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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(2,3,5,6-Tetrafluoro-4-iodoanilino)ethanol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H6 F4 I N O'
_chemical_formula_sum     'C8 H6 F4 I N O'
_chemical_formula_iupac     'C8 H6 F4 I N O'
_chemical_formula_weight     335.04
_chemical_melting_point        .343E-305
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     13.327(2)
_cell_length_b     17.663(3)
_cell_length_c     8.3044(14)
_cell_angle_alpha     90.00
_cell_angle_beta     96.94(2)
_cell_angle_gamma     90.00
_cell_volume     1940.5(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2964
_cell_measurement_theta_min     2.981
_cell_measurement_theta_max     29.119
_cell_measurement_temperature     158(2)
_exptl_crystal_description     'Irregular table'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     2.294
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1264
_exptl_absorpt_coefficient_mu     3.333
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.691
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
Data collection using an OXFORD low temperature device.
Below 158 K the structure possibly shows a phase transition.
;
_diffrn_ambient_temperature     158(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_reflns_number     8054
_diffrn_reflns_av_R_equivalents     0.0256
_diffrn_reflns_av_sigmaI/netI     0.0323
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     31.30
_diffrn_reflns_theta_full     29.00
_diffrn_measured_fraction_theta_max     0.922
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     12
_diffrn_standards_decay_%     0.00
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2924
_reflns_number_gt     2422
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0458
_refine_ls_R_factor_gt     0.0363
_refine_ls_wR_factor_gt     0.0871
_refine_ls_wR_factor_ref     0.0917
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     2924
_refine_ls_number_parameters     162
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0481P)²+2.2775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.647
_refine_diff_density_min     -0.467
_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' 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'
    'N' 'N' 0.0061 0.0033
                         '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'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SIR2002 (Burla et al.,  2003)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
            'ORTEP-3 (Farrugia, 1997) and MERCURY (Macrae et al.,  2006)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
loop_
    _atom_site_type_symbol
    _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
    I I1 0.116120(18) 0.431723(13) 1.05305(3) 0.03962(10) Uani d . 1 . .
    F F1 0.11489(13) 0.12833(11) 1.03239(18) 0.0310(4) Uani d . 1 . .
    F F2 0.10979(15) 0.26089(11) 1.1821(2) 0.0341(4) Uani d . 1 . .
    F F3 0.13483(15) 0.38552(11) 0.6853(2) 0.0375(4) Uani d . 1 . .
    F F4 0.13603(14) 0.25397(11) 0.53509(19) 0.0320(4) Uani d . 1 . .
    N N1 0.12288(19) 0.11508(15) 0.7067(3) 0.0256(5) Uani d . 1 . .
    H H1N 0.120(3) 0.080(2) 0.779(5) 0.032(10) Uiso d . 1 . .
    O O1 0.06410(19) 0.02423(13) 0.3901(2) 0.0322(5) Uani d D 1 . .
    H H1O 0.026(5) 0.027(5) 0.306(6) 0.048 Uiso d PD 0.50 . .
    H H2O 0.022(5) 0.020(5) 0.454(8) 0.048 Uiso d PD 0.50 . .
    C C1 0.12620(19) 0.18530(16) 0.7785(3) 0.0211(5) Uani d . 1 . .
    C C2 0.1188(2) 0.19221(15) 0.9451(3) 0.0220(5) Uani d . 1 . .
    C C3 0.11614(19) 0.26044(18) 1.0212(3) 0.0239(5) Uani d . 1 . .
    C C4 0.1225(2) 0.32801(16) 0.9396(4) 0.0257(5) Uani d . 1 . .
    C C5 0.1307(2) 0.32223(17) 0.7744(4) 0.0266(6) Uani d . 1 . .
    C C6 0.13237(19) 0.25369(15) 0.6968(3) 0.0235(5) Uani d . 1 . .
    C C7 0.1830(2) 0.0964(2) 0.5749(3) 0.0300(6) Uani d D 1 . .
    H H7A 0.216(3) 0.0485(14) 0.602(4) 0.031(9) Uiso d D 1 . .
    H H7B 0.237(2) 0.1319(17) 0.573(4) 0.032(9) Uiso d D 1 . .
    C C8 0.1226(3) 0.0915(2) 0.4085(3) 0.0303(6) Uani d D 1 . .
    H H8A 0.079(3) 0.136(2) 0.388(6) 0.072(15) Uiso d D 1 . .
    H H8B 0.161(2) 0.090(2) 0.319(3) 0.029(9) Uiso d D 1 . .
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 0.04639(16) 0.02605(13) 0.04478(15) 0.00436(8) -0.00122(10) -0.00885(8)
    F1 0.0507(11) 0.0251(9) 0.0177(7) -0.0040(7) 0.0061(7) 0.0048(6)
    F2 0.0505(10) 0.0345(10) 0.0177(7) 0.0006(8) 0.0052(7) -0.0053(7)
    F3 0.0486(11) 0.0235(9) 0.0403(10) -0.0035(8) 0.0052(8) 0.0108(8)
    F4 0.0446(10) 0.0336(10) 0.0190(8) -0.0037(8) 0.0089(7) 0.0048(7)
    N1 0.0371(13) 0.0243(12) 0.0161(10) -0.0009(10) 0.0068(9) 0.0017(9)
    O1 0.0516(14) 0.0244(10) 0.0190(9) 0.0051(10) -0.0024(9) -0.0019(8)
    C1 0.0215(11) 0.0249(13) 0.0171(11) 0.0001(10) 0.0032(9) 0.0004(9)
    C2 0.0263(12) 0.0208(12) 0.0192(11) -0.0011(10) 0.0040(9) 0.0039(9)
    C3 0.0248(13) 0.0273(14) 0.0195(12) -0.0018(10) 0.0021(10) -0.0017(10)
    C4 0.0229(12) 0.0215(13) 0.0325(14) 0.0001(10) 0.0021(10) -0.0011(11)
    C5 0.0243(12) 0.0253(13) 0.0297(14) -0.0023(11) 0.0020(10) 0.0084(11)
    C6 0.0240(12) 0.0275(14) 0.0194(12) -0.0035(11) 0.0045(10) 0.0030(10)
    C7 0.0345(15) 0.0359(16) 0.0204(12) 0.0057(13) 0.0061(11) -0.0026(11)
    C8 0.0408(16) 0.0331(15) 0.0172(12) 0.0021(13) 0.0049(11) 0.0016(11)
_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 C4 . 2.067(3) ?
    F1 C2 . 1.345(3) ?
    F2 C3 . 1.349(3) ?
    F3 C5 . 1.346(3) ?
    F4 C6 . 1.350(3) ?
    N1 C1 . 1.375(4) ?
    N1 C7 . 1.470(4) ?
    N1 H1N . 0.87(4) ?
    O1 C8 . 1.419(4) ?
    O1 H1O . 0.818(10) ?
    O1 H2O . 0.818(10) ?
    C1 C6 . 1.393(4) ?
    C1 C2 . 1.404(4) ?
    C2 C3 . 1.363(4) ?
    C3 C4 . 1.380(4) ?
    C4 C5 . 1.392(4) ?
    C5 C6 . 1.373(4) ?
    C7 C8 . 1.516(4) ?
    C7 H7A . 0.97(2) ?
    C7 H7B . 0.96(2) ?
    C8 H8A . 0.97(2) ?
    C8 H8B . 0.96(2) ?
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 N1 C7 . . 122.3(2) ?
    C1 N1 H1N . . 110(3) ?
    C7 N1 H1N . . 115(3) ?
    C8 O1 H1O . . 108(6) ?
    C8 O1 H2O . . 115(6) ?
    H1O O1 H2O . . 99(8) ?
    N1 C1 C6 . . 124.9(2) ?
    N1 C1 C2 . . 120.3(2) ?
    C6 C1 C2 . . 114.8(2) ?
    F1 C2 C3 . . 119.1(2) ?
    F1 C2 C1 . . 118.0(2) ?
    C3 C2 C1 . . 122.9(3) ?
    F2 C3 C2 . . 118.2(3) ?
    F2 C3 C4 . . 119.8(3) ?
    C2 C3 C4 . . 122.0(3) ?
    C3 C4 C5 . . 115.9(3) ?
    C3 C4 I1 . . 122.3(2) ?
    C5 C4 I1 . . 121.8(2) ?
    F3 C5 C6 . . 118.0(3) ?
    F3 C5 C4 . . 119.6(3) ?
    C6 C5 C4 . . 122.3(3) ?
    F4 C6 C5 . . 117.9(2) ?
    F4 C6 C1 . . 120.0(2) ?
    C5 C6 C1 . . 122.0(2) ?
    N1 C7 C8 . . 114.5(3) ?
    N1 C7 H7A . . 107(2) ?
    C8 C7 H7A . . 110(2) ?
    N1 C7 H7B . . 110(2) ?
    C8 C7 H7B . . 110(2) ?
    H7A C7 H7B . . 105(3) ?
    O1 C8 C7 . . 111.7(3) ?
    O1 C8 H8A . . 110(3) ?
    C7 C8 H8A . . 110(3) ?
    O1 C8 H8B . . 104(2) ?
    C7 C8 H8B . . 116(2) ?
    H8A C8 H8B . . 105(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7 N1 C1 C6 . . . . 38.5(4) ?
    C7 N1 C1 C2 . . . . -144.3(3) ?
    N1 C1 C2 F1 . . . . 4.1(4) ?
    C6 C1 C2 F1 . . . . -178.5(2) ?
    N1 C1 C2 C3 . . . . -176.3(3) ?
    C6 C1 C2 C3 . . . . 1.1(4) ?
    F1 C2 C3 F2 . . . . 0.1(4) ?
    C1 C2 C3 F2 . . . . -179.5(2) ?
    F1 C2 C3 C4 . . . . 178.3(2) ?
    C1 C2 C3 C4 . . . . -1.3(4) ?
    F2 C3 C4 C5 . . . . 178.8(2) ?
    C2 C3 C4 C5 . . . . 0.7(4) ?
    F2 C3 C4 I1 . . . . -2.8(4) ?
    C2 C3 C4 I1 . . . . 179.0(2) ?
    C3 C4 C5 F3 . . . . 178.5(2) ?
    I1 C4 C5 F3 . . . . 0.1(4) ?
    C3 C4 C5 C6 . . . . 0.0(4) ?
    I1 C4 C5 C6 . . . . -178.3(2) ?
    F3 C5 C6 F4 . . . . -1.3(4) ?
    C4 C5 C6 F4 . . . . 177.1(2) ?
    F3 C5 C6 C1 . . . . -178.6(2) ?
    C4 C5 C6 C1 . . . . -0.1(4) ?
    N1 C1 C6 F4 . . . . -0.3(4) ?
    C2 C1 C6 F4 . . . . -177.6(2) ?
    N1 C1 C6 C5 . . . . 176.9(3) ?
    C2 C1 C6 C5 . . . . -0.4(4) ?
    C1 N1 C7 C8 . . . . -106.0(3) ?
    N1 C7 C8 O1 . . . . -74.4(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1N O1 . . 6_555 0.87(2) 2.23(3) 3.046(3) 157(3) y
    O1 H1O O1 . . 2_555 0.82(5) 1.90(7) 2.715(4) 175(8) y
    O1 H2O O1 . . 5_556 0.82(5) 1.99(5) 2.781(4) 162(8) y
data_global
_journal_date_recd_electronic     2007-11-02
_journal_date_accepted     2007-11-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o211
_journal_page_last     o211
_journal_paper_category     QO
_journal_coeditor_code     CF2167
_publ_contact_author_name     'Dr. Tullio Pilati'
_publ_contact_author_address
;
  Istituto di Scienze e Tecnologie Molecolari del CNR
  Via C. Golgi, 19
  20133 Milano
  Italy
;
_publ_contact_author_email     tullio.pilati@istm.cnr.it
_publ_contact_author_fax     '++39 2 50314300'
_publ_contact_author_phone     '++39 2 50314245'
_publ_section_title
;
2-(2,3,5,6-Tetrafluoro-4-iodoanilino)ethanol
;
loop_
    _publ_author_name
    _publ_author_address
    'Pierangelo Metrangolo'
;          Dipartimento di Chimica, Materiali e Ingegeria Chimica 'G. Natta'
           Politecnico di Milano
           Via Mancinelli 7
   I-20131 Milano
           Italy
;
    'Franck Meyer'
;          Dipartimento di Chimica, Materiali e Ingegeria Chimica 'G. Natta'
           Politecnico di Milano
           Via Mancinelli 7
   I-20131 Milano
           Italy
;
    'Tullio Pilati'
;          Istituto di Scienze e Tecnologie Molecolari del CNR
           Via Golgi 19
     20133 Milano
           Italy
;
    'Giuseppe Resnati'
;          Dipartimento di Chimica, Materiali e Ingegeria Chimica 'G. Natta'
           Politecnico di Milano
           Via Mancinelli 7
   I-20131 Milano
           Italy
;
