# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_naphtho
_database_code_depnum_ccdc_archive 'CCDC 1426546'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(rac)-(5S,6S,7S,8R)-Naphtho[2,3-d]-1,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-5-(3,4,5-trimethoxyphenyl) -7-( dimethoxyphosphoryl)-, methyl ester'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H29 O11 P'
_chemical_formula_sum            'C24 H29 O11 P'
_chemical_formula_weight         524.44

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'
P P 0.2955 0.4335 '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'
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.0529(7)
_cell_length_b                   10.0781(8)
_cell_length_c                   13.2162(9)
_cell_angle_alpha                79.723(5)
_cell_angle_beta                 74.590(6)
_cell_angle_gamma                72.609(7)
_cell_volume                     1224.69(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    18102
_cell_measurement_theta_min      4.62
_cell_measurement_theta_max      67.06

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
'SCALE3 ABSPACK, CrysAlisPro, Agilent Technologies, V.1.171.36.20'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire 3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1835
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18102
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.62
_diffrn_reflns_theta_max         67.06
_reflns_number_total             4331
_reflns_number_gt                3651
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1469P)²+0.0965P] 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       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4331
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.2115
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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
O1 O 0.3763(3) 0.5459(2) -0.11198(18) 0.0800(7) Uani 1 1 d . . .
C2 C 0.2756(5) 0.6174(4) -0.1735(3) 0.0845(10) Uani 1 1 d . . .
H2A H 0.320(6) 0.639(5) -0.246(4) 0.127 Uiso 1 1 d . . .
H2B H 0.232(6) 0.707(6) -0.158(4) 0.127 Uiso 1 1 d . . .
O3 O 0.1740(3) 0.5405(3) -0.1615(2) 0.0897(8) Uani 1 1 d . . .
C4 C 0.1497(3) 0.3179(3) -0.0543(2) 0.0621(7) Uani 1 1 d . . .
H4 H 0.0688 0.3163 -0.0750 0.075 Uiso 1 1 calc R . .
C5 C 0.2101(3) 0.2114(3) 0.01685(18) 0.0516(6) Uani 1 1 d . . .
C6 C 0.3307(2) 0.2152(2) 0.04742(17) 0.0490(5) Uani 1 1 d . . .
C7 C 0.3947(3) 0.3264(3) 0.00687(19) 0.0555(6) Uani 1 1 d . . .
H7 H 0.4755 0.3303 0.0267 0.067 Uiso 1 1 calc R . .
C8 C 0.3335(3) 0.4276(3) -0.0623(2) 0.0592(6) Uani 1 1 d . . .
C9 C 0.2138(3) 0.4243(3) -0.0922(2) 0.0627(7) Uani 1 1 d . . .
C10 C 0.1404(3) 0.0922(3) 0.05831(19) 0.0530(6) Uani 1 1 d . . .
H10 H 0.031(4) 0.137(4) 0.069(3) 0.079 Uiso 1 1 d . . .
C11 C 0.1680(3) 0.0253(3) 0.16792(18) 0.0512(6) Uani 1 1 d . . .
H11 H 0.126(4) 0.098(4) 0.213(3) 0.077 Uiso 1 1 d . . .
C12 C 0.3303(2) -0.0195(2) 0.15916(17) 0.0490(5) Uani 1 1 d . . .
H12 H 0.378(4) -0.079(3) 0.103(3) 0.074 Uiso 1 1 d . . .
C13 C 0.3922(2) 0.1109(2) 0.13103(17) 0.0469(5) Uani 1 1 d . . .
H13 H 0.491(4) 0.073(3) 0.104(2) 0.070 Uiso 1 1 d . . .
O14 O 0.1972(2) -0.0161(2) -0.01036(15) 0.0629(5) Uani 1 1 d . . .
H14A H 0.152(4) 0.014(4) -0.064(3) 0.094 Uiso 1 1 d . . .
P15 P 0.07018(7) -0.10720(7) 0.21971(5) 0.0555(3) Uani 1 1 d . . .
O16 O -0.0472(2) -0.0940(2) 0.16969(16) 0.0723(6) Uani 1 1 d . . .
O17 O 0.1817(2) -0.2561(2) 0.22099(16) 0.0694(5) Uani 1 1 d . . .
C18 C 0.2301(4) -0.3369(4) 0.1329(3) 0.0822(9) Uani 1 1 d . . .
H18A H 0.1593 -0.3828 0.1325 0.123 Uiso 1 1 calc R . .
H18B H 0.3183 -0.4056 0.1387 0.123 Uiso 1 1 calc R . .
H18C H 0.2452 -0.2762 0.0685 0.123 Uiso 1 1 calc R . .
O19 O 0.0180(2) -0.0848(2) 0.33944(14) 0.0658(5) Uani 1 1 d . . .
C20 C -0.0292(4) -0.1858(4) 0.4199(3) 0.0948(12) Uani 1 1 d . . .
H20A H -0.1108 -0.2045 0.4064 0.142 Uiso 1 1 calc R . .
H20B H -0.0551 -0.1504 0.4872 0.142 Uiso 1 1 calc R . .
H20C H 0.0465 -0.2706 0.4203 0.142 Uiso 1 1 calc R . .
C21 C 0.3804(3) -0.1022(3) 0.25568(19) 0.0542(6) Uani 1 1 d . . .
O22 O 0.3089(2) -0.1065(3) 0.34387(15) 0.0751(6) Uani 1 1 d . . .
O23 O 0.5200(2) -0.1637(2) 0.22872(15) 0.0680(5) Uani 1 1 d . . .
C24 C 0.5920(4) -0.2319(4) 0.3133(3) 0.0801(9) Uani 1 1 d . . .
H24A H 0.5370 -0.1945 0.3782 0.120 Uiso 1 1 calc R . .
H24B H 0.6852 -0.2159 0.2971 0.120 Uiso 1 1 calc R . .
H24C H 0.6014 -0.3306 0.3207 0.120 Uiso 1 1 calc R . .
C25 C 0.3722(3) 0.1858(2) 0.22745(17) 0.0485(5) Uani 1 1 d . . .
C26 C 0.4837(3) 0.1611(3) 0.27679(18) 0.0512(6) Uani 1 1 d . . .
H26 H 0.5698 0.0961 0.2535 0.061 Uiso 1 1 calc R . .
C27 C 0.4670(3) 0.2341(3) 0.36179(18) 0.0517(6) Uani 1 1 d . . .
C28 C 0.3391(3) 0.3313(3) 0.39655(18) 0.0522(6) Uani 1 1 d . . .
C29 C 0.2252(2) 0.3527(2) 0.34874(18) 0.0505(5) Uani 1 1 d . . .
C30 C 0.2426(3) 0.2818(3) 0.26342(18) 0.0509(5) Uani 1 1 d . . .
H31 H 0.1677 0.2984 0.2301 0.061 Uiso 1 1 calc R . .
O31 O 0.5725(2) 0.2235(2) 0.41206(16) 0.0679(5) Uani 1 1 d . . .
C32 C 0.6873(3) 0.1000(4) 0.4057(3) 0.0810(9) Uani 1 1 d . . .
H32A H 0.6500 0.0198 0.4301 0.122 Uiso 1 1 calc R . .
H32B H 0.7496 0.1024 0.4488 0.122 Uiso 1 1 calc R . .
H32C H 0.7399 0.0943 0.3337 0.122 Uiso 1 1 calc R . .
O33 O 0.3233(2) 0.40492(19) 0.47926(14) 0.0630(5) Uani 1 1 d . . .
C34 C 0.3472(4) 0.5401(4) 0.4440(3) 0.0860(10) Uani 1 1 d . . .
H34A H 0.4425 0.5302 0.4013 0.129 Uiso 1 1 calc R . .
H34B H 0.3359 0.5873 0.5039 0.129 Uiso 1 1 calc R . .
H34C H 0.2794 0.5936 0.4030 0.129 Uiso 1 1 calc R . .
O35 O 0.10167(19) 0.4470(2) 0.39049(14) 0.0615(5) Uani 1 1 d . . .
C36 C -0.0186(3) 0.4664(3) 0.3481(2) 0.0713(8) Uani 1 1 d . . .
H36A H -0.0008 0.5095 0.2767 0.107 Uiso 1 1 calc R . .
H36B H -0.1009 0.5256 0.3897 0.107 Uiso 1 1 calc R . .
H36C H -0.0359 0.3775 0.3492 0.107 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
O1 C8 1.383(3) . ?
O1 C2 1.413(4) . ?
C2 O3 1.418(4) . ?
C2 H2A 0.96(5) . ?
C2 H2B 0.91(5) . ?
O3 C9 1.379(3) . ?
C4 C9 1.365(4) . ?
C4 C5 1.399(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 C10 1.516(3) . ?
C6 C7 1.412(3) . ?
C6 C13 1.506(3) . ?
C7 C8 1.359(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(4) . ?
C10 O14 1.431(3) . ?
C10 C11 1.544(3) . ?
C10 H10 1.04(4) . ?
C11 C12 1.536(3) . ?
C11 P15 1.822(2) . ?
C11 H11 0.96(4) . ?
C12 C21 1.512(3) . ?
C12 C13 1.563(3) . ?
C12 H12 0.97(3) . ?
C13 C25 1.533(3) . ?
C13 H13 0.95(3) . ?
O14 H14A 0.90(4) . ?
P15 O16 1.461(2) . ?
P15 O19 1.5639(19) . ?
P15 O17 1.582(2) . ?
O17 C18 1.433(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O19 C20 1.423(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O22 1.197(3) . ?
C21 O23 1.332(3) . ?
O23 C24 1.451(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.381(3) . ?
C25 C30 1.393(3) . ?
C26 C27 1.397(3) . ?
C26 H26 0.9300 . ?
C27 O31 1.364(3) . ?
C27 C28 1.384(4) . ?
C28 O33 1.378(3) . ?
C28 C29 1.394(3) . ?
C29 O35 1.367(3) . ?
C29 C30 1.385(3) . ?
C30 H31 0.9300 . ?
O31 C32 1.420(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
O33 C34 1.428(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O35 C36 1.412(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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
C8 O1 C2 105.3(2) . . ?
O1 C2 O3 109.6(3) . . ?
O1 C2 H2A 113(3) . . ?
O3 C2 H2A 113(3) . . ?
O1 C2 H2B 113(3) . . ?
O3 C2 H2B 111(3) . . ?
H2A C2 H2B 97(4) . . ?
C9 O3 C2 105.4(2) . . ?
C9 C4 C5 117.7(2) . . ?
C9 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 C10 121.4(2) . . ?
C4 C5 C10 117.9(2) . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 C13 122.9(2) . . ?
C7 C6 C13 116.4(2) . . ?
C8 C7 C6 117.3(2) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 C9 122.3(2) . . ?
C7 C8 O1 127.8(2) . . ?
C9 C8 O1 109.9(2) . . ?
C4 C9 C8 121.7(3) . . ?
C4 C9 O3 128.5(3) . . ?
C8 C9 O3 109.9(2) . . ?
O14 C10 C5 111.04(19) . . ?
O14 C10 C11 107.0(2) . . ?
C5 C10 C11 111.19(19) . . ?
O14 C10 H10 114.8(19) . . ?
C5 C10 H10 105.8(19) . . ?
C11 C10 H10 107.0(19) . . ?
C12 C11 C10 108.17(19) . . ?
C12 C11 P15 117.67(18) . . ?
C10 C11 P15 109.78(16) . . ?
C12 C11 H11 108(2) . . ?
C10 C11 H11 106(2) . . ?
P15 C11 H11 106(2) . . ?
C21 C12 C11 116.3(2) . . ?
C21 C12 C13 107.18(18) . . ?
C11 C12 C13 110.56(19) . . ?
C21 C12 H12 105.0(19) . . ?
C11 C12 H12 110.5(19) . . ?
C13 C12 H12 106.8(19) . . ?
C6 C13 C25 109.06(18) . . ?
C6 C13 C12 112.76(18) . . ?
C25 C13 C12 112.94(17) . . ?
C6 C13 H13 109.3(19) . . ?
C25 C13 H13 109.0(19) . . ?
C12 C13 H13 103.6(19) . . ?
C10 O14 H14A 106(3) . . ?
O16 P15 O19 112.93(12) . . ?
O16 P15 O17 115.18(12) . . ?
O19 P15 O17 102.68(11) . . ?
O16 P15 C11 114.25(11) . . ?
O19 P15 C11 101.80(10) . . ?
O17 P15 C11 108.60(11) . . ?
C18 O17 P15 122.6(2) . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 O19 P15 123.8(2) . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O22 C21 O23 124.6(2) . . ?
O22 C21 C12 126.0(2) . . ?
O23 C21 C12 109.3(2) . . ?
C21 O23 C24 117.4(2) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 120.00(19) . . ?
C26 C25 C13 120.1(2) . . ?
C30 C25 C13 119.9(2) . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
O31 C27 C28 115.1(2) . . ?
O31 C27 C26 124.6(2) . . ?
C28 C27 C26 120.2(2) . . ?
O33 C28 C27 120.2(2) . . ?
O33 C28 C29 120.0(2) . . ?
C27 C28 C29 119.7(2) . . ?
O35 C29 C30 124.3(2) . . ?
O35 C29 C28 115.7(2) . . ?
C30 C29 C28 120.0(2) . . ?
C29 C30 C25 120.1(2) . . ?
C29 C30 H31 119.9 . . ?
C25 C30 H31 119.9 . . ?
C27 O31 C32 117.8(2) . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 O33 C34 112.3(2) . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 O35 C36 117.62(19) . . ?
O35 C36 H36A 109.5 . . ?
O35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C8 O1 C2 O3 -0.8(4) . . . . ?
O1 C2 O3 C9 0.5(4) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C9 C4 C5 C10 -179.3(2) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C10 C5 C6 C7 179.3(2) . . . . ?
C4 C5 C6 C13 174.2(2) . . . . ?
C10 C5 C6 C13 -6.3(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C13 C6 C7 C8 -174.8(2) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C6 C7 C8 O1 179.9(2) . . . . ?
C2 O1 C8 C7 -178.8(3) . . . . ?
C2 O1 C8 C9 0.8(4) . . . . ?
C5 C4 C9 C8 0.1(4) . . . . ?
C5 C4 C9 O3 -179.3(3) . . . . ?
C7 C8 C9 C4 -0.4(4) . . . . ?
O1 C8 C9 C4 180.0(3) . . . . ?
C7 C8 C9 O3 179.1(3) . . . . ?
O1 C8 C9 O3 -0.5(3) . . . . ?
C2 O3 C9 C4 179.4(3) . . . . ?
C2 O3 C9 C8 0.0(4) . . . . ?
C6 C5 C10 O14 -91.8(3) . . . . ?
C4 C5 C10 O14 87.7(3) . . . . ?
C6 C5 C10 C11 27.2(3) . . . . ?
C4 C5 C10 C11 -153.3(2) . . . . ?
O14 C10 C11 C12 66.2(2) . . . . ?
C5 C10 C11 C12 -55.2(3) . . . . ?
O14 C10 C11 P15 -63.4(2) . . . . ?
C5 C10 C11 P15 175.21(17) . . . . ?
C10 C11 C12 C21 -173.41(19) . . . . ?
P15 C11 C12 C21 -48.4(2) . . . . ?
C10 C11 C12 C13 64.1(2) . . . . ?
P15 C11 C12 C13 -170.83(14) . . . . ?
C5 C6 C13 C25 -112.5(2) . . . . ?
C7 C6 C13 C25 62.1(2) . . . . ?
C5 C6 C13 C12 13.8(3) . . . . ?
C7 C6 C13 C12 -171.55(19) . . . . ?
C21 C12 C13 C6 -170.41(18) . . . . ?
C11 C12 C13 C6 -42.8(2) . . . . ?
C21 C12 C13 C25 -46.2(2) . . . . ?
C11 C12 C13 C25 81.4(2) . . . . ?
C12 C11 P15 O16 -143.47(18) . . . . ?
C10 C11 P15 O16 -19.2(2) . . . . ?
C12 C11 P15 O19 94.48(18) . . . . ?
C10 C11 P15 O19 -141.27(18) . . . . ?
C12 C11 P15 O17 -13.4(2) . . . . ?
C10 C11 P15 O17 110.86(18) . . . . ?
O16 P15 O17 C18 40.2(3) . . . . ?
O19 P15 O17 C18 163.3(2) . . . . ?
C11 P15 O17 C18 -89.4(2) . . . . ?
O16 P15 O19 C20 75.2(3) . . . . ?
O17 P15 O19 C20 -49.5(3) . . . . ?
C11 P15 O19 C20 -161.9(3) . . . . ?
C11 C12 C21 O22 -19.7(3) . . . . ?
C13 C12 C21 O22 104.6(3) . . . . ?
C11 C12 C21 O23 164.1(2) . . . . ?
C13 C12 C21 O23 -71.7(2) . . . . ?
O22 C21 O23 C24 -4.7(4) . . . . ?
C12 C21 O23 C24 171.6(2) . . . . ?
C6 C13 C25 C26 -134.9(2) . . . . ?
C12 C13 C25 C26 98.9(2) . . . . ?
C6 C13 C25 C30 43.3(3) . . . . ?
C12 C13 C25 C30 -82.9(3) . . . . ?
C30 C25 C26 C27 -0.9(3) . . . . ?
C13 C25 C26 C27 177.3(2) . . . . ?
C25 C26 C27 O31 -176.1(2) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
O31 C27 C28 O33 -2.6(4) . . . . ?
C26 C27 C28 O33 -178.9(2) . . . . ?
O31 C27 C28 C29 178.5(2) . . . . ?
C26 C27 C28 C29 2.2(4) . . . . ?
O33 C28 C29 O35 -1.0(3) . . . . ?
C27 C28 C29 O35 177.8(2) . . . . ?
O33 C28 C29 C30 178.0(2) . . . . ?
C27 C28 C29 C30 -3.2(4) . . . . ?
O35 C29 C30 C25 -179.0(2) . . . . ?
C28 C29 C30 C25 2.1(4) . . . . ?
C26 C25 C30 C29 -0.1(4) . . . . ?
C13 C25 C30 C29 -178.2(2) . . . . ?
C28 C27 O31 C32 160.5(3) . . . . ?
C26 C27 O31 C32 -23.4(4) . . . . ?
C27 C28 O33 C34 97.3(3) . . . . ?
C29 C28 O33 C34 -83.9(3) . . . . ?
C30 C29 O35 C36 4.3(4) . . . . ?
C28 C29 O35 C36 -176.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.06
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.412
_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_epoxy
_database_code_depnum_ccdc_archive 'CCDC 1426547'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(rac)-(5R,6R,7S,8R)-5,8-Epoxynaphtho[2,3-d]-1,3-dioxole-6-carboxylic  acid, 5,6,7,8-tetrahydro-7-(dimethoxyphosphoryl)  -5-(3,4,5-trimethoxyphenyl)-, methyl ester'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 O11 P'
_chemical_formula_sum            'C24 H27 O11 P'
_chemical_formula_weight         522.43

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.9953(4)
_cell_length_b                   27.3594(8)
_cell_length_c                   9.1869(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.321(4)
_cell_angle_gamma                90.00
_cell_volume                     2574.50(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4574
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      25.12


_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'SCALE3 ABSPACK, CrysAlisPro, Agilent Technologies, V.1.171.36.20'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(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  'Xcalibur, Sapphire 3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1835
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4574
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.12
_reflns_number_total             4574
_reflns_number_gt                3921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          SQUEEZE

_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)+(0.1375P)²+0.1878P] 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         4574
_refine_ls_number_parameters     354
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1879
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O1 O 0.6401(2) 0.06144(8) 1.0571(3) 0.0764(6) Uani 1 1 d . . .
C2 C 0.6828(5) 0.01693(16) 1.1409(5) 0.0906(11) Uani 1 1 d D . .
H2A H 0.611(3) -0.0028(15) 1.151(6) 0.109 Uiso 1 1 d D . .
H2B H 0.743(4) 0.0313(16) 1.239(4) 0.109 Uiso 1 1 d D . .
O3 O 0.7579(3) -0.00953(8) 1.0700(3) 0.0826(7) Uani 1 1 d . . .
C4 C 0.8388(2) 0.01144(8) 0.8607(3) 0.0534(5) Uani 1 1 d . . .
H4 H 0.8861 -0.0172 0.8671 0.064 Uiso 1 1 calc R . .
C5 C 0.83051(19) 0.04842(8) 0.7522(2) 0.0447(5) Uani 1 1 d . . .
C6 C 0.76135(19) 0.09134(7) 0.7472(2) 0.0417(5) Uani 1 1 d . . .
C7 C 0.6949(2) 0.10065(8) 0.8465(3) 0.0478(5) Uani 1 1 d . . .
H7 H 0.6500 0.1297 0.8436 0.057 Uiso 1 1 calc R . .
C8 C 0.7007(2) 0.06349(9) 0.9500(3) 0.0542(5) Uani 1 1 d . . .
C9 C 0.7710(2) 0.02104(9) 0.9572(3) 0.0567(6) Uani 1 1 d . . .
C10 C 0.8932(2) 0.05512(8) 0.6325(2) 0.0444(5) Uani 1 1 d . . .
H10 H 0.920(3) 0.0257(12) 0.589(4) 0.067 Uiso 1 1 d . . .
C11 C 1.0082(2) 0.09200(7) 0.7018(2) 0.0418(5) Uani 1 1 d . A .
H11 H 1.063(3) 0.0836(11) 0.810(4) 0.063 Uiso 1 1 d . . .
C12 C 0.93419(18) 0.14089(7) 0.6959(2) 0.0400(4) Uani 1 1 d . . .
H12 H 0.950(3) 0.1634(11) 0.629(4) 0.060 Uiso 1 1 d . . .
C13 C 0.78638(18) 0.12273(7) 0.6244(2) 0.0404(4) Uani 1 1 d . . .
O14 O 0.79945(14) 0.08585(5) 0.51808(16) 0.0450(4) Uani 1 1 d . . .
P15 P 1.11731(6) 0.09329(2) 0.59618(7) 0.0490(2) Uani 1 1 d . . .
O16 O 1.16077(18) 0.04513(7) 0.5653(2) 0.0617(5) Uani 1 1 d . A .
O17 O 1.2268(2) 0.12774(10) 0.7010(4) 0.0966(9) Uani 1 1 d . A .
C18 C 1.3516(4) 0.13121(19) 0.6891(9) 0.143(3) Uani 1 1 d . . .
H18A H 1.4051 0.1535 0.7669 0.215 Uiso 1 1 calc R A .
H18B H 1.3422 0.1430 0.5871 0.215 Uiso 1 1 calc R . .
H18C H 1.3920 0.0995 0.7053 0.215 Uiso 1 1 calc R . .
C21 C 0.97512(19) 0.16452(8) 0.8556(2) 0.0462(5) Uani 1 1 d . . .
O22 O 1.0019(2) 0.14291(8) 0.9757(2) 0.0758(6) Uani 1 1 d . . .
O23 O 0.98285(17) 0.21320(6) 0.8469(2) 0.0603(5) Uani 1 1 d . . .
C24 C 1.0247(4) 0.23851(14) 0.9957(4) 0.0899(10) Uani 1 1 d . . .
H24A H 1.0329 0.2728 0.9791 0.135 Uiso 1 1 calc R . .
H24B H 1.1076 0.2258 1.0627 0.135 Uiso 1 1 calc R . .
H24C H 0.9614 0.2337 1.0438 0.135 Uiso 1 1 calc R . .
C25 C 0.68186(19) 0.15893(8) 0.5386(2) 0.0431(5) Uani 1 1 d . . .
C26 C 0.6947(2) 0.20851(8) 0.5752(2) 0.0489(5) Uani 1 1 d . . .
H26 H 0.7709 0.2204 0.6506 0.059 Uiso 1 1 calc R . .
C27 C 0.5924(2) 0.24024(8) 0.4978(3) 0.0519(5) Uani 1 1 d . . .
C28 C 0.4789(2) 0.22251(9) 0.3836(3) 0.0527(5) Uani 1 1 d . . .
C29 C 0.4682(2) 0.17292(10) 0.3468(3) 0.0538(6) Uani 1 1 d . . .
C30 C 0.5694(2) 0.14110(9) 0.4241(3) 0.0491(5) Uani 1 1 d . . .
H30 H 0.5619 0.1080 0.3993 0.059 Uiso 1 1 calc R . .
O31 O 0.5955(2) 0.28947(7) 0.5250(2) 0.0698(5) Uani 1 1 d . . .
C32 C 0.7017(3) 0.30816(10) 0.6502(4) 0.0678(7) Uani 1 1 d . . .
H32A H 0.6858 0.3418 0.6665 0.102 Uiso 1 1 calc R . .
H32B H 0.7797 0.3056 0.6266 0.102 Uiso 1 1 calc R . .
H32C H 0.7123 0.2898 0.7431 0.102 Uiso 1 1 calc R . .
O33 O 0.37923(19) 0.25405(7) 0.3056(2) 0.0658(5) Uani 1 1 d . . .
C34 C 0.2899(3) 0.26096(15) 0.3830(4) 0.0844(10) Uani 1 1 d . . .
H34A H 0.2197 0.2817 0.3208 0.127 Uiso 1 1 calc R . .
H34B H 0.3340 0.2760 0.4828 0.127 Uiso 1 1 calc R . .
H34C H 0.2555 0.2299 0.3978 0.127 Uiso 1 1 calc R . .
O35 O 0.35410(17) 0.15954(8) 0.2321(2) 0.0730(6) Uani 1 1 d . . .
C36 C 0.3445(4) 0.11121(15) 0.1739(6) 0.1107(16) Uani 1 1 d . . .
H36A H 0.2595 0.1063 0.0954 0.166 Uiso 1 1 calc R . .
H36B H 0.3576 0.0885 0.2578 0.166 Uiso 1 1 calc R . .
H36C H 0.4099 0.1061 0.1290 0.166 Uiso 1 1 calc R . .
O19A O 1.0394(8) 0.1208(3) 0.4312(9) 0.0677(15) Uani 0.611(10) 1 d P A 1
C20A C 0.9746(11) 0.0984(4) 0.2957(9) 0.110(3) Uani 0.611(10) 1 d P A 1
H20A H 1.0123 0.0668 0.2952 0.164 Uiso 0.611(10) 1 calc PR A 1
H20B H 0.9803 0.1176 0.2110 0.164 Uiso 0.611(10) 1 calc PR A 1
H20C H 0.8846 0.0946 0.2838 0.164 Uiso 0.611(10) 1 calc PR A 1
O19B O 1.0727(14) 0.1319(5) 0.4726(15) 0.0677(15) Uani 0.389(10) 1 d P A 2
C20B C 1.0472(17) 0.1200(7) 0.3049(14) 0.110(3) Uani 0.389(10) 1 d P A 2
H20D H 1.0836 0.0885 0.2982 0.164 Uiso 0.389(10) 1 calc PR A 2
H20E H 1.0869 0.1444 0.2615 0.164 Uiso 0.389(10) 1 calc PR A 2
H20F H 0.9548 0.1194 0.2474 0.164 Uiso 0.389(10) 1 calc PR A 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 C8 1.375(3) . ?
O1 C2 1.426(4) . ?
C2 O3 1.422(5) . ?
C2 H2A 0.987(19) . ?
C2 H2B 0.983(19) . ?
O3 C9 1.380(3) . ?
C4 C9 1.375(4) . ?
C4 C5 1.400(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 C10 1.507(3) . ?
C6 C7 1.385(3) . ?
C6 C13 1.521(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(4) . ?
C10 O14 1.445(2) . ?
C10 C11 1.561(3) . ?
C10 H10 0.99(3) . ?
C11 C12 1.556(3) . ?
C11 P15 1.797(2) . ?
C11 H11 0.99(3) . ?
C12 C21 1.515(3) . ?
C12 C13 1.595(3) . ?
C12 H12 0.93(3) . ?
C13 O14 1.447(2) . ?
C13 C25 1.505(3) . ?
P15 O16 1.4640(18) . ?
P15 O19B 1.496(15) . ?
P15 O17 1.556(2) . ?
P15 O19A 1.629(8) . ?
O17 C18 1.419(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C21 O22 1.190(3) . ?
C21 O23 1.339(3) . ?
O23 C24 1.450(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C30 1.389(3) . ?
C25 C26 1.392(3) . ?
C26 C27 1.394(3) . ?
C26 H26 0.9300 . ?
C27 O31 1.368(3) . ?
C27 C28 1.393(3) . ?
C28 O33 1.374(3) . ?
C28 C29 1.393(4) . ?
C29 O35 1.362(3) . ?
C29 C30 1.388(3) . ?
C30 H30 0.9300 . ?
O31 C32 1.404(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
O33 C34 1.419(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O35 C36 1.416(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
O19A C20A 1.337(11) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
O19B C20B 1.498(17) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?

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
C8 O1 C2 105.8(2) . . ?
O3 C2 O1 108.6(3) . . ?
O3 C2 H2A 112(3) . . ?
O1 C2 H2A 114(3) . . ?
O3 C2 H2B 108(3) . . ?
O1 C2 H2B 98(3) . . ?
H2A C2 H2B 115(4) . . ?
C9 O3 C2 105.8(2) . . ?
C9 C4 C5 114.2(2) . . ?
C9 C4 H4 122.9 . . ?
C5 C4 H4 122.9 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 C10 105.23(18) . . ?
C4 C5 C10 132.8(2) . . ?
C7 C6 C5 123.1(2) . . ?
C7 C6 C13 131.81(19) . . ?
C5 C6 C13 104.91(18) . . ?
C8 C7 C6 114.6(2) . . ?
C8 C7 H7 122.7 . . ?
C6 C7 H7 122.7 . . ?
O1 C8 C7 127.7(2) . . ?
O1 C8 C9 109.8(2) . . ?
C7 C8 C9 122.5(2) . . ?
C4 C9 O3 126.7(2) . . ?
C4 C9 C8 123.7(2) . . ?
O3 C9 C8 109.6(2) . . ?
O14 C10 C5 101.94(16) . . ?
O14 C10 C11 100.29(15) . . ?
C5 C10 C11 107.40(17) . . ?
O14 C10 H10 114.6(18) . . ?
C5 C10 H10 118.8(19) . . ?
C11 C10 H10 111.9(19) . . ?
C12 C11 C10 101.87(15) . . ?
C12 C11 P15 114.05(14) . . ?
C10 C11 P15 113.16(15) . . ?
C12 C11 H11 110.8(18) . . ?
C10 C11 H11 111.8(18) . . ?
P15 C11 H11 105.4(18) . . ?
C21 C12 C11 111.44(16) . . ?
C21 C12 C13 115.56(17) . . ?
C11 C12 C13 100.85(15) . . ?
C21 C12 H12 107.2(19) . . ?
C11 C12 H12 111.9(19) . . ?
C13 C12 H12 110.0(18) . . ?
O14 C13 C25 110.49(15) . . ?
O14 C13 C6 101.31(16) . . ?
C25 C13 C6 116.77(17) . . ?
O14 C13 C12 99.14(15) . . ?
C25 C13 C12 118.71(17) . . ?
C6 C13 C12 107.61(15) . . ?
C10 O14 C13 97.72(14) . . ?
O16 P15 O19B 121.9(5) . . ?
O16 P15 O17 115.57(12) . . ?
O19B P15 O17 90.5(5) . . ?
O16 P15 O19A 109.5(3) . . ?
O17 P15 O19A 108.8(3) . . ?
O16 P15 C11 114.59(11) . . ?
O19B P15 C11 108.9(6) . . ?
O17 P15 C11 101.30(12) . . ?
O19A P15 C11 106.4(3) . . ?
C18 O17 P15 123.0(3) . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O22 C21 O23 123.4(2) . . ?
O22 C21 C12 124.9(2) . . ?
O23 C21 C12 111.68(19) . . ?
C21 O23 C24 115.1(2) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 120.62(19) . . ?
C30 C25 C13 117.76(19) . . ?
C26 C25 C13 121.58(18) . . ?
C25 C26 C27 119.4(2) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
O31 C27 C28 115.9(2) . . ?
O31 C27 C26 123.9(2) . . ?
C28 C27 C26 120.2(2) . . ?
O33 C28 C27 120.0(2) . . ?
O33 C28 C29 120.2(2) . . ?
C27 C28 C29 119.7(2) . . ?
O35 C29 C30 124.7(2) . . ?
O35 C29 C28 115.0(2) . . ?
C30 C29 C28 120.3(2) . . ?
C29 C30 C25 119.7(2) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?
C27 O31 C32 117.79(19) . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 O33 C34 112.9(2) . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 O35 C36 117.7(2) . . ?
O35 C36 H36A 109.5 . . ?
O35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C20A O19A P15 125.2(7) . . ?
P15 O19B C20B 121.0(11) . . ?
O19B C20B H20D 109.5 . . ?
O19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
O19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 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
C8 O1 C2 O3 -6.2(4) . . . . ?
O1 C2 O3 C9 6.1(4) . . . . ?
C9 C4 C5 C6 1.4(3) . . . . ?
C9 C4 C5 C10 176.0(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C10 C5 C6 C7 -176.57(19) . . . . ?
C4 C5 C6 C13 175.41(19) . . . . ?
C10 C5 C6 C13 -0.5(2) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C13 C6 C7 C8 -176.0(2) . . . . ?
C2 O1 C8 C7 -176.8(3) . . . . ?
C2 O1 C8 C9 4.0(4) . . . . ?
C6 C7 C8 O1 -177.0(2) . . . . ?
C6 C7 C8 C9 2.1(3) . . . . ?
C5 C4 C9 O3 177.3(3) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C2 O3 C9 C4 178.4(3) . . . . ?
C2 O3 C9 C8 -3.6(4) . . . . ?
O1 C8 C9 C4 177.8(2) . . . . ?
C7 C8 C9 C4 -1.4(4) . . . . ?
O1 C8 C9 O3 -0.3(3) . . . . ?
C7 C8 C9 O3 -179.5(2) . . . . ?
C6 C5 C10 O14 -31.26(19) . . . . ?
C4 C5 C10 O14 153.5(2) . . . . ?
C6 C5 C10 C11 73.66(19) . . . . ?
C4 C5 C10 C11 -101.6(3) . . . . ?
O14 C10 C11 C12 35.07(19) . . . . ?
C5 C10 C11 C12 -71.03(19) . . . . ?
O14 C10 C11 P15 -87.81(16) . . . . ?
C5 C10 C11 P15 166.10(13) . . . . ?
C10 C11 C12 C21 123.83(18) . . . . ?
P15 C11 C12 C21 -113.90(17) . . . . ?
C10 C11 C12 C13 0.66(19) . . . . ?
P15 C11 C12 C13 122.93(15) . . . . ?
C7 C6 C13 O14 -152.4(2) . . . . ?
C5 C6 C13 O14 31.95(18) . . . . ?
C7 C6 C13 C25 -32.4(3) . . . . ?
C5 C6 C13 C25 152.00(17) . . . . ?
C7 C6 C13 C12 104.1(2) . . . . ?
C5 C6 C13 C12 -71.56(19) . . . . ?
C21 C12 C13 O14 -156.28(17) . . . . ?
C11 C12 C13 O14 -36.00(17) . . . . ?
C21 C12 C13 C25 84.2(2) . . . . ?
C11 C12 C13 C25 -155.50(18) . . . . ?
C21 C12 C13 C6 -51.2(2) . . . . ?
C11 C12 C13 C6 69.04(19) . . . . ?
C5 C10 O14 C13 50.29(17) . . . . ?
C11 C10 O14 C13 -60.14(18) . . . . ?
C25 C13 O14 C10 -174.68(17) . . . . ?
C6 C13 O14 C10 -50.27(17) . . . . ?
C12 C13 O14 C10 59.90(17) . . . . ?
C12 C11 P15 O16 -164.57(14) . . . . ?
C10 C11 P15 O16 -48.72(18) . . . . ?
C12 C11 P15 O19B -24.2(5) . . . . ?
C10 C11 P15 O19B 91.7(5) . . . . ?
C12 C11 P15 O17 70.30(19) . . . . ?
C10 C11 P15 O17 -173.85(17) . . . . ?
C12 C11 P15 O19A -43.4(3) . . . . ?
C10 C11 P15 O19A 72.4(3) . . . . ?
O16 P15 O17 C18 39.6(5) . . . . ?
O19B P15 O17 C18 -86.6(8) . . . . ?
O19A P15 O17 C18 -84.1(6) . . . . ?
C11 P15 O17 C18 164.0(5) . . . . ?
C11 C12 C21 O22 -35.9(3) . . . . ?
C13 C12 C21 O22 78.4(3) . . . . ?
C11 C12 C21 O23 141.64(18) . . . . ?
C13 C12 C21 O23 -104.0(2) . . . . ?
O22 C21 O23 C24 -1.0(4) . . . . ?
C12 C21 O23 C24 -178.5(2) . . . . ?
O14 C13 C25 C30 39.5(3) . . . . ?
C6 C13 C25 C30 -75.5(2) . . . . ?
C12 C13 C25 C30 152.9(2) . . . . ?
O14 C13 C25 C26 -142.5(2) . . . . ?
C6 C13 C25 C26 102.5(2) . . . . ?
C12 C13 C25 C26 -29.0(3) . . . . ?
C30 C25 C26 C27 1.2(3) . . . . ?
C13 C25 C26 C27 -176.8(2) . . . . ?
C25 C26 C27 O31 -179.8(2) . . . . ?
C25 C26 C27 C28 -0.8(4) . . . . ?
O31 C27 C28 O33 0.3(4) . . . . ?
C26 C27 C28 O33 -178.8(2) . . . . ?
O31 C27 C28 C29 179.1(2) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
O33 C28 C29 O35 -0.4(4) . . . . ?
C27 C28 C29 O35 -179.1(2) . . . . ?
O33 C28 C29 C30 179.2(2) . . . . ?
C27 C28 C29 C30 0.5(4) . . . . ?
O35 C29 C30 C25 179.6(2) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C26 C25 C30 C29 -0.8(4) . . . . ?
C13 C25 C30 C29 177.2(2) . . . . ?
C28 C27 O31 C32 173.4(2) . . . . ?
C26 C27 O31 C32 -7.5(4) . . . . ?
C27 C28 O33 C34 -88.2(3) . . . . ?
C29 C28 O33 C34 93.1(3) . . . . ?
C30 C29 O35 C36 -8.4(5) . . . . ?
C28 C29 O35 C36 171.2(3) . . . . ?
O16 P15 O19A C20A 27.3(10) . . . . ?
O19B P15 O19A C20A 162(4) . . . . ?
O17 P15 O19A C20A 154.5(8) . . . . ?
C11 P15 O19A C20A -97.0(9) . . . . ?
O16 P15 O19B C20B 11.3(15) . . . . ?
O17 P15 O19B C20B 132.2(12) . . . . ?
O19A P15 O19B C20B -40(2) . . . . ?
C11 P15 O19B C20B -125.6(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.065


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 0.000 73 12 ' '
2 0.500 0.000 0.500 73 12 ' '
_platon_squeeze_details          
;
?
;
