Methyl 4-{2-chloro-4-[2-(4,6-dimethoxy­pyrimidin-2-yl­oxy)benzyl­amino]phen­oxy}benzoate

The title compound, C₂₇H₂₄ClN₃O₆, a probable new herbicide, was synthesized by the reaction of 4,6-dimeth­oxy-2-(methyl­sulfon­yl)pyrimidine and methyl 4-[2-chloro-4-(2-hydroxy­benzyl­amino)phen­oxy]benzoate in tetra­hydro­furan. π–π Inter­actions occur between neighbouring benzene rings.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.046
• wR factor = 0.136
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl 4-{2-chloro-4-[2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino]phenoxy}benzoate

Crystal data

C27H24ClN3O6	Z = 2
Mr = 521.94	F(000) = 544
Triclinic, P1	Dx = 1.379 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 10.763 (4) Å	Cell parameters from 9127 reflections
b = 11.066 (6) Å	θ = 3.1–27.5°
c = 12.051 (4) Å	µ = 0.20 mm^−1
α = 98.02 (3)°	T = 298 K
β = 116.33 (3)°	Block, colourless
γ = 94.746 (19)°	0.35 × 0.28 × 0.18 mm
V = 1256.8 (10) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	5677 independent reflections
Radiation source: fine-focus sealed tube	3660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
Tmin = 0.915, Tmax = 0.965	l = −15→13
12447 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0686P)^2 + 0.0343P] where P = (Fo^2 + 2Fc^2)/3
5677 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, 500 MHz): δ 3.81 [s, 6H, (OCH₃)₂-pyrimidine], 3.88 (s, 3H, OCH₃-benzoate), 4.34 (s, 2H, CH₂-benzyl group), 5.78 (s, 1H, CH-pyrimidine), 6.69–7.97 (m, 11H, ArH). MS–ESI m/z: 522 ([M+1]⁺)

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.

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

	x	y	z	Uiso*/Ueq
C1	0.87879 (16)	0.98627 (15)	0.08243 (14)	0.0445 (4)
C2	0.93510 (17)	0.87770 (16)	0.09020 (16)	0.0532 (4)
H2	0.8775	0.8041	0.0392	0.064*
C3	1.07312 (19)	0.87523 (19)	0.17073 (18)	0.0613 (5)
H3	1.1081	0.8011	0.1729	0.074*
C4	1.15886 (19)	0.9823 (2)	0.24777 (18)	0.0639 (5)
H4	1.2519	0.9810	0.3041	0.077*
C5	1.1065 (2)	1.0919 (2)	0.24139 (18)	0.0648 (5)
H5	1.1644	1.1653	0.2928	0.078*
C6	0.96858 (18)	1.09251 (16)	0.15876 (16)	0.0504 (4)
C7	0.72800 (17)	0.98752 (17)	−0.01013 (16)	0.0557 (4)
H7A	0.6953	1.0557	0.0234	0.067*
H7B	0.7249	1.0031	−0.0885	0.067*
C8	0.58037 (15)	0.84621 (16)	0.04219 (14)	0.0475 (4)
C9	0.61340 (16)	0.92419 (16)	0.15554 (15)	0.0507 (4)
H9	0.6770	0.9971	0.1821	0.061*
C10	0.55126 (16)	0.89300 (17)	0.22900 (15)	0.0515 (4)
C11	0.45984 (16)	0.78475 (17)	0.19410 (16)	0.0526 (4)
C12	0.42907 (18)	0.70660 (19)	0.08301 (17)	0.0612 (5)
H12	0.3679	0.6324	0.0584	0.073*
C13	0.48768 (17)	0.73678 (18)	0.00772 (16)	0.0593 (5)
H13	0.4648	0.6830	−0.0675	0.071*
C14	0.46471 (16)	0.71844 (16)	0.37519 (16)	0.0505 (4)
C15	0.40647 (17)	0.72369 (18)	0.45675 (18)	0.0583 (4)
H15	0.3210	0.7515	0.4348	0.070*
C16	0.47483 (17)	0.68778 (18)	0.57013 (17)	0.0580 (4)
H16	0.4356	0.6922	0.6252	0.070*
C17	0.60091 (17)	0.64512 (15)	0.60391 (16)	0.0502 (4)
C18	0.65664 (17)	0.63829 (17)	0.51941 (16)	0.0545 (4)
H18	0.7409	0.6084	0.5402	0.065*
C19	0.58984 (18)	0.67471 (17)	0.40602 (17)	0.0558 (4)
H19	0.6285	0.6700	0.3505	0.067*
C20	0.67387 (19)	0.61081 (17)	0.72866 (17)	0.0579 (4)
C21	0.8692 (3)	0.5286 (3)	0.8627 (2)	0.0882 (7)
H21A	0.8909	0.5973	0.9300	0.132*
H21B	0.9549	0.5056	0.8666	0.132*
H21C	0.8158	0.4599	0.8712	0.132*
C22	0.89913 (17)	1.27048 (17)	0.23502 (18)	0.0564 (4)
C23	0.83710 (18)	1.44241 (18)	0.3008 (2)	0.0699 (6)
C24	0.8481 (2)	1.4001 (2)	0.4053 (3)	0.0827 (7)
H24	0.8273	1.4451	0.4643	0.099*
C25	0.8913 (2)	1.2884 (2)	0.4187 (2)	0.0706 (5)
C26	0.7998 (3)	1.6049 (3)	0.1866 (3)	0.1100 (10)
H26A	0.8911	1.6080	0.1905	0.165*
H26B	0.7775	1.6870	0.1928	0.165*
H26C	0.7310	1.5543	0.1079	0.165*
C27	0.9717 (3)	1.1364 (3)	0.5408 (3)	0.1038 (9)
H27A	0.9146	1.0705	0.4702	0.156*
H27B	0.9778	1.1135	0.6169	0.156*
H27C	1.0641	1.1514	0.5476	0.156*
N1	0.63285 (14)	0.87581 (15)	−0.03773 (13)	0.0582 (4)
H1	0.6114	0.8150	−0.1067	0.080*
N2	0.86317 (15)	1.37949 (14)	0.21278 (16)	0.0628 (4)
N3	0.91562 (15)	1.21978 (14)	0.33237 (16)	0.0611 (4)
O1	0.39010 (11)	0.75721 (13)	0.26375 (12)	0.0623 (3)
O2	0.78841 (14)	0.56315 (14)	0.74323 (12)	0.0710 (4)
O3	0.63775 (17)	0.62523 (16)	0.80939 (14)	0.0860 (5)
O4	0.91852 (15)	1.20546 (12)	0.14222 (12)	0.0678 (4)
O5	0.79957 (16)	1.55387 (14)	0.28751 (19)	0.0938 (5)
O6	0.9099 (2)	1.24607 (17)	0.52271 (17)	0.0968 (5)
Cl1	0.58494 (6)	0.99567 (6)	0.36445 (5)	0.0860 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0534 (8)	0.0466 (9)	0.0468 (8)	0.0125 (7)	0.0327 (7)	0.0143 (7)
C2	0.0598 (10)	0.0433 (10)	0.0588 (10)	0.0106 (7)	0.0290 (8)	0.0097 (8)
C3	0.0644 (11)	0.0627 (12)	0.0702 (11)	0.0277 (9)	0.0373 (10)	0.0220 (10)
C4	0.0502 (9)	0.0859 (15)	0.0627 (11)	0.0164 (9)	0.0298 (8)	0.0198 (10)
C5	0.0649 (11)	0.0618 (13)	0.0626 (11)	−0.0041 (9)	0.0305 (9)	0.0011 (9)
C6	0.0645 (10)	0.0435 (10)	0.0530 (9)	0.0115 (7)	0.0351 (8)	0.0097 (7)
C7	0.0573 (9)	0.0622 (12)	0.0571 (10)	0.0189 (8)	0.0304 (8)	0.0212 (9)
C8	0.0388 (7)	0.0558 (10)	0.0440 (8)	0.0130 (7)	0.0151 (6)	0.0089 (7)
C9	0.0456 (8)	0.0471 (10)	0.0548 (9)	0.0068 (7)	0.0206 (7)	0.0058 (8)
C10	0.0496 (8)	0.0546 (10)	0.0474 (9)	0.0119 (7)	0.0215 (7)	0.0021 (7)
C11	0.0433 (8)	0.0611 (11)	0.0533 (9)	0.0101 (7)	0.0218 (7)	0.0112 (8)
C12	0.0527 (9)	0.0615 (12)	0.0609 (10)	−0.0052 (8)	0.0245 (8)	−0.0001 (9)
C13	0.0522 (9)	0.0646 (12)	0.0495 (9)	−0.0006 (8)	0.0196 (8)	−0.0051 (8)
C14	0.0475 (8)	0.0487 (10)	0.0553 (9)	0.0024 (7)	0.0273 (7)	0.0009 (8)
C15	0.0492 (9)	0.0637 (12)	0.0679 (11)	0.0080 (8)	0.0346 (8)	0.0055 (9)
C16	0.0598 (10)	0.0629 (12)	0.0594 (10)	0.0031 (8)	0.0390 (9)	0.0004 (9)
C17	0.0555 (9)	0.0399 (9)	0.0535 (9)	−0.0017 (7)	0.0289 (7)	−0.0039 (7)
C18	0.0553 (9)	0.0536 (11)	0.0589 (10)	0.0128 (8)	0.0316 (8)	0.0032 (8)
C19	0.0579 (9)	0.0614 (11)	0.0588 (10)	0.0137 (8)	0.0372 (8)	0.0065 (8)
C20	0.0697 (11)	0.0465 (10)	0.0569 (10)	−0.0006 (8)	0.0336 (9)	−0.0011 (8)
C21	0.0899 (15)	0.0994 (19)	0.0776 (14)	0.0260 (13)	0.0336 (12)	0.0366 (14)
C22	0.0545 (9)	0.0445 (10)	0.0680 (11)	0.0040 (7)	0.0299 (8)	0.0004 (8)
C23	0.0539 (10)	0.0489 (11)	0.1114 (17)	0.0099 (8)	0.0457 (11)	0.0023 (11)
C24	0.0910 (14)	0.0602 (14)	0.126 (2)	0.0162 (11)	0.0802 (15)	0.0013 (13)
C25	0.0758 (12)	0.0619 (13)	0.0952 (15)	0.0079 (10)	0.0614 (11)	0.0054 (11)
C26	0.128 (2)	0.0679 (17)	0.130 (2)	0.0460 (16)	0.0492 (19)	0.0253 (17)
C27	0.148 (2)	0.096 (2)	0.111 (2)	0.0381 (18)	0.090 (2)	0.0375 (17)
N1	0.0561 (8)	0.0670 (10)	0.0501 (8)	0.0029 (7)	0.0265 (7)	0.0038 (7)
N2	0.0548 (8)	0.0435 (9)	0.0820 (11)	0.0082 (6)	0.0268 (8)	0.0041 (8)
N3	0.0685 (9)	0.0495 (9)	0.0764 (10)	0.0083 (7)	0.0456 (8)	0.0041 (8)
O1	0.0473 (6)	0.0833 (10)	0.0633 (7)	0.0130 (6)	0.0302 (6)	0.0187 (7)
O2	0.0736 (8)	0.0783 (10)	0.0661 (8)	0.0219 (7)	0.0334 (7)	0.0198 (7)
O3	0.1064 (11)	0.1015 (13)	0.0660 (9)	0.0276 (9)	0.0524 (8)	0.0144 (8)
O4	0.0997 (10)	0.0434 (7)	0.0654 (8)	0.0201 (7)	0.0416 (7)	0.0090 (6)
O5	0.0931 (11)	0.0565 (9)	0.1511 (16)	0.0315 (8)	0.0716 (11)	0.0148 (10)
O6	0.1386 (14)	0.0880 (12)	0.1123 (13)	0.0275 (11)	0.0992 (12)	0.0187 (10)
Cl1	0.1059 (4)	0.0773 (4)	0.0759 (3)	−0.0077 (3)	0.0564 (3)	−0.0193 (3)

Geometric parameters (Å, º)

C1—C6	1.373 (2)	C16—C17	1.378 (2)
C1—C2	1.386 (2)	C16—H16	0.9300
C1—C7	1.510 (2)	C17—C18	1.389 (2)
C2—C3	1.373 (2)	C17—C20	1.477 (3)
C2—H2	0.9300	C18—C19	1.370 (2)
C3—C4	1.367 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.377 (3)	C20—O3	1.194 (2)
C4—H4	0.9300	C20—O2	1.330 (2)
C5—C6	1.374 (3)	C21—O2	1.440 (2)
C5—H5	0.9300	C21—H21A	0.9600
C6—O4	1.406 (2)	C21—H21B	0.9600
C7—N1	1.436 (2)	C21—H21C	0.9600
C7—H7A	0.9700	C22—N3	1.318 (2)
C7—H7B	0.9700	C22—N2	1.324 (2)
C8—N1	1.376 (2)	C22—O4	1.349 (2)
C8—C13	1.388 (3)	C23—N2	1.334 (3)
C8—C9	1.388 (2)	C23—O5	1.338 (3)
C9—C10	1.386 (2)	C23—C24	1.364 (3)
C9—H9	0.9300	C24—C25	1.362 (3)
C10—C11	1.370 (3)	C24—H24	0.9300
C10—Cl1	1.7253 (19)	C25—N3	1.334 (3)
C11—C12	1.373 (3)	C25—O6	1.337 (3)
C11—O1	1.398 (2)	C26—O5	1.411 (3)
C12—C13	1.375 (3)	C26—H26A	0.9600
C12—H12	0.9300	C26—H26B	0.9600
C13—H13	0.9300	C26—H26C	0.9600
C14—O1	1.376 (2)	C27—O6	1.429 (3)
C14—C15	1.378 (2)	C27—H27A	0.9600
C14—C19	1.378 (2)	C27—H27B	0.9600
C15—C16	1.369 (3)	C27—H27C	0.9600
C15—H15	0.9300	N1—H1	0.9192
C6—C1—C2	116.62 (15)	C16—C17—C20	119.54 (16)
C6—C1—C7	122.04 (15)	C18—C17—C20	122.11 (15)
C2—C1—C7	121.27 (16)	C19—C18—C17	121.23 (16)
C3—C2—C1	122.18 (17)	C19—C18—H18	119.4
C3—C2—H2	118.9	C17—C18—H18	119.4
C1—C2—H2	118.9	C18—C19—C14	119.26 (16)
C4—C3—C2	119.71 (18)	C18—C19—H19	120.4
C4—C3—H3	120.1	C14—C19—H19	120.4
C2—C3—H3	120.1	O3—C20—O2	122.78 (18)
C3—C4—C5	119.52 (17)	O3—C20—C17	125.04 (18)
C3—C4—H4	120.2	O2—C20—C17	112.17 (16)
C5—C4—H4	120.2	O2—C21—H21A	109.5
C6—C5—C4	119.78 (18)	O2—C21—H21B	109.5
C6—C5—H5	120.1	H21A—C21—H21B	109.5
C4—C5—H5	120.1	O2—C21—H21C	109.5
C1—C6—C5	122.15 (17)	H21A—C21—H21C	109.5
C1—C6—O4	117.65 (15)	H21B—C21—H21C	109.5
C5—C6—O4	119.97 (17)	N3—C22—N2	128.71 (18)
N1—C7—C1	114.91 (14)	N3—C22—O4	118.24 (16)
N1—C7—H7A	108.5	N2—C22—O4	113.04 (17)
C1—C7—H7A	108.5	N2—C23—O5	118.7 (2)
N1—C7—H7B	108.5	N2—C23—C24	123.59 (19)
C1—C7—H7B	108.5	O5—C23—C24	117.7 (2)
H7A—C7—H7B	107.5	C25—C24—C23	116.4 (2)
N1—C8—C13	119.56 (15)	C25—C24—H24	121.8
N1—C8—C9	122.24 (16)	C23—C24—H24	121.8
C13—C8—C9	118.17 (16)	N3—C25—O6	118.9 (2)
C10—C9—C8	119.80 (16)	N3—C25—C24	122.7 (2)
C10—C9—H9	120.1	O6—C25—C24	118.4 (2)
C8—C9—H9	120.1	O5—C26—H26A	109.5
C11—C10—C9	121.56 (16)	O5—C26—H26B	109.5
C11—C10—Cl1	119.28 (14)	H26A—C26—H26B	109.5
C9—C10—Cl1	119.12 (14)	O5—C26—H26C	109.5
C10—C11—C12	118.61 (17)	H26A—C26—H26C	109.5
C10—C11—O1	121.49 (16)	H26B—C26—H26C	109.5
C12—C11—O1	119.73 (16)	O6—C27—H27A	109.5
C11—C12—C13	120.76 (18)	O6—C27—H27B	109.5
C11—C12—H12	119.6	H27A—C27—H27B	109.5
C13—C12—H12	119.6	O6—C27—H27C	109.5
C12—C13—C8	121.09 (17)	H27A—C27—H27C	109.5
C12—C13—H13	119.5	H27B—C27—H27C	109.5
C8—C13—H13	119.5	C8—N1—C7	123.23 (15)
O1—C14—C15	116.19 (14)	C8—N1—H1	115.5
O1—C14—C19	123.47 (15)	C7—N1—H1	120.9
C15—C14—C19	120.33 (17)	C22—N2—C23	113.74 (18)
C16—C15—C14	119.79 (16)	C22—N3—C25	114.73 (17)
C16—C15—H15	120.1	C14—O1—C11	118.05 (12)
C14—C15—H15	120.1	C20—O2—C21	116.80 (17)
C15—C16—C17	121.03 (16)	C22—O4—C6	118.89 (14)
C15—C16—H16	119.5	C23—O5—C26	118.9 (2)
C17—C16—H16	119.5	C25—O6—C27	116.68 (18)
C16—C17—C18	118.34 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.92	2.30	3.126 (3)	150
C7—H7A···O4	0.97	2.49	2.828 (3)	100

Symmetry code: (i) x, y, z−1.