(6-Carboxyl­ato­pyridine-2-carboxyl­ic acid-κ²N,O)(pyridine-2,6-di­carboxyl­ic acid-κ²N,O)silver(I) dihydrate

In the title compound, [Ag(C₇H₄NO₄)(C₇H₅NO₄)]·2H₂O, the Ag^I atom has a distorted tetrahedral coordination geometry, defined by two pyridyl N and two carboxyl O atoms from bidentate ligands in a trans arrangement. The planar ligands in the complex are almost perpendicular to each other. The complexes are connected via symmetric O—H...O hydrogen bonds and linked through the water mol­ecules, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.025
• wR factor = 0.079
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O1     -   H5     ...       1.23 Ang.
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O6     -   H10    ...       1.24 Ang.

Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O10    -   H14    ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ag1    -   O2      ..       5.90 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ag1    -   O5      ..       5.44 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  O4      ..       2.65 Ang.
PLAT728_ALERT_1_C D-H..A  Calc      168.73, Rep      167.00 Dev...       1.73 Deg.
              O7   -H9   -O9      1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: Crystal Structure (Rigaku & Rigaku/MSC, 2000-2004) and CRYSTALS (Watkin et al., 1996); cell refinement: Crystal Structure and CRYSTALS; data reduction: Crystal Structure and CRYSTALS; program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Scheldrick, 1997); molecular graphics: ORTEP III (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

[Ag(C7H4NO4)(C7H5NO4)]·2H2O	Z = 2
Mr = 477.13	F(000) = 476.0
Triclinic, P1	Dx = 1.953 Mg m^−3
Hall symbol: -p_1	Mo Kα radiation, λ = 0.7107 Å
a = 6.934 (9) Å	Cell parameters from 7457 reflections
b = 8.103 (8) Å	θ = 3.0–27.5°
c = 15.10 (2) Å	µ = 1.31 mm^−1
α = 95.92 (4)°	T = 296 K
β = 102.76 (5)°	Platelet, colorless
γ = 98.04 (4)°	0.30 × 0.10 × 0.10 mm
V = 811.4 (17) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	3326 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.019
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.676, Tmax = 0.881	k = −10→10
7969 measured reflections	l = −19→19
3685 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 0.3231P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.079	(Δ/σ)max = 0.003
S = 1.11	Δρmax = 0.59 e Å^−3
3685 reflections	Δρmin = −0.51 e Å^−3
256 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.45684 (3)	0.64206 (2)	0.24886 (1)	0.0392 (1)
O1	0.4023 (3)	0.8574 (2)	−0.0147 (1)	0.0443 (4)
O2	0.5072 (3)	0.8348 (2)	0.1335 (1)	0.0412 (4)
O3	0.1775 (4)	0.0810 (2)	0.1335 (1)	0.0488 (5)
O4	0.3524 (4)	0.2964 (3)	0.2354 (1)	0.0625 (7)
O5	0.7522 (3)	0.5844 (3)	0.3637 (1)	0.0429 (4)
O6	0.8648 (3)	0.5775 (2)	0.5136 (1)	0.0399 (4)
O7	0.0226 (3)	0.9458 (3)	0.3629 (1)	0.0463 (4)
O8	0.1982 (3)	0.8685 (2)	0.2634 (1)	0.0396 (4)
O9	−0.1967 (3)	1.0707 (3)	0.2421 (2)	0.0640 (6)
O10	0.9636 (4)	0.4070 (3)	0.2687 (1)	0.0642 (6)
N1	0.3259 (3)	0.5031 (2)	0.1004 (1)	0.0248 (3)
N2	0.4447 (3)	0.7389 (2)	0.3976 (1)	0.0244 (3)
C1	0.3140 (3)	0.5951 (3)	0.0316 (1)	0.0271 (4)
C2	0.2197 (4)	0.5288 (3)	−0.0586 (1)	0.0331 (5)
C3	0.1347 (4)	0.3602 (3)	−0.0787 (1)	0.0358 (5)
C4	0.1485 (4)	0.2626 (3)	−0.0083 (1)	0.0337 (5)
C5	0.2442 (3)	0.3394 (3)	0.0798 (1)	0.0262 (4)
C6	0.4164 (3)	0.7782 (3)	0.0546 (1)	0.0302 (4)
C7	0.2665 (4)	0.2384 (3)	0.1583 (1)	0.0311 (4)
C8	0.5770 (3)	0.6990 (3)	0.4676 (1)	0.0257 (4)
C9	0.5667 (4)	0.7339 (3)	0.5582 (1)	0.0307 (4)
C10	0.4135 (4)	0.8107 (3)	0.5779 (1)	0.0341 (5)
C11	0.2759 (3)	0.8540 (3)	0.5069 (1)	0.0301 (4)
C12	0.2990 (3)	0.8182 (3)	0.4181 (1)	0.0256 (4)
C13	0.7437 (3)	0.6129 (3)	0.4439 (2)	0.0296 (4)
C14	0.1657 (3)	0.8782 (3)	0.3393 (1)	0.0278 (4)
H1	0.2138	0.5968	−0.1048	0.040*
H2	0.0694	0.3134	−0.1385	0.043*
H3	0.0949	0.1485	−0.0198	0.040*
H4	0.191	0.033	0.178	0.09*
H5	0.5000	1.0000	0.0000	0.04 (4)*
H6	0.6626	0.7057	0.6051	0.037*
H7	0.4029	0.8329	0.6382	0.041*
H8	0.1704	0.9059	0.5181	0.036*
H9	−0.049	0.974	0.320	0.06*
H10	1.0000	0.5000	0.5000	0.04 (4)*
H11	−0.2838	1.0246	0.1996	0.070*
H12	−0.1628	1.1796	0.2386	0.070*
H13	0.8849	0.4525	0.2970	0.081*
H14	1.0599	0.4055	0.3000	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0542 (1)	0.0419 (1)	0.0193 (1)	0.01057 (9)	0.00348 (8)	0.00204 (7)
O1	0.063 (1)	0.0364 (9)	0.0312 (9)	0.0027 (8)	0.0052 (8)	0.0150 (7)
O2	0.057 (1)	0.0340 (8)	0.0283 (8)	0.0004 (8)	0.0045 (8)	0.0059 (7)
O3	0.076 (1)	0.0311 (9)	0.0314 (9)	−0.0001 (9)	−0.0014 (9)	0.0117 (7)
O4	0.106 (2)	0.041 (1)	0.0252 (9)	−0.003 (1)	−0.009 (1)	0.0095 (8)
O5	0.044 (1)	0.056 (1)	0.0333 (9)	0.0264 (8)	0.0085 (8)	0.0063 (8)
O6	0.0362 (9)	0.047 (1)	0.0343 (9)	0.0166 (8)	−0.0027 (7)	0.0079 (8)
O7	0.041 (1)	0.064 (1)	0.038 (1)	0.0278 (9)	0.0045 (8)	0.0153 (9)
O8	0.050 (1)	0.045 (1)	0.0263 (8)	0.0207 (8)	0.0026 (7)	0.0105 (7)
O9	0.057 (1)	0.058 (1)	0.064 (1)	0.015 (1)	−0.020 (1)	0.015 (1)
O10	0.086 (2)	0.069 (1)	0.043 (1)	0.032 (1)	0.017 (1)	0.003 (1)
N1	0.0270 (8)	0.0290 (8)	0.0199 (8)	0.0099 (7)	0.0043 (7)	0.0056 (7)
N2	0.0287 (8)	0.0221 (8)	0.0203 (8)	0.0041 (7)	0.0007 (7)	0.0040 (6)
C1	0.028 (1)	0.031 (1)	0.023 (1)	0.0074 (8)	0.0057 (8)	0.0066 (8)
C2	0.037 (1)	0.041 (1)	0.021 (1)	0.007 (1)	0.0024 (9)	0.0100 (9)
C3	0.040 (1)	0.042 (1)	0.020 (1)	0.005 (1)	−0.0006 (9)	0.0032 (9)
C4	0.037 (1)	0.033 (1)	0.026 (1)	0.0011 (9)	0.0010 (9)	0.0031 (9)
C5	0.028 (1)	0.030 (1)	0.0218 (9)	0.0078 (8)	0.0043 (8)	0.0062 (8)
C6	0.035 (1)	0.030 (1)	0.029 (1)	0.0096 (9)	0.0093 (9)	0.0082 (8)
C7	0.039 (1)	0.031 (1)	0.025 (1)	0.0106 (9)	0.0057 (9)	0.0074 (8)
C8	0.029 (1)	0.0222 (9)	0.0222 (9)	0.0018 (8)	−0.0006 (8)	0.0040 (7)
C9	0.037 (1)	0.032 (1)	0.021 (1)	0.0087 (9)	−0.0004 (9)	0.0062 (8)
C10	0.045 (1)	0.036 (1)	0.022 (1)	0.009 (1)	0.0077 (9)	0.0052 (8)
C11	0.033 (1)	0.030 (1)	0.029 (1)	0.0083 (9)	0.0090 (9)	0.0042 (8)
C12	0.029 (1)	0.0230 (9)	0.0226 (9)	0.0028 (8)	0.0013 (8)	0.0048 (7)
C13	0.029 (1)	0.025 (1)	0.032 (1)	0.0053 (8)	0.0008 (9)	0.0046 (8)
C14	0.029 (1)	0.0237 (9)	0.026 (1)	0.0044 (8)	−0.0018 (8)	0.0036 (8)

Geometric parameters (Å, º)

Ag1—N1	2.326 (2)	N2—C8	1.337 (3)
Ag1—N2	2.326 (2)	N2—C12	1.344 (3)
Ag1—O2	2.504 (2)	C1—C2	1.388 (3)
Ag1—O4	2.768 (2)	C1—C6	1.521 (3)
Ag1—O5	2.507 (2)	C2—C3	1.384 (3)
Ag1—O8	2.765 (2)	C2—H1	0.9301
O1—C6	1.277 (3)	C3—C4	1.383 (3)
O1—H5	1.2268	C3—H2	0.9299
O2—C6	1.225 (3)	C4—C5	1.387 (3)
O3—C7	1.314 (3)	C4—H3	0.9300
O3—H4	0.80	C5—C7	1.501 (3)
O4—C7	1.197 (3)	C8—C9	1.387 (3)
O5—C13	1.226 (3)	C8—C13	1.519 (3)
O6—C13	1.278 (3)	C9—C10	1.375 (4)
O6—H10	1.2404	C9—H6	0.9300
O7—C14	1.297 (3)	C10—C11	1.380 (3)
O7—H9	0.80	C10—H7	0.9300
O8—C14	1.212 (3)	C11—C12	1.392 (3)
O9—H11	0.7953	C11—H8	0.9300
O9—H12	0.8907	C12—C14	1.505 (3)
O10—H13	0.8618	H5—O1^i	1.227
O10—H14	0.7310	H9—O7	0.80
N1—C1	1.336 (3)	H10—O6^ii	1.240
N1—C5	1.343 (3)
O2—Ag1—O5	120.32 (7)	C4—C3—C2	118.8 (2)
N1—Ag1—N2	155.06 (6)	C4—C3—H2	120.5777
O2—Ag1—N1	69.24 (7)	H2—C3—C2	120.5777
O4—Ag1—N1	64.95 (7)	C5—C4—H3	120.8831
O5—Ag1—N2	68.78 (8)	C5—C4—C3	118.2 (2)
O8—Ag1—N2	64.64 (7)	H3—C4—C3	120.8814
C6—O1—H5	115.32	C7—C5—N1	116.1 (2)
C7—O3—H4	108	C7—C5—C4	120.3 (2)
C13—O6—H10	118.02	C9—C8—N2	122.8 (2)
C14—O7—H9	111	C9—C8—C13	120.5 (2)
H11—O9—H12	112.2763	C13—C8—N2	116.8 (2)
H13—O10—H14	110.9626	C10—C9—C8	119.4 (2)
C1—N1—Ag1	117.8 (1)	C10—C9—H6	120.2944
C1—N1—C5	117.6 (2)	H6—C9—C8	120.2811
C5—N1—Ag1	124.3 (1)	C11—C10—C9	118.9 (2)
C8—N2—Ag1	118.7 (1)	C11—C10—H7	120.5445
C8—N2—C12	117.2 (2)	H7—C10—C9	120.5441
C12—N2—Ag1	123.7 (1)	C12—C11—H8	120.8790
C2—C1—N1	122.7 (2)	C12—C11—C10	118.2 (2)
C2—C1—C6	120.0 (2)	H8—C11—C10	120.8889
C6—C1—N1	117.2 (2)	C14—C12—N2	116.1 (2)
C3—C2—C1	119.1 (2)	C14—C12—C11	120.4 (2)
C3—C2—H1	120.4546	O1^i—H5—O1	180.0 (2)
H1—C2—C1	120.4469	O6^ii—H10—O6	180.0 (2)
N2—Ag1—N1—C1	114.4 (2)	N1—C5—C7—O4	−0.5 (4)
N1—Ag1—N2—C8	125.4 (1)	C4—C5—C7—O3	−3.7 (3)
Ag1—N1—C1—C2	−173.1 (2)	C4—C5—C7—O4	177.8 (3)
Ag1—N1—C5—C4	173.1 (2)	N2—C8—C9—C10	0.9 (3)
Ag1—N2—C8—C9	−172.2 (2)	N2—C8—C13—O5	0.4 (3)
Ag1—N2—C12—C11	170.3 (2)	N2—C8—C13—O6	−179.8 (2)
N1—C1—C2—C3	−0.2 (4)	C8—C9—C10—C11	−1.3 (3)
N1—C1—C6—O1	178.7 (2)	C9—C10—C11—C12	−0.1 (3)
N1—C1—C6—O2	0.8 (4)	C10—C11—C12—N2	2.1 (3)
C1—C2—C3—C4	−0.8 (4)	N2—C12—C14—O7	176.7 (2)
C2—C3—C4—C5	1.1 (4)	N2—C12—C14—O8	−6.1 (3)
C3—C4—C5—N1	−0.6 (4)	C11—C12—C14—O7	−7.0 (3)
N1—C5—C7—O3	177.9 (2)	C11—C12—C14—O8	170.2 (2)

Symmetry codes: (i) −x+1, −y+2, −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
O1—H5···O1^i	1.23	1.23	2.454 (4)	180
O6—H10···O6^ii	1.24	1.24	2.482 (3)	180
O7—H9···O9	0.80	1.71	2.501 (3)	167
O10—H13···O5	0.86	1.86	2.713 (4)	170
O3—H4···O8^iii	0.80	1.95	2.734 (3)	165
O9—H11···O2^iv	0.80	1.97	2.706 (3)	153
O9—H12···O10^v	0.89	1.89	2.749 (4)	161
O10—H14···O4^vi	0.73	2.65	3.084 (5)	120

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