Crystal structure of 5-benzoyl-2,4-di-phenyl-4,5-di-hydro-furan-3-carbo-nitrile.

In the title compound, C24H17NO2, the carbonyl O atom of the benzoyl group is cis with respect to the furanyl O atom, and the associated O-C-C-O torsion angle is 4.62 (19)°. The puckering of the dihydro-furan ring is close to twisted ((4) T 5), with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. Mol-ecules are inter-connected via a C-H⋯N and a C-H⋯O hydrogen bond, leading to layers parallel to the (200) plane and characterized by R 4 (4)(28) and R 4 (4)(36) graph-set motifs. The furan O atom does not participate in inter-molecular hydrogen bonding. The crystal lattice encompasses a solvent-accessible void of 24.7 (8) Å(3).

Related literature

For biological activity of di­hydro­furans, see: Simmonds et al. (1990 ▸); Gebbinck et al. (1999 ▸); Ley et al. (1987 ▸); Kumar et al. (2003 ▸); Pour et al. (2003 ▸); Loğoğlu et al. (2010 ▸). For Cambridge Structural Database, see: Groom & Allen (2014 ▸). For graph-set motifs, see: Bernstein et al. (1995 ▸). For puckering of rings, see: Cremer & Pople (1975 ▸). For related structures, see: Rajni Swamy et al. (2012 ▸); Suresh et al. (2012a ▸,b ▸,c ▸).

Experimental

Crystal data

C24H17NO2

M = 351.38

Monoclinic,

a = 10.0704 (7) Å

b = 15.7994 (12) Å

c = 11.8632 (9) Å

β = 98.886 (3)°

V = 1864.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.35 × 0.24 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.973, T max = 0.994

34345 measured reflections

4648 independent reflections

2305 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.147

S = 0.99

4648 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015014887/xu5865sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014887/xu5865Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014887/xu5865Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014887/xu5865fig1.tif

Mol­ecular structure of (I) showing the atom numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms and atoms of minor disordered components omitted for clarity.

Click here for additional data file.

b via . DOI: 10.1107/S2056989015014887/xu5865fig2.tif

A view down the b axis showing mol­ecules inter­connected via a C—H⋯N and a C—H⋯O hydrogen-bond leading to layers parallel to the (200) plane.

Click here for additional data file.

. DOI: 10.1107/S2056989015014887/xu5865fig3.tif

A view of the mol­ecules of the unit cell showing C—H⋯N and C—H⋯O hydrogen bonds.

CCDC reference: 1023392

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

C24H17NO2	F(000) = 736
Mr = 351.38	Dx = 1.252 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0704 (7) Å	Cell parameters from 2305 reflections
b = 15.7994 (12) Å	θ = 2.2–28.6°
c = 11.8632 (9) Å	µ = 0.08 mm−1
β = 98.886 (3)°	T = 298 K
V = 1864.9 (2) Å3	Block, colourless
Z = 4	0.35 × 0.24 × 0.08 mm

Bruker SMART APEXII CCD diffractometer	2305 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
ω and φ scans	θmax = 28.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
Tmin = 0.973, Tmax = 0.994	k = −21→21
34345 measured reflections	l = −15→15
4648 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0717P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.15 e Å−3
4648 reflections	Δρmin = −0.16 e Å−3
245 parameters	Extinction correction: SHELXL2014 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0097 (17)

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.

	x	y	z	Uiso*/Ueq
O1	0.65312 (11)	0.12681 (7)	−0.07149 (10)	0.0503 (3)
O2	0.63839 (11)	0.02849 (7)	0.10317 (10)	0.0584 (4)
N1	0.84295 (18)	0.37076 (11)	0.11942 (17)	0.0817 (6)
C1	0.74999 (16)	0.18513 (10)	−0.03978 (14)	0.0430 (4)
C2	0.70930 (15)	0.24665 (10)	0.02407 (13)	0.0423 (4)
C3	0.56268 (15)	0.23450 (9)	0.03502 (13)	0.0416 (4)
H3	0.5515	0.2365	0.1156	0.050*
C4	0.54406 (15)	0.14312 (9)	−0.00964 (14)	0.0432 (4)
H4	0.4586	0.1385	−0.0614	0.052*
C5	0.54745 (15)	0.07881 (10)	0.08555 (14)	0.0425 (4)
C6	0.43803 (15)	0.08113 (10)	0.15584 (14)	0.0436 (4)
C7	0.32474 (17)	0.13099 (11)	0.12818 (16)	0.0529 (5)
H7	0.3158	0.1651	0.0635	0.063*
C8	0.22520 (18)	0.13050 (12)	0.19565 (18)	0.0639 (5)
H8	0.1487	0.1635	0.1759	0.077*
C9	0.23861 (19)	0.08169 (13)	0.29133 (18)	0.0673 (6)
H9	0.1720	0.0821	0.3376	0.081*
C10	0.3498 (2)	0.03227 (13)	0.31933 (18)	0.0690 (6)
H10	0.3584	−0.0011	0.3846	0.083*
C11	0.44916 (18)	0.03135 (11)	0.25209 (16)	0.0557 (5)
H11	0.5242	−0.0030	0.2716	0.067*
C12	0.87832 (16)	0.16935 (11)	−0.07951 (14)	0.0466 (4)
C13	0.9140 (2)	0.08775 (12)	−0.10240 (16)	0.0633 (5)
H13	0.8558	0.0433	−0.0941	0.076*
C14	1.0350 (2)	0.07193 (15)	−0.13726 (19)	0.0773 (6)
H14	1.0591	0.0165	−0.1513	0.093*
C15	1.12049 (19)	0.13654 (15)	−0.15166 (17)	0.0702 (6)
H15	1.2021	0.1253	−0.1760	0.084*
C16	1.08594 (19)	0.21745 (15)	−0.13026 (17)	0.0691 (6)
H16	1.1441	0.2616	−0.1402	0.083*
C17	0.96536 (17)	0.23435 (12)	−0.09402 (16)	0.0594 (5)
H17	0.9425	0.2898	−0.0793	0.071*
C18	0.47459 (14)	0.29991 (9)	−0.03105 (13)	0.0414 (4)
C19	0.44746 (16)	0.29744 (10)	−0.14855 (15)	0.0488 (4)
H19	0.4797	0.2527	−0.1876	0.059*
C20	0.37323 (16)	0.36044 (11)	−0.20860 (16)	0.0565 (5)
H20	0.3551	0.3577	−0.2878	0.068*
C21	0.32609 (18)	0.42665 (12)	−0.15322 (19)	0.0635 (5)
H21	0.2763	0.4692	−0.1942	0.076*
C22	0.3523 (2)	0.43001 (12)	−0.03784 (19)	0.0745 (6)
H22	0.3207	0.4754	0.0003	0.089*
C23	0.42525 (19)	0.36704 (11)	0.02362 (17)	0.0646 (5)
H23	0.4413	0.3699	0.1029	0.078*
C24	0.78533 (16)	0.31484 (11)	0.07499 (16)	0.0513 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0546 (7)	0.0452 (7)	0.0539 (7)	−0.0099 (6)	0.0172 (6)	−0.0127 (5)
O2	0.0528 (7)	0.0550 (8)	0.0674 (9)	0.0109 (6)	0.0097 (6)	0.0034 (6)
N1	0.0806 (12)	0.0659 (11)	0.0966 (14)	−0.0206 (10)	0.0077 (10)	−0.0269 (10)
C1	0.0468 (9)	0.0375 (9)	0.0443 (10)	−0.0054 (8)	0.0060 (8)	0.0005 (8)
C2	0.0430 (9)	0.0367 (9)	0.0463 (10)	−0.0020 (7)	0.0035 (7)	−0.0019 (8)
C3	0.0487 (9)	0.0389 (9)	0.0379 (9)	−0.0027 (7)	0.0094 (7)	−0.0017 (7)
C4	0.0427 (9)	0.0431 (9)	0.0445 (10)	−0.0044 (7)	0.0089 (8)	−0.0045 (8)
C5	0.0413 (9)	0.0364 (9)	0.0482 (10)	−0.0045 (8)	0.0021 (8)	−0.0038 (8)
C6	0.0445 (9)	0.0393 (9)	0.0466 (10)	−0.0038 (8)	0.0059 (8)	0.0007 (8)
C7	0.0467 (10)	0.0562 (11)	0.0559 (11)	0.0022 (9)	0.0081 (9)	0.0100 (9)
C8	0.0515 (11)	0.0690 (13)	0.0716 (14)	0.0094 (10)	0.0111 (10)	0.0070 (11)
C9	0.0635 (13)	0.0747 (13)	0.0692 (14)	−0.0002 (11)	0.0281 (11)	0.0056 (11)
C10	0.0703 (13)	0.0761 (14)	0.0635 (13)	0.0015 (11)	0.0192 (11)	0.0218 (11)
C11	0.0564 (11)	0.0520 (11)	0.0589 (12)	0.0038 (9)	0.0092 (9)	0.0108 (9)
C12	0.0482 (10)	0.0476 (10)	0.0445 (10)	0.0023 (8)	0.0084 (8)	0.0031 (8)
C13	0.0719 (13)	0.0543 (12)	0.0687 (14)	0.0009 (10)	0.0264 (10)	−0.0070 (10)
C14	0.0773 (14)	0.0734 (15)	0.0873 (17)	0.0169 (13)	0.0319 (12)	−0.0070 (12)
C15	0.0540 (12)	0.1010 (18)	0.0580 (13)	0.0167 (13)	0.0167 (10)	0.0003 (12)
C16	0.0489 (11)	0.0859 (16)	0.0743 (15)	−0.0054 (11)	0.0151 (10)	0.0106 (12)
C17	0.0522 (11)	0.0547 (11)	0.0727 (14)	0.0007 (9)	0.0144 (10)	0.0062 (10)
C18	0.0399 (9)	0.0406 (9)	0.0450 (10)	−0.0033 (7)	0.0106 (7)	−0.0037 (8)
C19	0.0503 (10)	0.0482 (10)	0.0487 (11)	0.0018 (8)	0.0100 (8)	−0.0028 (8)
C20	0.0543 (11)	0.0626 (12)	0.0510 (11)	−0.0020 (10)	0.0032 (9)	0.0056 (10)
C21	0.0557 (11)	0.0582 (12)	0.0752 (15)	0.0094 (10)	0.0050 (10)	0.0093 (11)
C22	0.0857 (15)	0.0630 (13)	0.0764 (16)	0.0308 (12)	0.0173 (12)	−0.0053 (11)
C23	0.0802 (13)	0.0641 (12)	0.0503 (12)	0.0166 (11)	0.0125 (10)	−0.0083 (10)
C24	0.0503 (10)	0.0459 (10)	0.0564 (11)	−0.0014 (9)	0.0047 (9)	−0.0047 (9)

O1—C1	1.3523 (18)	C11—H11	0.9300
O1—C4	1.4352 (18)	C12—C13	1.377 (2)
O2—C5	1.2064 (17)	C12—C17	1.378 (2)
N1—C24	1.140 (2)	C13—C14	1.368 (3)
C1—C2	1.335 (2)	C13—H13	0.9300
C1—C12	1.464 (2)	C14—C15	1.363 (3)
C2—C24	1.403 (2)	C14—H14	0.9300
C2—C3	1.514 (2)	C15—C16	1.359 (3)
C3—C18	1.502 (2)	C15—H15	0.9300
C3—C4	1.539 (2)	C16—C17	1.375 (2)
C3—H3	0.9800	C16—H16	0.9300
C4—C5	1.516 (2)	C17—H17	0.9300
C4—H4	0.9800	C18—C23	1.375 (2)
C5—C6	1.481 (2)	C18—C19	1.379 (2)
C6—C11	1.377 (2)	C19—C20	1.376 (2)
C6—C7	1.384 (2)	C19—H19	0.9300
C7—C8	1.376 (2)	C20—C21	1.359 (3)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.362 (3)	C21—C22	1.354 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.363 (3)	C22—C23	1.377 (3)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.373 (2)	C23—H23	0.9300
C10—H10	0.9300
C1—O1—C4	108.15 (11)	C6—C11—H11	119.9
C2—C1—O1	112.48 (14)	C13—C12—C17	118.86 (16)
C2—C1—C12	132.09 (15)	C13—C12—C1	119.57 (16)
O1—C1—C12	115.42 (13)	C17—C12—C1	121.57 (16)
C1—C2—C24	127.47 (15)	C14—C13—C12	120.16 (19)
C1—C2—C3	110.19 (13)	C14—C13—H13	119.9
C24—C2—C3	122.34 (14)	C12—C13—H13	119.9
C18—C3—C2	111.91 (12)	C15—C14—C13	120.7 (2)
C18—C3—C4	115.79 (13)	C15—C14—H14	119.7
C2—C3—C4	99.09 (12)	C13—C14—H14	119.7
C18—C3—H3	109.9	C16—C15—C14	119.74 (18)
C2—C3—H3	109.9	C16—C15—H15	120.1
C4—C3—H3	109.9	C14—C15—H15	120.1
O1—C4—C5	109.25 (12)	C15—C16—C17	120.32 (19)
O1—C4—C3	106.39 (12)	C15—C16—H16	119.8
C5—C4—C3	112.63 (13)	C17—C16—H16	119.8
O1—C4—H4	109.5	C16—C17—C12	120.24 (18)
C5—C4—H4	109.5	C16—C17—H17	119.9
C3—C4—H4	109.5	C12—C17—H17	119.9
O2—C5—C6	121.97 (15)	C23—C18—C19	117.96 (15)
O2—C5—C4	120.00 (14)	C23—C18—C3	120.79 (15)
C6—C5—C4	118.02 (14)	C19—C18—C3	121.13 (14)
C11—C6—C7	118.72 (16)	C20—C19—C18	120.66 (16)
C11—C6—C5	118.71 (15)	C20—C19—H19	119.7
C7—C6—C5	122.57 (15)	C18—C19—H19	119.7
C8—C7—C6	120.46 (17)	C21—C20—C19	120.59 (18)
C8—C7—H7	119.8	C21—C20—H20	119.7
C6—C7—H7	119.8	C19—C20—H20	119.7
C9—C8—C7	120.05 (18)	C22—C21—C20	119.37 (18)
C9—C8—H8	120.0	C22—C21—H21	120.3
C7—C8—H8	120.0	C20—C21—H21	120.3
C8—C9—C10	119.96 (18)	C21—C22—C23	120.77 (18)
C8—C9—H9	120.0	C21—C22—H22	119.6
C10—C9—H9	120.0	C23—C22—H22	119.6
C9—C10—C11	120.62 (18)	C18—C23—C22	120.63 (18)
C9—C10—H10	119.7	C18—C23—H23	119.7
C11—C10—H10	119.7	C22—C23—H23	119.7
C10—C11—C6	120.17 (17)	N1—C24—C2	177.0 (2)
C10—C11—H11	119.9
C4—O1—C1—C2	−9.45 (18)	C8—C9—C10—C11	0.2 (3)
C4—O1—C1—C12	169.86 (13)	C9—C10—C11—C6	0.6 (3)
O1—C1—C2—C24	177.16 (15)	C7—C6—C11—C10	−0.6 (3)
C12—C1—C2—C24	−2.0 (3)	C5—C6—C11—C10	179.74 (17)
O1—C1—C2—C3	−3.50 (19)	C2—C1—C12—C13	153.06 (19)
C12—C1—C2—C3	177.34 (16)	O1—C1—C12—C13	−26.1 (2)
C1—C2—C3—C18	−109.07 (15)	C2—C1—C12—C17	−26.5 (3)
C24—C2—C3—C18	70.31 (19)	O1—C1—C12—C17	154.34 (15)
C1—C2—C3—C4	13.56 (16)	C17—C12—C13—C14	1.0 (3)
C24—C2—C3—C4	−167.06 (15)	C1—C12—C13—C14	−178.61 (17)
C1—O1—C4—C5	−103.83 (13)	C12—C13—C14—C15	−1.1 (3)
C1—O1—C4—C3	18.00 (16)	C13—C14—C15—C16	0.6 (3)
C18—C3—C4—O1	101.41 (15)	C14—C15—C16—C17	0.1 (3)
C2—C3—C4—O1	−18.39 (15)	C15—C16—C17—C12	−0.2 (3)
C18—C3—C4—C5	−138.92 (14)	C13—C12—C17—C16	−0.3 (3)
C2—C3—C4—C5	101.28 (14)	C1—C12—C17—C16	179.27 (16)
O1—C4—C5—O2	4.62 (19)	C2—C3—C18—C23	−103.03 (18)
C3—C4—C5—O2	−113.38 (16)	C4—C3—C18—C23	144.42 (16)
O1—C4—C5—C6	−176.36 (12)	C2—C3—C18—C19	72.97 (17)
C3—C4—C5—C6	65.64 (17)	C4—C3—C18—C19	−39.6 (2)
O2—C5—C6—C11	7.9 (2)	C23—C18—C19—C20	0.0 (2)
C4—C5—C6—C11	−171.09 (15)	C3—C18—C19—C20	−176.12 (14)
O2—C5—C6—C7	−171.69 (15)	C18—C19—C20—C21	0.5 (3)
C4—C5—C6—C7	9.3 (2)	C19—C20—C21—C22	−0.3 (3)
C11—C6—C7—C8	−0.1 (3)	C20—C21—C22—C23	−0.4 (3)
C5—C6—C7—C8	179.46 (16)	C19—C18—C23—C22	−0.7 (3)
C6—C7—C8—C9	1.0 (3)	C3—C18—C23—C22	175.45 (16)
C7—C8—C9—C10	−1.0 (3)	C21—C22—C23—C18	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N1i	0.93	2.63	3.487 (2)	154
C21—H21···O2ii	0.93	2.58	3.277 (2)	132

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C11H11N1i	0.93	2.63	3.487(2)	154
C21H21O2ii	0.93	2.58	3.277(2)	132

Symmetry codes: (i) ; (ii) .