2-{[(E)-1,3-Benzodioxol-5-yl]methyl­idene­amino}­benzoic acid

Abstract

In the title compound, C₁₅H₁₁NO₄, the dihedral angle between the aromatic rings is 23.8 (2)° and an intra­molecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network.

Related literature

For a related structure, see: Yang et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

• C₁₅H₁₁NO₄

• M _r = 269.25

• Orthorhombic,

• a = 22.884 (2) Å

• b = 3.9402 (4) Å

• c = 13.5696 (13) Å

• V = 1223.5 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.11 mm⁻¹

• T = 296 K

• 0.28 × 0.14 × 0.10 mm

Data collection

• Bruker Kappa APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.988

• 28104 measured reflections

• 1152 independent reflections

• 925 reflections with I > 2σ(I)

• R _int = 0.079

Refinement

• R[F ² > 2σ(F ²)] = 0.049

• wR(F ²) = 0.122

• S = 1.12

• 1152 reflections

• 184 parameters

• 1 restraint

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

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −0.21 e Å⁻³

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.

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⋯N1	0.83 (7)	1.83 (7)	2.544 (5)	143 (7)
C14—H14⋯O2i	0.93	2.42	3.337 (6)	170
C15—H15A⋯O2ii	0.97	2.60	3.532 (6)	162

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is being reported as a part of our on going project related to synthesize various Schiff bases of pipronal and anthranilic acid with different anilines and aldehydes, respectively. The title compound will be utilized for preparing the metal complexes.

The crystal structure of (II) i.e., (E)-4-methoxy-N-(3,4-methylenedioxybenzylidene)aniline (Yang et al., 2007) has been published which are related to the title compound.

In the title compound, the anthranilic acid moiety A (C1—C7/N1/O1/O2) and pipronal group B (C8—C15/O3/O4) are almost planar with r. m. s. deviations of 0.0105 and 0.0112 Å, respectively. The dihedral angle between A/B is 23.78 (9)°. The intramolecular H-bonding of O—H···N type (Table 1, Fig. 1) complete an S(6) ring motif (Bernstein et al., 1995). The title compound consist of three dimensional zigzag polymeric network (Fig. 2) due to H-bondings of C—H···O type (Table 2). There does not exist any C—H···π interaction.

Experimental

Equimolar quantities of anthranilic acid and pipronal were refluxed in methanol for 30 min resulting in orange yellow solution. The solution was kept at room temperature which affoarded orange yellow needles of (I) after a week.

Refinement

In the absence of significant anomalous scattering, all Friedal pairs were merged.

The coordinates of hydroxy H-atom were refined. The carbon H-atoms were positioned geometrically (C–H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = xU_eq(C, O), where x = 1.2 for all H-atoms.

Figures

Fig. 1.

View of (I) with displacement ellipsoids drawn at the 50% probability level. The dotted line represent the intramolecular H-bonding.

Fig. 2.

The partial packing of (I), which shows that molecules form polymeric chains.

Crystal data

C15H11NO4	F(000) = 560
Mr = 269.25	Dx = 1.462 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 925 reflections
a = 22.884 (2) Å	θ = 2.3–25.2°
b = 3.9402 (4) Å	µ = 0.11 mm−1
c = 13.5696 (13) Å	T = 296 K
V = 1223.5 (2) Å3	Needle, orange yellow
Z = 4	0.28 × 0.14 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1152 independent reflections
Radiation source: fine-focus sealed tube	925 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 8.20 pixels mm-1	θmax = 25.2°, θmin = 2.3°
ω scans	h = −27→27
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −4→4
Tmin = 0.980, Tmax = 0.988	l = −16→16
28104 measured reflections

Refinement

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.1607P] where P = (Fo2 + 2Fc2)/3
1152 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Special details

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 e.s.d.'s 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.51893 (16)	0.1333 (11)	0.1270 (2)	0.0783 (14)
O2	0.60847 (16)	0.3309 (12)	0.1082 (3)	0.0870 (16)
O3	0.28294 (13)	−0.2221 (9)	0.0939 (2)	0.0644 (11)
O4	0.22350 (12)	−0.5110 (9)	0.2031 (3)	0.0615 (11)
N1	0.47183 (15)	0.1225 (8)	0.2968 (3)	0.0477 (11)
C1	0.5677 (2)	0.2642 (12)	0.1623 (3)	0.0597 (17)
C2	0.56974 (18)	0.3361 (10)	0.2714 (3)	0.0453 (12)
C3	0.62059 (19)	0.4809 (11)	0.3079 (4)	0.0557 (16)
C4	0.6268 (2)	0.5551 (12)	0.4064 (4)	0.0603 (17)
C5	0.5811 (2)	0.4898 (11)	0.4697 (4)	0.0613 (17)
C6	0.53019 (19)	0.3494 (11)	0.4360 (3)	0.0550 (16)
C7	0.52366 (16)	0.2630 (10)	0.3363 (3)	0.0427 (12)
C8	0.43348 (17)	−0.0263 (9)	0.3505 (3)	0.0487 (12)
C9	0.37893 (17)	−0.1565 (9)	0.3122 (3)	0.0453 (12)
C10	0.36230 (17)	−0.1111 (11)	0.2122 (3)	0.0480 (12)
C11	0.30981 (17)	−0.2372 (11)	0.1848 (3)	0.0463 (12)
C12	0.27312 (17)	−0.4075 (11)	0.2501 (3)	0.0477 (14)
C13	0.28753 (18)	−0.4521 (11)	0.3468 (4)	0.0520 (14)
C14	0.34183 (19)	−0.3234 (11)	0.3770 (3)	0.0520 (14)
C15	0.2282 (2)	−0.3962 (14)	0.1039 (4)	0.0650 (17)
H1	0.491 (3)	0.140 (15)	0.166 (5)	0.0937*
H3	0.65112	0.52880	0.26487	0.0668*
H4	0.66140	0.64831	0.43000	0.0722*
H5	0.58489	0.54176	0.53624	0.0734*
H6	0.49957	0.31078	0.47961	0.0655*
H8	0.44114	−0.05185	0.41734	0.0582*
H10	0.38644	0.00051	0.16763	0.0575*
H13	0.26261	−0.56229	0.39043	0.0623*
H14	0.35328	−0.35079	0.44231	0.0623*
H15A	0.19620	−0.24411	0.08841	0.0780*
H15B	0.22671	−0.58749	0.05902	0.0780*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.071 (2)	0.130 (3)	0.034 (2)	−0.009 (2)	−0.0057 (16)	−0.008 (2)
O2	0.074 (2)	0.143 (4)	0.044 (2)	−0.012 (2)	0.0141 (19)	−0.003 (2)
O3	0.0587 (18)	0.094 (2)	0.0405 (18)	−0.0102 (18)	−0.0039 (15)	0.0052 (17)
O4	0.0574 (17)	0.080 (2)	0.047 (2)	−0.0098 (16)	−0.0032 (15)	0.0034 (18)
N1	0.0472 (19)	0.055 (2)	0.041 (2)	0.0002 (16)	0.0019 (17)	0.0018 (17)
C1	0.055 (3)	0.079 (3)	0.045 (3)	0.000 (2)	−0.002 (2)	0.004 (2)
C2	0.052 (2)	0.049 (2)	0.035 (2)	0.0056 (19)	0.0013 (18)	0.0029 (18)
C3	0.053 (2)	0.065 (3)	0.049 (3)	−0.002 (2)	0.002 (2)	−0.001 (2)
C4	0.057 (3)	0.068 (3)	0.056 (3)	−0.007 (2)	−0.011 (2)	−0.002 (2)
C5	0.079 (3)	0.062 (3)	0.043 (3)	−0.008 (3)	−0.007 (3)	−0.008 (2)
C6	0.063 (3)	0.059 (2)	0.043 (3)	−0.003 (2)	0.004 (2)	−0.002 (2)
C7	0.048 (2)	0.044 (2)	0.036 (2)	0.0044 (18)	−0.0005 (18)	0.0011 (16)
C8	0.055 (2)	0.049 (2)	0.042 (2)	0.007 (2)	0.000 (2)	0.002 (2)
C9	0.048 (2)	0.047 (2)	0.041 (2)	0.0048 (18)	0.0014 (19)	0.0020 (18)
C10	0.050 (2)	0.054 (2)	0.040 (2)	0.0019 (19)	0.006 (2)	0.0058 (19)
C11	0.052 (2)	0.054 (2)	0.033 (2)	0.009 (2)	0.0016 (19)	−0.0006 (19)
C12	0.045 (2)	0.055 (2)	0.043 (3)	−0.0001 (19)	0.0020 (19)	−0.001 (2)
C13	0.056 (2)	0.055 (2)	0.045 (3)	0.000 (2)	0.006 (2)	0.006 (2)
C14	0.056 (2)	0.054 (2)	0.046 (3)	0.008 (2)	0.006 (2)	0.010 (2)
C15	0.067 (3)	0.082 (3)	0.046 (3)	−0.003 (3)	−0.005 (2)	0.006 (2)

Geometric parameters (Å, °)

O1—C1	1.320 (6)	C9—C14	1.388 (6)
O2—C1	1.216 (6)	C9—C10	1.421 (6)
O3—C11	1.380 (5)	C10—C11	1.352 (6)
O3—C15	1.435 (6)	C11—C12	1.393 (6)
O4—C12	1.365 (5)	C12—C13	1.364 (7)
O4—C15	1.424 (7)	C13—C14	1.403 (6)
O1—H1	0.83 (7)	C3—H3	0.9300
N1—C7	1.414 (5)	C4—H4	0.9300
N1—C8	1.283 (5)	C5—H5	0.9300
C1—C2	1.508 (6)	C6—H6	0.9300
C2—C7	1.404 (6)	C8—H8	0.9300
C2—C3	1.387 (6)	C10—H10	0.9300
C3—C4	1.376 (8)	C13—H13	0.9300
C4—C5	1.378 (7)	C14—H14	0.9300
C5—C6	1.368 (6)	C15—H15A	0.9700
C6—C7	1.403 (6)	C15—H15B	0.9700
C8—C9	1.446 (5)
C11—O3—C15	106.5 (3)	C11—C12—C13	121.9 (4)
C12—O4—C15	106.5 (3)	O4—C12—C11	110.4 (4)
C1—O1—H1	114 (5)	C12—C13—C14	116.6 (4)
C7—N1—C8	122.5 (4)	C9—C14—C13	121.9 (4)
O1—C1—O2	121.0 (4)	O3—C15—O4	107.9 (4)
O1—C1—C2	117.1 (4)	C2—C3—H3	119.00
O2—C1—C2	121.9 (4)	C4—C3—H3	119.00
C1—C2—C3	117.0 (4)	C3—C4—H4	120.00
C1—C2—C7	123.7 (4)	C5—C4—H4	120.00
C3—C2—C7	119.4 (4)	C4—C5—H5	120.00
C2—C3—C4	121.4 (4)	C6—C5—H5	120.00
C3—C4—C5	119.2 (4)	C5—C6—H6	120.00
C4—C5—C6	120.9 (5)	C7—C6—H6	120.00
C5—C6—C7	120.7 (4)	N1—C8—H8	118.00
N1—C7—C2	118.2 (4)	C9—C8—H8	118.00
N1—C7—C6	123.4 (4)	C9—C10—H10	121.00
C2—C7—C6	118.4 (4)	C11—C10—H10	122.00
N1—C8—C9	123.3 (4)	C12—C13—H13	122.00
C8—C9—C14	117.9 (4)	C14—C13—H13	122.00
C10—C9—C14	120.1 (4)	C9—C14—H14	119.00
C8—C9—C10	122.0 (4)	C13—C14—H14	119.00
C9—C10—C11	117.0 (4)	O3—C15—H15A	110.00
O3—C11—C10	128.8 (4)	O3—C15—H15B	110.00
O3—C11—C12	108.7 (3)	O4—C15—H15A	110.00
C10—C11—C12	122.5 (4)	O4—C15—H15B	110.00
O4—C12—C13	127.7 (4)	H15A—C15—H15B	109.00
C15—O3—C11—C10	179.6 (5)	C3—C4—C5—C6	0.7 (7)
C15—O3—C11—C12	−1.2 (5)	C4—C5—C6—C7	1.1 (7)
C11—O3—C15—O4	0.5 (5)	C5—C6—C7—N1	−178.9 (4)
C15—O4—C12—C11	−1.1 (5)	C5—C6—C7—C2	−2.4 (6)
C15—O4—C12—C13	178.3 (5)	N1—C8—C9—C10	−3.7 (6)
C12—O4—C15—O3	0.4 (5)	N1—C8—C9—C14	177.8 (4)
C8—N1—C7—C2	162.9 (4)	C8—C9—C10—C11	−178.7 (4)
C8—N1—C7—C6	−20.6 (6)	C14—C9—C10—C11	−0.2 (6)
C7—N1—C8—C9	176.8 (3)	C8—C9—C14—C13	178.7 (4)
O1—C1—C2—C3	−178.6 (4)	C10—C9—C14—C13	0.2 (6)
O1—C1—C2—C7	1.8 (6)	C9—C10—C11—O3	178.6 (4)
O2—C1—C2—C3	−0.4 (7)	C9—C10—C11—C12	−0.5 (6)
O2—C1—C2—C7	−180.0 (5)	O3—C11—C12—O4	1.5 (5)
C1—C2—C3—C4	−179.8 (4)	O3—C11—C12—C13	−178.0 (4)
C7—C2—C3—C4	−0.1 (6)	C10—C11—C12—O4	−179.3 (4)
C1—C2—C7—N1	−1.8 (6)	C10—C11—C12—C13	1.3 (7)
C1—C2—C7—C6	−178.5 (4)	O4—C12—C13—C14	179.4 (4)
C3—C2—C7—N1	178.6 (4)	C11—C12—C13—C14	−1.2 (6)
C3—C2—C7—C6	1.9 (6)	C12—C13—C14—C9	0.5 (6)
C2—C3—C4—C5	−1.2 (7)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.83 (7)	1.83 (7)	2.544 (5)	143 (7)
C14—H14···O2i	0.93	2.42	3.337 (6)	170
C15—H15A···O2ii	0.97	2.60	3.532 (6)	162

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