Crystal structure of fenclorim.

In the title compound, C10H6Cl2N2 (systematic name: 4,6-di-chloro-2-phenyl-pyrimidine), which is used commercially as the herbicide safener, fenclorim, the dihedral angle between the di-chloro-pyrimidyl and phenyl rings is 9.45 (10)°. In the crystal, C-H⋯N hydrogen bonds link adjacent mol-ecules, forming chains along the c-axis direction. In addition, weak inter-molecular C-Cl⋯π [3.6185 (10) Å] and π-π [3.8796 (11) Å] inter-actions are present, forming a three-dimensional network.

Related literature

For information on the herbicidal properties of the title compound, see: Wu et al. (1999 ▸). For a related crystal structure, see: Leban & Polanc (1992 ▸).

Experimental

Crystal data

C10H6Cl2N2

M = 225.07

Monoclinic,

a = 5.6210 (6) Å

b = 17.0659 (18) Å

c = 10.2582 (12) Å

β = 99.690 (6)°

V = 970.00 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.62 mm−1

T = 173 K

0.16 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.690, T max = 0.746

9071 measured reflections

2212 independent reflections

1750 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.077

S = 1.07

2212 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015016187/sj5469sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016187/sj5469Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016187/sj5469Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016187/sj5469fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

a . DOI: 10.1107/S2056989015016187/sj5469fig2.tif

Crystal packing viewed along the a axis. The inter­molecular inter­actions are shown as dashed lines.

CCDC reference: 1421258

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H6Cl2N2	F(000) = 456
Mr = 225.07	Dx = 1.541 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.6210 (6) Å	Cell parameters from 2286 reflections
b = 17.0659 (18) Å	θ = 2.3–25.9°
c = 10.2582 (12) Å	µ = 0.62 mm−1
β = 99.690 (6)°	T = 173 K
V = 970.00 (19) Å3	Plate, colourless
Z = 4	0.16 × 0.06 × 0.04 mm

Bruker APEXII CCD diffractometer	1750 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.034
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.5°, θmin = 2.3°
Tmin = 0.690, Tmax = 0.746	h = −6→7
9071 measured reflections	k = −19→22
2212 independent reflections	l = −13→9

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0277P)2 + 0.269P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2212 reflections	Δρmax = 0.28 e Å−3
127 parameters	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.

	x	y	z	Uiso*/Ueq
Cl1	0.65642 (9)	0.34546 (3)	−0.36827 (4)	0.04016 (15)
Cl2	0.00001 (9)	0.21187 (3)	−0.11631 (4)	0.03800 (15)
N1	0.6078 (2)	0.37521 (8)	−0.12511 (13)	0.0265 (3)
N2	0.3094 (2)	0.31826 (8)	−0.01497 (13)	0.0251 (3)
C1	0.5151 (3)	0.33485 (10)	−0.23126 (16)	0.0266 (4)
C2	0.3205 (3)	0.28518 (10)	−0.24028 (16)	0.0274 (4)
H2	0.2551	0.2580	−0.3190	0.033*
C3	0.2296 (3)	0.27863 (10)	−0.12406 (16)	0.0258 (4)
C4	0.4978 (3)	0.36583 (9)	−0.01979 (15)	0.0239 (4)
C5	0.5944 (3)	0.41068 (10)	0.10104 (15)	0.0248 (4)
C6	0.4715 (3)	0.41288 (10)	0.20807 (16)	0.0294 (4)
H6	0.3240	0.3851	0.2044	0.035*
C7	0.5644 (4)	0.45554 (11)	0.31979 (17)	0.0355 (4)
H7	0.4809	0.4566	0.3929	0.043*
C8	0.7773 (4)	0.49654 (12)	0.32573 (18)	0.0381 (5)
H8	0.8395	0.5259	0.4026	0.046*
C9	0.9000 (3)	0.49498 (12)	0.22019 (19)	0.0391 (5)
H9	1.0460	0.5236	0.2239	0.047*
C10	0.8099 (3)	0.45159 (11)	0.10867 (18)	0.0332 (4)
H10	0.8964	0.4498	0.0367	0.040*

	U11	U22	U33	U12	U13	U23
Cl1	0.0519 (3)	0.0482 (3)	0.0248 (2)	−0.0100 (2)	0.0192 (2)	−0.0056 (2)
Cl2	0.0424 (3)	0.0384 (3)	0.0344 (3)	−0.0145 (2)	0.0099 (2)	−0.00277 (19)
N1	0.0314 (8)	0.0280 (8)	0.0213 (7)	−0.0007 (7)	0.0077 (6)	−0.0002 (6)
N2	0.0290 (8)	0.0250 (8)	0.0217 (7)	−0.0008 (6)	0.0056 (6)	0.0012 (6)
C1	0.0352 (10)	0.0268 (9)	0.0194 (8)	0.0042 (8)	0.0095 (7)	0.0021 (7)
C2	0.0346 (10)	0.0265 (9)	0.0210 (8)	−0.0003 (8)	0.0042 (7)	−0.0027 (7)
C3	0.0296 (9)	0.0234 (9)	0.0244 (8)	−0.0008 (7)	0.0043 (7)	0.0021 (7)
C4	0.0278 (9)	0.0240 (9)	0.0200 (8)	0.0047 (7)	0.0046 (7)	0.0033 (6)
C5	0.0307 (9)	0.0226 (9)	0.0209 (8)	0.0032 (7)	0.0035 (7)	0.0011 (6)
C6	0.0375 (10)	0.0264 (9)	0.0253 (9)	0.0013 (8)	0.0080 (7)	0.0005 (7)
C7	0.0500 (12)	0.0366 (11)	0.0206 (9)	0.0080 (9)	0.0078 (8)	−0.0013 (7)
C8	0.0442 (12)	0.0383 (11)	0.0276 (9)	0.0086 (10)	−0.0063 (8)	−0.0079 (8)
C9	0.0323 (10)	0.0415 (12)	0.0406 (11)	−0.0028 (9)	−0.0019 (8)	−0.0081 (9)
C10	0.0316 (10)	0.0375 (11)	0.0311 (9)	−0.0021 (8)	0.0073 (8)	−0.0037 (8)

Cl1—C1	1.7362 (17)	C5—C6	1.393 (2)
Cl2—C3	1.7333 (17)	C6—C7	1.384 (2)
N1—C1	1.319 (2)	C6—H6	0.9500
N1—C4	1.342 (2)	C7—C8	1.379 (3)
N2—C3	1.320 (2)	C7—H7	0.9500
N2—C4	1.342 (2)	C8—C9	1.378 (3)
C1—C2	1.375 (2)	C8—H8	0.9500
C2—C3	1.379 (2)	C9—C10	1.385 (2)
C2—H2	0.9500	C9—H9	0.9500
C4—C5	1.480 (2)	C10—H10	0.9500
C5—C10	1.389 (2)
C1—N1—C4	115.52 (14)	C6—C5—C4	120.90 (15)
C3—N2—C4	115.88 (14)	C7—C6—C5	119.93 (17)
N1—C1—C2	125.22 (15)	C7—C6—H6	120.0
N1—C1—Cl1	116.28 (13)	C5—C6—H6	120.0
C2—C1—Cl1	118.49 (13)	C8—C7—C6	120.49 (17)
C1—C2—C3	113.49 (15)	C8—C7—H7	119.8
C1—C2—H2	123.3	C6—C7—H7	119.8
C3—C2—H2	123.3	C9—C8—C7	120.06 (17)
N2—C3—C2	124.69 (16)	C9—C8—H8	120.0
N2—C3—Cl2	116.58 (13)	C7—C8—H8	120.0
C2—C3—Cl2	118.70 (13)	C8—C9—C10	119.83 (18)
N1—C4—N2	125.13 (15)	C8—C9—H9	120.1
N1—C4—C5	117.31 (15)	C10—C9—H9	120.1
N2—C4—C5	117.55 (14)	C9—C10—C5	120.63 (17)
C10—C5—C6	119.06 (16)	C9—C10—H10	119.7
C10—C5—C4	120.04 (15)	C5—C10—H10	119.7
C4—N1—C1—C2	−0.4 (2)	N1—C4—C5—C10	−8.8 (2)
C4—N1—C1—Cl1	−179.46 (12)	N2—C4—C5—C10	170.39 (16)
N1—C1—C2—C3	−1.8 (3)	N1—C4—C5—C6	170.99 (15)
Cl1—C1—C2—C3	177.25 (12)	N2—C4—C5—C6	−9.9 (2)
C4—N2—C3—C2	−2.3 (2)	C10—C5—C6—C7	0.1 (3)
C4—N2—C3—Cl2	175.70 (12)	C4—C5—C6—C7	−179.64 (15)
C1—C2—C3—N2	3.2 (3)	C5—C6—C7—C8	0.5 (3)
C1—C2—C3—Cl2	−174.72 (13)	C6—C7—C8—C9	−0.3 (3)
C1—N1—C4—N2	1.6 (2)	C7—C8—C9—C10	−0.6 (3)
C1—N1—C4—C5	−179.38 (14)	C8—C9—C10—C5	1.2 (3)
C3—N2—C4—N1	−0.3 (2)	C6—C5—C10—C9	−1.0 (3)
C3—N2—C4—C5	−179.36 (14)	C4—C5—C10—C9	178.79 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2i	0.95	2.46	3.317 (2)	151

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C2H2N2i	0.95	2.46	3.317(2)	151

Symmetry code: (i) .