3-Meth­oxy-N-p-tolyl­benzohydroxamic acid

Graisa, A.M.; Farina, Y.; Kassim, M.; Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536807064379

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o251

https://doi.org/10.1107/S1600536807064379

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3-Methoxy-N-p-tolylbenzohydroxamic acid

Abdualbasit M. Graisa,^a Yang Farina,^a Muhammad Kassim,^a Mohd. Razali Rizal ^b and Seik Weng Ng ^b ^*

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43500 Bangi, Selangor, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 November 2007; accepted 29 November 2007; online 12 December 2007)

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, P 2₁ /c
a = 11.332 (1) Å
b = 7.939 (1) Å
c = 15.567 (2) Å
β = 106.397 (2)°
V = 1343.5 (2) Å³
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[F² > 2σ(F²)] = 0.044
wR(F²) = 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

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064379/av2005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064379/av2005Isup2.hkl

checkCIF report

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top

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.

3-Methoxy-N-p-tolylbenzohydroxamic acid top

Crystal data top

C₁₅H₁₅NO₃	F(000) = 544
M_r = 257.28	D_x = 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 = 2.8–21.7°
b = 7.939 (1) Å	µ = 0.09 mm⁻¹
c = 15.567 (2) Å	T = 293 K
β = 106.397 (2)°	Irregular block, colorless
V = 1343.5 (2) Å³	0.47 × 0.36 × 0.27 mm
Z = 4

Data collection top

Bruker APEX diffractometer	1748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.1°, θ_min = 1.9°
φ and ω scans	h = −13→13
6832 measured reflections	k = −9→9
2378 independent reflections	l = −14→18

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1129P] where P = (F_o² + 2F_c²)/3
2378 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₅H₁₅NO₃	V = 1343.5 (2) Å³
M_r = 257.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.332 (1) Å	µ = 0.09 mm⁻¹
b = 7.939 (1) Å	T = 293 K
c = 15.567 (2) Å	0.47 × 0.36 × 0.27 mm
β = 106.397 (2)°

Data collection top

Bruker APEX diffractometer	1748 reflections with I > 2σ(I)
6832 measured reflections	R_int = 0.023
2378 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
2378 reflections	Δρ_min = −0.13 e Å⁻³
178 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₃
M_r	257.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.332 (1), 7.939 (1), 15.567 (2)
β (°)	106.397 (2)
V (Å³)	1343.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.36 × 0.27

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6832, 2378, 1748
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.06
No. of reflections	2378
No. of parameters	178
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.13

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge Professor Bohari M. Yamin's assistance with the diffraction measurements. The authors thank Universiti Kebangsaan Malaysia and the University of Malaya for supporting this study.

References

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