##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(2RS)-2-(2,4-Difluorophenyl)-1-[(4-iodobenzyl)(methyl)amino]-
3-(1H-1,2,4-triazol-1-yl)propan-2-ol
;
_chemical_name_common     'iodiconazole'
_chemical_formula_moiety     'C19 H19 F2 I N4 O'
_chemical_formula_sum     'C19 H19 F2 I N4 O'
_chemical_formula_iupac     'C19 H19 F2 I N4 O'
_chemical_formula_weight     484.28
_chemical_melting_point     ?
_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     34.398(14)
_cell_length_b     5.812(2)
_cell_length_c     21.619(9)
_cell_angle_alpha     90.00
_cell_angle_beta     114.895(5)
_cell_angle_gamma     90.00
_cell_volume     3921(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     935
_cell_measurement_theta_min     2.369
_cell_measurement_theta_max     27.292
_cell_measurement_temperature     293(2)
_cell_measurement_pressure     1
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.641
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1920
_exptl_absorpt_coefficient_mu     1.668
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6345
_exptl_absorpt_correction_T_max     0.6805
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 APEX'
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8473
_diffrn_reflns_av_R_equivalents     0.0351
_diffrn_reflns_av_sigmaI/netI     0.0310
_diffrn_reflns_theta_min     1.93
_diffrn_reflns_theta_max     26.25
_diffrn_reflns_theta_full     26.25
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -42
_diffrn_reflns_limit_h_max     37
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 > 2σ
(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     3929
_reflns_number_gt     3441
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0450
_refine_ls_R_factor_gt     0.0394
_refine_ls_wR_factor_gt     0.0995
_refine_ls_wR_factor_ref     0.1029
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     3929
_refine_ls_number_parameters     249
_refine_ls_number_restraints     1
_refine_ls_number_constraints     72
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0625P)²+1.2617P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.659
_refine_diff_density_min     -0.888
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0042(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.039478(7) 0.71329(5) 1.084656(12) 0.05727(14) Uani d . 1 8 . .
    O O1 0.14979(9) 0.4892(4) 0.86484(13) 0.0526(6) Uani d D 1 8 . .
    H H1 0.1635(13) 0.562(7) 0.8990(16) 0.079 Uiso d D 1 8 . .
    F F1 0.12653(7) 1.0421(3) 0.72386(10) 0.0579(5) Uani d . 1 8 . .
    F F2 0.21734(8) 0.6966(5) 0.64091(13) 0.0730(7) Uani d . 1 8 . .
    N N1 0.18407(7) 0.8775(4) 0.92893(12) 0.0381(5) Uani d . 1 8 . .
    N N2 0.06131(9) 0.6265(5) 0.81152(15) 0.0512(7) Uani d . 1 8 . .
    N N3 0.02469(12) 0.4885(7) 0.8643(2) 0.0786(11) Uani d . 1 8 . .
    N N4 0.04556(10) 0.8147(6) 0.8307(2) 0.0631(9) Uani d . 1 8 . .
    C C1 0.08547(10) 0.8148(6) 1.04983(16) 0.0428(7) Uani d . 1 8 . .
    C C2 0.11877(10) 0.6647(5) 1.05788(17) 0.0432(7) Uani d . 1 8 . .
    H H2A 0.1202 0.5207 1.0775 0.052 Uiso calc R 1 8 . .
    C C3 0.14984(11) 0.7318(5) 1.03632(17) 0.0423(7) Uani d . 1 8 . .
    H H3A 0.1722 0.6319 1.0421 0.051 Uiso calc R 1 8 . .
    C C4 0.14813(9) 0.9441(5) 1.00639(15) 0.0388(6) Uani d . 1 8 . .
    C C5 0.11418(11) 1.0879(5) 0.99801(16) 0.0451(7) Uani d . 1 8 . .
    H H5A 0.1122 1.2298 0.9769 0.054 Uiso calc R 1 8 . .
    C C6 0.08326(10) 1.0275(6) 1.01995(17) 0.0486(7) Uani d . 1 8 . .
    H H6A 0.0612 1.1288 1.0147 0.058 Uiso calc R 1 8 . .
    C C7 0.18278(10) 1.0181(5) 0.98510(15) 0.0432(7) Uani d . 1 8 . .
    H H7A 0.1782 1.1778 0.9708 0.052 Uiso calc R 1 8 . .
    H H7B 0.2103 1.0078 1.0242 0.052 Uiso calc R 1 8 . .
    C C8 0.22209(10) 0.9452(7) 0.91844(18) 0.0532(8) Uani d . 1 8 . .
    H H8A 0.2239 0.8528 0.8829 0.080 Uiso calc R 1 8 . .
    H H8B 0.2474 0.9226 0.9599 0.080 Uiso calc R 1 8 . .
    H H8C 0.2198 1.1045 0.9056 0.080 Uiso calc R 1 8 . .
    C C9 0.14435(9) 0.9017(5) 0.86661(15) 0.0383(6) Uani d . 1 8 . .
    H H9A 0.1464 1.0359 0.8415 0.046 Uiso calc R 1 8 . .
    H H9B 0.1205 0.9248 0.8787 0.046 Uiso calc R 1 8 . .
    C C10 0.13590(9) 0.6840(5) 0.82054(16) 0.0378(6) Uani d . 1 8 . .
    C C11 0.15886(9) 0.6898(5) 0.77369(15) 0.0375(6) Uani d . 1 8 . .
    C C12 0.18560(10) 0.5119(5) 0.77230(17) 0.0471(7) Uani d . 1 8 . .
    H H12A 0.1903 0.3885 0.8020 0.056 Uiso calc R 1 8 . .
    C C13 0.20542(11) 0.5125(6) 0.72800(19) 0.0535(8) Uani d . 1 8 . .
    H H13A 0.2232 0.3917 0.7280 0.064 Uiso calc R 1 8 . .
    C C14 0.19842(11) 0.6929(6) 0.68468(18) 0.0490(8) Uani d . 1 8 . .
    C C15 0.17194(11) 0.8736(6) 0.68202(16) 0.0473(7) Uani d . 1 8 . .
    H H15A 0.1671 0.9949 0.6516 0.057 Uiso calc R 1 8 . .
    C C16 0.15292(9) 0.8656(5) 0.72667(15) 0.0392(6) Uani d . 1 8 . .
    C C17 0.08801(11) 0.6515(6) 0.77506(18) 0.0499(8) Uani d . 1 8 . .
    H H17A 0.0779 0.7828 0.7448 0.060 Uiso calc R 1 8 . .
    H H17B 0.0845 0.5160 0.7470 0.060 Uiso calc R 1 8 . .
    C C18 0.02440(14) 0.7188(9) 0.8626(3) 0.0735(13) Uani d . 1 8 . .
    H H18A 0.0101 0.8059 0.8827 0.088 Uiso calc R 1 8 . .
    C C19 0.04840(13) 0.4356(8) 0.8317(2) 0.0675(11) Uani d . 1 8 . .
    H H19A 0.0551 0.2866 0.8239 0.081 Uiso calc R 1 8 . .
_geom_special_details
;
 All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell e.s.d.'s are taken
 into account individually in the estimation of e.s.d.'s in distances, angles
 and torsion angles; correlations between e.s.d.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C1 . 2.103(3) ?
    O1 C10 . 1.429(4) ?
    O1 H1 . 0.810(19) ?
    F1 C16 . 1.354(3) ?
    F2 C14 . 1.356(4) ?
    N1 C9 . 1.467(4) ?
    N1 C8 . 1.472(4) ?
    N1 C7 . 1.480(4) ?
    N2 C19 . 1.335(5) ?
    N2 N4 . 1.360(4) ?
    N2 C17 . 1.448(4) ?
    N3 C19 . 1.320(5) ?
    N3 C18 . 1.339(6) ?
    N4 C18 . 1.319(6) ?
    C1 C6 . 1.382(5) ?
    C1 C2 . 1.391(5) ?
    C2 C3 . 1.390(5) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.383(4) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.385(4) ?
    C4 C7 . 1.510(4) ?
    C5 C6 . 1.380(5) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 C10 . 1.560(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.525(4) ?
    C10 C17 . 1.534(4) ?
    C11 C12 . 1.393(4) ?
    C11 C16 . 1.394(4) ?
    C12 C13 . 1.390(5) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.358(5) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.375(5) ?
    C15 C16 . 1.376(4) ?
    C15 H15A . 0.9300 ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 H18A . 0.9300 ?
    C19 H19A . 0.9300 ?
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
    C10 O1 H1 . . 96(3) ?
    C9 N1 C8 . . 112.2(2) ?
    C9 N1 C7 . . 111.3(2) ?
    C8 N1 C7 . . 108.3(2) ?
    C19 N2 N4 . . 109.8(3) ?
    C19 N2 C17 . . 129.5(3) ?
    N4 N2 C17 . . 120.7(3) ?
    C19 N3 C18 . . 102.5(4) ?
    C18 N4 N2 . . 101.4(3) ?
    C6 C1 C2 . . 120.0(3) ?
    C6 C1 I1 . . 121.1(2) ?
    C2 C1 I1 . . 118.9(2) ?
    C3 C2 C1 . . 119.4(3) ?
    C3 C2 H2A . . 120.3 ?
    C1 C2 H2A . . 120.3 ?
    C4 C3 C2 . . 121.3(3) ?
    C4 C3 H3A . . 119.3 ?
    C2 C3 H3A . . 119.3 ?
    C3 C4 C5 . . 117.9(3) ?
    C3 C4 C7 . . 120.9(3) ?
    C5 C4 C7 . . 121.2(3) ?
    C6 C5 C4 . . 122.0(3) ?
    C6 C5 H5A . . 119.0 ?
    C4 C5 H5A . . 119.0 ?
    C5 C6 C1 . . 119.3(3) ?
    C5 C6 H6A . . 120.3 ?
    C1 C6 H6A . . 120.3 ?
    N1 C7 C4 . . 113.2(2) ?
    N1 C7 H7A . . 108.9 ?
    C4 C7 H7A . . 108.9 ?
    N1 C7 H7B . . 108.9 ?
    C4 C7 H7B . . 108.9 ?
    H7A C7 H7B . . 107.8 ?
    N1 C8 H8A . . 109.5 ?
    N1 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    N1 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N1 C9 C10 . . 111.1(2) ?
    N1 C9 H9A . . 109.4 ?
    C10 C9 H9A . . 109.4 ?
    N1 C9 H9B . . 109.4 ?
    C10 C9 H9B . . 109.4 ?
    H9A C9 H9B . . 108.0 ?
    O1 C10 C11 . . 110.0(2) ?
    O1 C10 C17 . . 107.3(3) ?
    C11 C10 C17 . . 107.1(2) ?
    O1 C10 C9 . . 107.2(2) ?
    C11 C10 C9 . . 113.4(2) ?
    C17 C10 C9 . . 111.7(3) ?
    C12 C11 C16 . . 115.1(3) ?
    C12 C11 C10 . . 122.0(3) ?
    C16 C11 C10 . . 122.9(3) ?
    C13 C12 C11 . . 122.2(3) ?
    C13 C12 H12A . . 118.9 ?
    C11 C12 H12A . . 118.9 ?
    C14 C13 C12 . . 118.8(3) ?
    C14 C13 H13A . . 120.6 ?
    C12 C13 H13A . . 120.6 ?
    F2 C14 C13 . . 119.7(3) ?
    F2 C14 C15 . . 117.6(3) ?
    C13 C14 C15 . . 122.7(3) ?
    C14 C15 C16 . . 116.5(3) ?
    C14 C15 H15A . . 121.7 ?
    C16 C15 H15A . . 121.7 ?
    F1 C16 C15 . . 116.8(3) ?
    F1 C16 C11 . . 118.5(3) ?
    C15 C16 C11 . . 124.7(3) ?
    N2 C17 C10 . . 114.8(3) ?
    N2 C17 H17A . . 108.6 ?
    C10 C17 H17A . . 108.6 ?
    N2 C17 H17B . . 108.6 ?
    C10 C17 H17B . . 108.6 ?
    H17A C17 H17B . . 107.5 ?
    N4 C18 N3 . . 116.0(4) ?
    N4 C18 H18A . . 122.0 ?
    N3 C18 H18A . . 122.0 ?
    N3 C19 N2 . . 110.3(4) ?
    N3 C19 H19A . . 124.9 ?
    N2 C19 H19A . . 124.9 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C9 H9B N2 . 0.97 2.60 3.045(4) 108.0
    C9 H9B N4 . 0.97 2.42 3.191(4) 135.7
    C12 H12A O1 . 0.93 2.39 2.759(4) 103.2
    C17 H17A F1 . 0.97 2.43 3.061(4) 122.3
    O1 H1 N1 . 0.810(19) 1.97(3) 2.651(4) 141(4)
data_global
_journal_date_recd_electronic     2012-06-08
_journal_date_accepted     2012-07-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      8
_journal_page_first     o2447
_journal_page_last     o2448
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681203139X
_journal_coeditor_code     FB2257
_publ_contact_author_name     'Zhi-Jun Wu'
_publ_contact_author_address
;
Department of Pharmacy
Changzheng Hospital
Second Military Medical University
Shanghai 200003, People's Republic of China
;
_publ_contact_author_email     wuzhijun999@sina.com
_publ_contact_author_fax     '+86 (021) 81871314'
_publ_contact_author_phone     '+86 (021) 81871347'
_publ_section_title
;\
(2RS)-2-(2,4-Difluorophenyl)-1-[(4-iodobenzyl)(methyl)amino]-3-\
(1H-1,2,4-triazol-1-yl)propan-2-ol
;
loop_
    _publ_author_name
    _publ_author_address
    'Hui-Ping Xiong'
;
School of Mathematics and Physics
Shanghai University of Electric Power
Shanghai 200090, People's Republic of China
;
    'Shou-Hong Gao'
;
Department of Pharmacy
Changzheng Hospital
Second Military Medical University
Shanghai 200003, People's Republic of China
;
    'Chun-Tong Li'
;
Department of Pharmacy
Changzheng Hospital
Second Military Medical University
Shanghai 200003, People's Republic of China
;
    'Zhi-Jun Wu'
;
Department of Pharmacy
Changzheng Hospital
Second Military Medical University
Shanghai 200003, People's Republic of China
;
