3,3′-[(4-Nitro­phen­yl)methyl­ene]bis­(4-hy­droxy-2H-chromen-2-one)

Ravikumar, N.; Gopikrishna, G.; Solomon, K.A.

doi:10.1107/S1600536811054778

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o265

doi:10.1107/S1600536811054778

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3,3′-[(4-Nitrophenyl)methylene]bis(4-hydroxy-2H-chromen-2-one)

N. Ravikumar,^a G. Gopikrishna ^a and K. Anand Solomon ^a ^*

^aSankar Foundation Research Institute, Naiduthota, Vepagunta, Visakhapatnam, Andhra Pradesh 530 047, India
^*Correspondence e-mail: anand.dcb@gmail.com

(Received 3 December 2011; accepted 20 December 2011; online 7 January 2012)

The molecular conformation of the title compound, C₂₅H₁₅NO₈, is stabilized by strong intramolecular O—H⋯O hydrogen bonds, resulting in the formation of S₁¹(7) ring motifs. In the crystal, π–π stacking interactions are observed between adjacent nitrobenzene and pyranone rings with a centroid–centroid distance of 3.513 (12) Å. The dihedral angles between the nitrobenzene ring and the coumarin ring systems are 65.61 (8) and 66.11 (8)° while the coumarin ring systems are inclined at 65.69 (8)°.

Related literature

For the synthesis of benzylidene-bis-(4-hydroxycoumarin) derivatives, see: Mehrabi & Abusaidi (2010 ); Završnik et al. (2011 ). For hydrogen bonds, see: Desiraju & Steiner (1999 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For the biological activity of substituted benzylidene-bis-(4-hydroxycoumarin) derivatives, see: Borges et al. (2005 ); Nolan et al. (2009 ); Prakash et al. (2008 ); Zhao et al. (1997 ).

Experimental

Crystal data

C₂₅H₁₅NO₈
M_r = 457.38
Orthorhombic, P n a 2₁
a = 14.0061 (6) Å
b = 14.1511 (6) Å
c = 10.4179 (4) Å
V = 2064.85 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.902, T_max = 0.973
15733 measured reflections
3316 independent reflections
2913 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.089
S = 1.04
3316 reflections
310 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5	0.82	1.79	2.597 (2)	166
O6—H6A⋯O1	0.82	1.80	2.617 (2)	173

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054778/rk2323sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054778/rk2323Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054778/rk2323Isup3.cml

checkCIF report

Comment top

Sevaral methods were reported in the literature (Mehrabi et al. 2010) and (Završnik et al. 2011) for the synthesis of the title compound. Coumarin ring forms an important pharmacophore in several naturally occurring as well as synthetic molecules (Prakash et al. 2008). These coumarin derivaties showed numerous therapeutic applications such as anticoagulant and antibacterial agents (Borges et al. 2005). Several multifunctionalized coumarin derivatives were reported to exhibit anti-HIV properties (Zhao et al. 1997) and also as inhibitors of quinone oxidoreductase-1 (Nolan et al. 2009).

In title compound, C₂₅H₁₅NO₈, I, two 4-hydroxycoumarin moieties are linked through a methylene bridge on which one hydrogen atom has been replaced with a phenyl ring bearing p-nitro group (Fig. 1). The 4-hydroxycoumarin moieties are stabilized by intramolecular hydrogen bonding by forming S¹₁(7) ring motifs (Etter et al. 1990) and (Bernstein et al. 1995) between hydroxyl and carbonyl oxygen atoms. The crystal structure of I is stabilized by C–H···O and π–π interactions (Fig. 2). The range of H···O distances (Table 1) found in I agrees with those found for C–H···O hydrogen bonds (Desiraju & Steiner, 1999). The supramolecular chains were extended by π–π-interactions, where the distance between the two centroids namely (C1/O2/C2/C7-C9) and (C20-C25) of the two corresponding coplanar rings is 3.513 (12)Å.

Related literature top

For the synthesis of benzylidene-bis-(4-hydroxycoumarin) derivatives, see: Mehrabi & Abusaidi (2010); Završnik et al. (2011). For hydrogen bonds, see: Desiraju & Steiner (1999). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For the biological activity of substituted benzylidene-bis-(4-hydroxycoumarin) derivatives, see: Borges et al. (2005); Nolan et al. (2009); Prakash et al. (2008); Zhao et al. (1997).

Experimental top

The 4-hydroxycoumarin (2 m.mol, 0.324 g) and 4-nitrobenzaldehyde (1 mmol, 0.151 g) were refluxed in ethanol (5 ml) at 333 K for 12 h. After completion of the reaction as monitored by TLC, the reaction mixture was cooled to room temperature. The obtained precipitate was collected by suction filtration and dried. The pure product was obtained by recrystallization from dichloromethane in 92% yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Crystal packing diagram of the title compound.

3,3'-[(4-Nitrophenyl)methylene]bis(4-hydroxy-2H-chromen-2-one) top

Crystal data top

C₂₅H₁₅NO₈	F(000) = 944
M_r = 457.38	D_x = 1.471 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6438 reflections
a = 14.0061 (6) Å	θ = 2.1–24.2°
b = 14.1511 (6) Å	µ = 0.11 mm⁻¹
c = 10.4179 (4) Å	T = 295 K
V = 2064.85 (15) Å³	Block, orange
Z = 4	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3316 independent reflections
Radiation source: fine-focus sealed tube	2913 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 24.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→16
T_min = 0.902, T_max = 0.973	k = −16→16
15733 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0543P)² + 0.1473P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3316 reflections	Δρ_max = 0.22 e Å⁻³
310 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (11)

Crystal data top

C₂₅H₁₅NO₈	V = 2064.85 (15) Å³
M_r = 457.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.0061 (6) Å	µ = 0.11 mm⁻¹
b = 14.1511 (6) Å	T = 295 K
c = 10.4179 (4) Å	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3316 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2913 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.973	R_int = 0.030
15733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
3316 reflections	Δρ_min = −0.14 e Å⁻³
310 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.65097 (16)	0.52018 (16)	0.9180 (2)	0.0425 (5)
C2	0.67257 (16)	0.67214 (16)	0.8278 (2)	0.0465 (5)
C3	0.73555 (19)	0.7470 (2)	0.8087 (3)	0.0672 (7)
H3	0.7965	0.7461	0.8442	0.081*
C4	0.7053 (2)	0.8221 (2)	0.7359 (4)	0.0817 (9)
H4	0.7464	0.8724	0.7210	0.098*
C5	0.6141 (2)	0.82367 (19)	0.6844 (3)	0.0757 (9)
H5	0.5947	0.8751	0.6353	0.091*
C6	0.55268 (19)	0.75111 (17)	0.7049 (3)	0.0585 (6)
H6	0.4915	0.7531	0.6704	0.070*
C7	0.58132 (16)	0.67400 (16)	0.7773 (2)	0.0455 (5)
C8	0.52015 (15)	0.59312 (15)	0.80351 (19)	0.0412 (5)
C9	0.55171 (14)	0.52169 (14)	0.87827 (19)	0.0374 (5)
C10	0.49380 (14)	0.43608 (14)	0.9198 (2)	0.0377 (5)
H10	0.5301	0.4097	0.9918	0.045*
C11	0.49566 (14)	0.35862 (15)	0.81912 (19)	0.0403 (5)
C12	0.42673 (16)	0.36412 (15)	0.7157 (2)	0.0422 (5)
C13	0.49157 (18)	0.22343 (14)	0.6267 (2)	0.0492 (6)
C14	0.4862 (2)	0.15815 (18)	0.5260 (3)	0.0643 (7)
H14	0.4379	0.1614	0.4650	0.077*
C15	0.5557 (2)	0.08853 (19)	0.5208 (3)	0.0742 (9)
H15	0.5537	0.0436	0.4556	0.089*
C16	0.6277 (2)	0.08488 (19)	0.6106 (3)	0.0698 (8)
H16	0.6742	0.0382	0.6047	0.084*
C17	0.6315 (2)	0.14788 (16)	0.7066 (3)	0.0623 (7)
H17	0.6806	0.1441	0.7665	0.075*
C18	0.56350 (17)	0.21869 (15)	0.7178 (2)	0.0486 (6)
C19	0.56297 (16)	0.29003 (15)	0.8164 (2)	0.0484 (6)
C20	0.39601 (14)	0.45796 (15)	0.9770 (2)	0.0389 (5)
C21	0.37848 (15)	0.54447 (15)	1.0351 (2)	0.0453 (5)
H21	0.4233	0.5926	1.0277	0.054*
C22	0.29604 (17)	0.56044 (17)	1.1036 (2)	0.0516 (6)
H22	0.2853	0.6184	1.1431	0.062*
C23	0.22999 (15)	0.48919 (18)	1.1123 (2)	0.0503 (6)
C24	0.24222 (17)	0.40444 (18)	1.0508 (2)	0.0534 (6)
H24	0.1951	0.3582	1.0537	0.064*
C25	0.32609 (17)	0.38952 (15)	0.9845 (2)	0.0472 (5)
H25	0.3358	0.3318	0.9438	0.057*
N1	0.14454 (16)	0.5031 (2)	1.1934 (2)	0.0652 (6)
O1	0.69024 (11)	0.45293 (11)	0.96905 (17)	0.0531 (4)
O2	0.70638 (10)	0.59589 (11)	0.89430 (15)	0.0509 (4)
O3	0.43458 (11)	0.59699 (11)	0.74979 (15)	0.0502 (4)
H3A	0.4116	0.5438	0.7469	0.075*
O4	0.42395 (12)	0.29414 (11)	0.62710 (16)	0.0528 (4)
O5	0.37047 (12)	0.42867 (11)	0.70029 (16)	0.0515 (4)
O6	0.63447 (12)	0.28370 (12)	0.90099 (19)	0.0663 (5)
H6A	0.6486	0.3367	0.9266	0.099*
O7	0.08403 (15)	0.44080 (18)	1.1938 (3)	0.0931 (7)
O8	0.13895 (14)	0.57467 (17)	1.2562 (2)	0.0814 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0420 (12)	0.0473 (13)	0.0382 (11)	0.0001 (11)	0.0025 (9)	−0.0094 (10)
C2	0.0413 (12)	0.0472 (13)	0.0511 (13)	−0.0003 (11)	0.0030 (11)	−0.0054 (11)
C3	0.0438 (14)	0.0689 (17)	0.089 (2)	−0.0088 (13)	0.0035 (14)	−0.0068 (16)
C4	0.0630 (19)	0.0618 (17)	0.120 (3)	−0.0202 (14)	0.0069 (18)	0.0188 (19)
C5	0.0685 (19)	0.0583 (16)	0.100 (2)	−0.0043 (14)	0.0060 (17)	0.0207 (16)
C6	0.0534 (15)	0.0545 (14)	0.0677 (16)	0.0010 (12)	0.0029 (12)	0.0087 (13)
C7	0.0428 (12)	0.0449 (12)	0.0488 (12)	−0.0003 (10)	0.0089 (10)	−0.0043 (10)
C8	0.0337 (11)	0.0490 (13)	0.0409 (12)	0.0026 (10)	0.0026 (9)	−0.0021 (10)
C9	0.0342 (11)	0.0427 (11)	0.0354 (11)	0.0005 (9)	0.0016 (9)	−0.0049 (9)
C10	0.0369 (12)	0.0417 (11)	0.0345 (10)	0.0026 (9)	−0.0070 (9)	0.0004 (9)
C11	0.0389 (11)	0.0412 (12)	0.0409 (12)	−0.0014 (9)	0.0022 (10)	0.0040 (9)
C12	0.0509 (14)	0.0389 (11)	0.0368 (11)	−0.0038 (11)	0.0033 (10)	0.0010 (10)
C13	0.0604 (14)	0.0345 (11)	0.0526 (13)	−0.0015 (10)	0.0142 (12)	0.0055 (10)
C14	0.0851 (18)	0.0583 (15)	0.0494 (14)	−0.0100 (15)	0.0073 (14)	−0.0014 (13)
C15	0.112 (3)	0.0490 (15)	0.0616 (18)	−0.0094 (16)	0.0349 (18)	−0.0098 (13)
C16	0.0773 (19)	0.0537 (15)	0.079 (2)	0.0051 (14)	0.0275 (18)	0.0036 (15)
C17	0.0576 (15)	0.0484 (14)	0.0809 (18)	0.0018 (12)	0.0105 (13)	0.0003 (15)
C18	0.0493 (13)	0.0425 (12)	0.0541 (13)	−0.0059 (11)	0.0042 (11)	0.0039 (11)
C19	0.0480 (13)	0.0442 (12)	0.0531 (14)	−0.0025 (11)	−0.0030 (11)	0.0054 (11)
C20	0.0373 (11)	0.0486 (12)	0.0307 (10)	−0.0013 (10)	−0.0040 (9)	0.0031 (9)
C21	0.0401 (12)	0.0518 (13)	0.0441 (12)	−0.0054 (10)	0.0010 (10)	−0.0027 (11)
C22	0.0475 (13)	0.0621 (14)	0.0452 (13)	0.0028 (11)	0.0019 (11)	−0.0027 (12)
C23	0.0352 (12)	0.0741 (16)	0.0417 (11)	0.0025 (11)	0.0000 (10)	0.0101 (13)
C24	0.0461 (13)	0.0652 (16)	0.0488 (13)	−0.0126 (12)	0.0014 (11)	0.0093 (12)
C25	0.0521 (14)	0.0474 (12)	0.0421 (12)	−0.0071 (11)	0.0002 (11)	0.0001 (10)
N1	0.0462 (13)	0.0952 (18)	0.0543 (13)	0.0153 (13)	0.0055 (11)	0.0188 (14)
O1	0.0451 (9)	0.0569 (9)	0.0572 (9)	0.0081 (8)	−0.0130 (8)	−0.0037 (8)
O2	0.0381 (8)	0.0581 (9)	0.0565 (9)	−0.0053 (8)	−0.0031 (7)	−0.0013 (8)
O3	0.0418 (9)	0.0545 (9)	0.0544 (10)	0.0002 (7)	−0.0068 (7)	0.0087 (8)
O4	0.0626 (10)	0.0494 (9)	0.0464 (9)	0.0000 (8)	−0.0093 (8)	−0.0036 (8)
O5	0.0520 (10)	0.0515 (9)	0.0510 (9)	0.0035 (8)	−0.0109 (7)	0.0003 (8)
O6	0.0612 (11)	0.0539 (10)	0.0837 (13)	0.0115 (9)	−0.0241 (10)	−0.0028 (10)
O7	0.0484 (12)	0.1247 (18)	0.1063 (17)	−0.0157 (12)	0.0204 (12)	0.0188 (15)
O8	0.0626 (12)	0.1100 (17)	0.0715 (14)	0.0265 (12)	0.0137 (10)	−0.0006 (13)

Geometric parameters (Å, º) top

C1—O1	1.221 (3)	C13—C14	1.400 (3)
C1—O2	1.346 (3)	C14—C15	1.386 (4)
C1—C9	1.451 (3)	C14—H14	0.9300
C2—O2	1.367 (3)	C15—C16	1.376 (4)
C2—C7	1.382 (3)	C15—H15	0.9300
C2—C3	1.393 (3)	C16—C17	1.341 (4)
C3—C4	1.373 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.388 (3)
C4—C5	1.385 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.440 (3)
C5—C6	1.356 (4)	C19—O6	1.337 (3)
C5—H5	0.9300	C20—C25	1.379 (3)
C6—C7	1.386 (3)	C20—C21	1.388 (3)
C6—H6	0.9300	C21—C22	1.376 (3)
C7—C8	1.456 (3)	C21—H21	0.9300
C8—O3	1.324 (3)	C22—C23	1.371 (3)
C8—C9	1.350 (3)	C22—H22	0.9300
C9—C10	1.521 (3)	C23—C24	1.371 (4)
C10—C11	1.517 (3)	C23—N1	1.478 (3)
C10—C20	1.525 (3)	C24—C25	1.379 (3)
C10—H10	0.9800	C24—H24	0.9300
C11—C19	1.353 (3)	C25—H25	0.9300
C11—C12	1.449 (3)	N1—O8	1.209 (3)
C12—O5	1.217 (2)	N1—O7	1.223 (3)
C12—O4	1.355 (3)	O3—H3A	0.8200
C13—O4	1.378 (3)	O6—H6A	0.8200
C13—C18	1.386 (3)

O1—C1—O2	116.14 (19)	C15—C14—H14	121.3
O1—C1—C9	124.6 (2)	C13—C14—H14	121.3
O2—C1—C9	119.3 (2)	C16—C15—C14	120.9 (3)
O2—C2—C7	121.88 (19)	C16—C15—H15	119.5
O2—C2—C3	117.0 (2)	C14—C15—H15	119.5
C7—C2—C3	121.1 (2)	C17—C16—C15	120.8 (3)
C4—C3—C2	118.2 (2)	C17—C16—H16	119.6
C4—C3—H3	120.9	C15—C16—H16	119.6
C2—C3—H3	120.9	C16—C17—C18	121.0 (3)
C3—C4—C5	120.8 (3)	C16—C17—H17	119.5
C3—C4—H4	119.6	C18—C17—H17	119.5
C5—C4—H4	119.6	C13—C18—C17	118.4 (2)
C6—C5—C4	120.8 (3)	C13—C18—C19	116.8 (2)
C6—C5—H5	119.6	C17—C18—C19	124.8 (2)
C4—C5—H5	119.6	O6—C19—C11	123.8 (2)
C5—C6—C7	119.9 (3)	O6—C19—C18	114.8 (2)
C5—C6—H6	120.1	C11—C19—C18	121.4 (2)
C7—C6—H6	120.1	C25—C20—C21	117.97 (19)
C2—C7—C6	119.3 (2)	C25—C20—C10	121.14 (19)
C2—C7—C8	117.3 (2)	C21—C20—C10	120.55 (18)
C6—C7—C8	123.4 (2)	C22—C21—C20	121.3 (2)
O3—C8—C9	124.8 (2)	C22—C21—H21	119.3
O3—C8—C7	114.90 (19)	C20—C21—H21	119.3
C9—C8—C7	120.27 (19)	C23—C22—C21	118.7 (2)
C8—C9—C1	119.29 (19)	C23—C22—H22	120.7
C8—C9—C10	125.86 (18)	C21—C22—H22	120.7
C1—C9—C10	114.72 (18)	C24—C23—C22	121.9 (2)
C11—C10—C9	111.69 (17)	C24—C23—N1	119.0 (2)
C11—C10—C20	115.59 (16)	C22—C23—N1	119.1 (2)
C9—C10—C20	115.37 (17)	C23—C24—C25	118.3 (2)
C11—C10—H10	104.2	C23—C24—H24	120.8
C9—C10—H10	104.2	C25—C24—H24	120.8
C20—C10—H10	104.2	C24—C25—C20	121.7 (2)
C19—C11—C12	119.1 (2)	C24—C25—H25	119.1
C19—C11—C10	123.00 (18)	C20—C25—H25	119.1
C12—C11—C10	117.63 (17)	O8—N1—O7	123.9 (2)
O5—C12—O4	116.10 (19)	O8—N1—C23	118.2 (2)
O5—C12—C11	124.8 (2)	O7—N1—C23	117.9 (3)
O4—C12—C11	119.12 (19)	C1—O2—C2	121.44 (17)
O4—C13—C18	122.2 (2)	C8—O3—H3A	109.5
O4—C13—C14	116.4 (2)	C12—O4—C13	120.87 (19)
C18—C13—C14	121.3 (2)	C19—O6—H6A	109.5
C15—C14—C13	117.5 (3)

O2—C2—C3—C4	176.3 (2)	O4—C13—C18—C17	−176.8 (2)
C7—C2—C3—C4	−1.3 (4)	C14—C13—C18—C17	0.7 (3)
C2—C3—C4—C5	0.8 (5)	O4—C13—C18—C19	1.8 (3)
C3—C4—C5—C6	0.0 (5)	C14—C13—C18—C19	179.3 (2)
C4—C5—C6—C7	−0.4 (5)	C16—C17—C18—C13	−0.5 (4)
O2—C2—C7—C6	−176.6 (2)	C16—C17—C18—C19	−179.0 (2)
C3—C2—C7—C6	1.0 (4)	C12—C11—C19—O6	174.1 (2)
O2—C2—C7—C8	3.1 (3)	C10—C11—C19—O6	−0.3 (3)
C3—C2—C7—C8	−179.3 (2)	C12—C11—C19—C18	−4.3 (3)
C5—C6—C7—C2	−0.1 (4)	C10—C11—C19—C18	−178.79 (19)
C5—C6—C7—C8	−179.8 (2)	C13—C18—C19—O6	−179.0 (2)
C2—C7—C8—O3	−177.99 (19)	C17—C18—C19—O6	−0.5 (3)
C6—C7—C8—O3	1.7 (3)	C13—C18—C19—C11	−0.4 (3)
C2—C7—C8—C9	2.4 (3)	C17—C18—C19—C11	178.1 (2)
C6—C7—C8—C9	−177.9 (2)	C11—C10—C20—C25	28.4 (3)
O3—C8—C9—C1	172.24 (19)	C9—C10—C20—C25	161.27 (19)
C7—C8—C9—C1	−8.2 (3)	C11—C10—C20—C21	−158.45 (19)
O3—C8—C9—C10	−3.4 (3)	C9—C10—C20—C21	−25.6 (3)
C7—C8—C9—C10	176.20 (19)	C25—C20—C21—C22	3.1 (3)
O1—C1—C9—C8	−168.8 (2)	C10—C20—C21—C22	−170.3 (2)
O2—C1—C9—C8	8.8 (3)	C20—C21—C22—C23	−0.8 (3)
O1—C1—C9—C10	7.3 (3)	C21—C22—C23—C24	−2.7 (3)
O2—C1—C9—C10	−175.05 (17)	C21—C22—C23—N1	175.6 (2)
C8—C9—C10—C11	84.8 (2)	C22—C23—C24—C25	3.7 (3)
C1—C9—C10—C11	−91.0 (2)	N1—C23—C24—C25	−174.5 (2)
C8—C9—C10—C20	−49.9 (3)	C23—C24—C25—C20	−1.3 (3)
C1—C9—C10—C20	134.28 (18)	C21—C20—C25—C24	−2.0 (3)
C9—C10—C11—C19	89.4 (2)	C10—C20—C25—C24	171.3 (2)
C20—C10—C11—C19	−136.0 (2)	C24—C23—N1—O8	173.4 (2)
C9—C10—C11—C12	−85.1 (2)	C22—C23—N1—O8	−4.9 (3)
C20—C10—C11—C12	49.5 (3)	C24—C23—N1—O7	−5.9 (3)
C19—C11—C12—O5	−171.1 (2)	C22—C23—N1—O7	175.9 (2)
C10—C11—C12—O5	3.7 (3)	O1—C1—O2—C2	174.34 (19)
C19—C11—C12—O4	7.8 (3)	C9—C1—O2—C2	−3.5 (3)
C10—C11—C12—O4	−177.41 (17)	C7—C2—O2—C1	−2.5 (3)
O4—C13—C14—C15	177.5 (2)	C3—C2—O2—C1	179.8 (2)
C18—C13—C14—C15	−0.1 (4)	O5—C12—O4—C13	172.42 (19)
C13—C14—C15—C16	−0.8 (4)	C11—C12—O4—C13	−6.6 (3)
C14—C15—C16—C17	1.0 (4)	C18—C13—O4—C12	1.8 (3)
C15—C16—C17—C18	−0.3 (4)	C14—C13—O4—C12	−175.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5	0.82	1.79	2.597 (2)	166
O6—H6A···O1	0.82	1.80	2.617 (2)	173
C10—H10···O1	0.98	2.34	2.809 (3)	109
C10—H10···O6	0.98	2.49	2.928 (3)	107

Experimental details

Crystal data
Chemical formula	C₂₅H₁₅NO₈
M_r	457.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	14.0061 (6), 14.1511 (6), 10.4179 (4)
V (Å³)	2064.85 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.902, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	15733, 3316, 2913
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.579

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.089, 1.04
No. of reflections	3316
No. of parameters	310
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5	0.82	1.79	2.597 (2)	166
O6—H6A···O1	0.82	1.80	2.617 (2)	173
C10—H10···O1	0.98	2.34	2.809 (3)	109
C10—H10···O6	0.98	2.49	2.928 (3)	107

Acknowledgements

The authors thank the Managing Trustee and the Founder Trustee of the Sankar Foundation for their financial support and encouragement. We also acknowledge, the Head, SAIF, IIT-Chennai, for the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals 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
Borges, F., Roleira, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887–916. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. A. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mehrabi, H. & Abusaidi, H. (2010). J. Iran. Chem. Soc. 4, 890–894. CrossRef Google Scholar
Nolan, A. K., Doncaster, R. J., Dunstan, S. M., Scot, A. K., Frenkel, D., Siegel, D., Ross, D., Barnes, J., Levy, C. & Leys, D. (2009). J. Med. Chem. 57, 7142–7156. Web of Science CrossRef Google Scholar
Prakash, O., Kumar, R. & Prakash, V. (2008). Eur. J. Med. Chem. 43, 435–440. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Završnik, D., Muratović, S., Damjan Makuc, D., Plavec, J., Cetina, M., Nagl, A., Clercq, E. D., Balzarini, J. & Mintas, M. (2011). Molecules, 16, 6023–6040. Web of Science PubMed Google Scholar
Zhao, H., Neamati, N., Hong, H., Mazumder, A., Wang, S., Sunder, S., Milne George, W. A., Pommier, Y. & Burke, T. R. Jr (1997). J. Med. Chem. 40, 242–249. CrossRef CAS PubMed Web of Science Google Scholar