1-[3-(4-Chloro-phen-yl)-6-methyl-1,6-di-hydro-1,2,4,5-tetra-zin-1-yl]ethanone.

In the title compound, C(11)H(11)ClN(4)O, the tetra-zine ring adopts a non-symmetrical boat conformation. The crystal packing exhibits relatively short inter-molecular C⋯N contacts of 3.118 (3) Å.

Related literature

For related structures, see: Hu et al. (2004 ▶, 2005 ▶); Jennison et al. (1986 ▶); Stam et al. (1982 ▶); Xu et al. (2010 ▶); Yang et al. (2010 ▶). For applications of 1,2,4,5-tetra­zine derivatives, see: Sauer (1996 ▶).

Experimental

Crystal data

C11H11ClN4O

M = 250.69

Orthorhombic,

a = 15.165 (3) Å

b = 8.0452 (15) Å

c = 19.349 (4) Å

V = 2360.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 93 K

0.47 × 0.40 × 0.37 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

17617 measured reflections

2705 independent reflections

2599 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.01

2705 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037839/cv2768sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037839/cv2768Isup2.hkl

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

C11H11ClN4O	F(000) = 1040
Mr = 250.69	Dx = 1.411 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6560 reflections
a = 15.165 (3) Å	θ = 3.1–27.5°
b = 8.0452 (15) Å	µ = 0.31 mm−1
c = 19.349 (4) Å	T = 93 K
V = 2360.7 (8) Å3	Block, orange
Z = 8	0.47 × 0.40 × 0.37 mm

Rigaku AFC10/Saturn724+ diffractometer	2599 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.038
graphite	θmax = 27.5°, θmin = 3.4°
Detector resolution: 28.5714 pixels mm-1	h = −15→19
phi and ω scans	k = −7→10
17617 measured reflections	l = −25→25
2705 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2 + 1.56P] where P = (Fo2 + 2Fc2)/3
2705 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.92289 (3)	0.63612 (7)	0.27240 (2)	0.02638 (19)
O1	0.28242 (9)	0.51349 (19)	0.42261 (8)	0.0260 (4)
N1	0.42522 (10)	0.5869 (2)	0.41004 (8)	0.0165 (3)
N2	0.50513 (10)	0.5506 (2)	0.38219 (8)	0.0167 (3)
N3	0.56159 (11)	0.7128 (2)	0.47435 (8)	0.0191 (4)
N4	0.48695 (11)	0.7527 (2)	0.49690 (9)	0.0203 (4)
C1	0.73156 (13)	0.6887 (3)	0.41229 (10)	0.0226 (4)
H1	0.7261	0.7262	0.4586	0.027*
C2	0.81377 (13)	0.6872 (3)	0.38052 (10)	0.0234 (4)
H2	0.8647	0.7229	0.4050	0.028*
C3	0.82041 (13)	0.6332 (2)	0.31290 (10)	0.0194 (4)
C4	0.74733 (13)	0.5800 (3)	0.27600 (9)	0.0202 (4)
H4	0.7531	0.5428	0.2296	0.024*
C5	0.66569 (13)	0.5822 (3)	0.30804 (10)	0.0200 (4)
H5	0.6149	0.5472	0.2832	0.024*
C6	0.65710 (12)	0.6353 (2)	0.37632 (10)	0.0168 (4)
C7	0.56927 (13)	0.6386 (2)	0.40816 (10)	0.0164 (4)
C8	0.41462 (13)	0.7456 (2)	0.44422 (10)	0.0184 (4)
H8	0.3564	0.7475	0.4685	0.022*
C9	0.42014 (14)	0.8936 (3)	0.39576 (12)	0.0251 (5)
H9A	0.4757	0.8890	0.3699	0.030*
H9B	0.4179	0.9966	0.4227	0.030*
H9C	0.3705	0.8906	0.3634	0.030*
C10	0.35516 (13)	0.4761 (2)	0.40099 (10)	0.0192 (4)
C11	0.37533 (13)	0.3182 (2)	0.36325 (11)	0.0217 (4)
H11A	0.3268	0.2393	0.3697	0.026*
H11B	0.4300	0.2700	0.3814	0.026*
H11C	0.3825	0.3418	0.3139	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0169 (3)	0.0416 (4)	0.0206 (3)	−0.00189 (19)	0.00381 (16)	−0.00357 (19)
O1	0.0156 (7)	0.0260 (8)	0.0363 (8)	−0.0012 (6)	0.0001 (6)	0.0006 (6)
N1	0.0153 (8)	0.0168 (8)	0.0175 (8)	0.0002 (6)	0.0009 (6)	0.0000 (6)
N2	0.0153 (8)	0.0174 (8)	0.0174 (8)	0.0010 (6)	0.0005 (6)	0.0019 (6)
N3	0.0181 (8)	0.0232 (9)	0.0158 (8)	−0.0004 (6)	0.0016 (6)	−0.0013 (6)
N4	0.0195 (8)	0.0231 (8)	0.0184 (8)	−0.0015 (7)	0.0008 (6)	−0.0024 (6)
C1	0.0195 (10)	0.0334 (11)	0.0148 (8)	−0.0025 (8)	0.0011 (7)	−0.0034 (8)
C2	0.0161 (9)	0.0357 (12)	0.0186 (9)	−0.0050 (8)	−0.0018 (7)	−0.0049 (8)
C3	0.0158 (9)	0.0237 (10)	0.0186 (9)	0.0000 (7)	0.0024 (7)	0.0008 (7)
C4	0.0200 (10)	0.0251 (10)	0.0153 (8)	0.0012 (8)	0.0005 (7)	−0.0035 (7)
C5	0.0178 (9)	0.0247 (10)	0.0175 (9)	−0.0008 (8)	−0.0015 (7)	−0.0027 (7)
C6	0.0163 (9)	0.0170 (9)	0.0172 (9)	−0.0010 (7)	0.0002 (7)	0.0005 (6)
C7	0.0170 (10)	0.0172 (9)	0.0150 (9)	0.0015 (7)	−0.0008 (6)	0.0004 (6)
C8	0.0178 (9)	0.0191 (9)	0.0184 (9)	0.0024 (7)	0.0010 (7)	−0.0025 (7)
C9	0.0264 (11)	0.0180 (10)	0.0309 (11)	0.0030 (8)	−0.0019 (8)	0.0014 (8)
C10	0.0174 (9)	0.0205 (10)	0.0198 (9)	−0.0011 (7)	−0.0027 (7)	0.0042 (7)
C11	0.0208 (10)	0.0182 (9)	0.0263 (10)	−0.0036 (8)	−0.0034 (7)	0.0007 (7)

Cl1—C3	1.741 (2)	C4—C5	1.385 (3)
O1—C10	1.218 (2)	C4—H4	0.9500
N1—N2	1.358 (2)	C5—C6	1.395 (3)
N1—C10	1.398 (3)	C5—H5	0.9500
N1—C8	1.447 (2)	C6—C7	1.468 (3)
N2—C7	1.304 (2)	C8—C9	1.518 (3)
N3—N4	1.255 (2)	C8—H8	1.0000
N3—C7	1.418 (2)	C9—H9A	0.9800
N4—C8	1.499 (2)	C9—H9B	0.9800
C1—C2	1.390 (3)	C9—H9C	0.9800
C1—C6	1.394 (3)	C10—C11	1.497 (3)
C1—H1	0.9500	C11—H11A	0.9800
C2—C3	1.382 (3)	C11—H11B	0.9800
C2—H2	0.9500	C11—H11C	0.9800
C3—C4	1.386 (3)
N2—N1—C10	119.42 (16)	N2—C7—N3	121.02 (17)
N2—N1—C8	118.06 (15)	N2—C7—C6	120.36 (17)
C10—N1—C8	122.38 (16)	N3—C7—C6	117.48 (16)
C7—N2—N1	113.33 (16)	N1—C8—N4	105.26 (15)
N4—N3—C7	119.73 (16)	N1—C8—C9	113.80 (16)
N3—N4—C8	114.46 (16)	N4—C8—C9	110.49 (16)
C2—C1—C6	120.20 (17)	N1—C8—H8	109.1
C2—C1—H1	119.9	N4—C8—H8	109.1
C6—C1—H1	119.9	C9—C8—H8	109.1
C3—C2—C1	119.11 (18)	C8—C9—H9A	109.5
C3—C2—H2	120.4	C8—C9—H9B	109.5
C1—C2—H2	120.4	H9A—C9—H9B	109.5
C2—C3—C4	121.77 (18)	C8—C9—H9C	109.5
C2—C3—Cl1	119.14 (15)	H9A—C9—H9C	109.5
C4—C3—Cl1	119.08 (15)	H9B—C9—H9C	109.5
C5—C4—C3	118.70 (17)	O1—C10—N1	119.20 (18)
C5—C4—H4	120.7	O1—C10—C11	124.23 (18)
C3—C4—H4	120.7	N1—C10—C11	116.56 (17)
C4—C5—C6	120.77 (18)	C10—C11—H11A	109.5
C4—C5—H5	119.6	C10—C11—H11B	109.5
C6—C5—H5	119.6	H11A—C11—H11B	109.5
C1—C6—C5	119.45 (17)	C10—C11—H11C	109.5
C1—C6—C7	121.32 (17)	H11A—C11—H11C	109.5
C5—C6—C7	119.21 (17)	H11B—C11—H11C	109.5
C10—N1—N2—C7	−163.54 (16)	N4—N3—C7—C6	163.93 (18)
C8—N1—N2—C7	20.6 (2)	C1—C6—C7—N2	−162.04 (18)
C7—N3—N4—C8	−11.1 (3)	C5—C6—C7—N2	19.9 (3)
C6—C1—C2—C3	0.4 (3)	C1—C6—C7—N3	5.9 (3)
C1—C2—C3—C4	−0.2 (3)	C5—C6—C7—N3	−172.22 (17)
C1—C2—C3—Cl1	178.44 (17)	N2—N1—C8—N4	−54.1 (2)
C2—C3—C4—C5	0.3 (3)	C10—N1—C8—N4	130.11 (17)
Cl1—C3—C4—C5	−178.33 (16)	N2—N1—C8—C9	67.0 (2)
C3—C4—C5—C6	−0.6 (3)	C10—N1—C8—C9	−108.8 (2)
C2—C1—C6—C5	−0.7 (3)	N3—N4—C8—N1	47.4 (2)
C2—C1—C6—C7	−178.79 (19)	N3—N4—C8—C9	−75.8 (2)
C4—C5—C6—C1	0.8 (3)	N2—N1—C10—O1	−175.83 (17)
C4—C5—C6—C7	178.96 (19)	C8—N1—C10—O1	−0.1 (3)
N1—N2—C7—N3	22.6 (2)	N2—N1—C10—C11	2.9 (2)
N1—N2—C7—C6	−169.92 (16)	C8—N1—C10—C11	178.63 (17)
N4—N3—C7—N2	−28.2 (3)