Bis(9-allyl-6-carb­oxy-9H-carbazole-3-carboxyl­ato-κ2O3,O3′)diaqua­zinc

Li, D.

doi:10.1107/S1600536812045357

metal-organic compounds

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Volume 68| Part 12| December 2012| Page m1462

doi:10.1107/S1600536812045357

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Bis(9-allyl-6-carboxy-9H-carbazole-3-carboxylato-κ²O³,O^3′)diaquazinc

Dailin Li ^a ^*

^aEnvironmental Engineering Department, Xiamen University of Technology, Xiamen 361024, People's Republic of China
^*Correspondence e-mail: chemlidl@163.com

(Received 29 October 2012; accepted 2 November 2012; online 10 November 2012)

In the title compound, [Zn(C₁₇H₁₂NO₄)₂(H₂O)₂], the Zn^II atom is located on a twofold rotation axis and is six-coordinated by four carboxylate O atoms from two chelating 9-allyl-6-carboxy-9H-carbazole-3-carboxylate ligands and two O atoms from two water molecules. In the crystal, O—H⋯O hydrogen bonds link the molecules into a layer structure parallel to (-101).

Related literature

For the design and properties of complexes with supramolecular metal-organic framework structures, see: Li et al. (2011 ); Yang et al. (2007 ). For related structures, see: Wang et al. (2010 ).

Experimental

Crystal data

[Zn(C₁₇H₁₂NO₄)₂(H₂O)₂]
M_r = 689.95
Monoclinic, C 2/c
a = 30.8562 (18) Å
b = 5.0491 (3) Å
c = 21.8915 (13) Å
β = 119.403 (1)°
V = 2971.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 173 K
0.22 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.828, T_max = 0.885
7758 measured reflections
2942 independent reflections
2390 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.02
2942 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.4040 (15)
Zn1—O2	2.0392 (15)
Zn1—O1W	1.9824 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O4ⁱ	0.84	1.81	2.654 (2)	177
O1W—H1B⋯O2ⁱⁱ	0.85	1.88	2.728 (2)	170
O3—H3A⋯O1ⁱ	0.87	1.77	2.634 (2)	173
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (ii) $[-x+1, y+1, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812045357/vn2058sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045357/vn2058Isup2.hkl

checkCIF report

Comment top

Crystal engineering based on metal-organic frameworks (MOFs) continues to attract considerable interest not only because of their intriguing variety of architectures but also for their potential functional properties, such as magnetism, nonlinear optics, hydrogen storage and catalysis (Li et al., 2011; Yang et al., 2007). Multifunctional ligands can link metal ions into one-, two- or three-dimensional structures. In order to extend the investigations in this field, we designed and synthesized the title zinc(II) compound and report here its structure.

The asymmetric unit of the title complex (Fig. 1) contains a Zn^II atom, one 9-allyl-9H-carbazole-6-carboxy-3-carboxylate ligand and one coordinated water molecule. The Zn^II atom, lying on a twofold rotation axis, is six-coordinated by four O atoms from two carboxylate ligands and two water molecules in an irregular geometry. The bond distances (Table 1) and angles are normal (Wang et al., 2010). In the crystal structure, O—H···O hydrogen bonds (Table 2) link the complex molecules into a layer structure parellel to (-1 0 1) (Fig. 2).

Related literature top

For the design and properties of complexes with supramolecular metal-organic framework structures, see: Li et al. (2011); Yang et al. (2007). For related structures, see: Wang et al. (2010).

Experimental top

The synthesis was performed under hydrothermal conditions. A mixture of 9-allyl-9H-carbazole-3,6-dicarboxylic acid (0.2 mmol, 0.062 g), Zn(NO₃)₂.6H₂O (0.1 mmol, 0.030 g) and H₂O (15 ml) in a 25 ml stainless steel reactor with a Teflon liner was heated from 293 to 433 K in 2 h and maintained at 433 K for 72 h. Hereafter the mixture was cooled to 298 K, and colorless crystals of the title compound were obtained (yield: 59%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1 - x, y, 3/2 - z.]
	Fig. 2. View of the layer structure in the title compound, built by hydrogen bonds (dashed lines).

Bis(9-allyl-6-carboxy-9H-carbazole-3-carboxylato- κ²O³,O^3')diaquazinc top

Crystal data top

[Zn(C₁₇H₁₂NO₄)₂(H₂O)₂]	F(000) = 1424
M_r = 689.95	D_x = 1.542 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3306 reflections
a = 30.8562 (18) Å	θ = 2.7–26.1°
b = 5.0491 (3) Å	µ = 0.89 mm⁻¹
c = 21.8915 (13) Å	T = 173 K
β = 119.403 (1)°	Block, colourless
V = 2971.3 (3) Å³	0.22 × 0.16 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	2390 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 26.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −38→37
T_min = 0.828, T_max = 0.885	k = −4→6
7758 measured reflections	l = −27→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.058P)²] where P = (F_o² + 2F_c²)/3
2942 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Zn(C₁₇H₁₂NO₄)₂(H₂O)₂]	V = 2971.3 (3) Å³
M_r = 689.95	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 30.8562 (18) Å	µ = 0.89 mm⁻¹
b = 5.0491 (3) Å	T = 173 K
c = 21.8915 (13) Å	0.22 × 0.16 × 0.14 mm
β = 119.403 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2942 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2390 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.885	R_int = 0.033
7758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
2942 reflections	Δρ_min = −0.26 e Å⁻³
213 parameters

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	0.5000	1.62460 (7)	0.7500	0.02411 (14)
C1	0.45216 (8)	1.3295 (4)	0.64103 (11)	0.0209 (5)
C2	0.43305 (8)	1.1274 (4)	0.58455 (11)	0.0208 (5)
C3	0.38251 (8)	1.0739 (4)	0.54621 (11)	0.0216 (5)
H3	0.3596	1.1705	0.5547	0.026*
C4	0.36580 (8)	0.8774 (4)	0.49528 (11)	0.0214 (5)
C5	0.31714 (8)	0.7713 (5)	0.44657 (11)	0.0225 (5)
C6	0.26914 (9)	0.8305 (5)	0.43223 (12)	0.0254 (5)
H6	0.2633	0.9672	0.4571	0.030*
C7	0.22985 (8)	0.6862 (5)	0.38084 (12)	0.0266 (5)
C8	0.23887 (9)	0.4838 (5)	0.34407 (13)	0.0330 (6)
H8	0.2115	0.3861	0.3095	0.040*
C9	0.28585 (9)	0.4234 (5)	0.35656 (13)	0.0316 (6)
H9	0.2915	0.2885	0.3310	0.038*
C10	0.32518 (9)	0.5698 (5)	0.40878 (11)	0.0251 (5)
C11	0.40064 (8)	0.7341 (5)	0.48402 (11)	0.0218 (5)
C12	0.45129 (8)	0.7873 (5)	0.52155 (11)	0.0255 (5)
H12	0.4743	0.6911	0.5132	0.031*
C13	0.46686 (8)	0.9849 (5)	0.57137 (11)	0.0245 (5)
H13	0.5013	1.0260	0.5975	0.029*
C14	0.17785 (9)	0.7384 (5)	0.36266 (12)	0.0297 (6)
C15	0.39846 (9)	0.3622 (5)	0.40603 (12)	0.0281 (5)
H15A	0.3796	0.1938	0.3946	0.034*
H15B	0.4327	0.3252	0.4441	0.034*
C16	0.40095 (10)	0.4511 (6)	0.34362 (13)	0.0386 (7)
H16	0.4190	0.3423	0.3285	0.046*
C17	0.38062 (11)	0.6661 (7)	0.30711 (15)	0.0517 (8)
H17A	0.3622	0.7812	0.3202	0.062*
H17B	0.3843	0.7069	0.2675	0.062*
N1	0.37548 (7)	0.5493 (4)	0.43157 (9)	0.0238 (4)
O1	0.42355 (6)	1.4699 (3)	0.65268 (8)	0.0284 (4)
O2	0.49925 (5)	1.3547 (3)	0.68019 (8)	0.0235 (4)
O3	0.17182 (6)	0.9470 (4)	0.39349 (9)	0.0400 (5)
H3A	0.1397	0.9621	0.3761	0.060*
O4	0.14358 (6)	0.6002 (4)	0.32174 (10)	0.0418 (5)
O1W	0.45497 (6)	1.8957 (3)	0.75397 (8)	0.0285 (4)
H1A	0.4237	1.9018	0.7291	0.043*
H1B	0.4664	2.0419	0.7755	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0264 (2)	0.0185 (2)	0.0267 (2)	0.000	0.01250 (18)	0.000
C1	0.0207 (12)	0.0198 (12)	0.0214 (11)	0.0020 (9)	0.0097 (9)	0.0046 (9)
C2	0.0213 (12)	0.0211 (12)	0.0170 (10)	0.0001 (9)	0.0072 (9)	0.0013 (9)
C3	0.0182 (11)	0.0258 (13)	0.0203 (11)	0.0023 (9)	0.0091 (9)	−0.0006 (9)
C4	0.0192 (11)	0.0231 (12)	0.0203 (11)	0.0007 (10)	0.0085 (9)	0.0003 (9)
C5	0.0199 (12)	0.0260 (13)	0.0200 (11)	−0.0011 (10)	0.0085 (9)	−0.0025 (10)
C6	0.0234 (12)	0.0278 (13)	0.0249 (12)	0.0009 (10)	0.0118 (10)	−0.0037 (10)
C7	0.0193 (12)	0.0304 (14)	0.0275 (12)	0.0006 (10)	0.0095 (10)	−0.0024 (10)
C8	0.0241 (13)	0.0347 (15)	0.0333 (13)	−0.0041 (12)	0.0087 (11)	−0.0099 (12)
C9	0.0267 (13)	0.0325 (15)	0.0316 (13)	0.0008 (11)	0.0112 (11)	−0.0095 (11)
C10	0.0254 (13)	0.0258 (13)	0.0231 (12)	0.0021 (10)	0.0111 (10)	−0.0015 (9)
C11	0.0224 (12)	0.0214 (12)	0.0199 (11)	0.0032 (10)	0.0092 (9)	0.0031 (9)
C12	0.0224 (12)	0.0303 (13)	0.0240 (11)	0.0052 (10)	0.0115 (10)	−0.0001 (10)
C13	0.0175 (11)	0.0293 (13)	0.0233 (11)	0.0010 (10)	0.0072 (9)	0.0016 (10)
C14	0.0243 (13)	0.0325 (14)	0.0298 (13)	0.0010 (11)	0.0115 (11)	−0.0028 (11)
C15	0.0287 (13)	0.0251 (13)	0.0299 (12)	0.0058 (11)	0.0140 (11)	−0.0020 (10)
C16	0.0380 (16)	0.0498 (18)	0.0353 (14)	0.0066 (14)	0.0236 (13)	−0.0029 (13)
C17	0.053 (2)	0.063 (2)	0.0472 (17)	0.0068 (16)	0.0314 (16)	0.0143 (16)
N1	0.0209 (10)	0.0261 (11)	0.0233 (10)	0.0026 (8)	0.0100 (8)	−0.0044 (8)
O1	0.0211 (9)	0.0290 (9)	0.0296 (9)	0.0026 (7)	0.0083 (7)	−0.0079 (7)
O2	0.0150 (8)	0.0241 (9)	0.0250 (8)	−0.0015 (7)	0.0047 (7)	−0.0010 (7)
O3	0.0206 (9)	0.0479 (12)	0.0461 (11)	0.0008 (8)	0.0122 (8)	−0.0178 (9)
O4	0.0200 (9)	0.0454 (12)	0.0514 (11)	−0.0048 (8)	0.0109 (8)	−0.0197 (9)
O1W	0.0164 (8)	0.0239 (9)	0.0367 (9)	−0.0017 (7)	0.0065 (7)	−0.0062 (7)

Geometric parameters (Å, º) top

Zn1—O1	2.4040 (15)	C9—H9	0.9500
Zn1—O2	2.0392 (15)	C10—N1	1.381 (3)
Zn1—O1W	1.9824 (16)	C11—N1	1.385 (3)
C1—O1	1.252 (3)	C11—C12	1.389 (3)
C1—O2	1.281 (3)	C12—C13	1.379 (3)
C1—C2	1.484 (3)	C12—H12	0.9500
C2—C3	1.387 (3)	C13—H13	0.9500
C2—C13	1.409 (3)	C14—O4	1.216 (3)
C3—C4	1.389 (3)	C14—O3	1.313 (3)
C3—H3	0.9500	C15—N1	1.448 (3)
C4—C11	1.414 (3)	C15—C16	1.475 (3)
C4—C5	1.452 (3)	C15—H15A	0.9900
C5—C6	1.387 (3)	C15—H15B	0.9900
C5—C10	1.408 (3)	C16—C17	1.311 (4)
C6—C7	1.388 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—H17A	0.9500
C7—C8	1.410 (3)	C17—H17B	0.9500
C7—C14	1.475 (3)	O3—H3A	0.8721
C8—C9	1.371 (3)	O1W—H1A	0.8438
C8—H8	0.9500	O1W—H1B	0.8534
C9—C10	1.401 (3)

O1W—Zn1—O1Wⁱ	92.67 (10)	C5—C6—H6	120.6
O1W—Zn1—O2	138.07 (6)	C7—C6—H6	120.6
O1Wⁱ—Zn1—O2	100.30 (6)	C6—C7—C8	120.3 (2)
O1W—Zn1—O2ⁱ	100.30 (6)	C6—C7—C14	121.8 (2)
O1Wⁱ—Zn1—O2ⁱ	138.07 (6)	C8—C7—C14	117.9 (2)
O2—Zn1—O2ⁱ	96.14 (9)	C9—C8—C7	122.2 (2)
O1W—Zn1—O1ⁱ	126.12 (6)	C9—C8—H8	118.9
O1Wⁱ—Zn1—O1ⁱ	81.91 (6)	C7—C8—H8	118.9
O2—Zn1—O1ⁱ	95.28 (6)	C8—C9—C10	116.9 (2)
O2ⁱ—Zn1—O1ⁱ	58.24 (6)	C8—C9—H9	121.5
O1W—Zn1—O1	81.91 (6)	C10—C9—H9	121.5
O1Wⁱ—Zn1—O1	126.12 (6)	N1—C10—C9	128.6 (2)
O2—Zn1—O1	58.24 (6)	N1—C10—C5	109.44 (19)
O2ⁱ—Zn1—O1	95.28 (6)	C9—C10—C5	121.9 (2)
O1ⁱ—Zn1—O1	142.07 (8)	N1—C11—C12	129.1 (2)
O1W—Zn1—C1ⁱ	117.02 (7)	N1—C11—C4	108.95 (19)
O1Wⁱ—Zn1—C1ⁱ	110.17 (7)	C12—C11—C4	121.9 (2)
O2—Zn1—C1ⁱ	95.62 (6)	C13—C12—C11	117.5 (2)
O2ⁱ—Zn1—C1ⁱ	29.40 (6)	C13—C12—H12	121.3
O1ⁱ—Zn1—C1ⁱ	28.87 (6)	C11—C12—H12	121.3
O1—Zn1—C1ⁱ	119.98 (7)	C12—C13—C2	121.7 (2)
O1W—Zn1—C1	110.17 (7)	C12—C13—H13	119.1
O1Wⁱ—Zn1—C1	117.01 (7)	C2—C13—H13	119.1
O2—Zn1—C1	29.39 (6)	O4—C14—O3	123.2 (2)
O2ⁱ—Zn1—C1	95.62 (7)	O4—C14—C7	122.3 (2)
O1ⁱ—Zn1—C1	119.98 (6)	O3—C14—C7	114.5 (2)
O1—Zn1—C1	28.87 (6)	N1—C15—C16	114.6 (2)
C1ⁱ—Zn1—C1	109.29 (10)	N1—C15—H15A	108.6
O1—C1—O2	119.3 (2)	C16—C15—H15A	108.6
O1—C1—C2	121.8 (2)	N1—C15—H15B	108.6
O2—C1—C2	118.8 (2)	C16—C15—H15B	108.6
O1—C1—Zn1	67.95 (12)	H15A—C15—H15B	107.6
O2—C1—Zn1	51.41 (10)	C17—C16—C15	126.1 (3)
C2—C1—Zn1	169.20 (16)	C17—C16—H16	116.9
C3—C2—C13	120.1 (2)	C15—C16—H16	116.9
C3—C2—C1	120.5 (2)	C16—C17—H17A	120.0
C13—C2—C1	119.4 (2)	C16—C17—H17B	120.0
C2—C3—C4	119.3 (2)	H17A—C17—H17B	120.0
C2—C3—H3	120.4	C10—N1—C11	108.79 (18)
C4—C3—H3	120.4	C10—N1—C15	125.86 (19)
C3—C4—C11	119.4 (2)	C11—N1—C15	125.34 (19)
C3—C4—C5	134.1 (2)	C1—O1—Zn1	83.19 (13)
C11—C4—C5	106.49 (19)	C1—O2—Zn1	99.20 (13)
C6—C5—C10	119.9 (2)	C14—O3—H3A	105.3
C6—C5—C4	133.7 (2)	Zn1—O1W—H1A	126.9
C10—C5—C4	106.33 (19)	Zn1—O1W—H1B	120.8
C5—C6—C7	118.7 (2)	H1A—O1W—H1B	110.9

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4ⁱⁱ	0.84	1.81	2.654 (2)	177
O1W—H1B···O2ⁱⁱⁱ	0.85	1.88	2.728 (2)	170
O3—H3A···O1ⁱⁱ	0.87	1.77	2.634 (2)	173

Symmetry codes: (ii) −x+1/2, −y+5/2, −z+1; (iii) −x+1, y+1, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₇H₁₂NO₄)₂(H₂O)₂]
M_r	689.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	30.8562 (18), 5.0491 (3), 21.8915 (13)
β (°)	119.403 (1)
V (Å³)	2971.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.22 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.828, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	7758, 2942, 2390
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.100, 1.02
No. of reflections	2942
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), XP in SHELXTL and Mercury (Macrae et al., 2006).

Selected bond lengths (Å) top

Zn1—O1	2.4040 (15)	Zn1—O1W	1.9824 (16)
Zn1—O2	2.0392 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4ⁱ	0.84	1.81	2.654 (2)	177
O1W—H1B···O2ⁱⁱ	0.85	1.88	2.728 (2)	170
O3—H3A···O1ⁱ	0.87	1.77	2.634 (2)	173

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

Acknowledgements

This work was supported by the Scientific Research Foundation for Introduced Talents of Xiamen University of Technology (grant No. YKJ10003R).

References

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