# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx_comp1
_database_code_depnum_ccdc_archive 'CCDC 1453366'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 N O2 Zn'
_chemical_formula_weight         218.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5170(6)
_cell_length_b                   6.2320(3)
_cell_length_c                   8.7800(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.358(3)
_cell_angle_gamma                90
_cell_volume                     430.99(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1823
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.804
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.610
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1818
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1068
_reflns_number_gt                932
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond Version 3.i'
_computing_publication_material  
'WinGX - Version 2014.1, L>J> Farrugia (2012), J.Appl. Cryst. 45, 849-854'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+1.2101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1068
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.3077(5) 0.2500 0.4652(5) 0.0162(8) Uani 1 2 d S T P . .
H1A H 1.3794 0.1215 0.4758 0.019 Uiso 0.5 1 calc R U P . .
H1B H 1.3794 0.3785 0.4758 0.019 Uiso 0.5 1 calc R U P . .
C2 C 1.2394(5) 0.2500 0.6035(5) 0.0220(9) Uani 1 2 d S T P . .
H2A H 1.3346 0.2500 0.7104 0.033 Uiso 1 2 calc R U P . .
H2B H 1.1699 0.3784 0.5942 0.033 Uiso 0.5 1 calc R U P . .
H2C H 1.1699 0.1216 0.5942 0.033 Uiso 0.5 1 calc R U P . .
C3 C 1.0342(5) 0.2500 -0.1241(5) 0.0142(8) Uani 1 2 d S T P . .
H3 H 1.1443 0.2500 -0.1277 0.017 Uiso 1 2 calc R U P . .
C4 C 0.8833(5) 0.2500 -0.2619(5) 0.0191(8) Uani 1 2 d S T P . .
H4 H 0.8716 0.2500 -0.3738 0.023 Uiso 1 2 calc R U P . .
C5 C 0.7509(5) 0.2500 -0.2026(5) 0.0181(8) Uani 1 2 d S T P . .
H5 H 0.6324 0.2500 -0.2666 0.022 Uiso 1 2 calc R U P . .
C6 C 0.8283(5) 0.2500 -0.0323(5) 0.0117(7) Uani 1 2 d S T P . .
C7 C 0.7678(5) 0.2500 0.1000(5) 0.0146(8) Uani 1 2 d S T P . .
C8 C 0.5320(5) 0.2500 0.1814(5) 0.0225(9) Uani 1 2 d S T P . .
H8A H 0.5217 0.1019 0.2140 0.034 Uiso 0.5 1 calc R U P . .
H8B H 0.4199 0.3182 0.1403 0.034 Uiso 0.5 1 calc R U P . .
H8C H 0.6087 0.3299 0.2769 0.034 Uiso 0.5 1 calc R U P . .
O1 O 0.8659(3) 0.2500 0.2464(3) 0.0221(7) Uani 1 2 d S T P . .
O2 O 0.5998(3) 0.2500 0.0524(3) 0.0186(6) Uani 1 2 d S T P . .
N1 N 1.0029(4) 0.2500 0.0152(4) 0.0136(7) Uani 1 2 d S T P . .
Zn1 Zn 1.12424(6) 0.2500 0.25092(6) 0.0351(2) Uani 1 2 d S T P . .


_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
C1 C2 1.533(5) . ?
C1 Zn1 1.935(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N1 1.347(5) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.383(5) . ?
C6 C7 1.439(5) . ?
C7 O1 1.238(5) . ?
C7 O2 1.329(4) . ?
C8 O2 1.454(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 Zn1 2.185(3) . ?
N1 Zn1 1.930(3) . ?
Zn1 C4 17.416(4) 2 ?

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
C2 C1 Zn1 111.1(3) . . ?
C2 C1 H1A 109.4 . . ?
Zn1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
Zn1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 110.7(3) . . ?
N1 C3 H3 124.7 . . ?
C4 C3 H3 124.7 . . ?
C3 C4 C5 106.5(3) . . ?
C3 C4 H4 126.8 . . ?
C5 C4 H4 126.8 . . ?
C6 C5 C4 106.2(3) . . ?
C6 C5 H5 126.9 . . ?
C4 C5 H5 126.9 . . ?
N1 C6 C5 110.0(3) . . ?
N1 C6 C7 115.5(3) . . ?
C5 C6 C7 134.5(4) . . ?
O1 C7 O2 123.2(3) . . ?
O1 C7 C6 122.0(3) . . ?
O2 C7 C6 114.8(3) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 O1 Zn1 107.3(2) . . ?
C7 O2 C8 117.0(3) . . ?
C3 N1 C6 106.7(3) . . ?
C3 N1 Zn1 139.8(3) . . ?
C6 N1 Zn1 113.5(2) . . ?
N1 Zn1 C1 161.37(15) . . ?
N1 Zn1 O1 81.70(12) . . ?
C1 Zn1 O1 116.93(14) . . ?
N1 Zn1 C4 83.08(9) . 2 ?
C1 Zn1 C4 115.22(11) . 2 ?
O1 Zn1 C4 10.384(9) . 2 ?

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
N1 C3 C4 C5 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 N1 0.000(0) . . . . ?
C4 C5 C6 C7 180.000(1) . . . . ?
N1 C6 C7 O1 0.000(0) . . . . ?
C5 C6 C7 O1 180.000(1) . . . . ?
N1 C6 C7 O2 180.0 . . . . ?
C5 C6 C7 O2 0.000(0) . . . . ?
O2 C7 O1 Zn1 180.000(0) . . . . ?
C6 C7 O1 Zn1 0.000(0) . . . . ?
O1 C7 O2 C8 0.000(0) . . . . ?
C6 C7 O2 C8 180.000(0) . . . . ?
C4 C3 N1 C6 0.000(0) . . . . ?
C4 C3 N1 Zn1 180.000(1) . . . . ?
C5 C6 N1 C3 0.000(0) . . . . ?
C7 C6 N1 C3 180.000(0) . . . . ?
C5 C6 N1 Zn1 180.000(0) . . . . ?
C7 C6 N1 Zn1 0.000(0) . . . . ?

_refine_diff_density_max         0.450
_refine_diff_density_min         -1.349
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_shelx_comp3
_database_code_depnum_ccdc_archive 'CCDC 1453367'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 N2 O2 Zn2'
_chemical_formula_weight         469.18

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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.3370(9)
_cell_length_b                   5.4990(4)
_cell_length_c                   20.667(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.267(3)
_cell_angle_gamma                90
_cell_volume                     1044.14(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10650
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.314
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3321
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.710
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2232
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond Version 3.i'
_computing_publication_material  'WinGX - Version 2014.1'
_refine_special_details          
;
The DENZO imageprocessing package had problems with certain strong reflections, therefore we observe alert B'
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+6.0076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9715(5) 0.4887(8) 0.1058(2) 0.0232(9) Uani 1 1 d . . . . .
H1A H 0.8671 0.4534 0.1045 0.028 Uiso 1 1 calc R U . . .
H1B H 0.9783 0.6077 0.0705 0.028 Uiso 1 1 calc R U . . .
C2 C 1.0478(5) 0.2536(9) 0.0912(2) 0.0279(10) Uani 1 1 d . . . . .
H2A H 1.0020 0.1908 0.0481 0.042 Uiso 1 1 calc R U . . .
H2B H 1.1509 0.2870 0.0911 0.042 Uiso 1 1 calc R U . . .
H2C H 1.0394 0.1325 0.1251 0.042 Uiso 1 1 calc R U . . .
C3 C 1.3254(4) 0.9655(7) 0.2403(2) 0.0191(8) Uani 1 1 d . . . . .
H3 H 1.3171 1.0826 0.2060 0.023 Uiso 1 1 calc R U . . .
C4 C 1.4366(4) 0.9653(8) 0.2969(2) 0.0201(9) Uani 1 1 d . . . . .
H4 H 1.5139 1.0792 0.3071 0.024 Uiso 1 1 calc R U . . .
C5 C 1.4108(4) 0.7671(8) 0.3344(2) 0.0184(8) Uani 1 1 d . . . . .
H5 H 1.4666 0.7177 0.3753 0.022 Uiso 1 1 calc R U . . .
C6 C 1.2843(4) 0.6529(7) 0.29944(19) 0.0161(8) Uani 1 1 d . . . . .
C7 C 1.2040(4) 0.4547(8) 0.3140(2) 0.0174(8) Uani 1 1 d . . . . .
H7 H 1.2364 0.3648 0.3531 0.021 Uiso 1 1 calc R U . . .
O1 O 1.0859(3) 0.3903(5) 0.27529(13) 0.0167(6) Uani 1 1 d . . . . .
Zn1 Zn 1.05127(5) 0.63769(8) 0.19096(2) 0.01623(14) Uani 1 1 d . . . . .
N1 N 1.2340(4) 0.7795(6) 0.24153(16) 0.0163(7) Uani 1 1 d . . . . .
C8 C 1.6973(10) 0.2205(17) 0.4481(4) 0.0250(19) Uiso 0.5 1 d . . P A -1
H8A H 1.6443 0.0887 0.4223 0.037 Uiso 0.5 1 calc R U P A -1
H8B H 1.7715 0.1514 0.4828 0.037 Uiso 0.5 1 calc R U P A -1
H8C H 1.7444 0.3232 0.4192 0.037 Uiso 0.5 1 calc R U P A -1
C9 C 1.6145(7) 0.3399(12) 0.4723(3) 0.024(2) Uiso 0.5 1 d G . P A -1
C10 C 1.4703(7) 0.2656(11) 0.4653(3) 0.025(2) Uiso 0.5 1 d G . P A -1
H10 H 1.4402 0.1177 0.4433 0.030 Uiso 0.5 1 calc R U P A -1
C11 C 1.3701(6) 0.4079(13) 0.4905(4) 0.024(2) Uiso 0.5 1 d G . P A -1
H11 H 1.2715 0.3572 0.4857 0.028 Uiso 0.5 1 calc R U P A -1
C12 C 1.4142(7) 0.6244(12) 0.5227(3) 0.025(2) Uiso 0.5 1 d G . P A -1
H12 H 1.3457 0.7217 0.5399 0.030 Uiso 0.5 1 calc R U P A -1
C13 C 1.5584(7) 0.6987(11) 0.5297(3) 0.021(2) Uiso 0.5 1 d G . P A -1
H13 H 1.5885 0.8466 0.5517 0.025 Uiso 0.5 1 calc R U P A -1
C14 C 1.6586(6) 0.5564(12) 0.5045(3) 0.024(2) Uiso 0.5 1 d G . P A -1
H14 H 1.7572 0.6071 0.5093 0.029 Uiso 0.5 1 calc R U P A -1


_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
C1 C2 1.532(6) . ?
C1 Zn1 1.964(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N1 1.335(5) . ?
C3 C4 1.420(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.417(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(6) . ?
C6 N1 1.392(5) . ?
C7 O1 1.291(5) . ?
C7 H7 0.9500 . ?
O1 Zn1 2.091(3) 2_745 ?
O1 Zn1 2.189(3) . ?
Zn1 N1 1.994(3) . ?
Zn1 O1 2.091(3) 2_755 ?
C8 C9 1.190(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 H14 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
C2 C1 Zn1 114.4(3) . . ?
C2 C1 H1A 108.7 . . ?
Zn1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
Zn1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 111.1(4) . . ?
N1 C3 H3 124.5 . . ?
C4 C3 H3 124.5 . . ?
C5 C4 C3 106.7(4) . . ?
C5 C4 H4 126.6 . . ?
C3 C4 H4 126.6 . . ?
C4 C5 C6 106.0(4) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
C7 C6 N1 117.8(3) . . ?
C7 C6 C5 132.2(4) . . ?
N1 C6 C5 109.9(3) . . ?
O1 C7 C6 121.2(4) . . ?
O1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 O1 Zn1 118.8(2) . 2_745 ?
C7 O1 Zn1 108.1(2) . . ?
Zn1 O1 Zn1 131.75(13) 2_745 . ?
C1 Zn1 N1 141.74(16) . . ?
C1 Zn1 O1 114.77(15) . 2_755 ?
N1 Zn1 O1 94.77(12) . 2_755 ?
C1 Zn1 O1 115.65(15) . . ?
N1 Zn1 O1 80.48(12) . . ?
O1 Zn1 O1 99.18(5) 2_755 . ?
C3 N1 C6 106.3(3) . . ?
C3 N1 Zn1 141.2(3) . . ?
C6 N1 Zn1 112.4(3) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C8 C9 C10 119.0(6) . . ?
C8 C9 C14 121.0(6) . . ?
C10 C9 C14 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?

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
N1 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 -176.8(4) . . . . ?
C4 C5 C6 N1 0.0(5) . . . . ?
N1 C6 C7 O1 -0.4(6) . . . . ?
C5 C6 C7 O1 176.3(4) . . . . ?
C6 C7 O1 Zn1 -167.6(3) . . . 2_745 ?
C6 C7 O1 Zn1 0.9(4) . . . . ?
C4 C3 N1 C6 -0.1(4) . . . . ?
C4 C3 N1 Zn1 176.6(3) . . . . ?
C7 C6 N1 C3 177.4(4) . . . . ?
C5 C6 N1 C3 0.0(4) . . . . ?
C7 C6 N1 Zn1 -0.4(4) . . . . ?
C5 C6 N1 Zn1 -177.8(3) . . . . ?
C8 C9 C10 C11 -177.0(7) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C8 C9 C14 C13 176.9(7) . . . . ?
C10 C9 C14 C13 0.0 . . . . ?

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_shelx_comp4
_database_code_depnum_ccdc_archive 'CCDC 1453368'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H78 N6 O6 Zn6'
_chemical_formula_weight         1299.44

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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3230(3)
_cell_length_b                   12.2960(6)
_cell_length_c                   12.9120(5)
_cell_angle_alpha                64.145(2)
_cell_angle_beta                 68.888(2)
_cell_angle_gamma                86.131(3)
_cell_volume                     1500.55(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    33461
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.409
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12899
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6821
_reflns_number_gt                5499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond Version 3.i'
_computing_publication_material  'WinGX - Version 2014.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6821
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1132(2) 0.8601(2) 0.1377(2) 0.0177(5) Uani 1 1 d . . . . .
C2 C 0.0395(2) 0.8216(2) 0.0777(2) 0.0219(6) Uani 1 1 d . . . . .
H2A H 0.0965 0.7866 0.0253 0.033 Uiso 1 1 calc R U . . .
H2B H 0.0069 0.8927 0.0271 0.033 Uiso 1 1 calc R U . . .
H2C H -0.0318 0.7608 0.1425 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1684(2) 0.7479(2) 0.2107(2) 0.0225(6) Uani 1 1 d . . . . .
H3A H 0.0987 0.6867 0.2780 0.034 Uiso 1 1 calc R U . . .
H3B H 0.2207 0.7714 0.2453 0.034 Uiso 1 1 calc R U . . .
H3C H 0.2211 0.7140 0.1553 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2245(2) 0.9549(3) 0.0338(2) 0.0233(6) Uani 1 1 d . . . . .
H4A H 0.2707 0.9833 0.0701 0.035 Uiso 1 1 calc R U . . .
H4B H 0.1914 1.0239 -0.0189 0.035 Uiso 1 1 calc R U . . .
H4C H 0.2823 0.9180 -0.0161 0.035 Uiso 1 1 calc R U . . .
C5 C -0.3089(2) 0.6221(2) 0.5498(2) 0.0191(5) Uani 1 1 d . . . . .
C6 C -0.3194(3) 0.4826(2) 0.6065(3) 0.0266(6) Uani 1 1 d . . . . .
H6A H -0.3789 0.4534 0.5824 0.040 Uiso 1 1 calc R U . . .
H6B H -0.3505 0.4489 0.6969 0.040 Uiso 1 1 calc R U . . .
H6C H -0.2354 0.4564 0.5762 0.040 Uiso 1 1 calc R U . . .
C7 C -0.2631(3) 0.6704(3) 0.4092(2) 0.0278(6) Uani 1 1 d . . . . .
H7A H -0.1786 0.6453 0.3786 0.042 Uiso 1 1 calc R U . . .
H7B H -0.2584 0.7593 0.3705 0.042 Uiso 1 1 calc R U . . .
H7C H -0.3230 0.6373 0.3884 0.042 Uiso 1 1 calc R U . . .
C8 C -0.4411(3) 0.6602(3) 0.5981(3) 0.0297(6) Uani 1 1 d . . . . .
H8A H -0.4371 0.7491 0.5598 0.045 Uiso 1 1 calc R U . . .
H8B H -0.4702 0.6290 0.6882 0.045 Uiso 1 1 calc R U . . .
H8C H -0.5008 0.6269 0.5773 0.045 Uiso 1 1 calc R U . . .
C9 C -0.3455(2) 0.6826(2) 0.9934(2) 0.0208(6) Uani 1 1 d . . . . .
C10 C -0.3430(3) 0.7022(3) 1.1009(3) 0.0368(7) Uani 1 1 d . . . . .
H10A H -0.3833 0.6291 1.1785 0.055 Uiso 1 1 calc R U . . .
H10B H -0.3896 0.7716 1.1040 0.055 Uiso 1 1 calc R U . . .
H10C H -0.2546 0.7186 1.0896 0.055 Uiso 1 1 calc R U . . .
C11 C -0.2778(3) 0.5707(3) 0.9938(3) 0.0357(7) Uani 1 1 d . . . . .
H11A H -0.1884 0.5854 0.9807 0.053 Uiso 1 1 calc R U . . .
H11B H -0.2824 0.5546 0.9274 0.053 Uiso 1 1 calc R U . . .
H11C H -0.3191 0.5003 1.0737 0.053 Uiso 1 1 calc R U . . .
C12 C -0.4850(3) 0.6558(3) 1.0131(3) 0.0357(7) Uani 1 1 d . . . . .
H12A H -0.5259 0.5857 1.0934 0.054 Uiso 1 1 calc R U . . .
H12B H -0.4873 0.6376 0.9470 0.054 Uiso 1 1 calc R U . . .
H12C H -0.5305 0.7269 1.0113 0.054 Uiso 1 1 calc R U . . .
C13 C -0.2684(2) 1.0171(2) 0.2606(2) 0.0206(5) Uani 1 1 d . . . . .
H13 H -0.3117 0.9479 0.2702 0.025 Uiso 1 1 calc R U . . .
C14 C -0.3206(2) 1.1288(3) 0.2454(2) 0.0228(6) Uani 1 1 d . . . . .
H14 H -0.4031 1.1470 0.2440 0.027 Uiso 1 1 calc R U . . .
C15 C -0.2285(2) 1.2053(2) 0.2332(2) 0.0218(6) Uani 1 1 d . . . . .
H15 H -0.2344 1.2872 0.2210 0.026 Uiso 1 1 calc R U . . .
C16 C -0.1231(2) 1.1383(2) 0.2422(2) 0.0178(5) Uani 1 1 d . . . . .
C17 C -0.0016(2) 1.1727(2) 0.2281(2) 0.0183(5) Uani 1 1 d . . . . .
H17 H 0.0179 1.2521 0.2163 0.022 Uiso 1 1 calc R U . . .
C18 C -0.0229(2) 0.5329(2) 0.7495(2) 0.0209(5) Uani 1 1 d . . . . .
H18 H -0.0858 0.4716 0.8189 0.025 Uiso 1 1 calc R U . . .
C19 C 0.1073(3) 0.5393(2) 0.7314(2) 0.0229(6) Uani 1 1 d . . . . .
H19 H 0.1466 0.4852 0.7851 0.027 Uiso 1 1 calc R U . . .
C20 C 0.1658(2) 0.6390(2) 0.6213(2) 0.0214(6) Uani 1 1 d . . . . .
H20 H 0.2539 0.6672 0.5837 0.026 Uiso 1 1 calc R U . . .
C21 C 0.0702(2) 0.6919(2) 0.5742(2) 0.0173(5) Uani 1 1 d . . . . .
C22 C 0.0750(2) 0.7906(2) 0.4650(2) 0.0195(5) Uani 1 1 d . . . . .
H22 H 0.1543 0.8381 0.4095 0.023 Uiso 1 1 calc R U . . .
C23 C -0.4124(2) 1.0686(2) 0.7658(2) 0.0219(6) Uani 1 1 d . . . . .
H23 H -0.4353 1.0789 0.8391 0.026 Uiso 1 1 calc R U . . .
C24 C -0.4417(2) 1.1466(2) 0.6616(2) 0.0226(6) Uani 1 1 d . . . . .
H24 H -0.4847 1.2174 0.6516 0.027 Uiso 1 1 calc R U . . .
C25 C -0.3951(2) 1.0991(2) 0.5770(2) 0.0220(6) Uani 1 1 d . . . . .
H25 H -0.4005 1.1305 0.4975 0.026 Uiso 1 1 calc R U . . .
C26 C -0.3378(2) 0.9945(2) 0.6321(2) 0.0175(5) Uani 1 1 d . . . . .
C27 C -0.2817(2) 0.9099(2) 0.5914(2) 0.0201(5) Uani 1 1 d . . . . .
H27 H -0.2723 0.9220 0.5108 0.024 Uiso 1 1 calc R U . . .
O1 O 0.08485(15) 1.09922(16) 0.23054(15) 0.0182(4) Uani 1 1 d . . . . .
O2 O -0.02336(15) 0.81986(16) 0.43611(15) 0.0183(4) Uani 1 1 d . . . . .
O3 O -0.24201(15) 0.81584(16) 0.65897(15) 0.0185(4) Uani 1 1 d . . . . .
Zn1 Zn 0.00075(3) 0.92902(3) 0.24783(3) 0.01696(9) Uani 1 1 d . . . . .
Zn2 Zn -0.18399(3) 0.68328(3) 0.59253(3) 0.01896(9) Uani 1 1 d . . . . .
Zn3 Zn -0.27330(3) 0.83027(3) 0.83347(3) 0.01802(9) Uani 1 1 d . . . . .
N1 N -0.15116(18) 1.02188(19) 0.25977(18) 0.0169(4) Uani 1 1 d . . . . .
N2 N -0.04634(18) 0.62386(19) 0.65692(19) 0.0175(4) Uani 1 1 d . . . . .
N3 N -0.34858(18) 0.97853(19) 0.74874(18) 0.0173(4) 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
C1 C3 1.535(3) . ?
C1 C2 1.536(3) . ?
C1 C4 1.537(4) . ?
C1 Zn1 1.990(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C8 1.529(3) . ?
C5 C7 1.531(4) . ?
C5 C6 1.537(4) . ?
C5 Zn2 1.984(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.518(4) . ?
C9 C11 1.528(4) . ?
C9 C12 1.542(4) . ?
C9 Zn3 1.986(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.329(3) . ?
C13 C14 1.419(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(3) . ?
C15 H15 0.9500 . ?
C16 N1 1.389(3) . ?
C16 C17 1.391(4) . ?
C17 O1 1.286(3) . ?
C17 H17 0.9500 . ?
C18 N2 1.332(3) . ?
C18 C19 1.408(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.369(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.414(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 N2 1.392(3) . ?
C22 O2 1.279(3) . ?
C22 H22 0.9500 . ?
C23 N3 1.337(3) . ?
C23 C24 1.412(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.416(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(4) . ?
C26 N3 1.391(3) . ?
C27 O3 1.278(3) . ?
C27 H27 0.9500 . ?
O1 Zn3 2.0838(16) 2_576 ?
O1 Zn1 2.2460(18) . ?
O2 Zn1 2.1241(17) . ?
O2 Zn2 2.2395(17) . ?
O3 Zn2 2.1197(18) . ?
O3 Zn3 2.2358(17) . ?
Zn1 N1 1.996(2) . ?
Zn2 N2 1.976(2) . ?
Zn3 N3 1.992(2) . ?
Zn3 O1 2.0838(17) 2_576 ?

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
C3 C1 C2 107.9(2) . . ?
C3 C1 C4 108.3(2) . . ?
C2 C1 C4 108.1(2) . . ?
C3 C1 Zn1 110.92(16) . . ?
C2 C1 Zn1 111.10(17) . . ?
C4 C1 Zn1 110.38(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
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 . . ?
C8 C5 C7 109.7(2) . . ?
C8 C5 C6 108.3(2) . . ?
C7 C5 C6 107.6(2) . . ?
C8 C5 Zn2 111.56(18) . . ?
C7 C5 Zn2 109.52(17) . . ?
C6 C5 Zn2 110.11(17) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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 . . ?
C10 C9 C11 108.7(2) . . ?
C10 C9 C12 108.9(2) . . ?
C11 C9 C12 107.6(2) . . ?
C10 C9 Zn3 111.79(19) . . ?
C11 C9 Zn3 113.07(18) . . ?
C12 C9 Zn3 106.68(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 111.3(2) . . ?
N1 C13 H13 124.3 . . ?
C14 C13 H13 124.3 . . ?
C15 C14 C13 106.4(2) . . ?
C15 C14 H14 126.8 . . ?
C13 C14 H14 126.8 . . ?
C14 C15 C16 106.4(2) . . ?
C14 C15 H15 126.8 . . ?
C16 C15 H15 126.8 . . ?
N1 C16 C17 119.0(2) . . ?
N1 C16 C15 109.6(2) . . ?
C17 C16 C15 131.2(2) . . ?
O1 C17 C16 121.5(2) . . ?
O1 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
N2 C18 C19 111.3(2) . . ?
N2 C18 H18 124.4 . . ?
C19 C18 H18 124.4 . . ?
C20 C19 C18 106.5(2) . . ?
C20 C19 H19 126.7 . . ?
C18 C19 H19 126.7 . . ?
C19 C20 C21 106.9(2) . . ?
C19 C20 H20 126.5 . . ?
C21 C20 H20 126.5 . . ?
C22 C21 N2 118.9(2) . . ?
C22 C21 C20 132.2(2) . . ?
N2 C21 C20 108.9(2) . . ?
O2 C22 C21 122.4(2) . . ?
O2 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
N3 C23 C24 111.8(2) . . ?
N3 C23 H23 124.1 . . ?
C24 C23 H23 124.1 . . ?
C25 C24 C23 106.2(2) . . ?
C25 C24 H24 126.9 . . ?
C23 C24 H24 126.9 . . ?
C24 C25 C26 106.5(2) . . ?
C24 C25 H25 126.8 . . ?
C26 C25 H25 126.8 . . ?
C27 C26 N3 119.1(2) . . ?
C27 C26 C25 131.2(2) . . ?
N3 C26 C25 109.6(2) . . ?
O3 C27 C26 121.9(2) . . ?
O3 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C17 O1 Zn3 118.48(16) . 2_576 ?
C17 O1 Zn1 106.81(15) . . ?
Zn3 O1 Zn1 131.39(8) 2_576 . ?
C22 O2 Zn1 119.30(15) . . ?
C22 O2 Zn2 105.69(15) . . ?
Zn1 O2 Zn2 130.70(8) . . ?
C27 O3 Zn2 116.56(16) . . ?
C27 O3 Zn3 106.66(16) . . ?
Zn2 O3 Zn3 136.42(8) . . ?
C1 Zn1 N1 138.90(9) . . ?
C1 Zn1 O2 111.92(8) . . ?
N1 Zn1 O2 103.01(7) . . ?
C1 Zn1 O1 115.48(9) . . ?
N1 Zn1 O1 80.13(7) . . ?
O2 Zn1 O1 96.39(7) . . ?
N2 Zn2 C5 138.86(10) . . ?
N2 Zn2 O3 99.56(8) . . ?
C5 Zn2 O3 116.43(9) . . ?
N2 Zn2 O2 81.17(7) . . ?
C5 Zn2 O2 117.45(8) . . ?
O3 Zn2 O2 87.97(7) . . ?
C9 Zn3 N3 132.48(9) . . ?
C9 Zn3 O1 120.00(9) . 2_576 ?
N3 Zn3 O1 100.82(7) . 2_576 ?
C9 Zn3 O3 118.28(9) . . ?
N3 Zn3 O3 80.45(7) . . ?
O1 Zn3 O3 92.04(6) 2_576 . ?
C13 N1 C16 106.2(2) . . ?
C13 N1 Zn1 140.43(19) . . ?
C16 N1 Zn1 112.36(15) . . ?
C18 N2 C21 106.4(2) . . ?
C18 N2 Zn2 141.50(18) . . ?
C21 N2 Zn2 111.79(16) . . ?
C23 N3 C26 105.9(2) . . ?
C23 N3 Zn3 142.24(18) . . ?
C26 N3 Zn3 111.77(16) . . ?

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
N1 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 N1 0.0(3) . . . . ?
C14 C15 C16 C17 175.0(3) . . . . ?
N1 C16 C17 O1 0.2(4) . . . . ?
C15 C16 C17 O1 -174.4(2) . . . . ?
N2 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 -177.1(3) . . . . ?
C19 C20 C21 N2 0.3(3) . . . . ?
N2 C21 C22 O2 -1.5(4) . . . . ?
C20 C21 C22 O2 175.7(3) . . . . ?
N3 C23 C24 C25 1.4(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C27 176.9(3) . . . . ?
C24 C25 C26 N3 -0.3(3) . . . . ?
N3 C26 C27 O3 1.7(4) . . . . ?
C25 C26 C27 O3 -175.3(2) . . . . ?
C16 C17 O1 Zn3 165.24(18) . . . 2_576 ?
C16 C17 O1 Zn1 3.5(3) . . . . ?
C21 C22 O2 Zn1 -159.21(19) . . . . ?
C21 C22 O2 Zn2 -0.1(3) . . . . ?
C26 C27 O3 Zn2 171.16(18) . . . . ?
C26 C27 O3 Zn3 -3.1(3) . . . . ?
C14 C13 N1 C16 -0.8(3) . . . . ?
C14 C13 N1 Zn1 -167.4(2) . . . . ?
C17 C16 N1 C13 -175.2(2) . . . . ?
C15 C16 N1 C13 0.5(3) . . . . ?
C17 C16 N1 Zn1 -4.4(3) . . . . ?
C15 C16 N1 Zn1 171.27(16) . . . . ?
C19 C18 N2 C21 0.7(3) . . . . ?
C19 C18 N2 Zn2 173.0(2) . . . . ?
C22 C21 N2 C18 177.2(2) . . . . ?
C20 C21 N2 C18 -0.6(3) . . . . ?
C22 C21 N2 Zn2 2.3(3) . . . . ?
C20 C21 N2 Zn2 -175.43(17) . . . . ?
C24 C23 N3 C26 -1.6(3) . . . . ?
C24 C23 N3 Zn3 -177.8(2) . . . . ?
C27 C26 N3 C23 -176.4(2) . . . . ?
C25 C26 N3 C23 1.2(3) . . . . ?
C27 C26 N3 Zn3 1.1(3) . . . . ?
C25 C26 N3 Zn3 178.67(16) . . . . ?

_refine_diff_density_max         1.105
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.105

_shelxl_version_number           2014/6

