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###           Electronic papers (Acta Crystallographica Section C)         ###
###                                                                        ###
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# This paper is published electronically. It meets the data-validation       #
# criteria for publication in Acta Crystallographica Section C.              #
# The submission has been checked by a Section C Co-editor though the text   #
# in _publ_section_comments is the responsibility of the authors.            #
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# Electronic papers are listed in the printed contents pages of an issue of  #
# Acta Crystallographica Section C within two months of acceptance and are   #
# available by email and via the online contents pages for that issue.       #
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data_global
_audit_creation_method     'from SHELXL97 CIF and QB0162 CIF'
_journal_data_validation_number     IUC0000033
_journal_date_recd_electronic     1999-12-20
_journal_date_accepted     2000-02-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      3
_journal_page_first     e105
_journal_page_last     e106
_journal_paper_category     CO
_publ_contact_author_name     'Dr Philip R. Lowe'
_publ_contact_author_address
;
School of Life and Health Sciences
Pharmaceutical Sciences Research Institute
Aston University
Aston Triangle
Birmingham
B4 7ET
;
_publ_contact_author_email     p.r.lowe@aston.ac.uk
_publ_contact_author_fax     '0121 359 0733'
_publ_contact_author_phone     '0121 359 3611'
_publ_section_title
;
A T-shaped selenenyl halide
;
loop_
    _publ_author_name
    _publ_author_address
    'Majeed, Zulfiqar'
;
Department of Chemical Engineering and Applied Chemistry
Aston University
Aston Triangle
Birmingham B4 7ET
England
;
    'McWhinnie, William R.'
;
Department of Chemical Engineering and Applied Chemistry
Aston University
Aston Triangle
Birmingham B4 7ET
England
;
    'Lowe, Philip R.'
;
Pharmaceutical Sciences Research Institute
Aston University
Aston Triangle
Birmingham B4 7ET
England
;
_publ_section_synopsis
;
3-Iodo-2-phenyl-3H-3-selenaindazole has an almost planar conformation
and a nearly ideal T-shape for the Se(INC) moiety [Se---I 2.8122(12),
Se---C 1.881(7) and Se---N2 2.051(6)Å; C---Se---N 79.6(3),
C---Se---I 96.8(2) and N---Se---I 176.17(17)°]. This arrangement,
together with the two selenium lone pairs, leads to a distorted
trigonal-bipyrimidal geometry about the Se atom.
;
_publ_section_abstract
;
The title selenenyl halide complex, 3-iodo-2-phenyl-3H-3-selenaindazole,
C₁₂H₉IN₂Se, has an almost planar conformation and a nearly ideal
T-shape for the Se(INC) moiety [Se---I 2.8122(12), Se---C 1.881(7) and
Se---N2 2.051(6)Å; C---Se---N 79.6(3), C---Se---I 96.8(2) and N---Se---I
176.17(17)°]. This arrangement, together with the two selenium lone pairs,
leads to a distorted trigonal-bipyrimidal geometry about the Se atom.
Intermolecular interactions are largely limited to stacking forces.
;
_publ_section_comment
;
X-ray structure determination of the title compound, (I), revealed the complex
to be a T-shaped selenenyl iodide with the I and N atoms
occupying the trans positions. The main nine-atom moeity (Se1, N1, N2, C1-C6)
is essentially planar (r.m.s. atomic deviations of 0.030Å), as is the phenyl
ring (r.m.s. deviations of 0.013Å), and the two are rotated relative to each
other by 6.4(3)° about the N2---C7 bond.
As with similar compounds investigated, (II) and (III) (Majeed, 1999), and
(IV) (Jones & Ramirez de Arellano, 1995), the Se atom is formally bonded to
the halogen atom and to the aromatic C1 atom, with a secondary
link to N2 which is trans to the halogen. The Se1---I1 bond length in (I) is
2.8122(12)Å, which compares very favourably with the equivalent bond in the
T-shaped selenium chloroiodide complex (II) of 2.837(2)Å.  The Se1---N2
distance of 2.051(6)Å is significantly longer than the mean value of
1.83Å for Se---N single bonds in the Cambridge Structural Database (Allen
et al., 1987), but again is close to the values determined for the selenenyl
halides (II), (III) and (IV) which are 2.040(6), 2.011(5) and 2.025(3)Å,
respectively.  The Se1---C1 bond length of 1.881(7)Å is as expected for an
Se---Csp² single covalent bond and compares favourably with the value quoted
by Allen et al. (1987) of 1.893Å.
In the Se1---N2 interaction, N2 donates an electron pair to Se1 to complete a
trigonal-bipyrimidal type of coordination about the central Se atom.
The two lone pairs and C1 are equatorial and the more electronegative
N and I atoms are axial, this being in accord with the valence-shell
electron-pair repulsion (VSEPR) theory (Gillespie, 1963). The angle
N2---Se1---I1 is close to linear [176.17(17)°], and the slight bending
in the direction of C1 is probably due to lone-pair repulsion as suggested
by Jones & Ramirez de Arellano (1995).  The main deviation from an ideal
T-shape is seen in the N2---Se1---C1 angle of 79.6(3)°. This is characteristic
of this group of compounds with (II), (III) and (IV) having angles of 80.3(3),
80.8(2) and 79.8(2)°, respectively.
The main intermolecular forces are largely associated with stacking along
the short a axis.
;
_publ_section_acknowledgements
;
We thank Dr Carl H. Schwalbe for his helpful discussions in preparing this
document.
;
_publ_section_references
;
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. &
Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989).  CAD-4 Software.  Version 5.0.  Enraf-Nonius, Delft,
The Netherlands.
Gillespie, R. J. (1963). J. Chem. Educ. 40, 295-301.
Gould, R. O. & Smith, D.E.  (1986).  CADABS. Univ. of Edinburgh, Scotland.
Jones, P. G. & Ramirez de Arellano, M. C.  (1995).  Chem. Ber. 128, 741-742.
Majeed, Z.  (1999).  PhD thesis,  Aston University, Birmingham, England.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta
Cryst. A24, 351-359.
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.
Watkin, D. J., Prout, C. K., Carruthers, J. R. &  Betteridge, P. W. (1996).
CRYSTALS. Issue 10.  Chemical Crystallography Laboratory, Univ. of Oxford,
England.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical
Crystallography Laboratory, Univ. of Oxford, England.
;
_publ_section_exptl_prep
;
Azobenzene (55 mmol), selenium(IV) tetrachloride (5 mmol) and anhydrous
aluminum chloride (5 mmol) were heated to 433 K under argon for 3 h
in 50 ml of 1,2-dichlorobenzene. The reaction mixture was cooled to 353 K
and methanol added until the vigorous reaction ceased.  The brown
precipitate of (III) which formed after cooling was recrystallized from
methanol; yield 10%. (III) (1.67 mmol) was added to a  solution of diiodine
(1.67 mmol) in AR-grade propanone (200 ml).  The  mixture was heated for
10 min and the solvent removed leaving a deep-red crystalline solid;
yield 33%.  Crystals suitable for diffraction work were obtained by slow
evaporation from propanone.
;
_publ_section_exptl_refinement
;
;
data_1
_chemical_name_systematic
;
(2-phenylazophenyl-C,N')selenium iodide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H9 I N2 Se'
_chemical_formula_sum     'C12 H9 I N2 Se'
_chemical_formula_weight     387.07
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     4.845(2)
_cell_length_b     18.369(6)
_cell_length_c     13.7745(12)
_cell_angle_alpha     90
_cell_angle_beta     91.77(2)
_cell_angle_gamma     90
_cell_volume     1225.3(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.79
_cell_measurement_theta_max     17.02
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     red
_exptl_crystal_size_max      .40
_exptl_crystal_size_mid      .32
_exptl_crystal_size_min      .25
_exptl_crystal_density_diffrn     2.098
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     5.557
_exptl_absorpt_correction_type     '\y scan'
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min      .186
_exptl_absorpt_correction_T_max      .250
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     2956
_diffrn_reflns_av_R_equivalents      .037
_diffrn_reflns_av_sigmaI/netI      .0334
_diffrn_reflns_theta_min     2.22
_diffrn_reflns_theta_max     24.95
_diffrn_reflns_theta_full     24.95
_diffrn_measured_fraction_theta_max      .998
_diffrn_measured_fraction_theta_full      .998
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1.1
_reflns_number_total     2140
_reflns_number_gt     1728
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .064
_refine_ls_R_factor_gt      .043
_refine_ls_wR_factor_ref      .122
_refine_ls_goodness_of_fit_ref     1.168
_refine_ls_restrained_S_all     1.168
_refine_ls_number_reflns     2140
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0489P)²+5.5805P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .894
_refine_diff_density_min      -.815
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I'  -.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Se' 'Se'  -.0929 2.2259
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'CADABS (Gould & Smith, 1986)'
_computing_structure_solution
                       'CRYSTALS (Watkin, Prout, Carruthers & Betteridge, 1996)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Prout & Pearce, 1996)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    I1  .44972(13)  .14327(3)  .18901(5)  .0632(2) Uani d . 1 . . I
    Se1  .77590(15)  .26988(4)  .19751(5)  .0424(2) Uani d . 1 . . Se
    N1  .9499(13)  .4079(3)  .1265(4)  .0433(14) Uani d . 1 . . N
    N2  .9955(12)  .3654(3)  .1972(4)  .0402(13) Uani d . 1 . . N
    C1  .6271(14)  .3136(4)  .0840(5)  .0393(16) Uani d . 1 . . C
    C2  .4182(16)  .2877(5)  .0231(5)  .0469(18) Uani d . 1 . . C
    H2  .3316  .2437  .0360  .056 Uiso calc R 1 . . H
    C3  .3405(17)  .3282(5)  -.0570(6)  .055(2) Uani d . 1 . . C
    H3  .2002  .3105  -.0982  .066 Uiso calc R 1 . . H
    C4  .4607(19)  .3933(5)  -.0789(6)  .060(2) Uani d . 1 . . C
    H4  .3996  .4194  -.1332  .072 Uiso calc R 1 . . H
    C5  .6699(18)  .4198(5)  -.0209(6)  .053(2) Uani d . 1 . . C
    H5  .7584  .4630  -.0364  .063 Uiso calc R 1 . . H
    C6  .7498(15)  .3803(4)  .0634(5)  .0433(17) Uani d . 1 . . C
    C7 1.1883(14)  .3855(4)  .2722(5)  .0385(15) Uani d . 1 . . C
    C8 1.2188(18)  .3429(5)  .3524(6)  .058(2) Uani d . 1 . . C
    H8 1.1145  .3006  .3571  .069 Uiso calc R 1 . . H
    C9 1.4039(17)  .3614(5)  .4278(7)  .060(2) Uani d . 1 . . C
    H9 1.4184  .3331  .4836  .072 Uiso calc R 1 . . H
    C10 1.5642(18)  .4224(6)  .4180(7)  .063(2) Uani d . 1 . . C
    H10 1.6919  .4349  .4670  .075 Uiso calc R 1 . . H
    C11 1.537(2)  .4647(5)  .3369(8)  .067(2) Uani d . 1 . . C
    H11 1.6487  .5056  .3309  .080 Uiso calc R 1 . . H
    C12 1.3479(17)  .4478(5)  .2637(6)  .055(2) Uani d . 1 . . C
    H12 1.3272  .4777  .2095  .066 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    I1  .0653(4)  .0558(4)  .0677(4)  -.0066(3)  -.0119(3)  .0085(3)
    Se1  .0430(4)  .0461(4)  .0380(4)  .0048(3)  -.0014(3)  .0033(3)
    N1  .049(3)  .045(4)  .037(3)  .001(3)  .005(3)  .001(3)
    N2  .041(3)  .043(3)  .036(3)  .004(3)  .004(2)  -.001(3)
    C1  .043(4)  .044(4)  .032(3)  .013(3)  .006(3)  -.002(3)
    C2  .049(4)  .053(5)  .038(4)  .000(4)  -.003(3)  .001(3)
    C3  .054(5)  .074(6)  .036(4)  .006(4)  -.006(3)  -.009(4)
    C4  .069(6)  .068(6)  .042(4)  .012(5)  -.005(4)  .014(4)
    C5  .069(5)  .051(5)  .038(4)  .002(4)  -.001(4)  .005(3)
    C6  .048(4)  .051(4)  .031(4)  .008(3)  .003(3)  -.004(3)
    C7  .034(3)  .044(4)  .037(4)  .004(3)  .003(3)  -.005(3)
    C8  .054(5)  .071(6)  .047(5)  -.012(4)  -.006(4)  .011(4)
    C9  .050(5)  .077(7)  .052(5)  .001(4)  -.010(4)  .007(4)
    C10  .055(5)  .077(6)  .055(5)  .005(5)  -.010(4)  -.016(5)
    C11  .065(5)  .056(5)  .079(7)  -.013(4)  -.008(5)  -.012(5)
    C12  .061(5)  .048(5)  .056(5)  -.003(4)  -.011(4)  .001(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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 Se1 . 2.8122(12) ?
    Se1 C1 . 1.881(7) ?
    Se1 N2 . 2.051(6) ?
    N1 N2 . 1.262(8) ?
    N1 C6 . 1.378(10) ?
    N2 C7 . 1.421(9) ?
    C1 C2 . 1.379(10) ?
    C1 C6 . 1.394(11) ?
    C2 C3 . 1.374(11) ?
    C2 H2 .  .9300 ?
    C3 C4 . 1.368(13) ?
    C3 H3 .  .9300 ?
    C4 C5 . 1.361(12) ?
    C4 H4 .  .9300 ?
    C5 C6 . 1.413(11) ?
    C5 H5 .  .9300 ?
    C7 C8 . 1.358(11) ?
    C7 C12 . 1.389(11) ?
    C8 C9 . 1.393(12) ?
    C8 H8 .  .9300 ?
    C9 C10 . 1.371(13) ?
    C9 H9 .  .9300 ?
    C10 C11 . 1.364(14) ?
    C10 H10 .  .9300 ?
    C11 C12 . 1.377(12) ?
    C11 H11 .  .9300 ?
    C12 H12 .  .9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 Se1 N2 . . 79.6(3) ?
    C1 Se1 I1 . . 96.8(2) ?
    N2 Se1 I1 . . 176.17(17) ?
    N2 N1 C6 . . 111.2(6) ?
    N1 N2 C7 . . 119.7(6) ?
    N1 N2 Se1 . . 116.9(5) ?
    C7 N2 Se1 . . 123.4(5) ?
    C2 C1 C6 . . 119.3(7) ?
    C2 C1 Se1 . . 127.8(6) ?
    C6 C1 Se1 . . 112.9(5) ?
    C3 C2 C1 . . 118.6(8) ?
    C3 C2 H2 . . 120.7 ?
    C1 C2 H2 . . 120.7 ?
    C4 C3 C2 . . 122.8(8) ?
    C4 C3 H3 . . 118.6 ?
    C2 C3 H3 . . 118.6 ?
    C5 C4 C3 . . 119.9(8) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C4 C5 C6 . . 118.6(8) ?
    C4 C5 H5 . . 120.7 ?
    C6 C5 H5 . . 120.7 ?
    N1 C6 C1 . . 119.4(7) ?
    N1 C6 C5 . . 119.9(7) ?
    C1 C6 C5 . . 120.7(7) ?
    C8 C7 C12 . . 119.8(7) ?
    C8 C7 N2 . . 119.7(7) ?
    C12 C7 N2 . . 120.5(7) ?
    C7 C8 C9 . . 121.1(8) ?
    C7 C8 H8 . . 119.5 ?
    C9 C8 H8 . . 119.5 ?
    C10 C9 C8 . . 118.7(9) ?
    C10 C9 H9 . . 120.6 ?
    C8 C9 H9 . . 120.6 ?
    C11 C10 C9 . . 120.3(8) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C10 C11 C12 . . 121.0(9) ?
    C10 C11 H11 . . 119.5 ?
    C12 C11 H11 . . 119.5 ?
    C11 C12 C7 . . 119.0(8) ?
    C11 C12 H12 . . 120.5 ?
    C7 C12 H12 . . 120.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 N1 N2 C7 . . . . -177.7(6) ?
    C6 N1 N2 Se1 . . . . 1.3(7) ?
    C1 Se1 N2 N1 . . . . -2.1(5) ?
    I1 Se1 N2 N1 . . . . -19(3) ?
    C1 Se1 N2 C7 . . . . 176.8(6) ?
    I1 Se1 N2 C7 . . . . 160(2) ?
    N2 Se1 C1 C2 . . . . -177.2(7) ?
    I1 Se1 C1 C2 . . . . 1.7(7) ?
    N2 Se1 C1 C6 . . . . 2.2(5) ?
    I1 Se1 C1 C6 . . . . -178.9(5) ?
    C6 C1 C2 C3 . . . . 1.0(11) ?
    Se1 C1 C2 C3 . . . . -179.7(6) ?
    C1 C2 C3 C4 . . . .  -.3(13) ?
    C2 C3 C4 C5 . . . . 1.2(14) ?
    C3 C4 C5 C6 . . . . -2.7(13) ?
    N2 N1 C6 C1 . . . .  .7(9) ?
    N2 N1 C6 C5 . . . . -179.7(7) ?
    C2 C1 C6 N1 . . . . 177.1(7) ?
    Se1 C1 C6 N1 . . . . -2.4(8) ?
    C2 C1 C6 C5 . . . . -2.5(11) ?
    Se1 C1 C6 C5 . . . . 178.0(6) ?
    C4 C5 C6 N1 . . . . -176.2(7) ?
    C4 C5 C6 C1 . . . . 3.4(12) ?
    N1 N2 C7 C8 . . . . 174.1(7) ?
    Se1 N2 C7 C8 . . . . -4.8(9) ?
    N1 N2 C7 C12 . . . . -6.7(10) ?
    Se1 N2 C7 C12 . . . . 174.4(5) ?
    C12 C7 C8 C9 . . . . 1.5(13) ?
    N2 C7 C8 C9 . . . . -179.3(8) ?
    C7 C8 C9 C10 . . . . -2.6(14) ?
    C8 C9 C10 C11 . . . . 1.5(14) ?
    C9 C10 C11 C12 . . . .  .7(15) ?
    C10 C11 C12 C7 . . . . -1.8(14) ?
    C8 C7 C12 C11 . . . .  .8(12) ?
    N2 C7 C12 C11 . . . . -178.5(8) ?
