A two-dimensional coordination polymer, μ-1,3-benzenedicarboxylato-μ-ethylenediaminezinc(II) trihydrate

A two-dimensional zinc(II) coordination polymer, {[Zn(C₈H₄O₄)(C₂H₈N₂)]·3H₂O}_n, has been constructed from zinc(II), 1,3-benzene­di­carboxyl­ic acid and ethyl­enedi­amine. Within the polymer, each Zn atom is coordinated by two monodentate 1,3-benzene­di­carboxyl­ate ligands and two ethyl­enedi­amine ligands which define a distorted tetrahedral geometry. The two-dimensional network is further held together by π–π stacking interactions and hydrogen-bonding interactions, giving two types of extended one-dimensional channels along the a axis with dimensions of 10.207 (1) × 7.286 (1) Å and 10.207 (1) × 6.240 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.068
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT411_ALERT_2_C Short Inter H...H Contact  H4     ..  H4       =       2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2001).

µ-1,3-benzenedicarboxylato-µ-ethylenediamine-zinc(II) trihydrate

Crystal data

[Zn(C8H4O4)(C2H8N2)]·3H2O	Z = 2
Mr = 343.65	F(000) = 356
Triclinic, P1	Dx = 1.632 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6038 (4) Å	Cell parameters from 3044 reflections
b = 10.2066 (7) Å	θ = 1.7–28.3°
c = 12.2719 (8) Å	µ = 1.79 mm^−1
α = 85.549 (1)°	T = 298 K
β = 88.404 (1)°	Block, colourless
γ = 89.026 (1)°	0.27 × 0.22 × 0.19 mm
V = 699.44 (8) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	2670 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
Tmin = 0.630, Tmax = 0.712	k = −13→13
4279 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0362P)^2] where P = (Fo^2 + 2Fc^2)/3
3078 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.48 e Å^−3
15 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.25154 (4)	0.52838 (2)	0.72784 (2)	0.02699 (9)
O1	0.0498 (3)	0.38117 (13)	0.68876 (12)	0.0305 (3)
O2	0.3631 (3)	0.26901 (14)	0.75111 (14)	0.0383 (4)
O3	0.3557 (3)	−0.22553 (14)	0.74451 (14)	0.0400 (4)
O4	0.0454 (3)	−0.31818 (13)	0.67852 (13)	0.0351 (4)
O1W	1.0037 (3)	0.27931 (16)	0.99905 (16)	0.0460 (4)
H1W1	1.103 (4)	0.229 (2)	1.0322 (19)	0.055*
H1W2	0.913 (4)	0.237 (2)	0.9624 (19)	0.055*
O2W	0.6456 (4)	0.14200 (18)	0.90620 (16)	0.0511 (5)
H2W1	0.564 (4)	0.177 (2)	0.8558 (16)	0.061*
H2W2	0.668 (5)	0.0616 (11)	0.901 (2)	0.061*
O3W	0.6308 (3)	−0.12905 (19)	0.90194 (16)	0.0507 (5)
H3W1	0.560 (4)	−0.147 (3)	0.8455 (12)	0.061*
H3W2	0.537 (4)	−0.139 (3)	0.9574 (12)	0.061*
N1	0.5721 (3)	0.52978 (17)	0.64547 (15)	0.0273 (4)
H1N1	0.644 (4)	0.4561 (11)	0.6614 (18)	0.038 (7)*
H1N2	0.657 (4)	0.5904 (15)	0.668 (2)	0.054 (8)*
N2	0.2637 (3)	0.51169 (17)	0.89188 (15)	0.0279 (4)
H2N1	0.189 (3)	0.4413 (11)	0.9140 (16)	0.028 (6)*
H2N2	0.188 (3)	0.5765 (12)	0.9166 (16)	0.024 (6)*
C1	0.1634 (4)	0.27343 (19)	0.71032 (17)	0.0266 (4)
C2	0.0471 (4)	0.15051 (19)	0.68089 (17)	0.0264 (4)
C3	−0.1633 (4)	0.1589 (2)	0.62465 (19)	0.0340 (5)
H3	−0.2320	0.2409	0.6059	0.041*
C4	−0.2725 (4)	0.0472 (2)	0.5961 (2)	0.0397 (6)
H4	−0.4155	0.0540	0.5593	0.048*
C5	−0.1712 (4)	−0.0742 (2)	0.62178 (19)	0.0336 (5)
H5	−0.2452	−0.1493	0.6018	0.040*
C6	0.0411 (4)	−0.08531 (19)	0.67743 (17)	0.0277 (5)
C7	0.1486 (4)	0.02747 (19)	0.70688 (17)	0.0277 (5)
H7	0.2905	0.0206	0.7446	0.033*
C8	0.1567 (4)	−0.21669 (19)	0.70286 (17)	0.0287 (5)
C9	0.5758 (4)	0.5492 (2)	0.52491 (17)	0.0353 (5)
H9a	0.7389	0.5412	0.4974	0.042*
H9b	0.5181	0.6372	0.5031	0.042*
C10	0.5030 (4)	0.5062 (2)	0.93840 (17)	0.0323 (5)
H10a	0.5879	0.5852	0.9128	0.039*
H10b	0.5909	0.4317	0.9120	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03038 (15)	0.02352 (13)	0.02750 (15)	−0.00196 (9)	−0.00439 (10)	−0.00310 (9)
O1	0.0341 (8)	0.0179 (7)	0.0402 (9)	0.0008 (6)	−0.0076 (7)	−0.0039 (6)
O2	0.0369 (9)	0.0250 (8)	0.0541 (11)	−0.0006 (6)	−0.0149 (8)	−0.0051 (7)
O3	0.0401 (10)	0.0238 (8)	0.0570 (11)	0.0001 (7)	−0.0135 (8)	−0.0043 (7)
O4	0.0400 (9)	0.0182 (7)	0.0478 (10)	−0.0026 (6)	−0.0095 (8)	−0.0035 (7)
O1W	0.0411 (11)	0.0370 (9)	0.0606 (13)	−0.0005 (8)	−0.0054 (9)	−0.0062 (9)
O2W	0.0609 (12)	0.0398 (10)	0.0530 (12)	−0.0008 (9)	−0.0200 (10)	0.0003 (9)
O3W	0.0595 (13)	0.0490 (11)	0.0448 (11)	−0.0003 (9)	−0.0132 (9)	−0.0066 (9)
N1	0.0299 (10)	0.0251 (9)	0.0274 (10)	−0.0014 (8)	−0.0051 (8)	−0.0037 (7)
N2	0.0329 (10)	0.0238 (9)	0.0275 (10)	−0.0021 (8)	−0.0025 (8)	−0.0031 (7)
C1	0.0320 (12)	0.0211 (10)	0.0269 (11)	−0.0019 (8)	0.0012 (9)	−0.0031 (8)
C2	0.0306 (11)	0.0205 (10)	0.0283 (11)	−0.0019 (8)	0.0014 (9)	−0.0041 (8)
C3	0.0355 (12)	0.0234 (10)	0.0442 (14)	0.0031 (9)	−0.0080 (10)	−0.0073 (9)
C4	0.0352 (13)	0.0328 (12)	0.0527 (16)	0.0001 (10)	−0.0154 (11)	−0.0083 (11)
C5	0.0345 (12)	0.0230 (10)	0.0445 (14)	−0.0058 (9)	−0.0036 (10)	−0.0087 (9)
C6	0.0326 (12)	0.0188 (10)	0.0314 (12)	−0.0019 (8)	0.0037 (9)	−0.0018 (8)
C7	0.0287 (11)	0.0227 (10)	0.0321 (12)	−0.0021 (8)	−0.0033 (9)	−0.0029 (8)
C8	0.0367 (12)	0.0191 (10)	0.0303 (12)	−0.0021 (8)	0.0003 (10)	−0.0014 (8)
C9	0.0413 (13)	0.0365 (13)	0.0284 (12)	−0.0089 (10)	−0.0022 (10)	−0.0016 (10)
C10	0.0354 (12)	0.0322 (11)	0.0296 (12)	−0.0017 (9)	−0.0046 (10)	−0.0020 (9)

Geometric parameters (Å, º)

Zn1—O1	1.9913 (13)	N2—H2N1	0.86 (1)
Zn1—O4^i	1.9959 (15)	N2—H2N2	0.85 (1)
Zn1—N2	2.0100 (18)	C1—C2	1.497 (3)
Zn1—N1	2.0364 (18)	C2—C3	1.381 (3)
Zn1—O3^i	2.6130 (15)	C2—C7	1.388 (3)
Zn1—O2	2.7049 (15)	C3—C4	1.377 (3)
O1—C1	1.275 (2)	C3—H3	0.93
O2—C1	1.237 (2)	C4—C5	1.372 (3)
O3—C8	1.239 (3)	C4—H4	0.93
O4—C8	1.277 (2)	C5—C6	1.387 (3)
O1W—H1W1	0.84 (2)	C5—H5	0.93
O1W—H1W2	0.84 (2)	C6—C7	1.385 (3)
O2W—H2W1	0.83 (2)	C6—C8	1.494 (3)
O2W—H2W2	0.83 (1)	C7—H7	0.93
O3W—H3W1	0.84 (1)	C9—C9^ii	1.502 (4)
O3W—H3W2	0.85 (1)	C9—H9a	0.97
N1—C9	1.477 (3)	C9—H9b	0.97
N1—H1N1	0.86 (1)	C10—C10^iii	1.507 (4)
N1—H1N2	0.85 (2)	C10—H10a	0.97
N2—C10	1.470 (3)	C10—H10b	0.97
O1—Zn1—O4^i	100.30 (6)	O1—C1—C2	116.84 (18)
O1—Zn1—N2	105.63 (7)	C3—C2—C7	118.85 (18)
O4^i—Zn1—N2	110.00 (7)	C3—C2—C1	119.67 (18)
O1—Zn1—N1	111.54 (6)	C7—C2—C1	121.46 (18)
O4^i—Zn1—N1	111.88 (7)	C4—C3—C2	120.63 (19)
N2—Zn1—N1	116.17 (7)	C4—C3—H3	119.7
O1—Zn1—O3^i	155.28 (5)	C2—C3—H3	119.7
O4^i—Zn1—O3^i	54.99 (5)	C5—C4—C3	120.3 (2)
N2—Zn1—O3^i	85.11 (6)	C5—C4—H4	119.9
N1—Zn1—O3^i	81.88 (6)	C3—C4—H4	119.9
O1—Zn1—O2	53.33 (5)	C4—C5—C6	120.24 (19)
O4^i—Zn1—O2	153.53 (5)	C4—C5—H5	119.9
N2—Zn1—O2	82.79 (6)	C6—C5—H5	119.9
N1—Zn1—O2	80.38 (6)	C7—C6—C5	119.15 (18)
O3^i—Zn1—O2	151.37 (5)	C7—C6—C8	120.18 (19)
C1—O1—Zn1	108.45 (12)	C5—C6—C8	120.65 (18)
C1—O2—Zn1	75.73 (11)	C6—C7—C2	120.84 (19)
C8—O4—Zn1^iv	105.59 (13)	C6—C7—H7	119.6
H1W1—O1W—H1W2	110.7 (15)	C2—C7—H7	119.6
H2W1—O2W—H2W2	113.0 (16)	O3—C8—O4	121.66 (18)
H3W1—O3W—H3W2	109.8 (15)	O3—C8—C6	120.51 (18)
C9—N1—Zn1	118.82 (13)	O4—C8—C6	117.82 (19)
C9—N1—H1N1	106.3 (16)	N1—C9—C9^ii	111.8 (2)
Zn1—N1—H1N1	108.2 (16)	N1—C9—H9a	109.2
C9—N1—H1N2	106.3 (18)	C9^ii—C9—H9a	109.2
Zn1—N1—H1N2	109.0 (17)	N1—C9—H9b	109.2
H1N1—N1—H1N2	107.8 (14)	C9^ii—C9—H9b	109.2
C10—N2—Zn1	116.24 (13)	H9a—C9—H9b	107.9
C10—N2—H2N1	108.9 (15)	N2—C10—C10^iii	113.0 (2)
Zn1—N2—H2N1	106.9 (14)	N2—C10—H10a	109.0
C10—N2—H2N2	108.0 (14)	C10^iii—C10—H10a	109.0
Zn1—N2—H2N2	108.7 (14)	N2—C10—H10b	109.0
H2N1—N2—H2N2	107.9 (13)	C10^iii—C10—H10b	109.0
O2—C1—O1	122.47 (18)	H10a—C10—H10b	107.8
O2—C1—C2	120.67 (18)
O4^i—Zn1—O1—C1	176.70 (14)	Zn1—O1—C1—C2	−176.73 (14)
N2—Zn1—O1—C1	−68.98 (15)	O2—C1—C2—C3	−172.9 (2)
N1—Zn1—O1—C1	58.09 (15)	O1—C1—C2—C3	5.3 (3)
O3^i—Zn1—O1—C1	177.71 (14)	O2—C1—C2—C7	5.7 (3)
O2—Zn1—O1—C1	−0.73 (12)	O1—C1—C2—C7	−176.0 (2)
O1—Zn1—O2—C1	0.73 (13)	C7—C2—C3—C4	0.9 (3)
O4^i—Zn1—O2—C1	−4.9 (2)	C1—C2—C3—C4	179.6 (2)
N2—Zn1—O2—C1	116.37 (14)	C2—C3—C4—C5	−1.0 (4)
N1—Zn1—O2—C1	−125.45 (14)	C3—C4—C5—C6	0.5 (4)
O3^i—Zn1—O2—C1	−177.90 (13)	C4—C5—C6—C7	0.2 (3)
O1—Zn1—N1—C9	62.24 (16)	C4—C5—C6—C8	−178.2 (2)
O4^i—Zn1—N1—C9	−49.20 (16)	C5—C6—C7—C2	−0.4 (3)
N2—Zn1—N1—C9	−176.65 (14)	C8—C6—C7—C2	178.03 (19)
O3^i—Zn1—N1—C9	−96.22 (15)	C3—C2—C7—C6	−0.2 (3)
O2—Zn1—N1—C9	106.35 (15)	C1—C2—C7—C6	−178.85 (19)
O1—Zn1—N2—C10	126.09 (14)	Zn1^iv—O4—C8—O3	2.5 (3)
O4^i—Zn1—N2—C10	−126.49 (14)	Zn1^iv—O4—C8—C6	−178.70 (15)
N1—Zn1—N2—C10	1.88 (17)	C7—C6—C8—O3	−4.3 (3)
O3^i—Zn1—N2—C10	−76.58 (14)	C5—C6—C8—O3	174.1 (2)
O2—Zn1—N2—C10	77.42 (14)	C7—C6—C8—O4	176.89 (19)
Zn1—O2—C1—O1	−1.09 (19)	C5—C6—C8—O4	−4.7 (3)
Zn1—O2—C1—C2	177.1 (2)	Zn1—N1—C9—C9^ii	−54.9 (3)
Zn1—O1—C1—O2	1.5 (3)	Zn1—N2—C10—C10^iii	179.94 (18)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1^v	0.85 (2)	2.41 (2)	3.093 (2)	137 (2)
N1—H1N2···O4^vi	0.85 (1)	2.39 (2)	3.147 (2)	148 (2)
N2—H2N1···O1W^vii	0.86 (1)	2.15 (1)	3.001 (3)	169 (2)
N2—H2N2···O1W^iii	0.85 (1)	2.12 (1)	2.968 (2)	171 (2)
O1W—H1W2···O2W	0.84 (2)	1.97 (1)	2.786 (2)	166 (3)
O1W—H1W1···O3W^viii	0.84 (2)	1.95 (1)	2.787 (3)	171 (3)
O2W—H2W1···O2	0.83 (2)	1.91 (1)	2.743 (2)	174 (2)
O2W—H2W2···O3W	0.83 (1)	1.96 (1)	2.774 (3)	165 (3)

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