(E)-1-Diphenyl­methyl­idene-2-[(1H-indol-3-yl)methyl­idene]hydrazine

Archana, R.; Anbazhagan, R.; Sankaran, K.R.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536810020702

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1586

doi:10.1107/S1600536810020702

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(E)-1-Diphenylmethylidene-2-[(1H-indol-3-yl)methylidene]hydrazine

R. Archana,^a R. Anbazhagan,^b K. R. Sankaran,^b A. Thiruvalluvar ^a ^* and R. J. Butcher ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: athiru@vsnl.net

(Received 19 May 2010; accepted 31 May 2010; online 5 June 2010)

In the title compound, C₂₂H₁₇N₃, 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 intermolecular 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_r = 323.39
Orthorhombic, P n a 2₁
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.06
2059 reflections
230 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.17 e Å⁻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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound is an unsymmetrical indole azine derived from benzophenone, indole-3-carboxaldehyde and hydrazine. Glaser et al., (1995) have reported the crystal structures of some aromatic azines. Lin et al., (2001) have reported heterocyclic aldehyde azines. Rizal et al., (2008) have reported the crystal structure of symmetrical 1H-Indole-3-carbaldehyde azine. Herein, we report the crystal structure of the title compound.

In the title molecule (Scheme I, Fig. 1), C₂₂H₁₇N₃, the 1H-indole unit is almost planar, as the pyrrole ring makes a dihedral angle of 0.95 (10)° with the fused benzene ring. The r.m.s. deviation of a mean plane fitted through all non hydrogen atoms of the indole unit is 0.0096 Å; C3 deviates from this plane by 0.015 (1) Å. The dihedral angle between the two phenyl rings of the diphenylmethylene residue is 65.09 (10)°. The crystal structure is stabilized by intermolecular N1—H1···N2(1/2 - x, 1/2 + y, -1/2 + z) hydrogen bond forming an infinite one-dimensional chain in the b-axis direction (Fig. 2).

Related literature top

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 top

The compound was prepared in accord with literature precedents Fleming & Harley-Mason (1961). The mixture of benzophenone hydrazone (1.96 g, 0.01 mol) and indole-3-carboxaldehyde (2.55 g, 0.01 mol) in ethanol was refluxed for 2 h. The mixture was cooled to room temperature over night. The solid obtained was separated, dried and then recrystallized from absolute ethanol. The yield of isolated product was (1.76 g, 79%).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

(E)-1-Diphenylmethylidene-2-[(1H-indol-3-yl)methylidene]hydrazine top

Crystal data top

C₂₂H₁₇N₃	D_x = 1.230 Mg m⁻³
M_r = 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 = 0.58 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

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2059 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.6°, θ_min = 4.9°
ω scans	h = −30→27
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −17→17
T_min = 0.796, T_max = 1.000	l = −5→6
8042 measured reflections

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)] = 0.032	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(F_o²) + (0.0712P)² + 0.0189P] where P = (F_o² + 2F_c²)/3
2059 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.12 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₁₇N₃	V = 1745.76 (5) Å³
M_r = 323.39	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 24.1594 (3) Å	µ = 0.58 mm⁻¹
b = 13.8501 (2) Å	T = 295 K
c = 5.2173 (1) Å	0.46 × 0.21 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2059 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1954 reflections with I > 2σ(I)
T_min = 0.796, T_max = 1.000	R_int = 0.015
8042 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.12 e Å⁻³
2059 reflections	Δρ_min = −0.17 e Å⁻³
230 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···H6^v	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···C6^viii	2.9000
C4···N3	3.226 (2)	H1A···C7^viii	2.7600
C6···C14^iv	3.470 (3)	H1A···H7^viii	2.5900
C12···C2ⁱⁱ	3.585 (3)	H2···C12ⁱ	3.0600
C13···C16ⁱⁱⁱ	3.474 (4)	H2···C13ⁱ	3.0900
C14···C6^v	3.470 (3)	H4···N3	2.7500
C16···C22	3.224 (2)	H5···H23^ix	2.5400
C16···C13^vi	3.474 (4)	H6···C14^iv	2.9300
C22···C25ⁱⁱⁱ	3.496 (3)	H7···H1A^vii	2.5900
C22···C16	3.224 (2)	H12···N2	2.5000
C25···C22^vi	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···H1A^vii	2.9000	H22···C16	3.0000
C7···H1A^vii	2.7600	H23···H5^x	2.5400
C10···H1ⁱⁱ	2.84 (2)	H26···N2	2.8900
C11···H22	2.9400	H26···N2^vi	2.9300
C11···H1ⁱⁱ	3.00 (2)	H26···N3	2.6300
C12···H1ⁱⁱ	2.96 (3)	H26···C1^vi	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)

Symmetry codes: (i) −x+1/2, y+1/2, z−1/2; (ii) −x+1/2, y−1/2, z+1/2; (iii) x, y, z−1; (iv) x, y+1, z; (v) x, y−1, z; (vi) x, y, z+1; (vii) −x+1/2, y+1/2, z+1/2; (viii) −x+1/2, y−1/2, z−1/2; (ix) −x, −y+1, z+1/2; (x) −x, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃
M_r	323.39
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	24.1594 (3), 13.8501 (2), 5.2173 (1)
V (Å³)	1745.76 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.46 × 0.21 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.796, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8042, 2059, 1954
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.06
No. of reflections	2059
No. of parameters	230
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z−1/2.

Acknowledgements

RJB acknowledges the NSF MRI program (grant CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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