1-Cyclo-hexyl-5-(4-meth-oxy-phen-yl)-1H-pyrazole-4-carb-oxy-lic acid.

In the title compound, C(17)H(20)N(2)O(3), the meth-oxy-phenyl unit is disordered over two sets of sites in a 0.715 (4):0.285 (4) ratio. The pyrazole ring forms dihedral angles of 55.88 (16) and 72.6 (4)° with the benzene rings of its major and minor components, respectively. The cyclo-hexane ring adopts a chair conformation and its C-N bond is in an equatorial orientation. In the crystal, mol-ecules are linked into inversion dimers by pairs of O-H⋯O hydrogen bonds, generating R(2) (2)(8) loops.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures and medicinal background to pyrazole derivatives, 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

C17H20N2O3

M = 300.35

Monoclinic,

a = 12.0722 (9) Å

b = 12.7180 (9) Å

c = 11.7739 (8) Å

β = 118.698 (1)°

V = 1585.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.39 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.987

24474 measured reflections

4585 independent reflections

2766 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.159

S = 1.03

4585 reflections

239 parameters

17 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.28 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/S1600536811050872/hb6534sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050872/hb6534Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050872/hb6534Isup3.cml

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

C17H20N2O3	F(000) = 640
Mr = 300.35	Dx = 1.258 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5000 reflections
a = 12.0722 (9) Å	θ = 2.5–29.8°
b = 12.7180 (9) Å	µ = 0.09 mm−1
c = 11.7739 (8) Å	T = 296 K
β = 118.698 (1)°	Needle, colourless
V = 1585.6 (2) Å3	0.39 × 0.20 × 0.15 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 29.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.967, Tmax = 0.987	k = −17→17
24474 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.3536P] where P = (Fo2 + 2Fc2)/3
4585 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.21 e Å−3
17 restraints	Δρmin = −0.28 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	Occ. (<1)
O1	0.07405 (12)	0.45236 (14)	0.92263 (12)	0.0870 (5)
O2	0.15254 (12)	0.47797 (13)	1.13352 (11)	0.0814 (5)
H1O2	0.0749	0.4999	1.1195	0.122*
O3A	0.1055 (2)	0.39532 (19)	0.44671 (17)	0.0769 (8)	0.715 (4)
C4A	0.2726 (5)	0.3627 (5)	0.8457 (5)	0.0409 (10)	0.715 (4)
C5A	0.1549 (3)	0.3174 (3)	0.7674 (3)	0.0528 (7)	0.715 (4)
H5AA	0.1137	0.2823	0.8057	0.063*	0.715 (4)
C6A	0.0978 (4)	0.3237 (3)	0.6330 (3)	0.0573 (9)	0.715 (4)
H6AA	0.0206	0.2909	0.5820	0.069*	0.715 (4)
C7A	0.1563 (3)	0.3787 (3)	0.5760 (2)	0.0489 (6)	0.715 (4)
C8A	0.2749 (3)	0.4202 (2)	0.6523 (3)	0.0523 (7)	0.715 (4)
H8AA	0.3168	0.4540	0.6139	0.063*	0.715 (4)
C9A	0.3314 (3)	0.4121 (2)	0.7843 (3)	0.0453 (6)	0.715 (4)
H9AA	0.4115	0.4405	0.8341	0.054*	0.715 (4)
C17A	−0.0253 (3)	0.3757 (3)	0.3667 (3)	0.0861 (11)	0.715 (4)
H17A	−0.0504	0.3991	0.2802	0.129*	0.715 (4)
H17B	−0.0727	0.4129	0.3999	0.129*	0.715 (4)
H17C	−0.0413	0.3016	0.3657	0.129*	0.715 (4)
O3B	0.0427 (5)	0.3332 (4)	0.4351 (5)	0.0707 (18)*	0.285 (4)
C4B	0.2589 (16)	0.3476 (14)	0.8323 (13)	0.043 (3)*	0.285 (4)
C5B	0.1646 (8)	0.2768 (6)	0.7716 (8)	0.051 (2)*	0.285 (4)
H5B	0.1475	0.2291	0.8211	0.061*	0.285 (4)
C6	0.0940 (9)	0.2735 (8)	0.6402 (9)	0.059 (2)	0.285 (4)
H6B	0.0277	0.2259	0.6006	0.070*	0.285 (4)
C7B	0.1219 (7)	0.3407 (6)	0.5680 (7)	0.0456 (18)*	0.285 (4)
C8B	0.2195 (9)	0.4113 (7)	0.6240 (8)	0.060 (2)*	0.285 (4)
H8B	0.2389	0.4551	0.5727	0.072*	0.285 (4)
C9B	0.2888 (8)	0.4168 (8)	0.7578 (9)	0.062 (3)*	0.285 (4)
H9B	0.3539	0.4654	0.7976	0.074*	0.285 (4)
C17B	0.0494 (10)	0.4149 (7)	0.3569 (10)	0.092 (3)*	0.285 (4)
H17D	−0.0130	0.4034	0.2684	0.138*	0.285 (4)
H17E	0.1319	0.4157	0.3637	0.138*	0.285 (4)
H17F	0.0338	0.4812	0.3857	0.138*	0.285 (4)
N1	0.44673 (12)	0.32694 (11)	1.06351 (12)	0.0524 (3)
N2	0.48284 (13)	0.34101 (14)	1.19163 (13)	0.0676 (4)
C1	0.38353 (16)	0.38444 (16)	1.19118 (16)	0.0650 (5)
H1A	0.3804	0.4035	1.2658	0.078*
C2	0.28347 (14)	0.39865 (14)	1.06610 (15)	0.0525 (4)
C3	0.32756 (13)	0.36065 (13)	0.98426 (14)	0.0460 (3)
C10	0.53239 (13)	0.27005 (13)	1.02944 (15)	0.0482 (4)
H10A	0.4887	0.2600	0.9354	0.058*
C11	0.56252 (17)	0.16218 (14)	1.09219 (18)	0.0602 (4)
H11A	0.4849	0.1227	1.0639	0.072*
H11B	0.6021	0.1698	1.1855	0.072*
C12	0.65043 (16)	0.10250 (14)	1.05635 (18)	0.0620 (5)
H12A	0.6723	0.0355	1.1013	0.074*
H12B	0.6072	0.0884	0.9640	0.074*
C13	0.76923 (16)	0.16370 (16)	1.0912 (2)	0.0734 (6)
H13A	0.8210	0.1254	1.0628	0.088*
H13B	0.8171	0.1715	1.1845	0.088*
C14	0.73834 (17)	0.27110 (16)	1.0285 (2)	0.0730 (6)
H14A	0.6976	0.2632	0.9351	0.088*
H14B	0.8159	0.3103	1.0555	0.088*
C15	0.65178 (16)	0.33218 (14)	1.0652 (2)	0.0622 (5)
H15A	0.6952	0.3460	1.1575	0.075*
H15B	0.6302	0.3992	1.0203	0.075*
C16	0.16128 (15)	0.44458 (16)	1.03370 (16)	0.0589 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0572 (7)	0.1573 (15)	0.0477 (7)	0.0425 (8)	0.0262 (6)	0.0055 (8)
O2	0.0613 (7)	0.1362 (13)	0.0527 (7)	0.0334 (8)	0.0323 (6)	−0.0050 (7)
O3A	0.0761 (14)	0.1104 (18)	0.0383 (10)	0.0057 (13)	0.0227 (9)	0.0049 (10)
C4A	0.0356 (19)	0.051 (2)	0.0423 (17)	0.0014 (13)	0.0234 (14)	−0.0032 (16)
C5A	0.0468 (14)	0.068 (2)	0.0531 (15)	−0.0086 (15)	0.0315 (12)	−0.0019 (14)
C6A	0.0447 (14)	0.077 (2)	0.0497 (16)	−0.0107 (18)	0.0226 (12)	−0.0097 (17)
C7A	0.0523 (16)	0.0575 (17)	0.0399 (13)	0.0057 (14)	0.0246 (12)	0.0014 (12)
C8A	0.0507 (16)	0.0666 (16)	0.0485 (14)	0.0042 (13)	0.0308 (13)	0.0101 (11)
C9A	0.0399 (14)	0.0515 (14)	0.0479 (14)	0.0012 (12)	0.0237 (12)	0.0039 (10)
C17A	0.0647 (18)	0.121 (3)	0.0512 (16)	0.0264 (19)	0.0110 (14)	−0.0099 (16)
C6	0.047 (4)	0.073 (6)	0.059 (4)	−0.013 (4)	0.027 (3)	−0.003 (4)
N1	0.0429 (7)	0.0684 (9)	0.0456 (7)	0.0084 (6)	0.0212 (6)	−0.0078 (6)
N2	0.0543 (8)	0.0971 (12)	0.0453 (8)	0.0182 (8)	0.0190 (6)	−0.0117 (7)
C1	0.0571 (10)	0.0919 (14)	0.0469 (9)	0.0174 (9)	0.0257 (8)	−0.0064 (9)
C2	0.0466 (8)	0.0704 (10)	0.0457 (8)	0.0107 (7)	0.0261 (7)	0.0011 (7)
C3	0.0401 (7)	0.0557 (9)	0.0461 (8)	0.0029 (6)	0.0238 (6)	0.0001 (6)
C10	0.0380 (7)	0.0575 (9)	0.0505 (8)	0.0035 (6)	0.0224 (6)	−0.0086 (7)
C11	0.0566 (9)	0.0603 (10)	0.0690 (11)	0.0006 (8)	0.0344 (9)	−0.0028 (8)
C12	0.0566 (10)	0.0564 (10)	0.0689 (11)	0.0086 (8)	0.0268 (9)	−0.0059 (8)
C13	0.0450 (9)	0.0802 (13)	0.0877 (14)	0.0097 (9)	0.0259 (9)	−0.0166 (11)
C14	0.0508 (9)	0.0802 (13)	0.1005 (15)	−0.0074 (9)	0.0463 (10)	−0.0130 (11)
C15	0.0515 (9)	0.0560 (10)	0.0826 (13)	−0.0032 (7)	0.0351 (9)	−0.0106 (9)
C16	0.0501 (9)	0.0872 (13)	0.0474 (9)	0.0161 (8)	0.0297 (8)	0.0036 (8)

O1—C16	1.227 (2)	C8B—H8B	0.9300
O2—C16	1.3007 (19)	C9B—H9B	0.9300
O2—H1O2	0.9133	C17B—H17D	0.9600
O3A—C7A	1.357 (3)	C17B—H17E	0.9600
O3A—C17A	1.419 (4)	C17B—H17F	0.9600
C4A—C9A	1.384 (4)	N1—C3	1.3546 (19)
C4A—C5A	1.394 (5)	N1—N2	1.3660 (18)
C4A—C3	1.436 (5)	N1—C10	1.4671 (18)
C5A—C6A	1.393 (4)	N2—C1	1.318 (2)
C5A—H5AA	0.9300	C1—C2	1.397 (2)
C6A—C7A	1.376 (4)	C1—H1A	0.9300
C6A—H6AA	0.9300	C2—C3	1.392 (2)
C7A—C8A	1.379 (4)	C2—C16	1.457 (2)
C8A—C9A	1.368 (4)	C10—C15	1.515 (2)
C8A—H8AA	0.9300	C10—C11	1.517 (2)
C9A—H9AA	0.9300	C10—H10A	0.9800
C17A—H17A	0.9600	C11—C12	1.520 (2)
C17A—H17B	0.9600	C11—H11A	0.9700
C17A—H17C	0.9600	C11—H11B	0.9700
O3B—C7B	1.391 (8)	C12—C13	1.505 (3)
O3B—C17B	1.416 (10)	C12—H12A	0.9700
C4B—C5B	1.355 (12)	C12—H12B	0.9700
C4B—C9B	1.407 (13)	C13—C14	1.512 (3)
C4B—C3	1.578 (14)	C13—H13A	0.9700
C5B—C6	1.363 (10)	C13—H13B	0.9700
C5B—H5B	0.9300	C14—C15	1.521 (2)
C6—C7B	1.358 (10)	C14—H14A	0.9700
C6—H6B	0.9300	C14—H14B	0.9700
C7B—C8B	1.373 (9)	C15—H15A	0.9700
C8B—C9B	1.386 (10)	C15—H15B	0.9700
C16—O2—H1O2	117.2	N2—C1—H1A	123.7
C7A—O3A—C17A	118.5 (3)	C2—C1—H1A	123.7
C9A—C4A—C5A	117.3 (4)	C3—C2—C1	105.08 (14)
C9A—C4A—C3	121.9 (4)	C3—C2—C16	129.32 (15)
C5A—C4A—C3	120.8 (3)	C1—C2—C16	125.60 (15)
C6A—C5A—C4A	121.2 (3)	N1—C3—C2	105.40 (13)
C6A—C5A—H5AA	119.4	N1—C3—C4A	123.2 (3)
C4A—C5A—H5AA	119.4	C2—C3—C4A	131.2 (3)
C7A—C6A—C5A	119.6 (3)	N1—C3—C4B	123.6 (8)
C7A—C6A—H6AA	120.2	C2—C3—C4B	130.8 (8)
C5A—C6A—H6AA	120.2	N1—C10—C15	111.61 (13)
O3A—C7A—C6A	124.4 (3)	N1—C10—C11	110.39 (13)
O3A—C7A—C8A	116.1 (3)	C15—C10—C11	111.26 (13)
C6A—C7A—C8A	119.5 (2)	N1—C10—H10A	107.8
C9A—C8A—C7A	120.4 (2)	C15—C10—H10A	107.8
C9A—C8A—H8AA	119.8	C11—C10—H10A	107.8
C7A—C8A—H8AA	119.8	C10—C11—C12	110.64 (15)
C8A—C9A—C4A	121.8 (3)	C10—C11—H11A	109.5
C8A—C9A—H9AA	119.1	C12—C11—H11A	109.5
C4A—C9A—H9AA	119.1	C10—C11—H11B	109.5
C7B—O3B—C17B	117.3 (7)	C12—C11—H11B	109.5
C5B—C4B—C9B	119.3 (11)	H11A—C11—H11B	108.1
C5B—C4B—C3	121.2 (9)	C13—C12—C11	111.52 (15)
C9B—C4B—C3	119.3 (9)	C13—C12—H12A	109.3
C4B—C5B—C6	121.9 (9)	C11—C12—H12A	109.3
C4B—C5B—H5B	119.0	C13—C12—H12B	109.3
C6—C5B—H5B	119.0	C11—C12—H12B	109.3
C7B—C6—C5B	118.9 (8)	H12A—C12—H12B	108.0
C7B—C6—H6B	120.5	C12—C13—C14	110.78 (15)
C5B—C6—H6B	120.5	C12—C13—H13A	109.5
C6—C7B—C8B	121.7 (7)	C14—C13—H13A	109.5
C6—C7B—O3B	114.7 (7)	C12—C13—H13B	109.5
C8B—C7B—O3B	123.6 (7)	C14—C13—H13B	109.5
C7B—C8B—C9B	119.3 (8)	H13A—C13—H13B	108.1
C7B—C8B—H8B	120.3	C13—C14—C15	111.37 (17)
C9B—C8B—H8B	120.3	C13—C14—H14A	109.4
C8B—C9B—C4B	118.8 (9)	C15—C14—H14A	109.4
C8B—C9B—H9B	120.6	C13—C14—H14B	109.4
C4B—C9B—H9B	120.6	C15—C14—H14B	109.4
O3B—C17B—H17D	109.5	H14A—C14—H14B	108.0
O3B—C17B—H17E	109.5	C10—C15—C14	110.26 (14)
H17D—C17B—H17E	109.5	C10—C15—H15A	109.6
O3B—C17B—H17F	109.5	C14—C15—H15A	109.6
H17D—C17B—H17F	109.5	C10—C15—H15B	109.6
H17E—C17B—H17F	109.5	C14—C15—H15B	109.6
C3—N1—N2	112.92 (12)	H15A—C15—H15B	108.1
C3—N1—C10	128.51 (13)	O1—C16—O2	122.41 (15)
N2—N1—C10	118.26 (12)	O1—C16—C2	123.66 (15)
C1—N2—N1	104.07 (13)	O2—C16—C2	113.93 (14)
N2—C1—C2	112.52 (15)
C9A—C4A—C5A—C6A	−1.4 (8)	C1—C2—C3—N1	0.32 (19)
C3—C4A—C5A—C6A	176.6 (4)	C16—C2—C3—N1	179.92 (18)
C4A—C5A—C6A—C7A	−2.3 (6)	C1—C2—C3—C4A	−173.6 (3)
C17A—O3A—C7A—C6A	14.3 (4)	C16—C2—C3—C4A	6.0 (4)
C17A—O3A—C7A—C8A	−166.1 (3)	C1—C2—C3—C4B	175.8 (7)
C5A—C6A—C7A—O3A	−175.6 (3)	C16—C2—C3—C4B	−4.6 (7)
C5A—C6A—C7A—C8A	4.8 (5)	C9A—C4A—C3—N1	−53.1 (7)
O3A—C7A—C8A—C9A	176.7 (2)	C5A—C4A—C3—N1	129.0 (5)
C6A—C7A—C8A—C9A	−3.6 (4)	C9A—C4A—C3—C2	119.9 (5)
C7A—C8A—C9A—C4A	−0.1 (5)	C5A—C4A—C3—C2	−58.0 (7)
C5A—C4A—C9A—C8A	2.6 (7)	C9A—C4A—C3—C4B	−149 (8)
C3—C4A—C9A—C8A	−175.4 (4)	C5A—C4A—C3—C4B	33 (7)
C9B—C4B—C5B—C6	−3(2)	C5B—C4B—C3—N1	107.3 (15)
C3—C4B—C5B—C6	171.7 (11)	C9B—C4B—C3—N1	−78.2 (17)
C4B—C5B—C6—C7B	2.3 (17)	C5B—C4B—C3—C2	−67.5 (19)
C5B—C6—C7B—C8B	0.3 (14)	C9B—C4B—C3—C2	107.0 (14)
C5B—C6—C7B—O3B	−178.5 (8)	C5B—C4B—C3—C4A	−163 (9)
C17B—O3B—C7B—C6	166.9 (8)	C9B—C4B—C3—C4A	11 (6)
C17B—O3B—C7B—C8B	−11.8 (12)	C3—N1—C10—C15	118.83 (18)
C6—C7B—C8B—C9B	−2.2 (14)	N2—N1—C10—C15	−68.1 (2)
O3B—C7B—C8B—C9B	176.4 (7)	C3—N1—C10—C11	−116.88 (18)
C7B—C8B—C9B—C4B	1.6 (16)	N2—N1—C10—C11	56.22 (19)
C5B—C4B—C9B—C8B	1(2)	N1—C10—C11—C12	179.54 (13)
C3—C4B—C9B—C8B	−173.8 (11)	C15—C10—C11—C12	−55.96 (19)
C3—N1—N2—C1	0.0 (2)	C10—C11—C12—C13	55.8 (2)
C10—N1—N2—C1	−174.16 (16)	C11—C12—C13—C14	−56.0 (2)
N1—N2—C1—C2	0.2 (2)	C12—C13—C14—C15	56.4 (2)
N2—C1—C2—C3	−0.4 (2)	N1—C10—C15—C14	−179.95 (15)
N2—C1—C2—C16	−179.98 (19)	C11—C10—C15—C14	56.3 (2)
N2—N1—C3—C2	−0.20 (19)	C13—C14—C15—C10	−56.4 (2)
C10—N1—C3—C2	173.21 (16)	C3—C2—C16—O1	3.2 (3)
N2—N1—C3—C4A	174.3 (3)	C1—C2—C16—O1	−177.3 (2)
C10—N1—C3—C4A	−12.2 (4)	C3—C2—C16—O2	−176.26 (18)
N2—N1—C3—C4B	−176.1 (6)	C1—C2—C16—O2	3.3 (3)
C10—N1—C3—C4B	−2.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1i	0.91	1.73	2.640 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1i	0.91	1.73	2.640 (2)	174

Symmetry code: (i) .