# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_crystalclear

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 O2 P Se'
_chemical_formula_sum            'C29 H23 O2 P Se'
_chemical_formula_weight         513.40
_chemical_absolute_configuration syn

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'p 21 21 2'
_symmetry_Int_Tables_number      18

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

_cell_length_a                   13.151(8)
_cell_length_b                   23.056(13)
_cell_length_c                   7.806(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2367(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7551
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.774

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.62
_diffrn_reflns_number            19181
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5357
_reflns_number_gt                5083
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0230P)^2^+2.4489P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(10)
_refine_ls_number_reflns         5357
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
Se1 Se 0.53975(3) 0.878174(17) 0.46600(5) 0.03685(10) Uani 1 1 d . . .
P1 P 0.38698(7) 0.87778(4) 0.40581(10) 0.02528(17) Uani 1 1 d . . .
O1 O 0.32380(18) 0.93657(9) 0.4423(3) 0.0277(5) Uani 1 1 d . . .
O2 O 0.32683(18) 0.83038(9) 0.5184(3) 0.0261(5) Uani 1 1 d . . .
C1 C 0.2691(3) 0.77433(16) -0.0688(5) 0.0333(8) Uani 1 1 d . . .
H1 H 0.2515 0.8120 -0.1086 0.040 Uiso 1 1 calc R . .
C2 C 0.2114(3) 0.72742(18) -0.1205(6) 0.0424(10) Uani 1 1 d . . .
H2 H 0.1554 0.7329 -0.1956 0.051 Uiso 1 1 calc R . .
C3 C 0.2354(4) 0.67231(19) -0.0625(7) 0.0545(12) Uani 1 1 d . . .
H3 H 0.1958 0.6399 -0.0970 0.065 Uiso 1 1 calc R . .
C4 C 0.3174(4) 0.66489(19) 0.0457(7) 0.0584(13) Uani 1 1 d . . .
H4 H 0.3345 0.6271 0.0846 0.070 Uiso 1 1 calc R . .
C5 C 0.3751(4) 0.7122(2) 0.0984(6) 0.0513(12) Uani 1 1 d . . .
H5 H 0.4305 0.7064 0.1748 0.062 Uiso 1 1 calc R . .
C6 C 0.3529(3) 0.76792(16) 0.0406(5) 0.0347(8) Uani 1 1 d . . .
C7 C 0.4172(3) 0.81958(19) 0.0927(5) 0.0388(9) Uani 1 1 d . . .
H6 H 0.4704 0.8055 0.1743 0.047 Uiso 1 1 calc R . .
C8 C 0.4715(4) 0.8462(2) -0.0625(6) 0.0581(13) Uani 1 1 d . . .
H7 H 0.4210 0.8583 -0.1476 0.087 Uiso 1 1 calc R . .
H8 H 0.5172 0.8174 -0.1134 0.087 Uiso 1 1 calc R . .
H9 H 0.5111 0.8800 -0.0256 0.087 Uiso 1 1 calc R . .
C9 C 0.3543(3) 0.86726(17) 0.1850(4) 0.0341(8) Uani 1 1 d . . .
H10 H 0.2813 0.8569 0.1777 0.041 Uiso 1 1 calc R . .
H11 H 0.3638 0.9044 0.1234 0.041 Uiso 1 1 calc R . .
C10 C 0.2939(3) 0.94933(14) 0.6103(4) 0.0258(7) Uani 1 1 d . . .
C11 C 0.3457(3) 0.99447(15) 0.6945(5) 0.0307(8) Uani 1 1 d . . .
H12 H 0.4020 1.0132 0.6419 0.037 Uiso 1 1 calc R . .
C12 C 0.3133(3) 1.01069(14) 0.8535(5) 0.0323(8) Uani 1 1 d . . .
H13 H 0.3459 1.0421 0.9100 0.039 Uiso 1 1 calc R . .
C13 C 0.2319(3) 0.98166(14) 0.9362(5) 0.0276(8) Uani 1 1 d . . .
C14 C 0.1819(3) 0.93489(14) 0.8517(4) 0.0238(7) Uani 1 1 d . . .
C15 C 0.2132(2) 0.91960(14) 0.6801(4) 0.0223(6) Uani 1 1 d . . .
C16 C 0.1993(3) 0.99791(16) 1.1039(5) 0.0347(8) Uani 1 1 d . . .
H14 H 0.2310 1.0298 1.1596 0.042 Uiso 1 1 calc R . .
C17 C 0.1238(3) 0.96864(17) 1.1855(5) 0.0399(10) Uani 1 1 d . . .
H15 H 0.1027 0.9801 1.2968 0.048 Uiso 1 1 calc R . .
C18 C 0.0772(3) 0.92142(17) 1.1043(5) 0.0374(9) Uani 1 1 d . . .
H16 H 0.0249 0.9008 1.1622 0.045 Uiso 1 1 calc R . .
C19 C 0.1055(3) 0.90437(15) 0.9427(4) 0.0291(7) Uani 1 1 d . . .
H17 H 0.0736 0.8718 0.8912 0.035 Uiso 1 1 calc R . .
C20 C 0.2196(3) 0.82928(13) 0.5066(4) 0.0248(7) Uani 1 1 d . . .
C21 C 0.1624(2) 0.87267(14) 0.5795(4) 0.0223(6) Uani 1 1 d . . .
C22 C 0.0547(2) 0.87167(14) 0.5488(4) 0.0261(7) Uani 1 1 d . . .
C23 C 0.0113(3) 0.82370(15) 0.4591(5) 0.0302(7) Uani 1 1 d . . .
C24 C 0.0749(3) 0.77869(15) 0.3990(5) 0.0347(8) Uani 1 1 d . . .
H18 H 0.0456 0.7460 0.3440 0.042 Uiso 1 1 calc R . .
C25 C 0.1780(3) 0.78160(15) 0.4188(5) 0.0325(8) Uani 1 1 d . . .
H19 H 0.2207 0.7520 0.3741 0.039 Uiso 1 1 calc R . .
C26 C -0.0103(3) 0.91824(15) 0.5954(5) 0.0295(8) Uani 1 1 d . . .
H20 H 0.0171 0.9510 0.6528 0.035 Uiso 1 1 calc R . .
C27 C -0.1120(3) 0.91655(17) 0.5587(5) 0.0369(9) Uani 1 1 d . . .
H21 H -0.1543 0.9482 0.5902 0.044 Uiso 1 1 calc R . .
C28 C -0.1542(3) 0.86831(19) 0.4746(5) 0.0420(9) Uani 1 1 d . . .
H22 H -0.2252 0.8673 0.4519 0.050 Uiso 1 1 calc R . .
C29 C -0.0951(3) 0.82333(18) 0.4258(5) 0.0385(9) Uani 1 1 d . . .
H23 H -0.1249 0.7911 0.3687 0.046 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.02425(16) 0.0480(2) 0.03835(19) -0.00965(18) -0.00113(16) -0.00054(18)
P1 0.0269(4) 0.0279(4) 0.0211(4) -0.0026(4) 0.0019(3) 0.0030(4)
O1 0.0292(13) 0.0286(11) 0.0254(13) -0.0015(9) 0.0079(10) 0.0043(10)
O2 0.0264(12) 0.0266(11) 0.0252(12) 0.0007(9) -0.0016(10) 0.0029(9)
C1 0.033(2) 0.039(2) 0.028(2) 0.0052(15) -0.0018(15) 0.0073(15)
C2 0.034(2) 0.051(2) 0.043(2) 0.0023(19) 0.0056(19) -0.0011(18)
C3 0.062(3) 0.045(2) 0.057(3) 0.001(2) 0.016(2) -0.005(2)
C4 0.085(4) 0.040(2) 0.050(3) 0.011(2) 0.017(3) 0.013(2)
C5 0.063(3) 0.062(3) 0.028(2) 0.0048(19) -0.006(2) 0.029(2)
C6 0.039(2) 0.046(2) 0.0185(16) -0.0013(16) 0.0014(16) 0.0154(16)
C7 0.032(2) 0.061(2) 0.0231(18) -0.0122(17) -0.0053(15) 0.0143(18)
C8 0.040(3) 0.087(3) 0.048(3) -0.027(2) 0.016(2) -0.016(2)
C9 0.033(2) 0.047(2) 0.0224(17) -0.0051(15) -0.0010(14) 0.0103(16)
C10 0.0282(18) 0.0262(16) 0.0229(17) -0.0005(13) 0.0013(14) 0.0027(13)
C11 0.0250(17) 0.0282(17) 0.039(2) -0.0038(14) 0.0035(15) -0.0014(14)
C12 0.035(2) 0.0241(16) 0.038(2) -0.0086(14) -0.0037(16) -0.0003(15)
C13 0.0260(17) 0.0268(16) 0.030(2) -0.0064(13) -0.0027(14) 0.0062(13)
C14 0.0219(17) 0.0279(15) 0.0216(16) -0.0002(12) -0.0014(13) 0.0036(13)
C15 0.0190(16) 0.0252(15) 0.0225(16) -0.0026(12) -0.0016(12) 0.0019(12)
C16 0.041(2) 0.0341(18) 0.0287(19) -0.0084(15) -0.0056(17) 0.0078(15)
C17 0.050(3) 0.052(2) 0.0178(18) -0.0045(16) 0.0045(17) 0.0132(19)
C18 0.037(2) 0.049(2) 0.0252(18) 0.0066(17) 0.0084(16) 0.0070(17)
C19 0.0293(18) 0.0334(17) 0.0245(19) 0.0029(14) 0.0013(14) 0.0034(14)
C20 0.0245(17) 0.0274(15) 0.0225(19) 0.0007(12) 0.0015(12) 0.0012(12)
C21 0.0234(16) 0.0275(15) 0.0161(14) 0.0000(12) -0.0007(11) 0.0014(13)
C22 0.0311(19) 0.0301(15) 0.0171(14) 0.0025(14) -0.0002(13) -0.0036(14)
C23 0.032(2) 0.0379(18) 0.0210(16) 0.0039(15) -0.0012(15) -0.0079(13)
C24 0.044(2) 0.0322(18) 0.0282(18) -0.0067(15) -0.0045(16) -0.0104(15)
C25 0.036(2) 0.0278(17) 0.033(2) -0.0049(14) -0.0001(16) 0.0007(15)
C26 0.0277(19) 0.0332(17) 0.0276(18) 0.0008(14) 0.0000(14) -0.0005(13)
C27 0.0244(18) 0.047(2) 0.039(2) 0.0052(17) 0.0042(16) 0.0070(16)
C28 0.0244(18) 0.066(3) 0.0354(19) 0.003(2) -0.0011(17) -0.0035(17)
C29 0.035(2) 0.051(2) 0.029(2) 0.0008(16) -0.0034(15) -0.0145(18)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 P1 2.0634(15) . ?
P1 O2 1.610(2) . ?
P1 O1 1.615(2) . ?
P1 C9 1.793(4) . ?
O1 C10 1.400(4) . ?
O2 C20 1.413(4) . ?
C1 C2 1.381(6) . ?
C1 C6 1.402(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.516(6) . ?
C7 C8 1.535(6) . ?
C7 C9 1.553(5) . ?
C7 H6 1.0000 . ?
C8 H7 0.9800 . ?
C8 H8 0.9800 . ?
C8 H9 0.9800 . ?
C9 H10 0.9900 . ?
C9 H11 0.9900 . ?
C10 C15 1.377(5) . ?
C10 C11 1.407(5) . ?
C11 C12 1.365(5) . ?
C11 H12 0.9500 . ?
C12 C13 1.418(5) . ?
C12 H13 0.9500 . ?
C13 C14 1.425(5) . ?
C13 C16 1.428(5) . ?
C14 C19 1.418(5) . ?
C14 C15 1.445(4) . ?
C15 C21 1.495(4) . ?
C16 C17 1.359(6) . ?
C16 H14 0.9500 . ?
C17 C18 1.401(6) . ?
C17 H15 0.9500 . ?
C18 C19 1.373(5) . ?
C18 H16 0.9500 . ?
C19 H17 0.9500 . ?
C20 C21 1.375(4) . ?
C20 C25 1.406(5) . ?
C21 C22 1.436(4) . ?
C22 C26 1.420(5) . ?
C22 C23 1.428(4) . ?
C23 C24 1.413(5) . ?
C23 C29 1.424(5) . ?
C24 C25 1.366(5) . ?
C24 H18 0.9500 . ?
C25 H19 0.9500 . ?
C26 C27 1.368(5) . ?
C26 H20 0.9500 . ?
C27 C28 1.406(6) . ?
C27 H21 0.9500 . ?
C28 C29 1.351(6) . ?
C28 H22 0.9500 . ?
C29 H23 0.9500 . ?

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
O2 P1 O1 102.74(13) . . ?
O2 P1 C9 108.38(17) . . ?
O1 P1 C9 99.19(15) . . ?
O2 P1 Se1 110.91(10) . . ?
O1 P1 Se1 117.20(10) . . ?
C9 P1 Se1 116.94(13) . . ?
C10 O1 P1 119.1(2) . . ?
C20 O2 P1 117.8(2) . . ?
C2 C1 C6 121.8(4) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 117.4(4) . . ?
C5 C6 C7 121.4(4) . . ?
C1 C6 C7 121.3(3) . . ?
C6 C7 C8 111.3(3) . . ?
C6 C7 C9 112.5(3) . . ?
C8 C7 C9 109.3(4) . . ?
C6 C7 H6 107.9 . . ?
C8 C7 H6 107.9 . . ?
C9 C7 H6 107.9 . . ?
C7 C8 H7 109.5 . . ?
C7 C8 H8 109.5 . . ?
H7 C8 H8 109.5 . . ?
C7 C8 H9 109.5 . . ?
H7 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
C7 C9 P1 114.4(3) . . ?
C7 C9 H10 108.6 . . ?
P1 C9 H10 108.6 . . ?
C7 C9 H11 108.6 . . ?
P1 C9 H11 108.6 . . ?
H10 C9 H11 107.6 . . ?
C15 C10 O1 118.8(3) . . ?
C15 C10 C11 123.8(3) . . ?
O1 C10 C11 117.2(3) . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H12 120.8 . . ?
C10 C11 H12 120.8 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H13 119.3 . . ?
C13 C12 H13 119.3 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 C16 121.4(3) . . ?
C14 C13 C16 119.0(3) . . ?
C19 C14 C13 118.1(3) . . ?
C19 C14 C15 123.0(3) . . ?
C13 C14 C15 118.9(3) . . ?
C10 C15 C14 117.7(3) . . ?
C10 C15 C21 119.8(3) . . ?
C14 C15 C21 122.5(3) . . ?
C17 C16 C13 121.2(4) . . ?
C17 C16 H14 119.4 . . ?
C13 C16 H14 119.4 . . ?
C16 C17 C18 119.6(3) . . ?
C16 C17 H15 120.2 . . ?
C18 C17 H15 120.2 . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 H16 119.4 . . ?
C17 C18 H16 119.4 . . ?
C18 C19 C14 120.7(4) . . ?
C18 C19 H17 119.6 . . ?
C14 C19 H17 119.6 . . ?
C21 C20 C25 123.9(3) . . ?
C21 C20 O2 120.4(3) . . ?
C25 C20 O2 115.7(3) . . ?
C20 C21 C22 117.3(3) . . ?
C20 C21 C15 120.0(3) . . ?
C22 C21 C15 122.7(3) . . ?
C26 C22 C23 118.1(3) . . ?
C26 C22 C21 122.6(3) . . ?
C23 C22 C21 119.2(3) . . ?
C24 C23 C29 121.1(4) . . ?
C24 C23 C22 119.7(3) . . ?
C29 C23 C22 119.2(3) . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H18 119.5 . . ?
C23 C24 H18 119.5 . . ?
C24 C25 C20 118.7(3) . . ?
C24 C25 H19 120.7 . . ?
C20 C25 H19 120.7 . . ?
C27 C26 C22 120.9(3) . . ?
C27 C26 H20 119.5 . . ?
C22 C26 H20 119.5 . . ?
C26 C27 C28 120.4(4) . . ?
C26 C27 H21 119.8 . . ?
C28 C27 H21 119.8 . . ?
C29 C28 C27 120.8(4) . . ?
C29 C28 H22 119.6 . . ?
C27 C28 H22 119.6 . . ?
C28 C29 C23 120.6(4) . . ?
C28 C29 H23 119.7 . . ?
C23 C29 H23 119.7 . . ?

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
O2 P1 O1 C10 44.0(3) . . . . ?
C9 P1 O1 C10 155.3(3) . . . . ?
Se1 P1 O1 C10 -77.9(3) . . . . ?
O1 P1 O2 C20 46.9(2) . . . . ?
C9 P1 O2 C20 -57.4(3) . . . . ?
Se1 P1 O2 C20 172.91(19) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 -1.3(7) . . . . ?
C4 C5 C6 C1 1.4(6) . . . . ?
C4 C5 C6 C7 -178.1(4) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C2 C1 C6 C7 178.4(4) . . . . ?
C5 C6 C7 C8 115.2(5) . . . . ?
C1 C6 C7 C8 -64.3(5) . . . . ?
C5 C6 C7 C9 -121.8(4) . . . . ?
C1 C6 C7 C9 58.8(5) . . . . ?
C6 C7 C9 P1 113.8(3) . . . . ?
C8 C7 C9 P1 -122.1(3) . . . . ?
O2 P1 C9 C7 -83.6(3) . . . . ?
O1 P1 C9 C7 169.6(3) . . . . ?
Se1 P1 C9 C7 42.6(3) . . . . ?
P1 O1 C10 C15 -76.0(4) . . . . ?
P1 O1 C10 C11 107.4(3) . . . . ?
C15 C10 C11 C12 -1.2(5) . . . . ?
O1 C10 C11 C12 175.3(3) . . . . ?
C10 C11 C12 C13 2.4(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C11 C12 C13 C16 178.8(3) . . . . ?
C12 C13 C14 C19 175.8(3) . . . . ?
C16 C13 C14 C19 -3.5(5) . . . . ?
C12 C13 C14 C15 -2.4(5) . . . . ?
C16 C13 C14 C15 178.3(3) . . . . ?
O1 C10 C15 C14 -178.1(3) . . . . ?
C11 C10 C15 C14 -1.7(5) . . . . ?
O1 C10 C15 C21 2.9(5) . . . . ?
C11 C10 C15 C21 179.3(3) . . . . ?
C19 C14 C15 C10 -174.7(3) . . . . ?
C13 C14 C15 C10 3.4(5) . . . . ?
C19 C14 C15 C21 4.3(5) . . . . ?
C13 C14 C15 C21 -177.6(3) . . . . ?
C12 C13 C16 C17 -177.5(4) . . . . ?
C14 C13 C16 C17 1.8(5) . . . . ?
C13 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C14 -1.1(5) . . . . ?
C13 C14 C19 C18 3.2(5) . . . . ?
C15 C14 C19 C18 -178.6(3) . . . . ?
P1 O2 C20 C21 -72.1(4) . . . . ?
P1 O2 C20 C25 108.5(3) . . . . ?
C25 C20 C21 C22 -6.3(5) . . . . ?
O2 C20 C21 C22 174.3(3) . . . . ?
C25 C20 C21 C15 176.0(3) . . . . ?
O2 C20 C21 C15 -3.3(4) . . . . ?
C10 C15 C21 C20 51.0(4) . . . . ?
C14 C15 C21 C20 -127.9(3) . . . . ?
C10 C15 C21 C22 -126.5(3) . . . . ?
C14 C15 C21 C22 54.6(4) . . . . ?
C20 C21 C22 C26 -170.6(3) . . . . ?
C15 C21 C22 C26 7.0(5) . . . . ?
C20 C21 C22 C23 5.7(4) . . . . ?
C15 C21 C22 C23 -176.7(3) . . . . ?
C26 C22 C23 C24 175.1(3) . . . . ?
C21 C22 C23 C24 -1.3(5) . . . . ?
C26 C22 C23 C29 -2.4(5) . . . . ?
C21 C22 C23 C29 -178.8(3) . . . . ?
C29 C23 C24 C25 174.5(4) . . . . ?
C22 C23 C24 C25 -2.9(6) . . . . ?
C23 C24 C25 C20 2.5(6) . . . . ?
C21 C20 C25 C24 2.2(5) . . . . ?
O2 C20 C25 C24 -178.3(3) . . . . ?
C23 C22 C26 C27 1.5(5) . . . . ?
C21 C22 C26 C27 177.7(3) . . . . ?
C22 C26 C27 C28 0.3(6) . . . . ?
C26 C27 C28 C29 -1.2(6) . . . . ?
C27 C28 C29 C23 0.3(6) . . . . ?
C24 C23 C29 C28 -175.9(4) . . . . ?
C22 C23 C29 C28 1.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 953220'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_crystalclear

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 O3 P Se'
_chemical_formula_sum            'C25 H21 O3 P Se'
_chemical_formula_weight         479.35
_chemical_absolute_configuration ad

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21   '
_symmetry_Int_Tables_number      19

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'

_cell_length_a                   17.479(8)
_cell_length_b                   10.231(5)
_cell_length_c                   12.459(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2227.9(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6096
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.781
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_T_max  0.732

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.62
_diffrn_reflns_number            17803
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5079
_reflns_number_gt                4573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0990P)^2^+2.0810P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(14)
_refine_ls_number_reflns         5079
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1711
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
Se1 Se 0.27278(4) 0.84180(7) 0.40067(5) 0.0646(3) Uani 1 1 d . . .
P1 P 0.31879(7) 0.93044(14) 0.26685(10) 0.0403(3) Uani 1 1 d . . .
O1 O 0.28895(17) 0.8838(3) 0.1509(3) 0.0398(8) Uani 1 1 d . . .
O2 O 0.40894(18) 0.9013(3) 0.2615(2) 0.0400(7) Uani 1 1 d . . .
O3 O 0.2083(2) 1.2736(4) 0.2203(3) 0.0455(8) Uani 1 1 d . . .
C1 C 0.3039(3) 1.1039(5) 0.2510(4) 0.0401(10) Uani 1 1 d . . .
H1 H 0.3317 1.1319 0.1848 0.048 Uiso 1 1 calc R . .
C2 C 0.2197(3) 1.1373(4) 0.2356(4) 0.0407(10) Uani 1 1 d . . .
H2 H 0.1998 1.0894 0.1724 0.049 Uiso 1 1 calc R . .
H3 H 0.1905 1.1083 0.2994 0.049 Uiso 1 1 calc R . .
C3 C 0.2332(3) 1.3445(5) 0.3124(4) 0.0436(10) Uani 1 1 d . . .
H4 H 0.2053 1.3129 0.3765 0.052 Uiso 1 1 calc R . .
H5 H 0.2212 1.4384 0.3029 0.052 Uiso 1 1 calc R . .
C4 C 0.3187(3) 1.3278(6) 0.3296(4) 0.0483(12) Uani 1 1 d . . .
H6 H 0.3350 1.3777 0.3937 0.058 Uiso 1 1 calc R . .
H7 H 0.3470 1.3619 0.2667 0.058 Uiso 1 1 calc R . .
C5 C 0.3368(3) 1.1816(6) 0.3453(4) 0.0499(13) Uani 1 1 d . . .
H8 H 0.3929 1.1686 0.3492 0.060 Uiso 1 1 calc R . .
H9 H 0.3140 1.1503 0.4134 0.060 Uiso 1 1 calc R . .
C6 C 0.3111(3) 0.7601(4) 0.1152(4) 0.0360(9) Uani 1 1 d . . .
C7 C 0.3853(2) 0.7437(4) 0.0784(4) 0.0334(9) Uani 1 1 d . . .
C8 C 0.4072(3) 0.6130(5) 0.0489(3) 0.0356(9) Uani 1 1 d . . .
C9 C 0.4841(3) 0.5823(5) 0.0182(4) 0.0398(10) Uani 1 1 d . . .
H10 H 0.5216 0.6493 0.0144 0.048 Uiso 1 1 calc R . .
C10 C 0.5034(3) 0.4546(6) -0.0058(4) 0.0509(13) Uani 1 1 d . . .
H11 H 0.5550 0.4340 -0.0231 0.061 Uiso 1 1 calc R . .
C11 C 0.4483(4) 0.3551(6) -0.0049(4) 0.0585(15) Uani 1 1 d . . .
H12 H 0.4622 0.2683 -0.0237 0.070 Uiso 1 1 calc R . .
C12 C 0.3752(4) 0.3827(6) 0.0227(5) 0.0543(13) Uani 1 1 d . . .
H13 H 0.3384 0.3144 0.0228 0.065 Uiso 1 1 calc R . .
C13 C 0.3522(3) 0.5105(5) 0.0514(4) 0.0419(11) Uani 1 1 d . . .
C14 C 0.2768(3) 0.5382(5) 0.0848(4) 0.0493(12) Uani 1 1 d . . .
H14 H 0.2397 0.4704 0.0848 0.059 Uiso 1 1 calc R . .
C15 C 0.2564(3) 0.6599(5) 0.1168(4) 0.0448(11) Uani 1 1 d . . .
H15 H 0.2056 0.6771 0.1401 0.054 Uiso 1 1 calc R . .
C16 C 0.4501(2) 0.9306(5) 0.1660(4) 0.0351(9) Uani 1 1 d . . .
C17 C 0.5023(3) 1.0354(5) 0.1732(4) 0.0417(11) Uani 1 1 d . . .
H16 H 0.5094 1.0811 0.2388 0.050 Uiso 1 1 calc R . .
C18 C 0.5430(2) 1.0699(5) 0.0821(5) 0.0443(11) Uani 1 1 d . . .
H17 H 0.5796 1.1384 0.0851 0.053 Uiso 1 1 calc R . .
C19 C 0.5298(3) 1.0030(5) -0.0153(4) 0.0392(10) Uani 1 1 d . . .
C20 C 0.5684(3) 1.0448(6) -0.1113(5) 0.0505(13) Uani 1 1 d . . .
H18 H 0.6041 1.1148 -0.1089 0.061 Uiso 1 1 calc R . .
C21 C 0.5534(3) 0.9827(7) -0.2059(5) 0.0561(15) Uani 1 1 d . . .
H19 H 0.5780 1.0112 -0.2697 0.067 Uiso 1 1 calc R . .
C22 C 0.5021(3) 0.8775(6) -0.2102(4) 0.0502(13) Uani 1 1 d . . .
H20 H 0.4932 0.8347 -0.2767 0.060 Uiso 1 1 calc R . .
C23 C 0.4647(2) 0.8358(6) -0.1204(4) 0.0411(10) Uani 1 1 d . . .
H21 H 0.4295 0.7653 -0.1253 0.049 Uiso 1 1 calc R . .
C24 C 0.4780(2) 0.8967(5) -0.0191(4) 0.0372(10) Uani 1 1 d . . .
C25 C 0.4383(2) 0.8581(4) 0.0768(3) 0.0339(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.0730(4) 0.0711(4) 0.0497(3) 0.0222(3) 0.0190(3) 0.0098(3)
P1 0.0435(6) 0.0461(7) 0.0313(6) 0.0050(5) 0.0039(5) 0.0069(5)
O1 0.0378(16) 0.0451(19) 0.0366(16) 0.0021(14) -0.0038(13) 0.0037(13)
O2 0.0414(16) 0.050(2) 0.0283(15) -0.0019(14) -0.0014(12) 0.0088(14)
O3 0.0508(19) 0.0397(19) 0.0458(19) -0.0001(16) -0.0079(15) 0.0051(14)
C1 0.040(2) 0.046(3) 0.034(2) 0.004(2) 0.0003(17) 0.0064(19)
C2 0.038(2) 0.035(2) 0.049(3) -0.002(2) -0.0056(19) 0.0055(18)
C3 0.046(2) 0.044(3) 0.041(2) -0.011(2) 0.005(2) -0.002(2)
C4 0.049(3) 0.051(3) 0.045(3) -0.010(2) 0.008(2) -0.006(2)
C5 0.043(2) 0.060(4) 0.046(3) -0.004(3) -0.007(2) 0.006(2)
C6 0.042(2) 0.031(2) 0.035(2) 0.0045(18) -0.0009(18) 0.0018(17)
C7 0.036(2) 0.033(2) 0.031(2) 0.0050(18) -0.0033(16) -0.0025(16)
C8 0.049(2) 0.035(2) 0.0223(19) 0.0043(17) -0.0068(17) 0.0014(19)
C9 0.044(2) 0.043(3) 0.032(2) -0.001(2) -0.0071(18) 0.0019(19)
C10 0.066(3) 0.051(3) 0.037(3) -0.003(2) -0.006(2) 0.013(3)
C11 0.098(5) 0.038(3) 0.040(3) -0.002(2) -0.011(3) 0.015(3)
C12 0.078(4) 0.036(3) 0.048(3) 0.002(2) -0.010(3) -0.002(3)
C13 0.058(3) 0.036(3) 0.031(2) 0.0100(19) -0.0080(19) -0.004(2)
C14 0.064(3) 0.042(3) 0.042(2) 0.006(2) -0.004(2) -0.013(2)
C15 0.044(2) 0.051(3) 0.040(2) 0.006(2) 0.0007(18) -0.009(2)
C16 0.037(2) 0.036(2) 0.033(2) 0.0031(19) -0.0002(17) 0.0013(18)
C17 0.040(2) 0.036(2) 0.048(3) -0.008(2) -0.011(2) 0.0002(19)
C18 0.034(2) 0.041(3) 0.058(3) 0.005(2) 0.000(2) -0.0026(18)
C19 0.034(2) 0.043(3) 0.040(2) 0.008(2) -0.0022(18) 0.0015(19)
C20 0.038(2) 0.057(3) 0.056(3) 0.018(3) 0.006(2) -0.004(2)
C21 0.048(3) 0.074(4) 0.047(3) 0.021(3) 0.008(2) -0.002(3)
C22 0.054(3) 0.063(4) 0.034(2) 0.009(2) 0.002(2) -0.002(2)
C23 0.034(2) 0.051(3) 0.039(2) 0.006(2) -0.0046(16) -0.003(2)
C24 0.035(2) 0.042(3) 0.035(2) 0.005(2) -0.0025(17) 0.0011(18)
C25 0.0338(18) 0.036(2) 0.032(2) 0.0007(19) -0.0028(15) 0.0022(16)

_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
Se1 P1 2.0612(15) . ?
P1 O2 1.605(3) . ?
P1 O1 1.608(4) . ?
P1 C1 1.805(5) . ?
O1 C6 1.396(6) . ?
O2 C16 1.422(5) . ?
O3 C2 1.422(6) . ?
O3 C3 1.425(6) . ?
C1 C2 1.522(6) . ?
C1 C5 1.530(7) . ?
C1 H1 1.0000 . ?
C2 H2 0.9900 . ?
C2 H3 0.9900 . ?
C3 C4 1.520(7) . ?
C3 H4 0.9900 . ?
C3 H5 0.9900 . ?
C4 C5 1.542(9) . ?
C4 H6 0.9900 . ?
C4 H7 0.9900 . ?
C5 H8 0.9900 . ?
C5 H9 0.9900 . ?
C6 C7 1.385(6) . ?
C6 C15 1.403(6) . ?
C7 C8 1.438(7) . ?
C7 C25 1.494(6) . ?
C8 C13 1.424(7) . ?
C8 C9 1.432(7) . ?
C9 C10 1.382(7) . ?
C9 H10 0.9500 . ?
C10 C11 1.402(9) . ?
C10 H11 0.9500 . ?
C11 C12 1.353(9) . ?
C11 H12 0.9500 . ?
C12 C13 1.414(8) . ?
C12 H13 0.9500 . ?
C13 C14 1.411(8) . ?
C14 C15 1.355(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C25 1.352(6) . ?
C16 C17 1.411(7) . ?
C17 C18 1.386(8) . ?
C17 H16 0.9500 . ?
C18 C19 1.411(8) . ?
C18 H17 0.9500 . ?
C19 C24 1.416(7) . ?
C19 C20 1.439(7) . ?
C20 C21 1.364(9) . ?
C20 H18 0.9500 . ?
C21 C22 1.402(9) . ?
C21 H19 0.9500 . ?
C22 C23 1.365(7) . ?
C22 H20 0.9500 . ?
C23 C24 1.427(7) . ?
C23 H21 0.9500 . ?
C24 C25 1.436(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O1 103.06(17) . . ?
O2 P1 C1 108.6(2) . . ?
O1 P1 C1 98.5(2) . . ?
O2 P1 Se1 109.57(14) . . ?
O1 P1 Se1 117.99(14) . . ?
C1 P1 Se1 117.70(17) . . ?
C6 O1 P1 117.7(3) . . ?
C16 O2 P1 119.5(3) . . ?
C2 O3 C3 110.4(4) . . ?
C2 C1 C5 110.1(4) . . ?
C2 C1 P1 112.0(3) . . ?
C5 C1 P1 111.9(3) . . ?
C2 C1 H1 107.6 . . ?
C5 C1 H1 107.6 . . ?
P1 C1 H1 107.6 . . ?
O3 C2 C1 111.9(4) . . ?
O3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
O3 C2 H3 109.2 . . ?
C1 C2 H3 109.2 . . ?
H2 C2 H3 107.9 . . ?
O3 C3 C4 110.9(4) . . ?
O3 C3 H4 109.5 . . ?
C4 C3 H4 109.5 . . ?
O3 C3 H5 109.5 . . ?
C4 C3 H5 109.5 . . ?
H4 C3 H5 108.0 . . ?
C3 C4 C5 109.2(5) . . ?
C3 C4 H6 109.8 . . ?
C5 C4 H6 109.8 . . ?
C3 C4 H7 109.8 . . ?
C5 C4 H7 109.8 . . ?
H6 C4 H7 108.3 . . ?
C1 C5 C4 109.2(4) . . ?
C1 C5 H8 109.8 . . ?
C4 C5 H8 109.8 . . ?
C1 C5 H9 109.8 . . ?
C4 C5 H9 109.8 . . ?
H8 C5 H9 108.3 . . ?
C7 C6 O1 118.4(4) . . ?
C7 C6 C15 123.7(4) . . ?
O1 C6 C15 117.9(4) . . ?
C6 C7 C8 116.6(4) . . ?
C6 C7 C25 119.3(4) . . ?
C8 C7 C25 124.0(4) . . ?
C13 C8 C9 118.6(4) . . ?
C13 C8 C7 119.9(4) . . ?
C9 C8 C7 121.5(4) . . ?
C10 C9 C8 119.7(5) . . ?
C10 C9 H10 120.2 . . ?
C8 C9 H10 120.2 . . ?
C9 C10 C11 121.1(5) . . ?
C9 C10 H11 119.5 . . ?
C11 C10 H11 119.5 . . ?
C12 C11 C10 120.0(5) . . ?
C12 C11 H12 120.0 . . ?
C10 C11 H12 120.0 . . ?
C11 C12 C13 121.7(6) . . ?
C11 C12 H13 119.1 . . ?
C13 C12 H13 119.1 . . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 C8 119.3(5) . . ?
C12 C13 C8 118.9(5) . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C6 119.2(5) . . ?
C14 C15 H15 120.4 . . ?
C6 C15 H15 120.4 . . ?
C25 C16 C17 124.6(4) . . ?
C25 C16 O2 119.7(4) . . ?
C17 C16 O2 115.7(4) . . ?
C18 C17 C16 118.3(5) . . ?
C18 C17 H16 120.9 . . ?
C16 C17 H16 120.9 . . ?
C17 C18 C19 119.8(4) . . ?
C17 C18 H17 120.1 . . ?
C19 C18 H17 120.1 . . ?
C18 C19 C24 120.4(5) . . ?
C18 C19 C20 119.6(5) . . ?
C24 C19 C20 120.0(5) . . ?
C21 C20 C19 119.3(5) . . ?
C21 C20 H18 120.3 . . ?
C19 C20 H18 120.3 . . ?
C20 C21 C22 120.9(5) . . ?
C20 C21 H19 119.5 . . ?
C22 C21 H19 119.5 . . ?
C23 C22 C21 121.0(5) . . ?
C23 C22 H20 119.5 . . ?
C21 C22 H20 119.5 . . ?
C22 C23 C24 120.8(5) . . ?
C22 C23 H21 119.6 . . ?
C24 C23 H21 119.6 . . ?
C19 C24 C23 118.0(4) . . ?
C19 C24 C25 119.5(4) . . ?
C23 C24 C25 122.5(4) . . ?
C16 C25 C24 117.4(4) . . ?
C16 C25 C7 120.9(4) . . ?
C24 C25 C7 121.7(4) . . ?

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
O2 P1 O1 C6 49.6(3) . . . . ?
C1 P1 O1 C6 161.1(3) . . . . ?
Se1 P1 O1 C6 -71.3(3) . . . . ?
O1 P1 O2 C16 41.4(4) . . . . ?
C1 P1 O2 C16 -62.3(4) . . . . ?
Se1 P1 O2 C16 167.8(3) . . . . ?
O2 P1 C1 C2 170.0(3) . . . . ?
O1 P1 C1 C2 63.1(4) . . . . ?
Se1 P1 C1 C2 -64.8(4) . . . . ?
O2 P1 C1 C5 -65.9(4) . . . . ?
O1 P1 C1 C5 -172.8(3) . . . . ?
Se1 P1 C1 C5 59.3(4) . . . . ?
C3 O3 C2 C1 -61.7(5) . . . . ?
C5 C1 C2 O3 56.4(6) . . . . ?
P1 C1 C2 O3 -178.4(3) . . . . ?
C2 O3 C3 C4 63.4(5) . . . . ?
O3 C3 C4 C5 -59.6(6) . . . . ?
C2 C1 C5 C4 -52.1(5) . . . . ?
P1 C1 C5 C4 -177.2(3) . . . . ?
C3 C4 C5 C1 53.7(5) . . . . ?
P1 O1 C6 C7 -75.8(5) . . . . ?
P1 O1 C6 C15 105.4(4) . . . . ?
O1 C6 C7 C8 176.1(4) . . . . ?
C15 C6 C7 C8 -5.1(7) . . . . ?
O1 C6 C7 C25 -0.7(6) . . . . ?
C15 C6 C7 C25 178.0(4) . . . . ?
C6 C7 C8 C13 4.3(6) . . . . ?
C25 C7 C8 C13 -179.0(4) . . . . ?
C6 C7 C8 C9 -174.8(4) . . . . ?
C25 C7 C8 C9 1.9(6) . . . . ?
C13 C8 C9 C10 -1.4(7) . . . . ?
C7 C8 C9 C10 177.6(4) . . . . ?
C8 C9 C10 C11 2.7(8) . . . . ?
C9 C10 C11 C12 -1.9(8) . . . . ?
C10 C11 C12 C13 -0.1(9) . . . . ?
C11 C12 C13 C14 -177.1(5) . . . . ?
C11 C12 C13 C8 1.3(8) . . . . ?
C9 C8 C13 C14 177.9(4) . . . . ?
C7 C8 C13 C14 -1.1(6) . . . . ?
C9 C8 C13 C12 -0.5(7) . . . . ?
C7 C8 C13 C12 -179.6(4) . . . . ?
C12 C13 C14 C15 176.9(5) . . . . ?
C8 C13 C14 C15 -1.5(7) . . . . ?
C13 C14 C15 C6 0.9(8) . . . . ?
C7 C6 C15 C14 2.6(7) . . . . ?
O1 C6 C15 C14 -178.6(4) . . . . ?
P1 O2 C16 C25 -70.1(5) . . . . ?
P1 O2 C16 C17 110.7(4) . . . . ?
C25 C16 C17 C18 2.0(7) . . . . ?
O2 C16 C17 C18 -178.8(4) . . . . ?
C16 C17 C18 C19 1.9(7) . . . . ?
C17 C18 C19 C24 -3.1(7) . . . . ?
C17 C18 C19 C20 175.9(5) . . . . ?
C18 C19 C20 C21 -177.7(5) . . . . ?
C24 C19 C20 C21 1.3(7) . . . . ?
C19 C20 C21 C22 -1.3(9) . . . . ?
C20 C21 C22 C23 1.2(9) . . . . ?
C21 C22 C23 C24 -1.1(8) . . . . ?
C18 C19 C24 C23 177.7(4) . . . . ?
C20 C19 C24 C23 -1.3(7) . . . . ?
C18 C19 C24 C25 0.6(7) . . . . ?
C20 C19 C24 C25 -178.4(4) . . . . ?
C22 C23 C24 C19 1.2(7) . . . . ?
C22 C23 C24 C25 178.2(5) . . . . ?
C17 C16 C25 C24 -4.5(7) . . . . ?
O2 C16 C25 C24 176.4(4) . . . . ?
C17 C16 C25 C7 176.3(4) . . . . ?
O2 C16 C25 C7 -2.9(6) . . . . ?
C19 C24 C25 C16 3.1(6) . . . . ?
C23 C24 C25 C16 -173.9(4) . . . . ?
C19 C24 C25 C7 -177.7(4) . . . . ?
C23 C24 C25 C7 5.3(7) . . . . ?
C6 C7 C25 C16 53.2(6) . . . . ?
C8 C7 C25 C16 -123.4(5) . . . . ?
C6 C7 C25 C24 -126.0(5) . . . . ?
C8 C7 C25 C24 57.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 953221'