Ethyl 1-cyclo-hexyl-5-(4-meth-oxy-phen-yl)-1H-pyrazole-4-carboxyl-ate.

In the title compound, C(19)H(24)N(2)O(3), the benzene ring forms a dihedral angle of 65.34 (7)° with the pyrazole ring. The cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are linked into a inversion dimers by pairs of C-H⋯O hydrogen bonds, generating R(2) (2)(22) ring motifs.

Related literature

For general background to pyrazole derivatives, see: Dhanya et al. (2009 ▶); Hall et al. (2008 ▶); Isloor et al. (2000 ▶, 2009 ▶); Ragavan et al. (2010 ▶); Premsai Rai et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2010a ▶,b ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H24N2O3

M = 328.40

Triclinic,

a = 6.8959 (7) Å

b = 11.0858 (7) Å

c = 12.0142 (12) Å

α = 100.690 (2)°

β = 93.107 (1)°

γ = 95.354 (1)°

V = 896.16 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.31 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.988

18767 measured reflections

5159 independent reflections

3928 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.164

S = 1.05

5159 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.23 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/S1600536811049282/is5014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049282/is5014Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049282/is5014Isup3.cml

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

C19H24N2O3	Z = 2
Mr = 328.40	F(000) = 352
Triclinic, P1	Dx = 1.217 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8959 (7) Å	Cell parameters from 6690 reflections
b = 11.0858 (7) Å	θ = 2.8–30.0°
c = 12.0142 (12) Å	µ = 0.08 mm−1
α = 100.690 (2)°	T = 296 K
β = 93.107 (1)°	Needle, colourless
γ = 95.354 (1)°	0.40 × 0.31 × 0.15 mm
V = 896.16 (14) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	5159 independent reflections
Radiation source: fine-focus sealed tube	3928 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.968, Tmax = 0.988	k = −15→15
18767 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0889P)2 + 0.118P] where P = (Fo2 + 2Fc2)/3
5159 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.24481 (16)	0.40833 (10)	0.42125 (10)	0.0637 (3)
O2	−0.1292 (2)	0.87054 (11)	0.39497 (11)	0.0756 (4)
O3	−0.17512 (15)	1.04017 (9)	0.32770 (9)	0.0579 (3)
N1	0.20159 (16)	0.93769 (11)	0.08374 (10)	0.0500 (3)
N2	0.24537 (14)	0.83382 (9)	0.12036 (9)	0.0416 (2)
C1	0.15217 (15)	0.81617 (10)	0.21339 (9)	0.0366 (2)
C2	0.04032 (16)	0.91465 (11)	0.23818 (10)	0.0387 (2)
C3	0.07815 (18)	0.98587 (12)	0.15498 (12)	0.0462 (3)
H3A	0.0227	1.0583	0.1507	0.055*
C4	0.37555 (16)	0.75420 (12)	0.05627 (10)	0.0424 (3)
H4A	0.3759	0.6789	0.0880	0.051*
C5	0.3032 (2)	0.71696 (17)	−0.06831 (13)	0.0634 (4)
H5A	0.2978	0.7901	−0.1014	0.076*
H5B	0.1724	0.6744	−0.0750	0.076*
C6	0.4396 (2)	0.63269 (18)	−0.13218 (14)	0.0705 (5)
H6A	0.4338	0.5560	−0.1041	0.085*
H6B	0.3960	0.6133	−0.2122	0.085*
C7	0.6475 (2)	0.69171 (17)	−0.11840 (13)	0.0630 (4)
H7A	0.7311	0.6333	−0.1555	0.076*
H7B	0.6564	0.7628	−0.1550	0.076*
C8	0.7178 (2)	0.73191 (17)	0.00499 (13)	0.0624 (4)
H8A	0.8481	0.7750	0.0109	0.075*
H8B	0.7248	0.6597	0.0393	0.075*
C9	0.58264 (18)	0.81614 (15)	0.06897 (13)	0.0562 (4)
H9A	0.6275	0.8367	0.1488	0.067*
H9B	0.5857	0.8922	0.0398	0.067*
C10	0.17434 (16)	0.70935 (10)	0.26810 (10)	0.0371 (2)
C11	0.35203 (17)	0.69279 (12)	0.32133 (11)	0.0438 (3)
H11A	0.4596	0.7504	0.3226	0.053*
C12	0.37068 (19)	0.59210 (12)	0.37225 (11)	0.0481 (3)
H12A	0.4899	0.5828	0.4080	0.058*
C13	0.21233 (19)	0.50493 (11)	0.37021 (10)	0.0438 (3)
C14	0.03437 (19)	0.52023 (12)	0.31811 (12)	0.0475 (3)
H14A	−0.0729	0.4624	0.3168	0.057*
C15	0.01701 (17)	0.62194 (12)	0.26809 (11)	0.0463 (3)
H15A	−0.1030	0.6318	0.2337	0.056*
C16	0.0922 (3)	0.31069 (15)	0.41146 (16)	0.0671 (4)
H16A	0.1307	0.2515	0.4552	0.101*
H16B	0.0667	0.2713	0.3332	0.101*
H16C	−0.0238	0.3433	0.4394	0.101*
C17	−0.09192 (17)	0.93662 (11)	0.32911 (10)	0.0424 (3)
C18	−0.3166 (3)	1.06986 (18)	0.41045 (15)	0.0714 (5)
H18A	−0.3792	0.9945	0.4285	0.086*
H18B	−0.2514	1.1194	0.4798	0.086*
C19	−0.4606 (3)	1.1369 (3)	0.3653 (2)	0.1087 (9)
H19A	−0.5482	1.1625	0.4225	0.163*
H19B	−0.5330	1.0848	0.3008	0.163*
H19C	−0.3971	1.2082	0.3425	0.163*

	U11	U22	U33	U12	U13	U23
O1	0.0735 (7)	0.0545 (6)	0.0701 (7)	0.0126 (5)	−0.0038 (5)	0.0302 (5)
O2	0.1033 (9)	0.0716 (7)	0.0721 (7)	0.0383 (6)	0.0486 (7)	0.0396 (6)
O3	0.0665 (6)	0.0570 (6)	0.0602 (6)	0.0274 (5)	0.0281 (5)	0.0204 (5)
N1	0.0516 (6)	0.0506 (6)	0.0567 (7)	0.0129 (5)	0.0173 (5)	0.0252 (5)
N2	0.0395 (5)	0.0447 (5)	0.0454 (5)	0.0100 (4)	0.0123 (4)	0.0157 (4)
C1	0.0346 (5)	0.0399 (5)	0.0369 (5)	0.0044 (4)	0.0046 (4)	0.0108 (4)
C2	0.0374 (5)	0.0404 (5)	0.0406 (6)	0.0067 (4)	0.0065 (4)	0.0114 (4)
C3	0.0460 (6)	0.0441 (6)	0.0541 (7)	0.0108 (5)	0.0121 (5)	0.0186 (5)
C4	0.0385 (5)	0.0477 (6)	0.0432 (6)	0.0088 (4)	0.0110 (4)	0.0103 (5)
C5	0.0411 (6)	0.0889 (11)	0.0523 (8)	0.0073 (7)	−0.0009 (6)	−0.0055 (7)
C6	0.0559 (8)	0.0873 (12)	0.0561 (9)	0.0050 (8)	0.0041 (7)	−0.0169 (8)
C7	0.0519 (7)	0.0856 (11)	0.0487 (8)	0.0122 (7)	0.0155 (6)	0.0000 (7)
C8	0.0382 (6)	0.0885 (11)	0.0556 (8)	0.0132 (6)	0.0064 (5)	−0.0025 (7)
C9	0.0371 (6)	0.0732 (9)	0.0508 (7)	0.0023 (6)	0.0061 (5)	−0.0066 (7)
C10	0.0382 (5)	0.0387 (5)	0.0358 (5)	0.0079 (4)	0.0045 (4)	0.0086 (4)
C11	0.0398 (5)	0.0452 (6)	0.0463 (6)	0.0042 (4)	−0.0009 (5)	0.0098 (5)
C12	0.0456 (6)	0.0515 (7)	0.0485 (7)	0.0114 (5)	−0.0056 (5)	0.0127 (5)
C13	0.0548 (7)	0.0409 (6)	0.0384 (6)	0.0121 (5)	0.0034 (5)	0.0110 (5)
C14	0.0466 (6)	0.0438 (6)	0.0536 (7)	0.0008 (5)	0.0007 (5)	0.0159 (5)
C15	0.0391 (5)	0.0485 (6)	0.0536 (7)	0.0045 (5)	−0.0016 (5)	0.0171 (6)
C16	0.0854 (11)	0.0509 (8)	0.0738 (10)	0.0118 (7)	0.0184 (8)	0.0292 (7)
C17	0.0428 (5)	0.0434 (6)	0.0428 (6)	0.0089 (4)	0.0073 (5)	0.0098 (5)
C18	0.0777 (10)	0.0834 (11)	0.0647 (10)	0.0400 (9)	0.0340 (8)	0.0200 (8)
C19	0.0807 (13)	0.167 (2)	0.0849 (15)	0.0658 (15)	0.0120 (11)	0.0140 (15)

O1—C13	1.3590 (15)	C7—H7B	0.9700
O1—C16	1.421 (2)	C8—C9	1.5183 (19)
O2—C17	1.1962 (16)	C8—H8A	0.9700
O3—C17	1.3328 (15)	C8—H8B	0.9700
O3—C18	1.4463 (17)	C9—H9A	0.9700
N1—C3	1.3178 (16)	C9—H9B	0.9700
N1—N2	1.3598 (14)	C10—C15	1.3856 (16)
N2—C1	1.3551 (14)	C10—C11	1.3945 (16)
N2—C4	1.4657 (15)	C11—C12	1.3814 (17)
C1—C2	1.3917 (15)	C11—H11A	0.9300
C1—C10	1.4729 (15)	C12—C13	1.3849 (18)
C2—C3	1.4048 (16)	C12—H12A	0.9300
C2—C17	1.4611 (16)	C13—C14	1.3862 (18)
C3—H3A	0.9300	C14—C15	1.3840 (17)
C4—C9	1.5128 (17)	C14—H14A	0.9300
C4—C5	1.520 (2)	C15—H15A	0.9300
C4—H4A	0.9800	C16—H16A	0.9600
C5—C6	1.524 (2)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600
C5—H5B	0.9700	C18—C19	1.436 (3)
C6—C7	1.507 (2)	C18—H18A	0.9700
C6—H6A	0.9700	C18—H18B	0.9700
C6—H6B	0.9700	C19—H19A	0.9600
C7—C8	1.506 (2)	C19—H19B	0.9600
C7—H7A	0.9700	C19—H19C	0.9600
C13—O1—C16	117.95 (11)	C4—C9—C8	110.74 (12)
C17—O3—C18	116.56 (11)	C4—C9—H9A	109.5
C3—N1—N2	104.76 (10)	C8—C9—H9A	109.5
C1—N2—N1	112.70 (9)	C4—C9—H9B	109.5
C1—N2—C4	128.17 (10)	C8—C9—H9B	109.5
N1—N2—C4	119.08 (10)	H9A—C9—H9B	108.1
N2—C1—C2	105.63 (10)	C15—C10—C11	117.99 (10)
N2—C1—C10	122.86 (10)	C15—C10—C1	120.39 (10)
C2—C1—C10	131.51 (10)	C11—C10—C1	121.63 (10)
C1—C2—C3	105.00 (10)	C12—C11—C10	120.98 (11)
C1—C2—C17	127.24 (10)	C12—C11—H11A	119.5
C3—C2—C17	127.73 (11)	C10—C11—H11A	119.5
N1—C3—C2	111.91 (11)	C11—C12—C13	120.19 (11)
N1—C3—H3A	124.0	C11—C12—H12A	119.9
C2—C3—H3A	124.0	C13—C12—H12A	119.9
N2—C4—C9	110.98 (10)	O1—C13—C12	116.10 (11)
N2—C4—C5	111.32 (10)	O1—C13—C14	124.31 (12)
C9—C4—C5	110.76 (11)	C12—C13—C14	119.60 (11)
N2—C4—H4A	107.9	C15—C14—C13	119.71 (11)
C9—C4—H4A	107.9	C15—C14—H14A	120.1
C5—C4—H4A	107.9	C13—C14—H14A	120.1
C4—C5—C6	110.07 (12)	C14—C15—C10	121.53 (11)
C4—C5—H5A	109.6	C14—C15—H15A	119.2
C6—C5—H5A	109.6	C10—C15—H15A	119.2
C4—C5—H5B	109.6	O1—C16—H16A	109.5
C6—C5—H5B	109.6	O1—C16—H16B	109.5
H5A—C5—H5B	108.2	H16A—C16—H16B	109.5
C7—C6—C5	111.75 (14)	O1—C16—H16C	109.5
C7—C6—H6A	109.3	H16A—C16—H16C	109.5
C5—C6—H6A	109.3	H16B—C16—H16C	109.5
C7—C6—H6B	109.3	O2—C17—O3	122.85 (12)
C5—C6—H6B	109.3	O2—C17—C2	126.16 (12)
H6A—C6—H6B	107.9	O3—C17—C2	110.95 (10)
C8—C7—C6	111.45 (13)	C19—C18—O3	109.52 (15)
C8—C7—H7A	109.3	C19—C18—H18A	109.8
C6—C7—H7A	109.3	O3—C18—H18A	109.8
C8—C7—H7B	109.3	C19—C18—H18B	109.8
C6—C7—H7B	109.3	O3—C18—H18B	109.8
H7A—C7—H7B	108.0	H18A—C18—H18B	108.2
C7—C8—C9	111.41 (13)	C18—C19—H19A	109.5
C7—C8—H8A	109.3	C18—C19—H19B	109.5
C9—C8—H8A	109.3	H19A—C19—H19B	109.5
C7—C8—H8B	109.3	C18—C19—H19C	109.5
C9—C8—H8B	109.3	H19A—C19—H19C	109.5
H8A—C8—H8B	108.0	H19B—C19—H19C	109.5
C3—N1—N2—C1	−0.18 (14)	C7—C8—C9—C4	56.03 (19)
C3—N1—N2—C4	177.65 (11)	N2—C1—C10—C15	−114.31 (13)
N1—N2—C1—C2	0.28 (13)	C2—C1—C10—C15	64.46 (18)
C4—N2—C1—C2	−177.31 (11)	N2—C1—C10—C11	65.81 (16)
N1—N2—C1—C10	179.32 (10)	C2—C1—C10—C11	−115.41 (14)
C4—N2—C1—C10	1.74 (18)	C15—C10—C11—C12	0.16 (19)
N2—C1—C2—C3	−0.25 (13)	C1—C10—C11—C12	−179.97 (11)
C10—C1—C2—C3	−179.18 (12)	C10—C11—C12—C13	0.6 (2)
N2—C1—C2—C17	178.12 (11)	C16—O1—C13—C12	−173.91 (13)
C10—C1—C2—C17	−0.8 (2)	C16—O1—C13—C14	6.2 (2)
N2—N1—C3—C2	0.01 (15)	C11—C12—C13—O1	179.25 (12)
C1—C2—C3—N1	0.15 (15)	C11—C12—C13—C14	−0.9 (2)
C17—C2—C3—N1	−178.20 (12)	O1—C13—C14—C15	−179.74 (12)
C1—N2—C4—C9	−112.62 (14)	C12—C13—C14—C15	0.4 (2)
N1—N2—C4—C9	69.93 (15)	C13—C14—C15—C10	0.4 (2)
C1—N2—C4—C5	123.52 (14)	C11—C10—C15—C14	−0.64 (19)
N1—N2—C4—C5	−53.94 (15)	C1—C10—C15—C14	179.49 (11)
N2—C4—C5—C6	−179.09 (13)	C18—O3—C17—O2	−0.4 (2)
C9—C4—C5—C6	56.92 (18)	C18—O3—C17—C2	177.29 (13)
C4—C5—C6—C7	−55.8 (2)	C1—C2—C17—O2	−2.4 (2)
C5—C6—C7—C8	54.9 (2)	C3—C2—C17—O2	175.59 (15)
C6—C7—C8—C9	−54.7 (2)	C1—C2—C17—O3	−179.98 (11)
N2—C4—C9—C8	178.50 (12)	C3—C2—C17—O3	−1.97 (19)
C5—C4—C9—C8	−57.32 (17)	C17—O3—C18—C19	−149.67 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2i	0.96	2.44	3.358 (2)	159.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2i	0.96	2.44	3.358 (2)	159

Symmetry code: (i) .