2-Hy­droxy-N-(4-methyl­phen­yl)benzamide

Raza, A.R.; Nisar, B.; Tahir, M.N.

doi:10.1107/S1600536811030716

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2253

doi:10.1107/S1600536811030716

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2-Hydroxy-N-(4-methylphenyl)benzamide

Abdul Rauf Raza,^a Bushra Nisar ^a and M. Nawaz Tahir ^b ^*

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 25 July 2011; accepted 30 July 2011; online 6 August 2011)

In the crystal structure of the title compound, C₁₄H₁₃NO₂, the molecules are approximately planar, the r.m.s. deviation for all non-H atoms being 0.0435 Å; the dihedral angle between the two rings is 3.45 (12)°. The planarity is accounted for in terms of the presence of intramolecular N—H⋯O and C—H⋯O hydrogen bonding, each of which completes an S(6) ring motif. The molecules are stabilized in the form of supramolecular chains extending along the crystallographic c axis due to intermolecular O—H⋯O and C—H⋯O hydrogen bonding; each type leads to an R₂¹(6) ring motif.

Related literature

For related benzamide structures, see: Raza et al. (2010a ,b ,c ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /c
a = 19.4067 (17) Å
b = 4.9122 (5) Å
c = 12.7261 (11) Å
β = 104.793 (4)°
V = 1172.96 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.34 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.979, T_max = 0.988
10416 measured reflections
2771 independent reflections
1243 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.159
S = 0.96
2771 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.78	2.596 (2)	179
N1—H1A⋯O1	0.86	1.92	2.647 (2)	141
C3—H3⋯O2ⁱ	0.93	2.51	3.179 (3)	129
C9—H9⋯O2	0.93	2.25	2.840 (3)	121
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811030716/tk2771sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030716/tk2771Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811030716/tk2771Isup3.cml

checkCIF report

Comment top

We have reported the crystal structures of (II) i.e. 2-hydroxy-N-(3-nitrophenyl)benzamide (Raza et al., 2010a), (III) i.e. N-(4-chlorophenyl)-2-hydroxybenzamide (Raza et al., 2010b) and (IV) i.e. N-(3-chlorophenyl)-2 -hydroxybenzamide (Raza et al., 2010c). In this connection, the title compound (I, Fig. 1) has been prepared as a precursor for the synthesis of symmetric as well as asymmetric benzoxazepines.

In (I), the 2-hydroxyphenyl group A (C1–C6/O1) and 4-methylanilinic group B (C8—C14/N1) are planar with r.m.s. deviations of 0.0048 and 0.0086 Å, respectively. The dihedral angle between A/B is 3.45 (12) °. There is intramolecular H-bonding of the type N—H···O and C—H···O types (Table 1, Fig. 1), each of which completes a S(6) ring motif (Bernstein et al., 1995). There is also intermolecular H-bonding of the type C—H···O and O—H···O (Table 1). These lead to the formation of two R₂¹(6) ring motifs and to supramolecular chains extending along the crystallographic c-axis (Fig. 2).

Related literature top

For related benzamide structures, see: Raza et al. (2010a,b,c). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a well stirred solution of 2-hydroxy benzoic acid (2.76 g, 0.02 mol, 1 equiv.) and SOCl₂ (1.74 mL, 2.84 g, 0.024 mol, 1.2 equiv.) in dry CHCl₃, 4-metylaniline (2.14 g, 0.02 mol, 1 equiv.) and Et₃N (4.16 mL, 3 g, 0.03 mol, 1.5 equiv.) were added slowly at room temperature followed by 3 h reflux. After completion of reaction, the reaction mixture was cooled to room temperature, neutralized with aqueous NaHCO₃ (10 %) and extracted with CHCl₃ (3×25 mL). The organic layers were combined, dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure to afford a brown solid. The column chromatographic purification with 1%, 2% and 3% CHCl₃ in petrol (300 mL each) over a silica gel packed column (of 25.5 cm length) afforded white needles of (I) in the 96th-280th fractions (50 mL each).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted line indicate the intramolecular H-bonding.
	Fig. 2. The partial packing diagram which shows that molecules form supramolecular chains extending along the c-axis. The dotted line indicate the intramolecular H-bonding.

2-Hydroxy-N-(4-methylphenyl)benzamide top

Crystal data top

C₁₄H₁₃NO₂	F(000) = 480
M_r = 227.25	D_x = 1.287 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1243 reflections
a = 19.4067 (17) Å	θ = 1.1–27.9°
b = 4.9122 (5) Å	µ = 0.09 mm⁻¹
c = 12.7261 (11) Å	T = 296 K
β = 104.793 (4)°	Needle, colorless
V = 1172.96 (19) Å³	0.34 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2771 independent reflections
Radiation source: fine-focus sealed tube	1243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 7.6 pixels mm^-1	θ_max = 27.9°, θ_min = 1.1°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −4→6
T_min = 0.979, T_max = 0.988	l = −16→16
10416 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0648P)²] where P = (F_o² + 2F_c²)/3
2771 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂	V = 1172.96 (19) Å³
M_r = 227.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.4067 (17) Å	µ = 0.09 mm⁻¹
b = 4.9122 (5) Å	T = 296 K
c = 12.7261 (11) Å	0.34 × 0.14 × 0.12 mm
β = 104.793 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2771 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1243 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.988	R_int = 0.060
10416 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 0.96	Δρ_max = 0.19 e Å⁻³
2771 reflections	Δρ_min = −0.16 e Å⁻³
156 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.29367 (9)	−0.2157 (4)	0.22720 (13)	0.0599 (7)
O2	0.29429 (9)	−0.0348 (3)	−0.09273 (12)	0.0598 (7)
N1	0.24804 (9)	0.0722 (4)	0.04697 (14)	0.0438 (7)
C1	0.33925 (11)	−0.2782 (5)	0.07185 (18)	0.0407 (8)
C2	0.33876 (12)	−0.3489 (5)	0.17802 (18)	0.0438 (8)
C3	0.38382 (13)	−0.5515 (5)	0.2327 (2)	0.0516 (9)
C4	0.42941 (13)	−0.6849 (5)	0.1833 (2)	0.0596 (11)
C5	0.43143 (13)	−0.6168 (6)	0.0796 (2)	0.0615 (11)
C6	0.38654 (13)	−0.4161 (5)	0.0249 (2)	0.0539 (10)
C7	0.29213 (12)	−0.0712 (5)	0.00262 (18)	0.0416 (8)
C8	0.19724 (12)	0.2725 (5)	−0.00178 (18)	0.0428 (8)
C9	0.18909 (14)	0.3743 (5)	−0.1055 (2)	0.0564 (10)
C10	0.13704 (14)	0.5697 (6)	−0.1449 (2)	0.0605 (11)
C11	0.09251 (13)	0.6670 (5)	−0.0859 (2)	0.0544 (10)
C12	0.10233 (14)	0.5654 (5)	0.0186 (2)	0.0592 (10)
C13	0.15368 (13)	0.3727 (5)	0.06023 (19)	0.0524 (9)
C14	0.03636 (15)	0.8783 (5)	−0.1313 (2)	0.0751 (11)
H1	0.29314	−0.29364	0.28396	0.0899*
H1A	0.25091	0.03812	0.11424	0.0525*
H3	0.38315	−0.59736	0.30329	0.0619*
H4	0.45896	−0.82174	0.22036	0.0714*
H5	0.46273	−0.70494	0.04648	0.0739*
H6	0.38794	−0.37165	−0.04556	0.0647*
H9	0.21810	0.31275	−0.14848	0.0677*
H10	0.13229	0.63728	−0.21461	0.0726*
H12	0.07355	0.62883	0.06158	0.0711*
H13	0.15915	0.30919	0.13074	0.0628*
H14A	0.03008	0.89281	−0.20839	0.1127*
H14B	0.05114	1.05104	−0.09782	0.1127*
H14C	−0.00787	0.82537	−0.11655	0.1127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0753 (12)	0.0677 (13)	0.0429 (11)	0.0164 (10)	0.0262 (9)	0.0130 (9)
O2	0.0889 (13)	0.0586 (13)	0.0371 (10)	0.0035 (10)	0.0256 (9)	0.0009 (8)
N1	0.0496 (12)	0.0504 (14)	0.0318 (10)	0.0029 (10)	0.0111 (9)	0.0039 (9)
C1	0.0437 (13)	0.0379 (15)	0.0409 (14)	−0.0064 (11)	0.0117 (11)	−0.0060 (11)
C2	0.0449 (14)	0.0444 (16)	0.0438 (14)	−0.0034 (12)	0.0147 (12)	−0.0036 (12)
C3	0.0500 (14)	0.0479 (18)	0.0534 (16)	−0.0010 (13)	0.0070 (12)	0.0053 (13)
C4	0.0506 (16)	0.0481 (19)	0.077 (2)	0.0041 (13)	0.0109 (15)	0.0031 (14)
C5	0.0525 (16)	0.061 (2)	0.076 (2)	0.0033 (15)	0.0257 (15)	−0.0090 (16)
C6	0.0557 (16)	0.0571 (19)	0.0522 (16)	−0.0014 (14)	0.0197 (13)	−0.0048 (14)
C7	0.0494 (14)	0.0400 (16)	0.0365 (14)	−0.0101 (12)	0.0132 (11)	−0.0050 (11)
C8	0.0474 (14)	0.0383 (15)	0.0400 (14)	−0.0038 (12)	0.0062 (11)	0.0006 (11)
C9	0.0608 (16)	0.0616 (19)	0.0465 (16)	−0.0014 (15)	0.0130 (13)	0.0051 (14)
C10	0.0673 (18)	0.056 (2)	0.0515 (17)	−0.0024 (15)	0.0028 (14)	0.0110 (14)
C11	0.0544 (16)	0.0360 (16)	0.0628 (19)	−0.0060 (13)	−0.0031 (14)	−0.0021 (13)
C12	0.0613 (17)	0.0524 (19)	0.0615 (18)	0.0060 (14)	0.0112 (14)	−0.0038 (14)
C13	0.0599 (16)	0.0563 (18)	0.0397 (14)	0.0043 (14)	0.0105 (12)	0.0046 (12)
C14	0.0718 (19)	0.0511 (19)	0.086 (2)	0.0023 (16)	−0.0097 (16)	0.0010 (16)

Geometric parameters (Å, º) top

O1—C2	1.366 (3)	C10—C11	1.368 (4)
O2—C7	1.238 (3)	C11—C12	1.387 (3)
O1—H1	0.8200	C11—C14	1.509 (4)
N1—C7	1.339 (3)	C12—C13	1.379 (4)
N1—C8	1.419 (3)	C3—H3	0.9300
N1—H1A	0.8600	C4—H4	0.9300
C1—C7	1.495 (3)	C5—H5	0.9300
C1—C6	1.392 (3)	C6—H6	0.9300
C1—C2	1.397 (3)	C9—H9	0.9300
C2—C3	1.389 (3)	C10—H10	0.9300
C3—C4	1.375 (4)	C12—H12	0.9300
C4—C5	1.372 (4)	C13—H13	0.9300
C5—C6	1.381 (4)	C14—H14A	0.9600
C8—C13	1.386 (3)	C14—H14B	0.9600
C8—C9	1.382 (3)	C14—H14C	0.9600
C9—C10	1.391 (4)

C2—O1—H1	109.00	C11—C12—C13	121.6 (2)
C7—N1—C8	128.90 (19)	C8—C13—C12	120.8 (2)
C8—N1—H1A	116.00	C2—C3—H3	120.00
C7—N1—H1A	116.00	C4—C3—H3	120.00
C2—C1—C6	117.5 (2)	C3—C4—H4	120.00
C2—C1—C7	125.8 (2)	C5—C4—H4	120.00
C6—C1—C7	116.7 (2)	C4—C5—H5	120.00
O1—C2—C3	120.6 (2)	C6—C5—H5	120.00
O1—C2—C1	119.2 (2)	C1—C6—H6	119.00
C1—C2—C3	120.3 (2)	C5—C6—H6	119.00
C2—C3—C4	120.6 (2)	C8—C9—H9	120.00
C3—C4—C5	120.2 (2)	C10—C9—H9	120.00
C4—C5—C6	119.3 (2)	C9—C10—H10	118.00
C1—C6—C5	122.1 (2)	C11—C10—H10	118.00
N1—C7—C1	118.03 (19)	C11—C12—H12	119.00
O2—C7—C1	120.5 (2)	C13—C12—H12	119.00
O2—C7—N1	121.5 (2)	C8—C13—H13	120.00
N1—C8—C9	124.5 (2)	C12—C13—H13	120.00
N1—C8—C13	117.0 (2)	C11—C14—H14A	109.00
C9—C8—C13	118.5 (2)	C11—C14—H14B	109.00
C8—C9—C10	119.3 (2)	C11—C14—H14C	109.00
C9—C10—C11	123.1 (2)	H14A—C14—H14B	109.00
C10—C11—C14	121.7 (2)	H14A—C14—H14C	109.00
C10—C11—C12	116.7 (2)	H14B—C14—H14C	109.00
C12—C11—C14	121.6 (2)

C8—N1—C7—O2	2.0 (4)	C1—C2—C3—C4	0.0 (4)
C8—N1—C7—C1	−178.1 (2)	C2—C3—C4—C5	0.8 (4)
C7—N1—C8—C9	−6.3 (4)	C3—C4—C5—C6	−1.0 (4)
C7—N1—C8—C13	174.3 (2)	C4—C5—C6—C1	0.4 (4)
C6—C1—C2—O1	179.2 (2)	N1—C8—C9—C10	179.6 (2)
C6—C1—C2—C3	−0.5 (4)	C13—C8—C9—C10	−1.0 (4)
C7—C1—C2—O1	−2.3 (4)	N1—C8—C13—C12	−179.2 (2)
C7—C1—C2—C3	177.9 (2)	C9—C8—C13—C12	1.4 (4)
C2—C1—C6—C5	0.3 (4)	C8—C9—C10—C11	−0.4 (4)
C7—C1—C6—C5	−178.3 (2)	C9—C10—C11—C12	1.4 (4)
C2—C1—C7—O2	−176.0 (2)	C9—C10—C11—C14	−179.7 (2)
C2—C1—C7—N1	4.1 (4)	C10—C11—C12—C13	−1.0 (4)
C6—C1—C7—O2	2.5 (3)	C14—C11—C12—C13	−179.9 (2)
C6—C1—C7—N1	−177.5 (2)	C11—C12—C13—C8	−0.4 (4)
O1—C2—C3—C4	−179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.78	2.596 (2)	179
N1—H1A···O1	0.86	1.92	2.647 (2)	141
C3—H3···O2ⁱ	0.93	2.51	3.179 (3)	129
C9—H9···O2	0.93	2.25	2.840 (3)	121

Symmetry code: (i) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	19.4067 (17), 4.9122 (5), 12.7261 (11)
β (°)	104.793 (4)
V (Å³)	1172.96 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.34 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.979, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10416, 2771, 1243
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.159, 0.96
No. of reflections	2771
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.78	2.596 (2)	179
N1—H1A···O1	0.86	1.92	2.647 (2)	141
C3—H3···O2ⁱ	0.93	2.51	3.179 (3)	129
C9—H9···O2	0.93	2.25	2.840 (3)	121

Symmetry code: (i) x, −y−1/2, z+1/2.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Ex-Vice Chancellor, University of Sargodha, Pakistan. ARR also acknowledges the Higher Education Commission, Government of Pakistan, for generous support of a research project (20-819).

References

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