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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
CCDC reference: 234826
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
Crystal data top
[Ni(C6H15NO3)2](C4O4) | Z = 1 |
Mr = 469.13 | F(000) = 248 |
Triclinic, P1 | Dx = 1.539 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5058 (7) Å | Cell parameters from 15818 reflections |
b = 8.5766 (8) Å | θ = 0.0–32.1° |
c = 8.9156 (8) Å | µ = 1.02 mm−1 |
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 tube | 3346 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.032 |
Detector resolution: 6.67 pixels mm-1 | θmax = 32.2°, θmin = 2.5° |
ω rotation scans | h = −11→11 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.516, Tmax = 0.772 | l = −13→13 |
6624 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H 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 reflections | Δρmax = 0.52 e Å−3 |
146 parameters | Δρmin = −0.57 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C8 | 0.9171 (2) | 0.2024 (2) | 0.6449 (2) | 0.0469 (3) | |
H8A | 0.8991 | 0.0913 | 0.5772 | 0.056* | |
H8B | 1.0229 | 0.2757 | 0.6347 | 0.056* | |
C7 | 0.7286 (2) | 0.25447 (18) | 0.57306 (18) | 0.0364 (3) | |
H7A | 0.7045 | 0.2506 | 0.4580 | 0.044* | |
H7B | 0.6205 | 0.1721 | 0.5699 | 0.044* | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.02565 (8) | |
O5 | 0.9764 (2) | 0.20398 (19) | 0.81404 (19) | 0.0547 (3) | |
N1 | 0.72030 (15) | 0.42007 (14) | 0.66026 (13) | 0.03006 (19) | |
C6 | 0.9044 (2) | 0.54865 (19) | 0.7057 (2) | 0.0394 (3) | |
H6A | 0.9413 | 0.5360 | 0.6106 | 0.047* | |
H6B | 1.0098 | 0.5336 | 0.7975 | 0.047* | |
O4 | 0.69503 (15) | 0.72964 (12) | 0.64365 (13) | 0.0355 (2) | |
O3 | 0.36826 (14) | 0.48024 (12) | 0.66497 (12) | 0.03259 (18) | |
C5 | 0.8806 (2) | 0.72131 (19) | 0.7572 (2) | 0.0464 (3) | |
H5A | 0.8860 | 0.7477 | 0.8704 | 0.056* | |
H5B | 0.9871 | 0.8015 | 0.7554 | 0.056* | |
C3 | 0.4506 (2) | 0.37127 (18) | 0.75402 (18) | 0.0365 (3) | |
H3A | 0.3945 | 0.2576 | 0.6822 | 0.044* | |
H3B | 0.4189 | 0.3800 | 0.8516 | 0.044* | |
C4 | 0.6719 (2) | 0.4173 (2) | 0.80839 (17) | 0.0373 (3) | |
H4A | 0.7299 | 0.5255 | 0.8916 | 0.045* | |
H4B | 0.7264 | 0.3372 | 0.8587 | 0.045* | |
O1 | 0.6483 (2) | 0.99418 (13) | 0.81537 (16) | 0.0471 (3) | |
O2 | 0.36287 (18) | 0.72086 (12) | 0.88896 (15) | 0.0432 (2) | |
C1 | 0.5674 (2) | 0.99736 (15) | 0.91714 (16) | 0.0332 (2) | |
C2 | 0.4384 (2) | 0.87302 (15) | 0.94906 (16) | 0.0320 (2) | |
H5 | 0.888 (4) | 0.145 (3) | 0.824 (3) | 0.067 (8)* | |
H4 | 0.667 (3) | 0.797 (3) | 0.691 (3) | 0.050 (6)* | |
H3 | 0.377 (3) | 0.561 (3) | 0.731 (3) | 0.047 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C8 | 0.0412 (7) | 0.0501 (8) | 0.0589 (10) | 0.0210 (6) | 0.0240 (7) | 0.0212 (7) |
C7 | 0.0367 (6) | 0.0371 (6) | 0.0354 (6) | 0.0124 (5) | 0.0152 (5) | 0.0078 (5) |
Ni1 | 0.02575 (11) | 0.02800 (11) | 0.02127 (11) | 0.00607 (7) | 0.00989 (7) | 0.00367 (7) |
O5 | 0.0411 (6) | 0.0611 (8) | 0.0587 (8) | 0.0126 (6) | 0.0107 (5) | 0.0278 (7) |
N1 | 0.0284 (4) | 0.0341 (5) | 0.0267 (4) | 0.0075 (4) | 0.0113 (4) | 0.0071 (4) |
C6 | 0.0270 (5) | 0.0422 (7) | 0.0426 (7) | 0.0048 (5) | 0.0091 (5) | 0.0118 (6) |
O4 | 0.0350 (4) | 0.0315 (4) | 0.0313 (4) | 0.0068 (4) | 0.0099 (4) | −0.0004 (3) |
O3 | 0.0366 (4) | 0.0360 (4) | 0.0276 (4) | 0.0114 (4) | 0.0171 (4) | 0.0059 (3) |
C5 | 0.0371 (7) | 0.0383 (7) | 0.0437 (8) | 0.0012 (5) | 0.0018 (6) | 0.0043 (6) |
C3 | 0.0404 (6) | 0.0414 (6) | 0.0347 (6) | 0.0120 (5) | 0.0211 (5) | 0.0139 (5) |
C4 | 0.0401 (6) | 0.0475 (7) | 0.0270 (5) | 0.0146 (5) | 0.0149 (5) | 0.0117 (5) |
O1 | 0.0662 (7) | 0.0336 (5) | 0.0490 (6) | 0.0045 (5) | 0.0415 (6) | 0.0028 (4) |
O2 | 0.0563 (6) | 0.0275 (4) | 0.0447 (6) | 0.0008 (4) | 0.0303 (5) | −0.0005 (4) |
C1 | 0.0400 (6) | 0.0277 (5) | 0.0317 (6) | 0.0056 (4) | 0.0193 (5) | 0.0029 (4) |
C2 | 0.0372 (6) | 0.0285 (5) | 0.0298 (5) | 0.0060 (4) | 0.0174 (5) | 0.0031 (4) |
Geometric parameters (Å, º) top
C8—O5 | 1.412 (2) | C6—H6B | 0.9700 |
C8—C7 | 1.522 (2) | O4—C5 | 1.4324 (18) |
C8—H8A | 0.9700 | O4—H4 | 0.75 (2) |
C8—H8B | 0.9700 | O3—C3 | 1.4357 (17) |
C7—N1 | 1.4863 (17) | O3—H3 | 0.78 (2) |
C7—H7A | 0.9700 | C5—H5A | 0.9700 |
C7—H7B | 0.9700 | C5—H5B | 0.9700 |
Ni1—O3 | 2.0581 (9) | C3—C4 | 1.511 (2) |
Ni1—O4 | 2.0707 (10) | C3—H3A | 0.9700 |
Ni1—N1 | 2.0992 (11) | C3—H3B | 0.9700 |
O5—H5 | 0.81 (3) | C4—H4A | 0.9700 |
N1—C6 | 1.4805 (18) | C4—H4B | 0.9700 |
N1—C4 | 1.4907 (17) | O1—C1 | 1.2537 (15) |
C6—C5 | 1.512 (2) | O2—C2 | 1.2437 (16) |
C6—H6A | 0.9700 | C1—C2 | 1.4604 (18) |
| | | |
O5—C8—C7 | 115.40 (14) | H6A—C6—H6B | 108.0 |
O5—C8—H8A | 108.4 | C5—O4—Ni1 | 113.84 (9) |
C7—C8—H8A | 108.4 | C5—O4—H4 | 105.9 (18) |
O5—C8—H8B | 108.4 | Ni1—O4—H4 | 123.1 (19) |
C7—C8—H8B | 108.4 | C3—O3—Ni1 | 106.95 (7) |
H8A—C8—H8B | 107.5 | C3—O3—H3 | 107.6 (16) |
N1—C7—C8 | 117.90 (13) | Ni1—O3—H3 | 118.8 (16) |
N1—C7—H7A | 107.8 | O4—C5—C6 | 109.37 (12) |
C8—C7—H7A | 107.8 | O4—C5—H5A | 109.8 |
N1—C7—H7B | 107.8 | C6—C5—H5A | 109.8 |
C8—C7—H7B | 107.8 | O4—C5—H5B | 109.8 |
H7A—C7—H7B | 107.2 | C6—C5—H5B | 109.8 |
O3—Ni1—O4 | 95.64 (4) | H5A—C5—H5B | 108.2 |
O3—Ni1—N1 | 84.26 (4) | O3—C3—C4 | 109.65 (11) |
O4—Ni1—N1 | 81.63 (4) | O3—C3—H3A | 109.7 |
C8—O5—H5 | 109 (2) | C4—C3—H3A | 109.7 |
C6—N1—C7 | 111.31 (11) | O3—C3—H3B | 109.7 |
C6—N1—C4 | 111.79 (11) | C4—C3—H3B | 109.7 |
C7—N1—C4 | 111.87 (11) | H3A—C3—H3B | 108.2 |
C6—N1—Ni1 | 104.10 (8) | N1—C4—C3 | 109.60 (11) |
C7—N1—Ni1 | 110.85 (8) | N1—C4—H4A | 109.8 |
C4—N1—Ni1 | 106.56 (8) | C3—C4—H4A | 109.8 |
N1—C6—C5 | 111.61 (12) | N1—C4—H4B | 109.8 |
N1—C6—H6A | 109.3 | C3—C4—H4B | 109.8 |
C5—C6—H6A | 109.3 | H4A—C4—H4B | 108.2 |
N1—C6—H6B | 109.3 | O1—C1—C2 | 134.71 (12) |
C5—C6—H6B | 109.3 | O2—C2—C1 | 135.95 (12) |
| | | |
O5—C8—C7—N1 | 56.6 (2) | O3—Ni1—O4—C5 | 90.78 (11) |
C8—C7—N1—C6 | 44.45 (16) | N1—Ni1—O4—C5 | 7.45 (11) |
C8—C7—N1—C4 | −81.42 (15) | O4—Ni1—O3—C3 | −101.60 (9) |
C8—C7—N1—Ni1 | 159.80 (11) | N1—Ni1—O3—C3 | −20.63 (9) |
O3—Ni1—N1—C6 | −125.67 (9) | Ni1—O4—C5—C6 | 16.29 (17) |
O4—Ni1—N1—C6 | −29.08 (9) | N1—C6—C5—O4 | −43.35 (18) |
O3—Ni1—N1—C7 | 114.56 (9) | Ni1—O3—C3—C4 | 45.02 (12) |
O4—Ni1—N1—C7 | −148.85 (9) | C6—N1—C4—C3 | 146.32 (12) |
O3—Ni1—N1—C4 | −7.38 (9) | C7—N1—C4—C3 | −88.08 (13) |
O4—Ni1—N1—C4 | 89.21 (9) | Ni1—N1—C4—C3 | 33.21 (13) |
C7—N1—C6—C5 | 166.79 (12) | O3—C3—C4—N1 | −53.80 (15) |
C4—N1—C6—C5 | −67.30 (15) | O1—C1—C2—O2 | 0.4 (3) |
Ni1—N1—C6—C5 | 47.33 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1i | 0.81 (3) | 2.00 (3) | 2.8000 (19) | 172 (3) |
O3—H3···O2 | 0.78 (2) | 1.79 (2) | 2.5579 (14) | 169 (2) |
O4—H4···O1 | 0.75 (2) | 1.86 (2) | 2.5976 (14) | 168 (3) |
Symmetry code: (i) x, y−1, z. |
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