#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013901.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013901
loop_
_publ_author_name
'K\"oysal, Yavuz'
'I\,s\?ik, \,Samil'
'K\"oksal, Meri\,c'
'Erd\~ogan, Hakk\?i'
'Gokhan, Nesrin'
_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
;
_journal_issue 4
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first o232
_journal_page_last o234
_journal_volume 60
_journal_year 2004
_chemical_formula_iupac 'C19 H20 F N3 O2'
_chemical_formula_moiety 'C19 H20 F N3 O2'
_chemical_formula_sum 'C19 H20 F N3 O2'
_chemical_formula_weight 341.22
_chemical_name_systematic
;
3-[4-(4-Fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens constr
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha 90.00
_cell_angle_beta 103.067(7)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.1788(6)
_cell_length_b 6.1512(4)
_cell_length_c 34.090(3)
_cell_measurement_reflns_used 10038
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 29.42
_cell_measurement_theta_min 0.00
_cell_volume 1670.6(2)
_computing_cell_refinement 'STOE X-AREA'
_computing_data_collection 'STOE X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction 'STOE X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type 'STOE IPDS 2'
_diffrn_measurement_method '\w scan'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0277
_diffrn_reflns_av_sigmaI/netI 0.0225
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 42
_diffrn_reflns_limit_l_min -42
_diffrn_reflns_number 7820
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 2.56
_exptl_absorpt_coefficient_mu 0.097
_exptl_absorpt_correction_T_max 0.9688
_exptl_absorpt_correction_T_min 0.9397
_exptl_absorpt_correction_type integration
_exptl_absorpt_process_details '(STOE X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.357
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 720
_exptl_crystal_size_max 0.620
_exptl_crystal_size_mid 0.480
_exptl_crystal_size_min 0.350
_refine_diff_density_max 0.945
_refine_diff_density_min -0.426
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_hydrogen_treatment 'see text'
_refine_ls_matrix_type full
_refine_ls_number_parameters 240
_refine_ls_number_reflns 3072
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.067
_refine_ls_R_factor_all 0.0954
_refine_ls_R_factor_gt 0.0796
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1428P)^2^+0.916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2331
_refine_ls_wR_factor_ref 0.2504
_reflns_number_gt 2368
_reflns_number_total 3072
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file av1163.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_database_code 2013901
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'
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_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
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 0.0737(13) 0.0909(16) 0.1090(19) 0.0017(11) 0.0390(13) 0.0125(13)
O1 0.107(2) 0.0838(19) 0.0788(19) -0.0306(16) 0.0064(15) -0.0247(15)
O2 0.0727(14) 0.0458(11) 0.0759(16) -0.0139(10) 0.0258(11) -0.0094(10)
N1 0.0670(16) 0.0463(13) 0.0774(19) -0.0094(11) 0.0245(14) -0.0192(12)
N2 0.107(2) 0.0521(15) 0.0659(18) -0.0184(15) 0.0459(17) -0.0141(12)
N3 0.0636(14) 0.0477(12) 0.0476(13) -0.0058(10) 0.0170(11) -0.0057(10)
C1 0.0516(15) 0.0680(19) 0.066(2) 0.0065(14) 0.0096(14) 0.0117(16)
C2 0.0610(18) 0.0642(19) 0.074(2) 0.0031(15) 0.0172(16) -0.0077(17)
C3 0.0609(17) 0.0521(16) 0.072(2) -0.0044(14) 0.0171(15) -0.0109(15)
C4 0.0486(14) 0.0472(14) 0.0533(16) -0.0017(12) 0.0021(12) -0.0038(12)
C5 0.0633(17) 0.0474(15) 0.0602(18) -0.0052(13) 0.0049(14) -0.0050(13)
C6 0.0591(17) 0.0591(18) 0.076(2) -0.0087(15) 0.0069(16) 0.0037(16)
C7 0.129(3) 0.0538(19) 0.094(3) -0.019(2) 0.066(3) -0.0174(18)
C8 0.090(2) 0.0450(15) 0.063(2) -0.0118(15) 0.0309(18) -0.0095(14)
C9 0.112(3) 0.055(2) 0.116(4) -0.007(2) 0.054(3) -0.020(2)
C10 0.080(2) 0.0411(15) 0.078(2) -0.0082(14) 0.0261(18) -0.0144(15)
C11 0.078(2) 0.0553(17) 0.0538(18) -0.0006(15) 0.0175(15) -0.0008(13)
C12 0.0718(19) 0.0530(16) 0.065(2) -0.0096(14) 0.0229(16) -0.0128(14)
C13 0.0553(15) 0.0426(14) 0.0669(19) -0.0001(12) 0.0268(14) -0.0011(13)
C14 0.0672(18) 0.0512(16) 0.076(2) 0.0076(14) 0.0251(16) 0.0152(15)
C15 0.0628(18) 0.0675(19) 0.0616(19) 0.0128(15) 0.0130(15) 0.0130(16)
C16 0.0482(14) 0.0577(16) 0.0614(18) 0.0057(12) 0.0132(12) -0.0028(14)
C17 0.0517(14) 0.0449(14) 0.0594(17) -0.0016(12) 0.0190(12) -0.0012(12)
C18 0.0492(13) 0.0427(13) 0.0551(16) 0.0010(11) 0.0226(12) -0.0022(11)
C19 0.0630(19) 0.078(2) 0.072(2) 0.0016(17) 0.0003(16) -0.0102(18)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_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_bond_atom_site_label_1
_geom_bond_atom_site_label_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_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
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
_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) ?