##############################################################################
###                                                                        ###
###        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     SHELXL-97
_journal_date_recd_electronic     2005-05-16
_journal_date_accepted     2005-05-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      6
_journal_page_first     o1947
_journal_page_last     o1949
_journal_paper_category     EO
_publ_contact_author
;
'Nazan Ocak Ískeleli'
Department of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs University
TR-55139
Kurupelit-Samsun
Turkey
;
_publ_contact_author_email     'nocak@omu.edu.tr'
_publ_section_title
;
3-Hydroxy-2-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]-6-methylpyran-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Ocak Ískeleli, Nazan'
;
Department of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs University
TR-55139 Kurupelit-Samsun
Turkey
;
    'Işık, Şamil'
;
Department of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs University
TR-55139 Kurupelit-Samsun
Turkey
;
    'Dilsiz Aytemir, Mutlu'
;
Department of Pharmaceutical Chemistry
Faculty of Pharmacy
Hacettepe University
TR-06100 Sıhhiye
Ankara
Turkey
;
data_I
_chemical_name_systematic
;
3-Hydroxy-2-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]-6-methylpyran-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H20 N2 O4'
_chemical_formula_sum     'C13 H20 N2 O4'
_chemical_formula_iupac     'C13 H20 N2 O4'
_chemical_formula_weight     268.31
_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     15.256(2)
_cell_length_b     5.8527(5)
_cell_length_c     15.7510(19)
_cell_angle_alpha     90.00
_cell_angle_beta     95.373(10)
_cell_angle_gamma     90.00
_cell_volume     1400.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10945
_cell_measurement_theta_min     1.78
_cell_measurement_theta_max     29.28
_cell_measurement_temperature     296
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.580
_exptl_crystal_size_mid     0.343
_exptl_crystal_size_min     0.110
_exptl_crystal_density_diffrn     1.273
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.9545
_exptl_absorpt_correction_T_max     0.9920
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_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-II'
_diffrn_measurement_method     φ
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     13472
_diffrn_reflns_av_R_equivalents     0.0492
_diffrn_reflns_av_sigmaI/netI     0.0572
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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     3057
_reflns_number_gt     1705
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0699
_refine_ls_R_factor_gt     0.0329
_refine_ls_wR_factor_gt     0.0681
_refine_ls_wR_factor_ref     0.0735
_refine_ls_goodness_of_fit_ref     0.783
_refine_ls_restrained_S_all     0.783
_refine_ls_number_reflns     3057
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'w = 1/[σ²(Fo²)+(0.0394P)²] 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     0.137
_refine_diff_density_min     -0.117
_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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED32'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                    'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    O1 0.16849(6) 0.57390(17) 0.52421(5) 0.0421(3) Uani d . 1 . . O
    O3 0.10015(7) 0.50016(17) 0.30123(6) 0.0469(3) Uani d . 1 . . O
    H3 0.0763 0.3896 0.2768 0.070 Uiso calc R 1 . . H
    N1 0.30807(7) 0.72223(18) 0.40817(6) 0.0305(3) Uani d . 1 . . N
    N2 0.47016(7) 0.71037(19) 0.32800(6) 0.0329(3) Uani d . 1 . . N
    C10 0.36495(9) 0.9233(2) 0.40539(8) 0.0359(3) Uani d . 1 . . C
    H10A 0.3593 1.0176 0.4552 0.043 Uiso calc R 1 . . H
    H10B 0.3466 1.0133 0.3551 0.043 Uiso calc R 1 . . H
    C1 0.16016(9) 0.6012(2) 0.43715(8) 0.0342(3) Uani d . 1 . . C
    O4 0.63244(9) 0.6016(2) 0.45920(6) 0.0619(3) Uani d . 1 . . O
    H4 0.6527 0.5090 0.4949 0.093 Uiso calc R 1 . . H
    C8 0.31844(9) 0.5804(2) 0.33268(8) 0.0351(3) Uani d . 1 . . C
    H8A 0.2992 0.6657 0.2815 0.042 Uiso calc R 1 . . H
    H8B 0.2818 0.4452 0.3343 0.042 Uiso calc R 1 . . H
    C12 0.56243(9) 0.6506(3) 0.31796(8) 0.0420(4) Uani d . 1 . . C
    H12A 0.5958 0.7917 0.3188 0.050 Uiso calc R 1 . . H
    H12B 0.5643 0.5843 0.2617 0.050 Uiso calc R 1 . . H
    C7 0.21554(9) 0.7924(2) 0.41100(9) 0.0365(3) Uani d . 1 . . C
    H7A 0.1925 0.8464 0.3551 0.044 Uiso calc R 1 . . H
    H7B 0.2128 0.9178 0.4509 0.044 Uiso calc R 1 . . H
    C11 0.45958(9) 0.8523(2) 0.40317(8) 0.0371(3) Uani d . 1 . . C
    H11A 0.4964 0.9871 0.4017 0.044 Uiso calc R 1 . . H
    H11B 0.4785 0.7670 0.4544 0.044 Uiso calc R 1 . . H
    O2 0.02049(8) 0.1356(2) 0.37360(6) 0.0624(4) Uani d . 1 . . O
    C9 0.41317(9) 0.5099(2) 0.32993(9) 0.0360(3) Uani d . 1 . . C
    H9A 0.4316 0.4182 0.3797 0.043 Uiso calc R 1 . . H
    H9B 0.4187 0.4173 0.2796 0.043 Uiso calc R 1 . . H
    C6 0.10900(9) 0.4622(2) 0.38626(8) 0.0348(3) Uani d . 1 . . C
    C5 0.06444(9) 0.2697(3) 0.42091(8) 0.0407(4) Uani d . 1 . . C
    C2 0.12664(10) 0.3989(3) 0.55904(9) 0.0439(4) Uani d . 1 . . C
    C4 0.07737(10) 0.2510(3) 0.51199(9) 0.0457(4) Uani d . 1 . . C
    H4A 0.0505 0.1319 0.5388 0.055 Uiso calc R 1 . . H
    C13 0.61011(11) 0.4895(3) 0.38162(9) 0.0469(4) Uani d . 1 . . C
    H13A 0.5727 0.3595 0.3908 0.056 Uiso calc R 1 . . H
    H13B 0.6631 0.4332 0.3591 0.056 Uiso calc R 1 . . H
    C3 0.14217(14) 0.3983(4) 0.65429(10) 0.0727(6) Uani d . 1 . . C
    H3A 0.1005 0.2983 0.6774 0.109 Uiso calc R 1 . . H
    H3B 0.1351 0.5504 0.6755 0.109 Uiso calc R 1 . . H
    H3C 0.2008 0.3458 0.6711 0.109 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
    O1 0.0440(6) 0.0517(7) 0.0308(5) -0.0060(5) 0.0046(4) -0.0012(4)
    O3 0.0629(8) 0.0478(6) 0.0294(5) -0.0142(6) 0.0005(5) 0.0011(4)
    N1 0.0338(6) 0.0280(6) 0.0295(6) -0.0017(5) 0.0023(5) -0.0024(5)
    N2 0.0345(7) 0.0354(7) 0.0285(6) -0.0010(6) 0.0014(5) 0.0000(5)
    C10 0.0445(9) 0.0286(8) 0.0342(7) -0.0042(7) 0.0021(6) -0.0048(6)
    C1 0.0345(8) 0.0400(8) 0.0288(7) 0.0046(7) 0.0062(6) 0.0000(6)
    O4 0.0796(9) 0.0598(8) 0.0427(6) 0.0162(7) -0.0136(6) -0.0003(5)
    C8 0.0391(8) 0.0319(8) 0.0333(7) -0.0034(7) -0.0007(6) -0.0065(6)
    C12 0.0378(9) 0.0558(10) 0.0323(7) 0.0011(7) 0.0026(6) 0.0038(7)
    C7 0.0390(9) 0.0349(8) 0.0357(7) 0.0030(7) 0.0032(6) -0.0012(6)
    C11 0.0417(9) 0.0345(8) 0.0342(7) -0.0082(7) -0.0002(6) -0.0039(6)
    O2 0.0790(9) 0.0661(8) 0.0406(6) -0.0346(7) -0.0026(6) 0.0030(5)
    C9 0.0411(9) 0.0312(8) 0.0356(7) -0.0013(7) 0.0029(6) -0.0060(6)
    C6 0.0352(8) 0.0411(9) 0.0285(7) 0.0010(7) 0.0052(6) 0.0015(6)
    C5 0.0385(8) 0.0479(9) 0.0357(8) -0.0056(8) 0.0037(6) 0.0023(7)
    C2 0.0421(9) 0.0576(10) 0.0327(8) -0.0028(8) 0.0074(7) 0.0033(7)
    C4 0.0471(9) 0.0539(10) 0.0367(8) -0.0089(8) 0.0070(7) 0.0079(7)
    C13 0.0392(9) 0.0544(10) 0.0462(9) 0.0045(8) -0.0007(7) -0.0016(8)
    C3 0.0843(14) 0.1008(15) 0.0329(9) -0.0230(12) 0.0051(9) 0.0047(9)
_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
    O1 C2 . 1.3502(17) ?
    O1 C1 . 1.3747(15) ?
    O3 C6 . 1.3518(15) ?
    O3 H3 . 0.8200 ?
    N1 C10 . 1.4651(17) ?
    N1 C8 . 1.4709(16) ?
    N1 C7 . 1.4749(17) ?
    N2 C9 . 1.4622(17) ?
    N2 C11 . 1.4674(16) ?
    N2 C12 . 1.4732(18) ?
    C10 C11 . 1.506(2) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C1 C6 . 1.3404(19) ?
    C1 C7 . 1.483(2) ?
    O4 C13 . 1.4007(17) ?
    O4 H4 . 0.8200 ?
    C8 C9 . 1.5072(19) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C12 C13 . 1.512(2) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    O2 C5 . 1.2358(17) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C6 C5 . 1.449(2) ?
    C5 C4 . 1.4338(19) ?
    C2 C4 . 1.326(2) ?
    C2 C3 . 1.497(2) ?
    C4 H4A . 0.9300 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C3 H3A . 0.9600 ?
    C3 H3B . 0.9600 ?
    C3 H3C . 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
    C2 O1 C1 . . 119.38(11) ?
    C6 O3 H3 . . 109.5 ?
    C10 N1 C8 . . 108.68(10) ?
    C10 N1 C7 . . 110.39(10) ?
    C8 N1 C7 . . 110.94(10) ?
    C9 N2 C11 . . 109.07(10) ?
    C9 N2 C12 . . 112.82(11) ?
    C11 N2 C12 . . 113.53(11) ?
    N1 C10 C11 . . 110.54(11) ?
    N1 C10 H10A . . 109.5 ?
    C11 C10 H10A . . 109.5 ?
    N1 C10 H10B . . 109.5 ?
    C11 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 108.1 ?
    C6 C1 O1 . . 121.34(13) ?
    C6 C1 C7 . . 127.36(12) ?
    O1 C1 C7 . . 111.28(11) ?
    C13 O4 H4 . . 109.5 ?
    N1 C8 C9 . . 110.71(11) ?
    N1 C8 H8A . . 109.5 ?
    C9 C8 H8A . . 109.5 ?
    N1 C8 H8B . . 109.5 ?
    C9 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 108.1 ?
    N2 C12 C13 . . 118.82(12) ?
    N2 C12 H12A . . 107.6 ?
    C13 C12 H12A . . 107.6 ?
    N2 C12 H12B . . 107.6 ?
    C13 C12 H12B . . 107.6 ?
    H12A C12 H12B . . 107.0 ?
    N1 C7 C1 . . 111.70(11) ?
    N1 C7 H7A . . 109.3 ?
    C1 C7 H7A . . 109.3 ?
    N1 C7 H7B . . 109.3 ?
    C1 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 107.9 ?
    N2 C11 C10 . . 110.67(11) ?
    N2 C11 H11A . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    N2 C9 C8 . . 110.78(11) ?
    N2 C9 H9A . . 109.5 ?
    C8 C9 H9A . . 109.5 ?
    N2 C9 H9B . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 108.1 ?
    C1 C6 O3 . . 119.41(12) ?
    C1 C6 C5 . . 120.96(12) ?
    O3 C6 C5 . . 119.62(12) ?
    O2 C5 C4 . . 124.83(14) ?
    O2 C5 C6 . . 120.92(12) ?
    C4 C5 C6 . . 114.25(13) ?
    C4 C2 O1 . . 122.20(13) ?
    C4 C2 C3 . . 125.92(15) ?
    O1 C2 C3 . . 111.88(14) ?
    C2 C4 C5 . . 121.80(14) ?
    C2 C4 H4A . . 119.1 ?
    C5 C4 H4A . . 119.1 ?
    O4 C13 C12 . . 110.41(13) ?
    O4 C13 H13A . . 109.6 ?
    C12 C13 H13A . . 109.6 ?
    O4 C13 H13B . . 109.6 ?
    C12 C13 H13B . . 109.6 ?
    H13A C13 H13B . . 108.1 ?
    C2 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    C2 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
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
    O3 H3 O2 . 0.82 2.35 2.7548(15) 112
    O4 H4 N1 3_666 0.82 2.09 2.9024(15) 174
    O3 H3 N2 2_545 0.82 2.03 2.7859(14) 154
