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

Maercz, M.; Wragg, D.S.; Dietzel, P.D.C.; Fjellvåg, H.

doi:10.1107/S1600536813003437

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page m153

doi:10.1107/S1600536813003437

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

Matthias Maercz,^a ^* David Stephen Wragg,^b Pascal Daniel Croumbie Dietzel ^c and Helmer Fjellvåg ^a

^aCentre for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway, ^bCentre for Materials Science and Nanotechnology &, inGAP National Centre of Research-based Innovation, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway, and ^cDepartment of Chemistry, University of Bergen, PO Box 7803, 5020 Bergen, Norway
^*Correspondence e-mail: matthias.maercz@smn.uio.no

(Received 7 January 2013; accepted 4 February 2013; online 16 February 2013)

In the title coordination polymer, [Zr(C₈H₂O₆)(C₆H₁₂N₂O)₂]_n, the Zr^IV atom, which lies on a crystallographic twofold rotation axis, is coordinated by two O,O′-bidentate 2,5-dioxidoterephthalate (DHTP⁴⁻) ligands and two O-bonded 1,3-dimethyl-1,3-diazinan-2-one (DMPU) ligands (the latter in a cis orientation) in a distorted ZrO₆ octahedral geometry. The deprotonated hydroxy and carboxy O atoms of the DHTP⁴⁻ ligand chelate the Zr^IV ion via a six-membered ring; the dihedral angle between the carboxylate group and the aromatic ring is 19.94 (11)°. The DHTP⁴⁻ ligand is completed by crystallographic inversion symmetry and coordinates to two Zr^IV atoms, thereby forming polymeric zigzag chains propagating in the c-axis direction.

Related literature

For examples of DHTP-containing MOFs, see: Dietzel et al. (2005 , 2006 ). For examples of zirconium MOFs, see: Chavan et al. (2012 ). For a related structure, see: Maercz et al. (2013 ).

Experimental

Crystal data

[Zr(C₈H₂O₆)(C₆H₁₂N₂O)₂]
M_r = 541.67
Monoclinic, C 2/c
a = 18.761 (2) Å
b = 8.4049 (10) Å
c = 14.8816 (17) Å
β = 102.239 (1)°
V = 2293.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 293 K
0.10 × 0.08 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.949, T_max = 0.969
8477 measured reflections
2730 independent reflections
2437 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.096
S = 1.07
2730 reflections
150 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Zr1—O1	2.0955 (18)
Zr2—O2	2.0723 (18)
Zr3—O3	2.0203 (17)

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003437/hb7026sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003437/hb7026Isup2.hkl

checkCIF report

Comment top

The title compound was synthesized as a part of a larger project (see also Maercz et al., 2013), in which the possibility to form new zirconium containing metal organic frameworks (MOFs) using the linker 2,5-dihydroxyterephthalic acid (DHTP) was investigated. Zirconium containing MOFs (Chavan et al., 2012) using terephthalic acid have shown extraordinary thermal stability whereas DHTP containing MOFs (Dietzel et al., 2005, 2006) have shown remarkable sorption properties.

Related literature top

For examples of DHTP-containing MOFs, see: Dietzel et al. (2005, 2006). For examples of zirconium MOFs, see: Chavan et al. (2012). For a related structure, see: Maercz et al. (2013).

Experimental top

Zirconium(IV) chloride (0.047 g, 0.2 mmol) and 2,5-dihydroxyterephthalic acid (0.040 g, 0.2 mmol) were dissolved in 5 ml N,N'-dimethylpropylene urea (DMPU) in a Teflon liner of 23 ml volume under inert atmosphere in a glovebox. The teflon liner was sealed and put into a steel autoclave. The mixture was reacted for 3 d at 160°C. Reaction yielded a brown substance consisting of block shaped crystals and a white impurity. The product was collected by filtration, washed with DMPU and dried over night at room temperature in ambient atmosphere.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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).

Figures top

	Fig. 1. The asymmetric unit of the title compound with 50% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Hydrogen atoms are omitted for clarity.

Poly[bis(1,3-dimethyl-1,3-diazinan-2-one)(2,5-dioxidoterephthalato)zirconium(IV)] top

Crystal data top

[Zr(C₈H₂O₆)(C₆H₁₂N₂O)₂]	F(000) = 1112
M_r = 541.67	D_x = 1.569 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.761 (2) Å	Cell parameters from 2840 reflections
b = 8.4049 (10) Å	θ = 2.8–24.3°
c = 14.8816 (17) Å	µ = 0.53 mm⁻¹
β = 102.239 (1)°	T = 293 K
V = 2293.3 (5) Å³	Block, colourless
Z = 4	0.10 × 0.08 × 0.06 mm

Data collection top

Bruker SMART CCD diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 28.8°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −24→25
T_min = 0.949, T_max = 0.969	k = −10→10
8477 measured reflections	l = −19→20

Refinement top

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 = 1.07	w = 1/[σ²(F_o²) + (0.0462P)² + 2.0694P] where P = (F_o² + 2F_c²)/3
2730 reflections	(Δ/σ)_max < 0.001
150 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Zr(C₈H₂O₆)(C₆H₁₂N₂O)₂]	V = 2293.3 (5) Å³
M_r = 541.67	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.761 (2) Å	µ = 0.53 mm⁻¹
b = 8.4049 (10) Å	T = 293 K
c = 14.8816 (17) Å	0.10 × 0.08 × 0.06 mm
β = 102.239 (1)°

Data collection top

Bruker SMART CCD diffractometer	2730 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2437 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.969	R_int = 0.024
8477 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
2730 reflections	Δρ_min = −0.32 e Å⁻³
150 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.01168 (12)	0.8750 (3)	0.06523 (15)	0.0370 (5)
C2	−0.04708 (11)	0.9809 (3)	0.06010 (16)	0.0389 (5)
C3	−0.10053 (13)	0.9651 (4)	0.12208 (19)	0.0494 (6)
C4	0.05755 (12)	0.8979 (3)	0.00446 (16)	0.0409 (5)
H4	0.0968	0.8292	0.0072	0.049*
C5	0.13245 (14)	0.4514 (3)	0.28509 (18)	0.0460 (6)
C6	0.1951 (3)	0.2463 (6)	0.2172 (4)	0.1152 (19)
H6A	0.1811	0.1438	0.2380	0.138*
H6B	0.2043	0.2328	0.1559	0.138*
C7	0.2608 (3)	0.3007 (6)	0.2785 (6)	0.137 (3)
H7A	0.2813	0.3874	0.2491	0.164*
H7B	0.2961	0.2146	0.2880	0.164*
C8	0.25001 (19)	0.3551 (5)	0.3685 (4)	0.0998 (15)
H8A	0.2447	0.2635	0.4061	0.120*
H8B	0.2927	0.4139	0.3993	0.120*
C9	0.1770 (2)	0.5490 (5)	0.4385 (2)	0.0860 (12)
H9A	0.2201	0.5396	0.4862	0.129*
H9B	0.1357	0.5104	0.4607	0.129*
H9C	0.1694	0.6587	0.4211	0.129*
C10	0.0730 (3)	0.3413 (7)	0.1388 (3)	0.1198 (18)
H10A	0.0849	0.2712	0.0932	0.180*
H10B	0.0594	0.4435	0.1117	0.180*
H10C	0.0331	0.2977	0.1617	0.180*
N1	0.18563 (12)	0.4566 (3)	0.35990 (19)	0.0583 (6)
N2	0.13613 (17)	0.3589 (3)	0.2142 (2)	0.0732 (8)
O1	0.07673 (10)	0.5374 (2)	0.28218 (12)	0.0532 (5)
O2	−0.07967 (9)	0.8873 (2)	0.19808 (13)	0.0519 (5)
O3	0.02342 (9)	0.7526 (2)	0.12481 (12)	0.0424 (4)
O4	−0.16069 (11)	1.0250 (4)	0.10048 (17)	0.0870 (9)
Zr1	0.0000	0.72101 (4)	0.2500	0.03776 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0321 (10)	0.0424 (14)	0.0359 (11)	0.0017 (9)	0.0060 (8)	−0.0032 (9)
C2	0.0295 (10)	0.0489 (15)	0.0387 (12)	0.0026 (10)	0.0086 (9)	−0.0011 (10)
C3	0.0397 (13)	0.0587 (17)	0.0531 (15)	0.0122 (12)	0.0173 (11)	0.0085 (12)
C4	0.0306 (10)	0.0495 (15)	0.0432 (12)	0.0076 (10)	0.0095 (9)	0.0001 (10)
C5	0.0470 (13)	0.0399 (14)	0.0542 (15)	0.0022 (11)	0.0176 (11)	0.0035 (11)
C6	0.145 (5)	0.082 (3)	0.140 (5)	0.039 (3)	0.078 (4)	−0.006 (3)
C7	0.083 (3)	0.077 (3)	0.277 (9)	0.013 (2)	0.098 (5)	−0.021 (4)
C8	0.0489 (19)	0.069 (3)	0.169 (5)	0.0175 (18)	−0.004 (2)	0.017 (3)
C9	0.086 (2)	0.094 (3)	0.062 (2)	0.013 (2)	−0.0200 (18)	−0.0037 (19)
C10	0.172 (5)	0.107 (4)	0.069 (3)	0.012 (4)	0.001 (3)	−0.037 (3)
N1	0.0422 (12)	0.0490 (15)	0.0787 (17)	0.0082 (10)	0.0014 (11)	0.0044 (12)
N2	0.097 (2)	0.0551 (17)	0.0735 (18)	0.0136 (16)	0.0320 (16)	−0.0102 (14)
O1	0.0458 (10)	0.0629 (13)	0.0478 (10)	0.0151 (9)	0.0028 (8)	−0.0043 (9)
O2	0.0445 (9)	0.0666 (13)	0.0492 (10)	0.0150 (9)	0.0205 (8)	0.0134 (9)
O3	0.0408 (9)	0.0467 (11)	0.0410 (9)	0.0073 (7)	0.0117 (7)	0.0035 (7)
O4	0.0529 (12)	0.134 (2)	0.0840 (16)	0.0459 (14)	0.0373 (11)	0.0487 (16)
Zr1	0.03075 (17)	0.0470 (2)	0.03504 (18)	0.000	0.00586 (12)	0.000

Geometric parameters (Å, º) top

C1—O3	1.346 (3)	C7—H7B	0.9700
C1—C4	1.388 (3)	C8—N1	1.462 (4)
C1—C2	1.406 (3)	C8—H8A	0.9700
C2—C4ⁱ	1.386 (3)	C8—H8B	0.9700
C2—C3	1.505 (3)	C9—N1	1.442 (4)
C3—O4	1.215 (3)	C9—H9A	0.9600
C3—O2	1.293 (3)	C9—H9B	0.9600
C4—C2ⁱ	1.386 (3)	C9—H9C	0.9600
C4—H4	0.9300	C10—N2	1.456 (5)
C5—O1	1.264 (3)	C10—H10A	0.9600
C5—N2	1.325 (4)	C10—H10B	0.9600
C5—N1	1.329 (3)	C10—H10C	0.9600
C6—C7	1.443 (8)	Zr1—O1	2.0955 (18)
C6—N2	1.449 (5)	Zr2—O2	2.0723 (18)
C6—H6A	0.9700	Zr3—O3	2.0203 (17)
C6—H6B	0.9700	Zr1—O3ⁱⁱ	2.0203 (17)
C7—C8	1.470 (8)	Zr1—O2ⁱⁱ	2.0723 (18)
C7—H7A	0.9700	Zr1—O1ⁱⁱ	2.0955 (18)

O3—C1—C4	119.9 (2)	H9A—C9—H9B	109.5
O3—C1—C2	122.5 (2)	N1—C9—H9C	109.5
C4—C1—C2	117.7 (2)	H9A—C9—H9C	109.5
C4ⁱ—C2—C1	119.8 (2)	H9B—C9—H9C	109.5
C4ⁱ—C2—C3	118.3 (2)	N2—C10—H10A	109.5
C1—C2—C3	121.8 (2)	N2—C10—H10B	109.5
O4—C3—O2	122.2 (2)	H10A—C10—H10B	109.5
O4—C3—C2	120.2 (2)	N2—C10—H10C	109.5
O2—C3—C2	117.6 (2)	H10A—C10—H10C	109.5
C2ⁱ—C4—C1	122.5 (2)	H10B—C10—H10C	109.5
C2ⁱ—C4—H4	118.7	C5—N1—C9	120.3 (2)
C1—C4—H4	118.7	C5—N1—C8	120.9 (3)
O1—C5—N2	119.4 (3)	C9—N1—C8	118.4 (3)
O1—C5—N1	118.6 (2)	C5—N2—C6	121.8 (4)
N2—C5—N1	122.0 (3)	C5—N2—C10	120.2 (3)
C7—C6—N2	110.9 (4)	C6—N2—C10	116.7 (4)
C7—C6—H6A	109.5	C5—O1—Zr1	162.17 (19)
N2—C6—H6A	109.5	C3—O2—Zr1	136.71 (16)
C7—C6—H6B	109.5	C1—O3—Zr1	132.13 (15)
N2—C6—H6B	109.5	O3—Zr1—O3ⁱⁱ	164.90 (10)
H6A—C6—H6B	108.0	O3—Zr1—O2ⁱⁱ	88.54 (7)
C6—C7—C8	114.2 (4)	O3ⁱⁱ—Zr1—O2ⁱⁱ	81.27 (7)
C6—C7—H7A	108.7	O3—Zr1—O2	81.27 (7)
C8—C7—H7A	108.7	O3ⁱⁱ—Zr1—O2	88.54 (7)
C6—C7—H7B	108.7	O2ⁱⁱ—Zr1—O2	95.19 (12)
C8—C7—H7B	108.7	O3—Zr1—O1ⁱⁱ	99.16 (7)
H7A—C7—H7B	107.6	O3ⁱⁱ—Zr1—O1ⁱⁱ	91.97 (7)
N1—C8—C7	111.9 (4)	O2ⁱⁱ—Zr1—O1ⁱⁱ	171.16 (7)
N1—C8—H8A	109.2	O2—Zr1—O1ⁱⁱ	90.30 (8)
C7—C8—H8A	109.2	O3—Zr1—O1	91.97 (7)
N1—C8—H8B	109.2	O3ⁱⁱ—Zr1—O1	99.16 (7)
C7—C8—H8B	109.2	O2ⁱⁱ—Zr1—O1	90.30 (8)
H8A—C8—H8B	107.9	O2—Zr1—O1	171.16 (7)
N1—C9—H9A	109.5	O1ⁱⁱ—Zr1—O1	85.13 (11)
N1—C9—H9B	109.5

O3—C1—C2—C4ⁱ	−178.2 (2)	C7—C6—N2—C10	164.6 (5)
C4—C1—C2—C4ⁱ	0.3 (4)	N2—C5—O1—Zr1	−75.3 (7)
O3—C1—C2—C3	0.7 (4)	N1—C5—O1—Zr1	104.9 (6)
C4—C1—C2—C3	179.2 (2)	O4—C3—O2—Zr1	160.2 (3)
C4ⁱ—C2—C3—O4	20.1 (4)	C2—C3—O2—Zr1	−20.1 (4)
C1—C2—C3—O4	−158.8 (3)	C4—C1—O3—Zr1	152.68 (18)
C4ⁱ—C2—C3—O2	−159.5 (3)	C2—C1—O3—Zr1	−28.8 (3)
C1—C2—C3—O2	21.6 (4)	C1—O3—Zr1—O3ⁱⁱ	−23.03 (19)
O3—C1—C4—C2ⁱ	178.2 (2)	C1—O3—Zr1—O2ⁱⁱ	−70.4 (2)
C2—C1—C4—C2ⁱ	−0.3 (4)	C1—O3—Zr1—O2	25.1 (2)
N2—C6—C7—C8	47.7 (6)	C1—O3—Zr1—O1ⁱⁱ	114.0 (2)
C6—C7—C8—N1	−44.6 (6)	C1—O3—Zr1—O1	−160.7 (2)
O1—C5—N1—C9	4.8 (4)	C3—O2—Zr1—O3	0.6 (3)
N2—C5—N1—C9	−175.0 (3)	C3—O2—Zr1—O3ⁱⁱ	169.4 (3)
O1—C5—N1—C8	177.6 (3)	C3—O2—Zr1—O2ⁱⁱ	88.3 (3)
N2—C5—N1—C8	−2.2 (5)	C3—O2—Zr1—O1ⁱⁱ	−98.6 (3)
C7—C8—N1—C5	21.3 (5)	C3—O2—Zr1—O1	−39.9 (6)
C7—C8—N1—C9	−165.7 (4)	C5—O1—Zr1—O3	29.7 (6)
O1—C5—N2—C6	−173.7 (3)	C5—O1—Zr1—O3ⁱⁱ	−140.1 (6)
N1—C5—N2—C6	6.0 (5)	C5—O1—Zr1—O2ⁱⁱ	−58.9 (6)
O1—C5—N2—C10	−7.7 (5)	C5—O1—Zr1—O2	69.6 (9)
N1—C5—N2—C10	172.1 (4)	C5—O1—Zr1—O1ⁱⁱ	128.7 (6)
C7—C6—N2—C5	−28.8 (6)

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

Experimental details

Crystal data
Chemical formula	[Zr(C₈H₂O₆)(C₆H₁₂N₂O)₂]
M_r	541.67
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.761 (2), 8.4049 (10), 14.8816 (17)
β (°)	102.239 (1)
V (Å³)	2293.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.10 × 0.08 × 0.06

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.949, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	8477, 2730, 2437
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.07
No. of reflections	2730
No. of parameters	150
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.32

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Zr1—O1	2.0955 (18)	Zr3—O3	2.0203 (17)
Zr2—O2	2.0723 (18)

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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