Bis(9-allyl-6-carb-oxy-9H-carbazole-3-carboxyl-ato-κ(2) O (3),O (3'))diaqua-zinc.

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 carboxyl-ate O atoms from two chelating 9-allyl-6-carb-oxy-9H-carbazole-3-carboxyl-ate ligands and two O atoms from two water mol-ecules. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules 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 = 689.95

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.02

2942 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045357/vn2058sup1.cif

Click here for additional data file.

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

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

[Zn(C17H12NO4)2(H2O)2]	F(000) = 1424
Mr = 689.95	Dx = 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

Bruker APEXII CCD diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	2390 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 26.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −38→37
Tmin = 0.828, Tmax = 0.885	k = −4→6
7758 measured reflections	l = −27→20

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(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
2942 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .