##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Dichlorido(2-{[2-(piperazin-4-ium-1-yl)ethyl]iminomethyl}phenolate)cadmium(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H19 Cd Cl2 N3 O'
_chemical_formula_sum     'C13 H19 Cd Cl2 N3 O'
_chemical_formula_iupac     '[Cd Cl2 (C13 H19 N3 O)]'
_chemical_formula_weight     416.61
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     14.7512(16)
_cell_length_b     13.1406(15)
_cell_length_c     16.6188(19)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3221.4(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9877
_cell_measurement_theta_min     2.41
_cell_measurement_theta_max     31.34
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.39
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.718
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1664
_exptl_absorpt_coefficient_mu     1.686
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.5175
_exptl_absorpt_correction_T_max     0.7512
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     38841
_diffrn_reflns_av_R_equivalents     0.0407
_diffrn_reflns_av_sigmaI/netI     0.0184
_diffrn_reflns_theta_min     2.41
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     25.25
_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     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_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 >
σ(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     3700
_reflns_number_gt     3409
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0196
_refine_ls_R_factor_gt     0.0169
_refine_ls_wR_factor_gt     0.0428
_refine_ls_wR_factor_ref     0.0445
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     3700
_refine_ls_number_parameters     187
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0187P)²+2.1332P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.442
_refine_diff_density_min     -0.277
_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'
    'Cd' 'Cd' -0.8075 1.2024
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material
                        'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _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
    Cd Cd1 0.915609(7) 0.521115(8) 0.335271(6) 0.01335(4) Uani d . 1 . .
    Cl Cl1 0.80478(3) 0.46142(3) 0.23256(2) 0.02000(8) Uani d . 1 . .
    Cl Cl2 1.05575(2) 0.57074(3) 0.26583(2) 0.01803(8) Uani d . 1 . .
    O O1 0.98159(7) 0.37354(9) 0.37625(7) 0.0192(2) Uani d . 1 . .
    N N1 0.87369(9) 0.52146(10) 0.46665(8) 0.0162(3) Uani d . 1 . .
    N N2 0.83315(8) 0.68754(10) 0.35360(8) 0.0139(2) Uani d . 1 . .
    N N3 0.88695(9) 0.83051(10) 0.22922(8) 0.0149(2) Uani d D 1 . .
    H H3A 0.8533(12) 0.8859(13) 0.2359(11) 0.022 Uiso d D 1 . .
    H H3B 0.9244(12) 0.8437(16) 0.1887(11) 0.022 Uiso d D 1 . .
    C C1 0.95272(10) 0.31114(12) 0.43163(9) 0.0169(3) Uani d . 1 . .
    C C2 0.96780(11) 0.20498(12) 0.42363(10) 0.0195(3) Uani d . 1 . .
    H H2 0.9967 0.1802 0.3765 0.023 Uiso calc R 1 . .
    C C3 0.94174(11) 0.13662(13) 0.48221(10) 0.0220(3) Uani d . 1 . .
    H H3 0.9523 0.0660 0.4742 0.026 Uiso calc R 1 . .
    C C4 0.90004(11) 0.16929(13) 0.55317(10) 0.0213(3) Uani d . 1 . .
    H H4 0.8837 0.1221 0.5940 0.026 Uiso calc R 1 . .
    C C5 0.88317(10) 0.27220(13) 0.56245(9) 0.0194(3) Uani d . 1 . .
    H H5 0.8550 0.2953 0.6105 0.023 Uiso calc R 1 . .
    C C6 0.90643(10) 0.34411(12) 0.50271(9) 0.0167(3) Uani d . 1 . .
    C C7 0.87494(10) 0.44702(13) 0.51703(9) 0.0172(3) Uani d . 1 . .
    H H7 0.8527 0.4611 0.5695 0.021 Uiso calc R 1 . .
    C C8 0.83000(10) 0.61616(12) 0.49269(9) 0.0178(3) Uani d . 1 . .
    H H8A 0.8766 0.6657 0.5100 0.021 Uiso calc R 1 . .
    H H8B 0.7895 0.6024 0.5389 0.021 Uiso calc R 1 . .
    C C9 0.77532(10) 0.66006(12) 0.42318(9) 0.0172(3) Uani d . 1 . .
    H H9A 0.7296 0.6095 0.4058 0.021 Uiso calc R 1 . .
    H H9B 0.7426 0.7214 0.4419 0.021 Uiso calc R 1 . .
    C C10 0.88602(10) 0.77994(12) 0.37278(9) 0.0164(3) Uani d . 1 . .
    H H10A 0.9254 0.7662 0.4198 0.020 Uiso calc R 1 . .
    H H10B 0.8440 0.8357 0.3874 0.020 Uiso calc R 1 . .
    C C11 0.94408(10) 0.81319(12) 0.30220(9) 0.0158(3) Uani d . 1 . .
    H H11A 0.9765 0.8768 0.3162 0.019 Uiso calc R 1 . .
    H H11B 0.9899 0.7602 0.2906 0.019 Uiso calc R 1 . .
    C C12 0.82875(10) 0.74064(12) 0.21146(9) 0.0166(3) Uani d . 1 . .
    H H12A 0.8674 0.6825 0.1954 0.020 Uiso calc R 1 . .
    H H12B 0.7878 0.7567 0.1660 0.020 Uiso calc R 1 . .
    C C13 0.77292(10) 0.71146(12) 0.28467(9) 0.0158(3) Uani d . 1 . .
    H H13A 0.7321 0.7684 0.2992 0.019 Uiso calc R 1 . .
    H H13B 0.7350 0.6514 0.2719 0.019 Uiso calc R 1 . .
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
    Cd1 0.01279(7) 0.01314(7) 0.01412(7) 0.00111(4) 0.00214(4) 0.00129(4)
    Cl1 0.01838(18) 0.01817(18) 0.02346(19) -0.00298(14) -0.00124(14)
                                                                    -0.00369(14)
    Cl2 0.01453(16) 0.01461(17) 0.02495(19) -0.00003(13) 0.00517(14) 0.00176(14)
    O1 0.0201(5) 0.0189(5) 0.0186(5) 0.0057(4) 0.0045(4) 0.0040(4)
    N1 0.0132(6) 0.0189(7) 0.0164(6) 0.0015(5) 0.0010(5) -0.0002(5)
    N2 0.0117(6) 0.0146(6) 0.0153(6) -0.0007(5) 0.0005(5) 0.0009(5)
    N3 0.0153(6) 0.0127(6) 0.0166(6) -0.0006(5) 0.0005(5) 0.0007(5)
    C1 0.0134(7) 0.0180(7) 0.0192(7) 0.0003(6) -0.0030(6) 0.0024(6)
    C2 0.0174(7) 0.0190(8) 0.0222(8) 0.0013(6) -0.0020(6) 0.0017(6)
    C3 0.0178(7) 0.0175(8) 0.0306(9) -0.0017(6) -0.0083(6) 0.0054(7)
    C4 0.0167(7) 0.0244(8) 0.0229(8) -0.0052(6) -0.0065(6) 0.0098(7)
    C5 0.0147(7) 0.0273(8) 0.0161(7) -0.0045(6) -0.0034(6) 0.0050(6)
    C6 0.0143(7) 0.0198(8) 0.0158(7) -0.0019(6) -0.0024(6) 0.0034(6)
    C7 0.0128(7) 0.0241(8) 0.0147(7) -0.0013(6) 0.0000(5) 0.0003(6)
    C8 0.0183(7) 0.0195(7) 0.0156(7) 0.0017(6) 0.0035(6) -0.0006(6)
    C9 0.0139(7) 0.0179(7) 0.0198(7) 0.0011(6) 0.0040(6) 0.0009(6)
    C10 0.0153(7) 0.0168(7) 0.0172(7) -0.0021(6) 0.0004(6) -0.0023(6)
    C11 0.0139(7) 0.0155(7) 0.0179(7) -0.0019(6) -0.0009(6) 0.0003(6)
    C12 0.0164(7) 0.0157(7) 0.0177(7) -0.0023(6) -0.0025(6) -0.0004(6)
    C13 0.0124(7) 0.0157(7) 0.0192(7) -0.0007(5) -0.0020(6) 0.0009(6)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Cd1 N1 . 2.2693(13) ?
    Cd1 O1 . 2.2740(11) ?
    Cd1 Cl2 . 2.4557(4) ?
    Cd1 Cl1 . 2.4904(4) ?
    Cd1 N2 . 2.5209(13) ?
    O1 C1 . 1.3042(19) ?
    N1 C7 . 1.288(2) ?
    N1 C8 . 1.4667(19) ?
    N2 C10 . 1.4779(19) ?
    N2 C9 . 1.4816(19) ?
    N2 C13 . 1.4833(19) ?
    N3 C12 . 1.4897(19) ?
    N3 C11 . 1.4943(19) ?
    N3 H3A . 0.889(15) ?
    N3 H3B . 0.887(15) ?
    C1 C2 . 1.419(2) ?
    C1 C6 . 1.432(2) ?
    C2 C3 . 1.379(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.398(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.384(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.413(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.450(2) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.522(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.517(2) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.518(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
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
    N1 Cd1 O1 . . 80.22(4) ?
    N1 Cd1 Cl2 . . 132.92(3) ?
    O1 Cd1 Cl2 . . 90.39(3) ?
    N1 Cd1 Cl1 . . 118.77(3) ?
    O1 Cd1 Cl1 . . 102.57(3) ?
    Cl2 Cd1 Cl1 . . 108.309(15) ?
    N1 Cd1 N2 . . 75.55(4) ?
    O1 Cd1 N2 . . 155.52(4) ?
    Cl2 Cd1 N2 . . 103.45(3) ?
    Cl1 Cd1 N2 . . 92.25(3) ?
    C1 O1 Cd1 . . 127.43(9) ?
    C7 N1 C8 . . 117.32(13) ?
    C7 N1 Cd1 . . 128.33(11) ?
    C8 N1 Cd1 . . 113.90(9) ?
    C10 N2 C9 . . 109.61(12) ?
    C10 N2 C13 . . 107.97(12) ?
    C9 N2 C13 . . 108.04(11) ?
    C10 N2 Cd1 . . 118.96(9) ?
    C9 N2 Cd1 . . 99.25(9) ?
    C13 N2 Cd1 . . 112.30(9) ?
    C12 N3 C11 . . 111.41(12) ?
    C12 N3 H3A . . 110.6(13) ?
    C11 N3 H3A . . 109.8(12) ?
    C12 N3 H3B . . 111.3(14) ?
    C11 N3 H3B . . 107.1(13) ?
    H3A N3 H3B . . 106.4(19) ?
    O1 C1 C2 . . 120.06(14) ?
    O1 C1 C6 . . 123.22(14) ?
    C2 C1 C6 . . 116.72(14) ?
    C3 C2 C1 . . 122.04(16) ?
    C3 C2 H2 . . 119.0 ?
    C1 C2 H2 . . 119.0 ?
    C2 C3 C4 . . 121.21(16) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C5 C4 C3 . . 118.25(15) ?
    C5 C4 H4 . . 120.9 ?
    C3 C4 H4 . . 120.9 ?
    C4 C5 C6 . . 122.12(15) ?
    C4 C5 H5 . . 118.9 ?
    C6 C5 H5 . . 118.9 ?
    C5 C6 C1 . . 119.56(15) ?
    C5 C6 C7 . . 115.51(14) ?
    C1 C6 C7 . . 124.80(14) ?
    N1 C7 C6 . . 127.33(14) ?
    N1 C7 H7 . . 116.3 ?
    C6 C7 H7 . . 116.3 ?
    N1 C8 C9 . . 109.30(12) ?
    N1 C8 H8A . . 109.8 ?
    C9 C8 H8A . . 109.8 ?
    N1 C8 H8B . . 109.8 ?
    C9 C8 H8B . . 109.8 ?
    H8A C8 H8B . . 108.3 ?
    N2 C9 C8 . . 112.31(12) ?
    N2 C9 H9A . . 109.1 ?
    C8 C9 H9A . . 109.1 ?
    N2 C9 H9B . . 109.1 ?
    C8 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.9 ?
    N2 C10 C11 . . 111.59(12) ?
    N2 C10 H10A . . 109.3 ?
    C11 C10 H10A . . 109.3 ?
    N2 C10 H10B . . 109.3 ?
    C11 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 108.0 ?
    N3 C11 C10 . . 110.68(12) ?
    N3 C11 H11A . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    N3 C11 H11B . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    N3 C12 C13 . . 110.73(12) ?
    N3 C12 H12A . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    N3 C12 H12B . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    N2 C13 C12 . . 110.34(12) ?
    N2 C13 H13A . . 109.6 ?
    C12 C13 H13A . . 109.6 ?
    N2 C13 H13B . . 109.6 ?
    C12 C13 H13B . . 109.6 ?
    H13A C13 H13B . . 108.1 ?
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
    N3 H3A Cl1 8_765 0.889(15) 2.534(16) 3.3108(14) 146.4(17)
    N3 H3A Cl2 3_755 0.889(15) 2.775(19) 3.2689(14) 116.4(15)
    N3 H3B O1 3_755 0.887(15) 1.802(15) 2.6743(17) 167.4(19)
    C11 H11B Cl2 . 0.99 2.70 3.6372(16) 157.4
    C13 H13B Cl1 . 0.99 2.78 3.4302(16) 123.9
    C4 H4 Cl1 7_566 0.95 2.80 3.7165(17) 161.2
    C13 H13A Cl1 8_765 0.99 2.82 3.5851(16) 134.4
data_global
_journal_date_recd_electronic     2010-08-08
_journal_date_accepted     2010-08-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     m1131
_journal_page_last     m1131
_journal_paper_category     QM
_journal_coeditor_code     PV2318
_publ_contact_author_name     'Hamid Khaledi'
_publ_contact_author_address
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email     'khaledi@siswa.um.edu.my'
_publ_contact_author_fax     '+603-79674193 '
_publ_contact_author_phone     '+603-79674246'
_publ_section_title
;
Dichlorido(2-{[2-(piperazin-4-ium-1-yl)ethyl]iminomethyl}phenolate)cadmium(II)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Saleh Salga, Muhammad' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Khaledi, Hamid' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Mohd Ali, Hapipah' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
