Crystal structure of catena-poly[silver(I)-μ-L-valinato-κ²N:O]

The reaction of Ag₂O with L-valine in a 1:2 molar ratio in water, followed by vapour diffusion, afforded polymeric N—Ag—O repeated units of the title silver(I) complex. It shows a weak Ag...Ag inter­action and hydrogen bonds between amino groups and carboxyl­ates.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.022
• wR factor = 0.054
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         80 %
PLAT976_ALERT_2_C Check Calcd Residual Density  1.05A From      O1      -0.41 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          2 Report
PLAT791_ALERT_4_G The Model has Chirality at C2      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C7      (Chiral SPGR)          S Verify
PLAT804_ALERT_5_G Number of ARU-Code Packing Problem(s) in PLATON           2 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015).

catena-Poly[silver(I)-µ-L-valinato-κ²N:O]

Crystal data

[Ag(C5H10NO2)]	F(000) = 440
Mr = 224.01	Dx = 2.196 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.4475 (5) Å	Cell parameters from 4323 reflections
b = 22.545 (2) Å	θ = 3.6–28.3°
c = 5.5411 (5) Å	µ = 2.90 mm^−1
β = 95.446 (2)°	T = 90 K
V = 677.47 (11) Å^3	Needle, colorless
Z = 4	0.36 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3034 independent reflections
Radiation source: Sealed Tube	3013 reflections with I > 2σ(I)
Detector resolution: 8.366 pixels mm^-1	Rint = 0.016
ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→3
Tmin = 0.422, Tmax = 0.780	k = −28→30
4981 measured reflections	l = −7→7

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0258P)^2 + 0.4276P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.022	(Δ/σ)max = 0.001
wR(F^2) = 0.054	Δρmax = 1.13 e Å^−3
S = 1.15	Δρmin = −1.11 e Å^−3
3034 reflections	Absolute structure: Flack x determined using 1275 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
179 parameters	Absolute structure parameter: 0.048 (19)
7 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Ag1	0.62135 (6)	0.72712 (2)	0.36519 (6)	0.01288 (9)
C1	1.1756 (9)	0.7379 (2)	1.0188 (9)	0.0097 (10)
C2	1.0368 (9)	0.7590 (2)	0.7813 (9)	0.0112 (9)
H2C	1.149003	0.755936	0.649045	0.013*
C3	0.9626 (9)	0.8245 (2)	0.8085 (10)	0.0146 (10)
H3	0.837026	0.826310	0.928715	0.018*
C4	0.8460 (11)	0.8514 (3)	0.5695 (11)	0.0244 (12)
H4A	0.962402	0.848370	0.445617	0.037*
H4B	0.806760	0.893266	0.594925	0.037*
H4C	0.694559	0.829836	0.515562	0.037*
C5	1.1823 (11)	0.8626 (3)	0.9056 (12)	0.0236 (12)
H5A	1.309746	0.861056	0.792249	0.035*
H5B	1.249657	0.847404	1.063895	0.035*
H5C	1.128339	0.903713	0.922864	0.035*
O1	1.0588 (6)	0.7234 (2)	1.1919 (6)	0.0166 (7)
O2	1.4109 (6)	0.73698 (16)	1.0246 (6)	0.0125 (7)
N1	0.8165 (8)	0.7214 (2)	0.7175 (7)	0.0115 (8)
H1A	0.721 (9)	0.726 (3)	0.830 (8)	0.014*
H1B	0.877 (10)	0.6856 (15)	0.732 (11)	0.014*
Ag2	0.89815 (6)	0.60339 (2)	0.21275 (6)	0.01329 (10)
C6	1.2547 (9)	0.5896 (2)	0.6450 (10)	0.0107 (9)
C7	1.5054 (9)	0.5750 (2)	0.7793 (9)	0.0102 (9)
H7	1.635708	0.590634	0.680772	0.012*
C8	1.5466 (9)	0.5077 (2)	0.8113 (9)	0.0120 (9)
H8	1.686570	0.502380	0.939835	0.014*
C9	1.6241 (10)	0.4791 (3)	0.5799 (10)	0.0185 (10)
H9A	1.487275	0.481332	0.451923	0.028*
H9B	1.667499	0.437482	0.611812	0.028*
H9C	1.767197	0.500216	0.527632	0.028*
C10	1.3225 (10)	0.4764 (2)	0.8998 (10)	0.0168 (10)
H10A	1.365825	0.435354	0.943053	0.025*
H10B	1.186513	0.476776	0.770720	0.025*
H10C	1.271796	0.497164	1.042428	0.025*
N2	1.5353 (7)	0.6050 (2)	1.0205 (7)	0.0118 (7)
H2A	1.442 (10)	0.587 (2)	1.112 (10)	0.014*
H2B	1.494 (11)	0.6423 (13)	1.004 (11)	0.014*
O3	1.2360 (7)	0.57934 (18)	0.4188 (7)	0.0154 (8)
O4	1.0857 (6)	0.61000 (18)	0.7610 (6)	0.0140 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.00939 (17)	0.01968 (19)	0.00880 (17)	0.00032 (14)	−0.00310 (11)	−0.00117 (15)
C1	0.010 (2)	0.012 (3)	0.007 (2)	−0.0023 (17)	−0.0027 (17)	−0.0017 (17)
C2	0.008 (2)	0.017 (3)	0.008 (2)	−0.0015 (18)	−0.0004 (17)	−0.0040 (18)
C3	0.013 (2)	0.015 (2)	0.016 (2)	−0.0009 (18)	−0.0019 (19)	−0.0001 (19)
C4	0.031 (3)	0.020 (3)	0.020 (3)	0.006 (3)	−0.012 (2)	0.004 (2)
C5	0.024 (3)	0.016 (3)	0.029 (3)	−0.003 (2)	−0.006 (2)	−0.002 (2)
O1	0.0121 (16)	0.027 (2)	0.0102 (16)	−0.0014 (16)	−0.0009 (12)	0.0029 (17)
O2	0.0035 (14)	0.021 (2)	0.0123 (16)	0.0017 (12)	−0.0014 (12)	−0.0017 (14)
N1	0.0099 (18)	0.014 (2)	0.0104 (18)	−0.0014 (16)	0.0010 (14)	−0.0020 (17)
Ag2	0.00789 (17)	0.0215 (2)	0.00975 (18)	0.00137 (14)	−0.00313 (12)	−0.00090 (15)
C6	0.009 (2)	0.008 (2)	0.015 (2)	−0.0007 (16)	−0.0017 (18)	0.0003 (16)
C7	0.010 (2)	0.012 (2)	0.008 (2)	0.0006 (17)	0.0005 (17)	−0.0026 (17)
C8	0.008 (2)	0.017 (2)	0.011 (2)	−0.0003 (18)	−0.0017 (17)	−0.0003 (18)
C9	0.019 (3)	0.019 (3)	0.017 (2)	0.007 (2)	0.000 (2)	−0.004 (2)
C10	0.014 (2)	0.018 (2)	0.019 (3)	−0.002 (2)	0.002 (2)	0.004 (2)
N2	0.0130 (19)	0.0164 (19)	0.0054 (18)	0.0006 (18)	−0.0028 (14)	0.0000 (18)
O3	0.0088 (16)	0.027 (2)	0.0099 (17)	0.0028 (14)	−0.0009 (13)	0.0020 (15)
O4	0.0092 (15)	0.0187 (19)	0.0142 (18)	0.0034 (14)	0.0006 (13)	−0.0009 (15)

Geometric parameters (Å, º)

Ag1—N1	2.136 (4)	Ag2—O3	2.142 (4)
Ag1—O2^i	2.124 (3)	Ag2—N2^i	2.155 (4)
C1—O1	1.245 (6)	C6—O4	1.259 (6)
C1—O2	1.280 (6)	C6—O3	1.269 (7)
C1—C2	1.530 (7)	C6—C7	1.527 (7)
C2—N1	1.485 (6)	C7—N2	1.493 (6)
C2—C3	1.543 (7)	C7—C8	1.541 (7)
C2—H2C	1.0000	C7—H7	1.0000
C3—C5	1.528 (8)	C8—C10	1.530 (7)
C3—C4	1.538 (7)	C8—C9	1.530 (7)
C3—H3	1.0000	C8—H8	1.0000
C4—H4A	0.9800	C9—H9A	0.9800
C4—H4B	0.9800	C9—H9B	0.9800
C4—H4C	0.9800	C9—H9C	0.9800
C5—H5A	0.9800	C10—H10A	0.9800
C5—H5B	0.9800	C10—H10B	0.9800
C5—H5C	0.9800	C10—H10C	0.9800
N1—H1A	0.86 (3)	N2—H2A	0.86 (3)
N1—H1B	0.87 (3)	N2—H2B	0.87 (3)
O2^i—Ag1—N1	176.13 (16)	O3—Ag2—N2^i	165.79 (18)
O1—C1—O2	124.1 (5)	O4—C6—O3	125.2 (5)
O1—C1—C2	119.9 (4)	O4—C6—C7	119.5 (5)
O2—C1—C2	116.0 (4)	O3—C6—C7	115.2 (4)
N1—C2—C1	110.4 (4)	N2—C7—C6	110.8 (4)
N1—C2—C3	110.9 (4)	N2—C7—C8	109.9 (4)
C1—C2—C3	109.1 (4)	C6—C7—C8	112.4 (4)
N1—C2—H2C	108.8	N2—C7—H7	107.8
C1—C2—H2C	108.8	C6—C7—H7	107.8
C3—C2—H2C	108.8	C8—C7—H7	107.8
C5—C3—C4	109.1 (5)	C10—C8—C9	111.5 (4)
C5—C3—C2	111.6 (4)	C10—C8—C7	112.2 (4)
C4—C3—C2	112.6 (5)	C9—C8—C7	111.5 (4)
C5—C3—H3	107.8	C10—C8—H8	107.1
C4—C3—H3	107.8	C9—C8—H8	107.1
C2—C3—H3	107.8	C7—C8—H8	107.1
C3—C4—H4A	109.5	C8—C9—H9A	109.5
C3—C4—H4B	109.5	C8—C9—H9B	109.5
H4A—C4—H4B	109.5	H9A—C9—H9B	109.5
C3—C4—H4C	109.5	C8—C9—H9C	109.5
H4A—C4—H4C	109.5	H9A—C9—H9C	109.5
H4B—C4—H4C	109.5	H9B—C9—H9C	109.5
C3—C5—H5A	109.5	C8—C10—H10A	109.5
C3—C5—H5B	109.5	C8—C10—H10B	109.5
H5A—C5—H5B	109.5	H10A—C10—H10B	109.5
C3—C5—H5C	109.5	C8—C10—H10C	109.5
H5A—C5—H5C	109.5	H10A—C10—H10C	109.5
H5B—C5—H5C	109.5	H10B—C10—H10C	109.5
C2—N1—Ag1	120.3 (3)	C7—N2—H2A	107 (4)
C2—N1—H1A	107 (4)	C7—N2—H2B	110 (4)
C2—N1—H1B	102 (4)	H2A—N2—H2B	112 (5)
H1A—N1—H1B	108 (5)	C6—O3—Ag2	117.7 (3)

Symmetry code: (i) x−1, y, z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O4	0.87 (3)	2.04 (3)	2.907 (6)	169 (5)
N2—H2B···O2	0.87 (3)	2.19 (3)	3.053 (7)	171 (6)
N1—H1A···O2^ii	0.86 (3)	2.10 (3)	2.935 (5)	164 (6)
N2—H2A···O3^iii	0.86 (3)	2.13 (4)	2.924 (5)	153 (6)

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