# Supplementary Information (SI) 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_dcf_20
_database_code_depnum_ccdc_archive 'CCDC 2364863'
loop_
_audit_author_name
_audit_author_address
'Hong-Ru Fu'
;Luoyang Normal University
China
;
_audit_update_record             
;
2024-07-29 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-07-18
# start Validation Reply Form
_vrf_FORMU01_ALERT_1_G           
; 
PROBLEM: There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C16 H21.5 N3.5 O3.5 Zn1
            Atom count from _chemical_formula_moiety:C13 H14 N3 O2.5 Zn1
RESPONSE: Difference is due to the addition of solvent molecules to structural formula.
;
_vrf_FORMU01_ALERT_2_G           
;
PROBLEM: There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C16 H21.5 N3.5 O3.5 Zn1
            Atom count from the _atom_site data:  C13 H13 N3 O2 Zn1
RESPONSE: Difference is due to the addition of solvent molecules to structural formula.
;
_vrf_CELLZ01_ALERT_1_G           
; 
PROBLEM: Difference between formula and atom_site contents detected.
PROBLEM: ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C16 H21.50 N3.50 O3.50 Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        128.00    104.00   24.00
           H        172.00    104.00   68.00
           N         28.00     24.00    4.00
           O         28.00     16.00   12.00
           Zn         8.00      8.00    0.00
RESPONSE: Difference is due to the addition of solvent molecules to structural formula.
;
# end Validation Reply Form
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C13 H13 N3 O2 Zn1, 0.5[H2O], 0.5[C2H6O], 0.5[C4H9NO]'
_chemical_formula_sum            'C16 H21.50 N3.50 O3.50 Zn'
_chemical_formula_weight         384.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   18.1052(4)
_cell_length_b                   18.1052(4)
_cell_length_c                   13.2724(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4350.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0830
_cell_measurement_theta_min      3.7960
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10487
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.223
_diffrn_reflns_theta_min         3.458
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1169
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  21.00   1.00   36.60    --   16.78  77.00 150.00   31
  2  ω     -2.00  73.00   1.00   36.60    --   16.78  38.00 -60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0254641000
_diffrn_orient_matrix_UB_12      -0.0289151000
_diffrn_orient_matrix_UB_13      -0.0098617000
_diffrn_orient_matrix_UB_21      0.0295259000
_diffrn_orient_matrix_UB_22      0.0256986000
_diffrn_orient_matrix_UB_23      0.0013781000
_diffrn_orient_matrix_UB_31      0.0039932000
_diffrn_orient_matrix_UB_32      -0.0061252000
_diffrn_orient_matrix_UB_33      0.0524955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.749
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                4162
_reflns_number_total             5903
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.178(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5016
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      0.991
_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)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.822(17)
 0.178(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O1-C9 = O2-C9
 1.25 with sigma of 0.01
 C17-C16 = C18-C16
 1.5 with sigma of 0.01
 C12-C10 \\sim C16-C10 \\sim C16-C14 \\sim C14-C13 \\sim C13-C12
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim O3 \\sim O4 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13
\\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: O1(0.5) O2(0.5) O3(0.5) O4(0.5) C9(0.5) C10(0.5) C11(0.5)
 H11A(0.5) H11B(0.5) H11C(0.5) C12(0.5) H12A(0.5) H12B(0.5) C13(0.5) H13A(0.5)
 H13B(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5) C17(0.5) H17A(0.5) H17B(0.5)
 H17C(0.5) C18(0.5) H18A(0.5) H18B(0.5) H18C(0.5)
6.a Ternary CH refined with riding coordinates:
 C14(H14)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.37945(2) 0.35795(2) 0.63401(3) 0.03137(13) Uani 1 1 d . . . . .
O1 O 0.3424(7) 0.4090(5) 0.7886(6) 0.093(3) Uani 0.5 1 d D U P A -1
O2 O 0.4518(7) 0.3722(6) 0.7556(7) 0.098(3) Uani 0.5 1 d D U P A -1
O3 O 0.3326(5) 0.4849(5) 1.2109(6) 0.078(3) Uani 0.5 1 d . U P A -1
O4 O 0.4040(5) 0.3873(4) 1.2345(5) 0.0405(16) Uani 0.5 1 d . U P A -1
N1 N 0.45642(17) 0.32894(18) 0.5336(2) 0.0356(7) Uani 1 1 d . . . . .
N2 N 0.44133(16) 0.32560(16) 0.4333(2) 0.0297(7) Uani 1 1 d . . . . .
N3 N 0.76314(17) 0.17846(19) 0.4001(2) 0.0457(8) Uani 1 1 d . . . . .
C1 C 0.4987(2) 0.2959(2) 0.3850(3) 0.0433(10) Uani 1 1 d . . . . .
H1 H 0.5016 0.2871 0.3161 0.052 Uiso 1 1 calc R . . . .
C2 C 0.5539(2) 0.2802(2) 0.4559(3) 0.0394(9) Uani 1 1 d . . . . .
C3 C 0.5240(2) 0.3013(2) 0.5482(3) 0.0413(10) Uani 1 1 d . . . . .
H3 H 0.5473 0.2969 0.6103 0.050 Uiso 1 1 calc R . . . .
C4 C 0.7103(2) 0.1751(3) 0.3369(3) 0.0629(14) Uani 1 1 d . . . . .
H4 H 0.7185 0.1489 0.2777 0.075 Uiso 1 1 calc R . . . .
C5 C 0.6405(2) 0.2080(3) 0.3499(3) 0.0617(13) Uani 1 1 d . . . . .
H5 H 0.6048 0.2043 0.2998 0.074 Uiso 1 1 calc R . . . .
C6 C 0.6257(2) 0.2462(2) 0.4384(3) 0.0467(10) Uani 1 1 d . . . . .
C7 C 0.6832(3) 0.2518(3) 0.5055(3) 0.0777(18) Uani 1 1 d . . . . .
H7 H 0.6773 0.2792 0.5643 0.093 Uiso 1 1 calc R . . . .
C8 C 0.7492(3) 0.2173(3) 0.4863(4) 0.0718(16) Uani 1 1 d . . . . .
H8 H 0.7864 0.2205 0.5345 0.086 Uiso 1 1 calc R . . . .
C9 C 0.4080(8) 0.4012(10) 0.8140(13) 0.089(4) Uani 0.5 1 d D U P A -1
C10 C 0.4456(13) 0.4277(15) 0.9155(19) 0.088(4) Uani 0.5 1 d D U P A -1
C11 C 0.4784(9) 0.5062(7) 0.8895(7) 0.109(5) Uani 0.5 1 d . U P A -1
H11A H 0.5292 0.5012 0.8698 0.163 Uiso 0.5 1 calc GR . P A -1
H11B H 0.4753 0.5375 0.9477 0.163 Uiso 0.5 1 calc GR . P A -1
H11C H 0.4508 0.5278 0.8352 0.163 Uiso 0.5 1 calc GR . P A -1
C12 C 0.5077(9) 0.3934(9) 0.9717(8) 0.109(4) Uani 0.5 1 d D U P A -1
H12A H 0.5544 0.4074 0.9414 0.131 Uiso 0.5 1 calc R . P A -1
H12B H 0.5035 0.3401 0.9694 0.131 Uiso 0.5 1 calc R . P A -1
C13 C 0.5047(8) 0.4201(9) 1.0809(8) 0.098(4) Uani 0.5 1 d D U P A -1
H13A H 0.5100 0.3792 1.1276 0.118 Uiso 0.5 1 calc R . P A -1
H13B H 0.5430 0.4563 1.0943 0.118 Uiso 0.5 1 calc R . P A -1
C14 C 0.4283(13) 0.4545(13) 1.0883(14) 0.069(3) Uani 0.5 1 d D U P A -1
H14 H 0.4361 0.5081 1.0851 0.082 Uiso 0.5 1 calc R . P A -1
C15 C 0.3827(9) 0.4411(7) 1.1826(10) 0.055(3) Uani 0.5 1 d . U P A -1
C16 C 0.3867(7) 0.4345(6) 0.9935(8) 0.082(3) Uani 0.5 1 d D U P A -1
C17 C 0.3324(10) 0.4940(10) 0.9786(11) 0.147(6) Uani 0.5 1 d D U P A -1
H17A H 0.3542 0.5327 0.9392 0.221 Uiso 0.5 1 calc GR . P A -1
H17B H 0.3175 0.5132 1.0428 0.221 Uiso 0.5 1 calc GR . P A -1
H17C H 0.2900 0.4747 0.9439 0.221 Uiso 0.5 1 calc GR . P A -1
C18 C 0.3401(9) 0.3688(8) 1.005(2) 0.077(7) Uani 0.5 1 d D U P A -1
H18A H 0.3307 0.3474 0.9404 0.115 Uiso 0.5 1 calc GR . P A -1
H18B H 0.2942 0.3826 1.0361 0.115 Uiso 0.5 1 calc GR . P A -1
H18C H 0.3650 0.3335 1.0471 0.115 Uiso 0.5 1 calc GR . 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 O1 2.348(10) . ?
Zn1 O2 2.095(11) . ?
Zn1 N1 1.998(3) . ?
Zn1 N2 2.007(3) 7_556 ?
Zn1 N3 2.023(3) 3_545 ?
O1 C9 1.242(12) . ?
O2 C9 1.226(12) . ?
O3 C15 1.263(16) . ?
O4 C15 1.253(15) . ?
N1 N2 1.361(4) . ?
N1 C3 1.335(5) . ?
N2 Zn1 2.007(3) 7_556 ?
N2 C1 1.333(4) . ?
N3 Zn1 2.023(3) 4_554 ?
N3 C4 1.273(5) . ?
N3 C8 1.366(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.402(5) . ?
C2 C3 1.393(5) . ?
C2 C6 1.456(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.408(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C6 C7 1.374(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.58(3) . ?
C10 C11 1.58(3) . ?
C10 C12 1.484(18) . ?
C10 C16 1.492(16) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.528(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.520(18) . ?
C14 H14 0.9800 . ?
C14 C15 1.52(3) . ?
C14 C16 1.511(14) . ?
C16 C17 1.471(11) . ?
C16 C18 1.466(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O1 57.1(4) . . ?
N1 Zn1 O1 152.3(3) . . ?
N1 Zn1 O2 96.3(3) . . ?
N1 Zn1 N2 103.87(12) . 7_556 ?
N1 Zn1 N3 102.06(13) . 3_545 ?
N2 Zn1 O1 87.4(3) 7_556 . ?
N2 Zn1 O2 123.6(3) 7_556 . ?
N2 Zn1 N3 115.70(13) 7_556 3_545 ?
N3 Zn1 O1 95.4(2) 3_545 . ?
N3 Zn1 O2 110.3(3) 3_545 . ?
C9 O1 Zn1 85.4(10) . . ?
C9 O2 Zn1 97.8(12) . . ?
N2 N1 Zn1 121.6(2) . . ?
C3 N1 Zn1 129.8(2) . . ?
C3 N1 N2 108.0(3) . . ?
N1 N2 Zn1 124.4(2) . 7_556 ?
C1 N2 Zn1 124.6(2) . 7_556 ?
C1 N2 N1 109.3(3) . . ?
C4 N3 Zn1 122.9(3) . 4_554 ?
C4 N3 C8 115.9(3) . . ?
C8 N3 Zn1 120.8(3) . 4_554 ?
N2 C1 H1 125.8 . . ?
N2 C1 C2 108.4(3) . . ?
C2 C1 H1 125.8 . . ?
C1 C2 C6 127.9(3) . . ?
C3 C2 C1 104.8(3) . . ?
C3 C2 C6 127.2(3) . . ?
N1 C3 C2 109.4(3) . . ?
N1 C3 H3 125.3 . . ?
C2 C3 H3 125.3 . . ?
N3 C4 H4 117.5 . . ?
N3 C4 C5 125.0(4) . . ?
C5 C4 H4 117.5 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C2 121.2(4) . . ?
C7 C6 C2 122.7(4) . . ?
C7 C6 C5 116.0(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
N3 C8 C7 123.4(4) . . ?
N3 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
O1 C9 C10 127.4(13) . . ?
O2 C9 O1 119.7(17) . . ?
O2 C9 C10 112.9(14) . . ?
C11 C10 C9 104.4(14) . . ?
C12 C10 C9 128.8(19) . . ?
C12 C10 C11 101.6(19) . . ?
C12 C10 C16 103.1(15) . . ?
C16 C10 C9 107.9(17) . . ?
C16 C10 C11 110.2(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 110.0 . . ?
C10 C12 H12B 110.0 . . ?
C10 C12 C13 108.6(17) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
C12 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 C12 102.9(13) . . ?
C14 C13 H13A 111.2 . . ?
C14 C13 H13B 111.2 . . ?
C13 C14 H14 105.8 . . ?
C15 C14 C13 118.8(15) . . ?
C15 C14 H14 105.8 . . ?
C16 C14 C13 107.5(11) . . ?
C16 C14 H14 105.8 . . ?
C16 C14 C15 112.1(18) . . ?
O3 C15 C14 122.3(12) . . ?
O4 C15 O3 123.1(12) . . ?
O4 C15 C14 114.2(13) . . ?
C10 C16 C14 104.0(9) . . ?
C17 C16 C10 116.4(13) . . ?
C17 C16 C14 105.7(11) . . ?
C18 C16 C10 114.7(17) . . ?
C18 C16 C14 113.1(17) . . ?
C18 C16 C17 102.9(15) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C9 O2 -2.6(17) . . . . ?
Zn1 O1 C9 C10 174.8(19) . . . . ?
Zn1 O2 C9 O1 3.0(19) . . . . ?
Zn1 O2 C9 C10 -174.8(14) . . . . ?
Zn1 N1 N2 Zn1 22.0(4) . . . 7_556 ?
Zn1 N1 N2 C1 -172.0(3) . . . . ?
Zn1 N1 C3 C2 171.9(3) . . . . ?
Zn1 N2 C1 C2 165.1(3) 7_556 . . . ?
Zn1 N3 C4 C5 173.0(4) 4_554 . . . ?
Zn1 N3 C8 C7 -173.7(5) 4_554 . . . ?
O1 C9 C10 C11 -93(2) . . . . ?
O1 C9 C10 C12 148(2) . . . . ?
O1 C9 C10 C16 24(3) . . . . ?
O2 C9 C10 C11 84.1(19) . . . . ?
O2 C9 C10 C12 -34(3) . . . . ?
O2 C9 C10 C16 -158.7(16) . . . . ?
N1 N2 C1 C2 -0.9(4) . . . . ?
N2 N1 C3 C2 0.6(5) . . . . ?
N2 C1 C2 C3 1.2(5) . . . . ?
N2 C1 C2 C6 178.7(4) . . . . ?
N3 C4 C5 C6 -1.5(9) . . . . ?
C1 C2 C3 N1 -1.1(5) . . . . ?
C1 C2 C6 C5 -16.5(7) . . . . ?
C1 C2 C6 C7 161.1(5) . . . . ?
C2 C6 C7 C8 178.6(5) . . . . ?
C3 N1 N2 Zn1 -165.8(3) . . . 7_556 ?
C3 N1 N2 C1 0.2(4) . . . . ?
C3 C2 C6 C5 160.5(5) . . . . ?
C3 C2 C6 C7 -21.9(8) . . . . ?
C4 N3 C8 C7 -0.6(9) . . . . ?
C4 C5 C6 C2 -179.0(4) . . . . ?
C4 C5 C6 C7 3.2(7) . . . . ?
C5 C6 C7 C8 -3.7(8) . . . . ?
C6 C2 C3 N1 -178.6(4) . . . . ?
C6 C7 C8 N3 2.6(10) . . . . ?
C8 N3 C4 C5 0.1(8) . . . . ?
C9 C10 C12 C13 -158.5(17) . . . . ?
C9 C10 C16 C14 176.1(16) . . . . ?
C9 C10 C16 C17 -68(2) . . . . ?
C9 C10 C16 C18 52(2) . . . . ?
C10 C12 C13 C14 14(3) . . . . ?
C11 C10 C12 C13 82.1(14) . . . . ?
C11 C10 C16 C14 -70(2) . . . . ?
C11 C10 C16 C17 45(2) . . . . ?
C11 C10 C16 C18 165.5(17) . . . . ?
C12 C10 C16 C14 37.4(16) . . . . ?
C12 C10 C16 C17 153.2(15) . . . . ?
C12 C10 C16 C18 -87(2) . . . . ?
C12 C13 C14 C15 138.7(14) . . . . ?
C12 C13 C14 C16 10(2) . . . . ?
C13 C14 C15 O3 155.4(15) . . . . ?
C13 C14 C15 O4 -18(2) . . . . ?
C13 C14 C16 C10 -29.9(17) . . . . ?
C13 C14 C16 C17 -153.0(17) . . . . ?
C13 C14 C16 C18 95(2) . . . . ?
C15 C14 C16 C10 -162.3(14) . . . . ?
C15 C14 C16 C17 74.6(18) . . . . ?
C15 C14 C16 C18 -37.2(18) . . . . ?
C16 C10 C12 C13 -32(2) . . . . ?
C16 C14 C15 O3 -78.1(18) . . . . ?
C16 C14 C15 O4 108.7(14) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 307 electrons were 
found in a volume of 2103Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[H2O], 0.5[C2H6O] and 0.5[C4H9NO]  per formula unit 
which account for 336 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 0.360 0.373 -0.943 2102.9 306.6 '8 H2O,8 EtOH'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.855
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.822(17)
2 0.178(17)


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b50_auto
_database_code_depnum_ccdc_archive 'CCDC 2364864'
loop_
_audit_author_name
_audit_author_address
'Hong-Ru Fu'
;Luoyang Normal University
China
;
_audit_update_record             
;
2024-07-29 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-07-18
# start Validation Reply Form
_vrf_FORMU01_ALERT_1_G           
; 
PROBLEM: There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C16 H22.5 N3.5 O4 Zn1
            Atom count from _chemical_formula_moiety:C13 H13 N3 O2 
RESPONSE: Difference is due to the addition of solvent molecules to structural formula.
;
_vrf_FORMU01_ALERT_2_G           
;
PROBLEM: There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C16 H22.5 N3.5 O4 Zn1
            Atom count from the _atom_site data:  C13 H13 N3 O2 
RESPONSE: Difference is due to the addition of solvent molecules to structural formula.
;
_vrf_CELLZ01_ALERT_1_G           
; 
PROBLEM: Difference between formula and atom_site contents detected.
PROBLEM: ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C16 H22.50 N3.50 O4 Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        128.00    104.00   24.00
           H        180.00    104.00   76.00
           N         28.00     24.00    4.00
           O         32.00     16.00   16.00
           Zn         8.00      8.00    0.00

RESPONSE: Difference is due to the addition of solvent molecules to structural formula.
;
# end Validation Reply Form

_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
"'C13 H13 N3 O2 Zn1, 1[H2O], 0.5[C2H6O], 0.5[C4H9NO]'"
_chemical_formula_sum            'C16 H22.50 N3.50 O4 Zn'
_chemical_formula_weight         393.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   18.1042(4)
_cell_length_b                   18.1042(4)
_cell_length_c                   13.2792(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4352.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4186
_cell_measurement_temperature    290
_cell_measurement_theta_max      24.7780
_cell_measurement_theta_min      3.7930
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11548
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.212
_diffrn_reflns_theta_min         3.268
_diffrn_ambient_temperature      290.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00  78.00   1.00   16.18    --   16.93-139.00 140.00   33
  2  ω      0.00  84.00   1.00   16.18    --   16.93  57.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0054472000
_diffrn_orient_matrix_UB_12      -0.0387614000
_diffrn_orient_matrix_UB_13      0.0032306000
_diffrn_orient_matrix_UB_21      0.0381960000
_diffrn_orient_matrix_UB_22      0.0058432000
_diffrn_orient_matrix_UB_23      0.0085609000
_diffrn_orient_matrix_UB_31      -0.0066057000
_diffrn_orient_matrix_UB_32      0.0014152000
_diffrn_orient_matrix_UB_33      0.0526093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.757
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                4317
_reflns_number_total             5901
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.209(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5024
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.008
_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)+(0.0519P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.791(18)
 0.209(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim O3 \\sim O4 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13
\\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O1(0.5) O2(0.5) O3(0.5) O4(0.5) C9(0.5) C10(0.5) H10(0.5) C11(0.5)
 H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5) C13(0.5) C14(0.5) C15(0.5)
 H15A(0.5) H15B(0.5) H15C(0.5) C16(0.5) C17(0.5) H17A(0.5) H17B(0.5) H17C(0.5)
 C18(0.5) H18A(0.5) H18B(0.5) H18C(0.5)
5.a Ternary CH refined with riding coordinates:
 C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.64148(2) 0.62011(2) 0.63511(3) 0.03033(13) Uani 1 1 d . . . . .
O1 O 0.5944(6) 0.6149(6) 0.7665(7) 0.051(2) Uani 0.5 1 d . U P A -1
O2 O 0.6630(6) 0.5152(6) 0.7830(7) 0.085(3) Uani 0.5 1 d . U P A -1
O3 O 0.6570(8) 0.5901(6) 1.2121(8) 0.090(4) Uani 0.5 1 d . U P A -1
O4 O 0.5461(7) 0.6289(6) 1.2439(6) 0.083(3) Uani 0.5 1 d . U P A -1
N1 N 0.67126(18) 0.54320(17) 0.5336(2) 0.0340(7) Uani 1 1 d . . . . .
N2 N 0.67438(18) 0.55846(17) 0.4339(2) 0.0339(7) Uani 1 1 d . . . . .
N3 N 0.82059(19) 0.23668(18) 0.4018(2) 0.0409(8) Uani 1 1 d . . . . .
C1 C 0.6979(2) 0.4763(2) 0.5470(3) 0.0418(10) Uani 1 1 d . . . . .
H1 H 0.7013 0.4522 0.6087 0.050 Uiso 1 1 calc R . . . .
C2 C 0.7204(2) 0.4469(2) 0.4553(3) 0.0413(9) Uani 1 1 d . . . . .
C3 C 0.7049(2) 0.5004(2) 0.3896(3) 0.0370(8) Uani 1 1 d . . . . .
H3 H 0.7143 0.4972 0.3209 0.044 Uiso 1 1 calc R . . . .
C4 C 0.8218(3) 0.2906(2) 0.3350(3) 0.0592(14) Uani 1 1 d . . . . .
H4 H 0.8452 0.2819 0.2738 0.071 Uiso 1 1 calc R . . . .
C5 C 0.7910(3) 0.3580(3) 0.3500(3) 0.0655(14) Uani 1 1 d . . . . .
H5 H 0.7952 0.3941 0.3005 0.079 Uiso 1 1 calc R . . . .
C6 C 0.7533(2) 0.3738(2) 0.4382(3) 0.0434(10) Uani 1 1 d . . . . .
C7 C 0.7499(3) 0.3172(3) 0.5062(4) 0.0710(16) Uani 1 1 d . . . . .
H7 H 0.7244 0.3240 0.5663 0.085 Uiso 1 1 calc R . . . .
C8 C 0.7834(3) 0.2508(3) 0.4875(4) 0.0655(15) Uani 1 1 d . . . . .
H8 H 0.7803 0.2138 0.5360 0.079 Uiso 1 1 calc R . . . .
C9 C 0.6127(10) 0.5579(9) 0.8139(15) 0.058(3) Uani 0.5 1 d . U P A -1
C10 C 0.573(2) 0.545(2) 0.915(3) 0.071(4) Uani 0.5 1 d . U P A -1
H10 H 0.5676 0.4909 0.9209 0.085 Uiso 0.5 1 calc R . P A -1
C11 C 0.4933(9) 0.5776(9) 0.9288(9) 0.093(4) Uani 0.5 1 d . U P A -1
H11A H 0.4841 0.6160 0.8795 0.111 Uiso 0.5 1 calc R . P A -1
H11B H 0.4563 0.5393 0.9209 0.111 Uiso 0.5 1 calc R . P A -1
C12 C 0.4912(8) 0.6074(9) 1.0290(8) 0.095(3) Uani 0.5 1 d . U P A -1
H12A H 0.4433 0.5987 1.0596 0.115 Uiso 0.5 1 calc R . P A -1
H12B H 0.5003 0.6602 1.0278 0.115 Uiso 0.5 1 calc R . P A -1
C13 C 0.555(2) 0.566(2) 1.091(3) 0.079(4) Uani 0.5 1 d . U P A -1
C14 C 0.5906(13) 0.5961(11) 1.1890(15) 0.077(5) Uani 0.5 1 d . U P A -1
C15 C 0.5294(9) 0.4903(8) 1.1116(9) 0.105(5) Uani 0.5 1 d . U P A -1
H15A H 0.5008 0.4729 1.0555 0.157 Uiso 0.5 1 calc GR . P A -1
H15B H 0.4994 0.4901 1.1711 0.157 Uiso 0.5 1 calc GR . P A -1
H15C H 0.5712 0.4585 1.1214 0.157 Uiso 0.5 1 calc GR . P A -1
C16 C 0.6133(7) 0.5666(7) 1.0042(7) 0.080(3) Uani 0.5 1 d . U P A -1
C17 C 0.6679(12) 0.5052(11) 1.0275(11) 0.145(7) Uani 0.5 1 d . U P A -1
H17A H 0.6418 0.4595 1.0360 0.217 Uiso 0.5 1 calc GR . P A -1
H17B H 0.6941 0.5168 1.0883 0.217 Uiso 0.5 1 calc GR . P A -1
H17C H 0.7024 0.5005 0.9729 0.217 Uiso 0.5 1 calc GR . P A -1
C18 C 0.6576(10) 0.6338(10) 0.9895(13) 0.070(5) Uani 0.5 1 d . U P A -1
H18A H 0.6956 0.6243 0.9407 0.105 Uiso 0.5 1 calc GR . P A -1
H18B H 0.6799 0.6478 1.0523 0.105 Uiso 0.5 1 calc GR . P A -1
H18C H 0.6264 0.6730 0.9659 0.105 Uiso 0.5 1 calc GR . 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 O1 1.944(10) . ?
Zn1 N1 2.011(3) . ?
Zn1 N2 2.016(3) 7_556 ?
Zn1 N3 2.042(3) 4_565 ?
O1 C9 1.25(2) . ?
O2 C9 1.26(2) . ?
O3 C14 1.25(3) . ?
O4 C14 1.24(3) . ?
N1 N2 1.354(4) . ?
N1 C1 1.316(5) . ?
N2 Zn1 2.016(3) 7_556 ?
N2 C3 1.326(4) . ?
N3 Zn1 2.042(3) 3_644 ?
N3 C4 1.319(5) . ?
N3 C8 1.347(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.389(5) . ?
C2 C3 1.333(5) . ?
C2 C6 1.469(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.357(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C6 C7 1.368(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.54(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.58(4) . ?
C10 C16 1.44(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.437(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.61(4) . ?
C13 C14 1.55(4) . ?
C13 C15 1.47(4) . ?
C13 C16 1.57(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.52(2) . ?
C16 C18 1.469(14) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 133.2(3) . . ?
O1 Zn1 N2 96.0(3) . 7_556 ?
O1 Zn1 N3 107.3(3) . 4_565 ?
N1 Zn1 N2 103.45(12) . 7_556 ?
N1 Zn1 N3 102.15(13) . 4_565 ?
N2 Zn1 N3 114.98(13) 7_556 4_565 ?
C9 O1 Zn1 112.1(11) . . ?
N2 N1 Zn1 121.7(2) . . ?
C1 N1 Zn1 130.2(3) . . ?
C1 N1 N2 107.7(3) . . ?
N1 N2 Zn1 125.2(2) . 7_556 ?
C3 N2 Zn1 126.3(2) . 7_556 ?
C3 N2 N1 106.8(3) . . ?
C4 N3 Zn1 122.9(3) . 3_644 ?
C4 N3 C8 115.9(3) . . ?
C8 N3 Zn1 120.9(3) . 3_644 ?
N1 C1 H1 125.0 . . ?
N1 C1 C2 110.0(3) . . ?
C2 C1 H1 125.0 . . ?
C1 C2 C6 126.8(4) . . ?
C3 C2 C1 103.5(4) . . ?
C3 C2 C6 129.6(3) . . ?
N2 C3 C2 111.9(3) . . ?
N2 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
N3 C4 H4 118.0 . . ?
N3 C4 C5 124.1(4) . . ?
C5 C4 H4 118.0 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C2 121.1(4) . . ?
C7 C6 C2 123.7(4) . . ?
C7 C6 C5 115.2(4) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(4) . . ?
C8 C7 H7 119.4 . . ?
N3 C8 C7 122.7(4) . . ?
N3 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
O1 C9 O2 122.1(17) . . ?
O1 C9 C10 116.5(18) . . ?
O2 C9 C10 121.4(17) . . ?
C9 C10 H10 105.6 . . ?
C9 C10 C11 118(2) . . ?
C11 C10 H10 105.6 . . ?
C16 C10 C9 116(3) . . ?
C16 C10 H10 105.6 . . ?
C16 C10 C11 105(3) . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 C10 105.7(18) . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
C11 C12 C13 106.3(19) . . ?
H12A C12 H12B 108.7 . . ?
C13 C12 H12A 110.5 . . ?
C13 C12 H12B 110.5 . . ?
C14 C13 C12 124(3) . . ?
C14 C13 C16 110(2) . . ?
C15 C13 C12 108(2) . . ?
C15 C13 C14 108(2) . . ?
C15 C13 C16 111(3) . . ?
C16 C13 C12 96(2) . . ?
O3 C14 C13 125(2) . . ?
O4 C14 O3 121.7(19) . . ?
O4 C14 C13 113(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 C13 105.2(14) . . ?
C10 C16 C17 106.9(17) . . ?
C10 C16 C18 113.3(18) . . ?
C17 C16 C13 106.2(16) . . ?
C18 C16 C13 118.4(19) . . ?
C18 C16 C17 106.1(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C9 O2 8(2) . . . . ?
Zn1 O1 C9 C10 -174.8(17) . . . . ?
Zn1 N1 N2 Zn1 -22.0(4) . . . 7_556 ?
Zn1 N1 N2 C3 171.8(3) . . . . ?
Zn1 N1 C1 C2 -171.5(3) . . . . ?
Zn1 N2 C3 C2 -164.6(3) 7_556 . . . ?
Zn1 N3 C4 C5 -171.0(4) 3_644 . . . ?
Zn1 N3 C8 C7 172.5(5) 3_644 . . . ?
O1 C9 C10 C11 27(3) . . . . ?
O1 C9 C10 C16 -99(3) . . . . ?
O2 C9 C10 C11 -156(2) . . . . ?
O2 C9 C10 C16 78(3) . . . . ?
N1 N2 C3 C2 1.4(5) . . . . ?
N1 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C2 C6 179.8(4) . . . . ?
N2 N1 C1 C2 1.1(5) . . . . ?
N3 C4 C5 C6 -2.0(9) . . . . ?
C1 N1 N2 Zn1 164.7(3) . . . 7_556 ?
C1 N1 N2 C3 -1.5(4) . . . . ?
C1 C2 C3 N2 -0.7(5) . . . . ?
C1 C2 C6 C5 -162.7(5) . . . . ?
C1 C2 C6 C7 16.9(8) . . . . ?
C2 C6 C7 C8 -178.2(5) . . . . ?
C3 C2 C6 C5 17.3(8) . . . . ?
C3 C2 C6 C7 -163.1(5) . . . . ?
C4 N3 C8 C7 -1.4(8) . . . . ?
C4 C5 C6 C2 179.4(5) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C5 C6 C7 C8 1.5(8) . . . . ?
C6 C2 C3 N2 179.3(4) . . . . ?
C6 C7 C8 N3 -0.7(9) . . . . ?
C8 N3 C4 C5 2.7(8) . . . . ?
C9 C10 C11 C12 -138(2) . . . . ?
C9 C10 C16 C13 166.4(17) . . . . ?
C9 C10 C16 C17 -81(2) . . . . ?
C9 C10 C16 C18 36(3) . . . . ?
C10 C11 C12 C13 -22(3) . . . . ?
C11 C10 C16 C13 34(3) . . . . ?
C11 C10 C16 C17 147.1(18) . . . . ?
C11 C10 C16 C18 -96(2) . . . . ?
C11 C12 C13 C14 159(2) . . . . ?
C11 C12 C13 C15 -74(3) . . . . ?
C11 C12 C13 C16 41(2) . . . . ?
C12 C13 C14 O3 -143(3) . . . . ?
C12 C13 C14 O4 37(3) . . . . ?
C12 C13 C16 C10 -45(3) . . . . ?
C12 C13 C16 C17 -158.3(18) . . . . ?
C12 C13 C16 C18 83(2) . . . . ?
C14 C13 C16 C10 -174.5(19) . . . . ?
C14 C13 C16 C17 72(3) . . . . ?
C14 C13 C16 C18 -47(3) . . . . ?
C15 C13 C14 O3 90(3) . . . . ?
C15 C13 C14 O4 -91(3) . . . . ?
C15 C13 C16 C10 66(3) . . . . ?
C15 C13 C16 C17 -47(3) . . . . ?
C15 C13 C16 C18 -166(2) . . . . ?
C16 C10 C11 C12 -7(2) . . . . ?
C16 C13 C14 O3 -31(3) . . . . ?
C16 C13 C14 O4 148(2) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 352 electrons were 
found in a volume of 2121Å³ in 1 void per unit cell. 
This is consistent with the presence of 
1[H2O], 0.5[C2H6O] and 0.5[C4H9NO]  per formula unit 
which account for 376 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 0.116 -0.871 -0.609 2120.9 351.5 '16 H2O,8 EtOH'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.777
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.791(18)
2 0.209(18)

