Poly­[[silver(I)-μ-4,4′-bi­pyridine-μ-formato] monohydrate formic acid solvate]

The reaction of silver formate with HCO₂H and 4,4′-bi­pyridine in CH₃CN produced the title compound, [Ag(CHO₂)(C₁₀H₈N₂)]·H₂O·CH₂O₂. In the structure, each 4,4′-bi­pyridine moiety acts as a bidentate ligand that binds two Ag atoms, thus forming a linear chain. The formate ions bridge the adjacent chains through Ag—O bonds [Ag—O = 2.709 (6)–3.089 (5) Å] to form molecular ladders. The mol­ecular ladders are stacked into layers and are interconnected by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.010 Å
• H-atom completeness 93%
• R factor = 0.070
• wR factor = 0.136
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.12
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.18 Ratio

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C12 H13 Ag1 N2 O5
            Atom count from the _atom_site data:  C12 H12 Ag1 N2 O5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C12 H13 Ag N2 O5
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         96.00     96.00    0.00
           H        104.00     96.00    8.00
           Ag         8.00      8.00    0.00
           N         16.00     16.00    0.00
           O         40.00     40.00    0.00

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Poly[[silver(I)-µ-4,4'-bipyridine-µ-formato] monohydrate formic acid solvate]

Crystal data

[Ag(CHO2)(C10H8N2)]·H2O·CH2O2	F(000) = 1488
Mr = 373.11	Dx = 1.834 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3186 reflections
a = 17.848 (4) Å	θ = 3.1–27.5°
b = 16.863 (3) Å	µ = 1.51 mm^−1
c = 9.485 (3) Å	T = 193 K
β = 108.79 (1)°	Prism, colorless
V = 2702.6 (12) Å^3	0.35 × 0.18 × 0.06 mm
Z = 8

Data collection

Rigaku Mercury area-detector diffractometer	2365 independent reflections
Radiation source: fine-focus sealed tube	2176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 7.31 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −21→21
Absorption correction: multi-scan (Blessing, 1995; Jacobson, 1998)	k = −16→20
Tmin = 0.784, Tmax = 0.915	l = −11→9
8855 measured reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.37	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 20.891P] where P = (Fo^2 + 2Fc^2)/3
2365 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 1.12 e Å^−3
39 restraints	Δρmin = −0.53 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.18428 (3)	0.23482 (4)	0.34366 (6)	0.0281 (2)
O1	0.1681 (3)	0.0766 (3)	0.2943 (6)	0.0387 (14)
O2	0.2576 (3)	0.1026 (3)	0.5123 (6)	0.0329 (13)
N1	0.0828 (3)	0.2475 (3)	0.4202 (6)	0.0214 (13)
N2	−0.2263 (3)	0.2588 (4)	0.7344 (6)	0.0226 (13)
C1	0.0391 (4)	0.1832 (4)	0.4219 (8)	0.0212 (15)
H1	0.0526	0.1344	0.3858	0.025*
C2	−0.0243 (4)	0.1848 (4)	0.4733 (8)	0.0212 (15)
H2	−0.0550	0.1383	0.4681	0.025*
C3	−0.0443 (4)	0.2544 (4)	0.5335 (7)	0.0195 (15)
C4	0.0008 (4)	0.3216 (4)	0.5279 (8)	0.0219 (15)
H4	−0.0114	0.3714	0.5622	0.026*
C5	0.0629 (4)	0.3151 (4)	0.4724 (8)	0.0221 (15)
H5	0.0933	0.3613	0.4711	0.027*
C6	−0.1815 (4)	0.1934 (4)	0.7412 (8)	0.0235 (15)
H6	−0.1907	0.1480	0.7926	0.028*
C7	−0.1228 (4)	0.1905 (4)	0.6759 (7)	0.0211 (15)
H7	−0.0919	0.1439	0.6837	0.025*
C8	−0.1088 (4)	0.2559 (4)	0.5988 (7)	0.0180 (15)
C9	−0.1556 (4)	0.3230 (4)	0.5915 (8)	0.0225 (16)
H9	−0.1482	0.3691	0.5399	0.027*
C10	−0.2126 (4)	0.3213 (4)	0.6600 (8)	0.0236 (16)
H10	−0.2441	0.3673	0.6542	0.028*
C11	0.2153 (5)	0.0565 (5)	0.4153 (10)	0.0321 (19)
H11	0.2201	0.0014	0.4370	0.038*
C12	0.4024 (15)	0.019 (2)	0.793 (4)	0.039 (8)	0.502 (15)
H12	0.4299	0.0022	0.8921	0.047*	0.502 (15)
O3	0.3426 (11)	0.0636 (14)	0.778 (3)	0.034 (5)	0.502 (15)
H3O	0.3206	0.0739	0.6875	0.041*	0.502 (15)
O4	0.4284 (7)	−0.0052 (8)	0.6994 (15)	0.051 (4)	0.502 (15)
C12'	0.3858 (17)	0.0173 (19)	0.813 (3)	0.031 (6)	0.498 (15)
H12'	0.4090	0.0026	0.7395	0.037*	0.498 (15)
O3'	0.3210 (13)	0.0558 (16)	0.776 (4)	0.049 (7)	0.498 (15)
H3O'	0.3063	0.0653	0.6840	0.058*	0.498 (15)
O4'	0.4172 (7)	−0.0003 (7)	0.9406 (12)	0.039 (4)	0.498 (15)
O1W	0.0412 (4)	−0.0173 (3)	0.1491 (7)	0.060 (2)
H1W1	0.0819	0.0100	0.1802	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0228 (3)	0.0355 (4)	0.0326 (4)	0.0005 (3)	0.0180 (2)	−0.0015 (3)
O1	0.031 (3)	0.041 (4)	0.043 (3)	0.000 (3)	0.011 (3)	0.007 (3)
O2	0.029 (3)	0.035 (3)	0.030 (3)	0.001 (2)	0.002 (2)	−0.001 (2)
N1	0.016 (3)	0.027 (4)	0.023 (3)	0.001 (2)	0.009 (2)	−0.001 (2)
N2	0.018 (3)	0.031 (4)	0.020 (3)	−0.005 (3)	0.007 (2)	0.002 (3)
C1	0.021 (4)	0.017 (4)	0.027 (4)	0.001 (3)	0.010 (3)	−0.001 (3)
C2	0.017 (3)	0.023 (4)	0.025 (4)	−0.005 (3)	0.010 (3)	−0.003 (3)
C3	0.016 (3)	0.028 (4)	0.015 (3)	0.003 (3)	0.005 (3)	0.006 (3)
C4	0.021 (3)	0.016 (4)	0.029 (4)	0.004 (3)	0.008 (3)	−0.001 (3)
C5	0.019 (3)	0.017 (4)	0.031 (4)	−0.007 (3)	0.009 (3)	0.000 (3)
C6	0.026 (4)	0.024 (4)	0.022 (4)	0.000 (3)	0.010 (3)	0.005 (3)
C7	0.023 (3)	0.020 (4)	0.022 (4)	0.001 (3)	0.008 (3)	0.003 (3)
C8	0.013 (3)	0.025 (4)	0.015 (3)	0.003 (3)	0.003 (3)	0.000 (3)
C9	0.024 (4)	0.021 (4)	0.028 (4)	0.002 (3)	0.015 (3)	0.007 (3)
C10	0.020 (4)	0.028 (4)	0.024 (4)	0.008 (3)	0.009 (3)	0.002 (3)
C11	0.032 (4)	0.024 (4)	0.048 (5)	0.004 (3)	0.022 (4)	0.002 (4)
C12	0.045 (11)	0.030 (10)	0.038 (11)	−0.006 (8)	0.009 (8)	−0.004 (7)
O3	0.034 (8)	0.049 (8)	0.022 (7)	0.002 (7)	0.014 (7)	−0.003 (6)
O4	0.050 (7)	0.053 (7)	0.048 (7)	0.006 (5)	0.015 (5)	−0.009 (5)
C12'	0.038 (10)	0.024 (9)	0.030 (10)	−0.004 (8)	0.010 (8)	−0.002 (7)
O3'	0.043 (10)	0.065 (10)	0.042 (8)	−0.003 (7)	0.019 (8)	0.008 (6)
O4'	0.041 (6)	0.038 (6)	0.031 (6)	−0.005 (5)	0.000 (5)	0.003 (5)
O1W	0.062 (4)	0.031 (4)	0.062 (4)	−0.006 (3)	−0.017 (4)	−0.005 (3)

Geometric parameters (Å, º)

Ag1—N2^i	2.167 (6)	C4—H4	0.95
Ag1—N1	2.167 (5)	C5—H5	0.95
Ag1—O1	2.709 (6)	C6—C7	1.379 (9)
Ag1—O2	2.809 (5)	C6—H6	0.95
Ag1—O2^ii	3.089 (5)	C7—C8	1.389 (9)
Ag1—Ag1^ii	3.1748 (14)	C7—H7	0.95
O1—C11	1.232 (10)	C8—C9	1.395 (9)
O2—C11	1.255 (10)	C9—C10	1.373 (9)
N1—C5	1.336 (9)	C9—H9	0.95
N1—C1	1.340 (8)	C10—H10	0.95
N2—C10	1.334 (9)	C11—H11	0.95
N2—C6	1.352 (9)	C12—O4	1.20 (3)
N2—Ag1^iii	2.167 (6)	C12—O3	1.278 (16)
C1—C2	1.369 (9)	C12—H12	0.95
C1—H1	0.95	O3—H3O	0.84
C2—C3	1.400 (10)	C12'—O4'	1.20 (3)
C2—H2	0.95	C12'—O3'	1.274 (16)
C3—C4	1.402 (9)	C12'—H12'	0.95
C3—C8	1.472 (9)	O3'—H3O'	0.84
C4—C5	1.376 (9)	O1W—H1W1	0.83
N2^i—Ag1—N1	168.1 (2)	C5—C4—C3	119.6 (6)
N2^i—Ag1—O1	91.2 (2)	C5—C4—H4	120.2
N1—Ag1—O1	95.83 (19)	C3—C4—H4	120.2
N2^i—Ag1—O2	91.83 (19)	N1—C5—C4	123.6 (6)
N1—Ag1—O2	100.03 (18)	N1—C5—H5	118.2
O1—Ag1—O2	47.21 (16)	C4—C5—H5	118.2
N2^i—Ag1—O2^ii	88.47 (18)	N2—C6—C7	122.0 (6)
N1—Ag1—O2^ii	87.80 (18)	N2—C6—H6	119.0
O1—Ag1—O2^ii	162.27 (16)	C7—C6—H6	119.0
O2—Ag1—O2^ii	115.08 (12)	C6—C7—C8	120.0 (6)
N2^i—Ag1—Ag1^ii	90.13 (15)	C6—C7—H7	120.0
N1—Ag1—Ag1^ii	96.70 (15)	C8—C7—H7	120.0
O1—Ag1—Ag1^ii	109.01 (13)	C7—C8—C9	117.6 (6)
O2—Ag1—Ag1^ii	61.80 (11)	C7—C8—C3	120.4 (6)
O2^ii—Ag1—Ag1^ii	53.28 (10)	C9—C8—C3	122.0 (6)
C11—O1—Ag1	96.1 (5)	C10—C9—C8	118.8 (6)
C11—O2—Ag1	90.8 (5)	C10—C9—H9	120.6
C5—N1—C1	117.5 (6)	C8—C9—H9	120.6
C5—N1—Ag1	124.0 (4)	N2—C10—C9	123.9 (6)
C1—N1—Ag1	118.5 (4)	N2—C10—H10	118.0
C10—N2—C6	117.6 (6)	C9—C10—H10	118.0
C10—N2—Ag1^iii	120.2 (5)	O1—C11—O2	125.6 (8)
C6—N2—Ag1^iii	122.2 (5)	O1—C11—H11	117.2
N1—C1—C2	122.6 (6)	O2—C11—H11	117.2
N1—C1—H1	118.7	O4—C12—O3	129 (3)
C2—C1—H1	118.7	O4—C12—H12	115.6
C1—C2—C3	120.8 (6)	O3—C12—H12	115.6
C1—C2—H2	119.6	C12—O3—H3O	109.5
C3—C2—H2	119.6	O4'—C12'—O3'	120 (3)
C2—C3—C4	115.9 (6)	O4'—C12'—H12'	120.2
C2—C3—C8	121.5 (6)	O3'—C12'—H12'	120.2
C4—C3—C8	122.6 (6)	C12'—O3'—H3O'	109.5
N2^i—Ag1—O1—C11	94.0 (5)	C1—C2—C3—C4	4.1 (10)
N1—Ag1—O1—C11	−95.7 (5)	C1—C2—C3—C8	−175.7 (6)
O2—Ag1—O1—C11	2.6 (4)	C2—C3—C4—C5	−3.2 (10)
O2^ii—Ag1—O1—C11	5.4 (8)	C8—C3—C4—C5	176.6 (6)
Ag1^ii—Ag1—O1—C11	3.5 (5)	C1—N1—C5—C4	0.5 (10)
N2^i—Ag1—O2—C11	−92.4 (4)	Ag1—N1—C5—C4	−176.5 (5)
N1—Ag1—O2—C11	86.2 (4)	C3—C4—C5—N1	1.0 (11)
O1—Ag1—O2—C11	−2.5 (4)	C10—N2—C6—C7	0.8 (10)
O2^ii—Ag1—O2—C11	178.4 (5)	Ag1^iii—N2—C6—C7	−177.7 (5)
Ag1^ii—Ag1—O2—C11	178.4 (5)	N2—C6—C7—C8	−0.7 (10)
N2^i—Ag1—N1—C5	−59.2 (12)	C6—C7—C8—C9	0.3 (10)
O1—Ag1—N1—C5	175.3 (5)	C6—C7—C8—C3	177.8 (6)
O2—Ag1—N1—C5	127.8 (5)	C2—C3—C8—C7	35.2 (10)
O2^ii—Ag1—N1—C5	12.7 (5)	C4—C3—C8—C7	−144.6 (7)
Ag1^ii—Ag1—N1—C5	65.3 (5)	C2—C3—C8—C9	−147.5 (7)
N2^i—Ag1—N1—C1	123.8 (10)	C4—C3—C8—C9	32.7 (10)
O1—Ag1—N1—C1	−1.7 (5)	C7—C8—C9—C10	0.0 (10)
O2—Ag1—N1—C1	−49.2 (5)	C3—C8—C9—C10	−177.4 (6)
O2^ii—Ag1—N1—C1	−164.3 (5)	C6—N2—C10—C9	−0.4 (10)
Ag1^ii—Ag1—N1—C1	−111.7 (5)	Ag1^iii—N2—C10—C9	178.0 (5)
C5—N1—C1—C2	0.4 (10)	C8—C9—C10—N2	0.1 (11)
Ag1—N1—C1—C2	177.6 (5)	Ag1—O1—C11—O2	−5.2 (8)
N1—C1—C2—C3	−2.8 (11)	Ag1—O2—C11—O1	5.0 (8)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2	0.84	1.75	2.57 (2)	167
O3′—H3O′···O2	0.84	1.70	2.52 (3)	163
O1W—H1W1···O1	0.83	1.93	2.74 (1)	166