1-Benzoyl-3-(pyridin-2-yl)-1H-pyrazole.

In the title compound, C(15)H(11)N(3)O, the dihedral angle betwen the heterocyclic rings is 9.23 (5)° and the dihedral angle between the benzoyl and pyrazole rings is 58.64 (5)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(10) loops. The dimers stack into a column running parallel to the b-axis direction.

Related literature

For related structures and background, see: Jones et al. (1997 ▶); Adams et al. (2006 ▶); Al-abbasi & Kassim (2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H11N3O

M = 249.27

Monoclinic,

a = 10.6325 (11) Å

b = 5.7775 (6) Å

c = 19.572 (2) Å

β = 98.426 (6)°

V = 1189.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.982, T max = 0.991

10450 measured reflections

2735 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.00

2735 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033368/hb6370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033368/hb6370Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033368/hb6370Isup3.cml

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

C15H11N3O	F(000) = 520
Mr = 249.27	Dx = 1.392 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7032 reflections
a = 10.6325 (11) Å	θ = 4.7–55.0°
b = 5.7775 (6) Å	µ = 0.09 mm−1
c = 19.572 (2) Å	T = 296 K
β = 98.426 (6)°	Block, colourless
V = 1189.3 (2) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.982, Tmax = 0.991	k = −7→7
10450 measured reflections	l = −25→25

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.430P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2735 reflections	Δρmax = 0.35 e Å−3
173 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (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
O1	0.13720 (7)	1.43117 (13)	0.06519 (4)	0.02310 (19)
N1	0.16990 (8)	1.10288 (14)	0.00732 (4)	0.01636 (19)
N2	0.24411 (8)	0.91307 (15)	−0.00018 (4)	0.01622 (19)
N3	0.22475 (8)	0.59436 (16)	−0.15957 (4)	0.0200 (2)
C4	0.43069 (10)	1.04513 (19)	0.25014 (5)	0.0206 (2)
H4	0.4799	1.0072	0.2919	0.025*
C3	0.34100 (10)	0.88896 (18)	0.21845 (5)	0.0187 (2)
H3	0.3304	0.7468	0.2392	0.022*
C2	0.26702 (9)	0.94408 (18)	0.15592 (5)	0.0172 (2)
H2	0.2096	0.8371	0.1338	0.021*
C1	0.27989 (9)	1.16160 (17)	0.12676 (5)	0.0162 (2)
C7	0.19083 (9)	1.24595 (17)	0.06590 (5)	0.0169 (2)
C10	0.20214 (9)	0.83729 (17)	−0.06333 (5)	0.0158 (2)
C11	0.26054 (9)	0.63418 (17)	−0.09172 (5)	0.0163 (2)
C15	0.27577 (11)	0.4098 (2)	−0.18654 (5)	0.0231 (2)
H15	0.2519	0.3799	−0.2333	0.028*
C14	0.36167 (10)	0.26093 (19)	−0.14932 (6)	0.0231 (2)
H14	0.3938	0.1344	−0.1705	0.028*
C5	0.44676 (10)	1.25791 (19)	0.21942 (5)	0.0209 (2)
H5	0.5091	1.3597	0.2397	0.025*
C6	0.36981 (10)	1.31859 (18)	0.15852 (5)	0.0189 (2)
H6	0.3781	1.4634	0.1389	0.023*
C13	0.39894 (10)	0.30481 (19)	−0.07940 (6)	0.0216 (2)
H13	0.4570	0.2089	−0.0529	0.026*
C12	0.34759 (9)	0.49456 (18)	−0.05019 (5)	0.0186 (2)
H12	0.3708	0.5284	−0.0036	0.022*
C9	0.10122 (9)	0.97734 (18)	−0.09703 (5)	0.0187 (2)
H9	0.0569	0.9577	−0.1413	0.022*
C8	0.08350 (9)	1.14563 (18)	−0.05088 (5)	0.0185 (2)
H8	0.0247	1.2657	−0.0573	0.022*

	U11	U22	U33	U12	U13	U23
O1	0.0271 (4)	0.0165 (4)	0.0252 (4)	0.0037 (3)	0.0025 (3)	−0.0009 (3)
N1	0.0175 (4)	0.0150 (4)	0.0165 (4)	0.0007 (3)	0.0020 (3)	0.0007 (3)
N2	0.0181 (4)	0.0141 (4)	0.0167 (4)	0.0002 (3)	0.0031 (3)	−0.0001 (3)
N3	0.0232 (4)	0.0211 (5)	0.0159 (4)	−0.0032 (3)	0.0029 (3)	−0.0016 (3)
C4	0.0183 (5)	0.0258 (5)	0.0175 (5)	0.0038 (4)	0.0021 (4)	−0.0022 (4)
C3	0.0211 (5)	0.0173 (5)	0.0184 (5)	0.0032 (4)	0.0055 (4)	0.0011 (4)
C2	0.0183 (5)	0.0155 (5)	0.0181 (5)	−0.0010 (4)	0.0039 (4)	−0.0024 (4)
C1	0.0181 (4)	0.0162 (5)	0.0150 (4)	0.0003 (4)	0.0047 (3)	−0.0022 (4)
C7	0.0187 (5)	0.0151 (5)	0.0177 (4)	−0.0018 (4)	0.0050 (4)	−0.0003 (4)
C10	0.0167 (4)	0.0161 (5)	0.0148 (4)	−0.0027 (4)	0.0025 (3)	0.0014 (4)
C11	0.0162 (4)	0.0168 (5)	0.0162 (4)	−0.0035 (4)	0.0035 (3)	−0.0005 (4)
C15	0.0265 (5)	0.0248 (5)	0.0189 (5)	−0.0055 (4)	0.0066 (4)	−0.0049 (4)
C14	0.0217 (5)	0.0205 (5)	0.0290 (5)	−0.0035 (4)	0.0105 (4)	−0.0065 (4)
C5	0.0181 (5)	0.0233 (5)	0.0216 (5)	−0.0034 (4)	0.0038 (4)	−0.0062 (4)
C6	0.0218 (5)	0.0161 (5)	0.0198 (5)	−0.0024 (4)	0.0066 (4)	−0.0022 (4)
C13	0.0170 (5)	0.0200 (5)	0.0281 (5)	−0.0009 (4)	0.0039 (4)	0.0006 (4)
C12	0.0179 (4)	0.0198 (5)	0.0178 (5)	−0.0027 (4)	0.0020 (3)	−0.0006 (4)
C9	0.0179 (5)	0.0209 (5)	0.0168 (4)	−0.0008 (4)	0.0010 (4)	0.0019 (4)
C8	0.0169 (4)	0.0190 (5)	0.0192 (5)	0.0000 (4)	0.0010 (4)	0.0033 (4)

O1—C7	1.2116 (12)	C10—C9	1.4260 (14)
N1—N2	1.3713 (12)	C10—C11	1.4740 (14)
N1—C8	1.3768 (12)	C11—C12	1.3955 (14)
N1—C7	1.4045 (13)	C15—C14	1.3819 (16)
N2—C10	1.3255 (12)	C15—H15	0.9300
N3—C15	1.3393 (14)	C14—C13	1.3910 (15)
N3—C11	1.3465 (12)	C14—H14	0.9300
C4—C5	1.3900 (15)	C5—C6	1.3883 (14)
C4—C3	1.3910 (15)	C5—H5	0.9300
C4—H4	0.9300	C6—H6	0.9300
C3—C2	1.3913 (14)	C13—C12	1.3850 (15)
C3—H3	0.9300	C13—H13	0.9300
C2—C1	1.3952 (14)	C12—H12	0.9300
C2—H2	0.9300	C9—C8	1.3589 (15)
C1—C6	1.3961 (14)	C9—H9	0.9300
C1—C7	1.4908 (13)	C8—H8	0.9300
N2—N1—C8	112.31 (8)	C12—C11—C10	121.39 (9)
N2—N1—C7	122.22 (8)	N3—C15—C14	124.21 (10)
C8—N1—C7	125.20 (9)	N3—C15—H15	117.9
C10—N2—N1	104.10 (8)	C14—C15—H15	117.9
C15—N3—C11	116.90 (9)	C15—C14—C13	118.44 (10)
C5—C4—C3	120.04 (9)	C15—C14—H14	120.8
C5—C4—H4	120.0	C13—C14—H14	120.8
C3—C4—H4	120.0	C6—C5—C4	120.02 (10)
C4—C3—C2	120.40 (10)	C6—C5—H5	120.0
C4—C3—H3	119.8	C4—C5—H5	120.0
C2—C3—H3	119.8	C5—C6—C1	119.82 (10)
C3—C2—C1	119.29 (9)	C5—C6—H6	120.1
C3—C2—H2	120.4	C1—C6—H6	120.1
C1—C2—H2	120.4	C12—C13—C14	118.53 (10)
C2—C1—C6	120.32 (9)	C12—C13—H13	120.7
C2—C1—C7	122.17 (9)	C14—C13—H13	120.7
C6—C1—C7	117.18 (9)	C13—C12—C11	119.02 (9)
O1—C7—N1	119.50 (9)	C13—C12—H12	120.5
O1—C7—C1	122.72 (9)	C11—C12—H12	120.5
N1—C7—C1	117.77 (9)	C8—C9—C10	105.47 (9)
N2—C10—C9	111.81 (9)	C8—C9—H9	127.3
N2—C10—C11	120.77 (9)	C10—C9—H9	127.3
C9—C10—C11	127.41 (9)	C9—C8—N1	106.31 (9)
N3—C11—C12	122.90 (9)	C9—C8—H8	126.8
N3—C11—C10	115.72 (9)	N1—C8—H8	126.8

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.44	3.3720 (13)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.44	3.3720 (13)	175

Symmetry code: (i) .