catena-Poly[silver(I)-μ-[1-(pyridin-2-ylmethyl-κN)-3-(3-sulfonato­prop­yl)imidazolin-2-yl­idene]-κC²]

The title compound, [Ag(C₁₂H₁₄N₃O₃S)]_n, was obtained by deprotonation and metalation of 1-(pyridin-2-ylmeth­yl)-3-(3-sulfoprop­yl)imidazolium, inner salt, using silver(I) oxide in methanol. The title compound is a one-dimensional helical coordination polymer. Several C—H...O hydrogen bonds and a short Ag—O contact are observed. The C—Ag—N angle is 168.3 (1)° and the N—C—N `carbene angle' is 103.8 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.032
• wR factor = 0.066
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C12 H14 Ag N3 O3 S
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6 Report

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT008_ALERT_5_G No _iucr_refine_reflections_details   in the CIF     Please Do !
PLAT069_ALERT_1_G Atom Label without Numerical Part ..............         Ag Do !
PLAT069_ALERT_1_G Atom Label without Numerical Part ..............          S Do !
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List out of Sequence ..         C8 Note
PLAT797_ALERT_4_G N-Atom in CIF Coordinate List out of Sequence ..         N2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
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
   9 ALERT level G = General information/check it is not something unexpected

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006).

catena-Poly[silver(I)-µ-[1-(pyridin-2-ylmethyl-κN)-3-(3-sulfonatopropyl)imidazolin-2-ylidene]-κC²]

Crystal data

[Ag(C12H14N3O3S)]	F(000) = 776
Mr = 388.19	Dx = 1.965 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2698 reflections
a = 11.1568 (6) Å	θ = 3.6–27.2°
b = 9.7852 (4) Å	µ = 1.71 mm^−1
c = 12.5715 (6) Å	T = 173 K
β = 107.055 (10)°	Fragment, colourless
V = 1312.09 (12) Å^3	0.15 × 0.04 × 0.03 mm
Z = 4

Data collection

Agilent Xcalibur Ruby Gemini ultra diffractometer	2398 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1921 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.3575 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→10
Tmin = 0.936, Tmax = 1	l = −11→15
8214 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0243P)^2 + 0.580P] where P = (Fo^2 + 2Fc^2)/3
2398 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Ag	0.14608 (3)	0.10604 (3)	0.58234 (2)	0.02486 (11)
S	−0.03575 (9)	0.10338 (8)	0.17887 (8)	0.0211 (2)
N3	0.4721 (3)	−0.2244 (3)	0.9083 (2)	0.0166 (7)
C5	0.1801 (4)	−0.0473 (3)	0.2667 (3)	0.0206 (8)
H5A	0.1213	−0.1022	0.2948	0.025*
H5B	0.2375	−0.1113	0.245	0.025*
N2	0.3417 (3)	−0.1303 (3)	0.6187 (2)	0.0180 (7)
O1	0.0012 (3)	0.2093 (3)	0.2626 (2)	0.0376 (8)
O2	−0.1035 (3)	0.1553 (3)	0.0696 (2)	0.0340 (7)
C11	0.6205 (4)	0.0030 (4)	0.9122 (3)	0.0251 (9)
H11	0.6711	0.0815	0.9136	0.03*
C8	0.4460 (3)	−0.1385 (3)	0.8205 (3)	0.0162 (8)
N1	0.3119 (3)	−0.0352 (3)	0.4606 (2)	0.0189 (7)
C1	0.2724 (4)	−0.0316 (3)	0.5520 (3)	0.0181 (8)
O3	−0.0995 (3)	−0.0096 (2)	0.2142 (2)	0.0279 (6)
C3	0.4222 (3)	−0.1927 (3)	0.5684 (3)	0.0210 (9)
H3	0.4797	−0.2642	0.5987	0.025*
C2	0.4038 (4)	−0.1338 (3)	0.4695 (3)	0.0200 (8)
H2	0.4455	−0.1549	0.4156	0.024*
C10	0.6490 (4)	−0.0863 (3)	1.0009 (3)	0.0217 (8)
H10	0.7202	−0.0721	1.0636	0.026*
C6	0.1058 (4)	0.0317 (3)	0.1644 (3)	0.0210 (8)
H6A	0.085	−0.0302	0.0993	0.025*
H6B	0.1589	0.1063	0.1498	0.025*
C7	0.3302 (4)	−0.1690 (3)	0.7271 (3)	0.0195 (8)
H7A	0.3121	−0.2681	0.7269	0.023*
H7B	0.2584	−0.1195	0.7402	0.023*
C9	0.5710 (4)	−0.1964 (3)	0.9958 (3)	0.0219 (9)
H9	0.5883	−0.256	1.0581	0.026*
C12	0.5181 (4)	−0.0224 (3)	0.8210 (3)	0.0217 (9)
H12	0.4973	0.0387	0.7595	0.026*
C4	0.2562 (4)	0.0444 (3)	0.3597 (3)	0.0237 (9)
H4A	0.3235	0.0897	0.3359	0.028*
H4B	0.2013	0.1162	0.3755	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag	0.0250 (2)	0.02315 (17)	0.02429 (18)	0.00894 (12)	0.00389 (13)	−0.00441 (11)
S	0.0181 (6)	0.0196 (5)	0.0245 (5)	−0.0014 (4)	0.0046 (4)	−0.0012 (4)
N3	0.0172 (18)	0.0154 (15)	0.0164 (16)	0.0015 (12)	0.0039 (14)	0.0006 (11)
C5	0.019 (2)	0.0209 (18)	0.022 (2)	0.0016 (15)	0.0071 (17)	0.0008 (14)
N2	0.0176 (18)	0.0200 (15)	0.0159 (16)	0.0023 (12)	0.0043 (14)	0.0007 (11)
O1	0.0311 (19)	0.0303 (15)	0.0457 (18)	0.0044 (13)	0.0028 (15)	−0.0195 (12)
O2	0.0238 (18)	0.0409 (16)	0.0336 (17)	0.0025 (13)	0.0028 (14)	0.0114 (12)
C11	0.023 (2)	0.0224 (19)	0.034 (2)	−0.0083 (16)	0.015 (2)	−0.0082 (16)
C8	0.017 (2)	0.0171 (17)	0.0159 (19)	0.0039 (14)	0.0067 (16)	−0.0023 (13)
N1	0.0181 (19)	0.0205 (16)	0.0162 (17)	0.0020 (12)	0.0022 (14)	0.0008 (11)
C1	0.022 (2)	0.0170 (18)	0.0130 (19)	−0.0001 (15)	0.0020 (16)	−0.0014 (13)
O3	0.0248 (17)	0.0280 (14)	0.0334 (16)	−0.0037 (12)	0.0126 (13)	0.0033 (11)
C3	0.015 (2)	0.0190 (18)	0.026 (2)	0.0052 (15)	0.0011 (17)	−0.0022 (15)
C2	0.016 (2)	0.0243 (19)	0.019 (2)	0.0009 (15)	0.0036 (17)	−0.0034 (14)
C10	0.014 (2)	0.027 (2)	0.022 (2)	0.0007 (16)	0.0033 (17)	−0.0062 (15)
C6	0.020 (2)	0.0224 (19)	0.021 (2)	−0.0006 (15)	0.0058 (17)	0.0002 (15)
C7	0.019 (2)	0.0205 (18)	0.019 (2)	−0.0006 (15)	0.0052 (17)	0.0000 (14)
C9	0.024 (2)	0.0205 (19)	0.019 (2)	0.0052 (16)	0.0027 (18)	−0.0005 (14)
C12	0.026 (2)	0.0191 (19)	0.023 (2)	−0.0027 (16)	0.0127 (18)	0.0008 (14)
C4	0.027 (3)	0.0194 (18)	0.021 (2)	0.0036 (16)	0.0016 (18)	0.0039 (14)

Geometric parameters (Å, º)

Ag—C1	2.065 (4)	C8—C12	1.391 (5)
Ag—N3^i	2.144 (3)	C8—C7	1.499 (5)
S—O1	1.448 (3)	N1—C1	1.345 (5)
S—O2	1.452 (3)	N1—C2	1.389 (5)
S—O3	1.453 (3)	N1—C4	1.463 (4)
S—C6	1.785 (4)	C3—C2	1.331 (5)
N3—C9	1.338 (5)	C3—H3	0.95
N3—C8	1.350 (4)	C2—H2	0.95
N3—Ag^ii	2.144 (3)	C10—C9	1.375 (5)
C5—C4	1.520 (5)	C10—H10	0.95
C5—C6	1.521 (5)	C6—H6A	0.99
C5—H5A	0.99	C6—H6B	0.99
C5—H5B	0.99	C7—H7A	0.99
N2—C1	1.361 (4)	C7—H7B	0.99
N2—C3	1.383 (5)	C9—H9	0.95
N2—C7	1.456 (4)	C12—H12	0.95
C11—C10	1.379 (5)	C4—H4A	0.99
C11—C12	1.383 (5)	C4—H4B	0.99
C11—H11	0.95
C1—Ag—N3^i	168.31 (12)	C2—C3—H3	126.5
O1—S—O2	113.30 (16)	N2—C3—H3	126.5
O1—S—O3	112.50 (17)	C3—C2—N1	106.4 (3)
O2—S—O3	112.94 (17)	C3—C2—H2	126.8
O1—S—C6	106.45 (17)	N1—C2—H2	126.8
O2—S—C6	105.77 (17)	C9—C10—C11	117.8 (3)
O3—S—C6	105.04 (16)	C9—C10—H10	121.1
C9—N3—C8	118.2 (3)	C11—C10—H10	121.1
C9—N3—Ag^ii	119.1 (2)	C5—C6—S	113.1 (3)
C8—N3—Ag^ii	122.5 (2)	C5—C6—H6A	109
C4—C5—C6	113.1 (3)	S—C6—H6A	109
C4—C5—H5A	108.9	C5—C6—H6B	109
C6—C5—H5A	108.9	S—C6—H6B	109
C4—C5—H5B	108.9	H6A—C6—H6B	107.8
C6—C5—H5B	108.9	N2—C7—C8	112.8 (3)
H5A—C5—H5B	107.8	N2—C7—H7A	109
C1—N2—C3	111.0 (3)	C8—C7—H7A	109
C1—N2—C7	124.8 (3)	N2—C7—H7B	109
C3—N2—C7	124.1 (3)	C8—C7—H7B	109
C10—C11—C12	119.7 (3)	H7A—C7—H7B	107.8
C10—C11—H11	120.1	N3—C9—C10	123.9 (3)
C12—C11—H11	120.1	N3—C9—H9	118.1
N3—C8—C12	121.3 (3)	C10—C9—H9	118.1
N3—C8—C7	116.5 (3)	C11—C12—C8	119.1 (3)
C12—C8—C7	122.1 (3)	C11—C12—H12	120.5
C1—N1—C2	111.7 (3)	C8—C12—H12	120.5
C1—N1—C4	124.4 (3)	N1—C4—C5	110.6 (3)
C2—N1—C4	123.7 (3)	N1—C4—H4A	109.5
N1—C1—N2	103.8 (3)	C5—C4—H4A	109.5
N1—C1—Ag	125.9 (2)	N1—C4—H4B	109.5
N2—C1—Ag	130.1 (3)	C5—C4—H4B	109.5
C2—C3—N2	107.1 (3)	H4A—C4—H4B	108.1
C9—N3—C8—C12	−1.1 (5)	C12—C11—C10—C9	−1.7 (5)
Ag^ii—N3—C8—C12	174.2 (3)	C4—C5—C6—S	−79.6 (4)
C9—N3—C8—C7	−176.5 (3)	O1—S—C6—C5	68.0 (3)
Ag^ii—N3—C8—C7	−1.3 (4)	O2—S—C6—C5	−171.2 (2)
C2—N1—C1—N2	0.0 (4)	O3—S—C6—C5	−51.5 (3)
C4—N1—C1—N2	174.1 (3)	C1—N2—C7—C8	−115.2 (4)
C2—N1—C1—Ag	175.6 (2)	C3—N2—C7—C8	67.1 (4)
C4—N1—C1—Ag	−10.3 (5)	N3—C8—C7—N2	−147.7 (3)
C3—N2—C1—N1	0.1 (4)	C12—C8—C7—N2	36.9 (5)
C7—N2—C1—N1	−177.9 (3)	C8—N3—C9—C10	−1.1 (5)
C3—N2—C1—Ag	−175.3 (3)	Ag^ii—N3—C9—C10	−176.6 (3)
C7—N2—C1—Ag	6.8 (5)	C11—C10—C9—N3	2.5 (6)
N3^i—Ag—C1—N1	−26.1 (8)	C10—C11—C12—C8	−0.4 (5)
N3^i—Ag—C1—N2	148.3 (5)	N3—C8—C12—C11	1.8 (5)
C1—N2—C3—C2	−0.1 (4)	C7—C8—C12—C11	177.0 (3)
C7—N2—C3—C2	177.9 (3)	C1—N1—C4—C5	−106.9 (4)
N2—C3—C2—N1	0.1 (4)	C2—N1—C4—C5	66.5 (5)
C1—N1—C2—C3	0.0 (4)	C6—C5—C4—N1	172.4 (3)
C4—N1—C2—C3	−174.2 (3)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3^iii	0.95	2.40	3.349 (4)	173
C6—H6A···O2^iv	0.99	2.51	3.458 (5)	160
C7—H7B···O3^v	0.99	2.38	3.367 (5)	175
C2—H2···O2^vi	0.95	2.53	3.179 (5)	126
C12—H12···O1^vii	0.95	2.47	3.143 (4)	128
C7—H7A···O3^viii	0.99	2.41	3.257 (4)	143

Symmetry codes: (iii) x+1, y, z+1; (iv) −x, −y, −z; (v) −x, −y, −z+1; (vi) −x+1/2, y−1/2, −z+1/2; (vii) x+1/2, −y+1/2, z+1/2; (viii) x+1/2, −y−1/2, z+1/2.