3-(4-Pyrid-yl)-4,5-dihydro-1H-benzo[g]indazole.

In the mol-ecular structure of the title compound, C(16)H(13)N(3), the cyclo-hexa-1,3-diene ring displays a screw-boat conformation and the pyridine ring is twisted by a dihedral angle of 29.13 (9)° with respect to the pyrazole ring. Mol-ecules are linked into a supra-molecular structure by N-H⋯N hydrogen bonding.

Related literature

For general background to indazole derivatives and their pharmacological properties, see: Bistochi et al. (1981 ▶); Keppler & Hartmann (1994 ▶); Sun et al. (1997 ▶); Gomtsyan et al. (2008 ▶).

Experimental

Crystal data

C16H13N3

M = 247.29

Orthorhombic,

a = 15.306 (2) Å

b = 8.8368 (13) Å

c = 18.543 (3) Å

V = 2508.1 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

24926 measured reflections

2217 independent reflections

1978 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.08

2217 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038944/xu2463sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038944/xu2463Isup2.hkl

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

C16H13N3	F000 = 1040
Mr = 247.29	Dx = 1.310 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2217 reflections
a = 15.306 (2) Å	θ = 2.2–25.0º
b = 8.8368 (13) Å	µ = 0.08 mm−1
c = 18.543 (3) Å	T = 293 (2) K
V = 2508.1 (6) Å3	Block, colorless
Z = 8	0.22 × 0.19 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	1978 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Monochromator: graphite	θmax = 25.0º
T = 293(2) K	θmin = 2.2º
φ and ω scans	h = −18→17
Absorption correction: none	k = −10→9
24926 measured reflections	l = −22→22
2217 independent reflections

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.7587P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2217 reflections	Δρmax = 0.44 e Å−3
172 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N2	0.37603 (9)	0.33266 (16)	0.11204 (7)	0.0442 (4)
H2	0.3299	0.3882	0.1124	0.053*
N1	0.43088 (9)	0.32191 (17)	0.05503 (8)	0.0458 (4)
C2	0.65724 (12)	0.2397 (2)	−0.07332 (10)	0.0563 (5)
H2A	0.6747	0.3078	−0.1087	0.068*
C11	0.41088 (14)	0.1591 (2)	0.29215 (10)	0.0567 (5)
C5	0.56409 (10)	0.18489 (19)	0.02662 (9)	0.0436 (4)
C7	0.40188 (10)	0.24622 (18)	0.16853 (9)	0.0415 (4)
C12	0.36103 (11)	0.2337 (2)	0.23932 (9)	0.0466 (4)
C8	0.47774 (11)	0.17516 (19)	0.14790 (9)	0.0438 (4)
C6	0.49343 (10)	0.22560 (19)	0.07685 (9)	0.0425 (4)
C4	0.60463 (11)	0.0446 (2)	0.02934 (10)	0.0484 (4)
H4	0.5881	−0.0261	0.0639	0.058*
C9	0.52238 (13)	0.0675 (2)	0.19845 (11)	0.0631 (5)
H9A	0.5018	−0.0346	0.1895	0.076*
H9B	0.5849	0.0696	0.1899	0.076*
C1	0.66954 (11)	0.0109 (2)	−0.01959 (10)	0.0534 (5)
H1	0.6958	−0.0838	−0.0165	0.064*
N3	0.69715 (9)	0.10469 (18)	−0.07098 (8)	0.0534 (4)
C3	0.59220 (12)	0.2840 (2)	−0.02683 (10)	0.0528 (5)
H3	0.5672	0.3795	−0.0311	0.063*
C13	0.27959 (13)	0.2938 (2)	0.25682 (11)	0.0614 (5)
H13	0.2468	0.3434	0.2219	0.074*
C14	0.37630 (18)	0.1460 (3)	0.36132 (11)	0.0726 (6)
H14	0.4082	0.0962	0.3968	0.087*
C15	0.29537 (18)	0.2057 (3)	0.37810 (12)	0.0771 (7)
H15	0.2733	0.1959	0.4246	0.092*
C16	0.24751 (16)	0.2795 (3)	0.32620 (12)	0.0761 (7)
H16	0.1932	0.3200	0.3378	0.091*
C10	0.50413 (16)	0.1100 (3)	0.27516 (12)	0.0759 (7)
H10A	0.5432	0.1918	0.2884	0.091*
H10B	0.5183	0.0240	0.3055	0.091*

	U11	U22	U33	U12	U13	U23
N2	0.0354 (7)	0.0488 (8)	0.0484 (8)	0.0074 (6)	−0.0015 (6)	0.0005 (6)
N1	0.0395 (8)	0.0497 (8)	0.0480 (8)	0.0035 (6)	−0.0009 (6)	0.0016 (6)
C2	0.0498 (11)	0.0611 (12)	0.0579 (11)	−0.0071 (9)	0.0052 (8)	0.0048 (9)
C11	0.0704 (12)	0.0498 (11)	0.0499 (10)	−0.0028 (9)	−0.0010 (9)	0.0031 (8)
C5	0.0331 (8)	0.0480 (9)	0.0496 (9)	−0.0036 (7)	−0.0023 (7)	−0.0032 (7)
C7	0.0375 (9)	0.0422 (9)	0.0447 (9)	−0.0016 (7)	−0.0033 (7)	−0.0008 (7)
C12	0.0474 (10)	0.0449 (9)	0.0474 (9)	−0.0077 (8)	0.0013 (7)	−0.0040 (7)
C8	0.0379 (9)	0.0430 (9)	0.0504 (10)	0.0011 (7)	−0.0024 (7)	0.0020 (7)
C6	0.0361 (8)	0.0416 (9)	0.0498 (9)	−0.0019 (7)	−0.0022 (7)	0.0007 (7)
C4	0.0412 (9)	0.0455 (10)	0.0585 (10)	−0.0024 (7)	0.0045 (8)	0.0002 (8)
C9	0.0590 (12)	0.0645 (12)	0.0658 (12)	0.0145 (10)	−0.0004 (9)	0.0158 (10)
C1	0.0428 (10)	0.0493 (10)	0.0681 (12)	−0.0001 (8)	0.0046 (8)	−0.0068 (9)
N3	0.0396 (8)	0.0601 (10)	0.0605 (9)	−0.0063 (7)	0.0053 (7)	−0.0069 (7)
C3	0.0455 (10)	0.0520 (11)	0.0610 (11)	0.0020 (8)	0.0051 (8)	0.0058 (9)
C13	0.0494 (11)	0.0756 (13)	0.0592 (11)	−0.0032 (10)	0.0058 (9)	−0.0080 (10)
C14	0.0972 (18)	0.0692 (14)	0.0515 (11)	−0.0096 (13)	0.0013 (11)	0.0068 (10)
C15	0.0888 (17)	0.0870 (16)	0.0554 (12)	−0.0268 (14)	0.0208 (12)	−0.0080 (11)
C16	0.0628 (13)	0.0966 (17)	0.0689 (13)	−0.0122 (12)	0.0210 (11)	−0.0184 (13)
C10	0.0849 (14)	0.0828 (16)	0.0600 (12)	0.0256 (12)	−0.0095 (11)	0.0120 (11)

N2—N1	1.353 (2)	C4—C1	1.378 (2)
N2—C7	1.356 (2)	C4—H4	0.9300
N2—H2	0.8600	C9—C10	1.497 (3)
N1—C6	1.343 (2)	C9—H9A	0.9700
C2—N3	1.341 (3)	C9—H9B	0.9700
C2—C3	1.374 (3)	C1—N3	1.332 (2)
C2—H2A	0.9300	C1—H1	0.9300
C11—C14	1.393 (3)	C3—H3	0.9300
C11—C12	1.406 (3)	C13—C16	1.383 (3)
C11—C10	1.525 (3)	C13—H13	0.9300
C5—C4	1.387 (2)	C14—C15	1.382 (4)
C5—C3	1.391 (2)	C14—H14	0.9300
C5—C6	1.472 (2)	C15—C16	1.374 (4)
C7—C8	1.374 (2)	C15—H15	0.9300
C7—C12	1.458 (2)	C16—H16	0.9300
C12—C13	1.393 (3)	C10—H10A	0.9700
C8—C6	1.412 (2)	C10—H10B	0.9700
C8—C9	1.500 (2)
N1—N2—C7	112.52 (13)	C8—C9—H9A	109.6
N1—N2—H2	123.7	C10—C9—H9B	109.6
C7—N2—H2	123.7	C8—C9—H9B	109.6
C6—N1—N2	104.56 (13)	H9A—C9—H9B	108.1
N3—C2—C3	124.28 (18)	N3—C1—C4	124.42 (18)
N3—C2—H2A	117.9	N3—C1—H1	117.8
C3—C2—H2A	117.9	C4—C1—H1	117.8
C14—C11—C12	118.3 (2)	C1—N3—C2	115.61 (16)
C14—C11—C10	121.50 (19)	C2—C3—C5	119.47 (18)
C12—C11—C10	119.84 (17)	C2—C3—H3	120.3
C4—C5—C3	116.76 (16)	C5—C3—H3	120.3
C4—C5—C6	121.60 (16)	C16—C13—C12	120.0 (2)
C3—C5—C6	121.63 (16)	C16—C13—H13	120.0
N2—C7—C8	106.80 (14)	C12—C13—H13	120.0
N2—C7—C12	127.82 (15)	C15—C14—C11	121.1 (2)
C8—C7—C12	125.33 (15)	C15—C14—H14	119.5
C13—C12—C11	120.13 (17)	C11—C14—H14	119.5
C13—C12—C7	124.38 (17)	C16—C15—C14	120.1 (2)
C11—C12—C7	115.47 (16)	C16—C15—H15	120.0
C7—C8—C6	105.03 (14)	C14—C15—H15	120.0
C7—C8—C9	120.04 (16)	C15—C16—C13	120.4 (2)
C6—C8—C9	134.91 (16)	C15—C16—H16	119.8
N1—C6—C8	111.09 (15)	C13—C16—H16	119.8
N1—C6—C5	119.20 (15)	C9—C10—C11	116.24 (18)
C8—C6—C5	129.68 (15)	C9—C10—H10A	108.2
C1—C4—C5	119.47 (17)	C11—C10—H10A	108.2
C1—C4—H4	120.3	C9—C10—H10B	108.2
C5—C4—H4	120.3	C11—C10—H10B	108.2
C10—C9—C8	110.47 (17)	H10A—C10—H10B	107.4
C10—C9—H9A	109.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3i	0.86	2.17	2.895 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3i	0.86	2.17	2.895 (2)	141

Symmetry code: (i) .