Ethyl 1-tert-butyl-5-phenyl-1H-pyrazole-4-carboxyl-ate.

In the title compound, C(16)H(20)N(2)O(2), the pyrazole ring is essentially planar [maximum deviation = 0.008 (2) Å] and is inclined at an angle of 82.82 (10)° with respect to the phenyl ring. The crystal packing is consolidated by pairs of inter-molecular C-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers stacked along the a axis.

Related literature

For general background to pyrazole derivatives and their biological activity, see: Isloor et al. (2009 ▶); Lambert & Fowler (2005 ▶); Lan et al. (1999 ▶). For related structures, see: Fun et al. (2009 ▶; 2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H20N2O2

M = 272.34

Triclinic,

a = 9.0665 (2) Å

b = 9.3351 (2) Å

c = 10.5408 (3) Å

α = 110.450 (1)°

β = 113.987 (1)°

γ = 97.645 (2)°

V = 723.22 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.41 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.990

12406 measured reflections

2655 independent reflections

2179 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.04

2655 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.20 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 datablocks global, I. DOI: 10.1107/S1600536810030643/ci5147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030643/ci5147Isup2.hkl

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

C16H20N2O2	Z = 2
Mr = 272.34	F(000) = 292
Triclinic, P1	Dx = 1.251 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0665 (2) Å	Cell parameters from 6289 reflections
b = 9.3351 (2) Å	θ = 2.4–34.3°
c = 10.5408 (3) Å	µ = 0.08 mm−1
α = 110.450 (1)°	T = 100 K
β = 113.987 (1)°	Needle, yellow
γ = 97.645 (2)°	0.41 × 0.20 × 0.12 mm
V = 723.22 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	2179 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.967, Tmax = 0.990	k = −11→11
12406 measured reflections	l = −12→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.3388P] where P = (Fo2 + 2Fc2)/3
2655 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.53056 (13)	0.32289 (13)	0.13622 (12)	0.0190 (3)
O2	0.52454 (14)	0.14419 (13)	0.23468 (13)	0.0247 (3)
N1	0.85134 (17)	0.68033 (16)	0.57591 (15)	0.0199 (3)
N2	0.87235 (16)	0.58254 (15)	0.64872 (15)	0.0169 (3)
C1	0.8628 (2)	0.18877 (19)	0.56614 (19)	0.0203 (4)
H1A	0.9334	0.2079	0.5259	0.024*
C2	0.8544 (2)	0.0604 (2)	0.60345 (19)	0.0223 (4)
H2A	0.9206	−0.0053	0.5895	0.027*
C3	0.7477 (2)	0.02988 (19)	0.66145 (19)	0.0216 (4)
H3A	0.7430	−0.0557	0.6872	0.026*
C4	0.6484 (2)	0.12657 (19)	0.68093 (19)	0.0209 (4)
H4A	0.5754	0.1050	0.7183	0.025*
C5	0.65692 (19)	0.25632 (19)	0.64487 (18)	0.0187 (4)
H5A	0.5899	0.3213	0.6583	0.022*
C6	0.76584 (19)	0.28886 (19)	0.58869 (18)	0.0166 (4)
C7	0.77480 (19)	0.42591 (18)	0.54764 (18)	0.0160 (3)
C8	0.69038 (19)	0.42220 (19)	0.40266 (18)	0.0166 (4)
C9	0.7435 (2)	0.58270 (19)	0.42835 (19)	0.0190 (4)
H9A	0.7070	0.6163	0.3507	0.023*
C10	0.98019 (19)	0.66369 (19)	0.82223 (18)	0.0178 (4)
C11	0.8627 (2)	0.6922 (2)	0.89211 (19)	0.0233 (4)
H11A	0.7959	0.7535	0.8527	0.035*
H11B	0.9299	0.7508	1.0030	0.035*
H11C	0.7884	0.5902	0.8646	0.035*
C12	1.0849 (2)	0.5612 (2)	0.87611 (19)	0.0213 (4)
H12A	1.1484	0.5365	0.8219	0.032*
H12B	1.0101	0.4628	0.8548	0.032*
H12C	1.1623	0.6199	0.9856	0.032*
C13	1.1020 (2)	0.8262 (2)	0.8701 (2)	0.0232 (4)
H13A	1.0376	0.8944	0.8428	0.035*
H13B	1.1678	0.8091	0.8175	0.035*
H13C	1.1771	0.8768	0.9802	0.035*
C14	0.57491 (19)	0.2808 (2)	0.25368 (19)	0.0178 (4)
C15	0.4271 (2)	0.19063 (19)	−0.01920 (18)	0.0204 (4)
H15A	0.3269	0.1272	−0.0275	0.024*
H15B	0.4921	0.1206	−0.0422	0.024*
C16	0.3759 (2)	0.2633 (2)	−0.1304 (2)	0.0261 (4)
H16A	0.3137	0.1788	−0.2348	0.039*
H16B	0.4759	0.3313	−0.1164	0.039*
H16C	0.3051	0.3263	−0.1112	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0228 (6)	0.0165 (6)	0.0116 (6)	0.0008 (5)	0.0054 (5)	0.0054 (5)
O2	0.0322 (6)	0.0163 (7)	0.0189 (7)	−0.0002 (5)	0.0098 (5)	0.0070 (5)
N1	0.0249 (7)	0.0164 (7)	0.0176 (8)	0.0037 (6)	0.0089 (6)	0.0094 (6)
N2	0.0197 (7)	0.0145 (7)	0.0143 (7)	0.0020 (6)	0.0070 (6)	0.0070 (6)
C1	0.0222 (8)	0.0189 (9)	0.0181 (9)	0.0033 (7)	0.0100 (7)	0.0075 (7)
C2	0.0250 (8)	0.0169 (9)	0.0211 (9)	0.0067 (7)	0.0085 (8)	0.0076 (7)
C3	0.0262 (8)	0.0142 (9)	0.0164 (9)	0.0001 (7)	0.0043 (7)	0.0080 (7)
C4	0.0222 (8)	0.0193 (9)	0.0156 (9)	−0.0014 (7)	0.0075 (7)	0.0069 (7)
C5	0.0191 (8)	0.0159 (9)	0.0159 (9)	0.0021 (7)	0.0069 (7)	0.0047 (7)
C6	0.0179 (7)	0.0134 (8)	0.0098 (8)	−0.0009 (6)	0.0022 (6)	0.0035 (6)
C7	0.0163 (7)	0.0142 (9)	0.0161 (8)	0.0028 (6)	0.0088 (7)	0.0049 (7)
C8	0.0185 (8)	0.0170 (9)	0.0151 (8)	0.0046 (7)	0.0088 (7)	0.0077 (7)
C9	0.0227 (8)	0.0189 (9)	0.0153 (9)	0.0044 (7)	0.0082 (7)	0.0095 (7)
C10	0.0192 (8)	0.0158 (9)	0.0124 (8)	0.0013 (7)	0.0057 (7)	0.0039 (7)
C11	0.0243 (8)	0.0228 (10)	0.0180 (9)	0.0039 (7)	0.0099 (7)	0.0061 (8)
C12	0.0230 (8)	0.0194 (9)	0.0140 (9)	0.0025 (7)	0.0051 (7)	0.0059 (7)
C13	0.0220 (8)	0.0198 (9)	0.0189 (9)	0.0001 (7)	0.0058 (7)	0.0067 (7)
C14	0.0182 (7)	0.0201 (9)	0.0168 (9)	0.0050 (7)	0.0093 (7)	0.0095 (7)
C15	0.0224 (8)	0.0170 (9)	0.0135 (9)	0.0013 (7)	0.0059 (7)	0.0034 (7)
C16	0.0282 (9)	0.0258 (10)	0.0173 (9)	0.0050 (8)	0.0076 (8)	0.0079 (8)

O1—C14	1.3511 (18)	C8—C14	1.467 (2)
O1—C15	1.4550 (18)	C9—H9A	0.93
O2—C14	1.2116 (18)	C10—C12	1.524 (2)
N1—C9	1.320 (2)	C10—C11	1.524 (2)
N1—N2	1.3695 (17)	C10—C13	1.530 (2)
N2—C7	1.363 (2)	C11—H11A	0.96
N2—C10	1.502 (2)	C11—H11B	0.96
C1—C2	1.388 (2)	C11—H11C	0.96
C1—C6	1.391 (2)	C12—H12A	0.96
C1—H1A	0.93	C12—H12B	0.96
C2—C3	1.386 (2)	C12—H12C	0.96
C2—H2A	0.93	C13—H13A	0.96
C3—C4	1.380 (2)	C13—H13B	0.96
C3—H3A	0.93	C13—H13C	0.96
C4—C5	1.392 (2)	C15—C16	1.499 (2)
C4—H4A	0.93	C15—H15A	0.97
C5—C6	1.393 (2)	C15—H15B	0.97
C5—H5A	0.93	C16—H16A	0.96
C6—C7	1.489 (2)	C16—H16B	0.96
C7—C8	1.388 (2)	C16—H16C	0.96
C8—C9	1.403 (2)
C14—O1—C15	115.77 (12)	C12—C10—C13	108.71 (13)
C9—N1—N2	105.07 (12)	C11—C10—C13	109.39 (14)
C7—N2—N1	111.67 (12)	C10—C11—H11A	109.5
C7—N2—C10	131.06 (13)	C10—C11—H11B	109.5
N1—N2—C10	116.93 (12)	H11A—C11—H11B	109.5
C2—C1—C6	120.21 (15)	C10—C11—H11C	109.5
C2—C1—H1A	119.9	H11A—C11—H11C	109.5
C6—C1—H1A	119.9	H11B—C11—H11C	109.5
C3—C2—C1	120.18 (16)	C10—C12—H12A	109.5
C3—C2—H2A	119.9	C10—C12—H12B	109.5
C1—C2—H2A	119.9	H12A—C12—H12B	109.5
C4—C3—C2	119.92 (15)	C10—C12—H12C	109.5
C4—C3—H3A	120.0	H12A—C12—H12C	109.5
C2—C3—H3A	120.0	H12B—C12—H12C	109.5
C3—C4—C5	120.25 (15)	C10—C13—H13A	109.5
C3—C4—H4A	119.9	C10—C13—H13B	109.5
C5—C4—H4A	119.9	H13A—C13—H13B	109.5
C4—C5—C6	120.01 (15)	C10—C13—H13C	109.5
C4—C5—H5A	120.0	H13A—C13—H13C	109.5
C6—C5—H5A	120.0	H13B—C13—H13C	109.5
C1—C6—C5	119.40 (14)	O2—C14—O1	123.37 (14)
C1—C6—C7	119.91 (14)	O2—C14—C8	126.18 (14)
C5—C6—C7	120.65 (14)	O1—C14—C8	110.45 (13)
N2—C7—C8	106.22 (13)	O1—C15—C16	107.43 (13)
N2—C7—C6	125.57 (14)	O1—C15—H15A	110.2
C8—C7—C6	128.21 (14)	C16—C15—H15A	110.2
C7—C8—C9	105.09 (14)	O1—C15—H15B	110.2
C7—C8—C14	127.70 (14)	C16—C15—H15B	110.2
C9—C8—C14	127.19 (14)	H15A—C15—H15B	108.5
N1—C9—C8	111.93 (14)	C15—C16—H16A	109.5
N1—C9—H9A	124.0	C15—C16—H16B	109.5
C8—C9—H9A	124.0	H16A—C16—H16B	109.5
N2—C10—C12	110.47 (13)	C15—C16—H16C	109.5
N2—C10—C11	108.18 (12)	H16A—C16—H16C	109.5
C12—C10—C11	111.78 (13)	H16B—C16—H16C	109.5
N2—C10—C13	108.24 (12)
C9—N1—N2—C7	−1.56 (17)	C6—C7—C8—C9	−179.96 (15)
C9—N1—N2—C10	−175.57 (13)	N2—C7—C8—C14	177.44 (15)
C6—C1—C2—C3	0.9 (2)	C6—C7—C8—C14	−1.8 (3)
C1—C2—C3—C4	0.5 (2)	N2—N1—C9—C8	1.04 (18)
C2—C3—C4—C5	−1.0 (2)	C7—C8—C9—N1	−0.18 (18)
C3—C4—C5—C6	0.1 (2)	C14—C8—C9—N1	−178.40 (15)
C2—C1—C6—C5	−1.8 (2)	C7—N2—C10—C12	44.2 (2)
C2—C1—C6—C7	−179.70 (15)	N1—N2—C10—C12	−143.23 (13)
C4—C5—C6—C1	1.3 (2)	C7—N2—C10—C11	−78.5 (2)
C4—C5—C6—C7	179.20 (14)	N1—N2—C10—C11	94.12 (15)
N1—N2—C7—C8	1.46 (17)	C7—N2—C10—C13	163.07 (15)
C10—N2—C7—C8	174.38 (15)	N1—N2—C10—C13	−24.31 (18)
N1—N2—C7—C6	−179.31 (14)	C15—O1—C14—O2	−4.6 (2)
C10—N2—C7—C6	−6.4 (3)	C15—O1—C14—C8	175.15 (12)
C1—C6—C7—N2	−97.7 (2)	C7—C8—C14—O2	5.7 (3)
C5—C6—C7—N2	84.4 (2)	C9—C8—C14—O2	−176.47 (16)
C1—C6—C7—C8	81.3 (2)	C7—C8—C14—O1	−174.06 (14)
C5—C6—C7—C8	−96.5 (2)	C9—C8—C14—O1	3.8 (2)
N2—C7—C8—C9	−0.76 (17)	C14—O1—C15—C16	173.80 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O2i	0.97	2.53	3.367 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2i	0.97	2.53	3.367 (2)	145

Symmetry code: (i) .