Poly[bis-(1,3-dimethyl-imidazolidin-2-one)(μ2-2,5-dioxidoterephthalato)zirconium(IV)].

In the title coordination polymer, [Zr(C8H2O6)(C5H10N2O)2] n , the Zr(IV) atom (site symmetry 2) is coordinated by two O,O'-bidentate 2,5-dioxidoterephthalate (DHTP(4-)) ligands and two O-bonded 1,3-dimethyl-2-imidazolidinone (DMI) ligands (the latter in a cis orientation) in a distorted ZrO6 octa-hedral geometry. The deprotonated hy-droxy and carb-oxy O atoms of the DHTP(4-) ligand chelate the Zr(IV) ion via a six-membered ring; the dihedral angle between the carboxyl-ate group and the aromatic ring is 14.46 (11)°. The DHTP(4-) ligand is completed by crystallographic inversion symmetry and coordinates to two Zr(IV) atoms, thereby forming polymeric zigzag chains propagating in [001].

Related literature

For examples of DHTP-containing MOFs, see: Dietzel et al. (2005 ▶, 2006 ▶). For examples of zirconium MOFs, see: Chavan et al. (2012 ▶).

Experimental

Crystal data

[Zr(C8H2O6)(C5H10N2O)2]

M = 513.62

Monoclinic,

a = 17.550 (3) Å

b = 8.0828 (12) Å

c = 15.425 (2) Å

β = 100.558 (2)°

V = 2151.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 293 K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.946, T max = 0.956

5721 measured reflections

2448 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.096

S = 1.03

2448 reflections

141 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006) ▶; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003449/hb7025sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003449/hb7025Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zr(C8H2O6)(C5H10N2O)2]	F(000) = 1048
Mr = 513.62	Dx = 1.586 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.550 (3) Å	Cell parameters from 1603 reflections
b = 8.0828 (12) Å	θ = 2.4–25.4°
c = 15.425 (2) Å	µ = 0.56 mm−1
β = 100.558 (2)°	T = 293 K
V = 2151.0 (6) Å3	Block, colourless
Z = 4	0.10 × 0.10 × 0.08 mm

Bruker SMART CCD diffractometer	2448 independent reflections
Radiation source: sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 27.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −22→22
Tmin = 0.946, Tmax = 0.956	k = −10→7
5721 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0465P)2 + 1.4169P] where P = (Fo2 + 2Fc2)/3
2448 reflections	(Δ/σ)max < 0.001
141 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1	0.10405 (16)	0.0141 (4)	0.37387 (19)	0.0479 (7)
C2	0.04841 (14)	0.0098 (3)	0.43769 (16)	0.0383 (6)
C3	−0.01428 (14)	0.1202 (3)	0.43241 (16)	0.0376 (6)
C4	0.06111 (15)	−0.1071 (3)	0.50427 (17)	0.0411 (6)
H4	0.1026	−0.1797	0.5068	0.049*
C5	0.14154 (18)	0.5409 (4)	0.2821 (2)	0.0499 (7)
C6	0.2275 (3)	0.7161 (6)	0.2379 (5)	0.123 (2)
H6A	0.2177	0.8342	0.2379	0.148*
H6B	0.2623	0.6929	0.1973	0.148*
C7	0.2605 (2)	0.6587 (6)	0.3262 (5)	0.119 (2)
H7A	0.2711	0.7506	0.3671	0.143*
H7B	0.3080	0.5972	0.3264	0.143*
C8	0.0982 (4)	0.6567 (8)	0.1358 (3)	0.145 (2)
H8A	0.1209	0.7198	0.0943	0.217*
H8B	0.0560	0.7178	0.1519	0.217*
H8C	0.0793	0.5535	0.1094	0.217*
C9	0.2002 (4)	0.4805 (7)	0.4328 (3)	0.138 (2)
H9A	0.2485	0.5044	0.4710	0.206*
H9B	0.1938	0.3629	0.4266	0.206*
H9C	0.1583	0.5257	0.4575	0.206*
N1	0.15590 (19)	0.6252 (4)	0.2134 (2)	0.0794 (10)
N2	0.19989 (19)	0.5522 (4)	0.3487 (3)	0.0834 (10)
O1	0.08341 (11)	0.0970 (3)	0.30113 (13)	0.0528 (5)
O2	−0.02943 (11)	0.2381 (2)	0.36978 (12)	0.0447 (4)
O3	0.08044 (12)	0.4612 (3)	0.28274 (14)	0.0596 (6)
O4	0.16535 (14)	−0.0572 (4)	0.39070 (16)	0.0871 (9)
Zr1	0.0000	0.26734 (5)	0.2500	0.03931 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0396 (16)	0.0571 (18)	0.0517 (16)	0.0091 (13)	0.0210 (13)	0.0038 (13)
C2	0.0318 (14)	0.0452 (15)	0.0397 (13)	0.0033 (11)	0.0117 (11)	−0.0024 (11)
C3	0.0352 (14)	0.0391 (15)	0.0400 (13)	0.0023 (11)	0.0105 (11)	−0.0030 (11)
C4	0.0327 (14)	0.0481 (16)	0.0448 (14)	0.0084 (12)	0.0135 (11)	−0.0006 (12)
C5	0.0468 (17)	0.0397 (16)	0.0657 (19)	0.0011 (13)	0.0169 (15)	−0.0060 (14)
C6	0.085 (4)	0.077 (3)	0.232 (8)	−0.017 (3)	0.090 (5)	−0.004 (4)
C7	0.041 (2)	0.080 (3)	0.232 (7)	−0.007 (2)	0.014 (3)	−0.057 (4)
C8	0.199 (7)	0.143 (5)	0.090 (4)	−0.003 (5)	0.021 (4)	0.057 (4)
C9	0.185 (6)	0.136 (5)	0.071 (3)	0.039 (4)	−0.033 (3)	−0.023 (3)
N1	0.081 (2)	0.065 (2)	0.103 (3)	−0.0082 (17)	0.046 (2)	0.0122 (17)
N2	0.062 (2)	0.074 (2)	0.105 (3)	−0.0014 (17)	−0.0073 (19)	−0.0117 (19)
O1	0.0457 (12)	0.0672 (14)	0.0519 (11)	0.0144 (10)	0.0262 (9)	0.0110 (10)
O2	0.0443 (11)	0.0482 (11)	0.0451 (10)	0.0089 (9)	0.0177 (8)	0.0031 (8)
O3	0.0546 (13)	0.0640 (14)	0.0624 (13)	−0.0195 (11)	0.0167 (10)	−0.0042 (11)
O4	0.0589 (15)	0.133 (2)	0.0792 (17)	0.0487 (16)	0.0389 (13)	0.0420 (16)
Zr1	0.0351 (2)	0.0449 (3)	0.0405 (2)	0.000	0.01366 (15)	0.000

C1—O4	1.206 (3)	C7—H7A	0.9700
C1—O1	1.300 (3)	C7—H7B	0.9700
C1—C2	1.509 (3)	C8—N1	1.442 (6)
C2—C4	1.383 (4)	C8—H8A	0.9600
C2—C3	1.407 (3)	C8—H8B	0.9600
C3—O2	1.348 (3)	C8—H8C	0.9600
C3—C4i	1.391 (3)	C9—N2	1.419 (6)
C4—C3i	1.391 (3)	C9—H9A	0.9600
C4—H4	0.9300	C9—H9B	0.9600
C5—O3	1.253 (3)	C9—H9C	0.9600
C5—N2	1.314 (4)	Zr1—O1	2.058 (2)
C5—N1	1.322 (4)	Zr1—O2	2.0215 (17)
C6—N1	1.445 (6)	Zr1—O3	2.108 (2)
C6—C7	1.455 (8)	Zr1—O2ii	2.0215 (17)
C6—H6A	0.9700	Zr1—O1ii	2.058 (2)
C6—H6B	0.9700	Zr1—O3ii	2.108 (2)
C7—N2	1.458 (6)
O4—C1—O1	121.9 (2)	H8B—C8—H8C	109.5
O4—C1—C2	120.5 (3)	N2—C9—H9A	109.5
O1—C1—C2	117.6 (2)	N2—C9—H9B	109.5
C4—C2—C3	119.6 (2)	H9A—C9—H9B	109.5
C4—C2—C1	117.7 (2)	N2—C9—H9C	109.5
C3—C2—C1	122.7 (2)	H9A—C9—H9C	109.5
O2—C3—C4i	119.5 (2)	H9B—C9—H9C	109.5
O2—C3—C2	122.6 (2)	C5—N1—C8	123.3 (4)
C4i—C3—C2	117.9 (2)	C5—N1—C6	109.7 (4)
C2—C4—C3i	122.5 (2)	C8—N1—C6	124.9 (5)
C2—C4—H4	118.7	C5—N2—C9	123.9 (4)
C3i—C4—H4	118.7	C5—N2—C7	110.6 (4)
O3—C5—N2	125.1 (3)	C9—N2—C7	125.3 (5)
O3—C5—N1	124.1 (3)	C1—O1—Zr1	137.87 (16)
N2—C5—N1	110.8 (3)	C3—O2—Zr1	133.46 (15)
N1—C6—C7	105.1 (4)	C5—O3—Zr1	156.5 (2)
N1—C6—H6A	110.7	O2—Zr1—O2ii	166.56 (10)
C7—C6—H6A	110.7	O2—Zr1—O1ii	89.38 (7)
N1—C6—H6B	110.7	O2ii—Zr1—O1ii	81.62 (7)
C7—C6—H6B	110.7	O2—Zr1—O1	81.62 (7)
H6A—C6—H6B	108.8	O2ii—Zr1—O1	89.38 (7)
C6—C7—N2	103.2 (4)	O1ii—Zr1—O1	96.05 (12)
C6—C7—H7A	111.1	O2—Zr1—O3	98.06 (8)
N2—C7—H7A	111.1	O2ii—Zr1—O3	91.94 (8)
C6—C7—H7B	111.1	O1ii—Zr1—O3	170.80 (8)
N2—C7—H7B	111.1	O1—Zr1—O3	90.42 (9)
H7A—C7—H7B	109.1	O2—Zr1—O3ii	91.94 (8)
N1—C8—H8A	109.5	O2ii—Zr1—O3ii	98.06 (8)
N1—C8—H8B	109.5	O1ii—Zr1—O3ii	90.42 (9)
H8A—C8—H8B	109.5	O1—Zr1—O3ii	170.80 (8)
N1—C8—H8C	109.5	O3—Zr1—O3ii	83.95 (13)
H8A—C8—H8C	109.5
O4—C1—C2—C4	−14.8 (4)	C6—C7—N2—C9	−172.3 (5)
O1—C1—C2—C4	165.3 (3)	O4—C1—O1—Zr1	−166.5 (3)
O4—C1—C2—C3	164.4 (3)	C2—C1—O1—Zr1	13.3 (5)
O1—C1—C2—C3	−15.4 (4)	C4i—C3—O2—Zr1	−160.28 (19)
C4—C2—C3—O2	179.3 (2)	C2—C3—O2—Zr1	20.8 (4)
C1—C2—C3—O2	0.1 (4)	N2—C5—O3—Zr1	−108.5 (6)
C4—C2—C3—C4i	0.4 (4)	N1—C5—O3—Zr1	71.3 (7)
C1—C2—C3—C4i	−178.8 (3)	C3—O2—Zr1—O2ii	29.7 (2)
C3—C2—C4—C3i	−0.4 (5)	C3—O2—Zr1—O1ii	77.5 (2)
C1—C2—C4—C3i	178.9 (3)	C3—O2—Zr1—O1	−18.7 (2)
N1—C6—C7—N2	−6.1 (5)	C3—O2—Zr1—O3	−108.0 (2)
O3—C5—N1—C8	10.0 (6)	C3—O2—Zr1—O3ii	167.9 (2)
N2—C5—N1—C8	−170.2 (4)	C1—O1—Zr1—O2	0.7 (3)
O3—C5—N1—C6	174.0 (3)	C1—O1—Zr1—O2ii	−169.3 (3)
N2—C5—N1—C6	−6.1 (4)	C1—O1—Zr1—O1ii	−87.7 (3)
C7—C6—N1—C5	7.7 (5)	C1—O1—Zr1—O3	98.8 (3)
C7—C6—N1—C8	171.5 (5)	C1—O1—Zr1—O3ii	46.7 (6)
O3—C5—N2—C9	−2.9 (6)	C5—O3—Zr1—O2	139.9 (6)
N1—C5—N2—C9	177.3 (4)	C5—O3—Zr1—O2ii	−31.1 (6)
O3—C5—N2—C7	−178.2 (3)	C5—O3—Zr1—O1ii	−76.5 (8)
N1—C5—N2—C7	1.9 (4)	C5—O3—Zr1—O1	58.3 (6)
C6—C7—N2—C5	2.9 (5)	C5—O3—Zr1—O3ii	−129.0 (6)

Table 1

Selected bond lengths (Å)

Zr1—O1	2.058 (2)
Zr1—O2	2.0215 (17)
Zr1—O3	2.108 (2)