A reinvestigation of the space group of catena-poly[[[triaqua(sulfato-κO)zinc(II)]-μ-4,4′-bipyridine-κ²N:N′] dihydrate]

In the title compound, {[Zn(SO₄)(C₁₀H₈N₂)(H₂O)₃]·2H₂O}_n, the N-heterocycle of (4,4′-bipyridine)triaqua­sulfatozinc dihydrate links the sulfate- and water-coordinated Zn atom into a helical chain that runs along the a axis of the hexa­gonal P6₁ unit cell; adjacent chains are linked by hydrogen bonds into a three-dimensional network. The structure is a twin, the components being nearly 50%.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.010 Å
• H-atom completeness 45%
• R factor = 0.045
• wR factor = 0.124
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O4W

Author Response: Hydrogen atoms of all water molecules are not calculated.

PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O5W

Author Response: Hydrogen atoms of all water molecules are not calculated.

Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C8
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O4W     ..       2.76 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O3W    ..  O5W     ..       2.76 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O4     ..  O4W     ..       2.77 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O4W    ..  O5W     ..       2.81 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.450     0.730
            Tmin(prime) and Tmax expected:      0.536     0.732
            RR(prime) =      0.841
            Please check that your absorption correction is appropriate.
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    6
           From the CIF: _chemical_formula_weight           407.69
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   10.00  120.11
           H         1.01    8.00    8.06
           N        14.01    2.00   28.01
           O        16.00    9.00  143.99
           S        32.07    1.00   32.07
           Zn       65.39    1.00   65.39
           Calculated formula weight              397.64
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     407.69
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.37
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom C6      has ADP max/min Ratio .............       3.20 prola
PLAT213_ALERT_2_C Atom C7      has ADP max/min Ratio .............       4.00 prola
PLAT213_ALERT_2_C Atom C9      has ADP max/min Ratio .............       4.00 prola
PLAT213_ALERT_2_C Atom C10     has ADP max/min Ratio .............       3.20 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.41
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10

Alert level G
FORMU01_ALERT_1_G  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:   C10 H18 N2 O9 S1 Zn1
            Atom count from _chemical_formula_moiety:H4 O2
FORMU01_ALERT_2_G  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:C10 H18 N2 O9 S1 Zn1
            Atom count from the _atom_site data:  C10 H8 N2 O9 S1 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    6
           From the CIF: _chemical_formula_sum  C10 H18 N2 O9 S Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         60.00     60.00    0.00
           H        108.00     48.00   60.00
           N         12.00     12.00    0.00
           O         54.00     54.00    0.00
           S          6.00      6.00    0.00
           Zn         6.00      6.00    0.00
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           27.40
           From the CIF: _reflns_number_total               3514
           Count of symmetry unique reflns         1838
           Completeness (_total/calc)            191.19%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1676
           Fraction of Friedel pairs measured     0.912
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       1.83
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         41

   2 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  20 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

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

---

S1. Comment

The crystal structure of (4,4'-bipyridine)triaquasulfatozinc dihydrate, which is described in the P6₅ space group, shows a bipyridine-bridged, helical chain structure having unidentate sulfate groups (Kondo et al., 1999; Ma et al., 2000). The compound with the formulation 2[C₁₀H₁₀N₂]²⁺ [(C₁₀H₈N₂)₃(H₂O)₆(SO₄)₄Zn₃]^4-.10H₂O, isolated at a different pH, has the sulfate groups in µ₂-bridging modes (Tong & Chen, 2000). Under solvothermal conditions, a monoaqua monohydrate is also known but the sulfate group engages in a different bonding mode (Huang et al., 1998).

In the present study, the crystal structure of (4,4'-bipyridine)triaquasulfatozinc dihydrate when refined in the P6₁ space group gave a Flack parameter (Flack, 1983) of nearly zero. Interestingly, two previous studies have described the compound in the P6₅ space group (Kondo et al., 1999; Ma et al., 2000), so that the present and previous studies hint at the possibility that helices of opposite handedness could be present in a synthesis. Such has not been mentioned in the literature. Unfortunately, the Flack parameter is not given in the earlier reports, and one (Ma et al., 2000) used a large weighting scheme.

The crystal structure of the analogous (4,4'-bipyridine)triaquasulfatocopper dihydrate is known in the P6₅ form its Flack parameter refined to nearly zero (Hagrman et al., 1998; Lin & Liu, 2003). A P6₁ polymorph has also been reported; however, as its Flack parameter refined to 0.93 (Yuan et al., 2003), the form may be the P6₅ form only.

The existence of pairs of enantiomorphic structures is rarely discussed in the literature as finding such compounds is regarded as being unlikely (Brock & Dunitz, 1991). Amonium dioxalatotitanate dihydrate was refined by SHELX-76 in P6₂22; the authors attempted a refinement in P6₄22 but in view of statistical tests available then, concluded that the space group was P6₂222 as it led to significantly better agreement (English & Eve, 1993). A later study on the charge density (Sheu et al., 1996) did not comment on the alternative choice of the P6₄22 setting. The title zinc compound (in P6₁) and the isostructural copper compound (in P6₅) can be regarded as exemplifying such a pair of achiral metal-organic compounds. In this case, the space groups can be distinguished on the basis of anomalous dispersion (Ha & Allewell, 1997).

Related literature

For adducts of zinc sulfate and 4,4'-bipyridine in molar stoichiometries, see Huang et al. (1998) and Tong & Chen (2000). For the title compound described in the P6₅ space group, see Kondo et al. (1999) and Ma et al. (2000). For the analogous copper compound that is described in the P6₁ space group, see Lin & Liu (2003), and for the same compound described in the P6₅ space group, see Hagrman et al. (1998) and Yuan et al. (2003).

For literature on enantiomorphous space groups, see Ha & Allewell (1997) and for a comment on the rarity of compounds crystallizing in both enantiomorphous space groups, see Brock & Dunitz (1991). For the possible existence of two enantiomorphic forms of ammonium dioxalatotitanate dihydrate, see English & Eve (1993) and Sheu et al. (1996).

For related literature, see: Flack (1983); Spek (2003).

S2. Experimental

The compound was the unexpected product from the reaction of zinc sulfate monohydrate (0.09 g, 5 mmol), 3-(3-carboxyphenoxy)propionic acid (0.10 g, 5 mmol), sodium hydroxide (0.04 g, 10 mmol) and 4,4'-bipyridine (0.08 g, 5 mmol) in methanol. Colorless prismatic crystals were obtained from the filtered solution after several days.

S3. Refinement

The structure is twinned; the use of the TwinRotMat routine of the PLATON suite (Spek, 2003) gave the TWIN command as (1 1 0 0 - 1 0 0 0 - 1). The twin component refined to 0.54 (1).

For the 4,4'-bipyridine molecule, the C–N bond distances were restrained to 0.005 Å of each other as were the C–C bond distances of the rings. There was some disorder in the carbon atoms as some temperature factors were too small whereas others were too large. As the molecule has approximate twofold rotational symmetry along the N···N vector, the temperature factors of pairs of carbon atoms (i.e., C1/C5, C2/C4, C6/C10 and C7/C9) were restrained to be the same.

The carbon-bound hydrogen atoms were placed at calculated positions (C–H 0.93 Å) and were inlcuded in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C). Although the hydronge atoms of the water molecules could be placed in chemically sensible positions on the basis of hydrogen bonds, more than one such scheme may be envisaged. As such, hydrogen atoms were not included in the refinement.

The final difference Fourier map had a large peak in the neighbourhood of O1W, but was otherwise diffuse.

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

Fig. 1. Thermal ellipsoid plot of a portion of the chain structure of [(C10H8N2)(H2O)3(SO4)Zn]^.2H2O. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are not drawn. Translational code (i): x – 1, y, z.

catena-poly[[[triaqua(sulfato-κO)zinc(II)]-µ- 4,4'-bipyridine-κ²N:N'] dihydrate]

Crystal data

[Zn(SO4)(C10H8N2)(H2O)3]·2H2O	Dx = 1.716 Mg m^−3
Mr = 407.69	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 21095 reflections
Hall symbol: P 61	θ = 3.6–27.4°
a = 11.4275 (3) Å	µ = 1.74 mm^−1
c = 20.9322 (6) Å	T = 295 K
V = 2367.27 (9) Å^3	Prism, colorless
Z = 6	0.35 × 0.29 × 0.18 mm
F(000) = 1260

Data collection

Rigaku RAXIS-RAPID IP diffractometer	3514 independent reflections
Radiation source: fine-focus sealed tube	3309 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scan	θmax = 27.4°, θmin = 3.6°
Absorption correction: multi-scan ABSCOR (Higashi, 1995)	h = −14→14
Tmin = 0.45, Tmax = 0.73	k = −14→14
22988 measured reflections	l = −25→27

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0882P)^2 + 0.7556P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
3514 reflections	Δρmax = 1.46 e Å^−3
185 parameters	Δρmin = −0.43 e Å^−3
41 restraints	Absolute structure: Flack parameter for 1473 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (2)

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

	x	y	z	Uiso*/Ueq
Zn1	0.57094 (6)	1.00177 (10)	0.49998 (4)	0.02328 (15)
S1	0.38825 (14)	0.64977 (15)	0.47291 (7)	0.0273 (3)
O1	0.4543 (5)	0.7708 (5)	0.51774 (19)	0.0286 (10)
O2	0.2571 (5)	0.5504 (5)	0.4983 (3)	0.0487 (13)
O3	0.3648 (5)	0.6913 (5)	0.4104 (2)	0.0472 (14)
O4	0.4787 (7)	0.5936 (6)	0.4647 (3)	0.0566 (16)
O1w	0.6807 (5)	1.2160 (5)	0.4796 (2)	0.0282 (10)
O2w	0.5570 (5)	0.9639 (6)	0.4045 (3)	0.0389 (13)
O3w	0.5760 (6)	1.0252 (6)	0.6000 (3)	0.0412 (15)
O4w	0.1575 (7)	0.6249 (9)	0.6013 (3)	0.074 (2)
O5w	0.5635 (6)	0.6791 (6)	0.3194 (3)	0.0489 (12)
N1	0.7614 (4)	1.0049 (5)	0.5031 (3)	0.0261 (9)
N2	1.3815 (4)	1.0025 (6)	0.4974 (4)	0.0316 (10)
C1	0.7649 (6)	0.8902 (6)	0.5018 (5)	0.0347 (9)
H1	0.6836	0.8088	0.5005	0.042*
C2	0.8846 (5)	0.8873 (6)	0.5022 (4)	0.0318 (8)
H2	0.8827	0.8050	0.5023	0.038*
C3	1.0071 (4)	1.0071 (6)	0.5026 (4)	0.0246 (8)
C4	1.0036 (6)	1.1263 (6)	0.5042 (4)	0.0318 (8)
H4	1.0831	1.2093	0.5054	0.038*
C5	0.8795 (5)	1.1195 (6)	0.5038 (5)	0.0347 (9)
H5	0.8784	1.2004	0.5041	0.042*
C6	1.2611 (5)	0.8924 (7)	0.4970 (7)	0.0646 (18)
H6	1.2595	0.8105	0.4935	0.078*
C7	1.1377 (7)	0.8860 (7)	0.5012 (8)	0.076 (2)
H7	1.0578	0.8038	0.5050	0.092*
C8	1.1372 (5)	1.0062 (6)	0.4997 (4)	0.0263 (9)
C9	1.2614 (6)	1.1228 (7)	0.4997 (8)	0.076 (2)
H9	1.2661	1.2062	0.5029	0.092*
C10	1.3794 (6)	1.1172 (7)	0.4948 (6)	0.0646 (18)
H10	1.4607	1.1975	0.4896	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0185 (3)	0.0317 (3)	0.0245 (2)	0.0161 (3)	−0.0012 (3)	−0.0016 (2)
S1	0.0231 (6)	0.0313 (7)	0.0282 (6)	0.0142 (6)	−0.0029 (5)	−0.0036 (6)
O1	0.028 (2)	0.038 (3)	0.026 (2)	0.022 (2)	0.0011 (17)	−0.0011 (18)
O2	0.046 (3)	0.044 (3)	0.036 (2)	0.007 (2)	0.008 (2)	0.003 (2)
O3	0.058 (3)	0.040 (3)	0.039 (3)	0.020 (3)	−0.025 (3)	−0.009 (2)
O4	0.062 (3)	0.062 (4)	0.068 (4)	0.048 (3)	−0.021 (3)	−0.026 (3)
O1w	0.023 (2)	0.023 (2)	0.036 (2)	0.0106 (18)	0.0037 (19)	0.0042 (17)
O2w	0.030 (3)	0.044 (3)	0.029 (3)	0.008 (2)	−0.011 (2)	0.000 (2)
O3w	0.069 (4)	0.049 (3)	0.017 (2)	0.038 (3)	−0.002 (2)	−0.002 (2)
O4w	0.047 (3)	0.086 (5)	0.070 (4)	0.018 (3)	0.013 (3)	−0.011 (4)
O5w	0.049 (3)	0.052 (3)	0.054 (3)	0.031 (3)	0.002 (2)	−0.013 (2)
N1	0.019 (2)	0.032 (2)	0.029 (2)	0.013 (2)	0.000 (2)	0.0033 (19)
N2	0.016 (2)	0.035 (2)	0.044 (2)	0.012 (2)	0.006 (3)	−0.0010 (19)
C1	0.017 (2)	0.032 (2)	0.051 (2)	0.009 (2)	0.000 (2)	0.0027 (18)
C2	0.024 (2)	0.0298 (19)	0.050 (2)	0.020 (2)	−0.007 (2)	−0.0013 (17)
C3	0.018 (3)	0.034 (3)	0.0283 (19)	0.018 (3)	0.005 (3)	−0.0024 (19)
C4	0.024 (2)	0.0298 (19)	0.050 (2)	0.020 (2)	−0.007 (2)	−0.0013 (17)
C5	0.017 (2)	0.032 (2)	0.051 (2)	0.009 (2)	0.000 (2)	0.0027 (18)
C6	0.020 (2)	0.032 (2)	0.147 (6)	0.017 (2)	−0.003 (4)	−0.013 (3)
C7	0.022 (2)	0.031 (2)	0.183 (7)	0.019 (2)	0.016 (4)	0.000 (3)
C8	0.010 (2)	0.032 (3)	0.035 (2)	0.009 (2)	0.002 (3)	0.001 (2)
C9	0.022 (2)	0.031 (2)	0.183 (7)	0.019 (2)	0.016 (4)	0.000 (3)
C10	0.020 (2)	0.032 (2)	0.147 (6)	0.017 (2)	−0.003 (4)	−0.013 (3)

Geometric parameters (Å, º)

Zn1—O1	2.316 (5)	C1—H1	0.9300
Zn1—O1W	2.163 (5)	C2—C3	1.384 (4)
Zn1—O2W	2.034 (6)	C2—H2	0.9300
Zn1—O3W	2.108 (5)	C3—C4	1.383 (9)
Zn1—N1	2.160 (4)	C3—C8	1.492 (5)
Zn1—N2^i	2.170 (4)	C4—C5	1.381 (10)
S1—O2	1.455 (5)	C4—H4	0.9300
S1—O3	1.461 (5)	C5—H5	0.9300
S1—O4	1.474 (5)	C6—C7	1.378 (11)
S1—O1	1.523 (5)	C6—H6	0.9300
N1—C1	1.331 (4)	C7—C8	1.377 (10)
N1—C5	1.330 (4)	C7—H7	0.9300
N2—C6	1.321 (9)	C8—C9	1.378 (10)
N2—C10	1.324 (9)	C9—C10	1.385 (11)
N2—Zn1^ii	2.170 (4)	C9—H9	0.9300
C1—C2	1.385 (10)	C10—H10	0.9300
O2w—Zn1—O3w	175.7 (3)	N1—C1—H1	118.7
O2w—Zn1—N1	90.3 (2)	C2—C1—H1	118.7
O3w—Zn1—N1	90.3 (3)	C3—C2—C1	119.9 (5)
O2w—Zn1—O1w	89.2 (2)	C3—C2—H2	120.0
O3w—Zn1—O1w	95.1 (2)	C1—C2—H2	120.0
N1—Zn1—O1w	88.8 (2)	C2—C3—C4	117.4 (4)
O2w—Zn1—N2^i	90.2 (3)	C2—C3—C8	120.8 (5)
O3w—Zn1—N2^i	89.3 (3)	C4—C3—C8	121.8 (5)
N1—Zn1—N2^i	178.9 (2)	C5—C4—C3	118.7 (5)
O1w—Zn1—N2^i	90.3 (2)	C5—C4—H4	120.7
O2w—Zn1—O1	88.6 (2)	C3—C4—H4	120.7
O3w—Zn1—O1	87.09 (19)	N1—C5—C4	124.2 (5)
N1—Zn1—O1	90.86 (19)	N1—C5—H5	117.9
O1w—Zn1—O1	177.80 (19)	C4—C5—H5	117.9
N2^i—Zn1—O1	90.1 (2)	N2—C6—C7	126.9 (6)
O2—S1—O3	107.2 (3)	N2—C6—H6	116.5
O2—S1—O4	112.1 (4)	C7—C6—H6	116.5
O3—S1—O4	108.6 (4)	C8—C7—C6	117.4 (6)
O2—S1—O1	109.4 (3)	C8—C7—H7	121.3
O3—S1—O1	110.2 (3)	C6—C7—H7	121.3
O4—S1—O1	109.3 (3)	C7—C8—C9	116.6 (4)
S1—O1—Zn1	132.7 (2)	C7—C8—C3	120.4 (5)
C1—N1—C5	117.1 (4)	C9—C8—C3	122.8 (5)
C1—N1—Zn1	120.6 (4)	C8—C9—C10	120.7 (6)
C5—N1—Zn1	122.3 (4)	C8—C9—H9	119.6
C6—N2—C10	114.6 (5)	C10—C9—H9	119.6
C6—N2—Zn1^ii	124.2 (4)	N2—C10—C9	122.9 (6)
C10—N2—Zn1^ii	121.1 (4)	N2—C10—H10	118.6
N1—C1—C2	122.6 (5)	C9—C10—H10	118.6
O2—S1—O1—Zn1	−136.6 (4)	C2—C3—C4—C5	−1.4 (16)
O3—S1—O1—Zn1	−18.9 (4)	C8—C3—C4—C5	177.0 (8)
O4—S1—O1—Zn1	100.3 (4)	C1—N1—C5—C4	−1.0 (18)
O2w—Zn1—O1—S1	−4.5 (4)	Zn1—N1—C5—C4	−178.3 (7)
O3w—Zn1—O1—S1	175.0 (4)	C3—C4—C5—N1	1.1 (17)
N1—Zn1—O1—S1	−94.8 (4)	C10—N2—C6—C7	−8 (2)
N2^i—Zn1—O1—S1	85.7 (4)	Zn1^ii—N2—C6—C7	173.6 (13)
O2w—Zn1—N1—C1	−76.9 (8)	N2—C6—C7—C8	7 (3)
O3w—Zn1—N1—C1	98.8 (8)	C6—C7—C8—C9	−5 (2)
O1w—Zn1—N1—C1	−166.1 (8)	C6—C7—C8—C3	178.6 (11)
O1—Zn1—N1—C1	11.7 (8)	C2—C3—C8—C7	−4.7 (16)
O2w—Zn1—N1—C5	100.3 (8)	C4—C3—C8—C7	177.0 (11)
O3w—Zn1—N1—C5	−84.0 (8)	C2—C3—C8—C9	179.7 (11)
O1w—Zn1—N1—C5	11.1 (8)	C4—C3—C8—C9	1.3 (16)
O1—Zn1—N1—C5	−171.1 (8)	C7—C8—C9—C10	6 (2)
C5—N1—C1—C2	1.2 (17)	C3—C8—C9—C10	−177.9 (12)
Zn1—N1—C1—C2	178.5 (7)	C6—N2—C10—C9	8 (2)
N1—C1—C2—C3	−1.5 (17)	Zn1^ii—N2—C10—C9	−173.2 (12)
C1—C2—C3—C4	1.6 (16)	C8—C9—C10—N2	−8 (2)
C1—C2—C3—C8	−176.8 (8)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.