4-(2,4-Difluoro­phen­yl)-2-(N-methyl­carbamo­yl)phenyl acetate

Zhong, G.-X.; Li, J.; Zheng, R.-H.; Zhao, K.

doi:10.1107/S1600536807052361

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4-(2,4-Difluorophenyl)-2-(N-methylcarbamoyl)phenyl acetate

G.-X. Zhong, J. Li, R.-H. Zheng and K. Zhao

In the title compound, C₁₆H₁₃F₂NO₃, the two benzene rings and all attached non-H atoms are indivdually planar. The two planes, viz. the benzene ring and the two substituent F atoms (A), and the benzene ring and the attached carbonyl C atom, oxy O atom and aromatic C atom (B), have largest deviations of -0.0278 (10) and 0.0272 (9) Å, respectively, and a dihedral angle between the planes of 37.78 (3)°. The dihedral angles between plane B and the methylaminocarbonyl and acetoxy groups are 61.83 (5) and 48.82 (8)°, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052361/sg2190sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052361/sg2190Isup2.hkl Contains datablock I

CCDC reference: 672851

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.044
wR factor = 0.130
Data-to-parameter ratio = 17.0

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Comment top

Diflunisal is a analgesic and non-steroidal anti-inflammatory drug. (Hannah & Ruyle, 1978). In a continuation of our work on the structure–activity relationship of diflunisal derivatives, we have obtained a colorless crystalline compound that was the product of the reaction of acetyl chloride, monomethylamine and diflunisal. The structural identity of our product, (I), was resolved using single-crystal X-ray diffraction.

The molecular structure of (I) is illustrated in Fig. 1. Atoms F1, F2, C5, C7, C8, C9, C10, C11 and C12 are coplanar, the largest deviation being -0.0278 (10) Å for C5. Atoms O1, C1, C2, C3, C4, C5, C6, C7 and C15 are coplanar, the largest deviation being 0.0272 (9) Å for C7. The dihedral angles between the two planes is 37.78 (3)°. The dihedral angles between the O1/C1–C7/C15 plane and the O3/C15/N1/C16 and O1/O2/C13/C14 planes are 61.83 (5) and 48.82 (8)°, respectively.

Related literature top

For related literature, see: Hannah & Ruyle (1978); Rao & Hu (2005).

Experimental top

The title compound was prepared from acetyl chloride, monomethylamine and diflunisal, according to the procedure of Rao & Hu (2005).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

Figures top

Fig. 1. The structure of (I), shown with 30% probability displacement ellipsoids.

4-(2,4-Difluorophenyl)-2-(N-methylcarbamoyl)phenyl acetate top

Crystal data top

C₁₆H₁₃F₂NO₃	F(000) = 632
M_r = 305.27	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.8972 (5) Å	θ = 9.9–13.9°
b = 19.9625 (11) Å	µ = 0.12 mm⁻¹
c = 7.4737 (4) Å	T = 298 K
β = 107.180 (2)°	Prismatic, colourless
V = 1410.72 (13) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2741 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 28.3°, θ_min = 2.0°
ω/2θ scans	h = −13→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −25→25
T_min = 0.971, T_max = 0.976	l = −9→9
18835 measured reflections	3 standard reflections every 60 min
3441 independent reflections	intensity decay: 0.3%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0643P)² + 0.396P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3441 reflections	Δρ_max = 0.30 e Å⁻³
202 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

Crystal data top

C₁₆H₁₃F₂NO₃	V = 1410.72 (13) Å³
M_r = 305.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8972 (5) Å	µ = 0.12 mm⁻¹
b = 19.9625 (11) Å	T = 298 K
c = 7.4737 (4) Å	0.25 × 0.20 × 0.20 mm
β = 107.180 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2741 reflections with I > 2σ(I)
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	R_int = 0.024
T_min = 0.971, T_max = 0.976	3 standard reflections every 60 min
18835 measured reflections	intensity decay: 0.3%
3441 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
3441 reflections	Δρ_min = −0.23 e Å⁻³
202 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.32311 (11)	0.74045 (5)	0.49721 (19)	0.0707 (4)
F2	0.76499 (10)	0.83535 (6)	0.5573 (2)	0.0824 (4)
O1	−0.26535 (10)	0.87205 (5)	0.07940 (16)	0.0442 (3)
O2	−0.25482 (12)	0.94857 (6)	−0.13686 (17)	0.0528 (3)
O3	−0.21960 (11)	0.99622 (6)	0.27918 (18)	0.0510 (3)
N1	−0.03370 (13)	1.04551 (6)	0.21903 (19)	0.0418 (3)
H1	0.0471	1.0401	0.1998	0.050*
C1	−0.03767 (13)	0.92526 (7)	0.23466 (19)	0.0339 (3)
C2	−0.11773 (14)	0.86970 (7)	0.1527 (2)	0.0382 (3)
C3	−0.05561 (16)	0.80854 (8)	0.1458 (2)	0.0468 (4)
H3	−0.1109	0.7722	0.0903	0.056*
C4	0.08875 (15)	0.80110 (7)	0.2211 (2)	0.0431 (3)
H4	0.1300	0.7595	0.2167	0.052*
C5	0.17344 (14)	0.85508 (7)	0.30349 (19)	0.0341 (3)
C6	0.10768 (13)	0.91656 (7)	0.30923 (18)	0.0331 (3)
H6	0.1629	0.9530	0.3648	0.040*
C7	0.32962 (14)	0.84948 (7)	0.37554 (19)	0.0346 (3)
C8	0.41649 (15)	0.90169 (8)	0.3515 (2)	0.0406 (3)
H8	0.3745	0.9407	0.2925	0.049*
C9	0.56228 (16)	0.89772 (9)	0.4118 (2)	0.0482 (4)
H9	0.6180	0.9332	0.3943	0.058*
C10	0.62193 (16)	0.84022 (9)	0.4978 (3)	0.0511 (4)
C11	0.54416 (17)	0.78679 (9)	0.5286 (3)	0.0524 (4)
H11	0.5873	0.7482	0.5889	0.063*
C12	0.39927 (16)	0.79306 (8)	0.4659 (2)	0.0432 (3)
C13	−0.32361 (15)	0.91518 (7)	−0.0630 (2)	0.0406 (3)
C14	−0.48084 (16)	0.91338 (10)	−0.1116 (3)	0.0536 (4)
H14A	−0.5095	0.9279	−0.0059	0.080*
H14B	−0.5135	0.8685	−0.1445	0.080*
H14C	−0.5208	0.9426	−0.2158	0.080*
C15	−0.10582 (14)	0.99183 (7)	0.2462 (2)	0.0353 (3)
C16	−0.08854 (18)	1.11262 (8)	0.2203 (3)	0.0502 (4)
H16A	−0.0248	1.1442	0.1914	0.075*
H16B	−0.0978	1.1223	0.3420	0.075*
H16C	−0.1795	1.1159	0.1283	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0535 (6)	0.0495 (6)	0.1028 (9)	−0.0014 (5)	0.0133 (6)	0.0329 (6)
F2	0.0277 (5)	0.0760 (8)	0.1328 (11)	0.0125 (5)	0.0070 (6)	−0.0009 (8)
O1	0.0253 (5)	0.0412 (6)	0.0621 (7)	−0.0064 (4)	0.0067 (4)	0.0045 (5)
O2	0.0378 (6)	0.0616 (7)	0.0559 (7)	−0.0040 (5)	0.0091 (5)	0.0097 (5)
O3	0.0343 (6)	0.0470 (6)	0.0782 (8)	−0.0002 (4)	0.0267 (5)	−0.0036 (6)
N1	0.0324 (6)	0.0342 (6)	0.0618 (8)	0.0017 (5)	0.0186 (5)	0.0021 (5)
C1	0.0278 (6)	0.0332 (7)	0.0409 (7)	−0.0013 (5)	0.0108 (5)	0.0023 (5)
C2	0.0250 (6)	0.0373 (7)	0.0507 (8)	−0.0041 (5)	0.0089 (6)	0.0048 (6)
C3	0.0356 (8)	0.0331 (7)	0.0679 (10)	−0.0085 (6)	0.0093 (7)	−0.0020 (7)
C4	0.0352 (7)	0.0308 (7)	0.0618 (9)	0.0001 (6)	0.0121 (7)	0.0022 (6)
C5	0.0284 (6)	0.0345 (7)	0.0393 (7)	0.0003 (5)	0.0096 (5)	0.0047 (5)
C6	0.0274 (6)	0.0331 (7)	0.0383 (6)	−0.0030 (5)	0.0090 (5)	0.0006 (5)
C7	0.0293 (7)	0.0355 (7)	0.0384 (7)	0.0023 (5)	0.0092 (5)	0.0011 (5)
C8	0.0319 (7)	0.0390 (8)	0.0500 (8)	0.0016 (6)	0.0108 (6)	0.0076 (6)
C9	0.0328 (7)	0.0477 (9)	0.0644 (10)	−0.0034 (6)	0.0145 (7)	0.0022 (7)
C10	0.0266 (7)	0.0557 (10)	0.0673 (10)	0.0074 (6)	0.0082 (7)	−0.0046 (8)
C11	0.0409 (8)	0.0442 (9)	0.0653 (10)	0.0139 (7)	0.0053 (7)	0.0051 (8)
C12	0.0384 (8)	0.0369 (8)	0.0524 (8)	0.0018 (6)	0.0107 (6)	0.0070 (6)
C13	0.0311 (7)	0.0405 (8)	0.0470 (7)	−0.0013 (6)	0.0064 (6)	−0.0051 (6)
C14	0.0299 (8)	0.0669 (11)	0.0591 (10)	0.0022 (7)	0.0057 (7)	−0.0045 (8)
C15	0.0271 (6)	0.0366 (7)	0.0406 (7)	−0.0003 (5)	0.0076 (5)	−0.0001 (5)
C16	0.0493 (9)	0.0363 (8)	0.0674 (10)	0.0049 (7)	0.0208 (8)	0.0040 (7)

Geometric parameters (Å, º) top

F1—C12	1.3529 (18)	C5—C7	1.4833 (18)
F2—C10	1.3565 (17)	C6—H6	0.9300
O1—C13	1.3579 (19)	C7—C12	1.387 (2)
O1—C2	1.4014 (16)	C7—C8	1.3961 (19)
O2—C13	1.1978 (18)	C8—C9	1.381 (2)
O3—C15	1.2248 (17)	C8—H8	0.9300
N1—C15	1.3361 (18)	C9—C10	1.362 (2)
N1—C16	1.4464 (19)	C9—H9	0.9300
N1—H1	0.8599	C10—C11	1.374 (3)
C1—C6	1.3916 (18)	C11—C12	1.376 (2)
C1—C2	1.3951 (19)	C11—H11	0.9300
C1—C15	1.5042 (19)	C13—C14	1.490 (2)
C2—C3	1.375 (2)	C14—H14A	0.9600
C3—C4	1.380 (2)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.392 (2)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.3959 (19)	C16—H16C	0.9600

C13—O1—C2	118.69 (11)	C10—C9—H9	121.0
C15—N1—C16	121.57 (12)	C8—C9—H9	121.0
C15—N1—H1	119.2	F2—C10—C9	118.69 (15)
C16—N1—H1	119.2	F2—C10—C11	118.15 (15)
C6—C1—C2	117.55 (12)	C9—C10—C11	123.16 (14)
C6—C1—C15	121.01 (12)	C10—C11—C12	116.82 (15)
C2—C1—C15	121.42 (12)	C10—C11—H11	121.6
C3—C2—C1	121.34 (13)	C12—C11—H11	121.6
C3—C2—O1	116.18 (12)	F1—C12—C11	116.62 (13)
C1—C2—O1	122.44 (12)	F1—C12—C7	119.49 (13)
C2—C3—C4	120.06 (13)	C11—C12—C7	123.89 (14)
C2—C3—H3	120.0	O2—C13—O1	123.12 (13)
C4—C3—H3	120.0	O2—C13—C14	126.56 (15)
C3—C4—C5	120.82 (13)	O1—C13—C14	110.31 (13)
C3—C4—H4	119.6	C13—C14—H14A	109.5
C5—C4—H4	119.6	C13—C14—H14B	109.5
C4—C5—C6	117.97 (12)	H14A—C14—H14B	109.5
C4—C5—C7	121.94 (12)	C13—C14—H14C	109.5
C6—C5—C7	120.03 (12)	H14A—C14—H14C	109.5
C1—C6—C5	122.25 (12)	H14B—C14—H14C	109.5
C1—C6—H6	118.9	O3—C15—N1	122.50 (13)
C5—C6—H6	118.9	O3—C15—C1	121.96 (12)
C12—C7—C8	115.62 (13)	N1—C15—C1	115.53 (11)
C12—C7—C5	123.54 (12)	N1—C16—H16A	109.5
C8—C7—C5	120.83 (12)	N1—C16—H16B	109.5
C9—C8—C7	122.60 (14)	H16A—C16—H16B	109.5
C9—C8—H8	118.7	N1—C16—H16C	109.5
C7—C8—H8	118.7	H16A—C16—H16C	109.5
C10—C9—C8	117.90 (15)	H16B—C16—H16C	109.5

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃F₂NO₃
M_r	305.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.8972 (5), 19.9625 (11), 7.4737 (4)
β (°)	107.180 (2)
V (Å³)	1410.72 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.971, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	18835, 3441, 2741
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.05
No. of reflections	3441
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

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