##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(2,4-dichlorophenylhydroxymethyl)-1-tetralone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 Cl2 O2'
_chemical_formula_sum     'C17 H14 Cl2 O2'
_chemical_formula_iupac     'C17 H14 Cl2 O2'
_chemical_formula_weight     321.18
_chemical_melting_point     '171\% C-173\% C'
_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     23.2570(10)
_cell_length_b     8.7150(10)
_cell_length_c     14.6680(10)
_cell_angle_alpha     90.00
_cell_angle_beta     100.270(10)
_cell_angle_gamma     90.00
_cell_volume     2925.4(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     8
_cell_measurement_theta_max     18
_cell_measurement_temperature     123(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.459
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1328
_exptl_absorpt_coefficient_mu     0.444
_exptl_absorpt_correction_type     '\y scan'
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.825
_exptl_absorpt_correction_T_max     0.903
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     123(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     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4488
_diffrn_reflns_av_R_equivalents     0.0104
_diffrn_reflns_av_sigmaI/netI     0.0165
_diffrn_reflns_theta_min     2.50
_diffrn_reflns_theta_max     27.97
_diffrn_reflns_theta_full     27.97
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -30
_diffrn_reflns_limit_h_max     30
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0
_refine_special_details
;
The ω-scan width was (0.65 + 0.72 tanθ)° with a ω-scan rate of 0.69-3.35°
min⁻¹.  The scan angle was extended 25% on each side of each peak for
background measurement.  Refinement was by full-matrix least-squares methods.
 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     3536
_reflns_number_gt     3144
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0329
_refine_ls_R_factor_gt     0.0265
_refine_ls_wR_factor_gt     0.0717
_refine_ls_wR_factor_ref     0.0746
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     1.049
_refine_ls_number_reflns     3536
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0403P)²+2.3455P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.389
_refine_diff_density_min     -0.242
_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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_reduction     'Xtal3.7 (Hall et al., 2000)'
_computing_structure_solution     'Xtal3.7'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Xtal3.7'
_computing_publication_material     'SHELXL97'
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
    Cl1 0.424247(12) 0.96722(3) 0.257182(18) 0.01696(8) Uani d . 1 . . Cl
    Cl2 0.427031(13) 0.35991(3) 0.30975(2) 0.02068(8) Uani d . 1 . . Cl
    O1 0.42030(4) 1.20358(10) -0.01012(6) 0.01646(17) Uani d . 1 . . O
    O2 0.45633(3) 0.86097(10) -0.02648(5) 0.01527(17) Uani d . 1 . . O
    H2 0.4924 0.8454 -0.0115 0.023 Uiso calc R 1 . . H
    C1 0.37522(5) 1.12808(13) -0.02107(7) 0.0133(2) Uani d . 1 . . C
    C2 0.37216(5) 0.96852(13) 0.01914(7) 0.0128(2) Uani d . 1 . . C
    H2A 0.3526 0.9786 0.0743 0.015 Uiso calc R 1 . . H
    C3 0.33305(5) 0.86561(14) -0.05103(8) 0.0170(2) Uani d . 1 . . C
    H3A 0.3495 0.8585 -0.1087 0.020 Uiso calc R 1 . . H
    H3B 0.3318 0.7610 -0.0252 0.020 Uiso calc R 1 . . H
    C4 0.27125(5) 0.93128(16) -0.07304(9) 0.0205(2) Uani d . 1 . . C
    H4A 0.2481 0.8717 -0.1243 0.025 Uiso calc R 1 . . H
    H4B 0.2524 0.9197 -0.0180 0.025 Uiso calc R 1 . . H
    C5 0.27059(5) 1.09797(16) -0.10004(8) 0.0184(2) Uani d . 1 . . C
    C6 0.22020(5) 1.16329(18) -0.15196(9) 0.0253(3) Uani d . 1 . . C
    H6 0.1866 1.1013 -0.1706 0.030 Uiso calc R 1 . . H
    C7 0.21863(6) 1.31690(19) -0.17651(9) 0.0282(3) Uani d . 1 . . C
    H7 0.1842 1.3588 -0.2124 0.034 Uiso calc R 1 . . H
    C8 0.26717(6) 1.41022(18) -0.14896(9) 0.0259(3) Uani d . 1 . . C
    H8 0.2657 1.5159 -0.1652 0.031 Uiso calc R 1 . . H
    C9 0.31761(6) 1.34814(15) -0.09776(8) 0.0202(2) Uani d . 1 . . C
    H9 0.3509 1.4114 -0.0788 0.024 Uiso calc R 1 . . H
    C10 0.31974(5) 1.19192(14) -0.07382(8) 0.0158(2) Uani d . 1 . . C
    C11 0.43316(5) 0.90157(13) 0.05355(7) 0.0126(2) Uani d . 1 . . C
    H11 0.4584 0.9826 0.0885 0.015 Uiso calc R 1 . . H
    C12 0.43036(5) 0.76496(13) 0.11695(7) 0.0127(2) Uani d . 1 . . C
    C13 0.42647(5) 0.78412(13) 0.21029(8) 0.0130(2) Uani d . 1 . . C
    C14 0.42570(5) 0.66120(13) 0.27017(8) 0.0144(2) Uani d . 1 . . C
    H14 0.4240 0.6773 0.3337 0.017 Uiso calc R 1 . . H
    C15 0.42755(5) 0.51429(13) 0.23477(8) 0.0152(2) Uani d . 1 . . C
    C16 0.43076(5) 0.48864(14) 0.14231(8) 0.0167(2) Uani d . 1 . . C
    H16 0.4317 0.3872 0.1189 0.020 Uiso calc R 1 . . H
    C17 0.43255(5) 0.61462(13) 0.08477(8) 0.0152(2) Uani d . 1 . . C
    H17 0.4353 0.5980 0.0217 0.018 Uiso calc R 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 C13 . 1.7421(11) ?
    Cl2 C15 . 1.7393(12) ?
    O1 C1 . 1.2239(14) ?
    O2 C11 . 1.4210(13) ?
    O2 H2 . 0.8400 ?
    C1 C10 . 1.4889(15) ?
    C1 C2 . 1.5172(15) ?
    C2 C11 . 1.5336(15) ?
    C2 C3 . 1.5353(15) ?
    C2 H2A . 1.0000 ?
    C3 C4 . 1.5271(16) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.5051(19) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.3998(16) ?
    C5 C10 . 1.4029(17) ?
    C6 C7 . 1.385(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.391(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.3852(17) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.4047(17) ?
    C9 H9 . 0.9500 ?
    C11 C12 . 1.5193(15) ?
    C11 H11 . 1.0000 ?
    C12 C17 . 1.3968(15) ?
    C12 C13 . 1.3980(15) ?
    C13 C14 . 1.3874(15) ?
    C14 C15 . 1.3851(16) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.3895(16) ?
    C16 C17 . 1.3900(16) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
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
    C11 O2 H2 . . 109.5 ?
    O1 C1 C10 . . 120.66(10) ?
    O1 C1 C2 . . 122.69(10) ?
    C10 C1 C2 . . 116.63(10) ?
    C1 C2 C11 . . 111.84(9) ?
    C1 C2 C3 . . 109.75(9) ?
    C11 C2 C3 . . 113.64(9) ?
    C1 C2 H2A . . 107.1 ?
    C11 C2 H2A . . 107.1 ?
    C3 C2 H2A . . 107.1 ?
    C4 C3 C2 . . 110.22(10) ?
    C4 C3 H3A . . 109.6 ?
    C2 C3 H3A . . 109.6 ?
    C4 C3 H3B . . 109.6 ?
    C2 C3 H3B . . 109.6 ?
    H3A C3 H3B . . 108.1 ?
    C5 C4 C3 . . 112.48(10) ?
    C5 C4 H4A . . 109.1 ?
    C3 C4 H4A . . 109.1 ?
    C5 C4 H4B . . 109.1 ?
    C3 C4 H4B . . 109.1 ?
    H4A C4 H4B . . 107.8 ?
    C6 C5 C10 . . 118.29(13) ?
    C6 C5 C4 . . 120.26(12) ?
    C10 C5 C4 . . 121.44(10) ?
    C7 C6 C5 . . 121.01(13) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C6 C7 C8 . . 120.47(12) ?
    C6 C7 H7 . . 119.8 ?
    C8 C7 H7 . . 119.8 ?
    C9 C8 C7 . . 119.60(13) ?
    C9 C8 H8 . . 120.2 ?
    C7 C8 H8 . . 120.2 ?
    C8 C9 C10 . . 120.19(13) ?
    C8 C9 H9 . . 119.9 ?
    C10 C9 H9 . . 119.9 ?
    C5 C10 C9 . . 120.43(11) ?
    C5 C10 C1 . . 120.83(11) ?
    C9 C10 C1 . . 118.73(11) ?
    O2 C11 C12 . . 111.99(9) ?
    O2 C11 C2 . . 106.72(8) ?
    C12 C11 C2 . . 111.19(9) ?
    O2 C11 H11 . . 109.0 ?
    C12 C11 H11 . . 109.0 ?
    C2 C11 H11 . . 109.0 ?
    C17 C12 C13 . . 117.11(10) ?
    C17 C12 C11 . . 121.34(10) ?
    C13 C12 C11 . . 121.55(10) ?
    C14 C13 C12 . . 122.55(10) ?
    C14 C13 Cl1 . . 116.92(8) ?
    C12 C13 Cl1 . . 120.51(9) ?
    C15 C14 C13 . . 118.14(10) ?
    C15 C14 H14 . . 120.9 ?
    C13 C14 H14 . . 120.9 ?
    C14 C15 C16 . . 121.68(10) ?
    C14 C15 Cl2 . . 118.28(9) ?
    C16 C15 Cl2 . . 120.03(9) ?
    C15 C16 C17 . . 118.57(11) ?
    C15 C16 H16 . . 120.7 ?
    C17 C16 H16 . . 120.7 ?
    C16 C17 C12 . . 121.93(10) ?
    C16 C17 H17 . . 119.0 ?
    C12 C17 H17 . . 119.0 ?
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
    O1 C1 C2 C11 . . . . -13.37(14) ?
    C10 C1 C2 C11 . . . . 167.92(9) ?
    O1 C1 C2 C3 . . . . -140.45(11) ?
    C10 C1 C2 C3 . . . . 40.84(12) ?
    C1 C2 C3 C4 . . . . -60.50(12) ?
    C11 C2 C3 C4 . . . . 173.44(9) ?
    C2 C3 C4 C5 . . . . 51.27(13) ?
    C3 C4 C5 C6 . . . . 157.98(11) ?
    C3 C4 C5 C10 . . . . -22.40(15) ?
    C10 C5 C6 C7 . . . . -0.36(18) ?
    C4 C5 C6 C7 . . . . 179.28(11) ?
    C5 C6 C7 C8 . . . . -0.8(2) ?
    C6 C7 C8 C9 . . . . 0.94(19) ?
    C7 C8 C9 C10 . . . . 0.01(18) ?
    C6 C5 C10 C9 . . . . 1.30(17) ?
    C4 C5 C10 C9 . . . . -178.33(11) ?
    C6 C5 C10 C1 . . . . -178.10(11) ?
    C4 C5 C10 C1 . . . . 2.27(16) ?
    C8 C9 C10 C5 . . . . -1.14(17) ?
    C8 C9 C10 C1 . . . . 178.27(11) ?
    O1 C1 C10 C5 . . . . 169.16(11) ?
    C2 C1 C10 C5 . . . . -12.10(15) ?
    O1 C1 C10 C9 . . . . -10.25(16) ?
    C2 C1 C10 C9 . . . . 168.49(10) ?
    C1 C2 C11 O2 . . . . -73.61(11) ?
    C3 C2 C11 O2 . . . . 51.34(12) ?
    C1 C2 C11 C12 . . . . 163.99(9) ?
    C3 C2 C11 C12 . . . . -71.06(12) ?
    O2 C11 C12 C17 . . . . -18.81(14) ?
    C2 C11 C12 C17 . . . . 100.49(12) ?
    O2 C11 C12 C13 . . . . 160.11(10) ?
    C2 C11 C12 C13 . . . . -80.59(12) ?
    C17 C12 C13 C14 . . . . 1.02(16) ?
    C11 C12 C13 C14 . . . . -177.94(10) ?
    C17 C12 C13 Cl1 . . . . 179.35(8) ?
    C11 C12 C13 Cl1 . . . . 0.39(14) ?
    C12 C13 C14 C15 . . . . -1.49(16) ?
    Cl1 C13 C14 C15 . . . . -179.87(9) ?
    C13 C14 C15 C16 . . . . 0.72(17) ?
    C13 C14 C15 Cl2 . . . . 179.62(8) ?
    C14 C15 C16 C17 . . . . 0.46(17) ?
    Cl2 C15 C16 C17 . . . . -178.43(9) ?
    C15 C16 C17 C12 . . . . -0.94(17) ?
    C13 C12 C17 C16 . . . . 0.23(16) ?
    C11 C12 C17 C16 . . . . 179.19(10) ?
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
    O2 H2 O1 5_675 0.84 2.04 2.8789(11) 173
    C11 H11 Cl1 . 1.00 2.73 3.0842(11) 101
    C17 H17 O2 . 0.95 2.47 2.8107(14) 101
    C14 H14 O1 6_576 0.95 2.53 3.4547(14) 164
    C16 H16 O1 1_545 0.95 2.46 3.3221(14) 151
data_tetralone
_journal_date_recd_electronic     2002-04-09
_journal_date_accepted     2002-04-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2002
_journal_volume     58
_journal_issue      5
_journal_page_first     o582
_journal_page_last     o583
_journal_paper_category     EO
_publ_contact_author_name     'J. Wilson Quail'
_publ_contact_author_address
;
Department of Chemistry
University of Saskatchewan
Saskatoon
Saskatchewan
Canada S7N 5C9
;
_publ_contact_author_email     quail@sask.usask.ca
_publ_contact_author_fax     (306)-966-4730
_publ_contact_author_phone     (306)-966-4663
_publ_section_title
;
2-(2,4-Dichlorophenylhydroxymethyl)-1-tetralone
;
loop_
    _publ_author_name
    _publ_author_address
    'Oloo, Eliud O. '
;
Department of Chemistry, University of Saskatchewan,
110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9
;
    'Quail, J. Wilson'
;
Department of Chemistry, University of Saskatchewan,
110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9
;
    'Perjési, Pál'
;
Department of Medical Chemistry, University Medical School of Pécs,
H-7601 Pécs, Hungary
;
    'Dimmock, Jonathan R.'
;
College of Pharmacy and Nutrition, University of Saskatchewan
110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9
;
