5-Benzoyl-2-(1H-indol-3-yl)-4-(4-methyl-phen-yl)-4,5-dihydro-furan-3-carbonitrile.

The furan ring in the title compound, C(27)H(20)N(2)O(2), adopts a twisted conformation about the sp(3)-sp(3) bond. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O inter-action which generates an S(6) ring motif. The crystal packing is stabilized by N-H⋯O and C-H⋯O inter-actions generating centrosymmetric R(2) (2)(18) and C(6) chain motifs, respectively. A weak C-H⋯π inter-action is also observed.

Related literature

For the biological importance of furan derivatives, see: Auvin & Chabrier De Lassauniere (2005 ▶). For hydrogen-bonding graph-set notation, see: Bernstein et al. (1995 ▶). For additional conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H20N2O2

M = 404.45

Monoclinic,

a = 9.8084 (4) Å

b = 15.9553 (7) Å

c = 13.8782 (7) Å

β = 107.185 (2)°

V = 2074.92 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.19 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.974

21144 measured reflections

4647 independent reflections

3017 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 1.02

4647 reflections

284 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.22 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011105/tk5068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011105/tk5068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011105/tk5068Isup3.cml

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

C27H20N2O2	F(000) = 848
Mr = 404.45	Dx = 1.295 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 9.8084 (4) Å	θ = 2–31°
b = 15.9553 (7) Å	µ = 0.08 mm−1
c = 13.8782 (7) Å	T = 293 K
β = 107.185 (2)°	Block, pale-yellow
V = 2074.92 (16) Å3	0.19 × 0.15 × 0.12 mm
Z = 4

Bruker Kappa APEXII diffractometer	4647 independent reflections
Radiation source: fine-focus sealed tube	3017 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 0 pixels mm-1	θmax = 27.3°, θmin = 2.0°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
Tmin = 0.967, Tmax = 0.974	l = −17→17
21144 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.5454P] where P = (Fo2 + 2Fc2)/3
4647 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 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
H2	1.231 (2)	−0.0946 (12)	0.5116 (14)	0.044 (5)*
C1	0.7913 (2)	−0.08013 (11)	0.21842 (13)	0.0408 (4)
C2	0.78765 (18)	0.00744 (10)	0.23169 (12)	0.0331 (4)
C3	0.88408 (17)	0.05202 (10)	0.30178 (12)	0.0301 (4)
C4	0.71584 (17)	0.14707 (10)	0.22283 (12)	0.0318 (4)
H4	0.7178	0.1947	0.1787	0.038*
C5	0.68263 (18)	0.06474 (10)	0.15994 (12)	0.0314 (4)
H5	0.5848	0.0465	0.1531	0.038*
C6	0.7683 (3)	0.09390 (17)	−0.23642 (17)	0.0734 (7)
H6A	0.8681	0.0883	−0.2296	0.110*
H6B	0.7350	0.1474	−0.2658	0.110*
H6C	0.7163	0.0501	−0.2791	0.110*
C31	1.01403 (17)	0.02910 (10)	0.37695 (12)	0.0310 (4)
C32	1.12543 (17)	0.08399 (11)	0.43391 (12)	0.0325 (4)
C33	1.14643 (19)	0.17039 (11)	0.44071 (14)	0.0405 (4)
H33	1.0781	0.2066	0.4014	0.049*
C34	1.2696 (2)	0.20113 (13)	0.50646 (16)	0.0535 (5)
H34	1.2841	0.2588	0.5116	0.064*
C35	1.3735 (2)	0.14808 (14)	0.56565 (17)	0.0615 (6)
H35	1.4558	0.1709	0.6097	0.074*
C36	1.3567 (2)	0.06253 (14)	0.56019 (15)	0.0527 (5)
H36	1.4263	0.0268	0.5991	0.063*
C37	1.23189 (18)	0.03164 (11)	0.49441 (13)	0.0367 (4)
C38	1.05756 (18)	−0.05100 (11)	0.40606 (13)	0.0357 (4)
H38	1.0052	−0.0992	0.3819	0.043*
C41	0.60327 (18)	0.16108 (10)	0.27659 (13)	0.0337 (4)
C42	0.45710 (18)	0.18082 (11)	0.21168 (13)	0.0372 (4)
C43	0.4312 (2)	0.21107 (12)	0.11489 (14)	0.0463 (5)
H43	0.5073	0.2244	0.0906	0.056*
C44	0.2925 (2)	0.22178 (14)	0.05363 (17)	0.0619 (6)
H44	0.2753	0.2419	−0.0118	0.074*
C45	0.1806 (3)	0.20254 (16)	0.0902 (2)	0.0759 (8)
H45	0.0873	0.2089	0.0490	0.091*
C46	0.2051 (3)	0.17414 (18)	0.1867 (2)	0.0786 (8)
H46	0.1287	0.1622	0.2112	0.094*
C47	0.3427 (2)	0.16313 (14)	0.24769 (17)	0.0574 (6)
H47	0.3589	0.1437	0.3133	0.069*
C51	0.70509 (18)	0.07130 (10)	0.05677 (12)	0.0320 (4)
C52	0.59093 (19)	0.08565 (11)	−0.02828 (13)	0.0380 (4)
H52	0.4993	0.0900	−0.0222	0.046*
C53	0.6116 (2)	0.09362 (12)	−0.12209 (14)	0.0447 (5)
H53	0.5334	0.1032	−0.1782	0.054*
C54	0.7455 (2)	0.08765 (12)	−0.13439 (15)	0.0465 (5)
C55	0.8592 (2)	0.07429 (13)	−0.04929 (16)	0.0503 (5)
H55	0.9509	0.0707	−0.0555	0.060*
C56	0.8396 (2)	0.06610 (12)	0.04483 (14)	0.0426 (4)
H56	0.9181	0.0570	0.1009	0.051*
N1	0.7928 (2)	−0.15113 (11)	0.20826 (15)	0.0670 (6)
N2	1.18746 (16)	−0.04969 (10)	0.47495 (11)	0.0387 (4)
O1	0.85398 (12)	0.13585 (7)	0.29520 (9)	0.0369 (3)
O2	0.62895 (14)	0.14959 (8)	0.36623 (9)	0.0452 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0479 (11)	0.0332 (10)	0.0347 (10)	0.0026 (8)	0.0019 (8)	−0.0008 (8)
C2	0.0382 (9)	0.0284 (8)	0.0297 (9)	0.0029 (7)	0.0054 (7)	0.0004 (7)
C3	0.0333 (9)	0.0274 (8)	0.0293 (9)	0.0050 (7)	0.0086 (7)	0.0024 (7)
C4	0.0329 (9)	0.0289 (9)	0.0287 (9)	0.0038 (6)	0.0014 (7)	0.0007 (7)
C5	0.0322 (9)	0.0284 (8)	0.0306 (9)	0.0002 (6)	0.0047 (7)	−0.0014 (7)
C6	0.0889 (19)	0.0920 (19)	0.0465 (14)	0.0128 (14)	0.0310 (13)	0.0068 (12)
C31	0.0336 (9)	0.0323 (9)	0.0273 (9)	0.0033 (7)	0.0093 (7)	0.0010 (7)
C32	0.0326 (9)	0.0384 (9)	0.0272 (9)	0.0009 (7)	0.0099 (7)	0.0021 (7)
C33	0.0412 (10)	0.0380 (10)	0.0403 (11)	−0.0008 (8)	0.0091 (8)	0.0031 (8)
C34	0.0522 (13)	0.0450 (12)	0.0566 (13)	−0.0126 (9)	0.0057 (10)	−0.0017 (10)
C35	0.0471 (13)	0.0626 (15)	0.0604 (15)	−0.0160 (10)	−0.0061 (11)	0.0037 (11)
C36	0.0389 (11)	0.0599 (13)	0.0495 (12)	−0.0012 (9)	−0.0021 (9)	0.0106 (10)
C37	0.0345 (10)	0.0417 (10)	0.0328 (9)	0.0018 (7)	0.0083 (8)	0.0054 (7)
C38	0.0385 (10)	0.0363 (9)	0.0306 (9)	0.0027 (7)	0.0075 (8)	0.0002 (7)
C41	0.0402 (10)	0.0257 (8)	0.0306 (9)	0.0035 (7)	0.0031 (7)	−0.0009 (7)
C42	0.0365 (10)	0.0361 (9)	0.0343 (10)	0.0075 (7)	0.0030 (8)	−0.0048 (7)
C43	0.0479 (11)	0.0472 (11)	0.0369 (11)	0.0155 (9)	0.0020 (9)	−0.0002 (8)
C44	0.0636 (15)	0.0593 (14)	0.0459 (13)	0.0249 (11)	−0.0098 (11)	−0.0050 (10)
C45	0.0428 (13)	0.0837 (18)	0.081 (2)	0.0188 (12)	−0.0127 (13)	−0.0223 (15)
C46	0.0410 (13)	0.105 (2)	0.085 (2)	0.0046 (13)	0.0114 (13)	−0.0088 (16)
C47	0.0429 (12)	0.0740 (15)	0.0535 (13)	0.0057 (10)	0.0115 (10)	0.0012 (11)
C51	0.0358 (9)	0.0263 (8)	0.0310 (9)	0.0028 (7)	0.0052 (7)	−0.0013 (7)
C52	0.0342 (10)	0.0407 (10)	0.0360 (10)	−0.0023 (7)	0.0054 (8)	−0.0015 (8)
C53	0.0501 (12)	0.0482 (11)	0.0300 (10)	−0.0001 (9)	0.0029 (9)	0.0024 (8)
C54	0.0597 (13)	0.0430 (11)	0.0390 (11)	0.0073 (9)	0.0180 (10)	0.0016 (8)
C55	0.0473 (12)	0.0582 (13)	0.0499 (12)	0.0167 (9)	0.0210 (10)	0.0063 (10)
C56	0.0373 (10)	0.0482 (11)	0.0391 (11)	0.0107 (8)	0.0062 (8)	0.0030 (8)
N1	0.0830 (14)	0.0337 (10)	0.0688 (13)	0.0048 (9)	−0.0014 (11)	−0.0071 (8)
N2	0.0395 (8)	0.0369 (8)	0.0357 (8)	0.0085 (7)	0.0051 (7)	0.0084 (7)
O1	0.0331 (6)	0.0279 (6)	0.0415 (7)	0.0036 (5)	−0.0016 (5)	−0.0029 (5)
O2	0.0515 (8)	0.0508 (8)	0.0290 (7)	0.0095 (6)	0.0051 (6)	0.0042 (6)

C1—N1	1.142 (2)	C37—N2	1.370 (2)
C1—C2	1.411 (2)	C38—N2	1.348 (2)
C2—C3	1.343 (2)	C38—H38	0.9300
C2—C5	1.511 (2)	C41—O2	1.208 (2)
C3—O1	1.3670 (18)	C41—C42	1.484 (2)
C3—C31	1.436 (2)	C42—C43	1.379 (3)
C4—O1	1.4397 (19)	C42—C47	1.386 (3)
C4—C41	1.521 (2)	C43—C44	1.385 (3)
C4—C5	1.557 (2)	C43—H43	0.9300
C4—H4	0.9800	C44—C45	1.374 (3)
C5—C51	1.515 (2)	C44—H44	0.9300
C5—H5	0.9800	C45—C46	1.366 (4)
C6—C54	1.501 (3)	C45—H45	0.9300
C6—H6A	0.9600	C46—C47	1.376 (3)
C6—H6B	0.9600	C46—H46	0.9300
C6—H6C	0.9600	C47—H47	0.9300
C31—C38	1.370 (2)	C51—C56	1.380 (2)
C31—C32	1.441 (2)	C51—C52	1.385 (2)
C32—C33	1.393 (2)	C52—C53	1.381 (3)
C32—C37	1.405 (2)	C52—H52	0.9300
C33—C34	1.372 (3)	C53—C54	1.377 (3)
C33—H33	0.9300	C53—H53	0.9300
C34—C35	1.391 (3)	C54—C55	1.381 (3)
C34—H34	0.9300	C55—C56	1.381 (3)
C35—C36	1.374 (3)	C55—H55	0.9300
C35—H35	0.9300	C56—H56	0.9300
C36—C37	1.383 (3)	N2—H2	0.91 (2)
C36—H36	0.9300
N1—C1—C2	179.0 (2)	N2—C38—C31	109.98 (15)
C3—C2—C1	125.41 (15)	N2—C38—H38	125.0
C3—C2—C5	110.74 (14)	C31—C38—H38	125.0
C1—C2—C5	123.49 (15)	O2—C41—C42	121.82 (17)
C2—C3—O1	112.21 (14)	O2—C41—C4	121.48 (15)
C2—C3—C31	132.51 (15)	C42—C41—C4	116.40 (14)
O1—C3—C31	115.18 (14)	C43—C42—C47	119.15 (18)
O1—C4—C41	110.25 (13)	C43—C42—C41	122.17 (17)
O1—C4—C5	106.50 (12)	C47—C42—C41	118.55 (17)
C41—C4—C5	109.70 (13)	C42—C43—C44	120.4 (2)
O1—C4—H4	110.1	C42—C43—H43	119.8
C41—C4—H4	110.1	C44—C43—H43	119.8
C5—C4—H4	110.1	C45—C44—C43	119.5 (2)
C2—C5—C51	113.80 (13)	C45—C44—H44	120.2
C2—C5—C4	98.75 (12)	C43—C44—H44	120.2
C51—C5—C4	113.99 (13)	C46—C45—C44	120.5 (2)
C2—C5—H5	109.9	C46—C45—H45	119.7
C51—C5—H5	109.9	C44—C45—H45	119.7
C4—C5—H5	109.9	C45—C46—C47	120.2 (2)
C54—C6—H6A	109.5	C45—C46—H46	119.9
C54—C6—H6B	109.5	C47—C46—H46	119.9
H6A—C6—H6B	109.5	C46—C47—C42	120.2 (2)
C54—C6—H6C	109.5	C46—C47—H47	119.9
H6A—C6—H6C	109.5	C42—C47—H47	119.9
H6B—C6—H6C	109.5	C56—C51—C52	117.94 (16)
C38—C31—C3	125.75 (15)	C56—C51—C5	121.36 (15)
C38—C31—C32	106.58 (15)	C52—C51—C5	120.67 (15)
C3—C31—C32	127.64 (15)	C53—C52—C51	120.77 (17)
C33—C32—C37	118.61 (16)	C53—C52—H52	119.6
C33—C32—C31	135.37 (16)	C51—C52—H52	119.6
C37—C32—C31	106.01 (15)	C54—C53—C52	121.43 (18)
C34—C33—C32	118.84 (17)	C54—C53—H53	119.3
C34—C33—H33	120.6	C52—C53—H53	119.3
C32—C33—H33	120.6	C53—C54—C55	117.63 (18)
C33—C34—C35	121.53 (19)	C53—C54—C6	121.72 (19)
C33—C34—H34	119.2	C55—C54—C6	120.64 (19)
C35—C34—H34	119.2	C54—C55—C56	121.37 (19)
C36—C35—C34	121.10 (19)	C54—C55—H55	119.3
C36—C35—H35	119.4	C56—C55—H55	119.3
C34—C35—H35	119.4	C51—C56—C55	120.85 (17)
C35—C36—C37	117.31 (18)	C51—C56—H56	119.6
C35—C36—H36	121.3	C55—C56—H56	119.6
C37—C36—H36	121.3	C38—N2—C37	109.46 (14)
N2—C37—C36	129.44 (17)	C38—N2—H2	125.2 (12)
N2—C37—C32	107.95 (15)	C37—N2—H2	124.4 (12)
C36—C37—C32	122.60 (17)	C3—O1—C4	107.96 (12)
N1—C1—C2—C3	106 (14)	C5—C4—C41—O2	105.78 (18)
N1—C1—C2—C5	−82 (14)	O1—C4—C41—C42	175.00 (13)
C1—C2—C3—O1	178.88 (16)	C5—C4—C41—C42	−68.02 (17)
C5—C2—C3—O1	5.6 (2)	O2—C41—C42—C43	166.10 (17)
C1—C2—C3—C31	2.8 (3)	C4—C41—C42—C43	−20.1 (2)
C5—C2—C3—C31	−170.48 (17)	O2—C41—C42—C47	−18.1 (3)
C3—C2—C5—C51	106.09 (16)	C4—C41—C42—C47	155.73 (17)
C1—C2—C5—C51	−67.3 (2)	C47—C42—C43—C44	−1.5 (3)
C3—C2—C5—C4	−15.07 (18)	C41—C42—C43—C44	174.33 (17)
C1—C2—C5—C4	171.50 (16)	C42—C43—C44—C45	0.4 (3)
O1—C4—C5—C2	18.97 (16)	C43—C44—C45—C46	0.9 (4)
C41—C4—C5—C2	−100.33 (14)	C44—C45—C46—C47	−1.1 (4)
O1—C4—C5—C51	−102.04 (15)	C45—C46—C47—C42	0.0 (4)
C41—C4—C5—C51	138.65 (14)	C43—C42—C47—C46	1.3 (3)
C2—C3—C31—C38	−12.6 (3)	C41—C42—C47—C46	−174.7 (2)
O1—C3—C31—C38	171.41 (15)	C2—C5—C51—C56	−32.8 (2)
C2—C3—C31—C32	165.29 (18)	C4—C5—C51—C56	79.46 (19)
O1—C3—C31—C32	−10.7 (2)	C2—C5—C51—C52	149.49 (15)
C38—C31—C32—C33	−179.13 (19)	C4—C5—C51—C52	−98.29 (18)
C3—C31—C32—C33	2.7 (3)	C56—C51—C52—C53	0.6 (3)
C38—C31—C32—C37	0.53 (18)	C5—C51—C52—C53	178.47 (16)
C3—C31—C32—C37	−177.68 (16)	C51—C52—C53—C54	0.0 (3)
C37—C32—C33—C34	−0.3 (3)	C52—C53—C54—C55	−0.7 (3)
C31—C32—C33—C34	179.29 (19)	C52—C53—C54—C6	178.30 (19)
C32—C33—C34—C35	0.3 (3)	C53—C54—C55—C56	0.8 (3)
C33—C34—C35—C36	0.2 (4)	C6—C54—C55—C56	−178.2 (2)
C34—C35—C36—C37	−0.7 (3)	C52—C51—C56—C55	−0.5 (3)
C35—C36—C37—N2	−179.33 (19)	C5—C51—C56—C55	−178.35 (16)
C35—C36—C37—C32	0.6 (3)	C54—C55—C56—C51	−0.2 (3)
C33—C32—C37—N2	179.83 (15)	C31—C38—N2—C37	1.1 (2)
C31—C32—C37—N2	0.10 (19)	C36—C37—N2—C38	179.26 (19)
C33—C32—C37—C36	−0.1 (3)	C32—C37—N2—C38	−0.7 (2)
C31—C32—C37—C36	−179.88 (17)	C2—C3—O1—C4	7.86 (18)
C3—C31—C38—N2	177.26 (15)	C31—C3—O1—C4	−175.33 (14)
C32—C31—C38—N2	−0.99 (19)	C41—C4—O1—C3	101.52 (14)
O1—C4—C41—O2	−11.2 (2)	C5—C4—O1—C3	−17.43 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.93	2.52	3.032 (2)	115
N2—H2···O2i	0.91 (2)	2.04 (2)	2.880 (2)	154
C44—H44···O2ii	0.93	2.55	3.329 (3)	142
C34—H34···Cg1iii	0.93	2.69	3.556 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C51–C56 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯O1	0.93	2.52	3.032 (2)	115
N2—H2⋯O2i	0.91 (2)	2.04 (2)	2.880 (2)	154
C44—H44⋯O2ii	0.93	2.55	3.329 (3)	142
C34—H34⋯Cg1iii	0.93	2.69	3.556 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .