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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.
Supporting information
CCDC reference: 227752
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (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
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]
top
Crystal data top
[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) Å3 | 0.58 × 0.46 × 0.20 mm |
Z = 4 | |
Data collection top
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 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)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0403P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0077 (7) |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—O5i | 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—O5i | 94.80 (8) | N—C3—C4 | 127.4 (2) |
O6—Cu—O5i | 87.34 (8) | N—C3—H3 | 116.3 |
O1—Cu—O5i | 82.43 (8) | C4—C3—H3 | 116.3 |
N—Cu—O5i | 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) top
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···O5ii | 0.81 (1) | 1.91 (1) | 2.713 (3) | 178 (3) |
O7—H7A···O2iii | 0.82 (1) | 2.08 (2) | 2.866 (4) | 161 (4) |
O7—H7B···O3iv | 0.81 (1) | 1.99 (2) | 2.768 (3) | 159 (6) |
C10—H10···O1v | 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. |
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