##############################################################################
###                                                                        ###
###        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
;
[1,8-Bis(2-benzyl)-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II)
diperchlorate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H34 N6 Ni 2+ , 2Cl O4 -'
_chemical_formula_sum     'C22 H34 Cl2 N6 Ni O8'
_chemical_formula_iupac     '[Ni (C22 H34 N6)] (Cl O4)2'
_chemical_formula_weight     640.16
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.2090(10)
_cell_length_b     11.6170(10)
_cell_length_c     11.9160(10)
_cell_angle_alpha     87.633(2)
_cell_angle_beta     75.940(2)
_cell_angle_gamma     88.501(2)
_cell_volume     1369.5(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     855
_cell_measurement_theta_min     4.0
_cell_measurement_theta_max     29.8
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.552
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     668
_exptl_absorpt_coefficient_mu     0.96
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.809
_exptl_absorpt_correction_T_max     0.893
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     8366
_diffrn_reflns_av_R_equivalents     0.011
_diffrn_reflns_av_sigmaI/netI     0.024
_diffrn_reflns_theta_min     4.1
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.974
_diffrn_measured_fraction_theta_full     0.974
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     6134
_reflns_number_gt     5089
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0440
_refine_ls_R_factor_gt     0.0357
_refine_ls_wR_factor_gt     0.1000
_refine_ls_wR_factor_ref     0.1046
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     6134
_refine_ls_number_parameters     357
_refine_ls_number_restraints     96
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0591P)²+0.4245P] 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     0.655
_refine_diff_density_min     -0.508
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Ni' 'Ni' 0.3393 1.1124
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows
(Farrugia, 1997) and PLUTON (Spek, 1990)
;
_computing_publication_material     SHELXL97
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
    Ni1 0.5000 0.5000 0.5000 0.02862(10) Uani d S 1 . . Ni
    Ni2 0.5000 0.0000 0.0000 0.02726(10) Uani d S 1 . . Ni
    C1 0.5635(3) 0.5956(2) 0.7049(2) 0.0451(5) Uani d . 1 . . C
    H1A 0.5782 0.6711 0.6666 0.054 Uiso calc R 1 . . H
    H1B 0.5305 0.6068 0.7872 0.054 Uiso calc R 1 . . H
    C2 0.3270(3) 0.6017(2) 0.6905(2) 0.0454(5) Uani d . 1 . . C
    H2A 0.3417 0.6824 0.6679 0.054 Uiso calc R 1 . . H
    H2B 0.2864 0.5957 0.7730 0.054 Uiso calc R 1 . . H
    C3 0.2370(2) 0.5499(2) 0.6242(2) 0.0456(5) Uani d . 1 . . C
    H3A 0.2105 0.4733 0.6554 0.055 Uiso calc R 1 . . H
    H3B 0.1561 0.5971 0.6294 0.055 Uiso calc R 1 . . H
    C4 0.2433(2) 0.4740(2) 0.4340(2) 0.0425(5) Uani d . 1 . . C
    H4A 0.2322 0.3969 0.4691 0.051 Uiso calc R 1 . . H
    H4B 0.1539 0.5072 0.4397 0.051 Uiso calc R 1 . . H
    C5 0.3153(2) 0.5733(2) 0.2428(2) 0.0432(5) Uani d . 1 . . C
    H5A 0.3691 0.5593 0.1653 0.052 Uiso calc R 1 . . H
    H5B 0.3600 0.6317 0.2751 0.052 Uiso calc R 1 . . H
    C6 0.1781(2) 0.6184(2) 0.23504(19) 0.0406(5) Uani d . 1 . . C
    C7 0.1166(3) 0.5790(2) 0.1530(2) 0.0539(6) Uani d . 1 . . C
    H7 0.1585 0.5212 0.1046 0.065 Uiso calc R 1 . . H
    C8 -0.0066(3) 0.6247(3) 0.1421(3) 0.0657(8) Uani d . 1 . . C
    H8 -0.0457 0.5992 0.0850 0.079 Uiso calc R 1 . . H
    C9 -0.0713(3) 0.7080(3) 0.2158(3) 0.0634(8) Uani d . 1 . . C
    H9 -0.1548 0.7377 0.2094 0.076 Uiso calc R 1 . . H
    C10 -0.0127(3) 0.7469(3) 0.2980(3) 0.0606(7) Uani d . 1 . . C
    H10 -0.0564 0.8030 0.3480 0.073 Uiso calc R 1 . . H
    C11 0.1121(3) 0.7029(2) 0.3073(2) 0.0511(6) Uani d . 1 . . C
    H11 0.1519 0.7306 0.3629 0.061 Uiso calc R 1 . . H
    C12 0.2410(2) -0.1159(2) 0.0301(2) 0.0429(5) Uani d . 1 . . C
    H12A 0.2788 -0.1878 0.0536 0.052 Uiso calc R 1 . . H
    H12B 0.1459 -0.1135 0.0691 0.052 Uiso calc R 1 . . H
    C13 0.2878(2) -0.0234(2) 0.19751(17) 0.0395(5) Uani d . 1 . . C
    H13A 0.3083 -0.1004 0.2239 0.047 Uiso calc R 1 . . H
    H13B 0.1945 -0.0044 0.2343 0.047 Uiso calc R 1 . . H
    C14 0.3805(2) 0.0622(2) 0.22703(18) 0.0398(5) Uani d . 1 . . C
    H14A 0.3513 0.1402 0.2118 0.048 Uiso calc R 1 . . H
    H14B 0.3814 0.0536 0.3082 0.048 Uiso calc R 1 . . H
    C15 0.6124(2) 0.13189(19) 0.1601(2) 0.0385(5) Uani d . 1 . . C
    H15A 0.5768 0.2044 0.1358 0.046 Uiso calc R 1 . . H
    H15B 0.6155 0.1377 0.2404 0.046 Uiso calc R 1 . . H
    C16 0.8320(2) 0.0343(2) 0.1414(2) 0.0421(5) Uani d . 1 . . C
    H16A 0.9017 0.0025 0.0795 0.051 Uiso calc R 1 . . H
    H16B 0.7778 -0.0289 0.1820 0.051 Uiso calc R 1 . . H
    C17 0.8971(2) 0.0935(2) 0.2244(2) 0.0390(5) Uani d . 1 . . C
    C18 0.8651(3) 0.0638(2) 0.3413(2) 0.0514(6) Uani d . 1 . . C
    H18 0.8008 0.0080 0.3704 0.062 Uiso calc R 1 . . H
    C19 0.9289(3) 0.1170(3) 0.4158(3) 0.0646(8) Uani d . 1 . . C
    H19 0.9072 0.0964 0.4943 0.078 Uiso calc R 1 . . H
    C20 1.0231(3) 0.1992(3) 0.3740(3) 0.0645(8) Uani d . 1 . . C
    H20 1.0661 0.2338 0.4240 0.077 Uiso calc R 1 . . H
    C21 1.0545(3) 0.2312(3) 0.2588(3) 0.0596(7) Uani d . 1 . . C
    H21 1.1180 0.2880 0.2308 0.071 Uiso calc R 1 . . H
    C22 0.9916(2) 0.1787(2) 0.1839(2) 0.0496(6) Uani d . 1 . . C
    H22 1.0129 0.2009 0.1058 0.059 Uiso calc R 1 . . H
    N1 0.45669(19) 0.53585(15) 0.66207(15) 0.0349(4) Uani d . 1 . . N
    H1 0.4418 0.4674 0.7027 0.042 Uiso calc R 1 . . H
    N2 0.31535(17) 0.54460(15) 0.50175(15) 0.0342(4) Uani d . 1 . . N
    H2 0.3177 0.6178 0.4710 0.041 Uiso calc R 1 . . H
    N3 0.3102(2) 0.46581(16) 0.31442(16) 0.0411(4) Uani d . 1 . . N
    N4 0.30957(17) -0.01765(15) 0.06928(14) 0.0323(4) Uani d . 1 . . N
    H4 0.2676 0.0481 0.0511 0.039 Uiso calc R 1 . . H
    N5 0.51754(17) 0.03758(15) 0.15204(14) 0.0321(4) Uani d . 1 . . N
    H5 0.5488 -0.0275 0.1828 0.039 Uiso calc R 1 . . H
    N6 0.74627(19) 0.11509(16) 0.09187(16) 0.0391(4) Uani d . 1 . . N
    Cl1 0.53145(6) 0.81334(4) 0.42677(5) 0.04294(14) Uani d U 1 . . Cl
    O11 0.5861(2) 0.90013(18) 0.34389(19) 0.0719(6) Uani d U 1 . . O
    O12 0.5997(3) 0.70582(17) 0.4011(2) 0.0792(7) Uani d U 1 . . O
    O13 0.3930(2) 0.7962(2) 0.4239(3) 0.0947(8) Uani d U 1 . . O
    O14 0.5366(5) 0.8438(2) 0.5369(2) 0.1286(13) Uani d U 1 . . O
    Cl2 0.36834(6) 0.29594(5) -0.04832(5) 0.04134(14) Uani d U 1 . . Cl
    O21 0.3469(2) 0.39121(17) -0.12005(19) 0.0674(6) Uani d U 1 . . O
    O22 0.4846(3) 0.2315(2) -0.1008(3) 0.1066(10) Uani d U 1 . . O
    O23 0.2580(2) 0.2180(2) -0.0296(3) 0.1031(10) Uani d U 1 . . O
    O24 0.3812(6) 0.3315(3) 0.0565(3) 0.1586(18) Uani d U 1 . . O
_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
    Ni1 N1 . 1.9340(17) y
    Ni1 N2 . 1.9372(17) y
    Ni1 O12 . 2.730(2) y
    Ni2 N4 . 1.9314(17) y
    Ni2 N5 . 1.9318(16) y
    Ni2 O22 . 2.916(2) y
    C1 N3 2_666 1.431(3) ?
    C1 N1 . 1.506(3) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 N1 . 1.484(3) ?
    C2 C3 . 1.501(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N2 . 1.487(3) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 N3 . 1.429(3) ?
    C4 N2 . 1.497(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 N3 . 1.478(3) ?
    C5 C6 . 1.506(3) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.381(3) ?
    C6 C11 . 1.382(4) ?
    C7 C8 . 1.386(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.378(5) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.363(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.388(4) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 N6 2_655 1.427(3) ?
    C12 N4 . 1.502(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 N4 . 1.489(3) ?
    C13 C14 . 1.500(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 N5 . 1.494(3) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 N6 . 1.424(3) ?
    C15 N5 . 1.502(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 N6 . 1.469(3) ?
    C16 C17 . 1.514(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C18 . 1.383(3) ?
    C17 C22 . 1.388(3) ?
    C18 C19 . 1.393(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.364(5) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.370(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.387(4) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    N1 H1 . 0.9100 ?
    N2 H2 . 0.9100 ?
    N3 C1 2_666 1.431(3) ?
    N4 H4 . 0.9100 ?
    N5 H5 . 0.9100 ?
    N6 C12 2_655 1.427(3) ?
    Cl1 O14 . 1.387(2) ?
    Cl1 O11 . 1.4082(18) ?
    Cl1 O12 . 1.422(2) ?
    Cl1 O13 . 1.441(2) ?
    Cl2 O24 . 1.369(3) ?
    Cl2 O22 . 1.411(2) ?
    Cl2 O21 . 1.4156(18) ?
    Cl2 O23 . 1.433(2) ?
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 Ni1 N2 . . 86.66(7) y
    N1 Ni1 N2 2_666 . 93.34(7) y
    N1 Ni1 O12 . . 100.60(8) y
    N1 Ni1 O12 2_666 . 79.40(8) y
    N2 Ni1 O12 . . 93.11(7) y
    N2 Ni1 O12 2_666 . 86.89(7) y
    N4 Ni2 N5 . . 86.70(7) y
    N4 Ni2 N5 2_655 . 93.30(7) y
    N4 Ni2 O22 . . 97.51(7) y
    N4 Ni2 O22 2_655 . 82.49(7) y
    N5 Ni2 O22 . . 99.83(9) y
    N5 Ni2 O22 2_655 . 80.17(9) y
    N3 C1 N1 2_666 . 113.94(17) ?
    N3 C1 H1A 2_666 . 108.8 ?
    N1 C1 H1A . . 108.8 ?
    N3 C1 H1B 2_666 . 108.8 ?
    N1 C1 H1B . . 108.8 ?
    H1A C1 H1B . . 107.7 ?
    N1 C2 C3 . . 106.59(18) ?
    N1 C2 H2A . . 110.4 ?
    C3 C2 H2A . . 110.4 ?
    N1 C2 H2B . . 110.4 ?
    C3 C2 H2B . . 110.4 ?
    H2A C2 H2B . . 108.6 ?
    N2 C3 C2 . . 107.05(19) ?
    N2 C3 H3A . . 110.3 ?
    C2 C3 H3A . . 110.3 ?
    N2 C3 H3B . . 110.3 ?
    C2 C3 H3B . . 110.3 ?
    H3A C3 H3B . . 108.6 ?
    N3 C4 N2 . . 114.45(18) ?
    N3 C4 H4A . . 108.6 ?
    N2 C4 H4A . . 108.6 ?
    N3 C4 H4B . . 108.6 ?
    N2 C4 H4B . . 108.6 ?
    H4A C4 H4B . . 107.6 ?
    N3 C5 C6 . . 113.32(19) ?
    N3 C5 H5A . . 108.9 ?
    C6 C5 H5A . . 108.9 ?
    N3 C5 H5B . . 108.9 ?
    C6 C5 H5B . . 108.9 ?
    H5A C5 H5B . . 107.7 ?
    C7 C6 C11 . . 118.2(2) ?
    C7 C6 C5 . . 120.8(2) ?
    C11 C6 C5 . . 121.0(2) ?
    C6 C7 C8 . . 120.8(3) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C9 C8 C7 . . 120.0(3) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C10 C9 C8 . . 119.9(3) ?
    C10 C9 H9 . . 120.0 ?
    C8 C9 H9 . . 120.0 ?
    C9 C10 C11 . . 120.0(3) ?
    C9 C10 H10 . . 120.0 ?
    C11 C10 H10 . . 120.0 ?
    C6 C11 C10 . . 121.0(3) ?
    C6 C11 H11 . . 119.5 ?
    C10 C11 H11 . . 119.5 ?
    N6 C12 N4 2_655 . 114.05(18) ?
    N6 C12 H12A 2_655 . 108.7 ?
    N4 C12 H12A . . 108.7 ?
    N6 C12 H12B 2_655 . 108.7 ?
    N4 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
    N4 C13 C14 . . 106.83(17) ?
    N4 C13 H13A . . 110.4 ?
    C14 C13 H13A . . 110.4 ?
    N4 C13 H13B . . 110.4 ?
    C14 C13 H13B . . 110.4 ?
    H13A C13 H13B . . 108.6 ?
    N5 C14 C13 . . 106.27(17) ?
    N5 C14 H14A . . 110.5 ?
    C13 C14 H14A . . 110.5 ?
    N5 C14 H14B . . 110.5 ?
    C13 C14 H14B . . 110.5 ?
    H14A C14 H14B . . 108.7 ?
    N6 C15 N5 . . 113.97(17) ?
    N6 C15 H15A . . 108.8 ?
    N5 C15 H15A . . 108.8 ?
    N6 C15 H15B . . 108.8 ?
    N5 C15 H15B . . 108.8 ?
    H15A C15 H15B . . 107.7 ?
    N6 C16 C17 . . 111.14(18) ?
    N6 C16 H16A . . 109.4 ?
    C17 C16 H16A . . 109.4 ?
    N6 C16 H16B . . 109.4 ?
    C17 C16 H16B . . 109.4 ?
    H16A C16 H16B . . 108.0 ?
    C18 C17 C22 . . 118.5(2) ?
    C18 C17 C16 . . 121.1(2) ?
    C22 C17 C16 . . 120.3(2) ?
    C17 C18 C19 . . 120.3(3) ?
    C17 C18 H18 . . 119.9 ?
    C19 C18 H18 . . 119.9 ?
    C20 C19 C18 . . 120.2(3) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 120.3(3) ?
    C19 C20 H20 . . 119.8 ?
    C21 C20 H20 . . 119.8 ?
    C20 C21 C22 . . 119.9(3) ?
    C20 C21 H21 . . 120.1 ?
    C22 C21 H21 . . 120.1 ?
    C21 C22 C17 . . 120.7(2) ?
    C21 C22 H22 . . 119.6 ?
    C17 C22 H22 . . 119.6 ?
    C2 N1 C1 . . 110.69(17) ?
    C2 N1 Ni1 . . 109.20(13) ?
    C1 N1 Ni1 . . 116.87(14) ?
    C2 N1 H1 . . 106.5 ?
    C1 N1 H1 . . 106.5 ?
    Ni1 N1 H1 . . 106.5 ?
    C3 N2 C4 . . 110.50(18) ?
    C3 N2 Ni1 . . 108.53(14) ?
    C4 N2 Ni1 . . 117.16(14) ?
    C3 N2 H2 . . 106.7 ?
    C4 N2 H2 . . 106.7 ?
    Ni1 N2 H2 . . 106.7 ?
    C4 N3 C1 . 2_666 113.60(18) ?
    C4 N3 C5 . . 116.03(19) ?
    C1 N3 C5 2_666 . 113.48(19) ?
    C13 N4 C12 . . 110.37(16) ?
    C13 N4 Ni2 . . 108.90(12) ?
    C12 N4 Ni2 . . 116.98(14) ?
    C13 N4 H4 . . 106.7 ?
    C12 N4 H4 . . 106.7 ?
    Ni2 N4 H4 . . 106.7 ?
    C14 N5 C15 . . 110.04(16) ?
    C14 N5 Ni2 . . 109.00(12) ?
    C15 N5 Ni2 . . 117.86(13) ?
    C14 N5 H5 . . 106.4 ?
    C15 N5 H5 . . 106.4 ?
    Ni2 N5 H5 . . 106.4 ?
    C15 N6 C12 . 2_655 115.04(18) ?
    C15 N6 C16 . . 115.85(19) ?
    C12 N6 C16 2_655 . 118.18(19) ?
    O14 Cl1 O11 . . 110.92(16) ?
    O14 Cl1 O12 . . 109.43(18) ?
    O11 Cl1 O12 . . 111.66(15) ?
    O14 Cl1 O13 . . 109.4(2) ?
    O11 Cl1 O13 . . 108.84(15) ?
    O12 Cl1 O13 . . 106.45(16) ?
    O24 Cl2 O22 . . 109.1(3) ?
    O24 Cl2 O21 . . 110.85(18) ?
    O22 Cl2 O21 . . 111.45(15) ?
    O24 Cl2 O23 . . 108.9(3) ?
    O22 Cl2 O23 . . 105.89(18) ?
    O21 Cl2 O23 . . 110.45(13) ?
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
    N1 H1 O21 1_556 0.91 2.25 3.024(3) 142
    N1 H1 O12 2_666 0.91 2.50 3.042(3) 118
    N2 H2 O13 . 0.91 2.23 3.094(3) 158
    N4 H4 O23 . 0.91 2.17 3.020(3) 155
    N5 H5 O11 1_545 0.91 2.18 2.947(3) 142
data_global
_journal_date_recd_electronic     2004-01-13
_journal_date_accepted     2004-01-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      3
_journal_page_first     m309
_journal_page_last     m311
_journal_paper_category     EM
_publ_contact_author
;
Dr. Seik Weng Ng
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 4204'
_publ_section_title
;
Nickel complexes of 1,8-diorganyl-1,3,6,8,10,13-hexaazacyclotetradecane.
1. [1,8-Bis(2-benzyl)-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II)
diperchlorate
;
loop_
    _publ_author_name
    _publ_author_address
    'Li, Yan-Wu'
;
Instrument Analysis and Research Center
Sun Yat-Sen University
Guangzhou 510275
People's Republic of China
;
    'Xiang, Hua'
;
Instrument Analysis and Research Center
Sun Yat-Sen University
Guangzhou 510275
People's Republic of China
;
    'Lu, Tong-Bu'
;
Instrument Analysis and Research Center
Sun Yat-Sen University
Guangzhou 510275
People's Republic of China
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
