[N,N′-Bis(3-amino­prop­yl)ethyl­ene­di­am­ine]disaccharinatozinc(II) monohydrate

In the title complex, [Zn(C₇H₄NO₃S)₂(C₈H₂₂N₄)]·H₂O or [Zn(sac)₂(paen)]·H₂O [sac = saccharinate and paen = N,N′-bis­(3-amino­prop­yl)ethyl­enediamine], the zinc cation is octa­hedrally coordinated. The equatorial plane of the octa­hedron is formed by N atoms of the paen ligand, whereas the axial positions are occupied by the carbonyl O atoms of the two sac ligands. One of the sulfonyl groups of the sac ligands shows disorder and was modelled with two different orientations and site occupancies of 0:38 (1):0.62 (1). The mol­ecular packing is stabilized by inter­molecular O—H...O and N—H...O hydrogen bonds between water mol­ecules and neighbouring [Zn(sac)₂(paen)] mol­ecules, which form chains running parallel to [010]. The crystal used was an inversion twin.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.068
• wR factor = 0.122
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.147
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.449
           From the CIF: _refine_ls_abs_structure_Flack_su    0.017
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.15
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT033_ALERT_2_C Flack Parameter Value Deviates 2 * su from zero.       0.45
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        S1B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N4     -   H4A    ...       0.76 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C1     -   C6     ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C5     -   C6     ...       1.37 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.54
           From the CIF: _reflns_number_total               6894
           Count of symmetry unique reflns         3969
           Completeness (_total/calc)            173.70%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2925
           Fraction of Friedel pairs measured     0.737
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N5     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         29

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

In title compound the Zn(II) cation is octahedrally coordinated by two sac and one paen ligands. Most interestingly, the two sac ligands are bonded to the Zn site via the carbonyl O atoms although N-coordination is usually preferred by this ligand with first-row transition metals. The equatorial plane, defined by the atoms (N3, N4, N5, N6), of the octahedron is formed by N atoms of paen ligands, whereas the axial positions belong to the carbonyl O atoms of the sac ligands. The Zn—N bonds are slightly shorter than the Zn—O bonds (Table 1). Whereas the (O–Zn–O) angle is nearly linear, the trans- (N–Zn–N) angles of the equatorial plane deviate significantly from linearity. One of the sulfonyl groups of the sac ligands shows disorder, and was refined with two different orientations (see Fig. 1). However, the bond lengths and angles of the sac ligands are similiar to those observed in related structures (Yeşilel et al., 2006; Yilmaz et al., 2002; 2006).

The molecular packing is stabilized by intermolecular hydrogen bonds (Table2, Fig. 2). Neighbouring Zn(sac)₂(paen) moieties are linked via water molecules through O—H···O and N—H···O hydrogen bonds, which leads to chains extending parallel to (010).

Related literature

For synthesis of [Zn(sac)₂(H₂O)₄]^.2H₂O used as an educt for crystal growth of the title compound, see: Koksal et al. (2001). For related structures containing sac ligands, see: Yeşilel et al., 2006; Yilmaz et al., 2002; 2006.

S2. Experimental

Under continous stirring at room temperature, an aqueous solution of paen (350 mg, 2.0 mmol) was added dropwise to 50 ml of an aqueous solution of [Zn(sac)₂(H₂O)₄]^.2H₂O (548 mg, 1.0 mmol). For synthesis of the latter compound, see: Koksal et al. (2001). The resulting solution was heated up to 353 K and stirred continuously for 4 h. Then the solution was allowed to cool to room temperature slowly. Small colourless crystals grown in the solution were filtered off and washed with cold distilled water and ethanol, and were finally dried.

S3. Refinement

The disordered sulfonyl group of the sacharinate ligand was modelled with two different orientations (S1A—S1B; O3A—O3B, O4A—O4B) and with refined occupancy factors of 0.383 (11) and 0.617 (11), respectively. All H atoms except those bonded to N4 and N5 atoms were placed in geometrically idealized positions with distances of d(N–H) = 0.90 Å; d(C–H) = 0.93 - 0.97 Å, and were refined as riding atoms with U_iso(H) = 1.2U_eq of the parent atoms. H atoms bonded to N4 and N5 were found from difference maps and were refined freely. H atoms of the water molecule were constrained to O—H distances of 0.85 (2) Å and were refined with U_iso(H) = 1.2U_eq(OW). The measured crystal was racemically twinned with an approximate twin ratio of 1:1.

Computing details

Data collection: X-AREA (Stoe, 2002); cell refinement: X-AREA (Stoe, 2002); data reduction: X-RED32 (Stoe, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of (I), with atom labels and displacement ellipsoids displayed at the 30% probability level. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 2. The packing diagram of the title compound showing the chain structure parallel to (010). Benzene rings and some hydrogen bonds have been omitted for clarity.

[N,N'-Bis(3-aminopropyl)ethylendiamine]disaccharinatozinc(II) monohydrate

Crystal data

[Zn(C7H4NO3S)2(C8H22N4)]·H2O	F(000) = 1296
Mr = 622.03	Dx = 1.485 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23038 reflections
a = 10.1025 (5) Å	θ = 1.4–26.6°
b = 14.3045 (10) Å	µ = 1.08 mm^−1
c = 19.2547 (11) Å	T = 296 K
V = 2782.5 (3) Å^3	Rectangular prism, colorless
Z = 4	0.32 × 0.30 × 0.25 mm

Data collection

Stoe IPDSII diffractometer	6894 independent reflections
Radiation source: fine-focus sealed tube	3763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.148
ω scans	θmax = 28.5°, θmin = 1.8°
Absorption correction: numerical (X-RED32; Stoe, 2002)	h = −12→13
Tmin = 0.710, Tmax = 0.811	k = −19→18
49189 measured reflections	l = −25→25

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.0535P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max = 0.001
S = 0.92	Δρmax = 0.37 e Å^−3
6894 reflections	Δρmin = −0.36 e Å^−3
381 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
29 restraints	Extinction coefficient: 0.0015 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 3014 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.449 (17)

Special details

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

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1672 (4)	0.4017 (3)	0.1425 (2)	0.0451 (10)
C2	0.1978 (5)	0.3115 (3)	0.1605 (3)	0.0590 (13)
H2	0.2750	0.2830	0.1449	0.071*
C3	0.1087 (6)	0.2641 (4)	0.2031 (3)	0.0728 (15)
H3	0.1278	0.2035	0.2175	0.087*
C4	−0.0065 (6)	0.3058 (4)	0.2241 (3)	0.0749 (15)
H4	−0.0662	0.2717	0.2507	0.090*
C5	−0.0361 (6)	0.3954 (4)	0.2072 (3)	0.0755 (17)
H5	−0.1127	0.4243	0.2232	0.091*
C6	0.0520 (5)	0.4412 (4)	0.1656 (3)	0.0624 (14)
C7	0.2450 (5)	0.4672 (3)	0.0984 (3)	0.0608 (13)
C8	0.8111 (4)	0.6093 (3)	−0.1499 (2)	0.0429 (10)
C9	0.7907 (5)	0.7016 (3)	−0.1649 (3)	0.0526 (12)
H9	0.7208	0.7345	−0.1451	0.063*
C10	0.8768 (6)	0.7441 (4)	−0.2101 (3)	0.0694 (15)
H10	0.8649	0.8068	−0.2212	0.083*
C11	0.9808 (7)	0.6953 (4)	−0.2394 (3)	0.0725 (16)
H11	1.0372	0.7255	−0.2703	0.087*
C12	1.0022 (6)	0.6024 (4)	−0.2234 (3)	0.0682 (13)
H12	1.0724	0.5691	−0.2424	0.082*
C13	0.9140 (4)	0.5615 (3)	−0.1776 (2)	0.0501 (11)
C14	0.7301 (4)	0.5471 (3)	−0.1025 (2)	0.0468 (10)
C15	0.4820 (6)	0.2962 (3)	−0.0276 (3)	0.0731 (15)
H15A	0.4710	0.2454	−0.0605	0.088*
H15B	0.4096	0.2931	0.0054	0.088*
C16	0.6118 (6)	0.2837 (4)	0.0107 (3)	0.0718 (15)
H16A	0.6182	0.2191	0.0257	0.086*
H16B	0.6837	0.2950	−0.0216	0.086*
C17	0.6310 (6)	0.3457 (4)	0.0730 (3)	0.0771 (17)
H17A	0.5550	0.3393	0.1034	0.093*
H17B	0.7083	0.3246	0.0985	0.093*
C18	0.3549 (6)	0.3961 (4)	−0.1050 (4)	0.0820 (17)
H18A	0.2796	0.3785	−0.0766	0.098*
H18B	0.3576	0.3547	−0.1449	0.098*
C19	0.3383 (6)	0.4956 (4)	−0.1292 (3)	0.0810 (16)
H19A	0.4118	0.5128	−0.1590	0.097*
H19B	0.2572	0.5014	−0.1559	0.097*
C20	0.3312 (6)	0.6581 (4)	−0.0891 (3)	0.0747 (16)
H20A	0.2514	0.6705	−0.1155	0.090*
H20B	0.4065	0.6710	−0.1188	0.090*
C21	0.3355 (6)	0.7216 (4)	−0.0276 (4)	0.084 (2)
H21A	0.2642	0.7040	0.0035	0.101*
H21B	0.3175	0.7847	−0.0435	0.101*
C22	0.4633 (6)	0.7233 (3)	0.0139 (3)	0.0760 (18)
H22A	0.5375	0.7310	−0.0176	0.091*
H22B	0.4623	0.7765	0.0451	0.091*
N1	0.1887 (5)	0.5510 (3)	0.0913 (3)	0.0946 (19)
N2	0.7764 (4)	0.4591 (3)	−0.0980 (2)	0.0628 (12)
N3	0.4813 (5)	0.6373 (3)	0.0542 (2)	0.0702 (12)
H3A	0.4140	0.6331	0.0847	0.084*
H3B	0.5563	0.6432	0.0791	0.084*
N4	0.4754 (5)	0.3859 (3)	−0.0651 (3)	0.0616 (12)
N5	0.3334 (4)	0.5583 (3)	−0.0687 (3)	0.0658 (12)
N6	0.6482 (4)	0.4462 (3)	0.0551 (2)	0.0693 (12)
H6A	0.7227	0.4519	0.0298	0.083*
H6B	0.6606	0.4782	0.0948	0.083*
O1	0.3520 (4)	0.4442 (3)	0.0723 (2)	0.0758 (11)
O2	0.6306 (3)	0.5774 (2)	−0.07302 (19)	0.0600 (9)
O1W	0.8016 (5)	0.3978 (5)	−0.3387 (3)	0.1273 (19)
O3A	0.107 (2)	0.6125 (9)	0.2157 (8)	0.101 (5)	0.383 (11)
O3B	0.0292 (14)	0.6268 (5)	0.1665 (10)	0.130 (6)	0.617 (11)
O4A	−0.0316 (15)	0.5925 (16)	0.1166 (15)	0.115 (4)	0.383 (11)
O4B	−0.0713 (8)	0.5555 (7)	0.0682 (7)	0.115 (4)	0.617 (11)
O5	0.8858 (5)	0.3817 (3)	−0.1988 (2)	0.1005 (16)
O6	1.0226 (4)	0.4277 (3)	−0.1006 (2)	0.1084 (17)
S1A	0.0774 (9)	0.5583 (5)	0.1553 (5)	0.079 (3)	0.383 (11)
S1B	0.0367 (4)	0.5542 (3)	0.1183 (3)	0.0725 (14)	0.617 (11)
S2	0.90760 (14)	0.44672 (10)	−0.14354 (8)	0.0665 (4)
Zn1	0.49146 (5)	0.51064 (3)	−0.00068 (4)	0.05359 (16)
H5A	0.252 (6)	0.548 (4)	−0.040 (3)	0.082 (16)*
H4A	0.548 (7)	0.393 (5)	−0.073 (4)	0.10 (3)*
H1W	0.816 (7)	0.405 (7)	−0.2951 (15)	0.154*
H2W	0.720 (2)	0.405 (7)	−0.341 (4)	0.154*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.049 (3)	0.044 (2)	0.042 (2)	−0.0024 (19)	0.009 (2)	−0.0002 (19)
C2	0.055 (3)	0.062 (3)	0.060 (3)	0.005 (2)	0.001 (3)	0.008 (2)
C3	0.077 (4)	0.067 (3)	0.075 (4)	−0.002 (3)	0.004 (3)	0.019 (3)
C4	0.074 (4)	0.082 (4)	0.068 (3)	−0.021 (4)	0.019 (3)	0.007 (3)
C5	0.072 (4)	0.070 (3)	0.084 (4)	−0.015 (3)	0.038 (3)	−0.005 (3)
C6	0.063 (3)	0.057 (3)	0.067 (3)	−0.003 (2)	0.037 (3)	−0.001 (3)
C7	0.053 (3)	0.059 (3)	0.070 (3)	−0.002 (2)	0.022 (2)	0.008 (3)
C8	0.037 (2)	0.047 (2)	0.045 (3)	−0.0072 (19)	−0.0025 (19)	0.001 (2)
C9	0.061 (3)	0.042 (2)	0.054 (3)	−0.003 (2)	−0.002 (2)	0.004 (2)
C10	0.089 (4)	0.052 (3)	0.068 (4)	−0.014 (3)	−0.008 (3)	0.016 (3)
C11	0.084 (4)	0.077 (3)	0.056 (3)	−0.021 (3)	0.018 (3)	0.013 (2)
C12	0.055 (3)	0.081 (3)	0.068 (3)	−0.003 (3)	0.016 (3)	0.007 (3)
C13	0.047 (3)	0.059 (3)	0.045 (2)	0.000 (2)	0.015 (2)	0.005 (2)
C14	0.033 (2)	0.055 (3)	0.052 (3)	−0.003 (2)	0.0064 (19)	0.003 (2)
C15	0.063 (4)	0.058 (3)	0.098 (4)	−0.002 (3)	0.021 (3)	0.010 (2)
C16	0.069 (3)	0.066 (3)	0.080 (4)	0.015 (2)	0.012 (3)	0.013 (3)
C17	0.066 (4)	0.085 (4)	0.080 (4)	0.020 (3)	0.006 (3)	0.030 (3)
C18	0.074 (4)	0.072 (4)	0.100 (5)	−0.012 (3)	−0.013 (4)	0.007 (3)
C19	0.067 (3)	0.087 (4)	0.089 (4)	−0.004 (3)	−0.015 (3)	0.011 (3)
C20	0.061 (3)	0.072 (4)	0.091 (4)	0.009 (3)	0.004 (3)	0.024 (3)
C21	0.073 (4)	0.059 (3)	0.121 (6)	0.016 (3)	0.029 (4)	0.030 (3)
C22	0.080 (4)	0.059 (3)	0.089 (5)	0.003 (2)	0.033 (3)	−0.006 (3)
N1	0.080 (3)	0.049 (2)	0.155 (5)	0.007 (2)	0.069 (3)	0.022 (3)
N2	0.053 (2)	0.046 (2)	0.090 (3)	0.0027 (18)	0.035 (2)	0.016 (2)
N3	0.069 (3)	0.068 (2)	0.074 (3)	0.012 (2)	0.020 (2)	0.002 (2)
N4	0.045 (3)	0.053 (2)	0.088 (3)	−0.0020 (19)	0.010 (2)	0.003 (2)
N5	0.050 (2)	0.063 (3)	0.084 (3)	0.005 (2)	0.014 (2)	0.022 (3)
N6	0.061 (3)	0.079 (3)	0.068 (3)	0.003 (2)	0.009 (2)	0.008 (2)
O1	0.057 (2)	0.075 (2)	0.095 (3)	0.008 (2)	0.037 (2)	0.021 (2)
O2	0.0461 (19)	0.059 (2)	0.075 (2)	0.0036 (15)	0.0220 (17)	0.0056 (17)
O1W	0.088 (4)	0.187 (5)	0.107 (4)	0.000 (4)	−0.009 (3)	0.013 (4)
O3A	0.120 (13)	0.070 (8)	0.113 (11)	0.009 (8)	0.033 (10)	0.006 (8)
O3B	0.114 (9)	0.048 (4)	0.227 (15)	−0.009 (5)	0.085 (9)	−0.047 (7)
O4A	0.050 (5)	0.086 (6)	0.209 (12)	0.012 (4)	0.004 (5)	0.067 (7)
O4B	0.050 (5)	0.086 (6)	0.209 (12)	0.012 (4)	0.004 (5)	0.067 (7)
O5	0.140 (4)	0.059 (2)	0.103 (3)	−0.002 (3)	0.048 (3)	−0.014 (2)
O6	0.071 (3)	0.136 (4)	0.118 (4)	0.045 (3)	0.018 (3)	0.063 (3)
S1A	0.087 (5)	0.057 (3)	0.095 (5)	0.031 (3)	0.059 (4)	0.021 (4)
S1B	0.064 (2)	0.0434 (13)	0.110 (3)	0.0058 (14)	0.038 (2)	0.008 (2)
S2	0.0651 (8)	0.0589 (7)	0.0756 (9)	0.0126 (6)	0.0299 (7)	0.0147 (7)
Zn1	0.0456 (3)	0.0536 (3)	0.0616 (3)	0.0076 (2)	0.0124 (3)	0.0074 (3)

Geometric parameters (Å, º)

C1—C6	1.368 (6)	C18—C19	1.507 (7)
C1—C2	1.372 (6)	C18—H18A	0.9700
C1—C7	1.490 (6)	C18—H18B	0.9700
C2—C3	1.393 (8)	C19—N5	1.471 (8)
C2—H2	0.9300	C19—H19A	0.9700
C3—C4	1.369 (8)	C19—H19B	0.9700
C3—H3	0.9300	C20—N5	1.481 (6)
C4—C5	1.356 (8)	C20—C21	1.492 (8)
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.364 (7)	C20—H20B	0.9700
C5—H5	0.9300	C21—C22	1.519 (8)
C6—S1A	1.706 (9)	C21—H21A	0.9700
C6—S1B	1.861 (7)	C21—H21B	0.9700
C7—O1	1.237 (6)	C22—N3	1.466 (6)
C7—N1	1.333 (6)	C22—H22A	0.9700
C8—C13	1.355 (6)	C22—H22B	0.9700
C8—C9	1.367 (6)	N1—S1B	1.623 (6)
C8—C14	1.514 (6)	N1—S1A	1.671 (7)
C9—C10	1.372 (7)	N2—S2	1.599 (4)
C9—H9	0.9300	N3—Zn1	2.100 (4)
C10—C11	1.382 (8)	N3—H3A	0.9000
C10—H10	0.9300	N3—H3B	0.9000
C11—C12	1.381 (8)	N4—Zn1	2.180 (5)
C11—H11	0.9300	N4—H4A	0.76 (7)
C12—C13	1.384 (6)	N5—Zn1	2.174 (5)
C12—H12	0.9300	N5—H5A	1.00 (6)
C13—S2	1.769 (5)	N6—Zn1	2.124 (4)
C14—O2	1.233 (5)	N6—H6A	0.9000
C14—N2	1.346 (6)	N6—H6B	0.9000
C15—N4	1.473 (6)	O1—Zn1	2.204 (4)
C15—C16	1.515 (8)	O2—Zn1	2.197 (3)
C15—H15A	0.9700	O1W—H1W	0.86 (2)
C15—H15B	0.9700	O1W—H2W	0.84 (2)
C16—C17	1.505 (8)	O3A—S1A	1.430 (14)
C16—H16A	0.9700	O3B—S1B	1.395 (11)
C16—H16B	0.9700	O4A—S1A	1.417 (14)
C17—N6	1.489 (7)	O4B—S1B	1.456 (11)
C17—H17A	0.9700	O5—S2	1.431 (5)
C17—H17B	0.9700	O6—S2	1.452 (4)
C18—N4	1.446 (7)
C6—C1—C2	119.9 (4)	C21—C20—H20B	109.2
C6—C1—C7	112.0 (4)	H20A—C20—H20B	107.9
C2—C1—C7	128.1 (4)	C20—C21—C22	116.8 (5)
C1—C2—C3	117.4 (5)	C20—C21—H21A	108.1
C1—C2—H2	121.3	C22—C21—H21A	108.1
C3—C2—H2	121.3	C20—C21—H21B	108.1
C4—C3—C2	120.8 (5)	C22—C21—H21B	108.1
C4—C3—H3	119.6	H21A—C21—H21B	107.3
C2—C3—H3	119.6	N3—C22—C21	111.7 (4)
C5—C4—C3	121.9 (5)	N3—C22—H22A	109.3
C5—C4—H4	119.1	C21—C22—H22A	109.3
C3—C4—H4	119.1	N3—C22—H22B	109.3
C4—C5—C6	116.8 (5)	C21—C22—H22B	109.3
C4—C5—H5	121.6	H22A—C22—H22B	107.9
C6—C5—H5	121.6	C7—N1—S1B	113.3 (4)
C5—C6—C1	123.2 (5)	C7—N1—S1A	105.5 (4)
C5—C6—S1A	129.6 (4)	C14—N2—S2	110.9 (3)
C1—C6—S1A	103.9 (4)	C22—N3—Zn1	117.6 (3)
C5—C6—S1B	130.5 (4)	C22—N3—H3A	107.9
C1—C6—S1B	105.7 (4)	Zn1—N3—H3A	107.9
O1—C7—N1	124.8 (4)	C22—N3—H3B	107.9
O1—C7—C1	121.7 (4)	Zn1—N3—H3B	107.9
N1—C7—C1	113.5 (4)	H3A—N3—H3B	107.2
C13—C8—C9	121.4 (4)	C18—N4—C15	112.7 (4)
C13—C8—C14	110.8 (4)	C18—N4—Zn1	106.4 (3)
C9—C8—C14	127.8 (4)	C15—N4—Zn1	115.5 (4)
C8—C9—C10	117.8 (5)	C18—N4—H4A	134 (6)
C8—C9—H9	121.1	C15—N4—H4A	100 (5)
C10—C9—H9	121.1	Zn1—N4—H4A	86 (5)
C9—C10—C11	121.2 (5)	C19—N5—C20	112.2 (5)
C9—C10—H10	119.4	C19—N5—Zn1	105.2 (3)
C11—C10—H10	119.4	C20—N5—Zn1	118.2 (4)
C12—C11—C10	120.9 (5)	C19—N5—H5A	112 (3)
C12—C11—H11	119.5	C20—N5—H5A	106 (3)
C10—C11—H11	119.5	Zn1—N5—H5A	103 (3)
C11—C12—C13	116.6 (5)	C17—N6—Zn1	116.7 (4)
C11—C12—H12	121.7	C17—N6—H6A	108.1
C13—C12—H12	121.7	Zn1—N6—H6A	108.1
C8—C13—C12	122.1 (5)	C17—N6—H6B	108.1
C8—C13—S2	107.1 (3)	Zn1—N6—H6B	108.1
C12—C13—S2	130.7 (4)	H6A—N6—H6B	107.3
O2—C14—N2	125.6 (4)	C7—O1—Zn1	134.7 (3)
O2—C14—C8	120.8 (4)	C14—O2—Zn1	131.4 (3)
N2—C14—C8	113.7 (4)	H1W—O1W—H2W	102 (7)
N4—C15—C16	112.4 (4)	O4A—S1A—O3A	113.8 (13)
N4—C15—H15A	109.1	O4A—S1A—N1	99.0 (11)
C16—C15—H15A	109.1	O3A—S1A—N1	119.6 (9)
N4—C15—H15B	109.1	O4A—S1A—C6	106.5 (10)
C16—C15—H15B	109.1	O3A—S1A—C6	117.9 (7)
H15A—C15—H15B	107.9	N1—S1A—C6	97.2 (4)
C17—C16—C15	115.5 (5)	O3B—S1B—O4B	113.0 (8)
C17—C16—H16A	108.4	O3B—S1B—N1	106.6 (6)
C15—C16—H16A	108.4	O4B—S1B—N1	119.8 (5)
C17—C16—H16B	108.4	O3B—S1B—C6	109.0 (7)
C15—C16—H16B	108.4	O4B—S1B—C6	113.4 (4)
H16A—C16—H16B	107.5	N1—S1B—C6	93.1 (3)
N6—C17—C16	113.5 (5)	O5—S2—O6	115.1 (3)
N6—C17—H17A	108.9	O5—S2—N2	110.7 (3)
C16—C17—H17A	108.9	O6—S2—N2	111.8 (2)
N6—C17—H17B	108.9	O5—S2—C13	109.5 (2)
C16—C17—H17B	108.9	O6—S2—C13	110.9 (3)
H17A—C17—H17B	107.7	N2—S2—C13	97.5 (2)
N4—C18—C19	110.7 (5)	N3—Zn1—N6	99.03 (19)
N4—C18—H18A	109.5	N3—Zn1—N5	89.83 (19)
C19—C18—H18A	109.5	N6—Zn1—N5	171.1 (2)
N4—C18—H18B	109.5	N3—Zn1—N4	171.58 (18)
C19—C18—H18B	109.5	N6—Zn1—N4	89.30 (18)
H18A—C18—H18B	108.1	N5—Zn1—N4	81.88 (19)
N5—C19—C18	109.5 (5)	N3—Zn1—O2	88.58 (15)
N5—C19—H19A	109.8	N6—Zn1—O2	91.83 (16)
C18—C19—H19A	109.8	N5—Zn1—O2	87.23 (15)
N5—C19—H19B	109.8	N4—Zn1—O2	92.45 (16)
C18—C19—H19B	109.8	N3—Zn1—O1	91.14 (17)
H19A—C19—H19B	108.2	N6—Zn1—O1	88.13 (15)
N5—C20—C21	112.1 (5)	N5—Zn1—O1	92.84 (17)
N5—C20—H20A	109.2	N4—Zn1—O1	87.83 (17)
C21—C20—H20A	109.2	O2—Zn1—O1	179.72 (18)
N5—C20—H20B	109.2
C6—C1—C2—C3	−0.8 (8)	C1—C6—S1A—O4A	127.3 (13)
C7—C1—C2—C3	179.6 (5)	S1B—C6—S1A—O4A	29.9 (12)
C1—C2—C3—C4	2.0 (9)	C5—C6—S1A—O3A	56.1 (12)
C2—C3—C4—C5	−3.0 (10)	C1—C6—S1A—O3A	−103.4 (10)
C3—C4—C5—C6	2.7 (10)	S1B—C6—S1A—O3A	159.2 (13)
C4—C5—C6—C1	−1.6 (9)	C5—C6—S1A—N1	−174.9 (6)
C4—C5—C6—S1A	−157.6 (7)	C1—C6—S1A—N1	25.7 (7)
C4—C5—C6—S1B	168.0 (5)	S1B—C6—S1A—N1	−71.8 (6)
C2—C1—C6—C5	0.7 (9)	C7—N1—S1B—O3B	125.5 (9)
C7—C1—C6—C5	−179.6 (5)	S1A—N1—S1B—O3B	45.7 (10)
C2—C1—C6—S1A	161.8 (6)	C7—N1—S1B—O4B	−104.7 (7)
C7—C1—C6—S1A	−18.5 (7)	S1A—N1—S1B—O4B	175.6 (10)
C2—C1—C6—S1B	−171.1 (5)	C7—N1—S1B—C6	14.6 (6)
C7—C1—C6—S1B	8.6 (6)	S1A—N1—S1B—C6	−65.1 (7)
C6—C1—C7—O1	−179.7 (5)	C5—C6—S1B—O3B	67.1 (9)
C2—C1—C7—O1	0.0 (9)	C1—C6—S1B—O3B	−122.0 (7)
C6—C1—C7—N1	1.1 (7)	S1A—C6—S1B—O3B	−32.4 (8)
C2—C1—C7—N1	−179.3 (6)	C5—C6—S1B—O4B	−59.8 (8)
C13—C8—C9—C10	1.1 (7)	C1—C6—S1B—O4B	111.2 (6)
C14—C8—C9—C10	−179.4 (4)	S1A—C6—S1B—O4B	−159.2 (9)
C8—C9—C10—C11	−0.1 (8)	C5—C6—S1B—N1	175.8 (6)
C9—C10—C11—C12	−0.7 (9)	C1—C6—S1B—N1	−13.3 (5)
C10—C11—C12—C13	0.6 (8)	S1A—C6—S1B—N1	76.4 (6)
C9—C8—C13—C12	−1.2 (7)	C14—N2—S2—O5	−115.8 (4)
C14—C8—C13—C12	179.2 (4)	C14—N2—S2—O6	114.4 (4)
C9—C8—C13—S2	178.4 (4)	C14—N2—S2—C13	−1.7 (4)
C14—C8—C13—S2	−1.2 (5)	C8—C13—S2—O5	116.8 (4)
C11—C12—C13—C8	0.3 (8)	C12—C13—S2—O5	−63.7 (6)
C11—C12—C13—S2	−179.2 (4)	C8—C13—S2—O6	−115.1 (4)
C13—C8—C14—O2	−178.9 (5)	C12—C13—S2—O6	64.4 (6)
C9—C8—C14—O2	1.6 (7)	C8—C13—S2—N2	1.7 (4)
C13—C8—C14—N2	0.1 (6)	C12—C13—S2—N2	−178.8 (5)
C9—C8—C14—N2	−179.4 (5)	C22—N3—Zn1—N6	138.1 (4)
N4—C15—C16—C17	70.4 (6)	C22—N3—Zn1—N5	−40.7 (4)
C15—C16—C17—N6	−68.9 (6)	C22—N3—Zn1—O2	46.5 (4)
N4—C18—C19—N5	−59.4 (7)	C22—N3—Zn1—O1	−133.6 (4)
N5—C20—C21—C22	68.2 (7)	C17—N6—Zn1—N3	136.5 (4)
C20—C21—C22—N3	−72.1 (6)	C17—N6—Zn1—N4	−42.2 (4)
O1—C7—N1—S1B	168.7 (5)	C17—N6—Zn1—O2	−134.6 (4)
C1—C7—N1—S1B	−12.1 (8)	C17—N6—Zn1—O1	45.6 (4)
O1—C7—N1—S1A	−161.8 (7)	C19—N5—Zn1—N3	163.8 (3)
C1—C7—N1—S1A	17.4 (8)	C20—N5—Zn1—N3	37.6 (4)
O2—C14—N2—S2	−179.9 (4)	C19—N5—Zn1—N4	−17.7 (3)
C8—C14—N2—S2	1.2 (5)	C20—N5—Zn1—N4	−143.8 (5)
C21—C22—N3—Zn1	60.2 (6)	C19—N5—Zn1—O2	75.2 (3)
C19—C18—N4—C15	167.5 (5)	C20—N5—Zn1—O2	−51.0 (4)
C19—C18—N4—Zn1	40.0 (6)	C19—N5—Zn1—O1	−105.1 (3)
C16—C15—N4—C18	176.7 (5)	C20—N5—Zn1—O1	128.8 (4)
C16—C15—N4—Zn1	−60.7 (5)	C18—N4—Zn1—N6	169.4 (4)
C18—C19—N5—C20	174.1 (5)	C15—N4—Zn1—N6	43.5 (4)
C18—C19—N5—Zn1	44.3 (5)	C18—N4—Zn1—N5	−11.9 (4)
C21—C20—N5—C19	−176.1 (5)	C15—N4—Zn1—N5	−137.8 (4)
C21—C20—N5—Zn1	−53.4 (6)	C18—N4—Zn1—O2	−98.8 (4)
C16—C17—N6—Zn1	58.9 (6)	C15—N4—Zn1—O2	135.3 (4)
N1—C7—O1—Zn1	−6.3 (10)	C18—N4—Zn1—O1	81.3 (4)
C1—C7—O1—Zn1	174.6 (4)	C15—N4—Zn1—O1	−44.6 (4)
N2—C14—O2—Zn1	2.1 (8)	C14—O2—Zn1—N3	142.0 (5)
C8—C14—O2—Zn1	−179.1 (3)	C14—O2—Zn1—N6	43.0 (4)
C7—N1—S1A—O4A	−133.4 (12)	C14—O2—Zn1—N5	−128.1 (5)
S1B—N1—S1A—O4A	−23.0 (11)	C14—O2—Zn1—N4	−46.4 (5)
C7—N1—S1A—O3A	102.6 (9)	C7—O1—Zn1—N3	46.4 (6)
S1B—N1—S1A—O3A	−147.1 (12)	C7—O1—Zn1—N6	145.4 (6)
C7—N1—S1A—C6	−25.4 (8)	C7—O1—Zn1—N5	−43.5 (6)
S1B—N1—S1A—C6	85.0 (9)	C7—O1—Zn1—N4	−125.3 (6)
C5—C6—S1A—O4A	−73.2 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.90	2.56	3.282 (7)	137
N6—H6A···N2	0.90	2.52	3.224 (6)	135
N5—H5A···N1	1.00 (6)	2.60 (6)	3.411 (7)	138 (4)
N4—H4A···N2	0.76 (7)	2.53 (7)	3.278 (6)	166 (7)
O1W—H1W···O5	0.86 (2)	2.01 (3)	2.833 (8)	161 (8)
N3—H3B···O1W^i	0.90	2.22	3.052 (7)	154
N6—H6B···O1W^i	0.90	2.22	3.071 (9)	157

Symmetry code: (i) −x+3/2, −y+1, z+1/2.