(E)-1-Diphenyl-methyl-idene-2-[(1H-indol-3-yl)methyl-idene]hydrazine.

In the title compound, C(22)H(17)N(3), the 1H-indole unit is essentially planar, with a dihedral angle of 0.95 (10)° between the pyrrole ring and the fused benzene ring. The dihedral angle between the two phenyl rings is 65.09 (10)°. In the crystal, an inter-molecular N-H⋯N hydrogen bond forms an infinite chain in the b-axis direction.

Related literature

For the synthesis, see: Fleming & Harley-Mason (1961 ▶). For the crystal structures of some aromatic azines, for example, acetophenone azine, see: Glaser et al. (1995 ▶). For other heterocyclic aldehyde azines, see: Lin et al. (2001 ▶). For the crystal structure of symmetrical 1H-Indole-3-carbaldehyde azine, see: Rizal et al. (2008 ▶).

Experimental

Crystal data

C22H17N3

M = 323.39

Orthorhombic,

a = 24.1594 (3) Å

b = 13.8501 (2) Å

c = 5.2173 (1) Å

V = 1745.76 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.58 mm−1

T = 295 K

0.46 × 0.21 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.796, T max = 1.000

8042 measured reflections

2059 independent reflections

1954 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.06

2059 reflections

230 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020702/nk2037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020702/nk2037Isup2.hkl

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

C22H17N3	Dx = 1.230 Mg m−3
Mr = 323.39	Melting point: 423 K
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2c -2n	Cell parameters from 6053 reflections
a = 24.1594 (3) Å	θ = 4.9–77.4°
b = 13.8501 (2) Å	µ = 0.57 mm−1
c = 5.2173 (1) Å	T = 295 K
V = 1745.76 (5) Å3	Needle, pale yellow
Z = 4	0.46 × 0.21 × 0.18 mm
F(000) = 680

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2059 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1954 reflections with I > 2σ(I)
graphite	Rint = 0.015
Detector resolution: 10.5081 pixels mm-1	θmax = 77.6°, θmin = 4.9°
ω scans	h = −30→27
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −17→17
Tmin = 0.796, Tmax = 1.000	l = −5→6
8042 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0712P)2 + 0.0189P] where P = (Fo2 + 2Fc2)/3
2059 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.12 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
N1	0.25795 (6)	0.62655 (10)	0.3007 (4)	0.0689 (4)
N2	0.15647 (5)	0.26575 (8)	0.6043 (3)	0.0551 (3)
N3	0.16478 (5)	0.36551 (8)	0.6361 (3)	0.0550 (4)
C1	0.20416 (6)	0.39405 (10)	0.4934 (4)	0.0582 (4)
C2	0.25644 (7)	0.52898 (11)	0.2923 (4)	0.0692 (5)
C3	0.21904 (6)	0.49427 (10)	0.4681 (4)	0.0578 (4)
C4	0.15783 (6)	0.59044 (12)	0.7935 (4)	0.0636 (5)
C5	0.14574 (8)	0.68387 (14)	0.8692 (5)	0.0778 (6)
C6	0.17085 (8)	0.76319 (13)	0.7519 (5)	0.0794 (7)
C7	0.20847 (8)	0.75255 (11)	0.5582 (5)	0.0711 (6)
C8	0.22152 (6)	0.65856 (11)	0.4834 (4)	0.0587 (4)
C9	0.19622 (5)	0.57731 (10)	0.5974 (3)	0.0540 (4)
C10	0.11010 (6)	0.23275 (9)	0.6904 (3)	0.0510 (3)
C11	0.09878 (6)	0.12935 (10)	0.6271 (3)	0.0576 (4)
C12	0.12405 (8)	0.08728 (13)	0.4155 (4)	0.0715 (6)
C13	0.11502 (10)	−0.00994 (14)	0.3603 (5)	0.0890 (8)
C14	0.08040 (10)	−0.06415 (13)	0.5133 (6)	0.0945 (9)
C15	0.05508 (10)	−0.02335 (13)	0.7208 (6)	0.0891 (8)
C16	0.06379 (8)	0.07414 (11)	0.7795 (5)	0.0710 (5)
C21	0.06955 (6)	0.28877 (10)	0.8444 (3)	0.0513 (4)
C22	0.01336 (6)	0.28961 (11)	0.7848 (4)	0.0609 (4)
C23	−0.02317 (7)	0.34404 (14)	0.9306 (5)	0.0728 (6)
C24	−0.00457 (8)	0.39643 (14)	1.1386 (4)	0.0735 (6)
C25	0.05106 (8)	0.39457 (13)	1.2010 (4)	0.0686 (5)
C26	0.08756 (6)	0.34155 (11)	1.0559 (3)	0.0593 (4)
H1	0.2797 (10)	0.6616 (17)	0.204 (6)	0.089 (7)*
H1A	0.22419	0.34832	0.40160	0.0698*
H2	0.27765	0.49087	0.18322	0.0830*
H4	0.14080	0.53787	0.87152	0.0764*
H5	0.12039	0.69401	1.00059	0.0933*
H6	0.16173	0.82502	0.80720	0.0953*
H7	0.22468	0.80575	0.47948	0.0853*
H12	0.14699	0.12400	0.31071	0.0858*
H13	0.13237	−0.03826	0.22001	0.1067*
H14	0.07425	−0.12885	0.47504	0.1133*
H15	0.03194	−0.06049	0.82360	0.1069*
H16	0.04622	0.10185	0.92001	0.0852*
H22	0.00029	0.25361	0.64707	0.0731*
H23	−0.06054	0.34525	0.88781	0.0873*
H24	−0.02924	0.43266	1.23595	0.0882*
H25	0.06382	0.42930	1.34165	0.0823*
H26	0.12488	0.34091	1.09955	0.0711*

	U11	U22	U33	U12	U13	U23
N1	0.0668 (7)	0.0567 (7)	0.0833 (9)	−0.0144 (6)	0.0116 (8)	0.0021 (8)
N2	0.0562 (6)	0.0416 (5)	0.0675 (7)	0.0010 (4)	−0.0022 (6)	0.0012 (6)
N3	0.0535 (5)	0.0425 (5)	0.0689 (8)	−0.0018 (4)	0.0006 (5)	0.0014 (6)
C1	0.0501 (6)	0.0493 (6)	0.0751 (10)	0.0016 (5)	0.0050 (7)	−0.0012 (7)
C2	0.0642 (8)	0.0578 (8)	0.0856 (11)	−0.0070 (6)	0.0161 (9)	−0.0013 (9)
C3	0.0483 (6)	0.0514 (7)	0.0737 (9)	−0.0034 (5)	0.0032 (7)	0.0006 (7)
C4	0.0556 (7)	0.0622 (8)	0.0731 (10)	−0.0023 (6)	0.0038 (8)	−0.0011 (8)
C5	0.0673 (9)	0.0766 (10)	0.0894 (14)	0.0047 (8)	0.0079 (9)	−0.0178 (10)
C6	0.0784 (10)	0.0573 (8)	0.1025 (16)	0.0033 (7)	−0.0065 (11)	−0.0201 (10)
C7	0.0747 (9)	0.0509 (7)	0.0877 (12)	−0.0090 (7)	−0.0107 (10)	−0.0036 (8)
C8	0.0535 (6)	0.0529 (7)	0.0697 (9)	−0.0084 (5)	−0.0072 (7)	0.0002 (7)
C9	0.0445 (6)	0.0507 (6)	0.0668 (9)	−0.0037 (5)	−0.0064 (6)	−0.0003 (7)
C10	0.0535 (6)	0.0432 (5)	0.0562 (7)	−0.0007 (5)	−0.0090 (6)	0.0058 (6)
C11	0.0620 (7)	0.0449 (6)	0.0660 (8)	−0.0027 (5)	−0.0177 (7)	0.0019 (7)
C12	0.0800 (10)	0.0593 (8)	0.0752 (11)	0.0023 (7)	−0.0156 (9)	−0.0079 (8)
C13	0.1040 (14)	0.0647 (10)	0.0982 (16)	0.0089 (9)	−0.0288 (13)	−0.0240 (11)
C14	0.1079 (15)	0.0465 (8)	0.129 (2)	−0.0049 (9)	−0.0440 (16)	−0.0108 (11)
C15	0.1001 (14)	0.0516 (9)	0.1155 (19)	−0.0200 (9)	−0.0224 (13)	0.0108 (11)
C16	0.0786 (10)	0.0512 (7)	0.0833 (11)	−0.0120 (7)	−0.0120 (10)	0.0077 (8)
C21	0.0551 (7)	0.0453 (6)	0.0535 (7)	−0.0041 (5)	−0.0037 (6)	0.0089 (5)
C22	0.0557 (7)	0.0612 (7)	0.0658 (8)	−0.0039 (6)	−0.0070 (7)	0.0032 (8)
C23	0.0559 (7)	0.0787 (10)	0.0837 (12)	0.0040 (7)	−0.0001 (9)	0.0088 (10)
C24	0.0738 (10)	0.0731 (9)	0.0737 (11)	0.0080 (8)	0.0134 (9)	0.0029 (9)
C25	0.0808 (10)	0.0693 (9)	0.0557 (8)	−0.0044 (8)	0.0030 (8)	−0.0016 (8)
C26	0.0596 (7)	0.0627 (8)	0.0556 (7)	−0.0049 (6)	−0.0055 (6)	0.0036 (7)

N1—C2	1.353 (2)	C21—C26	1.393 (2)
N1—C8	1.371 (3)	C21—C22	1.393 (2)
N2—N3	1.4060 (16)	C22—C23	1.388 (3)
N2—C10	1.2906 (19)	C23—C24	1.381 (3)
N3—C1	1.271 (2)	C24—C25	1.383 (3)
N1—H1	0.88 (3)	C25—C26	1.375 (2)
C1—C3	1.440 (2)	C1—H1A	0.9300
C2—C3	1.374 (3)	C2—H2	0.9300
C3—C9	1.443 (2)	C4—H4	0.9300
C4—C5	1.384 (3)	C5—H5	0.9300
C4—C9	1.393 (2)	C6—H6	0.9300
C5—C6	1.396 (3)	C7—H7	0.9300
C6—C7	1.367 (3)	C12—H12	0.9300
C7—C8	1.395 (2)	C13—H13	0.9300
C8—C9	1.412 (2)	C14—H14	0.9300
C10—C21	1.486 (2)	C15—H15	0.9300
C10—C11	1.4949 (19)	C16—H16	0.9300
C11—C12	1.390 (3)	C22—H22	0.9300
C11—C16	1.390 (3)	C23—H23	0.9300
C12—C13	1.394 (3)	C24—H24	0.9300
C13—C14	1.379 (3)	C25—H25	0.9300
C14—C15	1.366 (4)	C26—H26	0.9300
C15—C16	1.400 (2)
N1···N2i	3.0069 (19)	C12···H2ii	3.0600
N2···N1ii	3.0069 (19)	C13···H2ii	3.0900
N3···C4	3.226 (2)	C14···H6v	2.9300
N3···C26	2.896 (2)	C16···H22	3.0000
N2···H26iii	2.9300	C21···H16	2.6800
N2···H1ii	2.18 (2)	C22···H16	2.8100
N2···H26	2.8900	H1···N2i	2.18 (2)
N2···H12	2.5000	H1···C10i	2.84 (2)
N3···H4	2.7500	H1···C11i	3.00 (2)
N3···H26	2.6300	H1···C12i	2.96 (3)
C2···C12i	3.585 (3)	H1A···C6viii	2.9000
C4···N3	3.226 (2)	H1A···C7viii	2.7600
C6···C14iv	3.470 (3)	H1A···H7viii	2.5900
C12···C2ii	3.585 (3)	H2···C12i	3.0600
C13···C16iii	3.474 (4)	H2···C13i	3.0900
C14···C6v	3.470 (3)	H4···N3	2.7500
C16···C22	3.224 (2)	H5···H23ix	2.5400
C16···C13vi	3.474 (4)	H6···C14iv	2.9300
C22···C25iii	3.496 (3)	H7···H1Avii	2.5900
C22···C16	3.224 (2)	H12···N2	2.5000
C25···C22vi	3.496 (3)	H16···C21	2.6800
C26···N3	2.896 (2)	H16···C22	2.8100
C1···H26iii	2.9000	H22···C11	2.9400
C6···H1Avii	2.9000	H22···C16	3.0000
C7···H1Avii	2.7600	H23···H5x	2.5400
C10···H1ii	2.84 (2)	H26···N2	2.8900
C11···H22	2.9400	H26···N2vi	2.9300
C11···H1ii	3.00 (2)	H26···N3	2.6300
C12···H1ii	2.96 (3)	H26···C1vi	2.9000
C2—N1—C8	109.17 (15)	C23—C24—C25	119.44 (18)
N3—N2—C10	115.52 (12)	C24—C25—C26	120.24 (18)
N2—N3—C1	110.08 (13)	C21—C26—C25	121.07 (15)
C2—N1—H1	123.5 (16)	N3—C1—H1A	119.00
C8—N1—H1	127.4 (17)	C3—C1—H1A	119.00
N3—C1—C3	122.71 (15)	N1—C2—H2	125.00
N1—C2—C3	110.22 (16)	C3—C2—H2	125.00
C1—C3—C2	124.23 (16)	C5—C4—H4	121.00
C2—C3—C9	106.52 (13)	C9—C4—H4	121.00
C1—C3—C9	129.06 (15)	C4—C5—H5	119.00
C5—C4—C9	118.18 (16)	C6—C5—H5	119.00
C4—C5—C6	121.3 (2)	C5—C6—H6	119.00
C5—C6—C7	121.87 (18)	C7—C6—H6	119.00
C6—C7—C8	117.23 (17)	C6—C7—H7	121.00
C7—C8—C9	121.87 (17)	C8—C7—H7	121.00
N1—C8—C7	129.89 (17)	C11—C12—H12	120.00
N1—C8—C9	108.24 (13)	C13—C12—H12	120.00
C4—C9—C8	119.58 (14)	C12—C13—H13	120.00
C3—C9—C4	134.58 (14)	C14—C13—H13	120.00
C3—C9—C8	105.84 (13)	C13—C14—H14	120.00
N2—C10—C11	114.91 (13)	C15—C14—H14	120.00
N2—C10—C21	125.15 (12)	C14—C15—H15	120.00
C11—C10—C21	119.94 (12)	C16—C15—H15	120.00
C10—C11—C12	119.79 (14)	C11—C16—H16	120.00
C12—C11—C16	119.41 (15)	C15—C16—H16	120.00
C10—C11—C16	120.80 (15)	C21—C22—H22	120.00
C11—C12—C13	120.02 (18)	C23—C22—H22	120.00
C12—C13—C14	120.1 (2)	C22—C23—H23	120.00
C13—C14—C15	120.36 (19)	C24—C23—H23	120.00
C14—C15—C16	120.3 (2)	C23—C24—H24	120.00
C11—C16—C15	119.8 (2)	C25—C24—H24	120.00
C10—C21—C22	121.76 (14)	C24—C25—H25	120.00
C22—C21—C26	118.48 (14)	C26—C25—H25	120.00
C10—C21—C26	119.76 (13)	C21—C26—H26	119.00
C21—C22—C23	120.14 (17)	C25—C26—H26	119.00
C22—C23—C24	120.62 (17)
C8—N1—C2—C3	0.1 (2)	C7—C8—C9—C4	−1.2 (3)
C2—N1—C8—C7	−179.2 (2)	N2—C10—C11—C12	−24.1 (2)
C2—N1—C8—C9	0.6 (2)	N2—C10—C11—C16	155.04 (17)
C10—N2—N3—C1	−164.25 (15)	C21—C10—C11—C12	156.63 (16)
N3—N2—C10—C11	172.86 (13)	C21—C10—C11—C16	−24.3 (2)
N3—N2—C10—C21	−7.9 (2)	N2—C10—C21—C22	131.69 (18)
N2—N3—C1—C3	174.46 (16)	N2—C10—C21—C26	−48.9 (2)
N3—C1—C3—C2	−171.37 (18)	C11—C10—C21—C22	−49.1 (2)
N3—C1—C3—C9	3.0 (3)	C11—C10—C21—C26	130.34 (15)
N1—C2—C3—C1	174.67 (17)	C10—C11—C12—C13	177.96 (18)
N1—C2—C3—C9	−0.8 (2)	C16—C11—C12—C13	−1.2 (3)
C1—C3—C9—C4	6.0 (3)	C10—C11—C16—C15	−178.12 (19)
C1—C3—C9—C8	−174.06 (18)	C12—C11—C16—C15	1.0 (3)
C2—C3—C9—C4	−178.90 (18)	C11—C12—C13—C14	0.9 (3)
C2—C3—C9—C8	1.10 (19)	C12—C13—C14—C15	−0.5 (4)
C9—C4—C5—C6	0.5 (3)	C13—C14—C15—C16	0.4 (4)
C5—C4—C9—C3	−179.81 (19)	C14—C15—C16—C11	−0.6 (4)
C5—C4—C9—C8	0.2 (2)	C10—C21—C22—C23	−178.96 (16)
C4—C5—C6—C7	−0.2 (4)	C26—C21—C22—C23	1.6 (2)
C5—C6—C7—C8	−0.8 (3)	C10—C21—C26—C25	179.57 (15)
C6—C7—C8—N1	−178.7 (2)	C22—C21—C26—C25	−1.0 (2)
C6—C7—C8—C9	1.5 (3)	C21—C22—C23—C24	−1.2 (3)
N1—C8—C9—C3	−1.04 (19)	C22—C23—C24—C25	0.2 (3)
N1—C8—C9—C4	178.96 (15)	C23—C24—C25—C26	0.5 (3)
C7—C8—C9—C3	178.80 (18)	C24—C25—C26—C21	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88 (3)	2.18 (2)	3.0069 (19)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88 (3)	2.18 (2)	3.0069 (19)	159 (3)

Symmetry code: (i) .