# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_w20120218g
_database_code_depnum_ccdc_archive 'CCDC 1044169'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '[Zn(Im)(HIm)2(OAc)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N6 Zn, C2 H3 O2'
_chemical_formula_sum            'C11 H14 N6 O2 Zn'
_chemical_formula_weight         327.65

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'
O O 0.0106 0.0060 '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'
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(1)/c

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                   10.9252(9)
_cell_length_b                   9.3337(6)
_cell_length_c                   14.2595(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.0093(10)
_cell_angle_gamma                90.00
_cell_volume                     1439.89(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1046
_cell_measurement_theta_min      2.8672
_cell_measurement_theta_max      28.3871

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_T_max  0.8893
_exptl_absorpt_process_details   sadabs

_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            6203
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0952
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6203
_reflns_number_gt                3538
_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 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)+(0.0812P)²+0.0000P] where P=(Fo²+2Fc²)/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         6203
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1627
_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
Zn1 Zn 0.52024(5) 0.23397(6) 0.61963(3) 0.0330(2) Uani 1 1 d . . .
N1 N 0.5525(3) 0.3813(4) 0.7194(2) 0.0327(9) Uani 1 1 d . . .
N2 N 0.4648(4) 0.0594(4) 0.6792(2) 0.0313(9) Uani 1 1 d . . .
N3 N 0.3938(3) 0.2806(4) 0.5085(2) 0.0334(9) Uani 1 1 d . . .
N4 N 0.2187(4) 0.3211(4) 0.4216(3) 0.0421(11) Uani 1 1 d . . .
H4 H 0.1426 0.3449 0.4058 0.051 Uiso 1 1 calc R . .
N5 N 0.6815(4) 0.2103(4) 0.5693(2) 0.0357(10) Uani 1 1 d . . .
N6 N 0.8369(4) 0.2592(5) 0.4950(3) 0.0534(12) Uani 1 1 d . . .
H6 H 0.8815 0.3025 0.4587 0.064 Uiso 1 1 calc R . .
O1 O 0.0204(3) 0.6151(5) 0.6180(3) 0.0624(11) Uani 1 1 d . . .
O2 O 0.1797(3) 0.4835(5) 0.6758(2) 0.0713(13) Uani 1 1 d . . .
C1 C 0.4825(4) 0.4891(5) 0.7451(3) 0.0328(11) Uani 1 1 d . . .
H1 H 0.4049 0.5119 0.7130 0.039 Uiso 1 1 calc R . .
C2 C 0.3525(5) -0.0086(5) 0.6544(3) 0.0394(12) Uani 1 1 d . . .
H2 H 0.2933 0.0146 0.6033 0.047 Uiso 1 1 calc R . .
C3 C 0.6557(4) 0.3853(5) 0.7825(3) 0.0386(12) Uani 1 1 d . . .
H3 H 0.7229 0.3240 0.7828 0.046 Uiso 1 1 calc R . .
C4 C 0.2796(5) 0.3202(5) 0.5080(3) 0.0378(12) Uani 1 1 d . . .
H4A H 0.2453 0.3448 0.5619 0.045 Uiso 1 1 calc R . .
C5 C 0.2971(5) 0.2779(6) 0.3625(3) 0.0477(14) Uani 1 1 d . . .
H5 H 0.2791 0.2669 0.2972 0.057 Uiso 1 1 calc R . .
C6 C 0.4063(4) 0.2538(5) 0.4157(3) 0.0411(12) Uani 1 1 d . . .
H6A H 0.4783 0.2239 0.3936 0.049 Uiso 1 1 calc R . .
C7 C 0.7245(5) 0.2946(6) 0.5091(3) 0.0424(13) Uani 1 1 d . . .
H7 H 0.6806 0.3714 0.4795 0.051 Uiso 1 1 calc R . .
C8 C 0.8691(5) 0.1412(7) 0.5484(4) 0.0587(16) Uani 1 1 d . . .
H8 H 0.9425 0.0898 0.5514 0.070 Uiso 1 1 calc R . .
C9 C 0.7741(5) 0.1136(6) 0.5960(4) 0.0495(14) Uani 1 1 d . . .
H9 H 0.7716 0.0406 0.6401 0.059 Uiso 1 1 calc R . .
C10 C 0.0703(5) 0.5158(7) 0.6692(3) 0.0469(14) Uani 1 1 d . . .
C11 C -0.0136(6) 0.4381(7) 0.7273(4) 0.0715(19) Uani 1 1 d . . .
H11A H -0.0480 0.3555 0.6931 0.107 Uiso 1 1 calc R . .
H11B H -0.0792 0.5009 0.7395 0.107 Uiso 1 1 calc R . .
H11C H 0.0328 0.4084 0.7862 0.107 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
Zn1 N2 1.971(4) . ?
Zn1 N1 1.975(4) . ?
Zn1 N3 2.000(3) . ?
Zn1 N5 2.005(4) . ?
N1 C3 1.341(6) . ?
N1 C1 1.346(6) . ?
N2 C1 1.324(5) 2_646 ?
N2 C2 1.383(6) . ?
N3 C4 1.300(6) . ?
N3 C6 1.371(5) . ?
N4 C4 1.316(6) . ?
N4 C5 1.344(6) . ?
N4 H4 0.8600 . ?
N5 C7 1.300(6) . ?
N5 C9 1.369(6) . ?
N6 C7 1.314(6) . ?
N6 C8 1.357(7) . ?
N6 H6 0.8600 . ?
O1 C10 1.256(6) . ?
O2 C10 1.222(6) . ?
C1 N2 1.324(5) 2_656 ?
C1 H1 0.9300 . ?
C2 C3 1.349(6) 2_646 ?
C2 H2 0.9300 . ?
C3 C2 1.349(6) 2_656 ?
C3 H3 0.9300 . ?
C4 H4A 0.9300 . ?
C5 C6 1.341(7) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.342(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.505(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
N2 Zn1 N1 107.44(15) . . ?
N2 Zn1 N3 107.54(16) . . ?
N1 Zn1 N3 116.99(15) . . ?
N2 Zn1 N5 113.64(16) . . ?
N1 Zn1 N5 104.89(15) . . ?
N3 Zn1 N5 106.57(14) . . ?
C3 N1 C1 104.6(4) . . ?
C3 N1 Zn1 123.5(3) . . ?
C1 N1 Zn1 131.8(3) . . ?
C1 N2 C2 104.5(4) 2_646 . ?
C1 N2 Zn1 129.5(3) 2_646 . ?
C2 N2 Zn1 125.7(3) . . ?
C4 N3 C6 105.8(4) . . ?
C4 N3 Zn1 128.5(3) . . ?
C6 N3 Zn1 125.0(3) . . ?
C4 N4 C5 107.6(4) . . ?
C4 N4 H4 126.2 . . ?
C5 N4 H4 126.2 . . ?
C7 N5 C9 105.2(4) . . ?
C7 N5 Zn1 125.8(3) . . ?
C9 N5 Zn1 128.7(3) . . ?
C7 N6 C8 107.1(4) . . ?
C7 N6 H6 126.5 . . ?
C8 N6 H6 126.5 . . ?
N2 C1 N1 113.2(4) 2_656 . ?
N2 C1 H1 123.4 2_656 . ?
N1 C1 H1 123.4 . . ?
C3 C2 N2 107.8(4) 2_646 . ?
C3 C2 H2 126.1 2_646 . ?
N2 C2 H2 126.1 . . ?
N1 C3 C2 109.9(4) . 2_656 ?
N1 C3 H3 125.1 . . ?
C2 C3 H3 125.1 2_656 . ?
N3 C4 N4 111.5(4) . . ?
N3 C4 H4A 124.3 . . ?
N4 C4 H4A 124.3 . . ?
C6 C5 N4 106.8(4) . . ?
C6 C5 H5 126.6 . . ?
N4 C5 H5 126.6 . . ?
C5 C6 N3 108.4(4) . . ?
C5 C6 H6A 125.8 . . ?
N3 C6 H6A 125.8 . . ?
N5 C7 N6 112.3(5) . . ?
N5 C7 H7 123.8 . . ?
N6 C7 H7 123.8 . . ?
C9 C8 N6 106.3(5) . . ?
C9 C8 H8 126.8 . . ?
N6 C8 H8 126.8 . . ?
C8 C9 N5 109.1(5) . . ?
C8 C9 H9 125.5 . . ?
N5 C9 H9 125.5 . . ?
O2 C10 O1 124.5(5) . . ?
O2 C10 C11 120.2(6) . . ?
O1 C10 C11 115.3(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N2 Zn1 N1 C3 79.0(4) . . . . ?
N3 Zn1 N1 C3 -160.0(3) . . . . ?
N5 Zn1 N1 C3 -42.2(4) . . . . ?
N2 Zn1 N1 C1 -96.5(4) . . . . ?
N3 Zn1 N1 C1 24.5(4) . . . . ?
N5 Zn1 N1 C1 142.3(4) . . . . ?
N1 Zn1 N2 C1 -52.7(4) . . . 2_646 ?
N3 Zn1 N2 C1 -179.5(4) . . . 2_646 ?
N5 Zn1 N2 C1 62.8(4) . . . 2_646 ?
N1 Zn1 N2 C2 120.4(4) . . . . ?
N3 Zn1 N2 C2 -6.3(4) . . . . ?
N5 Zn1 N2 C2 -124.0(4) . . . . ?
N2 Zn1 N3 C4 66.1(4) . . . . ?
N1 Zn1 N3 C4 -54.8(4) . . . . ?
N5 Zn1 N3 C4 -171.7(4) . . . . ?
N2 Zn1 N3 C6 -102.6(4) . . . . ?
N1 Zn1 N3 C6 136.5(4) . . . . ?
N5 Zn1 N3 C6 19.6(4) . . . . ?
N2 Zn1 N5 C7 163.3(4) . . . . ?
N1 Zn1 N5 C7 -79.6(4) . . . . ?
N3 Zn1 N5 C7 45.1(4) . . . . ?
N2 Zn1 N5 C9 -23.5(5) . . . . ?
N1 Zn1 N5 C9 93.5(4) . . . . ?
N3 Zn1 N5 C9 -141.8(4) . . . . ?
C3 N1 C1 N2 -0.4(5) . . . 2_656 ?
Zn1 N1 C1 N2 175.7(3) . . . 2_656 ?
C1 N2 C2 C3 0.7(5) 2_646 . . 2_646 ?
Zn1 N2 C2 C3 -173.9(3) . . . 2_646 ?
C1 N1 C3 C2 0.9(5) . . . 2_656 ?
Zn1 N1 C3 C2 -175.6(3) . . . 2_656 ?
C6 N3 C4 N4 -0.2(5) . . . . ?
Zn1 N3 C4 N4 -170.6(3) . . . . ?
C5 N4 C4 N3 0.8(6) . . . . ?
C4 N4 C5 C6 -1.0(6) . . . . ?
N4 C5 C6 N3 0.9(6) . . . . ?
C4 N3 C6 C5 -0.4(6) . . . . ?
Zn1 N3 C6 C5 170.4(4) . . . . ?
C9 N5 C7 N6 0.3(6) . . . . ?
Zn1 N5 C7 N6 174.8(3) . . . . ?
C8 N6 C7 N5 1.3(6) . . . . ?
C7 N6 C8 C9 -2.3(7) . . . . ?
N6 C8 C9 N5 2.5(7) . . . . ?
C7 N5 C9 C8 -1.8(6) . . . . ?
Zn1 N5 C9 C8 -176.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.176
