# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 2121405'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
?
?
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 N4'
_chemical_formula_sum            'C11 H8 N4'
_chemical_formula_weight         196.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3682(7)
_cell_length_b                   7.3765(7)
_cell_length_c                   9.1496(9)
_cell_angle_alpha                77.206(4)
_cell_angle_beta                 77.592(4)
_cell_angle_gamma                69.480(3)
_cell_volume                     449.02(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2226
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0557 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.8558.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4514
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.583
_diffrn_reflns_theta_min         2.987
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1565
_reflns_number_total             2055
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.3177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1222
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.3938(2) 0.4801(2) 0.33330(17) 0.0221(4) Uani 1 1 d . . . . .
N2 N 0.1850(2) 0.5515(2) 0.55540(16) 0.0186(3) Uani 1 1 d . . . . .
N3 N 0.0806(2) 0.6842(2) 0.65173(18) 0.0236(4) Uani 1 1 d . . . . .
N4 N 0.0827(2) 0.2243(2) 0.88102(17) 0.0228(4) Uani 1 1 d . . . . .
C1 C 0.1660(3) 0.0516(3) 0.8356(2) 0.0224(4) Uani 1 1 d . . . . .
H1 H 0.157363 -0.061299 0.907004 0.027 Uiso 1 1 calc R U . . .
C2 C 0.2666(3) 0.0234(3) 0.6890(2) 0.0221(4) Uani 1 1 d . . . . .
H2 H 0.322126 -0.105621 0.664946 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2855(3) 0.1800(3) 0.5803(2) 0.0196(4) Uani 1 1 d . . . . .
H3 H 0.352292 0.164163 0.480580 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2004(2) 0.3633(3) 0.62579(19) 0.0170(4) Uani 1 1 d . . . . .
C5 C 0.1002(3) 0.3781(3) 0.7738(2) 0.0195(4) Uani 1 1 d . . . . .
C6 C 0.0307(3) 0.5818(3) 0.7805(2) 0.0241(4) Uani 1 1 d . . . . .
H6 H -0.043151 0.636982 0.867863 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2724(3) 0.6193(3) 0.41044(19) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.2304(3) 0.8189(3) 0.3574(2) 0.0227(4) Uani 1 1 d . . . . .
H8 H 0.142776 0.913284 0.417146 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3207(3) 0.8750(3) 0.2148(2) 0.0277(5) Uani 1 1 d . . . . .
H9 H 0.295820 1.010052 0.173995 0.033 Uiso 1 1 calc R U . . .
C10 C 0.4472(3) 0.7341(3) 0.1317(2) 0.0264(4) Uani 1 1 d . . . . .
H10 H 0.510847 0.769732 0.033072 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4792(3) 0.5403(3) 0.1951(2) 0.0250(4) Uani 1 1 d . . . . .
H11 H 0.566933 0.443333 0.137584 0.030 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
N1 C7 1.326(2) . ?
N1 C11 1.341(2) . ?
N2 N3 1.375(2) . ?
N2 C4 1.372(2) . ?
N2 C7 1.410(2) . ?
N3 C6 1.307(2) . ?
N4 C1 1.322(2) . ?
N4 C5 1.350(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C5 1.404(2) . ?
C5 C6 1.418(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C11 116.47(16) . . ?
N3 N2 C7 118.94(15) . . ?
C4 N2 N3 111.20(14) . . ?
C4 N2 C7 129.61(15) . . ?
C6 N3 N2 106.25(15) . . ?
C1 N4 C5 114.53(15) . . ?
N4 C1 H1 117.7 . . ?
N4 C1 C2 124.58(17) . . ?
C2 C1 H1 117.7 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.84(17) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 122.2 . . ?
C2 C3 C4 115.65(16) . . ?
C4 C3 H3 122.2 . . ?
N2 C4 C3 134.31(16) . . ?
N2 C4 C5 105.99(15) . . ?
C3 C4 C5 119.69(16) . . ?
N4 C5 C4 124.68(16) . . ?
N4 C5 C6 130.45(16) . . ?
C4 C5 C6 104.86(16) . . ?
N3 C6 C5 111.71(16) . . ?
N3 C6 H6 124.1 . . ?
C5 C6 H6 124.1 . . ?
N1 C7 N2 115.16(16) . . ?
N1 C7 C8 124.35(17) . . ?
C8 C7 N2 120.49(16) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 C7 117.47(18) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.60(18) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.27(18) . . ?
C11 C10 H10 120.9 . . ?
N1 C11 C10 123.84(18) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C9 0.3(3) . . . . ?
N2 N3 C6 C5 0.0(2) . . . . ?
N2 C4 C5 N4 -179.28(17) . . . . ?
N2 C4 C5 C6 -0.12(19) . . . . ?
N2 C7 C8 C9 -179.95(17) . . . . ?
N3 N2 C4 C3 178.81(19) . . . . ?
N3 N2 C4 C5 0.12(19) . . . . ?
N3 N2 C7 N1 170.46(15) . . . . ?
N3 N2 C7 C8 -9.3(2) . . . . ?
N4 C1 C2 C3 0.3(3) . . . . ?
N4 C5 C6 N3 179.18(19) . . . . ?
C1 N4 C5 C4 -1.2(3) . . . . ?
C1 N4 C5 C6 179.86(19) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 N2 -179.76(19) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 N4 1.8(3) . . . . ?
C3 C4 C5 C6 -179.04(16) . . . . ?
C4 N2 N3 C6 -0.1(2) . . . . ?
C4 N2 C7 N1 -3.2(3) . . . . ?
C4 N2 C7 C8 177.08(17) . . . . ?
C4 C5 C6 N3 0.1(2) . . . . ?
C5 N4 C1 C2 0.2(3) . . . . ?
C7 N1 C11 C10 -0.1(3) . . . . ?
C7 N2 N3 C6 -174.80(16) . . . . ?
C7 N2 C4 C3 -7.2(3) . . . . ?
C7 N2 C4 C5 174.13(17) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 N1 0.2(3) . . . . ?
C11 N1 C7 N2 -179.94(16) . . . . ?
C11 N1 C7 C8 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L5
_database_code_depnum_ccdc_archive 'CCDC 2121407'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 N4'
_chemical_formula_sum            'C11 H8 N4'
_chemical_formula_weight         196.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.9365(3)
_cell_length_b                   10.1955(5)
_cell_length_c                   12.7905(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.2890(10)
_cell_angle_gamma                90
_cell_volume                     892.70(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 27938 reflections, Rint = 0.0422
 (15474 with I > 3sig(I), Rint = 0.0320)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2003
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1837
_reflns_number_total             2003
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.3517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5482(17)
 0.4518(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.3240(2) 0.46945(15) 0.64164(12) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.2277(2) 0.51421(15) 0.46378(12) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.1874(3) 0.47327(16) 0.36028(12) 0.0243(4) Uani 1 1 d . . . . .
N4 N 0.2233(3) 0.86572(16) 0.53588(13) 0.0285(4) Uani 1 1 d . . . . .
C1 C 0.1780(3) 0.90797(18) 0.43406(15) 0.0280(4) Uani 1 1 d . . . . .
H1 H 0.163831 0.999775 0.422651 0.034 Uiso 1 1 calc R U . . .
C2 C 0.1512(3) 0.82857(18) 0.34691(15) 0.0229(4) Uani 1 1 d . . . . .
H2 H 0.120185 0.863218 0.277279 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1717(3) 0.69412(18) 0.36528(13) 0.0203(4) Uani 1 1 d . . . . .
C4 C 0.2186(3) 0.64880(18) 0.46953(14) 0.0184(4) Uani 1 1 d . . . . .
C5 C 0.2440(3) 0.73801(18) 0.55389(14) 0.0235(4) Uani 1 1 d . . . . .
H5 H 0.276173 0.706800 0.624538 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1552(3) 0.5785(2) 0.30216(14) 0.0245(4) Uani 1 1 d . . . . .
H6 H 0.124518 0.578055 0.227038 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2761(3) 0.42047(19) 0.54514(14) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.2719(3) 0.28719(18) 0.52107(15) 0.0246(4) Uani 1 1 d . . . . .
H8 H 0.238394 0.256998 0.450195 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3183(3) 0.20105(19) 0.60407(17) 0.0272(4) Uani 1 1 d . . . . .
H9 H 0.315770 0.109184 0.591512 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3687(3) 0.2491(2) 0.70594(15) 0.0266(4) Uani 1 1 d . . . . .
H10 H 0.401119 0.191311 0.764413 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3704(3) 0.38255(19) 0.72018(16) 0.0276(4) Uani 1 1 d . . . . .
H11 H 0.406811 0.415314 0.790118 0.033 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
N1 C7 1.323(2) . ?
N1 C11 1.339(2) . ?
N2 N3 1.373(2) . ?
N2 C4 1.376(2) . ?
N2 C7 1.413(2) . ?
N3 C6 1.304(2) . ?
N4 C1 1.360(2) . ?
N4 C5 1.326(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.366(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(2) . ?
C3 C4 1.399(2) . ?
C3 C6 1.423(3) . ?
C4 C5 1.400(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C11 116.35(16) . . ?
N3 N2 C4 110.53(15) . . ?
N3 N2 C7 119.45(15) . . ?
C4 N2 C7 129.99(16) . . ?
C6 N3 N2 106.80(15) . . ?
C5 N4 C1 118.64(16) . . ?
N4 C1 H1 117.5 . . ?
N4 C1 C2 125.03(17) . . ?
C2 C1 H1 117.5 . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.65(17) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 119.14(16) . . ?
C2 C3 C6 136.24(17) . . ?
C4 C3 C6 104.61(16) . . ?
N2 C4 C3 106.50(16) . . ?
N2 C4 C5 133.44(17) . . ?
C3 C4 C5 120.06(17) . . ?
N4 C5 C4 120.48(17) . . ?
N4 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N3 C6 C3 111.56(15) . . ?
N3 C6 H6 124.2 . . ?
C3 C6 H6 124.2 . . ?
N1 C7 N2 115.20(17) . . ?
N1 C7 C8 124.59(17) . . ?
C8 C7 N2 120.21(17) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 C7 117.29(18) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.56(18) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.13(18) . . ?
C11 C10 H10 120.9 . . ?
N1 C11 C10 124.08(19) . . ?
N1 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C9 1.0(3) . . . . ?
N2 N3 C6 C3 -0.4(2) . . . . ?
N2 C4 C5 N4 -179.0(2) . . . . ?
N2 C7 C8 C9 -179.21(18) . . . . ?
N3 N2 C4 C3 -0.3(2) . . . . ?
N3 N2 C4 C5 178.96(19) . . . . ?
N3 N2 C7 N1 176.10(16) . . . . ?
N3 N2 C7 C8 -3.7(3) . . . . ?
N4 C1 C2 C3 0.3(3) . . . . ?
C1 N4 C5 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C6 178.9(2) . . . . ?
C2 C3 C4 N2 179.53(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C6 N3 -179.1(2) . . . . ?
C3 C4 C5 N4 0.2(3) . . . . ?
C4 N2 N3 C6 0.4(2) . . . . ?
C4 N2 C7 N1 -1.5(3) . . . . ?
C4 N2 C7 C8 178.65(19) . . . . ?
C4 C3 C6 N3 0.2(2) . . . . ?
C5 N4 C1 C2 0.0(3) . . . . ?
C6 C3 C4 N2 0.1(2) . . . . ?
C6 C3 C4 C5 -179.31(17) . . . . ?
C7 N1 C11 C10 -0.7(3) . . . . ?
C7 N2 N3 C6 -177.63(17) . . . . ?
C7 N2 C4 C3 177.49(18) . . . . ?
C7 N2 C4 C5 -3.2(4) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 N1 0.9(3) . . . . ?
C11 N1 C7 N2 179.94(18) . . . . ?
C11 N1 C7 C8 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5482(17)
2 0.4518(17)
####################################################################### 
# 
# 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 2121410'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-10-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 N3 O2 Zn, C3 H7 N O'
_chemical_formula_sum            'C16 H15 N4 O3 Zn'
_chemical_formula_weight         376.69
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.9545(9)
_cell_length_b                   9.4496(5)
_cell_length_c                   11.2888(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.631(2)
_cell_angle_gamma                90
_cell_volume                     1592.79(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4701
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    1.564
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0622 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8646. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.553
_diffrn_reflns_theta_min         2.728
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3465
_reflns_number_total             4868
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.822
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+1.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1202
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zn01 Zn 0.58085(2) 0.63882(3) 1.01090(3) 0.01178(9) Uani 1 1 d . . . . .
O1 O 0.68288(13) 0.6851(2) 0.9601(2) 0.0196(4) Uani 1 1 d . . . . .
O2 O 0.72052(14) 0.7626(3) 1.1559(2) 0.0245(5) Uani 1 1 d . . . . .
N1 N 0.49105(15) 0.5608(2) 0.8504(2) 0.0127(4) Uani 1 1 d . . . . .
N2 N 0.41384(15) 0.4944(2) 0.8459(2) 0.0137(4) Uani 1 1 d . . . . .
N3 N 0.51022(15) 0.7046(3) 0.5604(2) 0.0145(5) Uani 1 1 d . . . . .
C1 C 0.42863(19) 0.6602(3) 0.4791(3) 0.0176(6) Uani 1 1 d . . . . .
H1 H 0.412371 0.683048 0.391888 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3694(2) 0.5847(3) 0.5164(3) 0.0197(6) Uani 1 1 d . . . . .
H2 H 0.313772 0.553695 0.457054 0.024 Uiso 1 1 calc R U . . .
C3 C 0.39395(18) 0.5546(3) 0.6466(3) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.47870(18) 0.5983(3) 0.7288(2) 0.0127(5) Uani 1 1 d . . . . .
C5 C 0.53675(18) 0.6727(3) 0.6820(3) 0.0147(5) Uani 1 1 d . . . . .
H5 H 0.594636 0.699730 0.737425 0.018 Uiso 1 1 calc R U . . .
C6 C 0.35580(18) 0.4888(3) 0.7275(3) 0.0179(6) Uani 1 1 d . . . . .
H6 H 0.297946 0.447161 0.701812 0.021 Uiso 1 1 calc R U . . .
C7 C 0.73635(18) 0.7504(3) 1.0566(3) 0.0155(5) Uani 1 1 d . . . . .
C8 C 0.81776(17) 0.8170(3) 1.0435(3) 0.0164(5) Uani 1 1 d . . . . .
C9 C 0.84170(18) 0.7888(3) 0.9389(3) 0.0182(6) Uani 1 1 d . . . . .
H9 H 0.809206 0.720588 0.878243 0.022 Uiso 1 1 calc R U . . .
C10 C 0.91294(19) 0.8600(3) 0.9228(3) 0.0192(5) Uani 1 1 d . . . . .
H10 H 0.928511 0.839497 0.850811 0.023 Uiso 1 1 calc R U . . .
C11 C 0.96236(19) 0.9609(3) 1.0096(3) 0.0200(6) Uani 1 1 d . . . . .
C12 C 0.9375(2) 0.9871(4) 1.1148(3) 0.0368(9) Uani 1 1 d . . . . .
H12 H 0.969962 1.054904 1.175854 0.044 Uiso 1 1 calc R U . . .
C13 C 0.8664(2) 0.9161(4) 1.1317(3) 0.0315(8) Uani 1 1 d . . . . .
H13 H 0.851019 0.935390 1.204036 0.038 Uiso 1 1 calc R U . . .
O3 O 0.2579(4) 0.6254(5) 0.2194(4) 0.1009(17) Uani 1 1 d . . . . .
N4 N 0.1860(3) 0.6208(4) 0.0079(3) 0.0429(8) Uani 1 1 d . . . . .
C14 C 0.2597(3) 0.6227(5) 0.1142(4) 0.0468(10) Uani 1 1 d . . . . .
H14 H 0.316547 0.621743 0.104917 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0994(4) 0.6150(7) 0.0193(6) 0.0768(19) Uani 1 1 d . . . . .
H15A H 0.106279 0.614355 0.109046 0.115 Uiso 1 1 calc R U . . .
H15B H 0.068407 0.528793 -0.021427 0.115 Uiso 1 1 calc R U . . .
H15C H 0.064409 0.698020 -0.021917 0.115 Uiso 1 1 calc R U . . .
C16 C 0.1941(4) 0.6172(6) -0.1150(5) 0.0604(14) Uani 1 1 d . . . . .
H16A H 0.257089 0.629373 -0.105914 0.091 Uiso 1 1 calc R U . . .
H16B H 0.158412 0.693826 -0.167349 0.091 Uiso 1 1 calc R U . . .
H16C H 0.172369 0.526015 -0.155494 0.091 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
Zn01 O1 1.9563(19) . ?
Zn01 N1 2.012(2) . ?
Zn01 N2 2.027(2) 3_667 ?
Zn01 N3 2.053(2) 4_576 ?
Zn01 C7 2.575(3) . ?
O1 C7 1.281(3) . ?
O2 C7 1.238(3) . ?
N1 N2 1.367(3) . ?
N1 C4 1.363(3) . ?
N2 C6 1.332(4) . ?
N3 C1 1.368(4) . ?
N3 C5 1.322(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.364(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(4) . ?
C3 C4 1.406(4) . ?
C3 C6 1.408(4) . ?
C4 C5 1.405(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.497(4) . ?
C8 C9 1.389(4) . ?
C8 C13 1.388(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(4) . ?
C11 C11 1.490(5) 3_777 ?
C11 C12 1.400(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
O3 C14 1.198(6) . ?
N4 C14 1.352(6) . ?
N4 C15 1.433(6) . ?
N4 C16 1.439(6) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 Zn01 N1 102.71(9) . . ?
O1 Zn01 N2 124.55(9) . 3_667 ?
O1 Zn01 N3 120.79(9) . 4_576 ?
O1 Zn01 C7 28.93(9) . . ?
N1 Zn01 N2 107.88(9) . 3_667 ?
N1 Zn01 N3 102.95(9) . 4_576 ?
N1 Zn01 C7 131.33(9) . . ?
N2 Zn01 N3 95.93(9) 3_667 4_576 ?
N2 Zn01 C7 109.14(9) 3_667 . ?
N3 Zn01 C7 103.47(9) 4_576 . ?
C7 O1 Zn01 103.43(17) . . ?
N2 N1 Zn01 123.22(16) . . ?
C4 N1 Zn01 128.02(18) . . ?
C4 N1 N2 105.9(2) . . ?
N1 N2 Zn01 118.13(17) . 3_667 ?
C6 N2 Zn01 126.47(19) . 3_667 ?
C6 N2 N1 110.7(2) . . ?
C1 N3 Zn01 121.50(18) . 4_575 ?
C5 N3 Zn01 116.23(19) . 4_575 ?
C5 N3 C1 120.5(2) . . ?
N3 C1 H1 118.2 . . ?
C2 C1 N3 123.5(3) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.3(3) . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 C6 103.7(2) . . ?
C6 C3 C2 137.8(3) . . ?
N1 C4 C3 110.7(2) . . ?
N1 C4 C5 128.9(2) . . ?
C5 C4 C3 120.4(2) . . ?
N3 C5 C4 119.5(3) . . ?
N3 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 C6 C3 109.1(2) . . ?
N2 C6 H6 125.5 . . ?
C3 C6 H6 125.5 . . ?
O1 C7 C8 117.4(2) . . ?
O2 C7 O1 121.9(2) . . ?
O2 C7 C8 120.7(3) . . ?
C9 C8 C7 120.8(3) . . ?
C13 C8 C7 119.9(3) . . ?
C13 C8 C9 119.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C11 121.5(3) . 3_777 ?
C10 C11 C12 117.2(3) . . ?
C12 C11 C11 121.3(3) . 3_777 ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 N4 C15 119.0(4) . . ?
C14 N4 C16 120.8(4) . . ?
C15 N4 C16 120.2(4) . . ?
O3 C14 N4 124.3(5) . . ?
O3 C14 H14 117.8 . . ?
N4 C14 H14 117.8 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn01 O1 C7 O2 5.0(3) . . . . ?
Zn01 O1 C7 C8 -172.7(2) . . . . ?
Zn01 N1 N2 Zn01 -40.0(3) . . . 3_667 ?
Zn01 N1 N2 C6 162.6(2) . . . . ?
Zn01 N1 C4 C3 -161.49(19) . . . . ?
Zn01 N1 C4 C5 17.2(4) . . . . ?
Zn01 N2 C6 C3 -155.4(2) 3_667 . . . ?
Zn01 N3 C1 C2 -162.8(2) 4_575 . . . ?
Zn01 N3 C5 C4 162.0(2) 4_575 . . . ?
O1 C7 C8 C9 -10.5(4) . . . . ?
O1 C7 C8 C13 164.7(3) . . . . ?
O2 C7 C8 C9 171.8(3) . . . . ?
O2 C7 C8 C13 -13.0(5) . . . . ?
N1 N2 C6 C3 -0.3(3) . . . . ?
N1 C4 C5 N3 -176.8(3) . . . . ?
N2 N1 C4 C3 -0.6(3) . . . . ?
N2 N1 C4 C5 178.1(3) . . . . ?
N3 C1 C2 C3 1.4(5) . . . . ?
C1 N3 C5 C4 -3.1(4) . . . . ?
C1 C2 C3 C4 -2.6(4) . . . . ?
C1 C2 C3 C6 176.7(3) . . . . ?
C2 C3 C4 N1 179.9(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C6 N2 -179.4(3) . . . . ?
C3 C4 C5 N3 1.8(4) . . . . ?
C4 N1 N2 Zn01 157.96(18) . . . 3_667 ?
C4 N1 N2 C6 0.6(3) . . . . ?
C4 C3 C6 N2 -0.1(3) . . . . ?
C5 N3 C1 C2 1.6(4) . . . . ?
C6 C3 C4 N1 0.4(3) . . . . ?
C6 C3 C4 C5 -178.4(3) . . . . ?
C7 C8 C9 C10 174.7(3) . . . . ?
C7 C8 C13 C12 -174.6(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C8 C13 C12 0.7(6) . . . . ?
C9 C10 C11 C11 -178.7(4) . . . 3_777 ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C11 C12 C13 178.9(4) 3_777 . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
C15 N4 C14 O3 -3.1(7) . . . . ?
C16 N4 C14 O3 -179.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L4
_database_code_depnum_ccdc_archive 'CCDC 2121406'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 N4'
_chemical_formula_sum            'C11 H8 N4'
_chemical_formula_weight         196.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.8153(3)
_cell_length_b                   18.8138(9)
_cell_length_c                   7.7716(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.8950(10)
_cell_angle_gamma                90
_cell_volume                     911.08(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8220
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.524
_cell_measurement_theta_min      3.064
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0567 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9358.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18810
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_min         3.065
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2406
_reflns_number_total             2783
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.4170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.14278(17) 0.42497(6) 0.72549(16) 0.0214(2) Uani 1 1 d . . . . .
N2 N 0.45355(16) 0.48422(6) 0.75610(14) 0.0172(2) Uani 1 1 d . . . . .
N3 N 0.67105(16) 0.48825(6) 0.83217(15) 0.0195(2) Uani 1 1 d . . . . .
N4 N 0.50810(18) 0.64468(6) 0.54602(16) 0.0225(2) Uani 1 1 d . . . . .
C1 C 0.6973(2) 0.67147(7) 0.5760(2) 0.0230(3) Uani 1 1 d . . . . .
H1 H 0.699632 0.714766 0.513989 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8986(2) 0.64139(7) 0.69313(19) 0.0232(3) Uani 1 1 d . . . . .
H2 H 1.027415 0.664701 0.705892 0.028 Uiso 1 1 calc R U . . .
C3 C 0.9088(2) 0.57939(7) 0.78741(19) 0.0218(3) Uani 1 1 d . . . . .
H3 H 1.041517 0.558325 0.866593 0.026 Uiso 1 1 calc R U . . .
C4 C 0.70948(19) 0.54859(7) 0.75959(17) 0.0177(2) Uani 1 1 d . . . . .
C5 C 0.51636(19) 0.58243(6) 0.63868(17) 0.0174(2) Uani 1 1 d . . . . .
C6 C 0.35273(19) 0.53862(7) 0.63950(17) 0.0186(2) Uani 1 1 d . . . . .
H6 H 0.202553 0.545333 0.572742 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3550(2) 0.42447(6) 0.80050(17) 0.0177(2) Uani 1 1 d . . . . .
C8 C 0.4825(2) 0.37079(7) 0.91322(18) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.634688 0.373266 0.962788 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3786(2) 0.31367(7) 0.95016(19) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.458714 0.275733 1.027436 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1567(2) 0.31220(8) 0.8735(2) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.081906 0.273179 0.896219 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0460(2) 0.36876(8) 0.7632(2) 0.0253(3) Uani 1 1 d . . . . .
H11 H -0.106367 0.367702 0.711426 0.030 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
N1 C7 1.3225(16) . ?
N1 C11 1.3399(17) . ?
N2 N3 1.3574(14) . ?
N2 C6 1.3551(15) . ?
N2 C7 1.4217(16) . ?
N3 C4 1.3399(16) . ?
N4 C1 1.3141(17) . ?
N4 C5 1.3641(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.4212(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3641(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.4109(17) . ?
C4 C5 1.4208(16) . ?
C5 C6 1.3888(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3878(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3795(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C11 116.44(12) . . ?
N3 N2 C7 118.57(10) . . ?
C6 N2 N3 114.68(10) . . ?
C6 N2 C7 126.73(11) . . ?
C4 N3 N2 103.25(10) . . ?
C1 N4 C5 114.07(11) . . ?
N4 C1 H1 117.1 . . ?
N4 C1 C2 125.75(12) . . ?
C2 C1 H1 117.1 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.70(12) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 122.2 . . ?
C2 C3 C4 115.61(12) . . ?
C4 C3 H3 122.2 . . ?
N3 C4 C3 128.59(11) . . ?
N3 C4 C5 111.80(11) . . ?
C3 C4 C5 119.60(12) . . ?
N4 C5 C4 124.26(11) . . ?
N4 C5 C6 130.58(12) . . ?
C6 C5 C4 105.16(11) . . ?
N2 C6 C5 105.11(10) . . ?
N2 C6 H6 127.4 . . ?
C5 C6 H6 127.4 . . ?
N1 C7 N2 115.29(11) . . ?
N1 C7 C8 125.22(12) . . ?
C8 C7 N2 119.48(11) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 C7 117.09(12) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.33(13) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.56(13) . . ?
C11 C10 H10 120.7 . . ?
N1 C11 C10 123.35(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?

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
N1 C7 C8 C9 -0.3(2) . . . . ?
N2 N3 C4 C3 -179.02(12) . . . . ?
N2 N3 C4 C5 0.18(13) . . . . ?
N2 C7 C8 C9 -179.28(11) . . . . ?
N3 N2 C6 C5 -0.25(14) . . . . ?
N3 N2 C7 N1 178.30(10) . . . . ?
N3 N2 C7 C8 -2.63(17) . . . . ?
N3 C4 C5 N4 179.96(12) . . . . ?
N3 C4 C5 C6 -0.33(14) . . . . ?
N4 C1 C2 C3 -0.1(2) . . . . ?
N4 C5 C6 N2 -179.98(12) . . . . ?
C1 N4 C5 C4 0.70(18) . . . . ?
C1 N4 C5 C6 -178.93(13) . . . . ?
C1 C2 C3 C4 0.10(19) . . . . ?
C2 C3 C4 N3 179.45(13) . . . . ?
C2 C3 C4 C5 0.31(18) . . . . ?
C3 C4 C5 N4 -0.76(19) . . . . ?
C3 C4 C5 C6 178.95(11) . . . . ?
C4 C5 C6 N2 0.33(13) . . . . ?
C5 N4 C1 C2 -0.2(2) . . . . ?
C6 N2 N3 C4 0.05(14) . . . . ?
C6 N2 C7 N1 -3.38(18) . . . . ?
C6 N2 C7 C8 175.68(12) . . . . ?
C7 N1 C11 C10 -0.2(2) . . . . ?
C7 N2 N3 C4 178.57(10) . . . . ?
C7 N2 C6 C5 -178.63(11) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 N1 0.4(2) . . . . ?
C11 N1 C7 N2 179.12(11) . . . . ?
C11 N1 C7 C8 0.12(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2121411'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 N6 O6 Zn'
_chemical_formula_sum            'C11 H8 N6 O6 Zn'
_chemical_formula_weight         385.60
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.5507(3)
_cell_length_b                   11.2088(4)
_cell_length_c                   13.9264(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.2400(10)
_cell_angle_gamma                90
_cell_volume                     1334.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.629
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0736 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.8150.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23573
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         2.926
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3559
_reflns_number_total             4056
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.34805(2) 0.19469(2) 0.62273(2) 0.01724(5) Uani 1 1 d . . . . .
O1 O 0.18364(14) 0.25477(10) 0.49654(8) 0.0268(2) Uani 1 1 d . . . . .
O2 O 0.28178(15) 0.07902(10) 0.50959(9) 0.0300(3) Uani 1 1 d . . . . .
O3 O 0.12005(17) 0.11888(15) 0.39131(10) 0.0453(4) Uani 1 1 d . . . . .
O4 O 0.48314(18) 0.16765(12) 0.76362(10) 0.0394(3) Uani 1 1 d . . . . .
O5 O 0.48860(18) 0.02607(14) 0.66212(9) 0.0452(4) Uani 1 1 d . . . . .
O6 O 0.57865(15) -0.00160(10) 0.80750(9) 0.0321(3) Uani 1 1 d . . . . .
N1 N 0.54837(15) 0.26366(10) 0.55681(9) 0.0182(2) Uani 1 1 d . . . . .
N2 N 0.49563(13) 0.43764(10) 0.63903(8) 0.0140(2) Uani 1 1 d . . . . .
N3 N 0.36460(13) 0.38045(10) 0.67034(8) 0.0155(2) Uani 1 1 d . . . . .
N4 N 0.36141(14) 0.65248(10) 0.80285(8) 0.0167(2) Uani 1 1 d . . . . .
N5 N 0.19192(16) 0.14985(13) 0.46305(9) 0.0252(3) Uani 1 1 d . . . . .
N6 N 0.52093(15) 0.06238(12) 0.74549(9) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.47228(17) 0.73524(13) 0.80189(10) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.462224 0.801906 0.843432 0.023 Uiso 1 1 calc R U . . .
C2 C 0.60351(17) 0.73027(13) 0.74323(11) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.678034 0.793096 0.745997 0.024 Uiso 1 1 calc R U . . .
C3 C 0.62610(16) 0.63623(12) 0.68193(10) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.712674 0.632769 0.640399 0.021 Uiso 1 1 calc R U . . .
C4 C 0.51333(16) 0.54567(11) 0.68453(9) 0.0139(2) Uani 1 1 d . . . . .
C5 C 0.38543(16) 0.55642(11) 0.74566(9) 0.0143(2) Uani 1 1 d . . . . .
C6 C 0.29867(16) 0.44971(11) 0.73377(10) 0.0164(2) Uani 1 1 d . . . . .
H6 H 0.205958 0.430895 0.766962 0.020 Uiso 1 1 calc R U . . .
C7 C 0.58992(15) 0.37685(11) 0.57245(9) 0.0142(2) Uani 1 1 d . . . . .
C8 C 0.71534(16) 0.43100(13) 0.52815(9) 0.0173(3) Uani 1 1 d . . . . .
H8 H 0.738277 0.513115 0.537777 0.021 Uiso 1 1 calc R U . . .
C9 C 0.80578(17) 0.36046(14) 0.46931(10) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.894299 0.393543 0.439001 0.025 Uiso 1 1 calc R U . . .
C10 C 0.76712(18) 0.24195(14) 0.45475(11) 0.0232(3) Uani 1 1 d . . . . .
H10 H 0.829407 0.192371 0.415587 0.028 Uiso 1 1 calc R U . . .
C11 C 0.63620(19) 0.19734(13) 0.49831(11) 0.0230(3) Uani 1 1 d . . . . .
H11 H 0.606998 0.116796 0.486548 0.028 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 2.3262(12) . ?
Zn1 O2 2.1086(13) . ?
Zn1 O4 2.2756(15) . ?
Zn1 O5 2.2999(18) . ?
Zn1 N1 2.1078(12) . ?
Zn1 N3 2.1888(11) . ?
Zn1 N4 2.1415(11) 2_546 ?
O1 N5 1.2676(18) . ?
O2 N5 1.2725(18) . ?
O3 N5 1.2124(19) . ?
O4 N6 1.2505(19) . ?
O5 N6 1.2555(18) . ?
O6 N6 1.2187(17) . ?
N1 C7 1.3341(18) . ?
N1 C11 1.3442(17) . ?
N2 N3 1.3702(15) . ?
N2 C4 1.3734(16) . ?
N2 C7 1.4165(16) . ?
N3 C6 1.3124(16) . ?
N4 C1 1.3267(19) . ?
N4 C5 1.3575(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.4033(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3728(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.4011(18) . ?
C4 C5 1.4056(17) . ?
C5 C6 1.4154(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3885(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3863(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(2) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O1 57.67(4) . . ?
O2 Zn1 O4 133.28(5) . . ?
O2 Zn1 O5 78.67(5) . . ?
O2 Zn1 N3 145.67(5) . . ?
O2 Zn1 N4 90.67(5) . 2_546 ?
O4 Zn1 O1 167.74(4) . . ?
O4 Zn1 O5 55.38(5) . . ?
O5 Zn1 O1 136.24(4) . . ?
N1 Zn1 O1 92.77(5) . . ?
N1 Zn1 O2 96.19(5) . . ?
N1 Zn1 O4 91.28(5) . . ?
N1 Zn1 O5 88.85(5) . . ?
N1 Zn1 N3 74.65(4) . . ?
N1 Zn1 N4 171.07(4) . 2_546 ?
N3 Zn1 O1 89.28(4) . . ?
N3 Zn1 O4 80.63(5) . . ?
N3 Zn1 O5 132.81(5) . . ?
N4 Zn1 O1 86.07(4) 2_546 . ?
N4 Zn1 O4 88.14(5) 2_546 . ?
N4 Zn1 O5 98.12(5) 2_546 . ?
N4 Zn1 N3 96.48(4) 2_546 . ?
N5 O1 Zn1 88.38(9) . . ?
N5 O2 Zn1 98.42(9) . . ?
N6 O4 Zn1 94.60(11) . . ?
N6 O5 Zn1 93.30(11) . . ?
C7 N1 Zn1 119.58(9) . . ?
C7 N1 C11 118.33(12) . . ?
C11 N1 Zn1 122.08(10) . . ?
N3 N2 C4 110.39(10) . . ?
N3 N2 C7 117.65(11) . . ?
C4 N2 C7 131.87(11) . . ?
N2 N3 Zn1 113.37(8) . . ?
C6 N3 Zn1 137.79(9) . . ?
C6 N3 N2 107.67(11) . . ?
C1 N4 Zn1 117.11(9) . 2_556 ?
C1 N4 C5 115.56(12) . . ?
C5 N4 Zn1 126.72(9) . 2_556 ?
O1 N5 O2 115.43(13) . . ?
O3 N5 O1 122.51(15) . . ?
O3 N5 O2 122.06(15) . . ?
O4 N6 O5 116.10(15) . . ?
O6 N6 O4 120.97(14) . . ?
O6 N6 O5 122.83(16) . . ?
N4 C1 H1 118.0 . . ?
N4 C1 C2 123.96(13) . . ?
C2 C1 H1 118.0 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.18(13) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 122.1 . . ?
C2 C3 C4 115.72(12) . . ?
C4 C3 H3 122.1 . . ?
N2 C4 C3 134.09(12) . . ?
N2 C4 C5 106.00(11) . . ?
C3 C4 C5 119.90(12) . . ?
N4 C5 C4 123.57(12) . . ?
N4 C5 C6 130.80(12) . . ?
C4 C5 C6 105.62(11) . . ?
N3 C6 C5 110.30(12) . . ?
N3 C6 H6 124.8 . . ?
C5 C6 H6 124.8 . . ?
N1 C7 N2 114.27(11) . . ?
N1 C7 C8 123.27(12) . . ?
C8 C7 N2 122.45(12) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 C7 117.35(13) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.00(13) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.53(13) . . ?
C11 C10 H10 120.7 . . ?
N1 C11 C10 122.39(14) . . ?
N1 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?

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
Zn1 O1 N5 O2 -2.86(12) . . . . ?
Zn1 O1 N5 O3 177.53(14) . . . . ?
Zn1 O2 N5 O1 3.19(14) . . . . ?
Zn1 O2 N5 O3 -177.20(13) . . . . ?
Zn1 O4 N6 O5 7.74(14) . . . . ?
Zn1 O4 N6 O6 -168.80(12) . . . . ?
Zn1 O5 N6 O4 -7.65(14) . . . . ?
Zn1 O5 N6 O6 168.82(13) . . . . ?
Zn1 N1 C7 N2 3.79(16) . . . . ?
Zn1 N1 C7 C8 -176.65(11) . . . . ?
Zn1 N1 C11 C10 179.82(12) . . . . ?
Zn1 N3 C6 C5 166.49(11) . . . . ?
Zn1 N4 C1 C2 -168.55(12) 2_556 . . . ?
Zn1 N4 C5 C4 167.21(10) 2_556 . . . ?
Zn1 N4 C5 C6 -13.9(2) 2_556 . . . ?
N1 C7 C8 C9 -3.8(2) . . . . ?
N2 N3 C6 C5 0.38(16) . . . . ?
N2 C4 C5 N4 -179.68(12) . . . . ?
N2 C4 C5 C6 1.19(14) . . . . ?
N2 C7 C8 C9 175.70(13) . . . . ?
N3 N2 C4 C3 177.82(15) . . . . ?
N3 N2 C4 C5 -1.02(14) . . . . ?
N3 N2 C7 N1 -7.59(17) . . . . ?
N3 N2 C7 C8 172.84(12) . . . . ?
N4 C1 C2 C3 -0.4(2) . . . . ?
N4 C5 C6 N3 179.96(14) . . . . ?
C1 N4 C5 C4 -3.5(2) . . . . ?
C1 N4 C5 C6 175.37(14) . . . . ?
C1 C2 C3 C4 -1.9(2) . . . . ?
C2 C3 C4 N2 -177.21(15) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 N4 1.3(2) . . . . ?
C3 C4 C5 C6 -177.85(12) . . . . ?
C4 N2 N3 Zn1 -169.47(9) . . . . ?
C4 N2 N3 C6 0.42(15) . . . . ?
C4 N2 C7 N1 168.70(13) . . . . ?
C4 N2 C7 C8 -10.9(2) . . . . ?
C4 C5 C6 N3 -0.99(16) . . . . ?
C5 N4 C1 C2 3.1(2) . . . . ?
C7 N1 C11 C10 0.3(2) . . . . ?
C7 N2 N3 Zn1 7.59(14) . . . . ?
C7 N2 N3 C6 177.47(12) . . . . ?
C7 N2 C4 C3 1.3(3) . . . . ?
C7 N2 C4 C5 -177.52(13) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C8 C9 C10 C11 1.2(2) . . . . ?
C9 C10 C11 N1 -2.3(2) . . . . ?
C11 N1 C7 N2 -176.72(13) . . . . ?
C11 N1 C7 C8 2.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L6
_database_code_depnum_ccdc_archive 'CCDC 2121408'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 N4'
_chemical_formula_sum            'C11 H8 N4'
_chemical_formula_weight         196.21
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   10.9868(7)
_cell_length_b                   4.5407(3)
_cell_length_c                   18.0875(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     902.34(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6526
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.511
_cell_measurement_theta_min      3.709
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0692 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8949.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12599
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.546
_diffrn_reflns_theta_min         3.709
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2562
_reflns_number_total             2733
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.1957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.46133(14) 0.3445(4) 0.61353(10) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.37203(13) 0.5682(3) 0.51267(9) 0.0173(3) Uani 1 1 d . . . . .
N3 N 0.27717(14) 0.5996(4) 0.46541(9) 0.0200(3) Uani 1 1 d . . . . .
N4 N 0.31273(18) 1.1097(4) 0.31111(11) 0.0278(4) Uani 1 1 d . . . . .
C1 C 0.4275(2) 1.2049(5) 0.32943(11) 0.0260(4) Uani 1 1 d . . . . .
H1 H 0.463056 1.351982 0.298943 0.031 Uiso 1 1 calc R U . . .
C2 C 0.49451(19) 1.1061(4) 0.38766(11) 0.0229(4) Uani 1 1 d . . . . .
H2 H 0.574391 1.177034 0.396988 0.028 Uiso 1 1 calc R U . . .
C3 C 0.43936(16) 0.8930(4) 0.43344(11) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.31937(17) 0.7994(4) 0.41667(10) 0.0193(4) Uani 1 1 d . . . . .
C5 C 0.26056(19) 0.9127(5) 0.35321(12) 0.0245(4) Uani 1 1 d . . . . .
H5 H 0.181415 0.844218 0.340913 0.029 Uiso 1 1 calc R U . . .
C6 C 0.47017(17) 0.7365(4) 0.49647(11) 0.0194(4) Uani 1 1 d . . . . .
H6 H 0.544813 0.745494 0.522880 0.023 Uiso 1 1 calc R U . . .
C7 C 0.36166(16) 0.3694(4) 0.57297(10) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.25354(17) 0.2217(4) 0.58565(11) 0.0211(4) Uani 1 1 d . . . . .
H8 H 0.184687 0.248226 0.554585 0.025 Uiso 1 1 calc R U . . .
C9 C 0.25059(18) 0.0334(5) 0.64586(12) 0.0245(4) Uani 1 1 d . . . . .
H9 H 0.178408 -0.072599 0.657200 0.029 Uiso 1 1 calc R U . . .
C10 C 0.35272(19) 0.0003(5) 0.68923(11) 0.0252(4) Uani 1 1 d . . . . .
H10 H 0.352485 -0.128204 0.730666 0.030 Uiso 1 1 calc R U . . .
C11 C 0.45558(19) 0.1595(5) 0.67076(12) 0.0251(4) Uani 1 1 d . . . . .
H11 H 0.526187 0.135852 0.700495 0.030 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
N1 C7 1.323(2) . ?
N1 C11 1.334(3) . ?
N2 N3 1.355(2) . ?
N2 C6 1.354(2) . ?
N2 C7 1.421(2) . ?
N3 C4 1.347(3) . ?
N4 C1 1.374(3) . ?
N4 C5 1.307(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.361(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(3) . ?
C3 C4 1.418(3) . ?
C3 C6 1.385(3) . ?
C4 C5 1.414(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C11 116.41(17) . . ?
N3 N2 C7 119.30(15) . . ?
C6 N2 N3 114.62(16) . . ?
C6 N2 C7 126.08(16) . . ?
C4 N3 N2 102.64(15) . . ?
C5 N4 C1 118.52(18) . . ?
N4 C1 H1 117.3 . . ?
C2 C1 N4 125.4(2) . . ?
C2 C1 H1 117.3 . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.6(2) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 118.66(18) . . ?
C6 C3 C2 136.89(19) . . ?
C6 C3 C4 104.45(17) . . ?
N3 C4 C3 112.45(17) . . ?
N3 C4 C5 128.24(18) . . ?
C5 C4 C3 119.30(18) . . ?
N4 C5 C4 121.4(2) . . ?
N4 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N2 C6 C3 105.85(16) . . ?
N2 C6 H6 127.1 . . ?
C3 C6 H6 127.1 . . ?
N1 C7 N2 114.44(16) . . ?
N1 C7 C8 125.28(17) . . ?
C8 C7 N2 120.28(17) . . ?
C7 C8 H8 121.6 . . ?
C7 C8 C9 116.73(18) . . ?
C9 C8 H8 121.6 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.73(18) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.13(19) . . ?
C11 C10 H10 120.9 . . ?
N1 C11 C10 123.7(2) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C9 0.0(3) . . . . ?
N2 N3 C4 C3 -0.2(2) . . . . ?
N2 N3 C4 C5 178.13(19) . . . . ?
N2 C7 C8 C9 -179.56(18) . . . . ?
N3 N2 C6 C3 -0.1(2) . . . . ?
N3 N2 C7 N1 176.81(17) . . . . ?
N3 N2 C7 C8 -3.6(3) . . . . ?
N3 C4 C5 N4 179.3(2) . . . . ?
N4 C1 C2 C3 -1.5(3) . . . . ?
C1 N4 C5 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C6 -179.4(2) . . . . ?
C2 C3 C4 N3 -178.97(17) . . . . ?
C2 C3 C4 C5 2.5(3) . . . . ?
C2 C3 C6 N2 178.8(2) . . . . ?
C3 C4 C5 N4 -2.5(3) . . . . ?
C4 C3 C6 N2 0.0(2) . . . . ?
C5 N4 C1 C2 1.7(3) . . . . ?
C6 N2 N3 C4 0.2(2) . . . . ?
C6 N2 C7 N1 -3.1(3) . . . . ?
C6 N2 C7 C8 176.51(18) . . . . ?
C6 C3 C4 N3 0.2(2) . . . . ?
C6 C3 C4 C5 -178.35(17) . . . . ?
C7 N1 C11 C10 -0.7(3) . . . . ?
C7 N2 N3 C4 -179.74(16) . . . . ?
C7 N2 C6 C3 179.83(17) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 N1 0.4(3) . . . . ?
C11 N1 C7 N2 -179.93(18) . . . . ?
C11 N1 C7 C8 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2121412'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 N6 O7 Zn'
_chemical_formula_sum            'C11 H10 N6 O7 Zn'
_chemical_formula_weight         403.62
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   24.908(3)
_cell_length_b                   7.1377(7)
_cell_length_c                   16.5359(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2939.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7137
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.958
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.584
_exptl_absorpt_coefficient_mu    1.725
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0683 after correction.
The Ratio of minimum to maximum transmission is 0.7524.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.596
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2525
_reflns_number_total             3202
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+10.5062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O7-H7B = O7-H7A
 0.95 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.37670(2) 0.71274(7) 0.22698(3) 0.02049(13) Uani 1 1 d . . . . .
O1 O 0.43885(13) 0.8679(5) 0.1834(2) 0.0446(9) Uani 1 1 d . . . . .
O2 O 0.50584(12) 0.8433(4) 0.10167(19) 0.0352(8) Uani 1 1 d . . . . .
O3 O 0.46328(15) 0.5972(5) 0.1399(2) 0.0487(10) Uani 1 1 d . . . . .
O4 O 0.35427(11) 0.5094(4) 0.14228(17) 0.0277(7) Uani 1 1 d . . . . .
O5 O 0.29001(12) 0.5038(5) 0.23014(19) 0.0369(8) Uani 1 1 d . . . . .
O6 O 0.28625(13) 0.3265(5) 0.1238(2) 0.0464(9) Uani 1 1 d . . . . .
O7 O 0.32429(11) 0.9033(4) 0.18007(17) 0.0259(7) Uani 1 1 d D . . . .
H7A H 0.3265(16) 0.917(6) 0.1238(12) 0.026(12) Uiso 1 1 d D . . . .
H7B H 0.2877(9) 0.878(7) 0.186(3) 0.044(15) Uiso 1 1 d D . . . .
N1 N 0.40815(12) 0.5091(5) 0.30577(19) 0.0199(7) Uani 1 1 d . . . . .
N2 N 0.37838(12) 0.7137(5) 0.40411(18) 0.0217(7) Uani 1 1 d . . . . .
N3 N 0.36129(12) 0.8224(5) 0.34264(18) 0.0195(7) Uani 1 1 d . . . . .
N4 N 0.32267(14) 1.0835(5) 0.5165(2) 0.0269(8) Uani 1 1 d . . . . .
N5 N 0.47020(13) 0.7706(5) 0.1407(2) 0.0285(8) Uani 1 1 d . . . . .
N6 N 0.30914(14) 0.4438(5) 0.1651(2) 0.0287(8) Uani 1 1 d . . . . .
C1 C 0.29995(17) 1.2299(6) 0.4831(3) 0.0279(9) Uani 1 1 d . . . . .
H1 H 0.285644 1.323250 0.517860 0.034 Uiso 1 1 calc R U . . .
C2 C 0.29524(16) 1.2587(6) 0.3977(2) 0.0247(9) Uani 1 1 d . . . . .
H2 H 0.278338 1.369094 0.378082 0.030 Uiso 1 1 calc R U . . .
C3 C 0.31448(15) 1.1312(6) 0.3443(2) 0.0221(9) Uani 1 1 d . . . . .
H3 H 0.311705 1.148285 0.287448 0.026 Uiso 1 1 calc R U . . .
C4 C 0.33889(14) 0.9716(5) 0.3786(2) 0.0171(8) Uani 1 1 d . . . . .
C5 C 0.34214(15) 0.9537(6) 0.4639(2) 0.0197(8) Uani 1 1 d . . . . .
C6 C 0.36769(16) 0.7840(6) 0.4777(2) 0.0250(9) Uani 1 1 d . . . . .
H6 H 0.375900 0.729049 0.528533 0.030 Uiso 1 1 calc R U . . .
C7 C 0.40529(14) 0.5424(6) 0.3844(2) 0.0195(8) Uani 1 1 d . . . . .
C8 C 0.42533(16) 0.4260(6) 0.4439(2) 0.0252(9) Uani 1 1 d . . . . .
H8 H 0.422387 0.456949 0.499581 0.030 Uiso 1 1 calc R U . . .
C9 C 0.44985(17) 0.2624(6) 0.4187(3) 0.0287(10) Uani 1 1 d . . . . .
H9 H 0.464527 0.177667 0.457058 0.034 Uiso 1 1 calc R U . . .
C10 C 0.45273(16) 0.2237(6) 0.3367(3) 0.0278(9) Uani 1 1 d . . . . .
H10 H 0.469000 0.111175 0.318243 0.033 Uiso 1 1 calc R U . . .
C11 C 0.43195(16) 0.3490(6) 0.2829(3) 0.0254(9) Uani 1 1 d . . . . .
H11 H 0.434417 0.321654 0.226802 0.031 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 2.035(3) . ?
Zn1 O4 2.093(3) . ?
Zn1 O7 2.038(3) . ?
Zn1 N1 2.103(3) . ?
Zn1 N3 2.102(3) . ?
O1 N5 1.261(5) . ?
O2 N5 1.215(4) . ?
O3 N5 1.250(5) . ?
O4 N6 1.274(4) . ?
O5 N6 1.252(5) . ?
O6 N6 1.221(5) . ?
O7 H7A 0.937(19) . ?
O7 H7B 0.934(19) . ?
N1 C7 1.323(5) . ?
N1 C11 1.342(5) . ?
N2 N3 1.348(4) . ?
N2 C6 1.343(5) . ?
N2 C7 1.432(5) . ?
N3 C4 1.341(5) . ?
N4 C1 1.311(6) . ?
N4 C5 1.359(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.432(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.355(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.410(5) . ?
C4 C5 1.420(5) . ?
C5 C6 1.387(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(6) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O4 110.11(13) . . ?
O1 Zn1 O7 89.39(13) . . ?
O1 Zn1 N1 108.17(13) . . ?
O1 Zn1 N3 104.96(13) . . ?
O4 Zn1 N1 91.99(12) . . ?
O4 Zn1 N3 144.93(12) . . ?
O7 Zn1 O4 92.13(12) . . ?
O7 Zn1 N1 159.27(12) . . ?
O7 Zn1 N3 88.90(12) . . ?
N3 Zn1 N1 76.22(12) . . ?
N5 O1 Zn1 111.7(3) . . ?
N6 O4 Zn1 107.0(2) . . ?
Zn1 O7 H7A 114(3) . . ?
Zn1 O7 H7B 117(3) . . ?
H7A O7 H7B 100(4) . . ?
C7 N1 Zn1 117.7(3) . . ?
C7 N1 C11 117.0(3) . . ?
C11 N1 Zn1 125.4(3) . . ?
N3 N2 C7 117.9(3) . . ?
C6 N2 N3 113.9(3) . . ?
C6 N2 C7 128.2(3) . . ?
N2 N3 Zn1 114.5(2) . . ?
C4 N3 Zn1 140.8(3) . . ?
C4 N3 N2 104.7(3) . . ?
C1 N4 C5 115.3(4) . . ?
O2 N5 O1 121.0(4) . . ?
O2 N5 O3 121.2(4) . . ?
O3 N5 O1 117.8(4) . . ?
O5 N6 O4 117.7(4) . . ?
O6 N6 O4 119.9(4) . . ?
O6 N6 O5 122.5(4) . . ?
N4 C1 H1 117.8 . . ?
N4 C1 C2 124.5(4) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 122.2 . . ?
C2 C3 C4 115.7(4) . . ?
C4 C3 H3 122.2 . . ?
N3 C4 C3 130.0(4) . . ?
N3 C4 C5 110.2(3) . . ?
C3 C4 C5 119.8(4) . . ?
N4 C5 C4 123.6(4) . . ?
N4 C5 C6 130.8(4) . . ?
C6 C5 C4 105.5(3) . . ?
N2 C6 C5 105.6(3) . . ?
N2 C6 H6 127.2 . . ?
C5 C6 H6 127.2 . . ?
N1 C7 N2 113.7(3) . . ?
N1 C7 C8 124.9(4) . . ?
C8 C7 N2 121.3(3) . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 116.9(4) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.1(4) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
N1 C11 C10 122.8(4) . . ?
N1 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7 H7A N4 0.937(19) 1.78(2) 2.707(4) 171(4) 7_575 yes
O7 H7B O5 0.934(19) 2.26(3) 3.050(4) 142(4) 8_665 yes
O7 H7B O6 0.934(19) 2.14(3) 2.957(4) 146(4) 8_665 yes
C10 H10 O2 0.95 2.41 3.078(5) 127.2 3_645 yes

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
Zn1 O1 N5 O2 171.0(3) . . . . ?
Zn1 O1 N5 O3 -8.9(5) . . . . ?
Zn1 O4 N6 O5 -2.8(4) . . . . ?
Zn1 O4 N6 O6 177.3(3) . . . . ?
Zn1 N1 C7 N2 2.5(4) . . . . ?
Zn1 N1 C7 C8 -178.1(3) . . . . ?
Zn1 N1 C11 C10 178.5(3) . . . . ?
Zn1 N3 C4 C3 -0.5(7) . . . . ?
Zn1 N3 C4 C5 179.5(3) . . . . ?
N1 C7 C8 C9 -0.4(6) . . . . ?
N2 N3 C4 C3 179.8(4) . . . . ?
N2 N3 C4 C5 -0.2(4) . . . . ?
N2 C7 C8 C9 179.0(3) . . . . ?
N3 N2 C6 C5 -0.8(4) . . . . ?
N3 N2 C7 N1 -2.4(5) . . . . ?
N3 N2 C7 C8 178.2(3) . . . . ?
N3 C4 C5 N4 -179.9(4) . . . . ?
N3 C4 C5 C6 -0.3(4) . . . . ?
N4 C1 C2 C3 0.3(7) . . . . ?
N4 C5 C6 N2 -179.8(4) . . . . ?
C1 N4 C5 C4 0.2(6) . . . . ?
C1 N4 C5 C6 -179.3(4) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 N3 179.8(4) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 N4 0.1(6) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C4 C5 C6 N2 0.6(4) . . . . ?
C5 N4 C1 C2 -0.4(6) . . . . ?
C6 N2 N3 Zn1 -179.2(3) . . . . ?
C6 N2 N3 C4 0.7(4) . . . . ?
C6 N2 C7 N1 178.0(4) . . . . ?
C6 N2 C7 C8 -1.4(6) . . . . ?
C7 N1 C11 C10 -0.2(6) . . . . ?
C7 N2 N3 Zn1 1.2(4) . . . . ?
C7 N2 N3 C4 -179.0(3) . . . . ?
C7 N2 C6 C5 178.8(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C9 C10 C11 N1 -0.6(6) . . . . ?
C11 N1 C7 N2 -178.7(3) . . . . ?
C11 N1 C7 C8 0.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5beta
_database_code_depnum_ccdc_archive 'CCDC 2121414'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-10-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C55 H44 N22 O8 Zn2, 2(N O3), 2(C2 H3 N)'
_chemical_formula_sum            'C59 H50 N26 O14 Zn2'
_chemical_formula_weight         1477.99
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.5157(9)
_cell_length_b                   23.5974(16)
_cell_length_c                   10.2149(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.652(2)
_cell_angle_gamma                90
_cell_volume                     3068.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6475
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0782 before and 0.0701 after correction.
The Ratio of minimum to maximum transmission is 0.9027.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1566
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            61152
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.286
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3772
_reflns_number_total             6257
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         6257
_refine_ls_number_restraints     187
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0939
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0099P)²+13.2189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1515
_refine_special_details          
;
Sample was a poorly diffracting specimen which likely suffered from
additonal un-resolved twinning. The model is presented to establish
connectivity of the minor phase only.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C34-C35 = C37-C36
 1.5 with sigma of 0.02
 Zn1-H1A \\sim Zn1-H1B
 with sigma of 0.02
 O6-N14 \\sim O5-N14 \\sim O5A-N14A \\sim O6A-N14A \\sim O7A-N14A \\sim O7-N14
 with sigma of 0.02
 N15A-C37 \\sim N15-C34
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C35) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(N15) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(N15A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O5, O6, O7, N14, O5A, O6A, O7A, N14A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N9, N10, N11, N12, C23, C24, C25, C26, C27, C28, C29, C33
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: Zn1(0.5) Zn2(0.5) O5(0.5) O6(0.5) O7(0.5) N14(0.5) O5A(0.5)
 O6A(0.5) O7A(0.5) N14A(0.5) N10(0.5) N11(0.5) N12(0.5) C33(0.5) H33(0.5)
 C32(0.5) H32(0.5) C31(0.5) H31(0.5) C30(0.5) H30(0.5) C29(0.5) C25(0.5)
 C24(0.5) C23(0.5) H23(0.5) N9(0.5) C27(0.5) H27(0.5) C26(0.5) H26(0.5)
 C28(0.5) H28(0.5) N15A(0.33333) C36(0.33333) H36A(0.33333) H36B(0.33333)
 H36C(0.33333) C37(0.33333) N15(0.6667) C34(0.6667) C35(0.6667) H35A(0.6667)
 H35B(0.6667) H35C(0.6667)
6.a Free rotating group:
 O1(H1A,H1B)
6.b Me refined with riding coordinates:
 C36(H36A,H36B,H36C), C35(H35A,H35B,H35C)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C33(H33),
  C32(H32), C31(H31), C30(H30), C23(H23), C27(H27), C26(H26), C28(H28)
6.d Fitted hexagon refined as free rotating group:
 N12(C33,C32,C31,C30,C29), C25(C24,C23,N9,C27,C26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.77385(14) 0.38800(11) 0.4865(2) 0.0231(5) Uani 0.5 1 d D . P . .
Zn2 Zn 0.27061(13) 0.61376(11) 0.5085(2) 0.0199(4) Uani 0.5 1 d . . P . .
O1 O 0.6562(3) 0.3179(3) 0.4879(4) 0.0624(15) Uani 1 1 d G . . . .
H1A H 0.608941 0.302474 0.416758 0.094 Uiso 1 1 d DG U . . .
H1B H 0.640884 0.306081 0.559359 0.094 Uiso 1 1 d DG U . . .
N1 N 0.8255(4) 0.3713(2) 0.7056(5) 0.0444(14) Uani 1 1 d . . . . .
N2 N 0.9430(3) 0.3989(2) 1.1744(4) 0.0388(13) Uani 1 1 d . . . . .
N3 N 0.9031(3) 0.4317(2) 1.0579(4) 0.0298(11) Uani 1 1 d . . . . .
N4 N 0.8662(3) 0.5189(2) 0.9526(5) 0.0302(11) Uani 1 1 d . . . . .
N5 N 0.6988(4) 0.39276(18) 0.2713(4) 0.0327(12) Uani 1 1 d . . . . .
N6 N 0.5999(4) 0.4698(2) -0.1632(4) 0.0294(11) Uani 1 1 d . . . . .
N7 N 0.6205(3) 0.48886(18) -0.0305(4) 0.0219(10) Uani 1 1 d . . . . .
N8 N 0.6300(3) 0.56079(18) 0.1263(5) 0.0278(11) Uani 1 1 d . . . . .
C1 C 0.8560(5) 0.3173(3) 0.7474(6) 0.0468(18) Uani 1 1 d . . . . .
H1 H 0.847359 0.289020 0.678295 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8985(5) 0.3019(3) 0.8841(6) 0.0389(15) Uani 1 1 d . . . . .
H2 H 0.918308 0.263727 0.909668 0.047 Uiso 1 1 calc R U . . .
C3 C 0.9117(4) 0.3433(3) 0.9832(5) 0.0299(13) Uani 1 1 d . . . . .
C4 C 0.8827(4) 0.3991(2) 0.9398(5) 0.0269(13) Uani 1 1 d . . . . .
C5 C 0.8383(4) 0.4122(2) 0.7989(5) 0.0331(14) Uani 1 1 d . . . . .
H5 H 0.817557 0.449937 0.770126 0.040 Uiso 1 1 calc R U . . .
C6 C 0.9478(5) 0.3472(3) 1.1313(6) 0.0397(15) Uani 1 1 d . . . . .
H6 H 0.972565 0.315801 1.191565 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8918(4) 0.4905(3) 1.0710(6) 0.0326(14) Uani 1 1 d . . . . .
C8 C 0.9052(4) 0.5139(3) 1.2005(6) 0.0422(17) Uani 1 1 d . . . . .
H8 H 0.921503 0.491086 1.281599 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8939(5) 0.5713(3) 1.2061(7) 0.0512(19) Uani 1 1 d . . . . .
H9 H 0.903229 0.589328 1.292514 0.061 Uiso 1 1 calc R U . . .
C10 C 0.8688(4) 0.6030(3) 1.0854(7) 0.0485(18) Uani 1 1 d . . . . .
H10 H 0.860878 0.642965 1.087323 0.058 Uiso 1 1 calc R U . . .
C11 C 0.8557(4) 0.5750(3) 0.9622(7) 0.0390(15) Uani 1 1 d . . . . .
H11 H 0.838274 0.596795 0.879292 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6942(4) 0.3447(2) 0.1957(5) 0.0321(14) Uani 1 1 d . . . . .
H12 H 0.710447 0.309628 0.243975 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6674(4) 0.3440(2) 0.0545(5) 0.0282(13) Uani 1 1 d . . . . .
H13 H 0.665418 0.309705 0.005174 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6429(4) 0.3960(2) -0.0147(5) 0.0228(12) Uani 1 1 d . . . . .
C15 C 0.6466(4) 0.4446(2) 0.0627(5) 0.0197(11) Uani 1 1 d . . . . .
C16 C 0.6747(4) 0.4421(2) 0.2065(5) 0.0267(13) Uani 1 1 d . . . . .
H16 H 0.676644 0.475781 0.258280 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6136(4) 0.4148(2) -0.1538(5) 0.0279(13) Uani 1 1 d . . . . .
H17 H 0.604793 0.390549 -0.231142 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6149(4) 0.5469(2) -0.0057(5) 0.0215(12) Uani 1 1 d . . . . .
C19 C 0.5967(4) 0.5861(3) -0.1133(6) 0.0344(14) Uani 1 1 d . . . . .
H19 H 0.586064 0.574381 -0.206069 0.041 Uiso 1 1 calc R U . . .
C20 C 0.5948(5) 0.6426(3) -0.0793(7) 0.0445(17) Uani 1 1 d . . . . .
H20 H 0.583168 0.670723 -0.149432 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6096(5) 0.6584(3) 0.0547(7) 0.0419(16) Uani 1 1 d . . . . .
H21 H 0.608733 0.697163 0.079195 0.050 Uiso 1 1 calc R U . . .
C22 C 0.6259(4) 0.6162(3) 0.1536(6) 0.0367(14) Uani 1 1 d . . . . .
H22 H 0.634644 0.627048 0.246372 0.044 Uiso 1 1 calc R U . . .
O5 O 0.8535(7) 0.3273(4) 0.4679(10) 0.033(2) Uani 0.5 1 d D . P A 1
O6 O 0.9233(13) 0.4112(4) 0.4901(19) 0.032(3) Uani 0.5 1 d D . P A 1
O7 O 1.0178(6) 0.3371(3) 0.4864(8) 0.0337(18) Uani 0.5 1 d D . P A 1
N14 N 0.9316(7) 0.3567(4) 0.4816(14) 0.025(2) Uani 0.5 1 d D . P A 1
O5A O 0.9063(10) 0.3377(5) 0.4580(13) 0.055(3) Uani 0.5 1 d D . P A 2
O6A O 0.9158(16) 0.4267(6) 0.485(2) 0.053(4) Uani 0.5 1 d D . P A 2
O7A O 1.0541(7) 0.3804(5) 0.4766(8) 0.061(2) Uani 0.5 1 d D . P A 2
N14A N 0.9624(8) 0.3818(5) 0.4741(11) 0.047(3) Uani 0.5 1 d D . P A 2
N10 N 0.4366(7) 0.5823(3) 0.5194(8) 0.0195(15) Uani 0.5 1 d . . P A -1
N11 N 0.4474(7) 0.5247(4) 0.5061(8) 0.0188(16) Uani 0.5 1 d . . P A -1
N12 N 0.2717(5) 0.5182(2) 0.4735(8) 0.020(2) Uani 0.5 1 d G . P A -1
C33 C 0.1790(4) 0.4877(3) 0.4460(9) 0.034(3) Uani 0.5 1 d G . P A -1
H33 H 0.115025 0.506844 0.435900 0.041 Uiso 0.5 1 calc R U P A -1
C32 C 0.1799(4) 0.4290(3) 0.4333(8) 0.034(3) Uani 0.5 1 d G . P A -1
H32 H 0.116504 0.408143 0.414560 0.041 Uiso 0.5 1 calc R U P A -1
C31 C 0.2734(6) 0.4010(2) 0.4481(9) 0.034(3) Uani 0.5 1 d G . P A -1
H31 H 0.274023 0.360902 0.439475 0.040 Uiso 0.5 1 calc R U P A -1
C30 C 0.3661(4) 0.4315(2) 0.4756(9) 0.021(3) Uani 0.5 1 d G . P A -1
H30 H 0.430065 0.412363 0.485732 0.025 Uiso 0.5 1 calc R U P A -1
C29 C 0.3652(4) 0.4902(2) 0.4883(7) 0.0196(17) Uani 0.5 1 d G . P A -1
C25 C 0.6029(6) 0.5640(2) 0.5338(9) 0.021(2) Uani 0.5 1 d G . P A -1
C24 C 0.5488(4) 0.5128(3) 0.5124(7) 0.0193(17) Uani 0.5 1 d G . P A -1
C23 C 0.6003(5) 0.4627(2) 0.5031(8) 0.022(2) Uani 0.5 1 d G . P A -1
H23 H 0.563371 0.427768 0.488488 0.026 Uiso 0.5 1 calc R U P A -1
N9 N 0.7058(5) 0.4639(2) 0.5152(8) 0.0184(18) Uani 0.5 1 d G . P A -1
C27 C 0.7599(4) 0.5150(3) 0.5366(7) 0.0185(18) Uani 0.5 1 d G U P A -1
H27 H 0.832026 0.515816 0.544851 0.022 Uiso 0.5 1 calc R U P A -1
C26 C 0.7084(6) 0.5651(2) 0.5459(8) 0.0222(19) Uani 0.5 1 d G . P A -1
H26 H 0.745347 0.600058 0.560489 0.027 Uiso 0.5 1 calc R U P A -1
C28 C 0.5286(8) 0.6054(4) 0.5356(9) 0.0213(16) Uani 0.5 1 d . . P A -1
H28 H 0.542962 0.644807 0.547139 0.026 Uiso 0.5 1 calc R U P A -1
O2 O 0.6258(4) 0.21441(18) 0.2284(4) 0.0456(11) Uani 1 1 d . . . . .
O3 O 0.4618(4) 0.2001(3) 0.1196(5) 0.107(2) Uani 1 1 d . . . . .
O4 O 0.5089(4) 0.2544(2) 0.2992(5) 0.0572(13) Uani 1 1 d . . . . .
N13 N 0.5314(5) 0.2230(3) 0.2141(6) 0.0563(18) Uani 1 1 d . . . . .
N15A N 0.819(3) 0.7619(16) 0.957(3) 0.122(14) Uani 0.3333 1 d D U P B 1
C36 C 0.845(2) 0.7365(12) 0.725(3) 0.087(8) Uani 0.3333 1 d D U P B 1
H36A H 0.794570 0.751396 0.638824 0.130 Uiso 0.3333 1 calc R U P B 1
H36B H 0.915489 0.750110 0.735446 0.130 Uiso 0.3333 1 calc R U P B 1
H36C H 0.843775 0.695017 0.722545 0.130 Uiso 0.3333 1 calc R U P B 1
C37 C 0.816(3) 0.7560(16) 0.843(3) 0.101(12) Uani 0.3333 1 d D U P B 1
N15 N 0.7686(11) 0.6916(6) 0.7211(13) 0.110(4) Uani 0.6667 1 d D U P C 2
C34 C 0.7802(12) 0.7269(5) 0.7997(14) 0.074(4) Uani 0.6667 1 d D U P C 2
C35 C 0.7739(12) 0.7678(6) 0.9047(17) 0.074(4) Uani 0.6667 1 d D U P C 2
H35A H 0.833717 0.793836 0.926728 0.111 Uiso 0.6667 1 calc R U P C 2
H35B H 0.708282 0.789318 0.868554 0.111 Uiso 0.6667 1 calc R U P C 2
H35C H 0.775371 0.747509 0.989113 0.111 Uiso 0.6667 1 calc R U P C 2


_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 Zn2 0.6214(17) 3_666 ?
Zn1 O1 2.297(5) . ?
Zn1 N1 2.145(5) . ?
Zn1 N5 2.092(4) . ?
Zn1 O5 1.841(10) . ?
Zn1 O6 2.081(17) . ?
Zn1 N14 2.273(9) . ?
Zn1 O5A 2.247(13) . ?
Zn1 O6A 2.13(2) . ?
Zn1 N9 2.078(5) . ?
Zn2 O1 1.885(6) 3_666 ?
Zn2 N1 2.164(5) 3_666 ?
Zn2 N5 2.152(5) 3_666 ?
Zn2 O5 2.254(10) 3_666 ?
Zn2 N10 2.331(8) . ?
Zn2 N12 2.283(5) . ?
O1 H1A 0.8701 . ?
O1 H1B 0.8695 . ?
N1 C1 1.362(7) . ?
N1 C5 1.326(7) . ?
N2 N3 1.369(6) . ?
N2 C6 1.305(8) . ?
N3 C4 1.378(6) . ?
N3 C7 1.407(7) . ?
N4 C7 1.323(7) . ?
N4 C11 1.339(7) . ?
N5 C12 1.362(7) . ?
N5 C16 1.325(6) . ?
N6 N7 1.365(5) . ?
N6 C17 1.310(7) . ?
N7 C15 1.377(6) . ?
N7 C18 1.399(6) . ?
N8 C18 1.335(6) . ?
N8 C22 1.342(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.368(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(8) . ?
C3 C4 1.403(8) . ?
C3 C6 1.428(7) . ?
C4 C5 1.395(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.389(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.364(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(7) . ?
C14 C15 1.384(7) . ?
C14 C17 1.413(7) . ?
C15 C16 1.389(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.393(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.367(9) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(8) . ?
C22 H22 0.9500 . ?
O5 N14 1.232(10) . ?
O6 N14 1.295(11) . ?
O7 N14 1.240(10) . ?
O5A N14A 1.267(11) . ?
O6A N14A 1.254(11) . ?
O7A N14A 1.232(10) . ?
N10 N11 1.380(11) . ?
N10 C28 1.315(12) . ?
N11 C29 1.339(9) . ?
N11 C24 1.379(10) . ?
N12 C33 1.3900 . ?
N12 C29 1.3900 . ?
C33 H33 0.9500 . ?
C33 C32 1.3900 . ?
C32 H32 0.9500 . ?
C32 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C30 1.3900 . ?
C30 H30 0.9500 . ?
C30 C29 1.3900 . ?
C25 C24 1.3900 . ?
C25 C26 1.3900 . ?
C25 C28 1.405(11) . ?
C24 C23 1.3900 . ?
C23 H23 0.9500 . ?
C23 N9 1.3900 . ?
N9 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C26 1.3900 . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
O2 N13 1.252(7) . ?
O3 N13 1.224(7) . ?
O4 N13 1.254(7) . ?
N15A C37 1.16(2) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C36 C37 1.456(19) . ?
N15 C34 1.131(14) . ?
C34 C35 1.467(15) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

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
Zn2 Zn1 O1 42.3(4) 3_666 . ?
Zn2 Zn1 N1 83.4(4) 3_666 . ?
Zn2 Zn1 N5 87.1(4) 3_666 . ?
Zn2 Zn1 O5 124.9(6) 3_666 . ?
Zn2 Zn1 O6 167.4(6) 3_666 . ?
Zn2 Zn1 N14 157.0(6) 3_666 . ?
Zn2 Zn1 O5A 144.1(6) 3_666 . ?
Zn2 Zn1 O6A 158.1(6) 3_666 . ?
Zn2 Zn1 N9 63.9(5) 3_666 . ?
N1 Zn1 O1 81.03(18) . . ?
N1 Zn1 N14 89.1(4) . . ?
N1 Zn1 O5A 92.5(4) . . ?
N5 Zn1 O1 87.32(18) . . ?
N5 Zn1 N1 168.3(2) . . ?
N5 Zn1 N14 97.0(4) . . ?
N5 Zn1 O5A 91.0(4) . . ?
N5 Zn1 O6A 95.0(6) . . ?
O5 Zn1 O1 82.6(3) . . ?
O5 Zn1 N1 88.2(3) . . ?
O5 Zn1 N5 91.5(3) . . ?
O5 Zn1 O6 66.9(4) . . ?
O5 Zn1 N14 32.8(3) . . ?
O5 Zn1 N9 170.9(3) . . ?
O6 Zn1 O1 149.2(3) . . ?
O6 Zn1 N1 93.2(5) . . ?
O6 Zn1 N5 97.4(5) . . ?
O6 Zn1 N14 34.2(3) . . ?
N14 Zn1 O1 115.0(3) . . ?
O5A Zn1 O1 101.7(4) . . ?
O6A Zn1 O1 159.3(3) . . ?
O6A Zn1 N1 96.3(6) . . ?
O6A Zn1 O5A 57.7(4) . . ?
N9 Zn1 O1 106.2(2) . . ?
N9 Zn1 N1 90.9(3) . . ?
N9 Zn1 N5 91.2(3) . . ?
N9 Zn1 O6 104.1(4) . . ?
N9 Zn1 N14 138.2(3) . . ?
Zn1 Zn2 O1 124.8(5) 3_666 3_666 ?
Zn1 Zn2 N1 80.0(4) 3_666 3_666 ?
Zn1 Zn2 N5 76.1(4) 3_666 3_666 ?
Zn1 Zn2 O5 42.0(5) 3_666 3_666 ?
Zn1 Zn2 N10 156.5(5) 3_666 . ?
Zn1 Zn2 N12 90.2(5) 3_666 . ?
O1 Zn2 N1 90.8(2) 3_666 3_666 ?
O1 Zn2 N5 97.21(19) 3_666 3_666 ?
O1 Zn2 O5 82.8(3) 3_666 3_666 ?
O1 Zn2 N10 77.4(3) 3_666 . ?
O1 Zn2 N12 144.7(2) 3_666 . ?
N1 Zn2 O5 78.0(3) 3_666 3_666 ?
N1 Zn2 N10 110.0(3) 3_666 . ?
N1 Zn2 N12 92.1(2) 3_666 . ?
N5 Zn2 N1 155.1(2) 3_666 3_666 ?
N5 Zn2 O5 79.6(3) 3_666 3_666 ?
N5 Zn2 N10 94.8(2) 3_666 . ?
N5 Zn2 N12 94.8(2) 3_666 . ?
O5 Zn2 N10 158.6(3) 3_666 . ?
O5 Zn2 N12 132.1(3) 3_666 . ?
N12 Zn2 N10 68.7(3) . . ?
Zn1 O1 H1A 127.7 . . ?
Zn1 O1 H1B 126.7 . . ?
Zn2 O1 Zn1 12.83(10) 3_666 . ?
Zn2 O1 H1A 127.5 3_666 . ?
Zn2 O1 H1B 122.0 3_666 . ?
H1A O1 H1B 104.5 . . ?
Zn1 N1 Zn2 16.58(6) . 3_666 ?
C1 N1 Zn1 117.2(4) . . ?
C1 N1 Zn2 119.0(4) . 3_666 ?
C5 N1 Zn1 122.3(4) . . ?
C5 N1 Zn2 119.8(4) . 3_666 ?
C5 N1 C1 120.2(5) . . ?
C6 N2 N3 106.5(5) . . ?
N2 N3 C4 110.5(5) . . ?
N2 N3 C7 119.9(4) . . ?
C4 N3 C7 129.6(4) . . ?
C7 N4 C11 115.9(5) . . ?
Zn1 N5 Zn2 16.76(5) . 3_666 ?
C12 N5 Zn1 117.7(3) . . ?
C12 N5 Zn2 119.3(3) . 3_666 ?
C16 N5 Zn1 121.5(4) . . ?
C16 N5 Zn2 120.9(4) . 3_666 ?
C16 N5 C12 119.5(4) . . ?
C17 N6 N7 106.1(4) . . ?
N6 N7 C15 110.8(4) . . ?
N6 N7 C18 119.8(4) . . ?
C15 N7 C18 129.4(4) . . ?
C18 N8 C22 116.5(5) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(6) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.9(6) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 C6 137.7(6) . . ?
C4 C3 C6 103.5(5) . . ?
N3 C4 C3 107.2(4) . . ?
N3 C4 C5 132.0(5) . . ?
C5 C4 C3 120.8(5) . . ?
N1 C5 C4 119.1(5) . . ?
N1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N2 C6 C3 112.3(5) . . ?
N2 C6 H6 123.8 . . ?
C3 C6 H6 123.8 . . ?
N4 C7 N3 114.6(5) . . ?
N4 C7 C8 125.4(6) . . ?
C8 C7 N3 120.0(6) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 C7 117.0(6) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(6) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.1(7) . . ?
C11 C10 H10 120.9 . . ?
N4 C11 C10 123.8(6) . . ?
N4 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N5 C12 H12 118.2 . . ?
N5 C12 C13 123.6(5) . . ?
C13 C12 H12 118.2 . . ?
C12 C13 H13 121.3 . . ?
C12 C13 C14 117.3(5) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 C17 136.3(5) . . ?
C15 C14 C13 118.8(4) . . ?
C15 C14 C17 105.0(5) . . ?
N7 C15 C14 106.4(4) . . ?
N7 C15 C16 132.7(5) . . ?
C14 C15 C16 120.9(5) . . ?
N5 C16 C15 119.9(5) . . ?
N5 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N6 C17 C14 111.7(5) . . ?
N6 C17 H17 124.2 . . ?
C14 C17 H17 124.2 . . ?
N8 C18 N7 115.1(4) . . ?
N8 C18 C19 124.1(5) . . ?
C19 C18 N7 120.8(5) . . ?
C18 C19 H19 121.4 . . ?
C20 C19 C18 117.1(6) . . ?
C20 C19 H19 121.4 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 121.0 . . ?
C20 C21 C22 118.0(6) . . ?
C22 C21 H21 121.0 . . ?
N8 C22 C21 123.9(6) . . ?
N8 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?
Zn1 O5 Zn2 13.07(13) . 3_666 ?
N14 O5 Zn1 93.3(6) . . ?
N14 O5 Zn2 106.2(7) . 3_666 ?
N14 O6 Zn1 81.0(9) . . ?
O5 N14 Zn1 53.9(5) . . ?
O5 N14 O6 118.5(11) . . ?
O5 N14 O7 123.4(10) . . ?
O6 N14 Zn1 64.7(9) . . ?
O7 N14 Zn1 175.5(9) . . ?
O7 N14 O6 118.1(12) . . ?
N14A O5A Zn1 91.0(8) . . ?
N14A O6A Zn1 96.9(12) . . ?
O6A N14A O5A 114.1(14) . . ?
O7A N14A O5A 122.3(13) . . ?
O7A N14A O6A 123.6(15) . . ?
N11 N10 Zn2 116.2(6) . . ?
C28 N10 Zn2 136.7(7) . . ?
C28 N10 N11 107.1(8) . . ?
C29 N11 N10 120.1(8) . . ?
C29 N11 C24 130.4(9) . . ?
C24 N11 N10 109.4(7) . . ?
C33 N12 Zn2 119.4(3) . . ?
C33 N12 C29 120.0 . . ?
C29 N12 Zn2 120.4(3) . . ?
N12 C33 H33 120.0 . . ?
N12 C33 C32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C29 C30 H30 120.0 . . ?
N11 C29 N12 114.1(6) . . ?
N11 C29 C30 125.8(6) . . ?
C30 C29 N12 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 C28 105.4(6) . . ?
C26 C25 C28 134.6(6) . . ?
N11 C24 C25 107.0(7) . . ?
N11 C24 C23 133.0(7) . . ?
C23 C24 C25 120.0 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 N9 120.0 . . ?
N9 C23 H23 120.0 . . ?
C23 N9 Zn1 117.4(4) . . ?
C27 N9 Zn1 122.5(4) . . ?
C27 N9 C23 120.0 . . ?
N9 C27 H27 120.0 . . ?
N9 C27 C26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
N10 C28 C25 111.1(9) . . ?
N10 C28 H28 124.5 . . ?
C25 C28 H28 124.5 . . ?
O2 N13 O4 119.4(6) . . ?
O3 N13 O2 120.1(8) . . ?
O3 N13 O4 120.5(7) . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C37 C36 H36C 109.5 . . ?
N15A C37 C36 159(4) . . ?
N15 C34 C35 167.4(18) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 N1 C1 C2 174.6(5) . . . . ?
Zn1 N1 C5 C4 -173.2(4) . . . . ?
Zn1 N5 C12 C13 -166.2(4) . . . . ?
Zn1 N5 C16 C15 165.8(4) . . . . ?
Zn1 O5 N14 O6 -5.2(15) . . . . ?
Zn1 O5 N14 O7 175.5(12) . . . . ?
Zn1 O6 N14 O5 4.6(14) . . . . ?
Zn1 O6 N14 O7 -176.0(12) . . . . ?
Zn1 O5A N14A O6A -5.2(12) . . . . ?
Zn1 O5A N14A O7A 176.0(10) . . . . ?
Zn1 O6A N14A O5A 5.5(13) . . . . ?
Zn1 O6A N14A O7A -175.7(10) . . . . ?
Zn1 N9 C27 C26 175.7(6) . . . . ?
Zn2 Zn1 O5 N14 -171.9(8) 3_666 . . . ?
Zn2 N1 C1 C2 -166.7(5) 3_666 . . . ?
Zn2 N1 C5 C4 167.6(4) 3_666 . . . ?
Zn2 N5 C12 C13 174.8(4) 3_666 . . . ?
Zn2 N5 C16 C15 -174.6(4) 3_666 . . . ?
Zn2 O5 N14 Zn1 -1.90(19) 3_666 . . . ?
Zn2 O5 N14 O6 -7.1(16) 3_666 . . . ?
Zn2 O5 N14 O7 173.6(11) 3_666 . . . ?
Zn2 N10 N11 C29 -0.1(10) . . . . ?
Zn2 N10 N11 C24 179.1(5) . . . . ?
Zn2 N10 C28 C25 179.9(6) . . . . ?
Zn2 N12 C33 C32 -175.9(5) . . . . ?
Zn2 N12 C29 N11 -8.0(7) . . . . ?
Zn2 N12 C29 C30 175.8(5) . . . . ?
O1 Zn1 O5 Zn2 -0.5(5) . . . 3_666 ?
O1 Zn1 O5 N14 -172.4(7) . . . . ?
N1 Zn1 O5 Zn2 80.7(5) . . . 3_666 ?
N1 Zn1 O5 N14 -91.2(7) . . . . ?
N1 C1 C2 C3 -0.7(10) . . . . ?
N2 N3 C4 C3 -0.5(6) . . . . ?
N2 N3 C4 C5 176.9(6) . . . . ?
N2 N3 C7 N4 171.3(4) . . . . ?
N2 N3 C7 C8 -10.2(7) . . . . ?
N3 N2 C6 C3 0.4(7) . . . . ?
N3 C4 C5 N1 -178.4(6) . . . . ?
N3 C7 C8 C9 179.5(5) . . . . ?
N4 C7 C8 C9 -2.1(9) . . . . ?
N5 Zn1 O5 Zn2 -87.6(5) . . . 3_666 ?
N5 Zn1 O5 N14 100.5(7) . . . . ?
N5 C12 C13 C14 -0.5(9) . . . . ?
N6 N7 C15 C14 0.4(5) . . . . ?
N6 N7 C15 C16 179.2(5) . . . . ?
N6 N7 C18 N8 176.0(4) . . . . ?
N6 N7 C18 C19 -5.2(7) . . . . ?
N7 N6 C17 C14 0.4(6) . . . . ?
N7 C15 C16 N5 -178.4(5) . . . . ?
N7 C18 C19 C20 -178.5(5) . . . . ?
N8 C18 C19 C20 0.2(8) . . . . ?
C1 N1 C5 C4 -0.4(9) . . . . ?
C1 C2 C3 C4 -0.9(9) . . . . ?
C1 C2 C3 C6 177.6(7) . . . . ?
C2 C3 C4 N3 179.7(5) . . . . ?
C2 C3 C4 C5 1.9(8) . . . . ?
C2 C3 C6 N2 -179.4(7) . . . . ?
C3 C4 C5 N1 -1.2(9) . . . . ?
C4 N3 C7 N4 -6.3(8) . . . . ?
C4 N3 C7 C8 172.3(5) . . . . ?
C4 C3 C6 N2 -0.7(7) . . . . ?
C5 N1 C1 C2 1.4(11) . . . . ?
C6 N2 N3 C4 0.1(6) . . . . ?
C6 N2 N3 C7 -177.9(5) . . . . ?
C6 C3 C4 N3 0.7(6) . . . . ?
C6 C3 C4 C5 -177.1(5) . . . . ?
C7 N3 C4 C3 177.2(5) . . . . ?
C7 N3 C4 C5 -5.3(10) . . . . ?
C7 N4 C11 C10 -0.9(8) . . . . ?
C7 C8 C9 C10 0.8(9) . . . . ?
C8 C9 C10 C11 0.2(9) . . . . ?
C9 C10 C11 N4 -0.2(9) . . . . ?
C11 N4 C7 N3 -179.5(5) . . . . ?
C11 N4 C7 C8 2.0(8) . . . . ?
C12 N5 C16 C15 -1.1(8) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C12 C13 C14 C17 179.0(6) . . . . ?
C13 C14 C15 N7 179.4(5) . . . . ?
C13 C14 C15 C16 0.4(8) . . . . ?
C13 C14 C17 N6 -179.5(6) . . . . ?
C14 C15 C16 N5 0.3(8) . . . . ?
C15 N7 C18 N8 -5.1(7) . . . . ?
C15 N7 C18 C19 173.6(5) . . . . ?
C15 C14 C17 N6 -0.1(6) . . . . ?
C16 N5 C12 C13 1.2(9) . . . . ?
C17 N6 N7 C15 -0.5(6) . . . . ?
C17 N6 N7 C18 178.5(4) . . . . ?
C17 C14 C15 N7 -0.2(5) . . . . ?
C17 C14 C15 C16 -179.1(5) . . . . ?
C18 N7 C15 C14 -178.5(5) . . . . ?
C18 N7 C15 C16 0.3(9) . . . . ?
C18 N8 C22 C21 -1.6(8) . . . . ?
C18 C19 C20 C21 -0.4(9) . . . . ?
C19 C20 C21 C22 -0.3(9) . . . . ?
C20 C21 C22 N8 1.3(9) . . . . ?
C22 N8 C18 N7 179.5(5) . . . . ?
C22 N8 C18 C19 0.8(8) . . . . ?
O6 Zn1 O5 Zn2 175.0(8) . . . 3_666 ?
O6 Zn1 O5 N14 3.1(9) . . . . ?
N14 Zn1 O5 Zn2 171.9(8) . . . 3_666 ?
N10 N11 C29 N12 5.1(10) . . . . ?
N10 N11 C29 C30 -179.0(6) . . . . ?
N10 N11 C24 C25 1.6(7) . . . . ?
N10 N11 C24 C23 -179.1(6) . . . . ?
N11 N10 C28 C25 -0.1(10) . . . . ?
N11 C24 C23 N9 -179.2(8) . . . . ?
N12 C33 C32 C31 0.0 . . . . ?
C33 N12 C29 N11 176.1(6) . . . . ?
C33 N12 C29 C30 0.0 . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C31 C30 C29 N11 -175.7(7) . . . . ?
C31 C30 C29 N12 0.0 . . . . ?
C29 N11 C24 C25 -179.4(8) . . . . ?
C29 N11 C24 C23 -0.1(13) . . . . ?
C29 N12 C33 C32 0.0 . . . . ?
C25 C24 C23 N9 0.0 . . . . ?
C24 N11 C29 N12 -173.9(6) . . . . ?
C24 N11 C29 C30 2.0(11) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C24 C25 C28 N10 1.0(8) . . . . ?
C24 C23 N9 Zn1 -175.9(5) . . . . ?
C24 C23 N9 C27 0.0 . . . . ?
C23 N9 C27 C26 0.0 . . . . ?
N9 C27 C26 C25 0.0 . . . . ?
C26 C25 C24 N11 179.4(6) . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C26 C25 C28 N10 179.9(6) . . . . ?
C28 N10 N11 C29 179.9(8) . . . . ?
C28 N10 N11 C24 -1.0(9) . . . . ?
C28 C25 C24 N11 -1.6(6) . . . . ?
C28 C25 C24 C23 179.0(7) . . . . ?
C28 C25 C26 C27 -178.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5alpha
_database_code_depnum_ccdc_archive 'CCDC 2121413'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 N4 O4 Zn, H2 O, 2(N O3)'
_chemical_formula_sum            'C11 H18 N6 O11 Zn'
_chemical_formula_weight         475.68
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.9228(7)
_cell_length_b                   15.0043(14)
_cell_length_c                   17.5340(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.558(2)
_cell_angle_gamma                90
_cell_volume                     1801.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.436
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.656
_exptl_absorpt_coefficient_mu    1.438
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0724 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8918.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23231
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.349
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3158
_reflns_number_total             4328
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0112P)²+9.0509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1220
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Zn1-H2A \\sim Zn1-H2B
 with sigma of 0.02
3.a Free rotating group:
 O2(H2A,H2B), O5(H5A,H5B)
3.b Rotating group:
 O1(H1A,H1B), O3(H3A,H3B), O4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.49983(8) 0.29225(3) 0.35193(3) 0.01189(13) Uani 1 1 d D . . . .
O1 O 0.2746(5) 0.3112(2) 0.42212(18) 0.0189(7) Uani 1 1 d . . . . .
H1A H 0.319979 0.343063 0.462248 0.028 Uiso 1 1 d R U . . .
H1B H 0.181801 0.343570 0.397138 0.028 Uiso 1 1 d R U . . .
O2 O 0.4840(5) 0.4234(2) 0.3187(2) 0.0217(8) Uani 1 1 d G . . . .
H2A H 0.570369 0.464716 0.332538 0.033 Uiso 1 1 d DG U . . .
H2B H 0.376459 0.452471 0.303475 0.033 Uiso 1 1 d DG U . . .
O3 O 0.2678(5) 0.2594(2) 0.26871(17) 0.0147(7) Uani 1 1 d . . . . .
H3A H 0.198570 0.217494 0.286041 0.022 Uiso 1 1 d R U . . .
H3B H 0.311552 0.235140 0.229381 0.022 Uiso 1 1 d R U . . .
O4 O 0.7000(5) 0.2712(2) 0.27579(19) 0.0189(7) Uani 1 1 d . . . . .
H4A H 0.791609 0.235425 0.296910 0.028 Uiso 1 1 d R U . . .
H4B H 0.760384 0.320870 0.269320 0.028 Uiso 1 1 d R U . . .
O5 O 0.0024(5) 0.1511(2) 0.32518(19) 0.0183(7) Uani 1 1 d G . . . .
H5A H -0.053787 0.102550 0.305827 0.027 Uiso 1 1 d G U . . .
H5B H 0.079921 0.133338 0.365999 0.027 Uiso 1 1 d G U . . .
N1 N 0.6984(6) 0.3016(2) 0.4571(2) 0.0153(8) Uani 1 1 d . . . . .
N2 N 0.6652(5) 0.1482(2) 0.4587(2) 0.0116(8) Uani 1 1 d . . . . .
N3 N 0.5581(5) 0.1568(2) 0.3872(2) 0.0121(8) Uani 1 1 d . . . . .
N4 N 0.8216(6) -0.0751(3) 0.5345(2) 0.0157(8) Uani 1 1 d . . . . .
C1 C 0.7418(7) -0.1200(3) 0.4703(3) 0.0181(10) Uani 1 1 d . . . . .
H1 H 0.754789 -0.183059 0.470295 0.022 Uiso 1 1 calc R U . . .
C2 C 0.6442(7) -0.0807(3) 0.4059(3) 0.0169(10) Uani 1 1 d . . . . .
H2 H 0.592378 -0.114722 0.361896 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6236(7) 0.0117(3) 0.4072(3) 0.0133(9) Uani 1 1 d . . . . .
C4 C 0.7069(6) 0.0591(3) 0.4733(3) 0.0114(9) Uani 1 1 d . . . . .
C5 C 0.8052(7) 0.0129(3) 0.5366(3) 0.0159(10) Uani 1 1 d . . . . .
H5 H 0.860634 0.044668 0.581376 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5330(7) 0.0774(3) 0.3561(3) 0.0143(9) Uani 1 1 d . . . . .
H6 H 0.463753 0.065608 0.306135 0.017 Uiso 1 1 calc R U . . .
C7 C 0.7273(6) 0.2277(3) 0.4990(3) 0.0127(9) Uani 1 1 d . . . . .
C8 C 0.8076(7) 0.2268(3) 0.5759(3) 0.0192(10) Uani 1 1 d . . . . .
H8 H 0.820830 0.172934 0.604644 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8678(8) 0.3071(3) 0.6095(3) 0.0231(11) Uani 1 1 d . . . . .
H9 H 0.925311 0.309079 0.662170 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8446(7) 0.3848(3) 0.5668(3) 0.0208(11) Uani 1 1 d . . . . .
H10 H 0.887172 0.440429 0.589164 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7584(7) 0.3797(3) 0.4909(3) 0.0192(10) Uani 1 1 d . . . . .
H11 H 0.740523 0.432840 0.461263 0.023 Uiso 1 1 calc R U . . .
O6 O -0.0155(5) 0.4116(2) 0.3354(2) 0.0243(8) Uani 1 1 d . . . . .
O7 O -0.1467(5) 0.4350(3) 0.2183(2) 0.0312(9) Uani 1 1 d . . . . .
O8 O 0.1265(5) 0.5002(2) 0.2625(2) 0.0275(9) Uani 1 1 d . . . . .
N5 N -0.0124(6) 0.4486(3) 0.2725(2) 0.0191(9) Uani 1 1 d . . . . .
O9 O 0.6951(5) 0.5775(2) 0.32498(18) 0.0188(7) Uani 1 1 d . . . . .
O10 O 0.6554(6) 0.5882(2) 0.44446(19) 0.0247(8) Uani 1 1 d . . . . .
O11 O 0.6613(6) 0.7067(2) 0.37517(19) 0.0261(8) Uani 1 1 d . . . . .
N6 N 0.6693(6) 0.6243(2) 0.3818(2) 0.0154(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
Zn1 O1 2.144(3) . ?
Zn1 O2 2.051(3) . ?
Zn1 O3 2.063(3) . ?
Zn1 O4 2.086(3) . ?
Zn1 N1 2.135(4) . ?
Zn1 N3 2.144(4) . ?
O1 H1A 0.8697 . ?
O1 H1B 0.8700 . ?
O2 H2A 0.8702 . ?
O2 H2B 0.8699 . ?
O3 H3A 0.8725 . ?
O3 H3B 0.8730 . ?
O4 H4A 0.8703 . ?
O4 H4B 0.8703 . ?
O5 H5A 0.8703 . ?
O5 H5B 0.8698 . ?
N1 C7 1.328(5) . ?
N1 C11 1.350(6) . ?
N2 N3 1.365(5) . ?
N2 C4 1.385(5) . ?
N2 C7 1.419(5) . ?
N3 C6 1.311(5) . ?
N4 C1 1.357(6) . ?
N4 C5 1.326(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.361(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(6) . ?
C3 C4 1.408(6) . ?
C3 C6 1.414(6) . ?
C4 C5 1.396(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.381(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(7) . ?
C11 H11 0.9500 . ?
O6 N5 1.239(5) . ?
O7 N5 1.243(5) . ?
O8 N5 1.268(5) . ?
O9 N6 1.253(5) . ?
O10 N6 1.241(5) . ?
O11 N6 1.243(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 N3 94.70(13) . . ?
O2 Zn1 O1 91.33(14) . . ?
O2 Zn1 O3 91.44(13) . . ?
O2 Zn1 O4 88.62(14) . . ?
O2 Zn1 N1 100.54(14) . . ?
O2 Zn1 N3 172.28(14) . . ?
O3 Zn1 O1 83.20(13) . . ?
O3 Zn1 O4 91.87(13) . . ?
O3 Zn1 N1 163.84(13) . . ?
O3 Zn1 N3 94.06(13) . . ?
O4 Zn1 O1 175.06(13) . . ?
O4 Zn1 N1 99.17(14) . . ?
O4 Zn1 N3 85.79(13) . . ?
N1 Zn1 O1 85.70(14) . . ?
N1 Zn1 N3 75.17(14) . . ?
Zn1 O1 H1A 109.4 . . ?
Zn1 O1 H1B 109.3 . . ?
H1A O1 H1B 104.5 . . ?
Zn1 O2 H2A 126.8 . . ?
Zn1 O2 H2B 125.1 . . ?
H2A O2 H2B 104.5 . . ?
Zn1 O3 H3A 109.6 . . ?
Zn1 O3 H3B 109.5 . . ?
H3A O3 H3B 104.3 . . ?
Zn1 O4 H4A 109.4 . . ?
Zn1 O4 H4B 109.4 . . ?
H4A O4 H4B 104.5 . . ?
H5A O5 H5B 104.5 . . ?
C7 N1 Zn1 116.6(3) . . ?
C7 N1 C11 118.1(4) . . ?
C11 N1 Zn1 123.5(3) . . ?
N3 N2 C4 109.3(3) . . ?
N3 N2 C7 117.5(3) . . ?
C4 N2 C7 132.8(4) . . ?
N2 N3 Zn1 114.0(3) . . ?
C6 N3 Zn1 137.2(3) . . ?
C6 N3 N2 108.5(4) . . ?
C5 N4 C1 119.5(4) . . ?
N4 C1 H1 117.9 . . ?
N4 C1 C2 124.2(4) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.2(4) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 C6 136.0(4) . . ?
C4 C3 C6 105.0(4) . . ?
N2 C4 C3 106.6(4) . . ?
N2 C4 C5 133.7(4) . . ?
C5 C4 C3 119.7(4) . . ?
N4 C5 C4 120.4(4) . . ?
N4 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N3 C6 C3 110.5(4) . . ?
N3 C6 H6 124.7 . . ?
C3 C6 H6 124.7 . . ?
N1 C7 N2 114.6(4) . . ?
N1 C7 C8 123.6(4) . . ?
C8 C7 N2 121.8(4) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.5(4) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(4) . . ?
C11 C10 H10 120.8 . . ?
N1 C11 C10 122.2(4) . . ?
N1 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
O6 N5 O7 119.8(4) . . ?
O6 N5 O8 120.7(4) . . ?
O7 N5 O8 119.5(4) . . ?
O10 N6 O9 119.9(4) . . ?
O10 N6 O11 120.6(4) . . ?
O11 N6 O9 119.5(4) . . ?

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
Zn1 N1 C7 N2 16.4(5) . . . . ?
Zn1 N1 C7 C8 -162.4(4) . . . . ?
Zn1 N1 C11 C10 163.1(4) . . . . ?
Zn1 N3 C6 C3 173.3(3) . . . . ?
N1 C7 C8 C9 -2.8(7) . . . . ?
N2 N3 C6 C3 0.4(5) . . . . ?
N2 C4 C5 N4 179.4(4) . . . . ?
N2 C7 C8 C9 178.5(4) . . . . ?
N3 N2 C4 C3 0.9(5) . . . . ?
N3 N2 C4 C5 -178.2(5) . . . . ?
N3 N2 C7 N1 -9.7(6) . . . . ?
N3 N2 C7 C8 169.1(4) . . . . ?
N4 C1 C2 C3 -1.0(7) . . . . ?
C1 N4 C5 C4 -0.1(7) . . . . ?
C1 C2 C3 C4 1.3(7) . . . . ?
C1 C2 C3 C6 -178.2(5) . . . . ?
C2 C3 C4 N2 179.7(4) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C2 C3 C6 N3 179.7(5) . . . . ?
C3 C4 C5 N4 0.5(7) . . . . ?
C4 N2 N3 Zn1 -175.5(3) . . . . ?
C4 N2 N3 C6 -0.8(5) . . . . ?
C4 N2 C7 N1 162.5(4) . . . . ?
C4 N2 C7 C8 -18.6(7) . . . . ?
C4 C3 C6 N3 0.1(5) . . . . ?
C5 N4 C1 C2 0.4(7) . . . . ?
C6 C3 C4 N2 -0.6(5) . . . . ?
C6 C3 C4 C5 178.6(4) . . . . ?
C7 N1 C11 C10 -1.1(7) . . . . ?
C7 N2 N3 Zn1 -1.5(5) . . . . ?
C7 N2 N3 C6 173.2(4) . . . . ?
C7 N2 C4 C3 -171.9(4) . . . . ?
C7 N2 C4 C5 9.1(8) . . . . ?
C7 C8 C9 C10 0.8(8) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C9 C10 C11 N1 -0.7(8) . . . . ?
C11 N1 C7 N2 -178.3(4) . . . . ?
C11 N1 C7 C8 2.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2121415'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N12 O12 Zn2, 1.5(C4 H6 N2)'
_chemical_formula_sum            'C28 H25 N15 O12 Zn2'
_chemical_formula_weight         894.37
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_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                   26.481(2)
_cell_length_b                   9.7011(9)
_cell_length_c                   16.5236(15)
_cell_angle_alpha                90
_cell_angle_beta                 124.005(2)
_cell_angle_gamma                90
_cell_volume                     3518.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5124
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    1.448
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0775 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8956.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25275
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         2.974
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2665
_reflns_number_total             3615
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+7.9949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.83653(2) 0.18348(5) 0.89213(4) 0.01979(16) Uani 1 1 d . . . . .
O1 O 0.94105(15) 0.1493(3) 1.0279(2) 0.0325(8) Uani 1 1 d . . . . .
O2 O 0.88324(13) 0.3206(3) 1.0068(2) 0.0291(7) Uani 1 1 d . . . . .
O3 O 0.97578(17) 0.3144(4) 1.1342(3) 0.0542(11) Uani 1 1 d . . . . .
N1 N 0.81332(15) 0.0464(3) 0.9727(2) 0.0203(8) Uani 1 1 d . . . . .
N2 N 0.72246(15) 0.1667(3) 0.8880(2) 0.0168(7) Uani 1 1 d . . . . .
N3 N 0.74734(15) 0.2420(3) 0.8489(2) 0.0181(7) Uani 1 1 d . . . . .
N4 N 0.65562(15) 0.5149(3) 0.6773(2) 0.0186(7) Uani 1 1 d . . . . .
N5 N 0.93492(18) 0.2616(4) 1.0586(3) 0.0295(9) Uani 1 1 d . . . . .
C1 C 0.60322(19) 0.4915(4) 0.6747(3) 0.0238(9) Uani 1 1 d . . . . .
H1 H 0.568613 0.547306 0.632854 0.029 Uiso 1 1 calc R U . . .
C2 C 0.59847(19) 0.3932(4) 0.7286(3) 0.0230(9) Uani 1 1 d . . . . .
H2 H 0.562046 0.381191 0.726152 0.028 Uiso 1 1 calc R U . . .
C3 C 0.64985(18) 0.3100(4) 0.7880(3) 0.0182(8) Uani 1 1 d . . . . .
C4 C 0.70286(18) 0.3310(4) 0.7885(3) 0.0177(8) Uani 1 1 d . . . . .
C5 C 0.70415(18) 0.4371(4) 0.7318(3) 0.0193(9) Uani 1 1 d . . . . .
H5 H 0.739909 0.452776 0.732859 0.023 Uiso 1 1 calc R U . . .
C6 C 0.66533(19) 0.2021(4) 0.8543(3) 0.0207(9) Uani 1 1 d . . . . .
H6 H 0.640012 0.161935 0.871805 0.025 Uiso 1 1 calc R U . . .
C7 C 0.75912(19) 0.0614(4) 0.9576(3) 0.0193(9) Uani 1 1 d . . . . .
C8 C 0.7380(2) -0.0145(4) 1.0034(3) 0.0228(9) Uani 1 1 d . . . . .
H8 H 0.698447 -0.000317 0.989766 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7773(2) -0.1125(4) 1.0704(3) 0.0236(9) Uani 1 1 d . . . . .
H9 H 0.765375 -0.166101 1.105074 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8338(2) -0.1317(4) 1.0864(3) 0.0262(10) Uani 1 1 d . . . . .
H10 H 0.860763 -0.200117 1.130837 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8506(2) -0.0497(4) 1.0366(3) 0.0271(10) Uani 1 1 d . . . . .
H11 H 0.889669 -0.062004 1.048193 0.032 Uiso 1 1 calc R U . . .
O4 O 0.82324(14) 0.3114(3) 0.7820(2) 0.0282(7) Uani 1 1 d . . . . .
O5 O 0.86521(15) 0.4282(4) 0.7236(2) 0.0390(9) Uani 1 1 d . . . . .
O6 O 0.92085(15) 0.3232(4) 0.8620(2) 0.0419(9) Uani 1 1 d . . . . .
N6 N 0.87071(16) 0.3558(3) 0.7893(3) 0.0213(8) Uani 1 1 d . . . . .
N7 N 0.500000 -0.3674(10) 0.750000 0.093(3) Uani 1 2 d S T P . .
C12 C 0.500000 -0.2541(10) 0.750000 0.054(2) Uani 1 2 d S T P . .
C13 C 0.500000 -0.1045(9) 0.750000 0.085(4) Uani 1 2 d S T P . .
H13A H 0.463508 -0.070847 0.689431 0.127 Uiso 0.5 1 calc R U P A -1
H13B H 0.536407 -0.070846 0.754575 0.127 Uiso 0.5 1 calc R U P A -1
H13C H 0.500085 -0.070846 0.805993 0.127 Uiso 0.5 1 calc R U P A -1
N8 N 0.6718(2) 0.1389(6) 0.6100(4) 0.0640(16) Uani 1 1 d . . . . .
C14 C 0.6207(2) 0.1401(5) 0.5735(4) 0.0335(11) Uani 1 1 d . . . . .
C15 C 0.5567(3) 0.1407(7) 0.5299(6) 0.070(2) Uani 1 1 d . . . . .
H15A H 0.548625 0.124094 0.580161 0.105 Uiso 1 1 calc R U . . .
H15B H 0.537611 0.068008 0.480391 0.105 Uiso 1 1 calc R U . . .
H15C H 0.539926 0.230402 0.499214 0.105 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 2.420(3) . ?
Zn1 O2 2.066(3) . ?
Zn1 N1 2.198(3) . ?
Zn1 N3 2.127(3) . ?
Zn1 N4 2.074(3) 4_646 ?
Zn1 O4 2.063(3) . ?
O1 N5 1.250(5) . ?
O2 N5 1.274(5) . ?
O3 N5 1.217(5) . ?
N1 C7 1.321(5) . ?
N1 C11 1.339(5) . ?
N2 N3 1.364(4) . ?
N2 C6 1.332(5) . ?
N2 C7 1.436(5) . ?
N3 C4 1.347(5) . ?
N4 C1 1.383(5) . ?
N4 C5 1.318(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.358(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(6) . ?
C3 C4 1.415(6) . ?
C3 C6 1.400(5) . ?
C4 C5 1.404(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.378(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(6) . ?
C11 H11 0.9500 . ?
O4 N6 1.270(5) . ?
O5 N6 1.231(5) . ?
O6 N6 1.233(5) . ?
N7 C12 1.099(12) . ?
C12 C13 1.451(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N8 C14 1.132(7) . ?
C14 C15 1.422(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O2 Zn1 O1 56.66(11) . . ?
O2 Zn1 N1 93.48(12) . . ?
O2 Zn1 N3 96.84(12) . . ?
O2 Zn1 N4 145.22(13) . 4_646 ?
N1 Zn1 O1 85.30(12) . . ?
N3 Zn1 O1 145.84(12) . . ?
N3 Zn1 N1 74.38(12) . . ?
N4 Zn1 O1 89.33(12) 4_646 . ?
N4 Zn1 N1 90.35(13) 4_646 . ?
N4 Zn1 N3 117.41(13) 4_646 . ?
O4 Zn1 O1 116.26(12) . . ?
O4 Zn1 O2 98.11(13) . . ?
O4 Zn1 N1 158.44(13) . . ?
O4 Zn1 N3 86.18(12) . . ?
O4 Zn1 N4 90.41(13) . 4_646 ?
N5 O1 Zn1 85.2(2) . . ?
N5 O2 Zn1 101.2(3) . . ?
C7 N1 Zn1 117.5(3) . . ?
C7 N1 C11 117.9(4) . . ?
C11 N1 Zn1 124.6(3) . . ?
N3 N2 C7 118.1(3) . . ?
C6 N2 N3 113.6(3) . . ?
C6 N2 C7 128.2(3) . . ?
N2 N3 Zn1 116.0(2) . . ?
C4 N3 Zn1 140.1(3) . . ?
C4 N3 N2 103.9(3) . . ?
C1 N4 Zn1 121.4(3) . 4_656 ?
C5 N4 Zn1 118.0(3) . 4_656 ?
C5 N4 C1 120.3(4) . . ?
O1 N5 O2 117.0(4) . . ?
O3 N5 O1 122.7(4) . . ?
O3 N5 O2 120.3(4) . . ?
N4 C1 H1 118.2 . . ?
C2 C1 N4 123.7(4) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 117.0(4) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 C4 119.4(4) . . ?
C6 C3 C2 136.2(4) . . ?
C6 C3 C4 104.3(3) . . ?
N3 C4 C3 111.5(3) . . ?
N3 C4 C5 128.8(4) . . ?
C5 C4 C3 119.7(4) . . ?
N4 C5 C4 119.8(4) . . ?
N4 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N2 C6 C3 106.7(3) . . ?
N2 C6 H6 126.7 . . ?
C3 C6 H6 126.7 . . ?
N1 C7 N2 113.9(3) . . ?
N1 C7 C8 124.8(4) . . ?
C8 C7 N2 121.3(4) . . ?
C7 C8 H8 121.6 . . ?
C7 C8 C9 116.7(4) . . ?
C9 C8 H8 121.6 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.8(4) . . ?
C11 C10 H10 120.6 . . ?
N1 C11 C10 122.0(4) . . ?
N1 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
N6 O4 Zn1 116.7(3) . . ?
O5 N6 O4 119.2(4) . . ?
O5 N6 O6 122.5(4) . . ?
O6 N6 O4 118.3(3) . . ?
N7 C12 C13 180.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N8 C14 C15 178.6(7) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 N5 O2 0.4(3) . . . . ?
Zn1 O1 N5 O3 -179.5(4) . . . . ?
Zn1 O2 N5 O1 -0.5(4) . . . . ?
Zn1 O2 N5 O3 179.4(4) . . . . ?
Zn1 N1 C7 N2 0.8(4) . . . . ?
Zn1 N1 C7 C8 -178.9(3) . . . . ?
Zn1 N1 C11 C10 179.0(3) . . . . ?
Zn1 N3 C4 C3 175.2(3) . . . . ?
Zn1 N3 C4 C5 -6.5(7) . . . . ?
Zn1 N4 C1 C2 -171.5(3) 4_656 . . . ?
Zn1 N4 C5 C4 173.1(3) 4_656 . . . ?
Zn1 O4 N6 O5 177.3(3) . . . . ?
Zn1 O4 N6 O6 -2.0(5) . . . . ?
N1 C7 C8 C9 0.5(6) . . . . ?
N2 N3 C4 C3 -1.2(4) . . . . ?
N2 N3 C4 C5 177.1(4) . . . . ?
N2 C7 C8 C9 -179.2(4) . . . . ?
N3 N2 C6 C3 -0.6(4) . . . . ?
N3 N2 C7 N1 -2.7(5) . . . . ?
N3 N2 C7 C8 177.0(3) . . . . ?
N3 C4 C5 N4 -179.5(4) . . . . ?
N4 C1 C2 C3 -1.4(6) . . . . ?
C1 N4 C5 C4 -0.7(6) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C1 C2 C3 C6 178.7(4) . . . . ?
C2 C3 C4 N3 -179.6(4) . . . . ?
C2 C3 C4 C5 1.9(6) . . . . ?
C2 C3 C6 N2 -179.6(5) . . . . ?
C3 C4 C5 N4 -1.2(6) . . . . ?
C4 C3 C6 N2 -0.2(4) . . . . ?
C5 N4 C1 C2 2.2(6) . . . . ?
C6 N2 N3 Zn1 -176.3(3) . . . . ?
C6 N2 N3 C4 1.1(4) . . . . ?
C6 N2 C7 N1 176.8(4) . . . . ?
C6 N2 C7 C8 -3.5(6) . . . . ?
C6 C3 C4 N3 0.9(4) . . . . ?
C6 C3 C4 C5 -177.6(4) . . . . ?
C7 N1 C11 C10 -0.2(6) . . . . ?
C7 N2 N3 Zn1 3.2(4) . . . . ?
C7 N2 N3 C4 -179.4(3) . . . . ?
C7 N2 C6 C3 180.0(4) . . . . ?
C7 C8 C9 C10 -1.4(6) . . . . ?
C8 C9 C10 C11 1.6(6) . . . . ?
C9 C10 C11 N1 -0.8(7) . . . . ?
C11 N1 C7 N2 -180.0(3) . . . . ?
C11 N1 C7 C8 0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2121409'
loop_
_audit_author_name
_audit_author_address
'Chris Hawes'
;Keele University
United Kingdom
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-10-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 N6 O4 Zn2'
_chemical_formula_sum            'C26 H16 N6 O4 Zn2'
_chemical_formula_weight         607.19
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_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                   35.314(4)
_cell_length_b                   9.6459(10)
_cell_length_c                   11.2289(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.392(3)
_cell_angle_gamma                90
_cell_volume                     3735.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0744 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.8904.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1180
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18019
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         3.104
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2715
_reflns_number_total             3827
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C9A)
\\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: C9(0.6667) H9(0.6667) C10(0.6667) H10(0.6667) C12(0.6667)
 H12(0.6667) C13(0.6667) H13(0.6667) C9A(0.3333) H9A(0.3333) C10A(0.3333)
 H10A(0.3333) C12A(0.3333) H12A(0.3333) C13A(0.3333) H13A(0.3333)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C9A(H9A), C10A(H10A), C12A(H12A), C13A(H13A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zn01 Zn 0.71266(2) 0.37002(5) 0.51857(4) 0.01609(15) Uani 1 1 d . . . . .
O1 O 0.66158(8) 0.3839(3) 0.5494(3) 0.0306(8) Uani 1 1 d . . . . .
O2 O 0.65177(9) 0.5199(4) 0.3904(3) 0.0432(10) Uani 1 1 d . . . . .
N1 N 0.72880(9) 0.3387(3) 0.3615(3) 0.0141(7) Uani 1 1 d . . . . .
N2 N 0.76296(9) 0.2709(3) 0.3569(3) 0.0150(7) Uani 1 1 d . . . . .
N3 N 0.74574(9) 0.4563(3) 0.0781(3) 0.0160(7) Uani 1 1 d . . . . .
C1 C 0.77516(12) 0.4155(4) 0.0310(4) 0.0209(9) Uani 1 1 d . . . . .
H1 H 0.777294 0.453198 -0.045439 0.025 Uiso 1 1 calc R U . . .
C2 C 0.80335(12) 0.3201(5) 0.0867(4) 0.0248(10) Uani 1 1 d . . . . .
H2 H 0.823066 0.292270 0.045995 0.030 Uiso 1 1 calc R U . . .
C3 C 0.80278(12) 0.2671(4) 0.1985(4) 0.0214(9) Uani 1 1 d . . . . .
H3 H 0.822478 0.206106 0.239298 0.026 Uiso 1 1 calc R U . . .
C4 C 0.77188(11) 0.3064(4) 0.2504(4) 0.0150(8) Uani 1 1 d . . . . .
C5 C 0.74413(11) 0.3985(4) 0.1872(3) 0.0134(8) Uani 1 1 d . . . . .
C6 C 0.71744(11) 0.4157(4) 0.2620(3) 0.0146(8) Uani 1 1 d . . . . .
H6 H 0.695005 0.472843 0.244681 0.018 Uiso 1 1 calc R U . . .
C7 C 0.63996(11) 0.4611(4) 0.4712(4) 0.0193(9) Uani 1 1 d . . . . .
C8 C 0.59851(12) 0.4744(5) 0.4811(4) 0.0255(10) Uani 1 1 d . U . . .
C11 C 0.52110(12) 0.4971(6) 0.4982(5) 0.0363(12) Uani 1 1 d . U . . .
C9 C 0.5834(3) 0.3856(10) 0.5572(10) 0.034(2) Uani 0.6667 1 d . U P A -2
H9 H 0.599264 0.316269 0.602902 0.041 Uiso 0.6667 1 calc R U P A -2
C10 C 0.5456(3) 0.3990(9) 0.5655(9) 0.032(2) Uani 0.6667 1 d . U P A -2
H10 H 0.535758 0.339418 0.618999 0.038 Uiso 0.6667 1 calc R U P A -2
C12 C 0.5369(2) 0.5915(9) 0.4292(8) 0.0286(18) Uani 0.6667 1 d . U P A -2
H12 H 0.521656 0.666260 0.390016 0.034 Uiso 0.6667 1 calc R U P A -2
C13 C 0.5750(2) 0.5763(8) 0.4176(7) 0.0260(16) Uani 0.6667 1 d . U P A -2
H13 H 0.585066 0.636799 0.365255 0.031 Uiso 0.6667 1 calc R U P A -2
C9A C 0.5861(6) 0.4368(18) 0.5845(18) 0.024(4) Uani 0.3333 1 d . U P A -1
H9A H 0.604001 0.396450 0.650763 0.029 Uiso 0.3333 1 calc R U P A -1
C10A C 0.5478(5) 0.457(2) 0.5938(18) 0.029(4) Uani 0.3333 1 d . U P A -1
H10A H 0.540665 0.441068 0.669635 0.035 Uiso 0.3333 1 calc R U P A -1
C12A C 0.5328(5) 0.521(2) 0.3879(16) 0.038(4) Uani 0.3333 1 d . U P A -1
H12A H 0.514018 0.548528 0.318083 0.046 Uiso 0.3333 1 calc R U P A -1
C13A C 0.5715(5) 0.504(2) 0.3783(17) 0.044(5) Uani 0.3333 1 d . U P A -1
H13A H 0.578627 0.513553 0.301838 0.053 Uiso 0.3333 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn01 O1 1.913(3) . ?
Zn01 N1 1.990(3) . ?
Zn01 N2 2.007(3) 7_656 ?
Zn01 N3 2.069(3) 6_566 ?
O1 C7 1.273(5) . ?
O2 C7 1.218(5) . ?
N1 N2 1.383(4) . ?
N1 C6 1.330(5) . ?
N2 C4 1.345(5) . ?
N3 C1 1.323(5) . ?
N3 C5 1.358(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.400(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.360(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(5) . ?
C4 C5 1.398(5) . ?
C5 C6 1.401(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.497(5) . ?
C8 C9 1.394(12) . ?
C8 C13 1.382(8) . ?
C8 C9A 1.37(2) . ?
C8 C13A 1.362(18) . ?
C11 C11 1.501(8) 5_666 ?
C11 C10 1.392(10) . ?
C11 C12 1.387(9) . ?
C11 C10A 1.33(2) . ?
C11 C12A 1.406(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.361(15) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.387(10) . ?
C13 H13 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C10A 1.39(3) . ?
C10A H10A 0.9500 . ?
C12A H12A 0.9500 . ?
C12A C13A 1.40(2) . ?
C13A H13A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn01 N1 129.16(13) . . ?
O1 Zn01 N2 101.62(13) . 7_656 ?
O1 Zn01 N3 111.95(13) . 6_566 ?
N1 Zn01 N2 110.68(12) . 7_656 ?
N1 Zn01 N3 99.23(12) . 6_566 ?
N2 Zn01 N3 101.25(13) 7_656 6_566 ?
C7 O1 Zn01 111.4(2) . . ?
N2 N1 Zn01 121.5(2) . . ?
C6 N1 Zn01 124.6(3) . . ?
C6 N1 N2 110.0(3) . . ?
N1 N2 Zn01 122.8(2) . 7_656 ?
C4 N2 Zn01 130.2(3) . 7_656 ?
C4 N2 N1 106.6(3) . . ?
C1 N3 Zn01 123.3(3) . 6_565 ?
C1 N3 C5 115.3(3) . . ?
C5 N3 Zn01 119.6(2) . 6_565 ?
N3 C1 H1 117.9 . . ?
N3 C1 C2 124.1(4) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 121.6 . . ?
C2 C3 C4 116.8(4) . . ?
C4 C3 H3 121.6 . . ?
N2 C4 C3 131.0(4) . . ?
N2 C4 C5 109.9(3) . . ?
C3 C4 C5 119.1(4) . . ?
N3 C5 C4 123.9(3) . . ?
N3 C5 C6 131.0(4) . . ?
C4 C5 C6 105.0(3) . . ?
N1 C6 C5 108.5(3) . . ?
N1 C6 H6 125.8 . . ?
C5 C6 H6 125.8 . . ?
O1 C7 C8 116.8(3) . . ?
O2 C7 O1 122.4(4) . . ?
O2 C7 C8 120.8(4) . . ?
C9 C8 C7 120.2(6) . . ?
C13 C8 C7 120.7(4) . . ?
C13 C8 C9 119.1(6) . . ?
C9A C8 C7 122.3(9) . . ?
C13A C8 C7 118.3(8) . . ?
C13A C8 C9A 118.6(12) . . ?
C10 C11 C11 121.1(6) . 5_666 ?
C12 C11 C11 120.8(6) . 5_666 ?
C12 C11 C10 118.1(6) . . ?
C10A C11 C11 121.7(10) . 5_666 ?
C10A C11 C12A 118.0(11) . . ?
C12A C11 C11 119.9(8) . 5_666 ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(9) . . ?
C10 C9 H9 120.2 . . ?
C11 C10 H10 119.0 . . ?
C9 C10 C11 122.1(8) . . ?
C9 C10 H10 119.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(6) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 120.9(6) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C8 C9A H9A 119.4 . . ?
C8 C9A C10A 121.2(17) . . ?
C10A C9A H9A 119.4 . . ?
C11 C10A C9A 120.8(17) . . ?
C11 C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C11 C12A H12A 119.2 . . ?
C13A C12A C11 121.6(14) . . ?
C13A C12A H12A 119.2 . . ?
C8 C13A C12A 118.4(15) . . ?
C8 C13A H13A 120.8 . . ?
C12A C13A H13A 120.8 . . ?

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
Zn01 O1 C7 O2 -1.9(6) . . . . ?
Zn01 O1 C7 C8 176.8(3) . . . . ?
Zn01 N1 N2 Zn01 27.4(4) . . . 7_656 ?
Zn01 N1 N2 C4 -159.8(3) . . . . ?
Zn01 N1 C6 C5 158.7(3) . . . . ?
Zn01 N2 C4 C3 -7.0(7) 7_656 . . . ?
Zn01 N2 C4 C5 173.1(3) 7_656 . . . ?
Zn01 N3 C1 C2 164.2(3) 6_565 . . . ?
Zn01 N3 C5 C4 -162.6(3) 6_565 . . . ?
Zn01 N3 C5 C6 15.6(6) 6_565 . . . ?
O1 C7 C8 C9 -11.8(8) . . . . ?
O1 C7 C8 C13 166.7(5) . . . . ?
O1 C7 C8 C9A 16.3(11) . . . . ?
O1 C7 C8 C13A -153.3(10) . . . . ?
O2 C7 C8 C9 166.9(6) . . . . ?
O2 C7 C8 C13 -14.6(8) . . . . ?
O2 C7 C8 C9A -165.0(9) . . . . ?
O2 C7 C8 C13A 25.4(12) . . . . ?
N1 N2 C4 C3 -179.1(4) . . . . ?
N1 N2 C4 C5 1.1(4) . . . . ?
N2 N1 C6 C5 0.9(4) . . . . ?
N2 C4 C5 N3 178.0(4) . . . . ?
N2 C4 C5 C6 -0.6(4) . . . . ?
N3 C1 C2 C3 -2.8(7) . . . . ?
N3 C5 C6 N1 -178.6(4) . . . . ?
C1 N3 C5 C4 2.5(6) . . . . ?
C1 N3 C5 C6 -179.3(4) . . . . ?
C1 C2 C3 C4 3.4(7) . . . . ?
C2 C3 C4 N2 179.0(4) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 N3 -1.8(6) . . . . ?
C3 C4 C5 C6 179.6(4) . . . . ?
C4 C5 C6 N1 -0.2(4) . . . . ?
C5 N3 C1 C2 -0.2(6) . . . . ?
C6 N1 N2 Zn01 -174.0(3) . . . 7_656 ?
C6 N1 N2 C4 -1.2(4) . . . . ?
C7 C8 C9 C10 179.9(7) . . . . ?
C7 C8 C13 C12 -178.2(7) . . . . ?
C7 C8 C9A C10A 176.7(12) . . . . ?
C7 C8 C13A C12A -178.2(13) . . . . ?
C8 C9 C10 C11 1.4(15) . . . . ?
C8 C9A C10A C11 8(3) . . . . ?
C11 C11 C10 C9 175.4(8) 5_666 . . . ?
C11 C11 C12 C13 -173.8(8) 5_666 . . . ?
C11 C11 C10A C9A 172.6(13) 5_666 . . . ?
C11 C11 C12A C13A -174.2(15) 5_666 . . . ?
C11 C12 C13 C8 -4.8(13) . . . . ?
C11 C12A C13A C8 -5(3) . . . . ?
C9 C8 C13 C12 0.4(11) . . . . ?
C10 C11 C12 C13 7.4(12) . . . . ?
C12 C11 C10 C9 -5.8(13) . . . . ?
C13 C8 C9 C10 1.4(12) . . . . ?
C9A C8 C13A C12A 12(2) . . . . ?
C10A C11 C12A C13A -1(2) . . . . ?
C12A C11 C10A C9A -1(2) . . . . ?
C13A C8 C9A C10A -14(2) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 292 electrons were 
found in a volume of 1670Å³ in 1 void per unit cell. 
This is consistent with the presence of 
1[1.5DMF+3H2O] per Formula Unit 
which account for 360 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.805 834.8 146.4 '2 1.5DMF+3H2O'
2 0.500 0.000 -0.290 834.8 146.4 '2 1.5DMF+3H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
