##############################################################################
###                                                                        ###
###        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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,4-Bis{2-hydroxy-3-[N-(2-hydroxyethyl)imino]-5-methylbenzyl}piperazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H36 N4 O4'
_chemical_formula_sum     'C26 H36 N4 O4'
_chemical_formula_weight     468.62
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     9.7575(2)
_cell_length_b     13.8091(3)
_cell_length_c     18.42700(10)
_cell_angle_alpha     90.00
_cell_angle_beta     99.9640(10)
_cell_angle_gamma     90.00
_cell_volume     2445.45(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6435
_cell_measurement_theta_min     1.94
_cell_measurement_theta_max     28.57
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.273
_exptl_crystal_density_meas     none
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1008
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     none
_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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17219
_diffrn_reflns_av_R_equivalents     0.0431
_diffrn_reflns_av_sigmaI/netI     0.0534
_diffrn_reflns_theta_min     1.85
_diffrn_reflns_theta_max     28.66
_diffrn_reflns_theta_full     28.66
_diffrn_measured_fraction_theta_max     0.950
_diffrn_measured_fraction_theta_full     0.950
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     none
_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     6219
_reflns_number_gt     3721
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1074
_refine_ls_R_factor_gt     0.0595
_refine_ls_wR_factor_gt     0.1627
_refine_ls_wR_factor_ref     0.1904
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     6219
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w = 1/[σ²(Fo²)+(0.1P)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     <0.001
_refine_diff_density_max     0.278
_refine_diff_density_min     -0.212
_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     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2002)
;
_computing_publication_material     'SHELXL97 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
    C1 0.4111(2) 0.98193(12) 0.20338(9) 0.0330(4) Uani d . 1 . . C
    C2 0.47411(19) 1.06918(13) 0.22891(9) 0.0355(4) Uani d . 1 . . C
    C3 0.4148(2) 1.15519(13) 0.20150(10) 0.0392(4) Uani d . 1 . . C
    H3 0.4578 1.2131 0.2180 0.047 Uiso calc R 1 . . H
    C4 0.2948(2) 1.15804(13) 0.15087(10) 0.0419(5) Uani d . 1 . . C
    C5 0.2332(2) 1.07062(13) 0.12736(10) 0.0393(4) Uani d . 1 . . C
    H5 0.1503 1.0713 0.0937 0.047 Uiso calc R 1 . . H
    C7 0.2149(2) 0.89211(13) 0.12458(9) 0.0381(4) Uani d . 1 . . C
    H7A 0.2494 0.8390 0.1571 0.046 Uiso calc R 1 . . H
    H7B 0.1167 0.9000 0.1261 0.046 Uiso calc R 1 . . H
    C6 0.29000(19) 0.98249(13) 0.15191(9) 0.0348(4) Uani d . 1 . . C
    N8 0.23179(15) 0.86740(10) 0.04911(7) 0.0317(3) Uani d . 1 . . N
    C9 0.37406(18) 0.83825(13) 0.04687(9) 0.0370(4) Uani d . 1 . . C
    H9A 0.3994 0.7846 0.0804 0.044 Uiso calc R 1 . . H
    H9B 0.4365 0.8917 0.0629 0.044 Uiso calc R 1 . . H
    C10 0.38983(19) 0.80838(13) -0.02988(9) 0.0368(4) Uani d . 1 . . C
    H10A 0.3689 0.8630 -0.0631 0.044 Uiso calc R 1 . . H
    H10B 0.4853 0.7889 -0.0301 0.044 Uiso calc R 1 . . H
    N11 0.29675(15) 0.72850(10) -0.05533(7) 0.0319(3) Uani d . 1 . . N
    C12 0.15462(18) 0.75816(13) -0.05392(9) 0.0364(4) Uani d . 1 . . C
    H12A 0.0919 0.7049 -0.0702 0.044 Uiso calc R 1 . . H
    H12B 0.1302 0.8119 -0.0876 0.044 Uiso calc R 1 . . H
    C13 0.13814(19) 0.78819(13) 0.02254(10) 0.0370(4) Uani d . 1 . . C
    H13A 0.0428 0.8083 0.0223 0.044 Uiso calc R 1 . . H
    H13B 0.1576 0.7334 0.0556 0.044 Uiso calc R 1 . . H
    C14 0.3143(2) 0.69910(13) -0.12949(9) 0.0377(4) Uani d . 1 . . C
    H14A 0.4126 0.6905 -0.1304 0.045 Uiso calc R 1 . . H
    H14B 0.2803 0.7504 -0.1639 0.045 Uiso calc R 1 . . H
    C15 0.2392(2) 0.60762(13) -0.15399(9) 0.0356(4) Uani d . 1 . . C
    C16 0.2960(2) 0.52013(13) -0.12836(10) 0.0401(4) Uani d . 1 . . C
    H16 0.3803 0.5201 -0.0959 0.048 Uiso calc R 1 . . H
    C17 0.2332(2) 0.43273(14) -0.14880(11) 0.0446(5) Uani d . 1 . . C
    C18 0.1113(2) 0.43423(14) -0.19768(11) 0.0451(5) Uani d . 1 . . C
    H18 0.0676 0.3759 -0.2125 0.054 Uiso calc R 1 . . H
    C19 0.0504(2) 0.51948(14) -0.22591(9) 0.0384(4) Uani d . 1 . . C
    C20 0.1157(2) 0.60701(13) -0.20366(9) 0.0350(4) Uani d . 1 . . C
    O21 0.46652(15) 0.89689(9) 0.22920(7) 0.0429(3) Uani d . 1 . . O
    H21 0.5358 0.9069 0.2604 0.064 Uiso calc R 1 . . H
    C22 0.2301(3) 1.25202(15) 0.12341(14) 0.0619(6) Uani d . 1 . . C
    H22A 0.1471 1.2398 0.0883 0.093 Uiso calc R 1 . . H
    H22B 0.2945 1.2883 0.1003 0.093 Uiso calc R 1 . . H
    H22C 0.2070 1.2884 0.1640 0.093 Uiso calc R 1 . . H
    C23 0.5973(2) 1.07195(14) 0.28494(10) 0.0408(4) Uani d . 1 . . C
    H23 0.6365 1.1319 0.2990 0.049 Uiso calc R 1 . . H
    N24 0.65432(18) 0.99723(12) 0.31571(8) 0.0432(4) Uani d . 1 . . N
    C25 0.7698(2) 1.01125(16) 0.37546(11) 0.0499(5) Uani d . 1 . . C
    H25A 0.8139 1.0730 0.3695 0.060 Uiso calc R 1 . . H
    H25B 0.8383 0.9606 0.3742 0.060 Uiso calc R 1 . . H
    C26 0.7208(3) 1.00910(17) 0.44802(11) 0.0560(6) Uani d . 1 . . C
    H26A 0.6801 0.9464 0.4548 0.067 Uiso calc R 1 . . H
    H26B 0.7994 1.0184 0.4875 0.067 Uiso calc R 1 . . H
    O27 0.62244(17) 1.08137(12) 0.45128(8) 0.0646(5) Uani d . 1 . . O
    H27 0.6544 1.1216 0.4824 0.097 Uiso calc R 1 . . H
    O28 0.05876(15) 0.69161(9) -0.22974(7) 0.0466(4) Uani d . 1 . . O
    H28 -0.0120 0.6810 -0.2598 0.070 Uiso calc R 1 . . H
    C29 0.2981(3) 0.33945(16) -0.11912(14) 0.0670(7) Uani d . 1 . . C
    H29A 0.3821 0.3528 -0.0851 0.101 Uiso calc R 1 . . H
    H29B 0.3193 0.3007 -0.1590 0.101 Uiso calc R 1 . . H
    H29C 0.2343 0.3050 -0.0942 0.101 Uiso calc R 1 . . H
    C30 -0.0769(2) 0.51578(15) -0.27915(10) 0.0435(5) Uani d . 1 . . C
    H30 -0.1155 0.4555 -0.2926 0.052 Uiso calc R 1 . . H
    N31 -0.13801(18) 0.58952(13) -0.30820(8) 0.0447(4) Uani d . 1 . . N
    C32 -0.2608(2) 0.57383(16) -0.36346(11) 0.0490(5) Uani d . 1 . . C
    H32A -0.3315 0.6211 -0.3574 0.059 Uiso calc R 1 . . H
    H32B -0.2981 0.5098 -0.3574 0.059 Uiso calc R 1 . . H
    C33 -0.2253(2) 0.58284(16) -0.43874(11) 0.0478(5) Uani d . 1 . . C
    H33A -0.3081 0.5714 -0.4752 0.057 Uiso calc R 1 . . H
    H33B -0.1936 0.6482 -0.4456 0.057 Uiso calc R 1 . . H
    O34 -0.12288(15) 0.51790(12) -0.44964(8) 0.0576(4) Uani d . 1 . . O
    H34 -0.1553 0.4786 -0.4813 0.086 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
    C1 O21 . 1.345(2) y
    C1 C6 . 1.381(3) ?
    C1 C2 . 1.397(2) ?
    C2 C3 . 1.379(2) ?
    C2 C23 . 1.443(3) ?
    C3 C4 . 1.365(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.384(3) ?
    C4 C22 . 1.493(3) y
    C5 C6 . 1.381(2) ?
    C5 H5 . 0.9300 ?
    C7 N8 . 1.469(2) y
    C7 C6 . 1.490(2) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    N8 C9 . 1.453(2) y
    N8 C13 . 1.455(2) y
    C9 C10 . 1.506(2) y
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N11 . 1.454(2) y
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    N11 C12 . 1.451(2) y
    N11 C14 . 1.464(2) y
    C12 C13 . 1.504(2) y
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 C15 . 1.491(2) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.378(2) ?
    C15 C20 . 1.382(3) ?
    C16 C17 . 1.376(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.363(3) ?
    C17 C29 . 1.496(3) y
    C18 C19 . 1.379(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.394(2) ?
    C19 C30 . 1.444(3) ?
    C20 O28 . 1.346(2) y
    O21 H21 . 0.8200 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    C23 N24 . 1.260(2) y
    C23 H23 . 0.9300 ?
    N24 C25 . 1.446(2) ?
    C25 C26 . 1.496(3) ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C26 O27 . 1.393(3) ?
    C26 H26A . 0.9700 ?
    C26 H26B . 0.9700 ?
    O27 H27 . 0.8200 ?
    O28 H28 . 0.8200 ?
    C29 H29A . 0.9600 ?
    C29 H29B . 0.9600 ?
    C29 H29C . 0.9600 ?
    C30 N31 . 1.252(3) y
    C30 H30 . 0.9300 ?
    N31 C32 . 1.448(2) ?
    C32 C33 . 1.492(3) ?
    C32 H32A . 0.9700 ?
    C32 H32B . 0.9700 ?
    C33 O34 . 1.383(2) ?
    C33 H33A . 0.9700 ?
    C33 H33B . 0.9700 ?
    O34 H34 . 0.8200 ?
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
    O21 C1 C6 . . 119.4(2) y
    O21 C1 C2 . . 120.5(2) y
    C6 C1 C2 . . 120.05(16) ?
    C3 C2 C1 . . 119.16(17) ?
    C3 C2 C23 . . 118.98(16) ?
    C1 C2 C23 . . 121.83(16) ?
    C4 C3 C2 . . 122.10(17) ?
    C4 C3 H3 . . 118.9 ?
    C2 C3 H3 . . 118.9 ?
    C3 C4 C5 . . 117.61(17) ?
    C3 C4 C22 . . 121.3(2) y
    C5 C4 C22 . . 121.1(2) y
    C6 C5 C4 . . 122.55(18) ?
    C6 C5 H5 . . 118.7 ?
    C4 C5 H5 . . 118.7 ?
    N8 C7 C6 . . 112.68(14) ?
    N8 C7 H7A . . 109.1 ?
    C6 C7 H7A . . 109.1 ?
    N8 C7 H7B . . 109.1 ?
    C6 C7 H7B . . 109.1 ?
    H7A C7 H7B . . 107.8 ?
    C5 C6 C1 . . 118.50(16) ?
    C5 C6 C7 . . 118.79(17) ?
    C1 C6 C7 . . 122.65(16) ?
    C9 N8 C13 . . 109.30(10)
                           y
    C9 N8 C7 . . 110.80(10)
                          y
    C13 N8 C7 . . 109.10(10)
                           y
    N8 C9 C10 . . 110.85(14) ?
    N8 C9 H9A . . 109.5 ?
    C10 C9 H9A . . 109.5 ?
    N8 C9 H9B . . 109.5 ?
    C10 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 108.1 ?
    N11 C10 C9 . . 110.54(14) ?
    N11 C10 H10A . . 109.5 ?
    C9 C10 H10A . . 109.5 ?
    N11 C10 H10B . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 108.1 ?
    C12 N11 C10 . . 109.00(10)
                             y
    C12 N11 C14 . . 111.20(10)
                             y
    C10 N11 C14 . . 110.10(10)
                             y
    N11 C12 C13 . . 110.62(14) ?
    N11 C12 H12A . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    N11 C12 H12B . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    N8 C13 C12 . . 111.09(15) ?
    N8 C13 H13A . . 109.4 ?
    C12 C13 H13A . . 109.4 ?
    N8 C13 H13B . . 109.4 ?
    C12 C13 H13B . . 109.4 ?
    H13A C13 H13B . . 108.0 ?
    N11 C14 C15 . . 112.78(14) ?
    N11 C14 H14A . . 109.0 ?
    C15 C14 H14A . . 109.0 ?
    N11 C14 H14B . . 109.0 ?
    C15 C14 H14B . . 109.0 ?
    H14A C14 H14B . . 107.8 ?
    C16 C15 C20 . . 118.34(17) ?
    C16 C15 C14 . . 119.47(17) ?
    C20 C15 C14 . . 122.17(16) ?
    C17 C16 C15 . . 122.78(19) ?
    C17 C16 H16 . . 118.6 ?
    C15 C16 H16 . . 118.6 ?
    C18 C17 C16 . . 117.7(2) ?
    C18 C17 C29 . . 121.4(2) y
    C16 C17 C29 . . 121.0(2) y
    C17 C18 C19 . . 122.15(18) ?
    C17 C18 H18 . . 118.9 ?
    C19 C18 H18 . . 118.9 ?
    C18 C19 C20 . . 118.94(17) ?
    C18 C19 C30 . . 119.32(17) ?
    C20 C19 C30 . . 121.72(18) ?
    O28 C20 C15 . . 119.3(2) y
    O28 C20 C19 . . 120.5(2) y
    C15 C20 C19 . . 120.12(17) ?
    C1 O21 H21 . . 109.5 ?
    C4 C22 H22A . . 109.5 ?
    C4 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C4 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    N24 C23 C2 . . 123.28(18) ?
    N24 C23 H23 . . 118.4 ?
    C2 C23 H23 . . 118.4 ?
    C23 N24 C25 . . 117.3(2) y
    N24 C25 C26 . . 110.50(18) ?
    N24 C25 H25A . . 109.6 ?
    C26 C25 H25A . . 109.6 ?
    N24 C25 H25B . . 109.6 ?
    C26 C25 H25B . . 109.6 ?
    H25A C25 H25B . . 108.1 ?
    O27 C26 C25 . . 110.70(17) ?
    O27 C26 H26A . . 109.5 ?
    C25 C26 H26A . . 109.5 ?
    O27 C26 H26B . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 108.1 ?
    C26 O27 H27 . . 109.5 ?
    C20 O28 H28 . . 109.5 ?
    C17 C29 H29A . . 109.5 ?
    C17 C29 H29B . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    C17 C29 H29C . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    N31 C30 C19 . . 123.47(18) ?
    N31 C30 H30 . . 118.3 ?
    C19 C30 H30 . . 118.3 ?
    C30 N31 C32 . . 117.0(2) y
    N31 C32 C33 . . 110.12(16) ?
    N31 C32 H32A . . 109.6 ?
    C33 C32 H32A . . 109.6 ?
    N31 C32 H32B . . 109.6 ?
    C33 C32 H32B . . 109.6 ?
    H32A C32 H32B . . 108.2 ?
    O34 C33 C32 . . 111.77(17) ?
    O34 C33 H33A . . 109.3 ?
    C32 C33 H33A . . 109.3 ?
    O34 C33 H33B . . 109.3 ?
    C32 C33 H33B . . 109.3 ?
    H33A C33 H33B . . 107.9 ?
    C33 O34 H34 . . 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
    O21 C1 C2 C3 . . . . -179.90(16) ?
    C6 C1 C2 C3 . . . . -0.7(3) ?
    O21 C1 C2 C23 . . . . -1.9(3) ?
    C6 C1 C2 C23 . . . . 177.30(16) ?
    C1 C2 C3 C4 . . . . 1.0(3) ?
    C23 C2 C3 C4 . . . . -177.05(17) ?
    C2 C3 C4 C5 . . . . 0.0(3) ?
    C2 C3 C4 C22 . . . . 178.29(18) ?
    C3 C4 C5 C6 . . . . -1.4(3) ?
    C22 C4 C5 C6 . . . . -179.71(18) ?
    C4 C5 C6 C1 . . . . 1.7(3) ?
    C4 C5 C6 C7 . . . . 178.90(17) ?
    O21 C1 C6 C5 . . . . 178.58(15) ?
    C2 C1 C6 C5 . . . . -0.6(3) ?
    O21 C1 C6 C7 . . . . 1.5(3) ?
    C2 C1 C6 C7 . . . . -177.67(15) ?
    N8 C7 C6 C5 . . . . 76.6(2) y
    N8 C7 C6 C1 . . . . -106.31(19) ?
    C6 C7 N8 C9 . . . . 68.82(19) ?
    C6 C7 N8 C13 . . . . -170.9(2) y
    C13 N8 C9 C10 . . . . 57.13(19) ?
    C7 N8 C9 C10 . . . . 177.32(14) ?
    N8 C9 C10 N11 . . . . -58.9(2) ?
    C9 C10 N11 C12 . . . . 58.57(18) ?
    C9 C10 N11 C14 . . . . -179.18(15) ?
    C10 N11 C12 C13 . . . . -58.37(19) ?
    C14 N11 C12 C13 . . . . -179.97(14) ?
    C9 N8 C13 C12 . . . . -57.03(19) ?
    C7 N8 C13 C12 . . . . -178.30(15) ?
    N11 C12 C13 N8 . . . . 58.6(2) ?
    C12 N11 C14 C15 . . . . -68.4(2) ?
    C10 N11 C14 C15 . . . . 170.7(2) y
    N11 C14 C15 C16 . . . . -78.3(2) y
    N11 C14 C15 C20 . . . . 103.66(19) ?
    C20 C15 C16 C17 . . . . -1.6(3) ?
    C14 C15 C16 C17 . . . . -179.65(16) ?
    C15 C16 C17 C18 . . . . 1.4(3) ?
    C15 C16 C17 C29 . . . . -179.50(19) ?
    C16 C17 C18 C19 . . . . -0.5(3) ?
    C29 C17 C18 C19 . . . . -179.65(19) ?
    C17 C18 C19 C20 . . . . -0.1(3) ?
    C17 C18 C19 C30 . . . . 178.22(18) ?
    C16 C15 C20 O28 . . . . -179.62(15) ?
    C14 C15 C20 O28 . . . . -1.6(3) ?
    C16 C15 C20 C19 . . . . 0.9(3) ?
    C14 C15 C20 C19 . . . . 178.92(16) ?
    C18 C19 C20 O28 . . . . -179.58(16) ?
    C30 C19 C20 O28 . . . . 2.2(3) ?
    C18 C19 C20 C15 . . . . -0.1(3) ?
    C30 C19 C20 C15 . . . . -178.36(16) ?
    C3 C2 C23 N24 . . . . 176.32(17) ?
    C1 C2 C23 N24 . . . . -1.7(3) ?
    C2 C23 N24 C25 . . . . -174.66(16) ?
    C23 N24 C25 C26 . . . . 95.0(2) ?
    N24 C25 C26 O27 . . . . -59.3(2) ?
    C18 C19 C30 N31 . . . . -179.08(18) ?
    C20 C19 C30 N31 . . . . -0.8(3) ?
    C19 C30 N31 C32 . . . . 176.92(16) ?
    C30 N31 C32 C33 . . . . -99.6(2) ?
    N31 C32 C33 O34 . . . . 58.2(2) ?
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
    O21 H21 N24 . 0.82 1.88 2.609(2) 148
    O28 H28 N31 . 0.82 1.88 2.608(2) 148
    C7 H7A O21 . 0.97 2.43 2.848(2) 105
    C14 H14B O28 . 0.97 2.43 2.837(2) 105
    O27 H27 N11 2_655 0.82 2.00 2.811(2) 171
    O34 H34 N8 2_544 0.82 2.04 2.852(2) 172
    C29 H29A O27 4_575 0.96 2.50 3.388(3) 154
data_global
_journal_date_recd_electronic     2002-12-02
_journal_date_accepted     2002-12-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2003
_journal_volume     59
_journal_issue      1
_journal_page_first     o83
_journal_page_last     o85
_journal_paper_category     EO
_publ_contact_author_name     'Professor D. Velmurugan'
_publ_contact_author_address
;
Department of Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
_publ_contact_author_email     d_velu@yahoo.com
_publ_contact_author_fax     '044 091 235 2494'
_publ_contact_author_phone     '044 091 235 1367'
_publ_section_title
;
1,4-Bis{2-hydroxy-3-[N-(2-hydroxyethyl)imino]-5-methylbenzyl}piperazine
;
loop_
    _publ_author_name
    _publ_author_address
    'M. Yogavel'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'S. Selvanayagam'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'D. Velmurugan'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'S. Shanmuga Sundara Raj'
;     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
;
    'M. Marappan'
;     Department of Inorganic Chemistry
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'M. Kandaswamy'
;     Department of Inorganic Chemistry
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
