Crystal structure of (E)-2-[(4-hy­droxy­benzyl­idene)aza­nium­yl]benzoate

Tahir, M.N.; Khan, A.H.; Shad, H.A.

doi:10.1107/S1600536814018273

organic compounds

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Volume 70| Part 9| September 2014| Page o1008

doi:10.1107/S1600536814018273

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Crystal structure of (E)-2-[(4-hydroxybenzylidene)azaniumyl]benzoate

M. Nawaz Tahir,^a ^* Abdul Haleem Khan ^b and Hazoor Ahmad Shad ^c

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Pharmacy Services, Jinnah Hospital, Lahore, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 5 August 2014; accepted 9 August 2014; online 16 August 2014)

The title Schiff base, C₁₄H₁₁NO₃, crystallizes as a zwitterion (i.e. proton transfer from the carboxylic acid group to the imine N atom). The dihedral angle between the aromatic rings is 19.59 (6)° and an intramolecular N—H⋯O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂⁴(24) loops. The dimers are linked by C—H⋯O interactions, generating (211) sheets.

Keywords: crystal structure; Schiff bases; azanium–carboxylate zwitterion; hydrogen bonding.

CCDC reference: 1018737

1. Related literature

For related structures, see: Hang et al. (2010 ); Ligtenbarg et al. (1999 ); Trzesowska-Kruszynska (2010 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₁NO₃
M_r = 241.24
Monoclinic, P 2₁ /n
a = 3.8612 (5) Å
b = 15.280 (3) Å
c = 18.604 (3) Å
β = 90.347 (8)°
V = 1097.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.38 × 0.17 × 0.15 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.962, T_max = 0.985
17364 measured reflections
2089 independent reflections
1363 reflections with I > 2σ(I)
R_int = 0.065

2.3. Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.124
S = 1.15
2089 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.95 (4)	1.71 (4)	2.656 (3)	173 (3)
N1—H1⋯O1	1.00 (3)	1.62 (3)	2.522 (3)	148 (2)
C6—H6⋯O2ⁱⁱ	0.93	2.51	3.397 (4)	160
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supporting information

CCDC reference: 1018737

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814018273/hb7268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018273/hb7268Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018273/hb7268Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized for forming different metal complexes.

The crystal structures of N-(2-Carboxyphenyl)salicylidenimine (Ligtenbarg et al., 1999), 2-((4-(dimethylamino)benzylidene)ammonio) benzoate pentahydrate (Trzesowska-Kruszynska, 2010) and 2-[(2-hydroxy-4-methoxybenzylidene)azaniumyl]benzoate monohydrate (Hang, et al., 2010) have been published which are related to the title compound (I).

The title compound has been crystalized in the zwitterion form. In (I) the moieties of 2-aminobenzoic acid A (C1—C7/N1/O1/O2) and the 4-hydroxybenzalehyde B (C8—C14/O3) are planar with r.m.s. deviation of 0.0133 and 0.0219 Å, respectively. The dihedral angle between A/B is 19.589 (58)°. In (I), S(6) ring motif is present due to H-bonding of N—H···O type (Table 1, Fig. 1). The molecules are dimerized from end to end due to H-bondings of O—H···O type (Table 1, Fig. 2) and form R₂⁴(24) loop. The dimers are further interlinked due to C—H···O bonds.

Related literature top

For related structures, see: Hang et al. (2010); Ligtenbarg et al. (1999); Trzesowska-Kruszynska (2010).

Experimental top

Equimolar quantities of 2-aminobenzoic acid and 4-hydroxybenzaldehyde were refluxed in methanol along with few drops of acetic acid as catalyst for 2 h. The resulting solution was kept at room temperature which afforded yellow needles after two days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line represents the intramolecular H-bond.
	Fig. 2. The partial packing, which shows that molecules form dimers which are interlinked.

(E)-2-[(4-hydroxybenzylidene)azaniumyl]benzoate top

Crystal data top

C₁₄H₁₁NO₃	F(000) = 504
M_r = 241.24	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.8612 (5) Å	Cell parameters from 1363 reflections
b = 15.280 (3) Å	θ = 1.8–26.0°
c = 18.604 (3) Å	µ = 0.10 mm⁻¹
β = 90.347 (8)°	T = 296 K
V = 1097.6 (3) Å³	Cut needle, yellow
Z = 4	0.38 × 0.17 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2089 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 1.7°
ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −18→18
T_min = 0.962, T_max = 0.985	l = −22→22
17364 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) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0187P)² + 1.0858P] where P = (F_o² + 2F_c²)/3
2089 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₁NO₃	V = 1097.6 (3) Å³
M_r = 241.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 3.8612 (5) Å	µ = 0.10 mm⁻¹
b = 15.280 (3) Å	T = 296 K
c = 18.604 (3) Å	0.38 × 0.17 × 0.15 mm
β = 90.347 (8)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2089 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1363 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.985	R_int = 0.065
17364 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.18 e Å⁻³
2089 reflections	Δρ_min = −0.23 e Å⁻³
169 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
O1	0.1341 (6)	−0.08844 (13)	0.32981 (10)	0.0469 (6)
O2	0.0144 (7)	−0.18735 (14)	0.24574 (12)	0.0580 (7)
O3	0.6380 (6)	0.22716 (14)	0.59807 (11)	0.0489 (6)
H3A	0.701 (9)	0.177 (2)	0.6251 (19)	0.073*
N1	−0.0068 (6)	0.07058 (16)	0.30803 (13)	0.0360 (6)
H1	0.067 (7)	0.016 (2)	0.3337 (15)	0.043*
C1	0.0114 (8)	−0.1120 (2)	0.26817 (16)	0.0394 (7)
C2	−0.1414 (7)	−0.04003 (18)	0.22116 (14)	0.0328 (7)
C3	−0.2813 (8)	−0.0637 (2)	0.15519 (15)	0.0398 (7)
H3	−0.2817	−0.1223	0.1417	0.048*
C4	−0.4196 (8)	−0.0021 (2)	0.10915 (16)	0.0460 (8)
H4	−0.5103	−0.0192	0.0649	0.055*
C5	−0.4233 (8)	0.0847 (2)	0.12868 (16)	0.0461 (8)
H5	−0.5171	0.1261	0.0975	0.055*
C6	−0.2890 (8)	0.1107 (2)	0.19417 (16)	0.0416 (8)
H6	−0.2931	0.1694	0.2074	0.050*
C7	−0.1485 (7)	0.04873 (18)	0.23973 (14)	0.0332 (7)
C8	0.0590 (7)	0.14802 (19)	0.33225 (15)	0.0370 (7)
H8	0.0125	0.1955	0.3025	0.044*
C9	0.1993 (7)	0.16514 (18)	0.40216 (15)	0.0342 (7)
C10	0.2987 (7)	0.25053 (19)	0.41916 (16)	0.0384 (7)
H10	0.2674	0.2947	0.3854	0.046*
C11	0.4416 (8)	0.27050 (19)	0.48472 (16)	0.0397 (7)
H11	0.5063	0.3278	0.4950	0.048*
C12	0.4901 (8)	0.20511 (19)	0.53595 (15)	0.0365 (7)
C13	0.3814 (7)	0.12005 (18)	0.52047 (15)	0.0375 (7)
H13	0.4051	0.0764	0.5550	0.045*
C14	0.2400 (8)	0.10038 (19)	0.45483 (15)	0.0376 (7)
H14	0.1700	0.0433	0.4451	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0702 (15)	0.0380 (12)	0.0324 (12)	0.0036 (11)	−0.0144 (11)	0.0019 (9)
O2	0.0942 (19)	0.0323 (12)	0.0474 (14)	0.0034 (13)	−0.0117 (13)	−0.0025 (11)
O3	0.0679 (16)	0.0367 (13)	0.0419 (13)	−0.0001 (11)	−0.0187 (11)	−0.0015 (10)
N1	0.0437 (15)	0.0313 (14)	0.0329 (13)	0.0036 (11)	−0.0026 (11)	−0.0010 (11)
C1	0.0498 (19)	0.0336 (17)	0.0347 (17)	−0.0006 (14)	0.0009 (15)	0.0032 (14)
C2	0.0340 (16)	0.0343 (16)	0.0300 (15)	0.0000 (13)	0.0007 (13)	0.0007 (12)
C3	0.0438 (18)	0.0382 (18)	0.0374 (17)	−0.0019 (14)	−0.0049 (14)	−0.0030 (14)
C4	0.0479 (19)	0.056 (2)	0.0344 (18)	0.0010 (16)	−0.0085 (15)	−0.0005 (15)
C5	0.050 (2)	0.048 (2)	0.0400 (18)	0.0060 (16)	−0.0051 (16)	0.0115 (16)
C6	0.0443 (19)	0.0354 (17)	0.0452 (19)	0.0038 (14)	−0.0015 (15)	0.0032 (14)
C7	0.0370 (17)	0.0347 (17)	0.0278 (15)	−0.0001 (13)	−0.0005 (13)	0.0003 (12)
C8	0.0401 (17)	0.0319 (16)	0.0390 (17)	0.0000 (13)	−0.0009 (14)	0.0033 (14)
C9	0.0350 (16)	0.0313 (16)	0.0362 (16)	0.0019 (13)	−0.0024 (13)	−0.0017 (13)
C10	0.0439 (18)	0.0305 (16)	0.0407 (18)	0.0027 (14)	−0.0066 (14)	0.0064 (13)
C11	0.0461 (18)	0.0271 (16)	0.0457 (19)	−0.0011 (13)	−0.0075 (15)	−0.0018 (14)
C12	0.0389 (17)	0.0359 (17)	0.0345 (16)	0.0020 (13)	−0.0027 (14)	−0.0028 (13)
C13	0.0472 (19)	0.0289 (16)	0.0365 (17)	0.0018 (14)	0.0006 (14)	0.0047 (13)
C14	0.0442 (18)	0.0280 (16)	0.0404 (17)	−0.0022 (13)	0.0000 (14)	−0.0035 (13)

Geometric parameters (Å, º) top

O1—C1	1.289 (3)	C5—H5	0.9300
O2—C1	1.225 (3)	C6—C7	1.380 (4)
O3—C12	1.329 (3)	C6—H6	0.9300
O3—H3A	0.95 (4)	C8—C9	1.430 (4)
N1—C8	1.291 (3)	C8—H8	0.9300
N1—C7	1.420 (3)	C9—C10	1.396 (4)
N1—H1	1.00 (3)	C9—C14	1.401 (4)
C1—C2	1.522 (4)	C10—C11	1.370 (4)
C2—C3	1.386 (4)	C10—H10	0.9300
C2—C7	1.400 (4)	C11—C12	1.393 (4)
C3—C4	1.378 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.395 (4)
C4—C5	1.375 (4)	C13—C14	1.368 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (4)	C14—H14	0.9300

C12—O3—H3A	111 (2)	C6—C7—N1	122.4 (3)
C8—N1—C7	127.0 (3)	C2—C7—N1	116.1 (2)
C8—N1—H1	122.7 (16)	N1—C8—C9	123.9 (3)
C7—N1—H1	109.9 (16)	N1—C8—H8	118.0
O2—C1—O1	124.2 (3)	C9—C8—H8	118.0
O2—C1—C2	119.2 (3)	C10—C9—C14	118.2 (3)
O1—C1—C2	116.6 (3)	C10—C9—C8	118.6 (3)
C3—C2—C7	117.6 (3)	C14—C9—C8	123.2 (3)
C3—C2—C1	117.9 (3)	C11—C10—C9	121.2 (3)
C7—C2—C1	124.5 (2)	C11—C10—H10	119.4
C4—C3—C2	121.4 (3)	C9—C10—H10	119.4
C4—C3—H3	119.3	C10—C11—C12	120.1 (3)
C2—C3—H3	119.3	C10—C11—H11	120.0
C5—C4—C3	119.9 (3)	C12—C11—H11	120.0
C5—C4—H4	120.0	O3—C12—C11	117.9 (3)
C3—C4—H4	120.0	O3—C12—C13	122.9 (3)
C4—C5—C6	120.5 (3)	C11—C12—C13	119.2 (3)
C4—C5—H5	119.8	C14—C13—C12	120.5 (3)
C6—C5—H5	119.8	C14—C13—H13	119.8
C5—C6—C7	119.2 (3)	C12—C13—H13	119.8
C5—C6—H6	120.4	C13—C14—C9	120.8 (3)
C7—C6—H6	120.4	C13—C14—H14	119.6
C6—C7—C2	121.4 (3)	C9—C14—H14	119.6

O2—C1—C2—C3	1.9 (4)	C8—N1—C7—C6	−11.1 (5)
O1—C1—C2—C3	−178.8 (3)	C8—N1—C7—C2	169.5 (3)
O2—C1—C2—C7	−177.6 (3)	C7—N1—C8—C9	179.4 (3)
O1—C1—C2—C7	1.7 (4)	N1—C8—C9—C10	172.3 (3)
C7—C2—C3—C4	0.6 (4)	N1—C8—C9—C14	−8.1 (5)
C1—C2—C3—C4	−179.0 (3)	C14—C9—C10—C11	1.9 (4)
C2—C3—C4—C5	−0.6 (5)	C8—C9—C10—C11	−178.6 (3)
C3—C4—C5—C6	0.1 (5)	C9—C10—C11—C12	0.0 (5)
C4—C5—C6—C7	0.4 (5)	C10—C11—C12—O3	178.3 (3)
C5—C6—C7—C2	−0.4 (4)	C10—C11—C12—C13	−2.1 (4)
C5—C6—C7—N1	−179.7 (3)	O3—C12—C13—C14	−178.0 (3)
C3—C2—C7—C6	0.0 (4)	C11—C12—C13—C14	2.3 (4)
C1—C2—C7—C6	179.5 (3)	C12—C13—C14—C9	−0.5 (4)
C3—C2—C7—N1	179.3 (3)	C10—C9—C14—C13	−1.6 (4)
C1—C2—C7—N1	−1.2 (4)	C8—C9—C14—C13	178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.95 (4)	1.71 (4)	2.656 (3)	173 (3)
N1—H1···O1	1.00 (3)	1.62 (3)	2.522 (3)	148 (2)
C6—H6···O2ⁱⁱ	0.93	2.51	3.397 (4)	160

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.95 (4)	1.71 (4)	2.656 (3)	173 (3)
N1—H1···O1	1.00 (3)	1.62 (3)	2.522 (3)	148 (2)
C6—H6···O2ⁱⁱ	0.93	2.51	3.397 (4)	160.1

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1/2, 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, Vice Chancellor, University of Sargodha, Pakistan.

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