1-(2,6-Di­methyl­phenyl­amino)­propane-1,2-dione dioxime

The title compound, C₁₁H₁₅N₃O₂, consists of 2,6-di­methyl­phenyl and amino­methyl­glyoxime groups. The intermolecular O—H...N and O—H...O hydrogen bonds [O...N 2.742 (3) and 2.889 (3) Å] are highly effective in forming the polymeric chains. The glyoxime group has an E configuration.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.189
• Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_706  Alert A H...A   Calc    13.48(3), Rep     2.09(4), Dev.    379.67 Sigma
                     H1'  -O2      1.555   1.545

PLAT_706  Alert A H...A   Calc     8.00(4), Rep     1.81(5), Dev.    154.75 Sigma
                     H2'  -N2      1.555   2.555

PLAT_707  Alert A D...A   Calc   13.002(4), Rep    2.889(3), Dev.   2528.25 Sigma
                     O1   -O2      1.555   1.545

PLAT_707  Alert A D...A   Calc    8.254(3), Rep    2.742(3), Dev.   1837.33 Sigma
                     O2   -N2      1.555   2.555

PLAT_708  Alert A D-H..A  Calc       55(2), Rep      154(3), Dev.     49.50 Sigma
                     O1   -H1'  -O2      1.555   1.555   1.545

PLAT_708  Alert A D-H..A  Calc      103(2), Rep      174(4), Dev.     35.50 Sigma
                     O2   -H2'  -N2      1.555   1.555   2.555

PLAT_737  Alert A D...A   Calc    2.529(3), Rep     2.53(3) ....       9.90 s.u-Ratio
                     N1   -O1      1.555   1.555


 7 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

(I)

Crystal data

C11H15N3O2	F(000) = 472
Mr = 221.26	Dx = 1.328 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.404 (2) Å	θ = 10–18°
b = 7.672 (2) Å	µ = 0.09 mm^−1
c = 17.592 (3) Å	T = 296 K
β = 102.620 (19)°	Prism, colorless
V = 1106.8 (4) Å^3	0.35 × 0.15 × 0.15 mm
Z = 4

Data collection

Enraf-Nonius Turbo-CAD-4 diffractometer	1769 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.3°, θmin = 2.4°
non–profiled ω scans	h = −10→10
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = 0→9
Tmin = 0.968, Tmax = 0.986	l = 0→21
2198 measured reflections	3 standard reflections every 120 min
2198 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0973P)^2 + 0.6954P] where P = (Fo^2 + 2Fc^2)/3
2198 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
H2'	−0.001 (6)	0.484 (5)	0.257 (2)	0.084 (12)*
H1'	0.171 (4)	1.238 (4)	0.2095 (19)	0.059 (9)*
O2	0.0943 (2)	0.4846 (2)	0.23763 (11)	0.0410 (5)
N3	0.0955 (2)	0.6571 (3)	0.21243 (12)	0.0350 (5)
O1	0.2174 (2)	1.1672 (2)	0.18322 (12)	0.0462 (5)
N2	0.1935 (2)	0.9994 (2)	0.21332 (12)	0.0353 (5)
N1	0.3288 (3)	0.9185 (3)	0.11603 (11)	0.0343 (5)
C2	0.1988 (3)	0.7485 (3)	−0.00021 (14)	0.0376 (6)
C9	0.2472 (3)	0.8819 (3)	0.17276 (13)	0.0296 (5)
C10	0.2328 (3)	0.6975 (3)	0.19670 (13)	0.0305 (5)
C1	0.3401 (3)	0.8122 (3)	0.05008 (12)	0.0317 (5)
C6	0.4952 (3)	0.7885 (3)	0.03508 (14)	0.0351 (5)
C11	0.3747 (3)	0.5792 (3)	0.20340 (18)	0.0469 (7)
H11A	0.3460	0.4633	0.2196	0.070*
H11B	0.4669	0.6255	0.2422	0.070*
H11C	0.4051	0.5706	0.1528	0.070*
C7	0.6462 (3)	0.8467 (4)	0.09158 (16)	0.0452 (6)
H7A	0.6159	0.9020	0.1366	0.068*
H7B	0.7055	0.9305	0.0661	0.068*
H7C	0.7159	0.7456	0.1090	0.068*
C3	0.2175 (4)	0.6656 (4)	−0.06836 (16)	0.0482 (7)
H3	0.1240	0.6211	−0.1034	0.058*
C5	0.5062 (3)	0.7056 (4)	−0.03430 (15)	0.0444 (6)
H5	0.6101	0.6890	−0.0463	0.053*
C4	0.3678 (4)	0.6472 (4)	−0.08579 (15)	0.0502 (7)
H4	0.3769	0.5942	−0.1334	0.060*
C8	0.0302 (3)	0.7682 (4)	0.01495 (17)	0.0509 (7)
H8A	0.0368	0.8288	0.0646	0.076*
H8B	−0.0183	0.6528	0.0174	0.076*
H8C	−0.0376	0.8360	−0.0272	0.076*
H1	0.341 (3)	1.021 (4)	0.1108 (16)	0.037 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0473 (10)	0.0298 (9)	0.0525 (11)	−0.0013 (7)	0.0253 (9)	0.0042 (7)
N3	0.0396 (11)	0.0297 (10)	0.0393 (11)	0.0005 (8)	0.0163 (9)	0.0020 (8)
O1	0.0620 (12)	0.0279 (9)	0.0553 (11)	0.0036 (8)	0.0271 (10)	0.0000 (8)
N2	0.0412 (11)	0.0295 (11)	0.0390 (11)	0.0006 (8)	0.0168 (9)	−0.0013 (8)
N1	0.0464 (12)	0.0267 (10)	0.0351 (10)	−0.0032 (8)	0.0202 (9)	−0.0018 (8)
C2	0.0434 (13)	0.0358 (13)	0.0335 (12)	−0.0010 (10)	0.0085 (10)	0.0039 (10)
C9	0.0295 (10)	0.0303 (11)	0.0304 (10)	0.0001 (9)	0.0097 (8)	−0.0009 (9)
C10	0.0353 (11)	0.0292 (11)	0.0296 (11)	0.0005 (9)	0.0126 (9)	−0.0008 (9)
C1	0.0422 (12)	0.0280 (11)	0.0276 (11)	0.0024 (9)	0.0135 (9)	0.0021 (8)
C6	0.0415 (13)	0.0316 (12)	0.0350 (12)	0.0003 (10)	0.0144 (10)	0.0024 (9)
C11	0.0436 (14)	0.0385 (14)	0.0650 (17)	0.0095 (11)	0.0257 (13)	0.0155 (12)
C7	0.0402 (14)	0.0526 (16)	0.0457 (14)	−0.0024 (11)	0.0159 (11)	0.0001 (12)
C3	0.0588 (17)	0.0460 (15)	0.0367 (13)	−0.0038 (13)	0.0039 (12)	−0.0034 (12)
C5	0.0563 (16)	0.0441 (15)	0.0388 (13)	0.0080 (12)	0.0235 (12)	0.0010 (11)
C4	0.0727 (19)	0.0463 (16)	0.0343 (13)	0.0043 (14)	0.0176 (13)	−0.0069 (11)
C8	0.0403 (14)	0.0629 (19)	0.0480 (15)	−0.0055 (13)	0.0062 (12)	0.0027 (13)

Geometric parameters (Å, º)

O2—N3	1.396 (3)	C6—C7	1.498 (4)
O2—H2'	0.94 (5)	C11—H11A	0.9800
N3—C10	1.282 (3)	C11—H11B	0.9800
O1—N2	1.423 (3)	C11—H11C	0.9800
O1—H1'	0.86 (3)	C7—H7A	0.9800
N2—C9	1.290 (3)	C7—H7B	0.9800
N1—C9	1.358 (3)	C7—H7C	0.9800
N1—C1	1.438 (3)	C3—C4	1.371 (4)
N1—H1	0.80 (3)	C3—H3	0.9500
C2—C3	1.396 (4)	C5—C4	1.383 (4)
C2—C1	1.404 (3)	C5—H5	0.9500
C2—C8	1.506 (4)	C4—H4	0.9500
C9—C10	1.489 (3)	C8—H8A	0.9800
C10—C11	1.482 (3)	C8—H8B	0.9800
C1—C6	1.398 (3)	C8—H8C	0.9800
C6—C5	1.397 (3)
N3—O2—H2'	101 (3)	C10—C11—H11C	109.5
C10—N3—O2	111.52 (19)	H11A—C11—H11C	109.5
N2—O1—H1'	105 (2)	H11B—C11—H11C	109.5
C9—N2—O1	109.37 (18)	C6—C7—H7A	109.5
C9—N1—C1	127.5 (2)	C6—C7—H7B	109.5
C9—N1—H1	113 (2)	H7A—C7—H7B	109.5
C1—N1—H1	115 (2)	C6—C7—H7C	109.5
C3—C2—C1	117.5 (2)	H7A—C7—H7C	109.5
C3—C2—C8	119.0 (2)	H7B—C7—H7C	109.5
C1—C2—C8	123.5 (2)	C4—C3—C2	121.4 (3)
N2—C9—N1	123.8 (2)	C4—C3—H3	119.3
N2—C9—C10	116.59 (19)	C2—C3—H3	119.3
N1—C9—C10	119.29 (19)	C4—C5—C6	120.8 (2)
N3—C10—C11	125.6 (2)	C4—C5—H5	119.6
N3—C10—C9	115.0 (2)	C6—C5—H5	119.6
C11—C10—C9	119.4 (2)	C3—C4—C5	120.3 (2)
C6—C1—C2	122.1 (2)	C3—C4—H4	119.9
C6—C1—N1	117.0 (2)	C5—C4—H4	119.9
C2—C1—N1	120.7 (2)	C2—C8—H8A	109.5
C5—C6—C1	117.8 (2)	C2—C8—H8B	109.5
C5—C6—C7	120.5 (2)	H8A—C8—H8B	109.5
C1—C6—C7	121.7 (2)	C2—C8—H8C	109.5
C10—C11—H11A	109.5	H8A—C8—H8C	109.5
C10—C11—H11B	109.5	H8B—C8—H8C	109.5
H11A—C11—H11B	109.5
O1—N2—C9—N1	6.4 (3)	C8—C2—C1—N1	−6.8 (4)
O1—N2—C9—C10	179.61 (19)	C9—N1—C1—C6	−132.5 (3)
C1—N1—C9—N2	−154.7 (2)	C9—N1—C1—C2	52.8 (3)
C1—N1—C9—C10	32.3 (4)	C2—C1—C6—C5	3.0 (4)
O2—N3—C10—C11	0.2 (3)	N1—C1—C6—C5	−171.7 (2)
O2—N3—C10—C9	−177.37 (18)	C2—C1—C6—C7	−175.9 (2)
N2—C9—C10—N3	44.3 (3)	N1—C1—C6—C7	9.4 (3)
N1—C9—C10—N3	−142.2 (2)	C1—C2—C3—C4	−0.1 (4)
N2—C9—C10—C11	−133.5 (2)	C8—C2—C3—C4	178.7 (3)
N1—C9—C10—C11	40.0 (3)	C1—C6—C5—C4	−0.7 (4)
C3—C2—C1—C6	−2.6 (3)	C7—C6—C5—C4	178.2 (2)
C8—C2—C1—C6	178.7 (2)	C2—C3—C4—C5	2.3 (4)
C3—C2—C1—N1	171.9 (2)	C6—C5—C4—C3	−1.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1′···O2^i	0.86 (4)	2.09 (4)	2.889 (3)	154 (3)
O2—H2′···N2^ii	0.94 (3)	1.81 (5)	2.742 (3)	174 (4)
N1—H1···O1	0.80 (3)	2.13 (3)	2.53 (3)	111 (3)

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2.