# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_deh390
_database_code_depnum_ccdc_archive 'CCDC 2320600'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2023-12-19 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         '0.5(C19 H19 Cl2 F3 N4 Zn)'
_chemical_formula_weight         248.343
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 14.07430 7.03180 5.16520 2.41000 3.26550 0.23330 10.31630
58.70970 1.30410 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   31.5266(16)
_cell_length_b                   16.1610(8)
_cell_length_c                   13.1152(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.276(2)
_cell_angle_gamma                90
_cell_volume                     6091.3(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9461
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.84
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5891
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0843 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.7903.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       plate
_exptl_crystal_F_000             2021.908
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_diffrn_reflns.reduction_process narrow--frame
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9954
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55874
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9954
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         2.45
_diffrn.ambient_temp_esd         2.0
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine--focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              36
_reflns_limit_h_min              -39
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4774
_reflns_number_total             6320
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.5441
_refine_diff_density_min         -0.5814
_refine_diff_density_rms         0.0869
_refine_ls_d_res_high            0.7956
_refine_ls_d_res_low             8.3250
_refine_ls_goodness_of_fit_ref   1.0331
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6320
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.0269
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+11.8126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1089
_olex2_refinement_description    
;
1. Restrained distances
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 C14-C12 \\sim C14-F1 \\sim C14-F2 \\sim C14-F3 \\sim C14-F1A \\sim C14-F2A
\\sim C14-F3A
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 F1, F3, F2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, F3A, F2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, F3A, F2A, C14, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1, F3, F2, C14, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C6(H6), C5(H5), C1(H1), C4(H4), C3(H3)
4.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C17(H17a,H17b,H17c), C16(H16a,H16b,H16c), C19(H19a,H19b,
 H19c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Zn1 Zn 0.370082(11) 0.626281(19) 0.51126(3) 0.03038(10) Uani 1.000000 . . .
Cl2 Cl 0.32883(2) 0.55558(5) 0.35794(6) 0.03949(18) Uani 1.000000 . . .
Cl1 Cl 0.44597(3) 0.63634(5) 0.55683(7) 0.0477(2) Uani 1.000000 . . .
N1 N 0.33753(8) 0.73684(13) 0.51358(18) 0.0288(5) Uani 1.000000 . . .
N2 N 0.36061(7) 0.60840(13) 0.65268(17) 0.0275(5) Uani 1.000000 . . .
N4 N 0.40413(8) 0.49270(14) 0.72906(19) 0.0309(5) Uani 1.000000 . . .
N3 N 0.42028(8) 0.61318(14) 0.83457(19) 0.0316(5) Uani 1.000000 . . .
C10 C 0.33342(9) 0.67035(15) 0.6710(2) 0.0258(5) Uani 1.000000 . . .
C11 C 0.31736(9) 0.66754(16) 0.7534(2) 0.0288(6) Uani 1.000000 . . .
H11 H 0.32524(9) 0.62231(16) 0.8041(2) 0.0345(7) Uiso 1.000000 R . .
C8 C 0.29431(9) 0.80409(16) 0.6077(2) 0.0264(5) Uani 1.000000 . . .
C13 C 0.27774(9) 0.79887(16) 0.6919(2) 0.0298(6) Uani 1.000000 . . .
H13 H 0.25866(9) 0.84157(16) 0.7001(2) 0.0358(7) Uiso 1.000000 R . .
C9 C 0.32129(8) 0.73855(16) 0.5965(2) 0.0251(5) Uani 1.000000 . . .
C7 C 0.28636(9) 0.87456(16) 0.5338(2) 0.0291(5) Uani 1.000000 . . .
C12 C 0.28926(9) 0.73170(17) 0.7624(2) 0.0314(6) Uani 1.000000 D U .
C15 C 0.39445(9) 0.57182(16) 0.7401(2) 0.0282(6) Uani 1.000000 . . .
C6 C 0.26275(10) 0.94667(17) 0.5410(2) 0.0360(6) Uani 1.000000 . . .
H6 H 0.24957(10) 0.95007(17) 0.5942(2) 0.0432(8) Uiso 1.000000 R . .
C18 C 0.36973(11) 0.43899(18) 0.6484(2) 0.0387(7) Uani 1.000000 . . .
H18a H 0.33849(11) 0.4607(7) 0.6311(13) 0.0581(10) Uiso 1.000000 GR . .
H18b H 0.3750(5) 0.4369(10) 0.5798(7) 0.0581(10) Uiso 1.000000 GR . .
H18c H 0.3725(5) 0.3832(4) 0.6797(7) 0.0581(10) Uiso 1.000000 GR . .
C2 C 0.30507(10) 0.87192(17) 0.4533(2) 0.0348(6) Uani 1.000000 . . .
F1 F 0.2368(2) 0.7780(4) 0.8347(7) 0.0701(18) Uani 0.507(10) D U 1
C5 C 0.25880(11) 1.01224(18) 0.4708(3) 0.0425(7) Uani 1.000000 . . .
H5 H 0.24331(11) 1.06110(18) 0.4772(3) 0.0510(9) Uiso 1.000000 R . .
C1 C 0.32963(10) 0.79969(18) 0.4467(2) 0.0369(7) Uani 1.000000 . . .
H1 H 0.34093(10) 0.79734(18) 0.3899(2) 0.0443(8) Uiso 1.000000 R . .
C17 C 0.43828(10) 0.5752(2) 0.9445(2) 0.0388(7) Uani 1.000000 . . .
H17a H 0.4279(6) 0.6070(8) 0.9938(5) 0.0582(10) Uiso 1.000000 GR . .
H17b H 0.4267(6) 0.5184(5) 0.9383(3) 0.0582(10) Uiso 1.000000 GR . .
H17c H 0.47236(10) 0.5747(12) 0.9758(8) 0.0582(10) Uiso 1.000000 GR . .
C16 C 0.42875(11) 0.70157(18) 0.8332(3) 0.0418(7) Uani 1.000000 . . .
H16a H 0.4212(7) 0.7194(3) 0.7562(4) 0.0627(11) Uiso 1.000000 GR . .
H16b H 0.4092(6) 0.7316(2) 0.8625(17) 0.0627(11) Uiso 1.000000 GR . .
H16c H 0.46158(19) 0.7132(2) 0.8798(15) 0.0627(11) Uiso 1.000000 GR . .
F2 F 0.2592(4) 0.6544(3) 0.8658(7) 0.075(2) Uani 0.507(10) D U 1
C19 C 0.45076(10) 0.4579(2) 0.7853(3) 0.0431(7) Uani 1.000000 . . .
H19a H 0.47333(14) 0.5028(2) 0.8165(16) 0.0646(11) Uiso 1.000000 GR . .
H19b H 0.4518(2) 0.4212(11) 0.8458(12) 0.0646(11) Uiso 1.000000 GR . .
H19c H 0.4585(3) 0.4263(11) 0.7315(5) 0.0646(11) Uiso 1.000000 GR . .
C14 C 0.27255(12) 0.72656(19) 0.8534(3) 0.0438(7) Uani 1.000000 D U .
C4 C 0.27698(12) 1.0084(2) 0.3910(3) 0.0493(8) Uani 1.000000 . . .
H4 H 0.27356(12) 1.0542(2) 0.3428(3) 0.0592(10) Uiso 1.000000 R . .
C3 C 0.29977(12) 0.9391(2) 0.3814(3) 0.0470(8) Uani 1.000000 . . .
H3 H 0.31198(12) 0.9364(2) 0.3262(3) 0.0564(10) Uiso 1.000000 R . .
F3 F 0.3049(2) 0.7524(8) 0.9486(4) 0.095(3) Uani 0.507(10) D U 1
F1A F 0.2611(4) 0.7941(3) 0.8854(7) 0.082(2) Uani 0.493(10) D U 2
F2A F 0.2358(3) 0.6754(6) 0.8276(6) 0.082(2) Uani 0.493(10) D U 2
F3A F 0.3030(2) 0.6906(6) 0.9476(4) 0.076(2) Uani 0.493(10) D U 2


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 Cl2 2.2113(8) . ?
Zn1 Cl1 2.2207(8) . ?
Zn1 N1 2.067(2) . ?
Zn1 N2 2.017(2) . ?
N1 C9 1.379(3) . ?
N1 C1 1.297(3) . ?
N2 C10 1.402(3) . ?
N2 C15 1.341(3) . ?
N4 C15 1.336(3) . ?
N4 C18 1.451(4) . ?
N4 C19 1.460(4) . ?
N3 C15 1.347(3) . ?
N3 C17 1.451(3) . ?
N3 C16 1.455(3) . ?
C10 C11 1.369(4) . ?
C10 C9 1.418(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(4) . ?
C8 C13 1.405(4) . ?
C8 C9 1.404(3) . ?
C8 C7 1.449(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.375(4) . ?
C7 C6 1.407(4) . ?
C7 C2 1.405(4) . ?
C12 C14 1.491(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.375(4) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C2 C1 1.423(4) . ?
C2 C3 1.403(4) . ?
F1 C14 1.339(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(5) . ?
C1 H1 0.9500 . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
F2 C14 1.272(6) . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C14 F3 1.315(6) . ?
C14 F1A 1.274(6) . ?
C14 F2A 1.348(6) . ?
C14 F3A 1.345(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.364(4) . ?
C3 H3 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
Cl1 Zn1 Cl2 116.63(3) . . ?
N1 Zn1 Cl2 110.50(6) . . ?
N1 Zn1 Cl1 114.79(7) . . ?
N2 Zn1 Cl2 120.54(7) . . ?
N2 Zn1 Cl1 108.27(7) . . ?
N2 Zn1 N1 81.27(8) . . ?
C9 N1 Zn1 112.11(16) . . ?
C1 N1 Zn1 128.70(19) . . ?
C1 N1 C9 119.1(2) . . ?
C10 N2 Zn1 112.81(16) . . ?
C15 N2 Zn1 118.90(17) . . ?
C15 N2 C10 119.7(2) . . ?
C18 N4 C15 121.1(2) . . ?
C19 N4 C15 122.8(2) . . ?
C19 N4 C18 115.7(2) . . ?
C17 N3 C15 123.1(2) . . ?
C16 N3 C15 121.4(2) . . ?
C16 N3 C17 115.4(2) . . ?
C11 C10 N2 124.2(2) . . ?
C9 C10 N2 116.6(2) . . ?
C9 C10 C11 119.2(2) . . ?
H11 C11 C10 120.19(15) . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.19(15) . . ?
C9 C8 C13 118.3(2) . . ?
C7 C8 C13 123.7(2) . . ?
C7 C8 C9 117.9(2) . . ?
H13 C13 C8 120.14(15) . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H13 120.14(15) . . ?
C10 C9 N1 116.5(2) . . ?
C8 C9 N1 122.4(2) . . ?
C8 C9 C10 121.2(2) . . ?
C6 C7 C8 123.8(3) . . ?
C2 C7 C8 117.9(2) . . ?
C2 C7 C6 118.2(3) . . ?
C13 C12 C11 121.9(2) . . ?
C14 C12 C11 118.1(2) . . ?
C14 C12 C13 120.0(2) . . ?
N4 C15 N2 117.8(2) . . ?
N3 C15 N2 122.4(2) . . ?
N3 C15 N4 119.7(2) . . ?
H6 C6 C7 120.06(17) . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.06(18) . . ?
H18a C18 N4 109.5 . . ?
H18b C18 N4 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 N4 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C1 C2 C7 118.5(3) . . ?
C3 C2 C7 120.7(3) . . ?
C3 C2 C1 120.8(3) . . ?
H5 C5 C6 119.36(18) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.36(17) . . ?
C2 C1 N1 124.0(3) . . ?
H1 C1 N1 118.00(16) . . ?
H1 C1 C2 118.00(16) . . ?
H17a C17 N3 109.5 . . ?
H17b C17 N3 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 N3 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H16a C16 N3 109.5 . . ?
H16b C16 N3 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 N3 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H19a C19 N4 109.5 . . ?
H19b C19 N4 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 N4 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
F1 C14 C12 111.5(4) . . ?
F2 C14 C12 113.5(4) . . ?
F2 C14 F1 107.1(5) . . ?
F3 C14 C12 110.5(3) . . ?
F3 C14 F1 104.0(5) . . ?
F3 C14 F2 109.7(5) . . ?
F1A C14 C12 117.1(4) . . ?
F1A C14 F1 36.6(4) . . ?
F1A C14 F2 126.1(5) . . ?
F1A C14 F3 68.2(5) . . ?
F2A C14 C12 112.5(4) . . ?
F2A C14 F1 76.3(5) . . ?
F2A C14 F2 34.4(4) . . ?
F2A C14 F3 133.2(5) . . ?
F2A C14 F1A 106.1(6) . . ?
F3A C14 C12 113.9(3) . . ?
F3A C14 F1 131.7(4) . . ?
F3A C14 F2 68.6(4) . . ?
F3A C14 F3 44.2(4) . . ?
F3A C14 F1A 105.0(5) . . ?
F3A C14 F2A 100.4(5) . . ?
H4 C4 C5 119.90(17) . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.90(19) . . ?
C4 C3 C2 119.7(3) . . ?
H3 C3 C2 120.16(18) . . ?
H3 C3 C4 120.16(19) . . ?

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 C9 C10 6.19(19) . . . . ?
Zn1 N1 C9 C8 -174.05(16) . . . . ?
Zn1 N1 C1 C2 177.3(2) . . . . ?
Zn1 N2 C10 C11 171.95(17) . . . . ?
Zn1 N2 C10 C9 -6.38(18) . . . . ?
Zn1 N2 C15 N4 -66.0(2) . . . . ?
Zn1 N2 C15 N3 110.04(19) . . . . ?
N1 C9 C10 N2 0.0(3) . . . . ?
N1 C9 C10 C11 -178.4(2) . . . . ?
N1 C9 C8 C13 177.5(2) . . . . ?
N1 C9 C8 C7 -4.4(3) . . . . ?
N1 C1 C2 C7 -2.8(3) . . . . ?
N1 C1 C2 C3 177.0(3) . . . . ?
N2 C10 C11 C12 -178.1(3) . . . . ?
N2 C10 C9 C8 -179.8(2) . . . . ?
N2 C15 N4 C18 -23.7(3) . . . . ?
N2 C15 N4 C19 148.2(2) . . . . ?
N2 C15 N3 C17 146.9(3) . . . . ?
N2 C15 N3 C16 -28.0(3) . . . . ?
N4 C15 N3 C17 -37.1(3) . . . . ?
N4 C15 N3 C16 148.0(2) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C12 C14 -179.9(3) . . . . ?
C10 C9 C8 C13 -2.8(3) . . . . ?
C10 C9 C8 C7 175.3(2) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C11 C12 C14 F1 -163.2(5) . . . . ?
C11 C12 C14 F2 -42.1(6) . . . . ?
C11 C12 C14 F3 81.7(6) . . . . ?
C11 C12 C14 F1A 157.0(7) . . . . ?
C11 C12 C14 F2A -79.6(6) . . . . ?
C11 C12 C14 F3A 33.9(5) . . . . ?
C8 C13 C12 C14 178.8(3) . . . . ?
C8 C7 C6 C5 176.8(3) . . . . ?
C8 C7 C2 C1 1.7(3) . . . . ?
C8 C7 C2 C3 -178.2(3) . . . . ?
C13 C12 C14 F1 18.1(5) . . . . ?
C13 C12 C14 F2 139.1(6) . . . . ?
C13 C12 C14 F3 -97.1(6) . . . . ?
C13 C12 C14 F1A -21.8(7) . . . . ?
C13 C12 C14 F2A 101.7(6) . . . . ?
C13 C12 C14 F3A -144.9(6) . . . . ?
C7 C6 C5 C4 1.2(3) . . . . ?
C7 C2 C3 C4 1.3(3) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?

_smtbx_masks_special_details     ?
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 -0.646 1180.2 292.6 ?
2 0.500 0.000 0.031 1180.2 292.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_exptl.absorpt_correction_type   multi-scan
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
F1 F2 1 1
F1 F3 1 1
F2 F3 1 1
C14 C12 1 2
C14 F1 1 2
C14 F2 1 2
C14 F3 1 2
C14 F1A 1 2
C14 F2A 1 2
C14 F3A 1 2
F1A F2A 1 1
F1A F3A 1 1
F2A F3A 1 1

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0400 2.0922 0.0153 0.0241
2 0.0200 1.3407 0.0682 0.1506

loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
C12 F1 0.004000 0.005686 0.000721 0.004475
C12 F2 0.004000 0.007533 0.007556 -0.000272
C12 C14 0.004000 -0.000684 0.000943 -0.002550
C12 C14 0.004000 -0.000684 0.000943 -0.002550
C12 F3 0.004000 -0.002289 -0.005080 0.000586
C12 F1A 0.004000 0.002008 0.008885 -0.004128
C12 F2A 0.004000 -0.004578 0.004332 -0.007674
C12 F3A 0.004000 -0.004932 0.000511 -0.003368
F1 F2 0.004000 -0.039568 -0.040688 0.019583
F1 C14 0.004000 0.001232 -0.015297 0.000813
F1 F3 0.004000 -0.080813 0.020785 -0.020194
F2 C14 0.004000 0.005478 -0.015528 -0.002231
F2 F3 0.004000 0.073644 -0.069050 -0.004972
C14 F3 0.004000 -0.002984 -0.017386 0.002354
C14 F1A 0.004000 0.002773 0.000410 0.001636
C14 F2A 0.004000 -0.021932 0.003454 -0.003986
C14 F3A 0.004000 -0.008380 0.000284 0.001908
F1A F2A 0.004000 -0.089739 -0.023408 -0.019781
F1A F3A 0.004000 -0.005099 0.079185 0.001230
F2A F3A 0.004000 0.041088 -0.051479 -0.010712

####################################################################### 
# 
# 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_deh380
_database_code_depnum_ccdc_archive 'CCDC 2320601'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2023-12-19 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H20 F6 N8 Zn, C4 H8 O'
_chemical_formula_sum            'C40 H28 F6 N8 O Zn'
_chemical_formula_weight         816.07
_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'
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           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                   22.2606(14)
_cell_length_b                   21.5288(14)
_cell_length_c                   10.5400(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.087(2)
_cell_angle_gamma                90
_cell_volume                     4574.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    167.64
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.8697.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns.reduction_process narrow--frame
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            50100
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.788
_diffrn_reflns_theta_max         24.788
_diffrn_reflns_theta_min         2.768
_diffrn_ambient_temperature      167.64
_diffrn.ambient_temp_esd         2.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine--focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3475
_reflns_number_total             3908
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.708
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.074
_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)+(0.1300P)²+16.5993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O1-C19 = O1-C22
 1.44 with sigma of 0.02
 C19-C20 = C21-C22
 1.53 with sigma of 0.02
 C20-C21
 1.54 with sigma of 0.02
 O1-C20 = O1-C21 = C19-C21 = C20-C22
 2.38 with sigma of 0.04
 C20-C22 \\sim C19-C21
 with sigma of 0.04
 O1-C20 \\sim O1-C21
 with sigma of 0.04
 C19-C20 \\sim C20-C21 \\sim C21-C22
 with sigma of 0.02
 O1-C19 \\sim O1-C22
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
O1 \\sim C19 \\sim C20 \\sim C21 \\sim C22: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 O1, C19, C20, C21, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O1(0.5) C19(0.5) H19A(0.5) H19B(0.5) C20(0.5) H20A(0.5) H20B(0.5)
 C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
5.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C17(H17), C16(H16), C1(H1), C18(H18), C5(H5), C4(H4),
 C6(H6), C3(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 0.500000 0.34345(3) 0.250000 0.0219(3) Uani 1 2 d S T P . .
N2 N 0.51389(15) 0.36134(15) 0.4414(3) 0.0219(7) Uani 1 1 d . . . . .
N1 N 0.58070(17) 0.28422(16) 0.3555(3) 0.0295(8) Uani 1 1 d . . . . .
N3 N 0.48039(18) 0.42511(17) 0.5829(3) 0.0338(8) Uani 1 1 d . . . . .
F1 F 0.6776(2) 0.2412(2) 1.0022(3) 0.0957(16) Uani 1 1 d . . . . .
F2 F 0.5809(2) 0.2767(2) 0.9442(3) 0.0913(14) Uani 1 1 d . . . . .
N4 N 0.42668(16) 0.42573(15) 0.3324(3) 0.0260(7) Uani 1 1 d . . . . .
C15 C 0.47331(18) 0.40496(17) 0.4569(4) 0.0220(8) Uani 1 1 d . . . . .
F3 F 0.6597(3) 0.3364(2) 0.9964(4) 0.1121(19) Uani 1 1 d . . . . .
C9 C 0.5982(2) 0.2850(2) 0.4992(4) 0.0308(9) Uani 1 1 d . . . . .
C10 C 0.5615(2) 0.32696(18) 0.5455(4) 0.0263(8) Uani 1 1 d . . . . .
C8 C 0.6482(2) 0.2461(2) 0.5908(4) 0.0403(11) Uani 1 1 d . . . . .
C13 C 0.6609(3) 0.2473(2) 0.7336(5) 0.0485(13) Uani 1 1 d . . . . .
H13 H 0.694268 0.221317 0.798724 0.058 Uiso 1 1 calc R U . . .
C11 C 0.5765(2) 0.3265(2) 0.6886(4) 0.0336(10) Uani 1 1 d . . . . .
H11 H 0.553972 0.353689 0.724819 0.040 Uiso 1 1 calc R U . . .
C17 C 0.3887(2) 0.4922(2) 0.4636(4) 0.0353(10) Uani 1 1 d . . . . .
H17 H 0.358518 0.522760 0.466498 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4382(2) 0.4685(2) 0.5832(4) 0.0386(10) Uani 1 1 d . . . . .
H16 H 0.442404 0.484053 0.670945 0.046 Uiso 1 1 calc R U . . .
C1 C 0.6119(2) 0.2483(2) 0.3059(4) 0.0388(11) Uani 1 1 d . . . . .
H1 H 0.598321 0.248069 0.207436 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6250(3) 0.2858(2) 0.7778(4) 0.0437(12) Uani 1 1 d . . . . .
C7 C 0.6844(3) 0.2081(2) 0.5358(5) 0.0466(12) Uani 1 1 d . . . . .
C18 C 0.3855(2) 0.4687(2) 0.3385(4) 0.0337(9) Uani 1 1 d . . . . .
H18 H 0.352180 0.484129 0.253277 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6651(3) 0.2091(2) 0.3893(5) 0.0441(12) Uani 1 1 d . . . . .
C5 C 0.7710(3) 0.1351(3) 0.5560(6) 0.0641(17) Uani 1 1 d . . . . .
H5 H 0.807942 0.110316 0.613042 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7502(3) 0.1351(3) 0.4107(6) 0.0625(16) Uani 1 1 d . . . . .
H4 H 0.772088 0.109864 0.369408 0.075 Uiso 1 1 calc R U . . .
C14 C 0.6360(3) 0.2841(3) 0.9285(5) 0.0594(16) Uani 1 1 d . . . . .
C6 C 0.7395(3) 0.1697(3) 0.6175(6) 0.0574(15) Uani 1 1 d . . . . .
H6 H 0.754435 0.168246 0.716278 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6988(3) 0.1715(3) 0.3297(5) 0.0528(14) Uani 1 1 d . . . . .
H3 H 0.684854 0.171783 0.231156 0.063 Uiso 1 1 calc R U . . .
O1 O 0.7632(3) 0.4702(3) 0.8502(6) 0.0500(16) Uani 0.5 1 d D U P A -1
C19 C 0.7485(5) 0.4239(4) 0.9255(8) 0.042(2) Uani 0.5 1 d D U P A -1
H19A H 0.757731 0.382467 0.896817 0.050 Uiso 0.5 1 calc R U P A -1
H19B H 0.700985 0.425730 0.905968 0.050 Uiso 0.5 1 calc R U P A -1
C20 C 0.7911(5) 0.4337(6) 1.0811(9) 0.061(3) Uani 0.5 1 d D U P A -1
H20A H 0.816051 0.395543 1.124874 0.073 Uiso 0.5 1 calc R U P A -1
H20B H 0.763340 0.445630 1.129911 0.073 Uiso 0.5 1 calc R U P A -1
C21 C 0.8382(6) 0.4863(6) 1.0870(10) 0.070(3) Uani 0.5 1 d D U P A -1
H21A H 0.884883 0.474991 1.146356 0.085 Uiso 0.5 1 calc R U P A -1
H21B H 0.827173 0.525051 1.123038 0.085 Uiso 0.5 1 calc R U P A -1
C22 C 0.8257(5) 0.4930(6) 0.9331(10) 0.064(3) Uani 0.5 1 d D U P A -1
H22A H 0.828547 0.537258 0.910792 0.077 Uiso 0.5 1 calc R U P A -1
H22B H 0.859554 0.469525 0.915289 0.077 Uiso 0.5 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
Zn1 N2 1.945(3) . ?
Zn1 N2 1.945(3) 2_655 ?
Zn1 N1 2.097(3) 2_655 ?
Zn1 N1 2.097(3) . ?
N2 C15 1.360(5) . ?
N2 C10 1.375(5) . ?
N1 C9 1.394(5) . ?
N1 C1 1.289(5) . ?
N3 C15 1.342(5) . ?
N3 C16 1.326(6) . ?
F1 C14 1.305(6) . ?
F2 C14 1.316(8) . ?
N4 C15 1.358(5) . ?
N4 C18 1.323(5) . ?
F3 C14 1.317(8) . ?
C9 C10 1.434(6) . ?
C9 C8 1.401(6) . ?
C10 C11 1.400(6) . ?
C8 C13 1.409(6) . ?
C8 C7 1.433(7) . ?
C13 H13 0.9500 . ?
C13 C12 1.364(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.373(6) . ?
C17 C18 1.386(6) . ?
C16 H16 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.415(6) . ?
C12 C14 1.502(6) . ?
C7 C2 1.417(6) . ?
C7 C6 1.426(6) . ?
C18 H18 0.9500 . ?
C2 C3 1.418(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.400(8) . ?
C5 C6 1.361(8) . ?
C4 H4 0.9500 . ?
C4 C3 1.350(7) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
O1 C19 1.397(9) . ?
O1 C22 1.381(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.526(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.532(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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 N2 157.15(19) . 2_655 ?
N2 Zn1 N1 113.22(13) . 2_655 ?
N2 Zn1 N1 113.22(13) 2_655 . ?
N2 Zn1 N1 81.18(12) 2_655 2_655 ?
N2 Zn1 N1 81.18(12) . . ?
N1 Zn1 N1 105.1(2) . 2_655 ?
C15 N2 Zn1 116.1(2) . . ?
C15 N2 C10 127.1(3) . . ?
C10 N2 Zn1 116.8(2) . . ?
C9 N1 Zn1 110.5(2) . . ?
C1 N1 Zn1 129.6(3) . . ?
C1 N1 C9 119.8(3) . . ?
C16 N3 C15 116.4(3) . . ?
C18 N4 C15 116.4(3) . . ?
N3 C15 N2 122.5(3) . . ?
N3 C15 N4 124.8(3) . . ?
N4 C15 N2 112.7(3) . . ?
N1 C9 C10 116.1(3) . . ?
N1 C9 C8 121.0(4) . . ?
C8 C9 C10 122.8(4) . . ?
N2 C10 C9 115.1(3) . . ?
N2 C10 C11 127.9(4) . . ?
C11 C10 C9 116.9(4) . . ?
C9 C8 C13 117.8(4) . . ?
C9 C8 C7 118.8(4) . . ?
C13 C8 C7 123.4(4) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.3 . . ?
C16 C17 H17 122.1 . . ?
C16 C17 C18 115.8(4) . . ?
C18 C17 H17 122.1 . . ?
N3 C16 C17 123.6(4) . . ?
N3 C16 H16 118.2 . . ?
C17 C16 H16 118.2 . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.0(4) . . ?
C2 C1 H1 118.0 . . ?
C13 C12 C11 123.3(4) . . ?
C13 C12 C14 119.3(4) . . ?
C11 C12 C14 117.4(4) . . ?
C2 C7 C8 118.0(4) . . ?
C2 C7 C6 117.0(4) . . ?
C6 C7 C8 125.1(4) . . ?
N4 C18 C17 123.0(4) . . ?
N4 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C1 C2 C7 118.3(4) . . ?
C1 C2 C3 121.7(4) . . ?
C7 C2 C3 120.0(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.5(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
F1 C14 F2 107.6(5) . . ?
F1 C14 F3 105.1(5) . . ?
F1 C14 C12 113.8(4) . . ?
F2 C14 F3 102.5(5) . . ?
F2 C14 C12 113.1(5) . . ?
F3 C14 C12 113.7(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C22 O1 C19 108.0(7) . . ?
O1 C19 H19A 109.9 . . ?
O1 C19 H19B 109.9 . . ?
O1 C19 C20 108.9(7) . . ?
H19A C19 H19B 108.3 . . ?
C20 C19 H19A 109.9 . . ?
C20 C19 H19B 109.9 . . ?
C19 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
C19 C20 C21 104.5(7) . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 H20A 110.9 . . ?
C21 C20 H20B 110.9 . . ?
C20 C21 H21A 111.3 . . ?
C20 C21 H21B 111.3 . . ?
C20 C21 C22 102.4(7) . . ?
H21A C21 H21B 109.2 . . ?
C22 C21 H21A 111.3 . . ?
C22 C21 H21B 111.3 . . ?
O1 C22 C21 108.6(7) . . ?
O1 C22 H22A 110.0 . . ?
O1 C22 H22B 110.0 . . ?
C21 C22 H22A 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.3 . . ?

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
Zn1 N2 C15 N3 -175.1(3) . . . . ?
Zn1 N2 C15 N4 4.0(4) . . . . ?
Zn1 N2 C10 C9 4.2(5) . . . . ?
Zn1 N2 C10 C11 -173.3(4) . . . . ?
Zn1 N1 C9 C10 -3.1(5) . . . . ?
Zn1 N1 C9 C8 175.9(4) . . . . ?
Zn1 N1 C1 C2 -178.4(4) . . . . ?
N2 C10 C11 C12 176.9(4) . . . . ?
N1 C9 C10 N2 -0.4(6) . . . . ?
N1 C9 C10 C11 177.4(4) . . . . ?
N1 C9 C8 C13 -176.9(4) . . . . ?
N1 C9 C8 C7 4.2(7) . . . . ?
N1 C1 C2 C7 1.6(8) . . . . ?
N1 C1 C2 C3 -178.6(5) . . . . ?
C15 N2 C10 C9 -178.7(4) . . . . ?
C15 N2 C10 C11 3.8(7) . . . . ?
C15 N3 C16 C17 0.9(7) . . . . ?
C15 N4 C18 C17 0.2(6) . . . . ?
C9 N1 C1 C2 -1.2(7) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C9 C8 C13 C12 -0.3(8) . . . . ?
C9 C8 C7 C2 -3.7(8) . . . . ?
C9 C8 C7 C6 175.3(5) . . . . ?
C10 N2 C15 N3 7.7(6) . . . . ?
C10 N2 C15 N4 -173.2(4) . . . . ?
C10 C9 C8 C13 2.1(7) . . . . ?
C10 C9 C8 C7 -176.8(4) . . . . ?
C10 C11 C12 C13 2.4(8) . . . . ?
C10 C11 C12 C14 -176.0(5) . . . . ?
C8 C9 C10 N2 -179.4(4) . . . . ?
C8 C9 C10 C11 -1.6(6) . . . . ?
C8 C13 C12 C11 -1.9(9) . . . . ?
C8 C13 C12 C14 176.5(5) . . . . ?
C8 C7 C2 C1 1.0(8) . . . . ?
C8 C7 C2 C3 -178.9(5) . . . . ?
C8 C7 C6 C5 -180.0(6) . . . . ?
C13 C8 C7 C2 177.4(5) . . . . ?
C13 C8 C7 C6 -3.6(9) . . . . ?
C13 C12 C14 F1 -4.3(9) . . . . ?
C13 C12 C14 F2 -127.5(6) . . . . ?
C13 C12 C14 F3 116.1(6) . . . . ?
C11 C12 C14 F1 174.2(5) . . . . ?
C11 C12 C14 F2 51.0(7) . . . . ?
C11 C12 C14 F3 -65.5(7) . . . . ?
C16 N3 C15 N2 178.9(4) . . . . ?
C16 N3 C15 N4 0.0(6) . . . . ?
C16 C17 C18 N4 0.6(7) . . . . ?
C1 N1 C9 C10 179.2(4) . . . . ?
C1 N1 C9 C8 -1.7(7) . . . . ?
C1 C2 C3 C4 178.8(6) . . . . ?
C7 C8 C13 C12 178.6(5) . . . . ?
C7 C2 C3 C4 -1.3(10) . . . . ?
C18 N4 C15 N2 -179.5(3) . . . . ?
C18 N4 C15 N3 -0.5(6) . . . . ?
C18 C17 C16 N3 -1.1(7) . . . . ?
C2 C7 C6 C5 -1.0(10) . . . . ?
C5 C4 C3 C2 -0.5(10) . . . . ?
C4 C5 C6 C7 -0.8(11) . . . . ?
C6 C7 C2 C1 -178.1(5) . . . . ?
C6 C7 C2 C3 2.0(9) . . . . ?
C6 C5 C4 C3 1.6(11) . . . . ?
O1 C19 C20 C21 -6.7(12) . . . . ?
C19 O1 C22 C21 -29.2(12) . . . . ?
C19 C20 C21 C22 -9.6(12) . . . . ?
C20 C21 C22 O1 23.7(13) . . . . ?
C22 O1 C19 C20 22.4(11) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 128 electrons were 
found in a volume of 988Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.8[C4H8O] per Asymmetric Unit 
which account for 128 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 -0.563 494.5 63.6 '1.6 thf'
2 0.500 0.000 -0.383 494.5 63.6 '1.6 thf'

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