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In the crystal structure of the title compound, [Cu(C11H9NO5)(H2O)2]·2H2O, in which N-(3-carb­oxy-2-hydroxy­benzyl­idene)alaninate (H3ALS) is the Schiff base synthesized from L-alanine with 3-carboxy­salicylaldehyde, the copper(II) ion is penta­coordinated in a square-pyramidal geometry, with the HALS2− dianion acting as a tridentate ONO-chelator in a plane, and two water mol­ecules occupying the apical site and the remaining basal site.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038931/kj2027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038931/kj2027Isup2.hkl
Contains datablock I

CCDC reference: 627957

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.094
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Diaqua[N-(3-carboxy-2-hydroxybenzylidene)alaninato-κ3O2,N,O']copper(II) dihydrate top
Crystal data top
[Cu(C11H9NO5)(H2O)2]·2H2OZ = 2
Mr = 370.80F(000) = 382
Triclinic, P1Dx = 1.663 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2353 (7) ÅCell parameters from 1961 reflections
b = 8.7889 (9) Åθ = 2.4–27.0°
c = 11.8112 (11) ŵ = 1.52 mm1
α = 81.125 (1)°T = 273 K
β = 87.533 (1)°Block, green
γ = 87.088 (1)°0.15 × 0.12 × 0.11 mm
V = 740.66 (13) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3280 independent reflections
Radiation source: fine-focus sealed tube2777 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 99
Tmin = 0.804, Tmax = 0.851k = 811
4674 measured reflectionsl = 1215
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0442P)2 + 0.3567P]
where P = (Fo2 + 2Fc2)/3
3280 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.52 e Å3
12 restraintsΔρmin = 0.48 e Å3
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
xyzUiso*/Ueq
Cu10.58925 (5)0.50187 (4)0.28527 (3)0.02919 (12)
N10.6259 (3)0.3285 (3)0.20239 (19)0.0274 (5)
O1W0.5110 (3)0.6766 (2)0.36493 (17)0.0418 (5)
H1A0.41920.73750.34420.050*
H1B0.51420.66670.43750.050*
O2W0.8418 (3)0.4860 (3)0.3870 (2)0.0461 (6)
H2A0.89270.40900.42860.055*
H2B0.86650.56650.41420.055*
O10.7966 (4)1.0166 (3)0.0809 (2)0.0557 (6)
O20.6992 (4)0.9284 (3)0.0934 (2)0.0577 (7)
H20.67640.84520.13200.087*
O30.6612 (3)0.6466 (2)0.15357 (17)0.0372 (5)
O40.4552 (3)0.3527 (2)0.39827 (17)0.0366 (5)
O50.3295 (3)0.1254 (2)0.41234 (18)0.0413 (5)
C10.7336 (4)0.4682 (3)0.0210 (2)0.0273 (6)
C20.7206 (4)0.6195 (3)0.0511 (2)0.0284 (6)
C30.7737 (4)0.7445 (3)0.0330 (2)0.0303 (6)
C40.8400 (4)0.7168 (4)0.1406 (2)0.0348 (7)
H40.87710.79920.19450.042*
C50.8522 (4)0.5704 (4)0.1693 (3)0.0390 (7)
H50.89640.55440.24180.047*
C60.7985 (4)0.4485 (4)0.0897 (2)0.0337 (6)
H60.80540.35000.10960.040*
C70.7586 (5)0.9065 (4)0.0101 (3)0.0433 (8)
C80.6802 (4)0.3323 (3)0.0975 (2)0.0291 (6)
H80.68570.23980.06830.035*
C90.7364 (5)0.0883 (4)0.3199 (3)0.0431 (8)
H9A0.81910.06290.25910.065*
H9B0.69610.00480.36580.065*
H9C0.79960.14740.36690.065*
C100.5699 (4)0.1822 (3)0.2693 (2)0.0303 (6)
H100.50560.12290.22040.036*
C110.4390 (4)0.2217 (3)0.3666 (2)0.0316 (6)
O3W0.2249 (3)0.8848 (2)0.31471 (19)0.0437 (5)
H3A0.26240.96210.34080.052*
H3B0.22140.90810.24230.052*
O4W0.0348 (3)0.2596 (3)0.5293 (2)0.0449 (6)
H4A0.01960.20280.58420.054*
H4B0.11750.20400.50000.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0399 (2)0.02579 (19)0.02138 (18)0.00000 (14)0.00224 (13)0.00341 (13)
N10.0311 (12)0.0254 (11)0.0247 (11)0.0006 (9)0.0020 (9)0.0025 (9)
O1W0.0606 (15)0.0374 (12)0.0265 (11)0.0149 (10)0.0025 (10)0.0072 (9)
O2W0.0517 (14)0.0378 (12)0.0510 (14)0.0063 (10)0.0197 (11)0.0115 (11)
O10.0746 (15)0.0418 (12)0.0480 (12)0.0096 (11)0.0028 (11)0.0042 (10)
O20.0869 (16)0.0384 (11)0.0481 (12)0.0083 (11)0.0076 (12)0.0085 (10)
O30.0593 (14)0.0282 (11)0.0242 (10)0.0033 (10)0.0044 (9)0.0058 (8)
O40.0512 (13)0.0335 (11)0.0251 (10)0.0046 (9)0.0081 (9)0.0061 (9)
O50.0511 (14)0.0350 (12)0.0367 (12)0.0105 (10)0.0130 (10)0.0035 (9)
C10.0258 (14)0.0318 (14)0.0238 (13)0.0005 (11)0.0011 (10)0.0028 (11)
C20.0292 (14)0.0305 (15)0.0248 (13)0.0020 (11)0.0020 (11)0.0014 (11)
C30.0292 (14)0.0346 (15)0.0260 (14)0.0018 (12)0.0042 (11)0.0002 (12)
C40.0317 (15)0.0418 (17)0.0268 (14)0.0008 (13)0.0018 (12)0.0068 (13)
C50.0379 (17)0.0529 (19)0.0236 (14)0.0048 (14)0.0059 (12)0.0022 (13)
C60.0340 (16)0.0367 (16)0.0302 (15)0.0027 (12)0.0024 (12)0.0064 (12)
C70.057 (2)0.0360 (17)0.0360 (17)0.0085 (15)0.0049 (15)0.0013 (14)
C80.0324 (15)0.0264 (14)0.0289 (14)0.0004 (11)0.0001 (11)0.0063 (11)
C90.0457 (19)0.0377 (17)0.0423 (18)0.0033 (14)0.0005 (14)0.0036 (14)
C100.0368 (16)0.0268 (14)0.0263 (14)0.0030 (12)0.0014 (11)0.0010 (11)
C110.0364 (16)0.0309 (15)0.0256 (14)0.0021 (12)0.0015 (12)0.0010 (12)
O3W0.0524 (14)0.0335 (12)0.0440 (13)0.0034 (10)0.0002 (10)0.0023 (10)
O4W0.0424 (13)0.0373 (12)0.0521 (14)0.0004 (10)0.0031 (11)0.0005 (11)
Geometric parameters (Å, º) top
Cu1—O31.922 (2)C2—C31.419 (4)
Cu1—N11.935 (2)C3—C41.391 (4)
Cu1—O1W1.969 (2)C3—C71.488 (4)
Cu1—O41.980 (2)C4—C51.378 (4)
Cu1—O2W2.217 (2)C4—H40.9300
N1—C81.279 (3)C5—C61.373 (4)
N1—C101.468 (3)C5—H50.9300
O1W—H1A0.8514C6—H60.9300
O1W—H1B0.8495C8—H80.9300
O2W—H2A0.8499C9—C101.516 (4)
O2W—H2B0.8510C9—H9A0.9600
O1—C71.213 (4)C9—H9B0.9600
O2—C71.317 (4)C9—H9C0.9600
O2—H20.8200C10—C111.528 (4)
O3—C21.319 (3)C10—H100.9800
O4—C111.276 (3)O3W—H3A0.8494
O5—C111.235 (3)O3W—H3B0.8498
C1—C61.403 (4)O4W—H4A0.8493
C1—C21.426 (4)O4W—H4B0.8497
C1—C81.441 (4)
O3—Cu1—N192.56 (9)C5—C4—H4119.1
O3—Cu1—O1W88.88 (9)C3—C4—H4119.1
N1—Cu1—O1W171.10 (10)C6—C5—C4119.3 (3)
O3—Cu1—O4164.92 (9)C6—C5—H5120.4
N1—Cu1—O483.54 (9)C4—C5—H5120.4
O1W—Cu1—O492.82 (9)C5—C6—C1121.8 (3)
O3—Cu1—O2W100.92 (9)C5—C6—H6119.1
N1—Cu1—O2W102.75 (9)C1—C6—H6119.1
O1W—Cu1—O2W85.57 (9)O1—C7—O2119.5 (3)
O4—Cu1—O2W94.15 (9)O1—C7—C3123.6 (3)
C8—N1—C10119.4 (2)O2—C7—C3116.9 (3)
C8—N1—Cu1127.1 (2)N1—C8—C1125.3 (3)
C10—N1—Cu1113.39 (17)N1—C8—H8117.3
Cu1—O1W—H1A122.4C1—C8—H8117.3
Cu1—O1W—H1B119.9C10—C9—H9A109.5
H1A—O1W—H1B107.6C10—C9—H9B109.5
Cu1—O2W—H2A130.1H9A—C9—H9B109.5
Cu1—O2W—H2B116.3C10—C9—H9C109.5
H2A—O2W—H2B107.6H9A—C9—H9C109.5
C7—O2—H2109.5H9B—C9—H9C109.5
C2—O3—Cu1128.81 (18)N1—C10—C9111.0 (2)
C11—O4—Cu1114.20 (17)N1—C10—C11107.1 (2)
C6—C1—C2119.1 (3)C9—C10—C11109.1 (2)
C6—C1—C8117.2 (3)N1—C10—H10109.9
C2—C1—C8123.8 (2)C9—C10—H10109.9
O3—C2—C3119.4 (2)C11—C10—H10109.9
O3—C2—C1122.3 (2)O5—C11—O4123.9 (3)
C3—C2—C1118.3 (2)O5—C11—C10119.2 (3)
C4—C3—C2119.8 (3)O4—C11—C10116.8 (2)
C4—C3—C7118.4 (3)H3A—O3W—H3B107.8
C2—C3—C7121.8 (3)H4A—O4W—H4B107.8
C5—C4—C3121.7 (3)
O3—Cu1—N1—C80.3 (3)C2—C3—C4—C51.4 (4)
O4—Cu1—N1—C8165.7 (3)C7—C3—C4—C5177.9 (3)
O2W—Cu1—N1—C8101.5 (2)C3—C4—C5—C60.4 (5)
O3—Cu1—N1—C10174.98 (19)C4—C5—C6—C10.9 (5)
O4—Cu1—N1—C109.59 (19)C2—C1—C6—C50.9 (4)
O2W—Cu1—N1—C1083.23 (19)C8—C1—C6—C5179.7 (3)
N1—Cu1—O3—C23.1 (3)C4—C3—C7—O11.9 (5)
O1W—Cu1—O3—C2174.3 (2)C2—C3—C7—O1177.4 (3)
O4—Cu1—O3—C277.6 (4)C4—C3—C7—O2178.5 (3)
O2W—Cu1—O3—C2100.4 (2)C2—C3—C7—O22.2 (5)
O3—Cu1—O4—C1170.7 (4)C10—N1—C8—C1178.0 (3)
N1—Cu1—O4—C114.9 (2)Cu1—N1—C8—C13.0 (4)
O1W—Cu1—O4—C11167.0 (2)C6—C1—C8—N1176.8 (3)
O2W—Cu1—O4—C11107.3 (2)C2—C1—C8—N14.4 (5)
Cu1—O3—C2—C3177.4 (2)C8—N1—C10—C985.0 (3)
Cu1—O3—C2—C12.5 (4)Cu1—N1—C10—C999.4 (2)
C6—C1—C2—O3179.8 (3)C8—N1—C10—C11156.0 (2)
C8—C1—C2—O31.5 (4)Cu1—N1—C10—C1119.6 (3)
C6—C1—C2—C30.2 (4)Cu1—O4—C11—O5164.4 (2)
C8—C1—C2—C3178.5 (3)Cu1—O4—C11—C1018.1 (3)
O3—C2—C3—C4178.7 (3)N1—C10—C11—O5157.6 (3)
C1—C2—C3—C41.3 (4)C9—C10—C11—O582.3 (3)
O3—C2—C3—C72.0 (4)N1—C10—C11—O424.8 (3)
C1—C2—C3—C7178.0 (3)C9—C10—C11—O495.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.821.732.495 (3)154
O1W—H1A···O3W0.851.872.715 (3)172.4
O1W—H1B···O4i0.851.942.789 (3)174.9
O2W—H2A···O4Wii0.851.922.761 (3)170.5
O2W—H2B···O4Wi0.851.942.781 (3)170.5
O3W—H3A···O5iii0.851.872.714 (3)173.9
O3W—H3B···O1iv0.851.932.772 (3)173.7
O4W—H4A···O3Wv0.851.982.785 (3)158.7
O4W—H4B···O50.851.972.800 (3)165.6
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x+1, y+2, z; (v) x, y+1, z+1.
 

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