rac-7-Methyl-3-[(7-methyl-4-oxo-chro-man-3-yl)meth-yl]-4H-chromen-4-one.

In the racemic title compound, C21H18O4, the chromone ring is essentially planar [maximum deviation from the least-squares plane = 0.026 (3) Å], with a dihedral angle of 78.18 (12)° between the benzene rings of the chromanone and chromenone moieties. In the crystal, there are weak π-π stacking inter-actions [minimum ring centroid separation = 3.9286 (17) Å].

Related literature

For backgound to bis-chromanones, see: Dean & Murray (1975 ▶); Santhosh & Balasubramanian (1991 ▶); Panja et al. (2009 ▶). For related structures, see: Ambartsumyan et al. (2012 ▶); Nyburg et al. (1986 ▶); Li et al. (2010 ▶).

Experimental

Crystal data

C21H18O4

M = 334.35

Monoclinic,

a = 10.664 (2) Å

b = 6.6428 (13) Å

c = 23.754 (5) Å

β = 91.11 (3)°

V = 1682.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.44 × 0.22 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.961, T max = 0.980

11780 measured reflections

4032 independent reflections

1982 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.180

S = 1.02

4032 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009422/zs2250sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009422/zs2250Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009422/zs2250Isup3.cml

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

Enhanced figure: interactive version of Fig. 1

C21H18O4	F(000) = 704
Mr = 334.35	Dx = 1.320 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2970 reflections
a = 10.664 (2) Å	θ = 2.5–28.2°
b = 6.6428 (13) Å	µ = 0.09 mm−1
c = 23.754 (5) Å	T = 293 K
β = 91.11 (3)°	Crystal, yellow
V = 1682.4 (6) Å3	0.44 × 0.22 × 0.22 mm
Z = 4

Bruker SMART CCD diffractometer	4032 independent reflections
Radiation source: fine-focus sealed tube	1982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 28.3°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→12
Tmin = 0.961, Tmax = 0.980	k = −8→8
11780 measured reflections	l = −29→31

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0748P)2 + 0.4282P] where P = (Fo2 + 2Fc2)/3
4032 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
O2	−0.12544 (16)	−0.0887 (3)	0.10824 (8)	0.0673 (5)
O1	0.34094 (18)	0.1176 (2)	−0.01163 (8)	0.0682 (5)
C1	0.0420 (2)	0.1514 (3)	0.10862 (11)	0.0573 (7)
C2	0.3259 (2)	0.4731 (3)	−0.03163 (10)	0.0472 (6)
O4	0.18080 (18)	0.6629 (2)	0.01958 (8)	0.0729 (6)
C3	0.0456 (2)	−0.1335 (3)	0.17464 (9)	0.0471 (6)
C4	0.2280 (2)	0.4997 (3)	0.00924 (10)	0.0537 (6)
C5	−0.1317 (2)	−0.3631 (3)	0.16993 (11)	0.0566 (7)
H5	−0.2075	−0.4003	0.1529	0.068*
C6	−0.0679 (2)	−0.1937 (3)	0.15148 (10)	0.0493 (6)
C7	0.3769 (2)	0.2828 (3)	−0.04092 (10)	0.0533 (6)
C8	0.0330 (3)	−0.4157 (4)	0.23729 (12)	0.0684 (8)
H8	0.0676	−0.4909	0.2667	0.082*
O3	0.2109 (2)	0.1038 (3)	0.17275 (9)	0.0836 (6)
C9	0.1091 (2)	0.0457 (4)	0.15384 (10)	0.0550 (6)
C10	0.0960 (2)	−0.2503 (4)	0.21857 (10)	0.0604 (7)
H10	0.1726	−0.2152	0.2351	0.072*
C11	0.4571 (3)	0.6020 (4)	−0.10497 (12)	0.0634 (7)
H11	0.4826	0.7100	−0.1269	0.076*
C12	0.0952 (3)	0.3414 (3)	0.08411 (11)	0.0606 (7)
H12A	0.0263	0.4252	0.0708	0.073*
H12B	0.1391	0.4145	0.1139	0.073*
C13	0.3700 (2)	0.6324 (3)	−0.06455 (11)	0.0581 (7)
H13	0.3392	0.7615	−0.0587	0.070*
C14	0.5085 (2)	0.4123 (4)	−0.11405 (11)	0.0631 (7)
C15	−0.0676 (3)	0.0812 (4)	0.09029 (12)	0.0684 (8)
H15	−0.1090	0.1553	0.0624	0.082*
C16	−0.0817 (3)	−0.4749 (4)	0.21350 (11)	0.0605 (7)
C17	0.4669 (3)	0.2547 (4)	−0.08142 (12)	0.0652 (7)
H17	0.5001	0.1268	−0.0868	0.078*
C18	0.6082 (3)	0.3821 (5)	−0.15727 (14)	0.0897 (10)
H18A	0.5698	0.3752	−0.1941	0.135*
H18B	0.6525	0.2591	−0.1495	0.135*
H18C	0.6660	0.4930	−0.1558	0.135*
C19	0.2677 (4)	0.1520 (4)	0.03518 (17)	0.0991 (12)
H19	0.2205	0.0297	0.0418	0.119*
H1	0.3247	0.1687	0.0672	0.62 (11)*
C20	0.1836 (3)	0.3097 (4)	0.03647 (15)	0.0846 (10)
H20	0.1236	0.2640	0.0074	0.102*
C21	−0.1514 (3)	−0.6556 (5)	0.23528 (16)	0.0968 (11)
H21A	−0.1730	−0.6333	0.2738	0.145*
H21B	−0.0990	−0.7727	0.2328	0.145*
H21C	−0.2264	−0.6758	0.2130	0.145*

	U11	U22	U33	U12	U13	U23
O2	0.0557 (11)	0.0714 (11)	0.0742 (12)	−0.0134 (9)	−0.0163 (10)	0.0252 (10)
O1	0.0876 (14)	0.0363 (8)	0.0811 (13)	0.0084 (8)	0.0148 (11)	0.0026 (8)
C1	0.0505 (16)	0.0538 (13)	0.0673 (17)	−0.0022 (12)	−0.0023 (13)	0.0107 (12)
C2	0.0488 (14)	0.0389 (11)	0.0536 (14)	−0.0033 (10)	−0.0045 (12)	−0.0018 (10)
O4	0.0857 (14)	0.0385 (9)	0.0954 (14)	0.0122 (9)	0.0249 (11)	0.0127 (9)
C3	0.0463 (14)	0.0516 (12)	0.0434 (13)	0.0032 (10)	0.0013 (11)	0.0001 (10)
C4	0.0595 (16)	0.0373 (11)	0.0643 (16)	0.0021 (11)	0.0007 (13)	0.0061 (11)
C5	0.0528 (15)	0.0562 (14)	0.0610 (16)	−0.0059 (12)	0.0092 (13)	0.0018 (12)
C6	0.0500 (15)	0.0513 (12)	0.0466 (13)	0.0053 (11)	0.0026 (12)	0.0044 (11)
C7	0.0597 (16)	0.0413 (12)	0.0587 (15)	−0.0011 (11)	−0.0027 (13)	−0.0043 (11)
C8	0.0706 (19)	0.0727 (17)	0.0621 (17)	0.0132 (15)	0.0064 (15)	0.0242 (14)
O3	0.0722 (14)	0.0901 (14)	0.0873 (14)	−0.0270 (11)	−0.0280 (12)	0.0159 (11)
C9	0.0530 (16)	0.0582 (14)	0.0536 (15)	−0.0038 (12)	−0.0053 (13)	0.0008 (12)
C10	0.0554 (16)	0.0719 (16)	0.0537 (15)	0.0039 (13)	−0.0019 (13)	0.0093 (13)
C11	0.0646 (18)	0.0589 (15)	0.0666 (17)	−0.0138 (13)	0.0011 (15)	0.0009 (13)
C12	0.0640 (17)	0.0497 (13)	0.0683 (17)	−0.0035 (12)	0.0051 (14)	0.0063 (12)
C13	0.0581 (16)	0.0439 (12)	0.0723 (17)	−0.0029 (11)	0.0012 (14)	0.0009 (12)
C14	0.0568 (17)	0.0703 (17)	0.0622 (17)	−0.0111 (13)	−0.0008 (14)	−0.0147 (14)
C15	0.0621 (18)	0.0651 (16)	0.0775 (19)	−0.0048 (14)	−0.0101 (15)	0.0263 (14)
C16	0.0658 (18)	0.0550 (14)	0.0615 (16)	0.0045 (13)	0.0187 (14)	0.0104 (12)
C17	0.0693 (18)	0.0516 (14)	0.0746 (18)	0.0030 (13)	0.0015 (15)	−0.0140 (13)
C18	0.084 (2)	0.099 (2)	0.087 (2)	−0.0138 (18)	0.0216 (19)	−0.0229 (18)
C19	0.133 (3)	0.0430 (14)	0.124 (3)	0.0074 (17)	0.060 (3)	0.0136 (16)
C20	0.105 (2)	0.0431 (14)	0.107 (2)	0.0176 (14)	0.041 (2)	0.0204 (14)
C21	0.102 (3)	0.078 (2)	0.111 (3)	−0.0075 (18)	0.027 (2)	0.0322 (19)

O2—C15	1.359 (3)	C10—H10	0.9300
O2—C6	1.376 (3)	C11—C13	1.364 (4)
O1—C7	1.359 (3)	C11—C14	1.393 (3)
O1—C19	1.390 (3)	C11—H11	0.9300
C1—C15	1.324 (3)	C12—C20	1.501 (4)
C1—C9	1.459 (4)	C12—H12A	0.9700
C1—C12	1.505 (3)	C12—H12B	0.9700
C2—C7	1.395 (3)	C13—H13	0.9300
C2—C13	1.402 (3)	C14—C17	1.381 (4)
C2—C4	1.451 (3)	C14—C18	1.505 (4)
O4—C4	1.222 (3)	C15—H15	0.9300
C3—C6	1.379 (3)	C16—C21	1.508 (4)
C3—C10	1.399 (3)	C17—H17	0.9300
C3—C9	1.460 (3)	C18—H18A	0.9600
C4—C20	1.499 (3)	C18—H18B	0.9600
C5—C16	1.373 (4)	C18—H18C	0.9600
C5—C6	1.390 (3)	C19—C20	1.380 (4)
C5—H5	0.9300	C19—H19	0.9700
C7—C17	1.385 (3)	C19—H1	0.9700
C8—C10	1.367 (4)	C20—H20	0.9800
C8—C16	1.394 (4)	C21—H21A	0.9600
C8—H8	0.9300	C21—H21B	0.9600
O3—C9	1.229 (3)	C21—H21C	0.9600
C15—O2—C6	117.2 (2)	H12A—C12—H12B	107.5
C7—O1—C19	116.44 (18)	C11—C13—C2	121.4 (2)
C15—C1—C9	119.3 (2)	C11—C13—H13	119.3
C15—C1—C12	120.3 (2)	C2—C13—H13	119.3
C9—C1—C12	120.3 (2)	C17—C14—C11	117.9 (2)
C7—C2—C13	117.4 (2)	C17—C14—C18	121.4 (3)
C7—C2—C4	120.3 (2)	C11—C14—C18	120.8 (3)
C13—C2—C4	122.3 (2)	C1—C15—O2	126.3 (2)
C6—C3—C10	117.3 (2)	C1—C15—H15	116.8
C6—C3—C9	120.7 (2)	O2—C15—H15	116.8
C10—C3—C9	122.1 (2)	C5—C16—C8	118.5 (2)
O4—C4—C2	123.2 (2)	C5—C16—C21	120.2 (3)
O4—C4—C20	121.7 (2)	C8—C16—C21	121.3 (3)
C2—C4—C20	115.07 (19)	C14—C17—C7	121.5 (2)
C16—C5—C6	119.4 (3)	C14—C17—H17	119.3
C16—C5—H5	120.3	C7—C17—H17	119.3
C6—C5—H5	120.3	C14—C18—H18A	109.5
O2—C6—C3	121.8 (2)	C14—C18—H18B	109.5
O2—C6—C5	115.6 (2)	H18A—C18—H18B	109.5
C3—C6—C5	122.7 (2)	C14—C18—H18C	109.5
O1—C7—C17	116.9 (2)	H18A—C18—H18C	109.5
O1—C7—C2	122.4 (2)	H18B—C18—H18C	109.5
C17—C7—C2	120.6 (2)	C20—C19—O1	121.2 (3)
C10—C8—C16	121.9 (2)	C20—C19—H19	107.0
C10—C8—H8	119.1	O1—C19—H19	107.0
C16—C8—H8	119.1	C20—C19—H1	107.0
O3—C9—C1	122.3 (2)	O1—C19—H1	107.0
O3—C9—C3	123.0 (2)	H19—C19—H1	106.8
C1—C9—C3	114.7 (2)	C19—C20—C4	114.7 (2)
C8—C10—C3	120.3 (3)	C19—C20—C12	122.7 (3)
C8—C10—H10	119.8	C4—C20—C12	114.6 (2)
C3—C10—H10	119.8	C19—C20—H20	99.5
C13—C11—C14	121.2 (2)	C4—C20—H20	99.5
C13—C11—H11	119.4	C12—C20—H20	99.5
C14—C11—H11	119.4	C16—C21—H21A	109.5
C20—C12—C1	114.9 (2)	C16—C21—H21B	109.5
C20—C12—H12A	108.5	H21A—C21—H21B	109.5
C1—C12—H12A	108.5	C16—C21—H21C	109.5
C20—C12—H12B	108.5	H21A—C21—H21C	109.5
C1—C12—H12B	108.5	H21B—C21—H21C	109.5
C19—O1—C7—C2	−11.4 (4)	C6—C3—C9—O3	−179.2 (2)
C19—O1—C7—C17	169.2 (3)	C6—C3—C9—C1	0.9 (3)
C7—O1—C19—C20	33.0 (4)	C10—C3—C9—O3	1.1 (4)
C15—O2—C6—C3	−2.0 (3)	C10—C3—C9—C1	−178.9 (2)
C15—O2—C6—C5	178.0 (2)	C6—C3—C10—C8	−0.5 (4)
C6—O2—C15—C1	3.3 (4)	C9—C3—C10—C8	179.2 (2)
C12—C1—C9—O3	−1.4 (4)	O4—C4—C20—C12	−10.6 (4)
C12—C1—C9—C3	178.6 (2)	O4—C4—C20—C19	−160.5 (3)
C15—C1—C9—O3	−179.8 (3)	C2—C4—C20—C12	172.1 (2)
C15—C1—C9—C3	0.2 (3)	C2—C4—C20—C19	22.2 (4)
C9—C1—C12—C20	87.7 (3)	C16—C5—C6—O2	−179.1 (2)
C15—C1—C12—C20	−93.9 (3)	C16—C5—C6—C3	1.0 (4)
C9—C1—C15—O2	−2.4 (4)	C6—C5—C16—C8	−0.9 (4)
C12—C1—C15—O2	179.3 (2)	C6—C5—C16—C21	178.2 (2)
C7—C2—C4—O4	179.2 (2)	O1—C7—C17—C14	179.0 (3)
C7—C2—C4—C20	−3.6 (3)	C2—C7—C17—C14	−0.4 (4)
C13—C2—C4—O4	−3.1 (4)	C16—C8—C10—C3	0.5 (4)
C13—C2—C4—C20	174.2 (2)	C10—C8—C16—C5	0.2 (4)
C4—C2—C7—O1	−2.0 (3)	C10—C8—C16—C21	−178.9 (3)
C4—C2—C7—C17	177.5 (2)	C14—C11—C13—C2	−1.9 (4)
C13—C2—C7—O1	−179.8 (2)	C13—C11—C14—C17	1.1 (4)
C13—C2—C7—C17	−0.4 (3)	C13—C11—C14—C18	−177.6 (3)
C4—C2—C13—C11	−176.3 (2)	C1—C12—C20—C4	175.3 (2)
C7—C2—C13—C11	1.5 (4)	C1—C12—C20—C19	−37.5 (4)
C9—C3—C6—O2	0.1 (3)	C11—C14—C17—C7	0.1 (4)
C9—C3—C6—C5	−180.0 (2)	C18—C14—C17—C7	178.8 (3)
C10—C3—C6—O2	179.8 (2)	O1—C19—C20—C4	−38.2 (5)
C10—C3—C6—C5	−0.2 (3)	O1—C19—C20—C12	174.7 (3)