# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_General
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

#=======================================================================

# SUBMISSION DETAILS

_publ_contact_author_name        'Pavel Anzenbacher, Jr.'
_publ_contact_author_address     
'Department of Chemistry, bowling Green State University, OH 43403, USA'
_publ_contact_author_email       pavel@bgsu.edu
_publ_contact_author_phone       419-372-1080
_publ_contact_author_fax         419-372-9809
loop_
_publ_author_name
_publ_author_address
'Ryota Kabe'
'Department of Chemistry, bowling Green State University, OH 43403, USA'
'Vincent M. Lynch'
;Department of Chemistry and Biochemistry, University of Texas
at Austin, Austin TX 78712, USA
;
'P.Anzenbacher Junior'
;
FIRST AUTHORS ADDRESS
;
#=================================================================

# TITLE AND AUTHOR LIST
_publ_section_title              
;
ENTER SECTION TITLE
;
_publ_section_title_footnote     
;
ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_footnote
;
FIRST AUTHORS FOOTNOTES
;
_publ_section_synopsis           
;
ENTER SYNOPSIS
;
_publ_section_abstract           
;
ENTER ABSTRACT
;

#======================================================================
data_3
_database_code_depnum_ccdc_archive 'CCDC 819622'
#TrackingRef '- CIFforCrystEngComm.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 P Se'
_chemical_formula_sum            'C18 H13 P Se'
_chemical_formula_weight         339.21
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'
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           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.377(2)
_cell_length_b                   9.509(2)
_cell_length_c                   15.331(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.624(5)
_cell_angle_gamma                90.00
_cell_volume                     1511.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    13622
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5
_exptl_crystal_description       prisms
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.410
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury CCD'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13259
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3460
_reflns_number_gt                3102
_reflns_threshold_expression     >2sigma(I)

_publ_section_references         
;
Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97.
(1999) J. Appl. Cryst. 32, 115-119.
Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System
of Windows Programs for the Solution, Refinement and Analysis of
Single Crystal X-ray Diffraction Data.
Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens
Analytical X-ray Instruments, Inc., Madison, WI, USA.
Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht
University, Utrecht, The Netherlands.
;
_publ_section_acknowledgements   
;
The data were collected using instrumentation purchased with funds provided
by the National Science Foundation Grant No. 0741973.
;
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;
SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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^)+(0.0294P)^2^+0.7157P] 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       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3460
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_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 0.19348(2) 0.37291(2) 0.447266(13) 0.03931(9) Uani 1 1 d . . .
P1 P 0.20549(4) 0.25262(4) 0.56275(3) 0.02650(11) Uani 1 1 d . . .
C1 C 0.05982(17) 0.22694(19) 0.62024(11) 0.0300(4) Uani 1 1 d . . .
C2 C -0.01994(19) 0.3292(2) 0.65307(13) 0.0375(4) Uani 1 1 d . . .
H2 H -0.0005 0.4252 0.6476 0.045 Uiso 1 1 calc R . .
C3 C -0.1299(2) 0.2853(3) 0.69446(14) 0.0495(6) Uani 1 1 d . . .
H3 H -0.1847 0.3525 0.7183 0.059 Uiso 1 1 calc R . .
C4 C -0.1590(2) 0.1440(3) 0.70075(16) 0.0537(6) Uani 1 1 d . . .
H4 H -0.2338 0.1166 0.7286 0.064 Uiso 1 1 calc R . .
C5 C -0.0803(2) 0.0418(3) 0.66698(14) 0.0459(5) Uani 1 1 d . . .
H5 H -0.1019 -0.0539 0.6713 0.055 Uiso 1 1 calc R . .
C6 C 0.03108(18) 0.0827(2) 0.62657(12) 0.0329(4) Uani 1 1 d . . .
C7 C 0.12733(18) -0.00933(19) 0.58662(12) 0.0329(4) Uani 1 1 d . . .
C8 C 0.1264(2) -0.1557(2) 0.58122(15) 0.0456(5) Uani 1 1 d . . .
H8 H 0.0597 -0.2075 0.6055 0.055 Uiso 1 1 calc R . .
C9 C 0.2240(3) -0.2241(2) 0.54002(16) 0.0546(6) Uani 1 1 d . . .
H9 H 0.2233 -0.3228 0.5367 0.066 Uiso 1 1 calc R . .
C10 C 0.3229(3) -0.1498(2) 0.50355(16) 0.0522(6) Uani 1 1 d . . .
H10 H 0.3885 -0.1981 0.4757 0.063 Uiso 1 1 calc R . .
C11 C 0.3253(2) -0.0040(2) 0.50813(13) 0.0404(4) Uani 1 1 d . . .
H11 H 0.3919 0.0471 0.4833 0.048 Uiso 1 1 calc R . .
C12 C 0.22784(18) 0.06484(18) 0.54996(11) 0.0297(4) Uani 1 1 d . . .
C13 C 0.32808(17) 0.31557(18) 0.64136(12) 0.0294(4) Uani 1 1 d . . .
C14 C 0.3263(2) 0.2750(2) 0.72854(13) 0.0394(4) Uani 1 1 d . . .
H14 H 0.2596 0.2171 0.7474 0.047 Uiso 1 1 calc R . .
C15 C 0.4226(2) 0.3197(3) 0.78747(14) 0.0488(5) Uani 1 1 d . . .
H15 H 0.4213 0.2919 0.8463 0.059 Uiso 1 1 calc R . .
C16 C 0.5205(2) 0.4049(3) 0.76028(16) 0.0525(6) Uani 1 1 d . . .
H16 H 0.5859 0.4348 0.8005 0.063 Uiso 1 1 calc R . .
C17 C 0.5226(2) 0.4459(3) 0.67473(16) 0.0562(6) Uani 1 1 d . . .
H17 H 0.5895 0.5041 0.6565 0.067 Uiso 1 1 calc R . .
C18 C 0.4266(2) 0.4021(2) 0.61491(14) 0.0428(5) Uani 1 1 d . . .
H18 H 0.4283 0.4311 0.5564 0.051 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 0.04747(14) 0.03761(13) 0.03288(12) 0.01100(8) 0.00222(9) -0.00121(8)
P1 0.0295(2) 0.0233(2) 0.0268(2) 0.00138(16) 0.00221(17) -0.00030(16)
C1 0.0290(9) 0.0354(9) 0.0253(8) 0.0018(7) -0.0020(7) -0.0026(7)
C2 0.0345(10) 0.0453(11) 0.0325(10) -0.0025(8) -0.0008(8) 0.0053(8)
C3 0.0360(11) 0.0766(16) 0.0360(11) -0.0040(11) 0.0038(9) 0.0094(10)
C4 0.0346(11) 0.0859(19) 0.0409(12) 0.0129(11) 0.0039(9) -0.0084(11)
C5 0.0412(11) 0.0551(13) 0.0410(12) 0.0139(10) -0.0023(9) -0.0139(10)
C6 0.0328(9) 0.0382(9) 0.0271(9) 0.0063(7) -0.0052(7) -0.0062(7)
C7 0.0411(10) 0.0281(9) 0.0284(9) 0.0027(7) -0.0102(8) -0.0047(7)
C8 0.0596(14) 0.0300(10) 0.0456(12) 0.0052(8) -0.0161(10) -0.0110(9)
C9 0.0804(17) 0.0264(10) 0.0546(14) -0.0073(9) -0.0219(13) 0.0070(10)
C10 0.0669(16) 0.0393(11) 0.0493(13) -0.0124(10) -0.0083(12) 0.0189(10)
C11 0.0439(11) 0.0395(10) 0.0376(11) -0.0041(8) -0.0004(9) 0.0080(9)
C12 0.0365(9) 0.0251(8) 0.0270(9) -0.0007(7) -0.0053(7) 0.0009(7)
C13 0.0302(9) 0.0259(8) 0.0324(9) -0.0031(7) 0.0038(7) -0.0012(7)
C14 0.0408(11) 0.0437(11) 0.0337(10) 0.0011(8) 0.0008(8) -0.0111(8)
C15 0.0507(13) 0.0606(14) 0.0344(11) -0.0009(10) -0.0043(10) -0.0113(11)
C16 0.0437(12) 0.0637(14) 0.0493(13) -0.0103(11) -0.0053(10) -0.0162(11)
C17 0.0456(13) 0.0667(16) 0.0563(15) -0.0003(12) 0.0031(11) -0.0275(11)
C18 0.0409(11) 0.0486(12) 0.0392(11) 0.0029(9) 0.0056(9) -0.0132(9)
_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 2.1068(6) . ?
P1 C1 1.8010(18) . ?
P1 C12 1.8125(18) . ?
P1 C13 1.8134(19) . ?
C1 C2 1.386(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.481(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9400 . ?
C13 C18 1.387(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
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
C1 P1 C12 91.94(8) . . ?
C1 P1 C13 107.37(8) . . ?
C12 P1 C13 107.92(8) . . ?
C1 P1 Se1 117.79(6) . . ?
C12 P1 Se1 116.55(6) . . ?
C13 P1 Se1 113.08(6) . . ?
C2 C1 C6 121.75(18) . . ?
C2 C1 P1 127.67(15) . . ?
C6 C1 P1 110.55(13) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.05(19) . . ?
C5 C6 C7 127.50(19) . . ?
C1 C6 C7 113.45(16) . . ?
C8 C7 C12 118.87(19) . . ?
C8 C7 C6 127.68(19) . . ?
C12 C7 C6 113.44(16) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C7 121.41(17) . . ?
C11 C12 P1 127.95(15) . . ?
C7 C12 P1 110.61(13) . . ?
C18 C13 C14 119.16(18) . . ?
C18 C13 P1 120.36(15) . . ?
C14 C13 P1 120.45(14) . . ?
C15 C14 C13 120.07(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 P1 C1 C2 -179.28(18) . . . . ?
C13 P1 C1 C2 71.26(18) . . . . ?
Se1 P1 C1 C2 -57.73(19) . . . . ?
C12 P1 C1 C6 -1.20(14) . . . . ?
C13 P1 C1 C6 -110.66(13) . . . . ?
Se1 P1 C1 C6 120.35(12) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
P1 C1 C2 C3 178.96(15) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.97(19) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
P1 C1 C6 C5 -178.30(15) . . . . ?
C2 C1 C6 C7 179.28(17) . . . . ?
P1 C1 C6 C7 1.07(19) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C1 C6 C7 C8 -179.34(18) . . . . ?
C5 C6 C7 C12 179.02(19) . . . . ?
C1 C6 C7 C12 -0.3(2) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 178.95(19) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C10 C11 C12 P1 -178.26(16) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
C6 C7 C12 C11 -178.68(17) . . . . ?
C8 C7 C12 P1 178.51(15) . . . . ?
C6 C7 C12 P1 -0.63(19) . . . . ?
C1 P1 C12 C11 178.93(18) . . . . ?
C13 P1 C12 C11 -72.11(19) . . . . ?
Se1 P1 C12 C11 56.36(19) . . . . ?
C1 P1 C12 C7 1.04(14) . . . . ?
C13 P1 C12 C7 110.00(13) . . . . ?
Se1 P1 C12 C7 -121.53(12) . . . . ?
C1 P1 C13 C18 -150.81(16) . . . . ?
C12 P1 C13 C18 111.24(17) . . . . ?
Se1 P1 C13 C18 -19.19(18) . . . . ?
C1 P1 C13 C14 30.76(18) . . . . ?
C12 P1 C13 C14 -67.19(17) . . . . ?
Se1 P1 C13 C14 162.38(14) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
P1 C13 C14 C15 177.83(17) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
P1 C13 C18 C17 -177.75(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.058

#===END
#======================================================================
data_mixedcrystal
_database_code_depnum_ccdc_archive 'CCDC 819623'
#TrackingRef '- CIFforCrystEngComm.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 P S, C18 H13 P S2'
_chemical_formula_sum            'C36 H26 P2 S Se'
_chemical_formula_weight         631.53
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'
Se Se -0.0929 2.2259 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.320(2)
_cell_length_b                   9.3942(15)
_cell_length_c                   15.135(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.101(4)
_cell_angle_gamma                90.00
_cell_volume                     1466.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14714
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5
_exptl_crystal_description       prisms
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    1.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71074
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC-12 with Saturn 724+ CCD'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14181
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3344
_reflns_number_gt                3247
_reflns_threshold_expression     >2sigma(I)

_publ_section_references         
;
Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97.
(1999) J. Appl. Cryst. 32, 115-119.
Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System
of Windows Programs for the Solution, Refinement and Analysis of
Single Crystal X-ray Diffraction Data.
Sheldrick, G. M. (2008). SHELXL-97. Acat Cryst., A64, 112-122.
Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht
University, Utrecht, The Netherlands.
;
_publ_section_acknowledgements   
;
The data were collected using instrumentation purchased with funds provided
by the National Science Foundation Grant No. 0741973.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;
SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C.,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_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.
A solution of equimolar amounts of the S and Se phosphine were crystallized.
Refinement of the site occupancy factors for S and Se resulted in 50-50 mix
in the data crystal. P-S and P-Se bond lengths reported here are comparable
to those listed in the Cambridge Crystallographic Database.

;
_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^)+(0.0231P)^2^+0.8668P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0592
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.44382(12) 0.27104(14) 0.38009(8) 0.0157(2) Uani 1 1 d . . .
C2 C 0.52466(13) 0.16716(15) 0.34714(9) 0.0197(3) Uani 1 1 d . . .
C3 C 0.63629(13) 0.21030(18) 0.30538(9) 0.0252(3) Uani 1 1 d . . .
C4 C 0.66618(14) 0.35410(18) 0.29833(10) 0.0272(3) Uani 1 1 d . . .
C5 C 0.58597(13) 0.45803(16) 0.33201(9) 0.0236(3) Uani 1 1 d . . .
C6 C 0.47289(12) 0.41684(14) 0.37295(8) 0.0172(2) Uani 1 1 d . . .
C7 C 0.37552(12) 0.51044(14) 0.41270(8) 0.0172(2) Uani 1 1 d . . .
C8 C 0.37709(15) 0.65888(15) 0.41752(9) 0.0234(3) Uani 1 1 d . . .
C9 C 0.27743(16) 0.72917(15) 0.45909(10) 0.0271(3) Uani 1 1 d . . .
C10 C 0.17678(15) 0.65418(15) 0.49592(10) 0.0261(3) Uani 1 1 d . . .
C11 C 0.17436(13) 0.50573(15) 0.49203(9) 0.0204(3) Uani 1 1 d . . .
C12 C 0.27333(12) 0.43578(13) 0.45005(8) 0.0159(2) Uani 1 1 d . . .
C13 C 0.17366(12) 0.18176(13) 0.35855(8) 0.0151(2) Uani 1 1 d . . .
C14 C 0.17598(13) 0.22444(14) 0.27036(9) 0.0189(3) Uani 1 1 d . . .
C15 C 0.07928(14) 0.17835(16) 0.21043(9) 0.0231(3) Uani 1 1 d . . .
C16 C -0.01960(14) 0.09068(17) 0.23839(10) 0.0253(3) Uani 1 1 d . . .
C17 C -0.02186(14) 0.04820(16) 0.32599(10) 0.0262(3) Uani 1 1 d . . .
C18 C 0.07472(13) 0.09324(15) 0.38621(9) 0.0213(3) Uani 1 1 d . . .
Se1 Se 0.3061(4) 0.1234(3) 0.5525(2) 0.0171(2) Uani 0.50 1 d P . .
P1 P 0.29606(3) 0.24607(3) 0.43808(2) 0.01332(8) Uani 1 1 d . . .
S1 S 0.3054(9) 0.1402(8) 0.5517(6) 0.0171(2) Uani 0.50 1 d P . .
H2 H 0.5059(16) 0.0721(18) 0.3548(11) 0.020(4) Uiso 1 1 d . . .
H3 H 0.6939(18) 0.1368(19) 0.2832(12) 0.032(5) Uiso 1 1 d . . .
H4 H 0.7455(19) 0.3809(18) 0.2705(12) 0.032(5) Uiso 1 1 d . . .
H5 H 0.6089(18) 0.557(2) 0.3291(12) 0.032(5) Uiso 1 1 d . . .
H9 H 0.4476(18) 0.711(2) 0.3933(12) 0.029(4) Uiso 1 1 d . . .
H10 H 0.2816(18) 0.831(2) 0.4651(12) 0.031(5) Uiso 1 1 d . . .
H11 H 0.1099(19) 0.703(2) 0.5283(13) 0.038(5) Uiso 1 1 d . . .
H12 H 0.1050(17) 0.4517(19) 0.5196(11) 0.026(4) Uiso 1 1 d . . .
H14 H 0.2424(17) 0.2838(18) 0.2505(11) 0.025(4) Uiso 1 1 d . . .
H15 H 0.0810(17) 0.2093(18) 0.1496(12) 0.024(4) Uiso 1 1 d . . .
H16 H -0.0838(18) 0.058(2) 0.1967(12) 0.032(5) Uiso 1 1 d . . .
H17 H -0.0882(18) -0.009(2) 0.3460(12) 0.032(5) Uiso 1 1 d . . .
H18 H 0.0754(16) 0.0627(18) 0.4473(11) 0.025(4) Uiso 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
C1 0.0134(5) 0.0203(6) 0.0133(6) -0.0001(5) -0.0019(4) -0.0013(5)
C2 0.0166(6) 0.0246(7) 0.0177(6) -0.0017(5) -0.0030(5) 0.0024(5)
C3 0.0167(6) 0.0403(8) 0.0185(7) -0.0035(6) -0.0003(5) 0.0051(6)
C4 0.0159(6) 0.0467(9) 0.0191(7) 0.0050(6) 0.0005(5) -0.0044(6)
C5 0.0194(6) 0.0307(7) 0.0203(7) 0.0067(5) -0.0029(5) -0.0066(5)
C6 0.0162(6) 0.0211(6) 0.0138(6) 0.0022(5) -0.0042(5) -0.0024(5)
C7 0.0193(6) 0.0169(6) 0.0149(6) 0.0014(5) -0.0061(5) -0.0015(5)
C8 0.0292(7) 0.0175(6) 0.0227(7) 0.0032(5) -0.0093(6) -0.0056(5)
C9 0.0392(8) 0.0147(6) 0.0265(7) -0.0027(5) -0.0135(6) 0.0025(6)
C10 0.0331(8) 0.0209(6) 0.0236(7) -0.0059(5) -0.0060(6) 0.0098(6)
C11 0.0223(6) 0.0203(6) 0.0184(6) -0.0016(5) -0.0027(5) 0.0044(5)
C12 0.0184(6) 0.0139(5) 0.0152(6) -0.0009(4) -0.0041(5) 0.0005(5)
C13 0.0135(5) 0.0134(5) 0.0184(6) -0.0024(4) 0.0001(4) 0.0008(4)
C14 0.0178(6) 0.0195(6) 0.0195(6) -0.0003(5) 0.0002(5) -0.0032(5)
C15 0.0231(7) 0.0271(7) 0.0191(7) -0.0021(5) -0.0019(5) -0.0031(5)
C16 0.0197(6) 0.0300(7) 0.0260(7) -0.0066(6) -0.0034(5) -0.0061(6)
C17 0.0188(6) 0.0292(7) 0.0307(8) -0.0013(6) 0.0016(6) -0.0099(6)
C18 0.0194(6) 0.0231(6) 0.0214(7) 0.0009(5) 0.0021(5) -0.0040(5)
Se1 0.02090(11) 0.0135(7) 0.01687(12) 0.0040(4) 0.00041(8) -0.0007(4)
P1 0.01302(14) 0.01228(14) 0.01463(16) 0.00038(11) -0.00002(11) -0.00009(10)
S1 0.02090(11) 0.0135(7) 0.01687(12) 0.0040(4) 0.00041(8) -0.0007(4)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3884(18) . ?
C1 C6 1.4071(18) . ?
C1 P1 1.8025(13) . ?
C2 C3 1.394(2) . ?
C2 H2 0.922(17) . ?
C3 C4 1.391(2) . ?
C3 H3 0.979(18) . ?
C4 C5 1.389(2) . ?
C4 H4 0.968(19) . ?
C5 C6 1.3959(18) . ?
C5 H5 0.963(19) . ?
C6 C7 1.4795(18) . ?
C7 C8 1.3965(18) . ?
C7 C12 1.4027(18) . ?
C8 C9 1.392(2) . ?
C8 H9 0.962(19) . ?
C9 C10 1.389(2) . ?
C9 H10 0.958(19) . ?
C10 C11 1.3960(19) . ?
C10 H11 0.98(2) . ?
C11 C12 1.3879(18) . ?
C11 H12 0.982(17) . ?
C12 P1 1.8075(13) . ?
C13 C18 1.3930(18) . ?
C13 C14 1.3947(18) . ?
C13 P1 1.8160(13) . ?
C14 C15 1.3927(19) . ?
C14 H14 0.942(18) . ?
C15 C16 1.389(2) . ?
C15 H15 0.967(18) . ?
C16 C17 1.386(2) . ?
C16 H16 0.949(19) . ?
C17 C18 1.391(2) . ?
C17 H17 0.930(19) . ?
C18 H18 0.968(17) . ?
Se1 P1 2.079(3) . ?
P1 S1 1.986(9) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.60(12) . . ?
C2 C1 P1 127.85(10) . . ?
C6 C1 P1 110.53(9) . . ?
C1 C2 C3 118.41(13) . . ?
C1 C2 H2 120.3(10) . . ?
C3 C2 H2 121.3(10) . . ?
C4 C3 C2 120.42(14) . . ?
C4 C3 H3 121.3(11) . . ?
C2 C3 H3 118.2(11) . . ?
C5 C4 C3 121.19(13) . . ?
C5 C4 H4 120.1(11) . . ?
C3 C4 H4 118.7(11) . . ?
C4 C5 C6 119.16(13) . . ?
C4 C5 H5 120.9(11) . . ?
C6 C5 H5 119.9(11) . . ?
C5 C6 C1 119.21(12) . . ?
C5 C6 C7 127.38(13) . . ?
C1 C6 C7 113.41(11) . . ?
C8 C7 C12 119.06(13) . . ?
C8 C7 C6 127.44(13) . . ?
C12 C7 C6 113.49(11) . . ?
C9 C8 C7 119.34(14) . . ?
C9 C8 H9 120.7(11) . . ?
C7 C8 H9 120.0(11) . . ?
C10 C9 C8 121.11(13) . . ?
C10 C9 H10 119.9(11) . . ?
C8 C9 H10 118.9(11) . . ?
C9 C10 C11 120.16(14) . . ?
C9 C10 H11 121.0(12) . . ?
C11 C10 H11 118.7(12) . . ?
C12 C11 C10 118.69(13) . . ?
C12 C11 H12 120.6(10) . . ?
C10 C11 H12 120.7(10) . . ?
C11 C12 C7 121.64(12) . . ?
C11 C12 P1 127.81(10) . . ?
C7 C12 P1 110.51(9) . . ?
C18 C13 C14 119.84(12) . . ?
C18 C13 P1 119.94(10) . . ?
C14 C13 P1 120.18(9) . . ?
C15 C14 C13 119.79(12) . . ?
C15 C14 H14 119.2(11) . . ?
C13 C14 H14 121.0(11) . . ?
C16 C15 C14 120.18(13) . . ?
C16 C15 H15 120.5(10) . . ?
C14 C15 H15 119.3(10) . . ?
C17 C16 C15 120.03(13) . . ?
C17 C16 H16 120.5(11) . . ?
C15 C16 H16 119.5(11) . . ?
C16 C17 C18 120.16(13) . . ?
C16 C17 H17 121.1(11) . . ?
C18 C17 H17 118.7(11) . . ?
C17 C18 C13 120.00(13) . . ?
C17 C18 H18 121.0(10) . . ?
C13 C18 H18 119.0(10) . . ?
C1 P1 C12 92.04(6) . . ?
C1 P1 C13 107.51(6) . . ?
C12 P1 C13 107.75(6) . . ?
C1 P1 S1 118.2(3) . . ?
C12 P1 S1 114.2(2) . . ?
C13 P1 S1 114.7(3) . . ?
C1 P1 Se1 117.41(11) . . ?
C12 P1 Se1 117.76(10) . . ?
C13 P1 Se1 112.32(10) . . ?
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
C6 C1 C2 C3 -0.63(19) . . . . ?
P1 C1 C2 C3 -178.92(10) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 0.82(19) . . . . ?
C4 C5 C6 C7 180.00(12) . . . . ?
C2 C1 C6 C5 -0.24(19) . . . . ?
P1 C1 C6 C5 178.32(10) . . . . ?
C2 C1 C6 C7 -179.52(11) . . . . ?
P1 C1 C6 C7 -0.97(13) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C1 C6 C7 C8 179.07(12) . . . . ?
C5 C6 C7 C12 -179.03(12) . . . . ?
C1 C6 C7 C12 0.19(15) . . . . ?
C12 C7 C8 C9 -0.06(19) . . . . ?
C6 C7 C8 C9 -178.88(12) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C7 0.72(19) . . . . ?
C10 C11 C12 P1 178.27(10) . . . . ?
C8 C7 C12 C11 -0.36(19) . . . . ?
C6 C7 C12 C11 178.61(11) . . . . ?
C8 C7 C12 P1 -178.30(10) . . . . ?
C6 C7 C12 P1 0.68(13) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
P1 C13 C14 C15 -177.89(10) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 0.3(2) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
P1 C13 C18 C17 177.60(11) . . . . ?
C2 C1 P1 C12 179.58(12) . . . . ?
C6 C1 P1 C12 1.14(10) . . . . ?
C2 C1 P1 C13 -71.08(13) . . . . ?
C6 C1 P1 C13 110.47(9) . . . . ?
C2 C1 P1 S1 60.7(3) . . . . ?
C6 C1 P1 S1 -117.8(3) . . . . ?
C2 C1 P1 Se1 56.66(16) . . . . ?
C6 C1 P1 Se1 -121.78(13) . . . . ?
C11 C12 P1 C1 -178.81(12) . . . . ?
C7 C12 P1 C1 -1.03(9) . . . . ?
C11 C12 P1 C13 72.07(13) . . . . ?
C7 C12 P1 C13 -110.15(9) . . . . ?
C11 C12 P1 S1 -56.6(3) . . . . ?
C7 C12 P1 S1 121.2(3) . . . . ?
C11 C12 P1 Se1 -56.17(17) . . . . ?
C7 C12 P1 Se1 121.60(14) . . . . ?
C18 C13 P1 C1 150.09(10) . . . . ?
C14 C13 P1 C1 -31.99(12) . . . . ?
C18 C13 P1 C12 -111.85(11) . . . . ?
C14 C13 P1 C12 66.07(12) . . . . ?
C18 C13 P1 S1 16.5(3) . . . . ?
C14 C13 P1 S1 -165.6(3) . . . . ?
C18 C13 P1 Se1 19.45(15) . . . . ?
C14 C13 P1 Se1 -162.63(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
#===END