Poly[propane-1,2-diammonium [(μ₄-benzene-1,2,4,5-tetra­carboxyl­ato-κ⁴O:O′:O′′:O′′′)zinc(II)] tetra­hydrate]

In the title compound, {[Zn(C₁₀H₂O₈)(C₃H₁₂N₂)]·4H₂O}_n, the Zn²⁺ ions are in a distorted tetra­hedral environment made up of four O atoms from four benzene-1,2,4,5-tetra­carboxyl­ate anions, which leads to the formation of a polymeric three-dimensional network. The disordered (3:1) propane-1,2-diammonium counter-cations and the water mol­ecules are located in the voids of the network. Inter­molecular N—H...O and O—H...O hydrogen bonds help to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT221_ALERT_4_C Large Solvent/Anion  N     Ueq(max)/Ueq(min) ...       3.84 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      18.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         17

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

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

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S1. Comment

In the past, considerable attention has been paid to the exploration of the structures and properties of metal complexes or salts containing benzenepolycarboxylate ligands. In the case of benzene-1,2,4,5-tetracarboxylate (btec) ligands, the coordination chemistry is well represented, although there are not as many structures as reported for benzene-1,3,5-tricarboxylate (btc). Among the many known compounds containing btec ligands, most are transition metal complexes, including Mn (Rochon & Massarweh, 2000; Hu et al., 2001), Fe (Chu et al., 2001), Co (Murugavel et al., 2002; Kumagai et al., 2002; Poleti & Karanović, 1989; Cheng et al., 2002), Ni (Murugavel et al., 2002; Rochon & Massarweh, 2000; Poleti et al., 1988), Cu (Zou et al., 1998; Cheng et al., 2001; Cao, Shi et al., 2002), Ag (Jaber et al., 1997) and Zn (Murugavel et al., 2002; Yang et al., 2004). Examples of compounds with main group metals such as Ca (Robl, 1988) and Tl (Day & Luehrs, 1988) also exist. Recently, compounds of the rare earth elements were also reported (Cao, Sun et al., 2002; Daiguebonne et al., 2003). However, compounds with btec ligands and organic ammonium counter cations are rare and may have an interesting polymeric structure.

Indeed, the title compound, (I), forms a polymeric three-dimensional structure. The Zn atom is in the center of a distorted tetrahedron made up of four O atoms from four benzene-1,2,4,5-tetracarboxylate anions. The Zn—O bond lengths and bond angles in (I) (Table 1) are within the normal range (Murugavel et al., 2002; Yang et al., 2004). The propane-1,2-diammonium counter cations and the water molecules are located in the voids of the polymeric anionic moieties (Fig. 1). Intermolecular hydrogen bonds of the type N—H···O and O—H···O (Table 2) stabilize the crystal packing (Fig. 2).

Related literature

Transition metal complexes with benzene-1,2,4,5-tetracarboxylate (btec) ligands include those with Mn (Rochon & Massarweh, 2000; Hu et al., 2001), Fe (Chu et al., 2001), Co (Murugavel et al., 2002; Kumagai et al., 2002; Poleti & Karanović, 1989; Cheng et al., 2002), Ni (Murugavel et al., 2002; Rochon & Massarweh, 2000; Poleti et al., 1988), Cu (Zou et al., 1998; Cheng et al., 2001; Cao, Shi et al., 2002), Ag (Jaber et al., 1997) and Zn (Murugavel et al., 2002; Yang et al., 2004). Main group and metal complexes with the same ligand include those with Ca (Robl, 1988) and Tl (Day & Luehrs, 1988); for rare earth metal complexes, see Cao, Sun et al. (2002) and Daiguebonne et al. (2003). The Zn—O bond lengths and angles are comparable to those in similar structures (Murugavel et al., 2002; Yang et al., 2004).

S2. Experimental

At room temperature propane-1,2-diamine (0.87 g (1.0 ml), 11.6 mmol) was added to a solution of benzene-1,2,4,5-tetracarboxylic acid (1.52 g, 5.81 mmol) in ethanol (20 ml), resulting in a milky suspension which subsequently was added to a solution of ZnCl₂ (0.41 g, 2.93 mmol) in water (30 ml). The resulting colorless solution was stirred for 5 min and was left to evaporate slowly at room temperature. After three days, colorless prismatic crystals of (I) were isolated (yield 1.15 g, 84.1%).

S3. Refinement

The H atoms bonded to C atoms were placed in calculated positions. The H atoms of the NH₃⁺ groups and of the water molecules were found in difference Fourier maps. All H atoms were refined in the riding model approximation with the U_iso(H) parameters equal to 1.2U_eq(X) (X = C, N and O). The propane-1,2-diammonium cation is disordered. One NH₃⁺, the CH₃ and the CH groups are split in two positions. They were refined with fixed occupancies of 0.75 and 0.25. Four restrains were used to fix distances d(C11—C12), d(C11—C12'), d(C12—C13) and d(C12'-C13) for the disordered cation. The highest peak and the deepest hole in the final Fourier map are located 1.02 and 0.48 Å from atom OW2.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 40% probability level. The disorder of the propane-1,2-diammonium cation is indicated with dotted lines.
	Fig. 2. Unit-cell packing diagram for (I). Hydrogen bonds are shown as dashed lines.

Poly[propane-1,2-diammonium [(µ₄-benzene-1,2,4,5-tetracarboxylato-κ⁴O:O':O'':O''')zinc(II)] tetrahydrate]

Crystal data

[Zn(C10H2O8)(C3H12N2)]·4H2O	F(000) = 960
Mr = 463.70	Dx = 1.664 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8669 reflections
a = 9.4116 (5) Å	θ = 2.8–33.7°
b = 13.2967 (7) Å	µ = 1.39 mm^−1
c = 14.9365 (7) Å	T = 100 K
β = 98.019 (1)°	Prism, colourless
V = 1850.92 (16) Å^3	0.21 × 0.18 × 0.17 mm
Z = 4

Data collection

Bruker APEX II CCD area-detector diffractometer	4454 independent reflections
Radiation source: fine-focus sealed tube	4001 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.758, Tmax = 0.797	k = −17→17
20525 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: mixed
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0657P)^2 + 2.3619P] where P = (Fo^2 + 2Fc^2)/3
4454 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 1.62 e Å^−3
4 restraints	Δρmin = −0.94 e Å^−3

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)
Zn1	0.03224 (3)	0.868391 (18)	0.655799 (16)	0.00834 (10)
O1	0.12169 (17)	1.06008 (13)	0.42654 (12)	0.0154 (3)
O2	0.2471 (2)	1.11654 (15)	0.32229 (13)	0.0230 (4)
O3	0.19966 (17)	0.92584 (13)	0.61094 (11)	0.0146 (3)
O4	0.17684 (18)	0.83944 (13)	0.48050 (12)	0.0161 (3)
C1	0.3718 (2)	1.02922 (17)	0.44759 (15)	0.0123 (4)
C2	0.3698 (2)	0.95572 (17)	0.51446 (15)	0.0117 (4)
C3	0.4976 (2)	0.92813 (17)	0.56651 (15)	0.0126 (4)
H3A	0.4963	0.8792	0.6127	0.015*
C4	0.2385 (2)	1.07046 (17)	0.39364 (15)	0.0130 (4)
C5	0.2357 (2)	0.90262 (17)	0.53424 (15)	0.0117 (4)
O5	0.20752 (18)	0.67090 (13)	0.66424 (12)	0.0177 (3)
O6	−0.01647 (18)	0.72814 (12)	0.62750 (12)	0.0154 (3)
O7	0.04691 (18)	0.62364 (12)	0.28851 (11)	0.0135 (3)
O8	0.0393 (2)	0.45944 (14)	0.26156 (12)	0.0253 (4)
C6	0.0402 (2)	0.57553 (16)	0.56367 (15)	0.0110 (4)
C7	0.0576 (2)	0.58931 (16)	0.47342 (15)	0.0117 (4)
H7A	0.0973	0.6504	0.4552	0.014*
C8	0.0176 (2)	0.51486 (16)	0.40971 (15)	0.0116 (4)
C9	0.0823 (2)	0.66294 (17)	0.62596 (15)	0.0121 (4)
C10	0.0358 (2)	0.53321 (17)	0.31313 (15)	0.0123 (4)
N1	0.2934 (3)	1.1642 (3)	0.8054 (2)	0.0430 (7)
H1NA	0.2231	1.1212	0.8016	0.052*
H1NB	0.3625	1.1541	0.8497	0.052*
H1NC	0.2726	1.2256	0.8189	0.052*
C11	0.3328 (3)	1.1789 (3)	0.7146 (2)	0.0347 (7)
H11A	0.4383	1.2117	0.7123	0.042*
H11B	0.3743	1.1080	0.6924	0.042*
C13	0.2738 (3)	1.2619 (2)	0.56495 (19)	0.0297 (6)
H13A	0.1951	1.2867	0.5206	0.045*	0.75
H13B	0.3275	1.2103	0.5370	0.045*	0.75
H13C	0.3380	1.3178	0.5857	0.045*	0.75
H13D	0.3753	1.2534	0.5585	0.045*	0.25
H13E	0.2591	1.3288	0.5896	0.045*	0.25
H13F	0.2152	1.2551	0.5057	0.045*	0.25
N2	0.1015 (3)	1.1399 (2)	0.6099 (2)	0.0171 (5)	0.75
H2NA	0.0212	1.1639	0.5766	0.021*	0.75
H2NB	0.0766	1.1045	0.6556	0.021*	0.75
H2NC	0.1427	1.0946	0.5692	0.021*	0.75
C12	0.2138 (3)	1.2175 (4)	0.6440 (2)	0.0248 (8)	0.75
H12A	0.1646	1.2717	0.6718	0.030*	0.75
N2'	0.0784 (8)	1.1905 (6)	0.6487 (5)	0.0112 (14)*	0.25
H2'A	0.0674	1.1496	0.6961	0.017*	0.25
H2'B	0.0166	1.1713	0.5994	0.017*	0.25
H2'C	0.0596	1.2551	0.6632	0.017*	0.25
C12'	0.2306 (12)	1.1829 (10)	0.6281 (6)	0.038 (4)*	0.25
H12B	0.2389	1.1173	0.5993	0.045*	0.25
O1W	0.3900 (3)	0.5682 (2)	0.3988 (2)	0.0468 (6)
H1WA	0.4572	0.5478	0.3743	0.056*
H1WB	0.3578	0.6178	0.3702	0.056*
O2W	0.4618 (3)	0.6631 (2)	0.56783 (19)	0.0480 (6)
H2WA	0.3901	0.6640	0.5933	0.058*
H2WB	0.4418	0.6355	0.5186	0.058*
O3W	0.3873 (3)	1.0068 (2)	0.1991 (2)	0.0512 (7)
H3WA	0.3241	0.9640	0.1902	0.061*
H3WB	0.3608	1.0369	0.2417	0.061*
O4W	0.3356 (2)	0.76559 (16)	0.33999 (13)	0.0266 (4)
H4WA	0.2875	0.7767	0.2909	0.032*
H4WB	0.3032	0.7964	0.3802	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.01004 (14)	0.00727 (14)	0.00786 (14)	0.00064 (8)	0.00181 (9)	−0.00028 (8)
O1	0.0107 (7)	0.0166 (8)	0.0189 (8)	0.0027 (6)	0.0019 (6)	0.0031 (6)
O2	0.0160 (8)	0.0314 (10)	0.0213 (9)	0.0027 (7)	0.0014 (7)	0.0113 (8)
O3	0.0124 (7)	0.0148 (8)	0.0177 (8)	−0.0012 (6)	0.0062 (6)	−0.0010 (6)
O4	0.0159 (8)	0.0142 (8)	0.0184 (8)	−0.0028 (6)	0.0031 (6)	−0.0011 (6)
C1	0.0097 (10)	0.0137 (10)	0.0137 (10)	0.0014 (8)	0.0027 (8)	0.0000 (8)
C2	0.0108 (10)	0.0111 (10)	0.0136 (10)	0.0000 (8)	0.0038 (8)	−0.0013 (8)
C3	0.0119 (10)	0.0120 (10)	0.0143 (10)	0.0016 (8)	0.0034 (8)	0.0013 (8)
C4	0.0117 (10)	0.0117 (10)	0.0152 (10)	0.0014 (8)	0.0001 (8)	−0.0001 (8)
C5	0.0081 (9)	0.0120 (10)	0.0149 (10)	0.0022 (8)	0.0011 (8)	0.0031 (8)
O5	0.0163 (8)	0.0196 (9)	0.0165 (8)	0.0016 (7)	0.0002 (6)	−0.0043 (7)
O6	0.0158 (8)	0.0096 (7)	0.0209 (8)	0.0010 (6)	0.0025 (6)	−0.0052 (6)
O7	0.0169 (8)	0.0143 (8)	0.0092 (7)	−0.0024 (6)	0.0016 (6)	0.0022 (6)
O8	0.0473 (12)	0.0180 (9)	0.0129 (8)	−0.0027 (8)	0.0120 (8)	−0.0032 (7)
C6	0.0143 (10)	0.0087 (9)	0.0099 (9)	0.0018 (8)	0.0017 (8)	−0.0002 (8)
C7	0.0163 (10)	0.0079 (9)	0.0116 (10)	0.0005 (8)	0.0038 (8)	0.0013 (8)
C8	0.0159 (10)	0.0098 (10)	0.0098 (10)	0.0011 (8)	0.0048 (8)	0.0007 (8)
C9	0.0180 (11)	0.0100 (9)	0.0089 (9)	−0.0008 (8)	0.0041 (8)	0.0000 (8)
C10	0.0144 (10)	0.0135 (10)	0.0094 (9)	0.0000 (8)	0.0029 (8)	0.0017 (8)
N1	0.0316 (14)	0.064 (2)	0.0327 (15)	−0.0096 (14)	0.0020 (12)	−0.0115 (14)
C11	0.0187 (13)	0.0481 (19)	0.0379 (17)	0.0005 (13)	0.0059 (12)	0.0085 (14)
C13	0.0271 (14)	0.0341 (15)	0.0283 (14)	−0.0050 (12)	0.0046 (11)	−0.0003 (12)
N2	0.0198 (14)	0.0159 (13)	0.0162 (13)	−0.0009 (10)	0.0045 (11)	0.0007 (10)
C12	0.0245 (19)	0.029 (2)	0.0220 (18)	−0.0111 (15)	0.0080 (14)	−0.0077 (16)
O1W	0.0398 (14)	0.0443 (14)	0.0599 (17)	0.0103 (11)	0.0192 (12)	0.0098 (12)
O2W	0.0338 (13)	0.0690 (18)	0.0413 (14)	−0.0020 (13)	0.0063 (11)	−0.0043 (13)
O3W	0.0552 (16)	0.0491 (16)	0.0555 (16)	−0.0195 (13)	0.0292 (13)	−0.0152 (13)
O4W	0.0228 (9)	0.0342 (11)	0.0221 (9)	0.0038 (8)	0.0010 (7)	−0.0006 (8)

Geometric parameters (Å, º)

Zn1—O3	1.9519 (16)	C11—C12'	1.501 (3)
Zn1—O6	1.9526 (16)	C11—C12	1.517 (3)
Zn1—O7^i	1.9705 (16)	C11—H11A	1.0900
Zn1—O1^ii	2.0047 (17)	C11—H11B	1.0900
O1—C4	1.273 (3)	C13—C12	1.500 (3)
O1—Zn1^ii	2.0047 (16)	C13—C12'	1.505 (3)
O2—C4	1.242 (3)	C13—H13A	0.9800
O3—C5	1.277 (3)	C13—H13B	0.9800
O4—C5	1.238 (3)	C13—H13C	0.9800
C1—C3^iii	1.396 (3)	C13—H13D	0.9800
C1—C2	1.399 (3)	C13—H13E	0.9800
C1—C4	1.497 (3)	C13—H13F	0.9799
C2—C3	1.388 (3)	N2—C12	1.513 (5)
C2—C5	1.511 (3)	N2—H2NA	0.9031
C3—C1^iii	1.396 (3)	N2—H2NB	0.8871
C3—H3A	0.9500	N2—H2NC	0.9737
O5—C9	1.240 (3)	C12—H12A	0.9801
O6—C9	1.274 (3)	N2'—C12'	1.510 (17)
O7—C10	1.266 (3)	N2'—H2NA	1.1886
O7—Zn1^iv	1.9705 (16)	N2'—H2NB	1.1475
O8—C10	1.250 (3)	N2'—H2'A	0.9100
C6—C7	1.392 (3)	N2'—H2'B	0.9100
C6—C8^v	1.400 (3)	N2'—H2'C	0.9100
C6—C9	1.507 (3)	C12'—H12B	0.9799
C7—C8	1.388 (3)	O1W—H1WA	0.8200
C7—H7A	0.9500	O1W—H1WB	0.8204
C8—C6^v	1.400 (3)	O2W—H2WA	0.8199
C8—C10	1.496 (3)	O2W—H2WB	0.8201
N1—C11	1.468 (4)	O3W—H3WA	0.8202
N1—H1NA	0.8701	O3W—H3WB	0.8198
N1—H1NB	0.8699	O4W—H4WA	0.8200
N1—H1NC	0.8701	O4W—H4WB	0.8204
O3—Zn1—O6	118.41 (7)	C12—C13—H13D	120.8
O3—Zn1—O7^i	112.19 (7)	C12'—C13—H13D	109.5
O6—Zn1—O7^i	104.51 (7)	H13A—C13—H13D	128.8
O3—Zn1—O1^ii	98.78 (7)	H13B—C13—H13D	46.3
O6—Zn1—O1^ii	101.10 (7)	H13C—C13—H13D	63.4
O7^i—Zn1—O1^ii	122.33 (7)	C12—C13—H13E	88.4
C4—O1—Zn1^ii	107.52 (14)	C12'—C13—H13E	109.5
C5—O3—Zn1	122.78 (15)	H13A—C13—H13E	79.4
C3^iii—C1—C2	119.4 (2)	H13B—C13—H13E	154.7
C3^iii—C1—C4	117.3 (2)	H13C—C13—H13E	46.1
C2—C1—C4	123.1 (2)	H13D—C13—H13E	109.5
C3—C2—C1	119.2 (2)	C12—C13—H13F	116.6
C3—C2—C5	116.7 (2)	C12'—C13—H13F	109.5
C1—C2—C5	124.1 (2)	H13B—C13—H13F	79.0
C2—C3—C1^iii	121.4 (2)	H13C—C13—H13F	126.9
C2—C3—H3A	119.3	H13D—C13—H13F	109.5
C1^iii—C3—H3A	119.3	H13E—C13—H13F	109.5
O2—C4—O1	123.2 (2)	C12—N2—H2NA	115.8
O2—C4—C1	119.5 (2)	C12—N2—H2NB	110.4
O1—C4—C1	117.2 (2)	H2NA—N2—H2NB	108.7
O4—C5—O3	126.5 (2)	C12—N2—H2NC	108.2
O4—C5—C2	120.0 (2)	H2NA—N2—H2NC	104.5
O3—C5—C2	113.33 (19)	H2NB—N2—H2NC	108.9
C9—O6—Zn1	120.26 (15)	C12—N2—H12B	63.8
C10—O7—Zn1^iv	110.26 (14)	H2NA—N2—H12B	138.7
C7—C6—C8^v	119.4 (2)	H2NB—N2—H12B	109.3
C7—C6—C9	116.09 (19)	H2NC—N2—H12B	47.3
C8^v—C6—C9	124.5 (2)	C13—C12—N2	109.0 (3)
C8—C7—C6	120.8 (2)	C13—C12—C11	111.0 (3)
C8—C7—H7A	119.6	N2—C12—C11	114.6 (3)
C6—C7—H7A	119.6	C13—C12—H12A	107.2
C7—C8—C6^v	119.8 (2)	N2—C12—H12A	107.1
C7—C8—C10	119.2 (2)	C11—C12—H12A	107.5
C6^v—C8—C10	121.0 (2)	C13—C12—H12B	84.3
O5—C9—O6	125.6 (2)	N2—C12—H12B	53.1
O5—C9—C6	120.1 (2)	C11—C12—H12B	82.2
O6—C9—C6	114.0 (2)	H12A—C12—H12B	160.1
O8—C10—O7	123.8 (2)	C12'—N2'—H2NA	96.7
O8—C10—C8	118.8 (2)	C12'—N2'—H2NB	88.7
O7—C10—C8	117.4 (2)	H2NA—N2'—H2NB	77.0
C11—N1—H1NA	108.3	C12'—N2'—H12A	63.8
C11—N1—H1NB	117.7	H2NA—N2'—H12A	129.9
H1NA—N1—H1NB	115.4	H2NB—N2'—H12A	141.3
C11—N1—H1NC	100.6	C12'—N2'—H2'A	109.5
H1NA—N1—H1NC	116.0	C12'—N2'—H2'B	109.5
H1NB—N1—H1NC	97.9	H2'A—N2'—H2'B	109.5
N1—C11—C12'	125.9 (5)	C12'—N2'—H2'C	109.5
N1—C11—C12	115.5 (3)	H2'A—N2'—H2'C	109.5
N1—C11—H11A	115.6	H2'B—N2'—H2'C	109.5
C12'—C11—H11A	115.8	C11—C12'—C13	111.6 (3)
C12—C11—H11A	115.5	C11—C12'—N2'	109.8 (8)
N1—C11—H11B	108.3	C13—C12'—N2'	115.4 (9)
C12'—C11—H11B	89.0	C11—C12'—H12A	84.7
C12—C11—H11B	110.0	C13—C12'—H12A	83.7
H11A—C11—H11B	88.2	N2'—C12'—H12A	53.5
C12—C13—H13A	109.5	C11—C12'—H12B	105.4
C12'—C13—H13A	114.4	C13—C12'—H12B	107.6
C12—C13—H13B	109.5	N2'—C12'—H12B	106.6
C12'—C13—H13B	88.8	H12A—C12'—H12B	160.0
H13A—C13—H13B	109.5	H1WA—O1W—H1WB	106.5
C12—C13—H13C	109.5	H2WA—O2W—H2WB	108.7
C12'—C13—H13C	122.7	H3WA—O3W—H3WB	99.9
H13A—C13—H13C	109.5	H4WA—O4W—H4WB	110.6
H13B—C13—H13C	109.5
O6—Zn1—O3—C5	35.90 (19)	C8^v—C6—C7—C8	0.3 (4)
O7^i—Zn1—O3—C5	157.79 (16)	C9—C6—C7—C8	−177.8 (2)
O1^ii—Zn1—O3—C5	−71.86 (18)	C6—C7—C8—C6^v	−0.3 (4)
C3^iii—C1—C2—C3	1.2 (4)	C6—C7—C8—C10	179.0 (2)
C4—C1—C2—C3	−174.5 (2)	Zn1—O6—C9—O5	21.3 (3)
C3^iii—C1—C2—C5	−178.5 (2)	Zn1—O6—C9—C6	−152.37 (15)
C4—C1—C2—C5	5.9 (3)	C7—C6—C9—O5	−88.7 (3)
C1—C2—C3—C1^iii	−1.2 (4)	C8^v—C6—C9—O5	93.2 (3)
C5—C2—C3—C1^iii	178.5 (2)	C7—C6—C9—O6	85.4 (3)
Zn1^ii—O1—C4—O2	−0.9 (3)	C8^v—C6—C9—O6	−92.7 (3)
Zn1^ii—O1—C4—C1	175.71 (16)	Zn1^iv—O7—C10—O8	10.9 (3)
C3^iii—C1—C4—O2	21.3 (3)	Zn1^iv—O7—C10—C8	−169.08 (15)
C2—C1—C4—O2	−163.0 (2)	C7—C8—C10—O8	160.0 (2)
C3^iii—C1—C4—O1	−155.4 (2)	C6^v—C8—C10—O8	−20.6 (3)
C2—C1—C4—O1	20.3 (3)	C7—C8—C10—O7	−20.0 (3)
Zn1—O3—C5—O4	−3.5 (3)	C6^v—C8—C10—O7	159.4 (2)
Zn1—O3—C5—C2	−179.39 (14)	C12'—C13—C12—N2	−54.4 (9)
C3—C2—C5—O4	−107.6 (3)	C12'—C13—C12—C11	72.8 (6)
C1—C2—C5—O4	72.1 (3)	N1—C11—C12—C13	161.0 (3)
C3—C2—C5—O3	68.6 (3)	N1—C11—C12—N2	−74.9 (4)
C1—C2—C5—O3	−111.7 (2)	N1—C11—C12'—C13	140.5 (7)
O3—Zn1—O6—C9	37.10 (19)	C12—C11—C12'—C13	74.2 (7)
O7^i—Zn1—O6—C9	−88.60 (17)	N1—C11—C12'—N2'	11.3 (12)
O1^ii—Zn1—O6—C9	143.54 (17)	C12—C11—C12'—N2'	−55.0 (13)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+2, −z+1; (iv) x, −y+3/2, z−1/2; (v) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O8^i	0.87	2.05	2.901 (4)	165
N1—H1NB···O2W^vi	0.87	1.92	2.771 (4)	164
N1—H1NC···O2^vii	0.87	2.11	2.964 (4)	165
N2—H2NA···O4^ii	0.90	1.94	2.788 (3)	156
N2—H2NB···O8^i	0.89	1.87	2.755 (3)	173
N2—H2NC···O1	0.97	2.16	2.968 (3)	139
N2—H2NC···O3	0.97	2.37	2.992 (3)	121
O1W—H1WA···O3W^viii	0.82	2.02	2.838 (4)	173
O1W—H1WB···O4W	0.82	2.02	2.792 (3)	157
O2W—H2WA···O5	0.82	2.14	2.962 (3)	177
O2W—H2WB···O1W	0.82	2.00	2.819 (4)	179
O3W—H3WA···O5^iv	0.82	2.11	2.911 (3)	165
O3W—H3WB···O2	0.82	2.02	2.817 (3)	164
O4W—H4WA···O5^iv	0.82	2.06	2.859 (3)	166
O4W—H4WB···O4	0.82	2.12	2.911 (3)	163

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y+2, −z+1; (iv) x, −y+3/2, z−1/2; (vi) −x+1, y+1/2, −z+3/2; (vii) x, −y+5/2, z+1/2; (viii) −x+1, y−1/2, −z+1/2.