A new one-dimensional coordination polymer: {[Cu(C₁₀H₉NO₅S)(H₂O)]·H₂O}_n

The title compound, catena-poly­[[copper(II)-μ-2-{[(E)-(5-formyl-2-oxido­phenyl)­methyl­idene]­amino}-1-ethanesulfonato(2−)] monohydrate], {[Cu(L)(H₂O)]·H₂O}_n, where H₂L = 2-{[(E)-(5-formyl-2-hydroxy­phenyl)­methyl­idene]­amino}-1-ethanesulfonic acid (C₁₀H₁₁NO₅S), was synthesized in water–methanol solution and the crystal structure determined by X-ray diffraction analysis. The Cu atom is five-coordinate, forming a distorted square-pyramidal geometry. This geometry includes a weak bond between the Cu atom and the O atom of the formyl group of another ligand, giving a one-dimensional infinite chain structure. The structure is further stabilized by intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.029
• wR factor = 0.073
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.81(5), Rep   0.813(10) ......       5.00 su-Rat
              O7   -H7B     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.81(5), Rep   0.813(10) ......       5.00 su-Rat
              O7   -H7B     1.555   1.555

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.405     0.686
            Tmin and Tmax expected:      0.364     0.686
            RR =      1.111
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.10
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          1
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.29
PLAT731_ALERT_1_C Bond    Calc     0.81(4), Rep   0.808(10) ......       4.00 su-Rat
              O6   -H6B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.81(4), Rep   0.808(10) ......       4.00 su-Rat
              O6   -H6B     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.91(4), Rep   1.905(11) ......       3.64 su-Rat
              H6B  -O5      1.555   4.665
PLAT736_ALERT_1_C H...A   Calc     2.00(5), Rep     1.99(2) ......       2.50 su-Rat
              H7B  -O3      1.555   2.745

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

   6 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

catena-poly[[copper(II)-µ-2-{[(E)-(5-formyl-2-oxidophenyl)methylidene]amino}- 1-ethanesulfonato(2-)] monohydrate]

Crystal data

[Cu(C10H11NO5S)(H2O)]·H2O	F(000) = 724
Mr = 354.81	Dx = 1.827 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33 reflections
a = 8.589 (2) Å	θ = 3.5–15.3°
b = 17.585 (2) Å	µ = 1.89 mm^−1
c = 9.479 (2) Å	T = 291 K
β = 115.69 (1)°	Plate-like, green
V = 1290.1 (4) Å^3	0.58 × 0.46 × 0.20 mm
Z = 4

Data collection

Siemens P4 diffractometer	1963 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 25.5°, θmin = 2.3°
ω scans	h = 0→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = 0→21
Tmin = 0.405, Tmax = 0.686	l = −11→10
2761 measured reflections	3 standard reflections every 97 reflections
2409 independent reflections	intensity decay: 5.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0403P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2409 reflections	Δρmax = 0.34 e Å^−3
202 parameters	Δρmin = −0.26 e Å^−3
4 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (7)

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
Cu	0.68077 (4)	0.294499 (17)	0.27034 (4)	0.02613 (13)
S	0.85727 (9)	0.43945 (4)	0.20767 (9)	0.03339 (19)
O1	0.8224 (3)	0.35685 (10)	0.2007 (2)	0.0385 (5)
O2	0.7577 (3)	0.47527 (11)	0.0596 (3)	0.0487 (6)
O3	1.0411 (3)	0.45376 (12)	0.2727 (3)	0.0549 (6)
O4	0.5705 (2)	0.21826 (10)	0.3327 (2)	0.0320 (4)
O5	−0.0095 (3)	0.29446 (12)	0.5598 (3)	0.0448 (5)
O6	0.7792 (3)	0.21035 (11)	0.2050 (3)	0.0385 (5)
O7	0.7509 (4)	0.06476 (14)	0.2639 (4)	0.0587 (7)
N	0.5678 (3)	0.37876 (12)	0.3250 (3)	0.0287 (5)
C1	0.7845 (4)	0.47539 (16)	0.3418 (4)	0.0401 (7)
H1A	0.8523	0.4531	0.4440	0.048*
H1B	0.8022	0.5300	0.3509	0.048*
C2	0.5969 (4)	0.45848 (15)	0.2926 (4)	0.0397 (7)
H2A	0.5529	0.4922	0.3478	0.048*
H2B	0.5329	0.4684	0.1814	0.048*
C3	0.4524 (3)	0.36867 (14)	0.3751 (3)	0.0303 (6)
H3	0.4038	0.4124	0.3944	0.036*
C4	0.3896 (3)	0.29738 (14)	0.4049 (3)	0.0267 (6)
C5	0.4535 (3)	0.22545 (14)	0.3831 (3)	0.0260 (6)
C6	0.3852 (4)	0.15931 (15)	0.4196 (3)	0.0335 (6)
H6	0.4271	0.1119	0.4092	0.040*
C7	0.2590 (3)	0.16365 (15)	0.4698 (3)	0.0321 (6)
H7	0.2142	0.1191	0.4906	0.039*
C8	0.1947 (3)	0.23476 (16)	0.4908 (3)	0.0286 (6)
C9	0.2622 (3)	0.29984 (15)	0.4583 (3)	0.0293 (6)
H9	0.2214	0.3468	0.4726	0.035*
C10	0.0592 (4)	0.23707 (18)	0.5443 (3)	0.0354 (7)
H7B	0.832 (5)	0.040 (3)	0.267 (6)	0.16 (3)*
H7A	0.765 (6)	0.063 (2)	0.355 (2)	0.083 (16)*
H6B	0.843 (4)	0.2100 (18)	0.163 (4)	0.056 (11)*
H6A	0.767 (4)	0.1659 (8)	0.222 (3)	0.048 (10)*
H10	0.016 (4)	0.1875 (16)	0.572 (3)	0.045 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0272 (2)	0.02503 (18)	0.0364 (2)	0.00109 (14)	0.02341 (16)	0.00048 (14)
S	0.0346 (4)	0.0281 (4)	0.0488 (4)	−0.0020 (3)	0.0287 (4)	0.0030 (3)
O1	0.0482 (13)	0.0283 (10)	0.0613 (14)	−0.0010 (9)	0.0447 (12)	0.0002 (9)
O2	0.0630 (15)	0.0427 (12)	0.0497 (13)	0.0074 (11)	0.0332 (12)	0.0081 (10)
O3	0.0409 (14)	0.0473 (13)	0.0847 (18)	−0.0062 (11)	0.0349 (13)	0.0080 (12)
O4	0.0343 (11)	0.0287 (10)	0.0484 (12)	0.0046 (8)	0.0324 (10)	0.0039 (8)
O5	0.0434 (12)	0.0540 (13)	0.0565 (14)	0.0053 (10)	0.0399 (11)	0.0046 (11)
O6	0.0489 (13)	0.0275 (11)	0.0643 (15)	0.0011 (9)	0.0481 (12)	−0.0002 (10)
O7	0.078 (2)	0.0393 (13)	0.086 (2)	0.0122 (13)	0.0613 (18)	0.0101 (14)
N	0.0303 (13)	0.0256 (11)	0.0400 (13)	−0.0005 (9)	0.0244 (11)	−0.0012 (10)
C1	0.0447 (19)	0.0337 (15)	0.0527 (19)	−0.0076 (14)	0.0313 (16)	−0.0041 (14)
C2	0.0456 (19)	0.0272 (15)	0.061 (2)	0.0000 (13)	0.0368 (17)	−0.0034 (13)
C3	0.0333 (15)	0.0282 (14)	0.0386 (16)	0.0046 (12)	0.0242 (14)	−0.0012 (12)
C4	0.0232 (13)	0.0332 (14)	0.0280 (14)	0.0009 (11)	0.0151 (12)	0.0004 (11)
C5	0.0226 (14)	0.0309 (14)	0.0284 (14)	0.0031 (11)	0.0146 (12)	0.0016 (11)
C6	0.0350 (16)	0.0303 (14)	0.0439 (17)	0.0039 (12)	0.0252 (14)	0.0025 (12)
C7	0.0297 (15)	0.0333 (15)	0.0395 (16)	−0.0033 (12)	0.0207 (13)	0.0043 (12)
C8	0.0224 (14)	0.0408 (15)	0.0279 (14)	0.0002 (12)	0.0159 (12)	0.0035 (12)
C9	0.0265 (14)	0.0358 (15)	0.0323 (14)	0.0051 (12)	0.0189 (12)	−0.0008 (12)
C10	0.0280 (16)	0.0493 (17)	0.0361 (16)	−0.0006 (14)	0.0207 (14)	0.0031 (14)

Geometric parameters (Å, º)

Cu—O4	1.8786 (18)	C1—H1A	0.9700
Cu—O6	1.9346 (19)	C1—H1B	0.9700
Cu—O1	1.9526 (18)	C2—H2A	0.9700
Cu—N	1.960 (2)	C2—H2B	0.9700
Cu—O5^i	2.877 (3)	C3—C4	1.440 (3)
S—O2	1.434 (2)	C3—H3	0.9300
S—O3	1.447 (2)	C4—C9	1.392 (4)
S—O1	1.4788 (19)	C4—C5	1.429 (3)
S—C1	1.759 (3)	C5—C6	1.412 (4)
O4—C5	1.293 (3)	C6—C7	1.361 (4)
O5—C10	1.210 (3)	C6—H6	0.9300
O6—H6B	0.808 (10)	C7—C8	1.415 (4)
O6—H6A	0.813 (10)	C7—H7	0.9300
O7—H7B	0.813 (10)	C8—C9	1.376 (4)
O7—H7A	0.820 (10)	C8—C10	1.458 (3)
N—C3	1.284 (3)	C9—H9	0.9300
N—C2	1.479 (3)	C10—H10	1.02 (3)
C1—C2	1.501 (4)
O4—Cu—O6	84.54 (8)	N—C2—C1	112.2 (2)
O4—Cu—O1	168.50 (8)	N—C2—H2A	109.2
O6—Cu—O1	84.18 (8)	C1—C2—H2A	109.2
O4—Cu—N	94.68 (8)	N—C2—H2B	109.2
O6—Cu—N	176.48 (10)	C1—C2—H2B	109.2
O1—Cu—N	96.72 (8)	H2A—C2—H2B	107.9
O4—Cu—O5^i	94.80 (8)	N—C3—C4	127.4 (2)
O6—Cu—O5^i	87.34 (8)	N—C3—H3	116.3
O1—Cu—O5^i	82.43 (8)	C4—C3—H3	116.3
N—Cu—O5^i	96.16 (8)	C9—C4—C5	119.5 (2)
O2—S—O3	114.73 (14)	C9—C4—C3	117.7 (2)
O2—S—O1	111.37 (13)	C5—C4—C3	122.9 (2)
O3—S—O1	110.65 (12)	O4—C5—C6	118.9 (2)
O2—S—C1	107.55 (14)	O4—C5—C4	123.3 (2)
O3—S—C1	107.06 (14)	C6—C5—C4	117.9 (2)
O1—S—C1	104.86 (12)	C7—C6—C5	121.2 (2)
S—O1—Cu	132.87 (12)	C7—C6—H6	119.4
C5—O4—Cu	128.71 (16)	C5—C6—H6	119.4
Cu—O6—H6B	131 (2)	C6—C7—C8	121.1 (2)
Cu—O6—H6A	124 (2)	C6—C7—H7	119.4
H6B—O6—H6A	105 (3)	C8—C7—H7	119.4
H7B—O7—H7A	102 (5)	C9—C8—C7	118.4 (2)
C3—N—C2	115.7 (2)	C9—C8—C10	122.1 (3)
C3—N—Cu	122.92 (18)	C7—C8—C10	119.5 (2)
C2—N—Cu	120.96 (16)	C8—C9—C4	121.9 (2)
C2—C1—S	112.0 (2)	C8—C9—H9	119.0
C2—C1—H1A	109.2	C4—C9—H9	119.0
S—C1—H1A	109.2	O5—C10—C8	124.8 (3)
C2—C1—H1B	109.2	O5—C10—H10	115.5 (17)
S—C1—H1B	109.2	C8—C10—H10	119.7 (17)
H1A—C1—H1B	107.9
O2—S—O1—Cu	−101.40 (19)	Cu—N—C3—C4	2.1 (4)
O3—S—O1—Cu	129.74 (18)	N—C3—C4—C9	−179.6 (3)
C1—S—O1—Cu	14.6 (2)	N—C3—C4—C5	1.0 (4)
O4—Cu—O1—S	−163.7 (4)	Cu—O4—C5—C6	178.31 (18)
O6—Cu—O1—S	−175.02 (19)	Cu—O4—C5—C4	−2.0 (4)
N—Cu—O1—S	8.40 (19)	C9—C4—C5—O4	179.4 (2)
O6—Cu—O4—C5	−172.7 (2)	C3—C4—C5—O4	−1.2 (4)
O1—Cu—O4—C5	176.0 (4)	C9—C4—C5—C6	−0.9 (4)
N—Cu—O4—C5	3.8 (2)	C3—C4—C5—C6	178.5 (3)
O4—Cu—N—C3	−3.7 (2)	O4—C5—C6—C7	−178.5 (3)
O1—Cu—N—C3	177.8 (2)	C4—C5—C6—C7	1.8 (4)
O4—Cu—N—C2	−176.4 (2)	C5—C6—C7—C8	−1.6 (4)
O1—Cu—N—C2	5.1 (2)	C6—C7—C8—C9	0.4 (4)
O2—S—C1—C2	60.6 (2)	C6—C7—C8—C10	179.8 (3)
O3—S—C1—C2	−175.6 (2)	C7—C8—C9—C4	0.5 (4)
O1—S—C1—C2	−58.1 (2)	C10—C8—C9—C4	−178.9 (3)
C3—N—C2—C1	140.7 (3)	C5—C4—C9—C8	−0.2 (4)
Cu—N—C2—C1	−46.1 (3)	C3—C4—C9—C8	−179.7 (2)
S—C1—C2—N	77.4 (3)	C9—C8—C10—O5	2.6 (5)
C2—N—C3—C4	175.2 (3)	C7—C8—C10—O5	−176.8 (3)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	0.81 (1)	1.84 (1)	2.654 (3)	177 (3)
O6—H6B···O5^ii	0.81 (1)	1.91 (1)	2.713 (3)	178 (3)
O7—H7A···O2^iii	0.82 (1)	2.08 (2)	2.866 (4)	161 (4)
O7—H7B···O3^iv	0.81 (1)	1.99 (2)	2.768 (3)	159 (6)
C10—H10···O1^v	1.02 (3)	2.58 (3)	3.417 (3)	139 (2)

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