Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024518/hb2419sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024518/hb2419Isup2.hkl |
CCDC reference: 650706
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.036
- wR factor = 0.099
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.845(10) ...... 3.00 su-Ra O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.845(10) ...... 3.00 su-Ra O2W -H2W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Ra O3W -H3W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.847(10) ...... 3.00 su-Ra O3W -H3W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Ra O1W -H4# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O2W -H6# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Ra O3W -H8# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.850(10) ...... 3.00 su-Ra O3W -H9# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.95(3), Rep 1.950(10) ...... 3.00 su-Ra H4# -O1 1.555 2.666 PLAT736_ALERT_1_C H...A Calc 1.93(3), Rep 1.930(10) ...... 3.00 su-Ra H6# -O3 1.555 2.676 PLAT736_ALERT_1_C H...A Calc 1.94(3), Rep 1.950(10) ...... 3.00 su-Ra H8# -O2 1.555 2.766 PLAT736_ALERT_1_C H...A Calc 1.85(3), Rep 1.850(10) ...... 3.00 su-Ra H9# -O4W 1.555 1.565 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.30 Deg. C2 -N1 -C2' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.40 Deg. C2 -C1 -C2' 1.555 1.555 1.555
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C2' = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 35
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
For the structures of other salicylidene-glycine-nickel complexes, see Cui et al. (1992, 1993); Rodríguez et al. (1990).
5-Formylsalicylaldehyde (0.2 mmol, 0.27 g), D,L-alanine (0.2 mmol, 0.18 g) and potassium hydroxide (0.2 mmol, 0.11 g) were dissolved in 80% aqueous methanol (15 ml). The mixture was stirred for 1 h to give a clear yellow solution. To the solution was added an aqueous solution (15 ml) of nickel(II) acetate hexahydrate (0.2 mmol, 0.57 g). The mixture heated at 323 K for 3 h. Green crystals of (I) were obtained in about 50% yield.
The ethylidene part of the molecule is disordered over two positions; the disorder refined to a 0.737 (11):0.263 (11) ratio. Pairs of equivalent carbon-carbon distances were restrained to within 0.01 Å of each other, and the disordered atoms were restrained to vibrate in a nearly isotropic manner.
The carbon-bound H atoms were placed in calculated positions (C—H 0.93 Å), and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C).
The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H = 0.85±0.01 Å; Uiso was freely varied for each H atom.
The salicylidene-glycine carboxylic acid when doubly deprotonated generally chelates to metal centers through its N,O,O' atoms. The planar ligand chelates to nickel in this manner in, for example, the tripyridinenickel complex for which it occupies the meridional sites (Cui et al., 1992). The 3-methoxy analog also affords a six-coordinate tripyridine complex, but it also contains ethanol as the solvate molecule (Cui et al., 1993). The N-(5-bromosalicylidene)tryptophanate complex is a triaqua complex that crystallizes with two uncoordinated water molecules (Rodríguez et al., 1990).
This chelating feature is also found in the title compound, (I), (Table 1) which has a formyl group as substituent in the aromatic ring. The formyl substitutent in involved in hydrogen bonding interactions with the water molecules to give rise to a three-dimenional network architecture (Table 2).
For the structures of other salicylidene-glycine-nickel complexes, see Cui et al. (1992, 1993); Rodríguez et al. (1990).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).
Fig. 1. View of (I) as a displacement ellipsoid plot (50% probability). Hydrogen atoms are drawn as spheres of arbitrary radii; the minor disorder component is not shown. |
[Ni(C11H9NO4)(H2O)3].H2O | Z = 2 |
Mr = 349.97 | F(000) = 364 |
Triclinic, P1 | Dx = 1.647 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.861 (2) Å | Cell parameters from 2418 reflections |
b = 8.664 (2) Å | θ = 2.3–27.1° |
c = 12.363 (3) Å | µ = 1.41 mm−1 |
α = 82.967 (3)° | T = 295 K |
β = 80.639 (3)° | Block, green |
γ = 77.706 (3)° | 0.20 × 0.10 × 0.05 mm |
V = 705.5 (3) Å3 |
Bruker SMART CCD diffractometer | 2966 independent reflections |
Radiation source: fine-focus sealed tube | 2635 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.1°, θmin = 1.7° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −5→8 |
Tmin = 0.870, Tmax = 0.933 | k = −9→11 |
4072 measured reflections | l = −14→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.059P)2 + 0.1949P] where P = (Fo2 + 2Fc2)/3 |
2966 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 0.55 e Å−3 |
35 restraints | Δρmin = −0.43 e Å−3 |
[Ni(C11H9NO4)(H2O)3].H2O | γ = 77.706 (3)° |
Mr = 349.97 | V = 705.5 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.861 (2) Å | Mo Kα radiation |
b = 8.664 (2) Å | µ = 1.41 mm−1 |
c = 12.363 (3) Å | T = 295 K |
α = 82.967 (3)° | 0.20 × 0.10 × 0.05 mm |
β = 80.639 (3)° |
Bruker SMART CCD diffractometer | 2966 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 2635 reflections with I > 2σ(I) |
Tmin = 0.870, Tmax = 0.933 | Rint = 0.020 |
4072 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 35 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.55 e Å−3 |
2966 reflections | Δρmin = −0.43 e Å−3 |
241 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.62546 (4) | 0.75271 (3) | 0.39426 (2) | 0.02769 (12) | |
O1 | 0.7525 (3) | 0.52716 (18) | 0.44937 (13) | 0.0347 (4) | |
O2 | 0.9267 (3) | 0.3003 (2) | 0.39286 (16) | 0.0463 (5) | |
O3 | 0.5195 (3) | 0.96942 (18) | 0.32259 (13) | 0.0315 (4) | |
O4 | 0.6313 (4) | 1.3584 (2) | −0.14612 (15) | 0.0495 (5) | |
O1W | 0.3722 (3) | 0.6685 (2) | 0.36805 (15) | 0.0396 (4) | |
O2W | 0.4613 (3) | 0.8013 (2) | 0.54397 (15) | 0.0382 (4) | |
O3W | 0.8478 (3) | 0.8416 (2) | 0.44387 (17) | 0.0445 (5) | |
O4W | 1.0881 (3) | 0.0138 (2) | 0.31021 (19) | 0.0474 (5) | |
N1 | 0.7874 (3) | 0.6852 (2) | 0.25235 (17) | 0.0356 (5) | |
C1 | 0.8554 (4) | 0.4445 (3) | 0.3764 (2) | 0.0355 (5) | |
C2 | 0.9180 (6) | 0.5251 (4) | 0.2619 (3) | 0.0302 (10) | 0.737 (11) |
H2 | 1.0598 | 0.5342 | 0.2535 | 0.036* | 0.737 (11) |
C3 | 0.8859 (14) | 0.4276 (7) | 0.1736 (6) | 0.065 (2) | 0.737 (11) |
H3A | 0.9225 | 0.3167 | 0.1967 | 0.097* | 0.737 (11) |
H3B | 0.9684 | 0.4520 | 0.1058 | 0.097* | 0.737 (11) |
H3C | 0.7468 | 0.4529 | 0.1630 | 0.097* | 0.737 (11) |
C2' | 0.817 (2) | 0.5062 (9) | 0.2564 (6) | 0.045 (4) | 0.263 (11) |
H2' | 0.6895 | 0.4803 | 0.2457 | 0.054* | 0.263 (11) |
C3' | 0.980 (2) | 0.430 (2) | 0.1702 (14) | 0.049 (4) | 0.263 (11) |
H3'1 | 0.9542 | 0.4786 | 0.0985 | 0.073* | 0.263 (11) |
H3'2 | 0.9805 | 0.3190 | 0.1744 | 0.073* | 0.263 (11) |
H3'3 | 1.1085 | 0.4456 | 0.1831 | 0.073* | 0.263 (11) |
C4 | 0.8019 (4) | 0.7699 (3) | 0.1609 (2) | 0.0361 (5) | |
H4 | 0.8834 | 0.7222 | 0.1015 | 0.043* | |
C5 | 0.7030 (3) | 0.9339 (3) | 0.14088 (18) | 0.0284 (5) | |
C6 | 0.7401 (4) | 1.0054 (3) | 0.03400 (19) | 0.0320 (5) | |
H6 | 0.8249 | 0.9459 | −0.0190 | 0.038* | |
C7 | 0.6553 (4) | 1.1611 (3) | 0.00411 (19) | 0.0326 (5) | |
C8 | 0.5282 (4) | 1.2502 (3) | 0.0832 (2) | 0.0372 (5) | |
H8 | 0.4712 | 1.3555 | 0.0643 | 0.045* | |
C9 | 0.4865 (4) | 1.1843 (3) | 0.1885 (2) | 0.0375 (6) | |
H9 | 0.4005 | 1.2458 | 0.2400 | 0.045* | |
C10 | 0.5710 (3) | 1.0242 (3) | 0.22144 (18) | 0.0279 (4) | |
C11 | 0.6961 (4) | 1.2240 (3) | −0.1101 (2) | 0.0386 (6) | |
H11 | 0.7779 | 1.1560 | −0.1590 | 0.046* | |
H1W1 | 0.336 (5) | 0.601 (3) | 0.418 (2) | 0.058 (10)* | |
H1W2 | 0.369 (6) | 0.640 (4) | 0.3058 (16) | 0.066 (11)* | |
H2W1 | 0.473 (6) | 0.875 (3) | 0.580 (3) | 0.065 (11)* | |
H2W2 | 0.3354 (18) | 0.810 (4) | 0.548 (3) | 0.069 (12)* | |
H3W1 | 0.933 (4) | 0.787 (3) | 0.482 (2) | 0.046 (9)* | |
H3W2 | 0.930 (4) | 0.886 (4) | 0.399 (2) | 0.061 (11)* | |
H4W1 | 1.048 (5) | 0.1082 (18) | 0.326 (3) | 0.052 (9)* | |
H4W2 | 1.207 (3) | −0.009 (4) | 0.325 (3) | 0.071 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.03501 (19) | 0.02257 (17) | 0.02212 (17) | −0.00216 (12) | −0.00137 (12) | 0.00139 (11) |
O1 | 0.0449 (10) | 0.0265 (8) | 0.0270 (8) | −0.0007 (7) | 0.0002 (7) | 0.0024 (6) |
O2 | 0.0660 (13) | 0.0256 (8) | 0.0379 (10) | 0.0062 (8) | −0.0041 (9) | 0.0025 (7) |
O3 | 0.0409 (9) | 0.0247 (7) | 0.0234 (8) | −0.0008 (7) | 0.0009 (7) | 0.0012 (6) |
O4 | 0.0741 (14) | 0.0393 (10) | 0.0324 (10) | −0.0108 (9) | −0.0107 (9) | 0.0109 (8) |
O1W | 0.0515 (11) | 0.0420 (10) | 0.0285 (9) | −0.0172 (8) | −0.0077 (8) | 0.0020 (8) |
O2W | 0.0443 (11) | 0.0399 (10) | 0.0305 (9) | −0.0111 (8) | 0.0032 (8) | −0.0105 (7) |
O3W | 0.0438 (11) | 0.0461 (11) | 0.0454 (11) | −0.0136 (9) | −0.0159 (9) | 0.0105 (9) |
O4W | 0.0417 (11) | 0.0376 (10) | 0.0598 (13) | −0.0030 (9) | −0.0008 (10) | −0.0093 (9) |
N1 | 0.0460 (12) | 0.0244 (9) | 0.0283 (10) | 0.0029 (8) | 0.0019 (9) | 0.0024 (7) |
C1 | 0.0442 (14) | 0.0258 (11) | 0.0322 (13) | −0.0020 (10) | −0.0042 (10) | 0.0034 (9) |
C2 | 0.0248 (19) | 0.0265 (16) | 0.0328 (18) | 0.0014 (13) | 0.0023 (14) | 0.0028 (12) |
C3 | 0.112 (6) | 0.033 (2) | 0.042 (3) | 0.013 (3) | −0.020 (4) | −0.0076 (19) |
C2' | 0.049 (7) | 0.036 (5) | 0.038 (5) | 0.004 (5) | 0.011 (5) | 0.004 (4) |
C3' | 0.057 (7) | 0.037 (6) | 0.036 (6) | 0.007 (6) | 0.007 (6) | 0.010 (4) |
C4 | 0.0437 (14) | 0.0333 (12) | 0.0236 (11) | 0.0018 (10) | 0.0034 (10) | −0.0006 (9) |
C5 | 0.0312 (11) | 0.0268 (10) | 0.0257 (11) | −0.0058 (9) | −0.0038 (9) | 0.0032 (8) |
C6 | 0.0356 (12) | 0.0342 (12) | 0.0249 (11) | −0.0065 (10) | −0.0016 (9) | −0.0012 (9) |
C7 | 0.0414 (13) | 0.0326 (12) | 0.0241 (11) | −0.0100 (10) | −0.0075 (10) | 0.0047 (9) |
C8 | 0.0507 (15) | 0.0253 (11) | 0.0326 (13) | −0.0046 (10) | −0.0068 (11) | 0.0051 (9) |
C9 | 0.0520 (15) | 0.0263 (11) | 0.0288 (12) | −0.0002 (10) | −0.0018 (11) | −0.0005 (9) |
C10 | 0.0313 (11) | 0.0268 (10) | 0.0248 (11) | −0.0050 (9) | −0.0052 (9) | 0.0008 (8) |
C11 | 0.0500 (15) | 0.0383 (13) | 0.0281 (12) | −0.0132 (11) | −0.0068 (10) | 0.0045 (10) |
Ni1—N1 | 1.999 (2) | C2—C3 | 1.528 (6) |
Ni1—O3 | 2.0149 (16) | C2—H2 | 0.9800 |
Ni1—O2W | 2.0450 (19) | C3—H3A | 0.9600 |
Ni1—O1 | 2.0455 (16) | C3—H3B | 0.9600 |
Ni1—O3W | 2.053 (2) | C3—H3C | 0.9600 |
Ni1—O1W | 2.1063 (19) | C2'—C3' | 1.512 (9) |
C1—O1 | 1.250 (3) | C2'—H2' | 0.9800 |
C1—O2 | 1.245 (3) | C3'—H3'1 | 0.9600 |
O3—C10 | 1.302 (3) | C3'—H3'2 | 0.9600 |
O4—C11 | 1.212 (3) | C3'—H3'3 | 0.9600 |
O1W—H1W1 | 0.845 (10) | C4—C5 | 1.449 (3) |
O1W—H1W2 | 0.842 (10) | C4—H4 | 0.9300 |
O2W—H2W1 | 0.845 (10) | C5—C6 | 1.397 (3) |
O2W—H2W2 | 0.845 (10) | C5—C10 | 1.421 (3) |
O3W—H3W1 | 0.840 (10) | C6—C7 | 1.382 (3) |
O3W—H3W2 | 0.847 (10) | C6—H6 | 0.9300 |
O4W—H4W1 | 0.841 (10) | C7—C8 | 1.390 (4) |
O4W—H4W2 | 0.844 (10) | C7—C11 | 1.454 (3) |
N1—C4 | 1.272 (3) | C8—C9 | 1.368 (3) |
N1—C2 | 1.485 (4) | C8—H8 | 0.9300 |
N1—C2' | 1.516 (8) | C9—C10 | 1.422 (3) |
C1—C2 | 1.538 (4) | C9—H9 | 0.9300 |
C1—C2' | 1.558 (8) | C11—H11 | 0.9300 |
N1—Ni1—O3 | 91.55 (7) | C1—C2—H2 | 110.1 |
N1—Ni1—O2W | 175.02 (7) | C2—C3—H3A | 109.5 |
O3—Ni1—O2W | 93.10 (7) | C2—C3—H3B | 109.5 |
N1—Ni1—O1 | 81.70 (7) | H3A—C3—H3B | 109.5 |
O3—Ni1—O1 | 173.25 (6) | C2—C3—H3C | 109.5 |
O2W—Ni1—O1 | 93.65 (7) | H3A—C3—H3C | 109.5 |
N1—Ni1—O3W | 95.22 (9) | H3B—C3—H3C | 109.5 |
O3—Ni1—O3W | 89.33 (8) | C3'—C2'—N1 | 114.9 (11) |
O2W—Ni1—O3W | 86.63 (8) | C3'—C2'—C1 | 113.1 (11) |
O1—Ni1—O3W | 91.04 (8) | N1—C2'—C1 | 105.0 (6) |
N1—Ni1—O1W | 93.73 (9) | C3'—C2'—H2' | 107.8 |
O3—Ni1—O1W | 91.45 (7) | N1—C2'—H2' | 107.8 |
O2W—Ni1—O1W | 84.37 (8) | C1—C2'—H2' | 107.8 |
O1—Ni1—O1W | 89.24 (7) | C2'—C3'—H3'1 | 109.5 |
O3W—Ni1—O1W | 170.99 (8) | C2'—C3'—H3'2 | 109.5 |
C1—O1—Ni1 | 114.98 (14) | H3'1—C3'—H3'2 | 109.5 |
C10—O3—Ni1 | 126.69 (14) | C2'—C3'—H3'3 | 109.5 |
Ni1—O1W—H1W1 | 114 (2) | H3'1—C3'—H3'3 | 109.5 |
Ni1—O1W—H1W2 | 119 (3) | H3'2—C3'—H3'3 | 109.5 |
H1W1—O1W—H1W2 | 110 (3) | N1—C4—C5 | 125.9 (2) |
Ni1—O2W—H2W1 | 124 (3) | N1—C4—H4 | 117.0 |
Ni1—O2W—H2W2 | 116 (3) | C5—C4—H4 | 117.0 |
H2W1—O2W—H2W2 | 104 (4) | C6—C5—C10 | 118.8 (2) |
Ni1—O3W—H3W1 | 123 (2) | C6—C5—C4 | 116.7 (2) |
Ni1—O3W—H3W2 | 122 (2) | C10—C5—C4 | 124.6 (2) |
H3W1—O3W—H3W2 | 96 (3) | C7—C6—C5 | 122.4 (2) |
H4W1—O4W—H4W2 | 103 (3) | C7—C6—H6 | 118.8 |
C4—N1—C2 | 118.8 (2) | C5—C6—H6 | 118.8 |
C4—N1—C2' | 121.0 (3) | C6—C7—C8 | 118.9 (2) |
C2—N1—C2' | 29.3 (5) | C6—C7—C11 | 118.7 (2) |
C4—N1—Ni1 | 126.63 (17) | C8—C7—C11 | 122.3 (2) |
C2—N1—Ni1 | 114.18 (17) | C9—C8—C7 | 120.5 (2) |
C2'—N1—Ni1 | 107.9 (4) | C9—C8—H8 | 119.8 |
O2—C1—O1 | 123.8 (2) | C7—C8—H8 | 119.8 |
O2—C1—C2 | 116.6 (2) | C8—C9—C10 | 121.8 (2) |
O1—C1—C2 | 119.3 (2) | C8—C9—H9 | 119.1 |
O2—C1—C2' | 116.3 (3) | C10—C9—H9 | 119.1 |
O1—C1—C2' | 115.2 (4) | O3—C10—C5 | 124.49 (19) |
C2—C1—C2' | 28.4 (5) | O3—C10—C9 | 117.9 (2) |
N1—C2—C3 | 109.6 (4) | C5—C10—C9 | 117.6 (2) |
N1—C2—C1 | 107.6 (2) | O4—C11—C7 | 124.9 (3) |
C3—C2—C1 | 109.3 (4) | O4—C11—H11 | 117.6 |
N1—C2—H2 | 110.1 | C7—C11—H11 | 117.6 |
C3—C2—H2 | 110.1 | ||
N1—Ni1—O1—C1 | −5.22 (18) | C4—N1—C2'—C3' | 37.6 (17) |
O2W—Ni1—O1—C1 | 172.96 (19) | C2—N1—C2'—C3' | −57.0 (15) |
O3W—Ni1—O1—C1 | −100.35 (19) | Ni1—N1—C2'—C3' | −164.6 (12) |
O1W—Ni1—O1—C1 | 88.66 (19) | C4—N1—C2'—C1 | 162.6 (5) |
N1—Ni1—O3—C10 | −4.48 (19) | C2—N1—C2'—C1 | 68.0 (8) |
O2W—Ni1—O3—C10 | 177.31 (19) | Ni1—N1—C2'—C1 | −39.7 (9) |
O3W—Ni1—O3—C10 | 90.72 (19) | O2—C1—C2'—C3' | −38.8 (16) |
O1W—Ni1—O3—C10 | −98.26 (19) | O1—C1—C2'—C3' | 164.5 (11) |
O3—Ni1—N1—C4 | 2.1 (2) | C2—C1—C2'—C3' | 58.9 (15) |
O1—Ni1—N1—C4 | −177.6 (3) | O2—C1—C2'—N1 | −164.9 (5) |
O3W—Ni1—N1—C4 | −87.3 (2) | O1—C1—C2'—N1 | 38.4 (10) |
O1W—Ni1—N1—C4 | 93.7 (2) | C2—C1—C2'—N1 | −67.1 (8) |
O3—Ni1—N1—C2 | 175.2 (2) | C2—N1—C4—C5 | −172.8 (3) |
O1—Ni1—N1—C2 | −4.6 (2) | C2'—N1—C4—C5 | 153.3 (7) |
O3W—Ni1—N1—C2 | 85.7 (2) | Ni1—N1—C4—C5 | 0.0 (4) |
O1W—Ni1—N1—C2 | −93.3 (2) | N1—C4—C5—C6 | 179.8 (3) |
O3—Ni1—N1—C2' | −154.0 (6) | N1—C4—C5—C10 | −1.1 (4) |
O1—Ni1—N1—C2' | 26.2 (6) | C10—C5—C6—C7 | 0.9 (4) |
O3W—Ni1—N1—C2' | 116.5 (6) | C4—C5—C6—C7 | −179.9 (2) |
O1W—Ni1—N1—C2' | −62.5 (6) | C5—C6—C7—C8 | −0.1 (4) |
Ni1—O1—C1—O2 | −172.5 (2) | C5—C6—C7—C11 | −177.7 (2) |
Ni1—O1—C1—C2 | 14.0 (3) | C6—C7—C8—C9 | −0.6 (4) |
Ni1—O1—C1—C2' | −17.7 (7) | C11—C7—C8—C9 | 176.9 (2) |
C4—N1—C2—C3 | −56.1 (6) | C7—C8—C9—C10 | 0.4 (4) |
C2'—N1—C2—C3 | 46.6 (8) | Ni1—O3—C10—C5 | 4.8 (3) |
Ni1—N1—C2—C3 | 130.3 (4) | Ni1—O3—C10—C9 | −176.50 (17) |
C4—N1—C2—C1 | −174.9 (3) | C6—C5—C10—O3 | 177.6 (2) |
C2'—N1—C2—C1 | −72.2 (6) | C4—C5—C10—O3 | −1.5 (4) |
Ni1—N1—C2—C1 | 11.5 (4) | C6—C5—C10—C9 | −1.1 (3) |
O2—C1—C2—N1 | 169.1 (3) | C4—C5—C10—C9 | 179.8 (2) |
O1—C1—C2—N1 | −16.9 (4) | C8—C9—C10—O3 | −178.3 (2) |
C2'—C1—C2—N1 | 72.4 (6) | C8—C9—C10—C5 | 0.5 (4) |
O2—C1—C2—C3 | 50.2 (5) | C6—C7—C11—O4 | −179.7 (3) |
O1—C1—C2—C3 | −135.9 (4) | C8—C7—C11—O4 | 2.8 (4) |
C2'—C1—C2—C3 | −46.5 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O1i | 0.85 (1) | 1.95 (1) | 2.784 (2) | 170 (3) |
O1w—H1w2···O4ii | 0.84 (1) | 1.97 (2) | 2.786 (3) | 162 (4) |
O2w—H2w1···O3iii | 0.85 (1) | 1.93 (1) | 2.769 (2) | 173 (4) |
O2w—H2w2···O2i | 0.85 (1) | 2.19 (2) | 2.937 (3) | 147 (3) |
O3w—H3w1···O2iv | 0.84 (1) | 1.95 (1) | 2.753 (3) | 161 (3) |
O3w—H3w2···O4wv | 0.85 (1) | 1.85 (1) | 2.689 (3) | 171 (4) |
O4w—H4w1···O2 | 0.84 (1) | 1.92 (1) | 2.741 (3) | 166 (3) |
O4w—H4w2···O3vi | 0.84 (1) | 2.11 (2) | 2.929 (3) | 165 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+2, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, y+1, z; (vi) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C11H9NO4)(H2O)3].H2O |
Mr | 349.97 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 6.861 (2), 8.664 (2), 12.363 (3) |
α, β, γ (°) | 82.967 (3), 80.639 (3), 77.706 (3) |
V (Å3) | 705.5 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.41 |
Crystal size (mm) | 0.20 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.870, 0.933 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4072, 2966, 2635 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.099, 1.04 |
No. of reflections | 2966 |
No. of parameters | 241 |
No. of restraints | 35 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.55, −0.43 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2006).
Ni1—N1 | 1.999 (2) | Ni1—O1 | 2.0455 (16) |
Ni1—O3 | 2.0149 (16) | Ni1—O3W | 2.053 (2) |
Ni1—O2W | 2.0450 (19) | Ni1—O1W | 2.1063 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O1i | 0.85 (1) | 1.95 (1) | 2.784 (2) | 170 (3) |
O1w—H1w2···O4ii | 0.84 (1) | 1.97 (2) | 2.786 (3) | 162 (4) |
O2w—H2w1···O3iii | 0.85 (1) | 1.93 (1) | 2.769 (2) | 173 (4) |
O2w—H2w2···O2i | 0.85 (1) | 2.19 (2) | 2.937 (3) | 147 (3) |
O3w—H3w1···O2iv | 0.84 (1) | 1.95 (1) | 2.753 (3) | 161 (3) |
O3w—H3w2···O4wv | 0.85 (1) | 1.85 (1) | 2.689 (3) | 171 (4) |
O4w—H4w1···O2 | 0.84 (1) | 1.92 (1) | 2.741 (3) | 166 (3) |
O4w—H4w2···O3vi | 0.84 (1) | 2.11 (2) | 2.929 (3) | 165 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+2, −z+1; (iv) −x+2, −y+1, −z+1; (v) x, y+1, z; (vi) x+1, y−1, z. |
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The salicylidene-glycine carboxylic acid when doubly deprotonated generally chelates to metal centers through its N,O,O' atoms. The planar ligand chelates to nickel in this manner in, for example, the tripyridinenickel complex for which it occupies the meridional sites (Cui et al., 1992). The 3-methoxy analog also affords a six-coordinate tripyridine complex, but it also contains ethanol as the solvate molecule (Cui et al., 1993). The N-(5-bromosalicylidene)tryptophanate complex is a triaqua complex that crystallizes with two uncoordinated water molecules (Rodríguez et al., 1990).
This chelating feature is also found in the title compound, (I), (Table 1) which has a formyl group as substituent in the aromatic ring. The formyl substitutent in involved in hydrogen bonding interactions with the water molecules to give rise to a three-dimenional network architecture (Table 2).