1-Phenyl-1H-pyrazole-4-carbaldehyde.

In the title mol-ecule, C(10)H(8)N(2)O, the five- and six-membered rings form a dihedral angle of 10.14 (9)°. The aldehyde group is almost coplanar with the pyrazole ring to which it is connected [O-C-C-C torsion angle = -179.35 (17)°]. In the crystal, inversion dimers are linked by four C-H⋯O inter-actions as the carbonyl O atom accepts two such bonds. The dimeric aggregates are linked into supra-molecular layers in the ac plane by C-H⋯π and π-π [ring centroid(pyrrole)⋯ring centroid(phen-yl) = 3.8058 (10) Å] inter-actions.

Related literature

For the anti-bacterial properties of pyrazole derivatives, see: Kane et al. (2003 ▶). For related structures, see: Asiri, Al-Youbi, et al. (2012 ▶); Asiri, Faidallah et al. (2012 ▶). For the synthesis, see: Vera-DiVaio et al. (2009 ▶).

Experimental

Crystal data

C10H8N2O

M = 172.18

Monoclinic,

a = 11.1657 (10) Å

b = 5.0858 (4) Å

c = 15.3034 (11) Å

β = 111.130 (9)°

V = 810.60 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.30 × 0.30 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.972, T max = 0.986

3485 measured reflections

1814 independent reflections

1359 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.136

S = 0.99

1814 reflections

151 parameters

All H-atom parameters refined

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010896/bt5843sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010896/bt5843Isup2.hkl

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

C10H8N2O	F(000) = 360
Mr = 172.18	Dx = 1.411 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1251 reflections
a = 11.1657 (10) Å	θ = 2.8–27.5°
b = 5.0858 (4) Å	µ = 0.10 mm−1
c = 15.3034 (11) Å	T = 100 K
β = 111.130 (9)°	Prism, light-brown
V = 810.60 (11) Å3	0.30 × 0.30 × 0.15 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	1814 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1359 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.050
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.8°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→6
Tmin = 0.972, Tmax = 0.986	l = −19→13
3485 measured 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)] = 0.050	All H-atom parameters refined
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0732P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
1814 reflections	Δρmax = 0.28 e Å−3
151 parameters	Δρmin = −0.26 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: 0.013 (4)

	x	y	z	Uiso*/Ueq
O1	0.11384 (11)	0.2706 (2)	0.62516 (8)	0.0286 (4)
N1	0.26714 (12)	0.9228 (3)	0.52304 (9)	0.0196 (3)
N2	0.38346 (13)	0.9268 (3)	0.59584 (9)	0.0247 (4)
C1	0.21644 (15)	0.3842 (3)	0.65682 (11)	0.0230 (4)
C2	0.25665 (15)	0.6026 (3)	0.61478 (11)	0.0209 (4)
C3	0.37465 (16)	0.7329 (3)	0.65005 (12)	0.0245 (4)
C4	0.18990 (15)	0.7336 (3)	0.53228 (11)	0.0204 (4)
C5	0.24267 (15)	1.1131 (3)	0.45059 (10)	0.0196 (4)
C6	0.34207 (16)	1.2698 (3)	0.44624 (11)	0.0226 (4)
C7	0.31714 (17)	1.4569 (4)	0.37669 (12)	0.0248 (4)
C8	0.19463 (17)	1.4863 (4)	0.31105 (11)	0.0247 (4)
C9	0.09706 (17)	1.3272 (4)	0.31553 (12)	0.0263 (4)
C10	0.11990 (16)	1.1412 (3)	0.38573 (12)	0.0242 (4)
H1	0.2818 (16)	0.327 (4)	0.7201 (13)	0.022 (4)*
H3	0.4456 (17)	0.689 (4)	0.7089 (13)	0.027 (5)*
H4	0.1060 (17)	0.707 (3)	0.4858 (12)	0.022 (5)*
H6	0.4267 (19)	1.239 (4)	0.4903 (14)	0.033 (5)*
H7	0.3846 (16)	1.567 (4)	0.3715 (12)	0.023 (5)*
H8	0.1801 (15)	1.619 (4)	0.2621 (12)	0.019 (4)*
H9	0.0057 (18)	1.351 (4)	0.2696 (14)	0.037 (5)*
H10	0.0500 (15)	1.030 (4)	0.3886 (12)	0.023 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0250 (7)	0.0306 (8)	0.0274 (6)	−0.0045 (5)	0.0063 (5)	−0.0006 (6)
N1	0.0183 (7)	0.0214 (8)	0.0154 (6)	0.0002 (5)	0.0015 (5)	−0.0005 (6)
N2	0.0193 (7)	0.0286 (8)	0.0194 (7)	−0.0011 (6)	−0.0013 (6)	0.0005 (6)
C1	0.0229 (9)	0.0254 (9)	0.0184 (8)	0.0017 (7)	0.0046 (7)	−0.0011 (7)
C2	0.0205 (8)	0.0216 (9)	0.0186 (7)	0.0007 (6)	0.0047 (6)	−0.0032 (7)
C3	0.0225 (9)	0.0270 (10)	0.0192 (8)	0.0005 (7)	0.0018 (7)	0.0001 (7)
C4	0.0182 (8)	0.0220 (9)	0.0185 (7)	−0.0007 (6)	0.0035 (7)	−0.0038 (7)
C5	0.0230 (8)	0.0197 (9)	0.0142 (7)	0.0011 (6)	0.0042 (6)	−0.0017 (6)
C6	0.0196 (9)	0.0263 (10)	0.0191 (8)	−0.0015 (7)	0.0038 (7)	−0.0026 (7)
C7	0.0271 (9)	0.0243 (9)	0.0238 (8)	−0.0024 (7)	0.0103 (7)	−0.0034 (8)
C8	0.0313 (9)	0.0205 (9)	0.0209 (8)	0.0021 (7)	0.0076 (7)	0.0027 (8)
C9	0.0242 (9)	0.0253 (10)	0.0236 (8)	0.0031 (7)	0.0017 (7)	0.0037 (8)
C10	0.0212 (9)	0.0222 (9)	0.0251 (8)	−0.0010 (7)	0.0034 (7)	0.0002 (8)

O1—C1	1.2168 (19)	C5—C10	1.380 (2)
N1—C4	1.333 (2)	C5—C6	1.387 (2)
N1—N2	1.3731 (17)	C6—C7	1.379 (2)
N1—C5	1.422 (2)	C6—H6	0.96 (2)
N2—C3	1.315 (2)	C7—C8	1.383 (2)
C1—C2	1.435 (2)	C7—H7	0.963 (18)
C1—H1	1.023 (18)	C8—C9	1.379 (3)
C2—C4	1.384 (2)	C8—H8	0.978 (18)
C2—C3	1.398 (2)	C9—C10	1.384 (2)
C3—H3	0.986 (18)	C9—H9	1.016 (18)
C4—H4	0.960 (17)	C10—H10	0.977 (17)
C4—N1—N2	112.57 (12)	C10—C5—N1	119.55 (14)
C4—N1—C5	128.61 (13)	C6—C5—N1	119.75 (14)
N2—N1—C5	118.81 (13)	C7—C6—C5	119.40 (15)
C3—N2—N1	103.68 (13)	C7—C6—H6	122.1 (12)
O1—C1—C2	126.22 (15)	C5—C6—H6	118.4 (12)
O1—C1—H1	119.3 (10)	C6—C7—C8	120.47 (16)
C2—C1—H1	114.5 (10)	C6—C7—H7	121.1 (11)
C4—C2—C3	104.28 (15)	C8—C7—H7	118.4 (11)
C4—C2—C1	129.01 (15)	C9—C8—C7	119.52 (17)
C3—C2—C1	126.71 (15)	C9—C8—H8	121.9 (10)
N2—C3—C2	112.73 (14)	C7—C8—H8	118.6 (10)
N2—C3—H3	121.7 (11)	C8—C9—C10	120.80 (16)
C2—C3—H3	125.6 (11)	C8—C9—H9	120.6 (11)
N1—C4—C2	106.74 (14)	C10—C9—H9	118.5 (11)
N1—C4—H4	121.3 (10)	C5—C10—C9	119.10 (16)
C2—C4—H4	131.9 (11)	C5—C10—H10	120.7 (10)
C10—C5—C6	120.70 (15)	C9—C10—H10	120.2 (10)
C4—N1—N2—C3	0.04 (18)	N2—N1—C5—C10	−169.04 (14)
C5—N1—N2—C3	179.12 (14)	C4—N1—C5—C6	−170.62 (15)
O1—C1—C2—C4	1.2 (3)	N2—N1—C5—C6	10.5 (2)
O1—C1—C2—C3	−179.35 (17)	C10—C5—C6—C7	0.6 (2)
N1—N2—C3—C2	0.16 (19)	N1—C5—C6—C7	−178.94 (14)
C4—C2—C3—N2	−0.3 (2)	C5—C6—C7—C8	−0.8 (3)
C1—C2—C3—N2	−179.83 (16)	C6—C7—C8—C9	0.0 (3)
N2—N1—C4—C2	−0.21 (18)	C7—C8—C9—C10	1.0 (3)
C5—N1—C4—C2	−179.18 (15)	C6—C5—C10—C9	0.4 (3)
C3—C2—C4—N1	0.29 (17)	N1—C5—C10—C9	179.95 (15)
C1—C2—C4—N1	179.81 (16)	C8—C9—C10—C5	−1.2 (3)
C4—N1—C5—C10	9.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.960 (19)	2.432 (19)	3.379 (2)	168.6 (13)
C10—H10···O1i	0.978 (19)	2.335 (19)	3.303 (2)	170.8 (16)
C8—H8···Cg1ii	0.978 (18)	2.947 (18)	3.761 (2)	141.4 (14)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.960 (19)	2.432 (19)	3.379 (2)	168.6 (13)
C10—H10⋯O1i	0.978 (19)	2.335 (19)	3.303 (2)	170.8 (16)
C8—H8⋯Cg1ii	0.978 (18)	2.947 (18)	3.761 (2)	141.4 (14)

Symmetry codes: (i) ; (ii) .