(5,5'-Dicarboxy-biphenyl-2,2'-dicarboxyl-ato-κO,O)bis-(1,10-phenanthroline-κN,N')zinc(II) dihydrate.

In the title compound, [Zn(C(16)H(8)O(8))(C(12)H(8)N(2))(2)]·2H(2)O, the Zn(II) atom is located on a twofold rotation axis and is six-coordinated by two O atoms from a 5,5'-dicarboxy-biphenyl-2,2'-dicarboxyl-ate ligand and four N atoms from two 1,10-phenanthroline mol-ecules in a distorted octa-hedral geometry. The crystal structure involves O-H⋯O hydrogen bonds.

Related literature

For related literature, see: Che et al. (2006 ▶); Chen et al. (2008 ▶); Lehn (1990 ▶); Zang et al. (2006 ▶).

Experimental

Crystal data

[Zn(C16H8O8)(C12H8N2)2]·2H2O

M = 790.03

Monoclinic,

a = 16.901 (5) Å

b = 9.473 (3) Å

c = 22.126 (7) Å

β = 96.429 (5)°

V = 3520.4 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 293 (2) K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.817, T max = 0.853

9664 measured reflections

3487 independent reflections

2437 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.124

S = 1.04

3487 reflections

255 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015742/hy2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015742/hy2133Isup2.hkl

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

[Zn(C16H8O8)(C12H8N2)2]·2H2O	F000 = 1624
Mr = 790.03	Dx = 1.491 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3487 reflections
a = 16.901 (5) Å	θ = 2.0–26.0º
b = 9.473 (3) Å	µ = 0.77 mm−1
c = 22.126 (7) Å	T = 293 (2) K
β = 96.429 (5)º	Block, colorless
V = 3520.4 (19) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 293(2) K	θmax = 26.2º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −20→18
Tmin = 0.817, Tmax = 0.853	k = −11→11
9664 measured reflections	l = −21→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.8309P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3487 reflections	Δρmax = 0.31 e Å−3
255 parameters	Δρmin = −0.22 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
C1	0.3739 (2)	0.3651 (5)	0.63923 (18)	0.0637 (11)
H1	0.3543	0.2958	0.6634	0.076*
C2	0.3354 (3)	0.3873 (6)	0.5804 (2)	0.0880 (16)
H2	0.2913	0.3337	0.5656	0.106*
C3	0.3645 (3)	0.4896 (6)	0.5454 (2)	0.0926 (17)
H3	0.3390	0.5077	0.5067	0.111*
C4	0.4311 (3)	0.5664 (5)	0.5667 (2)	0.0762 (14)
C5	0.4663 (4)	0.6727 (6)	0.5317 (2)	0.0988 (19)
H5	0.4424	0.6948	0.4929	0.119*
C6	0.5326 (4)	0.7401 (6)	0.5538 (3)	0.106 (2)
H6	0.5542	0.8074	0.5298	0.127*
C7	0.5713 (3)	0.7116 (4)	0.6134 (2)	0.0776 (14)
C8	0.6414 (4)	0.7740 (5)	0.6377 (3)	0.098 (2)
H8	0.6659	0.8408	0.6152	0.117*
C9	0.6744 (3)	0.7386 (5)	0.6936 (3)	0.0906 (17)
H9	0.7222	0.7793	0.7098	0.109*
C10	0.6361 (3)	0.6400 (4)	0.7274 (2)	0.0722 (13)
H10	0.6593	0.6164	0.7661	0.087*
C11	0.5368 (3)	0.6116 (4)	0.6493 (2)	0.0600 (11)
C12	0.4662 (3)	0.5378 (4)	0.62567 (18)	0.0588 (11)
C13	0.40756 (18)	0.1983 (3)	0.81456 (14)	0.0328 (7)
C14	0.47901 (16)	0.1060 (3)	0.82887 (12)	0.0264 (7)
C15	0.51756 (16)	0.0460 (3)	0.78249 (12)	0.0240 (6)
C16	0.58975 (17)	−0.0230 (3)	0.79802 (13)	0.0299 (7)
H16	0.6169	−0.0613	0.7676	0.036*
C17	0.62178 (18)	−0.0353 (3)	0.85843 (14)	0.0335 (7)
C18	0.58141 (19)	0.0192 (4)	0.90393 (14)	0.0421 (9)
H18	0.6021	0.0094	0.9445	0.051*
C19	0.51007 (18)	0.0882 (3)	0.88893 (13)	0.0383 (8)
H19	0.4824	0.1235	0.9197	0.046*
C20	0.6999 (2)	−0.1096 (4)	0.87475 (16)	0.0460 (9)
N1	0.43688 (18)	0.4390 (3)	0.66158 (13)	0.0510 (8)
N2	0.5682 (2)	0.5791 (3)	0.70633 (15)	0.0563 (8)
O1	0.40798 (12)	0.2849 (2)	0.77191 (9)	0.0370 (5)
O2	0.35134 (14)	0.1861 (3)	0.84667 (11)	0.0646 (8)
O1W	0.33466 (18)	0.0544 (3)	0.95823 (12)	0.0704 (8)
O3	0.73266 (15)	−0.1494 (3)	0.82746 (11)	0.0707 (9)
H3A	0.7749	−0.1893	0.8384	0.106*
O4	0.72855 (15)	−0.1289 (3)	0.92612 (11)	0.0786 (10)
Zn1	0.5000	0.41820 (6)	0.7500	0.0430 (2)
H1B	0.315 (2)	0.112 (3)	0.9823 (14)	0.064*
H1A	0.333 (2)	0.110 (3)	0.9282 (12)	0.064*

	U11	U22	U33	U12	U13	U23
C1	0.053 (3)	0.081 (3)	0.058 (3)	0.011 (2)	0.009 (2)	0.017 (2)
C2	0.054 (3)	0.135 (5)	0.074 (3)	0.021 (3)	0.002 (2)	0.021 (3)
C3	0.085 (4)	0.133 (5)	0.061 (3)	0.046 (4)	0.016 (3)	0.038 (3)
C4	0.092 (4)	0.076 (3)	0.065 (3)	0.033 (3)	0.030 (3)	0.029 (3)
C5	0.145 (6)	0.088 (4)	0.072 (4)	0.041 (4)	0.049 (4)	0.042 (3)
C6	0.168 (6)	0.065 (4)	0.097 (5)	0.018 (4)	0.071 (4)	0.030 (3)
C7	0.116 (4)	0.045 (3)	0.084 (4)	0.007 (3)	0.065 (3)	0.006 (2)
C8	0.151 (6)	0.051 (3)	0.109 (5)	−0.032 (3)	0.093 (4)	−0.018 (3)
C9	0.113 (4)	0.068 (3)	0.104 (4)	−0.040 (3)	0.071 (4)	−0.032 (3)
C10	0.093 (4)	0.052 (2)	0.081 (3)	−0.023 (2)	0.047 (3)	−0.020 (2)
C11	0.083 (3)	0.035 (2)	0.070 (3)	0.007 (2)	0.044 (2)	−0.0001 (19)
C12	0.076 (3)	0.051 (2)	0.056 (3)	0.027 (2)	0.033 (2)	0.0180 (19)
C13	0.0281 (18)	0.0396 (18)	0.0312 (18)	0.0106 (14)	0.0054 (14)	0.0015 (15)
C14	0.0225 (16)	0.0314 (17)	0.0255 (16)	0.0040 (12)	0.0037 (12)	−0.0001 (12)
C15	0.0231 (16)	0.0238 (15)	0.0253 (16)	0.0002 (11)	0.0036 (12)	0.0000 (11)
C16	0.0247 (17)	0.0352 (17)	0.0304 (18)	0.0077 (13)	0.0056 (13)	−0.0018 (13)
C17	0.0262 (18)	0.0431 (18)	0.0310 (18)	0.0093 (14)	0.0018 (13)	0.0017 (14)
C18	0.039 (2)	0.063 (2)	0.0236 (18)	0.0165 (17)	0.0000 (14)	−0.0008 (16)
C19	0.0358 (19)	0.054 (2)	0.0266 (17)	0.0185 (16)	0.0097 (14)	−0.0025 (15)
C20	0.033 (2)	0.070 (3)	0.035 (2)	0.0191 (17)	0.0034 (16)	0.0049 (17)
N1	0.051 (2)	0.0519 (19)	0.052 (2)	0.0120 (16)	0.0165 (15)	0.0146 (15)
N2	0.072 (2)	0.0382 (17)	0.066 (2)	−0.0056 (17)	0.0362 (18)	−0.0067 (16)
O1	0.0319 (13)	0.0374 (12)	0.0422 (13)	0.0101 (10)	0.0063 (10)	0.0116 (10)
O2	0.0449 (16)	0.098 (2)	0.0564 (17)	0.0427 (15)	0.0294 (12)	0.0411 (15)
O1W	0.079 (2)	0.088 (2)	0.0457 (19)	0.0195 (17)	0.0126 (15)	0.0143 (15)
O3	0.0530 (17)	0.121 (2)	0.0388 (15)	0.0559 (17)	0.0072 (12)	0.0098 (15)
O4	0.0610 (19)	0.133 (3)	0.0394 (16)	0.0561 (18)	−0.0040 (13)	0.0029 (16)
Zn1	0.0470 (4)	0.0373 (3)	0.0467 (4)	0.000	0.0144 (3)	0.000

C1—N1	1.323 (5)	C13—O2	1.254 (4)
C1—C2	1.405 (6)	C13—C14	1.496 (4)
C1—H1	0.9300	C14—C19	1.383 (4)
C2—C3	1.366 (7)	C14—C15	1.396 (4)
C2—H2	0.9300	C15—C16	1.393 (4)
C3—C4	1.378 (7)	C15—C15i	1.493 (5)
C3—H3	0.9300	C16—C17	1.390 (4)
C4—C12	1.399 (6)	C16—H16	0.9300
C4—C5	1.439 (7)	C17—C18	1.378 (4)
C5—C6	1.334 (7)	C17—C20	1.504 (4)
C5—H5	0.9300	C18—C19	1.379 (4)
C6—C7	1.431 (7)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.378 (7)	C20—O4	1.198 (4)
C7—C11	1.404 (5)	C20—O3	1.294 (4)
C8—C9	1.341 (7)	N1—Zn1	2.130 (3)
C8—H8	0.9300	N2—Zn1	2.199 (3)
C9—C10	1.399 (6)	O1—Zn1	2.102 (2)
C9—H9	0.9300	O1W—H1B	0.86 (3)
C10—N2	1.321 (5)	O1W—H1A	0.85 (3)
C10—H10	0.9300	O3—H3A	0.8200
C11—N2	1.348 (5)	Zn1—O1	2.102 (2)
C11—C12	1.431 (6)	Zn1—N1	2.130 (3)
C12—N1	1.357 (4)	Zn1—N2	2.199 (3)
C13—O1	1.251 (3)
N1—C1—C2	122.5 (4)	C16—C15—C14	118.5 (3)
N1—C1—H1	118.8	C16—C15—C15i	118.7 (3)
C2—C1—H1	118.8	C14—C15—C15i	122.7 (3)
C3—C2—C1	118.2 (5)	C17—C16—C15	120.9 (3)
C3—C2—H2	120.9	C17—C16—H16	119.6
C1—C2—H2	120.9	C15—C16—H16	119.6
C2—C3—C4	120.8 (5)	C18—C17—C16	120.0 (3)
C2—C3—H3	119.6	C18—C17—C20	119.5 (3)
C4—C3—H3	119.6	C16—C17—C20	120.5 (3)
C3—C4—C12	117.5 (4)	C17—C18—C19	119.5 (3)
C3—C4—C5	123.8 (5)	C17—C18—H18	120.2
C12—C4—C5	118.7 (5)	C19—C18—H18	120.2
C6—C5—C4	121.3 (5)	C18—C19—C14	121.1 (3)
C6—C5—H5	119.4	C18—C19—H19	119.5
C4—C5—H5	119.4	C14—C19—H19	119.5
C5—C6—C7	121.7 (5)	O4—C20—O3	124.0 (3)
C5—C6—H6	119.1	O4—C20—C17	123.3 (3)
C7—C6—H6	119.1	O3—C20—C17	112.7 (3)
C8—C7—C11	117.4 (5)	C1—N1—C12	118.5 (4)
C8—C7—C6	124.2 (5)	C1—N1—Zn1	126.4 (3)
C11—C7—C6	118.3 (5)	C12—N1—Zn1	115.1 (3)
C9—C8—C7	120.2 (5)	C10—N2—C11	117.7 (4)
C9—C8—H8	119.9	C10—N2—Zn1	128.7 (3)
C7—C8—H8	119.9	C11—N2—Zn1	113.5 (3)
C8—C9—C10	119.3 (5)	C13—O1—Zn1	129.41 (19)
C8—C9—H9	120.3	H1B—O1W—H1A	96 (4)
C10—C9—H9	120.3	C20—O3—H3A	109.5
N2—C10—C9	122.6 (5)	O1—Zn1—O1i	106.16 (11)
N2—C10—H10	118.7	O1—Zn1—N1i	98.70 (10)
C9—C10—H10	118.7	O1i—Zn1—N1i	87.72 (10)
N2—C11—C7	122.7 (5)	O1—Zn1—N1	87.72 (10)
N2—C11—C12	117.1 (3)	O1i—Zn1—N1	98.70 (10)
C7—C11—C12	120.2 (5)	N1i—Zn1—N1	169.36 (16)
N1—C12—C4	122.4 (4)	O1—Zn1—N2	162.88 (11)
N1—C12—C11	117.8 (4)	O1i—Zn1—N2	82.94 (10)
C4—C12—C11	119.7 (4)	N1i—Zn1—N2	96.08 (12)
O1—C13—O2	123.8 (3)	N1—Zn1—N2	76.44 (13)
O1—C13—C14	118.1 (3)	O1—Zn1—N2i	82.94 (10)
O2—C13—C14	118.1 (3)	O1i—Zn1—N2i	162.88 (11)
C19—C14—C15	119.9 (3)	N1i—Zn1—N2i	76.44 (13)
C19—C14—C13	119.0 (3)	N1—Zn1—N2i	96.08 (12)
C15—C14—C13	121.0 (2)	N2—Zn1—N2i	92.23 (15)
N1—C1—C2—C3	−0.2 (7)	C16—C17—C20—O4	−176.6 (4)
C1—C2—C3—C4	1.7 (8)	C18—C17—C20—O3	−177.0 (3)
C2—C3—C4—C12	−1.5 (7)	C16—C17—C20—O3	3.8 (5)
C2—C3—C4—C5	178.1 (4)	C2—C1—N1—C12	−1.4 (6)
C3—C4—C5—C6	−177.5 (5)	C2—C1—N1—Zn1	179.3 (3)
C12—C4—C5—C6	2.2 (8)	C4—C12—N1—C1	1.6 (5)
C4—C5—C6—C7	−0.8 (9)	C11—C12—N1—C1	−176.8 (3)
C5—C6—C7—C8	177.4 (5)	C4—C12—N1—Zn1	−179.0 (3)
C5—C6—C7—C11	−1.3 (8)	C11—C12—N1—Zn1	2.6 (4)
C11—C7—C8—C9	0.1 (7)	C9—C10—N2—C11	2.0 (6)
C6—C7—C8—C9	−178.6 (5)	C9—C10—N2—Zn1	178.0 (3)
C7—C8—C9—C10	−1.2 (7)	C7—C11—N2—C10	−3.2 (5)
C8—C9—C10—N2	0.2 (7)	C12—C11—N2—C10	175.9 (3)
C8—C7—C11—N2	2.2 (6)	C7—C11—N2—Zn1	−179.8 (3)
C6—C7—C11—N2	−179.1 (4)	C12—C11—N2—Zn1	−0.8 (4)
C8—C7—C11—C12	−176.9 (4)	O2—C13—O1—Zn1	135.8 (3)
C6—C7—C11—C12	1.9 (6)	C14—C13—O1—Zn1	−42.9 (4)
C3—C4—C12—N1	−0.2 (6)	C13—O1—Zn1—O1i	63.6 (2)
C5—C4—C12—N1	−179.8 (4)	C13—O1—Zn1—N1i	−26.5 (3)
C3—C4—C12—C11	178.2 (4)	C13—O1—Zn1—N1	162.0 (3)
C5—C4—C12—C11	−1.5 (6)	C13—O1—Zn1—N2	−176.0 (3)
N2—C11—C12—N1	−1.2 (5)	C13—O1—Zn1—N2i	−101.6 (3)
C7—C11—C12—N1	177.9 (3)	C1—N1—Zn1—O1	−9.4 (3)
N2—C11—C12—C4	−179.6 (3)	C12—N1—Zn1—O1	171.3 (2)
C7—C11—C12—C4	−0.5 (6)	C1—N1—Zn1—O1i	96.6 (3)
O1—C13—C14—C19	134.7 (3)	C12—N1—Zn1—O1i	−82.7 (2)
O2—C13—C14—C19	−44.2 (4)	C1—N1—Zn1—N1i	−136.8 (3)
O1—C13—C14—C15	−40.9 (4)	C12—N1—Zn1—N1i	43.9 (2)
O2—C13—C14—C15	140.3 (3)	C1—N1—Zn1—N2	177.1 (3)
C19—C14—C15—C16	−4.1 (4)	C12—N1—Zn1—N2	−2.2 (2)
C13—C14—C15—C16	171.4 (3)	C1—N1—Zn1—N2i	−92.1 (3)
C19—C14—C15—C15i	172.4 (2)	C12—N1—Zn1—N2i	88.6 (2)
C13—C14—C15—C15i	−12.1 (4)	C10—N2—Zn1—O1	162.7 (3)
C14—C15—C16—C17	1.7 (4)	C11—N2—Zn1—O1	−21.1 (5)
C15i—C15—C16—C17	−175.0 (2)	C10—N2—Zn1—O1i	−73.9 (3)
C15—C16—C17—C18	1.1 (5)	C11—N2—Zn1—O1i	102.3 (2)
C15—C16—C17—C20	−179.8 (3)	C10—N2—Zn1—N1i	13.1 (3)
C16—C17—C18—C19	−1.3 (5)	C11—N2—Zn1—N1i	−170.7 (2)
C20—C17—C18—C19	179.5 (3)	C10—N2—Zn1—N1	−174.6 (3)
C17—C18—C19—C14	−1.1 (5)	C11—N2—Zn1—N1	1.6 (2)
C15—C14—C19—C18	3.9 (5)	C10—N2—Zn1—N2i	89.7 (3)
C13—C14—C19—C18	−171.7 (3)	C11—N2—Zn1—N2i	−94.1 (3)
C18—C17—C20—O4	2.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ii	0.82	1.74	2.538 (3)	162
O1W—H1B···O4iii	0.86 (3)	2.24 (2)	2.966 (4)	143 (3)
O1W—H1A···O2	0.85 (3)	2.00 (2)	2.808 (4)	159 (4)

Zn1—O1	2.102 (2)
Zn1—N1	2.130 (3)
Zn1—N2	2.199 (3)

O1—Zn1—O1i	106.16 (11)
O1—Zn1—N1i	98.70 (10)
O1—Zn1—N1	87.72 (10)
N1i—Zn1—N1	169.36 (16)
O1—Zn1—N2	162.88 (11)
N1—Zn1—N2	76.44 (13)
O1—Zn1—N2i	82.94 (10)
N1—Zn1—N2i	96.08 (12)
N2—Zn1—N2i	92.23 (15)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ii	0.82	1.74	2.538 (3)	162
O1W—H1B⋯O4iii	0.86 (3)	2.24 (2)	2.966 (4)	143 (3)
O1W—H1A⋯O2	0.85 (3)	2.00 (2)	2.808 (4)	159 (4)

Symmetry codes: (ii) ; (iii) .