catena-Poly[[[aqua­(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)zinc]-μ-3-chloro­benzene-1,2-dicaboxylato-κ2O2:O3] [[(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)zinc]-μ-3-chloro­benzene-1,2-dicaboxylato-κ2O2:O3]]

Zhu, Y.; Li, H.-Y.; Ma, M.-L.

doi:10.1107/S1600536812014006

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m574-m575

doi:10.1107/S1600536812014006

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catena-Poly[[[aqua(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)zinc]-μ-3-chlorobenzene-1,2-dicaboxylato-κ²O²:O³] [[(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)zinc]-μ-3-chlorobenzene-1,2-dicaboxylato-κ²O²:O³]]

Yu Zhu,^a ^* Hai-Yang Li ^a and Ming-Li Ma ^a

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: zhuyu@zzu.edu.cn

(Received 27 February 2012; accepted 31 March 2012; online 13 April 2012)

In the title compound, {[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]}_n, one Zn²⁺ ion is five-coordinated by two O atoms from two different 3-chlorobenzene-1,2-dicarboxylate ligands, one O atom from a water molecule and two N atoms from a 4,4′-dimethyl-2,2′-bipyridine ligand, while the second Zn²⁺ ion is four-coordinated by two O atoms from two different 3-chlorobenzene-1,2-dicarboxylate ligands, and two N atoms from a 4,4′-bimethyl-2,2′-bipyridine ligand. The crystal structure exhibits a three-dimensional supramolecular structure composed of alternate Zn(C₈H₃O₄Cl)(C₁₂H₁₂N₂) and Zn(C₈H₃O₄Cl)(C₁₂H₁₂N₂)(H₂O) chains, which are linked together by face-to-face π–π interactions [shortest centroid–centroid distances of 3.661 (4) and 3.6901 (3) Å], O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ); Ockwig et al. (2005 ); Zang et al. (2011 ). For related O—H⋯O hydrogen bonds, see: Desiraju et al. (2004 ). For related π–π interactions, see: Zang et al. (2010 ). For related C—H⋯O hydrogen bonds, see: Desiraju et al. (1996 ). For related C—H⋯π interactions, see: Nishio et al. (1998 ).

Experimental

Crystal data

[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]
M_r = 914.38
Orthorhombic, P n a 2₁
a = 34.050 (4) Å
b = 14.1831 (10) Å
c = 7.8764 (6) Å
V = 3803.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.47 mm⁻¹
T = 291 K
0.20 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.971, T_max = 1.000
10533 measured reflections
6396 independent reflections
5076 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.104
S = 1.07
6396 reflections
518 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 2200 Friedel pairs
Flack parameter: 0.093 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4ⁱ	0.85	2.10	2.768 (6)	135
O1W—H1WB⋯O4ⁱⁱ	0.85	1.79	2.644 (6)	179
O1W—H1WB⋯O3ⁱⁱ	0.85	2.43	2.930 (5)	118
C17—H17⋯O4ⁱ	0.93	2.36	3.202 (8)	150
C20—H20⋯O6ⁱⁱⁱ	0.93	2.28	3.171 (8)	160
C23—H23⋯O6ⁱⁱⁱ	0.93	2.40	3.306 (8)	164
C32—H32⋯O2ⁱ	0.93	2.57	3.459 (8)	161
C35—H35⋯O2ⁱ	0.93	2.45	3.353 (8)	165
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014006/zq2156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014006/zq2156Isup2.hkl

checkCIF report

Comment top

In recent years, metallosupramolecular compounds have received much attention due to their variety of architectures and the potential applications as functional materials (Maspoch et al., 2007; Ockwig et al., 2005). Early reports have shown that carboxylate compounds and nitrogen heterocyclic ligands have been successfully employed in the generation of many novel structures (Zang et al., 2011). To further explore various factors that influence the properties and construction of coordination compounds, we undertake synthetic and structural studies on a novel Zn^II complex based on 3-chlorophthalic acid (H2cp) and 4,4'-dimethyl-2,2'-bipyridine (dmbpy).

The X-ray diffraction study revealed that the title compound crystallizes in the orthorhombic space group Pna2₁. The Zn1 atom is five-coordinated by two O atoms from two different 3-chlorobenzene-1,2-dicarboxylato ligands, one O atom from a water molecule and two N atoms from a 4,4'-dimethyl-2,2'-bipyridine ligand, while the Zn2 atom is four-coordinated by two O atoms from two different 3-chlorobenzene-1,2-dicarboxylato ligands, and two N atoms from a 4,4'-bimethyl-2,2'-bipyridine ligand (Fig. 1). Each cp^2- ligand acts as a µ₂-bridge linking two Zn atoms with both carboxylate groups in monodentate fashion resulting into two chains along the c axis. These two chains are further connected together by face-to-face π–π interactions (Zang et al., 2010) involving pyridine rings of different chains. The shortest Cg···Cg distances of 3.661 (4) and 3.6901 (3) are observed between Cg2 and Cg4, and Cg1 and Cg3, respectively (Cg1 is the centroid of the N1/C17–C21 ring, Cg2 of N2/C22–C26, Cg3 of N3/C34–C38, and Cg4 of N4/C29–C33). Adjacent zippered structures are linked together to form tetra-chain units by intermolecular O1w—H1wa···O4ⁱⁱⁱ hydrogen bonds (Desiraju et al., 2004) and C17—H17···O4ⁱⁱⁱ interactions (symmetry code: iii = -x + 1, -y + 1, z + 1/2). Each unit is further connected to other units through C20—H20···O6^iv, C23—H23···O6^iv (symmetry code: iv = -x + 1, -y + 1, z - 1/2), C32—H32···O2ⁱⁱⁱ, C35—H35···O2ⁱⁱⁱ (Desiraju et al., 1996) and C—H···π interactions (the shortest one being C37—H37···Cg5^v = 2.79 Å; Cg5 centroid of C11–C16; symmetry code: v = -x + 3/2, y - 1/2, z - 1/2) (Nishio et al., 1998) to form a three-dimensional supramolecular structure (Fig. 3).

Related literature top

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007); Ockwig et al. (2005); Zang et al. (2011). For related O—H···O hydrogen bonds, see: Desiraju et al. (2004). For related π–π interactions, see: Zang et al. (2010). For related C—H···O hydrogen bonds, see: Desiraju et al. (1996). For related C—H···π interactions, see: Nishio et al. (1998).

Experimental top

The title compound was synthesized hydrothermally in a Teflon-lined stainless steel container by heating a mixture of 3-chlorophthalic acid (H₂cp) (0.0100 g, 0.05 mmol), 4,4'-bimethyl-2,2'-bipyridine (dmbpy) (0.0092 g, 0.05 mmol), Zn(NO₃)₂.6H₂O (0.0149 g, 0.05 mmol) and NaOH (0.0040 g, 0.1 mmol) in 7 ml of distilled water at 120°C for 3 days, and then cooled to room temperature. Colourless block crystals were obtained in 71% yield (based on zinc).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Metal coordination and atom labeling in the title compound (thermal ellipsoids drawn at the 50% probability level). All hydrogen atoms are omitted for clarity. Symmetry code: x, y, z - 1.
	Fig. 2. A view of the layered structure of the title compound. Dotted lines represent the π–π interactions (symmetry code: -x + 1, -y + 1, z + 0.5.)
	Fig. 3. The three-dimensional supramolecular structure of the title compound (hydrogen bonds and C—H–π interactions as dotted lines).

catena-Poly[[[aqua(4,4'-dimethyl-2,2'-bipyridine- κ²N,N')zinc]-µ-3-chlorobenzene-1,2-dicaboxylato- κ²O²:O³] [[(4,4'-dimethyl-2,2'-bipyridine- κ²N,N')zinc]-µ-3-chlorobenzene-1,2-dicaboxylato- κ²O²:O³]] top

Crystal data top

[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]	D_x = 1.597 Mg m⁻³
M_r = 914.38	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, Pna2₁	Cell parameters from 1842 reflections
a = 34.050 (4) Å	θ = 2.9–29.3°
b = 14.1831 (10) Å	µ = 1.47 mm⁻¹
c = 7.8764 (6) Å	T = 291 K
V = 3803.8 (6) Å³	Prismatic, colourless
Z = 4	0.20 × 0.18 × 0.16 mm
F(000) = 1864

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	6396 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5076 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 16.2312 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −18→42
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −17→17
T_min = 0.971, T_max = 1.000	l = −7→9
10533 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
6396 reflections	Δρ_max = 0.63 e Å⁻³
518 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2200 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.093 (14)

Crystal data top

[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]	V = 3803.8 (6) Å³
M_r = 914.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 34.050 (4) Å	µ = 1.47 mm⁻¹
b = 14.1831 (10) Å	T = 291 K
c = 7.8764 (6) Å	0.20 × 0.18 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	6396 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	5076 reflections with I > 2σ(I)
T_min = 0.971, T_max = 1.000	R_int = 0.044
10533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.104	Δρ_max = 0.63 e Å⁻³
S = 1.07	Δρ_min = −0.37 e Å⁻³
6396 reflections	Absolute structure: Flack (1983), 2200 Friedel pairs
518 parameters	Absolute structure parameter: 0.093 (14)
1 restraint

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.446526 (19)	0.36444 (4)	0.62772 (9)	0.02863 (16)
Zn2	0.73030 (2)	0.67276 (5)	0.37248 (10)	0.03441 (18)
Cl1	0.53270 (7)	0.15962 (15)	−0.2478 (2)	0.0655 (6)
Cl2	0.84880 (6)	0.65033 (13)	1.2682 (2)	0.0487 (5)
O1	0.48307 (15)	0.3004 (3)	0.4755 (5)	0.0462 (13)
O1W	0.47741 (14)	0.4839 (3)	0.7036 (6)	0.0493 (13)
H1WA	0.4918	0.5028	0.6220	0.074*
H1WB	0.4881	0.4524	0.7830	0.074*
O2	0.45488 (16)	0.3521 (3)	0.2380 (6)	0.0524 (14)
O3	0.46114 (11)	0.2980 (3)	−0.1501 (5)	0.0289 (9)
O4	0.51092 (14)	0.3849 (3)	−0.0516 (5)	0.0450 (12)
O5	0.77114 (14)	0.6635 (4)	0.5400 (6)	0.0487 (13)
O6	0.73636 (14)	0.6683 (4)	0.7724 (6)	0.0651 (17)
O7	0.75751 (13)	0.7136 (3)	1.1661 (5)	0.0400 (11)
O8	0.76227 (13)	0.5605 (3)	1.1177 (7)	0.0553 (13)
N1	0.39925 (14)	0.4462 (3)	0.5397 (6)	0.0282 (12)
N2	0.39966 (14)	0.2639 (3)	0.6065 (7)	0.0315 (12)
N3	0.68490 (14)	0.5810 (3)	0.3955 (6)	0.0335 (12)
N4	0.68816 (15)	0.7651 (3)	0.4601 (6)	0.0329 (13)
C1	0.47656 (19)	0.2992 (5)	0.3164 (7)	0.0305 (15)
C1A	0.49032 (19)	0.3121 (4)	−0.0579 (7)	0.0266 (14)
C2	0.5919 (2)	0.9246 (5)	0.6602 (12)	0.072 (3)
H2A	0.5960	0.9384	0.7781	0.107*
H2B	0.5682	0.8888	0.6473	0.107*
H2C	0.5898	0.9824	0.5975	0.107*
C3	0.49776 (19)	0.2223 (4)	0.2198 (7)	0.0264 (14)
C4	0.50368 (18)	0.2278 (4)	0.0461 (7)	0.0263 (14)
C5	0.5226 (2)	0.1537 (4)	−0.0331 (9)	0.0388 (18)
C6	0.5346 (2)	0.0737 (5)	0.0544 (9)	0.0463 (19)
H6	0.5470	0.0246	−0.0028	0.056*
C7	0.5282 (2)	0.0680 (5)	0.2251 (9)	0.0447 (19)
H7	0.5356	0.0143	0.2846	0.054*
C8	0.5105 (2)	0.1420 (4)	0.3089 (8)	0.0404 (18)
H8	0.5071	0.1388	0.4258	0.049*
C9	0.7673 (2)	0.6666 (5)	0.7003 (9)	0.0356 (17)
C10	0.77225 (18)	0.6434 (4)	1.0906 (7)	0.0325 (15)
C11	0.80563 (19)	0.6689 (4)	0.7983 (7)	0.0292 (15)
C12	0.80732 (19)	0.6604 (4)	0.9751 (7)	0.0251 (14)
C13	0.8441 (2)	0.6620 (4)	1.0484 (8)	0.0308 (15)
C14	0.8786 (2)	0.6732 (4)	0.9570 (9)	0.0384 (17)
H14	0.9028	0.6751	1.0115	0.046*
C15	0.8759 (2)	0.6812 (5)	0.7839 (10)	0.0473 (19)
H15	0.8986	0.6874	0.7192	0.057*
C16	0.8403 (2)	0.6802 (4)	0.7065 (7)	0.0354 (16)
H16	0.8390	0.6873	0.5892	0.043*
C17	0.4015 (2)	0.5397 (4)	0.5072 (9)	0.0426 (17)
H17	0.4248	0.5717	0.5298	0.051*
C18	0.3702 (2)	0.5882 (4)	0.4417 (9)	0.0448 (18)
H18	0.3724	0.6526	0.4209	0.054*
C19	0.3356 (2)	0.5428 (4)	0.4066 (8)	0.0404 (17)
C20	0.33365 (19)	0.4466 (4)	0.4388 (8)	0.0378 (16)
H20	0.3105	0.4136	0.4181	0.045*
C21	0.36621 (18)	0.4002 (4)	0.5020 (7)	0.0281 (14)
C22	0.36610 (18)	0.2978 (4)	0.5409 (7)	0.0285 (14)
C23	0.33407 (19)	0.2400 (4)	0.5094 (8)	0.0371 (16)
H23	0.3112	0.2650	0.4631	0.045*
C24	0.3363 (2)	0.1447 (4)	0.5475 (9)	0.0441 (18)
C25	0.3715 (2)	0.1119 (4)	0.6178 (11)	0.0478 (18)
H25	0.3743	0.0485	0.6453	0.057*
C26	0.4011 (2)	0.1728 (4)	0.6454 (9)	0.0471 (18)
H26	0.4240	0.1497	0.6947	0.057*
C27	0.3001 (2)	0.5942 (5)	0.3372 (12)	0.074 (3)
H27A	0.2881	0.6302	0.4263	0.111*
H27B	0.2816	0.5492	0.2937	0.111*
H27C	0.3082	0.6357	0.2475	0.111*
C28	0.3008 (2)	0.0812 (5)	0.5202 (10)	0.064 (2)
H28A	0.2998	0.0345	0.6084	0.096*
H28B	0.3029	0.0506	0.4119	0.096*
H28C	0.2772	0.1184	0.5233	0.096*
C29	0.6922 (2)	0.8562 (5)	0.4932 (10)	0.0499 (19)
H29	0.7161	0.8853	0.4702	0.060*
C30	0.6618 (2)	0.9098 (4)	0.5612 (9)	0.049 (2)
H30	0.6656	0.9734	0.5847	0.059*
C31	0.62615 (19)	0.8681 (4)	0.5935 (9)	0.0410 (18)
C32	0.62257 (19)	0.7715 (4)	0.5612 (8)	0.0356 (16)
H32	0.5989	0.7408	0.5827	0.043*
C33	0.65364 (19)	0.7224 (4)	0.4983 (7)	0.0290 (14)
C34	0.65222 (19)	0.6193 (4)	0.4647 (7)	0.0296 (15)
C35	0.61938 (19)	0.5652 (4)	0.5012 (7)	0.0351 (16)
H35	0.5973	0.5938	0.5480	0.042*
C36	0.6189 (2)	0.4691 (4)	0.4691 (8)	0.0384 (17)
C37	0.6532 (2)	0.4317 (4)	0.3981 (10)	0.0473 (19)
H37	0.6547	0.3676	0.3745	0.057*
C38	0.6845 (2)	0.4887 (4)	0.3632 (10)	0.0460 (17)
H38	0.7067	0.4617	0.3144	0.055*
C39	0.5834 (2)	0.4107 (5)	0.5081 (10)	0.059 (2)
H39A	0.5900	0.3642	0.5920	0.088*
H39B	0.5746	0.3799	0.4066	0.088*
H39C	0.5629	0.4506	0.5509	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0277 (4)	0.0328 (3)	0.0254 (3)	0.0020 (3)	0.0000 (4)	0.0016 (3)
Zn2	0.0264 (4)	0.0442 (4)	0.0327 (4)	0.0009 (3)	0.0010 (4)	−0.0032 (4)
Cl1	0.0765 (16)	0.0915 (15)	0.0283 (10)	0.0279 (13)	0.0089 (10)	−0.0091 (10)
Cl2	0.0505 (13)	0.0658 (12)	0.0297 (9)	0.0041 (10)	−0.0054 (8)	−0.0054 (8)
O1	0.053 (3)	0.070 (3)	0.016 (2)	0.021 (3)	0.002 (2)	−0.005 (2)
O1W	0.060 (4)	0.040 (3)	0.048 (3)	−0.014 (2)	−0.011 (2)	0.015 (2)
O2	0.071 (4)	0.056 (3)	0.031 (3)	0.027 (3)	−0.005 (3)	−0.011 (2)
O3	0.029 (2)	0.038 (2)	0.020 (2)	−0.0047 (18)	−0.0028 (19)	0.0053 (19)
O4	0.048 (3)	0.044 (3)	0.043 (3)	−0.015 (2)	−0.017 (2)	0.007 (2)
O5	0.034 (3)	0.081 (4)	0.030 (3)	0.004 (3)	−0.003 (2)	−0.001 (2)
O6	0.025 (3)	0.127 (5)	0.043 (3)	−0.006 (3)	0.003 (3)	0.007 (3)
O7	0.041 (3)	0.048 (3)	0.032 (3)	0.008 (2)	0.004 (2)	−0.010 (2)
O8	0.048 (3)	0.041 (3)	0.077 (3)	−0.002 (2)	0.018 (3)	0.015 (3)
N1	0.024 (3)	0.027 (3)	0.033 (3)	0.001 (2)	0.008 (2)	0.000 (2)
N2	0.032 (3)	0.029 (3)	0.033 (3)	−0.001 (2)	−0.006 (3)	0.001 (2)
N3	0.031 (3)	0.033 (3)	0.037 (3)	0.003 (2)	0.000 (3)	−0.011 (3)
N4	0.024 (3)	0.030 (3)	0.045 (3)	0.001 (2)	0.000 (2)	−0.007 (2)
C1	0.025 (4)	0.039 (4)	0.028 (3)	−0.001 (3)	0.002 (3)	0.000 (3)
C1A	0.028 (4)	0.033 (3)	0.019 (3)	−0.002 (3)	0.002 (3)	−0.004 (3)
C2	0.050 (5)	0.046 (4)	0.120 (8)	−0.003 (4)	0.028 (5)	−0.024 (5)
C3	0.029 (4)	0.032 (3)	0.019 (3)	−0.002 (3)	−0.005 (3)	−0.003 (3)
C4	0.017 (3)	0.032 (3)	0.029 (3)	−0.003 (3)	−0.004 (3)	−0.004 (3)
C5	0.038 (5)	0.037 (4)	0.041 (4)	−0.001 (3)	−0.007 (3)	−0.004 (3)
C6	0.048 (5)	0.037 (4)	0.054 (5)	0.011 (4)	−0.003 (4)	−0.007 (3)
C7	0.057 (5)	0.039 (4)	0.038 (4)	0.013 (4)	−0.015 (4)	0.007 (3)
C8	0.049 (5)	0.044 (4)	0.027 (4)	0.000 (4)	−0.007 (3)	0.004 (3)
C9	0.035 (4)	0.040 (4)	0.033 (4)	0.005 (3)	0.008 (3)	0.002 (3)
C10	0.030 (4)	0.045 (4)	0.022 (4)	−0.003 (3)	−0.004 (3)	−0.003 (3)
C11	0.027 (4)	0.029 (3)	0.031 (3)	0.003 (3)	−0.002 (3)	−0.004 (3)
C12	0.029 (4)	0.023 (3)	0.023 (3)	0.000 (3)	0.000 (3)	−0.006 (2)
C13	0.039 (4)	0.025 (3)	0.028 (3)	0.005 (3)	0.000 (3)	−0.002 (3)
C14	0.034 (4)	0.048 (4)	0.033 (4)	−0.003 (3)	0.001 (3)	−0.005 (3)
C15	0.028 (4)	0.059 (5)	0.055 (5)	0.002 (4)	0.007 (4)	0.000 (4)
C16	0.043 (5)	0.049 (4)	0.014 (3)	−0.002 (3)	−0.001 (3)	−0.002 (3)
C17	0.033 (4)	0.030 (3)	0.064 (5)	0.003 (3)	0.009 (4)	0.004 (3)
C18	0.042 (5)	0.026 (3)	0.066 (5)	0.008 (3)	0.007 (4)	0.001 (3)
C19	0.036 (4)	0.042 (4)	0.043 (4)	0.012 (3)	0.000 (3)	0.000 (3)
C20	0.027 (4)	0.042 (4)	0.044 (4)	0.002 (3)	−0.002 (3)	0.008 (3)
C21	0.022 (3)	0.038 (3)	0.024 (3)	−0.003 (3)	0.002 (3)	−0.005 (3)
C22	0.028 (4)	0.041 (3)	0.017 (3)	0.000 (3)	0.002 (3)	−0.002 (3)
C23	0.026 (4)	0.038 (4)	0.047 (4)	−0.005 (3)	−0.001 (3)	−0.005 (3)
C24	0.051 (5)	0.035 (4)	0.047 (4)	−0.015 (4)	−0.001 (4)	−0.005 (3)
C25	0.064 (5)	0.025 (3)	0.055 (4)	0.002 (3)	−0.006 (5)	0.001 (4)
C26	0.054 (5)	0.039 (3)	0.048 (4)	−0.003 (3)	−0.014 (4)	0.005 (4)
C27	0.053 (5)	0.057 (5)	0.112 (8)	0.018 (4)	−0.018 (6)	0.022 (5)
C28	0.059 (6)	0.048 (4)	0.086 (6)	−0.023 (4)	−0.006 (5)	−0.005 (4)
C29	0.040 (5)	0.046 (4)	0.064 (5)	−0.011 (4)	0.011 (4)	−0.004 (4)
C30	0.043 (4)	0.028 (3)	0.076 (5)	−0.005 (3)	0.003 (4)	−0.011 (3)
C31	0.034 (4)	0.040 (3)	0.050 (5)	0.008 (3)	0.006 (3)	−0.015 (3)
C32	0.028 (4)	0.038 (4)	0.041 (4)	−0.005 (3)	0.001 (3)	−0.004 (3)
C33	0.030 (4)	0.031 (3)	0.026 (3)	0.000 (3)	−0.006 (3)	−0.002 (3)
C34	0.027 (4)	0.034 (3)	0.027 (3)	0.000 (3)	−0.002 (3)	−0.004 (3)
C35	0.025 (4)	0.043 (4)	0.038 (4)	−0.004 (3)	0.000 (3)	0.000 (3)
C36	0.039 (4)	0.031 (3)	0.045 (4)	−0.004 (3)	−0.011 (3)	−0.001 (3)
C37	0.047 (5)	0.029 (3)	0.066 (5)	−0.001 (3)	0.002 (4)	−0.002 (4)
C38	0.034 (4)	0.043 (4)	0.061 (5)	0.007 (3)	−0.001 (4)	−0.012 (4)
C39	0.044 (5)	0.034 (4)	0.098 (6)	0.000 (4)	−0.001 (5)	0.007 (4)

Geometric parameters (Å, º) top

Zn1—O1	1.952 (4)	C12—C13	1.378 (9)
Zn1—O1W	2.082 (4)	C13—C14	1.387 (9)
Zn1—O3ⁱ	2.049 (4)	C14—H14	0.9300
Zn1—N1	2.102 (5)	C14—C15	1.371 (8)
Zn1—N2	2.146 (4)	C15—H15	0.9300
Zn2—O5	1.921 (5)	C15—C16	1.357 (9)
Zn2—O7ⁱⁱ	1.958 (4)	C16—H16	0.9300
Zn2—N3	2.029 (5)	C17—H17	0.9300
Zn2—N4	2.062 (5)	C17—C18	1.370 (9)
Cl1—C5	1.729 (7)	C18—H18	0.9300
Cl2—C13	1.747 (6)	C18—C19	1.372 (9)
O1—C1	1.273 (7)	C19—C20	1.389 (8)
O1W—H1WA	0.8512	C19—C27	1.513 (9)
O1W—H1WB	0.8501	C20—H20	0.9300
O2—C1	1.220 (8)	C20—C21	1.382 (8)
O3—Zn1ⁱⁱ	2.049 (4)	C21—C22	1.484 (8)
O3—C1A	1.246 (7)	C22—C23	1.387 (8)
O4—C1A	1.249 (7)	C23—H23	0.9300
O5—C9	1.270 (7)	C23—C24	1.386 (9)
O6—C9	1.196 (8)	C24—C25	1.400 (9)
O7—Zn2ⁱ	1.958 (4)	C24—C28	1.523 (9)
O7—C10	1.264 (7)	C25—H25	0.9300
O8—C10	1.242 (7)	C25—C26	1.347 (8)
N1—C17	1.352 (8)	C26—H26	0.9300
N1—C21	1.334 (7)	C27—H27A	0.9600
N2—C22	1.343 (7)	C27—H27B	0.9600
N2—C26	1.329 (7)	C27—H27C	0.9600
N3—C34	1.353 (7)	C28—H28A	0.9600
N3—C38	1.334 (7)	C28—H28B	0.9600
N4—C29	1.325 (8)	C28—H28C	0.9600
N4—C33	1.357 (8)	C29—H29	0.9300
C1—C3	1.514 (8)	C29—C30	1.391 (9)
C1A—C4	1.520 (8)	C30—H30	0.9300
C2—H2A	0.9600	C30—C31	1.374 (9)
C2—H2B	0.9600	C31—C32	1.400 (8)
C2—H2C	0.9600	C32—H32	0.9300
C2—C31	1.507 (8)	C32—C33	1.360 (8)
C3—C4	1.385 (7)	C33—C34	1.487 (8)
C3—C8	1.407 (8)	C34—C35	1.386 (8)
C4—C5	1.381 (9)	C35—H35	0.9300
C5—C6	1.389 (9)	C35—C36	1.386 (8)
C6—H6	0.9300	C36—C37	1.399 (9)
C6—C7	1.365 (9)	C36—C39	1.498 (9)
C7—H7	0.9300	C37—H37	0.9300
C7—C8	1.377 (9)	C37—C38	1.364 (9)
C8—H8	0.9300	C38—H38	0.9300
C9—C11	1.518 (9)	C39—H39A	0.9600
C10—C12	1.521 (9)	C39—H39B	0.9600
C11—C12	1.399 (7)	C39—H39C	0.9600
C11—C16	1.394 (9)

O1—Zn1—O1W	103.5 (2)	C16—C15—C14	120.3 (7)
O1—Zn1—O3ⁱ	98.96 (17)	C16—C15—H15	119.9
O1—Zn1—N1	122.84 (18)	C11—C16—H16	119.2
O1—Zn1—N2	96.7 (2)	C15—C16—C11	121.7 (6)
O1W—Zn1—N1	91.85 (18)	C15—C16—H16	119.2
O1W—Zn1—N2	159.80 (19)	N1—C17—H17	119.4
O3ⁱ—Zn1—O1W	90.36 (16)	N1—C17—C18	121.3 (6)
O3ⁱ—Zn1—N1	136.19 (17)	C18—C17—H17	119.4
O3ⁱ—Zn1—N2	86.66 (17)	C17—C18—H18	119.7
N1—Zn1—N2	76.79 (18)	C17—C18—C19	120.6 (6)
O5—Zn2—O7ⁱⁱ	104.35 (19)	C19—C18—H18	119.7
O5—Zn2—N3	116.5 (2)	C18—C19—C20	117.7 (6)
O5—Zn2—N4	108.5 (2)	C18—C19—C27	122.1 (6)
O7ⁱⁱ—Zn2—N3	128.6 (2)	C20—C19—C27	120.1 (6)
O7ⁱⁱ—Zn2—N4	114.78 (19)	C19—C20—H20	120.1
N3—Zn2—N4	81.22 (19)	C21—C20—C19	119.7 (6)
C1—O1—Zn1	120.0 (4)	C21—C20—H20	120.1
Zn1—O1W—H1WA	109.3	N1—C21—C20	121.6 (6)
Zn1—O1W—H1WB	89.9	N1—C21—C22	115.8 (5)
H1WA—O1W—H1WB	118.4	C20—C21—C22	122.6 (6)
C1A—O3—Zn1ⁱⁱ	128.1 (4)	N2—C22—C21	115.3 (5)
C9—O5—Zn2	127.2 (5)	N2—C22—C23	121.8 (5)
C10—O7—Zn2ⁱ	110.2 (4)	C23—C22—C21	122.9 (6)
C17—N1—Zn1	124.0 (4)	C22—C23—H23	120.2
C21—N1—Zn1	116.7 (4)	C24—C23—C22	119.7 (6)
C21—N1—C17	119.1 (6)	C24—C23—H23	120.2
C22—N2—Zn1	115.1 (4)	C23—C24—C25	117.1 (6)
C26—N2—Zn1	126.8 (4)	C23—C24—C28	120.2 (7)
C26—N2—C22	118.0 (5)	C25—C24—C28	122.6 (6)
C34—N3—Zn2	113.9 (4)	C24—C25—H25	120.2
C38—N3—Zn2	128.4 (4)	C26—C25—C24	119.6 (6)
C38—N3—C34	117.5 (5)	C26—C25—H25	120.2
C29—N4—Zn2	127.8 (5)	N2—C26—C25	123.9 (6)
C29—N4—C33	118.8 (6)	N2—C26—H26	118.1
C33—N4—Zn2	113.2 (4)	C25—C26—H26	118.1
O1—C1—C3	114.9 (6)	C19—C27—H27A	109.5
O2—C1—O1	126.6 (6)	C19—C27—H27B	109.5
O2—C1—C3	118.5 (5)	C19—C27—H27C	109.5
O3—C1A—O4	127.1 (6)	H27A—C27—H27B	109.5
O3—C1A—C4	115.2 (5)	H27A—C27—H27C	109.5
O4—C1A—C4	117.4 (5)	H27B—C27—H27C	109.5
H2A—C2—H2B	109.5	C24—C28—H28A	109.5
H2A—C2—H2C	109.5	C24—C28—H28B	109.5
H2B—C2—H2C	109.5	C24—C28—H28C	109.5
C31—C2—H2A	109.5	H28A—C28—H28B	109.5
C31—C2—H2B	109.5	H28A—C28—H28C	109.5
C31—C2—H2C	109.5	H28B—C28—H28C	109.5
C4—C3—C1	121.7 (6)	N4—C29—H29	118.9
C4—C3—C8	119.5 (6)	N4—C29—C30	122.1 (6)
C8—C3—C1	118.7 (5)	C30—C29—H29	118.9
C3—C4—C1A	122.2 (6)	C29—C30—H30	120.2
C5—C4—C1A	119.7 (5)	C31—C30—C29	119.6 (6)
C5—C4—C3	118.1 (6)	C31—C30—H30	120.2
C4—C5—Cl1	119.9 (5)	C30—C31—C2	121.3 (6)
C4—C5—C6	122.3 (6)	C30—C31—C32	117.7 (6)
C6—C5—Cl1	117.8 (5)	C32—C31—C2	121.1 (6)
C5—C6—H6	120.3	C31—C32—H32	120.0
C7—C6—C5	119.3 (7)	C33—C32—C31	120.0 (6)
C7—C6—H6	120.3	C33—C32—H32	120.0
C6—C7—H7	120.1	N4—C33—C32	121.7 (5)
C6—C7—C8	119.8 (6)	N4—C33—C34	115.4 (5)
C8—C7—H7	120.1	C32—C33—C34	122.9 (6)
C3—C8—H8	119.6	N3—C34—C33	116.1 (5)
C7—C8—C3	120.9 (6)	N3—C34—C35	121.7 (5)
C7—C8—H8	119.6	C35—C34—C33	122.2 (6)
O5—C9—C11	114.7 (6)	C34—C35—H35	119.5
O6—C9—O5	124.3 (7)	C36—C35—C34	121.0 (6)
O6—C9—C11	121.0 (6)	C36—C35—H35	119.5
O7—C10—C12	117.9 (5)	C35—C36—C37	115.9 (6)
O8—C10—O7	123.8 (6)	C35—C36—C39	121.0 (6)
O8—C10—C12	117.9 (6)	C37—C36—C39	123.1 (6)
C12—C11—C9	122.7 (6)	C36—C37—H37	119.8
C16—C11—C9	117.9 (6)	C38—C37—C36	120.5 (6)
C16—C11—C12	119.4 (6)	C38—C37—H37	119.8
C11—C12—C10	125.2 (6)	N3—C38—C37	123.4 (6)
C13—C12—C10	117.7 (5)	N3—C38—H38	118.3
C13—C12—C11	117.0 (6)	C37—C38—H38	118.3
C12—C13—Cl2	119.9 (5)	C36—C39—H39A	109.5
C12—C13—C14	123.6 (6)	C36—C39—H39B	109.5
C14—C13—Cl2	116.6 (5)	C36—C39—H39C	109.5
C13—C14—H14	121.0	H39A—C39—H39B	109.5
C15—C14—C13	118.0 (8)	H39A—C39—H39C	109.5
C15—C14—H14	121.0	H39B—C39—H39C	109.5
C14—C15—H15	119.9

Zn1—O1—C1—O2	18.8 (10)	N3—C34—C35—C36	0.5 (9)
Zn1—O1—C1—C3	−159.9 (4)	N4—Zn2—O5—C9	34.9 (7)
Zn1ⁱⁱ—O3—C1A—O4	22.0 (9)	N4—Zn2—N3—C34	−4.7 (4)
Zn1ⁱⁱ—O3—C1A—C4	−152.6 (4)	N4—Zn2—N3—C38	−179.3 (6)
Zn1—N1—C17—C18	176.6 (5)	N4—C29—C30—C31	−1.0 (11)
Zn1—N1—C21—C20	−178.3 (5)	N4—C33—C34—N3	−1.9 (8)
Zn1—N1—C21—C22	4.9 (6)	N4—C33—C34—C35	178.3 (6)
Zn1—N2—C22—C21	−3.0 (6)	C1—C3—C4—C1A	1.6 (10)
Zn1—N2—C22—C23	175.9 (4)	C1—C3—C4—C5	−178.7 (6)
Zn1—N2—C26—C25	−175.1 (6)	C1—C3—C8—C7	176.6 (6)
Zn2—O5—C9—O6	6.5 (12)	C1A—C4—C5—Cl1	2.7 (9)
Zn2—O5—C9—C11	−173.1 (4)	C1A—C4—C5—C6	−178.4 (6)
Zn2ⁱ—O7—C10—O8	17.5 (8)	C2—C31—C32—C33	178.9 (7)
Zn2ⁱ—O7—C10—C12	−155.3 (4)	C3—C4—C5—Cl1	−177.0 (5)
Zn2—N3—C34—C33	5.0 (6)	C3—C4—C5—C6	1.9 (10)
Zn2—N3—C34—C35	−175.2 (4)	C4—C3—C8—C7	−1.3 (10)
Zn2—N3—C38—C37	173.7 (6)	C4—C5—C6—C7	−0.9 (12)
Zn2—N4—C29—C30	−176.3 (5)	C5—C6—C7—C8	−1.3 (12)
Zn2—N4—C33—C32	178.6 (5)	C6—C7—C8—C3	2.3 (11)
Zn2—N4—C33—C34	−2.0 (6)	C8—C3—C4—C1A	179.5 (6)
Cl1—C5—C6—C7	178.0 (6)	C8—C3—C4—C5	−0.8 (10)
Cl2—C13—C14—C15	179.1 (5)	C9—C11—C12—C10	3.1 (9)
O1—Zn1—N1—C17	−90.0 (5)	C9—C11—C12—C13	178.9 (5)
O1—Zn1—N1—C21	84.6 (4)	C9—C11—C16—C15	−178.7 (6)
O1—Zn1—N2—C22	−118.1 (4)	C10—C12—C13—Cl2	−3.1 (7)
O1—Zn1—N2—C26	59.4 (6)	C10—C12—C13—C14	177.4 (6)
O1—C1—C3—C4	−160.0 (6)	C11—C12—C13—Cl2	−179.2 (4)
O1—C1—C3—C8	22.1 (9)	C11—C12—C13—C14	1.3 (9)
O1W—Zn1—O1—C1	−108.3 (5)	C12—C11—C16—C15	1.5 (10)
O1W—Zn1—N1—C17	17.3 (5)	C12—C13—C14—C15	−1.4 (10)
O1W—Zn1—N1—C21	−168.0 (4)	C13—C14—C15—C16	1.4 (11)
O1W—Zn1—N2—C22	61.4 (8)	C14—C15—C16—C11	−1.5 (11)
O1W—Zn1—N2—C26	−121.2 (6)	C16—C11—C12—C10	−177.1 (6)
O2—C1—C3—C4	21.2 (10)	C16—C11—C12—C13	−1.3 (8)
O2—C1—C3—C8	−156.7 (6)	C17—N1—C21—C20	−3.4 (9)
O3ⁱ—Zn1—O1—C1	159.2 (5)	C17—N1—C21—C22	179.8 (5)
O3ⁱ—Zn1—N1—C17	109.8 (5)	C17—C18—C19—C20	−0.3 (10)
O3ⁱ—Zn1—N1—C21	−75.6 (5)	C17—C18—C19—C27	178.9 (7)
O3ⁱ—Zn1—N2—C22	143.3 (4)	C18—C19—C20—C21	−0.9 (9)
O3ⁱ—Zn1—N2—C26	−39.3 (6)	C19—C20—C21—N1	2.8 (9)
O3—C1A—C4—C3	−106.9 (7)	C19—C20—C21—C22	179.4 (5)
O3—C1A—C4—C5	73.4 (7)	C20—C21—C22—N2	−178.0 (6)
O4—C1A—C4—C3	77.9 (8)	C20—C21—C22—C23	3.2 (9)
O4—C1A—C4—C5	−101.8 (7)	C21—N1—C17—C18	2.1 (9)
O5—Zn2—N3—C34	101.7 (4)	C21—C22—C23—C24	179.3 (6)
O5—Zn2—N3—C38	−72.9 (6)	C22—N2—C26—C25	2.3 (11)
O5—Zn2—N4—C29	63.2 (6)	C22—C23—C24—C25	0.4 (9)
O5—Zn2—N4—C33	−111.5 (4)	C22—C23—C24—C28	177.5 (6)
O5—C9—C11—C12	−171.7 (6)	C23—C24—C25—C26	0.1 (11)
O5—C9—C11—C16	8.5 (9)	C24—C25—C26—N2	−1.4 (12)
O6—C9—C11—C12	8.7 (10)	C26—N2—C22—C21	179.3 (6)
O6—C9—C11—C16	−171.1 (7)	C26—N2—C22—C23	−1.8 (9)
O7ⁱⁱ—Zn2—O5—C9	157.7 (6)	C27—C19—C20—C21	179.9 (7)
O7ⁱⁱ—Zn2—N3—C34	−119.5 (4)	C28—C24—C25—C26	−177.0 (7)
O7ⁱⁱ—Zn2—N3—C38	65.9 (7)	C29—N4—C33—C32	3.5 (9)
O7ⁱⁱ—Zn2—N4—C29	−53.1 (6)	C29—N4—C33—C34	−177.2 (6)
O7ⁱⁱ—Zn2—N4—C33	132.3 (4)	C29—C30—C31—C2	−177.3 (7)
O7—C10—C12—C11	−99.1 (7)	C29—C30—C31—C32	2.2 (10)
O7—C10—C12—C13	85.1 (7)	C30—C31—C32—C33	−0.7 (10)
O8—C10—C12—C11	87.7 (8)	C31—C32—C33—N4	−2.2 (9)
O8—C10—C12—C13	−88.1 (7)	C31—C32—C33—C34	178.6 (5)
N1—Zn1—O1—C1	−7.1 (6)	C32—C33—C34—N3	177.4 (6)
N1—Zn1—N2—C22	4.2 (4)	C32—C33—C34—C35	−2.4 (9)
N1—Zn1—N2—C26	−178.4 (6)	C33—N4—C29—C30	−1.9 (10)
N1—C17—C18—C19	−0.3 (10)	C33—C34—C35—C36	−179.8 (5)
N1—C21—C22—N2	−1.2 (7)	C34—N3—C38—C37	−0.7 (11)
N1—C21—C22—C23	180.0 (6)	C34—C35—C36—C37	−0.2 (9)
N2—Zn1—O1—C1	71.5 (5)	C34—C35—C36—C39	−179.9 (6)
N2—Zn1—N1—C17	−179.5 (5)	C35—C36—C37—C38	−0.5 (10)
N2—Zn1—N1—C21	−4.9 (4)	C36—C37—C38—N3	1.0 (12)
N2—C22—C23—C24	0.5 (9)	C38—N3—C34—C33	−179.8 (6)
N3—Zn2—O5—C9	−54.4 (7)	C38—N3—C34—C35	0.0 (9)
N3—Zn2—N4—C29	178.3 (6)	C39—C36—C37—C38	179.2 (7)
N3—Zn2—N4—C33	3.6 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱⁱⁱ	0.85	2.10	2.768 (6)	135
O1W—H1WB···O4ⁱ	0.85	1.79	2.644 (6)	179
O1W—H1WB···O3ⁱ	0.85	2.43	2.930 (5)	118
C17—H17···O4ⁱⁱⁱ	0.93	2.36	3.202 (8)	150
C20—H20···O6^iv	0.93	2.28	3.171 (8)	160
C23—H23···O6^iv	0.93	2.40	3.306 (8)	164
C32—H32···O2ⁱⁱⁱ	0.93	2.57	3.459 (8)	161
C35—H35···O2ⁱⁱⁱ	0.93	2.45	3.353 (8)	165

Symmetry codes: (i) x, y, z+1; (iii) −x+1, −y+1, z+1/2; (iv) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)(H₂O)]·[Zn(C₈H₃ClO₄)(C₁₂H₁₂N₂)]
M_r	914.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	291
a, b, c (Å)	34.050 (4), 14.1831 (10), 7.8764 (6)
V (Å³)	3803.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.971, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10533, 6396, 5076
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.104, 1.07
No. of reflections	6396
No. of parameters	518
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.37
Absolute structure	Flack (1983), 2200 Friedel pairs
Absolute structure parameter	0.093 (14)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱ	0.85	2.10	2.768 (6)	134.8
O1W—H1WB···O4ⁱⁱ	0.85	1.79	2.644 (6)	179.2
O1W—H1WB···O3ⁱⁱ	0.85	2.43	2.930 (5)	118.1
C17—H17···O4ⁱ	0.93	2.36	3.202 (8)	149.7
C20—H20···O6ⁱⁱⁱ	0.93	2.28	3.171 (8)	159.5
C23—H23···O6ⁱⁱⁱ	0.93	2.40	3.306 (8)	163.8
C32—H32···O2ⁱ	0.93	2.57	3.459 (8)	160.8
C35—H35···O2ⁱ	0.93	2.45	3.353 (8)	165.0

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x, y, z+1; (iii) −x+1, −y+1, z−1/2.

References

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