catena-Poly[[aqua-1κO-μ2-succinimidato-1:2κ2O:N-disilver(I)]-μ3-succinimidato-1:2:1′κ3O:N:O′]

Whitcomb, D.R.; Rajeswaran, M.

doi:10.1107/S1600536807013347

catena-Poly[[aqua-1κO-μ₂-succinimidato-1:2κ²O:N-disilver(I)]-μ₃-succinimidato-1:2:1′κ³O:N:O′]

The structure of the title compound, [Ag₂(C₄H₄NO₂)₂(H₂O)]_n, exhibits a butterfly-shaped [Ag(C₄H₄NO₂)]₂ dimer which contains an eight-membered ring. One of the Ag atoms is four-coordinate having exclusively Ag—O bonds and the other is two-coordinate having exclusively Ag—N bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013347/ci2304sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013347/ci2304Isup2.hkl Contains datablock I

CCDC reference: 642944

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
H-atom completeness 81%
R factor = 0.036
wR factor = 0.070
Data-to-parameter ratio = 16.0

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 ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.59
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05

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:   C8 H10 Ag2 N2 O5
            Atom count from _chemical_formula_moiety:C8 H9 Ag2 N2 O4
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:C8 H10 Ag2 N2 O5
            Atom count from the _atom_site data:  C8 H8 Ag2 N2 O5
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      0.593
            Tmax scaled      0.406 Tmin scaled      0.229
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    4
           From the CIF: _chemical_formula_sum  C8 H10 Ag2 N2 O5
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         32.00     32.00    0.00
           H         40.00     32.00    8.00
           Ag         8.00      8.00    0.00
           N          8.00      8.00    0.00
           O         20.00     20.00    0.00
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
   6 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and MaterialsStudio (Accelrys, 2002); software used to prepare material for publication: SHELXTL.

catena-Poly[[aqua-1κO-µ₂-succinimidato-1:2κ²O:N-disilver(I)]- µ₃-succinimidato-1:2:1'κ³O:N:O'] top

Crystal data top

[Ag₂(C₄H₄NO₂)₂(H₂O)]	F(000) = 824
M_r = 429.92	D_x = 2.620 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5112 reflections
a = 7.6776 (2) Å	θ = 1.0–27.5°
b = 8.0431 (2) Å	µ = 3.60 mm⁻¹
c = 17.8184 (5) Å	T = 293 K
β = 97.916 (1)°	Block, white
V = 1089.83 (5) Å³	0.37 × 0.37 × 0.25 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2481 independent reflections
Radiation source: fine-focus sealed tube	1653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 4.5°
φ scans	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing 1995)	k = −10→10
T_min = 0.386, T_max = 0.685	l = −19→23
10974 measured reflections

Refinement top

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0262P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max = 0.001
2481 reflections	Δρ_max = 0.69 e Å⁻³
155 parameters	Δρ_min = −0.80 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0185 (6)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.87381 (5)	−0.03959 (4)	0.921975 (19)	0.03061 (15)
Ag2	0.84483 (5)	0.29065 (5)	0.99945 (2)	0.04026 (16)
O1	0.7851 (6)	−0.4117 (4)	0.9834 (2)	0.0529 (11)
O2	0.6696 (5)	0.1070 (4)	1.06085 (18)	0.0415 (9)
O3	1.0294 (6)	−0.1202 (4)	0.75477 (18)	0.0579 (11)
O4	0.8721 (5)	0.3471 (4)	0.87045 (17)	0.0439 (9)
O5	0.9515 (6)	0.3477 (5)	1.1305 (2)	0.0623 (12)
N1	0.7557 (5)	−0.1366 (4)	1.01049 (18)	0.0266 (9)
N2	0.9383 (5)	0.0905 (4)	0.8278 (2)	0.0296 (9)
C1	0.7264 (7)	−0.3015 (6)	1.0210 (3)	0.0318 (11)
C2	0.6175 (7)	−0.3305 (6)	1.0832 (3)	0.0384 (13)
H2A	0.6805	−0.3977	1.1233	0.046*
H2B	0.5075	−0.3850	1.0642	0.046*
C3	0.5858 (6)	−0.1564 (6)	1.1110 (3)	0.0349 (12)
H3A	0.4610	−0.1331	1.1071	0.042*
H3B	0.6386	−0.1423	1.1633	0.042*
C4	0.6724 (6)	−0.0453 (6)	1.0594 (2)	0.0295 (11)
C5	0.9951 (7)	0.0267 (6)	0.7630 (3)	0.0363 (12)
C6	1.0046 (8)	0.1605 (6)	0.7052 (3)	0.0432 (14)
H6A	0.9190	0.1418	0.6607	0.052*
H6B	1.1210	0.1661	0.6900	0.052*
C7	0.9632 (8)	0.3171 (6)	0.7460 (3)	0.0440 (14)
H7A	0.8646	0.3756	0.7178	0.053*
H7B	1.0641	0.3908	0.7533	0.053*
C8	0.9177 (6)	0.2555 (6)	0.8211 (3)	0.0321 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0407 (3)	0.0267 (2)	0.0268 (2)	−0.00013 (16)	0.01290 (16)	0.00202 (14)
Ag2	0.0531 (3)	0.0291 (2)	0.0409 (3)	0.00130 (18)	0.01451 (19)	0.00364 (17)
O1	0.087 (3)	0.030 (2)	0.049 (2)	0.009 (2)	0.034 (2)	0.0077 (17)
O2	0.058 (3)	0.021 (2)	0.050 (2)	−0.0038 (18)	0.0245 (19)	−0.0015 (16)
O3	0.107 (4)	0.030 (2)	0.044 (2)	0.013 (2)	0.035 (2)	0.0011 (18)
O4	0.075 (3)	0.0278 (19)	0.0325 (19)	0.0019 (18)	0.0193 (18)	−0.0012 (16)
O5	0.085 (3)	0.050 (2)	0.051 (2)	−0.025 (2)	0.004 (2)	−0.0008 (19)
N1	0.033 (2)	0.024 (2)	0.024 (2)	−0.0041 (18)	0.0112 (17)	0.0001 (16)
N2	0.040 (3)	0.024 (2)	0.027 (2)	0.0007 (17)	0.0122 (18)	−0.0012 (16)
C1	0.038 (3)	0.032 (3)	0.027 (3)	0.006 (2)	0.008 (2)	0.003 (2)
C2	0.052 (3)	0.031 (3)	0.036 (3)	−0.008 (2)	0.018 (2)	0.003 (2)
C3	0.038 (3)	0.034 (3)	0.035 (3)	0.001 (2)	0.014 (2)	0.000 (2)
C4	0.031 (3)	0.033 (3)	0.024 (2)	−0.005 (2)	0.004 (2)	0.002 (2)
C5	0.048 (3)	0.037 (3)	0.024 (3)	−0.005 (3)	0.007 (2)	−0.002 (2)
C6	0.065 (4)	0.038 (3)	0.030 (3)	0.005 (3)	0.019 (3)	0.007 (2)
C7	0.064 (4)	0.034 (3)	0.036 (3)	0.002 (3)	0.014 (3)	0.006 (2)
C8	0.039 (3)	0.029 (3)	0.027 (3)	−0.005 (2)	0.002 (2)	0.002 (2)

Geometric parameters (Å, º) top

Ag1—N1	2.077 (3)	N2—C8	1.340 (5)
Ag1—N2	2.095 (3)	N2—C5	1.386 (6)
Ag1—Ag2ⁱ	3.1418 (5)	C1—C2	1.496 (6)
Ag1—Ag1ⁱ	3.2261 (7)	C2—C3	1.516 (6)
Ag2—O2	2.365 (3)	C2—H2A	0.97
Ag2—O4	2.380 (3)	C2—H2B	0.97
Ag2—O5	2.410 (4)	C3—C4	1.501 (6)
Ag2—O1ⁱⁱ	2.447 (3)	C3—H3A	0.97
Ag2—Ag1ⁱ	3.1418 (5)	C3—H3B	0.97
O1—C1	1.233 (5)	C5—C6	1.499 (6)
O1—Ag2ⁱⁱⁱ	2.447 (3)	C6—C7	1.509 (6)
O2—C4	1.226 (5)	C6—H6A	0.97
O3—C5	1.223 (5)	C6—H6B	0.97
O4—C8	1.234 (5)	C7—C8	1.513 (6)
N1—C1	1.362 (5)	C7—H7A	0.97
N1—C4	1.365 (6)	C7—H7B	0.97

N1—Ag1—N2	166.55 (15)	C1—C2—H2B	111.1
N1—Ag1—Ag2ⁱ	76.43 (10)	C3—C2—H2B	111.1
N2—Ag1—Ag2ⁱ	117.01 (11)	H2A—C2—H2B	109.1
N1—Ag1—Ag1ⁱ	72.11 (10)	C4—C3—C2	104.2 (4)
N2—Ag1—Ag1ⁱ	114.32 (11)	C4—C3—H3A	110.9
Ag2ⁱ—Ag1—Ag1ⁱ	56.517 (13)	C2—C3—H3A	110.9
O2—Ag2—O4	134.20 (12)	C4—C3—H3B	110.9
O2—Ag2—O5	79.03 (12)	C2—C3—H3B	110.9
O4—Ag2—O5	146.73 (13)	H3A—C3—H3B	108.9
O2—Ag2—O1ⁱⁱ	123.74 (12)	O2—C4—N1	124.2 (4)
O4—Ag2—O1ⁱⁱ	74.98 (11)	O2—C4—C3	124.9 (4)
O5—Ag2—O1ⁱⁱ	87.71 (13)	N1—C4—C3	110.9 (4)
O2—Ag2—Ag1ⁱ	78.02 (9)	O3—C5—N2	123.7 (4)
O4—Ag2—Ag1ⁱ	113.98 (9)	O3—C5—C6	125.4 (4)
O5—Ag2—Ag1ⁱ	64.51 (10)	N2—C5—C6	110.9 (4)
O1ⁱⁱ—Ag2—Ag1ⁱ	141.93 (11)	C5—C6—C7	103.6 (4)
C1—O1—Ag2ⁱⁱⁱ	135.8 (3)	C5—C6—H6A	111.0
C4—O2—Ag2	127.0 (3)	C7—C6—H6A	111.0
C8—O4—Ag2	130.2 (3)	C5—C6—H6B	111.0
C1—N1—C4	109.6 (4)	C7—C6—H6B	111.0
C1—N1—Ag1	124.6 (3)	H6A—C6—H6B	109.0
C4—N1—Ag1	125.1 (3)	C6—C7—C8	104.0 (4)
C8—N2—C5	109.9 (4)	C6—C7—H7A	111.0
C8—N2—Ag1	121.8 (3)	C8—C7—H7A	111.0
C5—N2—Ag1	128.2 (3)	C6—C7—H7B	111.0
O1—C1—N1	123.0 (4)	C8—C7—H7B	111.0
O1—C1—C2	125.0 (4)	H7A—C7—H7B	109.0
N1—C1—C2	112.0 (4)	O4—C8—N2	124.8 (4)
C1—C2—C3	103.2 (4)	O4—C8—C7	123.9 (4)
C1—C2—H2A	111.1	N2—C8—C7	111.3 (4)
C3—C2—H2A	111.1

O4—Ag2—O2—C4	63.8 (4)	O1—C1—C2—C3	178.5 (5)
O5—Ag2—O2—C4	−114.1 (4)	N1—C1—C2—C3	−0.9 (6)
O1ⁱⁱ—Ag2—O2—C4	166.1 (4)	C1—C2—C3—C4	2.6 (5)
Ag1ⁱ—Ag2—O2—C4	−48.2 (4)	Ag2—O2—C4—N1	−12.6 (7)
O2—Ag2—O4—C8	−61.9 (5)	Ag2—O2—C4—C3	167.2 (3)
O5—Ag2—O4—C8	114.3 (4)	C1—N1—C4—O2	−177.0 (4)
O1ⁱⁱ—Ag2—O4—C8	175.3 (5)	Ag1—N1—C4—O2	−6.3 (7)
Ag1ⁱ—Ag2—O4—C8	34.7 (4)	C1—N1—C4—C3	3.3 (5)
N2—Ag1—N1—C1	123.6 (6)	Ag1—N1—C4—C3	173.9 (3)
Ag2ⁱ—Ag1—N1—C1	−56.9 (3)	C2—C3—C4—O2	176.5 (5)
Ag1ⁱ—Ag1—N1—C1	−115.7 (4)	C2—C3—C4—N1	−3.7 (5)
N2—Ag1—N1—C4	−45.7 (8)	C8—N2—C5—O3	177.8 (5)
Ag2ⁱ—Ag1—N1—C4	133.8 (4)	Ag1—N2—C5—O3	−6.1 (8)
Ag1ⁱ—Ag1—N1—C4	75.0 (3)	C8—N2—C5—C6	−3.3 (6)
N1—Ag1—N2—C8	47.9 (8)	Ag1—N2—C5—C6	172.7 (3)
Ag2ⁱ—Ag1—N2—C8	−131.6 (3)	O3—C5—C6—C7	−175.9 (6)
Ag1ⁱ—Ag1—N2—C8	−68.2 (4)	N2—C5—C6—C7	5.3 (6)
N1—Ag1—N2—C5	−127.7 (6)	C5—C6—C7—C8	−4.9 (5)
Ag2ⁱ—Ag1—N2—C5	52.8 (4)	Ag2—O4—C8—N2	10.5 (7)
Ag1ⁱ—Ag1—N2—C5	116.1 (4)	Ag2—O4—C8—C7	−167.5 (4)
Ag2ⁱⁱⁱ—O1—C1—N1	159.0 (4)	C5—N2—C8—O4	−178.3 (5)
Ag2ⁱⁱⁱ—O1—C1—C2	−20.4 (9)	Ag1—N2—C8—O4	5.3 (7)
C4—N1—C1—O1	179.1 (5)	C5—N2—C8—C7	−0.1 (6)
Ag1—N1—C1—O1	8.4 (7)	Ag1—N2—C8—C7	−176.5 (3)
C4—N1—C1—C2	−1.4 (6)	C6—C7—C8—O4	−178.4 (5)
Ag1—N1—C1—C2	−172.2 (3)	C6—C7—C8—N2	3.4 (6)

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

Selected bond distances (Å) in Ag-imide complexes top

Bond/Compound	{[AgSI]₂.H₂O}_n	[AgBOD]₂	[AgBOD.(Ph₃P)₂]
Ag—N	2.077 (3)-2.095 (3)	2.147 (6)	2.225 (7)
Ag—O	2.365 (3)-2.447 (3)	2.170 (5)	2.964 (8)
Ag—Ag	3.1418 (5)-3.2261 (7)	2.8042 (12)	-

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