Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2003

data_global
_publ_contact_author_email       DELGADO@ITQB.UNL.PT
_publ_contact_author_name        'Prof Rita Delgado'
_journal_name_full               'Dalton Trans.'
_journal_coden_Cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
R.Delgado
P.Antunes
P.M.Campello
M.G.B.Drew
V.Felix
I.Santos

data_[bz[14]N4H3]Cl3
_database_code_CSD               202378

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
? 
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H31 Cl3 N4 O2'
_chemical_formula_weight         393.78

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   P21/c

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                   10.264(11)
_cell_length_b                   16.020(17)
_cell_length_c                   12.105(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.140(10)
_cell_angle_gamma                90.00
_cell_volume                     1985(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_type   'No absorption correction'
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_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  'fine-focus sealed tube'
_diffrn_measurement_method       'MAR research image plate system'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6590
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         26.21
_reflns_number_total             3538
_reflns_number_gt                2338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'W. Kabsch, J. Appl. Crystallogr. 21,916,1983'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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 w=1/[\s^2^(Fo^2^)+(0.1232P)^2^+0.3122P] 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       0.007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3538
_refine_ls_number_parameters     224
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.2297
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77720(12) 0.21836(8) 0.22948(9) 0.0453(4) Uani 1 d . . .
Cl2 Cl 0.23670(13) 0.24805(9) 0.28181(11) 0.0573(4) Uani 1 d . . .
Cl3 Cl 0.46573(14) 0.01495(9) -0.32773(11) 0.0600(4) Uani 1 d . . .
C1 C 0.8445(5) 0.0820(3) -0.4332(3) 0.0403(11) Uani 1 d . . .
C2 C 0.9726(5) 0.1109(3) -0.4273(4) 0.0420(11) Uani 1 d . . .
C3 C 1.0689(5) 0.0646(3) -0.3680(4) 0.0516(13) Uani 1 d . . .
H3 H 1.1546 0.0837 -0.3636 0.062 Uiso 1 calc R . .
C4 C 1.0404(7) -0.0082(3) -0.3159(4) 0.0597(15) Uani 1 d . . .
H4 H 1.1064 -0.0380 -0.2767 0.072 Uiso 1 calc R . .
C5 C 0.9128(6) -0.0377(3) -0.3218(4) 0.0591(15) Uani 1 d . . .
H5 H 0.8924 -0.0868 -0.2858 0.071 Uiso 1 calc R . .
C6 C 0.8177(6) 0.0065(3) -0.3812(4) 0.0510(13) Uani 1 d . . .
H6 H 0.7328 -0.0141 -0.3872 0.061 Uiso 1 calc R . .
C7 C 0.7351(5) 0.1243(4) -0.5010(4) 0.0506(13) Uani 1 d . . .
H7A H 0.6980 0.0859 -0.5566 0.061 Uiso 1 calc R . .
H7B H 0.7692 0.1721 -0.5388 0.061 Uiso 1 calc R . .
N8 N 0.6301(4) 0.1527(3) -0.4285(3) 0.0430(9) Uani 1 d D . .
H8A H 0.6015 0.1082 -0.3918 0.052 Uiso 1 calc RD . .
H8B H 0.6654 0.1888 -0.3778 0.052 Uiso 1 calc RD . .
C9 C 0.5150(5) 0.1939(3) -0.4904(4) 0.0508(13) Uani 1 d . . .
H9A H 0.4516 0.2084 -0.4379 0.061 Uiso 1 calc R . .
H9B H 0.4742 0.1538 -0.5421 0.061 Uiso 1 calc R . .
C10 C 0.5479(5) 0.2715(3) -0.5536(4) 0.0487(12) Uani 1 d . . .
H10A H 0.6178 0.2587 -0.6006 0.058 Uiso 1 calc R . .
H10B H 0.4720 0.2879 -0.6011 0.058 Uiso 1 calc R . .
N11 N 0.5884(4) 0.3425(2) -0.4806(3) 0.0424(10) Uani 1 d D . .
H11A H 0.6591 0.3273 -0.4369 0.051 Uiso 1 calc RD . .
H11B H 0.5238 0.3539 -0.4365 0.051 Uiso 1 calc RD . .
C12 C 0.6202(5) 0.4203(3) -0.5421(4) 0.0507(12) Uani 1 d . . .
H12A H 0.5510 0.4309 -0.5993 0.061 Uiso 1 calc R . .
H12B H 0.6229 0.4672 -0.4912 0.061 Uiso 1 calc R . .
C13 C 0.7468(5) 0.4154(3) -0.5940(4) 0.0518(13) Uani 1 d . . .
H13A H 0.7395 0.3765 -0.6555 0.062 Uiso 1 calc R . .
H13B H 0.7692 0.4698 -0.6223 0.062 Uiso 1 calc R . .
N14 N 0.8483(4) 0.3878(3) -0.5128(4) 0.0553(11) Uani 1 d D . .
H14A H 0.858(6) 0.424(3) -0.459(4) 0.066 Uiso 1 d D . .
C15 C 0.9753(5) 0.3736(3) -0.5564(4) 0.0522(13) Uani 1 d . . .
H15A H 1.0083 0.4258 -0.5839 0.063 Uiso 1 calc R . .
H15B H 0.9657 0.3346 -0.6177 0.063 Uiso 1 calc R . .
C16 C 1.0705(5) 0.3394(3) -0.4685(4) 0.0467(12) Uani 1 d . . .
H16A H 1.1518 0.3267 -0.5011 0.056 Uiso 1 calc R . .
H16B H 1.0887 0.3819 -0.4124 0.056 Uiso 1 calc R . .
N17 N 1.0234(4) 0.2626(2) -0.4143(3) 0.0404(9) Uani 1 d D . .
H17A H 0.9436 0.2727 -0.3911 0.048 Uiso 1 calc RD . .
H17B H 1.0772 0.2515 -0.3541 0.048 Uiso 1 calc RD . .
C18 C 1.0161(5) 0.1874(3) -0.4875(4) 0.0499(13) Uani 1 d . . .
H18A H 1.1013 0.1771 -0.5145 0.060 Uiso 1 calc R . .
H18B H 0.9552 0.1981 -0.5509 0.060 Uiso 1 calc R . .
O100 O 0.4025(5) 0.3844(3) -0.3395(3) 0.0733(12) Uani 1 d D . .
H101 H 0.426(6) 0.416(3) -0.289(3) 0.088 Uiso 1 d D . .
H102 H 0.390(7) 0.3399(19) -0.308(4) 0.088 Uiso 1 d D . .
O200 O 0.7156(5) -0.0626(4) 0.1349(4) 0.0903(15) Uani 1 d D . .
H201 H 0.737(7) -0.109(2) 0.160(5) 0.108 Uiso 1 d D . .
H202 H 0.673(7) -0.042(4) 0.183(4) 0.108 Uiso 1 d 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
Cl1 0.0530(8) 0.0513(8) 0.0317(6) 0.0010(5) 0.0044(5) 0.0052(5)
Cl2 0.0558(9) 0.0563(9) 0.0574(8) -0.0056(6) -0.0122(6) 0.0000(6)
Cl3 0.0619(9) 0.0556(9) 0.0637(9) 0.0056(6) 0.0132(6) -0.0131(7)
C1 0.049(3) 0.041(3) 0.032(2) -0.0059(18) 0.0085(18) -0.002(2)
C2 0.050(3) 0.038(3) 0.039(3) -0.0024(19) 0.007(2) -0.004(2)
C3 0.060(3) 0.055(3) 0.040(3) -0.005(2) 0.004(2) 0.001(3)
C4 0.084(5) 0.048(3) 0.047(3) 0.005(2) 0.004(3) 0.020(3)
C5 0.094(5) 0.035(3) 0.050(3) 0.001(2) 0.021(3) 0.005(3)
C6 0.064(3) 0.045(3) 0.045(3) -0.004(2) 0.014(2) -0.007(3)
C7 0.047(3) 0.062(4) 0.043(3) -0.003(2) 0.005(2) 0.001(3)
N8 0.049(2) 0.039(2) 0.040(2) -0.0012(16) 0.0004(17) -0.0069(18)
C9 0.038(3) 0.051(3) 0.062(3) 0.003(2) -0.004(2) -0.009(2)
C10 0.059(3) 0.046(3) 0.039(3) -0.004(2) -0.010(2) 0.005(2)
N11 0.039(2) 0.046(3) 0.043(2) 0.0015(17) 0.0042(16) 0.0011(18)
C12 0.060(3) 0.040(3) 0.052(3) 0.001(2) 0.000(2) 0.005(2)
C13 0.050(3) 0.046(3) 0.060(3) 0.008(2) 0.010(2) 0.009(2)
N14 0.049(3) 0.059(3) 0.058(3) 0.008(2) 0.007(2) -0.004(2)
C15 0.047(3) 0.055(3) 0.055(3) 0.014(2) 0.006(2) -0.009(2)
C16 0.040(3) 0.045(3) 0.055(3) 0.003(2) 0.002(2) -0.009(2)
N17 0.046(2) 0.039(2) 0.036(2) 0.0026(16) 0.0023(16) -0.0016(18)
C18 0.069(4) 0.048(3) 0.033(3) -0.001(2) 0.007(2) -0.008(3)
O100 0.079(3) 0.084(3) 0.059(3) -0.011(2) 0.023(2) -0.005(3)
O200 0.093(4) 0.106(4) 0.072(3) 0.021(3) 0.007(2) 0.035(3)

_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
C1 C2 1.391(7) . ?
C1 C6 1.399(7) . ?
C1 C7 1.503(7) . ?
C2 C3 1.393(7) . ?
C2 C18 1.509(7) . ?
C3 C4 1.367(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N8 1.509(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N8 C9 1.504(6) . ?
N8 H8A 0.9000 . ?
N8 H8B 0.9000 . ?
C9 C10 1.511(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N11 1.482(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N11 C12 1.499(6) . ?
N11 H11A 0.9000 . ?
N11 H11B 0.9000 . ?
C12 C13 1.486(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N14 1.449(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N14 C15 1.458(7) . ?
N14 H14A 0.864(10) . ?
C15 C16 1.496(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N17 1.490(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N17 C18 1.494(6) . ?
N17 H17A 0.9000 . ?
N17 H17B 0.9000 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O100 H101 0.821(10) . ?
O100 H102 0.822(10) . ?
O200 H201 0.822(10) . ?
O200 H202 0.822(10) . ?

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
C2 C1 C6 118.7(5) . . ?
C2 C1 C7 122.9(4) . . ?
C6 C1 C7 118.1(5) . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 C18 123.9(4) . . ?
C3 C2 C18 117.3(5) . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.9(5) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C1 C7 N8 110.8(4) . . ?
C1 C7 H7A 109.5 . . ?
N8 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
N8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 N8 C7 114.2(4) . . ?
C9 N8 H8A 108.7 . . ?
C7 N8 H8A 108.7 . . ?
C9 N8 H8B 108.7 . . ?
C7 N8 H8B 108.7 . . ?
H8A N8 H8B 107.6 . . ?
N8 C9 C10 114.7(4) . . ?
N8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N11 C10 C9 113.2(4) . . ?
N11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C10 N11 C12 113.8(4) . . ?
C10 N11 H11A 108.8 . . ?
C12 N11 H11A 108.8 . . ?
C10 N11 H11B 108.8 . . ?
C12 N11 H11B 108.8 . . ?
H11A N11 H11B 107.7 . . ?
C13 C12 N11 113.2(4) . . ?
C13 C12 H12A 108.9 . . ?
N11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
N11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
N14 C13 C12 109.7(4) . . ?
N14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 N14 C15 114.8(4) . . ?
C13 N14 H14A 110(4) . . ?
C15 N14 H14A 109(4) . . ?
N14 C15 C16 110.8(4) . . ?
N14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N17 C16 C15 113.5(4) . . ?
N17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
N17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 N17 C18 114.1(4) . . ?
C16 N17 H17A 108.7 . . ?
C18 N17 H17A 108.7 . . ?
C16 N17 H17B 108.7 . . ?
C18 N17 H17B 108.7 . . ?
H17A N17 H17B 107.6 . . ?
N17 C18 C2 111.9(4) . . ?
N17 C18 H18A 109.2 . . ?
C2 C18 H18A 109.2 . . ?
N17 C18 H18B 109.2 . . ?
C2 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
H101 O100 H102 104.0(17) . . ?
H201 O200 H202 104.5(17) . . ?

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
C6 C1 C2 C3 -1.3(6) . . . . ?
C7 C1 C2 C3 -176.0(4) . . . . ?
C6 C1 C2 C18 174.8(4) . . . . ?
C7 C1 C2 C18 0.1(7) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C18 C2 C3 C4 -176.3(5) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
C4 C5 C6 C1 -2.2(8) . . . . ?
C2 C1 C6 C5 2.4(7) . . . . ?
C7 C1 C6 C5 177.3(4) . . . . ?
C2 C1 C7 N8 -119.7(5) . . . . ?
C6 C1 C7 N8 65.6(6) . . . . ?
C1 C7 N8 C9 -178.5(4) . . . . ?
C7 N8 C9 C10 -60.1(6) . . . . ?
N8 C9 C10 N11 -68.9(6) . . . . ?
C9 C10 N11 C12 -179.5(4) . . . . ?
C10 N11 C12 C13 -73.7(6) . . . . ?
N11 C12 C13 N14 -50.4(6) . . . . ?
C12 C13 N14 C15 175.0(4) . . . . ?
C13 N14 C15 C16 -175.8(4) . . . . ?
N14 C15 C16 N17 54.4(6) . . . . ?
C15 C16 N17 C18 69.6(5) . . . . ?
C16 N17 C18 C2 177.9(4) . . . . ?
C1 C2 C18 N17 97.3(5) . . . . ?
C3 C2 C18 N17 -86.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.855
_diffrn_reflns_theta_full        26.21
_diffrn_measured_fraction_theta_full 0.855
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.078