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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2003-12-08
_journal_date_accepted     2004-02-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2004
_journal_volume     60
_journal_issue      4
_journal_page_first     o232
_journal_page_last     o234
_journal_paper_category     FO
_publ_contact_author_name     'Yavuz Köysal'
_publ_contact_author_address
;     Department of Physics
      Faculty of Arts and Sciences
      Ondokuzmayıs University, 55139-Kurupelit
      Samsun-Turkey
;
_publ_contact_author_email     'yavuzk@omu.edu.tr'
_publ_contact_author_fax     ' '
_publ_contact_author_phone     ' '
_publ_section_title
;
3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
and
3-[4-(2-fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yavuz Köysal' ?
;     Department of Physics
      Faculty of Arts and Sciences
      Ondokuz Mayıs University, Kurupelit, 55139 Samsun
      Turkey
;
    'Şamil Işık' ?
;     Department of Physics
      Faculty of Arts and Sciences
      Ondokuz Mayıs University, Kurupelit, 55139 Samsun
      Turkey
;
    'Meriç Köksal' ?
;     Faculty of Pharmacy
      Yeditepe University, Ístanbul
      Turkey
;
    'Hakkı Erdog̃an' ?
;     Department of Pharmaceutical Chemistry
      Faculty of Pharmacy
      Hacettepe University, 06100 Sıhhiye, Ankara
      Turkey
;
    'Nesrin Gokhan' ?
;     Department of Pharmaceutical Chemistry
      Faculty of Pharmacy
      Hacettepe University, 06100 Sıhhiye, Ankara
      Turkey
;
data_I
_chemical_name_systematic
;
3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H20 F N3 O2'
_chemical_formula_sum     'C19 H20 F N3 O2'
_chemical_formula_iupac     'C19 H20 F N3 O2'
_chemical_formula_weight     341.22
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.1788(6)
_cell_length_b     6.1512(4)
_cell_length_c     34.090(3)
_cell_angle_alpha     90.00
_cell_angle_beta     103.067(7)
_cell_angle_gamma     90.00
_cell_volume     1670.6(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10038
_cell_measurement_theta_min     0.00
_cell_measurement_theta_max     29.42
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.620
_exptl_crystal_size_mid     0.480
_exptl_crystal_size_min     0.350
_exptl_crystal_density_diffrn     1.357
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(STOE X-RED; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.9397
_exptl_absorpt_correction_T_max     0.9688
_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     'STOE IPDS 2'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     7820
_diffrn_reflns_av_R_equivalents     0.0277
_diffrn_reflns_av_sigmaI/netI     0.0225
_diffrn_reflns_theta_min     2.56
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -42
_diffrn_reflns_limit_l_max     42
_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     3072
_reflns_number_gt     2368
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0954
_refine_ls_R_factor_gt     0.0796
_refine_ls_wR_factor_gt     0.2331
_refine_ls_wR_factor_ref     0.2504
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     3072
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'see text'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.1428P)²+0.916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     constr
_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     0.945
_refine_diff_density_min     -0.426
_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' 0.0030 0.0020
                         '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'
    'F' 'F' 0.0170 0.0100
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0060 0.0030
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0110 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'STOE X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'STOE X-AREA'
_computing_data_reduction     'STOE X-RED (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
                             'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)'
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
    F1 -0.4451(3) 0.1980(4) 0.25278(8) 0.0883(8) Uani d . 1 . . F
    O1 0.6376(4) 0.7349(5) 0.11743(9) 0.0921(9) Uani d . 1 . . O
    O2 0.5004(3) 0.8047(3) 0.05353(7) 0.0634(6) Uani d . 1 . . O
    N1 0.0705(3) 0.2670(4) 0.17372(9) 0.0623(7) Uani d . 1 . . N
    N2 0.3002(4) 0.3067(4) 0.12303(9) 0.0709(9) Uani d . 1 . . N
    N3 0.4476(3) 0.4915(4) 0.08023(7) 0.0523(6) Uani d . 1 . . N
    C1 -0.3220(4) 0.2157(6) 0.23245(11) 0.0624(8) Uani d . 1 . . C
    C2 -0.2266(4) 0.4004(6) 0.23707(11) 0.0661(9) Uani d . 1 . . C
    H2 -0.2467 0.5116 0.2538 0.076(11) Uiso d R 1 . . H
    C3 -0.0995(4) 0.4168(5) 0.21697(11) 0.0613(8) Uani d . 1 . . C
    H3 -0.0336 0.5416 0.2201 0.064(9) Uiso d R 1 . . H
    C4 -0.0671(3) 0.2523(4) 0.19178(9) 0.0512(7) Uani d . 1 . . C
    C5 -0.1692(4) 0.0694(5) 0.18714(10) 0.0584(8) Uani d . 1 . . C
    H5 -0.1527 -0.0418 0.1700 0.065(9) Uiso d R 1 . . H
    C6 -0.2963(4) 0.0526(6) 0.20758(11) 0.0661(9) Uani d . 1 . . C
    H6 -0.3639 -0.0705 0.2046 0.087(12) Uiso d R 1 . . H
    C7 0.1183(6) 0.4709(6) 0.16319(14) 0.0859(13) Uani d . 1 . . C
    H7A 0.1208 0.5700 0.1855 0.103 Uiso calc R 1 . . H
    H7B 0.0347 0.5239 0.1403 0.103 Uiso calc R 1 . . H
    C8 0.2901(5) 0.4735(5) 0.15245(11) 0.0641(9) Uani d . 1 . . C
    H8A 0.3007 0.6150 0.1408 0.077(11) Uiso d R 1 . . H
    H8B 0.3821 0.4572 0.1757 0.123(18) Uiso d R 1 . . H
    C9 0.2595(6) 0.1032(6) 0.13649(16) 0.0903(13) Uani d . 1 . . C
    H9A 0.3419 0.0649 0.1607 0.108 Uiso calc R 1 . . H
    H9B 0.2652 -0.0049 0.1161 0.108 Uiso calc R 1 . . H
    C10 0.0904(4) 0.0975(5) 0.14518(11) 0.0650(9) Uani d . 1 . . C
    H10A 0.0009 0.1073 0.1216 0.093(13) Uiso d R 1 . . H
    H10B 0.0827 -0.0417 0.1574 0.085(12) Uiso d R 1 . . H
    C11 0.4556(4) 0.3174(5) 0.10935(10) 0.0619(8) Uani d . 1 . . C
    H11A 0.4743 0.1801 0.0971 0.064(9) Uiso d R 1 . . H
    H11B 0.5490 0.3426 0.1321 0.083(12) Uiso d R 1 . . H
    C12 0.5398(4) 0.6778(5) 0.08766(11) 0.0621(8) Uani d . 1 . . C
    C13 0.3857(4) 0.6890(4) 0.02439(10) 0.0529(7) Uani d . 1 . . C
    C14 0.3172(4) 0.7473(5) -0.01371(11) 0.0634(8) Uani d . 1 . . C
    H14 0.3420 0.8795 -0.0242 0.073(10) Uiso d R 1 . . H
    C15 0.2082(4) 0.5990(6) -0.03666(11) 0.0641(8) Uani d . 1 . . C
    H15 0.1585 0.6333 -0.0633 0.068(10) Uiso d R 1 . . H
    C16 0.1698(4) 0.4003(5) -0.02106(10) 0.0556(7) Uani d . 1 . . C
    C17 0.2429(3) 0.3473(5) 0.01838(9) 0.0510(7) Uani d . 1 . . C
    H17 0.2191 0.2157 0.0293 0.054(8) Uiso d R 1 . . H
    C18 0.3520(3) 0.4937(4) 0.04108(9) 0.0473(6) Uani d . 1 . . C
    C19 0.0502(4) 0.2464(7) -0.04739(12) 0.0735(10) Uani d . 1 . . C
    H19A -0.0323 0.3280 -0.0662 0.110 Uiso calc R 1 . . H
    H19B -0.0047 0.1585 -0.0310 0.110 Uiso calc R 1 . . H
    H19C 0.1112 0.1545 -0.0618 0.110 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
    F1 C1 . 1.350(4) yes
    O1 C12 . 1.194(4) yes
    O2 C12 . 1.377(4) yes
    O2 C13 . 1.397(4) yes
    N1 C7 . 1.385(4) yes
    N1 C4 . 1.402(4) yes
    N1 C10 . 1.460(4) yes
    N2 C9 . 1.399(5) yes
    N2 C8 . 1.450(4) yes
    N2 C11 . 1.451(4) yes
    N3 C12 . 1.364(4) yes
    N3 C18 . 1.386(4) yes
    N3 C11 . 1.452(4) yes
    C1 C6 . 1.360(5) ?
    C1 C2 . 1.366(5) ?
    C2 C3 . 1.372(5) ?
    C2 H2 . 0.9298 ?
    C3 C4 . 1.391(4) ?
    C3 H3 . 0.9299 ?
    C4 C5 . 1.389(4) ?
    C5 C6 . 1.380(5) ?
    C5 H5 . 0.9296 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.530(5) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 H8A . 0.9680 ?
    C8 H8B . 0.9661 ?
    C9 C10 . 1.479(5) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9588 ?
    C10 H10B . 0.9594 ?
    C11 H11A . 0.9701 ?
    C11 H11B . 0.9697 ?
    C13 C14 . 1.342(5) ?
    C13 C18 . 1.384(4) ?
    C14 C15 . 1.387(5) ?
    C14 H14 . 0.9298 ?
    C15 C16 . 1.396(5) ?
    C15 H15 . 0.9301 ?
    C16 C17 . 1.381(4) ?
    C16 C19 . 1.504(5) ?
    C17 C18 . 1.376(4) ?
    C17 H17 . 0.9299 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
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
    C12 O2 C13 . . 107.7(2) ?
    C7 N1 C4 . . 118.3(3) ?
    C7 N1 C10 . . 113.2(3) ?
    C4 N1 C10 . . 117.9(2) ?
    C9 N2 C8 . . 110.6(3) ?
    C9 N2 C11 . . 115.9(3) ?
    C8 N2 C11 . . 112.4(3) ?
    C12 N3 C18 . . 109.8(3) ?
    C12 N3 C11 . . 123.7(3) ?
    C18 N3 C11 . . 126.4(2) ?
    F1 C1 C6 . . 119.9(3) ?
    F1 C1 C2 . . 118.7(3) ?
    C6 C1 C2 . . 121.3(3) ?
    C1 C2 C3 . . 118.8(3) ?
    C1 C2 H2 . . 120.5 ?
    C3 C2 H2 . . 120.8 ?
    C2 C3 C4 . . 121.8(3) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.1 ?
    C5 C4 C3 . . 117.8(3) ?
    C5 C4 N1 . . 121.6(3) ?
    C3 C4 N1 . . 120.5(3) ?
    C6 C5 C4 . . 120.3(3) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.9 ?
    C1 C6 C5 . . 120.0(3) ?
    C1 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 120.1 ?
    N1 C7 C8 . . 113.6(3) yes
    N1 C7 H7A . . 108.9 ?
    C8 C7 H7A . . 108.9 ?
    N1 C7 H7B . . 108.9 ?
    C8 C7 H7B . . 108.9 ?
    H7A C7 H7B . . 107.7 ?
    N2 C8 C7 . . 110.9(3) yes
    N2 C8 H8A . . 109.2 ?
    C7 C8 H8A . . 106.2 ?
    N2 C8 H8B . . 109.7 ?
    C7 C8 H8B . . 112.9 ?
    H8A C8 H8B . . 107.6 ?
    N2 C9 C10 . . 113.0(3) yes
    N2 C9 H9A . . 109.0 ?
    C10 C9 H9A . . 109.0 ?
    N2 C9 H9B . . 109.0 ?
    C10 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
    N1 C10 C9 . . 111.5(3) yes
    N1 C10 H10A . . 109.5 ?
    C9 C10 H10A . . 113.7 ?
    N1 C10 H10B . . 108.7 ?
    C9 C10 H10B . . 105.3 ?
    H10A C10 H10B . . 107.9 ?
    N2 C11 N3 . . 110.2(3) yes
    N2 C11 H11A . . 109.6 ?
    N3 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.9 ?
    N3 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    O1 C12 N3 . . 129.9(4) yes
    O1 C12 O2 . . 122.4(3) yes
    N3 C12 O2 . . 107.8(3) ?
    C14 C13 C18 . . 123.5(3) ?
    C14 C13 O2 . . 128.2(3) ?
    C18 C13 O2 . . 108.3(3) ?
    C13 C14 C15 . . 116.4(3) ?
    C13 C14 H14 . . 121.9 ?
    C15 C14 H14 . . 121.7 ?
    C14 C15 C16 . . 122.1(3) ?
    C14 C15 H15 . . 118.9 ?
    C16 C15 H15 . . 118.9 ?
    C17 C16 C15 . . 119.5(3) ?
    C17 C16 C19 . . 120.8(3) ?
    C15 C16 C19 . . 119.7(3) ?
    C18 C17 C16 . . 118.4(3) ?
    C18 C17 H17 . . 120.8 ?
    C16 C17 H17 . . 120.8 ?
    C17 C18 C13 . . 120.1(3) ?
    C17 C18 N3 . . 133.5(3) ?
    C13 C18 N3 . . 106.4(3) ?
    C16 C19 H19A . . 109.5 ?
    C16 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C16 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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
    F1 C1 C2 C3 . . . . 178.9(3) ?
    C6 C1 C2 C3 . . . . -2.0(5) ?
    C1 C2 C3 C4 . . . . 0.9(5) ?
    C2 C3 C4 C5 . . . . 0.6(5) ?
    C2 C3 C4 N1 . . . . -175.7(3) ?
    C7 N1 C4 C5 . . . . 150.7(4) yes
    C10 N1 C4 C5 . . . . 8.4(5) yes
    C7 N1 C4 C3 . . . . -33.2(5) ?
    C10 N1 C4 C3 . . . . -175.4(3) ?
    C3 C4 C5 C6 . . . . -1.0(5) ?
    N1 C4 C5 C6 . . . . 175.3(3) ?
    F1 C1 C6 C5 . . . . -179.2(3) ?
    C2 C1 C6 C5 . . . . 1.6(5) ?
    C4 C5 C6 C1 . . . . -0.1(5) ?
    C4 N1 C7 C8 . . . . 167.4(3) ?
    C10 N1 C7 C8 . . . . -48.7(5) ?
    C9 N2 C8 C7 . . . . -54.1(5) ?
    C11 N2 C8 C7 . . . . 174.7(3) ?
    N1 C7 C8 N2 . . . . 50.8(5) yes
    C8 N2 C9 C10 . . . . 57.7(5) ?
    C11 N2 C9 C10 . . . . -172.9(3) ?
    C7 N1 C10 C9 . . . . 50.0(5) ?
    C4 N1 C10 C9 . . . . -165.9(3) ?
    N2 C9 C10 N1 . . . . -54.9(5) yes
    C9 N2 C11 N3 . . . . 153.6(3) ?
    C8 N2 C11 N3 . . . . -77.9(4) ?
    C12 N3 C11 N2 . . . . 110.5(3) ?
    C18 N3 C11 N2 . . . . -71.4(4) ?
    C18 N3 C12 O1 . . . . -179.2(3) ?
    C11 N3 C12 O1 . . . . -0.9(5) ?
    C18 N3 C12 O2 . . . . 1.7(3) ?
    C11 N3 C12 O2 . . . . 180.0(2) ?
    C13 O2 C12 O1 . . . . 178.9(3) ?
    C13 O2 C12 N3 . . . . -1.9(3) ?
    C12 O2 C13 C14 . . . . -177.9(3) ?
    C12 O2 C13 C18 . . . . 1.5(3) ?
    C18 C13 C14 C15 . . . . -0.4(4) ?
    O2 C13 C14 C15 . . . . 178.9(3) ?
    C13 C14 C15 C16 . . . . 0.7(5) ?
    C14 C15 C16 C17 . . . . -0.5(5) ?
    C14 C15 C16 C19 . . . . 179.8(3) ?
    C15 C16 C17 C18 . . . . 0.0(4) ?
    C19 C16 C17 C18 . . . . 179.7(3) ?
    C16 C17 C18 C13 . . . . 0.3(4) ?
    C16 C17 C18 N3 . . . . -178.4(3) ?
    C14 C13 C18 C17 . . . . -0.1(4) ?
    O2 C13 C18 C17 . . . . -179.5(2) ?
    C14 C13 C18 N3 . . . . 178.9(3) ?
    O2 C13 C18 N3 . . . . -0.4(3) ?
    C12 N3 C18 C17 . . . . 178.1(3) ?
    C11 N3 C18 C17 . . . . -0.1(5) ?
    C12 N3 C18 C13 . . . . -0.8(3) ?
    C11 N3 C18 C13 . . . . -179.0(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
    C5 H5 O1 1_445 0.93 2.58 3.268(4) 131
    C14 H14 O2 3_675 0.93 2.65 3.547(4) 163
data_II
_chemical_name_systematic
;
3-[4-(2-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H20 F N3 O2'
_chemical_formula_sum     'C19 H20 F N3 O2'
_chemical_formula_iupac     'C19 H20 F N3 O2'
_chemical_formula_weight     341.22
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'p 21/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.7467(10)
_cell_length_b     9.5470(4)
_cell_length_c     11.4779(6)
_cell_angle_alpha     90.00
_cell_angle_beta     91.422(5)
_cell_angle_gamma     90.00
_cell_volume     1724.98(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     19436
_cell_measurement_theta_min     0.00
_cell_measurement_theta_max     29.45
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.600
_exptl_crystal_size_mid     0.417
_exptl_crystal_size_min     0.310
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(STOE X-RED; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.8784
_exptl_absorpt_correction_T_max     0.9802
_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     'STOE IPDS 2'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     24265
_diffrn_reflns_av_R_equivalents     0.0927
_diffrn_reflns_av_sigmaI/netI     0.0399
_diffrn_reflns_theta_min     2.50
_diffrn_reflns_theta_max     25.99
_diffrn_reflns_theta_full     25.99
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_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     3392
_reflns_number_gt     2779
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0488
_refine_ls_R_factor_gt     0.0410
_refine_ls_wR_factor_gt     0.1179
_refine_ls_wR_factor_ref     0.1235
_refine_ls_goodness_of_fit_ref     1.070
_refine_ls_restrained_S_all     1.070
_refine_ls_number_reflns     3392
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     'see text'
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0658P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     constr
_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     0.209
_refine_diff_density_min     -0.151
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.015(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' 0.0030 0.0020
                         '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'
    'F' 'F' 0.0170 0.0100
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0060 0.0030
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0110 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'STOE X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'STOE X-AREA'
_computing_data_reduction     'STOE X-RED (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
                             'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)'
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
    F1 -0.02623(7) 0.84447(13) 0.02487(12) 0.1032(4) Uani d . 1 . . F
    O1 0.41098(7) 0.76653(12) -0.10543(10) 0.0726(3) Uani d . 1 . . O
    O2 0.44069(6) 0.54729(11) -0.16695(8) 0.0625(3) Uani d . 1 . . O
    N1 0.07924(7) 0.67022(13) 0.15050(9) 0.0566(3) Uani d . 1 . . N
    N2 0.25221(6) 0.60123(11) 0.11386(8) 0.0514(3) Uani d . 1 . . N
    N3 0.37578(6) 0.56932(12) 0.00110(9) 0.0525(3) Uani d . 1 . . N
    C1 -0.06219(10) 0.75215(18) 0.09803(15) 0.0711(4) Uani d . 1 . . C
    C2 -0.14883(11) 0.7532(2) 0.10515(19) 0.0895(6) Uani d . 1 . . C
    H2 -0.1814 0.8125 0.0580 0.123(8) Uiso d R 1 . . H
    C3 -0.18693(11) 0.6660(3) 0.18300(19) 0.0957(7) Uani d . 1 . . C
    H3 -0.2456 0.6656 0.1895 0.100(6) Uiso d R 1 . . H
    C4 -0.13785(12) 0.5789(3) 0.24992(18) 0.0979(7) Uani d . 1 . . C
    H4 -0.1633 0.5208 0.3039 0.117(7) Uiso d R 1 . . H
    C5 -0.05018(10) 0.5767(2) 0.23999(15) 0.0797(5) Uani d . 1 . . C
    H5 -0.0182 0.5151 0.2860 0.102(7) Uiso d R 1 . . H
    C6 -0.00974(9) 0.66396(16) 0.16311(12) 0.0586(3) Uani d . 1 . . C
    C7 0.13017(9) 0.5996(2) 0.23995(12) 0.0679(4) Uani d . 1 . . C
    H7A 0.1108 0.6258 0.3164 0.075(5) Uiso d R 1 . . H
    H7B 0.1239 0.4991 0.2315 0.085(6) Uiso d R 1 . . H
    C8 0.22230(9) 0.63949(19) 0.22851(11) 0.0644(4) Uani d . 1 . . C
    H8A 0.2562 0.5918 0.2880 0.080(5) Uiso d R 1 . . H
    H8B 0.2288 0.7396 0.2401 0.083(5) Uiso d R 1 . . H
    C9 0.20062(8) 0.66981(17) 0.02394(12) 0.0608(4) Uani d . 1 . . C
    H9A 0.2201 0.6424 -0.0523 0.077(5) Uiso d R 1 . . H
    H9B 0.2067 0.7706 0.0310 0.071(5) Uiso d R 1 . . H
    C10 0.10865(9) 0.63019(18) 0.03537(11) 0.0615(4) Uani d . 1 . . C
    H10A 0.0747 0.6774 -0.0244 0.081(5) Uiso d R 1 . . H
    H10B 0.1020 0.5300 0.0246 0.077(5) Uiso d R 1 . . H
    C11 0.34135(8) 0.63315(15) 0.10457(11) 0.0547(3) Uani d . 1 . . C
    H11A 0.3491 0.7339 0.1013 0.063(4) Uiso d R 1 . . H
    H11B 0.3719 0.5984 0.1731 0.061(4) Uiso d R 1 . . H
    C12 0.40852(8) 0.64277(16) -0.08915(11) 0.0567(3) Uani d . 1 . . C
    C13 0.42527(8) 0.41439(15) -0.12344(11) 0.0547(3) Uani d . 1 . . C
    C14 0.44493(8) 0.28826(17) -0.17164(13) 0.0637(4) Uani d . 1 . . C
    H14 0.4730 0.2815 -0.2418 0.081(5) Uiso d R 1 . . H
    C15 0.42038(9) 0.17060(17) -0.11008(14) 0.0651(4) Uani d . 1 . . C
    H15 0.4328 0.0827 -0.1401 0.073(5) Uiso d R 1 . . H
    C16 0.37814(9) 0.17879(15) -0.00525(13) 0.0596(3) Uani d . 1 . . C
    C17 0.35979(8) 0.30978(15) 0.04181(11) 0.0550(3) Uani d . 1 . . C
    H17 0.3317 0.3178 0.1118 0.054(4) Uiso d R 1 . . H
    C18 0.38446(7) 0.42639(14) -0.01861(11) 0.0495(3) Uani d . 1 . . C
    C19 0.35196(13) 0.04793(18) 0.05641(16) 0.0813(5) Uani d . 1 . . C
    H19A 0.3211 0.0723 0.1246 0.122 Uiso calc R 1 . . H
    H19B 0.4016 -0.0049 0.0789 0.122 Uiso calc R 1 . . H
    H19C 0.3164 -0.0075 0.0053 0.122 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
    F1 C1 . 1.351(2) yes
    O1 C12 . 1.1970(18) yes
    O2 C12 . 1.3810(17) yes
    O2 C13 . 1.3872(17) yes
    N1 C6 . 1.4134(17) yes
    N1 C7 . 1.4530(18) yes
    N1 C10 . 1.4620(17) yes
    N2 C11 . 1.4429(16) yes
    N2 C9 . 1.4535(17) yes
    N2 C8 . 1.4553(16) yes
    N3 C12 . 1.3628(17) yes
    N3 C18 . 1.3905(17) yes
    N3 C11 . 1.4518(15) yes
    C1 C2 . 1.369(2) ?
    C1 C6 . 1.385(2) ?
    C2 C3 . 1.371(3) ?
    C2 H2 . 0.9289 ?
    C3 C4 . 1.359(3) ?
    C3 H3 . 0.9293 ?
    C4 C5 . 1.388(2) ?
    C4 H4 . 0.9297 ?
    C5 C6 . 1.381(2) ?
    C5 H5 . 0.9299 ?
    C7 C8 . 1.509(2) ?
    C7 H7A . 0.9691 ?
    C7 H7B . 0.9691 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9699 ?
    C9 C10 . 1.5056(19) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9699 ?
    C10 H10A . 0.9699 ?
    C10 H10B . 0.9697 ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9699 ?
    C13 C14 . 1.364(2) ?
    C13 C18 . 1.3828(17) ?
    C14 C15 . 1.387(2) ?
    C14 H14 . 0.9297 ?
    C15 C16 . 1.391(2) ?
    C15 H15 . 0.9298 ?
    C16 C17 . 1.3953(19) ?
    C16 C19 . 1.499(2) ?
    C17 C18 . 1.3728(19) ?
    C17 H17 . 0.9298 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
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
    C12 O2 C13 . . 107.49(10) ?
    C6 N1 C7 . . 116.06(11) ?
    C6 N1 C10 . . 114.75(11) ?
    C7 N1 C10 . . 109.61(11) ?
    C11 N2 C9 . . 112.33(10) ?
    C11 N2 C8 . . 110.56(10) ?
    C9 N2 C8 . . 109.96(11) ?
    C12 N3 C18 . . 109.92(10) ?
    C12 N3 C11 . . 124.18(12) ?
    C18 N3 C11 . . 125.82(11) ?
    F1 C1 C2 . . 117.77(17) ?
    F1 C1 C6 . . 118.57(14) ?
    C2 C1 C6 . . 123.65(18) ?
    C1 C2 C3 . . 119.18(19) ?
    C1 C2 H2 . . 120.4 ?
    C3 C2 H2 . . 120.4 ?
    C4 C3 C2 . . 119.20(17) ?
    C4 C3 H3 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    C3 C4 C5 . . 121.0(2) ?
    C3 C4 H4 . . 119.6 ?
    C5 C4 H4 . . 119.4 ?
    C6 C5 C4 . . 121.22(19) ?
    C6 C5 H5 . . 119.5 ?
    C4 C5 H5 . . 119.3 ?
    C5 C6 C1 . . 115.68(14) ?
    C5 C6 N1 . . 124.40(14) ?
    C1 C6 N1 . . 119.90(14) ?
    N1 C7 C8 . . 109.66(12) yes
    N1 C7 H7A . . 109.8 ?
    C8 C7 H7A . . 109.8 ?
    N1 C7 H7B . . 109.6 ?
    C8 C7 H7B . . 109.7 ?
    H7A C7 H7B . . 108.2 ?
    N2 C8 C7 . . 110.41(12) yes
    N2 C8 H8A . . 109.5 ?
    C7 C8 H8A . . 109.5 ?
    N2 C8 H8B . . 109.6 ?
    C7 C8 H8B . . 109.6 ?
    H8A C8 H8B . . 108.1 ?
    N2 C9 C10 . . 110.30(11) yes
    N2 C9 H9A . . 109.6 ?
    C10 C9 H9A . . 109.7 ?
    N2 C9 H9B . . 109.6 ?
    C10 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 108.1 ?
    N1 C10 C9 . . 109.88(11) yes
    N1 C10 H10A . . 109.6 ?
    C9 C10 H10A . . 109.7 ?
    N1 C10 H10B . . 109.7 ?
    C9 C10 H10B . . 109.7 ?
    H10A C10 H10B . . 108.2 ?
    N2 C11 N3 . . 110.83(10) ?
    N2 C11 H11A . . 109.6 ?
    N3 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.4 ?
    N3 C11 H11B . . 109.4 ?
    H11A C11 H11B . . 108.1 ?
    O1 C12 N3 . . 129.86(13) yes
    O1 C12 O2 . . 122.46(12) yes
    N3 C12 O2 . . 107.68(12) ?
    C14 C13 C18 . . 122.76(13) ?
    C14 C13 O2 . . 128.17(12) ?
    C18 C13 O2 . . 109.07(11) ?
    C13 C14 C15 . . 116.07(13) ?
    C13 C14 H14 . . 122.0 ?
    C15 C14 H14 . . 122.0 ?
    C14 C15 C16 . . 122.70(14) ?
    C14 C15 H15 . . 118.6 ?
    C16 C15 H15 . . 118.7 ?
    C15 C16 C17 . . 119.55(14) ?
    C15 C16 C19 . . 120.30(14) ?
    C17 C16 C19 . . 120.15(14) ?
    C18 C17 C16 . . 117.86(13) ?
    C18 C17 H17 . . 121.1 ?
    C16 C17 H17 . . 121.1 ?
    C17 C18 C13 . . 121.05(12) ?
    C17 C18 N3 . . 133.11(11) ?
    C13 C18 N3 . . 105.82(11) ?
    C16 C19 H19A . . 109.5 ?
    C16 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C16 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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
    F1 C1 C2 C3 . . . . -176.61(17) ?
    C6 C1 C2 C3 . . . . 2.1(3) ?
    C1 C2 C3 C4 . . . . -1.1(3) ?
    C2 C3 C4 C5 . . . . -0.4(3) ?
    C3 C4 C5 C6 . . . . 0.9(3) ?
    C4 C5 C6 C1 . . . . 0.0(2) ?
    C4 C5 C6 N1 . . . . 178.21(16) ?
    F1 C1 C6 C5 . . . . 177.16(15) ?
    C2 C1 C6 C5 . . . . -1.5(2) ?
    F1 C1 C6 N1 . . . . -1.1(2) ?
    C2 C1 C6 N1 . . . . -179.81(15) ?
    C7 N1 C6 C5 . . . . -12.2(2) yes
    C10 N1 C6 C5 . . . . 117.40(17) yes
    C7 N1 C6 C1 . . . . 165.97(14) ?
    C10 N1 C6 C1 . . . . -64.47(18) ?
    C6 N1 C7 C8 . . . . -168.68(12) ?
    C10 N1 C7 C8 . . . . 59.34(17) ?
    C11 N2 C8 C7 . . . . -177.27(12) ?
    C9 N2 C8 C7 . . . . 58.13(17) ?
    N1 C7 C8 N2 . . . . -59.02(18) yes
    C11 N2 C9 C10 . . . . 178.47(11) ?
    C8 N2 C9 C10 . . . . -57.96(16) ?
    C6 N1 C10 C9 . . . . 167.96(12) ?
    C7 N1 C10 C9 . . . . -59.37(17) ?
    N2 C9 C10 N1 . . . . 58.71(16) yes
    C9 N2 C11 N3 . . . . -68.75(14) ?
    C8 N2 C11 N3 . . . . 168.02(11) ?
    C12 N3 C11 N2 . . . . 117.10(13) ?
    C18 N3 C11 N2 . . . . -66.38(16) yes
    C18 N3 C12 O1 . . . . 177.94(14) ?
    C11 N3 C12 O1 . . . . -5.1(2) ?
    C18 N3 C12 O2 . . . . -1.47(14) ?
    C11 N3 C12 O2 . . . . 175.53(11) ?
    C13 O2 C12 O1 . . . . -178.22(13) ?
    C13 O2 C12 N3 . . . . 1.24(13) ?
    C12 O2 C13 C14 . . . . 179.13(13) ?
    C12 O2 C13 C18 . . . . -0.57(14) ?
    C18 C13 C14 C15 . . . . 1.0(2) ?
    O2 C13 C14 C15 . . . . -178.70(13) ?
    C13 C14 C15 C16 . . . . 0.0(2) ?
    C14 C15 C16 C17 . . . . -0.6(2) ?
    C14 C15 C16 C19 . . . . 179.02(14) ?
    C15 C16 C17 C18 . . . . 0.17(19) ?
    C19 C16 C17 C18 . . . . -179.43(13) ?
    C16 C17 C18 C13 . . . . 0.77(18) ?
    C16 C17 C18 N3 . . . . 178.97(13) ?
    C14 C13 C18 C17 . . . . -1.4(2) ?
    O2 C13 C18 C17 . . . . 178.32(11) ?
    C14 C13 C18 N3 . . . . 179.97(12) ?
    O2 C13 C18 N3 . . . . -0.31(14) ?
    C12 N3 C18 C17 . . . . -177.29(13) ?
    C11 N3 C18 C17 . . . . 5.8(2) ?
    C12 N3 C18 C13 . . . . 1.10(14) ?
    C11 N3 C18 C13 . . . . -175.84(11) ?
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
    C14 H14 O1 2_644 0.93 2.57 3.4680(18) 163
