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

The furan ring in the title compound, C(26)H(17)BrN(2)O(2), adopts a twisted envelope conformation. 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⋯Br inter-actions, generating an R(2) (2)(16) ring motif and a C(12) linear chain motif, respectively. Weak C-H⋯π bonding is also observed.

Related literature

For the importance of furan derivatives, see: Auvin & Chabrier De Lassauniere (2005 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H17BrN2O2

M = 469.33

Monoclinic,

a = 9.8003 (6) Å

b = 15.8876 (10) Å

c = 13.5588 (9) Å

β = 100.306 (3)°

V = 2077.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.01 mm−1

T = 293 K

0.18 × 0.16 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer

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

17242 measured reflections

3635 independent reflections

2366 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.108

S = 1.02

3635 reflections

284 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.78 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/S1600536812030073/tk5125sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030073/tk5125Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030073/tk5125Isup3.cml

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

C26H17BrN2O2	F(000) = 952
Mr = 469.33	Dx = 1.501 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 9.8003 (6) Å	θ = 2.4–25°
b = 15.8876 (10) Å	µ = 2.01 mm−1
c = 13.5588 (9) Å	T = 293 K
β = 100.306 (3)°	Block, pale-yellow
V = 2077.1 (2) Å3	0.18 × 0.16 × 0.13 mm
Z = 4

Bruker Kappa APEXII diffractometer	3635 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω and φ scans	h = −7→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.967, Tmax = 0.974	l = −16→16
17242 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0397P)2 + 1.5055P] where P = (Fo2 + 2Fc2)/3
3635 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.78 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	0.724 (3)	0.5931 (19)	0.496 (2)	0.038 (10)*
Br1	0.09434 (6)	0.43918 (4)	−0.23671 (3)	0.1182 (3)
O1	0.37349 (19)	0.36776 (12)	0.29701 (14)	0.0353 (5)
O2	0.1364 (2)	0.35231 (14)	0.36843 (15)	0.0477 (6)
N2	0.6871 (3)	0.55400 (18)	0.4627 (2)	0.0397 (7)
C53	0.2243 (4)	0.4273 (2)	−0.1174 (2)	0.0546 (9)
C41	0.1258 (3)	0.34022 (18)	0.2795 (2)	0.0342 (7)
C32	0.6256 (3)	0.41997 (18)	0.4271 (2)	0.0311 (7)
C42	−0.0082 (3)	0.31506 (18)	0.2155 (2)	0.0344 (7)
C4	0.2472 (3)	0.35510 (18)	0.2255 (2)	0.0322 (7)
H4	0.2578	0.3069	0.1825	0.039*
C38	0.5653 (3)	0.55612 (19)	0.3984 (2)	0.0374 (7)
H38	0.5176	0.6048	0.3751	0.045*
C2	0.3141 (3)	0.49622 (17)	0.2325 (2)	0.0308 (7)
C31	0.5221 (3)	0.47582 (18)	0.3725 (2)	0.0301 (7)
C51	0.2728 (3)	0.42821 (17)	0.0617 (2)	0.0331 (7)
C1	0.3123 (3)	0.5839 (2)	0.2189 (2)	0.0376 (7)
C34	0.7591 (3)	0.3023 (2)	0.4948 (2)	0.0459 (8)
H34	0.7713	0.2443	0.5003	0.055*
C37	0.7273 (3)	0.47240 (19)	0.4816 (2)	0.0342 (7)
C5	0.2256 (3)	0.43649 (17)	0.1618 (2)	0.0316 (7)
H5	0.1281	0.4539	0.1518	0.038*
C43	−0.0195 (3)	0.2963 (2)	0.1148 (2)	0.0418 (8)
H43	0.0592	0.2981	0.0853	0.050*
C3	0.4017 (3)	0.45201 (18)	0.3016 (2)	0.0313 (7)
C52	0.1805 (3)	0.4376 (2)	−0.0265 (2)	0.0459 (8)
H52	0.0884	0.4509	−0.0252	0.055*
C44	−0.1450 (3)	0.2749 (2)	0.0575 (2)	0.0479 (9)
H44	−0.1512	0.2633	−0.0104	0.057*
C56	0.4098 (3)	0.4092 (2)	0.0573 (2)	0.0412 (8)
H56	0.4742	0.4037	0.1162	0.049*
C47	−0.1259 (3)	0.3112 (2)	0.2575 (3)	0.0585 (10)
H47	−0.1209	0.3240	0.3250	0.070*
C36	0.8450 (3)	0.4407 (2)	0.5426 (2)	0.0469 (9)
H36	0.9115	0.4763	0.5783	0.056*
C33	0.6428 (3)	0.33344 (19)	0.4342 (2)	0.0365 (7)
H33	0.5771	0.2973	0.3988	0.044*
C54	0.3588 (4)	0.4073 (2)	−0.1217 (3)	0.0538 (9)
H54	0.3871	0.4000	−0.1830	0.065*
C35	0.8592 (3)	0.3552 (2)	0.5481 (3)	0.0524 (9)
H35	0.9371	0.3319	0.5881	0.063*
N1	0.3062 (3)	0.65498 (19)	0.2061 (2)	0.0598 (8)
C45	−0.2606 (4)	0.2708 (2)	0.1007 (3)	0.0601 (10)
H45	−0.3457	0.2561	0.0625	0.072*
C55	0.4510 (3)	0.3983 (2)	−0.0336 (3)	0.0508 (9)
H55	0.5428	0.3846	−0.0354	0.061*
C46	−0.2505 (4)	0.2885 (3)	0.2002 (3)	0.0742 (12)
H46	−0.3291	0.2851	0.2297	0.089*

	U11	U22	U33	U12	U13	U23
Br1	0.1313 (5)	0.1734 (6)	0.0363 (3)	0.0828 (4)	−0.0219 (3)	−0.0174 (3)
O1	0.0322 (11)	0.0287 (12)	0.0400 (12)	−0.0040 (9)	−0.0073 (9)	0.0007 (9)
O2	0.0534 (14)	0.0585 (15)	0.0302 (12)	−0.0101 (11)	0.0049 (10)	−0.0076 (10)
N2	0.0401 (16)	0.0376 (18)	0.0367 (15)	−0.0097 (14)	−0.0060 (12)	−0.0074 (13)
C53	0.071 (3)	0.056 (2)	0.0317 (18)	0.0146 (19)	−0.0045 (17)	−0.0030 (16)
C41	0.0402 (18)	0.0276 (17)	0.0332 (18)	−0.0026 (13)	0.0019 (14)	−0.0010 (13)
C32	0.0306 (16)	0.0357 (18)	0.0275 (15)	0.0005 (14)	0.0062 (13)	0.0003 (13)
C42	0.0328 (16)	0.0336 (18)	0.0358 (17)	−0.0035 (14)	0.0032 (14)	0.0012 (13)
C4	0.0301 (16)	0.0313 (17)	0.0317 (16)	−0.0021 (13)	−0.0040 (13)	−0.0039 (13)
C38	0.0384 (18)	0.038 (2)	0.0338 (16)	−0.0001 (14)	−0.0002 (14)	−0.0003 (14)
C2	0.0329 (16)	0.0280 (17)	0.0298 (16)	−0.0018 (13)	0.0012 (13)	−0.0035 (13)
C31	0.0321 (16)	0.0297 (17)	0.0276 (15)	−0.0005 (13)	0.0028 (13)	−0.0014 (13)
C51	0.0383 (17)	0.0269 (16)	0.0323 (16)	−0.0053 (13)	0.0011 (13)	−0.0015 (12)
C1	0.0363 (18)	0.038 (2)	0.0350 (17)	−0.0017 (16)	−0.0027 (14)	−0.0018 (15)
C34	0.050 (2)	0.041 (2)	0.0476 (19)	0.0092 (17)	0.0098 (17)	0.0072 (16)
C37	0.0335 (17)	0.0386 (19)	0.0296 (16)	−0.0027 (14)	0.0035 (13)	−0.0019 (14)
C5	0.0290 (15)	0.0297 (17)	0.0335 (16)	0.0006 (13)	−0.0011 (13)	−0.0022 (13)
C43	0.0348 (18)	0.048 (2)	0.0419 (18)	−0.0074 (15)	0.0036 (15)	−0.0050 (15)
C3	0.0322 (16)	0.0288 (17)	0.0324 (16)	−0.0029 (13)	0.0049 (13)	−0.0036 (13)
C52	0.047 (2)	0.051 (2)	0.0349 (18)	0.0143 (16)	−0.0045 (15)	−0.0044 (15)
C44	0.046 (2)	0.053 (2)	0.0420 (19)	−0.0076 (17)	−0.0018 (16)	−0.0031 (16)
C56	0.0344 (18)	0.048 (2)	0.0392 (18)	−0.0086 (15)	0.0019 (14)	−0.0010 (15)
C47	0.045 (2)	0.088 (3)	0.044 (2)	−0.0136 (19)	0.0106 (17)	−0.0030 (19)
C36	0.0358 (18)	0.060 (2)	0.0404 (19)	0.0025 (16)	−0.0059 (15)	−0.0049 (17)
C33	0.0387 (18)	0.0374 (19)	0.0334 (16)	0.0008 (15)	0.0062 (14)	0.0008 (14)
C54	0.073 (3)	0.051 (2)	0.041 (2)	0.0002 (19)	0.0190 (19)	−0.0006 (16)
C35	0.040 (2)	0.065 (3)	0.048 (2)	0.0150 (18)	−0.0030 (16)	0.0059 (18)
N1	0.069 (2)	0.0371 (19)	0.067 (2)	−0.0010 (16)	−0.0045 (16)	0.0038 (16)
C45	0.037 (2)	0.070 (3)	0.067 (3)	−0.0065 (18)	−0.0064 (19)	−0.001 (2)
C55	0.043 (2)	0.058 (2)	0.053 (2)	−0.0068 (17)	0.0142 (18)	−0.0010 (18)
C46	0.038 (2)	0.120 (4)	0.066 (3)	−0.015 (2)	0.012 (2)	−0.006 (3)

Br1—C53	1.881 (3)	C51—C5	1.516 (4)
O1—C3	1.366 (3)	C1—N1	1.143 (4)
O1—C4	1.443 (3)	C34—C33	1.372 (4)
O2—C41	1.207 (3)	C34—C35	1.392 (5)
N2—C38	1.347 (4)	C34—H34	0.9300
N2—C37	1.366 (4)	C37—C36	1.388 (4)
N2—H2	0.81 (3)	C5—H5	0.9800
C53—C54	1.367 (5)	C43—C44	1.375 (4)
C53—C52	1.386 (5)	C43—H43	0.9300
C41—C42	1.493 (4)	C52—H52	0.9300
C41—C4	1.523 (4)	C44—C45	1.367 (5)
C32—C33	1.386 (4)	C44—H44	0.9300
C32—C37	1.404 (4)	C56—C55	1.375 (4)
C32—C31	1.448 (4)	C56—H56	0.9300
C42—C47	1.376 (4)	C47—C46	1.374 (5)
C42—C43	1.383 (4)	C47—H47	0.9300
C4—C5	1.548 (4)	C36—C35	1.367 (5)
C4—H4	0.9800	C36—H36	0.9300
C38—C31	1.370 (4)	C33—H33	0.9300
C38—H38	0.9300	C54—C55	1.369 (5)
C2—C3	1.350 (4)	C54—H54	0.9300
C2—C1	1.405 (4)	C35—H35	0.9300
C2—C5	1.508 (4)	C45—C46	1.365 (5)
C31—C3	1.432 (4)	C45—H45	0.9300
C51—C52	1.373 (4)	C55—H55	0.9300
C51—C56	1.387 (4)	C46—H46	0.9300
C3—O1—C4	108.0 (2)	C51—C5—C4	113.2 (2)
C38—N2—C37	109.7 (3)	C2—C5—H5	110.3
C38—N2—H2	126 (2)	C51—C5—H5	110.3
C37—N2—H2	123 (2)	C4—C5—H5	110.3
C54—C53—C52	121.3 (3)	C44—C43—C42	121.1 (3)
C54—C53—Br1	119.8 (3)	C44—C43—H43	119.4
C52—C53—Br1	118.9 (3)	C42—C43—H43	119.4
O2—C41—C42	122.2 (3)	C2—C3—O1	112.3 (2)
O2—C41—C4	121.4 (3)	C2—C3—C31	132.4 (3)
C42—C41—C4	116.3 (2)	O1—C3—C31	115.2 (2)
C33—C32—C37	119.0 (3)	C51—C52—C53	120.1 (3)
C33—C32—C31	135.2 (3)	C51—C52—H52	120.0
C37—C32—C31	105.8 (2)	C53—C52—H52	120.0
C47—C42—C43	118.4 (3)	C45—C44—C43	119.7 (3)
C47—C42—C41	119.1 (3)	C45—C44—H44	120.1
C43—C42—C41	122.6 (3)	C43—C44—H44	120.1
O1—C4—C41	110.4 (2)	C55—C56—C51	120.6 (3)
O1—C4—C5	105.9 (2)	C55—C56—H56	119.7
C41—C4—C5	110.9 (2)	C51—C56—H56	119.7
O1—C4—H4	109.9	C46—C47—C42	120.3 (3)
C41—C4—H4	109.9	C46—C47—H47	119.9
C5—C4—H4	109.9	C42—C47—H47	119.9
N2—C38—C31	109.9 (3)	C35—C36—C37	117.3 (3)
N2—C38—H38	125.0	C35—C36—H36	121.3
C31—C38—H38	125.0	C37—C36—H36	121.3
C3—C2—C1	126.8 (3)	C34—C33—C32	118.5 (3)
C3—C2—C5	109.7 (2)	C34—C33—H33	120.7
C1—C2—C5	123.2 (3)	C32—C33—H33	120.7
C38—C31—C3	126.7 (3)	C53—C54—C55	118.6 (3)
C38—C31—C32	106.4 (2)	C53—C54—H54	120.7
C3—C31—C32	126.8 (3)	C55—C54—H54	120.7
C52—C51—C56	118.5 (3)	C36—C35—C34	121.1 (3)
C52—C51—C5	120.7 (3)	C36—C35—H35	119.4
C56—C51—C5	120.7 (3)	C34—C35—H35	119.4
N1—C1—C2	177.7 (3)	C46—C45—C44	119.7 (3)
C33—C34—C35	121.7 (3)	C46—C45—H45	120.1
C33—C34—H34	119.2	C44—C45—H45	120.1
C35—C34—H34	119.2	C54—C55—C56	120.9 (3)
N2—C37—C36	129.6 (3)	C54—C55—H55	119.5
N2—C37—C32	108.1 (3)	C56—C55—H55	119.5
C36—C37—C32	122.3 (3)	C45—C46—C47	120.8 (3)
C2—C5—C51	113.0 (2)	C45—C46—H46	119.6
C2—C5—C4	99.5 (2)	C47—C46—H46	119.6
O2—C41—C42—C47	4.7 (4)	C47—C42—C43—C44	0.5 (5)
C4—C41—C42—C47	−171.8 (3)	C41—C42—C43—C44	−178.7 (3)
O2—C41—C42—C43	−176.1 (3)	C1—C2—C3—O1	178.2 (3)
C4—C41—C42—C43	7.5 (4)	C5—C2—C3—O1	−8.3 (3)
C3—O1—C4—C41	−102.4 (2)	C1—C2—C3—C31	−6.9 (5)
C3—O1—C4—C5	17.7 (3)	C5—C2—C3—C31	166.6 (3)
O2—C41—C4—O1	11.2 (4)	C4—O1—C3—C2	−6.4 (3)
C42—C41—C4—O1	−172.3 (2)	C4—O1—C3—C31	177.8 (2)
O2—C41—C4—C5	−105.8 (3)	C38—C31—C3—C2	11.8 (5)
C42—C41—C4—C5	70.7 (3)	C32—C31—C3—C2	−164.9 (3)
C37—N2—C38—C31	−0.4 (3)	C38—C31—C3—O1	−173.4 (3)
N2—C38—C31—C3	−176.2 (3)	C32—C31—C3—O1	9.9 (4)
N2—C38—C31—C32	1.0 (3)	C56—C51—C52—C53	0.6 (5)
C33—C32—C31—C38	179.8 (3)	C5—C51—C52—C53	−178.0 (3)
C37—C32—C31—C38	−1.2 (3)	C54—C53—C52—C51	0.3 (5)
C33—C32—C31—C3	−3.0 (5)	Br1—C53—C52—C51	179.1 (2)
C37—C32—C31—C3	176.0 (3)	C42—C43—C44—C45	−1.0 (5)
C38—N2—C37—C36	179.8 (3)	C52—C51—C56—C55	−1.3 (5)
C38—N2—C37—C32	−0.4 (3)	C5—C51—C56—C55	177.3 (3)
C33—C32—C37—N2	−179.8 (3)	C43—C42—C47—C46	0.5 (5)
C31—C32—C37—N2	1.0 (3)	C41—C42—C47—C46	179.8 (3)
C33—C32—C37—C36	0.0 (4)	N2—C37—C36—C35	179.8 (3)
C31—C32—C37—C36	−179.2 (3)	C32—C37—C36—C35	0.0 (5)
C3—C2—C5—C51	−102.5 (3)	C35—C34—C33—C32	−0.4 (4)
C1—C2—C5—C51	71.3 (3)	C37—C32—C33—C34	0.2 (4)
C3—C2—C5—C4	17.8 (3)	C31—C32—C33—C34	179.1 (3)
C1—C2—C5—C4	−168.4 (3)	C52—C53—C54—C55	−0.6 (5)
C52—C51—C5—C2	−129.2 (3)	Br1—C53—C54—C55	−179.4 (3)
C56—C51—C5—C2	52.2 (4)	C37—C36—C35—C34	−0.2 (5)
C52—C51—C5—C4	118.7 (3)	C33—C34—C35—C36	0.4 (5)
C56—C51—C5—C4	−60.0 (3)	C43—C44—C45—C46	0.4 (6)
O1—C4—C5—C2	−20.8 (3)	C53—C54—C55—C56	−0.1 (5)
C41—C4—C5—C2	99.0 (2)	C51—C56—C55—C54	1.1 (5)
O1—C4—C5—C51	99.3 (3)	C44—C45—C46—C47	0.7 (6)
C41—C4—C5—C51	−140.9 (2)	C42—C47—C46—C45	−1.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.93	2.48	2.995 (3)	115
N2—H2···O2i	0.81 (3)	2.26 (3)	3.006 (3)	153 (3)
C36—H36···Br1ii	0.93	2.87	3.509 (3)	127
C34—H34···Cg1iii	0.93	2.66	3.570 (3)	166
C47—H47···Cg2iv	0.93	2.95	3.784 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C51–C56 and C32–C37 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯O1	0.93	2.48	2.995 (3)	115
N2—H2⋯O2i	0.81 (3)	2.26 (3)	3.006 (3)	153 (3)
C36—H36⋯Br1ii	0.93	2.87	3.509 (3)	127
C34—H34⋯Cg1iii	0.93	2.66	3.570 (3)	166
C47—H47⋯Cg2iv	0.93	2.95	3.784 (4)	149

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