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The tridentate Schiff base ligand derived from the conden­s­ation of salicyl­aldehyde and DL-tyrosine, in the presence of pyridine, forms a square-pyramidal five-coordinate Cu complex, [Cu(C16H13NO4)(C5H5N)(H2O)], with a water mol­ecule occupying the apical site.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022043/lh6018sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022043/lh6018Isup2.hkl
Contains datablock I

CCDC reference: 202972

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.082
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

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

Aqua(pyridine-κN)(N-salicylidenetyrosinato-κ3O,N,O')copper(II) top
Crystal data top
[Cu(C16H13NO4)(C5H5N)(H2O)]Z = 2
Mr = 443.93F(000) = 458
Triclinic, P1Dx = 1.540 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0319 (13) ÅCell parameters from 42 reflections
b = 10.0487 (11) Åθ = 4.8–17.3°
c = 10.1973 (14) ŵ = 1.18 mm1
α = 81.973 (10)°T = 293 K
β = 72.624 (9)°Plate, blue
γ = 78.310 (9)°0.58 × 0.46 × 0.15 mm
V = 957.3 (2) Å3
Data collection top
Siemens P4S
diffractometer
3782 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
2θ/ω scansh = 012
Absorption correction: integration
(Wuensch & Prewett, 1965)
k = 1213
Tmin = 0.688, Tmax = 0.883l = 1213
4594 measured reflections3 standard reflections every 97 reflections
4347 independent reflections intensity decay: 0.1%
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.4004P]
where P = (Fo2 + 2Fc2)/3
4347 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.27 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
Cu0.12889 (2)0.15882 (2)0.07618 (2)0.02815 (8)
O1W0.21634 (16)0.03484 (16)0.05347 (17)0.0428 (4)
H1W10.16390.09560.04970.051*
H1W20.30210.07920.07460.051*
O10.04181 (14)0.22775 (15)0.02269 (15)0.0349 (3)
O20.29058 (14)0.13489 (15)0.15710 (14)0.0344 (3)
O30.49918 (15)0.19917 (17)0.12361 (16)0.0406 (3)
O40.57802 (19)0.35678 (18)0.72791 (16)0.0501 (4)
H40.55050.30810.76900.060*
N10.23789 (15)0.27958 (16)0.06025 (15)0.0259 (3)
N1P0.02221 (17)0.04613 (17)0.23672 (16)0.0306 (3)
C10.0462 (2)0.4052 (2)0.1493 (2)0.0311 (4)
C20.0624 (2)0.33246 (19)0.0674 (2)0.0288 (4)
C30.2004 (2)0.3773 (2)0.0826 (2)0.0357 (4)
H3A0.27410.33420.02740.043*
C40.2281 (2)0.4830 (2)0.1773 (3)0.0425 (5)
H4A0.31970.50930.18580.051*
C50.1215 (3)0.5510 (2)0.2601 (3)0.0508 (6)
H5A0.14040.62120.32520.061*
C60.0123 (3)0.5132 (2)0.2443 (2)0.0448 (5)
H6A0.08330.56040.29820.054*
C70.1896 (2)0.3766 (2)0.1386 (2)0.0306 (4)
H7A0.25190.43290.19270.037*
C80.38453 (19)0.2630 (2)0.05547 (19)0.0288 (4)
H8A0.41510.35200.07140.035*
C90.3913 (2)0.1961 (2)0.08763 (19)0.0295 (4)
C100.4854 (2)0.1662 (2)0.1617 (2)0.0350 (4)
H10A0.57770.14680.14450.042*
H10B0.45000.08080.14660.042*
C110.5037 (2)0.2194 (2)0.3108 (2)0.0321 (4)
C120.4393 (2)0.1718 (2)0.3924 (2)0.0414 (5)
H12A0.37940.10840.35350.050*
C130.4614 (2)0.2161 (3)0.5317 (2)0.0424 (5)
H13A0.41710.18200.58470.051*
C140.5496 (2)0.3110 (2)0.5913 (2)0.0354 (4)
C150.6133 (2)0.3620 (2)0.5103 (2)0.0392 (5)
H15A0.67110.42710.54860.047*
C160.5907 (2)0.3159 (2)0.3719 (2)0.0365 (4)
H16A0.63460.35030.31870.044*
C2P0.0806 (2)0.0808 (2)0.2719 (2)0.0395 (5)
H2PA0.17030.11660.21880.047*
C3P0.0135 (3)0.1605 (2)0.3832 (3)0.0462 (5)
H3PA0.05570.24940.40270.055*
C4P0.1171 (2)0.1065 (2)0.4655 (2)0.0442 (5)
H4PA0.16310.15710.54330.053*
C5P0.1780 (2)0.0234 (2)0.4302 (2)0.0413 (5)
H5PA0.26650.06180.48380.050*
C6P0.1072 (2)0.0965 (2)0.3150 (2)0.0344 (4)
H6PB0.15030.18360.29060.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.02186 (12)0.03369 (13)0.02696 (12)0.00624 (9)0.00628 (8)0.00499 (9)
O1W0.0325 (8)0.0390 (8)0.0571 (10)0.0087 (6)0.0072 (7)0.0125 (7)
O10.0254 (7)0.0387 (8)0.0409 (8)0.0097 (6)0.0126 (6)0.0094 (6)
O20.0279 (7)0.0443 (8)0.0301 (7)0.0072 (6)0.0094 (6)0.0053 (6)
O30.0313 (7)0.0539 (9)0.0416 (8)0.0063 (7)0.0168 (6)0.0077 (7)
O40.0662 (11)0.0545 (10)0.0316 (8)0.0183 (9)0.0120 (8)0.0021 (7)
N10.0214 (7)0.0298 (8)0.0251 (7)0.0041 (6)0.0049 (6)0.0014 (6)
N1P0.0258 (8)0.0347 (9)0.0280 (8)0.0059 (6)0.0045 (6)0.0028 (6)
C10.0309 (10)0.0285 (9)0.0331 (10)0.0032 (7)0.0104 (8)0.0003 (7)
C20.0296 (9)0.0260 (9)0.0314 (9)0.0033 (7)0.0104 (8)0.0025 (7)
C30.0302 (10)0.0320 (10)0.0463 (12)0.0004 (8)0.0148 (9)0.0063 (9)
C40.0406 (12)0.0354 (11)0.0571 (14)0.0060 (9)0.0278 (11)0.0091 (10)
C50.0585 (15)0.0375 (12)0.0572 (15)0.0033 (11)0.0310 (13)0.0100 (11)
C60.0451 (13)0.0381 (12)0.0481 (13)0.0074 (10)0.0156 (10)0.0131 (10)
C70.0292 (9)0.0313 (9)0.0292 (9)0.0084 (8)0.0053 (7)0.0026 (7)
C80.0219 (8)0.0330 (10)0.0304 (9)0.0058 (7)0.0059 (7)0.0010 (7)
C90.0256 (9)0.0342 (10)0.0285 (9)0.0018 (7)0.0078 (7)0.0064 (7)
C100.0278 (10)0.0404 (11)0.0320 (10)0.0023 (8)0.0027 (8)0.0043 (8)
C110.0232 (9)0.0406 (11)0.0290 (9)0.0026 (8)0.0014 (7)0.0080 (8)
C120.0355 (11)0.0513 (13)0.0390 (11)0.0184 (10)0.0050 (9)0.0046 (10)
C130.0387 (11)0.0562 (14)0.0376 (11)0.0151 (10)0.0114 (9)0.0095 (10)
C140.0335 (10)0.0388 (11)0.0306 (10)0.0015 (8)0.0053 (8)0.0070 (8)
C150.0388 (11)0.0404 (11)0.0378 (11)0.0132 (9)0.0042 (9)0.0067 (9)
C160.0362 (11)0.0429 (12)0.0333 (10)0.0101 (9)0.0084 (8)0.0111 (9)
C2P0.0322 (10)0.0380 (11)0.0402 (11)0.0003 (9)0.0041 (9)0.0009 (9)
C3P0.0452 (13)0.0363 (11)0.0515 (14)0.0045 (10)0.0129 (11)0.0104 (10)
C4P0.0401 (12)0.0481 (13)0.0406 (12)0.0165 (10)0.0068 (10)0.0120 (10)
C5P0.0298 (10)0.0494 (13)0.0370 (11)0.0066 (9)0.0006 (9)0.0004 (9)
C6P0.0288 (9)0.0335 (10)0.0349 (10)0.0006 (8)0.0039 (8)0.0004 (8)
Geometric parameters (Å, º) top
Cu—O11.9187 (14)C7—H7A0.9300
Cu—N11.9394 (15)C8—C91.534 (3)
Cu—O21.9889 (14)C8—C101.544 (3)
Cu—N1P2.0086 (16)C8—H8A0.9800
Cu—O1W2.3745 (15)C10—C111.509 (3)
O1W—H1W10.8733C10—H10A0.9700
O1W—H1W20.8634C10—H10B0.9700
O1—C21.322 (2)C11—C121.377 (3)
O2—C91.266 (2)C11—C161.393 (3)
O3—C91.249 (2)C12—C131.393 (3)
O4—C141.368 (2)C12—H12A0.9300
O4—H40.8200C13—C141.386 (3)
N1—C71.283 (2)C13—H13A0.9300
N1—C81.461 (2)C14—C151.385 (3)
N1P—C2P1.339 (3)C15—C161.388 (3)
N1P—C6P1.344 (2)C15—H15A0.9300
C1—C61.409 (3)C16—H16A0.9300
C1—C21.424 (3)C2P—C3P1.375 (3)
C1—C71.442 (3)C2P—H2PA0.9300
C2—C31.414 (3)C3P—C4P1.377 (3)
C3—C41.376 (3)C3P—H3PA0.9300
C3—H3A0.9300C4P—C5P1.372 (3)
C4—C51.386 (4)C4P—H4PA0.9300
C4—H4A0.9300C5P—C6P1.378 (3)
C5—C61.370 (3)C5P—H5PA0.9300
C5—H5A0.9300C6P—H6PB0.9300
C6—H6A0.9300
O1—Cu—N193.61 (6)N1—C8—H8A110.2
O1—Cu—O2164.17 (6)C9—C8—H8A110.2
N1—Cu—O283.13 (6)C10—C8—H8A110.2
O1—Cu—N1P90.30 (6)O3—C9—O2124.84 (19)
N1—Cu—N1P172.18 (7)O3—C9—C8117.75 (17)
O2—Cu—N1P91.28 (6)O2—C9—C8117.27 (16)
O1—Cu—O1W99.82 (6)C11—C10—C8115.24 (17)
N1—Cu—O1W95.24 (6)C11—C10—H10A108.5
O2—Cu—O1W95.91 (6)C8—C10—H10A108.5
N1P—Cu—O1W90.76 (6)C11—C10—H10B108.5
Cu—O1W—H1W1121.9C8—C10—H10B108.5
Cu—O1W—H1W2127.0H10A—C10—H10B107.5
H1W1—O1W—H1W2104.4C12—C11—C16117.63 (19)
C2—O1—Cu126.90 (12)C12—C11—C10121.66 (19)
C9—O2—Cu114.88 (12)C16—C11—C10120.69 (18)
C14—O4—H4109.5C11—C12—C13121.7 (2)
C7—N1—C8120.10 (16)C11—C12—H12A119.2
C7—N1—Cu126.41 (13)C13—C12—H12A119.2
C8—N1—Cu113.03 (12)C14—C13—C12120.0 (2)
C2P—N1P—C6P117.85 (17)C14—C13—H13A120.0
C2P—N1P—Cu120.62 (14)C12—C13—H13A120.0
C6P—N1P—Cu121.49 (14)O4—C14—C15117.89 (19)
C6—C1—C2118.75 (19)O4—C14—C13122.9 (2)
C6—C1—C7117.65 (18)C15—C14—C13119.2 (2)
C2—C1—C7123.59 (18)C14—C15—C16120.0 (2)
O1—C2—C3118.67 (18)C14—C15—H15A120.0
O1—C2—C1123.87 (17)C16—C15—H15A120.0
C3—C2—C1117.45 (18)C15—C16—C11121.50 (19)
C4—C3—C2121.6 (2)C15—C16—H16A119.2
C4—C3—H3A119.2C11—C16—H16A119.2
C2—C3—H3A119.2N1P—C2P—C3P122.8 (2)
C3—C4—C5120.9 (2)N1P—C2P—H2PA118.6
C3—C4—H4A119.5C3P—C2P—H2PA118.6
C5—C4—H4A119.5C2P—C3P—C4P119.0 (2)
C6—C5—C4118.9 (2)C2P—C3P—H3PA120.5
C6—C5—H5A120.6C4P—C3P—H3PA120.5
C4—C5—H5A120.6C5P—C4P—C3P118.7 (2)
C5—C6—C1122.3 (2)C5P—C4P—H4PA120.7
C5—C6—H6A118.8C3P—C4P—H4PA120.7
C1—C6—H6A118.8C4P—C5P—C6P119.5 (2)
N1—C7—C1125.11 (17)C4P—C5P—H5PA120.2
N1—C7—H7A117.4C6P—C5P—H5PA120.2
C1—C7—H7A117.4N1P—C6P—C5P122.12 (19)
N1—C8—C9107.76 (14)N1P—C6P—H6PB118.9
N1—C8—C10111.61 (16)C5P—C6P—H6PB118.9
C9—C8—C10106.86 (15)
N1—Cu—O1—C26.36 (17)C6—C1—C7—N1177.8 (2)
O2—Cu—O1—C271.1 (3)C2—C1—C7—N13.5 (3)
N1P—Cu—O1—C2166.86 (17)C7—N1—C8—C9151.68 (17)
O1W—Cu—O1—C2102.32 (16)Cu—N1—C8—C921.07 (18)
O1—Cu—O2—C982.7 (2)C7—N1—C8—C1091.3 (2)
N1—Cu—O2—C93.76 (14)Cu—N1—C8—C1095.95 (16)
N1P—Cu—O2—C9178.28 (14)Cu—O2—C9—O3176.57 (16)
O1W—Cu—O2—C990.82 (14)Cu—O2—C9—C87.8 (2)
O1—Cu—N1—C76.87 (17)N1—C8—C9—O3165.10 (17)
O2—Cu—N1—C7157.57 (17)C10—C8—C9—O374.8 (2)
O1W—Cu—N1—C7107.09 (17)N1—C8—C9—O219.0 (2)
O1—Cu—N1—C8179.08 (12)C10—C8—C9—O2101.1 (2)
O2—Cu—N1—C814.64 (12)N1—C8—C10—C1167.4 (2)
O1W—Cu—N1—C880.70 (12)C9—C8—C10—C11175.01 (16)
O1—Cu—N1P—C2P140.15 (17)C8—C10—C11—C12104.5 (2)
O2—Cu—N1P—C2P55.61 (17)C8—C10—C11—C1677.5 (2)
O1W—Cu—N1P—C2P40.32 (17)C16—C11—C12—C131.1 (3)
O1—Cu—N1P—C6P42.17 (16)C10—C11—C12—C13176.9 (2)
O2—Cu—N1P—C6P122.07 (16)C11—C12—C13—C140.4 (4)
O1W—Cu—N1P—C6P142.00 (16)C12—C13—C14—O4178.7 (2)
Cu—O1—C2—C3173.34 (14)C12—C13—C14—C150.8 (3)
Cu—O1—C2—C15.6 (3)O4—C14—C15—C16178.28 (19)
C6—C1—C2—O1178.5 (2)C13—C14—C15—C161.3 (3)
C7—C1—C2—O12.9 (3)C14—C15—C16—C110.5 (3)
C6—C1—C2—C32.6 (3)C12—C11—C16—C150.7 (3)
C7—C1—C2—C3176.02 (19)C10—C11—C16—C15177.42 (19)
O1—C2—C3—C4178.10 (19)C6P—N1P—C2P—C3P0.3 (3)
C1—C2—C3—C42.9 (3)Cu—N1P—C2P—C3P178.10 (18)
C2—C3—C4—C50.9 (3)N1P—C2P—C3P—C4P2.4 (4)
C3—C4—C5—C61.4 (4)C2P—C3P—C4P—C5P2.4 (4)
C4—C5—C6—C11.6 (4)C3P—C4P—C5P—C6P0.5 (4)
C2—C1—C6—C50.4 (4)C2P—N1P—C6P—C5P1.7 (3)
C7—C1—C6—C5178.3 (2)Cu—N1P—C6P—C5P176.04 (17)
C8—N1—C7—C1178.30 (17)C4P—C5P—C6P—N1P1.6 (4)
Cu—N1—C7—C16.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O1i0.871.922.793 (2)175
O1W—H1W2···O3ii0.862.072.930 (2)176
O4—H4···O3iii0.821.892.705 (2)175
Symmetry codes: (i) x, y, z; (ii) x+1, y, z; (iii) x, y, z1.
 

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