1-(3-Phenyl­isoquinolin-1-yl)hydrazine

Manivel, P.; Hathwar, V.R.; Nithya, P.; Prabakaran, K.; Khan, F.N.

doi:10.1107/S1600536808042062

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o137-o138

doi:10.1107/S1600536808042062

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1-(3-Phenylisoquinolin-1-yl)hydrazine

P. Manivel,^a Venkatesha R. Hathwar,^b P. Nithya,^a K. Prabakaran ^a and F. Nawaz Khan ^a ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 17 November 2008; accepted 10 December 2008; online 17 December 2008)

The title compound, C₁₅H₁₃N₃, contains two independent molecules in the asymmetric unit. The isoquinoline moiety and phenyl rings form dihedral angles of 4.38 (2) and 10.14 (3)° in the two independent molecules. The crystal packing is stabilized by N—H⋯N molecular dimers formed across a center of symmetry.

Related literature

For general background to hydrazine compounds, see: Broadhurst et al. (2001 ); Behrens (1999 ); Broadhurst (1991 ); Chao et al. (1999 ); Kametani (1968 ). For related crystal structures, see: Yang et al. (2008 ); Choudhury & Guru Row (2006 ); Choudhury et al. (2002 ); Hathwar et al. (2008 ). For bond-length data, see: Allen et al. (1998 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₃N₃
M_r = 235.28
Triclinic, $[P \overline 1]$
a = 6.672 (2) Å
b = 13.825 (4) Å
c = 14.934 (5) Å
α = 63.836 (5)°
β = 86.895 (6)°
γ = 82.106 (5)°
V = 1224.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 (2) K
0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.996
12381 measured reflections
4546 independent reflections
2926 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.116
S = 1.02
4546 reflections
429 parameters
All H-atom parameters refined
Δρ_max = 0.14 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
N2′—H2′N⋯N3′ⁱ	0.91 (2)	2.15 (2)	2.967 (2)	151 (2)
N2—H2N⋯N3ⁱⁱ	0.90 (2)	2.20 (2)	3.027 (2)	152 (2)
N3′—H3′B⋯N1′ⁱⁱⁱ	0.89 (2)	2.24 (2)	3.119 (2)	169 (2)
N3—H3A⋯N1^iv	0.92 (2)	2.26 (2)	3.170 (3)	168 (2)
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z; (iv) -x+2, -y, -z+1.

Data collection: SMART (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,1999 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042062/cs2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042062/cs2101Isup2.hkl

checkCIF report

Comment top

The title compound belongs to the class isoquinolines. Isoquinolines and isoquinolinones are an integral part of many naturally occurring fused heterocycles and find applications in synthetic and pharmaceutical chemistry (Kametani et al., 1968). Isoquinolinones and isoquinoline amines were reported as cancer chemotherapeutic agents (Behrens, 1999) whereas quinolyl and isoquinolyl derivatives have been reported as insecticidal compounds (Broadhurst, 1991). 3-Substituted isoquinolines are of potent use in medicine (Chao, et al., 1999) and in general, hydrazine derivatives can be used as medicaments (Broadhurst et al., 2001). Choudhury, et al. (2002, 2006) reported crystal structures of substituted isoquinolines while Hathwar, et al. (2008) reports the crystal structure of an isoquinolinyl diselenide.

The asymmetric unit of the crystal structure of the title compound contains two independent molecules (Fig. 1). The isoquinoline moiety and phenyl rings form dihedral angles of 4.38 (2) and 10.14 (3)° ,respectively, in the two independent molecules. All bond lengths and angles are normal (Allen et al., 1998). The packing (Fig. 2) is consolidated by four N—H···N hydrogen bonds. All the four N—H···N hydrogen bonds generate dimers across centres of symmetry (Table 1) resulting in tight molecular packing in the crystal. The N2'-H2'N···N3' and the N2—H2N···N3 hydrogen bonds form a R²₂(6) motif whereas the N3'-H3'B···N1' and the N3—H3A···N1 hydrogen bond dimers form a R²₂(10) motif (Bernstein et al., 1995) in the crystal (Fig. 2).

Related literature top

For general background to hydrazine compounds, see: Broadhurst et al. (2001);Behrens (1999); Broadhurst (1991); Chao et al. (1999); Kametani (1968). For related crystal structures, see: Yang et al. (2008); Choudhury & Guru Row (2006); Choudhury et al. (2002); Hathwar et al. (2008). For bond-length data, see: Allen et al. (1998). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The solution of 1-chloro-3-phenylisoquioline in ethanol was treated with hydrazine hydrate and stirred at 323 K for 3hr. The product was filtered. The solid was washed with water and diethyl ether and dried under vacuum. Single crystals of the title compound were obtained via recrystalization from a dichloromethane solution.

Computing details top

Data collection: SMART (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,1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. ORTEP diagram of the asymmetric unit of (I) with 50% probability displacement ellipsoids.
	Fig. 2. A packing excerpt from the crystal with dotted lines indicating intermolecular N—H···N hydrogen bonds. H atoms not involved in the interactions are omitted for clarity.

1-(3-Phenylisoquinolin-1-yl)hydrazine top

Crystal data top

C₁₅H₁₃N₃	Z = 4
M_r = 235.28	F(000) = 496
Triclinic, P1	D_x = 1.276 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.672 (2) Å	Cell parameters from 832 reflections
b = 13.825 (4) Å	θ = 1.7–25.3°
c = 14.934 (5) Å	µ = 0.08 mm⁻¹
α = 63.836 (5)°	T = 290 K
β = 86.895 (6)°	Needle, colourless
γ = 82.106 (5)°	0.15 × 0.12 × 0.05 mm
V = 1224.5 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4546 independent reflections
Radiation source: fine-focus sealed tube	2926 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.953, T_max = 0.996	k = −16→16
12381 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
4546 reflections	(Δ/σ)_max < 0.001
429 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₃N₃	γ = 82.106 (5)°
M_r = 235.28	V = 1224.5 (7) Å³
Triclinic, P1	Z = 4
a = 6.672 (2) Å	Mo Kα radiation
b = 13.825 (4) Å	µ = 0.08 mm⁻¹
c = 14.934 (5) Å	T = 290 K
α = 63.836 (5)°	0.15 × 0.12 × 0.05 mm
β = 86.895 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4546 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2926 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.996	R_int = 0.032
12381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.116	All H-atom parameters refined
S = 1.02	Δρ_max = 0.14 e Å⁻³
4546 reflections	Δρ_min = −0.17 e Å⁻³
429 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.91992 (19)	0.17183 (10)	0.48294 (10)	0.0386 (3)
N2	0.6714 (2)	0.05976 (11)	0.52799 (11)	0.0433 (4)
N3	0.7300 (2)	0.02645 (15)	0.45200 (14)	0.0471 (4)
N1'	0.4205 (2)	0.13567 (10)	0.03997 (10)	0.0391 (3)
N2'	0.1689 (2)	0.07962 (11)	−0.01722 (11)	0.0466 (4)
N3'	0.2325 (2)	−0.03027 (12)	0.04958 (15)	0.0495 (4)
C1	0.7552 (2)	0.14107 (12)	0.53468 (12)	0.0366 (4)
C2	1.0076 (2)	0.25388 (13)	0.48758 (12)	0.0406 (4)
C3	0.9290 (3)	0.30370 (15)	0.54472 (14)	0.0529 (5)
C4	0.6656 (4)	0.32080 (18)	0.66201 (16)	0.0718 (7)
C5	0.4979 (4)	0.28801 (19)	0.71627 (17)	0.0768 (7)
C6	0.4084 (4)	0.20448 (17)	0.71345 (16)	0.0666 (6)
C7	0.4885 (3)	0.15463 (16)	0.65585 (14)	0.0515 (5)
C8	0.6624 (2)	0.18705 (12)	0.59912 (12)	0.0395 (4)
C9	0.7543 (3)	0.27114 (14)	0.60246 (13)	0.0482 (5)
C10	1.1910 (2)	0.28398 (13)	0.42535 (12)	0.0431 (4)
C11	1.2553 (3)	0.23496 (16)	0.36341 (13)	0.0523 (5)
C12	1.4255 (3)	0.26016 (18)	0.30579 (15)	0.0639 (6)
C13	1.5362 (4)	0.33508 (19)	0.30874 (17)	0.0679 (6)
C14	1.4761 (3)	0.38509 (18)	0.36893 (17)	0.0655 (6)
C15	1.3048 (3)	0.36044 (16)	0.42676 (15)	0.0561 (5)
C1'	0.2527 (2)	0.16171 (13)	−0.01268 (12)	0.0385 (4)
C2'	0.5085 (2)	0.21556 (13)	0.04790 (12)	0.0406 (4)
C3'	0.4252 (3)	0.32116 (15)	0.00313 (14)	0.0531 (5)
C4'	0.1531 (4)	0.45988 (17)	−0.10239 (18)	0.0780 (7)
C5'	−0.0202 (4)	0.48553 (19)	−0.15637 (19)	0.0876 (8)
C6'	−0.1088 (4)	0.40594 (18)	−0.16610 (16)	0.0735 (7)
C7'	−0.0217 (3)	0.30071 (16)	−0.12234 (14)	0.0547 (5)
C8'	0.1569 (3)	0.27129 (13)	−0.06543 (12)	0.0411 (4)
C9'	0.2471 (3)	0.35185 (14)	−0.05511 (13)	0.0502 (5)
C10'	0.6945 (2)	0.17691 (14)	0.11012 (12)	0.0412 (4)
C11'	0.7519 (3)	0.06689 (16)	0.16619 (14)	0.0525 (5)
C12'	0.9251 (3)	0.02867 (18)	0.22499 (15)	0.0599 (5)
C13'	1.0450 (3)	0.09997 (19)	0.22820 (15)	0.0587 (5)
C14'	0.9911 (3)	0.2093 (2)	0.17264 (15)	0.0608 (6)
C15'	0.8188 (3)	0.24744 (17)	0.11461 (15)	0.0532 (5)
H2N	0.542 (3)	0.0483 (14)	0.5454 (13)	0.060 (6)*
H3	0.992 (3)	0.3609 (14)	0.5471 (12)	0.056 (5)*
H3A	0.843 (3)	−0.0248 (16)	0.4726 (14)	0.075 (7)*
H3B	0.761 (3)	0.0880 (17)	0.3956 (15)	0.078 (7)*
H4	0.733 (3)	0.3797 (16)	0.6607 (14)	0.082 (7)*
H5	0.438 (3)	0.3227 (17)	0.7544 (16)	0.094 (7)*
H2'N	0.038 (3)	0.0910 (13)	−0.0365 (12)	0.053 (5)*
H6	0.286 (3)	0.1827 (16)	0.7500 (15)	0.084 (7)*
H3'A	0.269 (3)	−0.0320 (14)	0.1126 (14)	0.065 (6)*
H3'B	0.341 (3)	−0.0536 (16)	0.0238 (15)	0.076 (7)*
H7	0.423 (3)	0.1003 (14)	0.6516 (12)	0.055 (5)*
H11	1.172 (3)	0.1806 (14)	0.3645 (13)	0.062 (5)*
H12	1.470 (3)	0.2194 (16)	0.2639 (15)	0.090 (7)*
H13	1.658 (3)	0.3473 (17)	0.2734 (16)	0.095 (8)*
H14	1.549 (3)	0.4356 (15)	0.3753 (13)	0.069 (6)*
H15	1.263 (3)	0.3971 (14)	0.4688 (13)	0.059 (6)*
H3'	0.492 (3)	0.3731 (15)	0.0110 (13)	0.064 (6)*
H4'	0.219 (3)	0.5136 (17)	−0.0959 (14)	0.082 (7)*
H5'	−0.082 (4)	0.5558 (19)	−0.1851 (17)	0.102 (8)*
H6'	−0.234 (3)	0.4247 (16)	−0.2025 (15)	0.080 (7)*
H7'	−0.081 (3)	0.2459 (15)	−0.1303 (13)	0.065 (6)*
H11'	0.661 (3)	0.0177 (14)	0.1642 (12)	0.057 (5)*
H12'	0.964 (3)	−0.0520 (18)	0.2615 (15)	0.092 (7)*
H13'	1.164 (3)	0.0723 (15)	0.2692 (14)	0.070 (6)*
H14'	1.073 (3)	0.2590 (16)	0.1730 (14)	0.078 (6)*
H15'	0.786 (3)	0.3249 (15)	0.0727 (14)	0.069 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0333 (8)	0.0399 (8)	0.0440 (8)	−0.0050 (6)	−0.0015 (6)	−0.0194 (7)
N2	0.0385 (9)	0.0477 (9)	0.0538 (9)	−0.0105 (7)	0.0057 (7)	−0.0306 (8)
N3	0.0416 (9)	0.0510 (10)	0.0609 (11)	−0.0049 (8)	0.0013 (8)	−0.0358 (9)
N1'	0.0349 (8)	0.0393 (8)	0.0494 (8)	−0.0077 (6)	0.0027 (7)	−0.0245 (7)
N2'	0.0365 (9)	0.0386 (9)	0.0688 (11)	−0.0028 (7)	−0.0065 (8)	−0.0271 (8)
N3'	0.0420 (10)	0.0382 (9)	0.0720 (12)	−0.0014 (7)	−0.0050 (9)	−0.0281 (9)
C1	0.0341 (9)	0.0347 (9)	0.0398 (9)	−0.0008 (7)	−0.0057 (8)	−0.0155 (8)
C2	0.0388 (10)	0.0401 (10)	0.0416 (10)	−0.0052 (8)	−0.0054 (8)	−0.0161 (8)
C3	0.0572 (12)	0.0539 (12)	0.0606 (12)	−0.0214 (10)	0.0080 (10)	−0.0337 (10)
C4	0.0929 (18)	0.0715 (15)	0.0772 (15)	−0.0321 (13)	0.0289 (13)	−0.0532 (13)
C5	0.0979 (19)	0.0770 (16)	0.0769 (16)	−0.0248 (14)	0.0364 (14)	−0.0532 (14)
C6	0.0735 (15)	0.0659 (14)	0.0659 (14)	−0.0203 (12)	0.0312 (12)	−0.0341 (12)
C7	0.0539 (12)	0.0495 (11)	0.0541 (12)	−0.0111 (10)	0.0095 (9)	−0.0250 (10)
C8	0.0416 (10)	0.0374 (9)	0.0368 (9)	−0.0013 (8)	−0.0019 (8)	−0.0145 (8)
C9	0.0549 (12)	0.0462 (11)	0.0496 (11)	−0.0100 (9)	0.0041 (9)	−0.0259 (9)
C10	0.0393 (10)	0.0408 (10)	0.0415 (10)	−0.0048 (8)	−0.0055 (8)	−0.0106 (8)
C11	0.0525 (12)	0.0569 (12)	0.0458 (11)	−0.0127 (10)	0.0048 (9)	−0.0198 (10)
C12	0.0592 (14)	0.0723 (15)	0.0525 (13)	−0.0113 (11)	0.0097 (10)	−0.0205 (12)
C13	0.0505 (14)	0.0723 (15)	0.0578 (14)	−0.0092 (12)	0.0081 (11)	−0.0081 (12)
C14	0.0508 (13)	0.0575 (13)	0.0733 (15)	−0.0191 (11)	−0.0029 (12)	−0.0115 (12)
C15	0.0510 (12)	0.0508 (12)	0.0652 (14)	−0.0133 (10)	0.0005 (10)	−0.0223 (11)
C1'	0.0354 (10)	0.0413 (10)	0.0454 (10)	−0.0068 (8)	0.0065 (8)	−0.0252 (8)
C2'	0.0408 (10)	0.0411 (10)	0.0447 (10)	−0.0115 (8)	0.0077 (8)	−0.0223 (8)
C3'	0.0611 (13)	0.0420 (11)	0.0600 (12)	−0.0146 (10)	−0.0037 (10)	−0.0230 (10)
C4'	0.1021 (19)	0.0388 (12)	0.0861 (17)	−0.0059 (12)	−0.0263 (15)	−0.0189 (12)
C5'	0.115 (2)	0.0430 (14)	0.0886 (18)	0.0131 (14)	−0.0384 (16)	−0.0160 (13)
C6'	0.0877 (18)	0.0566 (14)	0.0677 (15)	0.0104 (13)	−0.0303 (13)	−0.0215 (12)
C7'	0.0602 (13)	0.0500 (12)	0.0537 (12)	−0.0013 (10)	−0.0095 (10)	−0.0231 (10)
C8'	0.0450 (10)	0.0400 (10)	0.0381 (10)	−0.0051 (8)	0.0030 (8)	−0.0174 (8)
C9'	0.0620 (13)	0.0359 (10)	0.0505 (11)	−0.0080 (9)	−0.0019 (10)	−0.0161 (9)
C10'	0.0406 (10)	0.0492 (11)	0.0424 (10)	−0.0116 (8)	0.0061 (8)	−0.0269 (9)
C11'	0.0573 (13)	0.0514 (12)	0.0513 (12)	−0.0153 (10)	−0.0051 (10)	−0.0217 (10)
C12'	0.0654 (14)	0.0609 (14)	0.0523 (12)	−0.0064 (11)	−0.0107 (10)	−0.0232 (11)
C13'	0.0533 (13)	0.0777 (16)	0.0502 (12)	−0.0078 (12)	−0.0060 (10)	−0.0322 (12)
C14'	0.0571 (13)	0.0779 (16)	0.0612 (13)	−0.0257 (12)	−0.0016 (11)	−0.0380 (13)
C15'	0.0556 (12)	0.0543 (13)	0.0575 (13)	−0.0162 (10)	−0.0002 (10)	−0.0288 (11)

Geometric parameters (Å, º) top

N1—C1	1.3163 (19)	C12—C13	1.369 (3)
N1—C2	1.3748 (19)	C12—H12	1.02 (2)
N2—C1	1.3652 (19)	C13—C14	1.371 (3)
N2—N3	1.420 (2)	C13—H13	0.94 (2)
N2—H2N	0.904 (18)	C14—C15	1.381 (3)
N3—H3A	0.920 (19)	C14—H14	0.94 (2)
N3—H3B	0.93 (2)	C15—H15	0.976 (17)
N1'—C1'	1.317 (2)	C1'—C8'	1.435 (2)
N1'—C2'	1.3712 (19)	C2'—C3'	1.358 (2)
N2'—C1'	1.360 (2)	C2'—C10'	1.481 (2)
N2'—N3'	1.420 (2)	C3'—C9'	1.413 (3)
N2'—H2'N	0.903 (18)	C3'—H3'	0.946 (18)
N3'—H3'A	0.976 (19)	C4'—C5'	1.360 (3)
N3'—H3'B	0.89 (2)	C4'—C9'	1.408 (3)
C1—C8	1.442 (2)	C4'—H4'	0.96 (2)
C2—C3	1.359 (2)	C5'—C6'	1.382 (3)
C2—C10	1.487 (2)	C5'—H5'	0.92 (2)
C3—C9	1.414 (2)	C6'—C7'	1.361 (3)
C3—H3	0.959 (17)	C6'—H6'	0.96 (2)
C4—C5	1.353 (3)	C7'—C8'	1.407 (2)
C4—C9	1.408 (2)	C7'—H7'	0.955 (18)
C4—H4	0.98 (2)	C8'—C9'	1.404 (2)
C5—C6	1.388 (3)	C10'—C11'	1.383 (2)
C5—H5	0.94 (2)	C10'—C15'	1.389 (2)
C6—C7	1.368 (3)	C11'—C12'	1.386 (3)
C6—H6	0.96 (2)	C11'—H11'	0.983 (17)
C7—C8	1.402 (2)	C12'—C13'	1.370 (3)
C7—H7	0.945 (17)	C12'—H12'	1.00 (2)
C8—C9	1.407 (2)	C13'—C14'	1.370 (3)
C10—C11	1.389 (2)	C13'—H13'	0.95 (2)
C10—C15	1.391 (2)	C14'—C15'	1.374 (3)
C11—C12	1.375 (3)	C14'—H14'	0.94 (2)
C11—H11	0.988 (18)	C15'—H15'	0.972 (18)

C1—N1—C2	119.22 (14)	C14—C13—H13	120.8 (13)
C1—N2—N3	121.14 (14)	C13—C14—C15	120.6 (2)
C1—N2—H2N	122.1 (11)	C13—C14—H14	123.3 (12)
N3—N2—H2N	109.5 (11)	C15—C14—H14	116.1 (12)
N2—N3—H3A	109.6 (12)	C14—C15—C10	120.6 (2)
N2—N3—H3B	107.2 (12)	C14—C15—H15	119.7 (11)
H3A—N3—H3B	109.9 (18)	C10—C15—H15	119.8 (11)
C1'—N1'—C2'	119.52 (14)	N1'—C1'—N2'	117.49 (15)
C1'—N2'—N3'	120.66 (15)	N1'—C1'—C8'	123.38 (14)
C1'—N2'—H2'N	119.4 (11)	N2'—C1'—C8'	119.13 (15)
N3'—N2'—H2'N	112.8 (11)	C3'—C2'—N1'	121.27 (16)
N2'—N3'—H3'A	107.7 (11)	C3'—C2'—C10'	123.79 (16)
N2'—N3'—H3'B	108.0 (13)	N1'—C2'—C10'	114.93 (15)
H3'A—N3'—H3'B	109.2 (17)	C2'—C3'—C9'	120.53 (17)
N1—C1—N2	117.71 (15)	C2'—C3'—H3'	117.9 (11)
N1—C1—C8	123.47 (14)	C9'—C3'—H3'	121.5 (11)
N2—C1—C8	118.81 (15)	C5'—C4'—C9'	121.0 (2)
C3—C2—N1	121.64 (16)	C5'—C4'—H4'	122.4 (12)
C3—C2—C10	123.14 (16)	C9'—C4'—H4'	116.6 (12)
N1—C2—C10	115.22 (15)	C4'—C5'—C6'	120.7 (2)
C2—C3—C9	120.43 (17)	C4'—C5'—H5'	120.1 (15)
C2—C3—H3	120.7 (10)	C6'—C5'—H5'	119.2 (15)
C9—C3—H3	118.9 (10)	C7'—C6'—C5'	120.1 (2)
C5—C4—C9	121.3 (2)	C7'—C6'—H6'	119.9 (12)
C5—C4—H4	123.4 (12)	C5'—C6'—H6'	120.0 (12)
C9—C4—H4	115.3 (12)	C6'—C7'—C8'	120.6 (2)
C4—C5—C6	120.2 (2)	C6'—C7'—H7'	120.2 (11)
C4—C5—H5	120.7 (14)	C8'—C7'—H7'	119.2 (11)
C6—C5—H5	119.0 (14)	C9'—C8'—C7'	119.44 (17)
C7—C6—C5	120.5 (2)	C9'—C8'—C1'	116.33 (15)
C7—C6—H6	119.1 (12)	C7'—C8'—C1'	124.19 (16)
C5—C6—H6	120.4 (12)	C8'—C9'—C4'	118.12 (19)
C6—C7—C8	120.42 (19)	C8'—C9'—C3'	118.93 (16)
C6—C7—H7	120.1 (10)	C4'—C9'—C3'	122.94 (18)
C8—C7—H7	119.4 (10)	C11'—C10'—C15'	117.18 (17)
C7—C8—C9	119.24 (16)	C11'—C10'—C2'	120.30 (16)
C7—C8—C1	124.44 (16)	C15'—C10'—C2'	122.51 (17)
C9—C8—C1	116.31 (15)	C10'—C11'—C12'	121.42 (18)
C8—C9—C4	118.37 (18)	C10'—C11'—H11'	116.7 (10)
C8—C9—C3	118.91 (16)	C12'—C11'—H11'	121.9 (10)
C4—C9—C3	122.71 (18)	C13'—C12'—C11'	120.2 (2)
C11—C10—C15	117.55 (18)	C13'—C12'—H12'	121.5 (12)
C11—C10—C2	120.17 (16)	C11'—C12'—H12'	118.2 (12)
C15—C10—C2	122.27 (17)	C12'—C13'—C14'	119.1 (2)
C12—C11—C10	121.6 (2)	C12'—C13'—H13'	119.1 (12)
C12—C11—H11	122.8 (10)	C14'—C13'—H13'	121.8 (12)
C10—C11—H11	115.6 (10)	C13'—C14'—C15'	120.8 (2)
C13—C12—C11	120.0 (2)	C13'—C14'—H14'	120.1 (12)
C13—C12—H12	121.3 (12)	C15'—C14'—H14'	119.1 (12)
C11—C12—H12	118.6 (12)	C14'—C15'—C10'	121.3 (2)
C12—C13—C14	119.8 (2)	C14'—C15'—H15'	119.9 (11)
C12—C13—H13	119.3 (13)	C10'—C15'—H15'	118.8 (11)

C2—N1—C1—N2	179.67 (14)	C2'—N1'—C1'—N2'	−179.00 (14)
C2—N1—C1—C8	−1.7 (2)	C2'—N1'—C1'—C8'	1.6 (2)
N3—N2—C1—N1	−14.0 (2)	N3'—N2'—C1'—N1'	14.0 (2)
N3—N2—C1—C8	167.31 (15)	N3'—N2'—C1'—C8'	−166.61 (15)
C1—N1—C2—C3	0.4 (2)	C1'—N1'—C2'—C3'	0.5 (2)
C1—N1—C2—C10	−179.08 (13)	C1'—N1'—C2'—C10'	179.06 (14)
N1—C2—C3—C9	0.7 (3)	N1'—C2'—C3'—C9'	−1.5 (3)
C10—C2—C3—C9	−179.86 (15)	C10'—C2'—C3'—C9'	−179.91 (15)
C9—C4—C5—C6	−0.6 (4)	C9'—C4'—C5'—C6'	0.1 (4)
C4—C5—C6—C7	−0.1 (4)	C4'—C5'—C6'—C7'	−0.7 (4)
C5—C6—C7—C8	0.2 (3)	C5'—C6'—C7'—C8'	1.1 (3)
C6—C7—C8—C9	0.3 (3)	C6'—C7'—C8'—C9'	−0.9 (3)
C6—C7—C8—C1	−178.62 (17)	C6'—C7'—C8'—C1'	176.68 (18)
N1—C1—C8—C7	−179.17 (15)	N1'—C1'—C8'—C9'	−2.6 (2)
N2—C1—C8—C7	−0.6 (2)	N2'—C1'—C8'—C9'	177.99 (15)
N1—C1—C8—C9	1.9 (2)	N1'—C1'—C8'—C7'	179.72 (16)
N2—C1—C8—C9	−179.52 (14)	N2'—C1'—C8'—C7'	0.3 (2)
C7—C8—C9—C4	−0.9 (3)	C7'—C8'—C9'—C4'	0.3 (3)
C1—C8—C9—C4	178.12 (17)	C1'—C8'—C9'—C4'	−177.49 (17)
C7—C8—C9—C3	−179.72 (16)	C7'—C8'—C9'—C3'	179.33 (17)
C1—C8—C9—C3	−0.7 (2)	C1'—C8'—C9'—C3'	1.6 (2)
C5—C4—C9—C8	1.0 (3)	C5'—C4'—C9'—C8'	0.1 (3)
C5—C4—C9—C3	179.8 (2)	C5'—C4'—C9'—C3'	−178.9 (2)
C2—C3—C9—C8	−0.5 (3)	C2'—C3'—C9'—C8'	0.4 (3)
C2—C3—C9—C4	−179.28 (18)	C2'—C3'—C9'—C4'	179.37 (19)
C3—C2—C10—C11	−175.55 (17)	C3'—C2'—C10'—C11'	169.50 (17)
N1—C2—C10—C11	3.9 (2)	N1'—C2'—C10'—C11'	−9.0 (2)
C3—C2—C10—C15	4.8 (3)	C3'—C2'—C10'—C15'	−11.0 (3)
N1—C2—C10—C15	−175.73 (15)	N1'—C2'—C10'—C15'	170.47 (15)
C15—C10—C11—C12	0.4 (3)	C15'—C10'—C11'—C12'	0.5 (3)
C2—C10—C11—C12	−179.27 (16)	C2'—C10'—C11'—C12'	180.00 (16)
C10—C11—C12—C13	0.1 (3)	C10'—C11'—C12'—C13'	−0.4 (3)
C11—C12—C13—C14	−0.3 (3)	C11'—C12'—C13'—C14'	0.1 (3)
C12—C13—C14—C15	0.1 (3)	C12'—C13'—C14'—C15'	0.3 (3)
C13—C14—C15—C10	0.4 (3)	C13'—C14'—C15'—C10'	−0.2 (3)
C11—C10—C15—C14	−0.6 (3)	C11'—C10'—C15'—C14'	−0.2 (3)
C2—C10—C15—C14	179.05 (16)	C2'—C10'—C15'—C14'	−179.68 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2′—H2′N···N3′ⁱ	0.91 (2)	2.15 (2)	2.967 (2)	151 (2)
N2—H2N···N3ⁱⁱ	0.90 (2)	2.20 (2)	3.027 (2)	152 (2)
N3′—H3′B···N1′ⁱⁱⁱ	0.89 (2)	2.24 (2)	3.119 (2)	169 (2)
N3—H3A···N1^iv	0.92 (2)	2.26 (2)	3.170 (3)	168 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃
M_r	235.28
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	6.672 (2), 13.825 (4), 14.934 (5)
α, β, γ (°)	63.836 (5), 86.895 (6), 82.106 (5)
V (Å³)	1224.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.15 × 0.12 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	12381, 4546, 2926
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 1.02
No. of reflections	4546
No. of parameters	429
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia,1999) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2'—H2'N···N3'ⁱ	0.91 (2)	2.15 (2)	2.967 (2)	151 (2)
N2—H2N···N3ⁱⁱ	0.90 (2)	2.20 (2)	3.027 (2)	152 (2)
N3'—H3'B···N1'ⁱⁱⁱ	0.89 (2)	2.24 (2)	3.119 (2)	169 (2)
N3—H3A···N1^iv	0.92 (2)	2.26 (2)	3.170 (3)	168 (2)

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

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

References

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