# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    2011
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
M.Herbert
F.Montilla
A.Galindo
R.Moyano
A.Pastor
E.Alvarez
_publ_contact_author_name        'Dr. Eleuterio Alvarez'
_publ_contact_author_email       ealvarez@iiq.csic.es

data_ea10308x
_database_code_depnum_ccdc_archive 'CCDC 807647'
#TrackingRef '- CCDC807647.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Mo N4 O5'
_chemical_formula_sum            'C8 H12 Mo N4 O5'
_chemical_formula_weight         340.16

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'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.4740(3)
_cell_length_b                   13.3115(4)
_cell_length_c                   8.5537(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.148(2)
_cell_angle_gamma                90.00
_cell_volume                     1266.83(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7479
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.8751
_exptl_absorpt_process_details   
;
SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical
X-ray Solutions, Madison, Wisconsin, USA.
;

_diffrn_ambient_temperature      173(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-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            39044
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.17
_diffrn_reflns_theta_max         30.62
_reflns_number_total             3882
_reflns_number_gt                3467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker (2006). APEX 2. Version 2.1.'
_computing_cell_refinement       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_reduction        'Bruker (2006). APEX 2. Version 2.1.'
_computing_structure_solution    'Bruker (2006). APEX 2. Version 2.1.'
_computing_structure_refinement  'XL, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL v. 6.14 (Bruker, 2003)'

_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^)+(0.0291P)^2^+0.4180P] 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         3882
_refine_ls_number_parameters     171
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0190
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Mo1 Mo 0.285181(9) 0.019291(8) 1.012762(12) 0.01653(4) Uani 1 1 d . . .
O1 O 0.37591(9) -0.08032(8) 1.06901(13) 0.0263(2) Uani 1 1 d . . .
O2 O 0.34689(9) 0.11631(8) 1.17826(13) 0.0277(2) Uani 1 1 d . . .
O3 O 0.40313(9) 0.12871(8) 1.04196(13) 0.0255(2) Uani 1 1 d . . .
O4 O 0.15281(10) -0.00606(8) 1.10936(13) 0.0241(2) Uani 1 1 d . . .
O5 O 0.12850(9) -0.04609(8) 0.94420(12) 0.02277(19) Uani 1 1 d . . .
N1 N 0.30240(11) -0.00228(9) 0.76731(14) 0.0216(2) Uani 1 1 d . . .
N2 N 0.38312(10) -0.06799(9) 0.73250(14) 0.0213(2) Uani 1 1 d D . .
H2N H 0.4369(15) -0.0914(13) 0.806(2) 0.026 Uiso 1 1 d D . .
N3 N 0.16363(10) 0.15235(8) 0.88995(14) 0.0209(2) Uani 1 1 d . . .
N4 N 0.04288(10) 0.14962(9) 0.86821(16) 0.0231(2) Uani 1 1 d D . .
H4N H 0.0108(16) 0.0988(12) 0.896(2) 0.028 Uiso 1 1 d D . .
C1 C 0.36596(13) -0.08142(12) 0.57329(17) 0.0262(3) Uani 1 1 d . . .
C2 C 0.26885(18) -0.02256(14) 0.50075(19) 0.0363(4) Uani 1 1 d . . .
H2 H 0.2339 -0.0161 0.3885 0.044 Uiso 1 1 calc R . .
C3 C 0.23256(16) 0.02533(13) 0.62510(19) 0.0329(3) Uani 1 1 d . . .
H3 H 0.1674 0.0712 0.6110 0.039 Uiso 1 1 calc R . .
C4 C 0.44144(16) -0.14979(15) 0.5016(2) 0.0376(4) Uani 1 1 d . . .
H4A H 0.5253 -0.1275 0.5330 0.056 Uiso 1 1 calc R . .
H4B H 0.4132 -0.1485 0.3838 0.056 Uiso 1 1 calc R . .
H4C H 0.4356 -0.2184 0.5406 0.056 Uiso 1 1 calc R . .
C5 C -0.00948(13) 0.23692(10) 0.81265(18) 0.0244(3) Uani 1 1 d . . .
C6 C 0.08132(14) 0.29928(12) 0.7927(2) 0.0335(3) Uani 1 1 d . . .
H6 H 0.0738 0.3662 0.7529 0.040 Uiso 1 1 calc R . .
C7 C 0.18655(14) 0.24369(11) 0.8432(2) 0.0313(3) Uani 1 1 d . . .
H7 H 0.2646 0.2680 0.8441 0.038 Uiso 1 1 calc R . .
C8 C -0.14222(14) 0.25235(13) 0.7835(2) 0.0375(4) Uani 1 1 d . . .
H8A H -0.1787 0.1930 0.8198 0.056 Uiso 1 1 calc R . .
H8B H -0.1769 0.2628 0.6681 0.056 Uiso 1 1 calc R . .
H8C H -0.1580 0.3114 0.8436 0.056 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
Mo1 0.01359(6) 0.01959(6) 0.01686(6) 0.00099(4) 0.00459(4) 0.00175(4)
O1 0.0239(5) 0.0293(5) 0.0259(5) 0.0044(4) 0.0064(4) 0.0087(4)
O2 0.0211(5) 0.0372(6) 0.0253(5) -0.0095(4) 0.0066(4) -0.0014(4)
O3 0.0173(4) 0.0298(5) 0.0303(5) -0.0019(4) 0.0077(4) -0.0028(4)
O4 0.0222(5) 0.0279(5) 0.0248(5) 0.0016(4) 0.0107(4) -0.0006(4)
O5 0.0207(5) 0.0222(4) 0.0253(5) -0.0010(4) 0.0054(4) -0.0031(4)
N1 0.0205(5) 0.0257(5) 0.0191(5) 0.0007(4) 0.0059(4) 0.0041(4)
N2 0.0173(5) 0.0271(5) 0.0194(5) -0.0021(4) 0.0045(4) 0.0018(4)
N3 0.0151(5) 0.0205(5) 0.0277(6) 0.0036(4) 0.0063(4) -0.0001(4)
N4 0.0156(5) 0.0197(5) 0.0347(6) 0.0083(5) 0.0076(4) 0.0003(4)
C1 0.0243(6) 0.0342(7) 0.0208(6) -0.0045(5) 0.0068(5) -0.0018(5)
C2 0.0409(10) 0.0477(10) 0.0190(7) 0.0001(6) 0.0047(6) 0.0101(7)
C3 0.0337(8) 0.0419(9) 0.0216(7) 0.0029(6) 0.0038(6) 0.0127(7)
C4 0.0324(8) 0.0521(10) 0.0292(8) -0.0148(7) 0.0092(6) 0.0032(7)
C5 0.0226(6) 0.0209(6) 0.0289(7) 0.0070(5) 0.0046(5) 0.0027(5)
C6 0.0274(7) 0.0227(6) 0.0481(9) 0.0144(6) 0.0047(7) -0.0008(6)
C7 0.0213(7) 0.0274(7) 0.0448(9) 0.0125(6) 0.0072(6) -0.0037(5)
C8 0.0231(7) 0.0317(7) 0.0576(11) 0.0159(7) 0.0095(7) 0.0079(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
Mo1 O1 1.6818(10) . ?
Mo1 O2 1.9192(10) . ?
Mo1 O4 1.9280(10) . ?
Mo1 O5 1.9540(10) . ?
Mo1 O3 1.9622(10) . ?
Mo1 N1 2.1754(12) . ?
Mo1 N3 2.3387(11) . ?
O2 O3 1.4734(15) . ?
O4 O5 1.4714(14) . ?
N1 C3 1.3343(19) . ?
N1 N2 1.3588(16) . ?
N2 C1 1.3395(17) . ?
N2 H2N 0.827(14) . ?
N3 C7 1.3261(18) . ?
N3 N4 1.3526(15) . ?
N4 C5 1.3408(17) . ?
N4 H4N 0.833(14) . ?
C1 C2 1.379(2) . ?
C1 C4 1.488(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.375(2) . ?
C5 C8 1.496(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
O1 Mo1 O2 103.21(5) . . ?
O1 Mo1 O4 103.69(5) . . ?
O2 Mo1 O4 89.37(5) . . ?
O1 Mo1 O5 101.21(5) . . ?
O2 Mo1 O5 131.88(4) . . ?
O4 Mo1 O5 44.54(4) . . ?
O1 Mo1 O3 100.92(5) . . ?
O2 Mo1 O3 44.60(4) . . ?
O4 Mo1 O3 131.80(4) . . ?
O5 Mo1 O3 157.55(4) . . ?
O1 Mo1 N1 88.63(5) . . ?
O2 Mo1 N1 134.15(5) . . ?
O4 Mo1 N1 131.10(5) . . ?
O5 Mo1 N1 86.87(5) . . ?
O3 Mo1 N1 89.90(5) . . ?
O1 Mo1 N3 170.08(5) . . ?
O2 Mo1 N3 83.90(4) . . ?
O4 Mo1 N3 83.07(4) . . ?
O5 Mo1 N3 78.38(4) . . ?
O3 Mo1 N3 79.16(4) . . ?
N1 Mo1 N3 81.45(4) . . ?
O3 O2 Mo1 69.25(6) . . ?
O2 O3 Mo1 66.15(6) . . ?
O5 O4 Mo1 68.67(6) . . ?
O4 O5 Mo1 66.79(6) . . ?
C3 N1 N2 105.49(12) . . ?
C3 N1 Mo1 131.88(11) . . ?
N2 N1 Mo1 121.61(9) . . ?
C1 N2 N1 111.72(12) . . ?
C1 N2 H2N 128.3(13) . . ?
N1 N2 H2N 119.9(13) . . ?
C7 N3 N4 104.78(11) . . ?
C7 N3 Mo1 133.58(10) . . ?
N4 N3 Mo1 121.32(8) . . ?
C5 N4 N3 112.38(11) . . ?
C5 N4 H4N 128.0(13) . . ?
N3 N4 H4N 119.5(13) . . ?
N2 C1 C2 106.46(13) . . ?
N2 C1 C4 123.03(14) . . ?
C2 C1 C4 130.50(14) . . ?
C1 C2 C3 106.07(14) . . ?
C1 C2 H2 127.0 . . ?
C3 C2 H2 127.0 . . ?
N1 C3 C2 110.25(14) . . ?
N1 C3 H3 124.9 . . ?
C2 C3 H3 124.9 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C5 C6 106.24(13) . . ?
N4 C5 C8 121.85(13) . . ?
C6 C5 C8 131.91(13) . . ?
C5 C6 C7 105.47(13) . . ?
C5 C6 H6 127.3 . . ?
C7 C6 H6 127.3 . . ?
N3 C7 C6 111.11(13) . . ?
N3 C7 H7 124.4 . . ?
C6 C7 H7 124.4 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
O1 Mo1 O2 O3 92.24(7) . . . . ?
O4 Mo1 O2 O3 -163.84(6) . . . . ?
O5 Mo1 O2 O3 -149.16(6) . . . . ?
N1 Mo1 O2 O3 -8.94(9) . . . . ?
N3 Mo1 O2 O3 -80.74(6) . . . . ?
O1 Mo1 O3 O2 -97.81(7) . . . . ?
O4 Mo1 O3 O2 21.92(9) . . . . ?
O5 Mo1 O3 O2 92.05(12) . . . . ?
N1 Mo1 O3 O2 173.60(6) . . . . ?
N3 Mo1 O3 O2 92.29(6) . . . . ?
O1 Mo1 O4 O5 -92.16(7) . . . . ?
O2 Mo1 O4 O5 164.39(6) . . . . ?
O3 Mo1 O4 O5 149.20(6) . . . . ?
N1 Mo1 O4 O5 8.21(8) . . . . ?
N3 Mo1 O4 O5 80.47(6) . . . . ?
O1 Mo1 O5 O4 98.20(7) . . . . ?
O2 Mo1 O5 O4 -21.18(9) . . . . ?
O3 Mo1 O5 O4 -91.66(12) . . . . ?
N1 Mo1 O5 O4 -173.81(6) . . . . ?
N3 Mo1 O5 O4 -91.90(6) . . . . ?
O1 Mo1 N1 C3 157.10(15) . . . . ?
O2 Mo1 N1 C3 -95.71(16) . . . . ?
O4 Mo1 N1 C3 50.04(17) . . . . ?
O5 Mo1 N1 C3 55.80(15) . . . . ?
O3 Mo1 N1 C3 -101.97(15) . . . . ?
N3 Mo1 N1 C3 -22.92(15) . . . . ?
O1 Mo1 N1 N2 -9.53(11) . . . . ?
O2 Mo1 N1 N2 97.66(11) . . . . ?
O4 Mo1 N1 N2 -116.59(10) . . . . ?
O5 Mo1 N1 N2 -110.84(11) . . . . ?
O3 Mo1 N1 N2 91.40(11) . . . . ?
N3 Mo1 N1 N2 170.45(11) . . . . ?
C3 N1 N2 C1 0.40(17) . . . . ?
Mo1 N1 N2 C1 170.11(10) . . . . ?
O2 Mo1 N3 C7 57.60(15) . . . . ?
O4 Mo1 N3 C7 147.70(16) . . . . ?
O5 Mo1 N3 C7 -167.38(16) . . . . ?
O3 Mo1 N3 C7 12.72(15) . . . . ?
N1 Mo1 N3 C7 -78.83(15) . . . . ?
O2 Mo1 N3 N4 -114.75(11) . . . . ?
O4 Mo1 N3 N4 -24.64(11) . . . . ?
O5 Mo1 N3 N4 20.28(10) . . . . ?
O3 Mo1 N3 N4 -159.62(11) . . . . ?
N1 Mo1 N3 N4 108.83(11) . . . . ?
C7 N3 N4 C5 -1.26(18) . . . . ?
Mo1 N3 N4 C5 173.01(10) . . . . ?
N1 N2 C1 C2 -0.60(18) . . . . ?
N1 N2 C1 C4 -179.78(14) . . . . ?
N2 C1 C2 C3 0.5(2) . . . . ?
C4 C1 C2 C3 179.64(18) . . . . ?
N2 N1 C3 C2 -0.03(19) . . . . ?
Mo1 N1 C3 C2 -168.24(12) . . . . ?
C1 C2 C3 N1 -0.3(2) . . . . ?
N3 N4 C5 C6 1.69(18) . . . . ?
N3 N4 C5 C8 -178.41(15) . . . . ?
N4 C5 C6 C7 -1.38(19) . . . . ?
C8 C5 C6 C7 178.73(19) . . . . ?
N4 N3 C7 C6 0.32(19) . . . . ?
Mo1 N3 C7 C6 -172.92(12) . . . . ?
C5 C6 C7 N3 0.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O3 0.827(14) 2.035(15) 2.8421(16) 165.3(18) 3_657
N2 H2N O2 0.827(14) 2.474(17) 3.0720(15) 130.1(16) 3_657
N4 H4N O4 0.833(14) 2.238(16) 2.9901(16) 150.4(17) 3_557
N4 H4N O5 0.833(14) 2.332(18) 2.8041(15) 116.5(16) .
N4 H4N O5 0.833(14) 2.446(17) 3.1438(15) 142.0(17) 3_557
N4 H4N O4 0.833(14) 2.545(18) 2.9781(16) 113.6(15) .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        30.62
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.068