1-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-phenyl­isoquinoline

Manivel, P.; Hathwar, V.R.; Maiyalagan, T.; Krishnakumar, V.; Khan, F.N.

doi:10.1107/S1600536809024842

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1798

doi:10.1107/S1600536809024842

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1-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-phenylisoquinoline

P. Manivel,^a Venkatesha R. Hathwar,^b T. Maiyalagan,^a V. Krishnakumar ^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 June 2009; accepted 27 June 2009; online 8 July 2009)

The molecular conformation of the title compound, C₂₀H₁₇N₃, is stabilized by an intramolecular C—H⋯N interaction. The crystal structure shows intermolecular C—H⋯π interactions. The dihedral angle between the isoquinoline unit and the phenyl ring is 11.42 (1)° whereas the isoquinoline unit and the pendent dimethyl pryrazole unit form a dihedral angle of 50.1 (4)°. Furthermore, the angle between the mean plane of the phenyl ring and the dimethyl pyrazole unit is 47.3 (6)°.

Related literature

For general background to isoquinolines, see: Kametani et al. (1968 ); Broadhurst et al. (2001 ); Chao et al. (1999 ); Choudhury et al. (2002 , 2006 ); Hathwar et al. (2008 ); Elguero et al. 2002 ).

Experimental

Crystal data

C₂₀H₁₇N₃
M_r = 299.37
Orthorhombic, P b c a
a = 18.3294 (14) Å
b = 8.3139 (7) Å
c = 21.6532 (17) Å
V = 3299.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 K
0.18 × 0.11 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.995
22808 measured reflections
3065 independent reflections
2608 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.129
S = 1.14
3065 reflections
276 parameters
All H-atom parameters refined
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N3	0.94 (2)	2.452 (17)	3.001 (2)	117.4 (13)
C4—H4⋯Cg2ⁱ	0.91 (2)	2.645 (17)	3.325 (2)	131.4 (13)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ . Cg2 is the centroid of the N1,C1–C3,C8,C9 ring.

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: CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024842/bt2974sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024842/bt2974Isup2.hkl

checkCIF report

Comment top

Isoquinolines are an integral part of many naturally occurring fused heterocycles and find applications in synthetic and pharmaceutical chemistry (Kametani et al., 1968). 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) report the crystal structure of an isoquinolinyl diselenide. Similarly, compounds containing the pyrazole motif are being developed in a wide range of therapeutic areas including CNS, metabolic diseases and endocrine functions, and oncology (Elguero et al., 2002). A number of pyrazole-containing compounds have been successfully commercialized, such as the blockbuster drugs Viagra, Celebrex, and Acomplia. In view of the diverse applications of this class of compounds, we report here the crystal structure of isoquinoline pyrazole, namely 1-(2,5-dimethyl-1H-pyrrol-1-yl)-3-phenylisoquinoline.

Although there are no intermolecular C—H···N hydrogen bonds, the molecules are linked by C—H···π interactions.

In the absence of strong hydrogen-bond donors in (I), the crystal packing is controlled by the involvement of weak C—H..pi intermolecular interactions.

Related literature top

For general background to hydrazine compounds, see: Kametani et al. (1968); Broadhurst et al. (2001); Chao et al. (1999); Choudhury et al. (2002, 2006); Hathwar et al. (2008); Elguero et al. 2002).

Experimental top

The 3-phenylisoquinolinehydrazine, and the 1, 3-diketones namely acetylacetone, were taken in ethanol (1:1 ratio) and refluxed under nitrogen overnight. Then the reaction mass was quenched with water, extracted with ethylacetate, washed, dried, concentrated and purified by column chromatography to get titlted compound, (I). 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: CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

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 C—H···π hydrogen bonds. H atoms not involved in the interactions are omitted for clarity.

1-(3,5-Dimethyl-1H</>-pyrazol-1-yl)-3-phenylisoquinoline top

Crystal data top

C₂₀H₁₇N₃	F(000) = 1264
M_r = 299.37	D_x = 1.205 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1248 reflections
a = 18.3294 (14) Å	θ = 2.2–27.2°
b = 8.3139 (7) Å	µ = 0.07 mm⁻¹
c = 21.6532 (17) Å	T = 290 K
V = 3299.7 (5) Å³	Block, colorless
Z = 8	0.18 × 0.11 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3065 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→20
T_min = 0.949, T_max = 0.995	k = −10→10
22808 measured reflections	l = −26→24

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	All H-atom parameters refined
S = 1.14	w = 1/[σ²(F_o²) + (0.0517P)² + 0.6765P] where P = (F_o² + 2F_c²)/3
3065 reflections	(Δ/σ)_max < 0.001
276 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₀H₁₇N₃	V = 3299.7 (5) Å³
M_r = 299.37	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.3294 (14) Å	µ = 0.07 mm⁻¹
b = 8.3139 (7) Å	T = 290 K
c = 21.6532 (17) Å	0.18 × 0.11 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3065 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2608 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.995	R_int = 0.027
22808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.129	All H-atom parameters refined
S = 1.14	Δρ_max = 0.15 e Å⁻³
3065 reflections	Δρ_min = −0.15 e Å⁻³
276 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
N1	0.09848 (7)	0.53396 (16)	0.26708 (6)	0.0490 (4)
N2	0.02198 (7)	0.52682 (18)	0.18301 (6)	0.0538 (4)
C1	0.08768 (9)	0.47659 (19)	0.21175 (7)	0.0470 (4)
C8	0.13594 (9)	0.37101 (19)	0.18015 (7)	0.0477 (4)
C3	0.21303 (10)	0.3989 (2)	0.27066 (8)	0.0525 (4)
C9	0.20196 (9)	0.3351 (2)	0.21115 (8)	0.0491 (4)
C2	0.16088 (9)	0.4924 (2)	0.29813 (8)	0.0485 (4)
C10	0.16626 (9)	0.5586 (2)	0.36145 (8)	0.0533 (4)
C4	0.25285 (11)	0.2347 (2)	0.18064 (9)	0.0611 (5)
C16	−0.04605 (9)	0.5383 (2)	0.20820 (9)	0.0555 (5)
C7	0.12169 (11)	0.3011 (2)	0.12208 (8)	0.0597 (5)
N3	0.02521 (8)	0.5925 (2)	0.12480 (7)	0.0677 (5)
C20	−0.06494 (13)	0.4719 (3)	0.26970 (12)	0.0742 (6)
C5	0.23812 (12)	0.1701 (3)	0.12503 (9)	0.0705 (6)
C11	0.22045 (12)	0.5099 (3)	0.40250 (9)	0.0673 (6)
C15	0.11577 (12)	0.6709 (3)	0.38203 (9)	0.0698 (6)
C6	0.17167 (12)	0.2015 (3)	0.09549 (10)	0.0699 (6)
C12	0.22252 (14)	0.5691 (3)	0.46184 (10)	0.0819 (7)
C18	−0.04247 (12)	0.6423 (3)	0.11454 (9)	0.0723 (6)
C13	0.17137 (16)	0.6770 (3)	0.48194 (11)	0.0876 (8)
C17	−0.08729 (12)	0.6106 (3)	0.16449 (10)	0.0700 (6)
C14	0.11810 (15)	0.7294 (3)	0.44162 (11)	0.0855 (7)
C19	−0.06113 (15)	0.7207 (4)	0.05432 (11)	0.1147 (10)
H19A	−0.0312	0.8144	0.0487	0.172*
H19B	−0.1116	0.7517	0.0545	0.172*
H19C	−0.0526	0.6464	0.0212	0.172*
H3	0.2583 (10)	0.378 (2)	0.2919 (8)	0.064 (5)*
H7	0.0783 (10)	0.330 (2)	0.1015 (8)	0.070 (6)*
H4	0.2958 (10)	0.212 (2)	0.2010 (9)	0.065 (5)*
H11	0.2580 (13)	0.431 (3)	0.3893 (10)	0.090 (7)*
H5	0.2750 (11)	0.100 (3)	0.1032 (9)	0.080 (6)*
H15	0.0784 (11)	0.712 (3)	0.3537 (9)	0.079 (6)*
H20C	−0.1161 (15)	0.482 (3)	0.2777 (10)	0.106 (8)*
H17	−0.1358 (12)	0.633 (2)	0.1678 (9)	0.073 (6)*
H20B	−0.0531 (14)	0.356 (4)	0.2713 (12)	0.128 (10)*
H14	0.0827 (11)	0.809 (3)	0.4543 (10)	0.083 (7)*
H12	0.2612 (13)	0.529 (3)	0.4907 (11)	0.104 (8)*
H20A	−0.0422 (13)	0.531 (3)	0.3038 (11)	0.098 (8)*
H6	0.1605 (11)	0.153 (3)	0.0533 (11)	0.090 (7)*
H13	0.1701 (12)	0.718 (3)	0.5233 (12)	0.099 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0454 (8)	0.0533 (8)	0.0483 (8)	−0.0005 (6)	−0.0008 (6)	0.0040 (6)
N2	0.0449 (8)	0.0652 (9)	0.0513 (8)	0.0098 (7)	−0.0043 (6)	−0.0032 (7)
C1	0.0424 (9)	0.0510 (9)	0.0474 (9)	0.0001 (7)	−0.0008 (7)	0.0054 (7)
C8	0.0459 (9)	0.0484 (9)	0.0489 (9)	0.0017 (7)	0.0051 (7)	0.0088 (7)
C3	0.0449 (9)	0.0588 (10)	0.0540 (10)	0.0024 (8)	−0.0011 (8)	0.0162 (8)
C9	0.0457 (9)	0.0503 (9)	0.0512 (10)	0.0033 (7)	0.0052 (7)	0.0168 (7)
C2	0.0468 (9)	0.0506 (9)	0.0480 (9)	−0.0056 (7)	−0.0009 (7)	0.0118 (7)
C10	0.0545 (10)	0.0578 (10)	0.0478 (10)	−0.0113 (8)	−0.0001 (8)	0.0106 (8)
C4	0.0567 (11)	0.0659 (11)	0.0607 (12)	0.0191 (9)	0.0073 (9)	0.0213 (9)
C16	0.0437 (9)	0.0549 (10)	0.0679 (12)	0.0022 (8)	−0.0008 (8)	−0.0161 (9)
C7	0.0632 (12)	0.0634 (11)	0.0524 (11)	0.0101 (9)	−0.0005 (9)	0.0026 (9)
N3	0.0647 (10)	0.0857 (12)	0.0528 (9)	0.0237 (9)	−0.0041 (7)	0.0024 (8)
C20	0.0531 (13)	0.0783 (16)	0.0912 (17)	−0.0012 (11)	0.0162 (12)	−0.0037 (13)
C5	0.0844 (15)	0.0722 (13)	0.0550 (12)	0.0320 (11)	0.0164 (11)	0.0138 (10)
C11	0.0665 (13)	0.0829 (14)	0.0526 (12)	−0.0092 (11)	−0.0073 (9)	0.0133 (10)
C15	0.0766 (14)	0.0766 (13)	0.0563 (12)	−0.0002 (11)	−0.0052 (10)	−0.0015 (10)
C6	0.0863 (15)	0.0710 (13)	0.0524 (11)	0.0241 (11)	0.0046 (10)	0.0018 (10)
C12	0.0833 (16)	0.1038 (18)	0.0586 (13)	−0.0167 (14)	−0.0144 (12)	0.0141 (13)
C18	0.0707 (13)	0.0816 (14)	0.0647 (12)	0.0302 (11)	−0.0169 (10)	−0.0101 (10)
C13	0.114 (2)	0.0989 (18)	0.0499 (13)	−0.0335 (16)	−0.0056 (13)	−0.0015 (12)
C17	0.0485 (11)	0.0761 (13)	0.0853 (15)	0.0197 (10)	−0.0127 (10)	−0.0192 (11)
C14	0.1017 (18)	0.0896 (16)	0.0651 (14)	−0.0013 (15)	0.0035 (13)	−0.0127 (12)
C19	0.117 (2)	0.149 (3)	0.0785 (16)	0.065 (2)	−0.0211 (15)	0.0087 (16)

Geometric parameters (Å, º) top

N1—C1	1.305 (2)	C20—H20C	0.96 (3)
N1—C2	1.371 (2)	C20—H20B	0.99 (3)
N2—C16	1.364 (2)	C20—H20A	0.98 (3)
N2—N3	1.375 (2)	C5—C6	1.400 (3)
N2—C1	1.418 (2)	C5—H5	1.01 (2)
C1—C8	1.422 (2)	C11—C12	1.376 (3)
C8—C7	1.410 (2)	C11—H11	1.00 (2)
C8—C9	1.416 (2)	C15—C14	1.380 (3)
C3—C2	1.368 (2)	C15—H15	0.98 (2)
C3—C9	1.408 (2)	C6—H6	1.02 (2)
C3—H3	0.966 (18)	C12—C13	1.369 (4)
C9—C4	1.416 (2)	C12—H12	1.00 (3)
C2—C10	1.481 (2)	C18—C17	1.383 (3)
C10—C15	1.388 (3)	C18—C19	1.498 (3)
C10—C11	1.393 (3)	C13—C14	1.380 (3)
C4—C5	1.346 (3)	C13—H13	0.96 (2)
C4—H4	0.922 (18)	C17—H17	0.91 (2)
C16—C17	1.353 (3)	C14—H14	0.97 (2)
C16—C20	1.482 (3)	C19—H19A	0.9600
C7—C6	1.362 (3)	C19—H19B	0.9600
C7—H7	0.943 (19)	C19—H19C	0.9600
N3—C18	1.326 (2)

C1—N1—C2	119.00 (14)	H20C—C20—H20A	103.7 (19)
C16—N2—N3	112.22 (14)	H20B—C20—H20A	112 (2)
C16—N2—C1	128.39 (15)	C4—C5—C6	120.56 (19)
N3—N2—C1	118.85 (13)	C4—C5—H5	121.0 (11)
N1—C1—N2	115.09 (14)	C6—C5—H5	118.4 (11)
N1—C1—C8	124.98 (15)	C12—C11—C10	120.7 (2)
N2—C1—C8	119.92 (15)	C12—C11—H11	119.0 (13)
C7—C8—C9	119.62 (16)	C10—C11—H11	120.2 (13)
C7—C8—C1	124.66 (16)	C14—C15—C10	121.1 (2)
C9—C8—C1	115.72 (15)	C14—C15—H15	119.0 (12)
C2—C3—C9	120.75 (16)	C10—C15—H15	119.9 (12)
C2—C3—H3	119.8 (11)	C7—C6—C5	120.4 (2)
C9—C3—H3	119.4 (11)	C7—C6—H6	119.0 (12)
C3—C9—C4	123.67 (16)	C5—C6—H6	120.6 (12)
C3—C9—C8	118.52 (15)	C13—C12—C11	120.8 (2)
C4—C9—C8	117.80 (17)	C13—C12—H12	120.2 (14)
C3—C2—N1	120.85 (16)	C11—C12—H12	118.9 (15)
C3—C2—C10	124.57 (15)	N3—C18—C17	111.41 (18)
N1—C2—C10	114.57 (15)	N3—C18—C19	119.7 (2)
C15—C10—C11	117.79 (19)	C17—C18—C19	128.89 (19)
C15—C10—C2	120.19 (16)	C12—C13—C14	119.4 (2)
C11—C10—C2	122.00 (18)	C12—C13—H13	123.1 (14)
C5—C4—C9	121.39 (19)	C14—C13—H13	117.5 (14)
C5—C4—H4	121.1 (12)	C16—C17—C18	107.44 (18)
C9—C4—H4	117.5 (12)	C16—C17—H17	125.4 (13)
C17—C16—N2	105.19 (18)	C18—C17—H17	127.1 (13)
C17—C16—C20	131.6 (2)	C15—C14—C13	120.1 (3)
N2—C16—C20	123.14 (17)	C15—C14—H14	119.1 (13)
C6—C7—C8	120.20 (19)	C13—C14—H14	120.8 (13)
C6—C7—H7	121.4 (12)	C18—C19—H19A	109.5
C8—C7—H7	118.3 (12)	C18—C19—H19B	109.5
C18—N3—N2	103.72 (16)	H19A—C19—H19B	109.5
C16—C20—H20C	111.2 (14)	C18—C19—H19C	109.5
C16—C20—H20B	110.1 (16)	H19A—C19—H19C	109.5
H20C—C20—H20B	107 (2)	H19B—C19—H19C	109.5
C16—C20—H20A	112.9 (14)

C2—N1—C1—N2	−179.60 (14)	N3—N2—C16—C17	1.0 (2)
C2—N1—C1—C8	0.5 (2)	C1—N2—C16—C17	172.43 (17)
C16—N2—C1—N1	−43.2 (2)	N3—N2—C16—C20	177.88 (18)
N3—N2—C1—N1	127.74 (16)	C1—N2—C16—C20	−10.7 (3)
C16—N2—C1—C8	136.70 (18)	C9—C8—C7—C6	−1.0 (3)
N3—N2—C1—C8	−52.4 (2)	C1—C8—C7—C6	179.82 (18)
N1—C1—C8—C7	175.60 (16)	C16—N2—N3—C18	−0.9 (2)
N2—C1—C8—C7	−4.3 (2)	C1—N2—N3—C18	−173.20 (16)
N1—C1—C8—C9	−3.6 (2)	C9—C4—C5—C6	0.4 (3)
N2—C1—C8—C9	176.55 (14)	C15—C10—C11—C12	1.4 (3)
C2—C3—C9—C4	−178.55 (16)	C2—C10—C11—C12	−177.56 (18)
C2—C3—C9—C8	0.6 (2)	C11—C10—C15—C14	−1.5 (3)
C7—C8—C9—C3	−176.34 (15)	C2—C10—C15—C14	177.43 (19)
C1—C8—C9—C3	2.9 (2)	C8—C7—C6—C5	−1.2 (3)
C7—C8—C9—C4	2.8 (2)	C4—C5—C6—C7	1.5 (3)
C1—C8—C9—C4	−177.96 (15)	C10—C11—C12—C13	0.1 (3)
C9—C3—C2—N1	−3.8 (2)	N2—N3—C18—C17	0.4 (2)
C9—C3—C2—C10	177.19 (15)	N2—N3—C18—C19	−179.4 (2)
C1—N1—C2—C3	3.3 (2)	C11—C12—C13—C14	−1.4 (4)
C1—N1—C2—C10	−177.61 (14)	N2—C16—C17—C18	−0.7 (2)
C3—C2—C10—C15	170.61 (17)	C20—C16—C17—C18	−177.2 (2)
N1—C2—C10—C15	−8.4 (2)	N3—C18—C17—C16	0.2 (3)
C3—C2—C10—C11	−10.5 (3)	C19—C18—C17—C16	180.0 (2)
N1—C2—C10—C11	170.48 (16)	C10—C15—C14—C13	0.2 (4)
C3—C9—C4—C5	176.59 (18)	C12—C13—C14—C15	1.3 (4)
C8—C9—C4—C5	−2.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N3	0.94 (2)	2.452 (17)	3.001 (2)	117.4 (13)
C4—H4···Cg2ⁱ	0.91 (2)	2.645 (17)	3.325 (2)	131.4 (13)

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃
M_r	299.37
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	290
a, b, c (Å)	18.3294 (14), 8.3139 (7), 21.6532 (17)
V (Å³)	3299.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.18 × 0.11 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	22808, 3065, 2608
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.129, 1.14
No. of reflections	3065
No. of parameters	276
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N3	0.94 (2)	2.452 (17)	3.001 (2)	117.4 (13)
C4—H4···Cg2ⁱ	0.91 (2)	2.645 (17)	3.325 (2)	131.4 (13)

Symmetry code: (i) −x+1/2, y−1/2, z.

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 Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

References

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