catena-Poly[[aqua-zinc(II)]-μ-N,N'-bis-(2-cyano-3-eth-oxy-3-oxoprop-1-en-yl)benzene-1,2-diaminido].

The slightly yellow-coloured title complex, [Zn(C18H16N4O4)(H2O)] n , crystallizes with one mol-ecule in the asymmetric unit. The structure clearly shows the mer-η(4) O,O,N,N-binding mode of the N,N'-bis-(2-cyano-ethyl-propeno-yl)-1,2-di-amido-benzene ligand stabilizing the Zn centre of a distorted octa-hedral environment. The fifth coordination site in one apical position is held by a coordinating solvent water mol-ecule whereas the complete octa-hedral coordination sphere is completed by coordination of one N atom from a CN group of a neighbouring mol-ecule, leading to the final polymeric structure consisting of zigzag staggered chains in parallel orientation along the c-axis direction. Between the coord-in-ated water solvent molecule and the N atoms of uncoord-in-ated cyano-groups of neighboured units, two H-bridge bonds are formed. One of these H-bridge bonds is of inter- whereas the other of intra-strand nature, leading to a two-dimensional network parallel to (110) stabilizing the supramolecular structure. Six Zn-O or Zn-N bonds are found with lengths ranging from 2.061 (1) to 2.185 (1) Å and bond angles about the Zn atom are clustered in the ranges 79.83 (4)-104.21 (4) and 167.05 (4)-170.28 (4)°.

Related literature

The structures of ZnII complexes with ligands stabilizing comparable complex geometries can be found in Barnard et al. (2009 ▶), Ryu et al. (2003 ▶) or Tanase et al. (2001 ▶). In Tanase et al. (2001 ▶), the ligands show comparable N,N,O,O-coordination with respect to a different ligand backbone whereas in Ryu et al. (2003 ▶) and Barnard et al. (2009 ▶), the ligands with N,N,N,N-coordination are di­amino­benzene derivatives. In Fuchs et al. (2014 ▶), a mononuclear Zn complex is presented with the same ligand but a dmso mol­ecule in the coordination sphere of the metal stabilizing a different complex geometry. For the synthesis, see: Jäger et al. (1985 ▶).

Experimental

Crystal data

[Zn(C18H16N4O4)(H2O)]

M = 435.73

Orthorhombic,

a = 13.9312 (11) Å

b = 9.2315 (7) Å

c = 27.423 (2) Å

V = 3526.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 1.43 mm−1

T = 100 K

0.10 × 0.09 × 0.07 mm

Data collection

Bruker APEXII Quazar diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.928, T max = 0.953

60234 measured reflections

4294 independent reflections

3812 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.063

S = 1.04

4294 reflections

268 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008381/nk2220sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008381/nk2220Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008381/nk2220Isup3.cdx

CCDC reference: 992382

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Zn(C18H16N4O4)(H2O)]	Dx = 1.641 Mg m−3
Mr = 435.73	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9786 reflections
a = 13.9312 (11) Å	θ = 5.5–56.7°
b = 9.2315 (7) Å	µ = 1.43 mm−1
c = 27.423 (2) Å	T = 100 K
V = 3526.7 (5) Å3	Quader, light yellow
Z = 8	0.10 × 0.09 × 0.07 mm
F(000) = 1792

Bruker APEXII Quazar diffractometer	4294 independent reflections
Radiation source: microfocus sealed Iµs tube	3812 reflections with I > 2σ(I)
Detector resolution: 66 pixels mm-1	Rint = 0.025
combined φ– and ω–scans	θmax = 28.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→18
Tmin = 0.928, Tmax = 0.953	k = −11→12
60234 measured reflections	l = −36→36

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0305P)2 + 2.5256P] where P = (Fo2 + 2Fc2)/3
4294 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. Spectroscopic data: 1H NMR (400 MHz, dmso-d6): δ = 7.56, dd, 3JHH= 6.1 Hz, 4JHH= 3.1 Hz, 2H, H(arom); 7.05, dd, 3JHH= 6.1 Hz, 4JHH= 3.1 Hz, 2H, H(arom); 4.25, q, 3JHH= 7.1 Hz, 4H, OCH2; 1.29, t, 3JHH= 7.1 Hz, 3H, CH3. 13C NMR (100 MHz, dmso-d6): δ = 177.77; 156.27; 138.01; 124.39; 121.19; 114.89; 68.05; 60.24; 14.13. ESI-MS (m/z, %): 417 (100) [M]+, 418 (23) [M+H]+, 835 (15) [2M+H]+. IR (KBr, cm-1): 2203; 1625; 1023; 748. UV/VIS (CH2Cl2): λmax (ε) (nm, mol-1dm3cm-1): 241 (16522),

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.

	x	y	z	Uiso*/Ueq
Zn1	0.50231 (2)	0.19828 (2)	0.37062 (2)	0.00984 (6)
O1	0.36966 (7)	−0.12202 (11)	0.28089 (3)	0.0161 (2)
O2	0.41756 (7)	0.03163 (10)	0.34019 (3)	0.01339 (19)
O3	0.34564 (7)	0.50414 (11)	0.45261 (4)	0.0178 (2)
O4	0.40466 (7)	0.31264 (10)	0.41189 (3)	0.01378 (19)
O5	0.51731 (9)	0.06806 (12)	0.43673 (4)	0.0195 (2)
H51	0.5088 (13)	−0.014 (3)	0.4428 (7)	0.026 (5)*
H52	0.5083 (14)	0.119 (3)	0.4611 (9)	0.035 (6)*
N1	0.61097 (8)	0.33622 (12)	0.39350 (4)	0.0107 (2)
N2	0.61290 (8)	0.12889 (12)	0.32640 (4)	0.0105 (2)
N3	0.53603 (9)	−0.15532 (13)	0.19114 (4)	0.0150 (2)
N4	0.50550 (9)	0.76393 (14)	0.47291 (4)	0.0168 (2)
C1	0.70235 (10)	0.29789 (13)	0.37492 (4)	0.0104 (2)
C2	0.79016 (10)	0.35644 (14)	0.38978 (5)	0.0127 (2)
H2	0.7915	0.4271	0.4150	0.017 (2)*
C3	0.87537 (10)	0.31270 (14)	0.36822 (5)	0.0131 (3)
H3	0.9342	0.3561	0.3779	0.017 (2)*
C4	0.87557 (10)	0.20536 (14)	0.33235 (5)	0.0133 (3)
H4	0.9342	0.1760	0.3177	0.017 (2)*
C5	0.78987 (10)	0.14213 (14)	0.31837 (5)	0.0129 (3)
H5	0.7900	0.0664	0.2949	0.017 (2)*
C6	0.70280 (10)	0.18889 (14)	0.33858 (4)	0.0106 (2)
C7	0.60147 (10)	0.06126 (13)	0.28535 (4)	0.0109 (2)
H7	0.6540	0.0611	0.2633	0.011 (3)*
C8	0.51716 (10)	−0.01222 (15)	0.27076 (5)	0.0117 (2)
C9	0.43345 (10)	−0.02889 (14)	0.30044 (4)	0.0116 (2)
C10	0.52453 (9)	−0.09216 (15)	0.22679 (5)	0.0117 (2)
C11	0.29041 (10)	−0.17030 (16)	0.31142 (5)	0.0173 (3)
H11A	0.2381	−0.2080	0.2906	0.027 (2)*
H11B	0.2650	−0.0872	0.3303	0.027 (2)*
C12	0.32314 (12)	−0.28751 (16)	0.34613 (6)	0.0219 (3)
H12A	0.3535	−0.3660	0.3276	0.027 (2)*
H12B	0.2677	−0.3256	0.3640	0.027 (2)*
H12C	0.3695	−0.2470	0.3693	0.027 (2)*
C13	0.59711 (10)	0.46053 (14)	0.41516 (4)	0.0111 (2)
H13	0.6510	0.5226	0.4188	0.011 (3)*
C14	0.50756 (10)	0.51032 (15)	0.43377 (5)	0.0121 (3)
C16	0.50610 (9)	0.64963 (16)	0.45565 (5)	0.0132 (3)
C15	0.41851 (10)	0.43285 (14)	0.43127 (4)	0.0126 (3)
C17	0.25169 (11)	0.43452 (17)	0.45179 (5)	0.0218 (3)
H17A	0.2435	0.3821	0.4206	0.037 (2)*
H17B	0.2010	0.5093	0.4539	0.037 (2)*
C18	0.24101 (12)	0.32972 (19)	0.49360 (5)	0.0272 (4)
H18A	0.2945	0.2609	0.4932	0.037 (2)*
H18B	0.1803	0.2770	0.4903	0.037 (2)*
H18C	0.2412	0.3832	0.5245	0.037 (2)*

	U11	U22	U33	U12	U13	U23
Zn1	0.01164 (9)	0.00914 (9)	0.00874 (8)	−0.00053 (5)	0.00045 (5)	−0.00140 (5)
O1	0.0152 (5)	0.0196 (5)	0.0134 (4)	−0.0059 (4)	0.0007 (3)	−0.0042 (4)
O2	0.0143 (5)	0.0136 (5)	0.0122 (4)	−0.0016 (4)	0.0011 (3)	−0.0024 (3)
O3	0.0141 (5)	0.0166 (5)	0.0226 (5)	0.0008 (4)	0.0038 (4)	−0.0058 (4)
O4	0.0156 (5)	0.0132 (5)	0.0126 (4)	−0.0006 (4)	0.0013 (4)	−0.0028 (3)
O5	0.0387 (7)	0.0089 (5)	0.0110 (5)	0.0003 (4)	0.0024 (4)	−0.0005 (4)
N1	0.0131 (5)	0.0096 (5)	0.0095 (5)	0.0002 (4)	0.0000 (4)	−0.0002 (4)
N2	0.0121 (5)	0.0092 (5)	0.0102 (5)	−0.0003 (4)	−0.0010 (4)	−0.0007 (4)
N3	0.0143 (6)	0.0172 (6)	0.0136 (5)	−0.0040 (5)	−0.0001 (4)	−0.0026 (4)
N4	0.0218 (7)	0.0124 (6)	0.0161 (6)	0.0003 (5)	0.0043 (4)	−0.0015 (5)
C1	0.0134 (6)	0.0088 (6)	0.0092 (5)	0.0013 (5)	−0.0007 (4)	0.0015 (4)
C2	0.0163 (7)	0.0097 (6)	0.0120 (6)	−0.0008 (5)	−0.0023 (5)	−0.0005 (4)
C3	0.0138 (6)	0.0111 (6)	0.0142 (6)	−0.0024 (5)	−0.0030 (5)	0.0020 (5)
C4	0.0122 (6)	0.0136 (6)	0.0140 (6)	0.0007 (5)	0.0015 (5)	0.0016 (5)
C5	0.0153 (6)	0.0116 (6)	0.0120 (6)	0.0004 (5)	−0.0004 (5)	−0.0018 (5)
C6	0.0137 (6)	0.0086 (6)	0.0097 (5)	−0.0005 (5)	−0.0010 (4)	0.0013 (4)
C7	0.0130 (6)	0.0095 (6)	0.0101 (5)	0.0006 (5)	0.0006 (4)	0.0004 (4)
C8	0.0140 (6)	0.0113 (6)	0.0098 (6)	−0.0011 (5)	−0.0008 (5)	−0.0012 (5)
C9	0.0137 (6)	0.0095 (6)	0.0116 (5)	−0.0001 (5)	−0.0022 (5)	0.0006 (4)
C10	0.0106 (6)	0.0118 (6)	0.0126 (6)	−0.0026 (5)	−0.0014 (5)	0.0021 (5)
C11	0.0121 (6)	0.0193 (7)	0.0205 (6)	−0.0047 (5)	0.0026 (5)	−0.0045 (5)
C12	0.0253 (8)	0.0162 (7)	0.0243 (7)	−0.0028 (6)	0.0065 (6)	−0.0015 (5)
C13	0.0147 (6)	0.0103 (6)	0.0085 (5)	−0.0008 (5)	−0.0014 (5)	0.0003 (4)
C14	0.0165 (7)	0.0095 (6)	0.0105 (6)	0.0014 (5)	0.0005 (4)	−0.0012 (5)
C16	0.0156 (7)	0.0137 (7)	0.0103 (6)	0.0005 (5)	0.0021 (4)	0.0016 (5)
C15	0.0151 (7)	0.0131 (6)	0.0096 (5)	0.0024 (5)	0.0008 (5)	0.0009 (5)
C17	0.0116 (7)	0.0269 (8)	0.0268 (7)	0.0002 (6)	0.0006 (5)	−0.0103 (6)
C18	0.0210 (8)	0.0365 (9)	0.0242 (7)	−0.0136 (7)	0.0030 (6)	−0.0085 (7)

Zn1—O4	2.0606 (9)	C3—H3	0.9500
Zn1—N2	2.0626 (11)	C4—C5	1.3831 (19)
Zn1—N1	2.0754 (11)	C4—H4	0.9500
Zn1—O2	2.1112 (9)	C5—C6	1.4016 (18)
Zn1—O5	2.1852 (11)	C5—H5	0.9500
Zn1—N3i	2.2317 (11)	C7—C8	1.4141 (18)
O1—C9	1.3476 (16)	C7—H7	0.9500
O1—C11	1.4555 (16)	C8—C10	1.4175 (18)
O2—C9	1.2447 (15)	C8—C9	1.4304 (18)
O3—C15	1.3440 (16)	C11—C12	1.511 (2)
O3—C17	1.4582 (18)	C11—H11A	0.9900
O4—C15	1.2455 (16)	C11—H11B	0.9900
O5—H51	0.79 (2)	C12—H12A	0.9800
O5—H52	0.83 (2)	C12—H12B	0.9800
N1—C13	1.3064 (16)	C12—H12C	0.9800
N1—C1	1.4161 (17)	C13—C14	1.4242 (18)
N2—C7	1.2970 (16)	C13—H13	0.9500
N2—C6	1.4097 (17)	C14—C16	1.4192 (19)
N3—C10	1.1493 (17)	C14—C15	1.4336 (19)
N3—Zn1ii	2.2317 (11)	C17—C18	1.508 (2)
N4—C16	1.157 (2)	C17—H17A	0.9900
C1—C2	1.3982 (18)	C17—H17B	0.9900
C1—C6	1.4163 (17)	C18—H18A	0.9800
C2—C3	1.3862 (19)	C18—H18B	0.9800
C2—H2	0.9500	C18—H18C	0.9800
C3—C4	1.3962 (18)
O4—Zn1—N2	167.20 (4)	N2—C6—C1	116.22 (12)
O4—Zn1—N1	90.06 (4)	N2—C7—C8	125.34 (12)
N2—Zn1—N1	79.83 (4)	N2—C7—H7	117.3
O4—Zn1—O2	102.78 (4)	C8—C7—H7	117.3
N2—Zn1—O2	87.65 (4)	C7—C8—C10	115.48 (12)
N1—Zn1—O2	167.05 (4)	C7—C8—C9	124.60 (12)
O4—Zn1—O5	83.64 (4)	C10—C8—C9	119.15 (12)
N2—Zn1—O5	104.21 (4)	O2—C9—O1	121.16 (12)
N1—Zn1—O5	90.97 (4)	O2—C9—C8	126.50 (12)
O2—Zn1—O5	88.89 (4)	O1—C9—C8	112.33 (11)
O4—Zn1—N3i	87.06 (4)	N3—C10—C8	176.10 (14)
N2—Zn1—N3i	85.45 (4)	O1—C11—C12	110.65 (12)
N1—Zn1—N3i	91.86 (4)	O1—C11—H11A	109.5
O2—Zn1—N3i	90.43 (4)	C12—C11—H11A	109.5
O5—Zn1—N3i	170.28 (4)	O1—C11—H11B	109.5
C9—O1—C11	117.81 (10)	C12—C11—H11B	109.5
C9—O2—Zn1	125.02 (9)	H11A—C11—H11B	108.1
C15—O3—C17	117.09 (11)	C11—C12—H12A	109.5
C15—O4—Zn1	126.05 (9)	C11—C12—H12B	109.5
Zn1—O5—H51	133.8 (15)	H12A—C12—H12B	109.5
Zn1—O5—H52	110.0 (16)	C11—C12—H12C	109.5
H51—O5—H52	111 (2)	H12A—C12—H12C	109.5
C13—N1—C1	121.06 (11)	H12B—C12—H12C	109.5
C13—N1—Zn1	124.65 (9)	N1—C13—C14	125.16 (12)
C1—N1—Zn1	113.18 (8)	N1—C13—H13	117.4
C7—N2—C6	120.25 (11)	C14—C13—H13	117.4
C7—N2—Zn1	124.61 (9)	C16—C14—C13	117.16 (12)
C6—N2—Zn1	113.73 (8)	C16—C14—C15	117.38 (12)
C10—N3—Zn1ii	156.83 (11)	C13—C14—C15	125.44 (12)
C2—C1—N1	125.81 (11)	N4—C16—C14	179.05 (15)
C2—C1—C6	118.41 (12)	O4—C15—O3	120.33 (12)
N1—C1—C6	115.77 (12)	O4—C15—C14	126.80 (12)
C3—C2—C1	120.83 (12)	O3—C15—C14	112.87 (11)
C3—C2—H2	119.6	O3—C17—C18	111.08 (12)
C1—C2—H2	119.6	O3—C17—H17A	109.4
C2—C3—C4	120.58 (13)	C18—C17—H17A	109.4
C2—C3—H3	119.7	O3—C17—H17B	109.4
C4—C3—H3	119.7	C18—C17—H17B	109.4
C5—C4—C3	119.55 (13)	H17A—C17—H17B	108.0
C5—C4—H4	120.2	C17—C18—H18A	109.5
C3—C4—H4	120.2	C17—C18—H18B	109.5
C4—C5—C6	120.49 (12)	H18A—C18—H18B	109.5
C4—C5—H5	119.8	C17—C18—H18C	109.5
C6—C5—H5	119.8	H18A—C18—H18C	109.5
C5—C6—N2	123.66 (11)	H18B—C18—H18C	109.5
C5—C6—C1	120.06 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···N4iii	0.79 (2)	2.21 (2)	2.9823 (17)	168 (2)
O5—H52···N4iv	0.83 (2)	2.12 (2)	2.9405 (16)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯N4i	0.79 (2)	2.21 (2)	2.9823 (17)	168 (2)
O5—H52⋯N4ii	0.83 (2)	2.12 (2)	2.9405 (16)	174 (2)

Symmetry codes: (i) ; (ii) .