5-[(2-Chloro-4-nitro-anilino)methyl-idene]-2,2-dimethyl-1,3-dioxane-4,6-dione.

In the title compound, C(13)H(11)ClN(2)O(6), the dihedral angles between the benzene ring and the amino-methyl-ene unit and between the amino-methyl-ene group and the dioxane ring are 8.19 (14) and 1.39 (17)°, respectively. The dioxane ring has a half-boat conformation, in which the C atom between the dioxane O atoms is 0.662 (4)Å out of the plane through the remaining ring atoms. Intra-molecular N-H⋯O and N-H⋯Cl inter-actions occur.

Related literature

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

Experimental

Crystal data

C13H11ClN2O6

M = 326.69

Monoclinic,

a = 13.5850 (5) Å

b = 5.04379 (14) Å

c = 21.0272 (7) Å

β = 104.427 (4)°

V = 1395.35 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) ▶ T min = 0.984, T max = 1.0

6136 measured reflections

2853 independent reflections

2141 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.04

2853 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.29 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 et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100095X/bq2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100095X/bq2269Isup2.hkl

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

C13H11ClN2O6	F(000) = 672
Mr = 326.69	Dx = 1.555 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 2432 reflections
a = 13.5850 (5) Å	θ = 3.0–29.2°
b = 5.04379 (14) Å	µ = 0.31 mm−1
c = 21.0272 (7) Å	T = 293 K
β = 104.427 (4)°	Block, colorless
V = 1395.35 (8) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	2853 independent reflections
Radiation source: fine-focus sealed tube	2141 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.984, Tmax = 1.0	l = −25→26
6136 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.1291P] where P = (Fo2 + 2Fc2)/3
2853 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) 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
Cl1	0.11303 (4)	0.78022 (10)	0.26632 (2)	0.05062 (18)
O1	−0.23464 (10)	0.7514 (2)	0.04172 (7)	0.0446 (4)
O2	−0.24014 (10)	0.4073 (3)	−0.03503 (6)	0.0469 (4)
O3	−0.09905 (11)	0.8273 (3)	0.12205 (7)	0.0517 (4)
O4	−0.10943 (10)	0.1444 (3)	−0.03156 (7)	0.0509 (4)
O5	0.46457 (14)	0.3369 (4)	0.35706 (9)	0.0855 (6)
O6	0.48067 (14)	0.0203 (4)	0.29216 (9)	0.0910 (6)
N1	0.43369 (14)	0.2060 (4)	0.30716 (10)	0.0592 (5)
N2	0.05320 (11)	0.4776 (3)	0.14363 (7)	0.0360 (4)
H2	0.0263	0.6155	0.1565	0.043*
C1	0.33473 (15)	0.2739 (4)	0.26352 (9)	0.0432 (5)
C2	0.27826 (15)	0.4698 (4)	0.28308 (9)	0.0431 (5)
H2A	0.3024	0.5569	0.3229	0.052*
C3	0.18530 (14)	0.5341 (3)	0.24251 (9)	0.0377 (4)
C4	0.14835 (13)	0.4042 (3)	0.18250 (8)	0.0337 (4)
C5	0.20803 (15)	0.2071 (4)	0.16447 (9)	0.0421 (5)
H5	0.1847	0.1193	0.1247	0.051*
C6	0.30095 (15)	0.1410 (4)	0.20485 (10)	0.0455 (5)
H6	0.3404	0.0086	0.1928	0.055*
C7	−0.00122 (13)	0.3622 (3)	0.08932 (8)	0.0336 (4)
H7	0.0254	0.2132	0.0736	0.040*
C8	−0.09479 (13)	0.4525 (3)	0.05552 (8)	0.0328 (4)
C9	−0.14016 (14)	0.6847 (3)	0.07640 (9)	0.0373 (4)
C10	−0.29653 (14)	0.5492 (4)	0.00333 (10)	0.0437 (5)
C11	−0.14546 (14)	0.3172 (4)	−0.00500 (9)	0.0359 (4)
C12	−0.33222 (18)	0.3613 (4)	0.04848 (13)	0.0656 (7)
H12B	−0.3779	0.2337	0.0229	0.098*
H12C	−0.3668	0.4590	0.0756	0.098*
H12A	−0.2748	0.2713	0.0758	0.098*
C13	−0.38047 (18)	0.6932 (5)	−0.04496 (12)	0.0695 (7)
H13B	−0.3514	0.8249	−0.0678	0.104*
H13C	−0.4245	0.7774	−0.0218	0.104*
H13A	−0.4188	0.5687	−0.0760	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.0589 (4)	0.0482 (3)	0.0464 (3)	0.0072 (2)	0.0162 (3)	−0.0079 (2)
O1	0.0400 (8)	0.0317 (6)	0.0572 (9)	0.0054 (6)	0.0025 (7)	−0.0053 (6)
O2	0.0393 (8)	0.0582 (8)	0.0405 (8)	0.0068 (6)	0.0048 (6)	−0.0090 (7)
O3	0.0527 (9)	0.0407 (7)	0.0556 (9)	0.0058 (6)	0.0018 (7)	−0.0167 (7)
O4	0.0477 (9)	0.0585 (9)	0.0464 (8)	0.0064 (7)	0.0118 (7)	−0.0192 (7)
O5	0.0679 (12)	0.1027 (14)	0.0660 (11)	0.0073 (10)	−0.0210 (10)	−0.0129 (11)
O6	0.0689 (12)	0.1144 (15)	0.0783 (13)	0.0444 (12)	−0.0031 (10)	0.0001 (11)
N1	0.0447 (11)	0.0748 (13)	0.0522 (12)	0.0057 (10)	0.0013 (9)	0.0098 (10)
N2	0.0349 (8)	0.0370 (8)	0.0364 (9)	0.0019 (7)	0.0092 (7)	−0.0035 (7)
C1	0.0369 (11)	0.0526 (12)	0.0382 (11)	0.0015 (9)	0.0060 (9)	0.0074 (9)
C2	0.0462 (12)	0.0481 (11)	0.0327 (10)	−0.0039 (9)	0.0051 (9)	−0.0018 (9)
C3	0.0409 (11)	0.0385 (10)	0.0358 (10)	−0.0014 (8)	0.0136 (9)	0.0005 (8)
C4	0.0317 (10)	0.0373 (9)	0.0333 (10)	−0.0022 (7)	0.0107 (8)	0.0030 (8)
C5	0.0404 (11)	0.0500 (11)	0.0357 (11)	0.0028 (9)	0.0090 (9)	−0.0051 (9)
C6	0.0412 (11)	0.0497 (11)	0.0467 (12)	0.0067 (9)	0.0128 (9)	−0.0008 (10)
C7	0.0340 (10)	0.0351 (9)	0.0340 (10)	−0.0001 (8)	0.0130 (8)	−0.0005 (8)
C8	0.0342 (10)	0.0314 (9)	0.0344 (10)	−0.0008 (7)	0.0115 (8)	−0.0017 (8)
C9	0.0388 (10)	0.0308 (9)	0.0416 (11)	−0.0010 (8)	0.0086 (9)	0.0004 (8)
C10	0.0365 (10)	0.0413 (10)	0.0529 (12)	0.0015 (8)	0.0099 (9)	−0.0124 (9)
C11	0.0339 (10)	0.0400 (10)	0.0356 (10)	−0.0012 (8)	0.0120 (8)	−0.0014 (9)
C12	0.0596 (15)	0.0528 (13)	0.0971 (19)	−0.0072 (11)	0.0431 (14)	−0.0094 (13)
C13	0.0470 (14)	0.0787 (17)	0.0703 (16)	0.0174 (12)	−0.0089 (12)	−0.0148 (13)

Cl1—C3	1.7321 (19)	C3—C4	1.399 (2)
O1—C9	1.351 (2)	C4—C5	1.394 (2)
O1—C10	1.436 (2)	C5—H5	0.9300
O2—C10	1.434 (2)	C5—C6	1.375 (3)
O2—C11	1.362 (2)	C6—H6	0.9300
O3—C9	1.218 (2)	C7—H7	0.9300
O4—C11	1.203 (2)	C7—C8	1.371 (2)
O5—N1	1.222 (2)	C8—C9	1.442 (2)
O6—N1	1.218 (2)	C8—C11	1.457 (2)
N1—C1	1.467 (3)	C10—C12	1.505 (3)
N2—H2	0.8600	C10—C13	1.511 (3)
N2—C4	1.396 (2)	C12—H12B	0.9600
N2—C7	1.330 (2)	C12—H12C	0.9600
C1—C2	1.375 (3)	C12—H12A	0.9600
C1—C6	1.378 (3)	C13—H13B	0.9600
C2—H2A	0.9300	C13—H13C	0.9600
C2—C3	1.375 (2)	C13—H13A	0.9600
O1—C9—C8	117.28 (15)	C5—C4—N2	123.12 (16)
O1—C10—C12	109.17 (17)	C5—C4—C3	118.49 (16)
O1—C10—C13	105.94 (16)	C5—C6—C1	118.96 (19)
O2—C10—O1	110.53 (15)	C5—C6—H6	120.5
O2—C10—C12	109.99 (15)	C6—C1—N1	119.67 (19)
O2—C10—C13	106.34 (17)	C6—C5—C4	120.78 (17)
O2—C11—C8	115.76 (16)	C6—C5—H5	119.6
O3—C9—O1	117.76 (16)	C7—N2—H2	115.8
O3—C9—C8	124.94 (17)	C7—N2—C4	128.46 (15)
O4—C11—O2	118.24 (17)	C7—C8—C9	121.58 (16)
O4—C11—C8	125.91 (17)	C7—C8—C11	118.19 (16)
O5—N1—C1	118.4 (2)	C8—C7—H7	118.5
O6—N1—O5	123.2 (2)	C9—O1—C10	118.10 (13)
O6—N1—C1	118.38 (19)	C9—C8—C11	120.12 (16)
N2—C4—C3	118.39 (16)	C10—C12—H12B	109.5
N2—C7—H7	118.5	C10—C12—H12C	109.5
N2—C7—C8	123.03 (16)	C10—C12—H12A	109.5
C1—C2—H2A	120.7	C10—C13—H13B	109.5
C1—C2—C3	118.59 (17)	C10—C13—H13C	109.5
C1—C6—H6	120.5	C10—C13—H13A	109.5
C2—C1—N1	118.25 (18)	C11—O2—C10	118.74 (14)
C2—C1—C6	122.08 (18)	C12—C10—C13	114.77 (19)
C2—C3—Cl1	119.27 (14)	H12B—C12—H12C	109.5
C2—C3—C4	121.10 (17)	H12B—C12—H12A	109.5
C3—C2—H2A	120.7	H12C—C12—H12A	109.5
C4—N2—H2	115.8	H13B—C13—H13C	109.5
C4—C3—Cl1	119.63 (14)	H13B—C13—H13A	109.5
C4—C5—H5	119.6	H13C—C13—H13A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1	0.86	2.46	2.9328 (15)	115
N2—H2···O3	0.86	1.99	2.670 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1	0.86	2.46	2.9328 (15)	115
N2—H2⋯O3	0.86	1.99	2.670 (2)	136