2,2-Dimethyl-5-{[(4-nitro-phen-yl)amino]-methyl-idene}-1,3-dioxane-4,6-dione.

In the title compound, C(13)H(12)N(2)O(6), the dihedral angle between the benzene ring and the amino-methyl-ene unit is 5.42 (16)°, while the angle between the amino-methyl-ene unit and the dioxane ring is 3.06 (43)°. The dioxane ring shows a half-boat conformation, in which the C atom between the dioxane ring O atoms is 0.464 (10) Å out of the plane. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation. In the crystal, a three-dimensional framework is built up via inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the synthesis and biological activity of related compounds, see: Cassis et al. (1985 ▶); Griera et al. (1997 ▶); Darque et al. (2009 ▶).

Experimental

Crystal data

C13H12N2O6

M = 292.25

Monoclinic,

a = 12.2822 (8) Å

b = 12.2762 (7) Å

c = 9.2760 (6) Å

β = 106.636 (7)°

V = 1340.08 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.22 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.933, T max = 1.0

6063 measured reflections

2741 independent reflections

1432 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.126

S = 1.00

2741 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov, 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001103/pb2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001103/pb2051Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H12N2O6	F(000) = 608
Mr = 292.25	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 1825 reflections
a = 12.2822 (8) Å	θ = 3.0–29.1°
b = 12.2762 (7) Å	µ = 0.12 mm−1
c = 9.2760 (6) Å	T = 293 K
β = 106.636 (7)°	Block, colorless
V = 1340.08 (15) Å3	0.22 × 0.15 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	2741 independent reflections
Radiation source: fine-focus sealed tube	1432 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −15→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −15→14
Tmin = 0.933, Tmax = 1.0	l = −11→11
6063 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0459P)2] where P = (Fo2 + 2Fc2)/3
2741 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
O1	0.69558 (14)	0.20994 (13)	0.55007 (17)	0.0590 (5)
O2	0.68603 (13)	0.02148 (12)	0.59936 (18)	0.0621 (5)
O3	0.58804 (16)	0.33063 (14)	0.6199 (2)	0.0731 (6)
O4	0.55320 (14)	−0.04417 (12)	0.69224 (19)	0.0669 (5)
O5	0.07063 (17)	0.30379 (18)	1.0992 (2)	0.0965 (7)
O6	0.02953 (19)	0.13441 (18)	1.1075 (2)	0.0978 (7)
N1	0.08472 (19)	0.2076 (2)	1.0746 (2)	0.0682 (6)
N2	0.42612 (16)	0.10150 (15)	0.80560 (19)	0.0532 (5)
H2	0.4389	0.0332	0.7979	0.064*
C1	0.1735 (2)	0.1808 (2)	1.0033 (3)	0.0512 (6)
C2	0.2364 (2)	0.2628 (2)	0.9673 (3)	0.0610 (7)
H2A	0.2225	0.3349	0.9872	0.073*
C3	0.3200 (2)	0.23774 (19)	0.9015 (3)	0.0599 (7)
H3	0.3625	0.2931	0.8752	0.072*
C4	0.3412 (2)	0.13024 (18)	0.8742 (2)	0.0475 (6)
C5	0.2780 (2)	0.04875 (19)	0.9127 (2)	0.0578 (7)
H5	0.2930	−0.0237	0.8959	0.069*
C6	0.1926 (2)	0.0739 (2)	0.9760 (3)	0.0619 (7)
H6	0.1485	0.0191	0.9998	0.074*
C7	0.4875 (2)	0.17060 (19)	0.7523 (2)	0.0519 (6)
H7	0.4728	0.2442	0.7615	0.062*
C8	0.5701 (2)	0.14631 (17)	0.6851 (2)	0.0473 (6)
C9	0.6166 (2)	0.2361 (2)	0.6219 (3)	0.0525 (6)
C10	0.60071 (19)	0.03607 (19)	0.6628 (2)	0.0511 (6)
C11	0.7596 (2)	0.11232 (19)	0.5931 (3)	0.0532 (6)
C12	0.8456 (2)	0.1284 (2)	0.7444 (3)	0.0690 (8)
H12A	0.8068	0.1446	0.8183	0.104*
H12C	0.8950	0.1878	0.7387	0.104*
H12B	0.8896	0.0632	0.7726	0.104*
C13	0.8114 (2)	0.0867 (2)	0.4690 (3)	0.0759 (8)
H13B	0.8543	0.0204	0.4920	0.114*
H13C	0.8607	0.1452	0.4593	0.114*
H13A	0.7523	0.0782	0.3762	0.114*

	U11	U22	U33	U12	U13	U23
O1	0.0627 (12)	0.0520 (10)	0.0669 (11)	−0.0033 (9)	0.0258 (10)	0.0107 (8)
O2	0.0610 (11)	0.0457 (10)	0.0923 (12)	−0.0069 (8)	0.0423 (10)	−0.0037 (9)
O3	0.0796 (14)	0.0420 (10)	0.1021 (14)	−0.0003 (10)	0.0332 (11)	0.0071 (10)
O4	0.0672 (12)	0.0411 (10)	0.1041 (14)	−0.0106 (9)	0.0433 (11)	−0.0009 (9)
O5	0.0895 (16)	0.0796 (15)	0.1366 (19)	0.0217 (12)	0.0585 (15)	−0.0083 (13)
O6	0.0944 (17)	0.0955 (16)	0.1287 (18)	−0.0093 (13)	0.0723 (15)	0.0001 (13)
N1	0.0586 (16)	0.0776 (17)	0.0710 (15)	0.0078 (14)	0.0227 (13)	−0.0020 (14)
N2	0.0587 (14)	0.0437 (11)	0.0612 (12)	−0.0031 (10)	0.0239 (11)	−0.0054 (10)
C1	0.0471 (15)	0.0550 (16)	0.0535 (15)	0.0051 (13)	0.0174 (12)	−0.0008 (12)
C2	0.0594 (17)	0.0466 (15)	0.0818 (18)	0.0016 (13)	0.0277 (15)	−0.0086 (14)
C3	0.0608 (17)	0.0451 (15)	0.0818 (18)	−0.0078 (13)	0.0331 (15)	−0.0046 (13)
C4	0.0484 (15)	0.0463 (14)	0.0487 (14)	0.0026 (12)	0.0153 (12)	−0.0019 (11)
C5	0.0762 (19)	0.0415 (14)	0.0645 (16)	0.0012 (13)	0.0342 (15)	0.0017 (12)
C6	0.0730 (19)	0.0531 (17)	0.0698 (17)	−0.0020 (14)	0.0369 (15)	0.0070 (13)
C7	0.0546 (16)	0.0451 (14)	0.0541 (15)	−0.0042 (12)	0.0123 (13)	−0.0046 (12)
C8	0.0506 (15)	0.0378 (13)	0.0560 (15)	−0.0043 (11)	0.0192 (13)	0.0001 (11)
C9	0.0492 (16)	0.0509 (16)	0.0528 (15)	−0.0054 (13)	0.0072 (12)	0.0013 (13)
C10	0.0473 (15)	0.0470 (15)	0.0599 (15)	−0.0066 (12)	0.0169 (13)	−0.0002 (12)
C11	0.0536 (16)	0.0483 (15)	0.0624 (16)	−0.0090 (13)	0.0238 (14)	0.0034 (13)
C12	0.0577 (18)	0.0740 (18)	0.0759 (18)	−0.0065 (15)	0.0199 (15)	0.0105 (15)
C13	0.078 (2)	0.0794 (19)	0.0812 (18)	−0.0113 (17)	0.0400 (17)	−0.0039 (16)

O1—C9	1.363 (3)	C3—C4	1.382 (3)
O1—C11	1.426 (3)	C4—C5	1.375 (3)
O2—C10	1.353 (2)	C5—H5	0.9300
O2—C11	1.447 (3)	C5—C6	1.375 (3)
O3—C9	1.211 (3)	C6—H6	0.9300
O4—C10	1.215 (2)	C7—H7	0.9300
O5—N1	1.224 (3)	C7—C8	1.366 (3)
O6—N1	1.216 (3)	C8—C9	1.442 (3)
N1—C1	1.465 (3)	C8—C10	1.435 (3)
N2—H2	0.8600	C11—C12	1.508 (3)
N2—C4	1.414 (3)	C11—C13	1.500 (3)
N2—C7	1.322 (3)	C12—H12A	0.9600
C1—C2	1.367 (3)	C12—H12C	0.9600
C1—C6	1.370 (3)	C12—H12B	0.9600
C2—H2A	0.9300	C13—H13B	0.9600
C2—C3	1.372 (3)	C13—H13C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
O1—C9—C8	116.1 (2)	C4—C5—H5	119.9
O1—C11—O2	110.98 (19)	C4—C5—C6	120.2 (2)
O1—C11—C12	109.5 (2)	C5—C4—N2	118.7 (2)
O1—C11—C13	106.38 (19)	C5—C4—C3	119.8 (2)
O2—C10—C8	117.1 (2)	C5—C6—H6	120.4
O2—C11—C12	110.04 (19)	C6—C1—N1	119.3 (2)
O2—C11—C13	106.03 (19)	C6—C5—H5	119.9
O3—C9—O1	117.5 (2)	C7—N2—H2	117.2
O3—C9—C8	126.3 (2)	C7—N2—C4	125.6 (2)
O4—C10—O2	118.2 (2)	C7—C8—C9	116.8 (2)
O4—C10—C8	124.7 (2)	C7—C8—C10	122.1 (2)
O5—N1—C1	117.7 (2)	C8—C7—H7	116.3
O6—N1—O5	123.2 (2)	C9—O1—C11	118.27 (17)
O6—N1—C1	119.2 (2)	C10—O2—C11	119.07 (18)
N2—C7—H7	116.3	C10—C8—C9	120.7 (2)
N2—C7—C8	127.4 (2)	C11—C12—H12A	109.5
C1—C2—H2A	120.3	C11—C12—H12C	109.5
C1—C2—C3	119.4 (2)	C11—C12—H12B	109.5
C1—C6—C5	119.2 (2)	C11—C13—H13B	109.5
C1—C6—H6	120.4	C11—C13—H13C	109.5
C2—C1—N1	119.4 (2)	C11—C13—H13A	109.5
C2—C1—C6	121.4 (2)	H12A—C12—H12C	109.5
C2—C3—H3	120.0	H12A—C12—H12B	109.5
C2—C3—C4	120.0 (2)	H12C—C12—H12B	109.5
C3—C2—H2A	120.3	C13—C11—C12	113.8 (2)
C3—C4—N2	121.5 (2)	H13B—C13—H13C	109.5
C4—N2—H2	117.2	H13B—C13—H13A	109.5
C4—C3—H3	120.0	H13C—C13—H13A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.86	2.65	3.411 (3)	148
N2—H2···O4	0.86	2.15	2.771 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.86	2.65	3.411 (3)	148
N2—H2⋯O4	0.86	2.15	2.771 (2)	129

Symmetry code: (i) .