Poly[[[(4,7-diphenyl-1,10-phenanthroline)zinc(II)]-μ-benzene-1,3-dicarboxyl­ato] monohydrate]

In the title compound, {[Zn(C₈H₄O₄)(C₂₄H₁₆N₂)]·H₂O}_n, the Zn center is coordinated by three O atoms from three different benzene-1,3-dicarboxyl­ate dianions and two N atoms from the bidentate 4,7-diphenyl-1,10-phenanthroline ligand to display a distorted trigonal–bipyramidal geometry. The benzene-1,3-dicarboxyl­ate ligand acts as a μ₃-bridge, resulting in a two-dimensional coordination polymer with rhombus-shaped channels.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.101
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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
   1 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

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Computing details

Data collection: SMART (Bruker, 1998 or 2000); cell refinement: SAINT (Bruker, 1998 or 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.

Poly[[(4,7-diphenyl-1,10-phenanthroline)zinc(II)]-µ-benzene-1,3-dicarboxylato] monohydrate]

Crystal data

[Zn(C8H4O4)(C24H16N2)]·H2O	F(000) = 1192
Mr = 579.89	Dx = 1.554 Mg m^−3
Monoclinic, P21/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.4746 (16) Å	θ = 2.4–26.4°
b = 12.5849 (17) Å	µ = 1.04 mm^−1
c = 17.284 (2) Å	T = 292 K
β = 96.647 (2)°	Block, yellow
V = 2479.2 (6) Å^3	0.37 × 0.25 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	4957 independent reflections
Radiation source: fine-focus sealed tube	4296 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −14→14
Tmin = 0.730, Tmax = 0.833	k = −15→15
13506 measured reflections	l = −21→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 0.0069P] where P = (Fo^2 + 2Fc^2)/3
4957 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.57 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	0.353507 (18)	0.412335 (18)	0.502509 (12)	0.02247 (10)
N2	0.18712 (14)	0.33027 (14)	0.48252 (10)	0.0261 (4)
N1	0.23449 (13)	0.52951 (13)	0.44713 (10)	0.0248 (4)
C20	−0.10580 (17)	0.41706 (16)	0.39164 (13)	0.0265 (4)
H20A	−0.1826	0.3926	0.3825	0.032*
C9	0.26227 (18)	0.62698 (17)	0.42781 (13)	0.0305 (5)
H9A	0.3378	0.6516	0.4434	0.037*
C32	0.09764 (16)	0.38748 (16)	0.44510 (11)	0.0229 (4)
C31	0.12296 (16)	0.49587 (15)	0.42615 (11)	0.0225 (4)
C18	0.03524 (16)	0.56011 (16)	0.38653 (11)	0.0232 (4)
C21	−0.01499 (16)	0.34514 (16)	0.42357 (11)	0.0247 (4)
C30	0.16656 (18)	0.22972 (18)	0.49813 (13)	0.0333 (5)
H30A	0.2261	0.1906	0.5260	0.040*
C19	−0.08236 (16)	0.51871 (16)	0.37470 (12)	0.0261 (4)
H19A	−0.1435	0.5631	0.3549	0.031*
C10	0.18320 (18)	0.69436 (17)	0.38504 (13)	0.0314 (5)
H10A	0.2077	0.7614	0.3710	0.038*
C23	−0.14390 (17)	0.18039 (17)	0.40776 (13)	0.0295 (5)
C17	−0.09055 (18)	0.6987 (2)	0.25297 (13)	0.0348 (5)
H17A	−0.0883	0.6278	0.2380	0.042*
C22	−0.03249 (17)	0.23567 (17)	0.43622 (12)	0.0279 (4)
C11	0.06824 (17)	0.66305 (16)	0.36299 (12)	0.0272 (4)
C12	−0.01400 (17)	0.73557 (17)	0.31617 (12)	0.0297 (5)
C29	0.06038 (18)	0.17966 (18)	0.47495 (13)	0.0338 (5)
H29A	0.0516	0.1078	0.4855	0.041*
C28	−0.1960 (2)	0.10966 (19)	0.45495 (15)	0.0403 (6)
H28A	−0.1622	0.0984	0.5058	0.048*
C24	−0.19580 (18)	0.19525 (18)	0.33151 (13)	0.0338 (5)
H24A	−0.1624	0.2423	0.2989	0.041*
C13	−0.0156 (2)	0.84260 (19)	0.33404 (14)	0.0380 (5)
H13A	0.0381	0.8692	0.3738	0.046*
C25	−0.2963 (2)	0.1407 (2)	0.30425 (15)	0.0407 (6)
H25A	−0.3298	0.1507	0.2532	0.049*
C26	−0.3474 (2)	0.0715 (2)	0.35192 (18)	0.0487 (7)
H26A	−0.4156	0.0354	0.3332	0.058*
C14	−0.0957 (2)	0.9110 (2)	0.29368 (17)	0.0469 (7)
H14A	−0.0968	0.9825	0.3072	0.056*
C16	−0.1694 (2)	0.7677 (2)	0.21271 (14)	0.0421 (6)
H16A	−0.2204	0.7427	0.1709	0.050*
C15	−0.1734 (2)	0.8729 (2)	0.23379 (15)	0.0454 (6)
H15A	−0.2286	0.9181	0.2075	0.054*
C27	−0.2971 (2)	0.0559 (2)	0.42753 (17)	0.0503 (7)
H27A	−0.3314	0.0092	0.4599	0.060*
OW	0.5926 (4)	0.8727 (3)	0.5575 (2)	0.1594 (15)
H1	0.5864	0.8160	0.5946	0.191*
H2	0.5708	0.8200	0.5162	0.191*
O2	0.44592 (12)	0.29654 (12)	0.55949 (8)	0.0318 (3)
C1	0.41517 (17)	0.27640 (16)	0.62722 (12)	0.0251 (4)
O1	0.33072 (13)	0.31725 (13)	0.65362 (9)	0.0370 (4)
C8	0.46991 (17)	0.17730 (16)	0.75216 (11)	0.0242 (4)
H8A	0.4122	0.2157	0.7735	0.029*
C3	0.57597 (17)	0.13817 (17)	0.64384 (12)	0.0275 (4)
H3A	0.5896	0.1497	0.5925	0.033*
C2	0.48935 (16)	0.19547 (15)	0.67518 (11)	0.0230 (4)
C7	0.51303 (18)	0.07964 (15)	0.87999 (12)	0.0254 (4)
C6	0.53602 (17)	0.10219 (15)	0.79749 (12)	0.0235 (4)
C5	0.62284 (17)	0.04555 (17)	0.76496 (12)	0.0289 (5)
H5A	0.6677	−0.0046	0.7946	0.035*
C4	0.64225 (18)	0.06389 (18)	0.68875 (13)	0.0325 (5)
H4A	0.7004	0.0260	0.6674	0.039*
O4	0.41708 (13)	0.11162 (13)	0.89993 (8)	0.0348 (4)
O3	0.59039 (14)	0.03176 (13)	0.92301 (9)	0.0399 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02035 (14)	0.02661 (16)	0.01926 (15)	−0.00097 (8)	−0.00280 (9)	0.00056 (8)
N2	0.0216 (8)	0.0299 (9)	0.0254 (9)	−0.0004 (7)	−0.0036 (7)	0.0029 (7)
N1	0.0192 (8)	0.0276 (9)	0.0262 (9)	−0.0026 (7)	−0.0029 (6)	−0.0008 (7)
C20	0.0173 (9)	0.0306 (11)	0.0308 (12)	−0.0017 (8)	−0.0009 (8)	−0.0016 (8)
C9	0.0241 (10)	0.0307 (11)	0.0348 (12)	−0.0059 (9)	−0.0042 (9)	−0.0003 (9)
C32	0.0216 (9)	0.0263 (10)	0.0202 (10)	−0.0003 (8)	−0.0003 (7)	−0.0016 (8)
C31	0.0210 (9)	0.0251 (10)	0.0208 (10)	−0.0003 (7)	−0.0003 (7)	−0.0033 (8)
C18	0.0213 (9)	0.0254 (10)	0.0220 (10)	0.0002 (8)	−0.0005 (8)	−0.0016 (8)
C21	0.0228 (9)	0.0279 (11)	0.0229 (10)	−0.0024 (8)	0.0011 (8)	−0.0012 (8)
C30	0.0311 (11)	0.0298 (12)	0.0365 (13)	−0.0005 (9)	−0.0062 (9)	0.0088 (9)
C19	0.0206 (9)	0.0284 (11)	0.0282 (11)	0.0036 (8)	−0.0022 (8)	−0.0015 (8)
C10	0.0275 (10)	0.0255 (11)	0.0399 (13)	−0.0047 (8)	−0.0014 (9)	0.0049 (9)
C23	0.0257 (10)	0.0260 (11)	0.0357 (12)	−0.0043 (8)	−0.0012 (9)	0.0002 (9)
C17	0.0308 (11)	0.0419 (13)	0.0315 (12)	−0.0002 (9)	0.0032 (9)	0.0041 (10)
C22	0.0263 (10)	0.0294 (11)	0.0274 (11)	−0.0053 (8)	0.0004 (8)	0.0009 (8)
C11	0.0254 (10)	0.0278 (11)	0.0279 (11)	0.0009 (8)	0.0003 (8)	−0.0001 (8)
C12	0.0248 (10)	0.0338 (12)	0.0303 (12)	0.0018 (8)	0.0025 (8)	0.0076 (9)
C29	0.0311 (11)	0.0276 (11)	0.0414 (13)	−0.0043 (9)	−0.0010 (10)	0.0078 (9)
C28	0.0387 (13)	0.0384 (13)	0.0429 (15)	−0.0108 (10)	0.0001 (11)	0.0054 (11)
C24	0.0311 (11)	0.0303 (12)	0.0387 (13)	−0.0024 (9)	−0.0009 (9)	−0.0003 (9)
C13	0.0386 (12)	0.0342 (12)	0.0397 (14)	0.0022 (10)	−0.0020 (10)	0.0065 (10)
C25	0.0349 (12)	0.0393 (14)	0.0446 (15)	0.0000 (10)	−0.0090 (10)	−0.0042 (11)
C26	0.0306 (12)	0.0449 (15)	0.068 (2)	−0.0108 (10)	−0.0045 (12)	−0.0116 (13)
C14	0.0480 (15)	0.0379 (14)	0.0556 (18)	0.0111 (11)	0.0087 (13)	0.0151 (11)
C16	0.0309 (11)	0.0652 (18)	0.0291 (13)	0.0026 (11)	−0.0008 (9)	0.0128 (11)
C15	0.0327 (12)	0.0605 (17)	0.0427 (15)	0.0113 (11)	0.0036 (11)	0.0239 (13)
C27	0.0445 (15)	0.0426 (14)	0.0639 (19)	−0.0177 (12)	0.0074 (13)	0.0062 (13)
OW	0.202 (4)	0.137 (3)	0.146 (3)	−0.017 (3)	0.047 (3)	−0.039 (3)
O2	0.0319 (8)	0.0396 (9)	0.0232 (8)	0.0053 (6)	−0.0003 (6)	0.0100 (6)
C1	0.0238 (9)	0.0255 (10)	0.0245 (11)	−0.0027 (8)	−0.0028 (8)	0.0029 (8)
O1	0.0355 (8)	0.0384 (9)	0.0373 (9)	0.0109 (7)	0.0054 (7)	0.0075 (7)
C8	0.0221 (9)	0.0252 (11)	0.0250 (11)	−0.0006 (7)	0.0012 (8)	0.0016 (8)
C3	0.0280 (10)	0.0311 (11)	0.0239 (11)	−0.0015 (9)	0.0051 (8)	0.0047 (8)
C2	0.0227 (9)	0.0233 (10)	0.0218 (10)	−0.0027 (7)	−0.0020 (8)	0.0031 (8)
C7	0.0294 (11)	0.0238 (11)	0.0213 (11)	−0.0061 (8)	−0.0049 (8)	0.0013 (7)
C6	0.0220 (9)	0.0254 (10)	0.0217 (10)	−0.0041 (8)	−0.0033 (8)	0.0025 (8)
C5	0.0240 (10)	0.0308 (11)	0.0307 (12)	0.0028 (8)	−0.0024 (8)	0.0058 (9)
C4	0.0253 (10)	0.0366 (12)	0.0361 (13)	0.0068 (9)	0.0061 (9)	0.0025 (10)
O4	0.0323 (8)	0.0508 (10)	0.0210 (8)	−0.0002 (7)	0.0022 (6)	0.0049 (7)
O3	0.0473 (9)	0.0416 (10)	0.0278 (9)	0.0075 (8)	−0.0090 (7)	0.0086 (7)

Geometric parameters (Å, º)

Zn1—O2	1.9941 (14)	C28—H28A	0.9300
Zn1—O4^i	2.0164 (15)	C24—C25	1.377 (3)
Zn1—O3^ii	2.0344 (15)	C24—H24A	0.9300
Zn1—N1	2.1571 (17)	C13—C14	1.388 (3)
Zn1—N2	2.1630 (17)	C13—H13A	0.9300
N2—C30	1.321 (3)	C25—C26	1.376 (4)
N2—C32	1.355 (2)	C25—H25A	0.9300
N1—C9	1.320 (3)	C26—C27	1.380 (4)
N1—C31	1.357 (2)	C26—H26A	0.9300
C20—C19	1.347 (3)	C14—C15	1.372 (4)
C20—C21	1.441 (3)	C14—H14A	0.9300
C20—H20A	0.9300	C16—C15	1.375 (4)
C9—C10	1.391 (3)	C16—H16A	0.9300
C9—H9A	0.9300	C15—H15A	0.9300
C32—C21	1.407 (3)	C27—H27A	0.9300
C32—C31	1.440 (3)	OW—H1	0.9672
C31—C18	1.406 (3)	OW—H2	0.9853
C18—C11	1.422 (3)	C1—O2	1.286 (2)
C18—C19	1.439 (3)	C1—O1	1.230 (2)
C21—C22	1.413 (3)	C1—C2	1.512 (3)
C30—C29	1.389 (3)	C8—C2	1.393 (3)
C30—H30A	0.9300	C8—C6	1.395 (3)
C19—H19A	0.9300	C8—H8A	0.9300
C10—C11	1.387 (3)	C3—C4	1.385 (3)
C10—H10A	0.9300	C3—C2	1.388 (3)
C23—C28	1.389 (3)	C3—H3A	0.9300
C23—C24	1.395 (3)	C7—O3	1.245 (2)
C23—C22	1.488 (3)	C7—O4	1.257 (3)
C17—C16	1.382 (3)	C7—C6	1.507 (3)
C17—C12	1.399 (3)	C6—C5	1.395 (3)
C17—H17A	0.9300	C5—C4	1.381 (3)
C22—C29	1.384 (3)	C5—H5A	0.9300
C11—C12	1.484 (3)	C4—H4A	0.9300
C12—C13	1.382 (3)	O4—Zn1^iii	2.0164 (15)
C29—H29A	0.9300	O3—Zn1^iv	2.0344 (15)
C28—C27	1.379 (3)
O2—Zn1—O4^i	95.69 (6)	C22—C29—C30	120.6 (2)
O2—Zn1—O3^ii	96.67 (7)	C22—C29—H29A	119.7
O4^i—Zn1—O3^ii	123.14 (7)	C30—C29—H29A	119.7
O2—Zn1—N1	172.70 (6)	C27—C28—C23	121.0 (2)
O4^i—Zn1—N1	89.25 (6)	C27—C28—H28A	119.5
O3^ii—Zn1—N1	85.04 (7)	C23—C28—H28A	119.5
O2—Zn1—N2	97.99 (6)	C25—C24—C23	120.4 (2)
O4^i—Zn1—N2	100.99 (6)	C25—C24—H24A	119.8
O3^ii—Zn1—N2	131.50 (7)	C23—C24—H24A	119.8
N1—Zn1—N2	75.74 (6)	C12—C13—C14	121.1 (2)
C30—N2—C32	117.58 (17)	C12—C13—H13A	119.4
C30—N2—Zn1	126.88 (14)	C14—C13—H13A	119.4
C32—N2—Zn1	115.37 (13)	C26—C25—C24	120.6 (2)
C9—N1—C31	118.05 (17)	C26—C25—H25A	119.7
C9—N1—Zn1	126.05 (13)	C24—C25—H25A	119.7
C31—N1—Zn1	115.75 (13)	C25—C26—C27	119.8 (2)
C19—C20—C21	121.75 (18)	C25—C26—H26A	120.1
C19—C20—H20A	119.1	C27—C26—H26A	120.1
C21—C20—H20A	119.1	C15—C14—C13	119.8 (2)
N1—C9—C10	122.64 (18)	C15—C14—H14A	120.1
N1—C9—H9A	118.7	C13—C14—H14A	120.1
C10—C9—H9A	118.7	C15—C16—C17	120.7 (2)
N2—C32—C21	123.14 (19)	C15—C16—H16A	119.6
N2—C32—C31	116.74 (16)	C17—C16—H16A	119.6
C21—C32—C31	120.11 (17)	C14—C15—C16	119.9 (2)
N1—C31—C18	123.42 (18)	C14—C15—H15A	120.0
N1—C31—C32	116.33 (16)	C16—C15—H15A	120.0
C18—C31—C32	120.23 (17)	C28—C27—C26	119.9 (2)
C31—C18—C11	117.64 (17)	C28—C27—H27A	120.1
C31—C18—C19	117.89 (18)	C26—C27—H27A	120.1
C11—C18—C19	124.44 (18)	H1—OW—H2	87.2
C32—C21—C22	118.09 (18)	C1—O2—Zn1	114.03 (13)
C32—C21—C20	117.69 (18)	O1—C1—O2	124.47 (18)
C22—C21—C20	124.21 (18)	O1—C1—C2	119.71 (18)
N2—C30—C29	123.17 (19)	O2—C1—C2	115.81 (17)
N2—C30—H30A	118.4	C2—C8—C6	120.72 (18)
C29—C30—H30A	118.4	C2—C8—H8A	119.6
C20—C19—C18	121.39 (18)	C6—C8—H8A	119.6
C20—C19—H19A	119.3	C4—C3—C2	120.24 (19)
C18—C19—H19A	119.3	C4—C3—H3A	119.9
C11—C10—C9	120.9 (2)	C2—C3—H3A	119.9
C11—C10—H10A	119.5	C3—C2—C8	119.24 (18)
C9—C10—H10A	119.5	C3—C2—C1	121.28 (18)
C28—C23—C24	118.4 (2)	C8—C2—C1	119.47 (17)
C28—C23—C22	121.17 (19)	O3—C7—O4	125.3 (2)
C24—C23—C22	120.41 (19)	O3—C7—C6	117.73 (19)
C16—C17—C12	120.0 (2)	O4—C7—C6	117.00 (17)
C16—C17—H17A	120.0	C8—C6—C5	119.16 (19)
C12—C17—H17A	120.0	C8—C6—C7	121.05 (18)
C29—C22—C21	117.14 (18)	C5—C6—C7	119.77 (18)
C29—C22—C23	120.37 (19)	C4—C5—C6	120.05 (19)
C21—C22—C23	122.47 (18)	C4—C5—H5A	120.0
C10—C11—C18	117.15 (18)	C6—C5—H5A	120.0
C10—C11—C12	119.98 (19)	C5—C4—C3	120.6 (2)
C18—C11—C12	122.86 (17)	C5—C4—H4A	119.7
C13—C12—C17	118.3 (2)	C3—C4—H4A	119.7
C13—C12—C11	120.08 (19)	C7—O4—Zn1^iii	127.63 (14)
C17—C12—C11	121.6 (2)	C7—O3—Zn1^iv	152.46 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW—H1···O4^ii	0.97	2.57	3.372 (4)	140
OW—H2···O2^v	0.99	1.96	2.935 (4)	170

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