# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Kim R. Dunbar'
_publ_contact_author_email       dunbar@chem.tamu.edu
loop_
_publ_author_name
N.Lopez
H.Zhao
D.Zhao
H.-C.Zhou
J.P.Riebenspies
K.R.Dunbar

data_c:\hanpr
_database_code_depnum_ccdc_archive 'CCDC 895842'
#TrackingRef 'Pr final revised cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N6 O4 Pr'
_chemical_formula_weight         557.31

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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   p63/mcm

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

_cell_length_a                   25.213(4)
_cell_length_b                   25.213(4)
_cell_length_c                   6.7519(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3717.2(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    486
_cell_measurement_theta_min      4.953
_cell_measurement_theta_max      57.08

_exptl_crystal_description       plate
_exptl_crystal_colour            light_green
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1650
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_T_max  0.9066
_exptl_absorpt_process_details   'SADABS v2.03 (Bruker, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(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 APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6599
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_av_sigmaI/netI    0.0077
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1182
_reflns_number_gt                1165
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.011 106 70 ' '
2 0.333 0.667 -0.079 365 164 ' '
3 0.667 0.333 -0.079 365 164 ' '

_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^)+(0.0606P)^2^+54.3381P] 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         1182
_refine_ls_number_parameters     113
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.146
_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
O1A O 0.0000 0.2682(3) 0.5864(12) 0.0398(19) Uani 1 2 d S . .
C1A C 0.0000 0.2463(6) 0.7500 0.029(3) Uani 1 4 d S . .
H1AA H 0.0000 0.2082 0.7500 0.034 Uiso 1 4 d SR . .
O2A O 0.0690(6) 0.2106(6) 0.455(2) 0.049(3) Uani 0.50 1 d PU . .
C2A C 0.0902(3) 0.1804(6) 0.5000 0.044(3) Uani 1 2 d S . .
H2AA H 0.0683 0.1365 0.5000 0.053 Uiso 1 2 d SR . .
Pr1 Pr 0.0000 0.22885(3) 0.2500 0.0189(3) Uani 1 4 d S . .
N1 N 0.1071(5) 0.3348(4) 0.2500 0.034(2) Uani 1 2 d S . .
C1 C 0.1594(7) 0.3337(6) 0.2500 0.057(3) Uani 1 2 d SU . .
H1 H 0.1570 0.2949 0.2500 0.069 Uiso 1 2 calc SR . .
N2 N 0.0000 0.3350(5) 0.2500 0.036(2) Uani 1 4 d SU . .
C2 C 0.2161(7) 0.3846(7) 0.2500 0.066(3) Uani 1 2 d SU . .
H2 H 0.2521 0.3814 0.2500 0.079 Uiso 1 2 calc SR . .
N3 N 0.0542(6) 0.4425(5) 0.2500 0.0493(18) Uani 1 2 d SU . .
C3 C 0.2195(9) 0.4416(7) 0.2500 0.068(3) Uani 1 2 d SU . .
H3 H 0.2582 0.4782 0.2500 0.082 Uiso 1 2 calc SR . .
N4 N -0.0535(8) 0.4981(6) 0.2500 0.0684(17) Uani 1 2 d SDU . .
C4 C 0.1677(8) 0.4443(6) 0.2500 0.062(2) Uani 1 2 d SU . .
H4 H 0.1693 0.4828 0.2500 0.074 Uiso 1 2 calc SR . .
C5 C 0.1109(7) 0.3895(6) 0.2500 0.0469(19) Uani 1 2 d SU . .
C6 C 0.0522(7) 0.3888(5) 0.2500 0.0421(17) Uani 1 2 d SU . .
C7 C 0.0000 0.4409(7) 0.2500 0.054(2) Uani 1 4 d SU . .
C8 C 0.0000 0.4997(8) 0.2500 0.064(2) Uani 1 4 d SDU . .
C9 C -0.0535(8) 0.4981(6) 0.2500 0.0684(17) Uani 0.00 2 d SPU . .
C10 C -0.0528(8) 0.5533(6) 0.2500 0.071(2) Uani 1 2 d SDU . .
C11 C 0.0000 0.6053(8) 0.2500 0.072(3) Uani 1 4 d SDU . .
H5 H -0.0907(9) 0.4567(19) 0.2500 0.13(8) Uiso 1 2 d SD . .
H6 H -0.0892(10) 0.5516(13) 0.2500 1.0(14) Uiso 1 2 d SD . .
H7 H 0.0000 0.6450(12) 0.2500 0.9(14) Uiso 1 4 d SD . .

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
O1A 0.073(6) 0.036(3) 0.023(4) 0.002(3) 0.000 0.036(3)
C1A 0.046(9) 0.022(5) 0.026(8) 0.000 0.000 0.023(5)
O2A 0.051(5) 0.078(5) 0.048(5) 0.008(4) -0.001(4) 0.054(4)
C2A 0.037(5) 0.041(6) 0.055(8) 0.000 -0.004(6) 0.021(3)
Pr1 0.0174(4) 0.0172(4) 0.0223(5) 0.000 0.000 0.0087(2)
N1 0.038(5) 0.018(4) 0.044(5) 0.000 0.000 0.011(4)
C1 0.043(5) 0.033(4) 0.083(7) 0.000 0.000 0.009(4)
N2 0.062(4) 0.026(3) 0.031(5) 0.000 0.000 0.031(2)
C2 0.049(5) 0.038(4) 0.089(6) 0.000 0.000 0.006(4)
N3 0.086(4) 0.031(3) 0.038(4) 0.000 0.000 0.035(3)
C3 0.058(4) 0.036(4) 0.085(6) 0.000 0.000 0.004(4)
N4 0.123(4) 0.054(3) 0.056(3) 0.000 0.000 0.065(2)
C4 0.064(4) 0.032(4) 0.070(5) 0.000 0.000 0.010(3)
C5 0.061(4) 0.026(3) 0.050(4) 0.000 0.000 0.019(3)
C6 0.068(4) 0.026(3) 0.036(3) 0.000 0.000 0.027(3)
C7 0.098(5) 0.043(3) 0.041(4) 0.000 0.000 0.049(2)
C8 0.117(4) 0.049(3) 0.050(4) 0.000 0.000 0.059(2)
C9 0.123(4) 0.054(3) 0.056(3) 0.000 0.000 0.065(2)
C10 0.129(5) 0.056(3) 0.057(4) 0.000 0.000 0.067(3)
C11 0.133(6) 0.054(4) 0.055(6) 0.000 0.000 0.066(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
O1A C1A 1.235(10) . ?
O1A Pr1 2.479(8) . ?
C1A O1A 1.235(10) 16_557 ?
O2A C2A 1.167(13) . ?
O2A Pr1 2.441(11) . ?
C2A O2A 1.167(13) 11_556 ?
Pr1 O2A 2.441(11) 8 ?
Pr1 O2A 2.441(11) 16_556 ?
Pr1 O2A 2.441(11) 24 ?
Pr1 O1A 2.479(8) 16_556 ?
Pr1 N2 2.676(12) . ?
Pr1 N1 2.686(10) . ?
Pr1 N1 2.686(10) 8 ?
N1 C1 1.331(18) . ?
N1 C5 1.334(15) . ?
C1 C2 1.36(2) . ?
N2 C6 1.337(15) . ?
N2 C6 1.337(15) 8 ?
C2 C3 1.40(2) . ?
N3 C6 1.329(16) . ?
N3 C7 1.347(15) . ?
C3 C4 1.34(3) . ?
N4 C8 1.328(18) . ?
N4 C10 1.385(14) . ?
C4 C5 1.41(2) . ?
C5 C6 1.47(2) . ?
C7 N3 1.347(15) 8 ?
C7 C8 1.48(3) . ?
C8 C9 1.328(18) 8 ?
C8 N4 1.328(18) 8 ?
C10 C11 1.321(15) . ?
C11 C10 1.321(15) 8 ?

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
C1A O1A Pr1 129.8(7) . . ?
O1A C1A O1A 126.8(13) 16_557 . ?
C2A O2A Pr1 150.8(11) . . ?
O2A C2A O2A 111.3(18) . 11_556 ?
O2A Pr1 O2A 76.3(6) 8 16_556 ?
O2A Pr1 O2A 113.9(7) 8 . ?
O2A Pr1 O2A 69.1(6) 16_556 . ?
O2A Pr1 O2A 69.1(6) 8 24 ?
O2A Pr1 O2A 113.9(7) 16_556 24 ?
O2A Pr1 O2A 76.3(6) . 24 ?
O2A Pr1 O1A 137.5(3) 8 . ?
O2A Pr1 O1A 137.5(3) 16_556 . ?
O2A Pr1 O1A 72.5(3) . . ?
O2A Pr1 O1A 72.5(3) 24 . ?
O2A Pr1 O1A 72.5(3) 8 16_556 ?
O2A Pr1 O1A 72.5(3) 16_556 16_556 ?
O2A Pr1 O1A 137.5(3) . 16_556 ?
O2A Pr1 O1A 137.5(3) 24 16_556 ?
O1A Pr1 O1A 132.8(3) . 16_556 ?
O2A Pr1 N2 123.0(3) 8 . ?
O2A Pr1 N2 123.0(3) 16_556 . ?
O2A Pr1 N2 123.0(3) . . ?
O2A Pr1 N2 123.0(3) 24 . ?
O1A Pr1 N2 66.38(17) . . ?
O1A Pr1 N2 66.38(17) 16_556 . ?
O2A Pr1 N1 143.7(3) 8 . ?
O2A Pr1 N1 74.3(4) 16_556 . ?
O2A Pr1 N1 74.3(4) . . ?
O2A Pr1 N1 143.7(3) 24 . ?
O1A Pr1 N1 78.64(11) . . ?
O1A Pr1 N1 78.64(11) 16_556 . ?
N2 Pr1 N1 60.6(2) . . ?
O2A Pr1 N1 74.3(4) 8 8 ?
O2A Pr1 N1 143.7(3) 16_556 8 ?
O2A Pr1 N1 143.7(3) . 8 ?
O2A Pr1 N1 74.3(4) 24 8 ?
O1A Pr1 N1 78.64(10) . 8 ?
O1A Pr1 N1 78.64(10) 16_556 8 ?
N2 Pr1 N1 60.6(2) . 8 ?
N1 Pr1 N1 121.1(4) . 8 ?
C1 N1 C5 117.4(12) . . ?
C1 N1 Pr1 119.6(8) . . ?
C5 N1 Pr1 123.0(9) . . ?
N1 C1 C2 124.4(14) . . ?
C6 N2 C6 117.0(15) . 8 ?
C6 N2 Pr1 121.5(7) . . ?
C6 N2 Pr1 121.5(7) 8 . ?
C1 C2 C3 117.6(16) . . ?
C6 N3 C7 116.7(13) . . ?
C4 C3 C2 119.5(15) . . ?
C8 N4 C10 117.9(17) . . ?
C3 C4 C5 119.2(14) . . ?
N1 C5 C4 121.8(14) . . ?
N1 C5 C6 115.9(11) . . ?
C4 C5 C6 122.3(12) . . ?
N3 C6 N2 123.4(13) . . ?
N3 C6 C5 117.6(12) . . ?
N2 C6 C5 119.1(10) . . ?
N3 C7 N3 122.9(16) . 8 ?
N3 C7 C8 118.5(8) . . ?
N3 C7 C8 118.5(8) 8 . ?
C9 C8 N4 0(2) 8 8 ?
C9 C8 N4 123(2) 8 . ?
N4 C8 N4 123(2) 8 . ?
C9 C8 C7 118.5(10) 8 . ?
N4 C8 C7 118.5(10) 8 . ?
N4 C8 C7 118.5(10) . . ?
C11 C10 N4 119.8(18) . . ?
C10 C11 C10 122(2) 8 . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         2.142
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.158

# Attachment 'Sm final revised cif.cif'

data_c:\docume~1\zhao\desktop\revise~1\sm
_database_code_depnum_ccdc_archive 'CCDC 895843'
#TrackingRef 'Sm final revised cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N6 O6 Sm'
_chemical_formula_weight         602.78

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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P63/mcm

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

_cell_length_a                   25.158(4)
_cell_length_b                   25.158(4)
_cell_length_c                   6.7043(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3674.8(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    506
_cell_measurement_theta_min      4.959
_cell_measurement_theta_max      50.471

_exptl_crystal_description       hexagonal_prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1788
_exptl_absorpt_coefficient_mu    2.444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_T_max  0.7748
_exptl_absorpt_process_details   'SADABS v2.03 (Bruker, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(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 APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32365
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1182
_reflns_number_gt                1060
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.625 (Bruker, 2000)'
_computing_cell_refinement       'SMART V5.625 (Bruker, 2000)'
_computing_data_reduction        'SAINT V6.32 (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+78.2928P] 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         1182
_refine_ls_number_parameters     118
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1766
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.005

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
O1A O 0.0000 0.2662(3) 0.5853(14) 0.036(2) Uani 1 2 d S . .
C1A C 0.0000 0.2431(7) 0.7500 0.024(4) Uani 1 4 d S . .
H1AA H 0.0000 0.2051 0.7500 0.029 Uiso 1 4 d SR . .
O2A O 0.0641(7) 0.2069(7) 0.450(2) 0.046(3) Uani 0.50 1 d PDU . .
C2A C 0.0887(3) 0.1774(7) 0.5000 0.050(4) Uani 1 2 d SD . .
H2AA H 0.0667 0.1333 0.5000 0.060 Uiso 1 2 d SR . .
Sm1 Sm 0.0000 0.22761(3) 0.2500 0.0186(4) Uani 1 4 d S . .
N1 N 0.1065(5) 0.3317(5) 0.2500 0.027(2) Uani 1 2 d S . .
C1 C 0.1589(7) 0.3292(6) 0.2500 0.037(3) Uani 1 2 d SU . .
H1 H 0.1562 0.2901 0.2500 0.045 Uiso 1 2 calc SR . .
N2 N 0.0000 0.3324(6) 0.2500 0.025(2) Uani 1 4 d SU . .
C2 C 0.2175(7) 0.3823(7) 0.2500 0.045(2) Uani 1 2 d SU . .
H2 H 0.2538 0.3795 0.2500 0.054 Uiso 1 2 calc SR . .
N3 N 0.0542(6) 0.4415(5) 0.2500 0.0329(17) Uani 1 2 d SU . .
C3 C 0.2204(8) 0.4390(7) 0.2500 0.046(2) Uani 1 2 d SU . .
H3 H 0.2592 0.4757 0.2500 0.055 Uiso 1 2 calc SR . .
N4 N -0.0550(7) 0.4968(6) 0.2500 0.0466(16) Uani 1 2 d SDU . .
C4 C 0.1675(7) 0.4421(7) 0.2500 0.042(2) Uani 1 2 d SU . .
H4 H 0.1693 0.4807 0.2500 0.050 Uiso 1 2 calc SR . .
C5 C 0.1099(7) 0.3866(6) 0.2500 0.0325(19) Uani 1 2 d SU . .
C6 C 0.0520(6) 0.3864(6) 0.2500 0.0291(17) Uani 1 2 d SU . .
C7 C 0.0000 0.4380(8) 0.2500 0.036(2) Uani 1 4 d SU . .
C8 C 0.0000 0.4989(9) 0.2500 0.0429(19) Uani 1 4 d SDU . .
C9 C -0.0550(7) 0.4968(6) 0.2500 0.0466(16) Uani 0.00 2 d SPU . .
C10 C -0.0521(9) 0.5529(7) 0.2500 0.048(2) Uani 1 2 d SU . .
C11 C 0.0000 0.6063(9) 0.2500 0.050(3) Uani 1 4 d SDU . .
H5 H -0.0905(9) 0.4538(16) 0.2500 2(3) Uiso 1 2 d SD . .
H6 H -0.0892(9) 0.5518(12) 0.2500 0.13(11) Uiso 1 2 d SD . .
H7 H 0.0000 0.6461(12) 0.2500 0.02(5) Uiso 1 4 d SD . .
O3W O 0.2246(9) 0.6123(4) 0.5000 0.122(6) Uani 1 2 d SU . .

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
O1A 0.065(6) 0.032(3) 0.023(5) 0.000(3) 0.000 0.032(3)
C1A 0.040(10) 0.020(6) 0.019(9) 0.000 0.000 0.020(5)
O2A 0.048(5) 0.068(5) 0.048(6) 0.012(4) -0.002(4) 0.047(4)
C2A 0.057(7) 0.036(8) 0.049(10) 0.000 0.003(8) 0.018(4)
Sm1 0.0210(5) 0.0187(4) 0.0168(5) 0.000 0.000 0.0105(3)
N1 0.028(6) 0.020(5) 0.029(6) 0.000 0.000 0.009(5)
C1 0.033(5) 0.029(4) 0.049(6) 0.000 0.000 0.014(4)
N2 0.038(4) 0.021(3) 0.022(5) 0.000 0.000 0.019(2)
C2 0.034(4) 0.036(4) 0.053(5) 0.000 0.000 0.009(4)
N3 0.049(4) 0.025(3) 0.028(4) 0.000 0.000 0.020(3)
C3 0.037(4) 0.033(4) 0.052(5) 0.000 0.000 0.006(4)
N4 0.072(3) 0.041(3) 0.040(3) 0.000 0.000 0.039(2)
C4 0.040(4) 0.030(4) 0.045(5) 0.000 0.000 0.010(3)
C5 0.038(3) 0.025(4) 0.033(4) 0.000 0.000 0.014(3)
C6 0.041(3) 0.023(3) 0.025(4) 0.000 0.000 0.017(2)
C7 0.056(4) 0.032(3) 0.029(4) 0.000 0.000 0.028(2)
C8 0.068(4) 0.036(3) 0.035(4) 0.000 0.000 0.0341(19)
C9 0.072(3) 0.041(3) 0.040(3) 0.000 0.000 0.039(2)
C10 0.076(4) 0.042(3) 0.041(4) 0.000 0.000 0.041(3)
C11 0.079(6) 0.042(4) 0.042(6) 0.000 0.000 0.040(3)
O3W 0.120(6) 0.121(7) 0.124(7) -0.010(5) 0.000 0.060(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
O1A C1A 1.247(12) . ?
O1A Sm1 2.448(9) . ?
C1A O1A 1.247(12) 16_557 ?
O2A C2A 1.227(10) . ?
O2A Sm1 2.346(11) . ?
C2A O2A 1.227(11) 11_556 ?
Sm1 O2A 2.346(11) 8 ?
Sm1 O2A 2.346(11) 16_556 ?
Sm1 O2A 2.346(11) 24 ?
Sm1 O1A 2.448(9) 16_556 ?
Sm1 N2 2.636(14) . ?
Sm1 N1 2.650(11) 8 ?
Sm1 N1 2.650(11) . ?
N1 C5 1.342(17) . ?
N1 C1 1.349(18) . ?
C1 C2 1.41(2) . ?
N2 C6 1.334(15) . ?
N2 C6 1.334(15) 8 ?
C2 C3 1.39(2) . ?
N3 C7 1.322(15) . ?
N3 C6 1.358(17) . ?
C3 C4 1.37(2) . ?
N4 C8 1.358(17) . ?
N4 C10 1.377(19) . ?
C4 C5 1.42(2) . ?
C5 C6 1.45(2) . ?
C7 N3 1.322(15) 8 ?
C7 C8 1.53(3) . ?
C8 C9 1.358(17) 8 ?
C8 N4 1.358(17) 8 ?
C10 C11 1.33(2) . ?
C11 C10 1.33(2) 8 ?

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
C1A O1A Sm1 129.0(8) . . ?
O1A C1A O1A 124.7(15) . 16_557 ?
C2A O2A Sm1 154.3(12) . . ?
O2A C2A O2A 116.8(19) 11_556 . ?
O2A Sm1 O2A 73.1(8) 8 16_556 ?
O2A Sm1 O2A 111.1(8) 8 . ?
O2A Sm1 O2A 69.5(8) 16_556 . ?
O2A Sm1 O2A 69.5(8) 8 24 ?
O2A Sm1 O2A 111.1(8) 16_556 24 ?
O2A Sm1 O2A 73.1(8) . 24 ?
O2A Sm1 O1A 138.4(4) 8 . ?
O2A Sm1 O1A 138.4(4) 16_556 . ?
O2A Sm1 O1A 72.6(4) . . ?
O2A Sm1 O1A 72.6(4) 24 . ?
O2A Sm1 O1A 72.6(4) 8 16_556 ?
O2A Sm1 O1A 72.6(4) 16_556 16_556 ?
O2A Sm1 O1A 138.4(4) . 16_556 ?
O2A Sm1 O1A 138.4(4) 24 16_556 ?
O1A Sm1 O1A 133.3(4) . 16_556 ?
O2A Sm1 N2 124.4(4) 8 . ?
O2A Sm1 N2 124.4(4) 16_556 . ?
O2A Sm1 N2 124.4(4) . . ?
O2A Sm1 N2 124.4(4) 24 . ?
O1A Sm1 N2 66.7(2) . . ?
O1A Sm1 N2 66.7(2) 16_556 . ?
O2A Sm1 N1 75.6(4) 8 8 ?
O2A Sm1 N1 142.6(4) 16_556 8 ?
O2A Sm1 N1 142.6(4) . 8 ?
O2A Sm1 N1 75.6(4) 24 8 ?
O1A Sm1 N1 78.99(12) . 8 ?
O1A Sm1 N1 78.99(12) 16_556 8 ?
N2 Sm1 N1 61.2(2) . 8 ?
O2A Sm1 N1 142.6(4) 8 . ?
O2A Sm1 N1 75.6(4) 16_556 . ?
O2A Sm1 N1 75.6(4) . . ?
O2A Sm1 N1 142.6(4) 24 . ?
O1A Sm1 N1 78.99(12) . . ?
O1A Sm1 N1 78.99(12) 16_556 . ?
N2 Sm1 N1 61.2(2) . . ?
N1 Sm1 N1 122.3(4) 8 . ?
C5 N1 C1 119.1(12) . . ?
C5 N1 Sm1 122.0(9) . . ?
C1 N1 Sm1 118.9(8) . . ?
N1 C1 C2 122.6(13) . . ?
C6 N2 C6 116.2(16) . 8 ?
C6 N2 Sm1 121.9(8) . . ?
C6 N2 Sm1 121.9(8) 8 . ?
C3 C2 C1 117.8(15) . . ?
C7 N3 C6 114.7(12) . . ?
C2 C3 C4 120.2(14) . . ?
C8 N4 C10 115.5(15) . . ?
C3 C4 C5 119.0(13) . . ?
N1 C5 C4 121.3(13) . . ?
N1 C5 C6 116.7(12) . . ?
C4 C5 C6 122.0(12) . . ?
N2 C6 N3 124.0(13) . . ?
N2 C6 C5 118.3(11) . . ?
N3 C6 C5 117.7(11) . . ?
N3 C7 N3 126.5(18) 8 . ?
N3 C7 C8 116.7(9) 8 . ?
N3 C7 C8 116.7(9) . . ?
C9 C8 N4 0(2) 8 8 ?
C9 C8 N4 123.8(19) 8 . ?
N4 C8 N4 123.8(19) 8 . ?
C9 C8 C7 118.1(9) 8 . ?
N4 C8 C7 118.1(9) 8 . ?
N4 C8 C7 118.1(9) . . ?
C11 C10 N4 123.8(17) . . ?
C10 C11 C10 118(2) . 8 ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.777
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.176