2-[1-(9-Anthrylmeth-yl)-1H-pyrazol-3-yl]pyridine.

The title compound, C(23)H(17)N(3), can be used in coordination chemistry. The anthracene ring makes dihedral angles of 86.08 (5) and 76.63 (6)°, respectively, with the pyridine and pyrazole rings. The dihedral angle between the pyrazole and pyrimidine rings is 11.79 (7)°. In the structure, weak inter-molecular C-H⋯N hydrogen bonds are observed.

Related literature

For the synthesis, see: Amoroso et al. (1994 ▶); Amir et al. (2008 ▶); Stell (2005 ▶); Ward et al. (2001 ▶). For related structures, see: Liu et al. (2008 ▶).

Experimental

Crystal data

C23H17N3

M = 335.40

Monoclinic,

a = 13.736 (3) Å

b = 13.679 (3) Å

c = 8.913 (2) Å

β = 98.496 (3)°

V = 1656.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.40 × 0.33 × 0.20 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: none

13094 measured reflections

3777 independent reflections

3156 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.122

S = 1.00

3777 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: CrystalStructure (Rigaku/MSC, 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039427/at2873sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039427/at2873Isup2.hkl

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

C23H17N3	F(000) = 704
Mr = 335.40	Dx = 1.345 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4717 reflections
a = 13.736 (3) Å	θ = 3.3–27.5°
b = 13.679 (3) Å	µ = 0.08 mm−1
c = 8.913 (2) Å	T = 93 K
β = 98.496 (3)°	Prism, yellow
V = 1656.2 (7) Å3	0.40 × 0.33 × 0.20 mm
Z = 4

Rigaku SPIDER diffractometer	3156 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.034
graphite	θmax = 27.5°, θmin = 3.3°
ω scans	h = −17→17
13094 measured reflections	k = −17→15
3777 independent reflections	l = −11→11

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.333P] where P = (Fo2 + 2Fc2)/3
3777 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
N1	0.25794 (8)	0.55924 (8)	0.72942 (13)	0.0216 (3)
N2	0.22498 (8)	0.64246 (8)	0.78636 (13)	0.0219 (3)
N3	0.02717 (8)	0.65643 (9)	1.01184 (13)	0.0264 (3)
C1	0.46616 (10)	0.43366 (9)	0.66749 (15)	0.0216 (3)
C2	0.51916 (10)	0.47480 (11)	0.80358 (16)	0.0280 (3)
H2	0.4936	0.5309	0.8469	0.034*
C3	0.60559 (11)	0.43505 (11)	0.87224 (17)	0.0313 (4)
H3	0.6392	0.4640	0.9621	0.038*
C4	0.64588 (11)	0.35107 (11)	0.81111 (17)	0.0308 (3)
H4	0.7064	0.3245	0.8595	0.037*
C5	0.59810 (10)	0.30887 (11)	0.68378 (16)	0.0270 (3)
H5	0.6256	0.2526	0.6437	0.032*
C6	0.50709 (10)	0.34731 (10)	0.60844 (15)	0.0229 (3)
C7	0.45791 (10)	0.30295 (10)	0.47849 (16)	0.0241 (3)
H7	0.4848	0.2453	0.4414	0.029*
C8	0.37068 (10)	0.34050 (10)	0.40140 (15)	0.0235 (3)
C9	0.32166 (11)	0.29600 (11)	0.26587 (17)	0.0311 (3)
H9	0.3473	0.2373	0.2304	0.037*
C10	0.23940 (12)	0.33579 (13)	0.18707 (18)	0.0375 (4)
H10	0.2084	0.3053	0.0967	0.045*
C11	0.19940 (11)	0.42289 (12)	0.23918 (17)	0.0341 (4)
H11	0.1421	0.4510	0.1828	0.041*
C12	0.24260 (10)	0.46640 (11)	0.36920 (16)	0.0282 (3)
H12	0.2138	0.5238	0.4034	0.034*
C13	0.33022 (10)	0.42817 (10)	0.45598 (15)	0.0221 (3)
C14	0.37813 (10)	0.47367 (10)	0.58909 (15)	0.0219 (3)
C15	0.33882 (10)	0.56910 (10)	0.63969 (17)	0.0255 (3)
H15A	0.3934	0.6050	0.7008	0.031*
H15B	0.3157	0.6090	0.5488	0.031*
C16	0.20496 (10)	0.48050 (10)	0.76085 (16)	0.0247 (3)
H16	0.2146	0.4149	0.7314	0.030*
C17	0.13437 (10)	0.51320 (10)	0.84353 (16)	0.0251 (3)
H17	0.0859	0.4755	0.8832	0.030*
C18	0.14980 (9)	0.61436 (10)	0.85633 (14)	0.0209 (3)
C19	0.09372 (9)	0.68884 (10)	0.92693 (15)	0.0217 (3)
C20	0.10796 (10)	0.78813 (11)	0.90066 (17)	0.0282 (3)
H20	0.1565	0.8087	0.8419	0.034*
C21	0.05025 (11)	0.85594 (11)	0.96156 (18)	0.0322 (4)
H21	0.0578	0.9238	0.9439	0.039*
C22	−0.01841 (10)	0.82348 (11)	1.04831 (17)	0.0299 (3)
H22	−0.0592	0.8684	1.0914	0.036*
C23	−0.02639 (10)	0.72459 (11)	1.07094 (17)	0.0289 (3)
H23	−0.0730	0.7030	1.1326	0.035*

	U11	U22	U33	U12	U13	U23
N1	0.0219 (6)	0.0206 (6)	0.0242 (6)	0.0015 (4)	0.0092 (5)	−0.0014 (5)
N2	0.0204 (6)	0.0214 (6)	0.0252 (6)	0.0009 (4)	0.0069 (5)	−0.0031 (4)
N3	0.0232 (6)	0.0312 (7)	0.0264 (6)	0.0013 (5)	0.0092 (5)	−0.0025 (5)
C1	0.0219 (7)	0.0223 (7)	0.0229 (7)	−0.0025 (5)	0.0104 (5)	0.0026 (5)
C2	0.0295 (8)	0.0317 (8)	0.0247 (7)	−0.0045 (6)	0.0107 (6)	−0.0008 (6)
C3	0.0284 (7)	0.0422 (9)	0.0239 (7)	−0.0092 (6)	0.0056 (6)	0.0022 (6)
C4	0.0225 (7)	0.0422 (9)	0.0285 (8)	0.0003 (6)	0.0066 (6)	0.0119 (6)
C5	0.0240 (7)	0.0290 (8)	0.0299 (8)	0.0032 (6)	0.0106 (6)	0.0086 (6)
C6	0.0226 (7)	0.0238 (7)	0.0248 (7)	0.0013 (5)	0.0117 (6)	0.0055 (5)
C7	0.0255 (7)	0.0208 (7)	0.0285 (7)	0.0009 (5)	0.0122 (6)	−0.0005 (5)
C8	0.0238 (7)	0.0246 (7)	0.0246 (7)	−0.0030 (5)	0.0114 (6)	−0.0013 (6)
C9	0.0298 (8)	0.0344 (8)	0.0314 (8)	−0.0049 (6)	0.0121 (6)	−0.0075 (6)
C10	0.0301 (8)	0.0536 (11)	0.0292 (8)	−0.0096 (7)	0.0059 (7)	−0.0061 (7)
C11	0.0218 (7)	0.0521 (10)	0.0289 (8)	−0.0026 (7)	0.0052 (6)	0.0086 (7)
C12	0.0223 (7)	0.0332 (8)	0.0308 (8)	0.0006 (6)	0.0094 (6)	0.0065 (6)
C13	0.0207 (6)	0.0237 (7)	0.0241 (7)	−0.0012 (5)	0.0105 (5)	0.0034 (5)
C14	0.0219 (6)	0.0212 (7)	0.0250 (7)	0.0000 (5)	0.0114 (5)	0.0019 (5)
C15	0.0254 (7)	0.0234 (7)	0.0312 (7)	0.0010 (5)	0.0153 (6)	0.0006 (6)
C16	0.0270 (7)	0.0203 (7)	0.0286 (7)	−0.0011 (5)	0.0100 (6)	−0.0002 (6)
C17	0.0238 (7)	0.0253 (7)	0.0279 (7)	−0.0007 (5)	0.0094 (6)	0.0015 (6)
C18	0.0194 (6)	0.0250 (7)	0.0185 (6)	0.0008 (5)	0.0035 (5)	−0.0004 (5)
C19	0.0179 (6)	0.0266 (7)	0.0205 (6)	0.0010 (5)	0.0021 (5)	−0.0033 (5)
C20	0.0226 (7)	0.0282 (8)	0.0350 (8)	−0.0020 (6)	0.0082 (6)	−0.0058 (6)
C21	0.0279 (8)	0.0271 (8)	0.0429 (9)	−0.0007 (6)	0.0092 (7)	−0.0080 (6)
C22	0.0224 (7)	0.0318 (8)	0.0362 (8)	0.0033 (6)	0.0072 (6)	−0.0096 (7)
C23	0.0233 (7)	0.0368 (9)	0.0281 (7)	0.0014 (6)	0.0090 (6)	−0.0061 (6)

N1—N2	1.3513 (15)	C10—C11	1.419 (2)
N1—C16	1.3522 (17)	C10—H10	0.9500
N1—C15	1.4678 (17)	C11—C12	1.359 (2)
N2—C18	1.3391 (17)	C11—H11	0.9500
N3—C23	1.3425 (18)	C12—C13	1.4301 (19)
N3—C19	1.3451 (17)	C12—H12	0.9500
C1—C14	1.4144 (19)	C13—C14	1.4132 (19)
C1—C2	1.4342 (19)	C14—C15	1.5069 (19)
C1—C6	1.4407 (19)	C15—H15A	0.9900
C2—C3	1.366 (2)	C15—H15B	0.9900
C2—H2	0.9500	C16—C17	1.3764 (18)
C3—C4	1.418 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.402 (2)
C4—C5	1.353 (2)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.4733 (18)
C5—C6	1.4290 (19)	C19—C20	1.397 (2)
C5—H5	0.9500	C20—C21	1.382 (2)
C6—C7	1.391 (2)	C20—H20	0.9500
C7—C8	1.389 (2)	C21—C22	1.378 (2)
C7—H7	0.9500	C21—H21	0.9500
C8—C9	1.429 (2)	C22—C23	1.374 (2)
C8—C13	1.4365 (19)	C22—H22	0.9500
C9—C10	1.353 (2)	C23—H23	0.9500
C9—H9	0.9500
N2—N1—C16	111.88 (11)	C11—C12—H12	119.1
N2—N1—C15	116.73 (11)	C13—C12—H12	119.1
C16—N1—C15	131.29 (11)	C14—C13—C12	122.90 (13)
C18—N2—N1	104.91 (11)	C14—C13—C8	119.77 (12)
C23—N3—C19	116.69 (13)	C12—C13—C8	117.32 (13)
C14—C1—C2	123.78 (13)	C13—C14—C1	120.16 (12)
C14—C1—C6	119.21 (12)	C13—C14—C15	119.33 (12)
C2—C1—C6	117.00 (12)	C1—C14—C15	120.35 (12)
C3—C2—C1	121.45 (14)	N1—C15—C14	114.65 (11)
C3—C2—H2	119.3	N1—C15—H15A	108.6
C1—C2—H2	119.3	C14—C15—H15A	108.6
C2—C3—C4	120.87 (14)	N1—C15—H15B	108.6
C2—C3—H3	119.6	C14—C15—H15B	108.6
C4—C3—H3	119.6	H15A—C15—H15B	107.6
C5—C4—C3	119.94 (14)	N1—C16—C17	107.18 (12)
C5—C4—H4	120.0	N1—C16—H16	126.4
C3—C4—H4	120.0	C17—C16—H16	126.4
C4—C5—C6	121.28 (14)	C16—C17—C18	104.73 (12)
C4—C5—H5	119.4	C16—C17—H17	127.6
C6—C5—H5	119.4	C18—C17—H17	127.6
C7—C6—C5	120.94 (13)	N2—C18—C17	111.30 (11)
C7—C6—C1	119.61 (12)	N2—C18—C19	119.23 (12)
C5—C6—C1	119.44 (13)	C17—C18—C19	129.41 (12)
C8—C7—C6	121.87 (13)	N3—C19—C20	122.57 (12)
C8—C7—H7	119.1	N3—C19—C18	117.01 (12)
C6—C7—H7	119.1	C20—C19—C18	120.38 (12)
C7—C8—C9	121.67 (13)	C21—C20—C19	118.95 (13)
C7—C8—C13	119.34 (13)	C21—C20—H20	120.5
C9—C8—C13	118.95 (13)	C19—C20—H20	120.5
C10—C9—C8	121.36 (14)	C22—C21—C20	118.93 (14)
C10—C9—H9	119.3	C22—C21—H21	120.5
C8—C9—H9	119.3	C20—C21—H21	120.5
C9—C10—C11	120.12 (14)	C23—C22—C21	118.39 (13)
C9—C10—H10	119.9	C23—C22—H22	120.8
C11—C10—H10	119.9	C21—C22—H22	120.8
C12—C11—C10	120.38 (14)	N3—C23—C22	124.45 (14)
C12—C11—H11	119.8	N3—C23—H23	117.8
C10—C11—H11	119.8	C22—C23—H23	117.8
C11—C12—C13	121.85 (14)
C16—N1—N2—C18	0.52 (15)	C12—C13—C14—C15	−2.84 (19)
C15—N1—N2—C18	177.37 (11)	C8—C13—C14—C15	176.04 (11)
C14—C1—C2—C3	−177.87 (13)	C2—C1—C14—C13	−179.68 (12)
C6—C1—C2—C3	1.33 (19)	C6—C1—C14—C13	1.14 (19)
C1—C2—C3—C4	−0.2 (2)	C2—C1—C14—C15	5.00 (19)
C2—C3—C4—C5	−0.6 (2)	C6—C1—C14—C15	−174.18 (11)
C3—C4—C5—C6	0.1 (2)	N2—N1—C15—C14	175.47 (11)
C4—C5—C6—C7	−179.35 (13)	C16—N1—C15—C14	−8.4 (2)
C4—C5—C6—C1	1.1 (2)	C13—C14—C15—N1	83.96 (15)
C14—C1—C6—C7	−2.08 (19)	C1—C14—C15—N1	−100.67 (15)
C2—C1—C6—C7	178.69 (12)	N2—N1—C16—C17	−0.56 (16)
C14—C1—C6—C5	177.49 (11)	C15—N1—C16—C17	−176.82 (13)
C2—C1—C6—C5	−1.75 (18)	N1—C16—C17—C18	0.35 (15)
C5—C6—C7—C8	−178.37 (12)	N1—N2—C18—C17	−0.28 (15)
C1—C6—C7—C8	1.2 (2)	N1—N2—C18—C19	−177.62 (11)
C6—C7—C8—C9	178.47 (12)	C16—C17—C18—N2	−0.04 (15)
C6—C7—C8—C13	0.6 (2)	C16—C17—C18—C19	176.95 (13)
C7—C8—C9—C10	−176.59 (14)	C23—N3—C19—C20	0.30 (19)
C13—C8—C9—C10	1.3 (2)	C23—N3—C19—C18	−177.46 (12)
C8—C9—C10—C11	−0.6 (2)	N2—C18—C19—N3	−171.91 (12)
C9—C10—C11—C12	−0.7 (2)	C17—C18—C19—N3	11.3 (2)
C10—C11—C12—C13	1.5 (2)	N2—C18—C19—C20	10.27 (19)
C11—C12—C13—C14	178.08 (13)	C17—C18—C19—C20	−166.52 (14)
C11—C12—C13—C8	−0.8 (2)	N3—C19—C20—C21	−1.3 (2)
C7—C8—C13—C14	−1.57 (19)	C18—C19—C20—C21	176.38 (13)
C9—C8—C13—C14	−179.47 (12)	C19—C20—C21—C22	1.0 (2)
C7—C8—C13—C12	177.37 (12)	C20—C21—C22—C23	0.2 (2)
C9—C8—C13—C12	−0.53 (18)	C19—N3—C23—C22	1.0 (2)
C12—C13—C14—C1	−178.22 (12)	C21—C22—C23—N3	−1.3 (2)
C8—C13—C14—C1	0.66 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2i	0.95	2.55	3.312 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2i	0.95	2.55	3.312 (2)	138

Symmetry code: (i) .