# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_jtm1146_5
_database_code_depnum_ccdc_archive 'CCDC 1934944'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Department of Chemistry, Tulane University
United States of America
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 Mn2 N6 O12, 2(H2 O)'
_chemical_formula_sum            'C34 H30 Mn2 N6 O14'
_chemical_formula_weight         856.52

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1430(12)
_cell_length_b                   9.3717(15)
_cell_length_c                   13.017(2)
_cell_angle_alpha                85.852(2)
_cell_angle_beta                 75.893(2)
_cell_angle_gamma                89.950(2)
_cell_volume                     842.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3403
_cell_measurement_theta_min      2.6159
_cell_measurement_theta_max      27.1364
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       column
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             438
_exptl_transmission_factor_min   0.651
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2009)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 60 sec/frame was used. Analysis 
of 694 reflections having I/σ(I) > 12 and chosen from the full 
data set with CELL_NOW (Sheldrick, 2008) showed the crystal 
to belong to the triclinic system and to be twinned by a 180° 
rotation about the a axis. The raw data were processed using 
the multi-component version of SAINT under control of the 
two-component orientation file generated by CELL_NOW.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15261
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             15261
_reflns_number_gt                10490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 Å) while those 
attached to oxygen were placed in locations derived from a difference 
map and their coordinates adjusted to give O---H = 0.87 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms. Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.4117P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15261
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1838
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.35052(8) 0.21380(7) 0.26548(5) 0.0229(2) Uani 1 1 d . . . . .
O1 O 0.0821(4) 0.3035(3) 0.2545(2) 0.0334(7) Uani 1 1 d . . . . .
O2 O -0.1250(4) 0.4473(3) 0.1984(2) 0.0296(7) Uani 1 1 d . . . . .
O3 O 0.4213(4) 0.4383(3) 0.2414(2) 0.0285(7) Uani 1 1 d . . . . .
O4 O 0.7920(4) 0.8235(3) 0.0078(2) 0.0314(7) Uani 1 1 d . . . . .
O5 O 0.6250(4) 0.8720(3) -0.1148(2) 0.0315(7) Uani 1 1 d . . . . .
O6 O 0.6572(4) 0.2001(3) 0.2522(2) 0.0248(6) Uani 1 1 d . . . . .
H6A H 0.724591 0.138654 0.212042 0.037 Uiso 1 1 d R U . . .
H6B H 0.728646 0.277605 0.237775 0.037 Uiso 1 1 d R U . . .
N1 N 0.2723(4) -0.0031(3) 0.3513(3) 0.0229(7) Uani 1 1 d . . . . .
N2 N 0.3071(4) 0.2387(3) 0.4420(3) 0.0215(7) Uani 1 1 d . . . . .
N3 N 0.3785(4) 0.5210(3) 0.1644(2) 0.0209(7) Uani 1 1 d . . . . .
C1 C 0.2492(6) -0.1200(5) 0.3024(3) 0.0302(10) Uani 1 1 d . . . . .
H1 H 0.266602 -0.112085 0.227506 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2008(6) -0.2525(5) 0.3572(4) 0.0338(10) Uani 1 1 d . . . . .
H2 H 0.184155 -0.333733 0.320526 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1773(6) -0.2642(4) 0.4652(4) 0.0314(10) Uani 1 1 d . . . . .
H3 H 0.143410 -0.353902 0.504300 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2032(6) -0.1450(4) 0.5166(3) 0.0251(9) Uani 1 1 d . . . . .
H4 H 0.189020 -0.151510 0.591302 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2504(5) -0.0151(4) 0.4573(3) 0.0209(8) Uani 1 1 d . . . . .
C6 C 0.2733(5) 0.1185(4) 0.5077(3) 0.0206(8) Uani 1 1 d . . . . .
C7 C 0.2563(6) 0.1216(5) 0.6158(3) 0.0285(9) Uani 1 1 d . . . . .
H7 H 0.234622 0.035435 0.660472 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2709(6) 0.2504(5) 0.6583(3) 0.0325(10) Uani 1 1 d . . . . .
H8 H 0.258890 0.254362 0.732362 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3035(6) 0.3736(5) 0.5913(4) 0.0324(10) Uani 1 1 d . . . . .
H9 H 0.313360 0.464176 0.618118 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3212(6) 0.3621(4) 0.4847(3) 0.0276(9) Uani 1 1 d . . . . .
H10 H 0.344983 0.447055 0.438768 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0396(5) 0.4149(4) 0.2051(3) 0.0217(8) Uani 1 1 d . . . . .
C12 C 0.1979(5) 0.5206(4) 0.1456(3) 0.0217(8) Uani 1 1 d . . . . .
C13 C 0.1621(6) 0.6211(4) 0.0696(3) 0.0253(9) Uani 1 1 d . . . . .
H13 H 0.037314 0.624465 0.056131 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3033(6) 0.7165(5) 0.0131(3) 0.0274(9) Uani 1 1 d . . . . .
H14 H 0.275531 0.785065 -0.038290 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4863(5) 0.7117(4) 0.0320(3) 0.0228(8) Uani 1 1 d . . . . .
C16 C 0.5192(5) 0.6128(4) 0.1089(3) 0.0233(8) Uani 1 1 d . . . . .
H16 H 0.643328 0.609016 0.123230 0.028 Uiso 1 1 calc R U . . .
C17 C 0.6481(6) 0.8110(4) -0.0295(3) 0.0261(9) Uani 1 1 d . . . . .
O7 O 0.9049(4) 0.0151(3) 0.1402(2) 0.0321(7) Uani 1 1 d . . . . .
H7A H 0.869970 -0.041560 0.097935 0.048 Uiso 1 1 d R U . . .
H7B H 1.014609 0.051785 0.103130 0.048 Uiso 1 1 d 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
Mn1 O1 2.126(3) . ?
Mn1 O5 2.141(3) 2_665 ?
Mn1 O3 2.147(3) . ?
Mn1 O6 2.160(3) . ?
Mn1 N1 2.250(3) . ?
Mn1 N2 2.272(3) . ?
O1 C11 1.262(5) . ?
O2 C11 1.235(5) . ?
O3 N3 1.317(4) . ?
O4 C17 1.247(5) . ?
O5 C17 1.260(5) . ?
O6 H6A 0.8700 . ?
O6 H6B 0.8702 . ?
N1 C1 1.336(5) . ?
N1 C5 1.347(5) . ?
N2 C10 1.333(5) . ?
N2 C6 1.348(5) . ?
N3 C16 1.353(5) . ?
N3 C12 1.371(5) . ?
C1 C2 1.386(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.482(5) . ?
C6 C7 1.385(6) . ?
C7 C8 1.378(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.524(5) . ?
C12 C13 1.385(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(5) . ?
C15 C17 1.512(5) . ?
C16 H16 0.9500 . ?
O7 H7A 0.8699 . ?
O7 H7B 0.8699 . ?

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 Mn1 O5 89.12(12) . 2_665 ?
O1 Mn1 O3 78.26(11) . . ?
O5 Mn1 O3 109.36(11) 2_665 . ?
O1 Mn1 O6 159.05(11) . . ?
O5 Mn1 O6 92.51(11) 2_665 . ?
O3 Mn1 O6 81.51(10) . . ?
O1 Mn1 N1 104.64(11) . . ?
O5 Mn1 N1 91.37(11) 2_665 . ?
O3 Mn1 N1 159.19(12) . . ?
O6 Mn1 N1 96.21(11) . . ?
O1 Mn1 N2 95.52(12) . . ?
O5 Mn1 N2 163.70(11) 2_665 . ?
O3 Mn1 N2 86.90(11) . . ?
O6 Mn1 N2 88.73(11) . . ?
N1 Mn1 N2 72.34(12) . . ?
C11 O1 Mn1 132.5(3) . . ?
N3 O3 Mn1 122.5(2) . . ?
C17 O5 Mn1 129.3(3) . 2_665 ?
Mn1 O6 H6A 119.7 . . ?
Mn1 O6 H6B 119.6 . . ?
H6A O6 H6B 103.9 . . ?
C1 N1 C5 118.7(3) . . ?
C1 N1 Mn1 123.4(3) . . ?
C5 N1 Mn1 117.8(3) . . ?
C10 N2 C6 117.8(3) . . ?
C10 N2 Mn1 124.9(3) . . ?
C6 N2 Mn1 117.3(3) . . ?
O3 N3 C16 116.3(3) . . ?
O3 N3 C12 122.0(3) . . ?
C16 N3 C12 121.6(3) . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 C6 116.5(3) . . ?
C4 C5 C6 121.8(4) . . ?
N2 C6 C7 121.6(4) . . ?
N2 C6 C5 115.8(3) . . ?
C7 C6 C5 122.6(3) . . ?
C8 C7 C6 119.6(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 118.4(4) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
N2 C10 C9 123.8(4) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
O2 C11 O1 125.2(4) . . ?
O2 C11 C12 114.7(3) . . ?
O1 C11 C12 120.1(3) . . ?
N3 C12 C13 117.5(3) . . ?
N3 C12 C11 122.3(3) . . ?
C13 C12 C11 120.2(3) . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.5(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 118.3(4) . . ?
C16 C15 C17 119.8(3) . . ?
C14 C15 C17 121.8(4) . . ?
N3 C16 C15 121.4(3) . . ?
N3 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
O4 C17 O5 126.2(4) . . ?
O4 C17 C15 117.5(3) . . ?
O5 C17 C15 116.2(3) . . ?
H7A O7 H7B 104.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O3 N3 C16 -135.3(3) . . . . ?
Mn1 O3 N3 C12 48.6(4) . . . . ?
C5 N1 C1 C2 1.0(6) . . . . ?
Mn1 N1 C1 C2 -179.9(3) . . . . ?
N1 C1 C2 C3 -0.5(7) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C1 N1 C5 C4 -0.5(6) . . . . ?
Mn1 N1 C5 C4 -179.7(3) . . . . ?
C1 N1 C5 C6 -178.7(3) . . . . ?
Mn1 N1 C5 C6 2.2(4) . . . . ?
C3 C4 C5 N1 -0.3(6) . . . . ?
C3 C4 C5 C6 177.7(3) . . . . ?
C10 N2 C6 C7 -0.9(6) . . . . ?
Mn1 N2 C6 C7 176.1(3) . . . . ?
C10 N2 C6 C5 177.5(3) . . . . ?
Mn1 N2 C6 C5 -5.5(4) . . . . ?
N1 C5 C6 N2 2.2(5) . . . . ?
C4 C5 C6 N2 -175.9(3) . . . . ?
N1 C5 C6 C7 -179.4(4) . . . . ?
C4 C5 C6 C7 2.5(6) . . . . ?
N2 C6 C7 C8 1.1(6) . . . . ?
C5 C6 C7 C8 -177.2(4) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C6 N2 C10 C9 0.0(6) . . . . ?
Mn1 N2 C10 C9 -176.7(3) . . . . ?
C8 C9 C10 N2 0.7(6) . . . . ?
Mn1 O1 C11 O2 173.0(3) . . . . ?
Mn1 O1 C11 C12 -5.7(6) . . . . ?
O3 N3 C12 C13 173.9(3) . . . . ?
C16 N3 C12 C13 -2.1(6) . . . . ?
O3 N3 C12 C11 -5.9(6) . . . . ?
C16 N3 C12 C11 178.1(4) . . . . ?
O2 C11 C12 N3 164.0(4) . . . . ?
O1 C11 C12 N3 -17.2(6) . . . . ?
O2 C11 C12 C13 -15.8(5) . . . . ?
O1 C11 C12 C13 163.0(4) . . . . ?
N3 C12 C13 C14 1.3(6) . . . . ?
C11 C12 C13 C14 -178.8(4) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C13 C14 C15 C17 178.4(4) . . . . ?
O3 N3 C16 C15 -175.1(4) . . . . ?
C12 N3 C16 C15 1.1(6) . . . . ?
C14 C15 C16 N3 0.7(6) . . . . ?
C17 C15 C16 N3 -179.1(3) . . . . ?
Mn1 O5 C17 O4 103.3(5) 2_665 . . . ?
Mn1 O5 C17 C15 -75.7(4) 2_665 . . . ?
C16 C15 C17 O4 -16.5(6) . . . . ?
C14 C15 C17 O4 163.6(4) . . . . ?
C16 C15 C17 O5 162.5(4) . . . . ?
C14 C15 C17 O5 -17.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6A O7 0.87 1.85 2.714(4) 169 . yes
O6 H6B O2 0.87 1.87 2.742(4) 176 1_655 yes
C4 H4 O6 0.95 2.55 3.399(5) 148 2_656 yes
C7 H7 O7 0.95 2.55 3.269(5) 132 2_656 yes
C10 H10 O3 0.95 2.50 3.102(5) 121 . yes
C16 H16 O2 0.95 2.56 3.377(5) 144 1_655 yes
O7 H7A O4 0.87 1.95 2.824(4) 177 1_545 yes
O7 H7B O4 0.87 2.04 2.870(4) 160 2_765 yes

_refine_diff_density_max         1.139
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.150

####################################################################### 
# 
# 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_JTM1189_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1979889'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Department of Chemistry, Tulane University
United States of America
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 N4 O8 Zn, 2(H2 O)'
_chemical_formula_sum            'C24 H16 N4 O10 Zn'
_chemical_formula_weight         585.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7121(19)
_cell_length_b                   17.737(3)
_cell_length_c                   9.5694(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.303(2)
_cell_angle_gamma                90
_cell_volume                     2323.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4574
_cell_measurement_theta_min      2.296
_cell_measurement_theta_max      25.636

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   0.731
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    1.127
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS  (Krause et al., 2015)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 60 sec/frame was used. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            21604
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.488
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_full        28.368
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5756
_reflns_number_gt                4015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT/5 (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 Å) while those 
attached to oxygen were placed in locations derived from a difference 
map and their coordinates adjusted to give O---H = 0.87 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.3514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5756
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.26946(2) 0.56025(2) 0.30579(3) 0.01890(12) Uani 1 1 d . . . . .
O1 O 0.18530(14) 0.49087(10) 0.42450(19) 0.0209(4) Uani 1 1 d . . . . .
O2 O 0.06852(16) 0.40588(12) 0.4483(2) 0.0328(5) Uani 1 1 d . . . . .
O3 O 0.14775(15) 0.55074(9) 0.1598(2) 0.0213(4) Uani 1 1 d . . . . .
O4 O 0.09074(18) 0.43505(11) -0.2902(2) 0.0354(6) Uani 1 1 d . . . . .
H4A H 0.085731 0.425150 -0.379387 0.053 Uiso 1 1 d R U . . .
O5 O 0.05278(17) 0.31394(11) -0.2546(2) 0.0329(5) Uani 1 1 d . . . . .
O6 O 0.33559(14) 0.46916(11) 0.20446(19) 0.0224(4) Uani 1 1 d . . . . .
O7 O 0.4495(2) 0.38035(15) 0.2253(2) 0.0550(8) Uani 1 1 d . . . . .
O8 O 0.38827(14) 0.54328(10) 0.4557(2) 0.0218(4) Uani 1 1 d . . . . .
O9 O 0.35337(16) 0.46110(11) 0.9326(2) 0.0306(5) Uani 1 1 d . . . . .
H9 H 0.349340 0.459443 1.022965 0.046 Uiso 1 1 d R U . . .
O10 O 0.31396(16) 0.33817(11) 0.9222(2) 0.0307(5) Uani 1 1 d . . . . .
N1 N 0.12600(16) 0.47987(12) 0.1247(2) 0.0180(5) Uani 1 1 d . . . . .
N2 N 0.37851(16) 0.47495(12) 0.5128(2) 0.0194(5) Uani 1 1 d . . . . .
N3 N 0.21018(17) 0.65669(12) 0.3961(2) 0.0195(5) Uani 1 1 d . . . . .
N4 N 0.34184(16) 0.64755(12) 0.2040(2) 0.0191(5) Uani 1 1 d . . . . .
C1 C 0.1238(2) 0.44341(14) 0.3776(3) 0.0199(6) Uani 1 1 d . . . . .
C2 C 0.1162(2) 0.42515(15) 0.2224(3) 0.0185(6) Uani 1 1 d . . . . .
C3 C 0.0989(2) 0.35195(15) 0.1785(3) 0.0218(6) Uani 1 1 d . . . . .
H3 H 0.093431 0.313244 0.246262 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0893(2) 0.33403(15) 0.0385(3) 0.0218(6) Uani 1 1 d . . . . .
H4 H 0.080214 0.283208 0.009287 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0931(2) 0.39176(15) -0.0593(3) 0.0201(6) Uani 1 1 d . . . . .
C6 C 0.1125(2) 0.46425(15) -0.0129(3) 0.0203(6) Uani 1 1 d . . . . .
H6 H 0.116447 0.503845 -0.079168 0.024 Uiso 1 1 calc R U . . .
C7 C 0.0769(2) 0.37540(16) -0.2120(3) 0.0238(6) Uani 1 1 d . . . . .
C8 C 0.3892(2) 0.42165(17) 0.2739(3) 0.0262(7) Uani 1 1 d . . . . .
C9 C 0.3741(2) 0.41287(16) 0.4294(3) 0.0220(6) Uani 1 1 d . . . . .
C10 C 0.3568(2) 0.34348(15) 0.4887(3) 0.0252(6) Uani 1 1 d . . . . .
H10 H 0.353715 0.299694 0.431493 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3440(2) 0.33705(15) 0.6301(3) 0.0238(6) Uani 1 1 d . . . . .
H11 H 0.329675 0.289506 0.669853 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3523(2) 0.40102(15) 0.7137(3) 0.0210(6) Uani 1 1 d . . . . .
C13 C 0.3705(2) 0.46939(15) 0.6518(3) 0.0204(6) Uani 1 1 d . . . . .
H13 H 0.377416 0.513320 0.708248 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3380(2) 0.39626(16) 0.8667(3) 0.0237(6) Uani 1 1 d . . . . .
C15 C 0.1440(2) 0.65613(16) 0.4934(3) 0.0235(6) Uani 1 1 d . . . . .
H15 H 0.120530 0.608982 0.524487 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1085(2) 0.72130(16) 0.5503(3) 0.0253(6) Uani 1 1 d . . . . .
H16 H 0.062147 0.719273 0.620314 0.030 Uiso 1 1 calc R U . . .
C17 C 0.1421(2) 0.78983(16) 0.5029(3) 0.0250(6) Uani 1 1 d . . . . .
H17 H 0.119290 0.835694 0.540608 0.030 Uiso 1 1 calc R U . . .
C18 C 0.2095(2) 0.79091(15) 0.3997(3) 0.0234(6) Uani 1 1 d . . . . .
H18 H 0.232435 0.837359 0.364598 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2426(2) 0.72285(14) 0.3491(3) 0.0191(6) Uani 1 1 d . . . . .
C20 C 0.3165(2) 0.71802(15) 0.2415(3) 0.0208(6) Uani 1 1 d . . . . .
C21 C 0.3571(2) 0.78084(15) 0.1808(3) 0.0238(6) Uani 1 1 d . . . . .
H21 H 0.339747 0.830100 0.209459 0.029 Uiso 1 1 calc R U . . .
C22 C 0.4231(2) 0.77105(16) 0.0782(3) 0.0265(7) Uani 1 1 d . . . . .
H22 H 0.450452 0.813557 0.034499 0.032 Uiso 1 1 calc R U . . .
C23 C 0.4489(2) 0.69902(17) 0.0400(3) 0.0256(6) Uani 1 1 d . . . . .
H23 H 0.494058 0.691058 -0.030177 0.031 Uiso 1 1 calc R U . . .
C24 C 0.4071(2) 0.63858(17) 0.1065(3) 0.0247(6) Uani 1 1 d . . . . .
H24 H 0.425610 0.588897 0.081942 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0706(18) . ?
Zn1 N3 2.101(2) . ?
Zn1 N4 2.108(2) . ?
Zn1 O6 2.1152(19) . ?
Zn1 O3 2.120(2) . ?
Zn1 O8 2.129(2) . ?
O1 C1 1.256(3) . ?
O2 C1 1.238(3) . ?
O3 N1 1.331(3) . ?
O4 C7 1.316(3) . ?
O4 H4A 0.8700 . ?
O5 C7 1.203(3) . ?
O6 C8 1.279(3) . ?
O7 C8 1.217(4) . ?
O8 N2 1.339(3) . ?
O9 C14 1.323(3) . ?
O9 H9 0.8701 . ?
O10 C14 1.214(3) . ?
N1 C6 1.348(3) . ?
N1 C2 1.360(3) . ?
N2 C13 1.344(3) . ?
N2 C9 1.359(3) . ?
N3 C15 1.337(4) . ?
N3 C19 1.341(3) . ?
N4 C24 1.339(4) . ?
N4 C20 1.351(3) . ?
C1 C2 1.518(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 C7 1.494(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.522(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(4) . ?
C12 C14 1.490(4) . ?
C13 H13 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.489(4) . ?
C20 C21 1.387(4) . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N3 90.99(8) . . ?
O1 Zn1 N4 169.20(8) . . ?
N3 Zn1 N4 78.21(9) . . ?
O1 Zn1 O6 93.71(7) . . ?
N3 Zn1 O6 175.29(8) . . ?
N4 Zn1 O6 97.09(8) . . ?
O1 Zn1 O3 82.63(7) . . ?
N3 Zn1 O3 91.56(8) . . ?
N4 Zn1 O3 97.33(8) . . ?
O6 Zn1 O3 88.81(7) . . ?
O1 Zn1 O8 88.58(7) . . ?
N3 Zn1 O8 97.88(8) . . ?
N4 Zn1 O8 93.04(8) . . ?
O6 Zn1 O8 82.50(7) . . ?
O3 Zn1 O8 167.22(7) . . ?
C1 O1 Zn1 125.90(18) . . ?
N1 O3 Zn1 113.46(14) . . ?
C7 O4 H4A 112.9 . . ?
C8 O6 Zn1 120.92(18) . . ?
N2 O8 Zn1 108.19(15) . . ?
C14 O9 H9 115.3 . . ?
O3 N1 C6 117.2(2) . . ?
O3 N1 C2 122.0(2) . . ?
C6 N1 C2 120.8(2) . . ?
O8 N2 C13 119.1(2) . . ?
O8 N2 C9 119.7(2) . . ?
C13 N2 C9 121.2(2) . . ?
C15 N3 C19 119.4(2) . . ?
C15 N3 Zn1 125.06(18) . . ?
C19 N3 Zn1 115.52(18) . . ?
C24 N4 C20 119.2(2) . . ?
C24 N4 Zn1 125.89(19) . . ?
C20 N4 Zn1 114.94(18) . . ?
O2 C1 O1 125.8(3) . . ?
O2 C1 C2 114.2(2) . . ?
O1 C1 C2 120.0(2) . . ?
N1 C2 C3 119.0(2) . . ?
N1 C2 C1 121.1(2) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 C7 120.7(2) . . ?
C4 C5 C7 120.4(2) . . ?
N1 C6 C5 121.2(3) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O5 C7 O4 125.5(3) . . ?
O5 C7 C5 122.0(3) . . ?
O4 C7 C5 112.5(2) . . ?
O7 C8 O6 125.5(3) . . ?
O7 C8 C9 116.5(3) . . ?
O6 C8 C9 117.9(2) . . ?
N2 C9 C10 118.9(3) . . ?
N2 C9 C8 119.1(2) . . ?
C10 C9 C8 121.9(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 C14 120.6(2) . . ?
C11 C12 C14 120.5(2) . . ?
N2 C13 C12 121.1(3) . . ?
N2 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O10 C14 O9 124.7(3) . . ?
O10 C14 C12 122.2(3) . . ?
O9 C14 C12 113.2(2) . . ?
N3 C15 C16 122.6(3) . . ?
N3 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C17 118.3(3) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
N3 C19 C18 121.5(3) . . ?
N3 C19 C20 115.7(2) . . ?
C18 C19 C20 122.8(2) . . ?
N4 C20 C21 121.1(3) . . ?
N4 C20 C19 115.6(2) . . ?
C21 C20 C19 123.3(2) . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 118.4(3) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
N4 C24 C23 122.5(3) . . ?
N4 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?

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 O3 N1 C6 -131.1(2) . . . . ?
Zn1 O3 N1 C2 49.8(3) . . . . ?
Zn1 O8 N2 C13 -120.5(2) . . . . ?
Zn1 O8 N2 C9 57.6(3) . . . . ?
Zn1 O1 C1 O2 -174.4(2) . . . . ?
Zn1 O1 C1 C2 8.7(4) . . . . ?
O3 N1 C2 C3 -176.5(2) . . . . ?
C6 N1 C2 C3 4.5(4) . . . . ?
O3 N1 C2 C1 3.7(4) . . . . ?
C6 N1 C2 C1 -175.4(2) . . . . ?
O2 C1 C2 N1 144.4(3) . . . . ?
O1 C1 C2 N1 -38.4(4) . . . . ?
O2 C1 C2 C3 -35.4(4) . . . . ?
O1 C1 C2 C3 141.8(3) . . . . ?
N1 C2 C3 C4 -1.4(4) . . . . ?
C1 C2 C3 C4 178.4(3) . . . . ?
C2 C3 C4 C5 -2.8(4) . . . . ?
C3 C4 C5 C6 4.0(4) . . . . ?
C3 C4 C5 C7 -176.2(3) . . . . ?
O3 N1 C6 C5 177.7(2) . . . . ?
C2 N1 C6 C5 -3.2(4) . . . . ?
C4 C5 C6 N1 -1.1(4) . . . . ?
C7 C5 C6 N1 179.1(2) . . . . ?
C6 C5 C7 O5 -174.4(3) . . . . ?
C4 C5 C7 O5 5.8(4) . . . . ?
C6 C5 C7 O4 4.9(4) . . . . ?
C4 C5 C7 O4 -174.9(3) . . . . ?
Zn1 O6 C8 O7 -159.7(3) . . . . ?
Zn1 O6 C8 C9 23.1(4) . . . . ?
O8 N2 C9 C10 -175.3(3) . . . . ?
C13 N2 C9 C10 2.8(4) . . . . ?
O8 N2 C9 C8 5.3(4) . . . . ?
C13 N2 C9 C8 -176.6(3) . . . . ?
O7 C8 C9 N2 128.5(3) . . . . ?
O6 C8 C9 N2 -54.1(4) . . . . ?
O7 C8 C9 C10 -50.9(4) . . . . ?
O6 C8 C9 C10 126.5(3) . . . . ?
N2 C9 C10 C11 0.2(4) . . . . ?
C8 C9 C10 C11 179.6(3) . . . . ?
C9 C10 C11 C12 -2.4(4) . . . . ?
C10 C11 C12 C13 1.7(4) . . . . ?
C10 C11 C12 C14 179.5(3) . . . . ?
O8 N2 C13 C12 174.6(2) . . . . ?
C9 N2 C13 C12 -3.5(4) . . . . ?
C11 C12 C13 N2 1.1(4) . . . . ?
C14 C12 C13 N2 -176.6(3) . . . . ?
C13 C12 C14 O10 173.7(3) . . . . ?
C11 C12 C14 O10 -4.0(4) . . . . ?
C13 C12 C14 O9 -5.6(4) . . . . ?
C11 C12 C14 O9 176.7(3) . . . . ?
C19 N3 C15 C16 -1.3(4) . . . . ?
Zn1 N3 C15 C16 179.2(2) . . . . ?
N3 C15 C16 C17 0.9(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C15 N3 C19 C18 0.3(4) . . . . ?
Zn1 N3 C19 C18 180.0(2) . . . . ?
C15 N3 C19 C20 179.7(2) . . . . ?
Zn1 N3 C19 C20 -0.7(3) . . . . ?
C17 C18 C19 N3 0.9(4) . . . . ?
C17 C18 C19 C20 -178.4(3) . . . . ?
C24 N4 C20 C21 0.0(4) . . . . ?
Zn1 N4 C20 C21 -178.8(2) . . . . ?
C24 N4 C20 C19 179.3(2) . . . . ?
Zn1 N4 C20 C19 0.5(3) . . . . ?
N3 C19 C20 N4 0.1(4) . . . . ?
C18 C19 C20 N4 179.5(2) . . . . ?
N3 C19 C20 C21 179.4(3) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
N4 C20 C21 C22 1.3(4) . . . . ?
C19 C20 C21 C22 -178.0(3) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C20 N4 C24 C23 -1.3(4) . . . . ?
Zn1 N4 C24 C23 177.3(2) . . . . ?
C22 C23 C24 N4 1.3(4) . . . . ?

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
O4 H4A O2 0.87 1.69 2.556(3) 176 1_554 yes
O9 H9 O6 0.87 1.77 2.631(3) 172 1_556 yes
C3 H3 O5 0.95 2.32 3.084(3) 137 4_566 yes
C10 H10 O10 0.95 2.51 3.330(3) 145 4_565 yes
C17 H17 O3 0.95 2.34 3.201(3) 151 4_576 y
C23 H23 O7 0.95 2.42 3.283(4) 151 3_665 yes

_refine_diff_density_max         1.007
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_JTM1270_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2009484'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Department of Chemistry, Tulane University
United States of America
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2021-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl N3 O5 Zn, 2(H2 O)'
_chemical_formula_sum            'C17 H16 Cl N3 O7 Zn'
_chemical_formula_weight         475.15

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5124(9)
_cell_length_b                   9.503(1)
_cell_length_c                   12.0869(13)
_cell_angle_alpha                75.923(2)
_cell_angle_beta                 84.467(2)
_cell_angle_gamma                80.995(2)
_cell_volume                     934.96(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.2308
_cell_measurement_theta_max      29.2719
_cell_measurement_temperature    150(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   0.787
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    1.504
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.76

_exptl_special_details           
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 10 sec/frame.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18159
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         29.323
_diffrn_reflns_theta_full        28.500
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5008
_reflns_number_gt                4475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.98 Å) while those 
attached to oxygen were placed in locations derived from a difference 
map and their coordinates adjusted to give O---H = 0.87 %A. All were 
included as riding contributions with isotropic displacement parameters 
1.2 - 1.5 times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.1335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5008
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.44630(2) 0.36707(2) 0.33354(2) 0.01540(6) Uani 1 1 d . . . . .
Cl1 Cl 0.25153(4) 0.24150(4) 0.30770(3) 0.02207(8) Uani 1 1 d . . . . .
O1 O 0.32242(13) 0.56613(11) 0.33697(9) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.18122(12) 0.73570(11) 0.41856(9) 0.0216(2) Uani 1 1 d . . . . .
O3 O 0.46481(11) 0.34124(11) 0.50331(8) 0.0173(2) Uani 1 1 d . . . . .
O4 O 0.28547(13) 0.09385(12) 0.87629(9) 0.0246(2) Uani 1 1 d . . . . .
H4A H 0.262359 0.033002 0.940085 0.037 Uiso 1 1 d R U . . .
O5 O 0.04266(13) 0.20645(13) 0.91658(9) 0.0268(2) Uani 1 1 d . . . . .
N1 N 0.33632(13) 0.37645(12) 0.56820(10) 0.0141(2) Uani 1 1 d . . . . .
N2 N 0.57377(14) 0.46258(12) 0.18431(10) 0.0160(2) Uani 1 1 d . . . . .
N3 N 0.65776(14) 0.21607(13) 0.33408(10) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.24951(16) 0.60959(15) 0.42123(12) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.23152(16) 0.50172(14) 0.53593(11) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.10139(17) 0.52819(16) 0.61080(12) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.028914 0.615803 0.590692 0.022 Uiso 1 1 calc R U . . .
C4 C 0.07510(17) 0.43052(16) 0.71330(12) 0.0191(3) Uani 1 1 d . . . . .
H4 H -0.017108 0.447690 0.761677 0.023 Uiso 1 1 calc R U . . .
C5 C 0.18662(16) 0.30594(15) 0.74458(12) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.31758(16) 0.28282(15) 0.67090(11) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.395662 0.199802 0.692808 0.019 Uiso 1 1 calc R U . . .
C7 C 0.16437(17) 0.19660(16) 0.85479(12) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.52563(18) 0.59297(15) 0.11511(12) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.430506 0.649648 0.136372 0.023 Uiso 1 1 calc R U . . .
C9 C 0.60974(18) 0.64764(16) 0.01394(13) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.573745 0.740479 -0.033317 0.027 Uiso 1 1 calc R U . . .
C10 C 0.74750(19) 0.56378(18) -0.01669(13) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.806933 0.598372 -0.086014 0.029 Uiso 1 1 calc R U . . .
C11 C 0.79853(18) 0.42930(17) 0.05396(12) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.892962 0.370773 0.033865 0.025 Uiso 1 1 calc R U . . .
C12 C 0.70863(16) 0.38131(15) 0.15527(12) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.75572(16) 0.24173(15) 0.23889(12) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.89219(17) 0.14480(16) 0.22400(13) 0.0219(3) Uani 1 1 d . . . . .
H14 H 0.959449 0.163574 0.156143 0.026 Uiso 1 1 calc R U . . .
C15 C 0.92824(18) 0.02065(16) 0.30968(14) 0.0241(3) Uani 1 1 d . . . . .
H15 H 1.020735 -0.047047 0.301168 0.029 Uiso 1 1 calc R U . . .
C16 C 0.82880(19) -0.00437(16) 0.40788(14) 0.0233(3) Uani 1 1 d . . . . .
H16 H 0.852332 -0.088548 0.467944 0.028 Uiso 1 1 calc R U . . .
C17 C 0.69430(18) 0.09591(16) 0.41668(13) 0.0211(3) Uani 1 1 d . . . . .
H17 H 0.625380 0.078855 0.483789 0.025 Uiso 1 1 calc R U . . .
O6 O 0.25728(14) 0.89469(13) 0.05528(10) 0.0292(2) Uani 1 1 d . . . . .
H6A H 0.285724 0.906193 0.119383 0.044 Uiso 1 1 d R U . . .
H6B H 0.164386 0.865236 0.072686 0.044 Uiso 1 1 d R U . . .
O7 O 0.34711(13) 0.92270(12) 0.25522(10) 0.0276(2) Uani 1 1 d . . . . .
H7A H 0.321104 1.007596 0.272045 0.041 Uiso 1 1 d R U . . .
H7B H 0.295515 0.864164 0.307777 0.041 Uiso 1 1 d 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 2.0242(10) . ?
Zn1 O3 2.0251(10) . ?
Zn1 N2 2.0951(12) . ?
Zn1 N3 2.1186(12) . ?
Zn1 Cl1 2.2739(4) . ?
O1 C1 1.2632(16) . ?
O2 C1 1.2418(16) . ?
O3 N1 1.3309(14) . ?
O4 C7 1.3026(18) . ?
O4 H4A 0.8700 . ?
O5 C7 1.2225(17) . ?
N1 C6 1.3517(18) . ?
N1 C2 1.3688(17) . ?
N2 C8 1.3438(18) . ?
N2 C12 1.3469(17) . ?
N3 C17 1.3385(18) . ?
N3 C13 1.3493(17) . ?
C1 C2 1.5208(19) . ?
C2 C3 1.3927(18) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3947(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3824(18) . ?
C5 C7 1.493(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3964(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.4837(19) . ?
C13 C14 1.3913(19) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O6 H6A 0.8698 . ?
O6 H6B 0.8697 . ?
O7 H7A 0.8697 . ?
O7 H7B 0.8698 . ?

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 O3 86.15(4) . . ?
O1 Zn1 N2 89.51(4) . . ?
O3 Zn1 N2 135.47(4) . . ?
O1 Zn1 N3 153.79(5) . . ?
O3 Zn1 N3 87.54(4) . . ?
N2 Zn1 N3 77.38(5) . . ?
O1 Zn1 Cl1 101.86(3) . . ?
O3 Zn1 Cl1 108.81(3) . . ?
N2 Zn1 Cl1 115.44(3) . . ?
N3 Zn1 Cl1 104.25(3) . . ?
C1 O1 Zn1 128.53(9) . . ?
N1 O3 Zn1 119.34(8) . . ?
C7 O4 H4A 108.0 . . ?
O3 N1 C6 115.79(11) . . ?
O3 N1 C2 122.79(11) . . ?
C6 N1 C2 121.38(11) . . ?
C8 N2 C12 119.42(12) . . ?
C8 N2 Zn1 124.55(10) . . ?
C12 N2 Zn1 115.95(9) . . ?
C17 N3 C13 119.18(12) . . ?
C17 N3 Zn1 125.25(10) . . ?
C13 N3 Zn1 115.44(9) . . ?
O2 C1 O1 125.34(13) . . ?
O2 C1 C2 114.55(12) . . ?
O1 C1 C2 120.01(12) . . ?
N1 C2 C3 118.01(12) . . ?
N1 C2 C1 122.70(11) . . ?
C3 C2 C1 119.28(12) . . ?
C4 C3 C2 121.66(13) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.65(13) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 119.10(13) . . ?
C6 C5 C7 119.95(12) . . ?
C4 C5 C7 120.93(12) . . ?
N1 C6 C5 121.06(12) . . ?
N1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O5 C7 O4 125.07(14) . . ?
O5 C7 C5 121.53(14) . . ?
O4 C7 C5 113.40(12) . . ?
N2 C8 C9 122.34(13) . . ?
N2 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 118.39(14) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 119.85(14) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 118.77(13) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N2 C12 C11 121.23(13) . . ?
N2 C12 C13 115.64(12) . . ?
C11 C12 C13 123.10(12) . . ?
N3 C13 C14 121.43(13) . . ?
N3 C13 C12 114.87(11) . . ?
C14 C13 C12 123.68(13) . . ?
C15 C14 C13 118.85(14) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.61(13) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 118.53(14) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N3 C17 C16 122.39(14) . . ?
N3 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
H6A O6 H6B 104.1 . . ?
H7A O7 H7B 104.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O3 N1 C6 138.55(10) . . . . ?
Zn1 O3 N1 C2 -43.63(15) . . . . ?
Zn1 O1 C1 O2 176.69(10) . . . . ?
Zn1 O1 C1 C2 -7.16(19) . . . . ?
O3 N1 C2 C3 -179.63(12) . . . . ?
C6 N1 C2 C3 -1.93(19) . . . . ?
O3 N1 C2 C1 2.06(19) . . . . ?
C6 N1 C2 C1 179.77(12) . . . . ?
O2 C1 C2 N1 -157.52(13) . . . . ?
O1 C1 C2 N1 25.9(2) . . . . ?
O2 C1 C2 C3 24.19(18) . . . . ?
O1 C1 C2 C3 -152.35(13) . . . . ?
N1 C2 C3 C4 -1.6(2) . . . . ?
C1 C2 C3 C4 176.77(13) . . . . ?
C2 C3 C4 C5 3.2(2) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C3 C4 C5 C7 179.86(13) . . . . ?
O3 N1 C6 C5 -178.40(12) . . . . ?
C2 N1 C6 C5 3.7(2) . . . . ?
C4 C5 C6 N1 -2.0(2) . . . . ?
C7 C5 C6 N1 176.71(12) . . . . ?
C6 C5 C7 O5 -172.85(13) . . . . ?
C4 C5 C7 O5 5.8(2) . . . . ?
C6 C5 C7 O4 7.24(19) . . . . ?
C4 C5 C7 O4 -174.07(13) . . . . ?
C12 N2 C8 C9 0.2(2) . . . . ?
Zn1 N2 C8 C9 -176.22(11) . . . . ?
N2 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C8 N2 C12 C11 -0.7(2) . . . . ?
Zn1 N2 C12 C11 175.99(10) . . . . ?
C8 N2 C12 C13 177.75(12) . . . . ?
Zn1 N2 C12 C13 -5.57(15) . . . . ?
C10 C11 C12 N2 0.6(2) . . . . ?
C10 C11 C12 C13 -177.73(13) . . . . ?
C17 N3 C13 C14 1.1(2) . . . . ?
Zn1 N3 C13 C14 -174.79(11) . . . . ?
C17 N3 C13 C12 -177.13(12) . . . . ?
Zn1 N3 C13 C12 6.96(15) . . . . ?
N2 C12 C13 N3 -0.98(17) . . . . ?
C11 C12 C13 N3 177.43(13) . . . . ?
N2 C12 C13 C14 -179.19(13) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
N3 C13 C14 C15 -0.8(2) . . . . ?
C12 C13 C14 C15 177.31(13) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C13 N3 C17 C16 -0.5(2) . . . . ?
Zn1 N3 C17 C16 174.93(11) . . . . ?
C15 C16 C17 N3 -0.3(2) . . . . ?

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
O4 H4A O6 0.87 1.67 2.5239(16) 167 1_546 yes
C6 H6 O7 0.95 2.38 3.2645(18) 155 2_666 yes
C8 H8 O6 0.95 2.58 3.350(2) 138 . y
C11 H11 O5 0.95 2.49 3.3508(18) 151 1_654 yes
C15 H15 O2 0.95 2.49 3.2695(19) 139 1_645 y
O6 H6A O7 0.87 1.82 2.6886(17) 178 . yes
O6 H6B O5 0.87 1.97 2.8283(16) 170 2_566 yes
O7 H7A Cl1 0.87 2.34 3.2103(12) 177 1_565 yes
O7 H7B O2 0.87 1.89 2.7552(16) 178 . yes

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.071

