4-[Bis(1H-indol-3-yl)meth­yl]benzonitrile

Deng, X.; Wu, D.; Huang, X.; Luo, F.

doi:10.1107/S1600536811020411

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1603

doi:10.1107/S1600536811020411

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4-[Bis(1H-indol-3-yl)methyl]benzonitrile

Xiang Deng,^a ^* Di Wu,^a Xiaomei Huang ^a and Feihua Luo ^a

^aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Sichuan Key Laboratory of Characteristic Plant Development Research, Sichuan Dazhou 635000, People's Republic of China
^*Correspondence e-mail: qwj616@swu.edu.cn

(Received 9 May 2011; accepted 28 May 2011; online 11 June 2011)

In the title molecule, C₂₄H₁₇N₃, the didhedral angles formed by the mean planes of the indole ring systems and the benzene ring are 86.44 (7) and 86.96 (7)°. The dihedral angle between the two indole ring systems is 72.08 (6)°. In the crystal, intermolecular bifurcated (N—H)₂⋯N hydrogen bonds link molecules into sheets lying parallel to (010).

Related literature

For background and the biological activity of bisindolylalkanes and their derivatives, see: Bell et al. (1994 ). For related structures, see: Govindasamy et al. (1998 ); Krishna, Velmurugan, Babu & Perumal (1999 ); Krishna, Velmurugan & Shanmuga Sundara (1999 ); Seetharaman & Rajan (1995 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₁₇N₃
M_r = 347.41
Monoclinic, P 2₁ /c
a = 9.5882 (12) Å
b = 19.155 (3) Å
c = 10.3801 (13) Å
β = 100.562 (3)°
V = 1874.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer
14081 measured reflections
3292 independent reflections
2613 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.05
3292 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1ⁱ	0.86 (2)	2.22 (2)	3.084 (2)	178.6 (18)
N2—H2A⋯N1ⁱⁱ	0.91 (2)	2.34 (2)	3.206 (2)	160.3 (19)
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020411/lh5252sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020411/lh5252Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020411/lh5252Isup3.cml

checkCIF report

Comment top

Bisindolylalkanes and their derivatives constitute an important group of bioactive metabolites of terrestrial and marine origin (Bell et al., 1994). We report here the crystal structure of the title compound (I). In the molecular structure, (Fig. 1) the bond lengths (Allen et al., 1987) and and angles are within normal ranges and those in the indole group are in agreement with related structures (Govindasamy et al., 1998; Krishna, Velmurugan, Babu & Perumal, 1999; Krishna, Velmurugan & Shanmuga Sundara, 1999; Seetharaman & Rajan, 1995). The didhedral angles formed by the mean planes of the indole ring systems and the benzene ring are 86.44 (7) and 86.96 (7)°. The dihedral angle between the two indole ring systems is 72.08 (6)°. In the crystal, intermolecular bifurcated (N—H)x2···N hydrogen bonds link molecules into two-dimensional sheets parallel to (010) (Fig. 2).

Related literature top

For background and the biological activity of bisindolylalkanes and their derivatives, see: Bell et al. (1994). For related structures, see: Govindasamy et al. (1998); Krishna, Velmurugan, Babu & Perumal (1999); Krishna, Velmurugan & Shanmuga Sundara (1999); Seetharaman & Rajan (1995). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixuture of 4-cyanobenzaldehyde (1 mmol), indole (2 mmol) and I₂ (0.2 mmol) in acetonitrile (10 ml) was stirred at room temperature for a few s. After completion of the reaction, the mixture treated with aq. Na₂S₂O₃ solution (5%, 10 ml) and the product was extracted with ethyl acetate (3×5 ml). The combined organic layer was dried with anhydrous sodium sulfate, concentrated in vacuo and purified by column chromatography (ethyl acetate: petroleum ether=1:9) to afford the pure product. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines. Only H atoms involved in the hydrogen bonds are shown.

4-[Bis(1H-indol-3-yl)methyl]benzonitrile top

Crystal data top

C₂₄H₁₇N₃	F(000) = 728
M_r = 347.41	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3543 reflections
a = 9.5882 (12) Å	θ = 2.9–24.6°
b = 19.155 (3) Å	µ = 0.07 mm⁻¹
c = 10.3801 (13) Å	T = 296 K
β = 100.562 (3)°	Block, colourless
V = 1874.1 (4) Å³	0.20 × 0.15 × 0.09 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ϕ and ω scans	h = −11→11
14081 measured reflections	k = −22→22
3292 independent reflections	l = −12→12

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0494P)² + 0.3483P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3292 reflections	Δρ_max = 0.15 e Å⁻³
253 parameters	Δρ_min = −0.13 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: 0.030 (2)

Crystal data top

C₂₄H₁₇N₃	V = 1874.1 (4) Å³
M_r = 347.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5882 (12) Å	µ = 0.07 mm⁻¹
b = 19.155 (3) Å	T = 296 K
c = 10.3801 (13) Å	0.20 × 0.15 × 0.09 mm
β = 100.562 (3)°

Data collection top

Bruker SMART CCD diffractometer	2613 reflections with I > 2σ(I)
14081 measured reflections	R_int = 0.036
3292 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.15 e Å⁻³
3292 reflections	Δρ_min = −0.13 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
C1	0.58636 (15)	0.10803 (8)	0.05439 (14)	0.0403 (4)
H1	0.5637	0.0581	0.0542	0.048*
C2	0.62867 (15)	0.12277 (7)	−0.07541 (15)	0.0403 (4)
C3	0.54762 (15)	0.10350 (8)	−0.20061 (15)	0.0421 (4)
C4	0.41722 (17)	0.06995 (9)	−0.23996 (16)	0.0520 (4)
H4	0.3633	0.0566	−0.1782	0.062*
C5	0.3700 (2)	0.05705 (10)	−0.37001 (18)	0.0652 (5)
H5	0.2839	0.0342	−0.3963	0.078*
C6	0.4482 (2)	0.07750 (11)	−0.46368 (19)	0.0690 (5)
H6	0.4132	0.0685	−0.5517	0.083*
C7	0.5762 (2)	0.11079 (10)	−0.42865 (17)	0.0627 (5)
H7	0.6286	0.1242	−0.4915	0.075*
C8	0.62532 (16)	0.12383 (8)	−0.29631 (16)	0.0467 (4)
C9	0.74842 (16)	0.15361 (8)	−0.10002 (17)	0.0477 (4)
H9	0.8208	0.1714	−0.0365	0.057*
C10	0.70384 (15)	0.11951 (8)	0.16965 (15)	0.0419 (4)
C11	0.82977 (15)	0.07764 (8)	0.20221 (15)	0.0425 (4)
C12	0.88333 (17)	0.02088 (9)	0.14286 (17)	0.0526 (4)
H12	0.8366	0.0042	0.0623	0.063*
C13	1.00687 (19)	−0.01001 (10)	0.2058 (2)	0.0657 (5)
H13	1.0432	−0.0481	0.1674	0.079*
C14	1.0784 (2)	0.01494 (11)	0.3263 (2)	0.0686 (5)
H14	1.1610	−0.0073	0.3671	0.082*
C15	1.02992 (19)	0.07111 (11)	0.38510 (18)	0.0624 (5)
H15	1.0783	0.0878	0.4650	0.075*
C16	0.90608 (16)	0.10251 (9)	0.32187 (15)	0.0496 (4)
C17	0.71121 (17)	0.16730 (9)	0.26731 (16)	0.0517 (4)
H17	0.6434	0.2015	0.2715	0.062*
C18	0.45208 (15)	0.14628 (8)	0.07105 (15)	0.0422 (4)
C19	0.42852 (19)	0.21445 (10)	0.0326 (2)	0.0742 (6)
H19	0.4949	0.2373	−0.0072	0.089*
C20	0.3091 (2)	0.24975 (10)	0.0516 (2)	0.0786 (7)
H20	0.2961	0.2962	0.0262	0.094*
C21	0.20928 (16)	0.21613 (9)	0.10831 (17)	0.0528 (4)
C22	0.23052 (18)	0.14779 (10)	0.14648 (19)	0.0647 (5)
H22	0.1631	0.1246	0.1846	0.078*
C23	0.35136 (17)	0.11352 (9)	0.12836 (17)	0.0569 (5)
H23	0.3653	0.0673	0.1554	0.068*
C24	0.08275 (18)	0.25223 (10)	0.12602 (18)	0.0602 (5)
N1	−0.01856 (16)	0.28075 (10)	0.13748 (17)	0.0757 (5)
N2	0.83216 (15)	0.15817 (8)	0.35857 (15)	0.0585 (4)
H2A	0.856 (2)	0.1831 (12)	0.434 (2)	0.088 (7)*
N3	0.74724 (15)	0.15470 (7)	−0.23225 (15)	0.0539 (4)
H3A	0.814 (2)	0.1722 (10)	−0.2680 (19)	0.069 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0363 (8)	0.0372 (8)	0.0485 (9)	0.0003 (6)	0.0109 (7)	0.0017 (7)
C2	0.0330 (7)	0.0403 (8)	0.0488 (9)	0.0030 (6)	0.0102 (7)	0.0026 (7)
C3	0.0387 (8)	0.0405 (8)	0.0478 (9)	0.0061 (7)	0.0101 (7)	0.0065 (7)
C4	0.0448 (9)	0.0555 (10)	0.0540 (10)	−0.0033 (8)	0.0051 (8)	0.0092 (8)
C5	0.0619 (11)	0.0678 (12)	0.0594 (12)	−0.0042 (9)	−0.0057 (9)	0.0031 (9)
C6	0.0797 (14)	0.0726 (13)	0.0498 (11)	0.0064 (11)	−0.0007 (10)	0.0013 (9)
C7	0.0752 (13)	0.0673 (12)	0.0496 (11)	0.0144 (10)	0.0219 (9)	0.0124 (9)
C8	0.0446 (9)	0.0450 (9)	0.0530 (10)	0.0077 (7)	0.0152 (7)	0.0085 (7)
C9	0.0383 (8)	0.0484 (9)	0.0574 (10)	−0.0027 (7)	0.0118 (7)	0.0019 (7)
C10	0.0369 (8)	0.0449 (9)	0.0455 (9)	−0.0026 (6)	0.0119 (7)	0.0005 (7)
C11	0.0366 (8)	0.0479 (9)	0.0443 (9)	−0.0022 (7)	0.0110 (7)	0.0054 (7)
C12	0.0470 (9)	0.0536 (10)	0.0576 (10)	0.0024 (8)	0.0109 (8)	0.0013 (8)
C13	0.0561 (11)	0.0599 (11)	0.0824 (14)	0.0144 (9)	0.0163 (10)	0.0089 (10)
C14	0.0497 (10)	0.0788 (14)	0.0744 (13)	0.0089 (10)	0.0035 (10)	0.0259 (11)
C15	0.0503 (10)	0.0829 (14)	0.0511 (10)	−0.0064 (10)	0.0017 (8)	0.0153 (10)
C16	0.0430 (9)	0.0604 (10)	0.0465 (9)	−0.0070 (8)	0.0110 (7)	0.0066 (8)
C17	0.0434 (9)	0.0565 (10)	0.0567 (10)	−0.0002 (8)	0.0131 (8)	−0.0054 (8)
C18	0.0351 (8)	0.0442 (9)	0.0483 (9)	−0.0013 (6)	0.0108 (7)	0.0011 (7)
C19	0.0574 (11)	0.0509 (11)	0.1275 (18)	0.0076 (9)	0.0519 (12)	0.0222 (11)
C20	0.0654 (12)	0.0509 (11)	0.1321 (19)	0.0138 (9)	0.0516 (13)	0.0227 (11)
C21	0.0400 (9)	0.0618 (11)	0.0593 (10)	0.0086 (8)	0.0163 (8)	0.0024 (8)
C22	0.0508 (10)	0.0704 (12)	0.0821 (13)	0.0072 (9)	0.0362 (9)	0.0218 (10)
C23	0.0503 (10)	0.0539 (10)	0.0723 (12)	0.0079 (8)	0.0264 (9)	0.0198 (9)
C24	0.0460 (10)	0.0738 (12)	0.0634 (12)	0.0099 (9)	0.0171 (8)	0.0044 (9)
N1	0.0533 (9)	0.0929 (13)	0.0860 (12)	0.0226 (9)	0.0265 (8)	0.0099 (9)
N2	0.0539 (9)	0.0728 (10)	0.0486 (9)	−0.0063 (8)	0.0088 (7)	−0.0127 (8)
N3	0.0445 (8)	0.0587 (9)	0.0643 (10)	−0.0013 (7)	0.0253 (7)	0.0109 (7)

Geometric parameters (Å, º) top

C1—C10	1.502 (2)	C12—H12	0.9300
C1—C2	1.503 (2)	C13—C14	1.396 (3)
C1—C18	1.519 (2)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.361 (3)
C2—C9	1.356 (2)	C14—H14	0.9300
C2—C3	1.435 (2)	C15—C16	1.384 (2)
C3—C4	1.399 (2)	C15—H15	0.9300
C3—C8	1.402 (2)	C16—N2	1.372 (2)
C4—C5	1.366 (2)	C17—N2	1.368 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.389 (3)	C18—C19	1.372 (2)
C5—H5	0.9300	C18—C23	1.375 (2)
C6—C7	1.371 (3)	C19—C20	1.375 (2)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.391 (2)	C20—C21	1.373 (2)
C7—H7	0.9300	C20—H20	0.9300
C8—N3	1.369 (2)	C21—C22	1.372 (2)
C9—N3	1.371 (2)	C21—C24	1.437 (2)
C9—H9	0.9300	C22—C23	1.374 (2)
C10—C17	1.358 (2)	C22—H22	0.9300
C10—C11	1.437 (2)	C23—H23	0.9300
C11—C12	1.393 (2)	C24—N1	1.140 (2)
C11—C16	1.404 (2)	N2—H2A	0.91 (2)
C12—C13	1.377 (2)	N3—H3A	0.86 (2)

C10—C1—C2	113.60 (12)	C12—C13—H13	119.4
C10—C1—C18	111.50 (12)	C14—C13—H13	119.4
C2—C1—C18	112.65 (12)	C15—C14—C13	121.38 (17)
C10—C1—H1	106.1	C15—C14—H14	119.3
C2—C1—H1	106.1	C13—C14—H14	119.3
C18—C1—H1	106.1	C14—C15—C16	117.70 (17)
C9—C2—C3	106.14 (13)	C14—C15—H15	121.2
C9—C2—C1	128.86 (14)	C16—C15—H15	121.2
C3—C2—C1	124.97 (13)	N2—C16—C15	130.37 (17)
C4—C3—C8	118.91 (15)	N2—C16—C11	107.29 (14)
C4—C3—C2	133.59 (14)	C15—C16—C11	122.30 (17)
C8—C3—C2	107.49 (13)	C10—C17—N2	110.63 (15)
C5—C4—C3	119.26 (16)	C10—C17—H17	124.7
C5—C4—H4	120.4	N2—C17—H17	124.7
C3—C4—H4	120.4	C19—C18—C23	117.96 (14)
C4—C5—C6	121.14 (18)	C19—C18—C1	121.60 (13)
C4—C5—H5	119.4	C23—C18—C1	120.43 (14)
C6—C5—H5	119.4	C18—C19—C20	121.58 (16)
C7—C6—C5	121.16 (18)	C18—C19—H19	119.2
C7—C6—H6	119.4	C20—C19—H19	119.2
C5—C6—H6	119.4	C21—C20—C19	119.69 (17)
C6—C7—C8	118.03 (17)	C21—C20—H20	120.2
C6—C7—H7	121.0	C19—C20—H20	120.2
C8—C7—H7	121.0	C22—C21—C20	119.55 (15)
N3—C8—C7	131.44 (16)	C22—C21—C24	120.41 (16)
N3—C8—C3	107.05 (14)	C20—C21—C24	120.04 (16)
C7—C8—C3	121.50 (16)	C21—C22—C23	120.03 (15)
C2—C9—N3	110.08 (15)	C21—C22—H22	120.0
C2—C9—H9	125.0	C23—C22—H22	120.0
N3—C9—H9	125.0	C22—C23—C18	121.19 (16)
C17—C10—C11	105.91 (14)	C22—C23—H23	119.4
C17—C10—C1	128.49 (14)	C18—C23—H23	119.4
C11—C10—C1	125.50 (13)	N1—C24—C21	178.7 (2)
C12—C11—C16	118.77 (14)	C17—N2—C16	108.82 (14)
C12—C11—C10	133.90 (15)	C17—N2—H2A	125.3 (14)
C16—C11—C10	107.31 (14)	C16—N2—H2A	125.7 (14)
C13—C12—C11	118.70 (17)	C8—N3—C9	109.24 (13)
C13—C12—H12	120.7	C8—N3—H3A	126.3 (13)
C11—C12—H12	120.7	C9—N3—H3A	124.4 (13)
C12—C13—C14	121.11 (18)

C10—C1—C2—C9	−10.3 (2)	C11—C12—C13—C14	−0.5 (3)
C18—C1—C2—C9	117.73 (17)	C12—C13—C14—C15	−0.8 (3)
C10—C1—C2—C3	167.30 (13)	C13—C14—C15—C16	0.5 (3)
C18—C1—C2—C3	−64.69 (18)	C14—C15—C16—N2	178.63 (17)
C9—C2—C3—C4	179.30 (17)	C14—C15—C16—C11	1.1 (2)
C1—C2—C3—C4	1.3 (3)	C12—C11—C16—N2	179.62 (14)
C9—C2—C3—C8	0.43 (16)	C10—C11—C16—N2	−1.61 (17)
C1—C2—C3—C8	−177.61 (13)	C12—C11—C16—C15	−2.3 (2)
C8—C3—C4—C5	0.9 (2)	C10—C11—C16—C15	176.45 (14)
C2—C3—C4—C5	−177.91 (16)	C11—C10—C17—N2	−0.21 (18)
C3—C4—C5—C6	−0.9 (3)	C1—C10—C17—N2	176.26 (14)
C4—C5—C6—C7	0.6 (3)	C10—C1—C18—C19	87.1 (2)
C5—C6—C7—C8	−0.3 (3)	C2—C1—C18—C19	−42.0 (2)
C6—C7—C8—N3	179.15 (17)	C10—C1—C18—C23	−91.44 (18)
C6—C7—C8—C3	0.3 (3)	C2—C1—C18—C23	139.46 (16)
C4—C3—C8—N3	−179.68 (14)	C23—C18—C19—C20	0.7 (3)
C2—C3—C8—N3	−0.62 (17)	C1—C18—C19—C20	−177.84 (19)
C4—C3—C8—C7	−0.6 (2)	C18—C19—C20—C21	−1.1 (4)
C2—C3—C8—C7	178.47 (14)	C19—C20—C21—C22	0.6 (3)
C3—C2—C9—N3	−0.08 (17)	C19—C20—C21—C24	−178.70 (19)
C1—C2—C9—N3	177.86 (14)	C20—C21—C22—C23	0.2 (3)
C2—C1—C10—C17	115.39 (17)	C24—C21—C22—C23	179.56 (18)
C18—C1—C10—C17	−13.2 (2)	C21—C22—C23—C18	−0.6 (3)
C2—C1—C10—C11	−68.78 (18)	C19—C18—C23—C22	0.2 (3)
C18—C1—C10—C11	162.63 (13)	C1—C18—C23—C22	178.74 (16)
C17—C10—C11—C12	179.63 (17)	C10—C17—N2—C16	−0.81 (19)
C1—C10—C11—C12	3.0 (3)	C15—C16—N2—C17	−176.35 (17)
C17—C10—C11—C16	1.12 (17)	C11—C16—N2—C17	1.50 (18)
C1—C10—C11—C16	−175.49 (14)	C7—C8—N3—C9	−178.39 (17)
C16—C11—C12—C13	2.0 (2)	C3—C8—N3—C9	0.58 (17)
C10—C11—C12—C13	−176.41 (16)	C2—C9—N3—C8	−0.32 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.86 (2)	2.22 (2)	3.084 (2)	178.6 (18)
N2—H2A···N1ⁱⁱ	0.91 (2)	2.34 (2)	3.206 (2)	160.3 (19)

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₇N₃
M_r	347.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.5882 (12), 19.155 (3), 10.3801 (13)
β (°)	100.562 (3)
V (Å³)	1874.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.15 × 0.09

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14081, 3292, 2613
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.05
No. of reflections	3292
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.86 (2)	2.22 (2)	3.084 (2)	178.6 (18)
N2—H2A···N1ⁱⁱ	0.91 (2)	2.34 (2)	3.206 (2)	160.3 (19)

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

Acknowledgements

We are grateful to the Key Program of the Education Department of Sichuan Province (grant No. 10ZA143) and Youth Foundation of the Education Department of Sichuan Province (grant No.10ZB105) for financial support.

References

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