(E)-3-[(2-Hy­droxy-3-meth­oxy­benzyl­idene)amino]­benzoic acid

Kargar, H.; Sharafi, Z.; Kia, R.; Ghelenji, S.; Tahir, M.N.

doi:10.1107/S1600536812010549

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1067

doi:10.1107/S1600536812010549

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(E)-3-[(2-Hydroxy-3-methoxybenzylidene)amino]benzoic acid

Hadi Kargar,^a ^* Zahra Sharafi,^b Reza Kia,^c Safoora Ghelenji ^d and Muhammad Nawaz Tahir ^e ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^dDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and ^eDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: h.kargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 6 March 2012; accepted 9 March 2012; online 14 March 2012)

In the title compound, C₁₅H₁₃NO₄, the dihedral angle between the substituted benzene rings is 9.9 (8)°. Part of the molecule (the salicylaldimine segment) is disordered over two sets of sites, with a refined site-occupancy ratio of 0.550 (14):0.450 (14). Intramolecular O—H⋯N hydrogen bonds form S(6) ring motifs. In the crystal, pairs of O—H⋯O hydrogen bonds link molecules into centrosymmetric dimers with R₂²(8) ring motifs. The crystal packing also features C—H⋯π interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For background to Schiff base ligands and their complexes, see, for example, Kargar et al. (2011 , 2012 ); Kia et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₃NO₄
M_r = 271.26
Triclinic, $[P \overline 1]$
a = 5.2738 (9) Å
b = 10.978 (2) Å
c = 12.084 (2) Å
α = 107.044 (10)°
β = 100.776 (11)°
γ = 97.539 (10)°
V = 644.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.19 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.981, T_max = 0.991
8775 measured reflections
2308 independent reflections
1253 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.258
S = 1.05
2308 reflections
279 parameters
405 restraints
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C9A–C14A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.96	1.69	2.638 (4)	169
O3—H3⋯N1	0.82	1.92	2.64 (2)	147
C15A—H15E⋯Cg1ⁱⁱ	0.96	2.90	3.757 (11)	139
C15A—H15E⋯Cg2ⁱⁱ	0.96	2.83	3.680 (12)	139
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010549/bq2344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010549/bq2344Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010549/bq2344Isup3.cml

checkCIF report

Comment top

In continuation of our work on the crystal structure of Schiff base ligands (Kargar et al., 2011; Kia et al., 2010; Kargar et al., 2012), we determined the X-ray structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a potentially bidentate N,O-donor Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges.

The intramolecular O—H···N hydrogen bonds make S(6) ring motifs (Bernstein et al., 1995). The dihedral angle between the substituted benzene rings is 9.9 (8)°. Pairs of the centrosymmetric intermolecular O—H···O hydrogen bonds link molecules into dimers with R²₂(8) ring motifs (Fig. 2). A part of the molecule was disordered over two positions with a refined site occupancy ratio 0.55 (1)/0.45 (1). The crystal packing was further stabilized by the intermolecular C—H···π interactions (Table 2).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to Schiff base ligands and their complexes, see, for example, Kargar et al. (2011, 2012); Kia et al. (2010).

Experimental top

The title compound was synthesized by adding 3-methoxyosalicylaldehyde (2 mmol) to a solution of 3-carboxyaniline (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered. Pale yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

The asymmetric unit of the title compound, Fig. 1, comprises a potentially bidentate N,O-donor Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges.

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to Schiff base ligands and their complexes, see, for example, Kargar et al. (2011, 2012); Kia et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The major component of the disordered part was used. The dashed line shows the intramolecular H-bonding.
	Fig. 2. The packing diagram of the title compound viewed down the c-axis showing linking of dimers with R²₂(8) ring motifs. Only the hydrogen atoms involved the H-bonding and the major component are shown.

(E)-3-[(2-Hydroxy-3-methoxybenzylidene)amino]benzoic acid top

Crystal data top

C₁₅H₁₃NO₄	Z = 2
M_r = 271.26	F(000) = 284
Triclinic, P1	D_x = 1.399 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2738 (9) Å	Cell parameters from 1456 reflections
b = 10.978 (2) Å	θ = 2.8–28.8°
c = 12.084 (2) Å	µ = 0.10 mm⁻¹
α = 107.044 (10)°	T = 296 K
β = 100.776 (11)°	Block, pale-yellow
γ = 97.539 (10)°	0.19 × 0.12 × 0.09 mm
V = 644.1 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
φ and ω scans	θ_max = 25.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
T_min = 0.981, T_max = 0.991	k = −13→13
8775 measured reflections	l = −14→14

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.258	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1461P)² + 0.0613P] where P = (F_o² + 2F_c²)/3
2308 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.59 e Å⁻³
405 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₃NO₄	γ = 97.539 (10)°
M_r = 271.26	V = 644.1 (2) Å³
Triclinic, P1	Z = 2
a = 5.2738 (9) Å	Mo Kα radiation
b = 10.978 (2) Å	µ = 0.10 mm⁻¹
c = 12.084 (2) Å	T = 296 K
α = 107.044 (10)°	0.19 × 0.12 × 0.09 mm
β = 100.776 (11)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2308 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1253 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.991	R_int = 0.047
8775 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	405 restraints
wR(F²) = 0.258	H-atom parameters constrained
S = 1.05	Δρ_max = 0.59 e Å⁻³
2308 reflections	Δρ_min = −0.28 e Å⁻³
279 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.2047 (6)	−0.0156 (3)	0.3825 (3)	0.0503 (9)
C2	0.3579 (6)	−0.0263 (3)	0.2901 (3)	0.0469 (8)
C3	0.3065 (7)	−0.1382 (3)	0.1929 (3)	0.0605 (10)
H3A	0.1755	−0.2078	0.1850	0.073*
C4	0.4508 (7)	−0.1461 (3)	0.1075 (3)	0.0659 (11)
H4A	0.4174	−0.2212	0.0421	0.079*
C5	0.6418 (7)	−0.0437 (3)	0.1192 (3)	0.0537 (9)
H5A	0.7389	−0.0505	0.0616	0.064*
C6	0.6948 (6)	0.0696 (3)	0.2142 (3)	0.0461 (8)
C7	0.5508 (6)	0.0785 (3)	0.3021 (3)	0.0472 (8)
H7A	0.5847	0.1537	0.3675	0.057*
O1	0.0350 (5)	−0.1160 (2)	0.3720 (2)	0.0663 (8)
O2	0.2431 (5)	0.0872 (2)	0.4652 (2)	0.0699 (8)
H2	0.1331	0.0870	0.5202	0.105*
N1	0.868 (3)	0.1754 (14)	0.215 (2)	0.038 (3)	0.550 (14)
C8	0.997 (2)	0.2711 (10)	0.3133 (11)	0.051 (3)	0.550 (14)
H8A	0.9624	0.2715	0.3861	0.061*	0.550 (14)
C9	1.192 (2)	0.3752 (9)	0.3088 (10)	0.054 (4)	0.550 (14)
C10	1.307 (8)	0.363 (2)	0.213 (3)	0.044 (5)	0.550 (14)
C11	1.473 (4)	0.4714 (14)	0.2060 (17)	0.058 (5)	0.550 (14)
C12	1.552 (7)	0.5805 (19)	0.305 (3)	0.062 (6)	0.550 (14)
H12A	1.6724	0.6497	0.3034	0.075*	0.550 (14)
C13	1.459 (2)	0.5914 (9)	0.4063 (10)	0.075 (3)	0.550 (14)
H13A	1.5152	0.6665	0.4722	0.090*	0.550 (14)
C14	1.281 (2)	0.4882 (9)	0.4072 (9)	0.073 (3)	0.550 (14)
H14A	1.2184	0.4940	0.4752	0.088*	0.550 (14)
C15	1.752 (2)	0.5546 (13)	0.0982 (14)	0.080 (4)	0.550 (14)
H15A	1.8146	0.5250	0.0272	0.121*	0.550 (14)
H15B	1.8972	0.5807	0.1667	0.121*	0.550 (14)
H15C	1.6696	0.6273	0.0964	0.121*	0.550 (14)
O3	1.207 (2)	0.2641 (12)	0.1078 (10)	0.065 (3)	0.550 (14)
H3	1.0896	0.2127	0.1154	0.097*	0.550 (14)
O4	1.565 (2)	0.4519 (10)	0.1044 (8)	0.080 (3)	0.550 (14)
N1A	0.929 (4)	0.1671 (17)	0.222 (3)	0.038 (3)	0.450 (14)
C8A	0.922 (2)	0.2889 (10)	0.2830 (11)	0.038 (3)	0.450 (14)
H8AA	0.7868	0.3062	0.3209	0.045*	0.450 (14)
C9A	1.128 (3)	0.3943 (10)	0.2899 (12)	0.044 (3)	0.450 (14)
C10A	1.287 (10)	0.374 (2)	0.210 (4)	0.041 (4)	0.450 (14)
C11A	1.503 (5)	0.4729 (15)	0.2231 (19)	0.044 (3)	0.450 (14)
C12A	1.521 (9)	0.595 (2)	0.300 (3)	0.062 (5)	0.450 (14)
H12B	1.6540	0.6625	0.3042	0.074*	0.450 (14)
C13A	1.344 (3)	0.6185 (9)	0.3695 (10)	0.061 (3)	0.450 (14)
H13B	1.3546	0.7023	0.4197	0.073*	0.450 (14)
C14A	1.151 (2)	0.5199 (7)	0.3662 (9)	0.057 (3)	0.450 (14)
H14B	1.0346	0.5371	0.4153	0.068*	0.450 (14)
C15A	1.854 (3)	0.5432 (16)	0.1425 (16)	0.077 (4)	0.450 (14)
H15D	1.9220	0.5133	0.0732	0.115*	0.450 (14)
H15E	1.9947	0.5697	0.2127	0.115*	0.450 (14)
H15F	1.7723	0.6156	0.1387	0.115*	0.450 (14)
O3A	1.295 (3)	0.2529 (14)	0.1380 (15)	0.062 (4)	0.450 (14)
H3B	1.1719	0.1997	0.1393	0.093*	0.450 (14)
O4A	1.661 (2)	0.4394 (11)	0.1466 (11)	0.062 (3)	0.450 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.049 (2)	0.0358 (17)	0.064 (2)	−0.0037 (15)	0.0263 (17)	0.0113 (16)
C2	0.0416 (18)	0.0415 (17)	0.061 (2)	0.0011 (15)	0.0226 (16)	0.0186 (16)
C3	0.058 (2)	0.0408 (18)	0.076 (2)	−0.0084 (16)	0.029 (2)	0.0086 (17)
C4	0.074 (3)	0.0459 (19)	0.069 (2)	−0.0080 (18)	0.035 (2)	0.0019 (17)
C5	0.054 (2)	0.0481 (19)	0.054 (2)	−0.0007 (16)	0.0273 (17)	0.0053 (16)
C6	0.0400 (18)	0.0430 (17)	0.057 (2)	0.0004 (14)	0.0226 (16)	0.0162 (15)
C7	0.0413 (18)	0.0389 (17)	0.059 (2)	−0.0023 (14)	0.0248 (16)	0.0097 (15)
O1	0.0638 (16)	0.0449 (13)	0.0852 (18)	−0.0150 (11)	0.0389 (14)	0.0117 (12)
O2	0.0772 (18)	0.0519 (15)	0.0748 (18)	−0.0139 (13)	0.0489 (14)	0.0046 (13)
N1	0.017 (7)	0.044 (2)	0.053 (3)	0.003 (3)	0.015 (5)	0.013 (2)
C8	0.045 (6)	0.055 (5)	0.046 (5)	−0.002 (4)	0.012 (4)	0.010 (4)
C9	0.048 (6)	0.050 (4)	0.057 (5)	0.001 (4)	0.025 (5)	0.003 (4)
C10	0.038 (8)	0.038 (6)	0.047 (5)	−0.002 (6)	0.014 (5)	0.002 (5)
C11	0.038 (6)	0.054 (5)	0.065 (7)	−0.007 (5)	0.025 (6)	−0.004 (5)
C12	0.045 (8)	0.051 (7)	0.080 (7)	−0.014 (7)	0.027 (6)	0.007 (6)
C13	0.058 (6)	0.057 (5)	0.082 (6)	−0.015 (4)	0.037 (5)	−0.018 (4)
C14	0.063 (6)	0.068 (5)	0.070 (5)	−0.015 (4)	0.038 (5)	−0.005 (4)
C15	0.057 (7)	0.079 (6)	0.105 (10)	−0.012 (5)	0.043 (7)	0.027 (6)
O3	0.057 (7)	0.052 (5)	0.067 (5)	−0.018 (4)	0.037 (5)	−0.009 (4)
O4	0.073 (6)	0.073 (4)	0.075 (5)	−0.030 (4)	0.040 (4)	0.004 (4)
N1A	0.017 (7)	0.044 (2)	0.053 (3)	0.003 (3)	0.015 (5)	0.013 (2)
C8A	0.027 (5)	0.042 (4)	0.047 (7)	0.008 (3)	0.021 (4)	0.010 (4)
C9A	0.040 (6)	0.034 (4)	0.057 (6)	0.000 (4)	0.020 (5)	0.013 (4)
C10A	0.030 (7)	0.033 (5)	0.062 (8)	0.004 (5)	0.021 (6)	0.013 (5)
C11A	0.042 (7)	0.042 (5)	0.054 (7)	0.001 (4)	0.017 (5)	0.023 (5)
C12A	0.055 (10)	0.044 (6)	0.077 (8)	−0.006 (6)	0.020 (7)	0.009 (6)
C13A	0.071 (7)	0.036 (4)	0.066 (6)	−0.004 (4)	0.022 (5)	0.005 (4)
C14A	0.060 (6)	0.039 (4)	0.070 (6)	0.006 (4)	0.028 (5)	0.010 (4)
C15A	0.067 (9)	0.069 (7)	0.099 (11)	−0.017 (7)	0.035 (7)	0.039 (7)
O3A	0.059 (8)	0.038 (4)	0.084 (8)	−0.002 (5)	0.041 (6)	0.002 (5)
O4A	0.050 (5)	0.064 (4)	0.076 (7)	−0.009 (4)	0.039 (5)	0.024 (4)

Geometric parameters (Å, º) top

C1—O2	1.232 (4)	C13—C14	1.378 (9)
C1—O1	1.284 (4)	C13—H13A	0.9300
C1—C2	1.482 (5)	C14—H14A	0.9300
C2—C3	1.382 (4)	C15—O4	1.426 (9)
C2—C7	1.385 (4)	C15—H15A	0.9600
C3—C4	1.382 (5)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.361 (4)	O3—H3	0.8200
C4—H4A	0.9300	N1A—C8A	1.333 (13)
C5—C6	1.376 (4)	C8A—C9A	1.450 (10)
C5—H5A	0.9300	C8A—H8AA	0.9300
C6—N1	1.38 (2)	C9A—C10A	1.382 (12)
C6—C7	1.405 (4)	C9A—C14A	1.391 (10)
C6—N1A	1.49 (3)	C10A—O3A	1.368 (19)
C7—H7A	0.9300	C10A—C11A	1.419 (14)
O2—H2	0.9612	C11A—O4A	1.362 (12)
N1—C8	1.329 (13)	C11A—C12A	1.367 (16)
C8—C9	1.454 (9)	C12A—C13A	1.374 (17)
C8—H8A	0.9300	C12A—H12B	0.9300
C9—C10	1.383 (11)	C13A—C14A	1.370 (10)
C9—C14	1.395 (9)	C13A—H13B	0.9300
C10—O3	1.365 (18)	C14A—H14B	0.9300
C10—C11	1.418 (13)	C15A—O4A	1.443 (10)
C11—C12	1.370 (15)	C15A—H15D	0.9600
C11—O4	1.373 (11)	C15A—H15E	0.9600
C12—C13	1.384 (16)	C15A—H15F	0.9600
C12—H12A	0.9300	O3A—H3B	0.8200

O2—C1—O1	122.7 (3)	C11—C12—H12A	118.8
O2—C1—C2	119.7 (3)	C13—C12—H12A	118.8
O1—C1—C2	117.6 (3)	C14—C13—C12	118.3 (8)
C3—C2—C7	120.6 (3)	C14—C13—H13A	120.9
C3—C2—C1	120.5 (3)	C12—C13—H13A	120.9
C7—C2—C1	118.9 (3)	C13—C14—C9	121.8 (7)
C2—C3—C4	119.7 (3)	C13—C14—H14A	119.1
C2—C3—H3A	120.2	C9—C14—H14A	119.1
C4—C3—H3A	120.2	C11—O4—C15	118.0 (9)
C5—C4—C3	120.0 (3)	C8A—N1A—C6	113.9 (18)
C5—C4—H4A	120.0	N1A—C8A—C9A	119.6 (14)
C3—C4—H4A	120.0	N1A—C8A—H8AA	120.2
C4—C5—C6	121.7 (3)	C9A—C8A—H8AA	120.2
C4—C5—H5A	119.2	C10A—C9A—C14A	118.6 (10)
C6—C5—H5A	119.2	C10A—C9A—C8A	119.5 (9)
C5—C6—N1	119.2 (10)	C14A—C9A—C8A	121.5 (10)
C5—C6—C7	118.9 (3)	O3A—C10A—C9A	123.2 (14)
N1—C6—C7	121.5 (9)	O3A—C10A—C11A	115 (2)
C5—C6—N1A	115.4 (10)	C9A—C10A—C11A	119.5 (10)
N1—C6—N1A	13.2 (17)	O4A—C11A—C12A	125.1 (11)
C7—C6—N1A	125.2 (11)	O4A—C11A—C10A	115.2 (10)
C2—C7—C6	119.2 (3)	C12A—C11A—C10A	119.3 (16)
C2—C7—H7A	120.4	C11A—C12A—C13A	120.0 (13)
C6—C7—H7A	120.4	C11A—C12A—H12B	120.0
C1—O2—H2	114.7	C13A—C12A—H12B	120.0
C8—N1—C6	123 (2)	C14A—C13A—C12A	120.9 (10)
N1—C8—C9	120.7 (14)	C14A—C13A—H13B	119.5
N1—C8—H8A	119.6	C12A—C13A—H13B	119.5
C9—C8—H8A	119.6	C13A—C14A—C9A	120.4 (9)
C10—C9—C14	118.3 (8)	C13A—C14A—H14B	119.8
C10—C9—C8	122.2 (8)	C9A—C14A—H14B	119.8
C14—C9—C8	119.4 (8)	O4A—C15A—H15D	109.5
O3—C10—C9	121.7 (12)	O4A—C15A—H15E	109.5
O3—C10—C11	115.0 (19)	H15D—C15A—H15E	109.5
C9—C10—C11	120.3 (8)	O4A—C15A—H15F	109.5
C12—C11—O4	125.4 (9)	H15D—C15A—H15F	109.5
C12—C11—C10	118.0 (14)	H15E—C15A—H15F	109.5
O4—C11—C10	116.1 (9)	C10A—O3A—H3B	109.5
C11—C12—C13	122.4 (10)	C11A—O4A—C15A	116.8 (11)

O2—C1—C2—C3	−176.1 (3)	O4—C11—C12—C13	−177 (3)
O1—C1—C2—C3	3.8 (5)	C10—C11—C12—C13	−5 (7)
O2—C1—C2—C7	3.1 (5)	C11—C12—C13—C14	0 (5)
O1—C1—C2—C7	−177.1 (3)	C12—C13—C14—C9	−1 (3)
C7—C2—C3—C4	0.6 (5)	C10—C9—C14—C13	7 (3)
C1—C2—C3—C4	179.8 (3)	C8—C9—C14—C13	−177.9 (9)
C2—C3—C4—C5	−0.2 (6)	C12—C11—O4—C15	−2 (4)
C3—C4—C5—C6	−0.7 (6)	C10—C11—O4—C15	−174 (3)
C4—C5—C6—N1	−172.3 (11)	C5—C6—N1A—C8A	156.3 (18)
C4—C5—C6—C7	1.2 (5)	N1—C6—N1A—C8A	46 (7)
C4—C5—C6—N1A	173.4 (14)	C7—C6—N1A—C8A	−32 (3)
C3—C2—C7—C6	−0.1 (5)	C6—N1A—C8A—C9A	−175.4 (16)
C1—C2—C7—C6	−179.3 (3)	N1A—C8A—C9A—C10A	17 (4)
C5—C6—C7—C2	−0.7 (5)	N1A—C8A—C9A—C14A	−170.5 (19)
N1—C6—C7—C2	172.6 (11)	C14A—C9A—C10A—O3A	175 (4)
N1A—C6—C7—C2	−172.2 (14)	C8A—C9A—C10A—O3A	−13 (7)
C5—C6—N1—C8	−157.2 (13)	C14A—C9A—C10A—C11A	13 (7)
C7—C6—N1—C8	29 (2)	C8A—C9A—C10A—C11A	−174 (4)
N1A—C6—N1—C8	−81 (10)	O3A—C10A—C11A—O4A	11 (6)
C6—N1—C8—C9	175.3 (12)	C9A—C10A—C11A—O4A	174 (4)
N1—C8—C9—C10	−19 (3)	O3A—C10A—C11A—C12A	−176 (4)
N1—C8—C9—C14	165.7 (13)	C9A—C10A—C11A—C12A	−13 (8)
C14—C9—C10—O3	−171 (3)	O4A—C11A—C12A—C13A	177 (3)
C8—C9—C10—O3	14 (5)	C10A—C11A—C12A—C13A	5 (8)
C14—C9—C10—C11	−12 (5)	C11A—C12A—C13A—C14A	2 (7)
C8—C9—C10—C11	173 (3)	C12A—C13A—C14A—C9A	−1 (3)
O3—C10—C11—C12	172 (4)	C10A—C9A—C14A—C13A	−6 (4)
C9—C10—C11—C12	11 (7)	C8A—C9A—C14A—C13A	−178.7 (11)
O3—C10—C11—O4	−16 (5)	C12A—C11A—O4A—C15A	−3 (5)
C9—C10—C11—O4	−176 (3)	C10A—C11A—O4A—C15A	169 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9–C14 and C9A–C14A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.96	1.69	2.638 (4)	169
O3—H3···N1	0.82	1.92	2.64 (2)	147
C15A—H15E···Cg1ⁱⁱ	0.96	2.90	3.757 (11)	139
C15A—H15E···Cg2ⁱⁱ	0.96	2.83	3.680 (12)	139

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₄
M_r	271.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.2738 (9), 10.978 (2), 12.084 (2)
α, β, γ (°)	107.044 (10), 100.776 (11), 97.539 (10)
V (Å³)	644.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.19 × 0.12 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.981, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8775, 2308, 1253
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.258, 1.05
No. of reflections	2308
No. of parameters	279
No. of restraints	405
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9–C14 and C9A–C14A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.96	1.69	2.638 (4)	169
O3—H3···N1	0.82	1.92	2.64 (2)	147
C15A—H15E···Cg1ⁱⁱ	0.96	2.90	3.757 (11)	139
C15A—H15E···Cg2ⁱⁱ	0.96	2.83	3.680 (12)	139

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

Acknowledgements

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R., Abbasian, S. & Tahir, M. N. (2012). Acta Cryst. E68, m182. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 4| April 2012| Page o1067

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