Monocrotophos: dimethyl (E)-1-methyl-2-(methyl-carbamo-yl)ethenyl phosphate.

In the title compound, C(7)H(14)NO(5)P, the phosphate group displays rotational disorder of three O atoms with an occupancy ratio of 0.832 (6):0.167 (6). The dihedral angle between the acryl-amide group and PO(2) plane of the phosphate group is 75.69 (7)°. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the molecules.

Related literature

For the toxicity and insecticidal properties of the title compound, see: Dureja (1989 ▶); Chakravarthi et al. (2007 ▶). For related structures, see: Osman & El-Samahy (2007 ▶).

Experimental

Crystal data

C7H14NO5P

M = 223.16

Monoclinic,

a = 10.0498 (2) Å

b = 11.3501 (2) Å

c = 10.4587 (2) Å

β = 115.377 (1)°

V = 1077.87 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.35 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.917, T max = 0.940

17626 measured reflections

2673 independent reflections

2411 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.08

2673 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003898/jh2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003898/jh2262Isup2.hkl

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

C7H14NO5P	F(000) = 472
Mr = 223.16	Dx = 1.375 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9925 reflections
a = 10.0498 (2) Å	θ = 2.4–28.3°
b = 11.3501 (2) Å	µ = 0.25 mm−1
c = 10.4587 (2) Å	T = 173 K
β = 115.377 (1)°	Block, colourless
V = 1077.87 (4) Å3	0.35 × 0.35 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	2673 independent reflections
Radiation source: fine-focus sealed tube	2411 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.917, Tmax = 0.940	k = −15→15
17626 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0647P)2 + 0.3928P] where P = (Fo2 + 2Fc2)/3
2673 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.38 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	Occ. (<1)
P1	0.72597 (4)	0.12670 (3)	0.30753 (4)	0.02990 (14)
O1	0.87089 (17)	0.17794 (17)	0.35222 (16)	0.0442 (4)	0.833 (2)
O2	0.60357 (16)	0.22189 (12)	0.25429 (17)	0.0421 (4)	0.833 (2)
O3	0.69477 (16)	0.05711 (13)	0.41970 (14)	0.0404 (4)	0.833 (2)
O1'	0.8042 (9)	0.2366 (7)	0.2975 (8)	0.0385 (17)	0.167 (2)
O2'	0.5877 (7)	0.1471 (7)	0.3323 (7)	0.0414 (18)	0.167 (2)
O3'	0.8319 (8)	0.0599 (7)	0.4465 (7)	0.0446 (19)	0.167 (2)
O4	0.68546 (12)	0.03323 (9)	0.18490 (11)	0.0319 (2)
O5	0.75176 (15)	0.08602 (13)	−0.19560 (13)	0.0486 (3)
N1	0.55391 (16)	0.20368 (14)	−0.26018 (15)	0.0423 (3)
H1N	0.4883	0.2357	−0.2360	0.051*
C1	0.44938 (19)	0.19657 (18)	0.2069 (2)	0.0494 (4)
H1A	0.3929	0.2700	0.1787	0.074*	0.833 (2)
H1B	0.4335	0.1597	0.2840	0.074*	0.833 (2)
H1C	0.4168	0.1428	0.1259	0.074*	0.833 (2)
H1D	0.3692	0.2054	0.2359	0.074*	0.167 (2)
H1E	0.4189	0.1421	0.1267	0.074*	0.167 (2)
H1F	0.4726	0.2735	0.1790	0.074*	0.167 (2)
C2	0.7899 (3)	−0.0384 (2)	0.4980 (2)	0.0655 (6)
H2A	0.7542	−0.0715	0.5641	0.098*	0.833 (2)
H2B	0.8904	−0.0087	0.5510	0.098*	0.833 (2)
H2C	0.7898	−0.0998	0.4321	0.098*	0.833 (2)
H2D	0.8730	−0.0660	0.5840	0.098*	0.167 (2)
H2E	0.7597	−0.1009	0.4265	0.098*	0.167 (2)
H2F	0.7073	−0.0181	0.5201	0.098*	0.167 (2)
C3	0.72637 (16)	0.04930 (12)	0.07257 (14)	0.0284 (3)
C4	0.86253 (19)	−0.01539 (16)	0.09550 (19)	0.0442 (4)
H4A	0.8863	−0.0020	0.0151	0.066*
H4B	0.8477	−0.0998	0.1041	0.066*
H4C	0.9438	0.0128	0.1825	0.066*
C5	0.63716 (16)	0.11200 (13)	−0.03706 (15)	0.0298 (3)
H5A	0.5546	0.1478	−0.0310	0.036*
C6	0.65555 (17)	0.13105 (13)	−0.16923 (16)	0.0324 (3)
C7	0.5494 (3)	0.2307 (3)	−0.3968 (2)	0.0675 (7)
H7A	0.4682	0.2854	−0.4472	0.101*
H7B	0.5341	0.1580	−0.4518	0.101*
H7C	0.6427	0.2670	−0.3841	0.101*

	U11	U22	U33	U12	U13	U23
P1	0.0279 (2)	0.0352 (2)	0.0273 (2)	−0.00341 (13)	0.01246 (16)	−0.00360 (13)
O1	0.0347 (8)	0.0594 (11)	0.0381 (8)	−0.0165 (8)	0.0151 (6)	−0.0108 (7)
O2	0.0392 (8)	0.0322 (7)	0.0528 (8)	0.0013 (5)	0.0176 (6)	−0.0072 (6)
O3	0.0375 (8)	0.0562 (9)	0.0320 (7)	0.0005 (6)	0.0194 (6)	0.0036 (6)
O1'	0.045 (4)	0.034 (4)	0.044 (4)	−0.014 (3)	0.027 (4)	−0.011 (3)
O2'	0.027 (3)	0.062 (4)	0.039 (4)	0.006 (3)	0.019 (3)	−0.006 (3)
O3'	0.038 (4)	0.053 (4)	0.031 (3)	−0.004 (3)	0.004 (3)	0.005 (3)
O4	0.0373 (6)	0.0325 (5)	0.0290 (5)	−0.0056 (4)	0.0172 (4)	−0.0023 (4)
O5	0.0465 (7)	0.0676 (8)	0.0418 (7)	0.0217 (6)	0.0284 (6)	0.0121 (6)
N1	0.0413 (7)	0.0568 (8)	0.0342 (7)	0.0167 (6)	0.0214 (6)	0.0118 (6)
C1	0.0347 (8)	0.0538 (10)	0.0550 (11)	0.0079 (7)	0.0149 (7)	−0.0083 (8)
C2	0.0593 (13)	0.0810 (15)	0.0554 (12)	0.0133 (11)	0.0237 (10)	0.0319 (11)
C3	0.0318 (7)	0.0271 (6)	0.0287 (6)	−0.0031 (5)	0.0152 (5)	−0.0037 (5)
C4	0.0429 (9)	0.0498 (9)	0.0429 (9)	0.0172 (7)	0.0214 (7)	0.0102 (7)
C5	0.0287 (7)	0.0333 (7)	0.0305 (7)	0.0020 (5)	0.0156 (6)	−0.0014 (5)
C6	0.0318 (7)	0.0369 (7)	0.0298 (7)	0.0020 (5)	0.0147 (6)	0.0005 (5)
C7	0.0618 (13)	0.1063 (19)	0.0439 (10)	0.0368 (13)	0.0317 (10)	0.0331 (11)

P1—O1	1.4472 (14)	C1—H1D	0.9800
P1—O1'	1.501 (7)	C1—H1E	0.9800
P1—O2'	1.536 (6)	C1—H1F	0.9800
P1—O2	1.5503 (14)	C2—H2A	0.9800
P1—O3	1.5536 (13)	C2—H2B	0.9800
P1—O4	1.5775 (11)	C2—H2C	0.9800
P1—O3'	1.580 (7)	C2—H2D	0.9800
O2—C1	1.439 (2)	C2—H2E	0.9800
O3—C2	1.446 (2)	C2—H2F	0.9800
O2'—C1	1.551 (7)	C3—C5	1.321 (2)
O3'—C2	1.382 (8)	C3—C4	1.479 (2)
O4—C3	1.4130 (16)	C4—H4A	0.9800
O5—C6	1.2250 (19)	C4—H4B	0.9800
N1—C6	1.340 (2)	C4—H4C	0.9800
N1—C7	1.442 (2)	C5—C6	1.487 (2)
N1—H1N	0.8800	C5—H5A	0.9500
C1—H1A	0.9800	C7—H7A	0.9800
C1—H1B	0.9800	C7—H7B	0.9800
C1—H1C	0.9800	C7—H7C	0.9800
O1—P1—O1'	37.3 (3)	H1B—C1—H1F	140.3
O1—P1—O2'	138.0 (3)	H1C—C1—H1F	109.3
O1'—P1—O2'	115.2 (4)	H1D—C1—H1F	109.5
O1—P1—O2	111.70 (10)	H1E—C1—H1F	109.5
O1'—P1—O2	75.8 (3)	O3'—C2—O3	54.0 (3)
O2'—P1—O2	47.1 (3)	O3'—C2—H2A	148.2
O1—P1—O3	117.47 (9)	O3—C2—H2A	109.5
O1'—P1—O3	139.1 (3)	O3'—C2—H2B	61.9
O2'—P1—O3	57.3 (3)	O3—C2—H2B	109.5
O2—P1—O3	103.86 (8)	H2A—C2—H2B	109.5
O1—P1—O4	113.96 (8)	O3'—C2—H2C	102.0
O1'—P1—O4	117.5 (3)	O3—C2—H2C	109.5
O2'—P1—O4	107.5 (3)	H2A—C2—H2C	109.5
O2—P1—O4	106.74 (7)	H2B—C2—H2C	109.5
O3—P1—O4	101.93 (7)	O3'—C2—H2D	109.5
O1—P1—O3'	73.0 (3)	O3—C2—H2D	148.9
O1'—P1—O3'	107.2 (4)	H2A—C2—H2D	69.9
O2'—P1—O3'	102.6 (4)	H2B—C2—H2D	47.5
O2—P1—O3'	141.6 (3)	H2C—C2—H2D	99.4
O3—P1—O3'	48.4 (3)	O3'—C2—H2E	109.5
O4—P1—O3'	105.2 (3)	O3—C2—H2E	101.3
C1—O2—P1	123.79 (13)	H2A—C2—H2E	100.0
C2—O3—P1	120.71 (13)	H2B—C2—H2E	126.0
P1—O2'—C1	117.4 (5)	H2C—C2—H2E	16.6
C2—O3'—P1	123.3 (5)	H2D—C2—H2E	109.5
C3—O4—P1	121.57 (9)	O3'—C2—H2F	109.5
C6—N1—C7	121.65 (15)	O3—C2—H2F	62.3
C6—N1—H1N	119.2	H2A—C2—H2F	47.2
C7—N1—H1N	119.2	H2B—C2—H2F	123.9
O2—C1—O2'	48.6 (3)	H2C—C2—H2F	126.0
O2—C1—H1A	109.5	H2D—C2—H2F	109.5
O2'—C1—H1A	139.2	H2E—C2—H2F	109.5
O2—C1—H1B	109.5	C5—C3—O4	117.41 (13)
O2'—C1—H1B	63.5	C5—C3—C4	130.16 (14)
H1A—C1—H1B	109.5	O4—C3—C4	112.32 (12)
O2—C1—H1C	109.5	C3—C4—H4A	109.5
O2'—C1—H1C	110.6	C3—C4—H4B	109.5
H1A—C1—H1C	109.5	H4A—C4—H4B	109.5
H1B—C1—H1C	109.5	C3—C4—H4C	109.5
O2—C1—H1D	141.2	H4A—C4—H4C	109.5
O2'—C1—H1D	109.5	H4B—C4—H4C	109.5
H1A—C1—H1D	63.8	C3—C5—C6	125.23 (13)
H1B—C1—H1D	49.0	C3—C5—H5A	117.4
H1C—C1—H1D	108.5	C6—C5—H5A	117.4
O2—C1—H1E	108.4	O5—C6—N1	122.15 (15)
O2'—C1—H1E	109.5	O5—C6—C5	124.98 (14)
H1A—C1—H1E	110.5	N1—C6—C5	112.87 (13)
H1B—C1—H1E	109.5	N1—C7—H7A	109.5
H1C—C1—H1E	1.2	N1—C7—H7B	109.5
H1D—C1—H1E	109.5	H7A—C7—H7B	109.5
O2—C1—H1F	64.3	N1—C7—H7C	109.5
O2'—C1—H1F	109.5	H7A—C7—H7C	109.5
H1A—C1—H1F	48.2	H7B—C7—H7C	109.5
O1—P1—O2—C1	−178.29 (15)	O2—P1—O3'—C2	84.0 (7)
O1'—P1—O2—C1	171.5 (3)	O3—P1—O3'—C2	31.1 (4)
O2'—P1—O2—C1	−42.1 (4)	O4—P1—O3'—C2	−61.4 (6)
O3—P1—O2—C1	−50.73 (17)	O1—P1—O4—C3	−38.76 (15)
O4—P1—O2—C1	56.53 (16)	O1'—P1—O4—C3	2.6 (4)
O3'—P1—O2—C1	−88.6 (5)	O2'—P1—O4—C3	134.5 (3)
O1—P1—O3—C2	−54.1 (2)	O2—P1—O4—C3	85.04 (12)
O1'—P1—O3—C2	−93.8 (5)	O3—P1—O4—C3	−166.34 (11)
O2'—P1—O3—C2	174.5 (4)	O3'—P1—O4—C3	−116.6 (3)
O2—P1—O3—C2	−178.02 (16)	P1—O2—C1—O2'	40.5 (4)
O4—P1—O3—C2	71.16 (17)	P1—O2'—C1—O2	−37.8 (3)
O3'—P1—O3—C2	−28.7 (4)	P1—O3'—C2—O3	−30.9 (4)
O1—P1—O2'—C1	109.6 (5)	P1—O3—C2—O3'	30.5 (4)
O1'—P1—O2'—C1	71.9 (6)	P1—O4—C3—C5	−85.84 (15)
O2—P1—O2'—C1	35.6 (3)	P1—O4—C3—C4	97.63 (14)
O3—P1—O2'—C1	−154.4 (7)	O4—C3—C5—C6	−175.23 (13)
O4—P1—O2'—C1	−61.2 (6)	C4—C3—C5—C6	0.6 (3)
O3'—P1—O2'—C1	−171.9 (5)	C7—N1—C6—O5	1.7 (3)
O1—P1—O3'—C2	−172.4 (7)	C7—N1—C6—C5	−177.96 (19)
O1'—P1—O3'—C2	172.7 (6)	C3—C5—C6—O5	3.9 (3)
O2'—P1—O3'—C2	51.0 (7)	C3—C5—C6—N1	−176.46 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88	2.03	2.902 (2)	169
C4—H4B···O2ii	0.98	2.43	3.319 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.88	2.03	2.902 (2)	169
C4—H4B⋯O2ii	0.98	2.43	3.319 (2)	151

Symmetry codes: (i) ; (ii) .