##############################################################################
###                                                                        ###
###        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/  #
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##############################################################################
                                             
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2004-11-08
_journal_date_accepted     2004-11-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2410
_journal_page_last     o2412
_journal_paper_category     EO
_publ_contact_author_name     'Deepak Chopra'
_publ_contact_author_address
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012, Karnataka
India
;
_publ_contact_author_email     deepak@sscu.iisc.ernet.in
_publ_contact_author_fax     '(91)803601310'
_publ_contact_author_phone     '(91)802932336'
_publ_section_title
;
2-(2,4-Dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (hexaconazole)
;
loop_
    _publ_author_name
    _publ_author_address
    'Chopra, Deepak'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012
Karnataka
India
;
    'Mohan, T. P.'
;
Rallis India Limited
Peenya Industrial Area
Bangalore 560 078
India
;
    'Rao, K. S.'
;
Rallis India Limited
Peenya Industrial Area
Bangalore 560 078
India
;
    'Guru Row, T. N.'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012
Karnataka
India
;
data_I
_chemical_name_systematic
;
2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H17 Cl2 N3 O'
_chemical_formula_sum     'C14 H17 Cl2 N3 O'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C14 H17 Cl2 N3 O'
_chemical_formula_weight     314.21
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    x,y,z
    -x,1/2+y,1/2-z
    -x,-y,-z
    x,1/2-y,1/2+z
_cell_length_a     10.895(6)
_cell_length_b     11.006(6)
_cell_length_c     13.595(8)
_cell_angle_alpha     90
_cell_angle_beta     106.526(9)
_cell_angle_gamma     90
_cell_volume     1562.9(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     788
_cell_measurement_theta_min     1.6
_cell_measurement_theta_max     25.2
_cell_measurement_temperature     293(2)
_cell_special_details
; ?
;
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.335
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.414
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8858
_exptl_absorpt_correction_T_max     0.9217
_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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11231
_diffrn_reflns_av_R_equivalents     0.0152
_diffrn_reflns_av_sigmaI/netI     0.0132
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     25.35
_diffrn_reflns_theta_full     25.35
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_standards_number     ?
_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 > 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     2867
_reflns_number_gt     2509
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0431
_refine_ls_R_factor_gt     0.0376
_refine_ls_wR_factor_gt     0.0959
_refine_ls_wR_factor_ref     0.1001
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     2867
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0469P)²+0.5742P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_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     0.349
_refine_diff_density_min     -0.329
_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
    O O 0.0106 0.0060 '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'
    Cl Cl 0.1484 0.1585 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
               'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993)'
_computing_publication_material     'PLATON (Spek, 1990)'
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
    H1O 0.451(2) 0.327(2) 0.1313(18) 0.069(7) Uiso d . 1 . . H
    Cl1 -0.00431(4) 0.20183(5) -0.01856(4) 0.06447(18) Uani d . 1 . . Cl
    Cl2 0.13472(7) -0.11878(6) -0.25756(5) 0.0899(2) Uani d . 1 . . Cl
    O1 0.42849(13) 0.27230(14) 0.09522(12) 0.0603(4) Uani d . 1 . . O
    N1 0.31708(14) 0.10339(14) 0.20512(11) 0.0500(4) Uani d . 1 . . N
    N2 0.24677(18) 0.00226(16) 0.17317(14) 0.0664(5) Uani d . 1 . . N
    N3 0.44610(19) -0.0471(2) 0.26484(16) 0.0785(6) Uani d . 1 . . N
    C1 0.1796(2) -0.00740(17) -0.16300(15) 0.0570(5) Uani d . 1 . . C
    C2 0.08621(19) 0.04991(17) -0.13092(14) 0.0537(4) Uani d . 1 . . C
    C3 0.12195(16) 0.13788(15) -0.05555(13) 0.0453(4) Uani d . 1 . . C
    C4 0.24868(15) 0.17190(15) -0.01137(12) 0.0422(4) Uani d . 1 . . C
    C5 0.33865(19) 0.11104(17) -0.04784(15) 0.0523(4) Uani d . 1 . . C
    C6 0.3059(2) 0.02200(19) -0.12209(16) 0.0601(5) Uani d . 1 . . C
    C7 0.29329(16) 0.26597(16) 0.07447(13) 0.0465(4) Uani d . 1 . . C
    C8 0.2636(2) 0.22263(18) 0.17286(15) 0.0532(4) Uani d . 1 . . C
    C9 0.3286(3) -0.0845(2) 0.2104(2) 0.0759(6) Uani d . 1 . . C
    C10 0.4337(2) 0.0721(2) 0.25928(17) 0.0673(6) Uani d . 1 . . C
    C11 0.2348(2) 0.39343(17) 0.04730(16) 0.0544(5) Uani d . 1 . . C
    C12 0.2410(3) 0.4430(2) -0.05493(19) 0.0721(6) Uani d . 1 . . C
    C13 0.1957(3) 0.5750(2) -0.0726(2) 0.0753(7) Uani d . 1 . . C
    C14 0.2852(3) 0.6656(3) -0.0076(3) 0.0847(8) Uani d . 1 . . C
    H2 0.002(2) 0.031(2) -0.1582(16) 0.063(6) Uiso d . 1 . . H
    H5 0.424(2) 0.1321(19) -0.0200(16) 0.059(6) Uiso d . 1 . . H
    H6 0.369(2) -0.016(2) -0.1419(18) 0.070(7) Uiso d . 1 . . H
    H8A 0.174(2) 0.2181(18) 0.1650(14) 0.053(5) Uiso d . 1 . . H
    H8B 0.299(2) 0.275(2) 0.2246(17) 0.065(6) Uiso d . 1 . . H
    H9 0.307(3) -0.167(3) 0.201(2) 0.092(8) Uiso d . 1 . . H
    H10 0.496(2) 0.130(2) 0.2889(19) 0.079(7) Uiso d . 1 . . H
    H11A 0.278(2) 0.447(2) 0.1016(17) 0.063(6) Uiso d . 1 . . H
    H11B 0.147(2) 0.394(2) 0.0469(17) 0.067(6) Uiso d . 1 . . H
    H12A 0.330(2) 0.443(2) -0.0498(17) 0.069(7) Uiso d . 1 . . H
    H12B 0.193(3) 0.389(3) -0.110(2) 0.107(10) Uiso d . 1 . . H
    H13A 0.108(3) 0.584(2) -0.063(2) 0.091(8) Uiso d . 1 . . H
    H13B 0.184(3) 0.595(3) -0.141(3) 0.114(11) Uiso d . 1 . . H
    H14A 0.298(3) 0.654(3) 0.070(3) 0.116(11) Uiso d . 1 . . H
    H14B 0.258(3) 0.744(3) -0.026(2) 0.098(9) Uiso d . 1 . . H
    H14C 0.367(4) 0.657(3) -0.012(3) 0.122(11) Uiso d . 1 . . H
_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
    Cl1 C3 . 1.7418(19) ?
    Cl2 C1 . 1.743(2) ?
    O1 C7 . 1.420(2) ?
    O1 H1O . 0.77(3) ?
    N1 C10 . 1.321(3) yes
    N1 N2 . 1.351(2) yes
    N1 C8 . 1.452(3) yes
    C4 C5 . 1.390(3) ?
    C4 C3 . 1.391(2) ?
    C4 C7 . 1.532(2) ?
    C2 C1 . 1.370(3) ?
    C2 C3 . 1.383(3) ?
    C2 H2 . 0.91(2) ?
    N2 C9 . 1.306(3) yes
    C5 C6 . 1.379(3) ?
    C5 H5 . 0.92(2) ?
    C8 C7 . 1.539(3) ?
    C8 H8A . 0.96(2) ?
    C8 H8B . 0.91(2) ?
    C7 C11 . 1.542(3) ?
    C11 C12 . 1.513(3) ?
    C11 H11B . 0.95(2) ?
    C11 H11A . 0.96(2) ?
    N3 C10 . 1.319(3) yes
    N3 C9 . 1.348(3) yes
    C6 C1 . 1.368(3) ?
    C6 H6 . 0.90(2) ?
    C12 C13 . 1.531(3) ?
    C12 H12A . 0.96(2) ?
    C12 H12B . 0.98(3) ?
    C14 C13 . 1.494(4) ?
    C14 H14C . 0.92(4) ?
    C14 H14B . 0.93(3) ?
    C14 H14A . 1.03(3) ?
    C10 H10 . 0.94(3) ?
    C13 H13B . 0.93(3) ?
    C13 H13A . 1.00(3) ?
    C9 H9 . 0.94(3) ?
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
    C7 O1 H1O . . 106.4(18) ?
    C10 N1 N2 . . 109.40(18) ?
    C10 N1 C8 . . 130.08(18) ?
    N2 N1 C8 . . 120.36(16) ?
    C5 C4 C3 . . 115.49(16) ?
    C5 C4 C7 . . 119.62(16) ?
    C3 C4 C7 . . 124.86(15) ?
    C1 C2 C3 . . 118.70(18) ?
    C1 C2 H2 . . 121.3(14) ?
    C3 C2 H2 . . 120.0(14) ?
    C9 N2 N1 . . 102.46(19) ?
    C2 C3 C4 . . 122.96(16) ?
    C2 C3 Cl1 . . 114.70(14) ?
    C4 C3 Cl1 . . 122.34(14) ?
    C6 C5 C4 . . 122.79(19) ?
    C6 C5 H5 . . 119.9(13) ?
    C4 C5 H5 . . 117.4(13) ?
    N1 C8 C7 . . 112.17(16) ?
    N1 C8 H8A . . 107.3(12) ?
    C7 C8 H8A . . 112.4(12) ?
    N1 C8 H8B . . 107.2(14) ?
    C7 C8 H8B . . 109.2(14) ?
    H8A C8 H8B . . 108.3(18) ?
    O1 C7 C4 . . 105.71(14) ?
    O1 C7 C8 . . 107.76(15) ?
    C4 C7 C8 . . 110.68(15) ?
    O1 C7 C11 . . 109.74(15) ?
    C4 C7 C11 . . 114.36(15) ?
    C8 C7 C11 . . 108.39(15) ?
    C12 C11 C7 . . 115.15(17) ?
    C12 C11 H11B . . 107.4(14) ?
    C7 C11 H11B . . 110.5(13) ?
    C12 C11 H11A . . 110.3(13) ?
    C7 C11 H11A . . 107.1(13) ?
    H11B C11 H11A . . 106.1(18) ?
    C10 N3 C9 . . 101.94(19) ?
    C1 C6 C5 . . 119.12(19) ?
    C1 C6 H6 . . 121.9(15) ?
    C5 C6 H6 . . 119.0(15) ?
    C6 C1 C2 . . 120.93(18) ?
    C6 C1 Cl2 . . 120.34(16) ?
    C2 C1 Cl2 . . 118.73(17) ?
    C11 C12 C13 . . 112.9(2) ?
    C11 C12 H12A . . 104.1(14) ?
    C13 C12 H12A . . 106.8(15) ?
    C11 C12 H12B . . 109.1(18) ?
    C13 C12 H12B . . 112.3(18) ?
    H12A C12 H12B . . 111(2) ?
    C13 C14 H14C . . 112(2) ?
    C13 C14 H14B . . 111.1(18) ?
    H14C C14 H14B . . 109(3) ?
    C13 C14 H14A . . 113.6(18) ?
    H14C C14 H14A . . 102(3) ?
    H14B C14 H14A . . 109(3) ?
    N3 C10 N1 . . 111.0(2) ?
    N3 C10 H10 . . 127.4(15) ?
    N1 C10 H10 . . 121.7(15) ?
    C14 C13 C12 . . 114.4(3) ?
    C14 C13 H13B . . 109(2) ?
    C12 C13 H13B . . 109(2) ?
    C14 C13 H13A . . 109.9(16) ?
    C12 C13 H13A . . 110.6(16) ?
    H13B C13 H13A . . 104(2) ?
    N2 C9 N3 . . 115.2(2) ?
    N2 C9 H9 . . 122.5(17) ?
    N3 C9 H9 . . 122.3(17) ?
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
    C10 N1 N2 C9 . . . . -0.6(2) ?
    C8 N1 N2 C9 . . . . 175.29(19) ?
    C1 C2 C3 C4 . . . . 0.7(3) ?
    C1 C2 C3 Cl1 . . . . -178.46(15) ?
    C5 C4 C3 C2 . . . . -0.2(3) ?
    C7 C4 C3 C2 . . . . -178.07(17) ?
    C5 C4 C3 Cl1 . . . . 178.90(13) ?
    C7 C4 C3 Cl1 . . . . 1.0(2) ?
    C3 C4 C5 C6 . . . . -0.6(3) ?
    C7 C4 C5 C6 . . . . 177.44(18) ?
    C10 N1 C8 C7 . . . . 83.2(3) ?
    N2 N1 C8 C7 . . . . -91.8(2) yes
    C5 C4 C7 O1 . . . . 2.5(2) ?
    C3 C4 C7 O1 . . . . -179.72(16) ?
    C5 C4 C7 C8 . . . . -113.95(18) ?
    C3 C4 C7 C8 . . . . 63.9(2) yes
    C5 C4 C7 C11 . . . . 123.30(18) ?
    C3 C4 C7 C11 . . . . -58.9(2) ?
    N1 C8 C7 O1 . . . . -60.4(2) ?
    N1 C8 C7 C4 . . . . 54.7(2) yes
    N1 C8 C7 C11 . . . . -179.15(16) ?
    O1 C7 C11 C12 . . . . 69.8(2) ?
    C4 C7 C11 C12 . . . . -48.7(3) ?
    C8 C7 C11 C12 . . . . -172.7(2) yes
    C4 C5 C6 C1 . . . . 0.8(3) ?
    C5 C6 C1 C2 . . . . -0.3(3) ?
    C5 C6 C1 Cl2 . . . . 179.58(16) ?
    C3 C2 C1 C6 . . . . -0.5(3) ?
    C3 C2 C1 Cl2 . . . . 179.71(14) ?
    C7 C11 C12 C13 . . . . -173.4(2) yes
    C9 N3 C10 N1 . . . . -0.2(3) ?
    N2 N1 C10 N3 . . . . 0.5(3) ?
    C8 N1 C10 N3 . . . . -174.89(19) ?
    C11 C12 C13 C14 . . . . 71.1(3) yes
    N1 N2 C9 N3 . . . . 0.6(3) ?
    C10 N3 C9 N2 . . . . -0.3(3) ?
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
    _geom_hbond_publ_flag
    O1 H1O N3 2_655 0.77(2) 2.07(2) 2.821(3) 166(2) yes
    C8 H8A Cl1 . 0.96(2) 2.70(2) 3.320(3) 123(2) yes
    C11 H11B Cl1 . 0.95(3) 2.67(2) 3.272(3) 122(2) yes
