# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1848465'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        HL
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N3 O2'
_chemical_formula_weight         259.30

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.6721(2)
_cell_length_b                   11.4426(2)
_cell_length_c                   15.8174(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1388.59(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6138
_cell_measurement_theta_min      3.9240
_cell_measurement_theta_max      28.2460
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_T_min  0.52239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            10420
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.951
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2439
_reflns_number_gt                2280
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_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)+(0.0529P)²+0.1683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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
O1 O 0.8114(2) 0.82970(16) 0.64771(14) 0.0628(5) Uani 1 1 d . . . . .
H1 H 0.8664 0.7703 0.6362 0.094 Uiso 1 1 calc R U . . .
O2 O 0.5982(3) 1.00380(17) 0.67676(15) 0.0745(7) Uani 1 1 d . . . . .
N2 N 1.1216(3) 0.27278(18) 0.60887(14) 0.0521(5) Uani 1 1 d . . . . .
N3 N 1.0456(4) 0.1308(2) 0.52268(19) 0.0735(8) Uani 1 1 d . . . . .
C1 C 0.4920(5) 1.1047(3) 0.6835(3) 0.0903(12) Uani 1 1 d . . . . .
H1A H 0.4442 1.1234 0.6291 0.135 Uiso 1 1 calc R U . . .
H1B H 0.5609 1.1691 0.7034 0.135 Uiso 1 1 calc R U . . .
H1C H 0.3989 1.0899 0.7227 0.135 Uiso 1 1 calc R U . . .
C2 C 0.5235(4) 0.9029(2) 0.64909(17) 0.0538(6) Uani 1 1 d . . . . .
C3 C 0.3477(4) 0.8855(3) 0.63516(19) 0.0689(8) Uani 1 1 d . . . . .
H3 H 0.2689 0.9452 0.6466 0.083 Uiso 1 1 calc R U . . .
C4 C 0.2879(4) 0.7794(3) 0.6042(2) 0.0793(10) Uani 1 1 d . . . . .
H4 H 0.1694 0.7689 0.5945 0.095 Uiso 1 1 calc R U . . .
C5 C 0.4005(4) 0.6909(3) 0.5879(2) 0.0715(9) Uani 1 1 d . . . . .
H5 H 0.3586 0.6205 0.5667 0.086 Uiso 1 1 calc R U . . .
C6 C 0.5793(4) 0.7047(2) 0.60279(17) 0.0522(6) Uani 1 1 d . . . . .
C7 C 0.6412(4) 0.8115(2) 0.63307(16) 0.0488(6) Uani 1 1 d . . . . .
C8 C 0.6974(4) 0.6081(2) 0.58684(17) 0.0580(7) Uani 1 1 d . . . . .
H8 H 0.6530 0.5389 0.5648 0.070 Uiso 1 1 calc R U . . .
C9 C 0.9709(4) 0.5152(2) 0.58210(18) 0.0592(7) Uani 1 1 d . . . . .
H9A H 1.0526 0.5369 0.5380 0.071 Uiso 1 1 calc R U . . .
H9B H 0.8997 0.4515 0.5611 0.071 Uiso 1 1 calc R U . . .
C10 C 1.0702(4) 0.4752(2) 0.65910(18) 0.0584(7) Uani 1 1 d . . . . .
H10A H 0.9882 0.4459 0.7007 0.070 Uiso 1 1 calc R U . . .
H10B H 1.1301 0.5416 0.6837 0.070 Uiso 1 1 calc R U . . .
C11 C 1.2022(4) 0.3806(2) 0.63952(18) 0.0579(7) Uani 1 1 d . . . . .
H11A H 1.2828 0.4093 0.5971 0.069 Uiso 1 1 calc R U . . .
H11B H 1.2685 0.3635 0.6902 0.069 Uiso 1 1 calc R U . . .
C12 C 1.1308(4) 0.2288(2) 0.53078(19) 0.0611(7) Uani 1 1 d . . . . .
H12 H 1.1914 0.2643 0.4868 0.073 Uiso 1 1 calc R U . . .
C13 C 0.9773(4) 0.1108(3) 0.6011(2) 0.0718(8) Uani 1 1 d . . . . .
H13 H 0.9094 0.0465 0.6155 0.086 Uiso 1 1 calc R U . . .
C14 C 1.0219(5) 0.1969(2) 0.6545(2) 0.0679(8) Uani 1 1 d . . . . .
H14 H 0.9911 0.2035 0.7112 0.081 Uiso 1 1 calc R U . . .
N1 N 0.8594(3) 0.61527(18) 0.60201(15) 0.0565(6) 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
O1 C7 1.343(3) . ?
O1 H1 0.8200 . ?
O2 C2 1.361(4) . ?
O2 C1 1.417(4) . ?
N2 C12 1.336(4) . ?
N2 C14 1.363(4) . ?
N2 C11 1.463(3) . ?
N3 C12 1.304(4) . ?
N3 C13 1.366(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.387(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(4) . ?
C6 C8 1.451(4) . ?
C8 N1 1.269(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.463(3) . ?
C9 C10 1.508(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.514(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C13 C14 1.342(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C7 O1 H1 109.5 . . ?
C2 O2 C1 118.2(3) . . ?
C12 N2 C14 106.2(2) . . ?
C12 N2 C11 127.0(2) . . ?
C14 N2 C11 126.8(2) . . ?
C12 N3 C13 104.3(3) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C3 125.8(3) . . ?
O2 C2 C7 114.8(2) . . ?
C3 C2 C7 119.4(3) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 C8 120.9(2) . . ?
C5 C6 C8 119.8(3) . . ?
O1 C7 C6 121.7(2) . . ?
O1 C7 C2 118.6(2) . . ?
C6 C7 C2 119.7(3) . . ?
N1 C8 C6 122.0(2) . . ?
N1 C8 H8 119.0 . . ?
C6 C8 H8 119.0 . . ?
N1 C9 C10 111.0(2) . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 112.9(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C10 112.8(2) . . ?
N2 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N3 C12 N2 112.9(3) . . ?
N3 C12 H12 123.6 . . ?
N2 C12 H12 123.6 . . ?
C14 C13 N3 110.5(3) . . ?
C14 C13 H13 124.7 . . ?
N3 C13 H13 124.7 . . ?
C13 C14 N2 106.1(3) . . ?
C13 C14 H14 127.0 . . ?
N2 C14 H14 127.0 . . ?
C8 N1 C9 118.8(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
C1 O2 C2 C3 -7.4(5) . . . . ?
C1 O2 C2 C7 171.7(3) . . . . ?
O2 C2 C3 C4 177.9(3) . . . . ?
C7 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C7 -1.2(5) . . . . ?
C4 C5 C6 C8 178.6(3) . . . . ?
C5 C6 C7 O1 -179.4(3) . . . . ?
C8 C6 C7 O1 0.7(4) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C8 C6 C7 C2 -179.1(2) . . . . ?
O2 C2 C7 O1 1.4(4) . . . . ?
C3 C2 C7 O1 -179.4(3) . . . . ?
O2 C2 C7 C6 -178.7(2) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C7 C6 C8 N1 2.2(4) . . . . ?
C5 C6 C8 N1 -177.6(3) . . . . ?
N1 C9 C10 C11 -173.6(2) . . . . ?
C12 N2 C11 C10 110.7(3) . . . . ?
C14 N2 C11 C10 -69.3(3) . . . . ?
C9 C10 C11 N2 -63.7(3) . . . . ?
C13 N3 C12 N2 0.0(4) . . . . ?
C14 N2 C12 N3 -0.2(4) . . . . ?
C11 N2 C12 N3 179.8(3) . . . . ?
C12 N3 C13 C14 0.2(4) . . . . ?
N3 C13 C14 N2 -0.3(4) . . . . ?
C12 N2 C14 C13 0.3(3) . . . . ?
C11 N2 C14 C13 -179.7(3) . . . . ?
C6 C8 N1 C9 -178.4(2) . . . . ?
C10 C9 N1 C8 -123.8(3) . . . . ?

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Ether'
_exptl_crystal_preparation       chemosensor
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1854143'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2019-01-21 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            'C56 H61.50 Cu2 N12 O8'
_chemical_formula_weight         1157.75

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   22.941(5)
_cell_length_b                   7.6098(12)
_cell_length_c                   34.505(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.03(2)
_cell_angle_gamma                90
_cell_volume                     5818(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1196
_cell_measurement_theta_min      3.1790
_cell_measurement_theta_max      16.7660

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not defined'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             2414
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_T_min  0.52239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            29351
_diffrn_reflns_av_unetI/netI     0.2206
_diffrn_reflns_av_R_equivalents  0.2812
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             5105
_reflns_number_gt                1820
_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    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2602
_refine_ls_R_factor_gt           0.1180
_refine_ls_wR_factor_ref         0.3998
_refine_ls_wR_factor_gt          0.2945
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
Cu1 Cu 0.41885(7) 0.38188(19) 0.32857(4) 0.0622(7) Uani 1 1 d . . . . .
O1 O 0.4324(5) 0.5619(13) 0.4520(3) 0.090(3) Uani 1 1 d . . . . .
O2 O 0.4393(4) 0.3996(10) 0.3861(2) 0.069(2) Uani 1 1 d . . . . .
O3 O 0.3931(3) 0.3622(10) 0.2715(2) 0.058(2) Uani 1 1 d . . . . .
O4 O 0.3217(4) 0.3359(11) 0.1987(2) 0.071(2) Uani 1 1 d . . . . .
N1 N 0.3963(5) 0.1272(12) 0.3319(3) 0.061(3) Uani 1 1 d . . . . .
N2 N 0.1683(5) -0.0306(12) 0.1749(3) 0.059(3) Uani 1 1 d . . . . .
N3 N 0.2644(5) -0.0878(11) 0.2025(3) 0.062(3) Uani 1 1 d . . . . .
N4 N 0.4838(4) 0.5565(12) 0.3256(3) 0.057(3) Uani 1 1 d . . . . .
N5 N 0.5803(6) 0.924(2) 0.4266(3) 0.091(4) Uani 1 1 d . . . . .
N6 N 0.6389(10) 1.157(2) 0.4332(5) 0.124(6) Uani 1 1 d . . . . .
C1 C 0.4120(5) 0.3156(19) 0.4096(4) 0.064(3) Uani 1 1 d . . . . .
C2 C 0.4083(6) 0.393(2) 0.4461(4) 0.076(4) Uani 1 1 d . . . . .
C3 C 0.4278(7) 0.654(2) 0.4883(4) 0.108(6) Uani 1 1 d . . . . .
H3A H 0.3873 0.6951 0.4848 0.162 Uiso 1 1 calc R U . . .
H3B H 0.4551 0.7517 0.4932 0.162 Uiso 1 1 calc R U . . .
H3C H 0.4381 0.5746 0.5107 0.162 Uiso 1 1 calc R U . . .
C4 C 0.3813(7) 0.302(2) 0.4716(4) 0.085(4) Uani 1 1 d . . . . .
H4 H 0.3791 0.3539 0.4956 0.102 Uiso 1 1 calc R U . . .
C5 C 0.3584(8) 0.141(2) 0.4626(5) 0.095(5) Uani 1 1 d . . . . .
H5 H 0.3428 0.0803 0.4810 0.114 Uiso 1 1 calc R U . . .
C6 C 0.3575(7) 0.0657(19) 0.4264(4) 0.084(4) Uani 1 1 d . . . . .
H6 H 0.3388 -0.0424 0.4197 0.100 Uiso 1 1 calc R U . . .
C7 C 0.3838(6) 0.1473(18) 0.4005(4) 0.065(3) Uani 1 1 d . . . . .
C8 C 0.3812(5) 0.0665(18) 0.3642(4) 0.072(4) Uani 1 1 d . . . . .
H8 H 0.3667 -0.0481 0.3619 0.086 Uiso 1 1 calc R U . . .
C9 C 0.3889(5) 0.0029(17) 0.2973(4) 0.067(4) Uani 1 1 d . . . . .
H9A H 0.3976 -0.1156 0.3075 0.081 Uiso 1 1 calc R U . . .
H9B H 0.4178 0.0325 0.2822 0.081 Uiso 1 1 calc R U . . .
C10 C 0.3245(6) 0.0083(15) 0.2689(4) 0.064(3) Uani 1 1 d . . . . .
H10A H 0.2959 -0.0444 0.2818 0.077 Uiso 1 1 calc R U . . .
H10B H 0.3124 0.1289 0.2621 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3256(6) -0.0904(17) 0.2326(4) 0.070(4) Uani 1 1 d . . . . .
H11A H 0.3373 -0.2110 0.2398 0.084 Uiso 1 1 calc R U . . .
H11B H 0.3555 -0.0393 0.2206 0.084 Uiso 1 1 calc R U . . .
C12 C 0.2121(6) -0.0238(16) 0.2094(4) 0.065(3) Uani 1 1 d . . . . .
H12 H 0.2077 0.0172 0.2339 0.078 Uiso 1 1 calc R U . . .
C13 C 0.2515(6) -0.1379(16) 0.1630(4) 0.072(4) Uani 1 1 d . . . . .
H13 H 0.2783 -0.1863 0.1498 0.086 Uiso 1 1 calc R U . . .
C14 C 0.1915(6) -0.1032(17) 0.1465(4) 0.073(4) Uani 1 1 d . . . . .
H14 H 0.1703 -0.1260 0.1202 0.088 Uiso 1 1 calc R U . . .
C15 C 0.4049(5) 0.4664(15) 0.2445(4) 0.056(3) Uani 1 1 d . . . . .
C16 C 0.3697(5) 0.4511(15) 0.2040(4) 0.056(3) Uani 1 1 d . . . . .
C17 C 0.2806(7) 0.327(2) 0.1593(4) 0.090(5) Uani 1 1 d . . . . .
H17A H 0.2658 0.4423 0.1509 0.135 Uiso 1 1 calc R U . . .
H17B H 0.2473 0.2515 0.1601 0.135 Uiso 1 1 calc R U . . .
H17C H 0.3013 0.2803 0.1407 0.135 Uiso 1 1 calc R U . . .
C18 C 0.3820(6) 0.5483(17) 0.1732(4) 0.069(4) Uani 1 1 d . . . . .
H18 H 0.3577 0.5373 0.1472 0.082 Uiso 1 1 calc R U . . .
C19 C 0.4306(6) 0.6613(18) 0.1812(4) 0.070(4) Uani 1 1 d . . . . .
H19 H 0.4406 0.7216 0.1604 0.084 Uiso 1 1 calc R U . . .
C20 C 0.4633(6) 0.6840(16) 0.2189(4) 0.071(4) Uani 1 1 d . . . . .
H20 H 0.4946 0.7654 0.2238 0.085 Uiso 1 1 calc R U . . .
C21 C 0.4527(5) 0.5897(14) 0.2521(4) 0.056(3) Uani 1 1 d . . . . .
C22 C 0.4898(5) 0.6225(15) 0.2933(4) 0.058(3) Uani 1 1 d . . . . .
H22 H 0.5215 0.7015 0.2957 0.070 Uiso 1 1 calc R U . . .
C23 C 0.5265(6) 0.6227(17) 0.3627(4) 0.071(4) Uani 1 1 d . . . . .
H23A H 0.5626 0.6679 0.3565 0.085 Uiso 1 1 calc R U . . .
H23B H 0.5381 0.5278 0.3819 0.085 Uiso 1 1 calc R U . . .
C24 C 0.4961(6) 0.7665(16) 0.3802(4) 0.074(4) Uani 1 1 d . . . . .
H24A H 0.4943 0.8707 0.3637 0.088 Uiso 1 1 calc R U . . .
H24B H 0.4548 0.7306 0.3782 0.088 Uiso 1 1 calc R U . . .
C25 C 0.5249(8) 0.816(2) 0.4230(4) 0.100(5) Uani 1 1 d . . . . .
H25A H 0.4963 0.8816 0.4336 0.120 Uiso 1 1 calc R U . . .
H25B H 0.5355 0.7099 0.4389 0.120 Uiso 1 1 calc R U . . .
C26 C 0.5806(9) 1.106(3) 0.4258(5) 0.109(6) Uani 1 1 d . . . . .
H26 H 0.5470 1.1792 0.4210 0.131 Uiso 1 1 calc R U . . .
C27 C 0.6716(11) 1.012(5) 0.4358(5) 0.131(8) Uani 1 1 d . . . . .
H27 H 0.7133 1.0110 0.4396 0.157 Uiso 1 1 calc R U . . .
C28 C 0.6374(9) 0.866(3) 0.4321(4) 0.101(5) Uani 1 1 d . . . . .
H28 H 0.6505 0.7498 0.4332 0.121 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
Cu1 O3 1.911(8) . ?
Cu1 O2 1.923(8) . ?
Cu1 N1 2.016(9) . ?
Cu1 N4 2.019(9) . ?
Cu1 N2 2.274(10) 7 ?
O1 C2 1.392(15) . ?
O1 C3 1.460(14) . ?
O2 C1 1.311(13) . ?
O3 C15 1.302(13) . ?
O4 C16 1.383(13) . ?
O4 C17 1.441(14) . ?
N1 C8 1.333(15) . ?
N1 C9 1.497(14) . ?
N2 C14 1.347(14) . ?
N2 C12 1.347(15) . ?
N2 Cu1 2.274(10) 7 ?
N3 C13 1.371(15) . ?
N3 C12 1.373(14) . ?
N3 C11 1.516(15) . ?
N4 C22 1.261(14) . ?
N4 C23 1.484(14) . ?
N5 C28 1.35(2) . ?
N5 C26 1.385(19) . ?
N5 C25 1.490(18) . ?
N6 C27 1.32(2) . ?
N6 C26 1.35(2) . ?
C1 C2 1.412(17) . ?
C1 C7 1.433(17) . ?
C2 C4 1.388(18) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.335(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.352(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.548(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.466(15) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C13 C14 1.371(17) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C21 1.415(16) . ?
C15 C16 1.426(15) . ?
C16 C18 1.384(16) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.378(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.335(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.425(16) . ?
C20 H20 0.9300 . ?
C21 C22 1.476(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.506(16) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.502(17) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26 0.9300 . ?
C27 C28 1.35(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
O3 Cu1 O2 176.2(3) . . ?
O3 Cu1 N1 88.1(4) . . ?
O2 Cu1 N1 90.4(4) . . ?
O3 Cu1 N4 91.9(4) . . ?
O2 Cu1 N4 91.2(4) . . ?
N1 Cu1 N4 147.0(4) . . ?
O3 Cu1 N2 87.3(4) . 7 ?
O2 Cu1 N2 89.7(4) . 7 ?
N1 Cu1 N2 104.3(4) . 7 ?
N4 Cu1 N2 108.7(4) . 7 ?
C2 O1 C3 116.9(12) . . ?
C1 O2 Cu1 125.2(8) . . ?
C15 O3 Cu1 128.5(7) . . ?
C16 O4 C17 117.3(9) . . ?
C8 N1 C9 116.5(10) . . ?
C8 N1 Cu1 120.4(9) . . ?
C9 N1 Cu1 122.7(8) . . ?
C14 N2 C12 108.3(11) . . ?
C14 N2 Cu1 132.4(9) . 7 ?
C12 N2 Cu1 118.1(8) . 7 ?
C13 N3 C12 107.4(11) . . ?
C13 N3 C11 127.0(10) . . ?
C12 N3 C11 125.5(11) . . ?
C22 N4 C23 115.3(10) . . ?
C22 N4 Cu1 123.9(9) . . ?
C23 N4 Cu1 120.6(8) . . ?
C28 N5 C26 108.6(16) . . ?
C28 N5 C25 127.4(17) . . ?
C26 N5 C25 124.0(16) . . ?
C27 N6 C26 106.8(18) . . ?
O2 C1 C2 119.7(13) . . ?
O2 C1 C7 124.1(12) . . ?
C2 C1 C7 116.2(12) . . ?
C4 C2 O1 126.4(14) . . ?
C4 C2 C1 119.8(13) . . ?
O1 C2 C1 113.8(13) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 121.5(14) . . ?
C5 C4 H4 119.2 . . ?
C2 C4 H4 119.2 . . ?
C4 C5 C6 120.7(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.4(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 118.3(13) . . ?
C6 C7 C1 121.3(12) . . ?
C8 C7 C1 120.4(12) . . ?
N1 C8 C7 130.2(13) . . ?
N1 C8 H8 114.9 . . ?
C7 C8 H8 114.9 . . ?
N1 C9 C10 112.3(10) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 107.5(10) . . ?
C11 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 N3 111.2(10) . . ?
C10 C11 H11A 109.4 . . ?
N3 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
N3 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 N3 108.4(11) . . ?
N2 C12 H12 125.8 . . ?
N3 C12 H12 125.8 . . ?
C14 C13 N3 107.0(11) . . ?
C14 C13 H13 126.5 . . ?
N3 C13 H13 126.5 . . ?
N2 C14 C13 108.8(12) . . ?
N2 C14 H14 125.6 . . ?
C13 C14 H14 125.6 . . ?
O3 C15 C21 124.5(11) . . ?
O3 C15 C16 118.7(10) . . ?
C21 C15 C16 116.8(12) . . ?
O4 C16 C18 123.5(11) . . ?
O4 C16 C15 114.2(10) . . ?
C18 C16 C15 122.2(12) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C16 119.7(12) . . ?
C19 C18 H18 120.2 . . ?
C16 C18 H18 120.2 . . ?
C20 C19 C18 119.8(12) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 123.3(12) . . ?
C19 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C15 C21 C20 118.1(12) . . ?
C15 C21 C22 121.1(11) . . ?
C20 C21 C22 120.8(11) . . ?
N4 C22 C21 128.0(11) . . ?
N4 C22 H22 116.0 . . ?
C21 C22 H22 116.0 . . ?
N4 C23 C24 108.8(10) . . ?
N4 C23 H23A 109.9 . . ?
C24 C23 H23A 109.9 . . ?
N4 C23 H23B 109.9 . . ?
C24 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C25 C24 C23 116.4(12) . . ?
C25 C24 H24A 108.2 . . ?
C23 C24 H24A 108.2 . . ?
C25 C24 H24B 108.2 . . ?
C23 C24 H24B 108.2 . . ?
H24A C24 H24B 107.3 . . ?
N5 C25 C24 111.6(12) . . ?
N5 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
N5 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
N6 C26 N5 107.1(18) . . ?
N6 C26 H26 126.5 . . ?
N5 C26 H26 126.5 . . ?
N6 C27 C28 112(2) . . ?
N6 C27 H27 124.0 . . ?
C28 C27 H27 124.0 . . ?
C27 C28 N5 105.3(19) . . ?
C27 C28 H28 127.3 . . ?
N5 C28 H28 127.3 . . ?

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
Cu1 O2 C1 C2 -149.0(10) . . . . ?
Cu1 O2 C1 C7 29.7(17) . . . . ?
C3 O1 C2 C4 -1(2) . . . . ?
C3 O1 C2 C1 177.4(12) . . . . ?
O2 C1 C2 C4 -177.8(12) . . . . ?
C7 C1 C2 C4 3.4(19) . . . . ?
O2 C1 C2 O1 3.3(18) . . . . ?
C7 C1 C2 O1 -175.5(11) . . . . ?
O1 C2 C4 C5 178.6(15) . . . . ?
C1 C2 C4 C5 0(2) . . . . ?
C2 C4 C5 C6 -4(3) . . . . ?
C4 C5 C6 C7 5(3) . . . . ?
C5 C6 C7 C8 -179.3(14) . . . . ?
C5 C6 C7 C1 -1(2) . . . . ?
O2 C1 C7 C6 178.6(12) . . . . ?
C2 C1 C7 C6 -3(2) . . . . ?
O2 C1 C7 C8 -4(2) . . . . ?
C2 C1 C7 C8 175.3(12) . . . . ?
C9 N1 C8 C7 178.9(13) . . . . ?
Cu1 N1 C8 C7 -7.7(18) . . . . ?
C6 C7 C8 N1 170.5(13) . . . . ?
C1 C7 C8 N1 -7(2) . . . . ?
C8 N1 C9 C10 87.0(13) . . . . ?
Cu1 N1 C9 C10 -86.3(11) . . . . ?
N1 C9 C10 C11 169.1(10) . . . . ?
C9 C10 C11 N3 -178.5(10) . . . . ?
C13 N3 C11 C10 167.3(11) . . . . ?
C12 N3 C11 C10 -8.4(16) . . . . ?
C14 N2 C12 N3 2.1(14) . . . . ?
Cu1 N2 C12 N3 -166.9(7) 7 . . . ?
C13 N3 C12 N2 -1.4(13) . . . . ?
C11 N3 C12 N2 175.1(10) . . . . ?
C12 N3 C13 C14 0.1(14) . . . . ?
C11 N3 C13 C14 -176.2(11) . . . . ?
C12 N2 C14 C13 -2.0(15) . . . . ?
Cu1 N2 C14 C13 164.9(8) 7 . . . ?
N3 C13 C14 N2 1.1(15) . . . . ?
Cu1 O3 C15 C21 18.3(15) . . . . ?
Cu1 O3 C15 C16 -165.0(7) . . . . ?
C17 O4 C16 C18 -4.1(17) . . . . ?
C17 O4 C16 C15 174.1(10) . . . . ?
O3 C15 C16 O4 6.4(15) . . . . ?
C21 C15 C16 O4 -176.6(9) . . . . ?
O3 C15 C16 C18 -175.4(10) . . . . ?
C21 C15 C16 C18 1.5(16) . . . . ?
O4 C16 C18 C19 179.4(11) . . . . ?
C15 C16 C18 C19 1.5(18) . . . . ?
C16 C18 C19 C20 -4(2) . . . . ?
C18 C19 C20 C21 3(2) . . . . ?
O3 C15 C21 C20 174.6(10) . . . . ?
C16 C15 C21 C20 -2.1(15) . . . . ?
O3 C15 C21 C22 -6.6(17) . . . . ?
C16 C15 C21 C22 176.7(10) . . . . ?
C19 C20 C21 C15 -0.2(19) . . . . ?
C19 C20 C21 C22 -179.0(12) . . . . ?
C23 N4 C22 C21 -177.0(10) . . . . ?
Cu1 N4 C22 C21 0.0(17) . . . . ?
C15 C21 C22 N4 -2.7(18) . . . . ?
C20 C21 C22 N4 176.0(11) . . . . ?
C22 N4 C23 C24 96.4(12) . . . . ?
Cu1 N4 C23 C24 -80.7(11) . . . . ?
N4 C23 C24 C25 163.9(11) . . . . ?
C28 N5 C25 C24 -89.9(18) . . . . ?
C26 N5 C25 C24 92.1(17) . . . . ?
C23 C24 C25 N5 75.9(16) . . . . ?
C27 N6 C26 N5 4(2) . . . . ?
C28 N5 C26 N6 -3.5(18) . . . . ?
C25 N5 C26 N6 174.8(13) . . . . ?
C26 N6 C27 C28 -3(2) . . . . ?
N6 C27 C28 N5 1(2) . . . . ?
C26 N5 C28 C27 1.7(18) . . . . ?
C25 N5 C28 C27 -176.5(13) . . . . ?

_refine_diff_density_max         1.644
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.137



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1848466'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H32 N6 O4 Zn'
_chemical_formula_weight         581.96

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   22.8871(14)
_cell_length_b                   7.6537(5)
_cell_length_c                   34.918(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.510(7)
_cell_angle_gamma                90
_cell_volume                     5893.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1580
_cell_measurement_theta_min      3.5230
_cell_measurement_theta_max      25.5730

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.875
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_T_min  0.52239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            19824
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.967
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5149
_reflns_number_gt                3800
_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    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0885P)²+1.0802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00006(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5149
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.002
_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
C4 C 0.6169(2) 0.7002(6) 0.52730(14) 0.0625(12) Uani 1 1 d . . . . .
H4 H 0.6197 0.6487 0.5037 0.075 Uiso 1 1 calc R U . . .
C2 C 0.5918(2) 0.6083(5) 0.55275(14) 0.0515(11) Uani 1 1 d . . . . .
C1 C 0.58757(17) 0.6832(5) 0.58958(13) 0.0457(10) Uani 1 1 d . . . . .
C7 C 0.61221(19) 0.8532(5) 0.59900(13) 0.0500(10) Uani 1 1 d . . . . .
C5 C 0.6385(3) 0.8732(7) 0.53666(17) 0.0747(15) Uani 1 1 d . . . . .
H5 H 0.6544 0.9359 0.5189 0.090 Uiso 1 1 calc R U . . .
C6 C 0.6360(2) 0.9463(6) 0.57125(15) 0.0618(12) Uani 1 1 d . . . . .
H6 H 0.6500 1.0598 0.5771 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5733(3) 0.3559(7) 0.51105(16) 0.0811(17) Uani 1 1 d . . . . .
H3A H 0.5494 0.4204 0.4887 0.122 Uiso 1 1 calc R U . . .
H3B H 0.5577 0.2392 0.5104 0.122 Uiso 1 1 calc R U . . .
H3C H 0.6146 0.3520 0.5098 0.122 Uiso 1 1 calc R U . . .
C8 C 0.61394(18) 0.9409(5) 0.63546(12) 0.0439(9) Uani 1 1 d . . . . .
H8 H 0.6253 1.0579 0.6369 0.053 Uiso 1 1 calc R U . . .
C9 C 0.60929(18) 0.9991(5) 0.70088(12) 0.0434(9) Uani 1 1 d . . . . .
H9A H 0.5802 0.9684 0.7155 0.052 Uiso 1 1 calc R U . . .
H9B H 0.6006 1.1176 0.6911 0.052 Uiso 1 1 calc R U . . .
C10 C 0.67288(17) 0.9923(5) 0.72882(12) 0.0432(10) Uani 1 1 d . . . . .
H10A H 0.6850 0.8716 0.7345 0.052 Uiso 1 1 calc R U . . .
H10B H 0.7013 1.0469 0.7163 0.052 Uiso 1 1 calc R U . . .
C11 C 0.67417(19) 1.0862(6) 0.76686(14) 0.0542(12) Uani 1 1 d . . . . .
H11A H 0.6623 1.2069 0.7609 0.065 Uiso 1 1 calc R U . . .
H11B H 0.6450 1.0327 0.7789 0.065 Uiso 1 1 calc R U . . .
C12 C 0.71436(17) 0.4849(5) 0.71053(13) 0.0453(10) Uani 1 1 d . . . . .
H12 H 0.7108 0.5299 0.7345 0.054 Uiso 1 1 calc R U . . .
C14 C 0.69303(19) 0.4037(5) 0.64857(14) 0.0488(11) Uani 1 1 d . . . . .
H14 H 0.6722 0.3833 0.6222 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7524(2) 0.3665(5) 0.66593(14) 0.0534(11) Uani 1 1 d . . . . .
H13 H 0.7793 0.3147 0.6536 0.064 Uiso 1 1 calc R U . . .
C15 C 0.59740(15) 0.5384(4) 0.75859(12) 0.0365(9) Uani 1 1 d . . . . .
C16 C 0.63225(17) 0.5482(5) 0.79880(12) 0.0417(9) Uani 1 1 d . . . . .
C18 C 0.61834(18) 0.4527(5) 0.82798(13) 0.0451(10) Uani 1 1 d . . . . .
H18 H 0.6420 0.4624 0.8541 0.054 Uiso 1 1 calc R U . . .
C19 C 0.5689(2) 0.3411(6) 0.81894(14) 0.0522(11) Uani 1 1 d . . . . .
H19 H 0.5590 0.2782 0.8391 0.063 Uiso 1 1 calc R U . . .
C20 C 0.53472(18) 0.3228(5) 0.78073(13) 0.0461(10) Uani 1 1 d . . . . .
H20 H 0.5021 0.2459 0.7752 0.055 Uiso 1 1 calc R U . . .
C21 C 0.54748(16) 0.4173(4) 0.74922(12) 0.0380(9) Uani 1 1 d . . . . .
C22 C 0.50967(17) 0.3864(5) 0.70946(13) 0.0406(10) Uani 1 1 d . . . . .
H22 H 0.4770 0.3113 0.7075 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7214(2) 0.6692(7) 0.84277(14) 0.0633(13) Uani 1 1 d . . . . .
H17A H 0.6999 0.7152 0.8607 0.095 Uiso 1 1 calc R U . . .
H17B H 0.7549 0.7445 0.8426 0.095 Uiso 1 1 calc R U . . .
H17C H 0.7363 0.5545 0.8513 0.095 Uiso 1 1 calc R U . . .
C23 C 0.47150(18) 0.3846(5) 0.63991(13) 0.0485(11) Uani 1 1 d . . . . .
H23A H 0.4594 0.4800 0.6212 0.058 Uiso 1 1 calc R U . . .
H23B H 0.4355 0.3389 0.6461 0.058 Uiso 1 1 calc R U . . .
C24 C 0.5016(2) 0.2422(5) 0.62185(13) 0.0550(11) Uani 1 1 d . . . . .
H24A H 0.5032 0.1370 0.6376 0.066 Uiso 1 1 calc R U . . .
H24B H 0.5430 0.2773 0.6238 0.066 Uiso 1 1 calc R U . . .
C25 C 0.4708(2) 0.1981(7) 0.57860(15) 0.0688(13) Uani 1 1 d . . . . .
H25A H 0.4601 0.3060 0.5638 0.083 Uiso 1 1 calc R U . . .
H25B H 0.4995 0.1365 0.5675 0.083 Uiso 1 1 calc R U . . .
C28 C 0.3583(3) 0.1489(10) 0.56671(16) 0.0922(19) Uani 1 1 d . . . . .
H28 H 0.3446 0.2637 0.5657 0.111 Uiso 1 1 calc R U . . .
C27 C 0.3250(3) -0.0003(13) 0.56215(19) 0.102(2) Uani 1 1 d . . . . .
H27 H 0.2830 -0.0024 0.5572 0.122 Uiso 1 1 calc R U . . .
C26 C 0.4150(3) -0.0848(8) 0.57244(19) 0.0908(19) Uani 1 1 d . . . . .
H26 H 0.4493 -0.1550 0.5764 0.109 Uiso 1 1 calc R U . . .
Zn1 Zn 0.58692(2) 0.60820(5) 0.67215(2) 0.0400(2) Uani 1 1 d . . . . .
O1 O 0.57030(17) 0.4399(4) 0.54715(10) 0.0694(9) Uani 1 1 d . . . . .
O2 O 0.56170(14) 0.5960(3) 0.61256(9) 0.0509(8) Uani 1 1 d . . . . .
O3 O 0.60975(12) 0.6381(3) 0.73155(8) 0.0446(7) Uani 1 1 d . . . . .
O4 O 0.68177(13) 0.6595(4) 0.80389(8) 0.0522(7) Uani 1 1 d . . . . .
N4 N 0.51525(14) 0.4485(4) 0.67676(10) 0.0431(8) Uani 1 1 d . . . . .
N5 N 0.4162(2) 0.0909(5) 0.57311(12) 0.0674(11) Uani 1 1 d . . . . .
N6 N 0.3596(4) -0.1447(9) 0.56552(18) 0.116(2) Uani 1 1 d . . . . .
N1 N 0.60174(15) 0.8778(4) 0.66621(10) 0.0412(8) Uani 1 1 d . . . . .
N3 N 0.76565(14) 0.4190(4) 0.70488(11) 0.0432(8) Uani 1 1 d . . . . .
N2 N 0.66925(14) 0.4777(4) 0.67751(10) 0.0434(8) 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
C4 C2 1.374(6) . ?
C4 C5 1.421(7) . ?
C4 H4 0.9300 . ?
C2 O1 1.375(5) . ?
C2 C1 1.435(6) . ?
C1 O2 1.302(5) . ?
C1 C7 1.421(6) . ?
C7 C6 1.422(6) . ?
C7 C8 1.430(6) . ?
C5 C6 1.347(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C3 O1 1.432(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C8 N1 1.274(5) . ?
C8 H8 0.9300 . ?
C9 N1 1.499(5) . ?
C9 C10 1.521(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.503(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.465(5) 7_666 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.327(5) . ?
C12 N3 1.340(5) . ?
C12 H12 0.9300 . ?
C14 C13 1.362(6) . ?
C14 N2 1.390(5) . ?
C14 H14 0.9300 . ?
C13 N3 1.372(6) . ?
C13 H13 0.9300 . ?
C15 O3 1.302(4) . ?
C15 C16 1.419(5) . ?
C15 C21 1.439(5) . ?
C16 C18 1.359(6) . ?
C16 O4 1.391(4) . ?
C18 C19 1.385(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.362(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.411(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.446(6) . ?
C22 N4 1.275(5) . ?
C22 H22 0.9300 . ?
C17 O4 1.419(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C23 N4 1.486(5) . ?
C23 C24 1.513(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.524(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N5 1.464(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C28 C27 1.358(9) . ?
C28 N5 1.360(7) . ?
C28 H28 0.9300 . ?
C27 N6 1.347(9) . ?
C27 H27 0.9300 . ?
C26 N6 1.308(8) . ?
C26 N5 1.345(7) . ?
C26 H26 0.9300 . ?
Zn1 O2 2.007(3) . ?
Zn1 O3 2.012(3) . ?
Zn1 N4 2.086(3) . ?
Zn1 N2 2.096(3) . ?
Zn1 N1 2.110(3) . ?
N3 C11 1.465(5) 7_666 ?

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 C4 C5 120.6(5) . . ?
C2 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C2 O1 125.7(4) . . ?
C4 C2 C1 121.0(4) . . ?
O1 C2 C1 113.3(4) . . ?
O2 C1 C7 123.0(4) . . ?
O2 C1 C2 119.9(4) . . ?
C7 C1 C2 117.1(4) . . ?
C1 C7 C6 120.1(4) . . ?
C1 C7 C8 123.4(4) . . ?
C6 C7 C8 116.5(4) . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.3(5) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C8 C7 127.7(4) . . ?
N1 C8 H8 116.1 . . ?
C7 C8 H8 116.1 . . ?
N1 C9 C10 112.4(3) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 109.9(3) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C10 112.0(3) 7_666 . ?
N3 C11 H11A 109.2 7_666 . ?
C10 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 7_666 . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 N3 111.4(4) . . ?
N2 C12 H12 124.3 . . ?
N3 C12 H12 124.3 . . ?
C13 C14 N2 107.4(4) . . ?
C13 C14 H14 126.3 . . ?
N2 C14 H14 126.3 . . ?
C14 C13 N3 108.0(4) . . ?
C14 C13 H13 126.0 . . ?
N3 C13 H13 126.0 . . ?
O3 C15 C16 120.8(3) . . ?
O3 C15 C21 121.7(4) . . ?
C16 C15 C21 117.5(3) . . ?
C18 C16 O4 125.4(4) . . ?
C18 C16 C15 122.1(3) . . ?
O4 C16 C15 112.5(3) . . ?
C16 C18 C19 120.1(4) . . ?
C16 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 121.8(4) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C15 118.0(4) . . ?
C20 C21 C22 118.0(3) . . ?
C15 C21 C22 124.0(4) . . ?
N4 C22 C21 128.4(4) . . ?
N4 C22 H22 115.8 . . ?
C21 C22 H22 115.8 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C23 C24 108.8(3) . . ?
N4 C23 H23A 109.9 . . ?
C24 C23 H23A 109.9 . . ?
N4 C23 H23B 109.9 . . ?
C24 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C23 C24 C25 115.6(4) . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C25 C24 H24B 108.4 . . ?
H24A C24 H24B 107.4 . . ?
N5 C25 C24 113.9(4) . . ?
N5 C25 H25A 108.8 . . ?
C24 C25 H25A 108.8 . . ?
N5 C25 H25B 108.8 . . ?
C24 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C27 C28 N5 103.7(7) . . ?
C27 C28 H28 128.1 . . ?
N5 C28 H28 128.1 . . ?
N6 C27 C28 112.4(7) . . ?
N6 C27 H27 123.8 . . ?
C28 C27 H27 123.8 . . ?
N6 C26 N5 111.6(7) . . ?
N6 C26 H26 124.2 . . ?
N5 C26 H26 124.2 . . ?
O2 Zn1 O3 175.83(11) . . ?
O2 Zn1 N4 92.21(13) . . ?
O3 Zn1 N4 88.85(12) . . ?
O2 Zn1 N2 94.19(13) . . ?
O3 Zn1 N2 89.01(12) . . ?
N4 Zn1 N2 114.88(13) . . ?
O2 Zn1 N1 87.29(12) . . ?
O3 Zn1 N1 89.18(12) . . ?
N4 Zn1 N1 136.95(13) . . ?
N2 Zn1 N1 108.07(13) . . ?
C2 O1 C3 116.5(4) . . ?
C1 O2 Zn1 124.3(3) . . ?
C15 O3 Zn1 129.3(2) . . ?
C16 O4 C17 116.4(3) . . ?
C22 N4 C23 116.5(3) . . ?
C22 N4 Zn1 123.9(3) . . ?
C23 N4 Zn1 119.2(3) . . ?
C26 N5 C28 108.0(5) . . ?
C26 N5 C25 125.1(5) . . ?
C28 N5 C25 126.9(5) . . ?
C26 N6 C27 104.3(6) . . ?
C8 N1 C9 116.2(3) . . ?
C8 N1 Zn1 122.1(3) . . ?
C9 N1 Zn1 120.9(3) . . ?
C12 N3 C13 106.6(3) . . ?
C12 N3 C11 127.9(4) . 7_666 ?
C13 N3 C11 125.3(3) . 7_666 ?
C12 N2 C14 106.5(3) . . ?
C12 N2 Zn1 122.0(3) . . ?
C14 N2 Zn1 130.3(3) . . ?

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
C5 C4 C2 O1 -178.9(5) . . . . ?
C5 C4 C2 C1 -0.9(7) . . . . ?
C4 C2 C1 O2 177.6(4) . . . . ?
O1 C2 C1 O2 -4.2(6) . . . . ?
C4 C2 C1 C7 -2.0(6) . . . . ?
O1 C2 C1 C7 176.2(4) . . . . ?
O2 C1 C7 C6 -175.5(4) . . . . ?
C2 C1 C7 C6 4.1(6) . . . . ?
O2 C1 C7 C8 3.5(6) . . . . ?
C2 C1 C7 C8 -176.9(4) . . . . ?
C2 C4 C5 C6 1.8(8) . . . . ?
C4 C5 C6 C7 0.3(8) . . . . ?
C1 C7 C6 C5 -3.4(7) . . . . ?
C8 C7 C6 C5 177.5(5) . . . . ?
C1 C7 C8 N1 9.4(7) . . . . ?
C6 C7 C8 N1 -171.5(4) . . . . ?
N1 C9 C10 C11 -168.1(3) . . . . ?
C9 C10 C11 N3 179.1(3) . . . 7_666 ?
N2 C14 C13 N3 -0.9(5) . . . . ?
O3 C15 C16 C18 176.3(4) . . . . ?
C21 C15 C16 C18 -2.4(5) . . . . ?
O3 C15 C16 O4 -5.7(5) . . . . ?
C21 C15 C16 O4 175.6(3) . . . . ?
O4 C16 C18 C19 -177.5(4) . . . . ?
C15 C16 C18 C19 0.2(6) . . . . ?
C16 C18 C19 C20 1.5(7) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C15 -1.4(6) . . . . ?
C19 C20 C21 C22 178.5(4) . . . . ?
O3 C15 C21 C20 -175.7(3) . . . . ?
C16 C15 C21 C20 2.9(5) . . . . ?
O3 C15 C21 C22 4.4(5) . . . . ?
C16 C15 C21 C22 -176.9(3) . . . . ?
C20 C21 C22 N4 -175.3(4) . . . . ?
C15 C21 C22 N4 4.5(6) . . . . ?
N4 C23 C24 C25 -163.2(4) . . . . ?
C23 C24 C25 N5 -77.1(5) . . . . ?
N5 C28 C27 N6 0.1(7) . . . . ?
C4 C2 O1 C3 -1.6(7) . . . . ?
C1 C2 O1 C3 -179.7(4) . . . . ?
C7 C1 O2 Zn1 -33.9(5) . . . . ?
C2 C1 O2 Zn1 146.5(3) . . . . ?
C16 C15 O3 Zn1 159.8(3) . . . . ?
C21 C15 O3 Zn1 -21.6(5) . . . . ?
C18 C16 O4 C17 1.7(6) . . . . ?
C15 C16 O4 C17 -176.2(3) . . . . ?
C21 C22 N4 C23 176.3(3) . . . . ?
C21 C22 N4 Zn1 3.6(6) . . . . ?
C24 C23 N4 C22 -98.6(4) . . . . ?
C24 C23 N4 Zn1 74.4(4) . . . . ?
N6 C26 N5 C28 0.8(7) . . . . ?
N6 C26 N5 C25 -177.5(5) . . . . ?
C27 C28 N5 C26 -0.5(6) . . . . ?
C27 C28 N5 C25 177.8(5) . . . . ?
C24 C25 N5 C26 -90.6(6) . . . . ?
C24 C25 N5 C28 91.5(6) . . . . ?
N5 C26 N6 C27 -0.7(8) . . . . ?
C28 C27 N6 C26 0.3(8) . . . . ?
C7 C8 N1 C9 178.2(4) . . . . ?
C7 C8 N1 Zn1 8.7(6) . . . . ?
C10 C9 N1 C8 -89.8(4) . . . . ?
C10 C9 N1 Zn1 79.8(4) . . . . ?
N2 C12 N3 C13 -0.1(5) . . . . ?
N2 C12 N3 C11 175.7(4) . . . 7_666 ?
C14 C13 N3 C12 0.6(5) . . . . ?
C14 C13 N3 C11 -175.3(4) . . . 7_666 ?
N3 C12 N2 C14 -0.5(4) . . . . ?
N3 C12 N2 Zn1 -168.9(2) . . . . ?
C13 C14 N2 C12 0.8(4) . . . . ?
C13 C14 N2 Zn1 167.9(3) . . . . ?

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.086



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       Luminescent
