# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_rwg2022jun_p157_189m
_database_code_depnum_ccdc_archive 'CCDC 2223411'
loop_
_audit_author_name
_audit_author_address
'Gable Robert W.'
;University of Melbourne
Australia
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-07-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
robertwg@unimelb.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H18 Cl N4 Zn), Cl4 Zn'
_chemical_formula_sum            'C12 H36 Cl6 N8 Zn3'
_chemical_formula_weight         701.30
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.0201(16)
_cell_length_b                   16.781(3)
_cell_length_c                   19.809(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.86(3)
_cell_angle_gamma                90
_cell_volume                     2652.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.313
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   
;
XDS does not report the values of _exptl_absorpt_correction_T_min and
_exptl_absorpt_correction_T_max.  Even though the data was processed by XDS
the values of the absorption corrections reported by SADABS are reported.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needles
_exptl_crystal_F_000             1424
_exptl_crystal_recrystallization_method 
'grown by slow evaporation from methanol'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            91824
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.249
_diffrn_reflns_theta_max         32.179
_diffrn_reflns_theta_min         1.594
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 13.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_detector_type 'Dectris Eiger 16M'
_diffrn_measurement_device_type  'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71092
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8165
_reflns_number_total             8417
_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       'XDS (Kabsch, 2010)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.822
_refine_diff_density_min         -1.224
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         8417
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.057
_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)+(0.0437P)²+1.4249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Zn3) = Uanis(Zn3A)
Uanis(Cl3) = Uanis(Cl3A)
Uanis(Cl4) = Uanis(Cl4A)
Uanis(Cl5) = Uanis(Cl5A)
Uanis(Cl6) = Uanis(Cl6A)
3. Same fragment restrains
{Zn3, Cl3, Cl4, Cl5, Cl6} sigma for 1-2: 0.02, 1-3: 0.04
as in
{Zn3A, Cl3A, Cl4A, Cl5A, Cl6A}
4. Others
 Sof(Zn3A)=Sof(Cl3A)=Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=1-FVAR(1)
 Sof(Zn3)=Sof(Cl3)=Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C1(H1A,H1B), C2(H2C,H2D), C3(H3C,H3D),
 C4(H4C,H4D), C5(H5A,H5B), C6(H6A,H6B), N6(H6C,H6D), N7(H7A,H7B), N8(H8A,H8B),
 C7(H7C,H7D), C8(H8C,H8D), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
;
_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 0.52794(2) 0.46146(2) 0.62528(2) 0.01911(5) Uani 1 1 d . . . . .
Cl1 Cl 0.51043(4) 0.35018(2) 0.54809(2) 0.02383(7) Uani 1 1 d . . . . .
N1 N 0.54291(14) 0.57581(7) 0.68843(6) 0.0198(2) Uani 1 1 d . . . . .
N2 N 0.27804(15) 0.48836(8) 0.62092(6) 0.0247(2) Uani 1 1 d . . . . .
H2A H 0.226370 0.473313 0.581058 0.030 Uiso 1 1 calc R U . . .
H2B H 0.231829 0.462412 0.653493 0.030 Uiso 1 1 calc R U . . .
N3 N 0.62645(17) 0.41428(8) 0.71747(6) 0.0254(2) Uani 1 1 d . . . . .
H3A H 0.582472 0.366406 0.723418 0.030 Uiso 1 1 calc R U . . .
H3B H 0.737005 0.408915 0.718120 0.030 Uiso 1 1 calc R U . . .
N4 N 0.69097(15) 0.52576(8) 0.57248(6) 0.0226(2) Uani 1 1 d . . . . .
H4A H 0.768933 0.493447 0.558862 0.027 Uiso 1 1 calc R U . . .
H4B H 0.635317 0.547478 0.535861 0.027 Uiso 1 1 calc R U . . .
C1 C 0.36891(18) 0.60135(10) 0.69282(8) 0.0248(3) Uani 1 1 d . . . . .
H1A H 0.364796 0.658877 0.697100 0.030 Uiso 1 1 calc R U . . .
H1B H 0.327604 0.578092 0.732736 0.030 Uiso 1 1 calc R U . . .
C2 C 0.25869(18) 0.57532(10) 0.62978(8) 0.0275(3) Uani 1 1 d . . . . .
H2C H 0.142482 0.587970 0.634575 0.033 Uiso 1 1 calc R U . . .
H2D H 0.291368 0.603258 0.590332 0.033 Uiso 1 1 calc R U . . .
C3 C 0.62872(18) 0.55414(9) 0.75487(7) 0.0241(3) Uani 1 1 d . . . . .
H3C H 0.594401 0.590019 0.789267 0.029 Uiso 1 1 calc R U . . .
H3D H 0.748892 0.559401 0.753893 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5865(2) 0.46888(10) 0.77264(7) 0.0275(3) Uani 1 1 d . . . . .
H4C H 0.650529 0.453655 0.814870 0.033 Uiso 1 1 calc R U . . .
H4D H 0.468325 0.464936 0.778777 0.033 Uiso 1 1 calc R U . . .
C5 C 0.63853(18) 0.63289(9) 0.65095(8) 0.0238(3) Uani 1 1 d . . . . .
H5A H 0.690905 0.672296 0.682070 0.029 Uiso 1 1 calc R U . . .
H5B H 0.563270 0.660387 0.617235 0.029 Uiso 1 1 calc R U . . .
C6 C 0.77189(18) 0.58926(9) 0.61636(8) 0.0246(3) Uani 1 1 d . . . . .
H6A H 0.829613 0.626283 0.589188 0.029 Uiso 1 1 calc R U . . .
H6B H 0.853597 0.566001 0.650182 0.029 Uiso 1 1 calc R U . . .
Zn2 Zn -0.05203(2) 0.26226(2) 0.54148(2) 0.02027(5) Uani 1 1 d . . . . .
Cl2 Cl -0.01747(4) 0.39737(2) 0.52168(2) 0.02160(7) Uani 1 1 d . . . . .
N5 N -0.0985(2) 0.13056(9) 0.57001(8) 0.0334(3) Uani 1 1 d . . . . .
N6 N 0.18590(17) 0.21818(9) 0.53772(8) 0.0307(3) Uani 1 1 d . . . . .
H6C H 0.202363 0.207404 0.494909 0.037 Uiso 1 1 calc R U . . .
H6D H 0.260779 0.254570 0.553411 0.037 Uiso 1 1 calc R U . . .
N7 N -0.22191(18) 0.22890(8) 0.46099(7) 0.0285(3) Uani 1 1 d . . . . .
H7A H -0.322772 0.247696 0.467529 0.034 Uiso 1 1 calc R U . . .
H7B H -0.191926 0.250413 0.422976 0.034 Uiso 1 1 calc R U . . .
N8 N -0.1443(2) 0.27694(9) 0.63400(7) 0.0350(3) Uani 1 1 d . . . . .
H8A H -0.059387 0.285201 0.665805 0.042 Uiso 1 1 calc R U . . .
H8B H -0.210126 0.319733 0.632383 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0604(2) 0.08935(10) 0.56198(10) 0.0361(4) Uani 1 1 d . . . . .
H7C H 0.060013 0.070806 0.515585 0.043 Uiso 1 1 calc R U . . .
H7D H 0.071247 0.043270 0.591670 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2088(3) 0.14486(11) 0.57905(10) 0.0381(4) Uani 1 1 d . . . . .
H8C H 0.217494 0.158445 0.626874 0.046 Uiso 1 1 calc R U . . .
H8D H 0.311534 0.118347 0.569886 0.046 Uiso 1 1 calc R U . . .
C9 C -0.2386(2) 0.10295(11) 0.52170(13) 0.0421(4) Uani 1 1 d . . . . .
H9A H -0.344078 0.116208 0.538935 0.051 Uiso 1 1 calc R U . . .
H9B H -0.233094 0.045472 0.517178 0.051 Uiso 1 1 calc R U . . .
C10 C -0.2315(2) 0.14121(11) 0.45308(11) 0.0373(4) Uani 1 1 d . . . . .
H10A H -0.134081 0.122020 0.432758 0.045 Uiso 1 1 calc R U . . .
H10B H -0.330784 0.127053 0.423362 0.045 Uiso 1 1 calc R U . . .
C11 C -0.1411(4) 0.13165(13) 0.64033(12) 0.0526(6) Uani 1 1 d . . . . .
H11A H -0.039335 0.130534 0.671289 0.063 Uiso 1 1 calc R U . . .
H11B H -0.206841 0.084836 0.648784 0.063 Uiso 1 1 calc R U . . .
C12 C -0.2408(3) 0.20646(13) 0.65260(11) 0.0500(6) Uani 1 1 d . . . . .
H12A H -0.348365 0.204908 0.625343 0.060 Uiso 1 1 calc R U . . .
H12B H -0.260895 0.209557 0.699999 0.060 Uiso 1 1 calc R U . . .
Zn3 Zn 0.15333(11) 0.34404(5) 0.79942(5) 0.02268(10) Uani 0.847(5) 1 d D . P A
1
Cl3 Cl 0.0375(2) 0.45839(10) 0.75134(7) 0.02791(18) Uani 0.847(5) 1 d D . P A 1
Cl4 Cl 0.30051(19) 0.29302(10) 0.71668(7) 0.02865(18) Uani 0.847(5) 1 d D . P A
1
Cl5 Cl -0.05583(14) 0.25660(5) 0.81324(9) 0.0390(2) Uani 0.847(5) 1 d D . P A 1
Cl6 Cl 0.30366(18) 0.37259(11) 0.89915(6) 0.0440(2) Uani 0.847(5) 1 d D . P A 1
Zn3A Zn 0.1690(6) 0.3501(3) 0.8082(2) 0.02268(10) Uani 0.153(5) 1 d D . P A 2
Cl3A Cl 0.0319(14) 0.4552(6) 0.7621(5) 0.02791(18) Uani 0.153(5) 1 d D . P A 2
Cl4A Cl 0.3168(12) 0.2939(6) 0.7277(4) 0.02865(18) Uani 0.153(5) 1 d D . P A 2
Cl5A Cl -0.0271(7) 0.2614(3) 0.8353(4) 0.0390(2) Uani 0.153(5) 1 d D . P A 2
Cl6A Cl 0.3250(12) 0.3863(7) 0.9043(4) 0.0440(2) Uani 0.153(5) 1 d D . P A 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 Cl1 2.4085(5) . ?
Zn1 N1 2.2871(13) . ?
Zn1 N2 2.0476(13) . ?
Zn1 N3 2.0716(14) . ?
Zn1 N4 2.0608(13) . ?
N1 C1 1.4708(18) . ?
N1 C3 1.4673(18) . ?
N1 C5 1.4741(19) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C2 1.480(2) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.486(2) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 C6 1.4823(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.519(2) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C3 C4 1.520(2) . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.516(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
Zn2 Cl2 2.3224(6) . ?
Zn2 N5 2.3206(15) . ?
Zn2 N6 2.0550(14) . ?
Zn2 N7 2.0659(15) . ?
Zn2 N8 2.0602(15) . ?
N5 C7 1.473(2) . ?
N5 C9 1.474(3) . ?
N5 C11 1.468(3) . ?
N6 H6C 0.8900 . ?
N6 H6D 0.8900 . ?
N6 C8 1.479(2) . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
N7 C10 1.481(2) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 C12 1.481(3) . ?
C7 H7C 0.9700 . ?
C7 H7D 0.9700 . ?
C7 C8 1.522(3) . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
Zn3 Cl3 2.2959(16) . ?
Zn3 Cl4 2.2821(15) . ?
Zn3 Cl5 2.2662(10) . ?
Zn3 Cl6 2.2582(12) . ?
Zn3A Cl3A 2.224(10) . ?
Zn3A Cl4A 2.285(9) . ?
Zn3A Cl5A 2.269(6) . ?
Zn3A Cl6A 2.253(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 Cl1 173.80(3) . . ?
N2 Zn1 Cl1 98.67(4) . . ?
N2 Zn1 N1 80.48(5) . . ?
N2 Zn1 N3 113.88(6) . . ?
N2 Zn1 N4 122.16(6) . . ?
N3 Zn1 Cl1 104.81(4) . . ?
N3 Zn1 N1 81.05(5) . . ?
N4 Zn1 Cl1 94.74(4) . . ?
N4 Zn1 N1 80.66(5) . . ?
N4 Zn1 N3 116.29(5) . . ?
C1 N1 Zn1 106.24(9) . . ?
C1 N1 C5 112.71(12) . . ?
C3 N1 Zn1 106.04(9) . . ?
C3 N1 C1 112.34(11) . . ?
C3 N1 C5 113.10(11) . . ?
C5 N1 Zn1 105.70(8) . . ?
Zn1 N2 H2A 109.9 . . ?
Zn1 N2 H2B 109.9 . . ?
H2A N2 H2B 108.3 . . ?
C2 N2 Zn1 109.05(9) . . ?
C2 N2 H2A 109.9 . . ?
C2 N2 H2B 109.9 . . ?
Zn1 N3 H3A 109.9 . . ?
Zn1 N3 H3B 109.9 . . ?
H3A N3 H3B 108.3 . . ?
C4 N3 Zn1 108.74(10) . . ?
C4 N3 H3A 109.9 . . ?
C4 N3 H3B 109.9 . . ?
Zn1 N4 H4A 109.7 . . ?
Zn1 N4 H4B 109.7 . . ?
H4A N4 H4B 108.2 . . ?
C6 N4 Zn1 109.95(9) . . ?
C6 N4 H4A 109.7 . . ?
C6 N4 H4B 109.7 . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.10(11) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C2 C1 108.78(12) . . ?
N2 C2 H2C 109.9 . . ?
N2 C2 H2D 109.9 . . ?
C1 C2 H2C 109.9 . . ?
C1 C2 H2D 109.9 . . ?
H2C C2 H2D 108.3 . . ?
N1 C3 H3C 109.6 . . ?
N1 C3 H3D 109.6 . . ?
N1 C3 C4 110.24(12) . . ?
H3C C3 H3D 108.1 . . ?
C4 C3 H3C 109.6 . . ?
C4 C3 H3D 109.6 . . ?
N3 C4 C3 109.88(12) . . ?
N3 C4 H4C 109.7 . . ?
N3 C4 H4D 109.7 . . ?
C3 C4 H4C 109.7 . . ?
C3 C4 H4D 109.7 . . ?
H4C C4 H4D 108.2 . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
N1 C5 C6 109.94(12) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
N4 C6 C5 108.98(11) . . ?
N4 C6 H6A 109.9 . . ?
N4 C6 H6B 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N5 Zn2 Cl2 174.72(4) . . ?
N6 Zn2 Cl2 102.59(4) . . ?
N6 Zn2 N5 80.73(6) . . ?
N6 Zn2 N7 114.59(6) . . ?
N6 Zn2 N8 119.63(7) . . ?
N7 Zn2 Cl2 102.41(4) . . ?
N7 Zn2 N5 79.65(6) . . ?
N8 Zn2 Cl2 95.36(5) . . ?
N8 Zn2 N5 79.40(6) . . ?
N8 Zn2 N7 116.78(7) . . ?
C7 N5 Zn2 104.99(11) . . ?
C7 N5 C9 113.13(15) . . ?
C9 N5 Zn2 105.78(11) . . ?
C11 N5 Zn2 106.14(12) . . ?
C11 N5 C7 113.35(17) . . ?
C11 N5 C9 112.58(19) . . ?
Zn2 N6 H6C 109.7 . . ?
Zn2 N6 H6D 109.7 . . ?
H6C N6 H6D 108.2 . . ?
C8 N6 Zn2 110.03(12) . . ?
C8 N6 H6C 109.7 . . ?
C8 N6 H6D 109.7 . . ?
Zn2 N7 H7A 109.2 . . ?
Zn2 N7 H7B 109.2 . . ?
H7A N7 H7B 107.9 . . ?
C10 N7 Zn2 111.96(11) . . ?
C10 N7 H7A 109.2 . . ?
C10 N7 H7B 109.2 . . ?
Zn2 N8 H8A 109.3 . . ?
Zn2 N8 H8B 109.3 . . ?
H8A N8 H8B 107.9 . . ?
C12 N8 Zn2 111.74(12) . . ?
C12 N8 H8A 109.3 . . ?
C12 N8 H8B 109.3 . . ?
N5 C7 H7C 109.5 . . ?
N5 C7 H7D 109.5 . . ?
N5 C7 C8 110.74(15) . . ?
H7C C7 H7D 108.1 . . ?
C8 C7 H7C 109.5 . . ?
C8 C7 H7D 109.5 . . ?
N6 C8 C7 109.66(14) . . ?
N6 C8 H8C 109.7 . . ?
N6 C8 H8D 109.7 . . ?
C7 C8 H8C 109.7 . . ?
C7 C8 H8D 109.7 . . ?
H8C C8 H8D 108.2 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
N5 C9 C10 110.77(15) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N7 C10 C9 109.50(15) . . ?
N7 C10 H10A 109.8 . . ?
N7 C10 H10B 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
N5 C11 H11A 109.7 . . ?
N5 C11 H11B 109.7 . . ?
N5 C11 C12 109.83(16) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
N8 C12 C11 108.82(18) . . ?
N8 C12 H12A 109.9 . . ?
N8 C12 H12B 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
Cl4 Zn3 Cl3 103.45(6) . . ?
Cl5 Zn3 Cl3 108.55(6) . . ?
Cl5 Zn3 Cl4 106.71(5) . . ?
Cl6 Zn3 Cl3 110.05(7) . . ?
Cl6 Zn3 Cl4 116.03(6) . . ?
Cl6 Zn3 Cl5 111.55(5) . . ?
Cl3A Zn3A Cl4A 108.1(4) . . ?
Cl3A Zn3A Cl5A 107.0(4) . . ?
Cl3A Zn3A Cl6A 110.0(4) . . ?
Cl5A Zn3A Cl4A 108.5(3) . . ?
Cl6A Zn3A Cl4A 114.7(4) . . ?
Cl6A Zn3A Cl5A 108.4(3) . . ?

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
N2 H2A Cl2 0.89 2.52 3.2956(15) 145.6 . yes
N2 H2B Cl3 0.89 2.61 3.416(2) 151.1 . yes
N2 H2B Cl3A 0.89 2.81 3.628(9) 152.5 . yes
N3 H3A Cl4 0.89 2.57 3.311(2) 141.7 . yes
N3 H3A Cl4A 0.89 2.46 3.223(10) 143.8 . yes
N3 H3B Cl3 0.89 2.57 3.379(2) 151.4 1_655 yes
N3 H3B Cl3A 0.89 2.56 3.353(12) 149.3 1_655 yes
N4 H4A Cl2 0.89 2.52 3.4062(14) 177.7 1_655 yes
N4 H4B Cl1 0.89 2.59 3.4438(15) 162.3 3_666 yes
C5 H5A Cl4A 0.97 2.72 3.610(10) 153.2 2_656 yes
C6 H6A Cl2 0.97 2.82 3.5366(18) 131.8 3_666 yes
N6 H6C Cl6 0.89 2.52 3.358(2) 156.1 4_565 yes
N6 H6C Cl6A 0.89 2.65 3.450(9) 150.2 4_565 yes
N6 H6D Cl1 0.89 2.58 3.4079(16) 155.9 . yes
N7 H7A Cl1 0.89 2.78 3.5332(16) 143.2 1_455 yes
N7 H7B Cl5 0.89 2.53 3.346(2) 152.2 4_565 yes
N7 H7B Cl5A 0.89 2.30 3.075(6) 146.2 4_565 yes
N8 H8B Cl1 0.89 2.70 3.3336(19) 128.8 1_455 yes
C10 H10B Cl6A 0.97 2.76 3.618(10) 148.3 4_465 yes
C12 H12B Cl5 0.97 2.76 3.474(3) 131.2 . 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 N1 C1 C2 -30.00(14) . . . . ?
Zn1 N1 C3 C4 -32.66(13) . . . . ?
Zn1 N1 C5 C6 -34.64(13) . . . . ?
Zn1 N2 C2 C1 -51.15(14) . . . . ?
Zn1 N3 C4 C3 -47.70(14) . . . . ?
Zn1 N4 C6 C5 -47.46(14) . . . . ?
N1 C1 C2 N2 54.48(16) . . . . ?
N1 C3 C4 N3 54.85(16) . . . . ?
N1 C5 C6 N4 55.63(16) . . . . ?
C1 N1 C3 C4 82.98(15) . . . . ?
C1 N1 C5 C6 -150.27(12) . . . . ?
C3 N1 C1 C2 -145.51(13) . . . . ?
C3 N1 C5 C6 80.95(14) . . . . ?
C5 N1 C1 C2 85.31(15) . . . . ?
C5 N1 C3 C4 -148.05(12) . . . . ?
Zn2 N5 C7 C8 32.51(17) . . . . ?
Zn2 N5 C9 C10 34.38(16) . . . . ?
Zn2 N5 C11 C12 34.9(3) . . . . ?
Zn2 N6 C8 C7 47.77(17) . . . . ?
Zn2 N7 C10 C9 44.64(18) . . . . ?
Zn2 N8 C12 C11 46.7(2) . . . . ?
N5 C7 C8 N6 -54.6(2) . . . . ?
N5 C9 C10 N7 -53.2(2) . . . . ?
N5 C11 C12 N8 -54.7(3) . . . . ?
C7 N5 C9 C10 -80.01(19) . . . . ?
C7 N5 C11 C12 149.6(2) . . . . ?
C9 N5 C7 C8 147.37(16) . . . . ?
C9 N5 C11 C12 -80.4(2) . . . . ?
C11 N5 C7 C8 -82.9(2) . . . . ?
C11 N5 C9 C10 149.88(16) . . . . ?

_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_rwg2022jul_p155_49m
_database_code_depnum_ccdc_archive 'CCDC 2227185'
loop_
_audit_author_name
_audit_author_address
'Gable Robert W.'
;University of Melbourne
Australia
;
_audit_update_record             
;
2022-12-17 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
robertwg@unimelb.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H21 F N7 O2 Zn, Cl, H2 O'
_chemical_formula_sum            'C11 H23 Cl F N7 O3 Zn'
_chemical_formula_weight         421.18
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      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                   7.5403(15)
_cell_length_b                   10.171(2)
_cell_length_c                   11.342(2)
_cell_angle_alpha                79.19(3)
_cell_angle_beta                 88.86(3)
_cell_angle_gamma                74.13(3)
_cell_volume                     821.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    812
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      24.58
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.696
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   
;
XDS does not report the values of _exptl_absorpt_correction_T_min and
_exptl_absorpt_correction_T_max.  Even though the data was processed by XDS
the values of the absorption corrections reported by SADABS are reported.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_recrystallization_method 
'grown by slow evaporation from methanol'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21370
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         29.207
_diffrn_reflns_theta_min         1.829
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 13.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_detector_type 'Dectris Eiger2 9M'
_diffrn_measurement_device_type  'MX1 Beamline Australian Synchrotron'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3503
_reflns_number_total             3766
_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       'XDS (Kabsch, 2010)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.072
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.097
_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)+(0.0708P)²+0.2144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3E,H3F)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C1(H1A,H1B), C2(H2C,H2D), C3(H3C,H3D),
 C4(H4C,H4D), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_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 0.24167(3) 0.24885(2) 0.27017(2) 0.02346(11) Uani 1 1 d . . . . .
F1 F -0.10029(19) 0.79603(13) 0.26227(12) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.3685(2) 0.32517(15) 0.48440(14) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.2155(2) 0.68274(16) 0.64448(14) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.3219(2) 0.03349(18) 0.21458(15) 0.0241(3) Uani 1 1 d . . . . .
N2 N 0.0367(2) 0.28075(19) 0.14283(17) 0.0277(4) Uani 1 1 d . . . . .
H2A H -0.065467 0.269107 0.178709 0.033 Uiso 1 1 calc R U . . .
H2B H 0.011745 0.367660 0.101725 0.033 Uiso 1 1 calc R U . . .
N3 N 0.5090(2) 0.23858(18) 0.21957(16) 0.0255(3) Uani 1 1 d . . . . .
H3A H 0.507391 0.289561 0.146473 0.031 Uiso 1 1 calc R U . . .
H3B H 0.563162 0.273849 0.270199 0.031 Uiso 1 1 calc R U . . .
N4 N 0.1901(3) 0.12520(18) 0.42693(16) 0.0274(4) Uani 1 1 d . . . . .
H4A H 0.277065 0.116200 0.482103 0.033 Uiso 1 1 calc R U . . .
H4B H 0.082299 0.167722 0.454287 0.033 Uiso 1 1 calc R U . . .
N5 N 0.1740(2) 0.44180(18) 0.32548(16) 0.0243(3) Uani 1 1 d . . . . .
N6 N 0.0838(2) 0.68027(18) 0.42503(16) 0.0261(3) Uani 1 1 d . . . . .
N7 N 0.3859(3) 0.45710(19) 0.66294(17) 0.0290(4) Uani 1 1 d . . . . .
H7A H 0.428908 0.454505 0.733256 0.035 Uiso 1 1 calc R U . . .
H7B H 0.418186 0.384575 0.630432 0.035 Uiso 1 1 calc R U . . .
C1 C 0.1747(3) 0.0360(2) 0.1302(2) 0.0267(4) Uani 1 1 d . . . . .
H1A H 0.078016 0.004141 0.174404 0.032 Uiso 1 1 calc R U . . .
H1B H 0.224204 -0.026787 0.075486 0.032 Uiso 1 1 calc R U . . .
C2 C 0.0946(3) 0.1818(2) 0.0593(2) 0.0283(4) Uani 1 1 d . . . . .
H2C H 0.186256 0.208734 0.006201 0.034 Uiso 1 1 calc R U . . .
H2D H -0.010823 0.184100 0.010502 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5018(3) 0.0222(2) 0.15791(19) 0.0258(4) Uani 1 1 d . . . . .
H3C H 0.482544 0.065101 0.073572 0.031 Uiso 1 1 calc R U . . .
H3D H 0.567685 -0.075199 0.163382 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6164(3) 0.0932(2) 0.2192(2) 0.0276(4) Uani 1 1 d . . . . .
H4C H 0.648525 0.043702 0.301076 0.033 Uiso 1 1 calc R U . . .
H4D H 0.729611 0.092229 0.176891 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3335(3) -0.0704(2) 0.32592(19) 0.0273(4) Uani 1 1 d . . . . .
H5A H 0.454256 -0.091712 0.364583 0.033 Uiso 1 1 calc R U . . .
H5B H 0.317712 -0.155657 0.306720 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1855(3) -0.0154(2) 0.41103(19) 0.0283(4) Uani 1 1 d . . . . .
H6A H 0.065207 -0.010719 0.378906 0.034 Uiso 1 1 calc R U . . .
H6B H 0.205778 -0.078248 0.488229 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2554(3) 0.4374(2) 0.43461(18) 0.0244(4) Uani 1 1 d . . . . .
C8 C 0.0576(3) 0.5599(2) 0.26857(19) 0.0264(4) Uani 1 1 d . . . . .
H8 H 0.004119 0.563595 0.194422 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0175(3) 0.6762(2) 0.32046(19) 0.0266(4) Uani 1 1 d . . . . .
C10 C 0.2010(3) 0.5640(2) 0.48352(18) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.2693(3) 0.5735(2) 0.60437(19) 0.0256(4) Uani 1 1 d . . . . .
Cl1 Cl 0.60481(7) 0.30566(5) -0.07919(4) 0.02845(13) Uani 1 1 d . . . . .
O3 O 0.2260(2) 0.47287(18) 0.00170(17) 0.0373(4) Uani 1 1 d G . . . .
H3E H 0.318822 0.424797 -0.029540 0.056 Uiso 1 1 d G U . . .
H3F H 0.260713 0.540780 0.017216 0.056 Uiso 1 1 d G 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 N1 2.3108(18) . ?
Zn1 N2 2.0542(19) . ?
Zn1 N3 2.0650(18) . ?
Zn1 N4 2.0725(19) . ?
Zn1 N5 2.0992(18) . ?
F1 C9 1.357(2) . ?
O1 C7 1.263(3) . ?
O2 C11 1.242(3) . ?
N1 C1 1.472(3) . ?
N1 C3 1.474(3) . ?
N1 C5 1.474(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C2 1.484(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C4 1.479(3) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 C6 1.484(3) . ?
N5 C7 1.380(3) . ?
N5 C8 1.336(3) . ?
N6 C9 1.309(3) . ?
N6 C10 1.333(3) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C11 1.332(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.514(3) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C3 C4 1.519(3) . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.520(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.451(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(3) . ?
C10 C11 1.503(3) . ?
O3 H3E 0.8500 . ?
O3 H3F 0.8503 . ?

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
N2 Zn1 N1 80.29(7) . . ?
N2 Zn1 N3 120.37(7) . . ?
N2 Zn1 N4 110.24(8) . . ?
N2 Zn1 N5 101.41(7) . . ?
N3 Zn1 N1 80.33(7) . . ?
N3 Zn1 N4 120.60(8) . . ?
N3 Zn1 N5 99.17(7) . . ?
N4 Zn1 N1 79.56(7) . . ?
N4 Zn1 N5 99.31(7) . . ?
N5 Zn1 N1 178.23(6) . . ?
C1 N1 Zn1 106.01(12) . . ?
C1 N1 C3 112.87(16) . . ?
C1 N1 C5 112.90(16) . . ?
C3 N1 Zn1 105.30(12) . . ?
C5 N1 Zn1 106.46(12) . . ?
C5 N1 C3 112.55(16) . . ?
Zn1 N2 H2A 109.6 . . ?
Zn1 N2 H2B 109.6 . . ?
H2A N2 H2B 108.1 . . ?
C2 N2 Zn1 110.40(13) . . ?
C2 N2 H2A 109.6 . . ?
C2 N2 H2B 109.6 . . ?
Zn1 N3 H3A 109.4 . . ?
Zn1 N3 H3B 109.4 . . ?
H3A N3 H3B 108.0 . . ?
C4 N3 Zn1 111.12(12) . . ?
C4 N3 H3A 109.4 . . ?
C4 N3 H3B 109.4 . . ?
Zn1 N4 H4A 108.9 . . ?
Zn1 N4 H4B 108.9 . . ?
H4A N4 H4B 107.7 . . ?
C6 N4 Zn1 113.39(13) . . ?
C6 N4 H4A 108.9 . . ?
C6 N4 H4B 108.9 . . ?
C7 N5 Zn1 113.51(13) . . ?
C8 N5 Zn1 126.34(14) . . ?
C8 N5 C7 120.08(18) . . ?
C9 N6 C10 117.21(18) . . ?
H7A N7 H7B 120.0 . . ?
C11 N7 H7A 120.0 . . ?
C11 N7 H7B 120.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.55(16) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N2 C2 C1 109.74(18) . . ?
N2 C2 H2C 109.7 . . ?
N2 C2 H2D 109.7 . . ?
C1 C2 H2C 109.7 . . ?
C1 C2 H2D 109.7 . . ?
H2C C2 H2D 108.2 . . ?
N1 C3 H3C 109.5 . . ?
N1 C3 H3D 109.5 . . ?
N1 C3 C4 110.60(16) . . ?
H3C C3 H3D 108.1 . . ?
C4 C3 H3C 109.5 . . ?
C4 C3 H3D 109.5 . . ?
N3 C4 C3 109.31(17) . . ?
N3 C4 H4C 109.8 . . ?
N3 C4 H4D 109.8 . . ?
C3 C4 H4C 109.8 . . ?
C3 C4 H4D 109.8 . . ?
H4C C4 H4D 108.3 . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
N1 C5 C6 110.39(17) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N4 C6 C5 110.23(17) . . ?
N4 C6 H6A 109.6 . . ?
N4 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
O1 C7 N5 118.44(18) . . ?
O1 C7 C10 125.20(18) . . ?
N5 C7 C10 116.36(18) . . ?
N5 C8 H8 120.2 . . ?
N5 C8 C9 119.53(19) . . ?
C9 C8 H8 120.2 . . ?
F1 C9 C8 119.37(18) . . ?
N6 C9 F1 116.10(18) . . ?
N6 C9 C8 124.5(2) . . ?
N6 C10 C7 122.25(18) . . ?
N6 C10 C11 115.01(18) . . ?
C7 C10 C11 122.74(18) . . ?
O2 C11 N7 124.26(19) . . ?
O2 C11 C10 120.77(19) . . ?
N7 C11 C10 114.96(18) . . ?
H3E O3 H3F 104.5 . . ?

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
N2 H2A O2 0.89 2.35 3.056(3) 136.5 2_566 yes
N2 H2B O3 0.89 2.34 2.946(3) 125.7 . yes
N2 H2B O3 0.89 2.24 2.960(3) 138.3 2_565 yes
N3 H3A Cl1 0.89 2.64 3.431(2) 149.2 . yes
N3 H3B O2 0.89 2.13 2.972(2) 157.2 2_666 yes
N4 H4A O1 0.89 2.41 2.898(2) 114.7 . yes
N4 H4B O2 0.89 2.49 3.172(3) 133.8 2_566 yes
N4 H4B N6 0.89 2.34 3.142(3) 149.1 2_566 yes
N7 H7A Cl1 0.86 2.53 3.281(2) 146.9 1_556 yes
N7 H7B O1 0.86 1.94 2.654(2) 139.3 . yes
C1 H1B Cl1 0.97 2.77 3.568(2) 140.1 2_655 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 N1 C1 C2 31.49(19) . . . . ?
Zn1 N1 C3 C4 34.97(19) . . . . ?
Zn1 N1 C5 C6 36.61(18) . . . . ?
Zn1 N2 C2 C1 47.52(19) . . . . ?
Zn1 N3 C4 C3 45.4(2) . . . . ?
Zn1 N4 C6 C5 38.8(2) . . . . ?
Zn1 N5 C7 O1 4.9(2) . . . . ?
Zn1 N5 C7 C10 -174.46(13) . . . . ?
Zn1 N5 C8 C9 175.52(14) . . . . ?
O1 C7 C10 N6 178.43(19) . . . . ?
O1 C7 C10 C11 -2.7(3) . . . . ?
N1 C1 C2 N2 -53.2(2) . . . . ?
N1 C3 C4 N3 -54.5(2) . . . . ?
N1 C5 C6 N4 -50.8(2) . . . . ?
N5 C7 C10 N6 -2.2(3) . . . . ?
N5 C7 C10 C11 176.58(17) . . . . ?
N5 C8 C9 F1 179.80(18) . . . . ?
N5 C8 C9 N6 -1.1(3) . . . . ?
N6 C10 C11 O2 0.9(3) . . . . ?
N6 C10 C11 N7 179.76(17) . . . . ?
C1 N1 C3 C4 150.16(17) . . . . ?
C1 N1 C5 C6 -79.3(2) . . . . ?
C3 N1 C1 C2 -83.3(2) . . . . ?
C3 N1 C5 C6 151.49(17) . . . . ?
C5 N1 C1 C2 147.67(18) . . . . ?
C5 N1 C3 C4 -80.6(2) . . . . ?
C7 N5 C8 C9 -1.0(3) . . . . ?
C7 C10 C11 O2 -178.00(18) . . . . ?
C7 C10 C11 N7 0.9(3) . . . . ?
C8 N5 C7 O1 -178.10(18) . . . . ?
C8 N5 C7 C10 2.5(3) . . . . ?
C9 N6 C10 C7 0.3(3) . . . . ?
C9 N6 C10 C11 -178.58(17) . . . . ?
C10 N6 C9 F1 -179.47(17) . . . . ?
C10 N6 C9 C8 1.4(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_rwg2022apr_p155x2gau
_database_code_depnum_ccdc_archive 'CCDC 2227186'
loop_
_audit_author_name
_audit_author_address
'Gable Robert W.'
;University of Melbourne
Australia
;
_audit_update_record             
;
2022-12-17 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
robertwg@unimelb.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H21 F N7 O2 Zn, Cl, C H4 O'
_chemical_formula_sum            'C12 H25 Cl F N7 O3 Zn'
_chemical_formula_weight         435.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H25 Cl F N7 O3 Zn'
_chemical_oxdiff_usercomment     P155
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   13.1029(4)
_cell_length_b                   18.5099(6)
_cell_length_c                   7.7230(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.067(3)
_cell_angle_gamma                90
_cell_volume                     1873.08(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11048
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      30.2260
_cell_measurement_theta_min      3.4010
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.473
_exptl_absorpt_coefficient_mu    1.490
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 0 0.0553
1 -1 0 0.0553
0 0 1 0.2942
0 0 -1 0.2942
1 1 0 0.0666
-1 -1 0 0.0666

_exptl_crystal_recrystallization_method 
'crystals were grown by slow evaporation from methanol'
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 1.0000 0.0000 -0.0514 -0.0159 -0.0388
1.0000 -1.0000 -0.0000 0.0514 0.0159 0.0388
-0.0000 -0.0000 1.0000 -0.0106 -0.0785 0.0465
0.0000 0.0000 -1.0000 0.0106 0.0785 -0.0465
1.0000 1.0000 -0.0000 -0.0218 0.0340 0.0526
-1.0000 -1.0000 0.0000 0.0218 -0.0340 -0.0526

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15847
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.372
_diffrn_reflns_theta_min         3.109
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  54.00   1.00    9.00    --   12.95 -99.00  30.00   74
  2  ω    -28.00  93.00   1.00    9.00    --   12.95  19.00   0.00  121
  3  ω    -28.00  93.00   1.00    9.00    --   12.95  19.00 120.00  121
  4  ω    -11.00  87.00   1.00    9.00    --   12.95  37.00-150.00   98
  5  ω    -84.00 -35.00   1.00    9.00    --  -13.58 148.00-176.61   49
  6  ω    -83.00 -42.00   1.00    9.00    --  -13.58 146.00  96.89   41
  7  ω   -101.00 -55.00   1.00    9.00    --  -13.58 178.00  30.00   46
  8  ω    -20.00  26.00   1.00    9.00    --  -13.58 -99.00   0.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0148001000
_diffrn_orient_matrix_UB_12      -0.0366124000
_diffrn_orient_matrix_UB_13      -0.0106473000
_diffrn_orient_matrix_UB_21      0.0249519000
_diffrn_orient_matrix_UB_22      0.0090593000
_diffrn_orient_matrix_UB_23      -0.0784693000
_diffrn_orient_matrix_UB_31      0.0456850000
_diffrn_orient_matrix_UB_32      0.0068696000
_diffrn_orient_matrix_UB_33      0.0464918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.840
_reflns_number_gt                4890
_reflns_number_total             5008
_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       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0183
_refine_ls_restrained_S_all      1.039
_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)+(0.0220P)²+0.8685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0461
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C1(H1A,H1B), C2(H2C,H2D), C3(H3C,H3D),
 C4(H4C,H4D), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.c X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.41606(2) 0.30840(2) 0.39182(2) 0.01107(6) Uani 1 1 d . . . . .
F1 F 0.83972(10) 0.48766(8) 0.3836(2) 0.0320(4) Uani 1 1 d . . . . .
O1 O 0.44874(11) 0.41447(8) 0.4175(2) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.53705(11) 0.63300(8) 0.4127(2) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.35728(12) 0.19119(9) 0.3662(2) 0.0114(3) Uani 1 1 d . . . . .
N2 N 0.51417(13) 0.26971(9) 0.2071(2) 0.0135(3) Uani 1 1 d . . . . .
H2A H 0.526899 0.305010 0.128033 0.016 Uiso 1 1 calc R U . . .
H2B H 0.574429 0.257438 0.257915 0.016 Uiso 1 1 calc R U . . .
N3 N 0.43254(13) 0.27373(10) 0.6450(2) 0.0153(3) Uani 1 1 d . . . . .
H3A H 0.488475 0.294695 0.693665 0.018 Uiso 1 1 calc R U . . .
H3B H 0.376781 0.286631 0.708023 0.018 Uiso 1 1 calc R U . . .
N4 N 0.26720(13) 0.32936(9) 0.3176(2) 0.0144(3) Uani 1 1 d . . . . .
H4A H 0.243335 0.368836 0.374941 0.017 Uiso 1 1 calc R U . . .
H4B H 0.264690 0.338626 0.201975 0.017 Uiso 1 1 calc R U . . .
N5 N 0.61491(13) 0.38041(9) 0.4181(2) 0.0152(3) Uani 1 1 d . . . . .
N6 N 0.67524(14) 0.52400(10) 0.4021(3) 0.0176(4) Uani 1 1 d . . . . .
N7 N 0.40517(15) 0.55449(10) 0.4208(3) 0.0226(5) Uani 1 1 d . . . . .
H7A H 0.359622 0.589411 0.422927 0.027 Uiso 1 1 calc R U . . .
H7B H 0.385255 0.509090 0.422449 0.027 Uiso 1 1 calc R U . . .
C1 C 0.42883(16) 0.15386(11) 0.2510(3) 0.0138(4) Uani 1 1 d . . . . .
H1A H 0.393341 0.113700 0.191417 0.017 Uiso 1 1 calc R U . . .
H1B H 0.485498 0.133185 0.319920 0.017 Uiso 1 1 calc R U . . .
C2 C 0.47113(15) 0.20596(11) 0.1182(3) 0.0142(4) Uani 1 1 d . . . . .
H2C H 0.524939 0.181845 0.049341 0.017 Uiso 1 1 calc R U . . .
H2D H 0.416117 0.221297 0.038275 0.017 Uiso 1 1 calc R U . . .
C3 C 0.35736(16) 0.16110(12) 0.5425(3) 0.0151(4) Uani 1 1 d . . . . .
H3C H 0.365905 0.108004 0.537276 0.018 Uiso 1 1 calc R U . . .
H3D H 0.291447 0.171668 0.599647 0.018 Uiso 1 1 calc R U . . .
C4 C 0.44402(17) 0.19426(11) 0.6457(3) 0.0159(4) Uani 1 1 d . . . . .
H4C H 0.442480 0.176031 0.766225 0.019 Uiso 1 1 calc R U . . .
H4D H 0.510306 0.180686 0.593675 0.019 Uiso 1 1 calc R U . . .
C5 C 0.25405(15) 0.19814(11) 0.2913(3) 0.0141(4) Uani 1 1 d . . . . .
H5A H 0.212689 0.155319 0.322427 0.017 Uiso 1 1 calc R U . . .
H5B H 0.258770 0.200442 0.163451 0.017 Uiso 1 1 calc R U . . .
C6 C 0.20316(15) 0.26561(11) 0.3587(3) 0.0159(4) Uani 1 1 d . . . . .
H6A H 0.135057 0.271112 0.304623 0.019 Uiso 1 1 calc R U . . .
H6B H 0.193869 0.261843 0.485553 0.019 Uiso 1 1 calc R U . . .
C7 C 0.54325(15) 0.43326(11) 0.4161(3) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.71201(15) 0.39879(11) 0.4075(3) 0.0155(4) Uani 1 1 d . . . . .
H8 H 0.763140 0.362410 0.406324 0.019 Uiso 1 1 calc R U . . .
C9 C 0.73953(15) 0.47045(12) 0.3981(3) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.57591(16) 0.50692(11) 0.4118(3) 0.0138(4) Uani 1 1 d . . . . .
C11 C 0.50432(16) 0.57035(11) 0.4152(3) 0.0148(4) Uani 1 1 d . . . . .
Cl1 Cl 0.22427(4) 0.31518(3) 0.88160(6) 0.01738(11) Uani 1 1 d . . . . .
O3 O 0.17274(16) 0.42553(10) 0.5811(2) 0.0322(4) Uani 1 1 d . . . . .
H3 H 0.186137 0.397682 0.663983 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1581(3) 0.49524(16) 0.6437(4) 0.0521(10) Uani 1 1 d . . . . .
H12A H 0.146725 0.528269 0.546395 0.078 Uiso 1 1 calc R U . . .
H12B H 0.218805 0.510547 0.708338 0.078 Uiso 1 1 calc R U . . .
H12C H 0.098624 0.496019 0.720381 0.078 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 2.0192(15) . ?
Zn1 N1 2.3107(16) . ?
Zn1 N2 2.0505(17) . ?
Zn1 N3 2.0693(17) . ?
Zn1 N4 2.0690(17) . ?
F1 C9 1.356(2) . ?
O1 C7 1.286(2) . ?
O2 C11 1.237(3) . ?
N1 C1 1.466(3) . ?
N1 C3 1.471(3) . ?
N1 C5 1.476(2) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C2 1.477(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 C4 1.479(3) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 C6 1.482(3) . ?
N5 C7 1.356(3) . ?
N5 C8 1.320(3) . ?
N6 C9 1.301(3) . ?
N6 C10 1.341(3) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C11 1.333(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.514(3) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C3 C4 1.517(3) . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.509(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.430(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C10 C11 1.503(3) . ?
O3 H3 0.8400 . ?
O3 C12 1.391(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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 Zn1 N1 172.75(6) . . ?
O1 Zn1 N2 105.95(7) . . ?
O1 Zn1 N3 100.78(7) . . ?
O1 Zn1 N4 92.56(6) . . ?
N2 Zn1 N1 79.73(6) . . ?
N2 Zn1 N3 118.97(7) . . ?
N2 Zn1 N4 117.67(7) . . ?
N3 Zn1 N1 79.87(6) . . ?
N4 Zn1 N1 80.70(6) . . ?
N4 Zn1 N3 114.66(7) . . ?
C7 O1 Zn1 117.78(13) . . ?
C1 N1 Zn1 106.32(12) . . ?
C1 N1 C3 112.55(16) . . ?
C1 N1 C5 112.91(16) . . ?
C3 N1 Zn1 106.05(12) . . ?
C3 N1 C5 113.30(16) . . ?
C5 N1 Zn1 104.88(11) . . ?
Zn1 N2 H2A 109.4 . . ?
Zn1 N2 H2B 109.4 . . ?
H2A N2 H2B 108.0 . . ?
C2 N2 Zn1 111.29(12) . . ?
C2 N2 H2A 109.4 . . ?
C2 N2 H2B 109.4 . . ?
Zn1 N3 H3A 109.9 . . ?
Zn1 N3 H3B 109.9 . . ?
H3A N3 H3B 108.3 . . ?
C4 N3 Zn1 108.81(12) . . ?
C4 N3 H3A 109.9 . . ?
C4 N3 H3B 109.9 . . ?
Zn1 N4 H4A 109.9 . . ?
Zn1 N4 H4B 109.9 . . ?
H4A N4 H4B 108.3 . . ?
C6 N4 Zn1 108.98(12) . . ?
C6 N4 H4A 109.9 . . ?
C6 N4 H4B 109.9 . . ?
C8 N5 C7 118.74(17) . . ?
C9 N6 C10 116.74(18) . . ?
H7A N7 H7B 120.0 . . ?
C11 N7 H7A 120.0 . . ?
C11 N7 H7B 120.0 . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.24(16) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C2 C1 109.51(16) . . ?
N2 C2 H2C 109.8 . . ?
N2 C2 H2D 109.8 . . ?
C1 C2 H2C 109.8 . . ?
C1 C2 H2D 109.8 . . ?
H2C C2 H2D 108.2 . . ?
N1 C3 H3C 109.8 . . ?
N1 C3 H3D 109.8 . . ?
N1 C3 C4 109.47(16) . . ?
H3C C3 H3D 108.2 . . ?
C4 C3 H3C 109.8 . . ?
C4 C3 H3D 109.8 . . ?
N3 C4 C3 108.94(17) . . ?
N3 C4 H4C 109.9 . . ?
N3 C4 H4D 109.9 . . ?
C3 C4 H4C 109.9 . . ?
C3 C4 H4D 109.9 . . ?
H4C C4 H4D 108.3 . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
N1 C5 C6 109.99(16) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
N4 C6 C5 109.55(16) . . ?
N4 C6 H6A 109.8 . . ?
N4 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
O1 C7 N5 118.13(18) . . ?
O1 C7 C10 123.11(18) . . ?
N5 C7 C10 118.76(18) . . ?
N5 C8 H8 119.9 . . ?
N5 C8 C9 120.29(18) . . ?
C9 C8 H8 119.9 . . ?
F1 C9 C8 118.99(19) . . ?
N6 C9 F1 116.73(19) . . ?
N6 C9 C8 124.28(19) . . ?
N6 C10 C7 121.10(18) . . ?
N6 C10 C11 114.99(17) . . ?
C7 C10 C11 123.90(18) . . ?
O2 C11 N7 123.04(19) . . ?
O2 C11 C10 121.05(19) . . ?
N7 C11 C10 115.91(18) . . ?
C12 O3 H3 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
N2 H2A O2 0.91 2.02 2.916(2) 166.0 2_564 yes
N2 H2B Cl1 0.91 2.56 3.4430(18) 162.8 4_554 yes
N3 H3A O2 0.91 2.25 3.020(2) 142.3 2_565 yes
N3 H3B Cl1 0.91 2.46 3.3742(19) 177.2 . yes
N4 H4A O3 0.91 2.12 2.975(3) 156.0 . yes
N4 H4B Cl1 0.91 2.57 3.4234(18) 157.1 1_554 yes
N7 H7A Cl1 0.88 2.52 3.395(2) 171.3 2_564 yes
N7 H7B O1 0.88 1.94 2.654(2) 137.3 . yes
C3 H3C F1 0.99 2.55 3.444(3) 150.7 3_445 yes
C5 H5A O2 0.99 2.44 3.229(3) 136.2 3_445 yes
C5 H5A N6 0.99 2.56 3.492(3) 157.7 3_445 yes
O3 H3 Cl1 0.84 2.32 3.1636(19) 176.7 . 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 C7 N5 -7.6(3) . . . . ?
Zn1 O1 C7 C10 172.09(16) . . . . ?
Zn1 N1 C1 C2 -32.45(17) . . . . ?
Zn1 N1 C3 C4 -32.24(19) . . . . ?
Zn1 N1 C5 C6 -34.64(18) . . . . ?
Zn1 N2 C2 C1 -46.86(18) . . . . ?
Zn1 N3 C4 C3 -51.82(19) . . . . ?
Zn1 N4 C6 C5 -48.94(18) . . . . ?
O1 C7 C10 N6 -176.78(19) . . . . ?
O1 C7 C10 C11 2.5(3) . . . . ?
N1 C1 C2 N2 53.2(2) . . . . ?
N1 C3 C4 N3 56.8(2) . . . . ?
N1 C5 C6 N4 57.2(2) . . . . ?
N5 C7 C10 N6 2.9(3) . . . . ?
N5 C7 C10 C11 -177.84(19) . . . . ?
N5 C8 C9 F1 -178.65(19) . . . . ?
N5 C8 C9 N6 1.4(4) . . . . ?
N6 C10 C11 O2 -1.4(3) . . . . ?
N6 C10 C11 N7 178.54(19) . . . . ?
C1 N1 C3 C4 83.6(2) . . . . ?
C1 N1 C5 C6 -149.98(17) . . . . ?
C3 N1 C1 C2 -148.14(17) . . . . ?
C3 N1 C5 C6 80.6(2) . . . . ?
C5 N1 C1 C2 82.03(19) . . . . ?
C5 N1 C3 C4 -146.75(17) . . . . ?
C7 N5 C8 C9 1.3(3) . . . . ?
C7 C10 C11 O2 179.4(2) . . . . ?
C7 C10 C11 N7 -0.7(3) . . . . ?
C8 N5 C7 O1 176.44(19) . . . . ?
C8 N5 C7 C10 -3.3(3) . . . . ?
C9 N6 C10 C7 -0.4(3) . . . . ?
C9 N6 C10 C11 -179.7(2) . . . . ?
C10 N6 C9 F1 178.27(18) . . . . ?
C10 N6 C9 C8 -1.7(3) . . . . ?

_olex2_exptl_crystal_mounting_method mounted
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.846
