3,3′-Benzyl­idene­bis(4-hydroxy-6-methyl­coumarin)

In the title compound, C₂₇H₂₀O₆, both benzo­pyran moieties are slightly distorted from planarity. Intramolecular O—H...O hydrogen bonds are formed between hydroxyl and carbonyl groups of the two hydroxy­coumarin moieties.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.106
• Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: MolEN (Fair,1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

3-[(4-hydroxy-6-methyl-2-oxo-2H-chromen-3-yl)phenylmethyl]-4-hydroxy-6-methyl chromen(2H)-2-one3-[(4-hydroxy-6-methyl-2-oxo-2H-chromen-3-yl)phenylmethyl]-6-methyl-2-oxo- 2H-chromen-4-olate

Crystal data

C27H20O6	F(000) = 920
Mr = 440.43	Dx = 1.420 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ybc	Cell parameters from 25 reflections
a = 10.647 (1) Å	θ = 2–25°
b = 7.595 (1) Å	µ = 0.83 mm^−1
c = 25.481 (2) Å	T = 293 K
β = 90.298 (9)°	Needle, colourless
V = 2060.4 (4) Å^3	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Enraf-Nonius-CAD-4 diffractometer	2788 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 67.9°, θmin = 3.5°
ω–2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.840, Tmax = 0.941	l = −30→27
3901 measured reflections	2 standard reflections every 60 reflections
3701 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.6209P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3701 reflections	Δρmax = 0.17 e Å^−3
303 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=3DkFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.25370 (11)	0.56601 (17)	0.18644 (5)	0.0424 (3)
O2	0.14404 (12)	0.70370 (19)	0.24604 (5)	0.0470 (3)
C2	0.14648 (16)	0.6497 (2)	0.20053 (7)	0.0381 (4)
C3	0.04507 (15)	0.6676 (2)	0.16326 (7)	0.0356 (4)
C4	0.05202 (15)	0.5770 (2)	0.11732 (7)	0.0372 (4)
O4	−0.04268 (11)	0.56059 (19)	0.08314 (5)	0.0474 (4)
C5	0.19086 (18)	0.4315 (3)	0.05076 (7)	0.0441 (5)
H5	0.1247	0.4262	0.0268	0.053*
C6	0.30806 (18)	0.3715 (3)	0.03609 (8)	0.0460 (5)
C7	0.40534 (18)	0.3804 (3)	0.07307 (8)	0.0491 (5)
H7	0.4851	0.3422	0.0636	0.059*
C8	0.38693 (17)	0.4435 (3)	0.12281 (8)	0.0463 (5)
H8	0.4526	0.4459	0.1470	0.056*
C9	0.26927 (16)	0.5032 (2)	0.13621 (7)	0.0385 (4)
C10	0.16983 (16)	0.5002 (2)	0.10094 (7)	0.0382 (4)
O11	−0.35261 (11)	0.50676 (18)	0.20802 (5)	0.0453 (3)
O12	−0.25925 (12)	0.57219 (18)	0.13440 (5)	0.0467 (3)
C12	−0.25585 (16)	0.5854 (2)	0.18219 (7)	0.0379 (4)
C13	−0.16123 (16)	0.6777 (2)	0.21156 (7)	0.0358 (4)
C14	−0.16003 (16)	0.6633 (2)	0.26488 (7)	0.0361 (4)
O14	−0.07071 (12)	0.73057 (18)	0.29610 (5)	0.0449 (3)
C15	−0.26107 (18)	0.5445 (2)	0.34626 (7)	0.0412 (4)
H15	−0.1975	0.5927	0.3669	0.049*
C16	−0.35541 (19)	0.4493 (3)	0.36992 (8)	0.0460 (5)
C17	−0.45187 (19)	0.3819 (3)	0.33812 (8)	0.0518 (5)
H17	−0.5175	0.3205	0.3536	0.062*
C18	−0.45187 (18)	0.4044 (3)	0.28474 (8)	0.0512 (5)
H18	−0.5164	0.3585	0.2642	0.061*
C19	−0.35426 (17)	0.4965 (3)	0.26200 (7)	0.0406 (4)
C20	−0.25893 (16)	0.5703 (2)	0.29181 (7)	0.0377 (4)
C21	−0.06312 (15)	0.7822 (2)	0.18151 (7)	0.0359 (4)
H21	−0.0253	0.8593	0.2081	0.043*
C22	−0.11686 (16)	0.9097 (2)	0.14047 (7)	0.0383 (4)
C23	−0.22815 (18)	0.9967 (3)	0.15104 (8)	0.0455 (5)
H23	−0.2727	0.9683	0.1812	0.055*
C24	−0.2741 (2)	1.1246 (3)	0.11782 (9)	0.0571 (6)
H24	−0.3498	1.1799	0.1254	0.069*
C25	−0.2091 (2)	1.1712 (3)	0.07345 (9)	0.0617 (6)
H25	−0.2401	1.2578	0.0510	0.074*
C26	−0.0980 (2)	1.0881 (3)	0.06277 (9)	0.0586 (6)
H26	−0.0530	1.1191	0.0330	0.070*
C27	−0.05175 (19)	0.9586 (3)	0.09583 (8)	0.0468 (5)
H27	0.0239	0.9036	0.0880	0.056*
C28	0.3312 (2)	0.3006 (3)	−0.01809 (8)	0.0628 (6)
H281	0.2584	0.2369	−0.0299	0.094*
H282	0.4024	0.2231	−0.0173	0.094*
H283	0.3474	0.3964	−0.0416	0.094*
C29	−0.3559 (2)	0.4170 (3)	0.42803 (8)	0.0618 (6)
H291	−0.2826	0.4691	0.4436	0.093*
H292	−0.3558	0.2925	0.4346	0.093*
H293	−0.4298	0.4686	0.4430	0.093*
H4	−0.1153	0.5837	0.1000	0.076 (8)*
H14	−0.0030	0.7290	0.2784	0.084 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0334 (6)	0.0517 (8)	0.0419 (7)	−0.0008 (6)	−0.0075 (5)	0.0036 (6)
O2	0.0413 (7)	0.0630 (9)	0.0366 (7)	−0.0030 (6)	−0.0067 (5)	0.0021 (6)
C2	0.0323 (9)	0.0396 (10)	0.0423 (11)	−0.0057 (8)	−0.0035 (7)	0.0055 (8)
C3	0.0323 (8)	0.0366 (9)	0.0379 (10)	−0.0029 (7)	−0.0049 (7)	0.0033 (8)
C4	0.0316 (9)	0.0380 (10)	0.0417 (10)	−0.0016 (7)	−0.0066 (7)	0.0035 (8)
O4	0.0349 (7)	0.0605 (9)	0.0468 (8)	0.0042 (6)	−0.0109 (6)	−0.0098 (7)
C5	0.0412 (10)	0.0470 (11)	0.0441 (11)	0.0028 (9)	−0.0042 (8)	0.0035 (9)
C6	0.0437 (10)	0.0464 (11)	0.0480 (11)	0.0043 (9)	0.0045 (8)	0.0065 (9)
C7	0.0384 (10)	0.0511 (12)	0.0579 (13)	0.0060 (9)	0.0039 (9)	0.0078 (10)
C8	0.0342 (9)	0.0500 (11)	0.0547 (12)	0.0008 (9)	−0.0063 (8)	0.0063 (10)
C9	0.0366 (9)	0.0396 (10)	0.0393 (10)	−0.0022 (8)	−0.0036 (7)	0.0059 (8)
C10	0.0338 (9)	0.0379 (9)	0.0430 (10)	−0.0004 (8)	−0.0023 (7)	0.0032 (8)
O11	0.0359 (7)	0.0542 (8)	0.0457 (8)	−0.0079 (6)	−0.0056 (5)	0.0025 (6)
O12	0.0443 (7)	0.0578 (9)	0.0380 (8)	−0.0064 (6)	−0.0081 (6)	−0.0026 (6)
C12	0.0333 (9)	0.0371 (10)	0.0433 (11)	0.0010 (7)	−0.0032 (8)	0.0023 (8)
C13	0.0351 (9)	0.0337 (9)	0.0387 (10)	0.0000 (7)	−0.0031 (7)	0.0010 (7)
C14	0.0347 (9)	0.0336 (9)	0.0400 (10)	0.0014 (7)	−0.0026 (7)	−0.0030 (8)
O14	0.0419 (7)	0.0554 (8)	0.0374 (7)	−0.0087 (6)	−0.0033 (6)	−0.0048 (6)
C15	0.0441 (10)	0.0381 (10)	0.0414 (10)	0.0022 (8)	0.0024 (8)	−0.0018 (8)
C16	0.0515 (11)	0.0393 (10)	0.0474 (11)	0.0042 (9)	0.0131 (9)	0.0014 (9)
C17	0.0432 (11)	0.0513 (12)	0.0610 (14)	−0.0029 (9)	0.0095 (9)	0.0085 (10)
C18	0.0383 (10)	0.0553 (13)	0.0601 (13)	−0.0070 (9)	−0.0005 (9)	0.0058 (10)
C19	0.0366 (9)	0.0425 (10)	0.0427 (11)	0.0024 (8)	−0.0004 (8)	0.0039 (8)
C20	0.0363 (9)	0.0347 (9)	0.0421 (10)	0.0038 (8)	0.0019 (7)	−0.0001 (8)
C21	0.0369 (9)	0.0362 (9)	0.0346 (9)	−0.0029 (8)	−0.0044 (7)	−0.0002 (8)
C22	0.0401 (9)	0.0342 (9)	0.0405 (10)	−0.0026 (8)	−0.0057 (8)	0.0009 (8)
C23	0.0445 (10)	0.0435 (11)	0.0485 (11)	0.0033 (9)	−0.0026 (9)	0.0015 (9)
C24	0.0574 (13)	0.0467 (12)	0.0671 (15)	0.0144 (10)	−0.0065 (11)	0.0031 (11)
C25	0.0788 (16)	0.0432 (12)	0.0630 (14)	0.0078 (11)	−0.0133 (12)	0.0124 (11)
C26	0.0722 (15)	0.0522 (13)	0.0514 (13)	−0.0027 (11)	0.0003 (11)	0.0132 (10)
C27	0.0477 (11)	0.0448 (11)	0.0480 (12)	−0.0002 (9)	0.0006 (9)	0.0068 (9)
C28	0.0606 (13)	0.0803 (17)	0.0475 (12)	0.0170 (12)	0.0053 (10)	0.0043 (12)
C29	0.0792 (16)	0.0558 (13)	0.0504 (13)	−0.0061 (12)	0.0168 (11)	0.0018 (11)

Geometric parameters (Å, º)

O1—C2	1.357 (2)	C15—C20	1.401 (3)
O1—C9	1.376 (2)	C15—H15	0.93
O2—C2	1.231 (2)	C16—C17	1.402 (3)
C2—C3	1.441 (2)	C16—C29	1.501 (3)
C3—C4	1.360 (2)	C17—C18	1.371 (3)
C3—C21	1.519 (2)	C17—H17	0.93
C4—O4	1.335 (2)	C18—C19	1.382 (3)
C4—C10	1.447 (2)	C18—H18	0.93
O4—H4	0.90	C19—C20	1.383 (3)
C5—C6	1.382 (3)	C21—C22	1.534 (2)
C5—C10	1.400 (3)	C21—H21	0.98
C5—H5	0.93	C22—C23	1.385 (3)
C6—C7	1.398 (3)	C22—C27	1.386 (3)
C6—C28	1.503 (3)	C23—C24	1.377 (3)
C7—C8	1.370 (3)	C23—H23	0.93
C7—H7	0.93	C24—C25	1.375 (3)
C8—C9	1.377 (3)	C24—H24	0.93
C8—H8	0.93	C25—C26	1.369 (3)
C9—C10	1.385 (2)	C25—H25	0.93
O11—C12	1.363 (2)	C26—C27	1.384 (3)
O11—C19	1.378 (2)	C26—H26	0.93
O12—C12	1.222 (2)	C27—H27	0.93
C12—C13	1.435 (2)	C28—H281	0.96
C13—C14	1.363 (2)	C28—H282	0.96
C13—C21	1.522 (2)	C28—H283	0.96
C14—O14	1.338 (2)	C29—H291	0.96
C14—C20	1.445 (2)	C29—H292	0.96
O14—H14	0.85	C29—H293	0.96
C15—C16	1.379 (3)
C2—O1—C9	120.92 (14)	C18—C17—H17	119.2
O2—C2—O1	115.31 (15)	C16—C17—H17	119.2
O2—C2—C3	124.78 (17)	C17—C18—C19	118.86 (19)
O1—C2—C3	119.91 (16)	C17—C18—H18	120.6
C4—C3—C2	118.41 (16)	C19—C18—H18	120.6
C4—C3—C21	126.74 (15)	O11—C19—C18	117.41 (17)
C2—C3—C21	114.78 (15)	O11—C19—C20	120.81 (16)
O4—C4—C3	124.37 (16)	C18—C19—C20	121.73 (18)
O4—C4—C10	115.29 (16)	C19—C20—C15	118.14 (17)
C3—C4—C10	120.22 (15)	C19—C20—C14	118.15 (16)
C4—O4—H4	108.48	C15—C20—C14	123.66 (17)
C6—C5—C10	121.26 (18)	C3—C21—C13	112.25 (14)
C6—C5—H5	119.4	C3—C21—C22	115.72 (14)
C10—C5—H5	119.4	C13—C21—C22	114.69 (14)
C5—C6—C7	117.95 (18)	C3—C21—H21	104.2
C5—C6—C28	121.25 (18)	C13—C21—H21	104.2
C7—C6—C28	120.79 (18)	C22—C21—H21	104.2
C8—C7—C6	122.09 (18)	C23—C22—C27	117.64 (17)
C8—C7—H7	119.0	C23—C22—C21	119.04 (16)
C6—C7—H7	119.0	C27—C22—C21	122.85 (16)
C7—C8—C9	118.65 (18)	C24—C23—C22	121.29 (19)
C7—C8—H8	120.7	C24—C23—H23	119.4
C9—C8—H8	120.7	C22—C23—H23	119.4
O1—C9—C8	117.31 (16)	C25—C24—C23	120.5 (2)
O1—C9—C10	120.90 (16)	C25—C24—H24	119.7
C8—C9—C10	121.78 (18)	C23—C24—H24	119.7
C9—C10—C5	118.25 (16)	C26—C25—C24	118.9 (2)
C9—C10—C4	117.83 (16)	C26—C25—H25	120.5
C5—C10—C4	123.83 (16)	C24—C25—H25	120.5
C12—O11—C19	121.35 (14)	C25—C26—C27	120.8 (2)
O12—C12—O11	115.26 (15)	C25—C26—H26	119.6
O12—C12—C13	125.21 (16)	C27—C26—H26	119.6
O11—C12—C13	119.51 (16)	C26—C27—C22	120.8 (2)
C14—C13—C12	118.91 (16)	C26—C27—H27	119.6
C14—C13—C21	122.72 (15)	C22—C27—H27	119.6
C12—C13—C21	118.32 (15)	C6—C28—H281	109.5
O14—C14—C13	124.39 (16)	C6—C28—H282	109.5
O14—C14—C20	114.95 (15)	H281—C28—H282	109.5
C13—C14—C20	120.66 (16)	C6—C28—H283	109.5
C14—O14—H14	106.28	H281—C28—H283	109.5
C16—C15—C20	121.44 (18)	H282—C28—H283	109.5
C16—C15—H15	119.3	C16—C29—H291	109.5
C20—C15—H15	119.3	C16—C29—H292	109.5
C15—C16—C17	118.16 (18)	H291—C29—H292	109.5
C15—C16—C29	121.6 (2)	C16—C29—H293	109.5
C17—C16—C29	120.27 (18)	H291—C29—H293	109.5
C18—C17—C16	121.63 (19)	H292—C29—H293	109.5
C9—O1—C2—O2	−178.42 (15)	C20—C15—C16—C17	−1.6 (3)
C9—O1—C2—C3	2.5 (2)	C20—C15—C16—C29	178.16 (18)
O2—C2—C3—C4	−169.30 (18)	C15—C16—C17—C18	1.9 (3)
O1—C2—C3—C4	9.7 (3)	C29—C16—C17—C18	−177.9 (2)
O2—C2—C3—C21	7.9 (3)	C16—C17—C18—C19	−0.2 (3)
O1—C2—C3—C21	−173.04 (15)	C12—O11—C19—C18	−175.84 (17)
C2—C3—C4—O4	169.47 (16)	C12—O11—C19—C20	1.8 (3)
C21—C3—C4—O4	−7.4 (3)	C17—C18—C19—O11	175.80 (18)
C2—C3—C4—C10	−14.7 (3)	C17—C18—C19—C20	−1.8 (3)
C21—C3—C4—C10	168.42 (16)	O11—C19—C20—C15	−175.44 (16)
C10—C5—C6—C7	0.4 (3)	C18—C19—C20—C15	2.1 (3)
C10—C5—C6—C28	−178.94 (19)	O11—C19—C20—C14	2.1 (3)
C5—C6—C7—C8	1.0 (3)	C18—C19—C20—C14	179.57 (17)
C28—C6—C7—C8	−179.7 (2)	C16—C15—C20—C19	−0.3 (3)
C6—C7—C8—C9	−1.4 (3)	C16—C15—C20—C14	−177.67 (17)
C2—O1—C9—C8	170.65 (16)	O14—C14—C20—C19	−179.72 (16)
C2—O1—C9—C10	−9.6 (3)	C13—C14—C20—C19	0.1 (3)
C7—C8—C9—O1	−179.94 (17)	O14—C14—C20—C15	−2.4 (3)
C7—C8—C9—C10	0.3 (3)	C13—C14—C20—C15	177.43 (17)
O1—C9—C10—C5	−178.71 (16)	C4—C3—C21—C13	88.7 (2)
C8—C9—C10—C5	1.0 (3)	C2—C3—C21—C13	−88.27 (18)
O1—C9—C10—C4	4.5 (3)	C4—C3—C21—C22	−45.6 (2)
C8—C9—C10—C4	−175.77 (17)	C2—C3—C21—C22	137.47 (16)
C6—C5—C10—C9	−1.4 (3)	C14—C13—C21—C3	93.8 (2)
C6—C5—C10—C4	175.22 (18)	C12—C13—C21—C3	−83.78 (19)
O4—C4—C10—C9	−175.93 (16)	C14—C13—C21—C22	−131.47 (18)
C3—C4—C10—C9	7.9 (3)	C12—C13—C21—C22	51.0 (2)
O4—C4—C10—C5	7.5 (3)	C3—C21—C22—C23	169.25 (16)
C3—C4—C10—C5	−168.74 (17)	C13—C21—C22—C23	36.1 (2)
C19—O11—C12—O12	173.60 (16)	C3—C21—C22—C27	−18.8 (2)
C19—O11—C12—C13	−7.5 (2)	C13—C21—C22—C27	−151.97 (17)
O12—C12—C13—C14	−171.80 (17)	C27—C22—C23—C24	1.4 (3)
O11—C12—C13—C14	9.5 (3)	C21—C22—C23—C24	173.79 (18)
O12—C12—C13—C21	5.8 (3)	C22—C23—C24—C25	−1.1 (3)
O11—C12—C13—C21	−172.89 (15)	C23—C24—C25—C26	0.1 (3)
C12—C13—C14—O14	174.07 (16)	C24—C25—C26—C27	0.4 (3)
C21—C13—C14—O14	−3.5 (3)	C25—C26—C27—C22	0.1 (3)
C12—C13—C14—C20	−5.7 (3)	C23—C22—C27—C26	−0.9 (3)
C21—C13—C14—C20	176.75 (15)	C21—C22—C27—C26	−172.98 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O12	0.90	1.77	2.658 (2)	165
O14—H14···O2	0.85	1.78	2.631 (2)	173
C21—H21···O2	0.98	2.36	2.808 (2)	107
C21—H21···O14	0.98	2.50	2.948 (2)	108