# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_0802
_database_code_depnum_ccdc_archive 'CCDC 1533723'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 O7'
_chemical_formula_weight         462.48

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.0146(12)
_cell_length_b                   11.5764(18)
_cell_length_c                   12.796(2)
_cell_angle_alpha                100.955(2)
_cell_angle_beta                 90.258(2)
_cell_angle_gamma                101.472(2)
_cell_volume                     1141.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1517
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.81

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8766
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5478
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3950
_reflns_number_gt                2758
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 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)+(0.0511P)²+0.9767P] 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         3950
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O5 O 0.1919(2) 0.02306(18) 0.26461(15) 0.0297(5) Uani 1 1 d . . .
O3 O -0.2654(2) -0.00352(18) 0.26036(15) 0.0291(5) Uani 1 1 d . . .
O4 O -0.0947(2) 0.01942(17) 0.12460(15) 0.0284(5) Uani 1 1 d . . .
O1 O -0.2278(2) 0.04723(18) 0.51318(16) 0.0295(5) Uani 1 1 d . . .
O6 O 0.2730(3) 0.20430(19) 0.21979(17) 0.0368(5) Uani 1 1 d . . .
O2 O -0.2766(2) 0.20412(17) 0.44827(16) 0.0292(5) Uani 1 1 d . . .
C8 C 0.1381(3) 0.3623(2) 0.4468(2) 0.0212(6) Uani 1 1 d . . .
C9 C 0.1040(3) 0.2493(2) 0.4781(2) 0.0183(6) Uani 1 1 d . . .
C10 C 0.1718(3) 0.2361(2) 0.5728(2) 0.0225(6) Uani 1 1 d . . .
H1 H 0.1484 0.1594 0.5921 0.027 Uiso 1 1 calc R . .
C18 C 0.0756(4) 0.3779(2) 0.3392(2) 0.0260(7) Uani 1 1 d . . .
H2 H 0.1758 0.3952 0.2955 0.031 Uiso 1 1 calc R . .
H3 H 0.0222 0.4491 0.3505 0.031 Uiso 1 1 calc R . .
C24 C -0.1381(4) 0.0459(2) 0.2255(2) 0.0233(6) Uani 1 1 d . . .
C19 C -0.0117(3) 0.1405(2) 0.4094(2) 0.0202(6) Uani 1 1 d . . .
H4 H 0.0374 0.0692 0.4162 0.024 Uiso 1 1 calc R . .
C1 C -0.0846(4) 0.2829(2) 0.1614(2) 0.0260(7) Uani 1 1 d . . .
C11 C 0.2753(3) 0.3336(2) 0.6422(2) 0.0212(6) Uani 1 1 d . . .
C22 C -0.1855(3) 0.1228(2) 0.4599(2) 0.0218(6) Uani 1 1 d . . .
C12 C 0.3090(3) 0.4474(2) 0.6117(2) 0.0216(6) Uani 1 1 d . . .
C13 C 0.3473(4) 0.3211(3) 0.7402(2) 0.0290(7) Uani 1 1 d . . .
H5 H 0.3269 0.2449 0.7603 0.035 Uiso 1 1 calc R . .
C14 C 0.4459(4) 0.4182(3) 0.8056(2) 0.0304(7) Uani 1 1 d . . .
H6 H 0.4934 0.4089 0.8709 0.037 Uiso 1 1 calc R . .
C15 C 0.4128(4) 0.5457(3) 0.6823(2) 0.0289(7) Uani 1 1 d . . .
H7 H 0.4376 0.6225 0.6633 0.035 Uiso 1 1 calc R . .
C25 C 0.1687(4) 0.1315(3) 0.2536(2) 0.0238(6) Uani 1 1 d . . .
C2 C -0.1679(4) 0.3014(3) -0.0470(2) 0.0295(7) Uani 1 1 d . . .
C3 C -0.0005(4) 0.3347(3) -0.0088(2) 0.0286(7) Uani 1 1 d . . .
H8 H 0.0868 0.3639 -0.0528 0.034 Uiso 1 1 calc R . .
C4 C 0.0391(4) 0.3250(3) 0.0947(2) 0.0287(7) Uani 1 1 d . . .
H9 H 0.1546 0.3481 0.1206 0.034 Uiso 1 1 calc R . .
C20 C -0.0066(3) 0.1488(2) 0.2899(2) 0.0213(6) Uani 1 1 d . . .
C16 C 0.4770(4) 0.5311(3) 0.7767(2) 0.0293(7) Uani 1 1 d . . .
H10 H 0.5436 0.5983 0.8235 0.035 Uiso 1 1 calc R . .
C5 C -0.2929(4) 0.2592(3) 0.0183(3) 0.0359(8) Uani 1 1 d . . .
H11 H -0.4082 0.2357 -0.0079 0.043 Uiso 1 1 calc R . .
C23 C -0.4366(4) 0.1942(3) 0.5028(3) 0.0342(8) Uani 1 1 d . . .
H12 H -0.5051 0.1129 0.4801 0.051 Uiso 1 1 calc R . .
H13 H -0.4996 0.2527 0.4850 0.051 Uiso 1 1 calc R . .
H14 H -0.4128 0.2101 0.5799 0.051 Uiso 1 1 calc R . .
C6 C -0.2520(4) 0.2507(3) 0.1208(2) 0.0312(7) Uani 1 1 d . . .
H15 H -0.3400 0.2223 0.1647 0.037 Uiso 1 1 calc R . .
C17 C 0.2398(4) 0.4577(2) 0.5133(2) 0.0236(6) Uani 1 1 d . . .
H16 H 0.2644 0.5335 0.4922 0.028 Uiso 1 1 calc R . .
C21 C -0.0510(4) 0.2720(3) 0.2761(2) 0.0270(7) Uani 1 1 d . . .
H17 H -0.1618 0.2746 0.3111 0.032 Uiso 1 1 calc R . .
O7 O -0.2227(3) 0.3070(2) -0.14726(17) 0.0446(6) Uani 1 1 d . . .
C26 C 0.3567(4) -0.0036(3) 0.2375(3) 0.0401(8) Uani 1 1 d . . .
H18 H 0.3720 -0.0061 0.1613 0.060 Uiso 1 1 calc R . .
H19 H 0.3637 -0.0817 0.2543 0.060 Uiso 1 1 calc R . .
H20 H 0.4461 0.0589 0.2787 0.060 Uiso 1 1 calc R . .
C27 C -0.2189(4) -0.0702(3) 0.0535(2) 0.0369(8) Uani 1 1 d . . .
H21 H -0.2437 -0.1446 0.0816 0.055 Uiso 1 1 calc R . .
H22 H -0.1727 -0.0863 -0.0174 0.055 Uiso 1 1 calc R . .
H23 H -0.3240 -0.0401 0.0485 0.055 Uiso 1 1 calc R . .
C28 C -0.0964(5) 0.3332(4) -0.2216(3) 0.0520(10) Uani 1 1 d . . .
H24 H -0.0259 0.4132 -0.1956 0.078 Uiso 1 1 calc R . .
H25 H -0.1517 0.3314 -0.2906 0.078 Uiso 1 1 calc R . .
H26 H -0.0244 0.2731 -0.2301 0.078 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
O5 C25 1.338(3) . ?
O5 C26 1.444(3) . ?
O3 C24 1.198(3) . ?
O4 C24 1.334(3) . ?
O4 C27 1.455(3) . ?
O1 C22 1.206(3) . ?
O6 C25 1.207(3) . ?
O2 C22 1.330(3) . ?
O2 C23 1.457(3) . ?
C8 C17 1.374(4) . ?
C8 C9 1.416(4) . ?
C8 C18 1.517(4) . ?
C9 C10 1.372(4) . ?
C9 C19 1.526(4) . ?
C10 C11 1.412(4) . ?
C18 C21 1.519(4) . ?
C24 C20 1.526(4) . ?
C19 C22 1.532(4) . ?
C19 C20 1.550(4) . ?
C1 C4 1.386(4) . ?
C1 C6 1.389(4) . ?
C1 C21 1.524(4) . ?
C11 C12 1.420(4) . ?
C11 C13 1.421(4) . ?
C12 C17 1.408(4) . ?
C12 C15 1.424(4) . ?
C13 C14 1.368(4) . ?
C14 C16 1.401(4) . ?
C15 C16 1.364(4) . ?
C25 C20 1.521(4) . ?
C2 O7 1.371(3) . ?
C2 C3 1.380(4) . ?
C2 C5 1.381(4) . ?
C3 C4 1.391(4) . ?
C20 C21 1.577(4) . ?
C5 C6 1.377(4) . ?
O7 C28 1.421(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
C25 O5 C26 116.1(2) . . ?
C24 O4 C27 115.8(2) . . ?
C22 O2 C23 115.0(2) . . ?
C17 C8 C9 118.5(2) . . ?
C17 C8 C18 119.7(2) . . ?
C9 C8 C18 121.7(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 C19 118.4(2) . . ?
C8 C9 C19 121.2(2) . . ?
C9 C10 C11 121.7(2) . . ?
C8 C18 C21 116.1(2) . . ?
O3 C24 O4 124.2(3) . . ?
O3 C24 C20 124.6(3) . . ?
O4 C24 C20 111.2(2) . . ?
C9 C19 C22 107.7(2) . . ?
C9 C19 C20 111.2(2) . . ?
C22 C19 C20 118.1(2) . . ?
C4 C1 C6 117.2(3) . . ?
C4 C1 C21 124.9(3) . . ?
C6 C1 C21 117.8(3) . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 C13 122.3(3) . . ?
C12 C11 C13 119.5(3) . . ?
O1 C22 O2 123.5(3) . . ?
O1 C22 C19 121.9(2) . . ?
O2 C22 C19 114.3(2) . . ?
C17 C12 C11 118.8(2) . . ?
C17 C12 C15 123.2(3) . . ?
C11 C12 C15 118.0(2) . . ?
C14 C13 C11 120.5(3) . . ?
C13 C14 C16 120.3(3) . . ?
C16 C15 C12 121.0(3) . . ?
O6 C25 O5 124.4(3) . . ?
O6 C25 C20 125.5(3) . . ?
O5 C25 C20 110.1(2) . . ?
O7 C2 C3 124.7(3) . . ?
O7 C2 C5 115.9(3) . . ?
C3 C2 C5 119.4(3) . . ?
C2 C3 C4 119.4(3) . . ?
C1 C4 C3 122.1(3) . . ?
C25 C20 C24 107.6(2) . . ?
C25 C20 C19 106.9(2) . . ?
C24 C20 C19 109.6(2) . . ?
C25 C20 C21 114.6(2) . . ?
C24 C20 C21 108.9(2) . . ?
C19 C20 C21 109.2(2) . . ?
C15 C16 C14 120.7(3) . . ?
C6 C5 C2 120.6(3) . . ?
C5 C6 C1 121.3(3) . . ?
C8 C17 C12 122.4(3) . . ?
C18 C21 C1 113.8(2) . . ?
C18 C21 C20 111.2(2) . . ?
C1 C21 C20 115.1(2) . . ?
C2 O7 C28 117.5(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
C17 C8 C9 C10 -0.2(4) . . . . ?
C18 C8 C9 C10 175.5(3) . . . . ?
C17 C8 C9 C19 178.4(3) . . . . ?
C18 C8 C9 C19 -5.9(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C19 C9 C10 C11 -177.9(2) . . . . ?
C17 C8 C18 C21 -173.7(3) . . . . ?
C9 C8 C18 C21 10.6(4) . . . . ?
C27 O4 C24 O3 4.2(4) . . . . ?
C27 O4 C24 C20 -174.6(2) . . . . ?
C10 C9 C19 C22 76.4(3) . . . . ?
C8 C9 C19 C22 -102.2(3) . . . . ?
C10 C9 C19 C20 -152.7(2) . . . . ?
C8 C9 C19 C20 28.7(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C11 C13 -179.6(3) . . . . ?
C23 O2 C22 O1 -1.6(4) . . . . ?
C23 O2 C22 C19 -175.5(2) . . . . ?
C9 C19 C22 O1 -101.4(3) . . . . ?
C20 C19 C22 O1 131.6(3) . . . . ?
C9 C19 C22 O2 72.7(3) . . . . ?
C20 C19 C22 O2 -54.3(3) . . . . ?
C10 C11 C12 C17 -0.8(4) . . . . ?
C13 C11 C12 C17 178.6(3) . . . . ?
C10 C11 C12 C15 179.7(3) . . . . ?
C13 C11 C12 C15 -0.9(4) . . . . ?
C10 C11 C13 C14 -179.5(3) . . . . ?
C12 C11 C13 C14 1.1(4) . . . . ?
C11 C13 C14 C16 0.0(5) . . . . ?
C17 C12 C15 C16 -179.9(3) . . . . ?
C11 C12 C15 C16 -0.4(4) . . . . ?
C26 O5 C25 O6 2.6(4) . . . . ?
C26 O5 C25 C20 -177.3(2) . . . . ?
O7 C2 C3 C4 179.9(3) . . . . ?
C5 C2 C3 C4 0.0(5) . . . . ?
C6 C1 C4 C3 -0.3(4) . . . . ?
C21 C1 C4 C3 -178.8(3) . . . . ?
C2 C3 C4 C1 0.0(5) . . . . ?
O6 C25 C20 C24 123.8(3) . . . . ?
O5 C25 C20 C24 -56.3(3) . . . . ?
O6 C25 C20 C19 -118.6(3) . . . . ?
O5 C25 C20 C19 61.3(3) . . . . ?
O6 C25 C20 C21 2.6(4) . . . . ?
O5 C25 C20 C21 -177.6(2) . . . . ?
O3 C24 C20 C25 142.3(3) . . . . ?
O4 C24 C20 C25 -38.8(3) . . . . ?
O3 C24 C20 C19 26.5(4) . . . . ?
O4 C24 C20 C19 -154.6(2) . . . . ?
O3 C24 C20 C21 -92.9(3) . . . . ?
O4 C24 C20 C21 85.9(3) . . . . ?
C9 C19 C20 C25 69.9(3) . . . . ?
C22 C19 C20 C25 -164.8(2) . . . . ?
C9 C19 C20 C24 -173.8(2) . . . . ?
C22 C19 C20 C24 -48.4(3) . . . . ?
C9 C19 C20 C21 -54.5(3) . . . . ?
C22 C19 C20 C21 70.8(3) . . . . ?
C12 C15 C16 C14 1.6(4) . . . . ?
C13 C14 C16 C15 -1.3(5) . . . . ?
O7 C2 C5 C6 -179.5(3) . . . . ?
C3 C2 C5 C6 0.4(5) . . . . ?
C2 C5 C6 C1 -0.8(5) . . . . ?
C4 C1 C6 C5 0.7(4) . . . . ?
C21 C1 C6 C5 179.3(3) . . . . ?
C9 C8 C17 C12 -0.9(4) . . . . ?
C18 C8 C17 C12 -176.7(3) . . . . ?
C11 C12 C17 C8 1.4(4) . . . . ?
C15 C12 C17 C8 -179.1(3) . . . . ?
C8 C18 C21 C1 -169.4(2) . . . . ?
C8 C18 C21 C20 -37.5(3) . . . . ?
C4 C1 C21 C18 41.3(4) . . . . ?
C6 C1 C21 C18 -137.2(3) . . . . ?
C4 C1 C21 C20 -88.7(3) . . . . ?
C6 C1 C21 C20 92.8(3) . . . . ?
C25 C20 C21 C18 -59.8(3) . . . . ?
C24 C20 C21 C18 179.7(2) . . . . ?
C19 C20 C21 C18 60.0(3) . . . . ?
C25 C20 C21 C1 71.5(3) . . . . ?
C24 C20 C21 C1 -49.1(3) . . . . ?
C19 C20 C21 C1 -168.7(2) . . . . ?
C3 C2 O7 C28 9.0(5) . . . . ?
C5 C2 O7 C28 -171.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1533724'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 O6'
_chemical_formula_weight         366.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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)/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                   10.3174(13)
_cell_length_b                   19.294(2)
_cell_length_c                   9.0603(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.414(2)
_cell_angle_gamma                90.00
_cell_volume                     1746.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2546
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.06

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8319
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3109
_reflns_number_gt                2396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 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)+(0.0400P)²+0.5072P] 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       0.0023(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3109
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C10 C 0.38678(16) 0.15349(9) 0.32694(19) 0.0204(4) Uani 1 1 d . . .
C12 C 0.69474(17) 0.12082(9) 0.5747(2) 0.0219(4) Uani 1 1 d . . .
H12 H 0.6111 0.0974 0.5523 0.026 Uiso 1 1 calc R . .
C11 C 0.44528(17) 0.21577(8) 0.30208(19) 0.0208(4) Uani 1 1 d . . .
C15 C 0.65899(16) 0.15332(8) 0.29143(19) 0.0192(4) Uani 1 1 d . . .
H15 H 0.7276 0.1544 0.2305 0.023 Uiso 1 1 calc R . .
C4 C 0.89449(16) 0.15539(8) 0.7583(2) 0.0206(4) Uani 1 1 d . . .
C6 C 0.38658(18) 0.27753(9) 0.3332(2) 0.0263(4) Uani 1 1 d . . .
H6 H 0.4245 0.3205 0.3147 0.032 Uiso 1 1 calc R . .
C3 C 0.73513(16) 0.15370(8) 0.45781(19) 0.0191(4) Uani 1 1 d . . .
C5 C 0.77298(17) 0.12108(8) 0.7239(2) 0.0222(4) Uani 1 1 d . . .
H5 H 0.7431 0.0978 0.8018 0.027 Uiso 1 1 calc R . .
C20 C 0.53587(17) 0.08370(8) 0.0685(2) 0.0226(4) Uani 1 1 d . . .
C7 C 0.27502(18) 0.27713(10) 0.3901(2) 0.0312(5) Uani 1 1 d . . .
H7 H 0.2360 0.3196 0.4099 0.037 Uiso 1 1 calc R . .
C16 C 0.57456(16) 0.08707(8) 0.2428(2) 0.0200(4) Uani 1 1 d . . .
C14 C 0.56958(17) 0.21707(8) 0.2437(2) 0.0226(4) Uani 1 1 d . . .
H14A H 0.6216 0.2593 0.2822 0.027 Uiso 1 1 calc R . .
H14B H 0.5433 0.2198 0.1310 0.027 Uiso 1 1 calc R . .
C9 C 0.27467(17) 0.15313(10) 0.3863(2) 0.0276(4) Uani 1 1 d . . .
H9 H 0.2360 0.1103 0.4048 0.033 Uiso 1 1 calc R . .
C1 C 0.85719(17) 0.18892(9) 0.4966(2) 0.0262(4) Uani 1 1 d . . .
H1 H 0.8873 0.2124 0.4192 0.031 Uiso 1 1 calc R . .
C17 C 0.65696(17) 0.02098(9) 0.2979(2) 0.0231(4) Uani 1 1 d . . .
C2 C 0.93525(18) 0.19059(9) 0.6444(2) 0.0283(4) Uani 1 1 d . . .
H2 H 1.0169 0.2158 0.6680 0.034 Uiso 1 1 calc R . .
C19 C 0.43886(16) 0.08420(8) 0.2836(2) 0.0211(4) Uani 1 1 d . . .
H19 H 0.4428 0.0497 0.3670 0.025 Uiso 1 1 calc R . .
C8 C 0.21947(19) 0.21494(10) 0.4185(2) 0.0311(5) Uani 1 1 d . . .
H8 H 0.1436 0.2146 0.4601 0.037 Uiso 1 1 calc R . .
C13 C 0.94063(19) 0.12300(10) 1.0210(2) 0.0326(5) Uani 1 1 d . . .
H13A H 0.8577 0.1437 1.0350 0.049 Uiso 1 1 calc R . .
H13B H 1.0112 0.1275 1.1155 0.049 Uiso 1 1 calc R . .
H13C H 0.9256 0.0738 0.9952 0.049 Uiso 1 1 calc R . .
C21 C 0.34294(18) 0.05898(8) 0.1384(2) 0.0252(4) Uani 1 1 d . . .
C18 C 0.8608(2) -0.03547(10) 0.3036(3) 0.0417(6) Uani 1 1 d . . .
H18A H 0.8894 -0.0395 0.4149 0.063 Uiso 1 1 calc R . .
H18B H 0.9396 -0.0301 0.2625 0.063 Uiso 1 1 calc R . .
H18C H 0.8118 -0.0774 0.2610 0.063 Uiso 1 1 calc R . .
O4 O 0.98050(11) 0.15799(6) 0.90032(14) 0.0267(3) Uani 1 1 d . . .
O2 O 0.60197(13) 0.09540(6) -0.01819(14) 0.0290(3) Uani 1 1 d . . .
O1 O 0.40412(12) 0.06310(6) 0.01707(14) 0.0269(3) Uani 1 1 d . . .
O3 O 0.23045(13) 0.03990(6) 0.11633(17) 0.0354(4) Uani 1 1 d . . .
O5 O 0.77440(12) 0.02449(6) 0.26293(15) 0.0298(3) Uani 1 1 d . . .
O6 O 0.61849(13) -0.02632(6) 0.36130(15) 0.0324(3) 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
C10 C11 1.388(2) . ?
C10 C9 1.392(2) . ?
C10 C19 1.528(2) . ?
C12 C3 1.384(2) . ?
C12 C5 1.392(2) . ?
C11 C6 1.397(2) . ?
C11 C14 1.504(2) . ?
C15 C3 1.517(2) . ?
C15 C14 1.534(2) . ?
C15 C16 1.548(2) . ?
C4 O4 1.370(2) . ?
C4 C5 1.383(2) . ?
C4 C2 1.385(3) . ?
C6 C7 1.373(3) . ?
C3 C1 1.397(2) . ?
C20 O2 1.183(2) . ?
C20 O1 1.381(2) . ?
C20 C16 1.531(2) . ?
C7 C8 1.381(3) . ?
C16 C19 1.535(2) . ?
C16 C17 1.545(2) . ?
C9 C8 1.384(3) . ?
C1 C2 1.380(3) . ?
C17 O6 1.198(2) . ?
C17 O5 1.328(2) . ?
C19 C21 1.516(2) . ?
C13 O4 1.430(2) . ?
C21 O3 1.186(2) . ?
C21 O1 1.399(2) . ?
C18 O5 1.451(2) . ?

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
C11 C10 C9 120.25(16) . . ?
C11 C10 C19 121.38(15) . . ?
C9 C10 C19 118.31(15) . . ?
C3 C12 C5 121.95(15) . . ?
C10 C11 C6 118.55(16) . . ?
C10 C11 C14 120.98(14) . . ?
C6 C11 C14 120.48(15) . . ?
C3 C15 C14 113.76(14) . . ?
C3 C15 C16 113.73(13) . . ?
C14 C15 C16 109.00(13) . . ?
O4 C4 C5 124.59(16) . . ?
O4 C4 C2 115.85(15) . . ?
C5 C4 C2 119.56(16) . . ?
C7 C6 C11 121.13(17) . . ?
C12 C3 C1 117.03(16) . . ?
C12 C3 C15 125.30(15) . . ?
C1 C3 C15 117.66(15) . . ?
C4 C5 C12 119.64(16) . . ?
O2 C20 O1 120.80(16) . . ?
O2 C20 C16 129.16(16) . . ?
O1 C20 C16 110.04(15) . . ?
C6 C7 C8 120.02(17) . . ?
C20 C16 C19 103.13(13) . . ?
C20 C16 C17 106.20(13) . . ?
C19 C16 C17 110.74(14) . . ?
C20 C16 C15 108.21(14) . . ?
C19 C16 C15 116.34(14) . . ?
C17 C16 C15 111.37(13) . . ?
C11 C14 C15 113.14(13) . . ?
C8 C9 C10 120.17(17) . . ?
C2 C1 C3 121.83(17) . . ?
O6 C17 O5 125.75(16) . . ?
O6 C17 C16 124.22(16) . . ?
O5 C17 C16 110.02(15) . . ?
C1 C2 C4 119.93(16) . . ?
C21 C19 C10 107.97(13) . . ?
C21 C19 C16 103.91(14) . . ?
C10 C19 C16 115.49(14) . . ?
C7 C8 C9 119.85(18) . . ?
O3 C21 O1 119.95(17) . . ?
O3 C21 C19 130.21(18) . . ?
O1 C21 C19 109.79(14) . . ?
C4 O4 C13 117.30(13) . . ?
C20 O1 C21 110.46(13) . . ?
C17 O5 C18 115.98(15) . . ?

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
C9 C10 C11 C6 -2.1(2) . . . . ?
C19 C10 C11 C6 175.08(15) . . . . ?
C9 C10 C11 C14 177.62(16) . . . . ?
C19 C10 C11 C14 -5.2(2) . . . . ?
C10 C11 C6 C7 1.3(3) . . . . ?
C14 C11 C6 C7 -178.39(16) . . . . ?
C5 C12 C3 C1 -1.5(2) . . . . ?
C5 C12 C3 C15 177.23(15) . . . . ?
C14 C15 C3 C12 95.84(19) . . . . ?
C16 C15 C3 C12 -29.8(2) . . . . ?
C14 C15 C3 C1 -85.41(19) . . . . ?
C16 C15 C3 C1 148.99(15) . . . . ?
O4 C4 C5 C12 -178.79(15) . . . . ?
C2 C4 C5 C12 1.6(2) . . . . ?
C3 C12 C5 C4 0.4(3) . . . . ?
C11 C6 C7 C8 0.5(3) . . . . ?
O2 C20 C16 C19 166.38(17) . . . . ?
O1 C20 C16 C19 -14.22(16) . . . . ?
O2 C20 C16 C17 -77.1(2) . . . . ?
O1 C20 C16 C17 102.30(15) . . . . ?
O2 C20 C16 C15 42.6(2) . . . . ?
O1 C20 C16 C15 -138.03(13) . . . . ?
C3 C15 C16 C20 -164.34(13) . . . . ?
C14 C15 C16 C20 67.57(17) . . . . ?
C3 C15 C16 C19 80.21(18) . . . . ?
C14 C15 C16 C19 -47.88(19) . . . . ?
C3 C15 C16 C17 -47.98(19) . . . . ?
C14 C15 C16 C17 -176.07(14) . . . . ?
C10 C11 C14 C15 -29.4(2) . . . . ?
C6 C11 C14 C15 150.29(16) . . . . ?
C3 C15 C14 C11 -74.01(18) . . . . ?
C16 C15 C14 C11 54.06(18) . . . . ?
C11 C10 C9 C8 1.1(3) . . . . ?
C19 C10 C9 C8 -176.13(16) . . . . ?
C12 C3 C1 C2 0.6(3) . . . . ?
C15 C3 C1 C2 -178.27(16) . . . . ?
C20 C16 C17 O6 -110.13(19) . . . . ?
C19 C16 C17 O6 1.2(2) . . . . ?
C15 C16 C17 O6 132.28(18) . . . . ?
C20 C16 C17 O5 69.23(17) . . . . ?
C19 C16 C17 O5 -179.49(14) . . . . ?
C15 C16 C17 O5 -48.36(19) . . . . ?
C3 C1 C2 C4 1.5(3) . . . . ?
O4 C4 C2 C1 177.83(16) . . . . ?
C5 C4 C2 C1 -2.6(3) . . . . ?
C11 C10 C19 C21 -103.72(18) . . . . ?
C9 C10 C19 C21 73.47(19) . . . . ?
C11 C10 C19 C16 12.0(2) . . . . ?
C9 C10 C19 C16 -170.77(15) . . . . ?
C20 C16 C19 C21 15.79(16) . . . . ?
C17 C16 C19 C21 -97.46(15) . . . . ?
C15 C16 C19 C21 134.05(14) . . . . ?
C20 C16 C19 C10 -102.26(16) . . . . ?
C17 C16 C19 C10 144.50(15) . . . . ?
C15 C16 C19 C10 16.0(2) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C10 C9 C8 C7 0.7(3) . . . . ?
C10 C19 C21 O3 -67.6(2) . . . . ?
C16 C19 C21 O3 169.25(17) . . . . ?
C10 C19 C21 O1 109.86(15) . . . . ?
C16 C19 C21 O1 -13.26(17) . . . . ?
C5 C4 O4 C13 -0.4(2) . . . . ?
C2 C4 O4 C13 179.15(16) . . . . ?
O2 C20 O1 C21 -174.18(15) . . . . ?
C16 C20 O1 C21 6.37(17) . . . . ?
O3 C21 O1 C20 -177.62(15) . . . . ?
C19 C21 O1 C20 4.59(17) . . . . ?
O6 C17 O5 C18 1.3(3) . . . . ?
C16 C17 O5 C18 -178.03(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
