# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_120227e_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O5 Zn'
_chemical_formula_weight         383.66

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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'

_cell_length_a                   8.902(2)
_cell_length_b                   11.887(3)
_cell_length_c                   14.757(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1561.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11359
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2896
_reflns_number_gt                2813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0487P)²+0.3754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(13)
_refine_ls_number_reflns         2896
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.235
_refine_ls_restrained_S_all      1.235
_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
O4 O 0.7535(2) 0.26376(18) 0.30066(14) 0.0267(5) Uani 1 1 d . . .
C4 C 0.6849(4) 0.1835(2) 0.33402(18) 0.0255(6) Uani 1 1 d . . .
N5 N 0.6226(3) 0.5021(2) 0.77791(17) 0.0271(6) Uani 1 1 d . . .
C9 C 0.6041(4) 0.3905(3) 0.7899(2) 0.0313(7) Uani 1 1 d . . .
H9 H 0.6036 0.3622 0.8487 0.038 Uiso 1 1 calc R . .
C8 C 0.6202(4) 0.5393(3) 0.6913(2) 0.0297(7) Uani 1 1 d . . .
H8 H 0.6321 0.6159 0.6811 0.036 Uiso 1 1 calc R . .
C3 C 0.6227(4) 0.1966(2) 0.42687(19) 0.0217(6) Uani 1 1 d . . .
C7 C 0.6013(4) 0.4706(2) 0.6182(2) 0.0288(7) Uani 1 1 d . . .
H7 H 0.5981 0.5008 0.5601 0.035 Uiso 1 1 calc R . .
Zn1 Zn 0.29642(4) 0.10087(3) 0.61256(2) 0.02156(12) Uani 1 1 d . . .
O1 O 0.3664(3) -0.01949(18) 0.51193(14) 0.0269(5) Uani 1 1 d . . .
N3 N 0.4995(3) 0.1798(2) 0.55729(15) 0.0201(5) Uani 1 1 d . . .
O2 O 0.4922(3) -0.03092(18) 0.38229(17) 0.0381(6) Uani 1 1 d . . .
H2 H 0.5242 0.0150 0.3456 0.057 Uiso 1 1 calc R . .
C6 C 0.5869(3) 0.3547(3) 0.63084(18) 0.0224(6) Uani 1 1 d . . .
C13 C -0.0319(3) -0.0059(3) 0.6186(2) 0.0290(7) Uani 1 1 d . . .
C5 C 0.5770(3) 0.2763(2) 0.55345(19) 0.0207(6) Uani 1 1 d . . .
O3 O 0.6617(3) 0.0905(2) 0.29418(16) 0.0439(7) Uani 1 1 d . . .
C2 C 0.5272(3) 0.1290(2) 0.47693(19) 0.0201(6) Uani 1 1 d . . .
C1 C 0.4579(4) 0.0199(2) 0.45697(19) 0.0232(6) Uani 1 1 d . . .
C10 C 0.5859(4) 0.3161(3) 0.7186(2) 0.0289(7) Uani 1 1 d . . .
H10 H 0.5730 0.2397 0.7301 0.035 Uiso 1 1 calc R . .
N4 N 0.6565(3) 0.2910(2) 0.47625(16) 0.0216(5) Uani 1 1 d . . .
N6 N -0.0961(4) -0.0982(3) 0.5862(2) 0.0467(8) Uani 1 1 d . . .
C14 C -0.1305(5) 0.0929(4) 0.6414(3) 0.0544(11) Uani 1 1 d . . .
H14A H -0.0747 0.1459 0.6772 0.082 Uiso 1 1 calc R . .
H14B H -0.2162 0.0675 0.6752 0.082 Uiso 1 1 calc R . .
H14C H -0.1635 0.1285 0.5865 0.082 Uiso 1 1 calc R . .
C12 C -0.2577(6) -0.1142(6) 0.5795(5) 0.0816(18) Uani 1 1 d . . .
H12A H -0.2904 -0.1650 0.6260 0.122 Uiso 1 1 calc R . .
H12B H -0.2819 -0.1450 0.5211 0.122 Uiso 1 1 calc R . .
H12C H -0.3074 -0.0431 0.5868 0.122 Uiso 1 1 calc R . .
C11 C -0.0039(7) -0.1961(4) 0.5695(5) 0.090(2) Uani 1 1 d . . .
H11A H 0.0959 -0.1727 0.5535 0.134 Uiso 1 1 calc R . .
H11B H -0.0462 -0.2391 0.5206 0.134 Uiso 1 1 calc R . .
H11C H -0.0001 -0.2417 0.6231 0.134 Uiso 1 1 calc R . .
O5 O 0.1038(3) -0.0017(2) 0.62998(19) 0.0446(7) Uani 1 1 d . . .


_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
O4 C4 1.235(4) . ?
O4 Zn1 2.092(2) 4_556 ?
C4 O3 1.269(4) . ?
C4 C3 1.486(4) . ?
N5 C9 1.349(4) . ?
N5 C8 1.352(4) . ?
N5 Zn1 2.124(3) 3_656 ?
C9 C10 1.384(4) . ?
C8 C7 1.364(4) . ?
C3 N4 1.372(4) . ?
C3 C2 1.383(4) . ?
C7 C6 1.396(4) . ?
Zn1 O4 2.092(2) 4_456 ?
Zn1 O5 2.120(2) . ?
Zn1 N5 2.124(3) 3_646 ?
Zn1 O1 2.154(2) . ?
Zn1 N3 2.194(2) . ?
Zn1 N4 2.219(2) 4_456 ?
O1 C1 1.241(4) . ?
N3 C5 1.340(4) . ?
N3 C2 1.353(4) . ?
O2 C1 1.293(4) . ?
C6 C10 1.374(4) . ?
C6 C5 1.477(4) . ?
C13 O5 1.221(4) . ?
C13 N6 1.326(5) . ?
C13 C14 1.505(5) . ?
C5 N4 1.352(4) . ?
C2 C1 1.467(4) . ?
N4 Zn1 2.219(2) 4_556 ?
N6 C11 1.446(7) . ?
N6 C12 1.454(6) . ?

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
C4 O4 Zn1 116.13(18) . 4_556 ?
O4 C4 O3 124.7(3) . . ?
O4 C4 C3 118.1(3) . . ?
O3 C4 C3 117.2(3) . . ?
C9 N5 C8 116.3(3) . . ?
C9 N5 Zn1 119.0(2) . 3_656 ?
C8 N5 Zn1 123.0(2) . 3_656 ?
N5 C9 C10 122.9(3) . . ?
N5 C8 C7 123.7(3) . . ?
N4 C3 C2 109.0(3) . . ?
N4 C3 C4 119.6(3) . . ?
C2 C3 C4 131.4(3) . . ?
C8 C7 C6 119.8(3) . . ?
O4 Zn1 O5 102.74(10) 4_456 . ?
O4 Zn1 N5 91.21(9) 4_456 3_646 ?
O5 Zn1 N5 82.21(10) . 3_646 ?
O4 Zn1 O1 170.34(9) 4_456 . ?
O5 Zn1 O1 86.30(10) . . ?
N5 Zn1 O1 93.41(9) 3_646 . ?
O4 Zn1 N3 92.82(9) 4_456 . ?
O5 Zn1 N3 163.26(10) . . ?
N5 Zn1 N3 103.86(10) 3_646 . ?
O1 Zn1 N3 77.84(9) . . ?
O4 Zn1 N4 79.25(8) 4_456 4_456 ?
O5 Zn1 N4 87.17(9) . 4_456 ?
N5 Zn1 N4 163.84(10) 3_646 4_456 ?
O1 Zn1 N4 98.04(9) . 4_456 ?
N3 Zn1 N4 89.73(9) . 4_456 ?
C1 O1 Zn1 112.95(19) . . ?
C5 N3 C2 104.5(2) . . ?
C5 N3 Zn1 143.7(2) . . ?
C2 N3 Zn1 106.60(18) . . ?
C10 C6 C7 117.2(3) . . ?
C10 C6 C5 121.2(3) . . ?
C7 C6 C5 121.7(3) . . ?
O5 C13 N6 120.7(3) . . ?
O5 C13 C14 121.0(3) . . ?
N6 C13 C14 118.4(3) . . ?
N3 C5 N4 114.6(2) . . ?
N3 C5 C6 122.6(3) . . ?
N4 C5 C6 122.6(3) . . ?
N3 C2 C3 108.8(3) . . ?
N3 C2 C1 119.6(3) . . ?
C3 C2 C1 131.7(3) . . ?
O1 C1 O2 122.4(3) . . ?
O1 C1 C2 118.6(3) . . ?
O2 C1 C2 119.0(3) . . ?
C6 C10 C9 120.2(3) . . ?
C5 N4 C3 103.1(2) . . ?
C5 N4 Zn1 150.0(2) . 4_556 ?
C3 N4 Zn1 106.45(18) . 4_556 ?
C13 N6 C11 118.9(4) . . ?
C13 N6 C12 124.0(4) . . ?
C11 N6 C12 116.4(5) . . ?
C13 O5 Zn1 143.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 980157'
