# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_new
_database_code_depnum_ccdc_archive 'CCDC 971194'
_audit_update_record             
;
2013-11-09 deposited with the CCDC.
2015-09-23 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 H15 Br O3'
_chemical_formula_weight         335.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   10.998(2)
_cell_length_b                   6.1970(12)
_cell_length_c                   21.583(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.25(3)
_cell_angle_gamma                90.00
_cell_volume                     1431.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            'clear light colour'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5334
_exptl_absorpt_correction_T_max  0.7620
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10343
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         28.21
_reflns_number_total             3478
_reflns_number_gt                2363
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0306P)²+0.6267P] 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         3478
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.47402(3) 0.20818(5) 0.189289(11) 0.05871(11) Uani 1 1 d . . .
C1 C 0.0753(2) 1.0440(4) -0.08025(11) 0.0436(6) Uani 1 1 d . . .
H1 H 0.0334 1.1676 -0.0723 0.052 Uiso 1 1 calc R . .
C2 C 0.0798(2) 0.9902(4) -0.14271(11) 0.0452(6) Uani 1 1 d . . .
H2 H 0.0405 1.0787 -0.1761 0.054 Uiso 1 1 calc R . .
C3 C 0.1412(2) 0.8089(4) -0.15531(10) 0.0407(5) Uani 1 1 d . . .
H3 H 0.1422 0.7760 -0.1972 0.049 Uiso 1 1 calc R . .
C4 C 0.20334(19) 0.6702(3) -0.10572(9) 0.0316(5) Uani 1 1 d . . .
C5 C 0.27017(19) 0.4775(3) -0.11627(9) 0.0325(5) Uani 1 1 d . . .
C6 C 0.3309(2) 0.3534(3) -0.06344(9) 0.0321(5) Uani 1 1 d . . .
C7 C 0.32783(19) 0.4103(3) 0.00009(9) 0.0317(5) Uani 1 1 d . . .
C8 C 0.3977(2) 0.2755(4) 0.05529(10) 0.0377(5) Uani 1 1 d . . .
H8A H 0.4811 0.2440 0.0499 0.045 Uiso 1 1 calc R . .
H8B H 0.3545 0.1399 0.0568 0.045 Uiso 1 1 calc R . .
C9 C 0.4059(2) 0.3994(4) 0.11681(9) 0.0368(5) Uani 1 1 d . . .
H9 H 0.4659 0.5168 0.1178 0.044 Uiso 1 1 calc R . .
C10 C 0.2816(2) 0.5018(4) 0.12158(9) 0.0368(5) Uani 1 1 d . . .
C11 C 0.26106(19) 0.5900(3) 0.00940(9) 0.0316(5) Uani 1 1 d . . .
C12 C 0.19802(19) 0.7262(3) -0.04225(10) 0.0311(4) Uani 1 1 d . . .
C13 C 0.1329(2) 0.9136(3) -0.03097(10) 0.0372(5) Uani 1 1 d . . .
H13 H 0.1292 0.9488 0.0104 0.045 Uiso 1 1 calc R . .
C14 C 0.2773(2) 0.4068(4) -0.17895(10) 0.0391(5) Uani 1 1 d . . .
C15 C 0.1742(2) 0.3405(4) 0.11446(12) 0.0544(7) Uani 1 1 d . . .
H15A H 0.1001 0.4142 0.1191 0.082 Uiso 1 1 calc R . .
H15B H 0.1956 0.2312 0.1466 0.082 Uiso 1 1 calc R . .
H15C H 0.1595 0.2746 0.0731 0.082 Uiso 1 1 calc R . .
C16 C 0.2932(3) 0.6417(4) 0.18081(11) 0.0552(7) Uani 1 1 d . . .
H16A H 0.3636 0.7363 0.1848 0.083 Uiso 1 1 calc R . .
H16B H 0.3047 0.5510 0.2178 0.083 Uiso 1 1 calc R . .
H16C H 0.2185 0.7257 0.1771 0.083 Uiso 1 1 calc R . .
O1 O 0.25091(14) 0.6568(2) 0.06849(6) 0.0386(4) Uani 1 1 d . . .
O2 O 0.33540(17) 0.2453(3) -0.18971(7) 0.0485(4) Uani 1 1 d . . .
O3 O 0.39561(16) 0.1743(3) -0.06995(8) 0.0433(4) Uani 1 1 d . . .
H1O H 0.385(3) 0.154(5) -0.1077(14) 0.076(10) Uiso 1 1 d . . .
H14C H 0.237(2) 0.492(4) -0.2138(12) 0.051(7) Uiso 1 1 d . . .


_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
Br1 C9 1.968(2) . ?
C1 C13 1.370(3) . ?
C1 C2 1.401(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.420(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.427(3) . ?
C4 C5 1.447(3) . ?
C5 C6 1.410(3) . ?
C5 C14 1.441(3) . ?
C6 O3 1.344(3) . ?
C6 C7 1.423(3) . ?
C7 C11 1.374(3) . ?
C7 C8 1.513(3) . ?
C8 C9 1.518(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.532(3) . ?
C9 H9 0.9800 . ?
C10 O1 1.474(3) . ?
C10 C15 1.528(3) . ?
C10 C16 1.526(3) . ?
C11 O1 1.369(2) . ?
C11 C12 1.442(3) . ?
C12 C13 1.414(3) . ?
C13 H13 0.9300 . ?
C14 O2 1.238(3) . ?
C14 H14C 0.94(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O3 H1O 0.81(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
C13 C1 C2 119.6(2) . . ?
C13 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C12 117.25(19) . . ?
C3 C4 C5 123.69(19) . . ?
C12 C4 C5 119.06(18) . . ?
C6 C5 C14 118.4(2) . . ?
C6 C5 C4 119.07(18) . . ?
C14 C5 C4 122.51(19) . . ?
O3 C6 C5 122.00(18) . . ?
O3 C6 C7 115.80(18) . . ?
C5 C6 C7 122.20(19) . . ?
C11 C7 C6 118.21(18) . . ?
C11 C7 C8 121.64(18) . . ?
C6 C7 C8 120.15(19) . . ?
C7 C8 C9 109.10(18) . . ?
C7 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 C10 113.17(17) . . ?
C8 C9 Br1 109.04(15) . . ?
C10 C9 Br1 112.27(14) . . ?
C8 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
Br1 C9 H9 107.4 . . ?
O1 C10 C15 108.34(18) . . ?
O1 C10 C16 103.96(18) . . ?
C15 C10 C16 111.74(19) . . ?
O1 C10 C9 105.45(16) . . ?
C15 C10 C9 113.78(19) . . ?
C16 C10 C9 112.77(19) . . ?
O1 C11 C7 122.78(18) . . ?
O1 C11 C12 114.57(18) . . ?
C7 C11 C12 122.64(18) . . ?
C13 C12 C4 119.90(19) . . ?
C13 C12 C11 121.31(19) . . ?
C4 C12 C11 118.78(18) . . ?
C1 C13 C12 120.9(2) . . ?
C1 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O2 C14 C5 124.3(2) . . ?
O2 C14 H14C 118.2(15) . . ?
C5 C14 H14C 117.5(15) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 O1 C10 118.30(16) . . ?
C6 O3 H1O 106(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C12 0.6(3) . . . . ?
C2 C3 C4 C5 -179.6(2) . . . . ?
C3 C4 C5 C6 178.7(2) . . . . ?
C12 C4 C5 C6 -1.6(3) . . . . ?
C3 C4 C5 C14 -1.3(3) . . . . ?
C12 C4 C5 C14 178.39(19) . . . . ?
C14 C5 C6 O3 0.8(3) . . . . ?
C4 C5 C6 O3 -179.24(19) . . . . ?
C14 C5 C6 C7 -179.5(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
O3 C6 C7 C11 -178.88(19) . . . . ?
C5 C6 C7 C11 1.4(3) . . . . ?
O3 C6 C7 C8 1.6(3) . . . . ?
C5 C6 C7 C8 -178.13(19) . . . . ?
C11 C7 C8 C9 -13.3(3) . . . . ?
C6 C7 C8 C9 166.16(18) . . . . ?
C7 C8 C9 C10 45.9(2) . . . . ?
C7 C8 C9 Br1 171.58(14) . . . . ?
C8 C9 C10 O1 -62.3(2) . . . . ?
Br1 C9 C10 O1 173.77(12) . . . . ?
C8 C9 C10 C15 56.3(2) . . . . ?
Br1 C9 C10 C15 -67.6(2) . . . . ?
C8 C9 C10 C16 -175.07(19) . . . . ?
Br1 C9 C10 C16 61.0(2) . . . . ?
C6 C7 C11 O1 179.12(18) . . . . ?
C8 C7 C11 O1 -1.4(3) . . . . ?
C6 C7 C11 C12 -2.2(3) . . . . ?
C8 C7 C11 C12 177.32(19) . . . . ?
C3 C4 C12 C13 -0.1(3) . . . . ?
C5 C4 C12 C13 -179.87(19) . . . . ?
C3 C4 C12 C11 -179.44(19) . . . . ?
C5 C4 C12 C11 0.8(3) . . . . ?
O1 C11 C12 C13 0.6(3) . . . . ?
C7 C11 C12 C13 -178.2(2) . . . . ?
O1 C11 C12 C4 179.90(17) . . . . ?
C7 C11 C12 C4 1.1(3) . . . . ?
C2 C1 C13 C12 0.6(3) . . . . ?
C4 C12 C13 C1 -0.5(3) . . . . ?
C11 C12 C13 C1 178.8(2) . . . . ?
C6 C5 C14 O2 -1.4(3) . . . . ?
C4 C5 C14 O2 178.6(2) . . . . ?
C7 C11 O1 C10 -17.5(3) . . . . ?
C12 C11 O1 C10 163.72(17) . . . . ?
C15 C10 O1 C11 -75.1(2) . . . . ?
C16 C10 O1 C11 165.88(19) . . . . ?
C9 C10 O1 C11 47.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 971195'
_audit_update_record             
;
2013-11-09 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 ?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C15 H12 O4'

_chemical_formula_weight         256.25



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source






C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)



loop_

_symmetry_equiv_pos_as_xyz


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



_cell_length_a                   10.439(3)

_cell_length_b                   5.0804(19)

_cell_length_c                   11.712(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 99.816(14)

_cell_angle_gamma                90.00

_cell_volume                     612.1(3)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    679

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      22.27



_exptl_crystal_description       Needle

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.45

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.390

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             268

_exptl_absorpt_coefficient_mu    0.101

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9558

_exptl_absorpt_correction_T_max  0.9899

_exptl_absorpt_process_details   'SADABS (Bruker,2004)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            3034

_diffrn_reflns_av_R_equivalents  0.0395

_diffrn_reflns_av_sigmaI/netI    0.0869

_diffrn_reflns_limit_h_min       -15

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -3

_diffrn_reflns_limit_k_max       5

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       12

_diffrn_reflns_theta_min         1.76

_diffrn_reflns_theta_max         30.93

_reflns_number_total             1706

_reflns_number_gt                990

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'APEXII, Bruker,2004'
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_structure_solution    'SHELXS-97  (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97  (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3   (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97  (Sheldrick, 1997)'




_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     SHELXL

_refine_ls_extinction_coef       0.070(16)

_refine_ls_extinction_expression 
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -1(4)

_refine_ls_number_reflns         1706

_refine_ls_number_parameters     175

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.1322

_refine_ls_R_factor_gt           0.0693

_refine_ls_wR_factor_ref         0.1963

_refine_ls_wR_factor_gt          0.1622

_refine_ls_goodness_of_fit_ref   1.091

_refine_ls_restrained_S_all      1.090

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group































C1 C 0.6360(6) 0.1914(17) 0.0283(5) 0.052(2) Uani 1 1 d . . .
H1 H 0.5683 0.0782 0.0369 0.062 Uiso 1 1 calc R . .
C2 C 0.6943(7) 0.172(2) -0.0678(5) 0.069(3) Uani 1 1 d . . .
H2 H 0.6645 0.0496 -0.1250 0.082 Uiso 1 1 calc R . .
C3 C 0.7947(7) 0.331(2) -0.0796(5) 0.068(3) Uani 1 1 d . . .
H3 H 0.8357 0.3104 -0.1436 0.082 Uiso 1 1 calc R . .
C4 C 0.8379(7) 0.5219(18) -0.0003(5) 0.058(2) Uani 1 1 d . . .
H4 H 0.9050 0.6344 -0.0112 0.069 Uiso 1 1 calc R . .
C5 C 0.7789(6) 0.5440(15) 0.0974(5) 0.0414(19) Uani 1 1 d . . .
C6 C 0.8243(6) 0.7479(16) 0.1854(5) 0.0427(18) Uani 1 1 d . . .
C7 C 0.7515(5) 0.7638(14) 0.2820(4) 0.0347(16) Uani 1 1 d . . .
C8 C 0.7066(5) 0.8843(16) 0.4586(4) 0.0410(17) Uani 1 1 d . . .
H8 H 0.6647 1.0447 0.4806 0.049 Uiso 1 1 calc R . .
C9 C 0.6011(5) 0.6851(15) 0.4015(5) 0.0388(18) Uani 1 1 d . . .
H9 H 0.5974 0.5340 0.4528 0.047 Uiso 1 1 calc R . .
C10 C 0.6535(5) 0.6016(15) 0.2955(4) 0.0371(17) Uani 1 1 d . . .
C11 C 0.6123(5) 0.3971(17) 0.2156(4) 0.0430(19) Uani 1 1 d . . .
C12 C 0.6769(5) 0.3761(16) 0.1118(5) 0.0399(18) Uani 1 1 d . . .
C13 C 0.7980(6) 0.7794(15) 0.5609(5) 0.047(2) Uani 1 1 d . . .
C14 C 0.8842(7) 0.5554(19) 0.5434(6) 0.070(3) Uani 1 1 d . . .
H14A H 0.8321 0.4061 0.5148 0.105 Uiso 1 1 calc R . .
H14B H 0.9378 0.5111 0.6159 0.105 Uiso 1 1 calc R . .
H14C H 0.9384 0.6044 0.4884 0.105 Uiso 1 1 calc R . .
C15 C 0.7956(8) 0.877(2) 0.6643(5) 0.086(3) Uani 1 1 d . . .
H15A H 0.8486 0.8055 0.7288 0.103 Uiso 1 1 calc R . .
H15B H 0.7408 1.0170 0.6731 0.103 Uiso 1 1 calc R . .
O1 O 0.7824(4) 0.9455(9) 0.3645(3) 0.0440(13) Uani 1 1 d . . .
O2 O 0.4760(4) 0.8079(11) 0.3751(3) 0.0521(15) Uani 1 1 d . . .
H2A H 0.4719 0.8957 0.3158 0.078 Uiso 1 1 calc R . .
O3 O 0.5263(4) 0.2337(11) 0.2303(3) 0.0508(14) Uani 1 1 d . . .
O4 O 0.9154(4) 0.8926(12) 0.1800(3) 0.0584(16) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag

































C1 C12 1.370(10) . ?
C1 C2 1.371(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.349(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(8) . ?
C4 H4 0.9300 . ?
C5 C12 1.397(9) . ?
C5 C6 1.481(9) . ?
C6 O4 1.212(8) . ?
C6 C7 1.468(7) . ?
C7 O1 1.335(7) . ?
C7 C10 1.344(9) . ?
C8 O1 1.495(6) . ?
C8 C13 1.497(8) . ?
C8 C9 1.560(9) . ?
C8 H8 0.9800 . ?
C9 O2 1.433(7) . ?
C9 C10 1.500(8) . ?
C9 H9 0.9800 . ?
C10 C11 1.416(10) . ?
C11 O3 1.256(8) . ?
C11 C12 1.491(8) . ?
C13 C15 1.313(9) . ?
C13 C14 1.486(11) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
O2 H2A 0.8200 . ?



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
























































C12 C1 C2 120.4(7) . . ?
C12 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.3(7) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.8(6) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.4(7) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C12 120.2(6) . . ?
C4 C5 C6 119.6(6) . . ?
C12 C5 C6 120.2(5) . . ?
O4 C6 C7 121.4(6) . . ?
O4 C6 C5 123.3(5) . . ?
C7 C6 C5 115.3(5) . . ?
O1 C7 C10 115.7(5) . . ?
O1 C7 C6 120.1(5) . . ?
C10 C7 C6 124.1(6) . . ?
O1 C8 C13 108.6(4) . . ?
O1 C8 C9 104.0(4) . . ?
C13 C8 C9 114.8(6) . . ?
O1 C8 H8 109.7 . . ?
C13 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
O2 C9 C10 113.1(4) . . ?
O2 C9 C8 111.2(6) . . ?
C10 C9 C8 102.0(5) . . ?
O2 C9 H9 110.1 . . ?
C10 C9 H9 110.1 . . ?
C8 C9 H9 110.1 . . ?
C7 C10 C11 121.6(5) . . ?
C7 C10 C9 108.4(6) . . ?
C11 C10 C9 129.9(6) . . ?
O3 C11 C10 122.6(5) . . ?
O3 C11 C12 119.9(6) . . ?
C10 C11 C12 117.6(6) . . ?
C1 C12 C5 118.9(5) . . ?
C1 C12 C11 120.1(6) . . ?
C5 C12 C11 121.0(6) . . ?
C15 C13 C14 121.5(7) . . ?
C15 C13 C8 119.6(7) . . ?
C14 C13 C8 118.7(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 120.0 . . ?
C13 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C7 O1 C8 107.2(5) . . ?
C9 O2 H2A 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















































C12 C1 C2 C3 1.6(12) . . . . ?
C1 C2 C3 C4 -2.9(14) . . . . ?
C2 C3 C4 C5 2.5(13) . . . . ?
C3 C4 C5 C12 -0.9(11) . . . . ?
C3 C4 C5 C6 179.5(7) . . . . ?
C4 C5 C6 O4 -3.3(10) . . . . ?
C12 C5 C6 O4 177.1(7) . . . . ?
C4 C5 C6 C7 177.0(6) . . . . ?
C12 C5 C6 C7 -2.6(8) . . . . ?
O4 C6 C7 O1 2.0(10) . . . . ?
C5 C6 C7 O1 -178.3(6) . . . . ?
O4 C6 C7 C10 -176.9(7) . . . . ?
C5 C6 C7 C10 2.8(9) . . . . ?
O1 C8 C9 O2 -105.4(5) . . . . ?
C13 C8 C9 O2 136.1(5) . . . . ?
O1 C8 C9 C10 15.4(6) . . . . ?
C13 C8 C9 C10 -103.1(5) . . . . ?
O1 C7 C10 C11 -178.9(6) . . . . ?
C6 C7 C10 C11 0.1(10) . . . . ?
O1 C7 C10 C9 2.8(8) . . . . ?
C6 C7 C10 C9 -178.1(6) . . . . ?
O2 C9 C10 C7 107.9(6) . . . . ?
C8 C9 C10 C7 -11.6(7) . . . . ?
O2 C9 C10 C11 -70.2(9) . . . . ?
C8 C9 C10 C11 170.3(7) . . . . ?
C7 C10 C11 O3 175.6(6) . . . . ?
C9 C10 C11 O3 -6.5(11) . . . . ?
C7 C10 C11 C12 -3.1(9) . . . . ?
C9 C10 C11 C12 174.7(6) . . . . ?
C2 C1 C12 C5 -0.1(10) . . . . ?
C2 C1 C12 C11 179.5(6) . . . . ?
C4 C5 C12 C1 -0.3(10) . . . . ?
C6 C5 C12 C1 179.3(6) . . . . ?
C4 C5 C12 C11 -179.8(6) . . . . ?
C6 C5 C12 C11 -0.3(9) . . . . ?
O3 C11 C12 C1 4.8(9) . . . . ?
C10 C11 C12 C1 -176.4(6) . . . . ?
O3 C11 C12 C5 -175.6(6) . . . . ?
C10 C11 C12 C5 3.2(8) . . . . ?
O1 C8 C13 C15 131.0(8) . . . . ?
C9 C8 C13 C15 -113.1(9) . . . . ?
O1 C8 C13 C14 -52.6(9) . . . . ?
C9 C8 C13 C14 63.3(8) . . . . ?
C10 C7 O1 C8 7.9(7) . . . . ?
C6 C7 O1 C8 -171.1(5) . . . . ?
C13 C8 O1 C7 108.1(6) . . . . ?
C9 C8 O1 C7 -14.6(6) . . . . ?



_diffrn_measured_fraction_theta_max 0.576

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.898

_refine_diff_density_max         0.670

_refine_diff_density_min         -0.204

_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 971196'
_audit_update_record             
;
2013-11-09 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 O5'
_chemical_formula_weight         274.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1031(12)
_cell_length_b                   10.4382(9)
_cell_length_c                   17.8607(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2629.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6616
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      24.11

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9143
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27379
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         27.60
_reflns_number_total             3036
_reflns_number_gt                2097
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0429P)²+0.7250P] 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         3036
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.92155(11) 0.40331(17) 0.82332(8) 0.0504(4) Uani 1 1 d . . .
C2 C 0.86849(12) 0.50382(17) 0.87039(9) 0.0511(4) Uani 1 1 d . . .
C3 C 0.76350(11) 0.49502(15) 0.87623(8) 0.0451(4) Uani 1 1 d . . .
C4 C 0.71379(13) 0.57660(18) 0.92290(9) 0.0577(5) Uani 1 1 d . . .
H4 H 0.7459 0.6388 0.9502 0.069 Uiso 1 1 calc R . .
C5 C 0.61663(15) 0.5657(2) 0.92894(10) 0.0669(5) Uani 1 1 d . . .
H5 H 0.5835 0.6200 0.9609 0.080 Uiso 1 1 calc R . .
C6 C 0.56841(13) 0.4754(2) 0.88806(11) 0.0668(5) Uani 1 1 d . . .
H6 H 0.5029 0.4692 0.8924 0.080 Uiso 1 1 calc R . .
C7 C 0.61657(11) 0.39348(18) 0.84042(10) 0.0544(4) Uani 1 1 d . . .
H7 H 0.5836 0.3328 0.8125 0.065 Uiso 1 1 calc R . .
C8 C 0.71422(10) 0.40276(15) 0.83470(8) 0.0423(4) Uani 1 1 d . . .
C9 C 0.76978(10) 0.31973(14) 0.78642(8) 0.0404(3) Uani 1 1 d . . .
C10 C 0.79859(10) 0.16659(15) 0.69865(8) 0.0419(3) Uani 1 1 d . . .
H10 H 0.7940 0.0741 0.7073 0.050 Uiso 1 1 calc R . .
C11 C 0.89478(11) 0.21543(17) 0.72768(9) 0.0508(4) Uani 1 1 d . . .
H11A H 0.9297 0.1481 0.7530 0.061 Uiso 1 1 calc R . .
H11B H 0.9332 0.2497 0.6873 0.061 Uiso 1 1 calc R . .
C12 C 0.86531(10) 0.31826(15) 0.78099(8) 0.0434(4) Uani 1 1 d . . .
C13 C 0.77926(10) 0.19505(13) 0.61626(8) 0.0378(3) Uani 1 1 d . . .
C14 C 0.67769(11) 0.16248(16) 0.59568(10) 0.0504(4) Uani 1 1 d . . .
H14A H 0.6351 0.2113 0.6264 0.076 Uiso 1 1 calc R . .
H14B H 0.6668 0.0727 0.6036 0.076 Uiso 1 1 calc R . .
H14C H 0.6669 0.1829 0.5440 0.076 Uiso 1 1 calc R . .
C15 C 0.84973(11) 0.12143(15) 0.56788(9) 0.0442(4) Uani 1 1 d . . .
H15A H 0.8337 0.1341 0.5156 0.053 Uiso 1 1 calc R . .
H15B H 0.9127 0.1560 0.5760 0.053 Uiso 1 1 calc R . .
O1 O 1.00910(8) 0.40251(15) 0.82412(7) 0.0750(4) Uani 1 1 d . . .
O2 O 0.91346(10) 0.58764(14) 0.90071(8) 0.0779(4) Uani 1 1 d . . .
O3 O 0.72610(7) 0.23334(10) 0.74394(6) 0.0484(3) Uani 1 1 d . . .
O4 O 0.80060(8) 0.32601(10) 0.60208(7) 0.0501(3) Uani 1 1 d . . .
H4A H 0.7512 0.3670 0.5990 0.075 Uiso 1 1 calc R . .
O5 O 0.85084(8) -0.01123(10) 0.58342(7) 0.0544(3) Uani 1 1 d . . .
H5A H 0.8987 -0.0290 0.6073 0.082 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
C1 O1 1.2349(19) . ?
C1 C12 1.410(2) . ?
C1 C2 1.539(2) . ?
C2 O2 1.2087(19) . ?
C2 C3 1.487(2) . ?
C3 C4 1.383(2) . ?
C3 C8 1.400(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.452(2) . ?
C9 O3 1.3298(17) . ?
C9 C12 1.351(2) . ?
C10 O3 1.4782(18) . ?
C10 C13 1.526(2) . ?
C10 C11 1.539(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.494(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 O4 1.4225(17) . ?
C13 C14 1.517(2) . ?
C13 C15 1.525(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O5 1.4124(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O4 H4A 0.8200 . ?
O5 H5A 0.8200 . ?

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
O1 C1 C12 124.36(16) . . ?
O1 C1 C2 118.98(15) . . ?
C12 C1 C2 116.65(14) . . ?
O2 C2 C3 122.40(16) . . ?
O2 C2 C1 118.89(15) . . ?
C3 C2 C1 118.71(14) . . ?
C4 C3 C8 119.42(15) . . ?
C4 C3 C2 120.61(15) . . ?
C8 C3 C2 119.97(14) . . ?
C5 C4 C3 120.03(17) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.47(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.54(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.35(17) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C3 120.19(15) . . ?
C7 C8 C9 122.60(14) . . ?
C3 C8 C9 117.20(13) . . ?
O3 C9 C12 114.42(13) . . ?
O3 C9 C8 119.57(13) . . ?
C12 C9 C8 125.99(14) . . ?
O3 C10 C13 108.21(11) . . ?
O3 C10 C11 105.61(12) . . ?
C13 C10 C11 114.70(12) . . ?
O3 C10 H10 109.4 . . ?
C13 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C12 C11 C10 101.98(12) . . ?
C12 C11 H11A 111.4 . . ?
C10 C11 H11A 111.4 . . ?
C12 C11 H11B 111.4 . . ?
C10 C11 H11B 111.4 . . ?
H11A C11 H11B 109.2 . . ?
C9 C12 C1 121.02(15) . . ?
C9 C12 C11 109.35(13) . . ?
C1 C12 C11 129.61(14) . . ?
O4 C13 C14 111.84(12) . . ?
O4 C13 C15 104.21(11) . . ?
C14 C13 C15 111.42(13) . . ?
O4 C13 C10 108.72(12) . . ?
C14 C13 C10 111.02(12) . . ?
C15 C13 C10 109.38(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 C13 112.95(13) . . ?
O5 C15 H15A 109.0 . . ?
C13 C15 H15A 109.0 . . ?
O5 C15 H15B 109.0 . . ?
C13 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C9 O3 C10 108.15(11) . . ?
C13 O4 H4A 109.5 . . ?
C15 O5 H5A 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
O1 C1 C2 O2 7.6(2) . . . . ?
C12 C1 C2 O2 -171.67(15) . . . . ?
O1 C1 C2 C3 -173.02(15) . . . . ?
C12 C1 C2 C3 7.7(2) . . . . ?
O2 C2 C3 C4 -6.1(2) . . . . ?
C1 C2 C3 C4 174.52(14) . . . . ?
O2 C2 C3 C8 174.40(16) . . . . ?
C1 C2 C3 C8 -4.9(2) . . . . ?
C8 C3 C4 C5 0.8(2) . . . . ?
C2 C3 C4 C5 -178.70(15) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C3 -0.6(2) . . . . ?
C6 C7 C8 C9 179.54(15) . . . . ?
C4 C3 C8 C7 0.0(2) . . . . ?
C2 C3 C8 C7 179.47(14) . . . . ?
C4 C3 C8 C9 179.85(14) . . . . ?
C2 C3 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 O3 2.1(2) . . . . ?
C3 C8 C9 O3 -177.78(13) . . . . ?
C7 C8 C9 C12 -176.11(15) . . . . ?
C3 C8 C9 C12 4.0(2) . . . . ?
O3 C10 C11 C12 -6.67(15) . . . . ?
C13 C10 C11 C12 112.39(14) . . . . ?
O3 C9 C12 C1 -179.28(14) . . . . ?
C8 C9 C12 C1 -1.0(2) . . . . ?
O3 C9 C12 C11 -0.67(18) . . . . ?
C8 C9 C12 C11 177.58(14) . . . . ?
O1 C1 C12 C9 175.92(16) . . . . ?
C2 C1 C12 C9 -4.8(2) . . . . ?
O1 C1 C12 C11 -2.4(3) . . . . ?
C2 C1 C12 C11 176.87(15) . . . . ?
C10 C11 C12 C9 4.69(17) . . . . ?
C10 C11 C12 C1 -176.86(16) . . . . ?
O3 C10 C13 O4 69.88(14) . . . . ?
C11 C10 C13 O4 -47.71(16) . . . . ?
O3 C10 C13 C14 -53.55(15) . . . . ?
C11 C10 C13 C14 -171.14(13) . . . . ?
O3 C10 C13 C15 -176.92(11) . . . . ?
C11 C10 C13 C15 65.50(16) . . . . ?
O4 C13 C15 O5 170.01(11) . . . . ?
C14 C13 C15 O5 -69.22(16) . . . . ?
C10 C13 C15 O5 53.90(16) . . . . ?
C12 C9 O3 C10 -3.97(17) . . . . ?
C8 C9 O3 C10 177.66(12) . . . . ?
C13 C10 O3 C9 -116.57(12) . . . . ?
C11 C10 O3 C9 6.71(15) . . . . ?

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
O4 H4A O5 0.82 1.94 2.7494(16) 169.2 7_765
O5 H5A O1 0.82 1.92 2.7275(16) 166.4 4_746

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 971197'
_audit_update_record             
;
2013-11-09 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 O5'
_chemical_formula_weight         274.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   7.3939(4)
_cell_length_b                   19.7414(11)
_cell_length_c                   8.5702(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.998(2)
_cell_angle_gamma                90.00
_cell_volume                     1244.11(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3999
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      29.72

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9123
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13277
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2851
_reflns_number_gt                2269
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0801P)²+0.1624P] 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         2851
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1364
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88425(19) 0.12172(7) 0.52442(16) 0.0282(3) Uani 1 1 d . . .
C2 C 0.8702(2) 0.10362(7) 0.68926(16) 0.0318(3) Uani 1 1 d . . .
C3 C 0.7851(2) 0.03660(8) 0.71153(17) 0.0327(3) Uani 1 1 d . . .
C4 C 0.7546(2) 0.01601(9) 0.86143(19) 0.0438(4) Uani 1 1 d . . .
H4 H 0.7879 0.0441 0.9467 0.053 Uiso 1 1 calc R . .
C5 C 0.6750(3) -0.04616(10) 0.8847(2) 0.0493(4) Uani 1 1 d . . .
H5 H 0.6541 -0.0596 0.9852 0.059 Uiso 1 1 calc R . .
C6 C 0.6266(2) -0.08807(9) 0.7587(2) 0.0451(4) Uani 1 1 d . . .
H6 H 0.5739 -0.1300 0.7747 0.054 Uiso 1 1 calc R . .
C7 C 0.6559(2) -0.06819(8) 0.6081(2) 0.0378(4) Uani 1 1 d . . .
H7 H 0.6217 -0.0966 0.5235 0.045 Uiso 1 1 calc R . .
C8 C 0.73580(19) -0.00621(7) 0.58306(17) 0.0304(3) Uani 1 1 d . . .
C9 C 0.76928(19) 0.01385(7) 0.41903(17) 0.0304(3) Uani 1 1 d . . .
C10 C 0.83922(19) 0.08163(7) 0.40082(16) 0.0289(3) Uani 1 1 d . . .
C11 C 0.8794(2) 0.11762(7) 0.25516(16) 0.0321(3) Uani 1 1 d . . .
H11A H 0.7700 0.1238 0.1837 0.039 Uiso 1 1 calc R . .
H11B H 0.9686 0.0932 0.2017 0.039 Uiso 1 1 calc R . .
C12 C 0.95552(19) 0.18618(7) 0.31933(16) 0.0298(3) Uani 1 1 d . . .
H12 H 1.0820 0.1903 0.2960 0.036 Uiso 1 1 calc R . .
C13 C 0.85137(19) 0.24879(7) 0.25783(16) 0.0301(3) Uani 1 1 d . . .
C14 C 0.9096(3) 0.31154(8) 0.3522(2) 0.0444(4) Uani 1 1 d . . .
H14A H 0.8434 0.3501 0.3083 0.067 Uiso 1 1 calc R . .
H14B H 1.0375 0.3189 0.3490 0.067 Uiso 1 1 calc R . .
H14C H 0.8848 0.3054 0.4590 0.067 Uiso 1 1 calc R . .
C15 C 0.8810(2) 0.25868(9) 0.08521(17) 0.0381(4) Uani 1 1 d . . .
H15A H 0.8581 0.2166 0.0283 0.046 Uiso 1 1 calc R . .
H15B H 0.7979 0.2928 0.0381 0.046 Uiso 1 1 calc R . .
O1 O 0.95252(14) 0.18278(5) 0.49147(11) 0.0336(3) Uani 1 1 d . . .
O2 O 0.92665(18) 0.14089(6) 0.79587(13) 0.0466(3) Uani 1 1 d . . .
O3 O 0.74122(17) -0.02545(6) 0.30954(13) 0.0458(3) Uani 1 1 d . . .
O4 O 0.66250(14) 0.23477(6) 0.26719(13) 0.0377(3) Uani 1 1 d . . .
H4A H 0.6019 0.2682 0.2391 0.057 Uiso 1 1 calc R . .
O5 O 1.06230(18) 0.27947(9) 0.07708(15) 0.0625(4) Uani 1 1 d . . .
H5A H 1.0887 0.2747 -0.0129 0.094 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
C1 C10 1.3363(19) . ?
C1 O1 1.3481(17) . ?
C1 C2 1.4713(19) . ?
C2 O2 1.2126(17) . ?
C2 C3 1.486(2) . ?
C3 C4 1.388(2) . ?
C3 C8 1.406(2) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.506(2) . ?
C9 O3 1.2185(17) . ?
C9 C10 1.449(2) . ?
C10 C11 1.493(2) . ?
C11 C12 1.545(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.4793(16) . ?
C12 C13 1.521(2) . ?
C12 H12 0.9800 . ?
C13 O4 1.4341(17) . ?
C13 C14 1.517(2) . ?
C13 C15 1.5306(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O5 1.410(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O4 H4A 0.8200 . ?
O5 H5A 0.8200 . ?

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
C10 C1 O1 115.55(13) . . ?
C10 C1 C2 125.49(13) . . ?
O1 C1 C2 118.93(12) . . ?
O2 C2 C1 121.53(13) . . ?
O2 C2 C3 124.08(13) . . ?
C1 C2 C3 114.38(12) . . ?
C4 C3 C8 119.68(15) . . ?
C4 C3 C2 119.44(14) . . ?
C8 C3 C2 120.89(13) . . ?
C5 C4 C3 120.34(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.96(16) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.40(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.29(16) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C3 119.33(14) . . ?
C7 C8 C9 119.42(14) . . ?
C3 C8 C9 121.25(13) . . ?
O3 C9 C10 122.62(14) . . ?
O3 C9 C8 121.33(14) . . ?
C10 C9 C8 116.03(12) . . ?
C1 C10 C9 121.58(13) . . ?
C1 C10 C11 109.04(13) . . ?
C9 C10 C11 129.35(13) . . ?
C10 C11 C12 102.49(11) . . ?
C10 C11 H11A 111.3 . . ?
C12 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
O1 C12 C13 108.82(11) . . ?
O1 C12 C11 105.81(11) . . ?
C13 C12 C11 115.85(12) . . ?
O1 C12 H12 108.7 . . ?
C13 C12 H12 108.7 . . ?
C11 C12 H12 108.7 . . ?
O4 C13 C14 110.58(12) . . ?
O4 C13 C12 106.53(11) . . ?
C14 C13 C12 111.94(12) . . ?
O4 C13 C15 108.51(11) . . ?
C14 C13 C15 110.47(13) . . ?
C12 C13 C15 108.67(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 C13 108.53(12) . . ?
O5 C15 H15A 110.0 . . ?
C13 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
C13 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C1 O1 C12 107.12(10) . . ?
C13 O4 H4A 109.5 . . ?
C15 O5 H5A 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 C1 C2 O2 174.35(15) . . . . ?
O1 C1 C2 O2 -3.7(2) . . . . ?
C10 C1 C2 C3 -4.8(2) . . . . ?
O1 C1 C2 C3 177.22(12) . . . . ?
O2 C2 C3 C4 4.8(2) . . . . ?
C1 C2 C3 C4 -176.11(14) . . . . ?
O2 C2 C3 C8 -174.93(15) . . . . ?
C1 C2 C3 C8 4.2(2) . . . . ?
C8 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C5 179.80(15) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C3 -0.7(2) . . . . ?
C6 C7 C8 C9 178.96(13) . . . . ?
C4 C3 C8 C7 0.6(2) . . . . ?
C2 C3 C8 C7 -179.67(13) . . . . ?
C4 C3 C8 C9 -179.04(14) . . . . ?
C2 C3 C8 C9 0.7(2) . . . . ?
C7 C8 C9 O3 -6.0(2) . . . . ?
C3 C8 C9 O3 173.60(14) . . . . ?
C7 C8 C9 C10 175.03(13) . . . . ?
C3 C8 C9 C10 -5.3(2) . . . . ?
O1 C1 C10 C9 178.15(12) . . . . ?
C2 C1 C10 C9 0.1(2) . . . . ?
O1 C1 C10 C11 0.03(17) . . . . ?
C2 C1 C10 C11 -178.04(13) . . . . ?
O3 C9 C10 C1 -173.93(14) . . . . ?
C8 C9 C10 C1 5.0(2) . . . . ?
O3 C9 C10 C11 3.8(2) . . . . ?
C8 C9 C10 C11 -177.31(13) . . . . ?
C1 C10 C11 C12 -0.18(15) . . . . ?
C9 C10 C11 C12 -178.11(14) . . . . ?
C10 C11 C12 O1 0.25(13) . . . . ?
C10 C11 C12 C13 -120.39(13) . . . . ?
O1 C12 C13 O4 -72.53(13) . . . . ?
C11 C12 C13 O4 46.48(15) . . . . ?
O1 C12 C13 C14 48.47(15) . . . . ?
C11 C12 C13 C14 167.47(12) . . . . ?
O1 C12 C13 C15 170.74(11) . . . . ?
C11 C12 C13 C15 -70.25(15) . . . . ?
O4 C13 C15 O5 173.89(13) . . . . ?
C14 C13 C15 O5 52.51(18) . . . . ?
C12 C13 C15 O5 -70.66(17) . . . . ?
C10 C1 O1 C12 0.15(16) . . . . ?
C2 C1 O1 C12 178.35(12) . . . . ?
C13 C12 O1 C1 124.87(12) . . . . ?
C11 C12 O1 C1 -0.25(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O2 0.82 2.29 3.0359(16) 150.6 4_565
O5 H5A O4 0.82 2.03 2.8447(17) 177.7 4_665

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
