2-(1H-indol-3-ylcarbon­yl)acetonitrile

Ramesh, P.; Subbiahpandi, A.; Thirumurugan, P.; Perumal, P.T.; Ponnuswamy, M.N.

doi:10.1107/S1600536809001342

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o447

doi:10.1107/S1600536809001342

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2-(1H-indol-3-ylcarbonyl)acetonitrile

P. Ramesh,^a A. Subbiahpandi,^a P. Thirumurugan,^b Paramasivan T. Perumal ^b and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 17 December 2008; accepted 12 January 2009; online 4 February 2009)

The title compound, C₁₁H₈N₂O, crystallizes with two crystallographically independent molecules in the asymmetric unit which are approximately perpendicular to each other [79.97 (6)°]. The indole ring system is planar [r.m.s. deviation = 0.010 (1) Å]. The crystal structure is stabilized by intermolecular C—H⋯N and N—H⋯O interactions.

Related literature

For the use of indole derivatives as bioactive drugs, see: Stevenson et al. (2000 ). For their biological properties, see: Harris & Uhle (1960 ); Ho et al. (1986 ). For their high aldose reductase inhibitory activity, see: Rajeswaran et al. (1999 ). For a related structure, see: Ramesh et al. (2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₈N₂O
M_r = 184.19
Triclinic, $[P \overline 1]$
a = 7.3439 (2) Å
b = 7.3534 (2) Å
c = 18.2475 (5) Å
α = 83.402 (2)°
β = 78.890 (2)°
γ = 73.501 (1)°
V = 925.23 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.974, T_max = 0.983
18838 measured reflections
3253 independent reflections
2717 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.06
3253 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.98	2.8146 (18)	163
C2—H2⋯N13ⁱ	0.93	2.59	3.236 (2)	127
N1′—H1′⋯O1′ⁱⁱ	0.86	2.00	2.8166 (15)	158
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z.

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001342/bt2839sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001342/bt2839Isup2.hkl

checkCIF report

Comment top

Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle 1960; Ho et al., 1986). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). Against this background and to ascertain the molecular conformation, the structure determination of the title compound has been carried out.

There are two crystallographically independent molecules in the asymmetric unit and they are approximately perpendicular to each other [79.97 (6)°]. In both molecules the indole ring systems are planar and the sum of the angles at N1 (359.95°) and N1' (359.94°) are in accordance with sp² hybridization. The bond angles of the cyano group [179.8 (2) and 179.6 (2)°] in both molecules show their linear character. The C≡N bond distances [1.133 (2) and 1.131 (2) Å] are comparable with the literature values (Ramesh et al., 2008).

The crystal packing is covered by C—H···N, C—H···O and C—H···π types intermolecular interactions in addition to van der Waals forces. N1 atom in one of the molecules donates one proton to O1 (-1 + x, y, z) which connects the molecules into a one dimensional C6 chain (Bernstein et al., 1995) running along the a axis, whereas in the other molecule at N1' forms similar network with O1' (x, 1 + y, z) along the b axis. The combination of N1—H1···O1 and C2—H2···N13 hydrogen bonds form a R₂² (9) dimer chain running along the a axis.

Related literature top

For the use of indole derivatives as bioactive drugs, see: Stevenson et al. (2000). For the biological properties, see: Harris & Uhle (1960); Ho et al. (1986). For their high aldose reductase inhibitory activity, see: Rajeswaran et al. (1999). For a related structure, see: Ramesh et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Indole (5.85 g, 50 mmol) was added to a solution prepared by dissolution of cyanoacetic acid (5.0 g, 50 mmol) in Ac₂O (50 ml) at 50 °C. The solution was heated at 85 °C for 5 min. During that period 3-cyanoacetylindole started to crystallize. After 5 more min, the mixture was allowed to cool and the solid was collected, washed with MeOH, and dried.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of the molecule showing the thermal ellipsoids are drawn at 50% probability level. The H atoms are shown as small circles of arbitrary radii.
	Fig. 2. The crystal packing of the molecules viewed down c axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

2-(1H-indol-3-ylcarbonyl)acetonitrile top

Crystal data top

C₁₁H₈N₂O	Z = 4
M_r = 184.19	F(000) = 384
Triclinic, P1	D_x = 1.322 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3439 (2) Å	Cell parameters from 3554 reflections
b = 7.3534 (2) Å	θ = 1.1–25.0°
c = 18.2475 (5) Å	µ = 0.09 mm⁻¹
α = 83.402 (2)°	T = 293 K
β = 78.890 (2)°	Block, colourless
γ = 73.501 (1)°	0.30 × 0.30 × 0.20 mm
V = 925.23 (4) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	3253 independent reflections
Radiation source: fine-focus sealed tube	2717 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −7→8
T_min = 0.974, T_max = 0.983	k = −8→8
18838 measured reflections	l = −21→21

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0404P)² + 0.2437P] where P = (F_o² + 2F_c²)/3
3253 reflections	(Δ/σ)_max = 0.008
253 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₁H₈N₂O	γ = 73.501 (1)°
M_r = 184.19	V = 925.23 (4) Å³
Triclinic, P1	Z = 4
a = 7.3439 (2) Å	Mo Kα radiation
b = 7.3534 (2) Å	µ = 0.09 mm⁻¹
c = 18.2475 (5) Å	T = 293 K
α = 83.402 (2)°	0.30 × 0.30 × 0.20 mm
β = 78.890 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	3253 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2717 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.025
18838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	Δρ_max = 0.12 e Å⁻³
3253 reflections	Δρ_min = −0.16 e Å⁻³
253 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	0.13478 (16)	0.2464 (2)	1.01403 (7)	0.0659 (4)
O1'	0.76317 (17)	0.33368 (14)	0.47980 (6)	0.0543 (3)
N1	0.7573 (2)	0.2397 (2)	1.00692 (9)	0.0619 (4)
H1	0.8678	0.2314	1.0183	0.074*
N1'	0.77718 (19)	−0.28849 (17)	0.48288 (7)	0.0479 (3)
H1'	0.7932	−0.4024	0.4709	0.057*
C2	0.6023 (2)	0.2202 (2)	1.05570 (11)	0.0567 (4)
H2	0.5977	0.1956	1.1071	0.068*
C2'	0.8188 (2)	−0.1468 (2)	0.43593 (9)	0.0441 (4)
H2'	0.8689	−0.1567	0.3853	0.053*
C3	0.4501 (2)	0.2418 (2)	1.01850 (9)	0.0475 (4)
C3'	0.7768 (2)	0.01550 (19)	0.47349 (8)	0.0385 (3)
C4	0.5195 (2)	0.2786 (2)	0.94094 (9)	0.0478 (4)
C4'	0.7012 (2)	−0.03211 (19)	0.54959 (8)	0.0389 (3)
C5'	0.6267 (2)	0.0675 (2)	0.61400 (9)	0.0479 (4)
H5'	0.6214	0.1956	0.6133	0.058*
C5	0.4391 (2)	0.3141 (2)	0.87583 (10)	0.0565 (4)
H5	0.3107	0.3175	0.8777	0.068*
C6'	0.5613 (3)	−0.0269 (2)	0.67853 (9)	0.0569 (4)
H6'	0.5098	0.0389	0.7216	0.068*
C6	0.5521 (3)	0.3437 (3)	0.80899 (11)	0.0678 (5)
H6	0.4991	0.3687	0.7653	0.081*
C7'	0.5702 (3)	−0.2187 (2)	0.68090 (10)	0.0583 (4)
H7'	0.5269	−0.2792	0.7257	0.070*
C7	0.7456 (3)	0.3370 (3)	0.80531 (13)	0.0742 (6)
H7	0.8195	0.3559	0.7591	0.089*
C8'	0.6417 (2)	−0.3200 (2)	0.61849 (10)	0.0527 (4)
H8'	0.6475	−0.4483	0.6199	0.063*
C8	0.8287 (3)	0.3032 (3)	0.86844 (13)	0.0684 (5)
H8	0.9574	0.2993	0.8660	0.082*
C9	0.7140 (2)	0.2751 (2)	0.93550 (11)	0.0540 (4)
C9'	0.7049 (2)	−0.2241 (2)	0.55332 (8)	0.0419 (3)
C10	0.2612 (2)	0.2273 (2)	1.05110 (9)	0.0482 (4)
C10'	0.8024 (2)	0.19645 (19)	0.44251 (8)	0.0396 (3)
C11'	0.8851 (2)	0.2118 (2)	0.35992 (8)	0.0455 (4)
H11A	1.0210	0.1451	0.3524	0.055*
H11B	0.8214	0.1505	0.3322	0.055*
C11	0.2210 (2)	0.1842 (3)	1.13506 (9)	0.0562 (4)
H11C	0.3072	0.0628	1.1480	0.067*
H11D	0.2474	0.2809	1.1602	0.067*
C12	0.0245 (3)	0.1779 (3)	1.16141 (9)	0.0605 (5)
C12'	0.8620 (2)	0.4067 (2)	0.33086 (9)	0.0513 (4)
N13	−0.1297 (3)	0.1725 (3)	1.18193 (9)	0.0878 (6)
N13'	0.8429 (3)	0.5597 (2)	0.30820 (9)	0.0806 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0436 (6)	0.1027 (10)	0.0585 (7)	−0.0291 (6)	−0.0166 (6)	0.0039 (7)
O1'	0.0829 (8)	0.0340 (6)	0.0491 (6)	−0.0248 (5)	−0.0035 (6)	−0.0054 (5)
N1	0.0409 (8)	0.0647 (9)	0.0868 (11)	−0.0155 (7)	−0.0217 (8)	−0.0100 (8)
N1'	0.0611 (8)	0.0298 (6)	0.0566 (8)	−0.0163 (6)	−0.0112 (6)	−0.0059 (6)
C2	0.0469 (9)	0.0597 (10)	0.0689 (11)	−0.0150 (8)	−0.0187 (8)	−0.0087 (8)
C2'	0.0521 (9)	0.0379 (8)	0.0453 (8)	−0.0158 (6)	−0.0082 (7)	−0.0056 (6)
C3	0.0412 (8)	0.0451 (9)	0.0602 (10)	−0.0126 (7)	−0.0144 (7)	−0.0072 (7)
C3'	0.0432 (8)	0.0323 (7)	0.0435 (8)	−0.0136 (6)	−0.0109 (6)	−0.0027 (6)
C4	0.0420 (8)	0.0367 (8)	0.0674 (11)	−0.0124 (6)	−0.0128 (7)	−0.0038 (7)
C4'	0.0409 (8)	0.0333 (7)	0.0461 (8)	−0.0130 (6)	−0.0123 (6)	−0.0011 (6)
C5'	0.0566 (9)	0.0388 (8)	0.0501 (9)	−0.0144 (7)	−0.0095 (7)	−0.0043 (7)
C5	0.0509 (9)	0.0527 (10)	0.0689 (11)	−0.0184 (8)	−0.0160 (8)	0.0048 (8)
C6'	0.0671 (11)	0.0573 (10)	0.0458 (9)	−0.0172 (8)	−0.0067 (8)	−0.0043 (8)
C6	0.0761 (13)	0.0590 (11)	0.0706 (13)	−0.0260 (9)	−0.0147 (10)	0.0103 (9)
C7'	0.0656 (11)	0.0587 (11)	0.0514 (10)	−0.0237 (8)	−0.0092 (8)	0.0103 (8)
C7	0.0741 (13)	0.0641 (12)	0.0810 (14)	−0.0287 (10)	0.0052 (11)	0.0041 (10)
C8'	0.0611 (10)	0.0385 (8)	0.0623 (11)	−0.0213 (7)	−0.0151 (8)	0.0093 (7)
C8	0.0486 (10)	0.0584 (11)	0.0983 (16)	−0.0215 (8)	−0.0032 (10)	−0.0021 (10)
C9	0.0424 (9)	0.0429 (9)	0.0794 (12)	−0.0144 (7)	−0.0114 (8)	−0.0055 (8)
C9'	0.0443 (8)	0.0348 (7)	0.0498 (9)	−0.0136 (6)	−0.0119 (7)	−0.0016 (6)
C10	0.0438 (8)	0.0472 (9)	0.0576 (10)	−0.0131 (7)	−0.0148 (7)	−0.0065 (7)
C10'	0.0432 (8)	0.0347 (7)	0.0446 (8)	−0.0140 (6)	−0.0106 (6)	−0.0026 (6)
C11'	0.0512 (9)	0.0421 (8)	0.0451 (9)	−0.0155 (7)	−0.0081 (7)	−0.0026 (7)
C11	0.0554 (10)	0.0621 (10)	0.0551 (10)	−0.0163 (8)	−0.0154 (8)	−0.0085 (8)
C12	0.0591 (12)	0.0765 (12)	0.0430 (9)	−0.0117 (9)	−0.0078 (8)	−0.0100 (8)
C12'	0.0641 (10)	0.0487 (10)	0.0432 (9)	−0.0227 (8)	−0.0044 (8)	0.0001 (7)
N13	0.0640 (11)	0.1429 (18)	0.0513 (10)	−0.0231 (11)	−0.0009 (8)	−0.0111 (10)
N13'	0.1215 (15)	0.0564 (10)	0.0620 (10)	−0.0331 (10)	−0.0029 (10)	0.0065 (8)

Geometric parameters (Å, º) top

O1—C10	1.2190 (18)	C5—H5	0.9300
O1'—C10'	1.2173 (17)	C6'—C7'	1.389 (2)
N1—C2	1.335 (2)	C6'—H6'	0.9300
N1—C9	1.379 (2)	C6—C7	1.396 (3)
N1—H1	0.8600	C6—H6	0.9300
N1'—C2'	1.3372 (19)	C7'—C8'	1.367 (2)
N1'—C9'	1.3755 (19)	C7'—H7'	0.9300
N1'—H1'	0.8600	C7—C8	1.371 (3)
C2—C3	1.379 (2)	C7—H7	0.9300
C2—H2	0.9300	C8'—C9'	1.381 (2)
C2'—C3'	1.373 (2)	C8'—H8'	0.9300
C2'—H2'	0.9300	C8—C9	1.376 (3)
C3—C10	1.429 (2)	C8—H8	0.9300
C3—C4	1.431 (2)	C10—C11	1.517 (2)
C3'—C10'	1.4331 (19)	C10'—C11'	1.516 (2)
C3'—C4'	1.436 (2)	C11'—C12'	1.445 (2)
C4—C5	1.393 (2)	C11'—H11A	0.9700
C4—C9	1.406 (2)	C11'—H11B	0.9700
C4'—C5'	1.393 (2)	C11—C12	1.443 (3)
C4'—C9'	1.3987 (19)	C11—H11C	0.9700
C5'—C6'	1.372 (2)	C11—H11D	0.9700
C5'—H5'	0.9300	C12—N13	1.133 (2)
C5—C6	1.369 (3)	C12'—N13'	1.132 (2)

C2—N1—C9	109.94 (14)	C8'—C7'—H7'	119.4
C2—N1—H1	125.0	C6'—C7'—H7'	119.4
C9—N1—H1	125.0	C8—C7—C6	121.35 (19)
C2'—N1'—C9'	109.56 (12)	C8—C7—H7	119.3
C2'—N1'—H1'	125.2	C6—C7—H7	119.3
C9'—N1'—H1'	125.2	C7'—C8'—C9'	117.34 (15)
N1—C2—C3	109.81 (16)	C7'—C8'—H8'	121.3
N1—C2—H2	125.1	C9'—C8'—H8'	121.3
C3—C2—H2	125.1	C7—C8—C9	117.29 (18)
N1'—C2'—C3'	110.07 (14)	C7—C8—H8	121.4
N1'—C2'—H2'	125.0	C9—C8—H8	121.4
C3'—C2'—H2'	125.0	C8—C9—N1	130.03 (16)
C2—C3—C10	126.55 (16)	C8—C9—C4	122.72 (17)
C2—C3—C4	106.56 (14)	N1—C9—C4	107.25 (15)
C10—C3—C4	126.89 (14)	N1'—C9'—C8'	129.55 (14)
C2'—C3'—C10'	126.66 (14)	N1'—C9'—C4'	107.66 (13)
C2'—C3'—C4'	106.34 (12)	C8'—C9'—C4'	122.78 (14)
C10'—C3'—C4'	126.99 (13)	O1—C10—C3	122.51 (15)
C5—C4—C9	118.60 (16)	O1—C10—C11	119.87 (15)
C5—C4—C3	134.95 (15)	C3—C10—C11	117.61 (13)
C9—C4—C3	106.45 (14)	O1'—C10'—C3'	122.74 (13)
C5'—C4'—C9'	118.54 (13)	O1'—C10'—C11'	120.06 (13)
C5'—C4'—C3'	135.07 (13)	C3'—C10'—C11'	117.20 (12)
C9'—C4'—C3'	106.36 (12)	C12'—C11'—C10'	112.33 (13)
C6'—C5'—C4'	118.70 (14)	C12'—C11'—H11A	109.1
C6'—C5'—H5'	120.6	C10'—C11'—H11A	109.1
C4'—C5'—H5'	120.6	C12'—C11'—H11B	109.1
C6—C5—C4	118.94 (17)	C10'—C11'—H11B	109.1
C6—C5—H5	120.5	H11A—C11'—H11B	107.9
C4—C5—H5	120.5	C12—C11—C10	112.34 (14)
C5'—C6'—C7'	121.46 (16)	C12—C11—H11C	109.1
C5'—C6'—H6'	119.3	C10—C11—H11C	109.1
C7'—C6'—H6'	119.3	C12—C11—H11D	109.1
C5—C6—C7	121.09 (19)	C10—C11—H11D	109.1
C5—C6—H6	119.5	H11C—C11—H11D	107.9
C7—C6—H6	119.5	N13—C12—C11	179.8 (2)
C8'—C7'—C6'	121.15 (16)	N13'—C12'—C11'	179.6 (2)

C9—N1—C2—C3	0.0 (2)	C2—N1—C9—C4	0.35 (18)
C9'—N1'—C2'—C3'	0.34 (17)	C5—C4—C9—C8	−0.7 (2)
N1—C2—C3—C10	178.76 (15)	C3—C4—C9—C8	179.28 (15)
N1—C2—C3—C4	−0.41 (19)	C5—C4—C9—N1	179.39 (14)
N1'—C2'—C3'—C10'	179.69 (14)	C3—C4—C9—N1	−0.59 (17)
N1'—C2'—C3'—C4'	−0.69 (17)	C2'—N1'—C9'—C8'	179.31 (16)
C2—C3—C4—C5	−179.36 (17)	C2'—N1'—C9'—C4'	0.18 (17)
C10—C3—C4—C5	1.5 (3)	C7'—C8'—C9'—N1'	−177.93 (15)
C2—C3—C4—C9	0.61 (17)	C7'—C8'—C9'—C4'	1.1 (2)
C10—C3—C4—C9	−178.56 (15)	C5'—C4'—C9'—N1'	177.78 (13)
C2'—C3'—C4'—C5'	−177.20 (16)	C3'—C4'—C9'—N1'	−0.59 (16)
C10'—C3'—C4'—C5'	2.4 (3)	C5'—C4'—C9'—C8'	−1.4 (2)
C2'—C3'—C4'—C9'	0.78 (16)	C3'—C4'—C9'—C8'	−179.80 (14)
C10'—C3'—C4'—C9'	−179.60 (14)	C2—C3—C10—O1	−179.17 (16)
C9'—C4'—C5'—C6'	0.4 (2)	C4—C3—C10—O1	−0.2 (3)
C3'—C4'—C5'—C6'	178.23 (16)	C2—C3—C10—C11	0.1 (2)
C9—C4—C5—C6	0.2 (2)	C4—C3—C10—C11	179.09 (15)
C3—C4—C5—C6	−179.88 (17)	C2'—C3'—C10'—O1'	−179.31 (15)
C4'—C5'—C6'—C7'	0.8 (3)	C4'—C3'—C10'—O1'	1.1 (2)
C4—C5—C6—C7	0.6 (3)	C2'—C3'—C10'—C11'	−0.3 (2)
C5'—C6'—C7'—C8'	−1.2 (3)	C4'—C3'—C10'—C11'	−179.83 (13)
C5—C6—C7—C8	−0.9 (3)	O1'—C10'—C11'—C12'	−14.8 (2)
C6'—C7'—C8'—C9'	0.2 (3)	C3'—C10'—C11'—C12'	166.12 (13)
C6—C7—C8—C9	0.3 (3)	O1—C10—C11—C12	−2.2 (2)
C7—C8—C9—N1	−179.67 (17)	C3—C10—C11—C12	178.56 (15)
C7—C8—C9—C4	0.5 (3)	C10—C11—C12—N13	51 (88)
C2—N1—C9—C8	−179.50 (18)	C10'—C11'—C12'—N13'	−58 (25)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.98	2.8146 (18)	163
C2—H2···N13ⁱ	0.93	2.59	3.236 (2)	127
N1′—H1′···O1′ⁱⁱ	0.86	2.00	2.8166 (15)	158

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

Experimental details

Crystal data
Chemical formula	C₁₁H₈N₂O
M_r	184.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3439 (2), 7.3534 (2), 18.2475 (5)
α, β, γ (°)	83.402 (2), 78.890 (2), 73.501 (1)
V (Å³)	925.23 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	18838, 3253, 2717
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.06
No. of reflections	3253
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.98	2.8146 (18)	163.0
C2—H2···N13ⁱ	0.93	2.59	3.236 (2)	126.9
N1'—H1'···O1'ⁱⁱ	0.86	2.00	2.8166 (15)	158.3

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

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

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