# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1400

#==============================================================================
data_global
#==============================================================================

# 1. SUBMISSION DETAILS

_publ_contact_author_name
;
        Dr Robin G. Pritchard
;
_publ_contact_author_address
;
        Department of Chemistry
        University of Manchester Institute of Science and Technology
        PO Box 88
        Manchester M60 1QD
        England
;
_publ_contact_author_phone        '0161 200 4568'
_publ_contact_author_fax          '0161 236 7677'
_publ_contact_author_email        'Robin.Pritchard@UMIST.AC.UK'
_publ_requested_journal           'Chem. Comm.'
_publ_author_name   'S.M. Godfrey et al'
_publ_section_title 'The Structural Characterisation of Ph3PSe(Ph)I....'

data_p

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C25 H22 Cl2 I P Se'
_chemical_formula_weight          630.16

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'
 'Cl'  'Cl'   0.1484   0.1585
 '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'
 'I'  'I'  -0.4742   1.8119
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting         'triclinic'
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                    9.2713(11)
_cell_length_b                    10.329(3)
_cell_length_c                    13.245(2)
_cell_angle_alpha                 91.773(16)
_cell_angle_beta                  93.314(11)
_cell_angle_gamma                 95.349(14)
_cell_volume                      1259.9(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     203(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description       'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.661
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              616
_exptl_absorpt_coefficient_mu     3.001
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   0.5208
_exptl_absorpt_correction_T_max   0.7534
_exptl_absorpt_process_details    ?

_exptl_special_details
;
 ?
;

_diffrn_ambient_temperature       203(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   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             4714
_diffrn_reflns_av_R_equivalents   0.0108
_diffrn_reflns_av_sigmaI/netI     0.0176
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        11
_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          1.54
_diffrn_reflns_theta_max          24.98
_reflns_number_total              4411
_reflns_number_gt                 3865
_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^)+(0.0265P)^2^+1.5026P] 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     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4411
_refine_ls_number_parameters      359
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0323
_refine_ls_R_factor_gt            0.0251
_refine_ls_wR_factor_ref          0.0569
_refine_ls_wR_factor_gt           0.0543
_refine_ls_goodness_of_fit_ref    1.041
_refine_ls_restrained_S_all       1.041
_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_symetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
I1 I 0.60532(2) 0.58650(2) 0.319674(15) 0.03022(7) Uani 1 1 d . . .
Se1 Se 0.78735(3) 0.37824(3) 0.20377(2) 0.02774(8) Uani 1 1 d . . .
Cl1 Cl 0.36221(15) 0.84422(13) 0.50373(10) 0.0791(4) Uani 1 1 d . . .
Cl2 Cl 0.59337(19) 0.84853(14) 0.65809(11) 0.0968(5) Uani 1 1 d . . .
P1 P 0.90080(8) 0.22342(7) 0.12460(6) 0.02480(17) Uani 1 1 d . . .
C1 C 0.9507(3) 0.4290(3) 0.2971(2) 0.0269(6) Uani 1 1 d . . .
C2 C 1.0394(4) 0.5400(3) 0.2790(3) 0.0351(7) Uani 1 1 d . . .
C3 C 1.1610(4) 0.5731(4) 0.3415(3) 0.0390(8) Uani 1 1 d . . .
C4 C 1.1963(4) 0.4968(4) 0.4202(3) 0.0406(8) Uani 1 1 d . . .
C5 C 1.1064(4) 0.3870(4) 0.4387(3) 0.0428(9) Uani 1 1 d . . .
C6 C 0.9819(4) 0.3537(3) 0.3782(2) 0.0348(8) Uani 1 1 d . . .
C7 C 1.0771(3) 0.2745(3) 0.0811(2) 0.0265(6) Uani 1 1 d . . .
C8 C 1.1912(3) 0.3177(3) 0.1506(3) 0.0336(7) Uani 1 1 d . . .
C9 C 1.3252(4) 0.3566(4) 0.1169(3) 0.0430(9) Uani 1 1 d . . .
C10 C 1.3462(4) 0.3527(4) 0.0147(3) 0.0476(10) Uani 1 1 d . . .
C11 C 1.2353(4) 0.3085(4) -0.0544(3) 0.0440(9) Uani 1 1 d . . .
C12 C 1.0999(4) 0.2693(3) -0.0215(2) 0.0336(7) Uani 1 1 d . . .
C13 C 0.9155(3) 0.0865(3) 0.2026(2) 0.0274(7) Uani 1 1 d . . .
C14 C 1.0420(4) 0.0244(3) 0.2100(3) 0.0351(7) Uani 1 1 d . . .
C15 C 1.0489(5) -0.0818(4) 0.2700(3) 0.0484(10) Uani 1 1 d . . .
C16 C 0.9321(5) -0.1261(4) 0.3218(3) 0.0519(10) Uani 1 1 d . . .
C17 C 0.8070(5) -0.0644(4) 0.3149(3) 0.0490(10) Uani 1 1 d . . .
C18 C 0.7983(4) 0.0421(3) 0.2565(3) 0.0384(8) Uani 1 1 d . . .
C19 C 0.7777(3) 0.1795(3) 0.0168(2) 0.0299(7) Uani 1 1 d . . .
C20 C 0.7225(4) 0.0524(4) -0.0055(3) 0.0346(7) Uani 1 1 d . . .
C21 C 0.6273(4) 0.0245(4) -0.0900(3) 0.0467(10) Uani 1 1 d . . .
C22 C 0.5902(4) 0.1221(5) -0.1506(3) 0.0530(11) Uani 1 1 d . . .
C23 C 0.6439(4) 0.2477(5) -0.1291(3) 0.0475(10) Uani 1 1 d . . .
C24 C 0.7385(4) 0.2779(4) -0.0455(3) 0.0391(8) Uani 1 1 d . . .
C25 C 0.4894(8) 0.7568(5) 0.5641(4) 0.0705(15) Uani 1 1 d . . .
H2 H 1.013(4) 0.597(3) 0.220(3) 0.042(10) Uiso 1 1 d . . .
H3 H 1.218(4) 0.642(4) 0.332(3) 0.045(11) Uiso 1 1 d . . .
H4 H 1.282(4) 0.522(4) 0.463(3) 0.047(10) Uiso 1 1 d . . .
H5 H 1.126(5) 0.337(4) 0.483(3) 0.064(14) Uiso 1 1 d . . .
H6 H 0.917(4) 0.282(3) 0.390(3) 0.037(9) Uiso 1 1 d . . .
H8 H 1.175(4) 0.321(3) 0.222(3) 0.035(9) Uiso 1 1 d . . .
H9 H 1.397(4) 0.390(4) 0.163(3) 0.052(12) Uiso 1 1 d . . .
H10 H 1.437(4) 0.380(4) -0.005(3) 0.053(11) Uiso 1 1 d . . .
H11 H 1.247(4) 0.306(3) -0.131(3) 0.035(9) Uiso 1 1 d . . .
H12 H 1.023(4) 0.241(3) -0.068(3) 0.042(10) Uiso 1 1 d . . .
H14 H 1.122(4) 0.051(3) 0.173(2) 0.030(9) Uiso 1 1 d . . .
H15 H 1.137(5) -0.119(5) 0.280(4) 0.077(15) Uiso 1 1 d . . .
H16 H 0.940(5) -0.190(4) 0.363(3) 0.062(13) Uiso 1 1 d . . .
H17 H 0.728(5) -0.089(4) 0.349(3) 0.058(12) Uiso 1 1 d . . .
H18 H 0.714(4) 0.084(4) 0.250(3) 0.044(10) Uiso 1 1 d . . .
H20 H 0.740(4) -0.012(3) 0.038(3) 0.033(9) Uiso 1 1 d . . .
H21 H 0.588(4) -0.059(4) -0.101(3) 0.039(10) Uiso 1 1 d . . .
H22 H 0.530(5) 0.102(4) -0.199(3) 0.062(13) Uiso 1 1 d . . .
H23 H 0.622(4) 0.314(4) -0.170(3) 0.044(11) Uiso 1 1 d . . .
H24 H 0.779(4) 0.365(4) -0.033(3) 0.040(10) Uiso 1 1 d . . .
H25B H 0.448(7) 0.684(6) 0.593(5) 0.11(2) Uiso 1 1 d . . .
H25A H 0.550(6) 0.726(5) 0.523(4) 0.081(17) 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
I1 0.02977(12) 0.03424(12) 0.02700(11) 0.00056(8) -0.00002(8) 0.00617(8)
Se1 0.02561(17) 0.02850(17) 0.02895(17) -0.00171(13) -0.00198(12) 0.00492(13)
Cl1 0.0808(9) 0.0703(8) 0.0818(9) -0.0117(6) -0.0113(7) -0.0009(7)
Cl2 0.1244(13) 0.0749(9) 0.0859(10) -0.0125(7) -0.0427(9) 0.0168(8)
P1 0.0236(4) 0.0259(4) 0.0248(4) 0.0003(3) -0.0010(3) 0.0032(3)
C1 0.0247(16) 0.0279(16) 0.0284(16) -0.0036(13) 0.0022(12) 0.0047(13)
C2 0.0372(19) 0.0310(18) 0.0369(18) 0.0028(14) -0.0014(15) 0.0039(14)
C3 0.039(2) 0.0307(19) 0.045(2) -0.0015(16) -0.0013(16) -0.0072(16)
C4 0.0333(19) 0.049(2) 0.0379(19) -0.0064(16) -0.0073(16) 0.0025(16)
C5 0.043(2) 0.059(2) 0.0268(17) 0.0107(17) -0.0027(15) 0.0052(18)
C6 0.0376(19) 0.0389(19) 0.0274(17) 0.0046(14) 0.0056(14) -0.0028(16)
C7 0.0271(16) 0.0231(15) 0.0303(16) 0.0030(12) 0.0044(13) 0.0048(12)
C8 0.0292(18) 0.0353(18) 0.0359(19) -0.0025(14) 0.0016(14) 0.0032(14)
C9 0.0270(19) 0.041(2) 0.059(2) -0.0074(18) 0.0018(17) -0.0007(15)
C10 0.038(2) 0.037(2) 0.069(3) 0.0029(18) 0.022(2) -0.0016(17)
C11 0.051(2) 0.042(2) 0.042(2) 0.0102(17) 0.0173(18) 0.0054(17)
C12 0.0365(19) 0.0351(18) 0.0299(17) 0.0076(14) 0.0018(15) 0.0053(15)
C13 0.0318(17) 0.0249(16) 0.0245(15) 0.0000(12) 0.0001(13) -0.0003(13)
C14 0.0364(19) 0.0336(18) 0.0369(18) 0.0056(14) 0.0078(15) 0.0065(15)
C15 0.056(3) 0.041(2) 0.051(2) 0.0130(18) 0.0027(19) 0.0185(19)
C16 0.070(3) 0.035(2) 0.053(2) 0.0160(18) 0.009(2) 0.009(2)
C17 0.056(3) 0.040(2) 0.052(2) 0.0086(18) 0.019(2) -0.0053(19)
C18 0.0334(19) 0.0356(19) 0.046(2) 0.0060(16) 0.0068(16) -0.0001(16)
C19 0.0215(15) 0.0397(18) 0.0285(16) -0.0055(14) -0.0005(12) 0.0061(13)
C20 0.0288(18) 0.040(2) 0.0343(18) -0.0050(16) 0.0037(14) 0.0015(15)
C21 0.033(2) 0.057(3) 0.046(2) -0.018(2) 0.0011(17) -0.0066(18)
C22 0.032(2) 0.090(4) 0.035(2) -0.017(2) -0.0091(17) 0.010(2)
C23 0.043(2) 0.069(3) 0.0327(19) -0.0004(19) -0.0056(16) 0.023(2)
C24 0.041(2) 0.044(2) 0.0339(18) -0.0005(16) -0.0056(15) 0.0142(17)
C25 0.121(5) 0.048(3) 0.042(2) -0.007(2) 0.009(3) 0.007(3)

_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 C1 1.921(3) . ?
Se1 P1 2.2585(9) . ?
Cl1 C25 1.726(6) . ?
Cl2 C25 1.731(5) . ?
P1 C13 1.788(3) . ?
P1 C19 1.795(3) . ?
P1 C7 1.803(3) . ?
C1 C6 1.379(4) . ?
C1 C2 1.383(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.369(5) . ?
C4 C5 1.381(5) . ?
C5 C6 1.377(5) . ?
C7 C12 1.387(4) . ?
C7 C8 1.393(4) . ?
C8 C9 1.374(5) . ?
C9 C10 1.378(6) . ?
C10 C11 1.372(6) . ?
C11 C12 1.382(5) . ?
C13 C18 1.385(4) . ?
C13 C14 1.389(5) . ?
C14 C15 1.379(5) . ?
C15 C16 1.366(6) . ?
C16 C17 1.374(6) . ?
C17 C18 1.370(5) . ?
C19 C20 1.381(5) . ?
C19 C24 1.390(5) . ?
C20 C21 1.390(5) . ?
C21 C22 1.365(6) . ?
C22 C23 1.361(6) . ?
C23 C24 1.381(5) . ?

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 Se1 P1 93.59(9) . . ?
C13 P1 C19 110.10(15) . . ?
C13 P1 C7 108.95(14) . . ?
C19 P1 C7 108.85(14) . . ?
C13 P1 Se1 110.75(10) . . ?
C19 P1 Se1 101.77(10) . . ?
C7 P1 Se1 116.15(10) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 Se1 120.6(2) . . ?
C2 C1 Se1 118.6(2) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C4 120.8(3) . . ?
C3 C4 C5 119.8(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 119.1(3) . . ?
C12 C7 C8 119.9(3) . . ?
C12 C7 P1 120.1(2) . . ?
C8 C7 P1 120.0(2) . . ?
C9 C8 C7 119.6(3) . . ?
C8 C9 C10 120.0(4) . . ?
C11 C10 C9 120.9(4) . . ?
C10 C11 C12 119.7(3) . . ?
C11 C12 C7 119.9(3) . . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 P1 119.2(3) . . ?
C14 C13 P1 121.1(2) . . ?
C15 C14 C13 119.5(3) . . ?
C16 C15 C14 120.4(4) . . ?
C15 C16 C17 120.1(4) . . ?
C18 C17 C16 120.5(4) . . ?
C17 C18 C13 119.7(4) . . ?
C20 C19 C24 119.8(3) . . ?
C20 C19 P1 122.1(3) . . ?
C24 C19 P1 118.1(3) . . ?
C19 C20 C21 119.4(4) . . ?
C22 C21 C20 120.1(4) . . ?
C23 C22 C21 120.9(4) . . ?
C22 C23 C24 120.1(4) . . ?
C23 C24 C19 119.7(4) . . ?
Cl1 C25 Cl2 112.4(3) . . ?

_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              24.98
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    1.150
_refine_diff_density_min   -0.900
_refine_diff_density_rms    0.067