##############################################################################
###                                                                        ###
###           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 2.1.    #
#                                                                            #
# 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_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.2
_journal_date_recd_electronic     2004-02-25
_journal_date_accepted     2004-03-22
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2004
_journal_volume     60
_journal_issue      5
_journal_page_first     o321
_journal_page_last     o324
_journal_paper_category     FO
_publ_contact_author_name     'Cox, Philip J.'
_publ_contact_author_address
;
School of Pharmacy
The Robert Gordon University
Schoolhill
Aberdeen
AB10 1FR
Scotland  UK
;
_publ_contact_author_email     p.j.cox@rgu.ac.uk
_publ_contact_author_fax     '44(1224)262535'
_publ_contact_author_phone     '44(1224)262555'
_publ_section_title
;
Two oxazane macrocycles
;
loop_
    _publ_author_name
    _publ_author_address
    'Philip J. Cox'
;
School of Pharmacy
The Robert Gordon University
Schoolhill
Aberdeen AB10 1FR
Scotland
;
    'Paul Kong Thoo Lin'
;
School of Life Sciences
The Robert Gordon University
St Andrews Street
Aberdeen AB25 1HG
Scotland
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_formula_moiety     'C12 H32 N4 O4 4+, 4Cl 1-'
_chemical_formula_sum     'C12 H32 Cl4 N4 O4'
_chemical_formula_iupac     'C12 H32 N4 O4 4+, 4Cl 1-'
_chemical_formula_weight     438.22
_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     9.1948(2)
_cell_length_b     9.8341(2)
_cell_length_c     12.2985(3)
_cell_angle_alpha     83.1450(10)
_cell_angle_beta     82.9330(10)
_cell_angle_gamma     80.8650(10)
_cell_volume     1083.95(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     13890
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.1
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.343
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.568
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1997)'
_exptl_absorpt_correction_T_min     0.8600
_exptl_absorpt_correction_T_max     0.9454
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
        Nonius KappaCCD area detector
;
_diffrn_measurement_method
;
        φ and ω scans to fill Ewald sphere
;
_diffrn_reflns_number     17127
_diffrn_reflns_av_R_equivalents     0.051
_diffrn_reflns_theta_min     2.95
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_decay_%     0
_reflns_number_total     4892
_reflns_number_gt     4134
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0417
_refine_ls_R_factor_gt     0.0315
_refine_ls_wR_factor_gt     0.0749
_refine_ls_wR_factor_ref     0.0790
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     4892
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0341P)²+0.2746P] 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     0.369
_refine_diff_density_min     -0.278
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0031(13)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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
;
        DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_cell_refinement     'DENZO and COLLECT'
_computing_data_reduction     'DENZO and COLLECT'
_computing_structure_solution     'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997)
;
_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
    Cl1 0.78182(4) 0.29749(4) 0.02612(3) 0.01915(10) Uani d . 1 . . Cl
    Cl2 0.64696(4) 0.19188(4) 0.52487(3) 0.01962(10) Uani d . 1 . . Cl
    Cl3 0.11847(4) 0.30594(4) 0.54479(3) 0.02089(10) Uani d . 1 . . Cl
    Cl4 0.73572(4) 0.81739(4) -0.05541(3) 0.01895(10) Uani d . 1 . . Cl
    O1 0.99254(12) 0.16537(10) 0.29883(8) 0.0203(2) Uani d . 1 . . O
    N2 0.92211(14) 0.25611(12) 0.37742(10) 0.0165(3) Uani d . 1 . . N
    H2A 0.9901 0.2741 0.4208 0.020 Uiso calc R 1 . . H
    H2B 0.8494 0.2160 0.4221 0.020 Uiso calc R 1 . . H
    C3 0.85642(16) 0.38629(15) 0.31712(12) 0.0171(3) Uani d . 1 . . C
    H3A 0.8151 0.4540 0.3704 0.020 Uiso calc R 1 . . H
    H3B 0.7740 0.3676 0.2790 0.020 Uiso calc R 1 . . H
    C4 0.96970(17) 0.44816(15) 0.23322(13) 0.0191(3) Uani d . 1 . . C
    H4A 1.0071 0.3823 0.1778 0.023 Uiso calc R 1 . . H
    H4B 1.0546 0.4620 0.2709 0.023 Uiso calc R 1 . . H
    C5 0.90526(17) 0.58581(15) 0.17511(13) 0.0186(3) Uani d . 1 . . C
    H5A 0.8783 0.6546 0.2295 0.022 Uiso calc R 1 . . H
    H5B 0.9819 0.6194 0.1191 0.022 Uiso calc R 1 . . H
    N6 0.77188(13) 0.57604(13) 0.12039(10) 0.0168(3) Uani d . 1 . . N
    H6A 0.7628 0.6427 0.0614 0.020 Uiso calc R 1 . . H
    H6B 0.7800 0.4905 0.0951 0.020 Uiso calc R 1 . . H
    O7 0.64545(11) 0.59624(11) 0.20007(8) 0.0188(2) Uani d . 1 . . O
    C8 0.51149(17) 0.58962(16) 0.15037(12) 0.0191(3) Uani d . 1 . . C
    H8A 0.5142 0.4970 0.1255 0.023 Uiso calc R 1 . . H
    H8B 0.5008 0.6602 0.0862 0.023 Uiso calc R 1 . . H
    C9 0.38482(17) 0.61760(15) 0.23943(13) 0.0202(3) Uani d . 1 . . C
    H9A 0.2903 0.6216 0.2075 0.024 Uiso calc R 1 . . H
    H9B 0.3867 0.7096 0.2639 0.024 Uiso calc R 1 . . H
    C10 0.38792(18) 0.51090(15) 0.33918(13) 0.0203(3) Uani d . 1 . . C
    H10A 0.4806 0.5054 0.3739 0.024 Uiso calc R 1 . . H
    H10B 0.3026 0.5346 0.3944 0.024 Uiso calc R 1 . . H
    O11 0.37975(12) 0.38171(10) 0.29722(8) 0.0210(2) Uani d . 1 . . O
    N12 0.38989(14) 0.26899(12) 0.38137(10) 0.0175(3) Uani d . 1 . . N
    H12A 0.3055 0.2751 0.4302 0.021 Uiso calc R 1 . . H
    H12B 0.4699 0.2694 0.4194 0.021 Uiso calc R 1 . . H
    C13 0.40765(16) 0.14083(15) 0.32589(12) 0.0182(3) Uani d . 1 . . C
    H13A 0.3290 0.1470 0.2766 0.022 Uiso calc R 1 . . H
    H13B 0.3992 0.0601 0.3814 0.022 Uiso calc R 1 . . H
    C14 0.55825(18) 0.12326(17) 0.25980(14) 0.0240(3) Uani d . 1 . . C
    H14A 0.5710 0.2108 0.2133 0.029 Uiso calc R 1 . . H
    H14B 0.6356 0.1055 0.3112 0.029 Uiso calc R 1 . . H
    C15 0.58077(16) 0.00686(16) 0.18701(13) 0.0190(3) Uani d . 1 . . C
    H15A 0.5706 -0.0819 0.2324 0.023 Uiso calc R 1 . . H
    H15B 0.5051 0.0236 0.1343 0.023 Uiso calc R 1 . . H
    N16 0.73087(13) -0.00011(13) 0.12633(10) 0.0171(3) Uani d . 1 . . N
    H16A 0.7394 -0.0554 0.0699 0.020 Uiso calc R 1 . . H
    H16B 0.7485 0.0869 0.0968 0.020 Uiso calc R 1 . . H
    O17 0.83421(11) -0.05667(10) 0.20308(8) 0.0182(2) Uani d . 1 . . O
    C18 0.98322(16) -0.03550(15) 0.15841(12) 0.0180(3) Uani d . 1 . . C
    H18A 0.9842 0.0607 0.1240 0.022 Uiso calc R 1 . . H
    H18B 1.0227 -0.0998 0.1021 0.022 Uiso calc R 1 . . H
    C19 1.07496(16) -0.06390(15) 0.25513(12) 0.0178(3) Uani d . 1 . . C
    H19A 1.0800 -0.1629 0.2835 0.021 Uiso calc R 1 . . H
    H19B 1.1771 -0.0461 0.2292 0.021 Uiso calc R 1 . . H
    C20 1.01366(17) 0.02342(15) 0.34797(12) 0.0174(3) Uani d . 1 . . C
    H20A 0.9183 -0.0035 0.3833 0.021 Uiso calc R 1 . . H
    H20B 1.0840 0.0115 0.4044 0.021 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
    Cl1 0.0233(2) 0.01433(18) 0.01929(19) -0.00213(14) -0.00157(14) -0.00128(15)
    Cl2 0.02013(19) 0.02069(19) 0.01824(19) -0.00444(14) -0.00278(14)
                                                                    -0.00006(15)
    Cl3 0.0207(2) 0.0268(2) 0.01643(19) -0.00656(15) -0.00062(14) -0.00458(16)
    Cl4 0.0264(2) 0.01640(18) 0.01435(18) -0.00346(14) -0.00417(14) -0.00019(14)
    O1 0.0312(6) 0.0130(5) 0.0143(5) 0.0003(4) 0.0019(4) -0.0007(4)
    N2 0.0190(6) 0.0169(6) 0.0136(6) -0.0023(5) -0.0016(5) -0.0021(5)
    C3 0.0176(7) 0.0145(7) 0.0182(7) -0.0010(6) -0.0028(6) 0.0009(6)
    C4 0.0185(8) 0.0175(7) 0.0209(8) -0.0033(6) -0.0022(6) 0.0007(6)
    C5 0.0200(8) 0.0161(7) 0.0199(8) -0.0055(6) -0.0008(6) -0.0006(6)
    N6 0.0202(7) 0.0148(6) 0.0140(6) -0.0015(5) 0.0007(5) -0.0004(5)
    O7 0.0166(5) 0.0241(6) 0.0149(5) -0.0013(4) 0.0001(4) -0.0025(5)
    C8 0.0193(8) 0.0202(7) 0.0179(7) -0.0029(6) -0.0049(6) 0.0005(6)
    C9 0.0207(8) 0.0166(7) 0.0220(8) -0.0006(6) -0.0020(6) -0.0006(6)
    C10 0.0244(8) 0.0173(7) 0.0193(8) -0.0032(6) 0.0004(6) -0.0048(6)
    O11 0.0328(6) 0.0155(5) 0.0151(5) -0.0048(4) -0.0043(5) 0.0009(4)
    N12 0.0185(6) 0.0196(6) 0.0139(6) -0.0038(5) -0.0005(5) 0.0009(5)
    C13 0.0206(8) 0.0155(7) 0.0185(7) -0.0041(6) -0.0015(6) -0.0001(6)
    C14 0.0227(8) 0.0245(8) 0.0264(8) -0.0066(7) 0.0015(7) -0.0089(7)
    C15 0.0180(8) 0.0188(7) 0.0217(8) -0.0029(6) -0.0050(6) -0.0044(6)
    N16 0.0215(7) 0.0139(6) 0.0159(6) -0.0004(5) -0.0051(5) -0.0016(5)
    O17 0.0169(5) 0.0201(5) 0.0168(5) -0.0021(4) -0.0047(4) 0.0032(4)
    C18 0.0185(8) 0.0173(7) 0.0175(7) -0.0032(6) 0.0020(6) -0.0016(6)
    C19 0.0172(7) 0.0156(7) 0.0191(8) -0.0003(6) -0.0016(6) 0.0011(6)
    C20 0.0208(8) 0.0139(7) 0.0168(7) -0.0020(6) -0.0041(6) 0.0035(6)
_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 N2 . 1.4206(15) ?
    O1 C20 . 1.4467(17) ?
    N2 C3 . 1.4805(18) ?
    N2 H2A . 0.92 ?
    N2 H2B . 0.92 ?
    C3 C4 . 1.519(2) ?
    C3 H3A . 0.99 ?
    C3 H3B . 0.99 ?
    C4 C5 . 1.521(2) ?
    C4 H4A . 0.99 ?
    C4 H4B . 0.99 ?
    C5 N6 . 1.4907(19) ?
    C5 H5A . 0.99 ?
    C5 H5B . 0.99 ?
    N6 O7 . 1.4296(15) ?
    N6 H6A . 0.92 ?
    N6 H6B . 0.92 ?
    O7 C8 . 1.4544(18) ?
    C8 C9 . 1.513(2) ?
    C8 H8A . 0.99 ?
    C8 H8B . 0.99 ?
    C9 C10 . 1.516(2) ?
    C9 H9A . 0.99 ?
    C9 H9B . 0.99 ?
    C10 O11 . 1.4430(18) ?
    C10 H10A . 0.99 ?
    C10 H10B . 0.99 ?
    O11 N12 . 1.4233(16) ?
    N12 C13 . 1.4809(19) ?
    N12 H12A . 0.92 ?
    N12 H12B . 0.92 ?
    C13 C14 . 1.513(2) ?
    C13 H13A . 0.99 ?
    C13 H13B . 0.99 ?
    C14 C15 . 1.509(2) ?
    C14 H14A . 0.99 ?
    C14 H14B . 0.99 ?
    C15 N16 . 1.4816(19) ?
    C15 H15A . 0.99 ?
    C15 H15B . 0.99 ?
    N16 O17 . 1.4250(15) ?
    N16 H16A . 0.92 ?
    N16 H16B . 0.92 ?
    O17 C18 . 1.4492(18) ?
    C18 C19 . 1.516(2) ?
    C18 H18A . 0.99 ?
    C18 H18B . 0.99 ?
    C19 C20 . 1.510(2) ?
    C19 H19A . 0.99 ?
    C19 H19B . 0.99 ?
    C20 H20A . 0.99 ?
    C20 H20B . 0.99 ?
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
    N2 O1 C20 . . 111.05(10) ?
    O1 N2 C3 . . 108.16(10) ?
    O1 N2 H2A . . 110.1 ?
    C3 N2 H2A . . 110.1 ?
    O1 N2 H2B . . 110.1 ?
    C3 N2 H2B . . 110.1 ?
    H2A N2 H2B . . 108.4 ?
    N2 C3 C4 . . 111.89(12) ?
    N2 C3 H3A . . 109.2 ?
    C4 C3 H3A . . 109.2 ?
    N2 C3 H3B . . 109.2 ?
    C4 C3 H3B . . 109.2 ?
    H3A C3 H3B . . 107.9 ?
    C3 C4 C5 . . 112.27(12) ?
    C3 C4 H4A . . 109.1 ?
    C5 C4 H4A . . 109.1 ?
    C3 C4 H4B . . 109.1 ?
    C5 C4 H4B . . 109.1 ?
    H4A C4 H4B . . 107.9 ?
    N6 C5 C4 . . 112.82(12) ?
    N6 C5 H5A . . 109.0 ?
    C4 C5 H5A . . 109.0 ?
    N6 C5 H5B . . 109.0 ?
    C4 C5 H5B . . 109.0 ?
    H5A C5 H5B . . 107.8 ?
    O7 N6 C5 . . 107.69(10) ?
    O7 N6 H6A . . 110.2 ?
    C5 N6 H6A . . 110.2 ?
    O7 N6 H6B . . 110.2 ?
    C5 N6 H6B . . 110.2 ?
    H6A N6 H6B . . 108.5 ?
    N6 O7 C8 . . 109.96(10) ?
    O7 C8 C9 . . 105.78(12) ?
    O7 C8 H8A . . 110.6 ?
    C9 C8 H8A . . 110.6 ?
    O7 C8 H8B . . 110.6 ?
    C9 C8 H8B . . 110.6 ?
    H8A C8 H8B . . 108.7 ?
    C8 C9 C10 . . 114.42(13) ?
    C8 C9 H9A . . 108.7 ?
    C10 C9 H9A . . 108.7 ?
    C8 C9 H9B . . 108.7 ?
    C10 C9 H9B . . 108.7 ?
    H9A C9 H9B . . 107.6 ?
    O11 C10 C9 . . 105.11(12) ?
    O11 C10 H10A . . 110.7 ?
    C9 C10 H10A . . 110.7 ?
    O11 C10 H10B . . 110.7 ?
    C9 C10 H10B . . 110.7 ?
    H10A C10 H10B . . 108.8 ?
    N12 O11 C10 . . 111.65(10) ?
    O11 N12 C13 . . 106.72(10) ?
    O11 N12 H12A . . 110.4 ?
    C13 N12 H12A . . 110.4 ?
    O11 N12 H12B . . 110.4 ?
    C13 N12 H12B . . 110.4 ?
    H12A N12 H12B . . 108.6 ?
    N12 C13 C14 . . 108.76(12) ?
    N12 C13 H13A . . 109.9 ?
    C14 C13 H13A . . 109.9 ?
    N12 C13 H13B . . 109.9 ?
    C14 C13 H13B . . 109.9 ?
    H13A C13 H13B . . 108.3 ?
    C15 C14 C13 . . 113.52(13) ?
    C15 C14 H14A . . 108.9 ?
    C13 C14 H14A . . 108.9 ?
    C15 C14 H14B . . 108.9 ?
    C13 C14 H14B . . 108.9 ?
    H14A C14 H14B . . 107.7 ?
    N16 C15 C14 . . 108.72(12) ?
    N16 C15 H15A . . 109.9 ?
    C14 C15 H15A . . 109.9 ?
    N16 C15 H15B . . 109.9 ?
    C14 C15 H15B . . 109.9 ?
    H15A C15 H15B . . 108.3 ?
    O17 N16 C15 . . 107.30(11) ?
    O17 N16 H16A . . 110.3 ?
    C15 N16 H16A . . 110.3 ?
    O17 N16 H16B . . 110.3 ?
    C15 N16 H16B . . 110.3 ?
    H16A N16 H16B . . 108.5 ?
    N16 O17 C18 . . 110.78(10) ?
    O17 C18 C19 . . 105.92(11) ?
    O17 C18 H18A . . 110.6 ?
    C19 C18 H18A . . 110.6 ?
    O17 C18 H18B . . 110.6 ?
    C19 C18 H18B . . 110.6 ?
    H18A C18 H18B . . 108.7 ?
    C20 C19 C18 . . 113.23(12) ?
    C20 C19 H19A . . 108.9 ?
    C18 C19 H19A . . 108.9 ?
    C20 C19 H19B . . 108.9 ?
    C18 C19 H19B . . 108.9 ?
    H19A C19 H19B . . 107.7 ?
    O1 C20 C19 . . 106.20(11) ?
    O1 C20 H20A . . 110.5 ?
    C19 C20 H20A . . 110.5 ?
    O1 C20 H20B . . 110.5 ?
    C19 C20 H20B . . 110.5 ?
    H20A C20 H20B . . 108.7 ?
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
    C20 O1 N2 C3 . . . . -160.12(11) y
    O1 N2 C3 C4 . . . . -53.62(15) y
    N2 C3 C4 C5 . . . . -176.99(12) y
    C3 C4 C5 N6 . . . . -56.12(17) y
    C4 C5 N6 O7 . . . . 87.14(14) y
    C5 N6 O7 C8 . . . . 179.20(11) y
    N6 O7 C8 C9 . . . . -177.85(11) y
    O7 C8 C9 C10 . . . . -62.88(16) y
    C8 C9 C10 O11 . . . . -60.32(16) y
    C9 C10 O11 N12 . . . . 176.75(11) y
    C10 O11 N12 C13 . . . . -169.99(11) y
    O11 N12 C13 C14 . . . . 68.59(14) y
    N12 C13 C14 C15 . . . . -171.99(13) y
    C13 C14 C15 N16 . . . . 179.77(12) y
    C14 C15 N16 O17 . . . . 73.33(14) y
    C15 N16 O17 C18 . . . . -165.74(11) y
    N16 O17 C18 C19 . . . . 165.42(10) y
    O17 C18 C19 C20 . . . . -55.81(15) y
    N2 O1 C20 C19 . . . . 174.63(11) y
    C18 C19 C20 O1 . . . . -52.01(16) y
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
    _geom_hbond_publ_flag
    N2 H2A Cl3 1_655 0.92 2.12 3.0287(12) 170 y
    N2 H2B Cl2 . 0.92 2.15 3.0321(13) 161 y
    N6 H6A Cl4 . 0.92 2.11 3.0199(13) 171 y
    N6 H6B Cl1 . 0.92 2.17 3.0836(13) 175 y
    N12 H12A Cl3 . 0.92 2.09 3.0086(13) 175 y
    N12 H12B Cl2 . 0.92 2.19 3.0683(13) 159 y
    N16 H16A Cl4 1_545 0.92 2.10 3.0210(13) 174 y
    N16 H16B Cl1 . 0.92 2.20 3.1202(13) 178 y
    C5 H5B Cl1 2_765 0.99 2.80 3.7866(16) 175 y
    C13 H13A Cl4 2_665 0.99 2.82 3.6814(15) 145 y
    C13 H13B Cl2 2_656 0.99 2.68 3.6315(15) 161 y
    C15 H15B Cl4 2_665 0.99 2.71 3.6013(15) 150 y
data_II
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_formula_moiety     'C10 H28 N4 O4 4+, 4Cl 1-'
_chemical_formula_sum     'C10 H28 Cl4 N4 O4'
_chemical_formula_iupac     'C10 H28 N4 O4 4+, 4Cl 1-'
_chemical_formula_weight     410.16
_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     7.6921(2)
_cell_length_b     8.3920(2)
_cell_length_c     8.6696(3)
_cell_angle_alpha     67.409(2)
_cell_angle_beta     68.128(2)
_cell_angle_gamma     88.967(2)
_cell_volume     474.37(3)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     3448
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.436
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     216
_exptl_absorpt_coefficient_mu     0.644
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SORTAV; Blessing, 1997)'
_exptl_absorpt_correction_T_min     0.941
_exptl_absorpt_correction_T_max     0.980
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
        Nonius KappaCCD area detector
;
_diffrn_measurement_method
;
        φ and ω scans to fill Ewald sphere
;
_diffrn_reflns_number     6137
_diffrn_reflns_av_R_equivalents     0.0482
_diffrn_reflns_theta_min     2.96
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.966
_diffrn_measured_fraction_theta_full     0.966
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_decay_%     0
_reflns_number_total     2090
_reflns_number_gt     1798
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0392
_refine_ls_R_factor_gt     0.0302
_refine_ls_wR_factor_gt     0.0720
_refine_ls_wR_factor_ref     0.0753
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     2090
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0262P)²+0.1427P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.313
_refine_diff_density_min     -0.258
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.019(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_cell_refinement     'DENZO and COLLECT'
_computing_data_reduction     'DENZO and COLLECT'
_computing_structure_solution     'SIR97 (Altomare et al.,1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997)
;
_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
    Cl1 0.32480(5) 0.15909(5) 0.36436(5) 0.01571(13) Uani d . 1 . . Cl
    Cl2 0.84740(5) 0.26379(5) 0.87007(5) 0.01947(14) Uani d . 1 . . Cl
    O1 0.54871(14) 0.29156(14) 0.58324(14) 0.0143(3) Uani d . 1 . . O
    N2 0.70790(17) 0.21150(16) 0.60752(17) 0.0123(3) Uani d . 1 . . N
    H2A 0.6895 0.0952 0.6308 0.015 Uiso calc R 1 . . H
    H2B 0.7236 0.2206 0.7041 0.015 Uiso calc R 1 . . H
    C3 0.8764(2) 0.3029(2) 0.4382(2) 0.0145(3) Uani d . 1 . . C
    H3A 0.9912 0.2701 0.4616 0.017 Uiso calc R 1 . . H
    H3B 0.8798 0.4302 0.4033 0.017 Uiso calc R 1 . . H
    C4 0.8817(2) 0.2629(2) 0.2805(2) 0.0151(3) Uani d . 1 . . C
    H4A 1.0095 0.3075 0.1816 0.018 Uiso calc R 1 . . H
    H4B 0.8609 0.1347 0.3210 0.018 Uiso calc R 1 . . H
    N5 0.73925(18) 0.33915(16) 0.20681(17) 0.0127(3) Uani d . 1 . . N
    H5A 0.7546 0.3175 0.1065 0.015 Uiso calc R 1 . . H
    H5B 0.6189 0.2908 0.2932 0.015 Uiso calc R 1 . . H
    O6 0.76719(14) 0.52168(13) 0.15796(14) 0.0135(2) Uani d . 1 . . O
    C7 0.6143(2) 0.6011(2) 0.1116(2) 0.0136(3) Uani d . 1 . . C
    H7A 0.4899 0.5393 0.2097 0.016 Uiso calc R 1 . . H
    H7B 0.6200 0.5973 -0.0029 0.016 Uiso calc R 1 . . H
    C8 0.6429(2) 0.7871(2) 0.0894(2) 0.0139(3) Uani d . 1 . . C
    H8A 0.5483 0.8502 0.0472 0.017 Uiso calc R 1 . . H
    H8B 0.7701 0.8441 -0.0060 0.017 Uiso calc R 1 . . H
    C9 0.6255(2) 0.8042(2) 0.2626(2) 0.0158(3) Uani d . 1 . . C
    H9A 0.7345 0.7610 0.2924 0.019 Uiso calc R 1 . . H
    H9B 0.6314 0.9291 0.2409 0.019 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
    O1 N2 . 1.4314(15) ?
    O1 C9 2_666 1.4518(18) ?
    N2 C3 . 1.4752(19) ?
    N2 H2A . 0.92 ?
    N2 H2B . 0.92 ?
    C3 C4 . 1.514(2) ?
    C3 H3A . 0.99 ?
    C3 H3B . 0.99 ?
    C4 N5 . 1.4836(19) ?
    C4 H4A . 0.99 ?
    C4 H4B . 0.99 ?
    N5 O6 . 1.4204(15) ?
    N5 H5A . 0.92 ?
    N5 H5B . 0.92 ?
    O6 C7 . 1.4516(17) ?
    C7 C8 . 1.508(2) ?
    C7 H7A . 0.99 ?
    C7 H7B . 0.99 ?
    C8 C9 . 1.519(2) ?
    C8 H8A . 0.99 ?
    C8 H8B . 0.99 ?
    C9 H9A . 0.99 ?
    C9 H9B . 0.99 ?
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
    N2 O1 C9 . 2_666 110.47(10) ?
    O1 N2 C3 . . 107.54(11) ?
    O1 N2 H2A . . 110.2 ?
    C3 N2 H2A . . 110.2 ?
    O1 N2 H2B . . 110.2 ?
    C3 N2 H2B . . 110.2 ?
    H2A N2 H2B . . 108.5 ?
    N2 C3 C4 . . 113.76(12) ?
    N2 C3 H3A . . 108.8 ?
    C4 C3 H3A . . 108.8 ?
    N2 C3 H3B . . 108.8 ?
    C4 C3 H3B . . 108.8 ?
    H3A C3 H3B . . 107.7 ?
    N5 C4 C3 . . 114.03(12) ?
    N5 C4 H4A . . 108.7 ?
    C3 C4 H4A . . 108.7 ?
    N5 C4 H4B . . 108.7 ?
    C3 C4 H4B . . 108.7 ?
    H4A C4 H4B . . 107.6 ?
    O6 N5 C4 . . 107.37(11) ?
    O6 N5 H5A . . 110.2 ?
    C4 N5 H5A . . 110.2 ?
    O6 N5 H5B . . 110.2 ?
    C4 N5 H5B . . 110.2 ?
    H5A N5 H5B . . 108.5 ?
    N5 O6 C7 . . 110.34(10) ?
    O6 C7 C8 . . 105.61(12) ?
    O6 C7 H7A . . 110.6 ?
    C8 C7 H7A . . 110.6 ?
    O6 C7 H7B . . 110.6 ?
    C8 C7 H7B . . 110.6 ?
    H7A C7 H7B . . 108.7 ?
    C7 C8 C9 . . 113.82(13) ?
    C7 C8 H8A . . 108.8 ?
    C9 C8 H8A . . 108.8 ?
    C7 C8 H8B . . 108.8 ?
    C9 C8 H8B . . 108.8 ?
    H8A C8 H8B . . 107.7 ?
    O1 C9 C8 2_666 . 113.05(12) ?
    O1 C9 H9A 2_666 . 109.0 ?
    C8 C9 H9A . . 109.0 ?
    O1 C9 H9B 2_666 . 109.0 ?
    C8 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
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
    C8 C9 O1 N2 2_666 2_666 . . 69.50(17) y
    C9 O1 N2 C3 2_666 . . . 173.78(11) y
    O1 N2 C3 C4 . . . . -72.23(15) y
    N2 C3 C4 N5 . . . . 70.57(17) y
    C3 C4 N5 O6 . . . . 55.80(15) y
    C4 N5 O6 C7 . . . . -171.03(11) y
    N5 O6 C7 C8 . . . . 171.92(11) y
    O6 C7 C8 C9 . . . . -63.37(15) y
    C7 C8 C9 O1 . . . 2_666 -52.29(17) y
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
    _geom_hbond_publ_flag
    N2 H2A Cl1 2_656 0.92 2.12 3.0323(13) 170 y
    N2 H2B Cl2 . 0.92 2.13 3.0214(13) 163 y
    N5 H5A Cl2 1_554 0.92 2.13 3.0340(13) 168 y
    N5 H5B Cl1 . 0.92 2.29 3.1074(13) 148 y
    N5 H5B O1 . 0.92 2.37 2.9007(16) 117 y
    C3 H3A Cl1 1_655 0.99 2.66 3.5445(15) 149 y
    C4 H4B Cl1 2_656 0.99 2.76 3.5673(16) 139 y
    C4 H4A O6 2_765 0.99 2.60 3.5012(19) 152 y
