# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Carlos Platas-Iglesias'
_publ_contact_author_email       CPLATAS@UDC.ES

_publ_section_title              
;
A hexaaza macrocyclic ligand containing acetohydrazide
pendants for Ln(III) complexation in aqueous solution. Solid state and
solution structures and DFT calculations
;

_publ_requested_category         FO
loop_
_publ_author_name
'Carlos Platas-Iglesias'
'Rufina Bastida'
'Alejandro Macias'
'Marta Mato-Iglesias'
'Cristina Nunez'
;
L.Valencia
;

data_ba14cn2n
_database_code_depnum_ccdc_archive 'CCDC 675887'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C26H42N14O4
_chemical_formula_sum            'C26 H42 N14 O4'
_chemical_formula_weight         614.74

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7622(2)
_cell_length_b                   9.1199(3)
_cell_length_c                   12.1420(3)
_cell_angle_alpha                101.326(2)
_cell_angle_beta                 103.901(2)
_cell_angle_gamma                97.016(2)
_cell_volume                     701.35(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1940
_cell_measurement_theta_min      3.1505
_cell_measurement_theta_max      26.2045

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9846
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_process_details   sadabs

_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 X8 KappaAPEXII'
_diffrn_measurement_method       'omega/phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14387
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3222
_reflns_number_gt                2242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER APEX'
_computing_cell_refinement       'BRUKER APEX'
_computing_data_reduction        'BRUKER Shelxtl'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_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^)+(0.0560P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3222
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8070(3) 0.2912(2) 0.46163(15) 0.0178(4) Uani 1 1 d . . .
C2 C 0.7356(3) 0.4268(2) 0.48358(17) 0.0208(4) Uani 1 1 d . . .
H2 H 0.6516 0.4581 0.4231 0.025 Uiso 1 1 calc R . .
C3 C 0.7905(3) 0.5162(2) 0.59690(17) 0.0239(4) Uani 1 1 d . . .
H3 H 0.7462 0.6088 0.6127 0.029 Uiso 1 1 calc R . .
C4 C 0.9110(3) 0.4658(2) 0.68514(16) 0.0220(4) Uani 1 1 d . . .
H4 H 0.9502 0.5240 0.7614 0.026 Uiso 1 1 calc R . .
C5 C 0.9731(3) 0.3265(2) 0.65854(15) 0.0183(4) Uani 1 1 d . . .
C6 C 1.1010(3) 0.2616(2) 0.75094(16) 0.0209(4) Uani 1 1 d . . .
H6A H 1.0804 0.3073 0.8256 0.025 Uiso 1 1 calc R . .
H6B H 1.0484 0.1535 0.7342 0.025 Uiso 1 1 calc R . .
C7 C 1.3870(3) 0.2175(2) 0.65946(15) 0.0204(4) Uani 1 1 d . . .
H7A H 1.5370 0.2336 0.6792 0.024 Uiso 1 1 calc R . .
H7B H 1.3404 0.2716 0.5996 0.024 Uiso 1 1 calc R . .
C8 C 0.6951(3) -0.0501(2) 0.39038(15) 0.0185(4) Uani 1 1 d . . .
H8A H 0.6555 -0.0190 0.4619 0.022 Uiso 1 1 calc R . .
H8B H 0.8452 -0.0336 0.4103 0.022 Uiso 1 1 calc R . .
C9 C 0.7635(3) 0.1930(2) 0.33870(15) 0.0184(4) Uani 1 1 d . . .
H9A H 0.7070 0.2516 0.2839 0.022 Uiso 1 1 calc R . .
H9B H 0.8943 0.1724 0.3255 0.022 Uiso 1 1 calc R . .
C10 C 1.4357(3) 0.4380(2) 0.81595(16) 0.0216(4) Uani 1 1 d . . .
H10A H 1.3467 0.4967 0.8508 0.026 Uiso 1 1 calc R . .
H10B H 1.4694 0.4846 0.7559 0.026 Uiso 1 1 calc R . .
C11 C 1.6328(3) 0.4428(2) 0.90841(16) 0.0200(4) Uani 1 1 d . A .
C12 C 0.4073(3) 0.0655(2) 0.30356(15) 0.0178(4) Uani 1 1 d . . .
H12A H 0.4075 0.1503 0.3659 0.021 Uiso 1 1 calc R . .
H12B H 0.3339 -0.0249 0.3167 0.021 Uiso 1 1 calc R . .
C13 C 0.2891(3) 0.0930(2) 0.18860(16) 0.0183(4) Uani 1 1 d . . .
N1 N 0.9248(2) 0.24185(16) 0.54838(13) 0.0191(3) Uani 1 1 d . . .
N2 N 1.3247(2) 0.28284(16) 0.76263(13) 0.0192(3) Uani 1 1 d . . .
N3 N 0.6209(2) 0.04653(16) 0.31111(12) 0.0162(3) Uani 1 1 d . . .
N4 N 1.6580(2) 0.31101(19) 0.93544(14) 0.0248(4) Uani 1 1 d . . .
N5 N 1.8189(5) 0.3124(14) 1.0372(10) 0.026(2) Uani 0.73(4) 1 d P A 1
N5' N 1.840(3) 0.258(3) 0.996(3) 0.030(5) Uani 0.27(4) 1 d P A 2
N6 N 0.3808(2) 0.07032(18) 0.10211(13) 0.0198(3) Uani 1 1 d . . .
N7 N 0.2946(3) 0.0933(2) -0.01061(14) 0.0234(4) Uani 1 1 d . . .
O1 O 1.75819(19) 0.56316(15) 0.95486(12) 0.0287(3) Uani 1 1 d . . .
O2 O 0.1174(2) 0.12888(16) 0.17692(12) 0.0303(4) Uani 1 1 d . . .
H6N H 0.507(3) 0.039(2) 0.1165(18) 0.031(6) Uiso 1 1 d . . .
H7N H 0.176(4) 0.028(3) -0.043(2) 0.040(7) Uiso 1 1 d . . .
H7M H 0.277(4) 0.186(3) 0.002(2) 0.046(7) Uiso 1 1 d . . .
H4N H 1.549(4) 0.225(3) 0.898(2) 0.048(7) Uiso 1 1 d . . .
H5M H 1.933(4) 0.355(3) 1.018(2) 0.049(7) Uiso 1 1 d . . .
H5N H 1.817(5) 0.221(4) 1.048(3) 0.086(12) 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
C1 0.0134(8) 0.0194(9) 0.0196(9) 0.0052(8) 0.0035(7) -0.0001(7)
C2 0.0160(9) 0.0214(10) 0.0255(10) 0.0075(8) 0.0036(8) 0.0056(7)
C3 0.0198(9) 0.0183(10) 0.0327(11) 0.0025(9) 0.0077(9) 0.0052(8)
C4 0.0166(9) 0.0245(10) 0.0205(10) -0.0013(8) 0.0040(8) -0.0001(8)
C5 0.0138(8) 0.0206(10) 0.0179(9) 0.0023(8) 0.0031(7) 0.0001(7)
C6 0.0202(9) 0.0247(10) 0.0153(9) 0.0028(8) 0.0023(8) 0.0025(8)
C7 0.0217(9) 0.0198(10) 0.0201(10) 0.0061(8) 0.0044(8) 0.0054(8)
C8 0.0201(9) 0.0195(9) 0.0164(9) 0.0048(7) 0.0043(7) 0.0056(7)
C9 0.0168(9) 0.0205(10) 0.0181(9) 0.0074(8) 0.0031(7) 0.0029(7)
C10 0.0235(10) 0.0186(10) 0.0195(10) 0.0028(8) 0.0015(8) 0.0038(8)
C11 0.0177(9) 0.0225(10) 0.0186(9) 0.0022(8) 0.0054(8) 0.0029(8)
C12 0.0204(9) 0.0176(9) 0.0172(9) 0.0044(7) 0.0073(8) 0.0044(7)
C13 0.0182(9) 0.0171(9) 0.0211(10) 0.0062(8) 0.0057(8) 0.0053(7)
N1 0.0172(8) 0.0181(8) 0.0190(8) 0.0034(7) 0.0011(6) 0.0011(6)
N2 0.0178(8) 0.0182(8) 0.0182(8) 0.0017(6) 0.0008(6) 0.0031(6)
N3 0.0146(7) 0.0174(8) 0.0162(8) 0.0059(6) 0.0019(6) 0.0029(6)
N4 0.0195(8) 0.0272(9) 0.0248(9) 0.0083(8) -0.0005(7) 0.0030(7)
N5 0.0185(14) 0.026(3) 0.031(3) 0.010(3) -0.0015(14) 0.0056(14)
N5' 0.027(5) 0.023(8) 0.029(8) -0.002(7) -0.006(5) 0.001(5)
N6 0.0189(8) 0.0284(9) 0.0152(8) 0.0091(7) 0.0039(7) 0.0106(7)
N7 0.0194(9) 0.0320(11) 0.0201(9) 0.0120(8) 0.0020(7) 0.0071(8)
O1 0.0224(7) 0.0266(8) 0.0307(8) 0.0029(6) 0.0021(6) -0.0029(6)
O2 0.0219(7) 0.0459(9) 0.0320(8) 0.0182(7) 0.0106(6) 0.0179(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
C1 N1 1.348(2) . ?
C1 C2 1.383(3) . ?
C1 C9 1.522(2) . ?
C2 C3 1.391(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.389(3) . ?
C5 N1 1.347(2) . ?
C5 C6 1.509(3) . ?
C6 N2 1.469(2) . ?
C7 N2 1.457(2) . ?
C7 C8 1.507(2) 2_756 ?
C8 N3 1.471(2) . ?
C8 C7 1.507(2) 2_756 ?
C9 N3 1.477(2) . ?
C10 N2 1.460(2) . ?
C10 C11 1.512(3) . ?
C11 O1 1.242(2) . ?
C11 N4 1.326(2) . ?
C12 N3 1.459(2) . ?
C12 C13 1.517(2) . ?
C13 O2 1.228(2) . ?
C13 N6 1.338(2) . ?
N4 N5 1.434(6) . ?
N4 N5' 1.463(19) . ?
N6 N7 1.420(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
N1 C1 C2 121.30(16) . . ?
N1 C1 C9 116.63(15) . . ?
C2 C1 C9 122.04(17) . . ?
C1 C2 C3 119.48(18) . . ?
C4 C3 C2 119.06(18) . . ?
C3 C4 C5 118.96(17) . . ?
N1 C5 C4 121.99(17) . . ?
N1 C5 C6 115.91(16) . . ?
C4 C5 C6 122.10(16) . . ?
N2 C6 C5 116.19(14) . . ?
N2 C7 C8 114.76(14) . 2_756 ?
N3 C8 C7 114.01(14) . 2_756 ?
N3 C9 C1 116.61(14) . . ?
N2 C10 C11 112.01(15) . . ?
O1 C11 N4 123.79(18) . . ?
O1 C11 C10 121.16(17) . . ?
N4 C11 C10 115.05(16) . . ?
N3 C12 C13 115.04(13) . . ?
O2 C13 N6 123.36(17) . . ?
O2 C13 C12 120.88(15) . . ?
N6 C13 C12 115.72(15) . . ?
C5 N1 C1 119.16(15) . . ?
C7 N2 C10 111.27(13) . . ?
C7 N2 C6 116.32(14) . . ?
C10 N2 C6 114.71(14) . . ?
C12 N3 C8 112.90(12) . . ?
C12 N3 C9 112.59(14) . . ?
C8 N3 C9 111.80(13) . . ?
C11 N4 N5 117.9(5) . . ?
C11 N4 N5' 132.1(6) . . ?
N5 N4 N5' 27.2(10) . . ?
C13 N6 N7 123.42(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053

# Attachment 'monoccn.cif'

data_.onoccn
_database_code_depnum_ccdc_archive 'CCDC 675888'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '[La(C26H42N14O4)]Br1.5(NO3)1.5(H2O)6'
_chemical_formula_sum            'C26 H54 Br1.50 La N15.50 O14.50'
_chemical_formula_weight         1074.57

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'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.656(2)
_cell_length_b                   10.6477(10)
_cell_length_c                   21.655(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.1460(10)
_cell_angle_gamma                90.00
_cell_volume                     4180.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      24.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2184
_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.4457
_exptl_absorpt_correction_T_max  0.8627
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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 CCD SMART1000'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15902
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.30
_reflns_number_total             4217
_reflns_number_gt                3656
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER Smart'
_computing_cell_refinement       'BRUKER Smart'
_computing_data_reduction        'BRUKER Shelxtl'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_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^)+(0.0775P)^2^+11.1164P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4217
_refine_ls_number_parameters     353
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.29824(16) 0.6285(3) 0.1777(2) 0.0384(8) Uani 0.369(8) 1 d P A 1
Br2 Br 0.2865(2) 0.6425(3) 0.1461(5) 0.0550(15) Uani 0.363(10) 1 d P B 2
N2N N 0.2865(2) 0.6425(3) 0.1461(5) 0.0550(15) Uani 0.261(8) 1 d PR C 3
O4N O 0.3057(2) 0.5878(4) 0.2036(5) 0.041(5) Uiso 0.261(8) 1 d PR C 3
O5N O 0.3268(2) 0.6422(3) 0.1226(5) 0.064(5) Uani 0.261(8) 1 d PR C 3
O6N O 0.2272(2) 0.6975(3) 0.1120(5) 0.138(12) Uani 0.261(8) 1 d PR C 3
N1N N 0.0414(4) 1.2062(9) 0.0503(5) 0.194(13) Uani 0.238(10) 1 d PRDU D 1
O1N O 0.0206(4) 1.2924(10) 0.0058(5) 0.171(14) Uani 0.238(10) 1 d PRDU D 1
O2N O 0.0106(5) 1.1039(7) 0.0310(5) 0.147(12) Uani 0.238(10) 1 d PRDU D 1
O3N O 0.0930(3) 1.2224(9) 0.1142(5) 0.163(14) Uani 0.238(10) 1 d PRDU D 1
N1N' N -0.0008(5) 1.2501(9) 0.0386(5) 0.194(11) Uani 0.304(10) 1 d PRDU E 2
O1N' O 0.0045(5) 1.3288(11) 0.0012(5) 0.194(13) Uani 0.304(10) 1 d PRDU E 2
O2N' O 0.0474(4) 1.1721(8) 0.0716(5) 0.214(12) Uani 0.304(10) 1 d PRDU E 2
O3N' O -0.0544(6) 1.2495(9) 0.0430(5) 0.220(13) Uani 0.304(10) 1 d PRDU E 2
O1W O 0.1375(11) 1.1445(17) 0.1409(9) 0.060(5) Uani 0.25 1 d P E 2
O2W O 0.0079(5) 1.2296(7) 0.0528(4) 0.057(2) Uani 0.50 1 d P F 3
O3W O 0.0169(9) 1.3760(16) -0.0106(9) 0.043(4) Uani 0.25 1 d P G 3
O4W O 0.1764(6) 1.0509(17) 0.1331(9) 0.127(6) Uani 0.50 1 d P . .
O5W O 0.1312(9) 0.9416(16) 0.0658(9) 0.123(6) Uani 0.50 1 d P E .
O6W O 0.1801(11) 0.8665(15) 0.0511(12) 0.138(6) Uani 0.50 1 d P . .
O7W O 0.2028(14) 0.834(2) 0.0175(12) 0.173(10) Uani 0.50 1 d P E .
La La 0.5000 0.17547(3) 0.2500 0.02015(13) Uani 1 2 d S . .
N1 N 0.6045(2) 0.1748(5) 0.3896(2) 0.0425(11) Uani 1 1 d . . .
C5 C 0.6228(3) 0.2806(9) 0.4285(3) 0.065(2) Uani 1 1 d . . .
C4 C 0.6719(4) 0.2811(13) 0.5037(4) 0.116(5) Uani 1 1 d . . .
H52 H 0.6824 0.3570 0.5307 0.139 Uiso 1 1 calc R . .
C3 C 0.7049(4) 0.1747(17) 0.5386(4) 0.157(8) Uani 1 1 d . . .
H53 H 0.7402 0.1758 0.5903 0.188 Uiso 1 1 calc R . .
C2 C 0.6883(3) 0.0626(13) 0.5002(4) 0.104(4) Uani 1 1 d . . .
H54 H 0.7118 -0.0137 0.5245 0.125 Uiso 1 1 calc R . .
C1 C 0.6353(3) 0.0662(8) 0.4239(3) 0.062(2) Uani 1 1 d . . .
C9 C 0.6094(3) -0.0526(7) 0.3801(4) 0.068(2) Uani 1 1 d . . .
H56A H 0.6510 -0.1128 0.4016 0.081 Uiso 1 1 calc R . .
H56B H 0.5703 -0.0898 0.3848 0.081 Uiso 1 1 calc R . .
N3 N 0.5806(2) -0.0368(4) 0.3015(3) 0.0422(11) Uani 1 1 d . . .
C8 C 0.5394(3) -0.1503(5) 0.2593(5) 0.069(2) Uani 1 1 d . . .
H58A H 0.5653 -0.2261 0.2886 0.083 Uiso 1 1 calc R . .
H58B H 0.5383 -0.1540 0.2130 0.083 Uiso 1 1 calc R . .
C12 C 0.6415(2) -0.0166(4) 0.2900(3) 0.0404(12) Uani 1 1 d . . .
H59A H 0.6705 -0.0947 0.3008 0.048 Uiso 1 1 calc R . .
H59B H 0.6749 0.0503 0.3234 0.048 Uiso 1 1 calc R . .
C13 C 0.6078(2) 0.0213(5) 0.2109(3) 0.0379(11) Uani 1 1 d . . .
O2 O 0.54653(17) 0.0745(3) 0.17595(18) 0.0381(8) Uani 1 1 d . . .
N6 N 0.6462(2) -0.0064(5) 0.1816(3) 0.0588(14) Uani 1 1 d . . .
N7 N 0.6171(3) 0.0253(7) 0.1064(3) 0.078(2) Uani 1 1 d . . .
C6 C 0.5908(3) 0.3994(8) 0.3873(4) 0.076(3) Uani 1 1 d . . .
H63A H 0.6210 0.4291 0.3686 0.091 Uiso 1 1 calc R . .
H63B H 0.5935 0.4639 0.4216 0.091 Uiso 1 1 calc R . .
N2 N 0.5130(2) 0.3868(4) 0.3242(3) 0.0466(12) Uani 1 1 d . . .
C7 C 0.4882(4) 0.4999(5) 0.2764(5) 0.073(2) Uani 1 1 d . . .
H65A H 0.5083 0.5756 0.3079 0.088 Uiso 1 1 calc R . .
H65B H 0.4337 0.5048 0.2484 0.088 Uiso 1 1 calc R . .
C10 C 0.4641(3) 0.3662(6) 0.3514(4) 0.0562(17) Uani 1 1 d . . .
H66A H 0.4594 0.4448 0.3729 0.067 Uiso 1 1 calc R . .
H66B H 0.4853 0.3008 0.3902 0.067 Uiso 1 1 calc R . .
C11 C 0.3897(3) 0.3254(4) 0.2877(3) 0.0378(11) Uani 1 1 d . . .
O1 O 0.38159(16) 0.2767(3) 0.23157(17) 0.0299(7) Uani 1 1 d . . .
N4 N 0.3345(3) 0.3405(5) 0.2972(3) 0.0522(13) Uani 1 1 d . . .
N5 N 0.2619(3) 0.3040(5) 0.2425(3) 0.0572(14) Uani 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
Br1 0.0285(9) 0.0531(14) 0.0375(15) -0.0114(13) 0.0205(10) -0.0029(7)
Br2 0.0431(14) 0.0380(12) 0.098(4) -0.0284(17) 0.048(2) -0.0130(9)
N2N 0.0431(14) 0.0380(12) 0.098(4) -0.0284(17) 0.048(2) -0.0130(9)
O5N 0.064(11) 0.064(11) 0.072(12) 0.003(9) 0.042(10) 0.000(9)
O6N 0.12(2) 0.15(3) 0.16(3) -0.01(2) 0.09(2) 0.04(2)
N1N 0.21(2) 0.096(15) 0.142(16) 0.024(12) 0.010(15) 0.052(14)
O1N 0.17(2) 0.101(17) 0.140(19) 0.025(14) 0.024(18) 0.053(17)
O2N 0.17(2) 0.113(17) 0.070(15) 0.038(12) 0.013(15) 0.024(15)
O3N 0.27(3) 0.067(16) 0.090(15) -0.019(12) 0.060(16) 0.011(18)
N1N' 0.199(19) 0.120(17) 0.157(17) -0.001(12) 0.029(14) 0.057(14)
O1N' 0.19(2) 0.14(2) 0.121(19) 0.008(13) 0.002(15) 0.074(17)
O2N' 0.22(2) 0.138(17) 0.163(17) 0.036(12) 0.025(16) 0.058(14)
O3N' 0.30(3) 0.15(2) 0.20(2) -0.098(18) 0.13(2) 0.05(2)
O1W 0.065(12) 0.043(9) 0.048(9) 0.015(7) 0.016(9) -0.004(8)
O2W 0.048(4) 0.025(4) 0.038(4) 0.000(3) -0.014(4) 0.010(3)
O3W 0.049(9) 0.044(8) 0.038(8) -0.004(7) 0.025(7) -0.004(7)
O4W 0.064(7) 0.168(14) 0.145(12) 0.116(11) 0.054(8) 0.010(8)
O5W 0.164(14) 0.134(12) 0.138(12) 0.084(11) 0.124(12) 0.043(11)
O6W 0.160(16) 0.077(9) 0.180(18) 0.010(11) 0.095(14) -0.021(10)
O7W 0.23(2) 0.20(2) 0.170(18) -0.067(15) 0.160(19) -0.046(16)
La 0.01875(19) 0.01882(19) 0.0253(2) 0.000 0.01356(14) 0.000
N1 0.025(2) 0.080(3) 0.0242(19) 0.003(2) 0.0144(17) -0.010(2)
C5 0.025(3) 0.134(7) 0.044(3) -0.039(4) 0.024(2) -0.023(4)
C4 0.026(3) 0.271(14) 0.044(4) -0.065(6) 0.015(3) -0.017(6)
C3 0.026(4) 0.42(3) 0.020(3) -0.020(7) 0.010(3) 0.003(7)
C2 0.031(3) 0.245(13) 0.042(4) 0.060(6) 0.022(3) 0.019(5)
C1 0.020(2) 0.128(6) 0.037(3) 0.039(4) 0.015(2) 0.001(3)
C9 0.030(3) 0.078(5) 0.087(5) 0.060(4) 0.027(3) 0.011(3)
N3 0.0223(19) 0.027(2) 0.075(3) 0.017(2) 0.025(2) 0.0041(16)
C8 0.035(3) 0.017(2) 0.161(7) 0.000(3) 0.057(4) 0.000(2)
C12 0.022(2) 0.024(2) 0.074(4) 0.007(2) 0.026(2) 0.0044(18)
C13 0.024(2) 0.035(2) 0.059(3) -0.018(2) 0.025(2) -0.0047(19)
O2 0.0240(16) 0.050(2) 0.0416(18) -0.0148(15) 0.0190(14) 0.0030(14)
N6 0.034(2) 0.071(4) 0.084(4) -0.031(3) 0.040(3) -0.007(2)
N7 0.047(3) 0.140(6) 0.063(3) -0.043(4) 0.040(3) -0.010(3)
C6 0.047(4) 0.103(6) 0.097(5) -0.078(5) 0.051(4) -0.046(4)
N2 0.040(2) 0.044(3) 0.074(3) -0.033(2) 0.044(2) -0.020(2)
C7 0.064(4) 0.021(3) 0.166(8) -0.019(3) 0.082(5) -0.005(3)
C10 0.044(3) 0.073(4) 0.072(4) -0.045(3) 0.045(3) -0.024(3)
C11 0.041(3) 0.030(2) 0.059(3) -0.013(2) 0.039(3) -0.005(2)
O1 0.0275(16) 0.0263(15) 0.0424(18) -0.0010(13) 0.0234(14) 0.0058(13)
N4 0.042(3) 0.062(3) 0.075(3) -0.025(2) 0.046(3) -0.007(2)
N5 0.032(2) 0.074(4) 0.074(3) -0.018(3) 0.034(2) 0.000(2)

_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
N2N O4N 1.225(2) . ?
N2N O6N 1.225(2) . ?
N2N O5N 1.225(2) . ?
N1N O1N 1.225(2) . ?
N1N O2N 1.225(2) . ?
N1N O3N 1.225(2) . ?
N1N' O1N' 1.214(2) . ?
N1N' O3N' 1.215(2) . ?
N1N' O2N' 1.215(2) . ?
O2N' O1W 1.72(2) . ?
O1W O4W 1.37(2) . ?
O4W O5W 1.69(2) . ?
O5W O6W 1.49(2) . ?
O6W O7W 1.14(2) . ?
La O2 2.551(3) 2_655 ?
La O2 2.551(3) . ?
La N1 2.603(4) . ?
La N1 2.603(4) 2_655 ?
La O1 2.604(3) . ?
La O1 2.604(3) 2_655 ?
La N2 2.688(4) . ?
La N2 2.688(4) 2_655 ?
La N3 2.697(4) 2_655 ?
La N3 2.697(4) . ?
N1 C5 1.331(9) . ?
N1 C1 1.339(8) . ?
C5 C4 1.374(9) . ?
C5 C6 1.484(12) . ?
C4 C3 1.331(19) . ?
C3 C2 1.385(18) . ?
C2 C1 1.407(8) . ?
C1 C9 1.493(11) . ?
C9 N3 1.469(8) . ?
N3 C8 1.483(7) . ?
N3 C12 1.485(6) . ?
C8 C8 1.523(10) 2_655 ?
C12 C13 1.505(8) . ?
C13 O2 1.247(6) . ?
C13 N6 1.327(7) . ?
N6 N7 1.428(8) . ?
C6 N2 1.485(8) . ?
N2 C10 1.484(6) . ?
N2 C7 1.484(9) . ?
C7 C7 1.485(14) 2_655 ?
C10 C11 1.503(8) . ?
C11 O1 1.243(6) . ?
C11 N4 1.329(6) . ?
N4 N5 1.411(7) . ?

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
O4N N2N O6N 120.0 . . ?
O4N N2N O5N 120.0 . . ?
O6N N2N O5N 120.0 . . ?
O1N N1N O2N 120.0 . . ?
O1N N1N O3N 120.0 . . ?
O2N N1N O3N 120.0 . . ?
O1N' N1N' O3N' 120.0 . . ?
O1N' N1N' O2N' 120.0 . . ?
O3N' N1N' O2N' 120.0 . . ?
N1N' O2N' O1W 146.3(7) . . ?
O4W O1W O2N' 119.7(14) . . ?
O1W O4W O5W 120.0(12) . . ?
O6W O5W O4W 114.1(14) . . ?
O7W O6W O5W 155(2) . . ?
O2 La O2 130.17(17) 2_655 . ?
O2 La N1 70.14(11) 2_655 . ?
O2 La N1 109.72(12) . . ?
O2 La N1 109.72(12) 2_655 2_655 ?
O2 La N1 70.14(11) . 2_655 ?
N1 La N1 179.7(2) . 2_655 ?
O2 La O1 64.94(10) 2_655 . ?
O2 La O1 140.58(10) . . ?
N1 La O1 109.70(12) . . ?
N1 La O1 70.44(11) 2_655 . ?
O2 La O1 140.58(10) 2_655 2_655 ?
O2 La O1 64.94(10) . 2_655 ?
N1 La O1 70.44(11) . 2_655 ?
N1 La O1 109.70(12) 2_655 2_655 ?
O1 La O1 131.07(14) . 2_655 ?
O2 La N2 85.72(13) 2_655 . ?
O2 La N2 141.24(12) . . ?
N1 La N2 64.39(16) . . ?
N1 La N2 115.90(15) 2_655 . ?
O1 La N2 61.16(11) . . ?
O1 La N2 77.83(11) 2_655 . ?
O2 La N2 141.24(12) 2_655 2_655 ?
O2 La N2 85.72(13) . 2_655 ?
N1 La N2 115.90(15) . 2_655 ?
N1 La N2 64.39(16) 2_655 2_655 ?
O1 La N2 77.83(11) . 2_655 ?
O1 La N2 61.16(11) 2_655 2_655 ?
N2 La N2 66.4(2) . 2_655 ?
O2 La N3 61.16(13) 2_655 2_655 ?
O2 La N3 77.06(12) . 2_655 ?
N1 La N3 115.65(15) . 2_655 ?
N1 La N3 64.07(15) 2_655 2_655 ?
O1 La N3 85.58(10) . 2_655 ?
O1 La N3 140.48(11) 2_655 2_655 ?
N2 La N3 141.36(12) . 2_655 ?
N2 La N3 128.46(15) 2_655 2_655 ?
O2 La N3 77.06(12) 2_655 . ?
O2 La N3 61.16(13) . . ?
N1 La N3 64.07(15) . . ?
N1 La N3 115.65(15) 2_655 . ?
O1 La N3 140.48(11) . . ?
O1 La N3 85.58(10) 2_655 . ?
N2 La N3 128.46(15) . . ?
N2 La N3 141.36(12) 2_655 . ?
N3 La N3 66.09(17) 2_655 . ?
C5 N1 C1 119.6(6) . . ?
C5 N1 La 120.2(4) . . ?
C1 N1 La 120.0(4) . . ?
N1 C5 C4 121.6(9) . . ?
N1 C5 C6 117.4(5) . . ?
C4 C5 C6 121.0(9) . . ?
C3 C4 C5 119.8(10) . . ?
C4 C3 C2 120.7(7) . . ?
C3 C2 C1 117.3(10) . . ?
N1 C1 C2 121.0(9) . . ?
N1 C1 C9 118.6(4) . . ?
C2 C1 C9 120.3(8) . . ?
N3 C9 C1 114.4(4) . . ?
C9 N3 C8 110.6(5) . . ?
C9 N3 C12 110.9(4) . . ?
C8 N3 C12 107.9(4) . . ?
C9 N3 La 110.1(4) . . ?
C8 N3 La 113.1(3) . . ?
C12 N3 La 104.0(3) . . ?
N3 C8 C8 111.9(5) . 2_655 ?
N3 C12 C13 107.8(4) . . ?
O2 C13 N6 123.3(5) . . ?
O2 C13 C12 120.3(4) . . ?
N6 C13 C12 116.4(5) . . ?
C13 O2 La 117.7(3) . . ?
C13 N6 N7 119.4(5) . . ?
C5 C6 N2 113.4(5) . . ?
C10 N2 C7 109.4(5) . . ?
C10 N2 C6 110.2(5) . . ?
C7 N2 C6 111.3(5) . . ?
C10 N2 La 104.5(3) . . ?
C7 N2 La 112.5(4) . . ?
C6 N2 La 108.7(3) . . ?
N2 C7 C7 113.0(4) . 2_655 ?
N2 C10 C11 108.6(5) . . ?
O1 C11 N4 123.0(5) . . ?
O1 C11 C10 121.7(4) . . ?
N4 C11 C10 115.3(5) . . ?
C11 O1 La 115.0(3) . . ?
C11 N4 N5 121.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.376
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.127