(±)-trans-5-Benzoyl-2-(1H-indol-3-yl)-4-phenyl-4,5-dihydro-furan-3-carbonitrile.

The furan ring in the title compound, C(26)H(18)N(2)O(2), is twisted about the C(H)-C(H) bond. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O inter-action, which generates an S(6) ring motif. The presence of N-H⋯N hydrogen bonds leads to inversion dimers, which are stabilized in the crystal packing by C-H⋯O and C-H⋯π inter-actions, forming layers that stack along the a axis.

Related literature

For graph-set notation, see: Bernstein et al. (1995 ▶). For the importance of furan derivatives, see: Kappe et al. (1997 ▶); Sato et al. (1999 ▶); Smith et al. (2002 ▶). For additional conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H18N2O2

M = 390.42

Monoclinic,

a = 12.4027 (5) Å

b = 8.3722 (4) Å

c = 19.7472 (8) Å

β = 107.570 (2)°

V = 1954.85 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.17 × 0.14 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer

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

20260 measured reflections

4403 independent reflections

3021 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.02

4403 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 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/S1600536812018430/tk5086sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018430/tk5086Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018430/tk5086Isup3.cml

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

C26H18N2O2	F(000) = 816
Mr = 390.42	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 12.4027 (5) Å	θ = 2–31°
b = 8.3722 (4) Å	µ = 0.09 mm−1
c = 19.7472 (8) Å	T = 293 K
β = 107.570 (2)°	Block, pale-yellow
V = 1954.85 (15) Å3	0.17 × 0.14 × 0.13 mm
Z = 4

Bruker Kappa APEXII diffractometer	4403 independent reflections
Radiation source: fine-focus sealed tube	3021 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 0 pixels mm-1	θmax = 27.3°, θmin = 2.2°
ω and φ scans	h = −12→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.967, Tmax = 0.974	l = −25→25
20260 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2502P] where P = (Fo2 + 2Fc2)/3
4403 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 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	0.67286 (12)	0.45451 (19)	0.17299 (7)	0.0470 (3)
C2	0.63051 (11)	0.34109 (17)	0.21081 (7)	0.0444 (3)
C3	0.52658 (12)	0.27563 (17)	0.18813 (7)	0.0450 (3)
C4	0.59768 (11)	0.18757 (18)	0.30149 (7)	0.0460 (3)
H4	0.6215	0.0796	0.3187	0.055*
C5	0.69611 (11)	0.27397 (18)	0.28285 (7)	0.0446 (3)
H5	0.7251	0.3614	0.3164	0.054*
C31	0.43701 (12)	0.28633 (17)	0.12162 (7)	0.0463 (3)
C32	0.32001 (12)	0.24303 (17)	0.10900 (8)	0.0484 (4)
C33	0.25537 (13)	0.1932 (2)	0.15212 (9)	0.0598 (4)
H33	0.2878	0.1823	0.2009	0.072*
C34	0.14258 (15)	0.1608 (2)	0.12050 (11)	0.0744 (5)
H34	0.0985	0.1280	0.1486	0.089*
C35	0.09299 (16)	0.1758 (3)	0.04764 (12)	0.0834 (6)
H35	0.0169	0.1508	0.0279	0.100*
C36	0.15389 (16)	0.2265 (2)	0.00444 (10)	0.0766 (6)
H36	0.1205	0.2373	−0.0443	0.092*
C37	0.26741 (13)	0.26136 (19)	0.03599 (8)	0.0569 (4)
C38	0.44868 (14)	0.32868 (19)	0.05720 (8)	0.0549 (4)
H38	0.5155	0.3629	0.0496	0.066*
C41	0.56106 (12)	0.27837 (19)	0.35731 (8)	0.0491 (4)
C42	0.64154 (12)	0.28240 (18)	0.43077 (7)	0.0464 (3)
C43	0.62343 (14)	0.3942 (2)	0.47757 (8)	0.0593 (4)
H43	0.5625	0.4641	0.4627	0.071*
C44	0.69484 (17)	0.4028 (2)	0.54600 (9)	0.0731 (5)
H44	0.6822	0.4786	0.5772	0.088*
C45	0.78458 (17)	0.3001 (2)	0.56826 (9)	0.0728 (5)
H45	0.8327	0.3062	0.6146	0.087*
C46	0.80372 (15)	0.1881 (2)	0.52240 (9)	0.0679 (5)
H46	0.8645	0.1182	0.5377	0.081*
C47	0.73263 (13)	0.1793 (2)	0.45343 (8)	0.0567 (4)
H47	0.7460	0.1040	0.4223	0.068*
C51	0.79172 (11)	0.16457 (18)	0.28071 (7)	0.0448 (3)
C52	0.90157 (12)	0.1926 (2)	0.32275 (8)	0.0612 (4)
H52	0.9172	0.2801	0.3532	0.073*
C53	0.98818 (14)	0.0916 (3)	0.31985 (10)	0.0726 (5)
H53	1.0616	0.1117	0.3484	0.087*
C54	0.96707 (15)	−0.0370 (2)	0.27562 (9)	0.0685 (5)
H54	1.0259	−0.1034	0.2732	0.082*
C55	0.85815 (15)	−0.0680 (2)	0.23456 (9)	0.0661 (5)
H55	0.8430	−0.1567	0.2049	0.079*
C56	0.77161 (13)	0.0315 (2)	0.23725 (8)	0.0556 (4)
H56	0.6982	0.0090	0.2094	0.067*
N1	0.34776 (12)	0.31303 (17)	0.00616 (6)	0.0629 (4)
H1	0.3359	0.3326	−0.0382	0.076*
N2	0.70692 (12)	0.54844 (18)	0.14254 (7)	0.0630 (4)
O1	0.50438 (8)	0.17832 (12)	0.23712 (5)	0.0523 (3)
O2	0.47216 (10)	0.34802 (17)	0.34197 (6)	0.0765 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0484 (8)	0.0492 (9)	0.0412 (7)	0.0003 (6)	0.0104 (6)	0.0016 (7)
C2	0.0464 (7)	0.0463 (8)	0.0394 (7)	0.0010 (6)	0.0112 (6)	0.0031 (6)
C3	0.0495 (8)	0.0443 (8)	0.0401 (7)	0.0024 (6)	0.0120 (6)	0.0019 (6)
C4	0.0439 (7)	0.0510 (9)	0.0386 (7)	−0.0013 (6)	0.0056 (6)	0.0071 (6)
C5	0.0459 (7)	0.0485 (8)	0.0365 (7)	−0.0046 (6)	0.0081 (6)	0.0004 (6)
C31	0.0492 (8)	0.0453 (8)	0.0407 (7)	0.0048 (6)	0.0077 (6)	−0.0002 (6)
C32	0.0478 (8)	0.0429 (8)	0.0480 (8)	0.0054 (6)	0.0048 (6)	−0.0030 (6)
C33	0.0540 (9)	0.0594 (11)	0.0638 (10)	0.0033 (7)	0.0146 (8)	−0.0020 (8)
C34	0.0556 (10)	0.0716 (12)	0.0970 (14)	−0.0004 (9)	0.0246 (10)	−0.0079 (11)
C35	0.0495 (10)	0.0815 (14)	0.1046 (16)	0.0016 (9)	0.0012 (11)	−0.0131 (12)
C36	0.0620 (11)	0.0755 (13)	0.0698 (12)	0.0075 (9)	−0.0140 (9)	−0.0043 (10)
C37	0.0569 (9)	0.0504 (9)	0.0531 (9)	0.0066 (7)	0.0009 (7)	−0.0010 (7)
C38	0.0605 (9)	0.0560 (10)	0.0432 (8)	−0.0007 (7)	0.0081 (7)	0.0017 (7)
C41	0.0444 (8)	0.0544 (9)	0.0477 (8)	0.0006 (7)	0.0128 (6)	0.0101 (7)
C42	0.0485 (8)	0.0507 (9)	0.0414 (7)	−0.0031 (6)	0.0157 (6)	0.0091 (6)
C43	0.0688 (10)	0.0625 (10)	0.0503 (9)	0.0030 (8)	0.0235 (8)	0.0045 (8)
C44	0.0986 (14)	0.0742 (13)	0.0470 (9)	−0.0058 (11)	0.0226 (9)	−0.0028 (9)
C45	0.0854 (13)	0.0796 (13)	0.0441 (9)	−0.0160 (10)	0.0055 (8)	0.0071 (9)
C46	0.0655 (10)	0.0733 (12)	0.0560 (10)	0.0025 (9)	0.0050 (8)	0.0166 (9)
C47	0.0604 (9)	0.0595 (10)	0.0472 (8)	0.0034 (7)	0.0118 (7)	0.0077 (7)
C51	0.0427 (7)	0.0535 (9)	0.0351 (7)	−0.0030 (6)	0.0071 (5)	0.0062 (6)
C52	0.0477 (8)	0.0690 (11)	0.0578 (9)	−0.0054 (8)	0.0020 (7)	−0.0060 (8)
C53	0.0426 (8)	0.0892 (14)	0.0756 (11)	0.0024 (9)	0.0022 (8)	0.0033 (11)
C54	0.0583 (10)	0.0767 (13)	0.0704 (11)	0.0155 (9)	0.0194 (8)	0.0117 (10)
C55	0.0697 (11)	0.0649 (11)	0.0615 (10)	0.0089 (9)	0.0167 (8)	−0.0048 (8)
C56	0.0491 (8)	0.0642 (10)	0.0470 (8)	−0.0022 (7)	0.0049 (6)	−0.0029 (8)
N1	0.0715 (9)	0.0669 (9)	0.0396 (7)	0.0017 (7)	0.0006 (6)	0.0059 (6)
N2	0.0694 (9)	0.0656 (9)	0.0540 (8)	−0.0076 (7)	0.0185 (7)	0.0088 (7)
O1	0.0495 (6)	0.0612 (7)	0.0406 (5)	−0.0114 (5)	0.0055 (4)	0.0070 (5)
O2	0.0551 (7)	0.1000 (10)	0.0680 (7)	0.0243 (7)	0.0089 (6)	−0.0007 (7)

C1—N2	1.1454 (18)	C38—H38	0.9300
C1—C2	1.404 (2)	C41—O2	1.2024 (17)
C2—C3	1.3469 (19)	C41—C42	1.4925 (19)
C2—C5	1.5174 (18)	C42—C43	1.380 (2)
C3—O1	1.3552 (17)	C42—C47	1.385 (2)
C3—C31	1.4443 (19)	C43—C44	1.376 (2)
C4—O1	1.4398 (15)	C43—H43	0.9300
C4—C41	1.517 (2)	C44—C45	1.370 (3)
C4—C5	1.5558 (19)	C44—H44	0.9300
C4—H4	0.9800	C45—C46	1.373 (3)
C5—C51	1.509 (2)	C45—H45	0.9300
C5—H5	0.9800	C46—C47	1.383 (2)
C31—C38	1.370 (2)	C46—H46	0.9300
C31—C32	1.442 (2)	C47—H47	0.9300
C32—C33	1.398 (2)	C51—C56	1.382 (2)
C32—C37	1.400 (2)	C51—C52	1.3847 (19)
C33—C34	1.376 (2)	C52—C53	1.381 (2)
C33—H33	0.9300	C52—H52	0.9300
C34—C35	1.389 (3)	C53—C54	1.361 (3)
C34—H34	0.9300	C53—H53	0.9300
C35—C36	1.367 (3)	C54—C55	1.374 (2)
C35—H35	0.9300	C54—H54	0.9300
C36—C37	1.388 (2)	C55—C56	1.372 (2)
C36—H36	0.9300	C55—H55	0.9300
C37—N1	1.372 (2)	C56—H56	0.9300
C38—N1	1.3557 (19)	N1—H1	0.8600
N2—C1—C2	179.19 (17)	O2—C41—C42	121.82 (14)
C3—C2—C1	124.91 (13)	O2—C41—C4	120.85 (13)
C3—C2—C5	110.46 (12)	C42—C41—C4	117.29 (12)
C1—C2—C5	124.63 (12)	C43—C42—C47	119.23 (14)
C2—C3—O1	112.80 (12)	C43—C42—C41	118.02 (13)
C2—C3—C31	132.33 (14)	C47—C42—C41	122.75 (14)
O1—C3—C31	114.84 (12)	C44—C43—C42	120.44 (16)
O1—C4—C41	109.35 (11)	C44—C43—H43	119.8
O1—C4—C5	107.16 (10)	C42—C43—H43	119.8
C41—C4—C5	111.55 (12)	C45—C44—C43	120.12 (17)
O1—C4—H4	109.6	C45—C44—H44	119.9
C41—C4—H4	109.6	C43—C44—H44	119.9
C5—C4—H4	109.6	C44—C45—C46	120.17 (16)
C51—C5—C2	113.71 (11)	C44—C45—H45	119.9
C51—C5—C4	113.81 (12)	C46—C45—H45	119.9
C2—C5—C4	99.04 (10)	C45—C46—C47	120.03 (17)
C51—C5—H5	109.9	C45—C46—H46	120.0
C2—C5—H5	109.9	C47—C46—H46	120.0
C4—C5—H5	109.9	C46—C47—C42	120.01 (16)
C38—C31—C32	106.70 (12)	C46—C47—H47	120.0
C38—C31—C3	126.34 (14)	C42—C47—H47	120.0
C32—C31—C3	126.81 (13)	C56—C51—C52	117.97 (14)
C33—C32—C37	119.04 (14)	C56—C51—C5	120.70 (12)
C33—C32—C31	134.57 (13)	C52—C51—C5	121.32 (14)
C37—C32—C31	106.39 (14)	C53—C52—C51	120.55 (16)
C34—C33—C32	118.29 (16)	C53—C52—H52	119.7
C34—C33—H33	120.9	C51—C52—H52	119.7
C32—C33—H33	120.9	C54—C53—C52	120.60 (15)
C33—C34—C35	121.58 (19)	C54—C53—H53	119.7
C33—C34—H34	119.2	C52—C53—H53	119.7
C35—C34—H34	119.2	C53—C54—C55	119.50 (16)
C36—C35—C34	121.28 (17)	C53—C54—H54	120.3
C36—C35—H35	119.4	C55—C54—H54	120.3
C34—C35—H35	119.4	C56—C55—C54	120.24 (17)
C35—C36—C37	117.53 (17)	C56—C55—H55	119.9
C35—C36—H36	121.2	C54—C55—H55	119.9
C37—C36—H36	121.2	C55—C56—C51	121.11 (14)
N1—C37—C36	130.07 (16)	C55—C56—H56	119.4
N1—C37—C32	107.68 (13)	C51—C56—H56	119.4
C36—C37—C32	122.24 (17)	C38—N1—C37	109.80 (13)
N1—C38—C31	109.43 (15)	C38—N1—H1	125.1
N1—C38—H38	125.3	C37—N1—H1	125.1
C31—C38—H38	125.3	C3—O1—C4	108.40 (10)
N2—C1—C2—C3	91 (13)	O1—C4—C41—O2	−10.0 (2)
N2—C1—C2—C5	−90 (13)	C5—C4—C41—O2	108.38 (16)
C1—C2—C3—O1	−175.50 (13)	O1—C4—C41—C42	172.28 (11)
C5—C2—C3—O1	5.01 (17)	C5—C4—C41—C42	−69.37 (16)
C1—C2—C3—C31	6.4 (3)	O2—C41—C42—C43	−13.3 (2)
C5—C2—C3—C31	−173.05 (15)	C4—C41—C42—C43	164.41 (13)
C3—C2—C5—C51	109.37 (14)	O2—C41—C42—C47	166.66 (16)
C1—C2—C5—C51	−70.13 (18)	C4—C41—C42—C47	−15.6 (2)
C3—C2—C5—C4	−11.72 (15)	C47—C42—C43—C44	−0.2 (2)
C1—C2—C5—C4	168.78 (14)	C41—C42—C43—C44	179.82 (15)
O1—C4—C5—C51	−106.79 (12)	C42—C43—C44—C45	−0.1 (3)
C41—C4—C5—C51	133.55 (12)	C43—C44—C45—C46	0.1 (3)
O1—C4—C5—C2	14.22 (14)	C44—C45—C46—C47	0.3 (3)
C41—C4—C5—C2	−105.43 (12)	C45—C46—C47—C42	−0.6 (3)
C2—C3—C31—C38	21.4 (3)	C43—C42—C47—C46	0.5 (2)
O1—C3—C31—C38	−156.61 (14)	C41—C42—C47—C46	−179.48 (14)
C2—C3—C31—C32	−163.71 (16)	C2—C5—C51—C56	−56.54 (18)
O1—C3—C31—C32	18.3 (2)	C4—C5—C51—C56	55.88 (17)
C38—C31—C32—C33	−178.57 (17)	C2—C5—C51—C52	124.44 (15)
C3—C31—C32—C33	5.7 (3)	C4—C5—C51—C52	−123.14 (15)
C38—C31—C32—C37	0.40 (16)	C56—C51—C52—C53	1.3 (2)
C3—C31—C32—C37	−175.29 (14)	C5—C51—C52—C53	−179.67 (15)
C37—C32—C33—C34	1.4 (2)	C51—C52—C53—C54	0.0 (3)
C31—C32—C33—C34	−179.72 (16)	C52—C53—C54—C55	−1.2 (3)
C32—C33—C34—C35	0.3 (3)	C53—C54—C55—C56	1.1 (3)
C33—C34—C35—C36	−1.3 (3)	C54—C55—C56—C51	0.3 (3)
C34—C35—C36—C37	0.5 (3)	C52—C51—C56—C55	−1.4 (2)
C35—C36—C37—N1	179.66 (18)	C5—C51—C56—C55	179.51 (14)
C35—C36—C37—C32	1.3 (3)	C31—C38—N1—C37	0.49 (18)
C33—C32—C37—N1	179.05 (14)	C36—C37—N1—C38	−178.77 (17)
C31—C32—C37—N1	−0.11 (17)	C32—C37—N1—C38	−0.22 (18)
C33—C32—C37—C36	−2.3 (2)	C2—C3—O1—C4	5.08 (16)
C31—C32—C37—C36	178.58 (15)	C31—C3—O1—C4	−176.50 (12)
C32—C31—C38—N1	−0.55 (17)	C41—C4—O1—C3	108.41 (13)
C3—C31—C38—N1	175.17 (14)	C5—C4—O1—C3	−12.65 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.93	2.56	3.040 (2)	112
C56—H56···O2i	0.93	2.45	3.330 (2)	158
N1—H1···N2ii	0.86	2.20	3.037 (2)	163
C43—H43···Cg1iii	0.93	2.96	3.410 (2)	112

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C31,C32,C37,C38 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯O1	0.93	2.56	3.040 (2)	112
C56—H56⋯O2i	0.93	2.45	3.330 (2)	158
N1—H1⋯N2ii	0.86	2.20	3.037 (2)	163
C43—H43⋯Cg1iii	0.93	2.96	3.410 (2)	112

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