Ethyl 2-(4-methyl-benzo-yl)-2,3-dihydro-1H-indene-2-carboxyl-ate.

The title compound, C20H20O3, contains two fused rings with a quaternary carbon centre connecting p-toluoyl and eth-oxy-carbonyl groups. The dihedral angle between the fused benzene ring and the three-C-atom plane (derived from O=C-C-C=O) is 82.5 (4)°, whereas the dihedral angle between the planes of the benzene rings is 53.4 (2)°. In the crystal, molecules are linked via C-H⋯Oester hydrogen bonds, forming chains propagating along [010].

Related literature

For the preparation and crystal engineering studies of the title compound, see: Singh & Paul (2006 ▶); Wang & Wu (2012 ▶).

Experimental

Crystal data

C20H20O3

M = 308.37

Monoclinic,

a = 8.1957 (14) Å

b = 6.1287 (10) Å

c = 32.995 (5) Å

β = 93.014 (3)°

V = 1655.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.12 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.990, T max = 0.992

11945 measured reflections

3241 independent reflections

2482 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.187

S = 1.09

3241 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT(Bruker, 2004 ▶); 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/S1600536813005801/gg2108sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005801/gg2108Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005801/gg2108Isup3.cml

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

C20H20O3	F(000) = 656
Mr = 308.37	Dx = 1.238 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3624 reflections
a = 8.1957 (14) Å	θ = 2.5–24.5°
b = 6.1287 (10) Å	µ = 0.08 mm−1
c = 32.995 (5) Å	T = 298 K
β = 93.014 (3)°	Block, colourless
V = 1655.0 (5) Å3	0.12 × 0.10 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	3241 independent reflections
Radiation source: fine-focus sealed tube	2482 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→10
Tmin = 0.990, Tmax = 0.992	k = −7→7
11945 measured reflections	l = −40→36

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1176P)2 + 0.1336P] where P = (Fo2 + 2Fc2)/3
3241 reflections	(Δ/σ)max = 0.008
210 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.7866 (3)	0.2221 (4)	0.25704 (6)	0.0666 (6)
H1	0.8421	0.2668	0.2809	0.080*
C2	0.8114 (3)	0.0156 (4)	0.24231 (7)	0.0693 (6)
H2	0.8860	−0.0765	0.2559	0.083*
C3	0.7266 (2)	−0.0567 (3)	0.20748 (6)	0.0555 (5)
H3	0.7424	−0.1972	0.1978	0.067*
C4	0.6182 (2)	0.0832 (3)	0.18736 (5)	0.0463 (4)
C5	0.5970 (2)	0.2939 (3)	0.20139 (5)	0.0452 (4)
C6	0.6805 (2)	0.3627 (3)	0.23682 (6)	0.0552 (5)
H6	0.6647	0.5027	0.2467	0.066*
C7	0.4828 (3)	0.4205 (3)	0.17361 (7)	0.0626 (6)
H7A	0.5406	0.5355	0.1602	0.075*
H7B	0.3963	0.4854	0.1885	0.075*
C8	0.5092 (3)	0.0359 (3)	0.15049 (7)	0.0655 (6)
H8A	0.4358	−0.0840	0.1556	0.079*
H8B	0.5732	−0.0015	0.1276	0.079*
C9	0.4114 (2)	0.2508 (3)	0.14203 (6)	0.0514 (5)
C10	0.2314 (3)	0.2265 (3)	0.14927 (6)	0.0555 (5)
C11	−0.0233 (3)	0.4180 (4)	0.14107 (7)	0.0726 (7)
H11A	−0.0434	0.4237	0.1698	0.087*
H11B	−0.0798	0.2922	0.1293	0.087*
C12	−0.0820 (3)	0.6211 (5)	0.12057 (9)	0.0863 (8)
H12A	−0.0303	0.7449	0.1336	0.129*
H12B	−0.1983	0.6324	0.1222	0.129*
H12C	−0.0554	0.6173	0.0926	0.129*
C13	0.4316 (2)	0.3270 (3)	0.09827 (6)	0.0516 (5)
C14	0.3593 (2)	0.1945 (3)	0.06402 (6)	0.0513 (5)
C15	0.3657 (3)	0.2784 (4)	0.02492 (7)	0.0676 (6)
H15	0.4123	0.4147	0.0212	0.081*
C16	0.3042 (3)	0.1633 (5)	−0.00819 (7)	0.0791 (7)
H16	0.3093	0.2236	−0.0340	0.095*
C17	0.2350 (3)	−0.0398 (5)	−0.00395 (7)	0.0705 (7)
C18	0.2282 (3)	−0.1239 (4)	0.03492 (7)	0.0665 (6)
H18	0.1819	−0.2607	0.0385	0.080*
C19	0.2881 (2)	−0.0102 (3)	0.06837 (6)	0.0578 (5)
H19	0.2811	−0.0703	0.0941	0.069*
C20	0.1698 (4)	−0.1689 (6)	−0.04011 (8)	0.1051 (11)
H20A	0.2398	−0.2916	−0.0442	0.158*
H20B	0.1664	−0.0777	−0.0638	0.158*
H20C	0.0616	−0.2196	−0.0354	0.158*
O1	0.1677 (3)	0.0787 (3)	0.16597 (5)	0.0896 (6)
O2	0.15098 (16)	0.4028 (2)	0.13532 (4)	0.0625 (4)
O3	0.5094 (2)	0.4910 (3)	0.09153 (5)	0.0775 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0753 (13)	0.0748 (15)	0.0488 (11)	−0.0053 (11)	−0.0071 (9)	−0.0038 (10)
C2	0.0733 (13)	0.0787 (15)	0.0548 (12)	0.0152 (12)	−0.0078 (10)	0.0051 (11)
C3	0.0662 (12)	0.0488 (11)	0.0516 (11)	0.0107 (9)	0.0038 (9)	0.0000 (8)
C4	0.0530 (9)	0.0411 (9)	0.0452 (9)	0.0012 (7)	0.0056 (7)	−0.0007 (7)
C5	0.0496 (9)	0.0402 (9)	0.0465 (10)	−0.0029 (7)	0.0097 (7)	−0.0031 (7)
C6	0.0675 (11)	0.0487 (11)	0.0502 (11)	−0.0103 (9)	0.0109 (9)	−0.0092 (8)
C7	0.0749 (13)	0.0380 (10)	0.0738 (14)	0.0074 (9)	−0.0077 (10)	−0.0111 (9)
C8	0.0928 (15)	0.0363 (10)	0.0649 (13)	0.0133 (9)	−0.0206 (11)	−0.0072 (9)
C9	0.0586 (10)	0.0358 (9)	0.0589 (11)	0.0047 (8)	−0.0059 (8)	−0.0017 (8)
C10	0.0712 (12)	0.0477 (11)	0.0480 (10)	−0.0093 (9)	0.0066 (9)	0.0021 (8)
C11	0.0517 (11)	0.1032 (19)	0.0637 (13)	−0.0118 (11)	0.0122 (9)	−0.0123 (13)
C12	0.0489 (12)	0.108 (2)	0.1017 (19)	0.0111 (12)	0.0005 (11)	−0.0099 (16)
C13	0.0441 (9)	0.0453 (10)	0.0659 (12)	0.0038 (8)	0.0074 (8)	0.0053 (9)
C14	0.0455 (9)	0.0539 (11)	0.0550 (11)	0.0080 (8)	0.0078 (7)	0.0051 (8)
C15	0.0675 (12)	0.0726 (14)	0.0641 (13)	0.0099 (11)	0.0151 (10)	0.0132 (11)
C16	0.0814 (15)	0.104 (2)	0.0525 (13)	0.0238 (15)	0.0096 (11)	0.0089 (13)
C17	0.0571 (11)	0.0984 (18)	0.0555 (13)	0.0277 (12)	−0.0020 (9)	−0.0150 (12)
C18	0.0634 (12)	0.0707 (14)	0.0649 (13)	0.0048 (10)	−0.0021 (9)	−0.0147 (11)
C19	0.0625 (11)	0.0587 (12)	0.0521 (11)	0.0014 (9)	0.0013 (8)	0.0008 (9)
C20	0.097 (2)	0.146 (3)	0.0700 (16)	0.0411 (19)	−0.0142 (14)	−0.0384 (17)
O1	0.1113 (14)	0.0733 (11)	0.0858 (13)	−0.0225 (10)	0.0211 (10)	0.0235 (9)
O2	0.0509 (8)	0.0652 (9)	0.0725 (9)	0.0009 (6)	0.0132 (6)	0.0094 (7)
O3	0.0783 (10)	0.0644 (9)	0.0909 (12)	−0.0230 (8)	0.0139 (9)	0.0072 (8)

C1—C6	1.372 (3)	C11—C12	1.484 (4)
C1—C2	1.374 (3)	C11—H11A	0.9700
C1—H1	0.9300	C11—H11B	0.9700
C2—C3	1.384 (3)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.379 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—O3	1.216 (2)
C4—C5	1.385 (2)	C13—C14	1.489 (3)
C4—C8	1.499 (3)	C14—C15	1.392 (3)
C5—C6	1.389 (3)	C14—C19	1.395 (3)
C5—C7	1.493 (3)	C15—C16	1.374 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—C9	1.564 (3)	C16—C17	1.378 (4)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—C18	1.386 (3)
C8—C9	1.559 (3)	C17—C20	1.506 (3)
C8—H8A	0.9700	C18—C19	1.374 (3)
C8—H8B	0.9700	C18—H18	0.9300
C9—C10	1.514 (3)	C19—H19	0.9300
C9—C13	1.535 (3)	C20—H20A	0.9600
C10—O1	1.195 (2)	C20—H20B	0.9600
C10—O2	1.335 (3)	C20—H20C	0.9600
C11—O2	1.454 (2)
C6—C1—C2	120.55 (19)	O2—C11—H11A	110.3
C6—C1—H1	119.7	C12—C11—H11A	110.3
C2—C1—H1	119.7	O2—C11—H11B	110.3
C1—C2—C3	120.7 (2)	C12—C11—H11B	110.3
C1—C2—H2	119.6	H11A—C11—H11B	108.6
C3—C2—H2	119.6	C11—C12—H12A	109.5
C4—C3—C2	118.89 (19)	C11—C12—H12B	109.5
C4—C3—H3	120.6	H12A—C12—H12B	109.5
C2—C3—H3	120.6	C11—C12—H12C	109.5
C3—C4—C5	120.47 (17)	H12A—C12—H12C	109.5
C3—C4—C8	127.69 (17)	H12B—C12—H12C	109.5
C5—C4—C8	111.81 (16)	O3—C13—C14	120.20 (19)
C4—C5—C6	119.98 (18)	O3—C13—C9	120.44 (18)
C4—C5—C7	111.40 (16)	C14—C13—C9	119.33 (16)
C6—C5—C7	128.61 (17)	C15—C14—C19	117.6 (2)
C1—C6—C5	119.33 (19)	C15—C14—C13	117.97 (19)
C1—C6—H6	120.3	C19—C14—C13	124.38 (17)
C5—C6—H6	120.3	C16—C15—C14	121.1 (2)
C5—C7—C9	105.30 (15)	C16—C15—H15	119.4
C5—C7—H7A	110.7	C14—C15—H15	119.4
C9—C7—H7A	110.7	C15—C16—C17	121.3 (2)
C5—C7—H7B	110.7	C15—C16—H16	119.4
C9—C7—H7B	110.7	C17—C16—H16	119.4
H7A—C7—H7B	108.8	C16—C17—C18	117.8 (2)
C4—C8—C9	105.09 (15)	C16—C17—C20	121.6 (3)
C4—C8—H8A	110.7	C18—C17—C20	120.5 (3)
C9—C8—H8A	110.7	C19—C18—C17	121.6 (2)
C4—C8—H8B	110.7	C19—C18—H18	119.2
C9—C8—H8B	110.7	C17—C18—H18	119.2
H8A—C8—H8B	108.8	C18—C19—C14	120.5 (2)
C10—C9—C13	109.40 (15)	C18—C19—H19	119.8
C10—C9—C8	112.61 (16)	C14—C19—H19	119.8
C13—C9—C8	110.23 (16)	C17—C20—H20A	109.5
C10—C9—C7	107.08 (16)	C17—C20—H20B	109.5
C13—C9—C7	111.68 (16)	H20A—C20—H20B	109.5
C8—C9—C7	105.78 (15)	C17—C20—H20C	109.5
O1—C10—O2	123.5 (2)	H20A—C20—H20C	109.5
O1—C10—C9	126.9 (2)	H20B—C20—H20C	109.5
O2—C10—C9	109.51 (15)	C10—O2—C11	118.56 (16)
O2—C11—C12	106.95 (18)
C6—C1—C2—C3	−1.9 (3)	C8—C9—C10—O2	−169.98 (16)
C1—C2—C3—C4	1.0 (3)	C7—C9—C10—O2	74.16 (19)
C2—C3—C4—C5	1.2 (3)	C10—C9—C13—O3	124.95 (19)
C2—C3—C4—C8	−177.0 (2)	C8—C9—C13—O3	−110.7 (2)
C3—C4—C5—C6	−2.5 (3)	C7—C9—C13—O3	6.6 (2)
C8—C4—C5—C6	176.01 (18)	C10—C9—C13—C14	−56.9 (2)
C3—C4—C5—C7	176.28 (18)	C8—C9—C13—C14	67.4 (2)
C8—C4—C5—C7	−5.2 (2)	C7—C9—C13—C14	−175.30 (15)
C2—C1—C6—C5	0.6 (3)	O3—C13—C14—C15	−8.0 (3)
C4—C5—C6—C1	1.6 (3)	C9—C13—C14—C15	173.84 (16)
C7—C5—C6—C1	−176.9 (2)	O3—C13—C14—C19	170.76 (19)
C4—C5—C7—C9	7.9 (2)	C9—C13—C14—C19	−7.4 (3)
C6—C5—C7—C9	−173.47 (17)	C19—C14—C15—C16	−0.1 (3)
C3—C4—C8—C9	178.54 (18)	C13—C14—C15—C16	178.77 (18)
C5—C4—C8—C9	0.2 (2)	C14—C15—C16—C17	−0.4 (3)
C4—C8—C9—C10	−112.09 (18)	C15—C16—C17—C18	0.5 (3)
C4—C8—C9—C13	125.43 (18)	C15—C16—C17—C20	−179.0 (2)
C4—C8—C9—C7	4.5 (2)	C16—C17—C18—C19	0.0 (3)
C5—C7—C9—C10	112.94 (18)	C20—C17—C18—C19	179.4 (2)
C5—C7—C9—C13	−127.31 (17)	C17—C18—C19—C14	−0.5 (3)
C5—C7—C9—C8	−7.4 (2)	C15—C14—C19—C18	0.6 (3)
C13—C9—C10—O1	135.3 (2)	C13—C14—C19—C18	−178.23 (18)
C8—C9—C10—O1	12.4 (3)	O1—C10—O2—C11	0.7 (3)
C7—C9—C10—O1	−103.5 (2)	C9—C10—O2—C11	−176.98 (16)
C13—C9—C10—O2	−47.0 (2)	C12—C11—O2—C10	−176.51 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O3	0.97	2.28	2.762 (3)	110
C8—H8A···O1	0.97	2.45	2.883 (3)	107
C1—H1···O1i	0.93	2.60	3.357 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.60	3.357 (3)	139

Symmetry code: (i) .