .
H14B H 0.7218 0.4915 -0.0350 0.126 Uiso 1 1 calc R . .
H14C H 0.7644 0.2217 -0.0157 0.126 Uiso 1 1 calc R . .
C15 C 0.9613(3) 0.0939(5) 0.07765(10) 0.0787(7) Uani 1 1 d . . .
H15A H 1.0258 -0.0242 0.0937 0.118 Uiso 1 1 calc R . .
H15B H 1.0085 0.2095 0.0597 0.118 Uiso 1 1 calc R . .
H15C H 0.8927 0.0046 0.0567 0.118 Uiso 1 1 calc R . .
C16 C 0.8277(3) 0.4674(7) 0.18757(9) 0.0941(10) Uani 1 1 d . . .
H16A H 0.8720 0.3056 0.1909 0.141 Uiso 1 1 calc R . .
H16B H 0.7786 0.4956 0.2138 0.141 Uiso 1 1 calc R . .
H16C H 0.8957 0.5969 0.1869 0.141 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 0.0847(11) 0.0704(11) 0.0623(10) 0.0140(8) 0.0144(8) 0.0262(8)
O2 0.0863(11) 0.1022(14) 0.0581(10) 0.0286(10) 0.0191(8) 0.0212(10)
O3 0.0565(8) 0.0753(10) 0.0594(9) -0.0062(8) 0.0202(7) -0.0101(7)
O4 0.0618(9) 0.0648(10) 0.0751(11) 0.0078(8) 0.0110(7) 0.0137(7)
C1 0.0513(10) 0.0482(11) 0.0500(11) 0.0020(9) 0.0100(8) 0.0003(8)
C2 0.0563(11) 0.0576(12) 0.0476(11) 0.0054(10) 0.0095(9) -0.0030(10)
C3 0.0496(10) 0.0511(11) 0.0499(11) -0.0027(9) 0.0116(9) -0.0083(9)
C4 0.0428(9) 0.0439(10) 0.0592(12) 0.0000(9) 0.0069(8) -0.0051(8)
C5 0.0531(11) 0.0547(12) 0.0487(11) 0.0059(9) 0.0072(9) -0.0007(9)
C6 0.0514(10) 0.0433(10) 0.0484(11) -0.0021(8) 0.0080(8) -0.0070(8)
C7 0.0699(13) 0.0509(11) 0.0485(11) -0.0084(9) 0.0113(10) -0.0055(10)
C8 0.0662(12) 0.0494(11) 0.0431(10) -0.0077(9) 0.0208(9) -0.0003(9)
C9 0.0793(15) 0.0676(15) 0.0611(14) 0.0062(11) 0.0258(12) 0.0091(12)
C10 0.109(2) 0.0623(15) 0.0844(18) 0.0140(13) 0.0543(17) 0.0072(15)
C11 0.0860(18) 0.0736(17) 0.095(2) -0.0141(15) 0.0504(16) -0.0174(14)
C12 0.0682(15) 0.096(2) 0.0728(16) -0.0113(15) 0.0236(13) -0.0159(14)
C13 0.0680(13) 0.0693(15) 0.0550(12) 0.0024(11) 0.0186(10) -0.0034(11)
C14 0.0853(17) 0.110(2) 0.0593(15) -0.0187(15) 0.0205(13) -0.0096(16)
C15 0.0738(15) 0.0637(15) 0.101(2) -0.0105(14) 0.0215(14) 0.0127(12)
C16 0.0856(18) 0.140(3) 0.0534(14) 0.0090(16) -0.0015(13) 0.0337(18)

_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 1.413(2) . ?
O2 C2 1.225(3) . ?
O3 C3 1.386(2) . ?
O3 C14 1.431(3) . ?
O4 C4 1.351(2) . ?
O4 C15 1.439(3) . ?
C1 C2 1.514(3) . ?
C1 C6 1.520(3) . ?
C2 C3 1.440(3) . ?
C3 C4 1.337(3) . ?
C4 C5 1.519(3) . ?
C5 C6 1.528(3) . ?
C5 C16 1.530(3) . ?
C6 C7 1.541(3) . ?
C7 C8 1.508(3) . ?
C8 C13 1.387(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.398(4) . ?
C10 C11 1.365(4) . ?
C11 C12 1.370(4) . ?
C12 C13 1.381(3) . ?

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 C14 116.00(16) . . ?
C4 O4 C15 122.54(19) . . ?
O1 C1 C2 110.45(16) . . ?
O1 C1 C6 109.80(17) . . ?
C2 C1 C6 110.59(15) . . ?
O2 C2 C3 122.26(19) . . ?
O2 C2 C1 120.15(19) . . ?
C3 C2 C1 117.58(17) . . ?
C4 C3 O3 121.45(18) . . ?
C4 C3 C2 120.85(18) . . ?
O3 C3 C2 117.36(18) . . ?
C3 C4 O4 126.62(19) . . ?
C3 C4 C5 123.39(18) . . ?
O4 C4 C5 109.97(17) . . ?
C4 C5 C6 111.44(16) . . ?
C4 C5 C16 110.68(17) . . ?
C6 C5 C16 111.5(2) . . ?
C1 C6 C7 111.66(15) . . ?
C1 C6 C5 108.94(16) . . ?
C7 C6 C5 115.15(17) . . ?
C8 C7 C6 116.32(16) . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C7 120.57(19) . . ?
C9 C8 C7 121.5(2) . . ?
C8 C9 C10 121.0(3) . . ?
C11 C10 C9 119.7(2) . . ?
C10 C11 C12 120.3(2) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C8 121.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.96
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_ic16470
_database_code_depnum_ccdc_archive 'CCDC 1036448'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   11.0565(7)
_cell_length_b                   25.7976(11)
_cell_length_c                   5.1911(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.206(7)
_cell_angle_gamma                90.00
_cell_volume                     1441.51(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1705
_cell_measurement_theta_min      4.0890
_cell_measurement_theta_max      73.0560

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6579
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         67.96
_reflns_number_total             2512
_reflns_number_gt                1697
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0972P)²+0.2656P] 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_number_reflns         2512
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1641
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.1345(2) 0.27710(7) 0.4621(4) 0.0688(6) Uani 1 1 d . . .
H1A H 0.1333 0.2741 0.6187 0.103 Uiso 1 1 calc R . .
O2 O 0.31148(19) 0.31016(8) 0.2538(5) 0.0757(6) Uani 1 1 d . . .
O3 O 0.42254(17) 0.41002(8) 0.4286(4) 0.0693(6) Uani 1 1 d . . .
O4 O 0.2724(2) 0.47630(8) 0.6131(5) 0.0902(8) Uani 1 1 d . . .
C1 C 0.1316(2) 0.33044(9) 0.3940(5) 0.0502(6) Uani 1 1 d . . .
H1B H 0.0725 0.3350 0.2235 0.060 Uiso 1 1 calc R . .
C2 C 0.2583(2) 0.34815(9) 0.3643(5) 0.0521(6) Uani 1 1 d . . .
C3 C 0.3031(2) 0.39575(9) 0.4378(5) 0.0530(6) Uani 1 1 d . . .
C4 C 0.2298(3) 0.43369(10) 0.5455(5) 0.0578(7) Uani 1 1 d . . .
C5 C 0.0987(3) 0.41928(9) 0.5652(5) 0.0528(6) Uani 1 1 d . . .
H5A H 0.0428 0.4288 0.3967 0.063 Uiso 1 1 calc R . .
C6 C 0.0842(3) 0.36075(9) 0.6024(5) 0.0520(6) Uani 1 1 d . . .
H6A H 0.1380 0.3517 0.7742 0.062 Uiso 1 1 calc R . .
C7 C -0.0478(3) 0.34438(10) 0.6119(5) 0.0599(7) Uani 1 1 d . . .
H7A H -0.0459 0.3082 0.6627 0.072 Uiso 1 1 calc R . .
H7B H -0.0728 0.3642 0.7498 0.072 Uiso 1 1 calc R . .
C8 C -0.1458(3) 0.35106(9) 0.3588(6) 0.0551(6) Uani 1 1 d . . .
C9 C -0.2008(3) 0.39864(11) 0.2845(6) 0.0674(8) Uani 1 1 d . . .
H9A H -0.1776 0.4271 0.3944 0.081 Uiso 1 1 calc R . .
C10 C -0.2884(3) 0.40475(13) 0.0535(7) 0.0788(9) Uani 1 1 d . . .
H10A H -0.3225 0.4373 0.0074 0.095 Uiso 1 1 calc R . .
C11 C -0.3265(3) 0.36340(15) -0.1107(7) 0.0800(10) Uani 1 1 d . . .
H11A H -0.3860 0.3677 -0.2678 0.096 Uiso 1 1 calc R . .
C12 C -0.2754(3) 0.31529(14) -0.0390(7) 0.0802(9) Uani 1 1 d . . .
H12A H -0.3016 0.2867 -0.1463 0.096 Uiso 1 1 calc R . .
C13 C -0.1854(3) 0.30958(11) 0.1916(6) 0.0644(7) Uani 1 1 d . . .
H13A H -0.1505 0.2771 0.2359 0.077 Uiso 1 1 calc R . .
C14 C 0.4181(3) 0.31726(14) 0.1487(8) 0.0921(11) Uani 1 1 d . . .
H14A H 0.4404 0.2849 0.0809 0.138 Uiso 1 1 calc R . .
H14B H 0.4859 0.3294 0.2857 0.138 Uiso 1 1 calc R . .
H14C H 0.4002 0.3423 0.0084 0.138 Uiso 1 1 calc R . .
C15 C 0.4327(4) 0.44973(14) 0.2409(8) 0.0950(12) Uani 1 1 d . . .
H15A H 0.5188 0.4569 0.2504 0.142 Uiso 1 1 calc R . .
H15B H 0.3923 0.4807 0.2809 0.142 Uiso 1 1 calc R . .
H15C H 0.3938 0.4382 0.0658 0.142 Uiso 1 1 calc R . .
C16 C 0.0611(3) 0.45176(11) 0.7811(6) 0.0703(8) Uani 1 1 d . . .
H16A H 0.0709 0.4879 0.7467 0.105 Uiso 1 1 calc R . .
H16B H 0.1129 0.4429 0.9502 0.105 Uiso 1 1 calc R . .
H16C H -0.0242 0.4449 0.7819 0.105 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 0.0882(14) 0.0440(10) 0.0825(12) 0.0093(9) 0.0366(11) 0.0022(9)
O2 0.0688(13) 0.0575(11) 0.1115(16) -0.0169(11) 0.0430(12) -0.0014(9)
O3 0.0499(11) 0.0645(12) 0.0910(14) 0.0017(10) 0.0113(10) -0.0037(9)
O4 0.0862(16) 0.0560(12) 0.133(2) -0.0260(13) 0.0338(15) -0.0157(11)
C1 0.0570(15) 0.0408(12) 0.0538(13) 0.0038(10) 0.0148(12) -0.0001(10)
C2 0.0530(15) 0.0459(13) 0.0579(14) 0.0016(11) 0.0137(12) 0.0071(11)
C3 0.0485(14) 0.0498(14) 0.0581(14) 0.0060(11) 0.0070(12) 0.0007(11)
C4 0.0654(17) 0.0466(14) 0.0604(15) 0.0008(12) 0.0119(13) -0.0001(12)
C5 0.0619(16) 0.0451(13) 0.0522(13) 0.0015(10) 0.0149(12) 0.0059(11)
C6 0.0615(16) 0.0489(14) 0.0479(13) 0.0078(11) 0.0171(12) 0.0076(11)
C7 0.0661(17) 0.0542(15) 0.0660(16) 0.0108(12) 0.0290(14) 0.0052(12)
C8 0.0548(15) 0.0481(14) 0.0697(16) 0.0061(12) 0.0291(13) 0.0018(11)
C9 0.0631(18) 0.0541(16) 0.085(2) 0.0025(14) 0.0169(16) 0.0046(13)
C10 0.067(2) 0.070(2) 0.100(2) 0.0187(19) 0.0190(18) 0.0134(16)
C11 0.0535(17) 0.107(3) 0.079(2) 0.0050(19) 0.0149(16) 0.0097(17)
C12 0.0639(19) 0.087(2) 0.091(2) -0.0177(18) 0.0202(18) -0.0025(17)
C13 0.0594(17) 0.0528(15) 0.0856(19) -0.0002(14) 0.0261(16) 0.0024(12)
C14 0.077(2) 0.088(2) 0.127(3) -0.027(2) 0.056(2) -0.0020(18)
C15 0.083(2) 0.079(2) 0.129(3) 0.017(2) 0.038(2) -0.0148(18)
C16 0.085(2) 0.0594(16) 0.0683(17) -0.0100(14) 0.0216(16) 0.0056(14)

_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 1.419(3) . ?
O2 C2 1.338(3) . ?
O2 C14 1.420(4) . ?
O3 C3 1.382(3) . ?
O3 C15 1.436(4) . ?
O4 C4 1.215(3) . ?
C1 C2 1.514(4) . ?
C1 C6 1.522(3) . ?
C2 C3 1.346(3) . ?
C3 C4 1.461(4) . ?
C4 C5 1.522(4) . ?
C5 C16 1.531(4) . ?
C5 C6 1.535(3) . ?
C6 C7 1.531(4) . ?
C7 C8 1.510(4) . ?
C8 C9 1.385(4) . ?
C8 C13 1.385(4) . ?
C9 C10 1.367(4) . ?
C10 C11 1.370(5) . ?
C11 C12 1.379(5) . ?
C12 C13 1.378(4) . ?

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 O2 C14 123.7(2) . . ?
C3 O3 C15 115.9(2) . . ?
O1 C1 C2 110.4(2) . . ?
O1 C1 C6 108.2(2) . . ?
C2 C1 C6 113.2(2) . . ?
O2 C2 C3 128.4(3) . . ?
O2 C2 C1 109.3(2) . . ?
C3 C2 C1 122.4(2) . . ?
C2 C3 O3 121.7(2) . . ?
C2 C3 C4 121.3(2) . . ?
O3 C3 C4 116.9(2) . . ?
O4 C4 C3 120.3(3) . . ?
O4 C4 C5 120.9(2) . . ?
C3 C4 C5 118.8(2) . . ?
C4 C5 C16 109.7(2) . . ?
C4 C5 C6 112.1(2) . . ?
C16 C5 C6 113.1(2) . . ?
C1 C6 C7 111.5(2) . . ?
C1 C6 C5 110.7(2) . . ?
C7 C6 C5 113.7(2) . . ?
C8 C7 C6 116.1(2) . . ?
C9 C8 C13 117.0(3) . . ?
C9 C8 C7 121.7(3) . . ?
C13 C8 C7 121.3(2) . . ?
C10 C9 C8 121.6(3) . . ?
C9 C10 C11 120.8(3) . . ?
C10 C11 C12 118.9(3) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C8 121.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        67.96
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_ic16471
_database_code_depnum_ccdc_archive 'CCDC 1036449'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8502(3)
_cell_length_b                   10.6878(8)
_cell_length_c                   11.8197(8)
_cell_angle_alpha                88.055(6)
_cell_angle_beta                 85.254(5)
_cell_angle_gamma                81.792(5)
_cell_volume                     728.77(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1777
_cell_measurement_theta_min      4.1810
_cell_measurement_theta_max      74.0940

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4363
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         67.98
_reflns_number_total             2644
_reflns_number_gt                2109
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0959P)²+0.2171P] 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_number_reflns         2644
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1770
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

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 -0.0076(3) 0.40180(16) 1.17143(14) 0.0571(5) Uani 1 1 d . . .
H1A H -0.1076 0.4443 1.1363 0.086 Uiso 1 1 calc R . .
O2 O 0.2954(3) 0.43393(17) 0.95649(13) 0.0589(5) Uani 1 1 d . . .
O3 O 0.6539(3) 0.24708(18) 0.96949(14) 0.0649(5) Uani 1 1 d . . .
O4 O 0.7329(3) 0.14822(16) 1.19889(14) 0.0604(5) Uani 1 1 d . . .
C1 C 0.2017(3) 0.4557(2) 1.15541(17) 0.0423(5) Uani 1 1 d . . .
H1B H 0.1632 0.5466 1.1401 0.051 Uiso 1 1 calc R . .
C2 C 0.3413(4) 0.3958(2) 1.05187(18) 0.0444(5) Uani 1 1 d . . .
C3 C 0.5235(4) 0.2909(2) 1.06764(18) 0.0480(5) Uani 1 1 d . . .
C4 C 0.5725(4) 0.2457(2) 1.17200(18) 0.0453(5) Uani 1 1 d . . .
C5 C 0.4463(4) 0.2992(2) 1.28003(17) 0.0443(5) Uani 1 1 d . . .
H5A H 0.5639 0.3013 1.3341 0.053 Uiso 1 1 calc R . .
C6 C 0.3344(4) 0.43676(19) 1.26143(17) 0.0424(5) Uani 1 1 d . . .
H6A H 0.4618 0.4873 1.2494 0.051 Uiso 1 1 calc R . .
C7 C 0.1867(4) 0.4879(2) 1.36841(19) 0.0535(6) Uani 1 1 d . . .
H7A H 0.0434 0.4514 1.3746 0.064 Uiso 1 1 calc R . .
H7B H 0.2694 0.4599 1.4346 0.064 Uiso 1 1 calc R . .
C8 C 0.1286(4) 0.6298(2) 1.36970(17) 0.0482(5) Uani 1 1 d . . .
C9 C 0.2734(4) 0.7032(3) 1.4164(2) 0.0616(7) Uani 1 1 d . . .
H9A H 0.4094 0.6642 1.4453 0.074 Uiso 1 1 calc R . .
C10 C 0.2188(5) 0.8334(3) 1.4205(2) 0.0674(7) Uani 1 1 d . . .
H10A H 0.3177 0.8808 1.4524 0.081 Uiso 1 1 calc R . .
C11 C 0.0211(5) 0.8927(2) 1.3781(2) 0.0641(7) Uani 1 1 d . . .
H11A H -0.0155 0.9802 1.3812 0.077 Uiso 1 1 calc R . .
C12 C -0.1236(5) 0.8224(3) 1.3308(2) 0.0645(7) Uani 1 1 d . . .
H12A H -0.2579 0.8627 1.3010 0.077 Uiso 1 1 calc R . .
C13 C -0.0716(4) 0.6918(2) 1.3268(2) 0.0570(6) Uani 1 1 d . . .
H13A H -0.1720 0.6453 1.2951 0.068 Uiso 1 1 calc R . .
C14 C 0.5374(7) 0.1809(3) 0.8972(3) 0.0926(11) Uani 1 1 d . . .
H14A H 0.6392 0.1546 0.8318 0.139 Uiso 1 1 calc R . .
H14B H 0.4036 0.2350 0.8734 0.139 Uiso 1 1 calc R . .
H14C H 0.4898 0.1079 0.9369 0.139 Uiso 1 1 calc R . .
C15 C 0.8997(5) 0.0884(3) 1.1163(2) 0.0722(8) Uani 1 1 d . . .
H15A H 0.9972 0.0212 1.1520 0.108 Uiso 1 1 calc R . .
H15B H 0.9926 0.1491 1.0827 0.108 Uiso 1 1 calc R . .
H15C H 0.8220 0.0545 1.0584 0.108 Uiso 1 1 calc R . .
C16 C 0.2804(5) 0.2095(2) 1.3318(2) 0.0624(7) Uani 1 1 d . . .
H16A H 0.3644 0.1263 1.3409 0.094 Uiso 1 1 calc R . .
H16B H 0.1592 0.2064 1.2824 0.094 Uiso 1 1 calc R . .
H16C H 0.2140 0.2397 1.4045 0.094 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 0.0378(8) 0.0712(11) 0.0616(10) 0.0177(8) -0.0067(7) -0.0083(7)
O2 0.0579(10) 0.0742(11) 0.0407(9) 0.0072(7) -0.0102(7) 0.0057(8)
O3 0.0630(11) 0.0799(12) 0.0467(9) -0.0048(8) 0.0004(8) 0.0056(9)
O4 0.0649(10) 0.0602(10) 0.0478(9) 0.0016(7) -0.0042(7) 0.0190(8)
C1 0.0391(10) 0.0441(11) 0.0419(11) 0.0053(8) -0.0005(8) -0.0024(8)
C2 0.0413(11) 0.0532(12) 0.0384(11) 0.0045(9) -0.0062(8) -0.0056(9)
C3 0.0476(12) 0.0568(13) 0.0368(11) -0.0058(9) -0.0022(9) 0.0023(9)
C4 0.0453(11) 0.0448(11) 0.0439(11) -0.0004(9) -0.0057(9) 0.0012(9)
C5 0.0453(11) 0.0503(12) 0.0351(10) 0.0027(8) -0.0044(8) 0.0007(9)
C6 0.0425(11) 0.0455(11) 0.0376(10) 0.0005(8) 0.0002(8) -0.0030(8)
C7 0.0592(13) 0.0569(13) 0.0398(11) 0.0007(9) 0.0057(10) 0.0017(10)
C8 0.0508(12) 0.0565(13) 0.0340(10) -0.0046(9) 0.0040(8) 0.0006(9)
C9 0.0544(14) 0.0801(17) 0.0486(13) -0.0121(12) -0.0061(10) -0.0006(12)
C10 0.0765(18) 0.0703(17) 0.0583(15) -0.0208(12) -0.0019(13) -0.0177(13)
C11 0.0831(19) 0.0545(14) 0.0512(13) -0.0105(11) 0.0069(12) -0.0025(12)
C12 0.0655(16) 0.0629(15) 0.0602(15) -0.0067(12) -0.0058(12) 0.0096(12)
C13 0.0533(13) 0.0593(14) 0.0579(14) -0.0091(11) -0.0065(10) -0.0035(10)
C14 0.117(3) 0.096(2) 0.0596(17) -0.0296(16) -0.0206(17) 0.016(2)
C15 0.0731(17) 0.0709(17) 0.0617(16) -0.0057(13) -0.0019(13) 0.0260(14)
C16 0.0696(16) 0.0541(14) 0.0587(14) 0.0140(11) 0.0071(12) -0.0028(11)

_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 1.422(3) . ?
O2 C2 1.223(3) . ?
O3 C3 1.391(3) . ?
O3 C14 1.403(4) . ?
O4 C4 1.347(3) . ?
O4 C15 1.422(3) . ?
C1 C6 1.521(3) . ?
C1 C2 1.521(3) . ?
C2 C3 1.451(3) . ?
C3 C4 1.347(3) . ?
C4 C5 1.508(3) . ?
C5 C16 1.538(3) . ?
C5 C6 1.538(3) . ?
C6 C7 1.541(3) . ?
C7 C8 1.507(3) . ?
C8 C13 1.386(3) . ?
C8 C9 1.391(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.362(4) . ?
C11 C12 1.372(4) . ?
C12 C13 1.388(4) . ?

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 C14 115.0(2) . . ?
C4 O4 C15 122.13(19) . . ?
O1 C1 C6 110.74(17) . . ?
O1 C1 C2 107.82(18) . . ?
C6 C1 C2 112.29(16) . . ?
O2 C2 C3 120.7(2) . . ?
O2 C2 C1 120.01(19) . . ?
C3 C2 C1 119.27(18) . . ?
C4 C3 O3 122.5(2) . . ?
C4 C3 C2 121.46(19) . . ?
O3 C3 C2 115.82(18) . . ?
O4 C4 C3 127.7(2) . . ?
O4 C4 C5 108.81(17) . . ?
C3 C4 C5 123.44(19) . . ?
C4 C5 C16 110.23(19) . . ?
C4 C5 C6 111.19(16) . . ?
C16 C5 C6 115.04(18) . . ?
C1 C6 C5 113.09(17) . . ?
C1 C6 C7 112.43(17) . . ?
C5 C6 C7 111.42(17) . . ?
C8 C7 C6 114.35(18) . . ?
C13 C8 C9 117.6(2) . . ?
C13 C8 C7 121.6(2) . . ?
C9 C8 C7 120.7(2) . . ?
C10 C9 C8 121.2(2) . . ?
C11 C10 C9 120.4(3) . . ?
C10 C11 C12 119.5(3) . . ?
C11 C12 C13 120.7(3) . . ?
C8 C13 C12 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        67.98
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_ic16473
_database_code_depnum_ccdc_archive 'CCDC 1036450'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9852(5)
_cell_length_b                   8.4612(7)
_cell_length_c                   13.1167(9)
_cell_angle_alpha                73.977(7)
_cell_angle_beta                 81.811(6)
_cell_angle_gamma                78.873(7)
_cell_volume                     727.84(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1817
_cell_measurement_theta_min      5.5140
_cell_measurement_theta_max      74.3710

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4603
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -7
_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       15
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         68.00
_reflns_number_total             2643
_reflns_number_gt                2010
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0698P)²+0.1055P] 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_number_reflns         2643
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 -0.25997(17) 0.14551(19) 0.90531(10) 0.0521(4) Uani 1 1 d . . .
H1A H -0.3515 0.1035 0.8975 0.078 Uiso 1 1 calc R . .
O2 O -0.0696(2) 0.44969(17) 0.82660(12) 0.0564(4) Uani 1 1 d . . .
O3 O 0.30687(18) 0.32728(17) 0.85836(10) 0.0479(4) Uani 1 1 d . . .
O4 O 0.44387(18) 0.00612(18) 0.85295(12) 0.0523(4) Uani 1 1 d . . .
C1 C -0.1417(2) 0.1847(2) 0.80684(14) 0.0395(4) Uani 1 1 d . . .
H1B H -0.2253 0.2515 0.7512 0.047 Uiso 1 1 calc R . .
C2 C -0.0036(3) 0.2900(2) 0.82372(14) 0.0391(4) Uani 1 1 d . . .
C3 C 0.1837(2) 0.2282(2) 0.84304(14) 0.0389(4) Uani 1 1 d . . .
C4 C 0.2681(2) 0.0548(2) 0.84703(13) 0.0393(4) Uani 1 1 d . . .
C5 C 0.1275(3) -0.0615(2) 0.84802(15) 0.0420(4) Uani 1 1 d . . .
H5A H 0.0621 -0.0873 0.9205 0.050 Uiso 1 1 calc R . .
C6 C -0.0347(2) 0.0282(2) 0.77450(14) 0.0404(4) Uani 1 1 d . . .
H6A H -0.1303 -0.0472 0.7855 0.048 Uiso 1 1 calc R . .
C7 C 0.0438(3) 0.0641(3) 0.65600(15) 0.0483(5) Uani 1 1 d . . .
H7A H 0.1499 0.1277 0.6452 0.058 Uiso 1 1 calc R . .
H7B H 0.0982 -0.0411 0.6390 0.058 Uiso 1 1 calc R . .
C8 C -0.1058(3) 0.1581(3) 0.57895(15) 0.0464(5) Uani 1 1 d . . .
C9 C -0.2848(3) 0.1092(4) 0.58359(18) 0.0666(6) Uani 1 1 d . . .
H9A H -0.3153 0.0147 0.6348 0.080 Uiso 1 1 calc R . .
C10 C -0.4200(4) 0.2002(5) 0.5122(2) 0.0839(9) Uani 1 1 d . . .
H10A H -0.5407 0.1665 0.5166 0.101 Uiso 1 1 calc R . .
C11 C -0.3772(4) 0.3386(4) 0.4356(2) 0.0837(9) Uani 1 1 d . . .
H11A H -0.4687 0.3999 0.3886 0.100 Uiso 1 1 calc R . .
C12 C -0.2003(5) 0.3855(4) 0.4290(2) 0.0869(9) Uani 1 1 d . . .
H12A H -0.1689 0.4782 0.3763 0.104 Uiso 1 1 calc R . .
C13 C -0.0662(4) 0.2963(3) 0.50026(19) 0.0676(6) Uani 1 1 d . . .
H13A H 0.0543 0.3307 0.4948 0.081 Uiso 1 1 calc R . .
C14 C -0.2523(3) 0.5338(3) 0.7874(2) 0.0684(7) Uani 1 1 d . . .
H14A H -0.2766 0.6454 0.7957 0.103 Uiso 1 1 calc R . .
H14B H -0.3555 0.4754 0.8267 0.103 Uiso 1 1 calc R . .
H14C H -0.2477 0.5373 0.7133 0.103 Uiso 1 1 calc R . .
C15 C 0.2938(3) 0.3327(3) 0.96712(17) 0.0544(5) Uani 1 1 d . . .
H15A H 0.3814 0.4029 0.9742 0.082 Uiso 1 1 calc R . .
H15B H 0.3293 0.2223 1.0111 0.082 Uiso 1 1 calc R . .
H15C H 0.1619 0.3768 0.9891 0.082 Uiso 1 1 calc R . .
C16 C 0.2341(3) -0.2268(3) 0.8292(2) 0.0639(6) Uani 1 1 d . . .
H16A H 0.3319 -0.2738 0.8785 0.096 Uiso 1 1 calc R . .
H16B H 0.2957 -0.2091 0.7576 0.096 Uiso 1 1 calc R . .
H16C H 0.1420 -0.3019 0.8396 0.096 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 0.0331(7) 0.0822(10) 0.0471(8) -0.0220(7) 0.0004(5) -0.0190(6)
O2 0.0456(8) 0.0485(8) 0.0783(10) -0.0205(7) -0.0197(7) 0.0010(6)
O3 0.0400(7) 0.0544(8) 0.0546(8) -0.0125(6) -0.0088(6) -0.0196(6)
O4 0.0300(7) 0.0575(9) 0.0680(9) -0.0123(7) -0.0125(6) -0.0038(6)
C1 0.0284(8) 0.0525(11) 0.0391(9) -0.0116(8) -0.0103(7) -0.0055(7)
C2 0.0358(9) 0.0440(10) 0.0375(9) -0.0098(8) -0.0054(7) -0.0058(7)
C3 0.0322(9) 0.0455(10) 0.0408(9) -0.0091(8) -0.0060(7) -0.0118(7)
C4 0.0304(9) 0.0495(10) 0.0367(9) -0.0060(8) -0.0088(7) -0.0062(7)
C5 0.0363(9) 0.0460(10) 0.0437(10) -0.0077(8) -0.0086(7) -0.0081(8)
C6 0.0328(9) 0.0489(10) 0.0428(10) -0.0112(8) -0.0090(7) -0.0115(8)
C7 0.0365(10) 0.0643(13) 0.0446(10) -0.0162(9) -0.0063(8) -0.0042(9)
C8 0.0445(10) 0.0583(12) 0.0391(10) -0.0199(9) -0.0042(8) -0.0033(9)
C9 0.0548(13) 0.0958(19) 0.0527(13) -0.0165(12) -0.0124(10) -0.0188(12)
C10 0.0491(13) 0.140(3) 0.0706(17) -0.0397(19) -0.0167(12) -0.0084(15)
C11 0.0772(18) 0.109(2) 0.0591(16) -0.0253(16) -0.0282(13) 0.0209(16)
C12 0.100(2) 0.0804(19) 0.0670(17) 0.0005(14) -0.0224(15) 0.0008(16)
C13 0.0687(15) 0.0710(15) 0.0598(14) -0.0076(12) -0.0103(11) -0.0140(12)
C14 0.0504(13) 0.0574(13) 0.0938(18) -0.0186(13) -0.0202(12) 0.0088(10)
C15 0.0540(12) 0.0567(12) 0.0593(13) -0.0181(10) -0.0164(9) -0.0124(10)
C16 0.0639(14) 0.0491(12) 0.0825(17) -0.0159(11) -0.0290(12) -0.0034(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
O1 C1 1.424(2) . ?
O2 C2 1.350(2) . ?
O2 C14 1.426(2) . ?
O3 C3 1.380(2) . ?
O3 C15 1.429(2) . ?
O4 C4 1.224(2) . ?
C1 C2 1.508(2) . ?
C1 C6 1.527(3) . ?
C2 C3 1.344(2) . ?
C3 C4 1.461(3) . ?
C4 C5 1.515(2) . ?
C5 C16 1.520(3) . ?
C5 C6 1.538(2) . ?
C6 C7 1.539(3) . ?
C7 C8 1.511(3) . ?
C8 C13 1.373(3) . ?
C8 C9 1.379(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.368(4) . ?
C11 C12 1.354(4) . ?
C12 C13 1.381(4) . ?

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 O2 C14 120.49(16) . . ?
C3 O3 C15 112.18(14) . . ?
O1 C1 C2 105.17(13) . . ?
O1 C1 C6 111.84(15) . . ?
C2 C1 C6 112.78(14) . . ?
C3 C2 O2 117.33(16) . . ?
C3 C2 C1 122.39(16) . . ?
O2 C2 C1 120.14(15) . . ?
C2 C3 O3 121.20(17) . . ?
C2 C3 C4 122.10(16) . . ?
O3 C3 C4 116.70(15) . . ?
O4 C4 C3 120.84(16) . . ?
O4 C4 C5 122.12(17) . . ?
C3 C4 C5 117.00(15) . . ?
C4 C5 C16 112.04(16) . . ?
C4 C5 C6 110.68(15) . . ?
C16 C5 C6 115.16(16) . . ?
C1 C6 C5 110.28(14) . . ?
C1 C6 C7 112.62(16) . . ?
C5 C6 C7 112.12(15) . . ?
C8 C7 C6 115.17(15) . . ?
C13 C8 C9 117.4(2) . . ?
C13 C8 C7 120.45(19) . . ?
C9 C8 C7 122.1(2) . . ?
C8 C9 C10 120.5(3) . . ?
C11 C10 C9 120.6(3) . . ?
C12 C11 C10 119.3(2) . . ?
C11 C12 C13 120.3(3) . . ?
C8 C13 C12 121.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_ic16707
_database_code_depnum_ccdc_archive 'CCDC 1036452'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

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   Pca2(1)

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

_cell_length_a                   7.4859(4)
_cell_length_b                   21.3424(16)
_cell_length_c                   9.3008(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1485.96(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1281
_cell_measurement_theta_min      5.1790
_cell_measurement_theta_max      74.7550

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3281
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         68.00
_reflns_number_total             1934
_reflns_number_gt                1637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0625P)²+0.0000P] 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   -0.3(3)
_refine_ls_number_reflns         1934
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.7540(2) 0.29795(11) 0.3579(2) 0.0649(5) Uani 1 1 d . . .
H1A H 0.8615 0.2992 0.3416 0.097 Uiso 1 1 calc R . .
O2 O 0.6218(3) 0.42011(10) 0.2292(3) 0.0771(6) Uani 1 1 d . . .
O3 O 0.2704(3) 0.41574(11) 0.2734(2) 0.0704(6) Uani 1 1 d . . .
O4 O 0.1134(2) 0.30189(12) 0.3091(3) 0.0840(8) Uani 1 1 d . . .
C1 C 0.6577(3) 0.30509(13) 0.2264(3) 0.0510(5) Uani 1 1 d . . .
H1B H 0.7440 0.3113 0.1485 0.061 Uiso 1 1 calc R . .
C2 C 0.5463(4) 0.36305(13) 0.2394(3) 0.0548(6) Uani 1 1 d . . .
C3 C 0.3687(3) 0.36122(14) 0.2676(3) 0.0558(6) Uani 1 1 d . . .
C4 C 0.2736(3) 0.30253(14) 0.2866(3) 0.0558(6) Uani 1 1 d . . .
C5 C 0.3789(3) 0.24222(13) 0.2877(3) 0.0521(6) Uani 1 1 d . . .
H5A H 0.3024 0.2094 0.2472 0.063 Uiso 1 1 calc R . .
C6 C 0.5442(3) 0.24799(13) 0.1906(3) 0.0495(5) Uani 1 1 d . . .
H6A H 0.4984 0.2551 0.0933 0.059 Uiso 1 1 calc R . .
C7 C 0.8023(5) 0.42586(17) 0.1768(5) 0.0871(10) Uani 1 1 d . . .
H7A H 0.8367 0.4692 0.1767 0.131 Uiso 1 1 calc R . .
H7B H 0.8090 0.4096 0.0807 0.131 Uiso 1 1 calc R . .
H7C H 0.8814 0.4026 0.2381 0.131 Uiso 1 1 calc R . .
C8 C 0.2335(6) 0.43639(18) 0.4147(4) 0.0887(11) Uani 1 1 d . . .
H8A H 0.1653 0.4744 0.4109 0.133 Uiso 1 1 calc R . .
H8B H 0.3437 0.4439 0.4645 0.133 Uiso 1 1 calc R . .
H8C H 0.1665 0.4048 0.4647 0.133 Uiso 1 1 calc R . .
C9 C 0.4182(4) 0.22454(17) 0.4453(3) 0.0645(7) Uani 1 1 d . . .
H9A H 0.3080 0.2217 0.4976 0.097 Uiso 1 1 calc R . .
H9B H 0.4927 0.2560 0.4881 0.097 Uiso 1 1 calc R . .
H9C H 0.4784 0.1848 0.4483 0.097 Uiso 1 1 calc R . .
C10 C 0.6563(3) 0.18818(13) 0.1822(4) 0.0624(7) Uani 1 1 d . . .
H10A H 0.7616 0.1964 0.1245 0.075 Uiso 1 1 calc R . .
H10B H 0.6959 0.1771 0.2782 0.075 Uiso 1 1 calc R . .
C11 C 0.5575(3) 0.13377(14) 0.1189(4) 0.0616(7) Uani 1 1 d . . .
C12 C 0.5154(5) 0.08131(16) 0.1993(5) 0.0813(9) Uani 1 1 d . . .
H12A H 0.5526 0.0789 0.2945 0.098 Uiso 1 1 calc R . .
C13 C 0.4185(6) 0.03218(18) 0.1403(6) 0.0956(13) Uani 1 1 d . . .
H13A H 0.3915 -0.0027 0.1963 0.115 Uiso 1 1 calc R . .
C14 C 0.3626(6) 0.0346(2) 0.0012(6) 0.0985(13) Uani 1 1 d . . .
H14A H 0.2964 0.0019 -0.0378 0.118 Uiso 1 1 calc R . .
C15 C 0.4057(5) 0.08629(19) -0.0815(5) 0.0897(11) Uani 1 1 d . . .
H15A H 0.3698 0.0881 -0.1771 0.108 Uiso 1 1 calc R . .
C16 C 0.5008(4) 0.13485(17) -0.0236(4) 0.0710(8) Uani 1 1 d . . .
H16A H 0.5283 0.1693 -0.0807 0.085 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 0.0342(7) 0.1082(15) 0.0523(9) 0.0042(10) -0.0038(8) -0.0060(9)
O2 0.0709(12) 0.0733(12) 0.0872(15) 0.0001(11) 0.0139(12) -0.0051(10)
O3 0.0681(12) 0.0869(13) 0.0564(11) -0.0009(9) 0.0053(10) 0.0247(10)
O4 0.0340(8) 0.1173(18) 0.1006(19) -0.0078(15) 0.0095(11) 0.0065(9)
C1 0.0342(10) 0.0772(15) 0.0417(11) 0.0040(11) 0.0059(10) -0.0009(10)
C2 0.0515(12) 0.0735(14) 0.0393(11) 0.0014(11) 0.0002(11) -0.0005(12)
C3 0.0473(11) 0.0793(16) 0.0407(13) 0.0014(12) 0.0007(10) 0.0108(11)
C4 0.0355(11) 0.0901(17) 0.0418(11) -0.0017(13) -0.0026(11) 0.0048(11)
C5 0.0324(9) 0.0776(15) 0.0462(13) 0.0016(12) -0.0023(10) -0.0054(10)
C6 0.0360(10) 0.0725(14) 0.0401(10) 0.0046(10) 0.0009(10) 0.0036(9)
C7 0.076(2) 0.086(2) 0.100(3) 0.009(2) 0.017(2) -0.0186(16)
C8 0.096(2) 0.103(3) 0.0676(19) -0.017(2) 0.0084(19) 0.023(2)
C9 0.0491(13) 0.096(2) 0.0481(13) 0.0114(14) 0.0033(12) -0.0056(14)
C10 0.0396(12) 0.0808(16) 0.0669(16) 0.0055(15) 0.0028(12) 0.0067(12)
C11 0.0466(12) 0.0703(15) 0.0680(17) 0.0019(14) 0.0125(13) 0.0121(11)
C12 0.089(2) 0.0720(18) 0.083(2) 0.0100(17) 0.016(2) 0.0154(16)
C13 0.106(3) 0.0643(18) 0.116(4) -0.002(2) 0.030(3) 0.0039(18)
C14 0.087(2) 0.081(2) 0.128(4) -0.030(2) 0.010(3) -0.0022(19)
C15 0.088(2) 0.095(3) 0.085(2) -0.017(2) 0.000(2) 0.010(2)
C16 0.0640(15) 0.0801(19) 0.0689(18) -0.0015(16) 0.0050(15) 0.0076(15)

_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 1.428(3) . ?
O2 C2 1.346(4) . ?
O2 C7 1.441(4) . ?
O3 C3 1.378(3) . ?
O3 C8 1.413(4) . ?
O4 C4 1.218(3) . ?
C1 C2 1.497(4) . ?
C1 C6 1.523(4) . ?
C2 C3 1.356(4) . ?
C3 C4 1.451(4) . ?
C4 C5 1.509(4) . ?
C5 C6 1.537(3) . ?
C5 C9 1.542(4) . ?
C6 C10 1.529(4) . ?
C10 C11 1.497(4) . ?
C11 C12 1.383(5) . ?
C11 C16 1.392(5) . ?
C12 C13 1.388(6) . ?
C13 C14 1.360(8) . ?
C14 C15 1.383(7) . ?
C15 C16 1.368(5) . ?

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 O2 C7 119.6(3) . . ?
C3 O3 C8 113.8(2) . . ?
O1 C1 C2 107.5(2) . . ?
O1 C1 C6 112.6(2) . . ?
C2 C1 C6 111.60(19) . . ?
O2 C2 C3 116.9(3) . . ?
O2 C2 C1 120.5(2) . . ?
C3 C2 C1 122.6(3) . . ?
C2 C3 O3 120.5(3) . . ?
C2 C3 C4 121.9(3) . . ?
O3 C3 C4 117.5(2) . . ?
O4 C4 C3 120.9(3) . . ?
O4 C4 C5 120.3(3) . . ?
C3 C4 C5 118.7(2) . . ?
C4 C5 C6 110.4(2) . . ?
C4 C5 C9 108.4(2) . . ?
C6 C5 C9 115.1(2) . . ?
C1 C6 C10 111.91(19) . . ?
C1 C6 C5 112.6(2) . . ?
C10 C6 C5 113.9(2) . . ?
C11 C10 C6 113.4(2) . . ?
C12 C11 C16 117.3(3) . . ?
C12 C11 C10 121.9(3) . . ?
C16 C11 C10 120.8(3) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C13 C12 120.6(4) . . ?
C13 C14 C15 119.1(4) . . ?
C16 C15 C14 120.5(4) . . ?
C15 C16 C11 121.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_ic17004
_database_code_depnum_ccdc_archive 'CCDC 1036453'
_audit_update_record             
;
2014-11-27 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.37

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   Pbca

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'
'-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                   11.7297(5)
_cell_length_b                   8.2689(5)
_cell_length_c                   34.713(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3366.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1831
_cell_measurement_theta_min      3.8000
_cell_measurement_theta_max      73.5010

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7993
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         68.00
_reflns_number_total             3052
_reflns_number_gt                2024
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0989P)²+3.4878P] 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_number_reflns         3052
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2200
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.064
_refine_ls_shift/su_mean         0.009

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 0.7155(2) 0.2454(4) 0.35188(7) 0.0564(8) Uani 1 1 d . . .
O2 O 0.71508(19) 0.0910(3) 0.42153(7) 0.0430(6) Uani 1 1 d . . .
O3 O 0.9284(2) 0.0672(3) 0.46005(6) 0.0421(6) Uani 1 1 d . . .
O4 O 1.1066(2) 0.0758(3) 0.41829(7) 0.0445(6) Uani 1 1 d . . .
O5 O 1.05721(19) 0.3473(3) 0.42119(7) 0.0427(6) Uani 1 1 d . . .
C1 C 0.8051(3) 0.2420(5) 0.36958(10) 0.0446(9) Uani 1 1 d . . .
C2 C 0.8128(3) 0.1588(5) 0.40738(10) 0.0401(8) Uani 1 1 d . . .
C3 C 0.9126(3) 0.1372(4) 0.42504(10) 0.0375(8) Uani 1 1 d . . .
C4 C 1.0254(3) 0.1910(4) 0.40704(10) 0.0369(8) Uani 1 1 d . . .
C5 C 1.0157(3) 0.2125(5) 0.36364(10) 0.0418(9) Uani 1 1 d . . .
H5A H 1.0862 0.2695 0.3548 0.050 Uiso 1 1 calc R . .
C6 C 0.9123(3) 0.3285(6) 0.35579(11) 0.0495(10) Uani 1 1 d . . .
H6A H 0.9228 0.4265 0.3723 0.059 Uiso 1 1 calc R . .
C7 C 0.8996(3) 0.3848(6) 0.31489(12) 0.0540(11) Uani 1 1 d . . .
H7A H 0.8400 0.4694 0.3139 0.065 Uiso 1 1 calc R . .
H7B H 0.8736 0.2929 0.2989 0.065 Uiso 1 1 calc R . .
C8 C 1.0081(3) 0.4519(5) 0.29785(12) 0.0475(10) Uani 1 1 d . . .
C9 C 1.0675(4) 0.5800(6) 0.31380(12) 0.0600(11) Uani 1 1 d . . .
H9A H 1.0395 0.6304 0.3365 0.072 Uiso 1 1 calc R . .
C10 C 1.1683(4) 0.6365(6) 0.29698(13) 0.0637(12) Uani 1 1 d . . .
H10A H 1.2097 0.7227 0.3085 0.076 Uiso 1 1 calc R . .
C11 C 1.2068(3) 0.5657(6) 0.26353(12) 0.0563(11) Uani 1 1 d . . .
H11A H 1.2749 0.6033 0.2517 0.068 Uiso 1 1 calc R . .
C12 C 1.1465(4) 0.4403(5) 0.24722(12) 0.0530(10) Uani 1 1 d . . .
H12A H 1.1724 0.3920 0.2240 0.064 Uiso 1 1 calc R . .
C13 C 1.0492(3) 0.3852(5) 0.26451(12) 0.0507(10) Uani 1 1 d . . .
H13A H 1.0089 0.2980 0.2530 0.061 Uiso 1 1 calc R . .
C14 C 0.6223(3) 0.2002(5) 0.42837(12) 0.0512(10) Uani 1 1 d . . .
H14A H 0.5569 0.1399 0.4385 0.077 Uiso 1 1 calc R . .
H14B H 0.6009 0.2529 0.4042 0.077 Uiso 1 1 calc R . .
H14C H 0.6458 0.2823 0.4471 0.077 Uiso 1 1 calc R . .
C15 C 0.8427(3) 0.0853(6) 0.48922(10) 0.0528(10) Uani 1 1 d . . .
H15A H 0.8663 0.0275 0.5125 0.079 Uiso 1 1 calc R . .
H15B H 0.7704 0.0405 0.4799 0.079 Uiso 1 1 calc R . .
H15C H 0.8327 0.2003 0.4952 0.079 Uiso 1 1 calc R . .
C16 C 1.2215(3) 0.1097(6) 0.40608(13) 0.0614(12) Uani 1 1 d . . .
H16A H 1.2724 0.0240 0.4152 0.092 Uiso 1 1 calc R . .
H16B H 1.2460 0.2137 0.4168 0.092 Uiso 1 1 calc R . .
H16C H 1.2243 0.1147 0.3779 0.092 Uiso 1 1 calc R . .
C17 C 1.0631(4) 0.3648(6) 0.46206(11) 0.0583(11) Uani 1 1 d . . .
H17A H 1.0851 0.4760 0.4685 0.087 Uiso 1 1 calc R . .
H17B H 1.1199 0.2896 0.4724 0.087 Uiso 1 1 calc R . .
H17C H 0.9884 0.3410 0.4733 0.087 Uiso 1 1 calc R . .
C18 C 1.0100(4) 0.0548(6) 0.34256(12) 0.0629(12) Uani 1 1 d . . .
H18A H 1.0774 -0.0102 0.3488 0.094 Uiso 1 1 calc R . .
H18B H 1.0076 0.0751 0.3148 0.094 Uiso 1 1 calc R . .
H18C H 0.9411 -0.0039 0.3504 0.094 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 0.0363(13) 0.085(2) 0.0475(15) 0.0099(14) -0.0071(12) -0.0057(14)
O2 0.0386(12) 0.0425(14) 0.0480(14) 0.0005(12) 0.0046(11) -0.0078(11)
O3 0.0456(13) 0.0452(15) 0.0355(12) 0.0102(11) 0.0048(11) 0.0025(12)
O4 0.0430(13) 0.0498(15) 0.0408(13) 0.0099(12) 0.0033(11) 0.0135(12)
O5 0.0384(12) 0.0399(14) 0.0498(14) 0.0029(12) 0.0008(11) -0.0049(11)
C1 0.0341(18) 0.058(2) 0.0418(19) 0.0037(18) -0.0036(16) -0.0009(17)
C2 0.0374(18) 0.043(2) 0.0402(18) 0.0023(16) 0.0022(15) -0.0077(16)
C3 0.0443(19) 0.0314(18) 0.0368(18) 0.0034(15) 0.0003(15) -0.0011(15)
C4 0.0351(16) 0.0392(19) 0.0363(18) 0.0019(15) -0.0038(15) 0.0010(15)
C5 0.0351(17) 0.057(2) 0.0337(17) 0.0106(17) -0.0004(15) -0.0052(16)
C6 0.0385(18) 0.064(3) 0.046(2) 0.0095(19) -0.0021(16) -0.0006(18)
C7 0.046(2) 0.061(3) 0.055(2) 0.010(2) 0.0003(18) 0.004(2)
C8 0.0417(18) 0.047(2) 0.054(2) 0.0184(19) 0.0002(17) 0.0070(18)
C9 0.074(3) 0.062(3) 0.044(2) 0.008(2) 0.010(2) 0.002(2)
C10 0.070(3) 0.062(3) 0.059(3) 0.012(2) -0.007(2) -0.018(2)
C11 0.045(2) 0.067(3) 0.057(2) 0.021(2) 0.0055(19) 0.001(2)
C12 0.057(2) 0.052(2) 0.050(2) 0.009(2) 0.0055(19) 0.007(2)
C13 0.051(2) 0.049(2) 0.052(2) 0.0076(19) -0.0018(18) 0.0015(19)
C14 0.044(2) 0.057(3) 0.053(2) -0.005(2) 0.0088(18) -0.0044(18)
C15 0.057(2) 0.065(3) 0.0360(18) 0.0057(19) 0.0112(17) 0.004(2)
C16 0.040(2) 0.078(3) 0.066(3) 0.015(2) 0.0009(19) 0.020(2)
C17 0.070(3) 0.059(3) 0.045(2) -0.009(2) -0.001(2) -0.014(2)
C18 0.065(3) 0.079(3) 0.045(2) -0.010(2) 0.010(2) -0.009(2)

_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 1.218(4) . ?
O2 C2 1.367(4) . ?
O2 C14 1.434(5) . ?
O3 C3 1.359(4) . ?
O3 C15 1.435(4) . ?
O4 C4 1.403(4) . ?
O4 C16 1.441(5) . ?
O5 C17 1.428(4) . ?
O5 C4 1.433(4) . ?
C1 C2 1.484(5) . ?
C1 C6 1.524(5) . ?
C2 C3 1.334(5) . ?
C3 C4 1.528(5) . ?
C4 C5 1.521(5) . ?
C5 C18 1.497(6) . ?
C5 C6 1.570(5) . ?
C6 C7 1.502(5) . ?
C7 C8 1.509(5) . ?
C8 C13 1.369(6) . ?
C8 C9 1.384(6) . ?
C9 C10 1.399(6) . ?
C10 C11 1.377(6) . ?
C11 C12 1.377(6) . ?
C12 C13 1.367(6) . ?

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 O2 C14 115.9(3) . . ?
C3 O3 C15 119.4(3) . . ?
C4 O4 C16 114.9(3) . . ?
C17 O5 C4 116.4(3) . . ?
O1 C1 C2 120.6(3) . . ?
O1 C1 C6 122.9(3) . . ?
C2 C1 C6 116.4(3) . . ?
C3 C2 O2 121.1(3) . . ?
C3 C2 C1 121.4(3) . . ?
O2 C2 C1 117.2(3) . . ?
C2 C3 O3 126.0(3) . . ?
C2 C3 C4 122.2(3) . . ?
O3 C3 C4 111.8(3) . . ?
O4 C4 O5 109.9(3) . . ?
O4 C4 C5 113.9(3) . . ?
O5 C4 C5 104.7(3) . . ?
O4 C4 C3 106.0(3) . . ?
O5 C4 C3 110.4(3) . . ?
C5 C4 C3 112.0(3) . . ?
C18 C5 C4 112.7(3) . . ?
C18 C5 C6 114.4(3) . . ?
C4 C5 C6 107.5(3) . . ?
C7 C6 C1 111.1(3) . . ?
C7 C6 C5 115.5(3) . . ?
C1 C6 C5 107.3(3) . . ?
C6 C7 C8 113.6(3) . . ?
C13 C8 C9 118.0(4) . . ?
C13 C8 C7 118.7(4) . . ?
C9 C8 C7 123.3(4) . . ?
C8 C9 C10 120.9(4) . . ?
C11 C10 C9 119.2(4) . . ?
C10 C11 C12 119.9(4) . . ?
C13 C12 C11 119.9(4) . . ?
C12 C13 C8 122.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.058
