3,3'-[(4-Nitro-phen-yl)methyl-ene]bis-(4-hy-droxy-2H-chromen-2-one).

The molecular conformation of the title compound, C(25)H(15)NO(8), is stabilized by strong intramolecular O-H⋯O hydrogen bonds, resulting in the formation of S(1) (1)(7) ring motifs. In the crystal, π-π stacking inter-actions 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 = 457.38

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.04

3316 reflections

310 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.14 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054778/rk2323sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811054778/rk2323Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H15NO8	F(000) = 944
Mr = 457.38	Dx = 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

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

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(Fo2) + (0.0543P)2 + 0.1473P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3316 reflections	Δρmax = 0.22 e Å−3
310 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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