##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 2.0.1.  #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_p14
_audit_creation_method     SHELXL
_chemical_name_systematic
;
1,4-Bis(2-hydroxy-5-methylbenzyl)piperazine
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C20 H26 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     326.43
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P21/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     5.8940(10)
_cell_length_b     8.8060(10)
_cell_length_c     17.1760(10)
_cell_angle_alpha     90.00
_cell_angle_beta     92.920(10)
_cell_angle_gamma     90.00
_cell_volume     890.3(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     42
_cell_measurement_theta_min     6.22
_cell_measurement_theta_max     13.51
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.218
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
The structure was solved by direct methods and refined by full-matrix
least-squares procedures.
;
_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     'Siemens P4'
_diffrn_measurement_method     'θ/2θ scans'
_diffrn_reflns_number     2946
_diffrn_reflns_av_R_equivalents     0.033
_diffrn_reflns_av_sigmaI/netI     0.043
_diffrn_reflns_theta_min     2.37
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     <1
_reflns_number_total     2036
_reflns_number_observed     1342
_reflns_observed_criterion     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.068
_refine_ls_R_factor_obs     0.044
_refine_ls_wR_factor_all     0.134
_refine_ls_wR_factor_obs     0.120
_refine_ls_goodness_of_fit_all     0.868
_refine_ls_goodness_of_fit_obs     0.975
_refine_ls_restrained_S_all     0.868
_refine_ls_restrained_S_obs     0.975
_refine_ls_number_reflns     2036
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme
               'calc w = 1/[\s^2^(Fo^2^)+(0.0961P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_shift/esd_max     0.01
_refine_ls_shift/esd_mean     0.001
_refine_diff_density_max     0.15
_refine_diff_density_min     -0.19
_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     'XSCANS (Siemens, 1994)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1985)'
_computing_structure_refinement     'SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics     'ZORTEP (Zsolnai, 1997)'
_computing_publication_material     'PARST (Nardelli, 1983, 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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 -0.2816(2) 0.7303(2) 0.30487(7) 0.0442(3) Uani d . 1 . C
    C2 -0.0953(2) 0.6401(2) 0.28920(7) 0.0407(3) Uani d . 1 . C
    C3 -0.0816(3) 0.5810(2) 0.21466(8) 0.0454(3) Uani d . 1 . C
    C4 -0.2459(3) 0.6097(2) 0.15537(7) 0.0490(4) Uani d . 1 . C
    C5 -0.4275(3) 0.6997(2) 0.17313(9) 0.0554(4) Uani d . 1 . C
    C6 -0.4472(3) 0.7614(2) 0.24633(9) 0.0528(4) Uani d . 1 . C
    C7 0.0933(2) 0.6117(2) 0.35038(8) 0.0504(4) Uani d . 1 . C
    N8 0.0098(2) 0.58653(13) 0.42875(6) 0.0411(3) Uani d . 1 . N
    C9 0.2025(2) 0.5784(2) 0.48658(8) 0.0504(4) Uani d . 1 . C
    C10 -0.1221(3) 0.4458(2) 0.43254(8) 0.0471(4) Uani d . 1 . C
    O11 -0.3070(2) 0.79147(14) 0.37748(6) 0.0615(4) Uani d . 1 . O
    C12 -0.2267(5) 0.5430(3) 0.07507(10) 0.0739(6) Uani d . 1 . C
    H3 0.042(3) 0.5212(19) 0.2054(8) 0.055(4) Uiso d . 1 . H
    H5 -0.541(4) 0.717(2) 0.1335(12) 0.085(6) Uiso d . 1 . H
    H6 -0.565(3) 0.8250(19) 0.2597(9) 0.061(5) Uiso d . 1 . H
    H7A 0.202(3) 0.696(2) 0.3545(10) 0.070(5) Uiso d . 1 . H
    H7B 0.191(3) 0.523(2) 0.3361(10) 0.070(5) Uiso d . 1 . H
    H9A 0.289(3) 0.665(2) 0.4839(9) 0.061(5) Uiso d . 1 . H
    H9B 0.307(3) 0.491(2) 0.4735(9) 0.069(5) Uiso d . 1 . H
    H10A -0.249(3) 0.4514(18) 0.3944(9) 0.055(4) Uiso d . 1 . H
    H10B -0.024(3) 0.360(2) 0.4193(8) 0.052(4) Uiso d . 1 . H
    H11 -0.208(4) 0.738(3) 0.4083(13) 0.103(8) Uiso d . 1 . H
    H12A -0.262(5) 0.613(3) 0.0391(15) 0.127(9) Uiso d . 1 . H
    H12B -0.327(5) 0.451(3) 0.0649(13) 0.121(8) Uiso d . 1 . H
    H12C -0.084(6) 0.499(4) 0.0657(16) 0.155(12) Uiso d . 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
    C1 0.0474(7) 0.0468(7) 0.0386(6) 0.0024(6) 0.0057(6) 0.0047(5)
    C2 0.0390(7) 0.0467(7) 0.0363(6) -0.0010(6) 0.0027(5) 0.0051(5)
    C3 0.0472(7) 0.0480(8) 0.0416(7) 0.0033(6) 0.0062(6) 0.0034(6)
    C4 0.0627(9) 0.0490(8) 0.0350(6) -0.0055(7) 0.0002(6) 0.0079(6)
    C5 0.0542(8) 0.0667(10) 0.0444(7) 0.0006(8) -0.0075(7) 0.0181(7)
    C6 0.0472(8) 0.0602(9) 0.0513(8) 0.0126(7) 0.0054(7) 0.0149(7)
    C7 0.0385(7) 0.0710(10) 0.0417(7) 0.0022(8) 0.0009(6) 0.0044(7)
    N8 0.0355(5) 0.0508(7) 0.0362(5) -0.0043(5) -0.0057(4) 0.0018(5)
    C9 0.0387(7) 0.0629(9) 0.0481(8) -0.0123(7) -0.0120(6) 0.0083(7)
    C10 0.0456(7) 0.0509(8) 0.0434(7) -0.0056(7) -0.0118(6) -0.0002(6)
    O11 0.0692(7) 0.0701(7) 0.0455(6) 0.0194(6) 0.0072(5) -0.0049(5)
    C12 0.107(2) 0.0754(12) 0.0391(8) -0.0016(13) -0.0020(9) -0.0019(8)
_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 O11 . 1.374(2) y
    C1 C2 . 1.393(2) ?
    C1 C6 . 1.392(2) ?
    C2 C3 . 1.388(2) ?
    C2 C7 . 1.511(2) y
    C3 C4 . 1.392(2) ?
    C3 H3 . 0.92(2) ?
    C4 C5 . 1.378(2) ?
    C4 C12 . 1.509(2) y
    C5 C6 . 1.380(2) ?
    C5 H5 . 0.94(2) ?
    C6 H6 . 0.93(2) ?
    C7 N8 . 1.474(2) y
    C7 H7A . 0.98(2) ?
    C7 H7B . 1.01(2) ?
    N8 C10 . 1.466(2) y
    N8 C9 . 1.472(2) y
    C9 C10 3_566 1.505(2) y
    C9 H9A . 0.92(2) ?
    C9 H9B . 1.02(2) ?
    C10 C9 3_566 1.505(2) y
    C10 H10A . 0.97(2) ?
    C10 H10B . 0.99(2) ?
    O11 H11 . 0.90(3) ?
    C12 H12A . 0.89(3) ?
    C12 H12B . 1.01(3) ?
    C12 H12C . 0.94(3) ?
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
    O11 C1 C2 . . 121.53(12) ?
    O11 C1 C6 . . 118.28(13) ?
    C2 C1 C6 . . 120.19(13) ?
    C3 C2 C1 . . 118.41(12) ?
    C3 C2 C7 . . 120.27(13) ?
    C1 C2 C7 . . 121.27(12) ?
    C2 C3 C4 . . 122.37(14) ?
    C2 C3 H3 . . 117.2(9) ?
    C4 C3 H3 . . 120.4(9) ?
    C5 C4 C3 . . 117.50(13) ?
    C5 C4 C12 . . 121.5(2) ?
    C3 C4 C12 . . 121.0(2) ?
    C4 C5 C6 . . 122.01(14) ?
    C4 C5 H5 . . 117.5(12) ?
    C6 C5 H5 . . 120.4(12) ?
    C5 C6 C1 . . 119.50(15) ?
    C5 C6 H6 . . 124.0(10) ?
    C1 C6 H6 . . 116.4(10) ?
    N8 C7 C2 . . 113.06(11) y
    N8 C7 H7A . . 107.2(10) ?
    C2 C7 H7A . . 112.3(10) ?
    N8 C7 H7B . . 109.0(10) ?
    C2 C7 H7B . . 111.5(10) ?
    H7A C7 H7B . . 103.2(14) ?
    C10 N8 C7 . . 111.74(12) y
    C10 N8 C9 . . 108.75(11) y
    C7 N8 C9 . . 109.95(11) y
    N8 C9 C10 . 3_566 111.16(12) y
    N8 C9 H9A . . 109.6(10) ?
    C10 C9 H9A 3_566 . 111.4(10) ?
    N8 C9 H9B . . 109.9(10) ?
    C10 C9 H9B 3_566 . 108.7(10) ?
    H9A C9 H9B . . 105.9(15) ?
    N8 C10 C9 . 3_566 110.66(12) y
    N8 C10 H10A . . 108.6(9) ?
    C9 C10 H10A 3_566 . 111.2(9) ?
    N8 C10 H10B . . 108.8(9) ?
    C9 C10 H10B 3_566 . 108.7(9) ?
    H10A C10 H10B . . 108.9(13) ?
    C1 O11 H11 . . 103.3(14) ?
    C4 C12 H12A . . 109.6(17) ?
    C4 C12 H12B . . 113.6(13) ?
    H12A C12 H12B . . 109(2) ?
    C4 C12 H12C . . 115.0(18) ?
    H12A C12 H12C . . 110(3) ?
    H12B C12 H12C . . 99(3) ?
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
    O11 C1 C2 C3 . . . . 179.46(12) ?
    C6 C1 C2 C3 . . . . -0.9(2) ?
    O11 C1 C2 C7 . . . . -3.1(2) ?
    C6 C1 C2 C7 . . . . 176.57(14) ?
    C1 C2 C3 C4 . . . . 0.5(2) ?
    C7 C2 C3 C4 . . . . -177.01(13) ?
    C2 C3 C4 C5 . . . . -0.4(2) ?
    C2 C3 C4 C12 . . . . -179.6(2) ?
    C3 C4 C5 C6 . . . . 0.8(2) ?
    C12 C4 C5 C6 . . . . 180.0(2) ?
    C4 C5 C6 C1 . . . . -1.2(2) ?
    O11 C1 C6 C5 . . . . -179.10(13) ?
    C2 C1 C6 C5 . . . . 1.2(2) ?
    C3 C2 C7 N8 . . . . -142.05(14) ?
    C1 C2 C7 N8 . . . . 40.5(2) ?
    C2 C7 N8 C10 . . . . 66.0(2) ?
    C2 C7 N8 C9 . . . . -173.14(14) ?
    C10 N8 C9 C10 . . . 3_566 -57.9(2) ?
    C7 N8 C9 C10 . . . 3_566 179.43(13) ?
    C7 N8 C10 C9 . . . 3_566 179.18(11) ?
    C9 N8 C10 C9 . . . 3_566 57.6(2) ?
data_global
_journal_date_recd_electronic     99-05-10
_journal_date_accepted     99-08-09
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1999
_journal_volume     C55
_journal_issue     DEC99
_journal_page_first     2147
_journal_page_last     2149
_journal_paper_category     FO
_publ_contact_author_name     'Dr M. N. Ponnuswamy'
_publ_contact_author_address
;   Department of Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
_publ_contact_author_email     crystal@giasmd01.vsnl.net.in
_publ_contact_author_fax     '091 44 235 2494'
_publ_contact_author_phone     '091 44 235 1367'
_publ_section_title
;
1,4-Bis(2-hydroxy-5-methylbenzyl)piperazine
;
loop_
    _publ_author_name
    _publ_author_address
    'Kuppayee, M.'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'Kumaran, D.'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'Ponnuswamy, M. N.'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'Kandaswamy, M.'
;     Department of Inorganic Chemistry
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'Jayanthi Violet, M.'
;     Department of Inorganic Chemistry
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'Chinnakali, K.'
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM
      Penang, Malaysia
;
    'Hoong-Kun Fun'
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM
      Penang, Malaysia
;
