N-(4-Meth­oxy­phen­yl)maleamic acid

Gowda, B.T.; Tokarčík, M.; Shakuntala, K.; Kožíšek, J.; Fuess, H.

doi:10.1107/S1600536810019999

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1529-o1530

doi:10.1107/S1600536810019999

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N-(4-Methoxyphenyl)maleamic acid

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b K. Shakuntala,^a Jozef Kožíšek ^b and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 26 May 2010; accepted 26 May 2010; online 5 June 2010)

In the title compound, C₁₁H₁₁NO₄, the asymmetric unit contains two unique molecules, both of which are almost planar, with r.m.s. deviations of 0.047 and 0.059 Å. The dihedral angles between the benzene ring and the plane of maleamic acid unit are 3.43 (5) and 5.79 (3)° in the two molecules. The molecular structures are stabilized by a short intramolecular O—H⋯O hydrogen bond within each maleamic acid unit. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into zigzag chains extending along [1 $[\overline{1}]$ 0]. Weak intermolecular C—H⋯O hydrogen bonds also exist.

Related literature

For studies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda et al. (2009a ,b ,c ); Prasad et al. (2002 ). For the modes of interlinking carboxylic acids by hydrogen bonds, see: Jagannathan et al. (1994 ); Leiserowitz (1976 ).

Experimental

Crystal data

C₁₁H₁₁NO₄
M_r = 221.21
Triclinic, $[P \overline 1]$
a = 7.34030 (17) Å
b = 11.8258 (4) Å
c = 12.1207 (4) Å
α = 89.103 (3)°
β = 88.358 (2)°
γ = 78.396 (2)°
V = 1030.15 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.54 × 0.25 × 0.22 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.962, T_max = 0.980
15439 measured reflections
3711 independent reflections
2923 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.097
S = 1.02
3711 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.92	1.55	2.4624 (13)	174
O6—H6A⋯O5	0.92	1.53	2.4466 (14)	177
N1—H1N⋯O7ⁱ	0.86	2.10	2.9305 (14)	162
N2—H2N⋯O3ⁱⁱ	0.86	2.10	2.9124 (14)	158
C2—H2⋯O6ⁱ	0.93	2.44	3.3592 (16)	171
C6—H6⋯O7ⁱ	0.93	2.52	3.2822 (17)	140
C22—H22⋯O2ⁱⁱ	0.93	2.51	3.3792 (16)	156
C26—H26⋯O3ⁱⁱ	0.93	2.57	3.2881 (16)	135
C11—H11B⋯O5ⁱⁱⁱ	0.96	2.56	3.0688 (18)	113
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019999/bq2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810019999/bq2215Isup2.hkl

checkCIF report

Comment top

As a part of studying the effect of the ring and side chain substitutions on the crystal structures of biologically significant amides (Gowda et al., 2009a,b,c; Prasad et al., 2002), in the present work, the crystal structure of N-(4-methoxyphenyl)maleamic acid (I) has been determined (Fig. 1). The asymmetric unit of the structure contains two unique molecules. Both the molecules are almost planar with r.m.s deviations of 0.047Å and 0.059Å for the two molecules (Fig. 1).

The conformations of the N—H and the C=O bonds in the amide segment are anti to each other. In the side chain, the amide C=O bond is anti to the adjacent C—H bond, while the carboxyl C=O bond is syn to the adjacent C—H bond. The observed rare anti conformation of the C=O and O—H bonds of the acid group is similar to that obsrved in N-(2,6-dimethylphenyl)-maleamic acid (Gowda et al., 2009a), N-(3,4-dimethylphenyl)-maleamic acid (Gowda et al., 2009b) and N-(2,4,6-trimethylphenyl)- maleamic acid (Gowda et al., 2009c).

The dihedral angles between the phenyl ring and the plane of maleamic acid moiety are 3.43 (5)° and 5.79 (3)° in the first and second molecules, respectively. The molecular structure is stabilized by a short O–H···O intramolecular hydrogen bond (Table 1) within each maleamic acid moiety. The orientations of the methoxy groups toward the phenyl rings are given by the torsion angles, C7—C8—O4—C11 = -8.2 (2)° and C27—C28—O8—C31 = 0.7 (2)°. In the crystal structure (Fig. 2), the intermolecular N–H···O hydrogen bonds link the molecules into zigzag chains extending along the [1 -1 0] direction. Weak intermolecular C-H···O hydrogen bonds also exist in the structure.

The various modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Related literature top

For studies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda et al. (2009a,b,c); Prasad et al. (2002). For the modes of interlinking carboxylic acids by hydrogen bonds, see: Jagannathan et al. (1994); Leiserowitz (1976).

Experimental top

The solution of maleic anhydride (0.025 mol) in toluene (25 ml) was treated dropwise with the solution of 4-methoxyaniline (0.025 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 30 min and set aside for an additional 30 min at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 4-methoxyaniline. The resultant solid N-(4-methoxyphenyl)maleamic acid was filtered under suction and washed thoroughly with water to remove the unreacted maleic anhydride and maleic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared spectra. Prism like yellowish green single crystals of the title compound used in X-ray diffraction studies were grown in an ethanol solution by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular O—H···O bonds are shown as dashed lines.
	Fig. 2. Part of the crystal structure of (I) showing zigzag chains of molecules linked by intermolecular N—H···O hydrogen bonds, represented by dashed lines. Symmetry codes (i): -x,-y + 2,-z + 1; (ii) -x + 1,-y + 1,-z + 1. H atoms not involved in intermolecular hydrogen bonding have been omitted.

N-(4-Methoxyphenyl)maleamic acid top

Crystal data top

C₁₁H₁₁NO₄	Z = 4
M_r = 221.21	F(000) = 464
Triclinic, P1	D_x = 1.426 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.34030 (17) Å	Cell parameters from 8581 reflections
b = 11.8258 (4) Å	θ = 1.8–29.5°
c = 12.1207 (4) Å	µ = 0.11 mm⁻¹
α = 89.103 (3)°	T = 295 K
β = 88.358 (2)°	Prism, yellow–green
γ = 78.396 (2)°	0.54 × 0.25 × 0.22 mm
V = 1030.15 (5) Å³

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	3711 independent reflections
Graphite monochromator	2923 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.020
ω scans	θ_max = 25.2°, θ_min = 2.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→8
T_min = 0.962, T_max = 0.980	k = −14→14
15439 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0619P)² + 0.0566P] where P = (F_o² + 2F_c²)/3
3711 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₁H₁₁NO₄	γ = 78.396 (2)°
M_r = 221.21	V = 1030.15 (5) Å³
Triclinic, P1	Z = 4
a = 7.34030 (17) Å	Mo Kα radiation
b = 11.8258 (4) Å	µ = 0.11 mm⁻¹
c = 12.1207 (4) Å	T = 295 K
α = 89.103 (3)°	0.54 × 0.25 × 0.22 mm
β = 88.358 (2)°

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	3711 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	2923 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.980	R_int = 0.020
15439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
3711 reflections	Δρ_min = −0.20 e Å⁻³
291 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
C1	0.25076 (17)	0.51156 (11)	0.57066 (10)	0.0407 (3)
C2	0.23780 (18)	0.54345 (11)	0.68793 (11)	0.0431 (3)
H2	0.1732	0.6177	0.7035	0.052*
C3	0.30661 (18)	0.47979 (12)	0.77505 (11)	0.0466 (3)
H3	0.2826	0.5179	0.8421	0.056*
C4	0.41425 (18)	0.35955 (12)	0.78463 (11)	0.0459 (3)
C5	0.15402 (16)	0.58696 (10)	0.38503 (10)	0.0386 (3)
C6	0.05175 (18)	0.68231 (11)	0.33150 (11)	0.0439 (3)
H6	−0.0084	0.7452	0.3727	0.053*
C7	0.03742 (18)	0.68568 (11)	0.21824 (11)	0.0457 (3)
H7	−0.0314	0.7506	0.1838	0.055*
C8	0.12554 (18)	0.59239 (11)	0.15582 (10)	0.0444 (3)
C9	0.2264 (2)	0.49671 (12)	0.20906 (11)	0.0518 (4)
H9	0.286	0.4337	0.1677	0.062*
C10	0.24030 (19)	0.49303 (12)	0.32182 (11)	0.0487 (3)
H10	0.3076	0.4275	0.3561	0.058*
C11	0.0013 (2)	0.67727 (14)	−0.01187 (12)	0.0599 (4)
H11A	0.0047	0.6609	−0.0893	0.09*
H11B	0.0408	0.7488	−0.001	0.09*
H11C	−0.1233	0.6832	0.0171	0.09*
N1	0.16464 (14)	0.59247 (9)	0.50150 (8)	0.0406 (3)
H1N	0.1085	0.656	0.5312	0.049*
O1	0.33527 (15)	0.41551 (8)	0.53737 (8)	0.0625 (3)
O2	0.45825 (14)	0.29623 (8)	0.69728 (8)	0.0593 (3)
H2A	0.4196	0.3394	0.6353	0.089*
O3	0.45985 (15)	0.32053 (9)	0.87533 (8)	0.0644 (3)
O4	0.12243 (14)	0.58681 (9)	0.04387 (8)	0.0602 (3)
C21	0.22420 (17)	0.98092 (11)	0.13550 (10)	0.0415 (3)
C22	0.21905 (18)	0.94474 (11)	0.25224 (10)	0.0436 (3)
H22	0.2751	0.8685	0.2671	0.052*
C23	0.14486 (18)	1.00662 (12)	0.33956 (11)	0.0464 (3)
H23	0.1513	0.9648	0.4055	0.056*
C24	0.05379 (18)	1.13023 (12)	0.35040 (11)	0.0452 (3)
C25	0.33278 (16)	0.91072 (11)	−0.05093 (10)	0.0390 (3)
C26	0.40524 (19)	0.81103 (11)	−0.10879 (11)	0.0501 (3)
H26	0.4333	0.7409	−0.071	0.06*
C27	0.4366 (2)	0.81386 (12)	−0.22171 (11)	0.0512 (3)
H27	0.4853	0.7461	−0.2593	0.061*
C28	0.39523 (18)	0.91759 (11)	−0.27842 (10)	0.0448 (3)
C29	0.3238 (2)	1.01727 (12)	−0.22083 (11)	0.0528 (4)
H29	0.2962	1.0874	−0.2587	0.063*
C30	0.2928 (2)	1.01469 (12)	−0.10878 (11)	0.0503 (3)
H30	0.2448	1.0828	−0.0714	0.06*
C31	0.4932 (2)	0.83253 (14)	−0.45312 (12)	0.0605 (4)
H31A	0.5083	0.855	−0.5287	0.091*
H31B	0.4089	0.7801	−0.4484	0.091*
H31C	0.6116	0.7952	−0.4253	0.091*
N2	0.30677 (14)	0.90022 (9)	0.06518 (8)	0.0425 (3)
H2N	0.3498	0.8334	0.0934	0.051*
O5	0.15438 (16)	1.08043 (9)	0.10395 (8)	0.0675 (3)
O6	0.03939 (18)	1.19821 (9)	0.26512 (9)	0.0740 (4)
H6A	0.0815	1.156	0.203	0.111*
O7	−0.00459 (15)	1.16789 (9)	0.44012 (8)	0.0625 (3)
O8	0.42056 (16)	0.93176 (9)	−0.38950 (8)	0.0622 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0464 (7)	0.0308 (7)	0.0407 (7)	0.0016 (5)	0.0001 (5)	0.0018 (5)
C2	0.0502 (7)	0.0308 (7)	0.0424 (7)	0.0056 (5)	0.0015 (5)	0.0002 (6)
C3	0.0562 (8)	0.0393 (7)	0.0378 (7)	0.0058 (6)	−0.0007 (6)	−0.0002 (6)
C4	0.0510 (7)	0.0391 (7)	0.0426 (8)	0.0026 (6)	−0.0006 (6)	0.0064 (6)
C5	0.0423 (7)	0.0328 (7)	0.0381 (7)	−0.0017 (5)	0.0005 (5)	0.0024 (5)
C6	0.0551 (8)	0.0307 (7)	0.0415 (7)	0.0020 (6)	−0.0001 (6)	−0.0008 (6)
C7	0.0561 (8)	0.0318 (7)	0.0438 (8)	0.0038 (6)	−0.0042 (6)	0.0047 (6)
C8	0.0518 (8)	0.0410 (8)	0.0372 (7)	−0.0015 (6)	−0.0012 (6)	0.0007 (6)
C9	0.0604 (8)	0.0417 (8)	0.0436 (8)	0.0128 (6)	−0.0003 (6)	−0.0046 (6)
C10	0.0566 (8)	0.0375 (7)	0.0438 (8)	0.0101 (6)	−0.0027 (6)	0.0028 (6)
C11	0.0771 (10)	0.0557 (9)	0.0396 (8)	0.0045 (7)	−0.0068 (7)	0.0071 (7)
N1	0.0487 (6)	0.0303 (5)	0.0375 (6)	0.0045 (4)	0.0011 (4)	0.0013 (5)
O1	0.0925 (8)	0.0384 (6)	0.0427 (6)	0.0204 (5)	−0.0047 (5)	−0.0015 (4)
O2	0.0821 (7)	0.0365 (5)	0.0472 (6)	0.0170 (5)	−0.0037 (5)	0.0029 (5)
O3	0.0822 (7)	0.0526 (6)	0.0468 (6)	0.0141 (5)	−0.0062 (5)	0.0118 (5)
O4	0.0797 (7)	0.0535 (6)	0.0361 (5)	0.0137 (5)	−0.0050 (5)	−0.0008 (5)
C21	0.0456 (7)	0.0337 (7)	0.0403 (7)	0.0037 (5)	0.0009 (5)	−0.0005 (6)
C22	0.0523 (7)	0.0307 (7)	0.0420 (7)	0.0050 (5)	0.0017 (6)	0.0036 (6)
C23	0.0565 (8)	0.0392 (7)	0.0381 (7)	0.0026 (6)	0.0034 (6)	0.0050 (6)
C24	0.0504 (7)	0.0392 (7)	0.0413 (8)	0.0020 (6)	0.0032 (6)	−0.0032 (6)
C25	0.0416 (7)	0.0351 (7)	0.0369 (7)	0.0002 (5)	−0.0007 (5)	−0.0011 (5)
C26	0.0687 (9)	0.0329 (7)	0.0424 (8)	0.0043 (6)	0.0006 (6)	0.0018 (6)
C27	0.0699 (9)	0.0348 (7)	0.0429 (8)	0.0036 (6)	0.0022 (6)	−0.0081 (6)
C28	0.0552 (8)	0.0406 (8)	0.0367 (7)	−0.0048 (6)	−0.0002 (6)	−0.0021 (6)
C29	0.0748 (9)	0.0344 (7)	0.0436 (8)	0.0015 (6)	0.0044 (7)	0.0038 (6)
C30	0.0675 (9)	0.0332 (7)	0.0443 (8)	0.0030 (6)	0.0069 (6)	−0.0036 (6)
C31	0.0817 (10)	0.0549 (9)	0.0413 (8)	−0.0047 (8)	0.0054 (7)	−0.0117 (7)
N2	0.0533 (6)	0.0313 (6)	0.0375 (6)	0.0041 (5)	0.0010 (5)	0.0014 (5)
O5	0.1026 (8)	0.0409 (6)	0.0420 (6)	0.0240 (5)	0.0096 (5)	0.0054 (5)
O6	0.1190 (9)	0.0380 (6)	0.0475 (6)	0.0228 (6)	0.0169 (6)	0.0035 (5)
O7	0.0846 (7)	0.0484 (6)	0.0447 (6)	0.0092 (5)	0.0093 (5)	−0.0084 (5)
O8	0.0996 (8)	0.0456 (6)	0.0354 (5)	−0.0009 (5)	0.0053 (5)	−0.0028 (4)

Geometric parameters (Å, º) top

C1—O1	1.2468 (15)	C21—O5	1.2444 (15)
C1—N1	1.3341 (16)	C21—N2	1.3295 (16)
C1—C2	1.4719 (18)	C21—C22	1.4735 (18)
C2—C3	1.3377 (18)	C22—C23	1.3353 (18)
C2—H2	0.93	C22—H22	0.93
C3—C4	1.4858 (18)	C23—C24	1.4862 (19)
C3—H3	0.93	C23—H23	0.93
C4—O3	1.2151 (16)	C24—O7	1.2151 (16)
C4—O2	1.3015 (16)	C24—O6	1.2930 (17)
C5—C6	1.3858 (17)	C25—C26	1.3845 (18)
C5—C10	1.3921 (18)	C25—C30	1.3890 (18)
C5—N1	1.4193 (16)	C25—N2	1.4217 (16)
C6—C7	1.3792 (18)	C26—C27	1.3824 (18)
C6—H6	0.93	C26—H26	0.93
C7—C8	1.3853 (19)	C27—C28	1.3803 (19)
C7—H7	0.93	C27—H27	0.93
C8—O4	1.3606 (16)	C28—O8	1.3662 (16)
C8—C9	1.3829 (19)	C28—C29	1.3812 (19)
C9—C10	1.3728 (19)	C29—C30	1.3715 (19)
C9—H9	0.93	C29—H29	0.93
C10—H10	0.93	C30—H30	0.93
C11—O4	1.4213 (17)	C31—O8	1.4174 (17)
C11—H11A	0.96	C31—H31A	0.96
C11—H11B	0.96	C31—H31B	0.96
C11—H11C	0.96	C31—H31C	0.96
N1—H1N	0.86	N2—H2N	0.86
O2—H2A	0.92	O6—H6A	0.92

O1—C1—N1	121.77 (12)	O5—C21—N2	121.73 (11)
O1—C1—C2	122.78 (12)	O5—C21—C22	122.37 (12)
N1—C1—C2	115.45 (11)	N2—C21—C22	115.89 (11)
C3—C2—C1	128.61 (12)	C23—C22—C21	128.78 (12)
C3—C2—H2	115.7	C23—C22—H22	115.6
C1—C2—H2	115.7	C21—C22—H22	115.6
C2—C3—C4	131.96 (13)	C22—C23—C24	131.60 (13)
C2—C3—H3	114	C22—C23—H23	114.2
C4—C3—H3	114	C24—C23—H23	114.2
O3—C4—O2	120.22 (12)	O7—C24—O6	119.93 (12)
O3—C4—C3	119.17 (13)	O7—C24—C23	119.81 (13)
O2—C4—C3	120.61 (11)	O6—C24—C23	120.25 (12)
C6—C5—C10	118.38 (12)	C26—C25—C30	118.52 (12)
C6—C5—N1	117.26 (11)	C26—C25—N2	117.52 (11)
C10—C5—N1	124.36 (11)	C30—C25—N2	123.95 (11)
C7—C6—C5	121.26 (12)	C27—C26—C25	121.19 (12)
C7—C6—H6	119.4	C27—C26—H26	119.4
C5—C6—H6	119.4	C25—C26—H26	119.4
C6—C7—C8	120.00 (12)	C28—C27—C26	119.77 (12)
C6—C7—H7	120	C28—C27—H27	120.1
C8—C7—H7	120	C26—C27—H27	120.1
O4—C8—C9	116.12 (12)	O8—C28—C27	125.33 (12)
O4—C8—C7	124.99 (12)	O8—C28—C29	115.50 (12)
C9—C8—C7	118.89 (12)	C27—C28—C29	119.17 (12)
C10—C9—C8	121.19 (13)	C30—C29—C28	121.17 (13)
C10—C9—H9	119.4	C30—C29—H29	119.4
C8—C9—H9	119.4	C28—C29—H29	119.4
C9—C10—C5	120.27 (12)	C29—C30—C25	120.18 (12)
C9—C10—H10	119.9	C29—C30—H30	119.9
C5—C10—H10	119.9	C25—C30—H30	119.9
O4—C11—H11A	109.5	O8—C31—H31A	109.5
O4—C11—H11B	109.5	O8—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
O4—C11—H11C	109.5	O8—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C1—N1—C5	128.19 (11)	C21—N2—C25	128.07 (11)
C1—N1—H1N	115.9	C21—N2—H2N	116
C5—N1—H1N	115.9	C25—N2—H2N	116
C4—O2—H2A	109.5	C24—O6—H6A	109.5
C8—O4—C11	117.28 (11)	C28—O8—C31	118.13 (11)

O1—C1—C2—C3	−1.0 (2)	O5—C21—C22—C23	−0.1 (2)
N1—C1—C2—C3	178.62 (13)	N2—C21—C22—C23	−179.46 (13)
C1—C2—C3—C4	−0.6 (2)	C21—C22—C23—C24	−3.5 (2)
C2—C3—C4—O3	−179.27 (15)	C22—C23—C24—O7	179.83 (14)
C2—C3—C4—O2	0.2 (2)	C22—C23—C24—O6	−1.4 (2)
C10—C5—C6—C7	−1.04 (19)	C30—C25—C26—C27	−0.4 (2)
N1—C5—C6—C7	178.47 (11)	N2—C25—C26—C27	−179.36 (12)
C5—C6—C7—C8	0.3 (2)	C25—C26—C27—C28	0.0 (2)
C6—C7—C8—O4	−179.29 (12)	C26—C27—C28—O8	179.68 (13)
C6—C7—C8—C9	0.3 (2)	C26—C27—C28—C29	0.3 (2)
O4—C8—C9—C10	179.56 (12)	O8—C28—C29—C30	−179.67 (12)
C7—C8—C9—C10	0.0 (2)	C27—C28—C29—C30	−0.2 (2)
C8—C9—C10—C5	−0.8 (2)	C28—C29—C30—C25	−0.1 (2)
C6—C5—C10—C9	1.27 (19)	C26—C25—C30—C29	0.4 (2)
N1—C5—C10—C9	−178.21 (12)	N2—C25—C30—C29	179.36 (12)
O1—C1—N1—C5	−0.7 (2)	O5—C21—N2—C25	1.0 (2)
C2—C1—N1—C5	179.61 (10)	C22—C21—N2—C25	−179.59 (11)
C6—C5—N1—C1	178.55 (12)	C26—C25—N2—C21	−173.12 (12)
C10—C5—N1—C1	−2.0 (2)	C30—C25—N2—C21	8.0 (2)
C9—C8—O4—C11	172.28 (13)	C27—C28—O8—C31	0.7 (2)
C7—C8—O4—C11	−8.2 (2)	C29—C28—O8—C31	−179.88 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.92	1.55	2.4624 (13)	174
O6—H6A···O5	0.92	1.53	2.4466 (14)	177
N1—H1N···O7ⁱ	0.86	2.10	2.9305 (14)	162
N2—H2N···O3ⁱⁱ	0.86	2.10	2.9124 (14)	158
C2—H2···O6ⁱ	0.93	2.44	3.3592 (16)	171
C6—H6···O7ⁱ	0.93	2.52	3.2822 (17)	140
C22—H22···O2ⁱⁱ	0.93	2.51	3.3792 (16)	156
C26—H26···O3ⁱⁱ	0.93	2.57	3.2881 (16)	135
C11—H11B···O5ⁱⁱⁱ	0.96	2.56	3.0688 (18)	113

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₄
M_r	221.21
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.34030 (17), 11.8258 (4), 12.1207 (4)
α, β, γ (°)	89.103 (3), 88.358 (2), 78.396 (2)
V (Å³)	1030.15 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.54 × 0.25 × 0.22

Data collection
Diffractometer	Oxford Diffraction Gemini R CCD diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.962, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15439, 3711, 2923
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.02
No. of reflections	3711
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.92	1.55	2.4624 (13)	174
O6—H6A···O5	0.92	1.53	2.4466 (14)	177
N1—H1N···O7ⁱ	0.86	2.10	2.9305 (14)	162
N2—H2N···O3ⁱⁱ	0.86	2.10	2.9124 (14)	158
C2—H2···O6ⁱ	0.93	2.44	3.3592 (16)	171
C6—H6···O7ⁱ	0.93	2.52	3.2822 (17)	140
C22—H22···O2ⁱⁱ	0.93	2.51	3.3792 (16)	156
C26—H26···O3ⁱⁱ	0.93	2.57	3.2881 (16)	135
C11—H11B···O5ⁱⁱⁱ	0.96	2.56	3.0688 (18)	113

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

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support to purchase the diffractometer. KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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