Diaqua­bis(5-carb­oxy-1H-imidazole-4-carboxyl­ato-κ²N,O)zinc(II)–4,4′-bipyridine (1/1)

In the title Zn^II complex, [Zn(C₅H₃N₂O₄)₂(H₂O)₂]·C₁₀H₈N₂, the Zn^II atom is octa­hedrally surrounded by two chelating monodeprotonated 5-carb­oxy-1H-imidazole-4-carboxyl­ate ligands and two water mol­ecules. Inter­molecular O—H...O hydrogen-bonding inter­actions link the mol­ecules in the crystal structure, forming two-dimensional layers. These layers self-assemble into a three-dimensional network through inter­molecular N—H...N hydrogen-bond inter­actions between imidazole N—H and pyridyl N atoms. The Zn atom and the mid-point of the central C—C bond of the bipyridine are located on inversion centers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.025
• wR factor = 0.066
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.82
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   N1      ..       5.43 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C20 H18 N6 O10 Zn1
            Atom count from _chemical_formula_moiety:C30 H26 N8 O10 Zn1
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.824
            Tmax scaled      0.824 Tmin scaled      0.814
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
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 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); cell refinement: SAINT (Bruker, 1998; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Diaquabis(5-carboxy-1H-imidazole-4-carboxylato-κ²N,O)zinc(II) 4,4'-bipyridine solvate

Crystal data

[Zn(C5H3N2O4)2(H2O)2]·C10H8N2	Z = 1
Mr = 567.78	F(000) = 290
Triclinic, P1	Dx = 1.741 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0195 (5) Å	Cell parameters from 1052 reflections
b = 6.6503 (7) Å	θ = 2.9–28.0°
c = 17.0480 (17) Å	µ = 1.21 mm^−1
α = 86.317 (2)°	T = 293 K
β = 86.687 (2)°	Block, colorless
γ = 72.588 (2)°	0.22 × 0.18 × 0.16 mm
V = 541.44 (10) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2096 independent reflections
Radiation source: fine-focus sealed tube	2055 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.009
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −6→6
Tmin = 0.988, Tmax = 1.000	k = −7→8
2982 measured reflections	l = −14→20

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.037P)^2 + 0.2715P] where P = (Fo^2 + 2Fc^2)/3
2096 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.31 e Å^−3
3 restraints	Δρmin = −0.39 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	0.0000	0.5000	0.0000	0.01828 (10)
C1	0.0660 (3)	0.2391 (2)	0.14291 (9)	0.0173 (3)
C2	0.1683 (3)	0.1837 (2)	0.21691 (9)	0.0184 (3)
C3	0.2999 (3)	0.4505 (2)	0.16625 (9)	0.0193 (3)
H3	0.3836	0.5582	0.1608	0.023*
C4	−0.1119 (3)	0.1550 (2)	0.09515 (9)	0.0181 (3)
C5	0.1486 (4)	0.0173 (3)	0.27743 (10)	0.0236 (3)
C6	0.6585 (4)	0.2559 (3)	0.42332 (10)	0.0266 (4)
H6	0.5871	0.1421	0.4323	0.032*
C7	0.8091 (4)	0.3014 (3)	0.48157 (10)	0.0247 (3)
H7	0.8368	0.2197	0.5284	0.030*
C8	0.9192 (3)	0.4704 (3)	0.46967 (9)	0.0208 (3)
C9	0.8697 (4)	0.5856 (3)	0.39810 (10)	0.0269 (4)
H9	0.9397	0.6995	0.3872	0.032*
C10	0.7160 (4)	0.5293 (3)	0.34337 (10)	0.0275 (4)
H10	0.6844	0.6086	0.2960	0.033*
N1	0.1504 (3)	0.4066 (2)	0.11185 (8)	0.0185 (3)
N2	0.3153 (3)	0.3200 (2)	0.23021 (8)	0.0195 (3)
H2	0.4021	0.3218	0.2721	0.023*
N3	0.6102 (3)	0.3671 (2)	0.35478 (8)	0.0251 (3)
O1	−0.1944 (3)	0.00447 (18)	0.12403 (7)	0.0247 (3)
O2	−0.1707 (2)	0.24418 (17)	0.02826 (7)	0.0203 (2)
O3	0.0048 (3)	−0.1086 (2)	0.25900 (8)	0.0353 (3)
H3A	−0.0639	−0.0693	0.2161	0.053*
O4	0.2596 (3)	−0.0011 (2)	0.33940 (7)	0.0324 (3)
O1W	−0.3645 (2)	0.71321 (18)	0.05378 (7)	0.0216 (2)
H1WA	−0.330 (4)	0.816 (2)	0.0697 (11)	0.026*
H1WB	−0.508 (3)	0.748 (3)	0.0291 (11)	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02199 (15)	0.02082 (15)	0.01564 (15)	−0.01142 (10)	−0.00674 (10)	0.00237 (9)
C1	0.0188 (7)	0.0178 (7)	0.0173 (7)	−0.0085 (6)	−0.0020 (6)	−0.0004 (6)
C2	0.0200 (7)	0.0198 (7)	0.0169 (8)	−0.0080 (6)	−0.0017 (6)	−0.0020 (6)
C3	0.0211 (7)	0.0223 (8)	0.0179 (8)	−0.0108 (6)	−0.0042 (6)	−0.0013 (6)
C4	0.0175 (7)	0.0181 (7)	0.0202 (8)	−0.0069 (6)	−0.0014 (6)	−0.0035 (6)
C5	0.0295 (8)	0.0224 (8)	0.0187 (8)	−0.0077 (7)	−0.0008 (6)	0.0015 (6)
C6	0.0300 (9)	0.0292 (9)	0.0243 (9)	−0.0136 (7)	−0.0055 (7)	−0.0013 (7)
C7	0.0297 (8)	0.0274 (8)	0.0191 (8)	−0.0114 (7)	−0.0061 (7)	0.0022 (6)
C8	0.0195 (7)	0.0251 (8)	0.0179 (8)	−0.0062 (6)	−0.0027 (6)	−0.0020 (6)
C9	0.0343 (9)	0.0305 (9)	0.0209 (8)	−0.0168 (7)	−0.0077 (7)	0.0039 (7)
C10	0.0330 (9)	0.0325 (9)	0.0187 (8)	−0.0118 (7)	−0.0089 (7)	0.0029 (7)
N1	0.0211 (6)	0.0198 (6)	0.0178 (7)	−0.0106 (5)	−0.0041 (5)	0.0004 (5)
N2	0.0218 (6)	0.0241 (7)	0.0152 (6)	−0.0099 (5)	−0.0058 (5)	−0.0007 (5)
N3	0.0248 (7)	0.0306 (8)	0.0214 (7)	−0.0089 (6)	−0.0067 (5)	−0.0037 (6)
O1	0.0337 (6)	0.0244 (6)	0.0231 (6)	−0.0189 (5)	−0.0031 (5)	−0.0009 (5)
O2	0.0223 (6)	0.0233 (6)	0.0194 (6)	−0.0120 (5)	−0.0065 (4)	−0.0006 (4)
O3	0.0572 (9)	0.0319 (7)	0.0257 (7)	−0.0275 (7)	−0.0084 (6)	0.0086 (5)
O4	0.0424 (7)	0.0356 (7)	0.0202 (6)	−0.0131 (6)	−0.0090 (5)	0.0072 (5)
O1W	0.0214 (6)	0.0225 (6)	0.0250 (6)	−0.0113 (5)	−0.0079 (5)	−0.0022 (5)

Geometric parameters (Å, º)

Zn1—N1^i	2.0798 (13)	C5—O3	1.320 (2)
Zn1—N1	2.0798 (13)	C6—N3	1.336 (2)
Zn1—O2	2.1400 (11)	C6—C7	1.383 (2)
Zn1—O2^i	2.1400 (11)	C6—H6	0.9300
Zn1—O1W^i	2.1491 (12)	C7—C8	1.392 (2)
Zn1—O1W	2.1491 (12)	C7—H7	0.9300
C1—N1	1.3713 (19)	C8—C9	1.392 (2)
C1—C2	1.376 (2)	C8—C8^ii	1.491 (3)
C1—C4	1.488 (2)	C9—C10	1.381 (2)
C2—N2	1.365 (2)	C9—H9	0.9300
C2—C5	1.485 (2)	C10—N3	1.337 (2)
C3—N1	1.325 (2)	C10—H10	0.9300
C3—N2	1.340 (2)	N2—H2	0.8600
C3—H3	0.9300	O3—H3A	0.8200
C4—O1	1.2559 (19)	O1W—H1WA	0.815 (9)
C4—O2	1.260 (2)	O1W—H1WB	0.818 (9)
C5—O4	1.205 (2)
N1^i—Zn1—N1	180.00 (9)	O3—C5—C2	116.11 (15)
N1^i—Zn1—O2	100.39 (4)	N3—C6—C7	123.30 (16)
N1—Zn1—O2	79.61 (4)	N3—C6—H6	118.4
N1^i—Zn1—O2^i	79.61 (4)	C7—C6—H6	118.4
N1—Zn1—O2^i	100.39 (4)	C6—C7—C8	119.62 (16)
O2—Zn1—O2^i	180.00 (6)	C6—C7—H7	120.2
N1^i—Zn1—O1W^i	88.44 (5)	C8—C7—H7	120.2
N1—Zn1—O1W^i	91.56 (5)	C7—C8—C9	117.02 (15)
O2—Zn1—O1W^i	90.15 (4)	C7—C8—C8^ii	122.38 (19)
O2^i—Zn1—O1W^i	89.85 (4)	C9—C8—C8^ii	120.59 (19)
N1^i—Zn1—O1W	91.56 (5)	C10—C9—C8	119.45 (16)
N1—Zn1—O1W	88.44 (5)	C10—C9—H9	120.3
O2—Zn1—O1W	89.85 (4)	C8—C9—H9	120.3
O2^i—Zn1—O1W	90.15 (4)	N3—C10—C9	123.55 (16)
O1W^i—Zn1—O1W	180.00 (6)	N3—C10—H10	118.2
N1—C1—C2	109.16 (13)	C9—C10—H10	118.2
N1—C1—C4	118.39 (13)	C3—N1—C1	105.83 (13)
C2—C1—C4	132.43 (14)	C3—N1—Zn1	143.05 (11)
N2—C2—C1	105.96 (13)	C1—N1—Zn1	111.12 (10)
N2—C2—C5	120.42 (14)	C3—N2—C2	107.67 (13)
C1—C2—C5	133.62 (15)	C3—N2—H2	126.2
N1—C3—N2	111.38 (14)	C2—N2—H2	126.2
N1—C3—H3	124.3	C6—N3—C10	117.06 (15)
N2—C3—H3	124.3	C4—O2—Zn1	114.46 (9)
O1—C4—O2	124.99 (14)	C5—O3—H3A	109.5
O1—C4—C1	118.59 (14)	Zn1—O1W—H1WA	111.6 (14)
O2—C4—C1	116.42 (13)	Zn1—O1W—H1WB	117.3 (14)
O4—C5—O3	122.45 (15)	H1WA—O1W—H1WB	111.5 (17)
O4—C5—C2	121.44 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3	0.86	1.89	2.7435 (19)	170
O3—H3A···O1	0.82	1.72	2.5403 (18)	177
O1W—H1WA···O1^iii	0.82 (1)	1.91 (1)	2.7058 (16)	166 (2)
O1W—H1WB···O2^iv	0.82 (1)	1.92 (1)	2.7224 (15)	166 (2)

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