##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
r-2,c-6-Bis(4-fluorophenyl)-t-3,t-5-dimethylpiperidin-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 F2 N O'
_chemical_formula_sum     'C19 H19 F2 N O'
_chemical_formula_iupac     'C19 H19 F2 N O'
_chemical_formula_weight     315.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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     7.3830(6)
_cell_length_b     24.0102(19)
_cell_length_c     9.4278(7)
_cell_angle_alpha     90.00
_cell_angle_beta     101.7270(10)
_cell_angle_gamma     90.00
_cell_volume     1636.4(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2923
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     28.06
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.280
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_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 CCD area-detector'
_diffrn_measurement_device     'Bruker SMART APEX'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18490
_diffrn_reflns_av_R_equivalents     0.0200
_diffrn_reflns_av_sigmaI/netI     0.0143
_diffrn_reflns_theta_min     2.36
_diffrn_reflns_theta_max     28.06
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.968
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -31
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_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 > 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     3851
_reflns_number_gt     2773
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0772
_refine_ls_R_factor_gt     0.0607
_refine_ls_wR_factor_gt     0.1894
_refine_ls_wR_factor_ref     0.2120
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     3851
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1249P)²+0.2050P] 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     0.516
_refine_diff_density_min     -0.432
_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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material
                         'SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995)'
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
    C C1 0.6972(2) 0.02549(6) 0.79954(16) 0.0546(4) Uani d . 1 . .
    H H1 0.7019 0.0285 0.9039 0.066 Uiso calc R 1 . .
    C C2 0.4928(2) 0.01783(7) 0.72123(19) 0.0624(4) Uani d . 1 . .
    H H2 0.4918 0.0147 0.6174 0.075 Uiso calc R 1 . .
    C C3 0.3828(2) 0.06935(7) 0.74162(19) 0.0637(4) Uani d . 1 . .
    C C4 0.4655(2) 0.12406(7) 0.7076(2) 0.0637(4) Uani d . 1 . .
    H H4 0.4654 0.1244 0.6036 0.076 Uiso calc R 1 . .
    C C5 0.6706(2) 0.12620(6) 0.78990(18) 0.0585(4) Uani d . 1 . .
    H H5 0.6736 0.1247 0.8942 0.070 Uiso calc R 1 . .
    C C6 0.8102(2) -0.02404(6) 0.77288(17) 0.0558(4) Uani d . 1 . .
    C C7 0.8517(2) -0.03400(7) 0.63869(18) 0.0617(4) Uani d . 1 . .
    H H7 0.8203 -0.0075 0.5658 0.074 Uiso calc R 1 . .
    C C8 0.9388(3) -0.08247(8) 0.6106(2) 0.0734(5) Uani d . 1 . .
    H H8 0.9653 -0.0891 0.5197 0.088 Uiso calc R 1 . .
    C C9 0.9851(3) -0.12059(8) 0.7203(3) 0.0784(6) Uani d . 1 . .
    C C10 0.9494(3) -0.11202(8) 0.8545(3) 0.0834(6) Uani d . 1 . .
    H H10 0.9829 -0.1385 0.9270 0.100 Uiso calc R 1 . .
    C C11 0.8626(3) -0.06341(8) 0.8813(2) 0.0701(5) Uani d . 1 . .
    H H11 0.8389 -0.0569 0.9731 0.084 Uiso calc R 1 . .
    C C12 0.4069(3) -0.03515(10) 0.7657(3) 0.0970(7) Uani d . 1 . .
    H H12A 0.4217 -0.0361 0.8692 0.145 Uiso calc R 1 . .
    H H12B 0.4671 -0.0669 0.7339 0.145 Uiso calc R 1 . .
    H H12C 0.2776 -0.0360 0.7220 0.145 Uiso calc R 1 . .
    C C13 0.3516(3) 0.17334(10) 0.7391(3) 0.1006(8) Uani d . 1 . .
    H H13A 0.2274 0.1698 0.6843 0.151 Uiso calc R 1 . .
    H H13B 0.4054 0.2072 0.7124 0.151 Uiso calc R 1 . .
    H H13C 0.3498 0.1742 0.8406 0.151 Uiso calc R 1 . .
    C C14 0.7637(2) 0.17899(7) 0.75681(19) 0.0638(4) Uani d . 1 . .
    C C15 0.8070(3) 0.22048(8) 0.8600(3) 0.0826(6) Uani d . 1 . .
    H H15 0.7817 0.2156 0.9519 0.099 Uiso calc R 1 . .
    C C16 0.8895(4) 0.27015(9) 0.8253(4) 0.1013(8) Uani d . 1 . .
    H H16 0.9191 0.2984 0.8936 0.122 Uiso calc R 1 . .
    C C17 0.9248(3) 0.27607(8) 0.6917(4) 0.0966(8) Uani d . 1 . .
    C C18 0.8849(3) 0.23645(8) 0.5878(3) 0.0898(6) Uani d . 1 . .
    H H18 0.9113 0.2419 0.4965 0.108 Uiso calc R 1 . .
    C C19 0.8036(3) 0.18753(7) 0.6218(2) 0.0720(5) Uani d . 1 . .
    H H19 0.7752 0.1598 0.5519 0.086 Uiso calc R 1 . .
    N N1 0.76605(17) 0.07730(5) 0.74933(14) 0.0547(3) Uani d . 1 . .
    H H1A 0.8532 0.0789 0.7012 0.066 Uiso calc R 1 . .
    O O1 0.23876(19) 0.06688(7) 0.78279(19) 0.0912(5) Uani d . 1 . .
    F F1 1.0695(2) -0.16840(5) 0.6943(2) 0.1173(5) Uani d . 1 . .
    F F2 1.0055(3) 0.32416(6) 0.6583(3) 0.1454(7) Uani d . 1 . .
_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
    C1 N1 . 1.4588(19) ?
    C1 C6 . 1.503(2) ?
    C1 C2 . 1.550(2) ?
    C1 H1 . 0.9800 ?
    C2 C3 . 1.513(2) ?
    C2 C12 . 1.518(3) ?
    C2 H2 . 0.9800 ?
    C3 O1 . 1.206(2) ?
    C3 C4 . 1.510(2) ?
    C4 C13 . 1.516(2) ?
    C4 C5 . 1.556(2) ?
    C4 H4 . 0.9800 ?
    C5 N1 . 1.4595(19) ?
    C5 C14 . 1.504(2) ?
    C5 H5 . 0.9800 ?
    C6 C7 . 1.382(2) ?
    C6 C11 . 1.388(2) ?
    C7 C8 . 1.381(2) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.371(3) ?
    C8 H8 . 0.9300 ?
    C9 F1 . 1.352(2) ?
    C9 C10 . 1.359(3) ?
    C10 C11 . 1.379(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C19 . 1.379(3) ?
    C14 C15 . 1.384(3) ?
    C15 C16 . 1.408(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.345(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.354(4) ?
    C17 F2 . 1.365(3) ?
    C18 C19 . 1.386(3) ?
    C18 H18 . 0.9300 ?
    C19 H19 . 0.9300 ?
    N1 H1A . 0.8600 ?
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
    N1 C1 C6 . . 112.25(12) ?
    N1 C1 C2 . . 108.44(12) ?
    C6 C1 C2 . . 110.25(12) ?
    N1 C1 H1 . . 108.6 ?
    C6 C1 H1 . . 108.6 ?
    C2 C1 H1 . . 108.6 ?
    C3 C2 C12 . . 112.65(15) ?
    C3 C2 C1 . . 109.75(13) ?
    C12 C2 C1 . . 112.88(15) ?
    C3 C2 H2 . . 107.1 ?
    C12 C2 H2 . . 107.1 ?
    C1 C2 H2 . . 107.1 ?
    O1 C3 C4 . . 122.16(16) ?
    O1 C3 C2 . . 122.14(16) ?
    C4 C3 C2 . . 115.70(13) ?
    C3 C4 C13 . . 111.89(16) ?
    C3 C4 C5 . . 108.50(13) ?
    C13 C4 C5 . . 113.54(15) ?
    C3 C4 H4 . . 107.6 ?
    C13 C4 H4 . . 107.6 ?
    C5 C4 H4 . . 107.6 ?
    N1 C5 C14 . . 111.00(13) ?
    N1 C5 C4 . . 108.39(12) ?
    C14 C5 C4 . . 111.32(13) ?
    N1 C5 H5 . . 108.7 ?
    C14 C5 H5 . . 108.7 ?
    C4 C5 H5 . . 108.7 ?
    C7 C6 C11 . . 118.41(16) ?
    C7 C6 C1 . . 121.60(14) ?
    C11 C6 C1 . . 119.79(15) ?
    C8 C7 C6 . . 121.34(16) ?
    C8 C7 H7 . . 119.3 ?
    C6 C7 H7 . . 119.3 ?
    C9 C8 C7 . . 118.15(19) ?
    C9 C8 H8 . . 120.9 ?
    C7 C8 H8 . . 120.9 ?
    F1 C9 C10 . . 118.7(2) ?
    F1 C9 C8 . . 118.9(2) ?
    C10 C9 C8 . . 122.38(18) ?
    C9 C10 C11 . . 118.93(18) ?
    C9 C10 H10 . . 120.5 ?
    C11 C10 H10 . . 120.5 ?
    C10 C11 C6 . . 120.77(18) ?
    C10 C11 H11 . . 119.6 ?
    C6 C11 H11 . . 119.6 ?
    C2 C12 H12A . . 109.5 ?
    C2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C4 C13 H13A . . 109.5 ?
    C4 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C4 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C19 C14 C15 . . 118.66(18) ?
    C19 C14 C5 . . 120.60(15) ?
    C15 C14 C5 . . 120.73(18) ?
    C14 C15 C16 . . 119.7(2) ?
    C14 C15 H15 . . 120.1 ?
    C16 C15 H15 . . 120.1 ?
    C17 C16 C15 . . 118.8(2) ?
    C17 C16 H16 . . 120.6 ?
    C15 C16 H16 . . 120.6 ?
    C16 C17 C18 . . 123.2(2) ?
    C16 C17 F2 . . 118.8(2) ?
    C18 C17 F2 . . 118.0(3) ?
    C17 C18 C19 . . 118.0(2) ?
    C17 C18 H18 . . 121.0 ?
    C19 C18 H18 . . 121.0 ?
    C14 C19 C18 . . 121.55(19) ?
    C14 C19 H19 . . 119.2 ?
    C18 C19 H19 . . 119.2 ?
    C5 N1 C1 . . 112.48(13) ?
    C5 N1 H1A . . 123.8 ?
    C1 N1 H1A . . 123.8 ?
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
    N1 C1 C2 C3 . . . . -53.46(17) ?
    C6 C1 C2 C3 . . . . -176.73(13) ?
    N1 C1 C2 C12 . . . . 179.98(15) ?
    C6 C1 C2 C12 . . . . 56.71(19) ?
    C12 C2 C3 O1 . . . . -3.1(3) ?
    C1 C2 C3 O1 . . . . -129.78(18) ?
    C12 C2 C3 C4 . . . . 176.70(16) ?
    C1 C2 C3 C4 . . . . 50.01(19) ?
    O1 C3 C4 C13 . . . . 3.0(3) ?
    C2 C3 C4 C13 . . . . -176.83(16) ?
    O1 C3 C4 C5 . . . . 129.00(18) ?
    C2 C3 C4 C5 . . . . -50.79(19) ?
    C3 C4 C5 N1 . . . . 55.74(18) ?
    C13 C4 C5 N1 . . . . -179.19(16) ?
    C3 C4 C5 C14 . . . . 178.09(13) ?
    C13 C4 C5 C14 . . . . -56.8(2) ?
    N1 C1 C6 C7 . . . . -50.19(19) ?
    C2 C1 C6 C7 . . . . 70.83(18) ?
    N1 C1 C6 C11 . . . . 135.01(16) ?
    C2 C1 C6 C11 . . . . -103.97(17) ?
    C11 C6 C7 C8 . . . . 1.7(2) ?
    C1 C6 C7 C8 . . . . -173.18(15) ?
    C6 C7 C8 C9 . . . . -0.6(3) ?
    C7 C8 C9 F1 . . . . 179.65(16) ?
    C7 C8 C9 C10 . . . . -0.5(3) ?
    F1 C9 C10 C11 . . . . -179.75(17) ?
    C8 C9 C10 C11 . . . . 0.4(3) ?
    C9 C10 C11 C6 . . . . 0.8(3) ?
    C7 C6 C11 C10 . . . . -1.8(3) ?
    C1 C6 C11 C10 . . . . 173.17(16) ?
    N1 C5 C14 C19 . . . . 50.64(19) ?
    C4 C5 C14 C19 . . . . -70.19(19) ?
    N1 C5 C14 C15 . . . . -130.90(16) ?
    C4 C5 C14 C15 . . . . 108.27(18) ?
    C19 C14 C15 C16 . . . . 0.2(3) ?
    C5 C14 C15 C16 . . . . -178.30(17) ?
    C14 C15 C16 C17 . . . . -0.1(3) ?
    C15 C16 C17 C18 . . . . 0.0(4) ?
    C15 C16 C17 F2 . . . . -179.76(19) ?
    C16 C17 C18 C19 . . . . 0.0(4) ?
    F2 C17 C18 C19 . . . . 179.78(18) ?
    C15 C14 C19 C18 . . . . -0.2(3) ?
    C5 C14 C19 C18 . . . . 178.32(16) ?
    C17 C18 C19 C14 . . . . 0.1(3) ?
    C14 C5 N1 C1 . . . . 171.33(12) ?
    C4 C5 N1 C1 . . . . -66.12(17) ?
    C6 C1 N1 C5 . . . . -173.32(12) ?
    C2 C1 N1 C5 . . . . 64.62(16) ?
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
    C11 H11 O1 3_657 0.93 2.49 3.400(3) 164.6
    C18 H18 F1 3_756 0.93 2.54 3.197(3) 127.54
data_global
_journal_date_recd_electronic     2007-12-11
_journal_date_accepted     2007-12-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o429
_journal_page_last     o429
_journal_paper_category     QO
_journal_coeditor_code     AT2525
_publ_contact_author_name     'Professor D. Velmurugan'
_publ_contact_author_address
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai - 600 025
India
;
_publ_contact_author_email     d_velu@yahoo.com
_publ_contact_author_fax     '+914422300122'
_publ_contact_author_phone     '+914422300122'
_publ_section_title
;\
r-2,c-6-Bis(4-fluorophenyl)-t-3,t-5-\
dimethylpiperidin-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'D. Gayathri'
;     Centre of Advanced Study in Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'D. Velmurugan'
;     Centre of Advanced Study in Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'G. Aridoss'
;     Department of Chemistry
      Annamalai University
      Annamalai Nagar 608 002
      India
;
    'S. Kabilan'
;     Department of Chemistry
      Annamalai University
      Annamalai Nagar 608 002
      India
;
    'K. Ravikumar'
;     Laboratory of X-ray Crystallography
      Indian Institute of Chemical Technology
      Hyderabad 500 007
      India
;
