# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1562872'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2017-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 N5 O Zn'
_chemical_formula_sum            'C21 H29 N5 O Zn'
_chemical_formula_weight         432.86

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'

_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                   13.201(3)
_cell_length_b                   15.952(3)
_cell_length_c                   10.310(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.966(3)
_cell_angle_gamma                90
_cell_volume                     2169.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    1940
_cell_measurement_theta_min      2.353
_cell_measurement_theta_max      18.962

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.152
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector, APEX'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14175
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3822
_reflns_number_gt                2767
_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       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'WINGX v2014.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2014.1 (Farrugia, 2012)'


_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)+(0.0469P)²+0.2230P] 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         3822
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.006
_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
Zn1 Zn 0.17549(3) 0.10225(3) 0.72336(3) 0.04396(15) Uani 1 1 d . . . . .
O1 O 0.23426(15) 0.20966(13) 0.68434(18) 0.0395(5) Uani 1 1 d . . . . .
N4 N 0.10272(17) 0.14809(17) 0.4601(2) 0.0362(6) Uani 1 1 d . . . . .
N2 N 0.26786(18) 0.08879(15) 0.4660(2) 0.0331(6) Uani 1 1 d . . . . .
N1 N 0.26577(18) 0.04457(17) 0.5795(2) 0.0383(6) Uani 1 1 d . . . . .
N3 N 0.06587(19) 0.12075(16) 0.5745(2) 0.0397(7) Uani 1 1 d . . . . .
C13 C 0.3588(2) 0.2524(2) 0.5337(3) 0.0342(7) Uani 1 1 d . . . . .
C8 C -0.0324(2) 0.1056(2) 0.5510(3) 0.0406(8) Uani 1 1 d . . . . .
C12 C 0.2482(2) 0.23212(19) 0.5573(3) 0.0340(7) Uani 1 1 d . . . . .
H12 H 0.2094 0.2837 0.5412 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0292(2) 0.1480(2) 0.3648(3) 0.0410(8) Uani 1 1 d . . . . .
C11 C 0.2103(2) 0.16637(19) 0.4536(3) 0.0331(7) Uani 1 1 d . . . . .
H11 H 0.2222 0.1898 0.3676 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3764(2) -0.0117(2) 0.4474(3) 0.0467(8) Uani 1 1 d . . . . .
H2 H 0.4248 -0.0480 0.4155 0.056 Uiso 1 1 calc R U . . .
C1 C 0.3353(2) 0.0557(2) 0.3847(3) 0.0392(8) Uani 1 1 d . . . . .
C3 C 0.3327(2) -0.0164(2) 0.5680(3) 0.0440(8) Uani 1 1 d . . . . .
C7 C -0.0567(2) 0.1223(2) 0.4221(3) 0.0494(9) Uani 1 1 d . . . . .
H7 H -0.1205 0.1169 0.3818 0.059 Uiso 1 1 calc R U . . .
C10 C -0.0968(3) 0.0748(2) 0.6571(3) 0.0572(10) Uani 1 1 d . . . . .
H10A H -0.0621 0.0305 0.7034 0.086 Uiso 1 1 calc R U . . .
H10B H -0.1598 0.0540 0.6205 0.086 Uiso 1 1 calc R U . . .
H10C H -0.1100 0.1199 0.7156 0.086 Uiso 1 1 calc R U . . .
C4 C 0.3528(3) 0.0930(2) 0.2551(3) 0.0561(10) Uani 1 1 d . . . . .
H4A H 0.2911 0.0913 0.2032 0.084 Uiso 1 1 calc R U . . .
H4B H 0.4044 0.0618 0.2129 0.084 Uiso 1 1 calc R U . . .
H4C H 0.3744 0.1502 0.2656 0.084 Uiso 1 1 calc R U . . .
C17 C 0.5363(3) 0.2321(2) 0.5885(4) 0.0559(10) Uani 1 1 d . . . . .
H17 H 0.5858 0.2027 0.6360 0.067 Uiso 1 1 calc R U . . .
C16 C 0.5647(2) 0.2954(2) 0.5056(3) 0.0516(9) Uani 1 1 d . . . . .
C14 C 0.3867(3) 0.3151(3) 0.4523(3) 0.0565(10) Uani 1 1 d . . . . .
H14 H 0.3366 0.3438 0.4047 0.068 Uiso 1 1 calc R U . . .
C18 C 0.4351(2) 0.2119(2) 0.6017(3) 0.0478(9) Uani 1 1 d . . . . .
H18 H 0.4185 0.1694 0.6589 0.057 Uiso 1 1 calc R U . . .
C9 C 0.0465(3) 0.1700(3) 0.2275(3) 0.0619(11) Uani 1 1 d . . . . .
H9A H 0.0866 0.2201 0.2243 0.093 Uiso 1 1 calc R U . . .
H9B H -0.0175 0.1792 0.1827 0.093 Uiso 1 1 calc R U . . .
H9C H 0.0816 0.1249 0.1867 0.093 Uiso 1 1 calc R U . . .
C5 C 0.3520(3) -0.0781(2) 0.6766(4) 0.0653(11) Uani 1 1 d . . . . .
H5A H 0.4067 -0.0582 0.7322 0.098 Uiso 1 1 calc R U . . .
H5B H 0.3696 -0.1315 0.6411 0.098 Uiso 1 1 calc R U . . .
H5C H 0.2919 -0.0837 0.7259 0.098 Uiso 1 1 calc R U . . .
C15 C 0.4873(3) 0.3378(3) 0.4380(3) 0.0652(12) Uani 1 1 d . . . . .
H15 H 0.5031 0.3816 0.3828 0.078 Uiso 1 1 calc R U . . .
N5 N 0.6661(2) 0.3167(3) 0.4911(4) 0.0860(12) Uani 1 1 d . . . . .
C21 C 0.1416(3) 0.0464(3) 0.8849(3) 0.0729(12) Uani 1 1 d . . . . .
H21A H 0.1999 0.0460 0.9431 0.109 Uiso 1 1 calc R U . . .
H21B H 0.1208 -0.0102 0.8666 0.109 Uiso 1 1 calc R U . . .
H21C H 0.0873 0.0760 0.9244 0.109 Uiso 1 1 calc R U . . .
C20 C 0.7439(3) 0.2714(3) 0.5596(5) 0.0941(16) Uani 1 1 d . . . . .
H20A H 0.7381 0.2803 0.6512 0.141 Uiso 1 1 calc R U . . .
H20B H 0.8089 0.2907 0.5332 0.141 Uiso 1 1 calc R U . . .
H20C H 0.7370 0.2127 0.5407 0.141 Uiso 1 1 calc R U . . .
C19 C 0.6918(3) 0.3862(4) 0.4141(5) 0.111(2) Uani 1 1 d . . . . .
H19A H 0.6720 0.3754 0.3252 0.166 Uiso 1 1 calc R U . . .
H19B H 0.7636 0.3953 0.4211 0.166 Uiso 1 1 calc R U . . .
H19C H 0.6571 0.4351 0.4438 0.166 Uiso 1 1 calc R U . . .


_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 O1 1.929(2) . ?
Zn1 C21 1.954(3) . ?
Zn1 N3 2.094(3) . ?
Zn1 N1 2.142(3) . ?
O1 C12 1.376(3) . ?
N4 C6 1.357(4) . ?
N4 N3 1.363(3) . ?
N4 C11 1.454(3) . ?
N2 C1 1.351(4) . ?
N2 N1 1.367(3) . ?
N2 C11 1.455(4) . ?
N1 C3 1.323(4) . ?
N3 C8 1.334(4) . ?
C13 C14 1.366(4) . ?
C13 C18 1.369(4) . ?
C13 C12 1.524(4) . ?
C8 C7 1.382(5) . ?
C8 C10 1.492(4) . ?
C12 C11 1.567(4) . ?
C6 C7 1.360(4) . ?
C6 C9 1.484(4) . ?
C2 C1 1.358(4) . ?
C2 C3 1.391(4) . ?
C1 C4 1.489(4) . ?
C3 C5 1.505(4) . ?
C17 C16 1.383(5) . ?
C17 C18 1.385(4) . ?
C16 C15 1.392(5) . ?
C16 N5 1.394(4) . ?
C14 C15 1.389(4) . ?
N5 C19 1.411(6) . ?
N5 C20 1.423(5) . ?

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
O1 Zn1 C21 133.48(14) . . ?
O1 Zn1 N3 89.69(9) . . ?
C21 Zn1 N3 121.08(14) . . ?
O1 Zn1 N1 89.99(9) . . ?
C21 Zn1 N1 122.93(16) . . ?
N3 Zn1 N1 86.55(9) . . ?
C12 O1 Zn1 119.83(17) . . ?
C6 N4 N3 111.0(2) . . ?
C6 N4 C11 130.0(2) . . ?
N3 N4 C11 118.8(2) . . ?
C1 N2 N1 111.2(3) . . ?
C1 N2 C11 129.1(3) . . ?
N1 N2 C11 119.2(2) . . ?
C3 N1 N2 105.6(2) . . ?
C3 N1 Zn1 140.1(2) . . ?
N2 N1 Zn1 113.51(19) . . ?
C8 N3 N4 106.0(2) . . ?
C8 N3 Zn1 138.7(2) . . ?
N4 N3 Zn1 114.92(17) . . ?
C14 C13 C18 116.8(3) . . ?
C14 C13 C12 122.3(3) . . ?
C18 C13 C12 120.7(3) . . ?
N3 C8 C7 109.4(3) . . ?
N3 C8 C10 120.2(3) . . ?
C7 C8 C10 130.5(3) . . ?
O1 C12 C13 111.5(2) . . ?
O1 C12 C11 115.2(2) . . ?
C13 C12 C11 108.5(2) . . ?
N4 C6 C7 105.8(3) . . ?
N4 C6 C9 124.1(3) . . ?
C7 C6 C9 130.1(3) . . ?
N4 C11 N2 109.5(2) . . ?
N4 C11 C12 113.1(2) . . ?
N2 C11 C12 110.9(2) . . ?
C1 C2 C3 107.3(3) . . ?
N2 C1 C2 106.0(3) . . ?
N2 C1 C4 121.8(3) . . ?
C2 C1 C4 132.2(3) . . ?
N1 C3 C2 109.8(3) . . ?
N1 C3 C5 120.6(3) . . ?
C2 C3 C5 129.5(3) . . ?
C6 C7 C8 107.8(3) . . ?
C16 C17 C18 120.9(3) . . ?
C17 C16 C15 117.0(3) . . ?
C17 C16 N5 121.8(3) . . ?
C15 C16 N5 121.2(4) . . ?
C13 C14 C15 122.3(3) . . ?
C13 C18 C17 122.3(3) . . ?
C14 C15 C16 120.6(3) . . ?
C16 N5 C19 120.1(4) . . ?
C16 N5 C20 120.1(4) . . ?
C19 N5 C20 119.7(4) . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1562873'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2017-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H31 N5 O Zn'
_chemical_formula_sum            'C22 H31 N5 O Zn'
_chemical_formula_weight         446.89

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'

_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                   12.951(3)
_cell_length_b                   16.222(4)
_cell_length_c                   10.789(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.045(4)
_cell_angle_gamma                90
_cell_volume                     2265.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    703
_cell_measurement_theta_min      2.268
_cell_measurement_theta_max      15.738

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.106
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector, APEX'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13960
_diffrn_reflns_av_unetI/netI     0.1336
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.013
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3981
_reflns_number_gt                1872
_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       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_data_reduction        'Bruker SAINT V8.37 (Bruker AXS Inc. 2016)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'WINGX v2014.1 (Farrugia, 2012)'
_computing_publication_material  'WINGX v2014.1 (Farrugia, 2012)'


_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)+(0.0638P)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         3981
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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
Zn1 Zn 0.80858(5) 0.08934(5) 0.28981(6) 0.0528(3) Uani 1 1 d . . . . .
N1 N 0.9246(3) 0.1127(3) 0.4277(4) 0.0465(13) Uani 1 1 d . . . . .
N2 N 0.8892(3) 0.1504(3) 0.5318(4) 0.0394(11) Uani 1 1 d . . . . .
N3 N 0.7202(3) 0.0415(3) 0.4342(4) 0.0410(12) Uani 1 1 d . . . . .
N4 N 0.7220(3) 0.0893(3) 0.5392(4) 0.0353(10) Uani 1 1 d . . . . .
N5 N 0.3160(4) 0.3181(5) 0.5013(6) 0.098(2) Uani 1 1 d . . . . .
O1 O 0.7520(3) 0.1971(2) 0.3148(3) 0.0474(10) Uani 1 1 d . . . . .
C1 C 0.9665(4) 0.1612(4) 0.6182(5) 0.0472(15) Uani 1 1 d . . . . .
C2 C 1.0534(4) 0.1326(4) 0.5653(6) 0.0539(17) Uani 1 1 d . . . . .
H2 H 1.1197 0.1327 0.6013 0.065 Uiso 1 1 calc R U . . .
C3 C 1.0254(4) 0.1036(4) 0.4493(5) 0.0473(16) Uani 1 1 d . . . . .
C4 C 0.9519(5) 0.1973(5) 0.7425(6) 0.078(2) Uani 1 1 d . . . . .
H4A H 0.8806 0.2116 0.7507 0.116 Uiso 1 1 calc R U . . .
H4B H 0.9938 0.2458 0.7523 0.116 Uiso 1 1 calc R U . . .
H4C H 0.9719 0.1578 0.8052 0.116 Uiso 1 1 calc R U . . .
C5 C 1.0895(4) 0.0634(4) 0.3535(5) 0.0632(19) Uani 1 1 d . . . . .
H5A H 1.0469 0.0512 0.2812 0.095 Uiso 1 1 calc R U . . .
H5B H 1.1186 0.0132 0.3865 0.095 Uiso 1 1 calc R U . . .
H5C H 1.1442 0.1000 0.3315 0.095 Uiso 1 1 calc R U . . .
C6 C 0.6621(4) 0.0570(4) 0.6269(5) 0.0435(15) Uani 1 1 d . . . . .
C7 C 0.6199(4) -0.0131(4) 0.5762(5) 0.0501(16) Uani 1 1 d . . . . .
H7 H 0.5743 -0.0487 0.6138 0.060 Uiso 1 1 calc R U . . .
C8 C 0.6582(4) -0.0212(4) 0.4576(6) 0.0472(15) Uani 1 1 d . . . . .
C9 C 0.6495(4) 0.0977(4) 0.7489(5) 0.0575(17) Uani 1 1 d . . . . .
H9A H 0.6904 0.1470 0.7531 0.086 Uiso 1 1 calc R U . . .
H9B H 0.6718 0.0608 0.8141 0.086 Uiso 1 1 calc R U . . .
H9C H 0.5781 0.1114 0.7583 0.086 Uiso 1 1 calc R U . . .
C10 C 0.6367(4) -0.0859(4) 0.3631(5) 0.0626(18) Uani 1 1 d . . . . .
H10A H 0.6741 -0.0740 0.2900 0.094 Uiso 1 1 calc R U . . .
H10B H 0.5640 -0.0872 0.3424 0.094 Uiso 1 1 calc R U . . .
H10C H 0.6580 -0.1386 0.3957 0.094 Uiso 1 1 calc R U . . .
C11 C 0.7785(4) 0.1664(3) 0.5393(5) 0.0371(14) Uani 1 1 d . . . . .
H11 H 0.7675 0.1938 0.6186 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7387(4) 0.2247(4) 0.4348(5) 0.0414(15) Uani 1 1 d . . . . .
H12 H 0.7792 0.2755 0.4437 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6273(4) 0.2485(4) 0.4573(5) 0.0393(14) Uani 1 1 d . . . . .
C14 C 0.5997(5) 0.3046(5) 0.5430(6) 0.070(2) Uani 1 1 d . . . . .
H14 H 0.6513 0.3282 0.5936 0.084 Uiso 1 1 calc R U . . .
C15 C 0.4994(5) 0.3282(5) 0.5589(6) 0.076(2) Uani 1 1 d . . . . .
H15 H 0.4850 0.3670 0.6193 0.092 Uiso 1 1 calc R U . . .
C16 C 0.4190(5) 0.2952(5) 0.4863(6) 0.0610(18) Uani 1 1 d . . . . .
C17 C 0.4468(5) 0.2386(4) 0.3987(6) 0.0639(19) Uani 1 1 d . . . . .
H17 H 0.3956 0.2150 0.3476 0.077 Uiso 1 1 calc R U . . .
C18 C 0.5487(4) 0.2155(4) 0.3843(5) 0.0497(16) Uani 1 1 d . . . . .
H18 H 0.5641 0.1769 0.3240 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2909(6) 0.3760(7) 0.5919(7) 0.137(4) Uani 1 1 d . . . . .
H19A H 0.2176 0.3847 0.5895 0.206 Uiso 1 1 calc R U . . .
H19B H 0.3254 0.4271 0.5760 0.206 Uiso 1 1 calc R U . . .
H19C H 0.3127 0.3557 0.6723 0.206 Uiso 1 1 calc R U . . .
C20 C 0.2375(5) 0.2855(5) 0.4201(7) 0.097(3) Uani 1 1 d . . . . .
H20A H 0.1717 0.3075 0.4416 0.145 Uiso 1 1 calc R U . . .
H20B H 0.2363 0.2265 0.4276 0.145 Uiso 1 1 calc R U . . .
H20C H 0.2515 0.3003 0.3362 0.145 Uiso 1 1 calc R U . . .
C21 C 0.8373(6) 0.0260(5) 0.1414(6) 0.088(2) Uani 1 1 d . . . . .
H21A H 0.8776 -0.0219 0.1671 0.106 Uiso 1 1 calc R U . . .
H21B H 0.7719 0.0059 0.1068 0.106 Uiso 1 1 calc R U . . .
C22 C 0.8909(8) 0.0664(6) 0.0428(7) 0.142(4) Uani 1 1 d . . . . .
H22A H 0.9003 0.0282 -0.0238 0.212 Uiso 1 1 calc R U . . .
H22B H 0.9572 0.0853 0.0740 0.212 Uiso 1 1 calc R U . . .
H22C H 0.8510 0.1126 0.0129 0.212 Uiso 1 1 calc R U . . .


_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 O1 1.918(4) . ?
Zn1 C21 1.949(7) . ?
Zn1 N1 2.110(5) . ?
Zn1 N3 2.114(4) . ?
N1 C3 1.326(6) . ?
N1 N2 1.372(5) . ?
N2 C1 1.354(6) . ?
N2 C11 1.461(6) . ?
N3 C8 1.326(7) . ?
N3 N4 1.372(5) . ?
N4 C6 1.350(6) . ?
N4 C11 1.449(7) . ?
N5 C19 1.401(9) . ?
N5 C16 1.401(8) . ?
N5 C20 1.420(8) . ?
O1 C12 1.387(6) . ?
C1 C2 1.361(7) . ?
C1 C4 1.482(8) . ?
C2 C3 1.374(8) . ?
C3 C5 1.498(7) . ?
C6 C7 1.368(7) . ?
C6 C9 1.486(7) . ?
C7 C8 1.395(7) . ?
C8 C10 1.482(8) . ?
C11 C12 1.547(7) . ?
C12 C13 1.521(7) . ?
C13 C14 1.354(8) . ?
C13 C18 1.373(7) . ?
C14 C15 1.371(8) . ?
C15 C16 1.387(8) . ?
C16 C17 1.374(8) . ?
C17 C18 1.386(7) . ?
C21 C22 1.448(9) . ?

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
O1 Zn1 C21 132.9(3) . . ?
O1 Zn1 N1 90.19(17) . . ?
C21 Zn1 N1 121.4(3) . . ?
O1 Zn1 N3 90.69(16) . . ?
C21 Zn1 N3 122.4(3) . . ?
N1 Zn1 N3 86.37(17) . . ?
C3 N1 N2 105.2(4) . . ?
C3 N1 Zn1 140.8(4) . . ?
N2 N1 Zn1 114.0(3) . . ?
C1 N2 N1 111.1(4) . . ?
C1 N2 C11 129.9(5) . . ?
N1 N2 C11 118.7(4) . . ?
C8 N3 N4 105.6(4) . . ?
C8 N3 Zn1 140.3(4) . . ?
N4 N3 Zn1 114.0(3) . . ?
C6 N4 N3 111.5(5) . . ?
C6 N4 C11 129.6(5) . . ?
N3 N4 C11 118.8(4) . . ?
C19 N5 C16 120.2(7) . . ?
C19 N5 C20 120.1(6) . . ?
C16 N5 C20 119.6(7) . . ?
C12 O1 Zn1 119.1(3) . . ?
N2 C1 C2 105.7(5) . . ?
N2 C1 C4 124.0(5) . . ?
C2 C1 C4 130.4(5) . . ?
C1 C2 C3 107.6(5) . . ?
N1 C3 C2 110.4(5) . . ?
N1 C3 C5 119.6(5) . . ?
C2 C3 C5 130.0(5) . . ?
N4 C6 C7 105.8(5) . . ?
N4 C6 C9 122.2(5) . . ?
C7 C6 C9 131.9(5) . . ?
C6 C7 C8 107.2(5) . . ?
N3 C8 C7 109.8(5) . . ?
N3 C8 C10 120.8(5) . . ?
C7 C8 C10 129.3(6) . . ?
N4 C11 N2 110.1(4) . . ?
N4 C11 C12 111.9(4) . . ?
N2 C11 C12 111.8(4) . . ?
O1 C12 C13 112.5(4) . . ?
O1 C12 C11 115.7(5) . . ?
C13 C12 C11 109.4(4) . . ?
C14 C13 C18 116.4(5) . . ?
C14 C13 C12 123.7(5) . . ?
C18 C13 C12 119.9(5) . . ?
C13 C14 C15 123.2(6) . . ?
C14 C15 C16 121.1(6) . . ?
C17 C16 C15 115.9(6) . . ?
C17 C16 N5 122.0(6) . . ?
C15 C16 N5 122.1(7) . . ?
C16 C17 C18 122.1(6) . . ?
C13 C18 C17 121.4(6) . . ?
C22 C21 Zn1 118.4(6) . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-4

