Crystal structure of cyprodinil.

In the title compound, C14H15N3 (systematic name: 4-cyclo-propyl-6-methyl-N-phenyl-pyrimidin-2-amine), which is the anilino-pyrimidine fungicide cyprodinil, the dihedral angles between the planes of the central pyrimidine ring and the terminal phenyl ring and the mean plane of the cyclo-propane ring system are 14.52 (11) and 88.79 (10)°, respectively. In the crystal, weak π-π inter-actions [3.8551 (11) Å] connect the dimers into chains along the b-axis direction.

Related literature

For information on the fungicidal properties of the title compound, see: Sapp et al. (2003 ▸). For a related crystal structure, see: Kang et al. (2014 ▸).

Experimental

Crystal data

C14H15N3

M = 225.29

Monoclinic,

a = 13.1920 (6) Å

b = 5.3176 (2) Å

c = 16.8641 (7) Å

β = 100.288 (2)°

V = 1163.99 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.45 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.965, T max = 0.986

18116 measured reflections

2864 independent reflections

2463 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.166

S = 1.14

2864 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014025742/hg5422sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025742/hg5422Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014025742/hg5422Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014025742/hg5422fig1.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/S2056989014025742/hg5422fig2.tif

Crystal packing viewed along the a axis. The inter­molecular N—H⋯N hydrogen bonds, and weak π–π inter­actions are shown as dashed lines.

CCDC reference: 1035821

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

C14H15N3	F(000) = 480
Mr = 225.29	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8168 reflections
a = 13.1920 (6) Å	θ = 2.5–28.2°
b = 5.3176 (2) Å	µ = 0.08 mm−1
c = 16.8641 (7) Å	T = 173 K
β = 100.288 (2)°	Block, colourless
V = 1163.99 (8) Å3	0.45 × 0.22 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2463 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.965, Tmax = 0.986	k = −7→7
18116 measured reflections	l = −21→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0577P)2 + 1.3715P] where P = (Fo2 + 2Fc2)/3
2864 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.31 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
N1	0.64381 (12)	0.1086 (3)	0.81833 (9)	0.0210 (3)
H1N	0.5882	0.0697	0.7834	0.025*
N2	0.70730 (12)	0.3584 (3)	0.93020 (9)	0.0201 (3)
N3	0.53921 (12)	0.4215 (3)	0.84955 (9)	0.0206 (3)
C1	0.83033 (14)	0.0059 (4)	0.85440 (11)	0.0246 (4)
H1	0.8436	0.1437	0.8906	0.030*
C2	0.90995 (15)	−0.1513 (4)	0.84207 (12)	0.0277 (4)
H2	0.9778	−0.1183	0.8700	0.033*
C3	0.89324 (15)	−0.3555 (4)	0.79011 (12)	0.0256 (4)
H3	0.9486	−0.4621	0.7827	0.031*
C4	0.79368 (15)	−0.4010 (4)	0.74907 (11)	0.0241 (4)
H4	0.7808	−0.5396	0.7131	0.029*
C5	0.71331 (14)	−0.2457 (4)	0.76022 (11)	0.0208 (4)
H5	0.6458	−0.2787	0.7318	0.025*
C6	0.73029 (14)	−0.0402 (4)	0.81301 (10)	0.0195 (4)
C7	0.63140 (14)	0.3035 (4)	0.86853 (10)	0.0189 (4)
C8	0.69016 (14)	0.5539 (4)	0.97648 (10)	0.0208 (4)
C9	0.59859 (15)	0.6871 (4)	0.96202 (11)	0.0233 (4)
H9	0.5873	0.8251	0.9951	0.028*
C10	0.52353 (14)	0.6127 (4)	0.89742 (11)	0.0209 (4)
C11	0.77222 (15)	0.6184 (4)	1.04550 (11)	0.0246 (4)
H11	0.7567	0.7622	1.0796	0.029*
C12	0.83749 (15)	0.4101 (4)	1.08962 (12)	0.0276 (4)
H12A	0.8585	0.4258	1.1488	0.033*
H12B	0.8239	0.2360	1.0698	0.033*
C13	0.88371 (16)	0.5880 (4)	1.03804 (12)	0.0300 (5)
H13A	0.8989	0.5239	0.9863	0.036*
H13B	0.9334	0.7136	1.0653	0.036*
C14	0.42255 (15)	0.7483 (4)	0.87894 (12)	0.0255 (4)
H14A	0.4283	0.8895	0.8427	0.038*
H14B	0.4043	0.8118	0.9291	0.038*
H14C	0.3690	0.6324	0.8530	0.038*

	U11	U22	U33	U12	U13	U23
N1	0.0185 (7)	0.0259 (8)	0.0165 (7)	0.0004 (6)	−0.0023 (5)	−0.0027 (6)
N2	0.0205 (7)	0.0238 (8)	0.0145 (7)	0.0001 (6)	−0.0009 (5)	0.0008 (6)
N3	0.0196 (7)	0.0250 (8)	0.0164 (7)	0.0014 (6)	0.0010 (5)	0.0005 (6)
C1	0.0218 (9)	0.0278 (10)	0.0221 (9)	−0.0006 (8)	−0.0016 (7)	−0.0040 (8)
C2	0.0209 (9)	0.0329 (11)	0.0270 (9)	0.0014 (8)	−0.0016 (7)	−0.0027 (8)
C3	0.0242 (9)	0.0279 (10)	0.0243 (9)	0.0047 (8)	0.0031 (7)	0.0001 (8)
C4	0.0290 (10)	0.0234 (10)	0.0194 (8)	−0.0003 (8)	0.0027 (7)	−0.0025 (7)
C5	0.0226 (9)	0.0220 (9)	0.0166 (8)	−0.0016 (7)	0.0002 (6)	0.0006 (7)
C6	0.0207 (8)	0.0227 (9)	0.0146 (7)	0.0004 (7)	0.0014 (6)	0.0019 (7)
C7	0.0200 (8)	0.0221 (9)	0.0138 (7)	0.0002 (7)	0.0007 (6)	0.0016 (7)
C8	0.0227 (9)	0.0233 (9)	0.0151 (8)	−0.0009 (7)	0.0005 (6)	0.0016 (7)
C9	0.0258 (9)	0.0246 (10)	0.0181 (8)	0.0028 (8)	0.0001 (7)	−0.0033 (7)
C10	0.0219 (9)	0.0235 (9)	0.0167 (8)	0.0015 (7)	0.0018 (6)	0.0022 (7)
C11	0.0250 (9)	0.0284 (10)	0.0180 (8)	0.0005 (8)	−0.0025 (7)	−0.0035 (7)
C12	0.0244 (9)	0.0333 (11)	0.0216 (9)	0.0006 (8)	−0.0053 (7)	0.0005 (8)
C13	0.0245 (9)	0.0382 (12)	0.0247 (9)	−0.0057 (8)	−0.0022 (7)	−0.0022 (9)
C14	0.0232 (9)	0.0289 (10)	0.0226 (9)	0.0054 (8)	−0.0005 (7)	−0.0004 (8)

N1—C7	1.367 (2)	C5—H5	0.9500
N1—C6	1.404 (2)	C8—C9	1.384 (3)
N1—H1N	0.8800	C8—C11	1.481 (2)
N2—C7	1.341 (2)	C9—C10	1.392 (3)
N2—C8	1.343 (2)	C9—H9	0.9500
N3—C10	1.337 (2)	C10—C14	1.498 (3)
N3—C7	1.355 (2)	C11—C13	1.507 (3)
C1—C2	1.387 (3)	C11—C12	1.514 (3)
C1—C6	1.400 (2)	C11—H11	1.0000
C1—H1	0.9500	C12—C13	1.488 (3)
C2—C3	1.388 (3)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.392 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.383 (3)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—C6	1.402 (3)	C14—H14C	0.9800
C7—N1—C6	130.97 (15)	C8—C9—H9	121.0
C7—N1—H1N	114.5	C10—C9—H9	121.0
C6—N1—H1N	114.5	N3—C10—C9	121.56 (17)
C7—N2—C8	116.06 (16)	N3—C10—C14	117.93 (16)
C10—N3—C7	116.01 (16)	C9—C10—C14	120.50 (17)
C2—C1—C6	119.45 (18)	C8—C11—C13	119.78 (16)
C2—C1—H1	120.3	C8—C11—C12	119.22 (18)
C6—C1—H1	120.3	C13—C11—C12	58.99 (14)
C1—C2—C3	121.81 (18)	C8—C11—H11	115.7
C1—C2—H2	119.1	C13—C11—H11	115.7
C3—C2—H2	119.1	C12—C11—H11	115.7
C2—C3—C4	118.62 (18)	C13—C12—C11	60.26 (14)
C2—C3—H3	120.7	C13—C12—H12A	117.7
C4—C3—H3	120.7	C11—C12—H12A	117.7
C5—C4—C3	120.47 (18)	C13—C12—H12B	117.7
C5—C4—H4	119.8	C11—C12—H12B	117.7
C3—C4—H4	119.8	H12A—C12—H12B	114.9
C4—C5—C6	120.82 (17)	C12—C13—C11	60.74 (14)
C4—C5—H5	119.6	C12—C13—H13A	117.7
C6—C5—H5	119.6	C11—C13—H13A	117.7
C1—C6—C5	118.84 (17)	C12—C13—H13B	117.7
C1—C6—N1	125.02 (17)	C11—C13—H13B	117.7
C5—C6—N1	116.12 (16)	H13A—C13—H13B	114.8
N2—C7—N3	126.65 (17)	C10—C14—H14A	109.5
N2—C7—N1	119.35 (16)	C10—C14—H14B	109.5
N3—C7—N1	114.00 (16)	H14A—C14—H14B	109.5
N2—C8—C9	121.73 (17)	C10—C14—H14C	109.5
N2—C8—C11	117.43 (17)	H14A—C14—H14C	109.5
C9—C8—C11	120.82 (17)	H14B—C14—H14C	109.5
C8—C9—C10	117.96 (18)
C6—C1—C2—C3	−0.5 (3)	C6—N1—C7—N3	172.68 (17)
C1—C2—C3—C4	0.5 (3)	C7—N2—C8—C9	1.2 (3)
C2—C3—C4—C5	−0.2 (3)	C7—N2—C8—C11	179.58 (16)
C3—C4—C5—C6	−0.1 (3)	N2—C8—C9—C10	0.0 (3)
C2—C1—C6—C5	0.2 (3)	C11—C8—C9—C10	−178.32 (18)
C2—C1—C6—N1	−178.05 (18)	C7—N3—C10—C9	1.0 (3)
C4—C5—C6—C1	0.1 (3)	C7—N3—C10—C14	−179.81 (17)
C4—C5—C6—N1	178.52 (17)	C8—C9—C10—N3	−1.2 (3)
C7—N1—C6—C1	−8.8 (3)	C8—C9—C10—C14	179.64 (18)
C7—N1—C6—C5	172.85 (18)	N2—C8—C11—C13	35.3 (3)
C8—N2—C7—N3	−1.5 (3)	C9—C8—C11—C13	−146.3 (2)
C8—N2—C7—N1	179.34 (16)	N2—C8—C11—C12	−33.6 (3)
C10—N3—C7—N2	0.4 (3)	C9—C8—C11—C12	144.84 (19)
C10—N3—C7—N1	179.63 (16)	C8—C11—C12—C13	109.1 (2)
C6—N1—C7—N2	−8.0 (3)	C8—C11—C13—C12	−108.2 (2)