Aqua­(2,2′-bipyrid­yl)bis­(furan-2-carboxyl­ato)zinc(II)

The title complex, [Zn(C₅H₃O₃)₂(C₁₀H₈N₂)(H₂O)], has a slightly distorted square-pyramidal geometry around the Zn^II ion and forms a three-dimensional supra­molecular structure via O—H...O, C—H...O and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.087
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   0 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, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Aqua(2,2'-bipyridyl)bis(furan-2-carboxylato)zinc(II)

Crystal data

[Zn(C5H3O3)2(C10H8N2)(H2O)]	F(000) = 944
Mr = 461.72	Dx = 1.614 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4453 reflections
a = 6.8540 (5) Å	θ = 1.7–28.2°
b = 17.028 (1) Å	µ = 1.34 mm^−1
c = 16.370 (1) Å	T = 293 K
β = 96.016 (1)°	Block, brown
V = 1900.1 (2) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4134 independent reflections
Radiation source: fine-focus sealed tube	3489 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −5→8
Tmin = 0.689, Tmax = 0.878	k = −21→21
10995 measured reflections	l = −20→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.0586P] where P = (Fo^2 + 2Fc^2)/3
4134 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.34 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	0.29692 (3)	0.318574 (12)	0.091311 (13)	0.03196 (9)
C1	0.2515 (3)	0.48197 (12)	0.17332 (13)	0.0427 (5)
H1	0.2566	0.4532	0.2218	0.051*
C2	0.2370 (3)	0.56314 (13)	0.17724 (14)	0.0486 (5)
H2	0.2321	0.5885	0.2273	0.058*
C3	0.2300 (3)	0.60505 (12)	0.10554 (15)	0.0463 (5)
H3	0.2191	0.6595	0.1064	0.056*
C4	0.2392 (3)	0.56624 (11)	0.03224 (13)	0.0388 (4)
H4	0.2356	0.5942	−0.0167	0.047*
C5	0.2537 (2)	0.48486 (10)	0.03237 (11)	0.0310 (4)
C6	0.2651 (2)	0.43703 (10)	−0.04257 (11)	0.0306 (4)
C7	0.2509 (3)	0.46833 (12)	−0.12133 (13)	0.0393 (4)
H7	0.2374	0.5222	−0.1293	0.047*
C8	0.2570 (3)	0.41895 (14)	−0.18743 (13)	0.0464 (5)
H8	0.2453	0.4391	−0.2405	0.056*
C9	0.2806 (3)	0.33978 (14)	−0.17453 (13)	0.0475 (5)
H9	0.2853	0.3055	−0.2185	0.057*
C10	0.2972 (3)	0.31228 (11)	−0.09494 (13)	0.0397 (5)
H10	0.3148	0.2587	−0.0860	0.048*
C11	0.3406 (3)	0.14687 (11)	0.09188 (11)	0.0338 (4)
C12	0.4836 (3)	0.08109 (11)	0.10056 (11)	0.0334 (4)
C13	0.4612 (3)	0.00381 (11)	0.11292 (13)	0.0396 (4)
H13	0.3448	−0.0218	0.1208	0.048*
C14	0.6476 (3)	−0.03125 (12)	0.11168 (13)	0.0444 (5)
H14	0.6779	−0.0843	0.1182	0.053*
C15	0.7719 (3)	0.02690 (13)	0.09929 (14)	0.0477 (5)
H15	0.9055	0.0204	0.0957	0.057*
C16	0.6028 (3)	0.32531 (10)	0.21101 (12)	0.0338 (4)
C17	0.7164 (3)	0.32416 (10)	0.29261 (12)	0.0341 (4)
C18	0.9067 (3)	0.33754 (14)	0.31868 (14)	0.0494 (5)
H18	1.0065	0.3484	0.2860	0.059*
C19	0.9250 (4)	0.33175 (14)	0.40520 (15)	0.0533 (6)
H19	1.0394	0.3383	0.4404	0.064*
C20	0.7487 (4)	0.31525 (11)	0.42679 (14)	0.0431 (5)
H20	0.7199	0.3082	0.4806	0.052*
N1	0.2893 (2)	0.35928 (9)	−0.03003 (9)	0.0321 (3)
N2	0.2584 (2)	0.44357 (9)	0.10269 (9)	0.0338 (3)
O1	0.6758 (2)	0.09713 (8)	0.09259 (9)	0.0446 (3)
O2	0.1738 (2)	0.13365 (8)	0.11212 (10)	0.0483 (4)
O3	0.4011 (2)	0.21048 (7)	0.06357 (9)	0.0427 (3)
O4	0.6152 (2)	0.31010 (7)	0.35902 (9)	0.0378 (3)
O5	0.6900 (2)	0.33914 (8)	0.14945 (9)	0.0428 (3)
O6	0.4199 (2)	0.31383 (7)	0.20867 (9)	0.0395 (3)
O7	0.0232 (2)	0.27744 (11)	0.10118 (12)	0.0507 (4)
H7A	−0.076 (5)	0.2993 (16)	0.1214 (19)	0.075 (9)*
H7B	0.042 (5)	0.234 (2)	0.108 (2)	0.088 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03371 (14)	0.02930 (14)	0.03297 (14)	0.00136 (8)	0.00393 (9)	0.00531 (8)
C1	0.0486 (12)	0.0408 (11)	0.0382 (11)	0.0012 (9)	0.0019 (9)	−0.0021 (8)
C2	0.0492 (13)	0.0445 (12)	0.0517 (13)	−0.0008 (9)	0.0024 (10)	−0.0153 (10)
C3	0.0433 (12)	0.0289 (10)	0.0659 (15)	−0.0018 (8)	0.0026 (10)	−0.0065 (9)
C4	0.0355 (10)	0.0305 (10)	0.0495 (12)	0.0011 (7)	0.0005 (9)	0.0062 (8)
C5	0.0236 (8)	0.0304 (9)	0.0383 (10)	−0.0015 (7)	−0.0002 (7)	0.0030 (7)
C6	0.0237 (9)	0.0322 (9)	0.0355 (10)	−0.0007 (7)	0.0006 (7)	0.0052 (7)
C7	0.0372 (10)	0.0394 (11)	0.0416 (11)	0.0022 (8)	0.0057 (8)	0.0105 (8)
C8	0.0482 (12)	0.0595 (14)	0.0321 (10)	0.0030 (10)	0.0067 (9)	0.0091 (9)
C9	0.0498 (13)	0.0567 (13)	0.0367 (11)	0.0021 (10)	0.0080 (9)	−0.0075 (10)
C10	0.0414 (11)	0.0364 (10)	0.0424 (11)	0.0013 (8)	0.0091 (9)	−0.0032 (8)
C11	0.0420 (11)	0.0307 (10)	0.0279 (9)	0.0012 (8)	−0.0006 (8)	−0.0002 (7)
C12	0.0376 (10)	0.0331 (9)	0.0292 (9)	0.0011 (8)	0.0014 (7)	0.0027 (7)
C13	0.0424 (11)	0.0326 (10)	0.0436 (11)	−0.0025 (8)	0.0029 (8)	0.0044 (8)
C14	0.0524 (13)	0.0340 (10)	0.0465 (12)	0.0099 (9)	0.0036 (9)	0.0042 (9)
C15	0.0404 (12)	0.0488 (13)	0.0547 (14)	0.0126 (9)	0.0080 (10)	0.0071 (10)
C16	0.0373 (11)	0.0264 (9)	0.0375 (10)	0.0029 (7)	0.0026 (8)	0.0052 (7)
C17	0.0354 (10)	0.0322 (10)	0.0347 (10)	0.0006 (7)	0.0044 (8)	0.0022 (7)
C18	0.0357 (11)	0.0646 (14)	0.0475 (13)	−0.0062 (10)	0.0026 (9)	0.0031 (11)
C19	0.0491 (14)	0.0607 (14)	0.0464 (13)	−0.0015 (11)	−0.0125 (10)	−0.0021 (10)
C20	0.0552 (13)	0.0404 (12)	0.0322 (10)	0.0041 (9)	−0.0021 (9)	−0.0041 (8)
N1	0.0308 (8)	0.0307 (8)	0.0349 (8)	0.0020 (6)	0.0045 (6)	0.0036 (6)
N2	0.0360 (9)	0.0310 (8)	0.0336 (8)	0.0005 (6)	0.0000 (6)	0.0014 (6)
O1	0.0417 (8)	0.0386 (8)	0.0542 (9)	0.0014 (6)	0.0085 (7)	0.0124 (7)
O2	0.0396 (8)	0.0371 (8)	0.0691 (10)	0.0006 (6)	0.0100 (7)	0.0085 (7)
O3	0.0514 (9)	0.0287 (7)	0.0501 (9)	0.0059 (6)	0.0156 (7)	0.0081 (6)
O4	0.0398 (8)	0.0381 (7)	0.0355 (7)	−0.0004 (5)	0.0045 (6)	0.0001 (5)
O5	0.0473 (8)	0.0437 (8)	0.0383 (8)	0.0029 (6)	0.0090 (6)	0.0106 (6)
O6	0.0332 (7)	0.0456 (8)	0.0389 (8)	0.0011 (6)	−0.0008 (6)	0.0081 (6)
O7	0.0352 (8)	0.0390 (9)	0.0794 (12)	0.0005 (7)	0.0126 (8)	0.0024 (8)

Geometric parameters (Å, º)

Zn1—O6	2.0171 (14)	C10—H10	0.9300
Zn1—O7	2.0249 (16)	C11—O2	1.244 (2)
Zn1—O3	2.0425 (13)	C11—O3	1.265 (2)
Zn1—N1	2.0993 (15)	C11—C12	1.485 (3)
Zn1—N2	2.1553 (15)	C12—C13	1.343 (3)
C1—N2	1.333 (2)	C12—O1	1.365 (2)
C1—C2	1.388 (3)	C13—C14	1.413 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.370 (3)	C14—C15	1.335 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.377 (3)	C15—O1	1.364 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.389 (3)	C16—O5	1.247 (2)
C4—H4	0.9300	C16—O6	1.265 (2)
C5—N2	1.346 (2)	C16—C17	1.474 (3)
C5—C6	1.481 (3)	C17—C18	1.349 (3)
C6—N1	1.347 (2)	C17—O4	1.370 (2)
C6—C7	1.389 (3)	C18—C19	1.412 (3)
C7—C8	1.374 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.324 (3)
C8—C9	1.371 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—O4	1.365 (3)
C9—C10	1.378 (3)	C20—H20	0.9300
C9—H9	0.9300	O7—H7A	0.87 (3)
C10—N1	1.336 (3)	O7—H7B	0.76 (3)
O6—Zn1—O7	102.02 (7)	O3—C11—C12	116.26 (17)
O6—Zn1—O3	93.14 (6)	C13—C12—O1	109.73 (17)
O7—Zn1—O3	93.12 (7)	C13—C12—C11	131.94 (18)
O6—Zn1—N1	151.76 (6)	O1—C12—C11	118.29 (16)
O7—Zn1—N1	104.97 (7)	C12—C13—C14	107.08 (18)
O3—Zn1—N1	93.55 (6)	C12—C13—H13	126.5
O6—Zn1—N2	90.00 (5)	C14—C13—H13	126.5
O7—Zn1—N2	102.23 (7)	C15—C14—C13	106.33 (18)
O3—Zn1—N2	163.34 (6)	C15—C14—H14	126.8
N1—Zn1—N2	76.38 (6)	C13—C14—H14	126.8
N2—C1—C2	122.5 (2)	C14—C15—O1	110.62 (19)
N2—C1—H1	118.7	C14—C15—H15	124.7
C2—C1—H1	118.7	O1—C15—H15	124.7
C3—C2—C1	118.4 (2)	O5—C16—O6	124.20 (18)
C3—C2—H2	120.8	O5—C16—C17	118.86 (17)
C1—C2—H2	120.8	O6—C16—C17	116.92 (18)
C2—C3—C4	119.72 (18)	C18—C17—O4	109.35 (18)
C2—C3—H3	120.1	C18—C17—C16	133.3 (2)
C4—C3—H3	120.1	O4—C17—C16	117.28 (16)
C3—C4—C5	119.15 (19)	C17—C18—C19	106.7 (2)
C3—C4—H4	120.4	C17—C18—H18	126.7
C5—C4—H4	120.4	C19—C18—H18	126.7
N2—C5—C4	121.16 (18)	C20—C19—C18	107.2 (2)
N2—C5—C6	114.98 (15)	C20—C19—H19	126.4
C4—C5—C6	123.86 (17)	C18—C19—H19	126.4
N1—C6—C7	120.93 (18)	C19—C20—O4	110.5 (2)
N1—C6—C5	115.49 (16)	C19—C20—H20	124.8
C7—C6—C5	123.58 (17)	O4—C20—H20	124.8
C8—C7—C6	119.41 (19)	C10—N1—C6	118.82 (17)
C8—C7—H7	120.3	C10—N1—Zn1	123.76 (13)
C6—C7—H7	120.3	C6—N1—Zn1	117.33 (12)
C9—C8—C7	119.54 (19)	C1—N2—C5	119.04 (16)
C9—C8—H8	120.2	C1—N2—Zn1	125.10 (13)
C7—C8—H8	120.2	C5—N2—Zn1	115.72 (12)
C8—C9—C10	118.4 (2)	C15—O1—C12	106.24 (16)
C8—C9—H9	120.8	C11—O3—Zn1	123.69 (13)
C10—C9—H9	120.8	C20—O4—C17	106.37 (17)
N1—C10—C9	122.84 (19)	C16—O6—Zn1	109.65 (12)
N1—C10—H10	118.6	Zn1—O7—H7A	130.6 (19)
C9—C10—H10	118.6	Zn1—O7—H7B	102 (2)
O2—C11—O3	126.74 (18)	H7A—O7—H7B	119 (3)
O2—C11—C12	116.99 (17)
N2—C1—C2—C3	−0.1 (3)	O3—Zn1—N1—C10	16.53 (16)
C1—C2—C3—C4	−0.6 (3)	N2—Zn1—N1—C10	−176.91 (16)
C2—C3—C4—C5	0.5 (3)	O6—Zn1—N1—C6	−63.50 (18)
C3—C4—C5—N2	0.2 (3)	O7—Zn1—N1—C6	98.94 (13)
C3—C4—C5—C6	−179.84 (17)	O3—Zn1—N1—C6	−166.88 (12)
N2—C5—C6—N1	−3.5 (2)	N2—Zn1—N1—C6	−0.31 (12)
C4—C5—C6—N1	176.57 (16)	C2—C1—N2—C5	0.9 (3)
N2—C5—C6—C7	176.09 (17)	C2—C1—N2—Zn1	176.41 (15)
C4—C5—C6—C7	−3.9 (3)	C4—C5—N2—C1	−0.9 (3)
N1—C6—C7—C8	1.5 (3)	C6—C5—N2—C1	179.14 (16)
C5—C6—C7—C8	−178.01 (17)	C4—C5—N2—Zn1	−176.86 (13)
C6—C7—C8—C9	−1.2 (3)	C6—C5—N2—Zn1	3.20 (19)
C7—C8—C9—C10	0.1 (3)	O6—Zn1—N2—C1	−22.29 (16)
C8—C9—C10—N1	0.7 (3)	O7—Zn1—N2—C1	80.01 (17)
O2—C11—C12—C13	13.6 (3)	O3—Zn1—N2—C1	−123.3 (2)
O3—C11—C12—C13	−165.5 (2)	N1—Zn1—N2—C1	−177.32 (17)
O2—C11—C12—O1	−168.87 (17)	O6—Zn1—N2—C5	153.36 (13)
O3—C11—C12—O1	12.0 (2)	O7—Zn1—N2—C5	−104.34 (13)
O1—C12—C13—C14	−0.8 (2)	O3—Zn1—N2—C5	52.4 (3)
C11—C12—C13—C14	176.86 (19)	N1—Zn1—N2—C5	−1.66 (12)
C12—C13—C14—C15	0.5 (2)	C14—C15—O1—C12	−0.5 (2)
C13—C14—C15—O1	0.0 (3)	C13—C12—O1—C15	0.8 (2)
O5—C16—C17—C18	2.1 (3)	C11—C12—O1—C15	−177.20 (17)
O6—C16—C17—C18	−176.2 (2)	O2—C11—O3—Zn1	29.5 (3)
O5—C16—C17—O4	178.91 (15)	C12—C11—O3—Zn1	−151.44 (13)
O6—C16—C17—O4	0.6 (2)	O6—Zn1—O3—C11	69.33 (15)
O4—C17—C18—C19	−0.2 (2)	O7—Zn1—O3—C11	−32.91 (15)
C16—C17—C18—C19	176.8 (2)	N1—Zn1—O3—C11	−138.12 (15)
C17—C18—C19—C20	0.2 (3)	N2—Zn1—O3—C11	169.88 (17)
C18—C19—C20—O4	−0.2 (3)	C19—C20—O4—C17	0.1 (2)
C9—C10—N1—C6	−0.4 (3)	C18—C17—O4—C20	0.0 (2)
C9—C10—N1—Zn1	176.15 (16)	C16—C17—O4—C20	−177.48 (15)
C7—C6—N1—C10	−0.7 (3)	O5—C16—O6—Zn1	1.5 (2)
C5—C6—N1—C10	178.84 (16)	C17—C16—O6—Zn1	179.74 (12)
C7—C6—N1—Zn1	−177.52 (13)	O7—Zn1—O6—C16	169.03 (12)
C5—C6—N1—Zn1	2.07 (19)	O3—Zn1—O6—C16	75.16 (11)
O6—Zn1—N1—C10	119.91 (16)	N1—Zn1—O6—C16	−28.32 (18)
O7—Zn1—N1—C10	−77.66 (16)	N2—Zn1—O6—C16	−88.47 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1^i	0.93	2.48	3.182 (3)	132
C9—H9···O6^ii	0.93	2.57	3.434 (3)	154
C4—H4···O5^iii	0.93	2.55	3.461 (2)	167
O7—H7A···O5^iv	0.87 (3)	1.84 (3)	2.706 (2)	171 (3)
O7—H7B···O2	0.76 (3)	1.93 (4)	2.656 (2)	160 (3)

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