Crystal structure of 2-(11-oxo-10H,11H-indeno-[1,2-b]chromen-10-yl)-2,3-di-hydro-1H-indene-1,3-dione.

In the title mol-ecule, C25H14O4, the fused-ring system consisting of four rings is approximately planar, with a dihedral angle of 9.62 (5)° between the planes of the indene ring system and the benzene ring. The di-hydro-indene-1,3-dione unit makes a dihedral angle of 63.50 (2)° with the mean plane of the fused-ring system. A weak C-H⋯O inter-action organizes the mol-ecules into a helical chain along the b axis. In addition, there is a π-π stacking inter-action between the five-membered rings of adjacent fused-ring systems, with a centroid-centroid distance of 3.666 (1) Å.

Related literature

For synthesis and biological properties of chromene scaffolds, see: RamaGanesh et al. (2010 ▸); O’Kenedy & Thornes (1997 ▸); Zabradnik (1992 ▸). For the bioactivity of fused chromenes, see: Bargagna et al. (1992 ▸); Ermili et al. (1979 ▸).

Experimental

Crystal data

C25H14O4

M = 378.36

Monoclinic,

a = 8.7409 (2) Å

b = 14.4740 (3) Å

c = 14.2774 (3) Å

β = 101.141 (1)°

V = 1772.28 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.78 mm−1

T = 150 K

0.23 × 0.22 × 0.11 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.86, T max = 0.92

28946 measured reflections

3495 independent reflections

3189 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.06

3495 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007495/is5397sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007495/is5397Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007495/is5397Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007495/is5397fig1.tif

The mol­ecular structure of the title compound with labeling scheme and 50% probability ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S2056989015007495/is5397fig2.tif

A packing diagram of the title compound, showing a chain structure formed by C—H⋯O inter­actions (dashed lines).

CCDC reference: 1059989

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H14O4	F(000) = 784
Mr = 378.36	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.7409 (2) Å	Cell parameters from 9790 reflections
b = 14.4740 (3) Å	θ = 3.1–72.3°
c = 14.2774 (3) Å	µ = 0.78 mm−1
β = 101.141 (1)°	T = 150 K
V = 1772.28 (7) Å3	Block, orange
Z = 4	0.23 × 0.22 × 0.11 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3495 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3189 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.030
Detector resolution: 10.4167 pixels mm-1	θmax = 72.4°, θmin = 4.4°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −17→17
Tmin = 0.86, Tmax = 0.92	l = −17→17
28946 measured reflections

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) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.5107P] where P = (Fo2 + 2Fc2)/3
3495 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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. H-atoms were placed in calculated positions (C—H = 0.95 - 1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached carbon atoms.

	x	y	z	Uiso*/Ueq
O1	0.47506 (10)	0.32965 (6)	0.40020 (6)	0.0302 (2)
O2	0.16356 (11)	0.59782 (6)	0.38392 (6)	0.0352 (2)
O3	0.08695 (12)	0.33852 (7)	0.24206 (6)	0.0440 (3)
O4	0.27958 (11)	0.57260 (6)	0.06450 (6)	0.0343 (2)
C1	0.35974 (13)	0.48118 (7)	0.26329 (8)	0.0240 (2)
H1	0.4079	0.5433	0.2586	0.029*
C2	0.33109 (13)	0.47028 (8)	0.36229 (8)	0.0243 (2)
C3	0.23649 (13)	0.52859 (8)	0.41347 (8)	0.0263 (2)
C4	0.24407 (13)	0.48383 (8)	0.50974 (8)	0.0266 (2)
C5	0.17816 (15)	0.50868 (9)	0.58577 (9)	0.0320 (3)
H5	0.1152	0.5624	0.5835	0.038*
C6	0.20691 (15)	0.45208 (10)	0.66709 (9)	0.0354 (3)
H6	0.1624	0.4677	0.7207	0.043*
C7	0.29864 (15)	0.37426 (9)	0.67053 (8)	0.0352 (3)
H7	0.3168	0.3373	0.7266	0.042*
C8	0.36576 (14)	0.34857 (9)	0.59259 (8)	0.0314 (3)
H8	0.4289	0.2949	0.5947	0.038*
C9	0.33631 (13)	0.40432 (8)	0.51294 (8)	0.0260 (2)
C10	0.38543 (13)	0.39924 (8)	0.42012 (8)	0.0248 (2)
C11	0.52713 (13)	0.33794 (8)	0.31358 (8)	0.0262 (2)
C12	0.63660 (14)	0.27212 (8)	0.30077 (9)	0.0314 (3)
H12	0.6658	0.2247	0.3468	0.038*
C13	0.70268 (14)	0.27624 (9)	0.22043 (9)	0.0337 (3)
H13	0.7782	0.2317	0.2110	0.040*
C14	0.65849 (14)	0.34552 (9)	0.15348 (9)	0.0330 (3)
H14	0.7039	0.3487	0.0983	0.040*
C15	0.54789 (14)	0.41008 (8)	0.16735 (8)	0.0291 (3)
H15	0.5188	0.4572	0.1210	0.035*
C16	0.47777 (13)	0.40800 (8)	0.24747 (8)	0.0248 (2)
C17	0.20346 (13)	0.47769 (8)	0.18908 (8)	0.0255 (2)
H17	0.1298	0.5231	0.2091	0.031*
C18	0.12395 (13)	0.38332 (8)	0.17816 (8)	0.0280 (3)
C19	0.10045 (12)	0.35606 (8)	0.07625 (8)	0.0253 (2)
C20	0.03310 (14)	0.27627 (8)	0.03180 (9)	0.0307 (3)
H20	−0.0095	0.2302	0.0666	0.037*
C21	0.03053 (14)	0.26658 (8)	−0.06495 (9)	0.0332 (3)
H21	−0.0141	0.2126	−0.0969	0.040*
C22	0.09206 (15)	0.33439 (9)	−0.11675 (9)	0.0334 (3)
H22	0.0893	0.3255	−0.1830	0.040*
C23	0.15714 (14)	0.41447 (8)	−0.07265 (8)	0.0303 (3)
H23	0.1982	0.4610	−0.1077	0.036*
C24	0.16014 (13)	0.42425 (7)	0.02446 (8)	0.0251 (2)
C25	0.22245 (13)	0.50203 (8)	0.08798 (8)	0.0258 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0330 (4)	0.0288 (4)	0.0296 (4)	0.0069 (3)	0.0081 (3)	0.0060 (3)
O2	0.0399 (5)	0.0292 (4)	0.0385 (5)	0.0078 (4)	0.0125 (4)	0.0058 (4)
O3	0.0468 (6)	0.0541 (6)	0.0294 (5)	−0.0207 (5)	0.0036 (4)	0.0110 (4)
O4	0.0468 (5)	0.0261 (4)	0.0291 (4)	−0.0079 (4)	0.0049 (4)	0.0039 (3)
C1	0.0249 (5)	0.0234 (5)	0.0231 (5)	−0.0017 (4)	0.0033 (4)	0.0008 (4)
C2	0.0236 (5)	0.0248 (5)	0.0234 (5)	−0.0020 (4)	0.0015 (4)	−0.0006 (4)
C3	0.0254 (5)	0.0256 (5)	0.0272 (6)	−0.0028 (4)	0.0037 (4)	−0.0008 (4)
C4	0.0256 (5)	0.0280 (6)	0.0249 (5)	−0.0048 (4)	0.0014 (4)	−0.0016 (4)
C5	0.0331 (6)	0.0334 (6)	0.0296 (6)	−0.0035 (5)	0.0060 (5)	−0.0047 (5)
C6	0.0355 (7)	0.0474 (7)	0.0237 (6)	−0.0090 (6)	0.0065 (5)	−0.0042 (5)
C7	0.0346 (6)	0.0458 (7)	0.0234 (6)	−0.0079 (6)	0.0010 (5)	0.0059 (5)
C8	0.0286 (6)	0.0358 (6)	0.0274 (6)	−0.0023 (5)	−0.0004 (5)	0.0047 (5)
C9	0.0233 (5)	0.0290 (6)	0.0241 (5)	−0.0045 (4)	0.0004 (4)	−0.0006 (4)
C10	0.0221 (5)	0.0255 (5)	0.0255 (5)	−0.0016 (4)	0.0011 (4)	−0.0009 (4)
C11	0.0250 (5)	0.0270 (6)	0.0263 (6)	−0.0018 (4)	0.0039 (4)	−0.0002 (4)
C12	0.0291 (6)	0.0273 (6)	0.0366 (6)	0.0019 (5)	0.0028 (5)	0.0004 (5)
C13	0.0276 (6)	0.0328 (6)	0.0408 (7)	0.0030 (5)	0.0067 (5)	−0.0064 (5)
C14	0.0285 (6)	0.0383 (7)	0.0332 (6)	−0.0027 (5)	0.0088 (5)	−0.0041 (5)
C15	0.0267 (6)	0.0317 (6)	0.0286 (6)	−0.0027 (5)	0.0043 (5)	0.0009 (5)
C16	0.0217 (5)	0.0247 (5)	0.0271 (5)	−0.0033 (4)	0.0022 (4)	−0.0014 (4)
C17	0.0263 (6)	0.0264 (5)	0.0233 (5)	0.0017 (4)	0.0032 (4)	0.0032 (4)
C18	0.0223 (5)	0.0336 (6)	0.0269 (6)	−0.0018 (5)	0.0014 (4)	0.0070 (5)
C19	0.0214 (5)	0.0257 (5)	0.0277 (6)	0.0019 (4)	0.0021 (4)	0.0045 (4)
C20	0.0268 (6)	0.0264 (6)	0.0367 (6)	−0.0022 (5)	0.0010 (5)	0.0059 (5)
C21	0.0324 (6)	0.0259 (6)	0.0387 (7)	−0.0007 (5)	0.0006 (5)	−0.0046 (5)
C22	0.0370 (7)	0.0345 (6)	0.0287 (6)	−0.0001 (5)	0.0063 (5)	−0.0046 (5)
C23	0.0337 (6)	0.0304 (6)	0.0272 (6)	−0.0027 (5)	0.0069 (5)	0.0014 (5)
C24	0.0243 (5)	0.0237 (5)	0.0265 (6)	0.0012 (4)	0.0031 (4)	0.0025 (4)
C25	0.0272 (5)	0.0242 (5)	0.0251 (5)	0.0012 (4)	0.0025 (4)	0.0037 (4)

O1—C10	1.3400 (14)	C11—C16	1.3956 (16)
O1—C11	1.4030 (13)	C12—C13	1.3817 (18)
O2—C3	1.2185 (14)	C12—H12	0.9500
O3—C18	1.2131 (14)	C13—C14	1.3877 (18)
O4—C25	1.2123 (14)	C13—H13	0.9500
C1—C2	1.4906 (15)	C14—C15	1.3861 (17)
C1—C16	1.5256 (15)	C14—H14	0.9500
C1—C17	1.5595 (15)	C15—C16	1.3986 (16)
C1—H1	1.0000	C15—H15	0.9500
C2—C10	1.3464 (16)	C17—C25	1.5256 (15)
C2—C3	1.4709 (16)	C17—C18	1.5268 (16)
C3—C4	1.5093 (16)	C17—H17	1.0000
C4—C5	1.3715 (17)	C18—C19	1.4829 (16)
C4—C9	1.4008 (16)	C19—C20	1.3924 (16)
C5—C6	1.4034 (18)	C19—C24	1.3937 (15)
C5—H5	0.9500	C20—C21	1.3843 (18)
C6—C7	1.378 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.3977 (18)
C7—C8	1.4047 (18)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.3874 (17)
C8—C9	1.3775 (16)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.3888 (16)
C9—C10	1.4717 (15)	C23—H23	0.9500
C11—C12	1.3873 (16)	C24—C25	1.4818 (16)
C10—O1—C11	115.17 (9)	C12—C13—H13	120.1
C2—C1—C16	108.01 (9)	C14—C13—H13	120.1
C2—C1—C17	110.81 (9)	C15—C14—C13	119.85 (11)
C16—C1—C17	113.92 (9)	C15—C14—H14	120.1
C2—C1—H1	108.0	C13—C14—H14	120.1
C16—C1—H1	108.0	C14—C15—C16	122.03 (11)
C17—C1—H1	108.0	C14—C15—H15	119.0
C10—C2—C3	107.40 (10)	C16—C15—H15	119.0
C10—C2—C1	123.94 (10)	C11—C16—C15	116.22 (10)
C3—C2—C1	128.60 (10)	C11—C16—C1	122.27 (10)
O2—C3—C2	127.35 (11)	C15—C16—C1	121.46 (10)
O2—C3—C4	126.60 (11)	C25—C17—C18	103.92 (9)
C2—C3—C4	106.03 (9)	C25—C17—C1	113.22 (9)
C5—C4—C9	121.12 (11)	C18—C17—C1	114.84 (9)
C5—C4—C3	131.06 (11)	C25—C17—H17	108.2
C9—C4—C3	107.82 (10)	C18—C17—H17	108.2
C4—C5—C6	117.79 (12)	C1—C17—H17	108.2
C4—C5—H5	121.1	O3—C18—C19	126.10 (11)
C6—C5—H5	121.1	O3—C18—C17	125.71 (11)
C7—C6—C5	121.10 (11)	C19—C18—C17	108.20 (9)
C7—C6—H6	119.4	C20—C19—C24	120.94 (11)
C5—C6—H6	119.4	C20—C19—C18	129.36 (10)
C6—C7—C8	121.16 (11)	C24—C19—C18	109.70 (10)
C6—C7—H7	119.4	C21—C20—C19	117.57 (11)
C8—C7—H7	119.4	C21—C20—H20	121.2
C9—C8—C7	117.31 (12)	C19—C20—H20	121.2
C9—C8—H8	121.3	C20—C21—C22	121.54 (11)
C7—C8—H8	121.3	C20—C21—H21	119.2
C8—C9—C4	121.52 (11)	C22—C21—H21	119.2
C8—C9—C10	132.35 (11)	C23—C22—C21	120.82 (11)
C4—C9—C10	106.13 (10)	C23—C22—H22	119.6
O1—C10—C2	126.54 (10)	C21—C22—H22	119.6
O1—C10—C9	120.86 (10)	C22—C23—C24	117.73 (11)
C2—C10—C9	112.60 (10)	C22—C23—H23	121.1
C12—C11—C16	122.74 (11)	C24—C23—H23	121.1
C12—C11—O1	114.01 (10)	C23—C24—C19	121.38 (11)
C16—C11—O1	123.21 (10)	C23—C24—C25	128.48 (10)
C13—C12—C11	119.30 (11)	C19—C24—C25	110.14 (10)
C13—C12—H12	120.3	O4—C25—C24	126.38 (10)
C11—C12—H12	120.3	O4—C25—C17	125.60 (10)
C12—C13—C14	119.85 (11)	C24—C25—C17	108.02 (9)
C16—C1—C2—C10	−8.40 (14)	O1—C11—C16—C15	176.14 (10)
C17—C1—C2—C10	117.03 (12)	C12—C11—C16—C1	−178.73 (10)
C16—C1—C2—C3	174.83 (10)	O1—C11—C16—C1	−1.09 (17)
C17—C1—C2—C3	−59.74 (14)	C14—C15—C16—C11	0.92 (17)
C10—C2—C3—O2	−177.52 (11)	C14—C15—C16—C1	178.17 (10)
C1—C2—C3—O2	−0.33 (19)	C2—C1—C16—C11	7.86 (14)
C10—C2—C3—C4	0.95 (12)	C17—C1—C16—C11	−115.70 (11)
C1—C2—C3—C4	178.15 (10)	C2—C1—C16—C15	−169.22 (10)
O2—C3—C4—C5	−1.7 (2)	C17—C1—C16—C15	67.21 (13)
C2—C3—C4—C5	179.85 (12)	C2—C1—C17—C25	171.83 (9)
O2—C3—C4—C9	178.00 (11)	C16—C1—C17—C25	−66.13 (12)
C2—C3—C4—C9	−0.49 (12)	C2—C1—C17—C18	−69.02 (12)
C9—C4—C5—C6	0.34 (17)	C16—C1—C17—C18	53.01 (13)
C3—C4—C5—C6	179.97 (11)	C25—C17—C18—O3	−179.89 (12)
C4—C5—C6—C7	0.17 (18)	C1—C17—C18—O3	55.90 (16)
C5—C6—C7—C8	−0.39 (19)	C25—C17—C18—C19	0.28 (11)
C6—C7—C8—C9	0.09 (18)	C1—C17—C18—C19	−123.93 (10)
C7—C8—C9—C4	0.42 (17)	O3—C18—C19—C20	0.1 (2)
C7—C8—C9—C10	−179.89 (11)	C17—C18—C19—C20	179.97 (11)
C5—C4—C9—C8	−0.65 (17)	O3—C18—C19—C24	−178.97 (12)
C3—C4—C9—C8	179.64 (10)	C17—C18—C19—C24	0.86 (12)
C5—C4—C9—C10	179.59 (10)	C24—C19—C20—C21	1.22 (17)
C3—C4—C9—C10	−0.12 (12)	C18—C19—C20—C21	−177.80 (11)
C11—O1—C10—C2	6.15 (16)	C19—C20—C21—C22	−0.44 (18)
C11—O1—C10—C9	−173.60 (9)	C20—C21—C22—C23	−0.48 (19)
C3—C2—C10—O1	179.16 (10)	C21—C22—C23—C24	0.59 (18)
C1—C2—C10—O1	1.80 (18)	C22—C23—C24—C19	0.20 (17)
C3—C2—C10—C9	−1.08 (13)	C22—C23—C24—C25	179.92 (11)
C1—C2—C10—C9	−178.44 (10)	C20—C19—C24—C23	−1.13 (17)
C8—C9—C10—O1	0.82 (19)	C18—C19—C24—C23	178.07 (10)
C4—C9—C10—O1	−179.45 (10)	C20—C19—C24—C25	179.10 (10)
C8—C9—C10—C2	−178.95 (12)	C18—C19—C24—C25	−1.70 (13)
C4—C9—C10—C2	0.77 (13)	C23—C24—C25—O4	1.7 (2)
C10—O1—C11—C12	171.53 (10)	C19—C24—C25—O4	−178.55 (11)
C10—O1—C11—C16	−6.30 (15)	C23—C24—C25—C17	−177.87 (11)
C16—C11—C12—C13	1.24 (18)	C19—C24—C25—C17	1.87 (12)
O1—C11—C12—C13	−176.60 (10)	C18—C17—C25—O4	179.17 (11)
C11—C12—C13—C14	−0.34 (18)	C1—C17—C25—O4	−55.58 (15)
C12—C13—C14—C15	−0.22 (18)	C18—C17—C25—C24	−1.26 (11)
C13—C14—C15—C16	−0.09 (18)	C1—C17—C25—C24	124.00 (10)
C12—C11—C16—C15	−1.50 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O4i	0.95	2.54	3.4687 (15)	166

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C12H12O4i	0.95	2.54	3.4687(15)	166

Symmetry code: (i) .