5-(3,4-Dimeth-oxy-benzyl-idene)-1,3-dimethyl-1,3-diazinane-2,4,6-trione.

In the title compound, C(15)H(16)N(2)O(5), the dihedral angle between 1,3-diazinane and benzene rings is only 4.27 (1)°. The essentially planar mol-ecular structure is characterized by a short intra-molecular C-H⋯O separation and by an exceptionally large bond angle of 138.25 (14)° at the bridging methine C atom. The meth-oxy groups deviate somewhat from the plane of the benzene ring, with C-C-O-C torsion angles of -15.6 (1) and 9.17 (6)°. In the crystal, mol-ecules form centrosymmetric dimers via donor-acceptor π-π inter-actions, with a centroid-centroid distance of 3.401 (1) Å.

Related literature

For the biological activity of 1,3-diazinane derivatives, see: Negwar (2001 ▶); Tanaka et al. (1986 ▶, 1988 ▶). For the use of pyridine-type ligands in catalysis models, see: Roodt et al. (2011 ▶); van der Westhuizen et al. (2010 ▶). For related structures, see: Panchatcharam et al. (2009 ▶); Rezende et al. (2005 ▶). For the synthesis, see: Prajapati et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H16N2O5

M = 304.3

Triclinic,

a = 7.3086 (2) Å

b = 8.4033 (3) Å

c = 11.8705 (5) Å

α = 82.5685 (18)°

β = 77.6686 (17)°

γ = 71.1469 (15)°

V = 672.58 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.15 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.984, T max = 0.994

12172 measured reflections

3233 independent reflections

2478 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.05

3233 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052986/ld2039sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052986/ld2039Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052986/ld2039Isup3.cml

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

C15H16N2O5	Z = 2
Mr = 304.3	F(000) = 320
Triclinic, P1	Dx = 1.508 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3086 (2) Å	Cell parameters from 3146 reflections
b = 8.4033 (3) Å	θ = 2.6–28.2°
c = 11.8705 (5) Å	µ = 0.11 mm−1
α = 82.5685 (18)°	T = 100 K
β = 77.6686 (17)°	Plate, yellow
γ = 71.1469 (15)°	0.15 × 0.12 × 0.06 mm
V = 672.58 (4) Å3

Bruker APEXII CCD diffractometer	2478 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 28°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.984, Tmax = 0.994	k = −11→11
12172 measured reflections	l = −15→15
3233 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.239P] where P = (Fo2 + 2Fc2)/3
3233 reflections	(Δ/σ)max = 0.003
203 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 15 s/frame. A total of 1821 frames were collected with a frame width of 0.5° covering up to θ = 28.18° with 99.7% completeness accomplished.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.4027 (2)	0.72599 (19)	0.80997 (12)	0.0160 (3)
C2	0.5148 (2)	0.43533 (18)	0.75097 (12)	0.0150 (3)
C3	0.61438 (19)	0.49161 (18)	0.63713 (12)	0.0135 (3)
C4	0.59797 (19)	0.67081 (18)	0.61360 (12)	0.0144 (3)
C5	0.70824 (19)	0.36478 (18)	0.56448 (12)	0.0139 (3)
H5	0.6895	0.2635	0.5979	0.017*
C6	0.82904 (19)	0.34247 (18)	0.44990 (12)	0.0138 (3)
C7	0.89371 (19)	0.46673 (18)	0.37541 (12)	0.0142 (3)
H7	0.8572	0.576	0.3985	0.017*
C8	1.01025 (19)	0.42763 (18)	0.26903 (12)	0.0138 (3)
C9	1.06655 (19)	0.26239 (18)	0.23180 (12)	0.0142 (3)
C10	1.0028 (2)	0.13956 (18)	0.30414 (12)	0.0160 (3)
H10	1.0382	0.0306	0.2807	0.019*
C11	0.8865 (2)	0.17974 (18)	0.41127 (12)	0.0155 (3)
H11	0.8452	0.0963	0.459	0.019*
C12	0.4873 (2)	0.95348 (18)	0.68221 (13)	0.0186 (3)
H12A	0.3864	1.0081	0.6375	0.028*
H12B	0.6109	0.9644	0.6403	0.028*
H12C	0.4551	1.0052	0.7544	0.028*
C13	0.3059 (2)	0.5045 (2)	0.93915 (13)	0.0215 (3)
H13A	0.2832	0.5852	0.9949	0.032*
H13B	0.3826	0.396	0.9664	0.032*
H13C	0.1822	0.498	0.9283	0.032*
C14	0.9864 (2)	0.71432 (18)	0.21141 (14)	0.0203 (3)
H14A	0.8468	0.7402	0.2177	0.03*
H14B	1.0356	0.7815	0.1479	0.03*
H14C	1.0144	0.7384	0.2817	0.03*
C15	1.2176 (2)	0.08217 (19)	0.07552 (14)	0.0215 (3)
H15A	1.29	−0.0087	0.122	0.032*
H15B	1.2928	0.0848	−0.0012	0.032*
H15C	1.0949	0.0657	0.0724	0.032*
N1	0.41279 (17)	0.55732 (16)	0.82856 (10)	0.0161 (3)
N2	0.50181 (17)	0.77434 (15)	0.70439 (10)	0.0151 (3)
O5	1.18050 (15)	0.23929 (13)	0.12565 (9)	0.0181 (2)
O1	0.31031 (16)	0.82697 (14)	0.88192 (9)	0.0229 (3)
O2	0.51855 (15)	0.28912 (13)	0.77753 (9)	0.0216 (3)
O3	0.66023 (15)	0.73491 (13)	0.52101 (9)	0.0210 (3)
O4	1.07951 (14)	0.53932 (13)	0.19183 (9)	0.0174 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0140 (6)	0.0205 (8)	0.0140 (7)	−0.0057 (6)	−0.0022 (5)	−0.0026 (6)
C2	0.0151 (6)	0.0175 (7)	0.0130 (7)	−0.0061 (6)	−0.0020 (5)	−0.0008 (6)
C3	0.0134 (6)	0.0152 (7)	0.0116 (7)	−0.0049 (5)	−0.0022 (5)	0.0006 (5)
C4	0.0129 (6)	0.0161 (7)	0.0135 (7)	−0.0035 (5)	−0.0013 (5)	−0.0022 (6)
C5	0.0138 (6)	0.0149 (7)	0.0135 (7)	−0.0058 (5)	−0.0027 (5)	0.0013 (6)
C6	0.0128 (6)	0.0156 (7)	0.0128 (7)	−0.0041 (5)	−0.0024 (5)	−0.0010 (5)
C7	0.0148 (6)	0.0137 (7)	0.0141 (7)	−0.0048 (5)	−0.0006 (5)	−0.0028 (5)
C8	0.0136 (6)	0.0147 (7)	0.0134 (7)	−0.0061 (5)	−0.0014 (5)	0.0009 (5)
C9	0.0134 (6)	0.0164 (7)	0.0124 (7)	−0.0042 (5)	−0.0015 (5)	−0.0023 (6)
C10	0.0172 (7)	0.0137 (7)	0.0167 (7)	−0.0040 (5)	−0.0024 (5)	−0.0032 (6)
C11	0.0161 (6)	0.0151 (7)	0.0160 (7)	−0.0070 (6)	−0.0023 (5)	0.0012 (6)
C12	0.0216 (7)	0.0140 (7)	0.0201 (8)	−0.0058 (6)	−0.0013 (6)	−0.0034 (6)
C13	0.0228 (8)	0.0279 (9)	0.0138 (8)	−0.0110 (7)	0.0020 (6)	−0.0015 (6)
C14	0.0237 (7)	0.0153 (8)	0.0203 (8)	−0.0067 (6)	0.0005 (6)	−0.0010 (6)
C15	0.0267 (8)	0.0176 (8)	0.0184 (8)	−0.0053 (6)	0.0009 (6)	−0.0067 (6)
N1	0.0171 (6)	0.0192 (7)	0.0118 (6)	−0.0075 (5)	0.0008 (5)	−0.0008 (5)
N2	0.0164 (6)	0.0144 (6)	0.0143 (6)	−0.0055 (5)	−0.0007 (5)	−0.0013 (5)
O5	0.0226 (5)	0.0156 (5)	0.0142 (5)	−0.0063 (4)	0.0041 (4)	−0.0049 (4)
O1	0.0253 (6)	0.0234 (6)	0.0184 (6)	−0.0077 (5)	0.0040 (4)	−0.0085 (5)
O2	0.0284 (6)	0.0173 (6)	0.0177 (6)	−0.0099 (5)	0.0016 (4)	0.0015 (4)
O3	0.0271 (6)	0.0154 (5)	0.0160 (6)	−0.0056 (4)	0.0031 (4)	0.0008 (4)
O4	0.0214 (5)	0.0133 (5)	0.0154 (5)	−0.0067 (4)	0.0033 (4)	−0.0008 (4)

C1—O1	1.2150 (18)	C10—C11	1.385 (2)
C1—N1	1.386 (2)	C10—H10	0.93
C1—N2	1.3897 (19)	C11—H11	0.93
C2—O2	1.2212 (19)	C12—N2	1.467 (2)
C2—N1	1.3826 (19)	C12—H12A	0.96
C2—C3	1.489 (2)	C12—H12B	0.96
C3—C5	1.365 (2)	C12—H12C	0.96
C3—C4	1.466 (2)	C13—N1	1.4716 (19)
C4—O3	1.2235 (17)	C13—H13A	0.96
C4—N2	1.3914 (19)	C13—H13B	0.96
C5—C6	1.453 (2)	C13—H13C	0.96
C5—H5	0.93	C14—O4	1.4331 (19)
C6—C11	1.402 (2)	C14—H14A	0.96
C6—C7	1.413 (2)	C14—H14B	0.96
C7—C8	1.377 (2)	C14—H14C	0.96
C7—H7	0.93	C15—O5	1.4400 (19)
C8—O4	1.3650 (18)	C15—H15A	0.96
C8—C9	1.416 (2)	C15—H15B	0.96
C9—O5	1.3525 (17)	C15—H15C	0.96
C9—C10	1.389 (2)
O1—C1—N1	121.71 (14)	N2—C12—H12A	109.5
O1—C1—N2	121.60 (14)	N2—C12—H12B	109.5
N1—C1—N2	116.69 (12)	H12A—C12—H12B	109.5
O2—C2—N1	119.59 (13)	N2—C12—H12C	109.5
O2—C2—C3	123.24 (13)	H12A—C12—H12C	109.5
N1—C2—C3	117.16 (13)	H12B—C12—H12C	109.5
C5—C3—C4	127.56 (13)	N1—C13—H13A	109.5
C5—C3—C2	113.69 (13)	N1—C13—H13B	109.5
C4—C3—C2	118.73 (12)	H13A—C13—H13B	109.5
O3—C4—N2	118.37 (14)	N1—C13—H13C	109.5
O3—C4—C3	125.11 (13)	H13A—C13—H13C	109.5
N2—C4—C3	116.51 (13)	H13B—C13—H13C	109.5
C3—C5—C6	138.25 (14)	O4—C14—H14A	109.5
C3—C5—H5	110.9	O4—C14—H14B	109.5
C6—C5—H5	110.9	H14A—C14—H14B	109.5
C11—C6—C7	117.75 (13)	O4—C14—H14C	109.5
C11—C6—C5	115.55 (13)	H14A—C14—H14C	109.5
C7—C6—C5	126.71 (13)	H14B—C14—H14C	109.5
C8—C7—C6	120.66 (13)	O5—C15—H15A	109.5
C8—C7—H7	119.7	O5—C15—H15B	109.5
C6—C7—H7	119.7	H15A—C15—H15B	109.5
O4—C8—C7	124.60 (13)	O5—C15—H15C	109.5
O4—C8—C9	114.77 (12)	H15A—C15—H15C	109.5
C7—C8—C9	120.64 (13)	H15B—C15—H15C	109.5
O5—C9—C10	125.58 (13)	C2—N1—C1	124.99 (13)
O5—C9—C8	115.28 (12)	C2—N1—C13	117.62 (13)
C10—C9—C8	119.14 (13)	C1—N1—C13	117.39 (12)
C11—C10—C9	119.85 (14)	C1—N2—C4	125.56 (13)
C11—C10—H10	120.1	C1—N2—C12	117.23 (12)
C9—C10—H10	120.1	C4—N2—C12	116.91 (12)
C10—C11—C6	121.96 (13)	C9—O5—C15	117.89 (11)
C10—C11—H11	119	C8—O4—C14	116.37 (11)
C6—C11—H11	119

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.93	2.08	2.871 (2)	142.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3	0.93	2.08	2.871 (2)	142