3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde.

In the title mol-ecule, C(12)H(12)N(2)O, the five- and six-membered rings form a dihedral angle of 68.41 (16)°. The aldehyde group is nearly coplanar with the pyrazole ring [C-C-C-O torsion angle = -0.4 (5)°]. The three-dimensional architecture is sustained by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For the anti-bacterial properties of pyrazole derivatives, see: Kane et al. (2003 ▶). For related structures, see: Asiri et al. (2012a ▶,b ▶).

Experimental

Crystal data

C12H12N2O

M = 200.24

Monoclinic,

a = 6.6264 (4) Å

b = 6.7497 (4) Å

c = 22.6203 (12) Å

β = 94.785 (5)°

V = 1008.19 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.25 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.979, T max = 0.996

6376 measured reflections

2335 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.194

S = 1.23

2335 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.31 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/S1600536812010240/xu5480sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010240/xu5480Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010240/xu5480Isup3.cml

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

C12H12N2O	F(000) = 424
Mr = 200.24	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2660 reflections
a = 6.6264 (4) Å	θ = 2.7–27.5°
b = 6.7497 (4) Å	µ = 0.09 mm−1
c = 22.6203 (12) Å	T = 100 K
β = 94.785 (5)°	Prism, colourless
V = 1008.19 (10) Å3	0.25 × 0.15 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2335 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1951 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→6
Tmin = 0.979, Tmax = 0.996	l = −29→29
6376 measured reflections

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H-atom parameters constrained
S = 1.23	w = 1/[σ2(Fo2) + (0.0317P)2 + 2.9806P] where P = (Fo2 + 2Fc2)/3
2335 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.2480 (3)	0.6126 (4)	0.58330 (9)	0.0215 (5)
N1	0.2395 (4)	0.2683 (4)	0.40971 (10)	0.0148 (5)
N2	0.2307 (4)	0.1335 (4)	0.45524 (11)	0.0195 (6)
C1	0.2332 (6)	0.1451 (5)	0.56361 (14)	0.0276 (8)
H1A	0.1190	0.0526	0.5626	0.041*
H1B	0.2177	0.2463	0.5940	0.041*
H1C	0.3600	0.0727	0.5730	0.041*
C2	0.2378 (5)	0.2431 (5)	0.50395 (13)	0.0172 (6)
C3	0.2500 (4)	0.4477 (5)	0.49014 (13)	0.0148 (6)
C4	0.2499 (4)	0.4563 (5)	0.42869 (13)	0.0153 (6)
C5	0.2611 (6)	0.6283 (5)	0.38750 (14)	0.0236 (7)
H5A	0.1524	0.6179	0.3555	0.035*
H5B	0.3925	0.6280	0.3706	0.035*
H5C	0.2456	0.7519	0.4094	0.035*
C6	0.2550 (4)	0.6179 (5)	0.52932 (13)	0.0167 (6)
H6	0.2644	0.7448	0.5116	0.020*
C7	0.2304 (4)	0.1953 (4)	0.34975 (12)	0.0143 (6)
C8	0.4000 (5)	0.2103 (5)	0.31798 (14)	0.0208 (7)
H8	0.5214	0.2683	0.3354	0.025*
C9	0.3893 (5)	0.1389 (5)	0.25999 (14)	0.0235 (7)
H9	0.5033	0.1502	0.2374	0.028*
C10	0.2120 (5)	0.0509 (5)	0.23500 (13)	0.0203 (7)
H10	0.2060	0.0009	0.1956	0.024*
C11	0.0447 (5)	0.0363 (5)	0.26753 (13)	0.0182 (6)
H11	−0.0756	−0.0246	0.2505	0.022*
C12	0.0520 (5)	0.1106 (4)	0.32508 (13)	0.0165 (6)
H12	−0.0636	0.1034	0.3472	0.020*

	U11	U22	U33	U12	U13	U23
O1	0.0239 (11)	0.0255 (12)	0.0150 (10)	−0.0002 (10)	0.0007 (8)	−0.0037 (9)
N1	0.0210 (12)	0.0131 (12)	0.0105 (11)	−0.0012 (10)	0.0024 (9)	0.0006 (9)
N2	0.0305 (14)	0.0157 (13)	0.0126 (12)	−0.0021 (11)	0.0031 (10)	0.0009 (10)
C1	0.048 (2)	0.0210 (17)	0.0140 (15)	−0.0048 (16)	0.0052 (14)	0.0023 (13)
C2	0.0219 (15)	0.0166 (14)	0.0134 (14)	−0.0009 (12)	0.0020 (11)	0.0008 (11)
C3	0.0144 (13)	0.0171 (14)	0.0133 (13)	−0.0012 (12)	0.0031 (10)	−0.0005 (11)
C4	0.0157 (13)	0.0157 (15)	0.0140 (14)	−0.0013 (12)	−0.0020 (11)	0.0000 (11)
C5	0.0401 (19)	0.0145 (15)	0.0160 (15)	−0.0003 (15)	0.0016 (13)	−0.0004 (12)
C6	0.0170 (14)	0.0173 (15)	0.0157 (14)	−0.0012 (12)	0.0012 (11)	−0.0024 (12)
C7	0.0218 (14)	0.0092 (13)	0.0118 (13)	0.0006 (11)	0.0004 (11)	0.0001 (10)
C8	0.0211 (15)	0.0238 (16)	0.0175 (15)	−0.0033 (13)	0.0017 (12)	−0.0043 (13)
C9	0.0230 (15)	0.0280 (18)	0.0205 (15)	−0.0003 (14)	0.0075 (12)	−0.0071 (14)
C10	0.0298 (17)	0.0183 (15)	0.0129 (14)	0.0024 (13)	0.0012 (12)	−0.0031 (12)
C11	0.0242 (15)	0.0139 (14)	0.0155 (14)	−0.0013 (12)	−0.0038 (11)	−0.0001 (12)
C12	0.0206 (14)	0.0140 (14)	0.0149 (13)	−0.0016 (12)	0.0024 (11)	0.0008 (11)

O1—C6	1.226 (4)	C5—H5B	0.9800
N1—C4	1.339 (4)	C5—H5C	0.9800
N1—N2	1.379 (3)	C6—H6	0.9500
N1—C7	1.439 (4)	C7—C12	1.387 (4)
N2—C2	1.325 (4)	C7—C8	1.388 (4)
C1—C2	1.506 (4)	C8—C9	1.394 (4)
C1—H1A	0.9800	C8—H8	0.9500
C1—H1B	0.9800	C9—C10	1.393 (5)
C1—H1C	0.9800	C9—H9	0.9500
C2—C3	1.419 (4)	C10—C11	1.385 (4)
C3—C4	1.391 (4)	C10—H10	0.9500
C3—C6	1.450 (4)	C11—C12	1.392 (4)
C4—C5	1.494 (4)	C11—H11	0.9500
C5—H5A	0.9800	C12—H12	0.9500
C4—N1—N2	112.9 (2)	H5A—C5—H5C	109.5
C4—N1—C7	128.6 (2)	H5B—C5—H5C	109.5
N2—N1—C7	118.5 (2)	O1—C6—C3	125.8 (3)
C2—N2—N1	104.6 (2)	O1—C6—H6	117.1
C2—C1—H1A	109.5	C3—C6—H6	117.1
C2—C1—H1B	109.5	C12—C7—C8	121.4 (3)
H1A—C1—H1B	109.5	C12—C7—N1	119.2 (3)
C2—C1—H1C	109.5	C8—C7—N1	119.4 (3)
H1A—C1—H1C	109.5	C7—C8—C9	118.8 (3)
H1B—C1—H1C	109.5	C7—C8—H8	120.6
N2—C2—C3	111.0 (3)	C9—C8—H8	120.6
N2—C2—C1	119.9 (3)	C10—C9—C8	120.3 (3)
C3—C2—C1	129.1 (3)	C10—C9—H9	119.9
C4—C3—C2	105.4 (3)	C8—C9—H9	119.9
C4—C3—C6	125.2 (3)	C11—C10—C9	120.0 (3)
C2—C3—C6	129.4 (3)	C11—C10—H10	120.0
N1—C4—C3	106.1 (3)	C9—C10—H10	120.0
N1—C4—C5	122.7 (3)	C10—C11—C12	120.3 (3)
C3—C4—C5	131.3 (3)	C10—C11—H11	119.8
C4—C5—H5A	109.5	C12—C11—H11	119.8
C4—C5—H5B	109.5	C7—C12—C11	119.1 (3)
H5A—C5—H5B	109.5	C7—C12—H12	120.4
C4—C5—H5C	109.5	C11—C12—H12	120.4
C4—N1—N2—C2	−0.6 (3)	C6—C3—C4—C5	2.2 (5)
C7—N1—N2—C2	−178.7 (3)	C4—C3—C6—O1	177.3 (3)
N1—N2—C2—C3	0.3 (3)	C2—C3—C6—O1	−0.4 (5)
N1—N2—C2—C1	−179.5 (3)	C4—N1—C7—C12	−110.1 (4)
N2—C2—C3—C4	0.0 (4)	N2—N1—C7—C12	67.7 (4)
C1—C2—C3—C4	179.8 (3)	C4—N1—C7—C8	70.2 (4)
N2—C2—C3—C6	178.1 (3)	N2—N1—C7—C8	−112.1 (3)
C1—C2—C3—C6	−2.2 (6)	C12—C7—C8—C9	0.2 (5)
N2—N1—C4—C3	0.6 (3)	N1—C7—C8—C9	179.9 (3)
C7—N1—C4—C3	178.5 (3)	C7—C8—C9—C10	−1.1 (5)
N2—N1—C4—C5	179.9 (3)	C8—C9—C10—C11	0.8 (5)
C7—N1—C4—C5	−2.2 (5)	C9—C10—C11—C12	0.5 (5)
C2—C3—C4—N1	−0.3 (3)	C8—C7—C12—C11	1.1 (5)
C6—C3—C4—N1	−178.5 (3)	N1—C7—C12—C11	−178.7 (3)
C2—C3—C4—C5	−179.6 (3)	C10—C11—C12—C7	−1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.95	2.43	3.315 (4)	155
C11—H11···Cg1ii	0.95	2.71	3.509 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.95	2.43	3.315 (4)	155
C11—H11⋯Cg1ii	0.95	2.71	3.509 (4)	142

Symmetry codes: (i) ; (ii) .