# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_ym626sadp2n
#TrackingRef '911186.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O6 Zn'
_chemical_formula_weight         409.69

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           Monoclinic
_symmetry_space_group_name_H-M   P2/n

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

_cell_length_a                   8.0460(16)
_cell_length_b                   5.7930(12)
_cell_length_c                   19.177(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.46(3)
_cell_angle_gamma                90.00
_cell_volume                     886.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1443
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      19.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4697
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1741
_reflns_number_gt                1610
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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.
;

_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^)+(0.0661P)^2^+0.0963P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1741
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
Zn1 Zn 0.7500 0.71176(6) 0.7500 0.03055(16) Uani 1 2 d S . .
O11 O 0.5604(2) 0.5035(3) 0.75591(9) 0.0442(4) Uani 1 1 d . . .
O12 O 0.4738(4) 0.7479(4) 0.83065(16) 0.0825(8) Uani 1 1 d . . .
N21 N 0.8468(2) 0.9316(3) 0.82916(9) 0.0330(4) Uani 1 1 d . . .
C11 C 0.4617(3) 0.5629(4) 0.79944(12) 0.0403(5) Uani 1 1 d . . .
C12 C 0.3251(3) 0.3950(5) 0.81273(13) 0.0415(6) Uani 1 1 d . . .
H12A H 0.2354 0.4815 0.8298 0.050 Uiso 1 1 calc R . .
H12B H 0.3703 0.2905 0.8499 0.050 Uiso 1 1 calc R . .
C13 C 0.2500 0.2515(6) 0.7500 0.0445(9) Uani 1 2 d S . .
H13A H 0.1634 0.1527 0.7645 0.053 Uiso 0.50 1 calc PR . .
H13B H 0.3366 0.1527 0.7355 0.053 Uiso 0.50 1 calc PR . .
C21 C 0.7536(3) 1.1076(5) 0.84699(13) 0.0444(6) Uani 1 1 d . . .
H21 H 0.6451 1.1225 0.8239 0.053 Uiso 1 1 calc R . .
C22 C 0.8092(4) 1.2677(4) 0.89755(15) 0.0441(6) Uani 1 1 d . . .
H22 H 0.7392 1.3873 0.9079 0.053 Uiso 1 1 calc R . .
C23 C 0.9718(3) 1.2497(4) 0.93336(12) 0.0343(5) Uani 1 1 d . . .
C24 C 1.0680(3) 1.0662(4) 0.91452(12) 0.0381(5) Uani 1 1 d . . .
H24 H 1.1768 1.0465 0.9367 0.046 Uiso 1 1 calc R . .
C25 C 1.0025(3) 0.9131(4) 0.86289(12) 0.0375(5) Uani 1 1 d . . .
H25 H 1.0696 0.7921 0.8511 0.045 Uiso 1 1 calc R . .
C26 C 1.0416(3) 1.4129(4) 0.98751(11) 0.0392(5) Uani 1 1 d . . .
H26 H 1.1533 1.3936 1.0061 0.047 Uiso 1 1 calc R . .
O1W O 0.5012(6) 0.7538(7) 0.9768(2) 0.1290(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
Zn1 0.0335(2) 0.0282(2) 0.0292(2) 0.000 0.00111(14) 0.000
O11 0.0336(8) 0.0440(10) 0.0564(10) 0.0065(8) 0.0111(7) -0.0025(7)
O12 0.105(2) 0.0629(16) 0.0839(19) -0.0246(12) 0.0304(16) -0.0307(14)
N21 0.0378(10) 0.0288(10) 0.0308(9) -0.0017(7) -0.0010(7) 0.0007(8)
C11 0.0396(12) 0.0414(15) 0.0388(12) 0.0082(10) 0.0003(9) 0.0028(10)
C12 0.0335(12) 0.0464(15) 0.0459(13) 0.0061(11) 0.0103(10) 0.0053(11)
C13 0.0358(19) 0.036(2) 0.064(3) 0.000 0.0150(17) 0.000
C21 0.0404(13) 0.0375(14) 0.0510(14) -0.0089(11) -0.0104(10) 0.0057(11)
C22 0.0445(15) 0.0354(14) 0.0496(16) -0.0118(11) -0.0052(11) 0.0088(10)
C23 0.0401(13) 0.0322(13) 0.0301(12) -0.0001(8) 0.0032(10) -0.0043(9)
C24 0.0331(11) 0.0413(14) 0.0383(11) -0.0023(10) -0.0016(9) 0.0008(10)
C25 0.0396(12) 0.0358(14) 0.0367(11) -0.0041(10) 0.0031(9) 0.0034(10)
C26 0.0415(13) 0.0394(14) 0.0350(12) -0.0033(10) -0.0015(9) -0.0047(10)
O1W 0.141(3) 0.167(3) 0.079(2) -0.0263(19) 0.014(2) 0.006(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
Zn1 O11 1.9599(17) 2_656 ?
Zn1 O11 1.9599(17) . ?
Zn1 N21 2.0557(18) 2_656 ?
Zn1 N21 2.0557(19) . ?
O11 C11 1.272(3) . ?
O12 C11 1.225(3) . ?
N21 C21 1.336(3) . ?
N21 C25 1.338(3) . ?
C11 C12 1.514(3) . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C12 1.521(3) 2_556 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.401(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(3) . ?
C23 C26 1.461(3) . ?
C24 C25 1.382(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C26 1.334(5) 3_787 ?
C26 H26 0.9300 . ?

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
O11 Zn1 O11 104.01(11) 2_656 . ?
O11 Zn1 N21 124.19(7) 2_656 2_656 ?
O11 Zn1 N21 101.59(7) . 2_656 ?
O11 Zn1 N21 101.59(7) 2_656 . ?
O11 Zn1 N21 124.18(7) . . ?
N21 Zn1 N21 103.44(11) 2_656 . ?
C11 O11 Zn1 115.37(17) . . ?
C21 N21 C25 117.33(19) . . ?
C21 N21 Zn1 119.36(15) . . ?
C25 N21 Zn1 123.28(16) . . ?
O12 C11 O11 122.7(3) . . ?
O12 C11 C12 119.5(2) . . ?
O11 C11 C12 117.7(2) . . ?
C11 C12 C13 116.12(19) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 C12 113.8(3) . 2_556 ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 2_556 . ?
C12 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 2_556 . ?
H13A C13 H13B 107.7 . . ?
N21 C21 C22 123.6(2) . . ?
N21 C21 H21 118.2 . . ?
C22 C21 H21 118.2 . . ?
C21 C22 C23 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 116.5(2) . . ?
C24 C23 C26 120.3(2) . . ?
C22 C23 C26 123.3(2) . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
N21 C25 C24 122.7(2) . . ?
N21 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C26 C26 C23 125.5(3) 3_787 . ?
C26 C26 H26 117.3 3_787 . ?
C23 C26 H26 117.3 . . ?

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
O11 Zn1 O11 C11 138.61(19) 2_656 . . . ?
N21 Zn1 O11 C11 -91.43(17) 2_656 . . . ?
N21 Zn1 O11 C11 23.8(2) . . . . ?
O11 Zn1 N21 C21 177.54(18) 2_656 . . . ?
O11 Zn1 N21 C21 -66.5(2) . . . . ?
N21 Zn1 N21 C21 47.84(17) 2_656 . . . ?
O11 Zn1 N21 C25 -0.1(2) 2_656 . . . ?
O11 Zn1 N21 C25 115.86(19) . . . . ?
N21 Zn1 N21 C25 -129.8(2) 2_656 . . . ?
Zn1 O11 C11 O12 6.8(3) . . . . ?
Zn1 O11 C11 C12 -172.85(15) . . . . ?
O12 C11 C12 C13 145.7(3) . . . . ?
O11 C11 C12 C13 -34.6(3) . . . . ?
C11 C12 C13 C12 -57.71(17) . . . 2_556 ?
C25 N21 C21 C22 0.0(4) . . . . ?
Zn1 N21 C21 C22 -177.8(2) . . . . ?
N21 C21 C22 C23 -0.1(5) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C21 C22 C23 C26 179.6(2) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C26 C23 C24 C25 -179.5(2) . . . . ?
C21 N21 C25 C24 0.2(3) . . . . ?
Zn1 N21 C25 C24 177.92(17) . . . . ?
C23 C24 C25 N21 -0.2(4) . . . . ?
C24 C23 C26 C26 -176.1(3) . . . 3_787 ?
C22 C23 C26 C26 4.4(5) . . . 3_787 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.081


_database_code_depnum_ccdc_archive 'CCDC 911186'