2-(2,4-Dichloro­phen­oxy)-N-(4,6-dimethoxy­pyrimidin-2-yl)propionamide

The title compound, C₁₅H₁₅Cl₂N₃O₄, is an amide herbicide with a pyrimidine ring attached to the N atom of the CONH group. The crystal structure determination reveals that there is an intra­molecular hydrogen bond, forming a five-membered ring.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.057
• wR factor = 0.173
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

2-(2,4-Dichlorophenoxy)-N-(4,6-dimethoxypyrimidin-2-yl)propionamide

Crystal data

C15H15Cl2N3O4	Z = 2
Mr = 372.20	F(000) = 384
Triclinic, P1	Dx = 1.421 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.345 (2) Å	Cell parameters from 3006 reflections
b = 9.944 (4) Å	θ = 2.0–25.0°
c = 11.779 (3) Å	µ = 0.40 mm^−1
α = 84.580 (7)°	T = 298 K
β = 71.698 (5)°	Block, colorless
γ = 70.013 (4)°	0.35 × 0.10 × 0.10 mm
V = 872.0 (5) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3006 independent reflections
Radiation source: fine-focus sealed tube	2150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −7→9
Tmin = 0.874, Tmax = 0.962	k = −11→11
3645 measured reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.0917P)^2 + 0.5362P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
3006 reflections	Δρmax = 0.48 e Å^−3
221 parameters	Δρmin = −0.48 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (1)

Special details

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.64983 (19)	0.65339 (11)	1.18042 (11)	0.1061 (5)
Cl2	0.90567 (19)	0.38824 (12)	0.74946 (9)	0.1100 (5)
N1	0.7480 (3)	0.0605 (3)	0.7022 (2)	0.0552 (7)
H1	0.7884	0.1279	0.7070	0.066*
O1	0.7872 (3)	0.1671 (3)	0.87638 (19)	0.0727 (7)
O2	0.6298 (4)	−0.0984 (3)	0.8208 (2)	0.0969 (10)
O3	0.6813 (4)	−0.2128 (3)	0.4333 (2)	0.0765 (7)
O4	0.8539 (4)	0.1891 (3)	0.3091 (2)	0.0751 (7)
C1	0.7448 (4)	0.2782 (3)	0.9530 (3)	0.0538 (7)
C2	0.6540 (5)	0.2849 (4)	1.0730 (3)	0.0685 (10)
H2	0.6133	0.2102	1.1083	0.082*
C3	0.6229 (5)	0.4013 (4)	1.1414 (3)	0.0643 (9)
H3	0.5591	0.4057	1.2222	0.077*
C4	0.6850 (5)	0.5099 (3)	1.0913 (3)	0.0638 (9)
C5	0.7742 (5)	0.5069 (4)	0.9712 (3)	0.0781 (11)
H5	0.8148	0.5820	0.9367	0.094*
C6	0.8028 (4)	0.3915 (4)	0.9026 (3)	0.0618 (8)
C7	0.7089 (5)	0.0560 (4)	0.9162 (3)	0.0639 (9)
H7	0.5898	0.0970	0.9732	0.077*
C8	0.8221 (6)	−0.0619 (5)	0.9758 (4)	0.0893 (12)
H8A	0.9393	−0.1020	0.9206	0.134*
H8B	0.7679	−0.1351	1.0005	0.134*
H8C	0.8314	−0.0237	1.0445	0.134*
C9	0.6904 (4)	−0.0020 (4)	0.8073 (3)	0.0603 (8)
C10	0.7518 (4)	0.0320 (3)	0.5875 (3)	0.0498 (7)
N2	0.7143 (3)	−0.0822 (3)	0.5703 (2)	0.0522 (6)
C12	0.7223 (4)	−0.1009 (3)	0.4579 (3)	0.0579 (8)
C13	0.7679 (5)	−0.0129 (4)	0.3664 (3)	0.0651 (9)
H13	0.7728	−0.0286	0.2886	0.078*
C14	0.8063 (4)	0.1010 (3)	0.3966 (3)	0.0572 (8)
N3	0.7988 (3)	0.1260 (3)	0.5070 (2)	0.0517 (6)
C16	0.6503 (6)	−0.3122 (4)	0.5260 (4)	0.0852 (12)
H16A	0.7616	−0.3688	0.5393	0.128*
H16B	0.5983	−0.3736	0.5030	0.128*
H16C	0.5701	−0.2611	0.5983	0.128*
C17	0.8989 (6)	0.3055 (4)	0.3381 (4)	0.0818 (11)
H17A	0.7979	0.3671	0.3966	0.123*
H17B	0.9309	0.3588	0.2673	0.123*
H17C	0.9980	0.2687	0.3700	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1550 (12)	0.0609 (6)	0.0937 (8)	−0.0379 (6)	−0.0183 (7)	−0.0154 (5)
Cl2	0.1570 (12)	0.0912 (8)	0.0679 (6)	−0.0721 (8)	0.0197 (6)	0.0001 (5)
N1	0.0680 (16)	0.0655 (16)	0.0461 (14)	−0.0399 (13)	−0.0165 (12)	0.0015 (11)
O1	0.1037 (18)	0.0922 (17)	0.0470 (12)	−0.0730 (15)	−0.0115 (12)	0.0008 (11)
O2	0.148 (3)	0.123 (2)	0.0558 (14)	−0.108 (2)	−0.0087 (15)	−0.0026 (14)
O3	0.0937 (18)	0.0842 (17)	0.0652 (15)	−0.0484 (14)	−0.0164 (13)	−0.0168 (12)
O4	0.0979 (18)	0.0800 (16)	0.0575 (14)	−0.0417 (14)	−0.0278 (13)	0.0162 (12)
C1	0.0623 (18)	0.0667 (19)	0.0488 (16)	−0.0370 (16)	−0.0229 (14)	0.0049 (14)
C2	0.096 (3)	0.086 (2)	0.0498 (18)	−0.062 (2)	−0.0257 (17)	0.0108 (16)
C3	0.078 (2)	0.077 (2)	0.0483 (17)	−0.0342 (18)	−0.0232 (16)	0.0039 (16)
C4	0.074 (2)	0.0514 (18)	0.070 (2)	−0.0196 (16)	−0.0280 (18)	0.0016 (15)
C5	0.095 (3)	0.053 (2)	0.082 (3)	−0.0366 (19)	−0.007 (2)	0.0039 (17)
C6	0.067 (2)	0.0620 (19)	0.0577 (19)	−0.0306 (16)	−0.0117 (15)	0.0068 (15)
C7	0.089 (2)	0.080 (2)	0.0453 (17)	−0.060 (2)	−0.0156 (16)	0.0061 (15)
C8	0.118 (3)	0.109 (3)	0.067 (2)	−0.066 (3)	−0.036 (2)	0.016 (2)
C9	0.070 (2)	0.077 (2)	0.0476 (17)	−0.0474 (18)	−0.0091 (15)	−0.0006 (15)
C10	0.0449 (16)	0.0565 (17)	0.0501 (16)	−0.0209 (14)	−0.0121 (13)	−0.0009 (13)
N2	0.0520 (14)	0.0598 (15)	0.0485 (14)	−0.0239 (12)	−0.0125 (11)	−0.0052 (11)
C12	0.0549 (18)	0.0631 (19)	0.0573 (19)	−0.0225 (15)	−0.0121 (14)	−0.0116 (15)
C13	0.074 (2)	0.082 (2)	0.0465 (18)	−0.0313 (18)	−0.0196 (16)	−0.0052 (16)
C14	0.0564 (18)	0.0627 (19)	0.0527 (18)	−0.0198 (15)	−0.0176 (14)	0.0049 (14)
N3	0.0520 (14)	0.0581 (15)	0.0498 (14)	−0.0224 (12)	−0.0180 (11)	0.0034 (11)
C16	0.100 (3)	0.072 (2)	0.095 (3)	−0.045 (2)	−0.024 (2)	−0.005 (2)
C17	0.101 (3)	0.075 (2)	0.080 (3)	−0.043 (2)	−0.034 (2)	0.0225 (19)

Geometric parameters (Å, º)

Cl1—C4	1.740 (3)	C5—H5	0.9300
Cl2—C6	1.735 (3)	C7—C8	1.505 (6)
N1—C9	1.353 (4)	C7—C9	1.525 (4)
N1—C10	1.395 (4)	C7—H7	0.9800
N1—H1	0.8600	C8—H8A	0.9600
O1—C1	1.371 (4)	C8—H8B	0.9600
O1—C7	1.439 (3)	C8—H8C	0.9600
O2—C9	1.206 (4)	C10—N2	1.325 (4)
O3—C12	1.350 (4)	C10—N3	1.333 (4)
O3—C16	1.425 (5)	N2—C12	1.332 (4)
O4—C14	1.341 (4)	C12—C13	1.366 (5)
O4—C17	1.432 (4)	C13—C14	1.381 (5)
C1—C2	1.374 (4)	C13—H13	0.9300
C1—C6	1.386 (4)	C14—N3	1.326 (4)
C2—C3	1.377 (5)	C16—H16A	0.9600
C2—H2	0.9300	C16—H16B	0.9600
C3—C4	1.361 (5)	C16—H16C	0.9600
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.375 (5)	C17—H17B	0.9600
C5—C6	1.376 (5)	C17—H17C	0.9600
C9—N1—C10	129.8 (3)	C7—C8—H8C	109.5
C9—N1—H1	115.1	H8A—C8—H8C	109.5
C10—N1—H1	115.1	H8B—C8—H8C	109.5
C1—O1—C7	119.2 (2)	O2—C9—N1	126.0 (3)
C12—O3—C16	118.0 (3)	O2—C9—C7	118.6 (3)
C14—O4—C17	118.6 (3)	N1—C9—C7	115.4 (3)
O1—C1—C2	125.9 (3)	N2—C10—N3	128.2 (3)
O1—C1—C6	115.6 (3)	N2—C10—N1	118.6 (3)
C2—C1—C6	118.5 (3)	N3—C10—N1	113.2 (3)
C3—C2—C1	120.5 (3)	C10—N2—C12	114.2 (3)
C3—C2—H2	119.8	N2—C12—O3	118.0 (3)
C1—C2—H2	119.8	N2—C12—C13	123.9 (3)
C4—C3—C2	120.3 (3)	O3—C12—C13	118.1 (3)
C4—C3—H3	119.8	C12—C13—C14	115.8 (3)
C2—C3—H3	119.8	C12—C13—H13	122.1
C3—C4—C5	120.4 (3)	C14—C13—H13	122.1
C3—C4—Cl1	119.5 (3)	N3—C14—O4	119.1 (3)
C5—C4—Cl1	120.0 (3)	N3—C14—C13	123.1 (3)
C4—C5—C6	119.1 (3)	O4—C14—C13	117.8 (3)
C4—C5—H5	120.4	C14—N3—C10	114.8 (3)
C6—C5—H5	120.4	O3—C16—H16A	109.5
C5—C6—C1	121.1 (3)	O3—C16—H16B	109.5
C5—C6—Cl2	120.3 (3)	H16A—C16—H16B	109.5
C1—C6—Cl2	118.6 (3)	O3—C16—H16C	109.5
O1—C7—C8	111.1 (3)	H16A—C16—H16C	109.5
O1—C7—C9	107.8 (2)	H16B—C16—H16C	109.5
C8—C7—C9	110.6 (3)	O4—C17—H17A	109.5
O1—C7—H7	109.1	O4—C17—H17B	109.5
C8—C7—H7	109.1	H17A—C17—H17B	109.5
C9—C7—H7	109.1	O4—C17—H17C	109.5
C7—C8—H8A	109.5	H17A—C17—H17C	109.5
C7—C8—H8B	109.5	H17B—C17—H17C	109.5
H8A—C8—H8B	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.07	2.551 (3)	115