# Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2001
# CCDC Number: 186/2331

_publ_contact_author_name   'Robin G. Pritchard'
_publ_contact_author_address  'Department of Chemistry, UMIST, Manchester'
_publ_requested_journal 'Dalton'
_publ_section_title
;
Structural Isomerism in R3PSe(Ph)I compounds  Your code B008525L
;
 
data_smg30a
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C12 H23 I1 N3 P1 Se1'
_chemical_formula_sum
 'C12 H29 I N3 P Se'
_chemical_formula_weight          403.83
 
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'
 'I'  'I'  -0.4742   1.8119
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 '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    'C m c a'
 
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'
 'x+1/2, y+1/2, z'
 '-x+1/2, -y+1, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x+1/2, y+1, -z+1/2'
 '-x, -y, -z'
 'x, y-1/2, -z-1/2'
 '-x, y, z'
 'x, -y-1/2, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, y, -z-1/2'
 '-x+1/2, y+1/2, z'
 'x+1/2, -y, z-1/2'
 
_cell_length_a                    10.164
_cell_length_b                    12.526
_cell_length_c                    26.427
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3364.7
_cell_formula_units_Z             8
_cell_measurement_temperature     203(2)
_cell_measurement_reflns_used     0
_cell_measurement_theta_min       0
_cell_measurement_theta_max       0
 
_exptl_crystal_description        prism
_exptl_crystal_colour             'pale yellow'
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.785
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1744
_exptl_absorpt_coefficient_mu     4.153
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   0.4233
_exptl_absorpt_correction_T_max   0.4906
_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   'Enraf Nonius CAD4'
_diffrn_measurement_method        'non-profiled omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          3
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   60
_diffrn_standards_decay_%         0
_diffrn_reflns_number             2949
_diffrn_reflns_av_R_equivalents   0.0647
_diffrn_reflns_av_sigmaI/netI     0.0603
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          1.54
_diffrn_reflns_theta_max          24.97
_reflns_number_total              1569
_reflns_number_gt                 1269
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement        'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction         'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX publication routines (Farrugia, 1999)'
 
_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.

 The cation lies on a crystallographic mirror plane , which bisects
 the P atom and two of the N(Me)2 groups. This has led to the remaining 
 N(Me)2 and the SePh being disordered so that half of each occupies each
 side of the mirror plane
;
 
_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^)+(0.0730P)^2^+6.7690P] 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      SHELXL
_refine_ls_extinction_coef        0.00058(16)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          1569
_refine_ls_number_parameters      136
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0628
_refine_ls_R_factor_gt            0.0478
_refine_ls_wR_factor_ref          0.1321
_refine_ls_wR_factor_gt           0.1217
_refine_ls_goodness_of_fit_ref    1.092
_refine_ls_restrained_S_all       1.092
_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
I1 I 0.0000 0.52336(6) 0.33267(2) 0.0494(3) Uani 1 2 d S . .
Se1 Se 0.31262(15) 0.59166(12) 0.40641(6) 0.0310(4) Uani 0.50 1 d P . .
P1 P 0.5000 0.57412(15) 0.36185(7) 0.0238(5) Uani 1 2 d S . .
N1 N 0.5000 0.6691(5) 0.3206(3) 0.0301(15) Uani 1 2 d S . .
N2 N 0.5000 0.4507(6) 0.3422(3) 0.0323(15) Uani 1 2 d S . .
C1 C 0.3866(9) 0.6923(9) 0.4534(4) 0.026(2) Uani 0.50 1 d P . .
C2 C 0.4135(11) 0.7958(9) 0.4381(4) 0.034(3) Uani 0.50 1 d P . .
H2 H 0.4001 0.8171 0.4044 0.041 Uiso 0.50 1 calc PR . .
C3 C 0.4616(12) 0.8682(9) 0.4744(5) 0.048(4) Uani 0.50 1 d P . .
H3 H 0.4833 0.9382 0.4647 0.057 Uiso 0.50 1 calc PR . .
C4 C 0.477(3) 0.8369(9) 0.5248(5) 0.039(7) Uani 0.50 1 d P . .
H4 H 0.5071 0.8862 0.5491 0.047 Uiso 0.50 1 calc PR . .
C5 C 0.4499(12) 0.7351(9) 0.5385(4) 0.040(3) Uani 0.50 1 d P . .
H5 H 0.4625 0.7138 0.5722 0.048 Uiso 0.50 1 calc PR . .
C6 C 0.4026(12) 0.6603(10) 0.5029(4) 0.037(3) Uani 0.50 1 d P . .
H6 H 0.3825 0.5901 0.5128 0.044 Uiso 0.50 1 calc PR . .
C7 C 0.3809(6) 0.6990(6) 0.2927(3) 0.0517(18) Uani 1 1 d . . .
H7A H 0.3738 0.7762 0.2915 0.078 Uiso 1 1 calc R . .
H7B H 0.3043 0.6697 0.3096 0.078 Uiso 1 1 calc R . .
H7C H 0.3857 0.6710 0.2585 0.078 Uiso 1 1 calc R . .
C8 C 0.6187(7) 0.4071(6) 0.3185(3) 0.065(2) Uani 1 1 d . . .
H8A H 0.6170 0.3298 0.3206 0.098 Uiso 1 1 calc R . .
H8B H 0.6958 0.4339 0.3360 0.098 Uiso 1 1 calc R . .
H8C H 0.6220 0.4287 0.2833 0.098 Uiso 1 1 calc R . .
N3 N 0.6281(12) 0.5858(9) 0.3933(5) 0.033(3) Uani 0.50 1 d P . .
C9 C 0.6971(11) 0.6853(10) 0.4051(5) 0.042(3) Uani 0.50 1 d P . .
H9A H 0.6572 0.7437 0.3865 0.064 Uiso 1 1 calc R . .
H9B H 0.7889 0.6788 0.3956 0.064 Uiso 1 1 calc R . .
H9C H 0.6910 0.6994 0.4412 0.064 Uiso 1 1 calc R . .
C10 C 0.6785(13) 0.4996(11) 0.4257(5) 0.046(3) Uani 0.50 1 d P . .
H10A H 0.6140 0.4426 0.4276 0.068 Uiso 1 1 calc R . .
H10B H 0.6951 0.5272 0.4594 0.068 Uiso 1 1 calc R . .
H10C H 0.7598 0.4720 0.4116 0.068 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
I1 0.0568(5) 0.0528(5) 0.0385(4) 0.0004(3) 0.000 0.000
Se1 0.0213(7) 0.0333(8) 0.0383(8) -0.0077(6) 0.0039(6) -0.0059(7)
P1 0.0193(9) 0.0253(10) 0.0268(10) -0.0037(8) 0.000 0.000
N1 0.022(3) 0.029(3) 0.039(4) 0.003(3) 0.000 0.000
N2 0.026(3) 0.028(3) 0.043(4) -0.009(3) 0.000 0.000
C1 0.016(5) 0.032(6) 0.032(5) -0.002(5) 0.002(4) 0.000(4)
C2 0.040(6) 0.032(6) 0.030(6) 0.000(5) 0.003(5) 0.002(5)
C3 0.059(12) 0.025(5) 0.060(7) -0.007(5) -0.004(6) -0.008(5)
C4 0.03(2) 0.037(5) 0.046(6) -0.015(4) -0.015(7) -0.003(6)
C5 0.053(7) 0.037(6) 0.030(6) -0.003(5) -0.004(5) 0.009(5)
C6 0.042(6) 0.029(6) 0.038(6) 0.001(5) 0.002(5) 0.006(6)
C7 0.032(3) 0.073(5) 0.050(4) 0.020(4) -0.002(3) 0.010(3)
C8 0.056(5) 0.037(4) 0.102(6) -0.028(4) 0.029(5) -0.001(4)
N3 0.018(6) 0.030(6) 0.052(7) 0.004(5) -0.004(5) 0.000(5)
C9 0.017(5) 0.062(9) 0.048(7) -0.016(7) -0.007(5) -0.002(6)
C10 0.041(7) 0.061(8) 0.034(6) 0.021(6) -0.009(6) 0.000(6)
 
_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 N3 0.699(13) 11_655 ?
Se1 C9 1.178(13) 11_655 ?
Se1 C10 1.265(13) 11_655 ?
Se1 C1 1.923(11) . ?
Se1 P1 2.2500(19) . ?
P1 N3 1.551(14) . ?
P1 N3 1.551(14) 11_655 ?
P1 N1 1.614(7) . ?
P1 N2 1.631(7) . ?
P1 Se1 2.2500(19) 11_655 ?
N1 C7 1.466(7) 11_655 ?
N1 C7 1.466(7) . ?
N2 C8 1.465(8) 11_655 ?
N2 C8 1.465(8) . ?
C1 C6 1.377(15) . ?
C1 C2 1.386(15) . ?
C1 C9 1.536(15) 11_655 ?
C2 C3 1.406(16) . ?
C2 C2 1.76(2) 11_655 ?
C2 C3 1.830(17) 11_655 ?
C2 C9 1.985(16) 11_655 ?
C3 C4 1.399(18) . ?
C4 C5 1.354(18) . ?
C5 C6 1.411(17) . ?
N3 Se1 0.699(12) 11_655 ?
N3 C9 1.465(16) . ?
N3 C10 1.471(16) . ?
 
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
N3 Se1 C9 99.4(12) 11_655 11_655 ?
N3 Se1 C10 92.4(12) 11_655 11_655 ?
C9 Se1 C10 157.8(8) 11_655 11_655 ?
N3 Se1 C1 93.0(11) 11_655 . ?
C9 Se1 C1 53.0(7) 11_655 . ?
C10 Se1 C1 108.0(7) 11_655 . ?
N3 Se1 P1 1.9(10) 11_655 . ?
C9 Se1 P1 98.8(6) 11_655 . ?
C10 Se1 P1 93.6(6) 11_655 . ?
C1 Se1 P1 94.1(3) . . ?
N3 P1 N3 114.1(9) . 11_655 ?
N3 P1 N1 107.0(5) . . ?
N3 P1 N1 107.0(4) 11_655 . ?
N3 P1 N2 105.1(4) . . ?
N3 P1 N2 105.1(5) 11_655 . ?
N1 P1 N2 118.9(4) . . ?
N3 P1 Se1 0.9(5) . 11_655 ?
N3 P1 Se1 114.9(4) 11_655 11_655 ?
N1 P1 Se1 106.36(14) . 11_655 ?
N2 P1 Se1 105.05(14) . 11_655 ?
N3 P1 Se1 114.9(4) . . ?
N3 P1 Se1 0.9(5) 11_655 . ?
N1 P1 Se1 106.36(14) . . ?
N2 P1 Se1 105.05(14) . . ?
Se1 P1 Se1 115.66(11) 11_655 . ?
C7 N1 C7 111.3(7) 11_655 . ?
C7 N1 P1 121.9(4) 11_655 . ?
C7 N1 P1 121.9(4) . . ?
C8 N2 C8 111.0(7) 11_655 . ?
C8 N2 P1 119.3(4) 11_655 . ?
C8 N2 P1 119.3(4) . . ?
C6 C1 C2 121.7(10) . . ?
C6 C1 C9 146.9(11) . 11_655 ?
C2 C1 C9 85.4(9) . 11_655 ?
C6 C1 Se1 118.0(9) . . ?
C2 C1 Se1 120.2(8) . . ?
C9 C1 Se1 37.8(6) 11_655 . ?
C1 C2 C3 118.2(10) . . ?
C1 C2 C2 101.4(6) . 11_655 ?
C3 C2 C2 69.7(7) . 11_655 ?
C1 C2 C3 116.6(9) . 11_655 ?
C3 C2 C3 23.6(8) . 11_655 ?
C2 C2 C3 46.1(5) 11_655 11_655 ?
C1 C2 C9 50.5(7) . 11_655 ?
C3 C2 C9 161.0(10) . 11_655 ?
C2 C2 C9 124.5(5) 11_655 11_655 ?
C3 C2 C9 165.5(8) 11_655 11_655 ?
C4 C3 C2 120.6(11) . . ?
C5 C4 C3 119.6(12) . . ?
C4 C5 C6 121.2(11) . . ?
C1 C6 C5 118.7(11) . . ?
Se1 N3 C9 52.5(10) 11_655 . ?
Se1 N3 C10 59.2(11) 11_655 . ?
C9 N3 C10 109.5(12) . . ?
Se1 N3 P1 177.2(15) 11_655 . ?
C9 N3 P1 126.6(9) . . ?
C10 N3 P1 122.4(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              24.97
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    1.377
_refine_diff_density_min   -1.523
_refine_diff_density_rms    0.144