3-Meth­oxy-N-p-tolyl­benzohydroxamic acid

Abstract

Two mol­ecules of the title compound, C₁₅H₁₅NO₃, are linked by a pair of O—H⋯O_carbon­yl hydrogen bonds over a centre of inversion to form a hydrogen-bonded dimer. With respect to the –C(=O)—N(OH)– unit, the methoxy-substituted ring is twisted by 42.2 (1)°, whereas the methyl-substituted ring is twisted by 52.2 (1)°.

Related literature

The parent N-phenyl­benzohydroxamic acid exists in the cis form as well as the common trans form (see Yamasaki et al., 2006 ▶). For the synthesis and spectroscopic data of the title compound, see: Agrawal & Tandon (1971 ▶, 1972 ▶, 1973 ▶).

Experimental

Crystal data

• C₁₅H₁₅NO₃

• M _r = 257.28

• Monoclinic,

• a = 11.332 (1) Å

• b = 7.939 (1) Å

• c = 15.567 (2) Å

• β = 106.397 (2)°

• V = 1343.5 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 293 (2) K

• 0.47 × 0.36 × 0.27 mm

Data collection

• Bruker APEX diffractometer

• Absorption correction: none

• 6832 measured reflections

• 2378 independent reflections

• 1748 reflections with I > 2σ(I)

• R _int = 0.023

Refinement

• R[F ² > 2σ(F ²)] = 0.044

• wR(F ²) = 0.121

• S = 1.06

• 2378 reflections

• 178 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.17 e Å⁻³

• Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2007 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.86 (1)	1.99 (2)	2.699 (2)	139 (2)

Symmetry code: (i) .

supplementary crystallographic information

Experimental

3-Methoxybenzoyl chloride (1.4 g, 0.01 mmol) dissolved in ether was added to N-(4-tolyl)hydroxylamine (1.0 g, 0.01 mmol) dissolved in ether in the presence of sodium bicarbonate (0.7 g, 0.01 mmol). The reaction was carried out in an ice-bath. The solid that formed on removal of the solvent was extracted with ethyl acetate (10 ml). The solution yielded crystals after being set aside in a refrigerator.

Refinement

The carbon-bound H atoms were placed at calculated positions (C–H 0.93– 0.97 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2–1.5U_eq(C). The hydropxy hydrogen atom was located in a difference Fouier map, and was refined with a distance restraint of O–H 0.85±0.01 Å.

Figures

Fig. 1.

Thermal ellipsoid plot of two molecules of C15H15NO3. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are shown as spheres of arbitrary radii.

Crystal data

C15H15NO3	F000 = 544
Mr = 257.28	Dx = 1.272 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7258 reflections
a = 11.332 (1) Å	θ = 2.8–21.7º
b = 7.939 (1) Å	µ = 0.09 mm−1
c = 15.567 (2) Å	T = 293 (2) K
β = 106.397 (2)º	Irregular block, colorless
V = 1343.5 (2) Å3	0.47 × 0.36 × 0.27 mm
Z = 4

Data collection

Bruker APEX diffractometer	1748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Monochromator: Graphite	θmax = 25.1º
T = 293(2) K	θmin = 1.9º
φ and ω scans	h = −13→13
Absorption correction: none	k = −9→9
6832 measured reflections	l = −14→18
2378 independent reflections

Refinement

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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1129P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2378 reflections	Δρmax = 0.17 e Å−3
178 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
O1	0.50151 (12)	0.30374 (18)	0.40770 (9)	0.0623 (4)
H1	0.494 (2)	0.390 (2)	0.4393 (15)	0.108 (9)*
O2	0.62368 (12)	0.42304 (16)	0.56320 (8)	0.0635 (4)
O3	0.94373 (12)	0.18762 (18)	0.82493 (8)	0.0681 (4)
N1	0.60896 (13)	0.22480 (18)	0.45952 (9)	0.0484 (4)
C1	0.62980 (15)	0.0686 (2)	0.42159 (11)	0.0436 (4)
C2	0.63120 (16)	0.0638 (2)	0.33340 (12)	0.0521 (5)
H2	0.6186	0.1618	0.2993	0.063*
C3	0.65135 (16)	−0.0866 (3)	0.29608 (13)	0.0585 (5)
H3	0.6524	−0.0890	0.2366	0.070*
C4	0.67003 (16)	−0.2340 (2)	0.34493 (15)	0.0588 (5)
C5	0.66643 (17)	−0.2264 (2)	0.43301 (15)	0.0616 (6)
H5	0.6788	−0.3245	0.4670	0.074*
C6	0.64499 (16)	−0.0772 (2)	0.47175 (13)	0.0532 (5)
H6	0.6409	−0.0751	0.5306	0.064*
C7	0.6942 (2)	−0.3978 (3)	0.30416 (18)	0.0897 (8)
H7A	0.6333	−0.4791	0.3082	0.135*
H7B	0.7744	−0.4387	0.3359	0.135*
H7C	0.6904	−0.3802	0.2424	0.135*
C8	0.66747 (16)	0.2968 (2)	0.53701 (11)	0.0453 (4)
C9	0.78932 (15)	0.2288 (2)	0.58918 (11)	0.0429 (4)
C10	0.88037 (16)	0.1831 (2)	0.55018 (13)	0.0546 (5)
H10	0.8647	0.1839	0.4882	0.065*
C11	0.99379 (17)	0.1367 (3)	0.60382 (14)	0.0639 (6)
H11	1.0548	0.1060	0.5775	0.077*
C12	1.01962 (17)	0.1344 (3)	0.69602 (14)	0.0606 (5)
H12	1.0968	0.1015	0.7314	0.073*
C13	0.92907 (17)	0.1818 (2)	0.73517 (12)	0.0502 (5)
C14	0.81453 (16)	0.2289 (2)	0.68151 (12)	0.0468 (4)
H14	0.7537	0.2610	0.7077	0.056*
C15	1.0630 (2)	0.1592 (4)	0.88294 (15)	0.0953 (9)
H15A	1.0606	0.1657	0.9440	0.143*
H15B	1.1184	0.2432	0.8725	0.143*
H15C	1.0911	0.0495	0.8717	0.143*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0614 (9)	0.0629 (9)	0.0531 (8)	0.0250 (7)	0.0004 (7)	−0.0025 (7)
O2	0.0637 (8)	0.0571 (8)	0.0624 (8)	0.0228 (7)	0.0058 (7)	−0.0098 (6)
O3	0.0640 (9)	0.0829 (10)	0.0491 (8)	0.0086 (7)	0.0024 (7)	0.0036 (7)
N1	0.0468 (9)	0.0480 (9)	0.0461 (9)	0.0125 (7)	0.0061 (7)	0.0007 (7)
C1	0.0391 (9)	0.0429 (10)	0.0466 (10)	0.0025 (7)	0.0086 (8)	−0.0022 (8)
C2	0.0516 (11)	0.0528 (11)	0.0498 (11)	0.0051 (8)	0.0109 (9)	−0.0004 (9)
C3	0.0513 (11)	0.0701 (14)	0.0514 (11)	0.0044 (10)	0.0104 (9)	−0.0129 (10)
C4	0.0418 (10)	0.0537 (12)	0.0753 (14)	−0.0004 (9)	0.0076 (10)	−0.0191 (10)
C5	0.0546 (12)	0.0439 (11)	0.0822 (15)	0.0003 (9)	0.0123 (11)	0.0040 (10)
C6	0.0535 (11)	0.0508 (11)	0.0543 (11)	0.0023 (9)	0.0134 (9)	0.0051 (9)
C7	0.0737 (15)	0.0686 (15)	0.121 (2)	0.0060 (12)	0.0177 (14)	−0.0378 (14)
C8	0.0469 (10)	0.0425 (10)	0.0464 (10)	0.0050 (8)	0.0129 (9)	0.0009 (8)
C9	0.0425 (9)	0.0355 (9)	0.0492 (10)	0.0021 (7)	0.0103 (8)	−0.0015 (7)
C10	0.0479 (11)	0.0607 (12)	0.0549 (12)	0.0027 (9)	0.0142 (9)	−0.0065 (9)
C11	0.0469 (11)	0.0752 (14)	0.0718 (14)	0.0071 (10)	0.0202 (10)	−0.0125 (11)
C12	0.0430 (10)	0.0606 (12)	0.0713 (15)	0.0075 (9)	0.0051 (10)	−0.0037 (10)
C13	0.0520 (11)	0.0425 (10)	0.0514 (12)	0.0008 (8)	0.0071 (9)	−0.0011 (8)
C14	0.0434 (10)	0.0445 (10)	0.0525 (11)	0.0043 (8)	0.0136 (8)	0.0001 (8)
C15	0.0872 (18)	0.118 (2)	0.0605 (14)	0.0368 (15)	−0.0128 (13)	−0.0057 (13)

Geometric parameters (Å, °)

O1—N1	1.4041 (18)	C7—H7A	0.9600
O1—H1	0.86 (1)	C7—H7B	0.9600
O2—C8	1.238 (2)	C7—H7C	0.9600
O3—C13	1.361 (2)	C8—C9	1.491 (2)
O3—C15	1.416 (2)	C9—C10	1.385 (2)
N1—C8	1.330 (2)	C9—C14	1.384 (2)
N1—C1	1.422 (2)	C10—C11	1.371 (3)
C1—C2	1.378 (2)	C10—H10	0.9300
C1—C6	1.380 (2)	C11—C12	1.382 (3)
C2—C3	1.375 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.385 (3)
C3—C4	1.379 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.382 (2)
C4—C5	1.385 (3)	C14—H14	0.9300
C4—C7	1.506 (3)	C15—H15A	0.9600
C5—C6	1.381 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300
N1—O1—H1	103.5 (18)	H7B—C7—H7C	109.5
C13—O3—C15	117.87 (16)	O2—C8—N1	120.20 (15)
C8—N1—O1	117.30 (14)	O2—C8—C9	120.62 (15)
C8—N1—C1	130.73 (14)	N1—C8—C9	119.10 (15)
O1—N1—C1	111.69 (13)	C10—C9—C14	119.63 (16)
C2—C1—C6	120.42 (16)	C10—C9—C8	123.08 (16)
C2—C1—N1	119.18 (15)	C14—C9—C8	116.95 (15)
C6—C1—N1	120.38 (16)	C11—C10—C9	119.33 (18)
C3—C2—C1	119.64 (17)	C11—C10—H10	120.3
C3—C2—H2	120.2	C9—C10—H10	120.3
C1—C2—H2	120.2	C10—C11—C12	121.57 (18)
C2—C3—C4	121.47 (18)	C10—C11—H11	119.2
C2—C3—H3	119.3	C12—C11—H11	119.2
C4—C3—H3	119.3	C11—C12—C13	119.17 (18)
C3—C4—C5	117.80 (17)	C11—C12—H12	120.4
C3—C4—C7	121.2 (2)	C13—C12—H12	120.4
C5—C4—C7	121.0 (2)	O3—C13—C14	115.67 (16)
C6—C5—C4	121.85 (18)	O3—C13—C12	124.76 (17)
C6—C5—H5	119.1	C14—C13—C12	119.57 (17)
C4—C5—H5	119.1	C13—C14—C9	120.72 (16)
C1—C6—C5	118.78 (18)	C13—C14—H14	119.6
C1—C6—H6	120.6	C9—C14—H14	119.6
C5—C6—H6	120.6	O3—C15—H15A	109.5
C4—C7—H7A	109.5	O3—C15—H15B	109.5
C4—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7B	109.5	O3—C15—H15C	109.5
C4—C7—H7C	109.5	H15A—C15—H15C	109.5
H7A—C7—H7C	109.5	H15B—C15—H15C	109.5
C8—N1—C1—C2	−133.3 (2)	C1—N1—C8—C9	13.6 (3)
O1—N1—C1—C2	53.0 (2)	O2—C8—C9—C10	−133.46 (18)
C8—N1—C1—C6	48.5 (3)	N1—C8—C9—C10	43.3 (2)
O1—N1—C1—C6	−125.21 (17)	O2—C8—C9—C14	39.8 (2)
C6—C1—C2—C3	−1.8 (3)	N1—C8—C9—C14	−143.42 (16)
N1—C1—C2—C3	179.96 (15)	C14—C9—C10—C11	0.8 (3)
C1—C2—C3—C4	0.2 (3)	C8—C9—C10—C11	173.91 (18)
C2—C3—C4—C5	0.8 (3)	C9—C10—C11—C12	0.0 (3)
C2—C3—C4—C7	−178.94 (18)	C10—C11—C12—C13	−0.7 (3)
C3—C4—C5—C6	0.0 (3)	C15—O3—C13—C14	−172.98 (19)
C7—C4—C5—C6	179.68 (18)	C15—O3—C13—C12	6.5 (3)
C2—C1—C6—C5	2.5 (3)	C11—C12—C13—O3	−178.85 (18)
N1—C1—C6—C5	−179.29 (15)	C11—C12—C13—C14	0.6 (3)
C4—C5—C6—C1	−1.6 (3)	O3—C13—C14—C9	179.64 (15)
O1—N1—C8—O2	3.7 (3)	C12—C13—C14—C9	0.1 (3)
C1—N1—C8—O2	−169.65 (16)	C10—C9—C14—C13	−0.8 (2)
O1—N1—C8—C9	−173.02 (14)	C8—C9—C14—C13	−174.38 (15)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.86 (1)	1.99 (2)	2.699 (2)	139 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.