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The crystal structure determination of the title compound, [Ni(C6H15NO3)2](C4O4), is reported; the squarate dianion is located on an inversion centre and a supramolecular architecture is formed. All the O atoms of the squarate dianion are involved in hydrogen bonding and connect two centrosymmetric nickel triethano­lamine complex cations through two symmetry-related hydrogen bonds. There is also a hydrogen-bond interaction between the free hydroxyl O atom of the complex cation and one of the O atoms of the squarate dianion. All these hydrogen bonds link the molecular units in chains. The inter-chain packing is formed by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001503/na6286sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001503/na6286Isup2.hkl
Contains datablock I

CCDC reference: 234826

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.089
  • Data-to-parameter ratio = 24.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O3 = 6.51 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O4 = 6.98 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N1 = 6.72 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 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-RED (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
[Ni(C6H15NO3)2](C4O4)Z = 1
Mr = 469.13F(000) = 248
Triclinic, P1Dx = 1.539 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5058 (7) ÅCell parameters from 15818 reflections
b = 8.5766 (8) Åθ = 0.0–32.1°
c = 8.9156 (8) ŵ = 1.02 mm1
α = 102.551 (7)°T = 293 K
β = 110.398 (7)°Prismatic, violet
γ = 99.698 (7)°0.45 × 0.43 × 0.28 mm
V = 506.04 (9) Å3
Data collection top
Stoe IPDS-2
diffractometer
3549 independent reflections
Radiation source: fine-focus sealed tube3346 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.032
Detector resolution: 6.67 pixels mm-1θmax = 32.2°, θmin = 2.5°
ω rotation scansh = 1111
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1212
Tmin = 0.516, Tmax = 0.772l = 1313
6624 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0472P)2 + 0.0971P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3549 reflectionsΔρmax = 0.52 e Å3
146 parametersΔρmin = 0.57 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.108 (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
xyzUiso*/Ueq
C80.9171 (2)0.2024 (2)0.6449 (2)0.0469 (3)
H8A0.89910.09130.57720.056*
H8B1.02290.27570.63470.056*
C70.7286 (2)0.25447 (18)0.57306 (18)0.0364 (3)
H7A0.70450.25060.45800.044*
H7B0.62050.17210.56990.044*
Ni10.50000.50000.50000.02565 (8)
O50.9764 (2)0.20398 (19)0.81404 (19)0.0547 (3)
N10.72030 (15)0.42007 (14)0.66026 (13)0.03006 (19)
C60.9044 (2)0.54865 (19)0.7057 (2)0.0394 (3)
H6A0.94130.53600.61060.047*
H6B1.00980.53360.79750.047*
O40.69503 (15)0.72964 (12)0.64365 (13)0.0355 (2)
O30.36826 (14)0.48024 (12)0.66497 (12)0.03259 (18)
C50.8806 (2)0.72131 (19)0.7572 (2)0.0464 (3)
H5A0.88600.74770.87040.056*
H5B0.98710.80150.75540.056*
C30.4506 (2)0.37127 (18)0.75402 (18)0.0365 (3)
H3A0.39450.25760.68220.044*
H3B0.41890.38000.85160.044*
C40.6719 (2)0.4173 (2)0.80839 (17)0.0373 (3)
H4A0.72990.52550.89160.045*
H4B0.72640.33720.85870.045*
O10.6483 (2)0.99418 (13)0.81537 (16)0.0471 (3)
O20.36287 (18)0.72086 (12)0.88896 (15)0.0432 (2)
C10.5674 (2)0.99736 (15)0.91714 (16)0.0332 (2)
C20.4384 (2)0.87302 (15)0.94906 (16)0.0320 (2)
H50.888 (4)0.145 (3)0.824 (3)0.067 (8)*
H40.667 (3)0.797 (3)0.691 (3)0.050 (6)*
H30.377 (3)0.561 (3)0.731 (3)0.047 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C80.0412 (7)0.0501 (8)0.0589 (10)0.0210 (6)0.0240 (7)0.0212 (7)
C70.0367 (6)0.0371 (6)0.0354 (6)0.0124 (5)0.0152 (5)0.0078 (5)
Ni10.02575 (11)0.02800 (11)0.02127 (11)0.00607 (7)0.00989 (7)0.00367 (7)
O50.0411 (6)0.0611 (8)0.0587 (8)0.0126 (6)0.0107 (5)0.0278 (7)
N10.0284 (4)0.0341 (5)0.0267 (4)0.0075 (4)0.0113 (4)0.0071 (4)
C60.0270 (5)0.0422 (7)0.0426 (7)0.0048 (5)0.0091 (5)0.0118 (6)
O40.0350 (4)0.0315 (4)0.0313 (4)0.0068 (4)0.0099 (4)0.0004 (3)
O30.0366 (4)0.0360 (4)0.0276 (4)0.0114 (4)0.0171 (4)0.0059 (3)
C50.0371 (7)0.0383 (7)0.0437 (8)0.0012 (5)0.0018 (6)0.0043 (6)
C30.0404 (6)0.0414 (6)0.0347 (6)0.0120 (5)0.0211 (5)0.0139 (5)
C40.0401 (6)0.0475 (7)0.0270 (5)0.0146 (5)0.0149 (5)0.0117 (5)
O10.0662 (7)0.0336 (5)0.0490 (6)0.0045 (5)0.0415 (6)0.0028 (4)
O20.0563 (6)0.0275 (4)0.0447 (6)0.0008 (4)0.0303 (5)0.0005 (4)
C10.0400 (6)0.0277 (5)0.0317 (6)0.0056 (4)0.0193 (5)0.0029 (4)
C20.0372 (6)0.0285 (5)0.0298 (5)0.0060 (4)0.0174 (5)0.0031 (4)
Geometric parameters (Å, º) top
C8—O51.412 (2)C6—H6B0.9700
C8—C71.522 (2)O4—C51.4324 (18)
C8—H8A0.9700O4—H40.75 (2)
C8—H8B0.9700O3—C31.4357 (17)
C7—N11.4863 (17)O3—H30.78 (2)
C7—H7A0.9700C5—H5A0.9700
C7—H7B0.9700C5—H5B0.9700
Ni1—O32.0581 (9)C3—C41.511 (2)
Ni1—O42.0707 (10)C3—H3A0.9700
Ni1—N12.0992 (11)C3—H3B0.9700
O5—H50.81 (3)C4—H4A0.9700
N1—C61.4805 (18)C4—H4B0.9700
N1—C41.4907 (17)O1—C11.2537 (15)
C6—C51.512 (2)O2—C21.2437 (16)
C6—H6A0.9700C1—C21.4604 (18)
O5—C8—C7115.40 (14)H6A—C6—H6B108.0
O5—C8—H8A108.4C5—O4—Ni1113.84 (9)
C7—C8—H8A108.4C5—O4—H4105.9 (18)
O5—C8—H8B108.4Ni1—O4—H4123.1 (19)
C7—C8—H8B108.4C3—O3—Ni1106.95 (7)
H8A—C8—H8B107.5C3—O3—H3107.6 (16)
N1—C7—C8117.90 (13)Ni1—O3—H3118.8 (16)
N1—C7—H7A107.8O4—C5—C6109.37 (12)
C8—C7—H7A107.8O4—C5—H5A109.8
N1—C7—H7B107.8C6—C5—H5A109.8
C8—C7—H7B107.8O4—C5—H5B109.8
H7A—C7—H7B107.2C6—C5—H5B109.8
O3—Ni1—O495.64 (4)H5A—C5—H5B108.2
O3—Ni1—N184.26 (4)O3—C3—C4109.65 (11)
O4—Ni1—N181.63 (4)O3—C3—H3A109.7
C8—O5—H5109 (2)C4—C3—H3A109.7
C6—N1—C7111.31 (11)O3—C3—H3B109.7
C6—N1—C4111.79 (11)C4—C3—H3B109.7
C7—N1—C4111.87 (11)H3A—C3—H3B108.2
C6—N1—Ni1104.10 (8)N1—C4—C3109.60 (11)
C7—N1—Ni1110.85 (8)N1—C4—H4A109.8
C4—N1—Ni1106.56 (8)C3—C4—H4A109.8
N1—C6—C5111.61 (12)N1—C4—H4B109.8
N1—C6—H6A109.3C3—C4—H4B109.8
C5—C6—H6A109.3H4A—C4—H4B108.2
N1—C6—H6B109.3O1—C1—C2134.71 (12)
C5—C6—H6B109.3O2—C2—C1135.95 (12)
O5—C8—C7—N156.6 (2)O3—Ni1—O4—C590.78 (11)
C8—C7—N1—C644.45 (16)N1—Ni1—O4—C57.45 (11)
C8—C7—N1—C481.42 (15)O4—Ni1—O3—C3101.60 (9)
C8—C7—N1—Ni1159.80 (11)N1—Ni1—O3—C320.63 (9)
O3—Ni1—N1—C6125.67 (9)Ni1—O4—C5—C616.29 (17)
O4—Ni1—N1—C629.08 (9)N1—C6—C5—O443.35 (18)
O3—Ni1—N1—C7114.56 (9)Ni1—O3—C3—C445.02 (12)
O4—Ni1—N1—C7148.85 (9)C6—N1—C4—C3146.32 (12)
O3—Ni1—N1—C47.38 (9)C7—N1—C4—C388.08 (13)
O4—Ni1—N1—C489.21 (9)Ni1—N1—C4—C333.21 (13)
C7—N1—C6—C5166.79 (12)O3—C3—C4—N153.80 (15)
C4—N1—C6—C567.30 (15)O1—C1—C2—O20.4 (3)
Ni1—N1—C6—C547.33 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O1i0.81 (3)2.00 (3)2.8000 (19)172 (3)
O3—H3···O20.78 (2)1.79 (2)2.5579 (14)169 (2)
O4—H4···O10.75 (2)1.86 (2)2.5976 (14)168 (3)
Symmetry code: (i) x, y1, z.
 

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