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In the title compound, [Ni(C4H12N2O)2](C4O4)·H2O or [Ni(Hydet-en)2](Sq)·H2O, where Hydet-en is N-(2-hydroxy­ethyl)ethyl­enediamine and Sq is the squarate dianion, the NiII centre has a distorted octa­hedral coordination geometry comprising four amine N and two hydroxyl O atoms from two tridentate Hydet-en ligands. All the O atoms of the squarate dianion are involved in N—H...O and O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039036/ci6709sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039036/ci6709Isup2.hkl
Contains datablock I

CCDC reference: 293870

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 97%
  • Disorder in solvent or counterion
  • R factor = 0.042
  • wR factor = 0.094
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O5 .. O7 .. 2.70 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O6 .. O7 .. 2.63 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 10.00 Perc.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C12 H26 N4 Ni1 O7 Atom count from the _atom_site data: C12 H25 N4 Ni1 O7 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C12 H26 N4 Ni O7 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 48.00 48.00 0.00 H 104.00 100.00 4.00 N 16.00 16.00 0.00 Ni 4.00 4.00 0.00 O 28.00 28.00 0.00
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[N-(2-hydroxyethyl)ethylenediamine-κ3N,N',O]nickel(II) squarate monohydrate top
Crystal data top
[Ni(C4H12N2O)2](C4O4)·H2OF(000) = 840
Mr = 397.08Dx = 1.500 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5487 reflections
a = 11.9740 (8) Åθ = 2.3–28.0°
b = 8.7618 (4) ŵ = 1.14 mm1
c = 16.9051 (12) ÅT = 297 K
β = 97.454 (6)°Prism, violet
V = 1758.59 (19) Å30.30 × 0.28 × 0.16 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
4128 independent reflections
Radiation source: fine-focus sealed tube3478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 6.67 pixels mm-1θmax = 27.8°, θmin = 2.4°
ω scansh = 1515
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1111
Tmin = 0.659, Tmax = 0.763l = 2222
28256 measured reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0321P)2 + 1.2308P]
where P = (Fo2 + 2Fc2)/3
4128 reflections(Δ/σ)max = 0.004
250 parametersΔρmax = 0.48 e Å3
3 restraintsΔρmin = 0.65 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*/UeqOcc. (<1)
C10.1482 (3)0.3552 (3)0.14839 (18)0.0505 (6)
H1A0.13960.33670.09140.061*
H1B0.10370.28010.17270.061*
C20.2709 (3)0.3417 (3)0.18295 (18)0.0528 (7)
H2A0.27900.35250.24050.063*
H2B0.30020.24270.17030.063*
C30.4475 (2)0.4920 (4)0.1870 (2)0.0629 (8)
H3A0.49530.40480.18040.076*
H3B0.44700.50940.24360.076*
C40.4911 (3)0.6302 (5)0.1490 (2)0.0747 (10)
H4A0.56270.66090.17820.090*
H4B0.50280.60720.09450.090*
C50.1261 (3)0.8248 (3)0.01590 (17)0.0536 (7)
H5A0.04920.79170.01760.064*
H5B0.13060.87080.03580.064*
C60.1595 (3)0.9401 (3)0.08124 (17)0.0535 (7)
H6A0.23410.97990.07700.064*
H6B0.10671.02460.07670.064*
C70.2093 (3)0.9424 (3)0.23007 (17)0.0517 (7)
H7A0.16331.02940.24050.062*
H7B0.28380.97900.22300.062*
C80.2168 (3)0.8323 (3)0.29851 (17)0.0558 (7)
H8A0.25700.87850.34610.067*
H8B0.14200.80460.30950.067*
C90.1494 (2)0.3266 (3)0.37272 (15)0.0458 (6)
C100.1670 (2)0.1909 (3)0.42371 (14)0.0400 (5)
C110.2775 (2)0.2510 (3)0.45657 (15)0.0441 (6)
C120.2595 (2)0.3832 (3)0.40525 (16)0.0472 (6)
N10.10912 (17)0.5102 (2)0.16446 (13)0.0407 (4)
H1C0.09080.51610.21440.049*
H1D0.04800.53430.12990.049*
N20.33288 (18)0.4630 (3)0.14809 (13)0.0425 (5)
N30.20283 (19)0.6935 (3)0.02770 (12)0.0437 (5)
H3C0.26610.71240.00590.052*
H3D0.16970.60990.00430.052*
N40.1586 (2)0.8623 (2)0.15808 (13)0.0402 (4)
O10.27553 (18)0.7001 (2)0.27665 (11)0.0496 (5)
O20.41059 (17)0.7518 (3)0.14956 (14)0.0570 (5)
O30.07164 (17)0.3762 (3)0.32267 (13)0.0711 (7)
O40.11124 (17)0.0759 (2)0.43492 (12)0.0553 (5)
O50.35550 (17)0.2085 (3)0.50836 (13)0.0664 (6)
O60.3149 (2)0.5016 (3)0.39384 (14)0.0715 (7)
O70.4344 (4)0.6832 (8)0.4959 (3)0.0913 (19)0.50
O80.5368 (4)0.5355 (6)0.4022 (3)0.0672 (13)0.50
H8C0.480 (4)0.517 (9)0.424 (4)0.10 (3)*0.50
H8D0.571 (5)0.609 (6)0.426 (4)0.08 (2)*0.50
Ni10.24129 (3)0.65868 (3)0.150954 (18)0.03395 (9)
H40.092 (3)0.842 (4)0.1614 (19)0.053 (9)*
H10.282 (3)0.628 (5)0.318 (2)0.079 (12)*
H20.421 (3)0.831 (5)0.121 (2)0.080 (13)*
H30.338 (2)0.440 (3)0.0999 (17)0.039 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0629 (17)0.0320 (12)0.0559 (16)0.0090 (12)0.0056 (13)0.0006 (11)
C20.0663 (18)0.0365 (13)0.0555 (16)0.0102 (13)0.0067 (13)0.0065 (12)
C30.0426 (15)0.070 (2)0.072 (2)0.0173 (14)0.0091 (13)0.0101 (16)
C40.0363 (15)0.100 (3)0.087 (2)0.0009 (17)0.0070 (15)0.018 (2)
C50.0635 (17)0.0514 (16)0.0426 (14)0.0022 (13)0.0056 (12)0.0148 (12)
C60.0659 (18)0.0377 (13)0.0547 (16)0.0010 (12)0.0007 (13)0.0132 (12)
C70.0701 (18)0.0333 (12)0.0509 (15)0.0027 (12)0.0052 (13)0.0068 (11)
C80.076 (2)0.0487 (15)0.0438 (14)0.0080 (14)0.0105 (13)0.0056 (12)
C90.0378 (12)0.0596 (16)0.0395 (12)0.0040 (11)0.0034 (10)0.0100 (11)
C100.0382 (12)0.0449 (13)0.0369 (12)0.0021 (10)0.0048 (9)0.0004 (10)
C110.0368 (12)0.0570 (16)0.0377 (12)0.0044 (11)0.0024 (9)0.0101 (11)
C120.0428 (13)0.0545 (15)0.0427 (13)0.0097 (12)0.0004 (10)0.0103 (11)
N10.0387 (10)0.0371 (10)0.0456 (11)0.0011 (8)0.0029 (8)0.0032 (8)
N20.0425 (11)0.0436 (11)0.0404 (11)0.0070 (9)0.0015 (9)0.0044 (9)
N30.0461 (12)0.0477 (12)0.0368 (10)0.0027 (9)0.0034 (9)0.0012 (9)
N40.0431 (12)0.0301 (10)0.0467 (11)0.0014 (9)0.0036 (9)0.0045 (8)
O10.0666 (13)0.0425 (10)0.0388 (9)0.0066 (9)0.0030 (8)0.0032 (8)
O20.0466 (11)0.0615 (13)0.0627 (13)0.0134 (10)0.0064 (9)0.0026 (11)
O30.0416 (10)0.1067 (19)0.0618 (13)0.0049 (11)0.0054 (9)0.0405 (13)
O40.0489 (11)0.0507 (11)0.0636 (12)0.0129 (9)0.0021 (9)0.0069 (9)
O50.0414 (10)0.0929 (16)0.0607 (12)0.0123 (11)0.0090 (9)0.0363 (12)
O60.0632 (13)0.0741 (15)0.0714 (14)0.0289 (12)0.0130 (10)0.0310 (12)
O70.053 (3)0.131 (5)0.093 (4)0.014 (3)0.019 (3)0.047 (4)
O80.040 (2)0.074 (3)0.088 (3)0.007 (2)0.010 (2)0.039 (3)
Ni10.03465 (15)0.03061 (14)0.03573 (15)0.00025 (12)0.00133 (10)0.00017 (12)
Geometric parameters (Å, º) top
C1—N11.473 (3)C8—H8A0.97
C1—C21.514 (4)C8—H8B0.97
C1—H1A0.97C9—O31.252 (3)
C1—H1B0.97C9—C121.449 (4)
C2—N21.463 (4)C9—C101.467 (4)
C2—H2A0.97C10—O41.237 (3)
C2—H2B0.97C10—C111.465 (3)
C3—N21.465 (3)C11—O51.251 (3)
C3—C41.497 (5)C11—C121.447 (4)
C3—H3A0.97C12—O61.259 (3)
C3—H3B0.97N1—Ni12.084 (2)
C4—O21.438 (4)N1—H1C0.90
C4—H4A0.97N1—H1D0.90
C4—H4B0.97N2—Ni12.039 (2)
C5—N31.470 (4)N2—H30.85 (3)
C5—C61.512 (4)N3—Ni12.097 (2)
C5—H5A0.97N3—H3C0.90
C5—H5B0.97N3—H3D0.90
C6—N41.469 (3)N4—Ni12.051 (2)
C6—H6A0.97N4—H40.82 (3)
C6—H6B0.97O1—Ni12.1422 (19)
C7—N41.467 (3)O1—H10.93 (4)
C7—C81.500 (4)O2—Ni12.188 (2)
C7—H7A0.97O2—H20.87 (4)
C7—H7B0.97O8—H8C0.836 (10)
C8—O11.428 (3)O8—H8D0.836 (10)
N1—C1—C2108.4 (2)C11—C10—C989.2 (2)
N1—C1—H1A110.0O5—C11—C12134.2 (2)
C2—C1—H1A110.0O5—C11—C10135.6 (3)
N1—C1—H1B110.0C12—C11—C1090.17 (19)
C2—C1—H1B110.0O6—C12—C11135.3 (2)
H1A—C1—H1B108.4O6—C12—C9134.1 (2)
N2—C2—C1107.8 (2)C11—C12—C990.6 (2)
N2—C2—H2A110.1C1—N1—Ni1106.96 (16)
C1—C2—H2A110.1C1—N1—H1C110.3
N2—C2—H2B110.1Ni1—N1—H1C110.3
C1—C2—H2B110.1C1—N1—H1D110.3
H2A—C2—H2B108.5Ni1—N1—H1D110.3
N2—C3—C4107.8 (3)H1C—N1—H1D108.6
N2—C3—H3A110.1C2—N2—C3116.1 (2)
C4—C3—H3A110.1C2—N2—Ni1107.39 (17)
N2—C3—H3B110.1C3—N2—Ni1108.58 (18)
C4—C3—H3B110.1C2—N2—H3108.4 (19)
H3A—C3—H3B108.5C3—N2—H3107.1 (19)
O2—C4—C3109.0 (3)Ni1—N2—H3109.1 (19)
O2—C4—H4A109.9C5—N3—Ni1107.56 (16)
C3—C4—H4A109.9C5—N3—H3C110.2
O2—C4—H4B109.9Ni1—N3—H3C110.2
C3—C4—H4B109.9C5—N3—H3D110.2
H4A—C4—H4B108.3Ni1—N3—H3D110.2
N3—C5—C6108.8 (2)H3C—N3—H3D108.5
N3—C5—H5A109.9C7—N4—C6117.5 (2)
C6—C5—H5A109.9C7—N4—Ni1108.31 (16)
N3—C5—H5B109.9C6—N4—Ni1107.04 (17)
C6—C5—H5B109.9C7—N4—H4110 (2)
H5A—C5—H5B108.3C6—N4—H4106 (2)
N4—C6—C5107.7 (2)Ni1—N4—H4107 (2)
N4—C6—H6A110.2C8—O1—Ni1110.90 (16)
C5—C6—H6A110.2C8—O1—H1111 (2)
N4—C6—H6B110.2Ni1—O1—H1128 (2)
C5—C6—H6B110.2C4—O2—Ni1110.29 (19)
H6A—C6—H6B108.5C4—O2—H2117 (3)
N4—C7—C8108.0 (2)Ni1—O2—H2120 (3)
N4—C7—H7A110.1H8C—O8—H8D109 (3)
C8—C7—H7A110.1N2—Ni1—N4176.12 (9)
N4—C7—H7B110.1N2—Ni1—N184.03 (9)
C8—C7—H7B110.1N4—Ni1—N199.04 (9)
H7A—C7—H7B108.4N2—Ni1—N398.52 (9)
O1—C8—C7107.7 (2)N4—Ni1—N383.48 (9)
O1—C8—H8A110.2N1—Ni1—N397.34 (9)
C7—C8—H8A110.2N2—Ni1—O197.57 (8)
O1—C8—H8B110.2N4—Ni1—O179.99 (8)
C7—C8—H8B110.2N1—Ni1—O192.71 (8)
H8A—C8—H8B108.5N3—Ni1—O1161.81 (8)
O3—C9—C12134.2 (3)N2—Ni1—O279.14 (9)
O3—C9—C10135.7 (3)N4—Ni1—O297.54 (9)
C12—C9—C1090.0 (2)N1—Ni1—O2162.13 (9)
O4—C10—C11135.5 (2)N3—Ni1—O291.11 (9)
O4—C10—C9135.3 (2)O1—Ni1—O283.64 (8)
N1—C1—C2—N256.2 (3)C2—N2—Ni1—N3115.36 (18)
N2—C3—C4—O251.7 (4)C3—N2—Ni1—N3118.4 (2)
N3—C5—C6—N455.9 (3)C2—N2—Ni1—O173.15 (18)
N4—C7—C8—O154.0 (3)C3—N2—Ni1—O153.1 (2)
O3—C9—C10—O40.8 (6)C2—N2—Ni1—O2155.14 (18)
C12—C9—C10—O4179.7 (3)C3—N2—Ni1—O228.9 (2)
O3—C9—C10—C11178.3 (4)C7—N4—Ni1—N1115.06 (19)
C12—C9—C10—C110.6 (2)C6—N4—Ni1—N1117.35 (18)
O4—C10—C11—O50.7 (6)C7—N4—Ni1—N3148.51 (19)
C9—C10—C11—O5178.3 (4)C6—N4—Ni1—N320.92 (18)
O4—C10—C11—C12179.7 (3)C7—N4—Ni1—O123.88 (18)
C9—C10—C11—C120.6 (2)C6—N4—Ni1—O1151.47 (19)
O5—C11—C12—O60.4 (7)C7—N4—Ni1—O258.25 (19)
C10—C11—C12—O6179.4 (4)C6—N4—Ni1—O269.34 (18)
O5—C11—C12—C9178.4 (4)C1—N1—Ni1—N211.02 (17)
C10—C11—C12—C90.6 (2)C1—N1—Ni1—N4171.36 (17)
O3—C9—C12—O60.5 (7)C1—N1—Ni1—N386.84 (17)
C10—C9—C12—O6179.4 (4)C1—N1—Ni1—O1108.35 (17)
O3—C9—C12—C11178.3 (4)C1—N1—Ni1—O230.7 (4)
C10—C9—C12—C110.6 (2)C5—N3—Ni1—N2174.72 (17)
C2—C1—N1—Ni138.1 (3)C5—N3—Ni1—N48.63 (18)
C1—C2—N2—C3166.4 (2)C5—N3—Ni1—N189.69 (18)
C1—C2—N2—Ni144.7 (3)C5—N3—Ni1—O133.3 (4)
C4—C3—N2—C2173.5 (3)C5—N3—Ni1—O2106.09 (18)
C4—C3—N2—Ni152.5 (3)C8—O1—Ni1—N2177.7 (2)
C6—C5—N3—Ni136.1 (3)C8—O1—Ni1—N45.33 (19)
C8—C7—N4—C6170.4 (2)C8—O1—Ni1—N193.4 (2)
C8—C7—N4—Ni149.0 (3)C8—O1—Ni1—N330.3 (4)
C5—C6—N4—C7168.3 (2)C8—O1—Ni1—O2104.2 (2)
C5—C6—N4—Ni146.3 (3)C4—O2—Ni1—N21.1 (2)
C7—C8—O1—Ni132.6 (3)C4—O2—Ni1—N4176.9 (2)
C3—C4—O2—Ni126.4 (3)C4—O2—Ni1—N118.9 (4)
C2—N2—Ni1—N118.80 (17)C4—O2—Ni1—N399.5 (2)
C3—N2—Ni1—N1145.1 (2)C4—O2—Ni1—O197.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O30.902.243.007 (3)143
N1—H1D···O4i0.902.102.994 (3)170
N3—H3C···O7ii0.902.243.087 (6)157
N3—H3D···O4iii0.902.072.965 (3)170
O8—H8C···O60.84 (1)1.97 (5)2.659 (5)139 (7)
O8—H8C···O70.84 (1)2.02 (6)2.488 (7)115 (5)
O8—H8D···O5iv0.84 (1)2.08 (1)2.910 (5)174 (6)
N4—H4···O3i0.82 (3)2.04 (3)2.820 (3)159 (3)
O1—H1···O60.93 (4)1.71 (4)2.633 (3)172 (4)
O2—H2···O8v0.87 (4)1.91 (4)2.735 (5)158 (4)
O2—H2···O7ii0.87 (4)2.14 (4)2.711 (6)123 (3)
N2—H3···O5iii0.85 (3)2.05 (3)2.842 (3)154 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y+1, z+1; (v) x+1, y+1/2, z+1/2.
 

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