Poly[[triaqua­[μ4-N-(4-carboxyl­ato­phenyl)­iminodiacetato]sodium(I)zinc(II)] dihydrate]

Ma, D.-S.

doi:10.1107/S1600536808036441

Poly[[triaqua[μ₄-N-(4-carboxylatophenyl)iminodiacetato]sodium(I)zinc(II)] dihydrate]

In the title coordination polymer, {[NaZn(C₁₁H₈NO₆)(H₂O)₃]·2H₂O}_n, the Zn atom is coordinated in a distorted tetrahedral environment by three carboxylate O atoms from two (4-carboxylatophenylimino)diacetate ligands and one water molecule; the Na atom is in an distorted octahedral coordination environment formed by four carboxylate O atoms from three (4-carboxylatophenylimino)diacetate ligands and two water molecules. The Zn atoms and Na atoms are linked by (4-carboxylatophenylimino)diacetate ligands into a three-dimensional framework; the uncoordinated water molecules fill the voids of the skeleton and stabilize it by O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808036441/ng2512sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808036441/ng2512Isup2.hkl Contains datablock I

CCDC reference: 712288

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Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R factor = 0.026
wR factor = 0.065
Data-to-parameter ratio = 16.2

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No syntax errors found



Alert level G
PLAT793_ALERT_4_G The Model has Chirality at N1      (Verify) ....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

2,2'-(4-Carboxyphenylazanediyl)diacetic acid is a multidentate flexible ligand with versatile binding abilities and capability of participating in hydrongen bonds, thus representing an excellent candidate for the construction of supramolecular complexe. In this paper, we report a novel title compound, (I), which is prepared by 2,2'-(4-carboxyphenylazanediyl)diacetic acid ligand and Zinc dinitrate under neutral aqueous conditions, which forms a three-dimensional framework structure.

The asymmetric unit of (1) consists of one Zn(II) ion, one Na(I) ion, one 4-carboxylatophenylimino)diacetate anion, three coordinated water molecules and two uncoordinated water molecules (Fig. 1). The Zn(II) ion is in a tetrahedral coordination environment, formed by three carboxylate O atoms from two 4-carboxylatophenylimino)diacetate ligands and one water molecules. The Na(I) ion exists in a distorted octahedral configuration with the equatorial plane being defined by the atoms O1, O2, O4^II and O8, and with O9 and o4^III occupy the axial sites. Each 4-carboxylatophenylimino)diacetate anion bridged two Zn(II) ions and three Na(I) ions to form a three-dimensional supramolecular framework network in which uncoordinated water molecules filled the space of the skelecton and stabilized by O—H···O hydrogen bonds(Fig. 2, Table 1).

Related literature top

For the synthesis of 2,2'-(4-carboxyphenylazanediyl)diacetic acid, see: Young & Sweet (1958).

Experimental top

2,2'-(4-Carboxyphenylazanediyl)diacetic acid was synthesized by the literature method (Young et al., 1958). The complex (I) was synthesized with znic(II) dinitrate (0.375 g, 2 mmol) and 2,2'-(4-Carboxyphenylazanediyl)diacetic acid (0.253 g, 1 mmol) were dissolved in methanol and the pH was adjusted to about 7 with 0.01M sodium hydroxide. Colorless crystals were separated from the filtered solution after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms. Dashed lines indicate the hydrogen-bonding interactions [Symmetry code: (I) -x + 2, -y, -z + 2; (II) x, y + 1, z;(III) -x + 1, -y, z + 1].
	Fig. 2. Part of the polymeric structure of (I), showing a three-dimensional framework.Dashed lines indicate the hydrogen-bonding interactions

Poly[[triaqua[µ₄-N-(4-carboxylatophenyl)iminodiacetato]sodium(I)zinc(II)] dihydrate] top

Crystal data top

[NaZn(C₁₁H₈NO₆)(H₂O)₃]·2H₂O	Z = 2
M_r = 428.62	F(000) = 440
Triclinic, P1	D_x = 1.762 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.925 (4) Å	Cell parameters from 7215 reflections
b = 8.989 (6) Å	θ = 3.1–27.5°
c = 11.726 (6) Å	µ = 1.61 mm⁻¹
α = 96.28 (3)°	T = 291 K
β = 98.63 (2)°	Block, colorless
γ = 98.97 (2)°	0.22 × 0.18 × 0.16 mm
V = 808.1 (8) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3668 independent reflections
Radiation source: fine-focus sealed tube	3320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→9
T_min = 0.718, T_max = 0.782	k = −11→11
8055 measured reflections	l = −14→15

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0288P)² + 0.3237P] where P = (F_o² + 2F_c²)/3
3668 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[NaZn(C₁₁H₈NO₆)(H₂O)₃]·2H₂O	γ = 98.97 (2)°
M_r = 428.62	V = 808.1 (8) Å³
Triclinic, P1	Z = 2
a = 7.925 (4) Å	Mo Kα radiation
b = 8.989 (6) Å	µ = 1.61 mm⁻¹
c = 11.726 (6) Å	T = 291 K
α = 96.28 (3)°	0.22 × 0.18 × 0.16 mm
β = 98.63 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3668 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3320 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.782	R_int = 0.021
8055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.11	Δρ_max = 0.28 e Å⁻³
3668 reflections	Δρ_min = −0.44 e Å⁻³
226 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
C1	0.5758 (2)	0.2908 (2)	0.70951 (15)	0.0234 (4)
C2	0.4639 (2)	0.1504 (2)	0.73561 (15)	0.0228 (4)
H1	0.4196	0.1764	0.8066	0.027*
H2	0.3653	0.1200	0.6730	0.027*
C3	0.5765 (2)	−0.1842 (2)	0.59130 (15)	0.0225 (4)
C4	0.4695 (2)	−0.1219 (2)	0.67581 (15)	0.0249 (4)
H8	0.3614	−0.1063	0.6318	0.030*
H7	0.4413	−0.1979	0.7259	0.030*
C5	0.6392 (2)	0.00980 (19)	0.86167 (14)	0.0189 (3)
C6	0.6706 (2)	0.13196 (19)	0.95095 (15)	0.0223 (3)
H3	0.6319	0.2219	0.9372	0.027*
C7	0.7589 (2)	0.1201 (2)	1.05973 (15)	0.0232 (4)
H4	0.7757	0.2014	1.1189	0.028*
C8	0.8230 (2)	−0.0111 (2)	1.08227 (14)	0.0210 (3)
C9	0.7931 (2)	−0.1318 (2)	0.99287 (16)	0.0247 (4)
H5	0.8350	−0.2205	1.0063	0.030*
C10	0.7025 (2)	−0.1227 (2)	0.88446 (15)	0.0237 (4)
H6	0.6834	−0.2053	0.8261	0.028*
C11	0.9258 (2)	−0.0177 (2)	1.19854 (15)	0.0223 (4)
N1	0.5524 (2)	0.02088 (16)	0.74928 (12)	0.0218 (3)
Na1	0.70264 (10)	0.49576 (8)	0.57052 (7)	0.02913 (17)
O1	0.52052 (19)	0.41253 (16)	0.71895 (12)	0.0337 (3)
O2	0.71665 (17)	0.27959 (15)	0.67283 (12)	0.0294 (3)
O3	0.70204 (18)	−0.09667 (16)	0.56440 (12)	0.0310 (3)
O4	0.53062 (19)	−0.31883 (15)	0.54829 (12)	0.0340 (3)
O5	0.9395 (2)	0.08672 (16)	1.28035 (11)	0.0331 (3)
O6	1.00014 (17)	−0.13340 (15)	1.21007 (11)	0.0272 (3)
O7	0.9495 (2)	0.17005 (17)	0.52465 (12)	0.0381 (3)
H9	0.9528	0.1236	0.4581	0.057*
H10	1.0276	0.2489	0.5443	0.057*
O8	0.9626 (2)	0.60310 (17)	0.69752 (13)	0.0380 (3)
H12	0.9924	0.6993	0.7101	0.057*
H11	0.9728	0.5703	0.7630	0.057*
O9	0.81948 (19)	0.56713 (17)	0.40602 (13)	0.0371 (3)
H13	0.8786	0.5073	0.3756	0.056*
H14	0.7250	0.5671	0.3609	0.056*
O10	0.6141 (3)	0.4735 (3)	0.09255 (19)	0.0770 (7)
H15	1.0046	0.6401	0.1287	0.116*
H16	0.8541	0.5354	0.0951	0.116*
O11	0.9641 (2)	0.54605 (19)	0.10841 (14)	0.0459 (4)
H17	0.5653	0.5064	0.1476	0.069*
H18	0.5412	0.4016	0.0505	0.069*
Zn1	0.81967 (3)	0.09629 (2)	0.651229 (17)	0.02072 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0252 (9)	0.0272 (9)	0.0201 (8)	0.0090 (7)	0.0039 (7)	0.0070 (7)
C2	0.0215 (8)	0.0277 (9)	0.0206 (8)	0.0076 (7)	0.0028 (7)	0.0054 (7)
C3	0.0231 (9)	0.0225 (8)	0.0186 (8)	0.0043 (7)	−0.0058 (7)	0.0019 (6)
C4	0.0249 (9)	0.0242 (9)	0.0217 (8)	−0.0020 (7)	0.0002 (7)	0.0000 (7)
C5	0.0194 (8)	0.0215 (8)	0.0163 (7)	0.0018 (6)	0.0045 (6)	0.0046 (6)
C6	0.0267 (9)	0.0198 (8)	0.0210 (8)	0.0070 (7)	0.0020 (7)	0.0037 (6)
C7	0.0248 (9)	0.0239 (9)	0.0198 (8)	0.0040 (7)	0.0018 (7)	0.0005 (7)
C8	0.0181 (8)	0.0269 (9)	0.0189 (8)	0.0032 (7)	0.0043 (7)	0.0070 (7)
C9	0.0289 (9)	0.0217 (8)	0.0260 (9)	0.0080 (7)	0.0058 (8)	0.0077 (7)
C10	0.0319 (9)	0.0209 (8)	0.0193 (8)	0.0073 (7)	0.0054 (7)	0.0013 (6)
C11	0.0172 (8)	0.0266 (9)	0.0226 (8)	−0.0008 (7)	0.0031 (7)	0.0085 (7)
N1	0.0267 (8)	0.0208 (7)	0.0165 (6)	0.0044 (6)	−0.0005 (6)	0.0019 (5)
Na1	0.0296 (4)	0.0250 (4)	0.0319 (4)	0.0013 (3)	0.0037 (3)	0.0070 (3)
O1	0.0411 (8)	0.0296 (7)	0.0385 (8)	0.0181 (6)	0.0157 (7)	0.0107 (6)
O2	0.0273 (7)	0.0265 (7)	0.0412 (8)	0.0108 (5)	0.0144 (6)	0.0143 (6)
O3	0.0303 (7)	0.0297 (7)	0.0298 (7)	−0.0017 (6)	0.0099 (6)	−0.0067 (5)
O4	0.0383 (8)	0.0212 (7)	0.0369 (8)	0.0023 (6)	−0.0018 (6)	−0.0049 (6)
O5	0.0431 (8)	0.0325 (7)	0.0206 (6)	0.0053 (6)	−0.0041 (6)	0.0043 (5)
O6	0.0240 (6)	0.0305 (7)	0.0269 (6)	0.0076 (5)	−0.0019 (5)	0.0081 (5)
O7	0.0432 (9)	0.0404 (8)	0.0272 (7)	−0.0084 (7)	0.0159 (6)	−0.0012 (6)
O8	0.0471 (9)	0.0291 (7)	0.0329 (7)	0.0003 (6)	−0.0020 (7)	0.0049 (6)
O9	0.0320 (8)	0.0427 (9)	0.0359 (8)	0.0032 (6)	0.0076 (6)	0.0048 (6)
O10	0.0630 (13)	0.0963 (18)	0.0657 (13)	0.0182 (12)	0.0178 (11)	−0.0318 (12)
O11	0.0583 (10)	0.0381 (9)	0.0392 (8)	0.0073 (8)	0.0024 (8)	0.0052 (7)
Zn1	0.02166 (11)	0.02060 (11)	0.01927 (10)	0.00437 (7)	0.00116 (8)	0.00223 (7)

Geometric parameters (Å, º) top

C1—O1	1.240 (2)	Na1—O4ⁱ	2.3239 (19)
C1—O2	1.269 (2)	Na1—O8	2.353 (2)
C1—C2	1.513 (3)	Na1—O9	2.3687 (19)
C2—N1	1.461 (2)	Na1—O4ⁱⁱ	2.3901 (19)
C2—H1	0.9700	Na1—O2	2.4009 (19)
C2—H2	0.9700	Na1—O1	2.5245 (19)
C3—O4	1.235 (2)	Na1—Na1ⁱⁱⁱ	3.401 (2)
C3—O3	1.270 (2)	Na1—H14	2.6320
C3—C4	1.514 (3)	O2—Zn1	1.9584 (16)
C4—N1	1.465 (2)	O3—Zn1	1.9336 (17)
C4—H8	0.9700	O4—Na1^iv	2.3239 (19)
C4—H7	0.9700	O4—Na1ⁱⁱ	2.3901 (19)
C5—C6	1.396 (2)	O6—Zn1^v	1.9574 (15)
C5—C10	1.399 (2)	O7—Zn1	2.0400 (16)
C5—N1	1.413 (2)	O7—H9	0.8500
C6—C7	1.383 (2)	O7—H10	0.8500
C6—H3	0.9300	O8—H12	0.8500
C7—C8	1.391 (3)	O8—H11	0.8500
C7—H4	0.9300	O9—H13	0.8500
C8—C9	1.389 (3)	O9—H14	0.8500
C8—C11	1.492 (2)	O10—H17	0.8498
C9—C10	1.380 (3)	O10—H18	0.8504
C9—H5	0.9300	O11—H15	0.8504
C10—H6	0.9300	O11—H16	0.8499
C11—O5	1.246 (2)	Zn1—O6^v	1.9574 (15)
C11—O6	1.283 (2)

O1—C1—O2	122.18 (17)	O4ⁱ—Na1—O2	138.34 (6)
O1—C1—C2	117.99 (17)	O8—Na1—O2	84.49 (6)
O2—C1—C2	119.71 (16)	O9—Na1—O2	132.16 (6)
N1—C2—C1	114.73 (15)	O4ⁱⁱ—Na1—O2	80.48 (7)
N1—C2—H1	108.6	O4ⁱ—Na1—O1	85.66 (6)
C1—C2—H1	108.6	O8—Na1—O1	98.94 (7)
N1—C2—H2	108.6	O9—Na1—O1	168.52 (6)
C1—C2—H2	108.6	O4ⁱⁱ—Na1—O1	78.25 (7)
H1—C2—H2	107.6	O2—Na1—O1	52.90 (5)
O4—C3—O3	123.36 (18)	O4ⁱ—Na1—Na1ⁱⁱⁱ	44.60 (5)
O4—C3—C4	116.88 (17)	O8—Na1—Na1ⁱⁱⁱ	153.40 (6)
O3—C3—C4	119.70 (16)	O9—Na1—Na1ⁱⁱⁱ	89.94 (6)
N1—C4—C3	115.30 (15)	O4ⁱⁱ—Na1—Na1ⁱⁱⁱ	43.06 (5)
N1—C4—H8	108.4	O2—Na1—Na1ⁱⁱⁱ	113.22 (5)
C3—C4—H8	108.4	O1—Na1—Na1ⁱⁱⁱ	78.77 (6)
N1—C4—H7	108.4	O4ⁱ—Na1—H14	75.5
C3—C4—H7	108.4	O8—Na1—H14	109.2
H8—C4—H7	107.5	O9—Na1—H14	18.6
C6—C5—C10	118.34 (15)	O4ⁱⁱ—Na1—H14	77.8
C6—C5—N1	121.25 (15)	O2—Na1—H14	138.5
C10—C5—N1	120.35 (15)	O1—Na1—H14	149.9
C7—C6—C5	120.44 (16)	Na1ⁱⁱⁱ—Na1—H14	71.4
C7—C6—H3	119.8	C1—O1—Na1	87.44 (12)
C5—C6—H3	119.8	C1—O2—Zn1	127.16 (12)
C6—C7—C8	121.26 (17)	C1—O2—Na1	92.39 (10)
C6—C7—H4	119.4	Zn1—O2—Na1	134.30 (7)
C8—C7—H4	119.4	C3—O3—Zn1	126.24 (12)
C9—C8—C7	118.10 (16)	C3—O4—Na1^iv	124.19 (12)
C9—C8—C11	121.76 (16)	C3—O4—Na1ⁱⁱ	143.46 (12)
C7—C8—C11	120.11 (16)	Na1^iv—O4—Na1ⁱⁱ	92.34 (7)
C10—C9—C8	121.31 (16)	C11—O6—Zn1^v	111.56 (12)
C10—C9—H5	119.3	Zn1—O7—H9	128.8
C8—C9—H5	119.3	Zn1—O7—H10	117.0
C9—C10—C5	120.52 (16)	H9—O7—H10	112.8
C9—C10—H6	119.7	Na1—O8—H12	119.1
C5—C10—H6	119.7	Na1—O8—H11	114.2
O5—C11—O6	121.83 (16)	H12—O8—H11	107.7
O5—C11—C8	120.69 (16)	Na1—O9—H13	116.7
O6—C11—C8	117.47 (16)	Na1—O9—H14	98.5
C5—N1—C2	117.69 (14)	H13—O9—H14	111.0
C5—N1—C4	116.93 (14)	H17—O10—H18	106.8
C2—N1—C4	115.93 (14)	H15—O11—H16	107.9
O4ⁱ—Na1—O8	108.97 (7)	O3—Zn1—O6^v	128.18 (6)
O4ⁱ—Na1—O9	87.74 (7)	O3—Zn1—O2	125.40 (7)
O8—Na1—O9	92.08 (7)	O6^v—Zn1—O2	100.31 (7)
O4ⁱ—Na1—O4ⁱⁱ	87.66 (7)	O3—Zn1—O7	97.01 (7)
O8—Na1—O4ⁱⁱ	162.99 (6)	O6^v—Zn1—O7	103.35 (7)
O9—Na1—O4ⁱⁱ	92.12 (7)	O2—Zn1—O7	93.95 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H10···O9^vi	0.85	1.87	2.716 (3)	174
O7—H9···O5^vii	0.85	2.06	2.867 (2)	159
O8—H12···O5^viii	0.85	1.90	2.748 (3)	173
O8—H11···O11^vi	0.85	1.97	2.798 (2)	163
O9—H14···O1ⁱⁱⁱ	0.85	2.07	2.910 (2)	168
O9—H13···O8^vi	0.85	1.96	2.801 (2)	172
O10—H17···O1ⁱⁱⁱ	0.85	1.92	2.762 (3)	174
O10—H18···O10^ix	0.85	2.41	2.744 (5)	104
O11—H15···O6^x	0.85	2.16	2.949 (3)	154
O11—H16···O10	0.85	1.89	2.721 (3)	165

Symmetry codes: (iii) −x+1, −y+1, −z+1; (vi) −x+2, −y+1, −z+1; (vii) x, y, z−1; (viii) −x+2, −y+1, −z+2; (ix) −x+1, −y+1, −z; (x) x, y+1, z−1.

Experimental details

Crystal data
Chemical formula	[NaZn(C₁₁H₈NO₆)(H₂O)₃]·2H₂O
M_r	428.62
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.925 (4), 8.989 (6), 11.726 (6)
α, β, γ (°)	96.28 (3), 98.63 (2), 98.97 (2)
V (Å³)	808.1 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.718, 0.782
No. of measured, independent and observed [I > 2σ(I)] reflections	8055, 3668, 3320
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.065, 1.11
No. of reflections	3668
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.44

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).