Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2004

data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
'Luigi Fabbrizzi'
'Massimo Boiocchi'
'Marco Bonizzoni'
'Francesco Foti'
'Maurizio Licchelli'
'Angelo Taglietti'
'Michele Zema'

_publ_contact_author_name        'Prof Luigi Fabbrizzi'
_publ_contact_author_address     
;
Dipartimento di Chimica Generale
Universita di Pavia
via Taramelli 12
Pavia
I-27100
ITALY
;

_publ_contact_author_email       LUIGI.FABBRIZZI@UNIPV.IT

_publ_requested_journal          'Dalton Transactions'

_publ_section_title              
;
The influence of the boat-to-chair conversion on the
demetallation of the nickel(II) complex of an open-chain tetramine
containing a piperazine fragment
;

data_NiCLO4
_database_code_depnum_ccdc_archive 'CCDC 221987'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
3-(4-butylpiperazin-1-yl)-propylamine-nickel(II)-diperchlorate
;
_chemical_formula_moiety         'C10 H24 N4 Ni, 2(Cl O4)'
_chemical_formula_sum            'C10 H24 Cl2 N4 Ni O8'
_chemical_formula_weight         457.92

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

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                   14.4256(22)
_cell_length_b                   15.3904(23)
_cell_length_c                   16.1714(24)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3590.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      10
_cell_measurement_theta_max      22

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1904
_exptl_absorpt_coefficient_mu    1.425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22120
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         29.97
_reflns_number_total             5098
_reflns_number_gt                3885
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker-Axs Inc.)'
_computing_cell_refinement       'SAINT (Bruker-Axs Inc.)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc.)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farruggia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The C(4) atomic displacement parameters suggest positional disorder,
but several attempts to refine two alternative positions for C(4)
do not improve the agreement index and result feasible only using
strong geometrical constraints. Due to the failure in the characterization
of the alternative C(4) positions, we chose to refine C(4) using a
single-site anisotropic model and this is the reasons of the chemically
unacceptable bond values involving C(4).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0854P)^2^+6.0954P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00055(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5098
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1721
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.75873(3) 0.12313(2) 0.54890(3) 0.03386(15) Uani 1 1 d . . .
Cl1 Cl 0.94066(8) 0.12611(6) 0.29470(6) 0.0536(3) Uani 1 1 d . . .
Cl2 Cl 0.26338(7) 0.12167(5) 0.53328(8) 0.0540(3) Uani 1 1 d . . .
O1 O 0.9199(5) 0.1327(3) 0.2104(3) 0.128(2) Uani 1 1 d . . .
O2 O 1.0368(4) 0.1126(3) 0.3038(6) 0.158(3) Uani 1 1 d . . .
O3 O 0.8957(3) 0.0530(2) 0.3312(2) 0.0918(12) Uani 1 1 d . . .
O4 O 0.9164(3) 0.2033(2) 0.3380(2) 0.0927(12) Uani 1 1 d . . .
O5 O 0.3126(4) 0.1867(3) 0.4915(3) 0.1214(17) Uani 1 1 d . . .
O6 O 0.2076(4) 0.0721(4) 0.4817(4) 0.1349(19) Uani 1 1 d . . .
O7 O 0.3235(4) 0.0696(3) 0.5819(4) 0.1297(19) Uani 1 1 d . . .
O8 O 0.2038(4) 0.1660(4) 0.5902(4) 0.1303(18) Uani 1 1 d . . .
N1 N 0.7868(2) 0.11869(18) 0.66570(18) 0.0446(7) Uani 1 1 d . . .
N2 N 0.6389(2) 0.1375(2) 0.5996(2) 0.0582(9) Uani 1 1 d . . .
N3 N 0.7195(3) 0.1288(2) 0.4360(2) 0.0512(8) Uani 1 1 d . . .
H3AN H 0.7509 0.1734 0.4133 0.061 Uiso 1 1 calc R . .
H3BN H 0.7413 0.0803 0.4117 0.061 Uiso 1 1 calc R . .
N4 N 0.8831(2) 0.1165(2) 0.5090(2) 0.0528(8) Uani 1 1 d . . .
H4AN H 0.8835 0.0757 0.4691 0.063 Uiso 1 1 calc R . .
H4BN H 0.8951 0.1675 0.4839 0.063 Uiso 1 1 calc R . .
C1 C 0.7478(3) 0.2033(3) 0.6938(3) 0.0618(11) Uani 1 1 d . . .
H1A H 0.7887 0.2506 0.6781 0.074 Uiso 1 1 calc R . .
H1B H 0.7412 0.2036 0.7535 0.074 Uiso 1 1 calc R . .
C2 C 0.6550(3) 0.2141(3) 0.6534(3) 0.0677(12) Uani 1 1 d . . .
H2A H 0.6068 0.2180 0.6951 0.081 Uiso 1 1 calc R . .
H2B H 0.6540 0.2669 0.6207 0.081 Uiso 1 1 calc R . .
C3 C 0.5537(4) 0.1507(6) 0.5474(5) 0.113(3) Uani 1 1 d . . .
H3A H 0.5049 0.1148 0.5706 0.136 Uiso 1 1 calc R . .
H3B H 0.5345 0.2107 0.5541 0.136 Uiso 1 1 calc R . .
C4 C 0.5568(5) 0.1351(8) 0.4693(6) 0.211(8) Uani 1 1 d . . .
H4A H 0.5076 0.1713 0.4474 0.254 Uiso 1 1 calc R . .
H4B H 0.5335 0.0761 0.4655 0.254 Uiso 1 1 calc R . .
C5 C 0.6232(4) 0.1380(3) 0.4075(4) 0.0753(15) Uani 1 1 d . . .
H5A H 0.6173 0.1929 0.3785 0.090 Uiso 1 1 calc R . .
H5B H 0.6102 0.0921 0.3681 0.090 Uiso 1 1 calc R . .
C6 C 0.6323(3) 0.0594(3) 0.6535(4) 0.0804(15) Uani 1 1 d . . .
H6A H 0.6182 0.0084 0.6207 0.096 Uiso 1 1 calc R . .
H6B H 0.5835 0.0670 0.6942 0.096 Uiso 1 1 calc R . .
C7 C 0.7246(4) 0.0487(3) 0.6959(3) 0.0703(13) Uani 1 1 d . . .
H7A H 0.7171 0.0530 0.7554 0.084 Uiso 1 1 calc R . .
H7B H 0.7508 -0.0078 0.6831 0.084 Uiso 1 1 calc R . .
C8 C 0.8826(3) 0.1061(3) 0.6982(3) 0.0660(12) Uani 1 1 d . . .
H8A H 0.8946 0.0444 0.7041 0.079 Uiso 1 1 calc R . .
H8B H 0.8870 0.1323 0.7526 0.079 Uiso 1 1 calc R . .
C9 C 0.9551(3) 0.1450(3) 0.6434(3) 0.0686(12) Uani 1 1 d . . .
H9A H 0.9400 0.2054 0.6329 0.082 Uiso 1 1 calc R . .
H9B H 1.0145 0.1433 0.6715 0.082 Uiso 1 1 calc R . .
C10 C 0.9628(3) 0.0979(4) 0.5629(3) 0.0637(11) Uani 1 1 d . . .
H10A H 1.0195 0.1153 0.5352 0.076 Uiso 1 1 calc R . .
H10B H 0.9661 0.0359 0.5732 0.076 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0311(2) 0.0371(2) 0.0334(2) -0.00226(15) 0.00056(14) 0.00060(14)
Cl1 0.0618(6) 0.0505(5) 0.0484(5) 0.0009(4) 0.0071(4) -0.0061(4)
Cl2 0.0513(5) 0.0415(5) 0.0691(6) 0.0012(4) -0.0035(4) 0.0030(4)
O1 0.224(7) 0.098(3) 0.060(2) 0.009(2) 0.003(3) 0.017(3)
O2 0.079(3) 0.107(4) 0.288(10) -0.004(4) -0.021(5) 0.007(3)
O3 0.129(3) 0.076(2) 0.071(2) -0.0111(18) 0.023(2) -0.040(2)
O4 0.130(3) 0.062(2) 0.086(3) -0.0111(18) 0.016(2) 0.002(2)
O5 0.118(4) 0.099(3) 0.147(4) 0.041(3) 0.008(3) -0.031(3)
O6 0.137(4) 0.120(4) 0.148(5) -0.038(4) -0.037(4) -0.035(4)
O7 0.117(4) 0.086(3) 0.186(5) 0.034(3) -0.044(4) 0.023(3)
O8 0.126(4) 0.134(4) 0.131(4) -0.019(4) 0.031(4) 0.022(4)
N1 0.0540(17) 0.0464(16) 0.0333(14) 0.0010(11) 0.0044(12) -0.0045(12)
N2 0.0361(15) 0.076(2) 0.062(2) -0.0118(17) 0.0092(14) 0.0009(14)
N3 0.0540(18) 0.056(2) 0.0440(17) 0.0030(13) -0.0093(14) 0.0008(13)
N4 0.0404(15) 0.077(2) 0.0404(16) -0.0042(14) 0.0033(13) 0.0028(14)
C1 0.077(3) 0.057(2) 0.051(2) -0.0185(19) 0.0084(19) -0.001(2)
C2 0.064(3) 0.064(3) 0.075(3) -0.013(2) 0.018(2) 0.013(2)
C3 0.033(2) 0.169(6) 0.137(7) -0.054(5) -0.009(3) 0.019(3)
C4 0.039(3) 0.51(2) 0.090(5) 0.054(8) -0.015(3) 0.009(6)
C5 0.067(3) 0.079(3) 0.080(3) -0.002(2) -0.038(3) 0.008(2)
C6 0.068(3) 0.083(3) 0.091(4) -0.007(3) 0.033(3) -0.027(3)
C7 0.089(3) 0.061(3) 0.061(3) 0.016(2) 0.020(2) -0.013(2)
C8 0.074(3) 0.084(3) 0.040(2) 0.004(2) -0.0164(19) 0.004(2)
C9 0.050(2) 0.087(3) 0.069(3) -0.006(2) -0.024(2) -0.004(2)
C10 0.0360(18) 0.086(3) 0.069(3) -0.001(2) -0.0043(18) 0.0097(19)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N4 1.910(3) . ?
Ni1 N3 1.914(3) . ?
Ni1 N2 1.926(3) . ?
Ni1 N1 1.933(3) . ?
Cl1 O1 1.400(5) . ?
Cl1 O2 1.410(6) . ?
Cl1 O4 1.422(4) . ?
Cl1 O3 1.427(3) . ?
Cl2 O6 1.388(5) . ?
Cl2 O5 1.401(4) . ?
Cl2 O7 1.419(4) . ?
Cl2 O8 1.432(5) . ?
N1 C7 1.485(5) . ?
N1 C1 1.490(5) . ?
N1 C8 1.491(6) . ?
N2 C2 1.484(6) . ?
N2 C6 1.488(6) . ?
N2 C3 1.505(7) . ?
N3 C5 1.471(6) . ?
N3 H3AN 0.9000 . ?
N3 H3BN 0.9000 . ?
N4 C10 1.471(5) . ?
N4 H4AN 0.9000 . ?
N4 H4BN 0.9000 . ?
C1 C2 1.499(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.287(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.384(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.507(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.496(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.493(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Ni1 N3 87.57(15) . . ?
N4 Ni1 N2 173.45(15) . . ?
N3 Ni1 N2 97.77(17) . . ?
N4 Ni1 N1 97.55(14) . . ?
N3 Ni1 N1 174.87(15) . . ?
N2 Ni1 N1 77.10(15) . . ?
O1 Cl1 O2 108.8(5) . . ?
O1 Cl1 O4 111.5(3) . . ?
O2 Cl1 O4 108.3(3) . . ?
O1 Cl1 O3 111.3(3) . . ?
O2 Cl1 O3 106.7(3) . . ?
O4 Cl1 O3 110.1(2) . . ?
O6 Cl2 O5 113.3(4) . . ?
O6 Cl2 O7 112.2(4) . . ?
O5 Cl2 O7 111.2(3) . . ?
O6 Cl2 O8 107.5(4) . . ?
O5 Cl2 O8 105.9(4) . . ?
O7 Cl2 O8 106.2(4) . . ?
C7 N1 C1 107.8(4) . . ?
C7 N1 C8 110.5(3) . . ?
C1 N1 C8 110.8(3) . . ?
C7 N1 Ni1 102.7(3) . . ?
C1 N1 Ni1 100.9(2) . . ?
C8 N1 Ni1 122.9(3) . . ?
C2 N2 C6 107.9(4) . . ?
C2 N2 C3 110.5(4) . . ?
C6 N2 C3 112.7(5) . . ?
C2 N2 Ni1 101.5(2) . . ?
C6 N2 Ni1 102.4(3) . . ?
C3 N2 Ni1 120.7(4) . . ?
C5 N3 Ni1 125.6(3) . . ?
C5 N3 H3AN 105.9 . . ?
Ni1 N3 H3AN 105.9 . . ?
C5 N3 H3BN 105.9 . . ?
Ni1 N3 H3BN 105.9 . . ?
H3AN N3 H3BN 106.2 . . ?
C10 N4 Ni1 122.9(3) . . ?
C10 N4 H4AN 106.6 . . ?
Ni1 N4 H4AN 106.6 . . ?
C10 N4 H4BN 106.6 . . ?
Ni1 N4 H4BN 106.6 . . ?
H4AN N4 H4BN 106.6 . . ?
N1 C1 C2 107.5(3) . . ?
N1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N2 C2 C1 107.9(3) . . ?
N2 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
N2 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C4 C3 N2 119.8(5) . . ?
C4 C3 H3A 107.4 . . ?
N2 C3 H3A 107.4 . . ?
C4 C3 H3B 107.4 . . ?
N2 C3 H3B 107.4 . . ?
H3A C3 H3B 106.9 . . ?
C3 C4 C5 136.6(7) . . ?
C3 C4 H4A 103.0 . . ?
C5 C4 H4A 103.0 . . ?
C3 C4 H4B 103.0 . . ?
C5 C4 H4B 103.0 . . ?
H4A C4 H4B 105.1 . . ?
C4 C5 N3 115.1(5) . . ?
C4 C5 H5A 108.5 . . ?
N3 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
N3 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
N2 C6 C7 107.4(3) . . ?
N2 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N1 C7 C6 107.8(4) . . ?
N1 C7 H7A 110.2 . . ?
C6 C7 H7A 110.2 . . ?
N1 C7 H7B 110.2 . . ?
C6 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
N1 C8 C9 112.8(3) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 112.0(4) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N4 C10 C9 111.4(4) . . ?
N4 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N4 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        29.97
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.141

#===END

data_LHCLO4
_database_code_depnum_ccdc_archive 'CCDC 221988'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
3-(4-butylpiperazin-1-yl)-propylammonium-perchlorate
;
_chemical_formula_moiety         'C10 H25 N4, Cl O4'
_chemical_formula_sum            'C10 H25 Cl N4 O4'
_chemical_formula_weight         300.79

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   8.1268(4)
_cell_length_b                   12.7796(6)
_cell_length_c                   14.7831(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.3610(10)
_cell_angle_gamma                90.00
_cell_volume                     1487.36(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6004
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      13.5

_exptl_crystal_description       prism
_exptl_crystal_colour            'light red'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22623
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4341
_reflns_number_gt                3467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker-Axs Inc.)'
_computing_cell_refinement       'SAINT (Bruker-Axs Inc.)'
_computing_data_reduction        'SAINT (Bruker-axs Inc.)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+0.1393P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4341
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17629(15) 0.21994(10) -0.24464(8) 0.0418(2) Uani 1 1 d . . .
N2 N 0.20327(15) 0.29249(9) -0.05491(7) 0.0432(3) Uani 1 1 d . . .
N3 N -0.01852(14) 0.22353(8) 0.06009(7) 0.0387(2) Uani 1 1 d . . .
N4 N -0.2986(2) -0.00964(13) 0.24127(14) 0.0659(4) Uani 1 1 d . . .
Cl1 Cl -0.25608(4) 0.10452(3) -0.25752(2) 0.04653(12) Uani 1 1 d . . .
O1 O -0.2849(2) 0.04311(11) -0.18241(10) 0.0765(4) Uani 1 1 d . . .
O2 O -0.40872(16) 0.10952(13) -0.32896(9) 0.0778(4) Uani 1 1 d . . .
O3 O -0.2037(2) 0.20718(11) -0.22480(11) 0.0825(4) Uani 1 1 d . . .
O4 O -0.12636(18) 0.05905(13) -0.29411(12) 0.0841(4) Uani 1 1 d . . .
C1 C 0.33386(19) 0.28286(13) -0.23323(10) 0.0482(3) Uani 1 1 d . . .
C2 C 0.44038(19) 0.28202(15) -0.13390(10) 0.0546(4) Uani 1 1 d . . .
C3 C 0.3618(2) 0.34079(15) -0.06616(11) 0.0561(4) Uani 1 1 d . . .
C4 C 0.1087(2) 0.36590(11) -0.01098(11) 0.0526(4) Uani 1 1 d . . .
C5 C -0.0534(2) 0.31737(11) 0.00087(10) 0.0481(3) Uani 1 1 d . . .
C6 C 0.07771(18) 0.14943(10) 0.01702(9) 0.0433(3) Uani 1 1 d . . .
C7 C 0.23884(19) 0.19819(12) 0.00305(10) 0.0462(3) Uani 1 1 d . . .
C8 C -0.18018(18) 0.17710(11) 0.06764(10) 0.0454(3) Uani 1 1 d . . .
C9 C -0.15823(18) 0.09305(11) 0.14244(11) 0.0465(3) Uani 1 1 d . . .
C10 C -0.3261(2) 0.06090(13) 0.16080(15) 0.0574(4) Uani 1 1 d . . .
H1A H 0.304(2) 0.3486(16) -0.2540(13) 0.057(5) Uiso 1 1 d . . .
H1B H 0.387(2) 0.2503(13) -0.2794(12) 0.052(4) Uiso 1 1 d . . .
H2A H 0.460(2) 0.2043(14) -0.1130(12) 0.054(5) Uiso 1 1 d . . .
H2B H 0.544(3) 0.3137(16) -0.1338(16) 0.079(6) Uiso 1 1 d . . .
H3A H 0.442(3) 0.3501(16) -0.0092(15) 0.070(6) Uiso 1 1 d . . .
H3B H 0.339(2) 0.4094(16) -0.0844(14) 0.060(5) Uiso 1 1 d . . .
H4A H 0.187(2) 0.3905(15) 0.0501(14) 0.063(5) Uiso 1 1 d . . .
H4B H 0.086(2) 0.4258(14) -0.0524(13) 0.056(5) Uiso 1 1 d . . .
H5A H -0.1094(19) 0.3659(12) 0.0299(11) 0.043(4) Uiso 1 1 d . . .
H5B H -0.124(2) 0.3005(13) -0.0579(13) 0.053(5) Uiso 1 1 d . . .
H6A H 0.004(2) 0.1239(14) -0.0435(13) 0.054(4) Uiso 1 1 d . . .
H6B H 0.106(2) 0.0905(13) 0.0562(12) 0.048(4) Uiso 1 1 d . . .
H7A H 0.291(2) 0.1482(15) -0.0275(14) 0.059(5) Uiso 1 1 d . . .
H7B H 0.317(2) 0.2173(14) 0.0597(13) 0.061(5) Uiso 1 1 d . . .
H8A H -0.241(2) 0.1478(15) 0.0073(14) 0.064(5) Uiso 1 1 d . . .
H8B H -0.250(2) 0.2329(14) 0.0806(12) 0.054(4) Uiso 1 1 d . . .
H9A H -0.098(2) 0.0339(15) 0.1258(13) 0.062(5) Uiso 1 1 d . . .
H9B H -0.083(2) 0.1218(14) 0.2013(14) 0.057(5) Uiso 1 1 d . . .
H10A H -0.392(3) 0.0239(17) 0.1094(17) 0.080(6) Uiso 1 1 d . . .
H10B H -0.384(3) 0.1195(17) 0.1688(14) 0.068(6) Uiso 1 1 d . . .
H11A H 0.111(2) 0.2297(14) -0.3010(13) 0.053(4) Uiso 1 1 d . . .
H11B H 0.127(2) 0.2377(12) -0.2045(12) 0.041(4) Uiso 1 1 d . . .
H11C H 0.202(2) 0.1577(15) -0.2429(11) 0.044(4) Uiso 1 1 d . . .
H12A H -0.373(3) -0.0165(19) 0.2533(17) 0.080(8) Uiso 1 1 d . . .
H12B H -0.229(4) 0.028(2) 0.290(2) 0.106(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0404(6) 0.0501(7) 0.0351(5) 0.0027(4) 0.0097(4) 0.0035(5)
N2 0.0529(6) 0.0458(6) 0.0313(5) 0.0016(4) 0.0114(4) -0.0007(5)
N3 0.0462(6) 0.0369(5) 0.0334(5) 0.0008(4) 0.0107(4) 0.0054(4)
N4 0.0588(9) 0.0556(8) 0.0938(12) 0.0107(8) 0.0389(9) -0.0039(7)
Cl1 0.04289(19) 0.0515(2) 0.04395(19) 0.00415(12) 0.00833(13) -0.00411(12)
O1 0.0880(9) 0.0764(8) 0.0648(8) 0.0226(6) 0.0180(7) -0.0120(7)
O2 0.0526(7) 0.1124(11) 0.0602(7) 0.0090(7) -0.0017(6) -0.0015(7)
O3 0.1082(11) 0.0644(8) 0.0778(9) -0.0105(7) 0.0289(8) -0.0264(7)
O4 0.0643(8) 0.0990(11) 0.0961(11) -0.0035(9) 0.0331(7) 0.0113(7)
C1 0.0484(7) 0.0592(9) 0.0379(6) 0.0072(6) 0.0127(5) -0.0047(6)
C2 0.0409(7) 0.0797(11) 0.0415(7) 0.0059(7) 0.0069(5) -0.0077(7)
C3 0.0596(9) 0.0673(10) 0.0387(7) -0.0027(6) 0.0073(6) -0.0168(7)
C4 0.0785(11) 0.0377(6) 0.0451(7) 0.0012(5) 0.0219(7) 0.0028(6)
C5 0.0629(9) 0.0405(6) 0.0422(7) 0.0047(5) 0.0157(6) 0.0133(6)
C6 0.0539(7) 0.0381(6) 0.0400(6) 0.0019(5) 0.0154(6) 0.0087(5)
C7 0.0511(7) 0.0512(8) 0.0369(6) 0.0048(5) 0.0119(6) 0.0089(6)
C8 0.0431(7) 0.0461(7) 0.0456(7) -0.0006(5) 0.0085(5) 0.0055(5)
C9 0.0435(7) 0.0417(7) 0.0563(8) 0.0027(6) 0.0161(6) 0.0024(5)
C10 0.0440(7) 0.0485(8) 0.0824(12) 0.0033(8) 0.0206(7) 0.0002(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4858(19) . ?
N1 H11A 0.878(19) . ?
N1 H11B 0.823(17) . ?
N1 H11C 0.822(19) . ?
N2 C4 1.4632(18) . ?
N2 C7 1.4653(17) . ?
N2 C3 1.475(2) . ?
N3 C6 1.4700(16) . ?
N3 C5 1.4703(16) . ?
N3 C8 1.4707(18) . ?
N4 C10 1.465(3) . ?
N4 H12A 0.68(3) . ?
N4 H12B 0.93(3) . ?
Cl1 O2 1.4171(12) . ?
Cl1 O4 1.4227(14) . ?
Cl1 O1 1.4259(13) . ?
Cl1 O3 1.4263(14) . ?
C1 C2 1.508(2) . ?
C1 H1A 0.91(2) . ?
C1 H1B 0.988(17) . ?
C2 C3 1.514(2) . ?
C2 H2A 1.041(17) . ?
C2 H2B 0.93(2) . ?
C3 H3A 0.94(2) . ?
C3 H3B 0.92(2) . ?
C4 C5 1.505(2) . ?
C4 H4A 1.02(2) . ?
C4 H4B 0.970(18) . ?
C5 H5A 0.934(16) . ?
C5 H5B 0.939(19) . ?
C6 C7 1.510(2) . ?
C6 H6A 1.001(19) . ?
C6 H6B 0.944(17) . ?
C7 H7A 0.94(2) . ?
C7 H7B 0.947(19) . ?
C8 C9 1.520(2) . ?
C8 H8A 0.98(2) . ?
C8 H8B 0.961(18) . ?
C9 C10 1.512(2) . ?
C9 H9A 0.963(19) . ?
C9 H9B 1.001(19) . ?
C10 H10A 0.94(2) . ?
C10 H10B 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H11A 109.3(11) . . ?
C1 N1 H11B 109.0(11) . . ?
H11A N1 H11B 111.1(15) . . ?
C1 N1 H11C 108.1(12) . . ?
H11A N1 H11C 104.9(16) . . ?
H11B N1 H11C 114.3(16) . . ?
C4 N2 C7 108.48(10) . . ?
C4 N2 C3 110.58(12) . . ?
C7 N2 C3 111.04(12) . . ?
C6 N3 C5 108.19(10) . . ?
C6 N3 C8 110.74(11) . . ?
C5 N3 C8 109.29(11) . . ?
C10 N4 H12A 109(2) . . ?
C10 N4 H12B 104.0(18) . . ?
H12A N4 H12B 106(3) . . ?
O2 Cl1 O4 109.23(10) . . ?
O2 Cl1 O1 108.81(9) . . ?
O4 Cl1 O1 110.59(10) . . ?
O2 Cl1 O3 110.12(10) . . ?
O4 Cl1 O3 108.52(10) . . ?
O1 Cl1 O3 109.58(9) . . ?
N1 C1 C2 112.15(12) . . ?
N1 C1 H1A 108.0(12) . . ?
C2 C1 H1A 112.2(12) . . ?
N1 C1 H1B 102.1(10) . . ?
C2 C1 H1B 115.1(10) . . ?
H1A C1 H1B 106.6(16) . . ?
C1 C2 C3 113.95(14) . . ?
C1 C2 H2A 107.8(10) . . ?
C3 C2 H2A 109.7(10) . . ?
C1 C2 H2B 107.3(14) . . ?
C3 C2 H2B 108.1(13) . . ?
H2A C2 H2B 109.9(16) . . ?
N2 C3 C2 112.99(13) . . ?
N2 C3 H3A 112.7(12) . . ?
C2 C3 H3A 110.1(13) . . ?
N2 C3 H3B 108.4(12) . . ?
C2 C3 H3B 111.4(12) . . ?
H3A C3 H3B 100.7(17) . . ?
N2 C4 C5 111.03(12) . . ?
N2 C4 H4A 108.1(11) . . ?
C5 C4 H4A 113.4(11) . . ?
N2 C4 H4B 105.5(11) . . ?
C5 C4 H4B 111.2(10) . . ?
H4A C4 H4B 107.3(15) . . ?
N3 C5 C4 111.13(12) . . ?
N3 C5 H5A 108.1(10) . . ?
C4 C5 H5A 108.7(9) . . ?
N3 C5 H5B 110.3(10) . . ?
C4 C5 H5B 109.6(11) . . ?
H5A C5 H5B 108.9(14) . . ?
N3 C6 C7 111.46(11) . . ?
N3 C6 H6A 109.3(10) . . ?
C7 C6 H6A 111.2(10) . . ?
N3 C6 H6B 108.8(10) . . ?
C7 C6 H6B 109.1(10) . . ?
H6A C6 H6B 106.9(14) . . ?
N2 C7 C6 111.56(11) . . ?
N2 C7 H7A 109.0(12) . . ?
C6 C7 H7A 107.1(11) . . ?
N2 C7 H7B 107.2(11) . . ?
C6 C7 H7B 113.4(11) . . ?
H7A C7 H7B 108.5(16) . . ?
N3 C8 C9 113.23(11) . . ?
N3 C8 H8A 110.0(11) . . ?
C9 C8 H8A 109.5(11) . . ?
N3 C8 H8B 107.5(11) . . ?
C9 C8 H8B 110.4(10) . . ?
H8A C8 H8B 106.0(15) . . ?
C10 C9 C8 111.98(13) . . ?
C10 C9 H9A 111.5(11) . . ?
C8 C9 H9A 110.2(11) . . ?
C10 C9 H9B 109.2(10) . . ?
C8 C9 H9B 108.0(10) . . ?
H9A C9 H9B 105.8(14) . . ?
N4 C10 C9 110.51(14) . . ?
N4 C10 H10A 106.7(14) . . ?
C9 C10 H10A 110.7(14) . . ?
N4 C10 H10B 112.4(13) . . ?
C9 C10 H10B 108.7(12) . . ?
H10A C10 H10B 107.9(18) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -69.05(19) . . . . ?
C4 N2 C3 C2 -164.07(13) . . . . ?
C7 N2 C3 C2 75.45(16) . . . . ?
C1 C2 C3 N2 65.24(19) . . . . ?
C7 N2 C4 C5 -57.98(16) . . . . ?
C3 N2 C4 C5 -179.98(12) . . . . ?
C6 N3 C5 C4 -57.78(15) . . . . ?
C8 N3 C5 C4 -178.45(11) . . . . ?
N2 C4 C5 N3 60.18(16) . . . . ?
C5 N3 C6 C7 56.60(14) . . . . ?
C8 N3 C6 C7 176.35(10) . . . . ?
C4 N2 C7 C6 56.91(15) . . . . ?
C3 N2 C7 C6 178.63(11) . . . . ?
N3 C6 C7 N2 -57.90(15) . . . . ?
C6 N3 C8 C9 72.46(14) . . . . ?
C5 N3 C8 C9 -168.44(12) . . . . ?
N3 C8 C9 C10 169.57(13) . . . . ?
C8 C9 C10 N4 -172.57(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.053

#===END