3-Methyl-5-phen-oxy-1-phenyl-1H-pyrazole-4-carbaldehyde.

In the title compound, C(17)H(14)N(2)O(2), the pyrazole ring makes dihedral angles of 73.67 (4) and 45.99 (4)°, respectively, with the adjacent phenyl and phen-oxy rings. In the crystal, there are no classical hydrogen bonds, but a weak C-H⋯π inter-action is observed.

Related literature

For biological applications of pyrazole derivatives, see: Rai et al. (2008 ▶); Isloor et al. (2009 ▶); Girisha et al. (2010 ▶). For a related structure, see: Shahani et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H14N2O2

M = 278.30

Monoclinic,

a = 8.6207 (1) Å

b = 7.1695 (1) Å

c = 22.9228 (3) Å

β = 99.168 (1)°

V = 1398.67 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.46 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.961, T max = 0.988

24894 measured reflections

6610 independent reflections

5063 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.06

6610 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036786/is2775sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036786/is2775Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036786/is2775Isup3.cml

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

C17H14N2O2	F(000) = 584
Mr = 278.30	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7046 reflections
a = 8.6207 (1) Å	θ = 3.7–36.0°
b = 7.1695 (1) Å	µ = 0.09 mm−1
c = 22.9228 (3) Å	T = 100 K
β = 99.168 (1)°	Block, colourless
V = 1398.67 (3) Å3	0.46 × 0.20 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6610 independent reflections
Radiation source: fine-focus sealed tube	5063 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 36.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.961, Tmax = 0.988	k = −10→11
24894 measured reflections	l = −37→37

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1411P] where P = (Fo2 + 2Fc2)/3
6610 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.25 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
O1	0.05681 (7)	0.69565 (8)	0.13280 (3)	0.01742 (12)
O2	0.06804 (8)	0.18778 (10)	0.24152 (3)	0.02350 (14)
N1	−0.13873 (7)	0.51835 (10)	0.07691 (3)	0.01459 (12)
N2	−0.21777 (8)	0.35085 (10)	0.07780 (3)	0.01602 (12)
C1	−0.08495 (9)	0.74369 (12)	0.00220 (3)	0.01637 (14)
H1A	0.0246	0.7199	0.0118	0.020*
C2	−0.14204 (10)	0.87209 (12)	−0.04165 (3)	0.01873 (15)
H2A	−0.0707	0.9369	−0.0620	0.022*
C3	−0.30261 (10)	0.90625 (12)	−0.05596 (3)	0.02026 (15)
H3A	−0.3404	0.9951	−0.0856	0.024*
C4	−0.40764 (10)	0.81003 (12)	−0.02678 (3)	0.01878 (15)
H4A	−0.5173	0.8318	−0.0370	0.023*
C5	−0.35271 (9)	0.68226 (12)	0.01719 (3)	0.01632 (14)
H5A	−0.4243	0.6168	0.0372	0.020*
C6	−0.19152 (9)	0.65081 (11)	0.03172 (3)	0.01421 (13)
C7	−0.14856 (9)	0.26348 (11)	0.12608 (3)	0.01569 (13)
C8	−0.02490 (8)	0.37265 (11)	0.15780 (3)	0.01490 (13)
C9	−0.02436 (8)	0.53407 (11)	0.12425 (3)	0.01441 (13)
C10	0.22016 (9)	0.68417 (11)	0.15060 (3)	0.01485 (13)
C11	0.30911 (9)	0.55321 (12)	0.12616 (3)	0.01733 (14)
H11A	0.2605	0.4651	0.0981	0.021*
C12	0.47161 (9)	0.55367 (13)	0.14369 (3)	0.01931 (15)
H12A	0.5342	0.4630	0.1281	0.023*
C13	0.54285 (10)	0.68545 (13)	0.18366 (4)	0.02145 (16)
H13A	0.6538	0.6863	0.1949	0.026*
C14	0.45058 (10)	0.81631 (13)	0.20720 (4)	0.02241 (17)
H14A	0.4992	0.9067	0.2344	0.027*
C15	0.28718 (10)	0.81597 (12)	0.19112 (3)	0.01855 (15)
H15A	0.2238	0.9038	0.2075	0.022*
C16	−0.20510 (10)	0.07608 (13)	0.14161 (4)	0.02157 (16)
H16A	−0.2763	0.0253	0.1078	0.032*
H16B	−0.2610	0.0877	0.1755	0.032*
H16C	−0.1151	−0.0078	0.1518	0.032*
C17	0.07517 (9)	0.33089 (12)	0.21332 (3)	0.01724 (14)
H17A	0.1514	0.4212	0.2288	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0151 (2)	0.0131 (3)	0.0227 (2)	−0.00067 (19)	−0.00134 (19)	−0.0014 (2)
O2	0.0227 (3)	0.0224 (3)	0.0238 (3)	−0.0006 (2)	−0.0010 (2)	0.0070 (2)
N1	0.0127 (2)	0.0135 (3)	0.0167 (2)	−0.0012 (2)	−0.00011 (19)	0.0005 (2)
N2	0.0139 (3)	0.0141 (3)	0.0194 (3)	−0.0023 (2)	0.0007 (2)	0.0013 (2)
C1	0.0155 (3)	0.0157 (3)	0.0180 (3)	−0.0027 (2)	0.0028 (2)	−0.0014 (2)
C2	0.0222 (3)	0.0163 (4)	0.0179 (3)	−0.0049 (3)	0.0038 (3)	0.0003 (3)
C3	0.0251 (4)	0.0160 (4)	0.0184 (3)	−0.0009 (3)	−0.0004 (3)	0.0022 (3)
C4	0.0173 (3)	0.0180 (4)	0.0197 (3)	0.0016 (3)	−0.0012 (3)	0.0006 (3)
C5	0.0142 (3)	0.0176 (4)	0.0169 (3)	−0.0006 (2)	0.0015 (2)	0.0008 (2)
C6	0.0143 (3)	0.0136 (3)	0.0144 (3)	−0.0003 (2)	0.0013 (2)	0.0000 (2)
C7	0.0135 (3)	0.0149 (3)	0.0183 (3)	0.0003 (2)	0.0017 (2)	0.0013 (2)
C8	0.0136 (3)	0.0146 (3)	0.0160 (3)	0.0003 (2)	0.0008 (2)	0.0001 (2)
C9	0.0122 (3)	0.0143 (3)	0.0162 (3)	−0.0003 (2)	0.0007 (2)	−0.0018 (2)
C10	0.0138 (3)	0.0150 (3)	0.0151 (3)	−0.0018 (2)	0.0004 (2)	0.0004 (2)
C11	0.0165 (3)	0.0183 (4)	0.0168 (3)	−0.0016 (3)	0.0018 (2)	−0.0028 (3)
C12	0.0166 (3)	0.0222 (4)	0.0196 (3)	−0.0003 (3)	0.0044 (2)	0.0003 (3)
C13	0.0154 (3)	0.0261 (4)	0.0220 (3)	−0.0046 (3)	0.0003 (3)	0.0010 (3)
C14	0.0207 (4)	0.0236 (4)	0.0215 (3)	−0.0067 (3)	−0.0009 (3)	−0.0043 (3)
C15	0.0190 (3)	0.0175 (4)	0.0186 (3)	−0.0034 (3)	0.0014 (2)	−0.0036 (3)
C16	0.0189 (3)	0.0168 (4)	0.0274 (3)	−0.0031 (3)	−0.0011 (3)	0.0052 (3)
C17	0.0160 (3)	0.0179 (4)	0.0170 (3)	0.0013 (3)	0.0001 (2)	0.0007 (2)

O1—C9	1.3514 (10)	C7—C16	1.4916 (12)
O1—C10	1.4047 (9)	C8—C9	1.3899 (11)
O2—C17	1.2194 (10)	C8—C17	1.4505 (10)
N1—C9	1.3496 (9)	C10—C15	1.3850 (11)
N1—N2	1.3825 (10)	C10—C11	1.3858 (11)
N1—C6	1.4254 (10)	C11—C12	1.3945 (11)
N2—C7	1.3276 (10)	C11—H11A	0.9500
C1—C2	1.3937 (11)	C12—C13	1.3892 (12)
C1—C6	1.3942 (10)	C12—H12A	0.9500
C1—H1A	0.9500	C13—C14	1.3931 (13)
C2—C3	1.3925 (12)	C13—H13A	0.9500
C2—H2A	0.9500	C14—C15	1.3981 (12)
C3—C4	1.3914 (12)	C14—H14A	0.9500
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.3882 (11)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.3947 (10)	C16—H16C	0.9800
C5—H5A	0.9500	C17—H17A	0.9500
C7—C8	1.4250 (11)
C9—O1—C10	117.63 (6)	N1—C9—C8	107.99 (7)
C9—N1—N2	111.06 (6)	O1—C9—C8	132.91 (7)
C9—N1—C6	129.53 (7)	C15—C10—C11	122.33 (7)
N2—N1—C6	119.24 (6)	C15—C10—O1	116.53 (7)
C7—N2—N1	105.37 (6)	C11—C10—O1	121.06 (7)
C2—C1—C6	118.77 (7)	C10—C11—C12	118.50 (7)
C2—C1—H1A	120.6	C10—C11—H11A	120.8
C6—C1—H1A	120.6	C12—C11—H11A	120.8
C3—C2—C1	120.64 (7)	C13—C12—C11	120.65 (8)
C3—C2—H2A	119.7	C13—C12—H12A	119.7
C1—C2—H2A	119.7	C11—C12—H12A	119.7
C4—C3—C2	119.88 (7)	C12—C13—C14	119.59 (8)
C4—C3—H3A	120.1	C12—C13—H13A	120.2
C2—C3—H3A	120.1	C14—C13—H13A	120.2
C5—C4—C3	120.22 (7)	C13—C14—C15	120.68 (8)
C5—C4—H4A	119.9	C13—C14—H14A	119.7
C3—C4—H4A	119.9	C15—C14—H14A	119.7
C4—C5—C6	119.46 (7)	C10—C15—C14	118.23 (8)
C4—C5—H5A	120.3	C10—C15—H15A	120.9
C6—C5—H5A	120.3	C14—C15—H15A	120.9
C1—C6—C5	121.02 (7)	C7—C16—H16A	109.5
C1—C6—N1	120.81 (7)	C7—C16—H16B	109.5
C5—C6—N1	118.16 (7)	H16A—C16—H16B	109.5
N2—C7—C8	111.50 (7)	C7—C16—H16C	109.5
N2—C7—C16	120.23 (7)	H16A—C16—H16C	109.5
C8—C7—C16	128.27 (7)	H16B—C16—H16C	109.5
C9—C8—C7	104.08 (6)	O2—C17—C8	124.45 (8)
C9—C8—C17	127.11 (7)	O2—C17—H17A	117.8
C7—C8—C17	128.78 (7)	C8—C17—H17A	117.8
N1—C9—O1	118.89 (7)
C9—N1—N2—C7	−0.74 (8)	C6—N1—C9—O1	0.07 (12)
C6—N1—N2—C7	−176.34 (6)	N2—N1—C9—C8	0.53 (9)
C6—C1—C2—C3	−0.36 (12)	C6—N1—C9—C8	175.55 (7)
C1—C2—C3—C4	−0.75 (12)	C10—O1—C9—N1	−137.81 (7)
C2—C3—C4—C5	1.03 (12)	C10—O1—C9—C8	48.05 (11)
C3—C4—C5—C6	−0.20 (12)	C7—C8—C9—N1	−0.11 (8)
C2—C1—C6—C5	1.21 (11)	C17—C8—C9—N1	−178.21 (7)
C2—C1—C6—N1	−179.97 (7)	C7—C8—C9—O1	174.49 (8)
C4—C5—C6—C1	−0.93 (12)	C17—C8—C9—O1	−3.61 (14)
C4—C5—C6—N1	−179.79 (7)	C9—O1—C10—C15	−142.16 (7)
C9—N1—C6—C1	49.63 (11)	C9—O1—C10—C11	41.12 (10)
N2—N1—C6—C1	−135.69 (8)	C15—C10—C11—C12	0.73 (12)
C9—N1—C6—C5	−131.51 (8)	O1—C10—C11—C12	177.26 (7)
N2—N1—C6—C5	43.17 (10)	C10—C11—C12—C13	−1.55 (12)
N1—N2—C7—C8	0.67 (9)	C11—C12—C13—C14	1.12 (13)
N1—N2—C7—C16	179.53 (7)	C12—C13—C14—C15	0.17 (13)
N2—C7—C8—C9	−0.37 (9)	C11—C10—C15—C14	0.52 (12)
C16—C7—C8—C9	−179.11 (8)	O1—C10—C15—C14	−176.16 (7)
N2—C7—C8—C17	177.70 (7)	C13—C14—C15—C10	−0.97 (13)
C16—C7—C8—C17	−1.05 (14)	C9—C8—C17—O2	178.74 (8)
N2—N1—C9—O1	−174.96 (6)	C7—C8—C17—O2	1.10 (14)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cg1i	0.95	2.62	3.5052 (8)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg1i	0.95	2.62	3.5052 (8)	156

Symmetry code: (i) .