5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phen­yl]-4,5-dihydro­furan-3-carbonitrile

Rajni Swamy, V.; Krishnakumar, R.V.; Srinivasan, N.; Gunasekaran, P.; Perumal, S.

doi:10.1107/S1600536812046764

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3441

doi:10.1107/S1600536812046764

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5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phenyl]-4,5-dihydrofuran-3-carbonitrile

V. Rajni Swamy,^a R. V. Krishnakumar,^a ^* N. Srinivasan,^a P. Gunasekaran ^b and S. Perumal ^b

^aDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: mailtorvkk@yahoo.co.in

(Received 8 November 2012; accepted 13 November 2012; online 24 November 2012)

In the title compound, C₂₉H₂₄N₂O₂, the hydrofuran ring is twisted with puckering parameters Q = 0.1553 (16) Å and φ = 305.0 (6)°. In the crystal, the graph-set motifs of the interaction pattern are an R₂²(16) motif involving dimers through N—H⋯N hydrogen bonds across centres of inversion and a C(6) motif through C—H⋯O hydrogen-bond between glide-related molecules. Together, these generate [101] ladder-like chains.

Related literature

For related structures, see: Suresh et al. (2012a ,b ,c ). For discussion on aromatic interactions, see: Bloom & Wheeler (2011 ); Martinez & Iverson (2012 ). For graph-set motifs, see: Bernstein et al. (1995 ). For puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₉H₂₄N₂O₂
M_r = 432.50
Monoclinic, P 2₁ /n
a = 17.1073 (4) Å
b = 8.1230 (2) Å
c = 17.6160 (4) Å
β = 110.325 (1)°
V = 2295.55 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.978, T_max = 0.986
21711 measured reflections
4455 independent reflections
2979 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 1.03
4455 reflections
313 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1ⁱ	0.91 (2)	2.09 (2)	2.973 (2)	165.2 (17)
C56—H56⋯O2ⁱⁱ	0.978 (15)	2.411 (16)	3.371 (2)	166.9 (13)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046764/rz5022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046764/rz5022Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812046764/rz5022Isup3.cml

checkCIF report

Comment top

In the molecule of the title compound (Fig. 1), the puckering (Cremer & Pople, 1975) of the furan ring is twisted (⁴T₅) about the C4—C5 bond with Q = 0.1553 (16) Å and ϕ = 305.0 (6)°. The geometry of the N—H···N and C—H···O interactions that characterize the crystal packing (Table 1) are similar to its 4-phenyl analogue (Suresh et al., 2012a). The graph-set motifs (Bernstein et al., 1995) that characterize the intermolecular interaction pattern are a R²₂(16) involving dimers through N—H···N hydrogen bonds across centres of inversion and a C(6) motif through C—H···O hydrogen-bond between glide-related molecules (Fig. 2). The crystal structure may be visualized as zero-dimensional N—H···N mediated centrosymmetric dimeric units linked via C—H···O linkages to form a supramolecular ladder parallel to the b axis that extends along the [101] direction (Fig. 3). The non-covalent crystal packing interactions are closely related to that observed in the 4-phenyl analogue and distinctly differs from those of the 4-methylphenyl (Suresh et al., 2012b) and 4-bromophenyl (Suresh et al., 2012c) analogues. The intramolecular C—H···O hydrogen bond generates a S(6) motif and its geometry is similar to those observed in all of the above analogues. No significant weak non-covalent crystal packing interactions involving centroids of planar rings are observed. Though it has become an acceptable norm in describing weak non-covalent interactions in terms of C—H···π and π···π interactions, some recent views (Martinez & Iverson, 2012; Bloom & Wheeler, 2011) on these interactions calls for a careful analysis while describing them in crystal structures.

The crystal structure of the title compound together with those of its analogues demonstrate the effect of substituents in drastically altering the interaction patterns while retaining the crystal system and lattice type.

Related literature top

For related structures, see: Suresh et al. (2012a,b,c). For discussion on aromatic interactions, see: Bloom & Wheeler (2011); Martinez & Iverson (2012). For graph-set motifs, see: Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975).

Experimental top

To a stirred mixture of 2-(1H-indole-3-carbonyl)-3-(4-isopropylphenyl)acrylonitrile (1.0 eq) and phenacylpyridinium bromide (1.0 eq) in water (10 ml) was added drop wise triethylamine (0.25 eq) at room temperature. The resulting clear solution, that slowly became turbid, was stirred at room temperature for 1.5 h. Then the separated free flowing solid was filtered and washed with methanol (3 ml) to afford the compound as pale yellow solid. Yield 87%; m.p. 508 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. The R²₂(16) N—H···N mediated centrosymmetric dimeric units linked via C(6) C—H···O linkages to form a supramolecular ladder. Non-participating groups and H-atoms are omitted for clarity.
	Fig. 3. Perspective view of supramolecular ladders parallel to the b axis extending along the [101] direction. Non-participating groups and H-atoms are omitted for clarity.

5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phenyl]-4,5-dihydrofuran- 3-carbonitrile top

Crystal data top

C₂₉H₂₄N₂O₂	F(000) = 912
M_r = 432.50	D_x = 1.251 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4455 reflections
a = 17.1073 (4) Å	θ = 2.5–25.9°
b = 8.1230 (2) Å	µ = 0.08 mm⁻¹
c = 17.6160 (4) Å	T = 298 K
β = 110.325 (1)°	Block, yellow
V = 2295.55 (9) Å³	0.30 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4455 independent reflections
Radiation source: fine-focus sealed tube	2979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 25.9°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→20
T_min = 0.978, T_max = 0.986	k = −9→9
21711 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0478P)² + 0.3844P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4455 reflections	Δρ_max = 0.14 e Å⁻³
313 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (8)

Crystal data top

C₂₉H₂₄N₂O₂	V = 2295.55 (9) Å³
M_r = 432.50	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.1073 (4) Å	µ = 0.08 mm⁻¹
b = 8.1230 (2) Å	T = 298 K
c = 17.6160 (4) Å	0.30 × 0.24 × 0.18 mm
β = 110.325 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4455 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2979 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.986	R_int = 0.031
21711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.14 e Å⁻³
4455 reflections	Δρ_min = −0.15 e Å⁻³
313 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.27185 (7)	0.17860 (13)	0.26234 (6)	0.0553 (3)
O2	0.14529 (8)	0.34499 (18)	0.16547 (7)	0.0792 (4)
N1	0.49191 (10)	0.5602 (2)	0.31131 (9)	0.0752 (5)
N2	0.40406 (11)	0.3263 (2)	0.52408 (9)	0.0694 (5)
H2	0.4434 (13)	0.352 (3)	0.5722 (13)	0.088 (6)*
C38	0.41572 (11)	0.3360 (2)	0.45193 (10)	0.0611 (5)
H38	0.4652	0.3669	0.4451	0.073*
C37	0.32392 (12)	0.2788 (2)	0.51144 (10)	0.0623 (5)
C36	0.28453 (16)	0.2536 (3)	0.56731 (12)	0.0808 (6)
H36	0.3124	0.2690	0.6224	0.097*
C35	0.20349 (17)	0.2056 (3)	0.53802 (15)	0.0907 (7)
H35	0.1756	0.1862	0.5740	0.109*
C34	0.16088 (14)	0.1847 (3)	0.45517 (14)	0.0828 (6)
H34	0.1051	0.1537	0.4371	0.099*
C33	0.20012 (12)	0.2091 (2)	0.39978 (12)	0.0640 (5)
H33	0.1721 (10)	0.194 (2)	0.3426 (10)	0.063 (5)*
C32	0.28362 (11)	0.25594 (19)	0.42818 (9)	0.0527 (4)
C31	0.34395 (10)	0.29363 (19)	0.39077 (9)	0.0510 (4)
C3	0.33352 (9)	0.28117 (19)	0.30620 (9)	0.0481 (4)
C2	0.37493 (10)	0.34966 (19)	0.26182 (9)	0.0486 (4)
C1	0.43942 (11)	0.4654 (2)	0.28977 (9)	0.0544 (4)
C5	0.34552 (9)	0.27757 (19)	0.17735 (9)	0.0477 (4)
H5	0.3302	0.3663	0.1371	0.057*
C4	0.26595 (9)	0.18830 (19)	0.17900 (8)	0.0483 (4)
H4	0.2641	0.0769	0.1571	0.058*
C41	0.18682 (10)	0.2796 (2)	0.13117 (9)	0.0505 (4)
C42	0.16376 (9)	0.28783 (19)	0.04210 (9)	0.0472 (4)
C43	0.20139 (11)	0.1912 (2)	0.00015 (10)	0.0613 (5)
H43	0.2440	0.1194	0.0281	0.074*
C44	0.17592 (13)	0.2007 (3)	−0.08313 (11)	0.0751 (6)
H44	0.2012	0.1348	−0.1111	0.090*
C45	0.11360 (13)	0.3069 (2)	−0.12478 (11)	0.0725 (5)
H45	0.0966	0.3129	−0.1809	0.087*
C46	0.07638 (12)	0.4040 (3)	−0.08392 (11)	0.0741 (5)
H46	0.0343	0.4767	−0.1121	0.089*
C47	0.10122 (11)	0.3943 (2)	−0.00096 (10)	0.0633 (5)
H47	0.0755	0.4604	0.0265	0.076*
C51	0.41055 (9)	0.16822 (19)	0.16311 (9)	0.0486 (4)
C52	0.44866 (12)	0.2118 (2)	0.10860 (11)	0.0718 (5)
H52	0.4313	0.3059	0.0772	0.086*
C53	0.51201 (13)	0.1176 (3)	0.10024 (12)	0.0803 (6)
H53	0.5365	0.1498	0.0630	0.096*
C54	0.54025 (11)	−0.0221 (2)	0.14503 (10)	0.0631 (5)
C55	0.49997 (10)	−0.0680 (2)	0.19778 (10)	0.0579 (4)
H55	0.5163	−0.1640	0.2280	0.070*
C56	0.43633 (10)	0.0251 (2)	0.20650 (9)	0.0518 (4)
H56	0.4086 (9)	−0.0097 (19)	0.2440 (9)	0.059 (4)*
C6	0.61471 (13)	−0.1150 (3)	0.14021 (12)	0.0827 (6)
H6	0.6245	−0.0765	0.0916	0.099*
C7	0.69188 (13)	−0.0692 (4)	0.21299 (13)	0.1129 (9)
H7A	0.6812	−0.0901	0.2621	0.169*
H7B	0.7043	0.0453	0.2101	0.169*
H7C	0.7385	−0.1343	0.2123	0.169*
C8	0.60164 (18)	−0.2977 (3)	0.1318 (2)	0.1309 (11)
H8A	0.5946	−0.3408	0.1797	0.196*
H8B	0.6492	−0.3484	0.1244	0.196*
H8C	0.5528	−0.3208	0.0857	0.196*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0631 (7)	0.0602 (7)	0.0400 (6)	−0.0138 (6)	0.0145 (5)	−0.0035 (5)
O2	0.0800 (9)	0.1019 (10)	0.0621 (8)	0.0212 (8)	0.0331 (7)	−0.0097 (7)
N1	0.0769 (11)	0.0719 (11)	0.0629 (10)	−0.0211 (9)	0.0067 (8)	−0.0012 (8)
N2	0.0827 (12)	0.0747 (11)	0.0406 (9)	−0.0067 (9)	0.0087 (8)	−0.0032 (7)
C38	0.0699 (11)	0.0623 (11)	0.0458 (10)	−0.0031 (9)	0.0134 (8)	−0.0008 (8)
C37	0.0830 (14)	0.0546 (10)	0.0484 (10)	0.0046 (10)	0.0217 (9)	0.0016 (8)
C36	0.1129 (18)	0.0812 (14)	0.0558 (12)	0.0064 (13)	0.0389 (12)	0.0030 (10)
C35	0.1152 (19)	0.0943 (17)	0.0842 (16)	0.0108 (15)	0.0619 (15)	0.0097 (13)
C34	0.0788 (14)	0.0842 (15)	0.0955 (17)	0.0055 (12)	0.0432 (13)	0.0062 (12)
C33	0.0687 (12)	0.0613 (11)	0.0629 (12)	0.0076 (9)	0.0242 (10)	0.0011 (9)
C32	0.0651 (11)	0.0443 (9)	0.0472 (9)	0.0069 (8)	0.0176 (8)	0.0011 (7)
C31	0.0603 (10)	0.0470 (9)	0.0413 (9)	0.0028 (8)	0.0120 (7)	0.0004 (7)
C3	0.0512 (9)	0.0442 (9)	0.0435 (9)	0.0018 (7)	0.0094 (7)	−0.0024 (7)
C2	0.0511 (9)	0.0465 (9)	0.0438 (8)	−0.0020 (8)	0.0107 (7)	−0.0027 (7)
C1	0.0584 (10)	0.0531 (10)	0.0450 (9)	−0.0036 (9)	0.0095 (8)	−0.0004 (8)
C5	0.0520 (9)	0.0473 (9)	0.0402 (8)	−0.0047 (7)	0.0115 (7)	0.0002 (7)
C4	0.0556 (9)	0.0490 (9)	0.0394 (8)	−0.0055 (7)	0.0155 (7)	−0.0059 (7)
C41	0.0511 (9)	0.0531 (9)	0.0485 (9)	−0.0050 (8)	0.0188 (8)	−0.0101 (7)
C42	0.0453 (9)	0.0486 (9)	0.0460 (9)	−0.0057 (7)	0.0137 (7)	−0.0074 (7)
C43	0.0677 (11)	0.0652 (11)	0.0506 (10)	0.0086 (9)	0.0199 (8)	−0.0026 (8)
C44	0.0912 (14)	0.0846 (14)	0.0548 (11)	0.0057 (12)	0.0320 (11)	−0.0082 (10)
C45	0.0856 (14)	0.0795 (14)	0.0462 (10)	−0.0104 (11)	0.0149 (10)	0.0021 (10)
C46	0.0728 (12)	0.0755 (13)	0.0581 (12)	0.0063 (10)	0.0030 (10)	0.0016 (10)
C47	0.0568 (10)	0.0696 (12)	0.0568 (11)	0.0039 (9)	0.0110 (8)	−0.0088 (9)
C51	0.0525 (9)	0.0532 (9)	0.0392 (8)	−0.0068 (8)	0.0148 (7)	−0.0013 (7)
C52	0.0848 (13)	0.0751 (13)	0.0671 (12)	0.0079 (11)	0.0410 (11)	0.0220 (10)
C53	0.0857 (14)	0.1008 (16)	0.0742 (13)	0.0119 (12)	0.0528 (11)	0.0227 (12)
C54	0.0628 (11)	0.0780 (13)	0.0539 (10)	0.0029 (10)	0.0271 (9)	−0.0005 (9)
C55	0.0620 (11)	0.0598 (11)	0.0529 (10)	0.0034 (9)	0.0212 (8)	0.0046 (8)
C56	0.0579 (10)	0.0575 (10)	0.0445 (9)	−0.0049 (8)	0.0234 (8)	0.0026 (8)
C6	0.0760 (13)	0.1117 (18)	0.0713 (13)	0.0184 (13)	0.0393 (11)	0.0067 (12)
C7	0.0725 (15)	0.190 (3)	0.0792 (16)	0.0226 (16)	0.0300 (13)	0.0053 (16)
C8	0.125 (2)	0.110 (2)	0.182 (3)	0.0356 (18)	0.084 (2)	−0.005 (2)

Geometric parameters (Å, º) top

O1—C3	1.3557 (18)	C42—C43	1.381 (2)
O1—C4	1.4384 (17)	C43—C44	1.380 (2)
O2—C41	1.2043 (18)	C43—H43	0.9300
N1—C1	1.143 (2)	C44—C45	1.370 (3)
N2—C38	1.356 (2)	C44—H44	0.9300
N2—C37	1.366 (2)	C45—C46	1.365 (3)
N2—H2	0.91 (2)	C45—H45	0.9300
C38—C31	1.367 (2)	C46—C47	1.375 (2)
C38—H38	0.9300	C46—H46	0.9300
C37—C36	1.388 (3)	C47—H47	0.9300
C37—C32	1.399 (2)	C51—C56	1.377 (2)
C36—C35	1.358 (3)	C51—C52	1.381 (2)
C36—H36	0.9300	C52—C53	1.376 (3)
C35—C34	1.397 (3)	C52—H52	0.9300
C35—H35	0.9300	C53—C54	1.371 (3)
C34—C33	1.378 (3)	C53—H53	0.9300
C34—H34	0.9300	C54—C55	1.387 (2)
C33—C32	1.392 (2)	C54—C6	1.508 (3)
C33—H33	0.961 (16)	C55—C56	1.377 (2)
C32—C31	1.437 (2)	C55—H55	0.9300
C31—C3	1.441 (2)	C56—H56	0.978 (15)
C3—C2	1.344 (2)	C6—C8	1.501 (3)
C2—C1	1.402 (2)	C6—C7	1.533 (3)
C2—C5	1.513 (2)	C6—H6	0.9800
C5—C51	1.511 (2)	C7—H7A	0.9600
C5—C4	1.552 (2)	C7—H7B	0.9600
C5—H5	0.9800	C7—H7C	0.9600
C4—C41	1.516 (2)	C8—H8A	0.9600
C4—H4	0.9800	C8—H8B	0.9600
C41—C42	1.480 (2)	C8—H8C	0.9600
C42—C47	1.380 (2)

C3—O1—C4	108.23 (11)	C43—C42—C41	122.63 (15)
C38—N2—C37	109.26 (16)	C44—C43—C42	120.21 (17)
C38—N2—H2	124.0 (13)	C44—C43—H43	119.9
C37—N2—H2	126.6 (12)	C42—C43—H43	119.9
N2—C38—C31	109.88 (16)	C45—C44—C43	120.31 (17)
N2—C38—H38	125.1	C45—C44—H44	119.8
C31—C38—H38	125.1	C43—C44—H44	119.8
N2—C37—C36	129.28 (18)	C46—C45—C44	120.01 (17)
N2—C37—C32	108.03 (15)	C46—C45—H45	120.0
C36—C37—C32	122.68 (19)	C44—C45—H45	120.0
C35—C36—C37	117.1 (2)	C45—C46—C47	119.89 (18)
C35—C36—H36	121.4	C45—C46—H46	120.1
C37—C36—H36	121.4	C47—C46—H46	120.1
C36—C35—C34	121.69 (19)	C46—C47—C42	120.99 (17)
C36—C35—H35	119.2	C46—C47—H47	119.5
C34—C35—H35	119.2	C42—C47—H47	119.5
C33—C34—C35	121.1 (2)	C56—C51—C52	117.70 (15)
C33—C34—H34	119.4	C56—C51—C5	121.09 (13)
C35—C34—H34	119.4	C52—C51—C5	121.15 (15)
C34—C33—C32	118.44 (19)	C53—C52—C51	120.76 (17)
C34—C33—H33	122.3 (10)	C53—C52—H52	119.6
C32—C33—H33	119.2 (10)	C51—C52—H52	119.6
C33—C32—C37	118.90 (16)	C54—C53—C52	122.15 (16)
C33—C32—C31	134.73 (15)	C54—C53—H53	118.9
C37—C32—C31	106.34 (15)	C52—C53—H53	118.9
C38—C31—C32	106.48 (14)	C53—C54—C55	116.79 (16)
C38—C31—C3	125.98 (15)	C53—C54—C6	121.17 (16)
C32—C31—C3	127.46 (15)	C55—C54—C6	121.95 (17)
C2—C3—O1	112.70 (13)	C56—C55—C54	121.53 (17)
C2—C3—C31	132.15 (15)	C56—C55—H55	119.2
O1—C3—C31	115.13 (13)	C54—C55—H55	119.2
C3—C2—C1	125.62 (14)	C51—C56—C55	121.00 (15)
C3—C2—C5	110.44 (13)	C51—C56—H56	118.8 (9)
C1—C2—C5	123.86 (14)	C55—C56—H56	120.2 (9)
N1—C1—C2	178.90 (18)	C8—C6—C54	113.64 (18)
C51—C5—C2	112.23 (12)	C8—C6—C7	112.2 (2)
C51—C5—C4	115.45 (13)	C54—C6—C7	109.29 (17)
C2—C5—C4	99.01 (11)	C8—C6—H6	107.1
C51—C5—H5	109.9	C54—C6—H6	107.1
C2—C5—H5	109.9	C7—C6—H6	107.1
C4—C5—H5	109.9	C6—C7—H7A	109.5
O1—C4—C41	109.06 (12)	C6—C7—H7B	109.5
O1—C4—C5	107.08 (11)	H7A—C7—H7B	109.5
C41—C4—C5	112.38 (12)	C6—C7—H7C	109.5
O1—C4—H4	109.4	H7A—C7—H7C	109.5
C41—C4—H4	109.4	H7B—C7—H7C	109.5
C5—C4—H4	109.4	C6—C8—H8A	109.5
O2—C41—C42	121.68 (15)	C6—C8—H8B	109.5
O2—C41—C4	120.35 (14)	H8A—C8—H8B	109.5
C42—C41—C4	117.96 (13)	C6—C8—H8C	109.5
C47—C42—C43	118.59 (15)	H8A—C8—H8C	109.5
C47—C42—C41	118.78 (14)	H8B—C8—H8C	109.5

C37—N2—C38—C31	−0.6 (2)	C2—C5—C4—O1	−15.46 (14)
C38—N2—C37—C36	−179.78 (19)	C51—C5—C4—C41	−135.75 (13)
C38—N2—C37—C32	0.6 (2)	C2—C5—C4—C41	104.28 (13)
N2—C37—C36—C35	−179.8 (2)	O1—C4—C41—O2	7.6 (2)
C32—C37—C36—C35	−0.3 (3)	C5—C4—C41—O2	−110.94 (17)
C37—C36—C35—C34	−1.0 (3)	O1—C4—C41—C42	−173.49 (12)
C36—C35—C34—C33	1.3 (3)	C5—C4—C41—C42	67.93 (17)
C35—C34—C33—C32	−0.2 (3)	O2—C41—C42—C47	10.5 (2)
C34—C33—C32—C37	−1.0 (3)	C4—C41—C42—C47	−168.32 (14)
C34—C33—C32—C31	−179.20 (18)	O2—C41—C42—C43	−168.36 (17)
N2—C37—C32—C33	−179.12 (16)	C4—C41—C42—C43	12.8 (2)
C36—C37—C32—C33	1.3 (3)	C47—C42—C43—C44	−0.6 (3)
N2—C37—C32—C31	−0.42 (19)	C41—C42—C43—C44	178.27 (16)
C36—C37—C32—C31	179.96 (16)	C42—C43—C44—C45	0.5 (3)
N2—C38—C31—C32	0.32 (19)	C43—C44—C45—C46	0.0 (3)
N2—C38—C31—C3	−176.61 (15)	C44—C45—C46—C47	−0.4 (3)
C33—C32—C31—C38	178.46 (19)	C45—C46—C47—C42	0.3 (3)
C37—C32—C31—C38	0.07 (18)	C43—C42—C47—C46	0.3 (3)
C33—C32—C31—C3	−4.7 (3)	C41—C42—C47—C46	−178.69 (16)
C37—C32—C31—C3	176.94 (15)	C2—C5—C51—C56	63.99 (19)
C4—O1—C3—C2	−5.21 (17)	C4—C5—C51—C56	−48.45 (19)
C4—O1—C3—C31	176.25 (13)	C2—C5—C51—C52	−113.25 (17)
C38—C31—C3—C2	−23.4 (3)	C4—C5—C51—C52	134.30 (16)
C32—C31—C3—C2	160.29 (17)	C56—C51—C52—C53	−2.1 (3)
C38—C31—C3—O1	154.78 (15)	C5—C51—C52—C53	175.27 (17)
C32—C31—C3—O1	−21.5 (2)	C51—C52—C53—C54	−0.1 (3)
O1—C3—C2—C1	177.33 (14)	C52—C53—C54—C55	2.1 (3)
C31—C3—C2—C1	−4.4 (3)	C52—C53—C54—C6	−174.53 (19)
O1—C3—C2—C5	−5.75 (18)	C53—C54—C55—C56	−1.9 (3)
C31—C3—C2—C5	172.48 (16)	C6—C54—C55—C56	174.67 (17)
C3—C2—C5—C51	−109.41 (15)	C52—C51—C56—C55	2.2 (2)
C1—C2—C5—C51	67.58 (19)	C5—C51—C56—C55	−175.12 (14)
C3—C2—C5—C4	12.92 (16)	C54—C55—C56—C51	−0.2 (3)
C1—C2—C5—C4	−170.09 (15)	C53—C54—C6—C8	−133.9 (2)
C3—O1—C4—C41	−108.29 (13)	C55—C54—C6—C8	49.6 (3)
C3—O1—C4—C5	13.55 (15)	C53—C54—C6—C7	99.9 (2)
C51—C5—C4—O1	104.52 (14)	C55—C54—C6—C7	−76.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.961 (16)	2.569 (15)	3.081 (2)	113.5 (11)
N2—H2···N1ⁱ	0.91 (2)	2.09 (2)	2.973 (2)	165.2 (17)
C56—H56···O2ⁱⁱ	0.978 (15)	2.411 (16)	3.371 (2)	166.9 (13)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₄N₂O₂
M_r	432.50
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	17.1073 (4), 8.1230 (2), 17.6160 (4)
β (°)	110.325 (1)
V (Å³)	2295.55 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.978, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	21711, 4455, 2979
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 1.03
No. of reflections	4455
No. of parameters	313
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O1	0.961 (16)	2.569 (15)	3.081 (2)	113.5 (11)
N2—H2···N1ⁱ	0.91 (2)	2.09 (2)	2.973 (2)	165.2 (17)
C56—H56···O2ⁱⁱ	0.978 (15)	2.411 (16)	3.371 (2)	166.9 (13)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors thank the SAIF, IIT, Chennai, for the data collection. PG thanks the CSIR, India, for a Research Fellowship. SP thanks the Department of Science and Technology, New Delhi, for funding the Indo-Spanish collaborative major research project (grant DST/INT/SPAIN/ 09).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bloom, J. W. G. & Wheeler, S. E. (2011). Angew. Chem. Int. Ed. 50, 7847–7849. Web of Science CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Cremer, D. & &Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Martinez, C. R. & Iverson, B. L. (2012). Chem. Sci. 3, 2191–2201. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012a). Acta Cryst. E68, o1576. CSD CrossRef IUCr Journals Google Scholar
Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012b). Acta Cryst. E68, o1124. CSD CrossRef IUCr Journals Google Scholar
Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012c). Acta Cryst. E68, o2397. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page o3441

doi:10.1107/S1600536812046764

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phen­yl]-4,5-di­hydro­furan-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phenyl]-4,5-dihydrofuran-3-carbonitrile