# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1581344'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2017-12-21 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            'C28 H22 Co N2 O4 '
_chemical_formula_weight         509.40

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'
S S 0.1246 0.1234 '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'
Co Co 0.3494 0.9721 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2960(6)
_cell_length_b                   15.9061(9)
_cell_length_c                   13.4636(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.951(6)
_cell_angle_gamma                90
_cell_volume                     2314.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5191
_cell_measurement_theta_min      2.9990
_cell_measurement_theta_max      33.2723

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.780
_shelx_estimated_absorpt_T_min   0.777
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95504
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3611
_diffrn_reflns_number            11655
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.010
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4061
_reflns_number_gt                3119
_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       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'
_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)+(0.0396P)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         4061
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.2351(2) -0.11264(15) 0.12334(19) 0.0239(6) Uani 1 1 d . . . . .
C2 C 0.3101(2) -0.17881(15) 0.1084(2) 0.0279(6) Uani 1 1 d . . . . .
H2 H 0.2973 -0.2017 0.0409 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4013(2) -0.21058(15) 0.1899(2) 0.0276(6) Uani 1 1 d . . . . .
H3 H 0.4527 -0.2549 0.1793 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4184(2) -0.17708(15) 0.28951(19) 0.0232(6) Uani 1 1 d . . . . .
C5 C 0.5086(2) -0.20841(16) 0.3802(2) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.5625 -0.2525 0.3736 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5179(2) -0.17620(16) 0.4749(2) 0.0283(6) Uani 1 1 d . . . . .
H6 H 0.5790 -0.1974 0.5339 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4373(2) -0.11073(15) 0.48742(18) 0.0219(6) Uani 1 1 d . . . . .
C8 C 0.4412(2) -0.07658(16) 0.58467(19) 0.0268(6) Uani 1 1 d . . . . .
H8 H 0.5003 -0.0961 0.6460 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3593(2) -0.01534(16) 0.58991(19) 0.0269(6) Uani 1 1 d . . . . .
H9 H 0.3606 0.0074 0.6555 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2729(2) 0.01469(15) 0.49974(18) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.3495(2) -0.07764(14) 0.40031(17) 0.0192(5) Uani 1 1 d . . . . .
C12 C 0.3407(2) -0.11099(14) 0.29899(18) 0.0192(5) Uani 1 1 d . . . . .
C13 C 0.1316(2) -0.08055(17) 0.03540(19) 0.0335(7) Uani 1 1 d . . . . .
H13A H 0.0587 -0.0707 0.0593 0.050 Uiso 1 1 calc R U . . .
H13B H 0.1115 -0.1221 -0.0208 0.050 Uiso 1 1 calc R U . . .
H13C H 0.1565 -0.0277 0.0098 0.050 Uiso 1 1 calc R U . . .
C14 C 0.1825(3) 0.08117(17) 0.5060(2) 0.0368(7) Uani 1 1 d . . . . .
H14A H 0.1764 0.1226 0.4509 0.055 Uiso 1 1 calc R U . . .
H14B H 0.2104 0.1090 0.5737 0.055 Uiso 1 1 calc R U . . .
H14C H 0.1012 0.0556 0.4974 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2365(2) 0.14067(15) 0.17293(19) 0.0220(6) Uani 1 1 d . . . . .
C16 C 0.2840(2) 0.20358(15) 0.11165(19) 0.0232(6) Uani 1 1 d . . . . .
C17 C 0.2390(3) 0.20343(16) 0.0044(2) 0.0318(6) Uani 1 1 d . . . . .
H17 H 0.1757 0.1649 -0.0291 0.038 Uiso 1 1 calc R U . . .
C18 C 0.2844(3) 0.25818(18) -0.0543(2) 0.0413(7) Uani 1 1 d . . . . .
H18 H 0.2529 0.2569 -0.1279 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3755(3) 0.31496(17) -0.0070(2) 0.0417(8) Uani 1 1 d . . . . .
H19 H 0.4078 0.3523 -0.0477 0.050 Uiso 1 1 calc R U . . .
C20 C 0.4196(3) 0.31716(17) 0.1000(2) 0.0377(7) Uani 1 1 d . . . . .
H20 H 0.4814 0.3568 0.1330 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3742(2) 0.26196(16) 0.1594(2) 0.0294(6) Uani 1 1 d . . . . .
H21 H 0.4048 0.2639 0.2330 0.035 Uiso 1 1 calc R U . . .
C22 C -0.0682(2) 0.03308(16) 0.23697(18) 0.0225(6) Uani 1 1 d . . . . .
C23 C -0.2064(2) 0.03132(16) 0.20246(18) 0.0242(6) Uani 1 1 d . . . . .
C24 C -0.2733(3) 0.10524(18) 0.1941(2) 0.0348(7) Uani 1 1 d . . . . .
H24 H -0.2315 0.1572 0.2136 0.042 Uiso 1 1 calc R U . . .
C25 C -0.4015(3) 0.1034(2) 0.1571(2) 0.0501(9) Uani 1 1 d . . . . .
H25 H -0.4473 0.1542 0.1506 0.060 Uiso 1 1 calc R U . . .
C26 C -0.4623(3) 0.0283(3) 0.1300(2) 0.0554(10) Uani 1 1 d . . . . .
H26 H -0.5502 0.0272 0.1057 0.066 Uiso 1 1 calc R U . . .
C27 C -0.2688(2) -0.04377(18) 0.17383(19) 0.0325(7) Uani 1 1 d . . . . .
H27 H -0.2236 -0.0948 0.1788 0.039 Uiso 1 1 calc R U . . .
C28 C -0.3967(3) -0.0448(2) 0.1379(2) 0.0479(9) Uani 1 1 d . . . . .
H28 H -0.4391 -0.0966 0.1187 0.057 Uiso 1 1 calc R U . . .
O1 O -0.01086(15) -0.03242(11) 0.22407(13) 0.0284(4) Uani 1 1 d . . . . .
O2 O -0.01151(17) 0.09804(11) 0.27528(14) 0.0361(5) Uani 1 1 d . . . . .
O3 O 0.14780(16) 0.09480(11) 0.12677(13) 0.0323(4) Uani 1 1 d . . . . .
O4 O 0.28713(15) 0.13159(11) 0.26900(13) 0.0311(4) Uani 1 1 d . . . . .
N1 N 0.25203(17) -0.07838(12) 0.21678(14) 0.0205(5) Uani 1 1 d . . . . .
N2 N 0.26828(17) -0.01571(12) 0.40618(14) 0.0206(4) Uani 1 1 d . . . . .
Co1 Co 0.15898(3) 0.02452(2) 0.25988(2) 0.02065(11) 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 N1 1.333(3) . ?
C1 C2 1.402(3) . ?
C1 C13 1.491(3) . ?
C2 C3 1.364(3) . ?
C3 C4 1.403(3) . ?
C4 C12 1.399(3) . ?
C4 C5 1.432(3) . ?
C5 C6 1.349(3) . ?
C6 C7 1.425(3) . ?
C7 C11 1.399(3) . ?
C7 C8 1.406(3) . ?
C8 C9 1.359(3) . ?
C9 C10 1.401(3) . ?
C10 N2 1.336(3) . ?
C10 C14 1.490(3) . ?
C11 N2 1.364(3) . ?
C11 C12 1.440(3) . ?
C12 N1 1.361(3) . ?
C15 O3 1.249(3) . ?
C15 O4 1.261(3) . ?
C15 C16 1.492(3) . ?
C15 Co1 2.480(2) . ?
C16 C17 1.384(3) . ?
C16 C21 1.390(3) . ?
C17 C18 1.372(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.382(4) . ?
C20 C21 1.382(4) . ?
C22 O2 1.246(3) . ?
C22 O1 1.265(3) . ?
C22 C23 1.493(3) . ?
C22 Co1 2.498(2) . ?
C23 C27 1.383(3) . ?
C23 C24 1.384(3) . ?
C24 C25 1.387(4) . ?
C25 C26 1.373(5) . ?
C26 C28 1.367(5) . ?
C27 C28 1.384(4) . ?
O1 Co1 2.0479(16) . ?
O2 Co1 2.3135(19) . ?
O3 Co1 2.0846(17) . ?
O4 Co1 2.2153(18) . ?
N1 Co1 2.1157(19) . ?
N2 Co1 2.0966(19) . ?

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
N1 C1 C2 121.1(2) . . ?
N1 C1 C13 118.3(2) . . ?
C2 C1 C13 120.7(2) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 119.3(2) . . ?
C12 C4 C3 117.2(2) . . ?
C12 C4 C5 119.5(2) . . ?
C3 C4 C5 123.3(2) . . ?
C6 C5 C4 120.9(2) . . ?
C5 C6 C7 120.9(2) . . ?
C11 C7 C8 117.2(2) . . ?
C11 C7 C6 119.8(2) . . ?
C8 C7 C6 123.0(2) . . ?
C9 C8 C7 119.2(2) . . ?
C8 C9 C10 120.8(2) . . ?
N2 C10 C9 121.3(2) . . ?
N2 C10 C14 118.1(2) . . ?
C9 C10 C14 120.6(2) . . ?
N2 C11 C7 123.2(2) . . ?
N2 C11 C12 117.3(2) . . ?
C7 C11 C12 119.5(2) . . ?
N1 C12 C4 123.0(2) . . ?
N1 C12 C11 117.5(2) . . ?
C4 C12 C11 119.4(2) . . ?
O3 C15 O4 120.1(2) . . ?
O3 C15 C16 118.8(2) . . ?
O4 C15 C16 121.0(2) . . ?
O3 C15 Co1 57.11(12) . . ?
O4 C15 Co1 63.07(13) . . ?
C16 C15 Co1 173.62(17) . . ?
C17 C16 C21 118.7(2) . . ?
C17 C16 C15 119.6(2) . . ?
C21 C16 C15 121.7(2) . . ?
C18 C17 C16 121.0(3) . . ?
C17 C18 C19 120.3(3) . . ?
C18 C19 C20 119.5(3) . . ?
C19 C20 C21 120.4(3) . . ?
C20 C21 C16 120.2(3) . . ?
O2 C22 O1 121.2(2) . . ?
O2 C22 C23 120.6(2) . . ?
O1 C22 C23 118.2(2) . . ?
O2 C22 Co1 66.93(14) . . ?
O1 C22 Co1 54.77(12) . . ?
C23 C22 Co1 168.68(18) . . ?
C27 C23 C24 119.3(2) . . ?
C27 C23 C22 120.3(2) . . ?
C24 C23 C22 120.4(2) . . ?
C23 C24 C25 120.0(3) . . ?
C26 C25 C24 120.2(3) . . ?
C28 C26 C25 120.1(3) . . ?
C23 C27 C28 120.2(3) . . ?
C26 C28 C27 120.3(3) . . ?
C22 O1 Co1 94.92(14) . . ?
C22 O2 Co1 83.38(15) . . ?
C15 O3 Co1 92.68(15) . . ?
C15 O4 Co1 86.43(14) . . ?
C1 N1 C12 118.8(2) . . ?
C1 N1 Co1 128.99(16) . . ?
C12 N1 Co1 112.26(15) . . ?
C10 N2 C11 118.3(2) . . ?
C10 N2 Co1 128.75(16) . . ?
C11 N2 Co1 112.81(14) . . ?
O1 Co1 O3 102.53(7) . . ?
O1 Co1 N2 109.93(7) . . ?
O3 Co1 N2 147.44(7) . . ?
O1 Co1 N1 95.71(7) . . ?
O3 Co1 N1 95.13(7) . . ?
N2 Co1 N1 79.51(7) . . ?
O1 Co1 O4 154.85(7) . . ?
O3 Co1 O4 60.67(6) . . ?
N2 Co1 O4 89.21(7) . . ?
N1 Co1 O4 103.95(7) . . ?
O1 Co1 O2 59.83(6) . . ?
O3 Co1 O2 87.86(7) . . ?
N2 Co1 O2 110.35(7) . . ?
N1 Co1 O2 155.33(7) . . ?
O4 Co1 O2 98.86(6) . . ?
O1 Co1 C15 130.84(7) . . ?
O3 Co1 C15 30.21(7) . . ?
N2 Co1 C15 118.59(8) . . ?
N1 Co1 C15 100.06(7) . . ?
O4 Co1 C15 30.49(7) . . ?
O2 Co1 C15 94.79(7) . . ?
O1 Co1 C22 30.31(7) . . ?
O3 Co1 C22 93.56(7) . . ?
N2 Co1 C22 115.79(7) . . ?
N1 Co1 C22 125.66(8) . . ?
O4 Co1 C22 126.60(7) . . ?
O2 Co1 C22 29.69(7) . . ?
C15 Co1 C22 113.13(8) . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1581345'
_audit_update_record             
;
2017-12-01 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N2 O4 Zn'
_chemical_formula_iupac          ?
_chemical_formula_weight         515.86

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.722(3)
_cell_length_b                   14.424(3)
_cell_length_c                   9.2768(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.848(6)
_cell_angle_gamma                90
_cell_volume                     2370.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6464
_cell_measurement_theta_min      2.3010
_cell_measurement_theta_max      28.0409
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064

_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   ?
_diffrn_source_type              MoK\a

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            25904
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2953
_reflns_number_gt                2408
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1302
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.427
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.5 0.26328(3) 0.75 0.01959(15) Uani d T P S 1 . .
N N1 0.44421(11) 0.37238(14) 0.64770(18) 0.0182(4) Uani d . . . 1 . .
O O1 0.47335(11) 0.17899(14) 0.9047(2) 0.0353(5) Uani d . . . 1 . .
O O2 0.36703(15) 0.25716(14) 0.8869(3) 0.0428(6) Uani d . . . 1 . .
C C1 0.40627(16) 0.19644(17) 0.9437(3) 0.0257(5) Uani d . . . 1 . .
C C2 0.37702(14) 0.13749(16) 1.0629(2) 0.0218(5) Uani d . . . 1 . .
C C3 0.30652(15) 0.15512(18) 1.1161(3) 0.0273(5) Uani d . . . 1 . .
H H5 0.2773 0.2055 1.0788 0.033 Uiso calc U . R 1 . .
C C4 0.27833(15) 0.0997(2) 1.2234(3) 0.0316(6) Uani d . . . 1 . .
H H1 0.2299 0.1123 1.2597 0.038 Uiso calc U . R 1 . .
C C5 0.31975(18) 0.0270(2) 1.2776(3) 0.0429(8) Uani d . . . 1 . .
H H2 0.3 -0.0112 1.3508 0.051 Uiso calc U . R 1 . .
C C6 0.3903(2) 0.0091(3) 1.2258(4) 0.0606(11) Uani d . . . 1 . .
H H3 0.4192 -0.0413 1.2635 0.073 Uiso calc U . R 1 . .
C C7 0.41926(18) 0.0649(2) 1.1183(3) 0.0446(8) Uani d . . . 1 . .
H H4 0.4681 0.0529 1.0833 0.053 Uiso calc U . R 1 . .
C C8 0.38857(13) 0.36884(18) 0.5473(2) 0.0231(5) Uani d . . . 1 . .
C C9 0.36142(16) 0.2750(2) 0.5006(3) 0.0324(6) Uani d . . . 1 . .
H H6 0.4044 0.2377 0.4706 0.049 Uiso calc U . R 1 . .
H H8 0.325 0.2816 0.4195 0.049 Uiso calc U . R 1 . .
H H7 0.3371 0.2443 0.5811 0.049 Uiso calc U . R 1 . .
C C10 0.35689(14) 0.45174(19) 0.4910(2) 0.0265(5) Uani d . . . 1 . .
H H10 0.3173 0.4487 0.4197 0.032 Uiso calc U . R 1 . .
C C11 0.38230(15) 0.53567(19) 0.5375(2) 0.0269(5) Uani d . . . 1 . .
H H9 0.3606 0.5909 0.4988 0.032 Uiso calc U . R 1 . .
C C12 0.44117(14) 0.54059(17) 0.6437(2) 0.0224(5) Uani d . . . 1 . .
C C13 0.47181(16) 0.62575(17) 0.6988(2) 0.0275(5) Uani d . . . 1 . .
H H11 0.4524 0.683 0.6632 0.033 Uiso calc U . R 1 . .
C C14 0.46995(13) 0.45597(16) 0.6959(2) 0.0183(5) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 . 1.9508(18) ?
Zn1 O1 2_656 1.9508(18) ?
Zn1 N1 . 2.0722(19) ?
Zn1 N1 2_656 2.0722(19) ?
N1 C8 . 1.335(3) ?
N1 C14 . 1.360(3) ?
O1 C1 . 1.278(3) ?
O2 C1 . 1.227(4) ?
C1 C2 . 1.501(3) ?
C2 C7 . 1.378(4) ?
C2 C3 . 1.382(4) ?
C3 C4 . 1.382(3) ?
C3 H5 . 0.95 ?
C4 C5 . 1.367(4) ?
C4 H1 . 0.95 ?
C5 C6 . 1.378(5) ?
C5 H2 . 0.95 ?
C6 C7 . 1.392(4) ?
C6 H3 . 0.95 ?
C7 H4 . 0.95 ?
C8 C10 . 1.414(3) ?
C8 C9 . 1.495(4) ?
C9 H6 . 0.98 ?
C9 H8 . 0.98 ?
C9 H7 . 0.98 ?
C10 C11 . 1.357(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.413(4) ?
C11 H9 . 0.95 ?
C12 C14 . 1.403(3) ?
C12 C13 . 1.431(4) ?
C13 C13 2_656 1.357(5) ?
C13 H11 . 0.95 ?
C14 C14 2_656 1.440(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Zn1 O1 . 2_656 102.89(12) ?
O1 Zn1 N1 . . 133.40(8) ?
O1 Zn1 N1 2_656 . 105.04(8) ?
O1 Zn1 N1 . 2_656 105.05(8) ?
O1 Zn1 N1 2_656 2_656 133.39(8) ?
N1 Zn1 N1 . 2_656 81.18(11) ?
C8 N1 C14 . . 119.7(2) ?
C8 N1 Zn1 . . 128.40(16) ?
C14 N1 Zn1 . . 111.89(15) ?
C1 O1 Zn1 . . 109.55(17) ?
O2 C1 O1 . . 122.6(2) ?
O2 C1 C2 . . 121.1(2) ?
O1 C1 C2 . . 116.3(2) ?
C7 C2 C3 . . 119.6(2) ?
C7 C2 C1 . . 120.6(2) ?
C3 C2 C1 . . 119.8(2) ?
C2 C3 C4 . . 120.2(2) ?
C2 C3 H5 . . 119.9 ?
C4 C3 H5 . . 119.9 ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 H1 . . 119.8 ?
C3 C4 H1 . . 119.8 ?
C4 C5 C6 . . 119.8(3) ?
C4 C5 H2 . . 120.1 ?
C6 C5 H2 . . 120.1 ?
C5 C6 C7 . . 120.1(3) ?
C5 C6 H3 . . 119.9 ?
C7 C6 H3 . . 119.9 ?
C2 C7 C6 . . 119.9(3) ?
C2 C7 H4 . . 120.1 ?
C6 C7 H4 . . 120.1 ?
N1 C8 C10 . . 120.1(2) ?
N1 C8 C9 . . 117.4(2) ?
C10 C8 C9 . . 122.5(2) ?
C8 C9 H6 . . 109.5 ?
C8 C9 H8 . . 109.5 ?
H6 C9 H8 . . 109.5 ?
C8 C9 H7 . . 109.5 ?
H6 C9 H7 . . 109.5 ?
H8 C9 H7 . . 109.5 ?
C11 C10 C8 . . 120.9(2) ?
C11 C10 H10 . . 119.6 ?
C8 C10 H10 . . 119.6 ?
C10 C11 C12 . . 119.8(2) ?
C10 C11 H9 . . 120.1 ?
C12 C11 H9 . . 120.1 ?
C14 C12 C11 . . 116.7(2) ?
C14 C12 C13 . . 119.6(2) ?
C11 C12 C13 . . 123.7(2) ?
C13 C13 C12 2_656 . 120.84(14) ?
C13 C13 H11 2_656 . 119.6 ?
C12 C13 H11 . . 119.6 ?
N1 C14 C12 . . 122.9(2) ?
N1 C14 C14 . 2_656 117.52(13) ?
C12 C14 C14 . 2_656 119.55(14) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Zn1 O1 C1 O2 . . . . 0.8(3) ?
Zn1 O1 C1 C2 . . . . -179.84(16) ?
O2 C1 C2 C7 . . . . 175.0(3) ?
O1 C1 C2 C7 . . . . -4.4(4) ?
O2 C1 C2 C3 . . . . -4.0(4) ?
O1 C1 C2 C3 . . . . 176.7(2) ?
C7 C2 C3 C4 . . . . -0.6(4) ?
C1 C2 C3 C4 . . . . 178.4(2) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C3 C4 C5 C6 . . . . 0.5(5) ?
C4 C5 C6 C7 . . . . -0.1(6) ?
C3 C2 C7 C6 . . . . 0.9(5) ?
C1 C2 C7 C6 . . . . -178.0(3) ?
C5 C6 C7 C2 . . . . -0.6(6) ?
C14 N1 C8 C10 . . . . 0.3(3) ?
Zn1 N1 C8 C10 . . . . 179.34(15) ?
C14 N1 C8 C9 . . . . -178.7(2) ?
Zn1 N1 C8 C9 . . . . 0.3(3) ?
N1 C8 C10 C11 . . . . 0.0(4) ?
C9 C8 C10 C11 . . . . 179.1(2) ?
C8 C10 C11 C12 . . . . 0.0(4) ?
C10 C11 C12 C14 . . . . -0.3(3) ?
C10 C11 C12 C13 . . . . 179.7(2) ?
C14 C12 C13 C13 . . . 2_656 -0.2(4) ?
C11 C12 C13 C13 . . . 2_656 179.8(3) ?
C8 N1 C14 C12 . . . . -0.7(3) ?
Zn1 N1 C14 C12 . . . . -179.89(17) ?
C8 N1 C14 C14 . . . 2_656 -179.9(2) ?
Zn1 N1 C14 C14 . . . 2_656 0.9(3) ?
C11 C12 C14 N1 . . . . 0.7(3) ?
C13 C12 C14 N1 . . . . -179.3(2) ?
C11 C12 C14 C14 . . . 2_656 179.9(2) ?
C13 C12 C14 C14 . . . 2_656 -0.1(4) ?

