catena-Poly[[(thio­cyanato-κN)copper(II)]-μ₃-[2-(2-pyridylmethyl­amino)ethanesulfonato-κ⁵N,N′,O:O′:O′′]]

The title polymer, [Cu(C₈H₁₁N₂O₃S)(SCN)]_n or [Cu(PMT)(SCN)]_n, contains six-coordinate Cu^II units. The Cu^II ion is coordinated by one thio­cyanate N atom, an N,N′,O-tridentate 2-(2-pyridylmethyl­amino)ethanesulfonate (PMT) anion and two axial bridging sulfonate O atoms from two adjacent PMT ligands in a distorted octa­hedron. The deprotonated PMT ligand acts as a μ₃-bridging ligand and forms an eight-membered (–Cu—O—S—O–)₂ ring between two neighbouring Cu^II atoms. These rings are inter­connected, generating a one-dimensional linear chain structure. These polymetric chains are connected into a three-dimensional network via inter­chain π–π stacking of the pyridine rings and inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.077
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT220_ALERT_2_C Large Non-Solvent    S     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8

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

   0 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
   0 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

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

catena-Poly[[(thiocyanato-κN)copper(II)]-µ₃-[2-(2- pyridylmethylamino)ethanesulfonato-κ⁵N,N',O:O':O'']]

Crystal data

[Cu(C8H11N2O3S)(NCS)]	F(000) = 684
Mr = 336.87	Dx = 1.749 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5010 reflections
a = 7.2245 (9) Å	θ = 2.6–28.2°
b = 11.4470 (14) Å	µ = 2.04 mm^−1
c = 15.5537 (19) Å	T = 291 K
β = 95.970 (1)°	Block, green
V = 1279.3 (3) Å^3	0.25 × 0.20 × 0.17 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	2923 independent reflections
Radiation source: fine-focus sealed tube	2541 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.631, Tmax = 0.720	k = −14→14
10694 measured reflections	l = −20→20

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0345P)^2 + 1.2013P] where P = (Fo^2 + 2Fc^2)/3
2923 reflections	(Δ/σ)max = 0.002
167 parameters	Δρmax = 1.01 e Å^−3
0 restraints	Δρmin = −0.77 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.

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.24863 (4)	0.32837 (2)	1.011898 (17)	0.02629 (10)
S1	0.26736 (7)	0.60645 (5)	0.98655 (4)	0.02434 (13)
S2	0.08971 (13)	0.27928 (13)	1.28808 (6)	0.0811 (4)
O1	0.0884 (2)	0.66018 (16)	0.99373 (13)	0.0388 (4)
O2	0.2913 (2)	0.49814 (14)	1.03817 (10)	0.0310 (4)
O3	0.4229 (2)	0.68607 (14)	1.00680 (11)	0.0330 (4)
N1	0.2239 (3)	0.16010 (17)	0.97528 (14)	0.0312 (4)
N2	0.2131 (3)	0.35288 (16)	0.88239 (13)	0.0275 (4)
N3	0.2595 (3)	0.2965 (2)	1.13597 (14)	0.0412 (5)
C1	0.1494 (3)	0.1447 (2)	0.89369 (17)	0.0341 (5)
C2	0.1160 (4)	0.0330 (2)	0.8591 (2)	0.0498 (7)
H2	0.0622	0.0235	0.8026	0.060*
C3	0.1639 (5)	−0.0623 (2)	0.9101 (2)	0.0573 (9)
H3	0.1423	−0.1373	0.8883	0.069*
C4	0.2441 (4)	−0.0468 (3)	0.9936 (2)	0.0530 (8)
H4	0.2790	−0.1108	1.0284	0.064*
C5	0.2718 (4)	0.0658 (2)	1.0246 (2)	0.0416 (6)
H5	0.3249	0.0768	1.0811	0.050*
C6	0.0995 (4)	0.2546 (2)	0.84399 (16)	0.0354 (5)
H6A	0.1221	0.2444	0.7841	0.043*
H6B	−0.0316	0.2717	0.8457	0.043*
C7	0.1392 (3)	0.4665 (2)	0.84818 (15)	0.0306 (5)
H7A	0.0195	0.4815	0.8691	0.037*
H7B	0.1210	0.4634	0.7855	0.037*
C8	0.1868 (4)	0.2886 (3)	1.19814 (17)	0.0409 (6)
C9	0.2733 (3)	0.5653 (2)	0.87656 (15)	0.0312 (5)
H9A	0.2429	0.6328	0.8401	0.037*
H9B	0.3987	0.5411	0.8680	0.037*
H2N	0.325 (4)	0.345 (2)	0.8687 (18)	0.035 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02701 (16)	0.02252 (15)	0.02914 (16)	−0.00019 (10)	0.00193 (10)	0.00208 (10)
S1	0.0183 (2)	0.0219 (3)	0.0331 (3)	0.00058 (18)	0.0039 (2)	−0.0008 (2)
S2	0.0488 (5)	0.1521 (11)	0.0436 (5)	−0.0113 (6)	0.0111 (4)	0.0218 (6)
O1	0.0214 (8)	0.0380 (10)	0.0574 (12)	0.0045 (7)	0.0061 (8)	−0.0040 (8)
O2	0.0402 (9)	0.0237 (8)	0.0287 (8)	0.0008 (7)	0.0007 (7)	−0.0005 (6)
O3	0.0228 (8)	0.0294 (9)	0.0473 (10)	−0.0042 (6)	0.0059 (7)	−0.0063 (7)
N1	0.0231 (9)	0.0242 (10)	0.0473 (12)	−0.0010 (7)	0.0080 (8)	0.0005 (8)
N2	0.0241 (10)	0.0265 (10)	0.0323 (10)	−0.0011 (7)	0.0045 (8)	−0.0025 (7)
N3	0.0467 (13)	0.0413 (12)	0.0356 (12)	−0.0004 (10)	0.0051 (10)	0.0098 (9)
C1	0.0291 (12)	0.0290 (12)	0.0462 (15)	−0.0042 (9)	0.0126 (10)	−0.0067 (10)
C2	0.0562 (18)	0.0351 (15)	0.0607 (19)	−0.0101 (12)	0.0192 (14)	−0.0154 (13)
C3	0.063 (2)	0.0257 (14)	0.088 (3)	−0.0072 (13)	0.0294 (18)	−0.0116 (14)
C4	0.0468 (17)	0.0255 (13)	0.090 (3)	0.0055 (11)	0.0201 (16)	0.0084 (14)
C5	0.0330 (13)	0.0307 (13)	0.0613 (17)	0.0039 (10)	0.0058 (12)	0.0070 (12)
C6	0.0368 (13)	0.0352 (13)	0.0337 (13)	−0.0057 (10)	0.0010 (10)	−0.0087 (10)
C7	0.0316 (12)	0.0308 (12)	0.0285 (11)	−0.0009 (9)	−0.0016 (9)	0.0008 (9)
C8	0.0322 (13)	0.0531 (16)	0.0358 (14)	−0.0032 (11)	−0.0042 (10)	0.0102 (12)
C9	0.0333 (12)	0.0311 (12)	0.0295 (11)	−0.0026 (9)	0.0042 (9)	0.0040 (9)

Geometric parameters (Å, º)

Cu1—N3	1.958 (2)	N3—C8	1.151 (3)
Cu1—O2	2.0032 (16)	C1—C2	1.398 (3)
Cu1—N1	2.011 (2)	C1—C6	1.502 (4)
Cu1—N2	2.024 (2)	C2—C3	1.371 (5)
Cu1—O3^i	2.4260 (16)	C2—H2	0.9300
Cu1—O1^ii	2.4306 (17)	C3—C4	1.377 (5)
S1—O1	1.4468 (17)	C3—H3	0.9300
S1—O3	1.4558 (16)	C4—C5	1.384 (4)
S1—O2	1.4775 (17)	C4—H4	0.9300
S1—C9	1.779 (2)	C5—H5	0.9300
S2—C8	1.632 (3)	C6—H6A	0.9700
O1—Cu1^ii	2.4306 (16)	C6—H6B	0.9700
O3—Cu1^i	2.4260 (16)	C7—C9	1.524 (3)
N1—C1	1.338 (3)	C7—H7A	0.9700
N1—C5	1.348 (3)	C7—H7B	0.9700
N2—C6	1.481 (3)	C9—H9A	0.9700
N2—C7	1.484 (3)	C9—H9B	0.9700
N2—H2N	0.86 (3)
N3—Cu1—O2	89.43 (8)	N1—C1—C2	121.5 (3)
N3—Cu1—N1	95.39 (9)	N1—C1—C6	115.4 (2)
O2—Cu1—N1	173.79 (7)	C2—C1—C6	123.1 (3)
N3—Cu1—N2	174.33 (9)	C3—C2—C1	118.8 (3)
O2—Cu1—N2	93.98 (7)	C3—C2—H2	120.6
N1—Cu1—N2	81.52 (8)	C1—C2—H2	120.6
N3—Cu1—O3^i	99.57 (8)	C2—C3—C4	119.9 (3)
O2—Cu1—O3^i	87.63 (6)	C2—C3—H3	120.0
N1—Cu1—O3^i	87.71 (7)	C4—C3—H3	120.0
N2—Cu1—O3^i	85.10 (7)	C3—C4—C5	118.7 (3)
N3—Cu1—O1^ii	89.01 (8)	C3—C4—H4	120.6
O2—Cu1—O1^ii	95.02 (7)	C5—C4—H4	120.6
N1—Cu1—O1^ii	88.98 (7)	N1—C5—C4	121.8 (3)
N2—Cu1—O1^ii	86.19 (7)	N1—C5—H5	119.1
O3^i—Cu1—O1^ii	171.06 (6)	C4—C5—H5	119.1
O1—S1—O3	113.16 (11)	N2—C6—C1	109.6 (2)
O1—S1—O2	111.72 (11)	N2—C6—H6A	109.7
O3—S1—O2	111.32 (10)	C1—C6—H6A	109.7
O1—S1—C9	107.33 (11)	N2—C6—H6B	109.7
O3—S1—C9	106.18 (11)	C1—C6—H6B	109.7
O2—S1—C9	106.68 (10)	H6A—C6—H6B	108.2
S1—O1—Cu1^ii	156.95 (11)	N2—C7—C9	110.65 (18)
S1—O2—Cu1	134.13 (10)	N2—C7—H7A	109.5
S1—O3—Cu1^i	132.39 (10)	C9—C7—H7A	109.5
C1—N1—C5	119.2 (2)	N2—C7—H7B	109.5
C1—N1—Cu1	114.22 (16)	C9—C7—H7B	109.5
C5—N1—Cu1	126.52 (19)	H7A—C7—H7B	108.1
C6—N2—C7	110.97 (18)	N3—C8—S2	178.1 (3)
C6—N2—Cu1	107.69 (14)	C7—C9—S1	113.39 (16)
C7—N2—Cu1	118.83 (14)	C7—C9—H9A	108.9
C6—N2—H2N	108.6 (19)	S1—C9—H9A	108.9
C7—N2—H2N	108.1 (19)	C7—C9—H9B	108.9
Cu1—N2—H2N	102.0 (19)	S1—C9—H9B	108.9
C8—N3—Cu1	150.2 (2)	H9A—C9—H9B	107.7
O3—S1—O1—Cu1^ii	179.7 (3)	O3^i—Cu1—N2—C7	−115.63 (16)
O2—S1—O1—Cu1^ii	−53.7 (3)	O1^ii—Cu1—N2—C7	66.42 (16)
C9—S1—O1—Cu1^ii	62.9 (3)	O2—Cu1—N3—C8	88.5 (5)
O1—S1—O2—Cu1	94.35 (16)	N1—Cu1—N3—C8	−95.4 (5)
O3—S1—O2—Cu1	−138.07 (14)	O3^i—Cu1—N3—C8	176.0 (5)
C9—S1—O2—Cu1	−22.65 (17)	O1^ii—Cu1—N3—C8	−6.5 (5)
N3—Cu1—O2—S1	−163.86 (16)	C5—N1—C1—C2	1.6 (4)
N2—Cu1—O2—S1	11.61 (15)	Cu1—N1—C1—C2	−177.5 (2)
O3^i—Cu1—O2—S1	96.54 (15)	C5—N1—C1—C6	179.6 (2)
O1^ii—Cu1—O2—S1	−74.91 (15)	Cu1—N1—C1—C6	0.6 (3)
O1—S1—O3—Cu1^i	−168.86 (13)	N1—C1—C2—C3	−1.1 (4)
O2—S1—O3—Cu1^i	64.35 (16)	C6—C1—C2—C3	−179.0 (3)
C9—S1—O3—Cu1^i	−51.38 (16)	C1—C2—C3—C4	−0.3 (5)
N3—Cu1—N1—C1	158.20 (17)	C2—C3—C4—C5	1.0 (5)
N2—Cu1—N1—C1	−17.01 (16)	C1—N1—C5—C4	−0.8 (4)
O3^i—Cu1—N1—C1	−102.40 (16)	Cu1—N1—C5—C4	178.2 (2)
O1^ii—Cu1—N1—C1	69.29 (16)	C3—C4—C5—N1	−0.6 (4)
N3—Cu1—N1—C5	−20.8 (2)	C7—N2—C6—C1	−167.23 (19)
N2—Cu1—N1—C5	164.0 (2)	Cu1—N2—C6—C1	−35.6 (2)
O3^i—Cu1—N1—C5	78.6 (2)	N1—C1—C6—N2	23.8 (3)
O1^ii—Cu1—N1—C5	−109.7 (2)	C2—C1—C6—N2	−158.2 (2)
O2—Cu1—N2—C6	−155.54 (15)	C6—N2—C7—C9	−170.94 (19)
N1—Cu1—N2—C6	28.77 (15)	Cu1—N2—C7—C9	63.4 (2)
O3^i—Cu1—N2—C6	117.18 (15)	N2—C7—C9—S1	−75.9 (2)
O1^ii—Cu1—N2—C6	−60.77 (15)	O1—S1—C9—C7	−68.10 (19)
O2—Cu1—N2—C7	−28.36 (16)	O3—S1—C9—C7	170.60 (16)
N1—Cu1—N2—C7	155.96 (17)	O2—S1—C9—C7	51.78 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3^i	0.86 (3)	2.54 (3)	3.024 (3)	116 (2)
N2—H2N···S2^iii	0.86 (3)	2.79 (3)	3.560 (2)	150 (2)

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