# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_2
_audit_creation_date             2012-09-05
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled 2012.08.15 svn.r2450, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H13 N4 O4 Zn, Cl O4'
_chemical_formula_sum            'C11 H13 Cl N4 O8 Zn'
_chemical_formula_weight         430.07
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6048(6)
_cell_length_b                   6.5235(3)
_cell_length_c                   19.0029(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.595(6)
_cell_angle_gamma                90.00
_cell_volume                     1578.73(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4110
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.1322
_cell_measurement_theta_min      2.9886
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'recrystallised from water'
_exptl_crystal_size_max          0.4207
_exptl_crystal_size_mid          0.2537
_exptl_crystal_size_min          0.1934
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9906
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.20
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.1511
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -89.00  -63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366 -179.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -94.00  -32.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366  179.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -87.00  -35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366 -179.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega   24.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5616 -100.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   29.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5616   19.0000  -30.0000 62

#__ type_ start__ end____ width___ exp.time_
  6 omega  -88.00   12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366  -77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  7 omega  -39.00  -14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366   57.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega  -88.00  -85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.9366  -77.0000 -180.0000 3
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0271888000
_diffrn_orient_matrix_UB_12      0.0753661000
_diffrn_orient_matrix_UB_13      -0.0266382000
_diffrn_orient_matrix_UB_21      -0.0337663000
_diffrn_orient_matrix_UB_22      -0.0768203000
_diffrn_orient_matrix_UB_23      -0.0221498000
_diffrn_orient_matrix_UB_31      -0.0349804000
_diffrn_orient_matrix_UB_32      0.0155786000
_diffrn_orient_matrix_UB_33      0.0197314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2709
_reflns_number_total             3080
_reflns_odcompleteness_completeness 98.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0246P)²+1.3195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0705
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Zn Zn 0.77748(2) 0.27131(4) 0.150051(16) 0.01366(10) Uani 1 1 d . . .
Cl1S Cl 0.66698(4) 0.69283(10) -0.16118(3) 0.01947(15) Uani 1 1 d . . .
N21 N 0.63620(14) 0.2308(3) 0.06732(11) 0.0134(4) Uani 1 1 d . . .
N11 N 0.91618(14) 0.3980(3) 0.15764(11) 0.0156(4) Uani 1 1 d . . .
C25 C 0.62736(18) 0.2166(4) -0.00764(14) 0.0149(5) Uani 1 1 d . . .
N13 N 1.07899(15) 0.4665(4) 0.17030(12) 0.0234(5) Uani 1 1 d . . .
H13 H 1.1475 0.4524 0.1839 0.028 Uiso 1 1 calc R . .
O11 O 0.73943(12) 0.6257(3) 0.07963(10) 0.0188(4) Uani 1 1 d . . .
C12 C 1.01406(19) 0.3327(4) 0.18606(15) 0.0206(6) Uani 1 1 d . . .
H12 H 1.0357 0.2091 0.2137 0.025 Uiso 1 1 calc R . .
C22 C 0.53947(18) 0.2568(3) 0.06592(15) 0.0156(5) Uani 1 1 d . . .
H22 H 0.5208 0.2727 0.1093 0.019 Uiso 1 1 calc R . .
O2 O 0.75611(12) -0.0710(3) 0.27059(9) 0.0168(4) Uani 1 1 d . . .
O21 O 0.80761(13) 0.1748(3) 0.02142(10) 0.0228(4) Uani 1 1 d . . .
N23 N 0.47044(15) 0.2579(3) -0.00533(12) 0.0160(5) Uani 1 1 d . . .
H23 H 0.4020 0.2723 -0.0187 0.019 Uiso 1 1 calc R . .
C24 C 0.52436(18) 0.2332(4) -0.05332(14) 0.0162(5) Uani 1 1 d . . .
C27 C 0.72067(19) 0.1892(4) -0.02703(15) 0.0189(5) Uani 1 1 d . . .
H27 H 0.7139 0.1822 -0.0785 0.023 Uiso 1 1 calc R . .
C1 C 0.81777(17) -0.1143(4) 0.23687(14) 0.0156(5) Uani 1 1 d . . .
H1 H 0.8534 -0.2420 0.2483 0.019 Uiso 1 1 calc R . .
C26 C 0.4730(2) 0.2306(4) -0.13669(15) 0.0227(6) Uani 1 1 d . . .
H26A H 0.4969 0.3489 -0.1581 0.034 Uiso 1 1 calc R . .
H26B H 0.3967 0.2373 -0.1501 0.034 Uiso 1 1 calc R . .
H26C H 0.4918 0.1039 -0.1567 0.034 Uiso 1 1 calc R . .
O1 O 0.83622(12) -0.0025(3) 0.18927(9) 0.0177(4) Uani 1 1 d . . .
O1S O 0.68342(17) 0.6922(4) -0.08308(12) 0.0533(7) Uani 1 1 d . . .
C15 C 0.92025(18) 0.5805(4) 0.12172(14) 0.0160(5) Uani 1 1 d . . .
O4S O 0.73086(16) 0.8432(4) -0.17833(14) 0.0486(7) Uani 1 1 d . . .
O2S O 0.69537(17) 0.4971(4) -0.18264(16) 0.0555(7) Uani 1 1 d . . .
C14 C 1.02278(19) 0.6260(4) 0.13032(15) 0.0212(6) Uani 1 1 d . . .
C16 C 1.0696(2) 0.8049(5) 0.10535(18) 0.0348(7) Uani 1 1 d . . .
H16A H 1.1270 0.8608 0.1482 0.052 Uiso 1 1 calc R . .
H16B H 1.0157 0.9104 0.0850 0.052 Uiso 1 1 calc R . .
H16C H 1.0968 0.7615 0.0663 0.052 Uiso 1 1 calc R . .
O3S O 0.55772(15) 0.7285(4) -0.20289(12) 0.0395(6) Uani 1 1 d . . .
C17 C 0.82489(19) 0.6893(4) 0.08125(14) 0.0172(5) Uani 1 1 d . . .
H17 H 0.8284 0.8122 0.0554 0.021 Uiso 1 1 calc R . .


_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
Zn N21 2.0273(19) . ?
Zn N11 2.0181(19) . ?
Zn O2 2.0063(17) 2_655 ?
Zn O1 1.9914(17) . ?
Cl1S O1S 1.421(2) . ?
Cl1S O4S 1.422(2) . ?
Cl1S O2S 1.434(2) . ?
Cl1S O3S 1.4364(19) . ?
N21 C25 1.390(3) . ?
N21 C22 1.318(3) . ?
N11 C12 1.319(3) . ?
N11 C15 1.383(3) . ?
C25 C24 1.369(3) . ?
C25 C27 1.452(3) . ?
N13 H13 0.8800 . ?
N13 C12 1.349(3) . ?
N13 C14 1.355(3) . ?
O11 C17 1.225(3) . ?
C12 H12 0.9500 . ?
C22 H22 0.9500 . ?
C22 N23 1.349(3) . ?
O2 Zn 2.0064(17) 2_645 ?
O2 C1 1.254(3) . ?
O21 C27 1.220(3) . ?
N23 H23 0.8800 . ?
N23 C24 1.366(3) . ?
C24 C26 1.490(4) . ?
C27 H27 0.9500 . ?
C1 H1 0.9500 . ?
C1 O1 1.254(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C15 C14 1.379(3) . ?
C15 C17 1.441(3) . ?
C14 C16 1.485(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?

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
N11 Zn N21 135.75(8) . . ?
O2 Zn N21 104.19(7) 2_655 . ?
O2 Zn N11 101.00(7) 2_655 . ?
O1 Zn N21 108.63(7) . . ?
O1 Zn N11 95.65(7) . . ?
O1 Zn O2 110.24(7) . 2_655 ?
O1S Cl1S O4S 110.91(16) . . ?
O1S Cl1S O2S 109.60(17) . . ?
O1S Cl1S O3S 109.21(13) . . ?
O4S Cl1S O2S 107.53(15) . . ?
O4S Cl1S O3S 111.04(13) . . ?
O2S Cl1S O3S 108.50(14) . . ?
C25 N21 Zn 121.34(15) . . ?
C22 N21 Zn 131.79(17) . . ?
C22 N21 C25 105.2(2) . . ?
C12 N11 Zn 132.90(18) . . ?
C12 N11 C15 105.7(2) . . ?
C15 N11 Zn 121.06(15) . . ?
N21 C25 C27 120.0(2) . . ?
C24 C25 N21 110.2(2) . . ?
C24 C25 C27 129.8(2) . . ?
C12 N13 H13 125.2 . . ?
C12 N13 C14 109.7(2) . . ?
C14 N13 H13 125.2 . . ?
N11 C12 N13 110.2(2) . . ?
N11 C12 H12 124.9 . . ?
N13 C12 H12 124.9 . . ?
N21 C22 H22 124.5 . . ?
N21 C22 N23 111.0(2) . . ?
N23 C22 H22 124.5 . . ?
C1 O2 Zn 129.72(16) . 2_645 ?
C22 N23 H23 125.6 . . ?
C22 N23 C24 108.75(19) . . ?
C24 N23 H23 125.6 . . ?
C25 C24 C26 131.8(2) . . ?
N23 C24 C25 104.8(2) . . ?
N23 C24 C26 123.4(2) . . ?
C25 C27 H27 119.3 . . ?
O21 C27 C25 121.3(2) . . ?
O21 C27 H27 119.3 . . ?
O2 C1 H1 117.4 . . ?
O2 C1 O1 125.3(2) . . ?
O1 C1 H1 117.4 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 O1 Zn 129.47(16) . . ?
N11 C15 C17 120.2(2) . . ?
C14 C15 N11 110.0(2) . . ?
C14 C15 C17 129.8(2) . . ?
N13 C14 C15 104.4(2) . . ?
N13 C14 C16 124.2(2) . . ?
C15 C14 C16 131.4(3) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O11 C17 C15 121.0(2) . . ?
O11 C17 H17 119.5 . . ?
C15 C17 H17 119.5 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 0 0.0967 -0.0000 -1.0000 0.4999 -0.0887 0.0657 -0.0057
0 1 0 0.0967 0.0000 1.0000 -0.4999 0.0887 -0.0657 0.0057
0 0 0 0.1074 -0.0000 0.0000 -0.5000 0.0133 0.0111 -0.0099
0 0 0 0.1074 0.0000 -0.0000 0.5000 -0.0133 -0.0111 0.0099
1 0 -1 0.1572 1.0000 -0.0000 -1.0000 -0.0005 -0.0116 -0.0547
-1 0 1 0.1572 -1.0000 0.0000 1.0000 0.0005 0.0116 0.0547

_shelx_res_file_MD5              bf06eadec392d8bcef26fcb903049ecb
_database_code_depnum_ccdc_archive 'CCDC 979508'
