1-(4-tert-Butyl-benz-yl)-3-phenyl-1H-pyrazole-5-carboxylic acid.

In the title compound, C(21)H(22)N(2)O(2), the mean plane of the pyrazole ring makes dihedral angles of 18.80 (12) and 77.13 (5)°, respectively, with the mean planes of the phenyl and tert-butyl-benzyl rings. The carboxylate group is inclined at 8.51 (14)° with respect to the pyrazole ring. The crystal structure displays inter-molecular O-H⋯O hydrogen bonding, generating centrosymmetric dimers.

Related literature

For the synthesis and biological activity of related compounds, see: Wei et al. (2006 ▶); Xia et al. (2007b ▶); Zhang et al. (2008 ▶); Zhao et al. (2008 ▶). For related structures, see: Ding et al. (2007 ▶); Tang et al. (2007 ▶); Xia et al. (2007a ▶).

Experimental

Crystal data

C21H22N2O2

M = 334.41

Monoclinic,

a = 12.336 (2) Å

b = 17.632 (3) Å

c = 8.7876 (17) Å

β = 97.910 (3)°

V = 1893.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.16 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.988, T max = 0.992

10007 measured reflections

3552 independent reflections

2644 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.166

S = 1.02

3552 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017000/pv2149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017000/pv2149Isup2.hkl

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

C21H22N2O2	F(000) = 712
Mr = 334.41	Dx = 1.173 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3769 reflections
a = 12.336 (2) Å	θ = 2.3–27.1°
b = 17.632 (3) Å	µ = 0.08 mm−1
c = 8.7876 (17) Å	T = 298 K
β = 97.910 (3)°	Block, colourless
V = 1893.2 (6) Å3	0.16 × 0.13 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3552 independent reflections
Radiation source: fine-focus sealed tube	2644 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→15
Tmin = 0.988, Tmax = 0.992	k = −21→21
10007 measured reflections	l = −10→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.0935P)2 + 0.4012P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3552 reflections	Δρmax = 0.56 e Å−3
231 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (19)

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 > 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	1.06981 (13)	0.07159 (8)	0.39610 (19)	0.0671 (4)
H1	1.0670	0.0259	0.4125	0.101*
O2	0.94281 (12)	0.07589 (8)	0.5566 (2)	0.0633 (4)
N1	0.95215 (12)	0.23985 (8)	0.53903 (17)	0.0443 (4)
N2	0.98423 (12)	0.31199 (8)	0.52234 (17)	0.0467 (4)
C1	1.00463 (15)	0.10731 (11)	0.4774 (2)	0.0512 (5)
C2	1.01498 (14)	0.19024 (10)	0.4691 (2)	0.0469 (4)
C3	1.09088 (14)	0.23321 (11)	0.4044 (2)	0.0489 (4)
H3	1.1445	0.2157	0.3484	0.059*
C4	1.06969 (14)	0.30870 (10)	0.4412 (2)	0.0451 (4)
C5	1.12601 (14)	0.37881 (11)	0.4041 (2)	0.0491 (5)
C6	1.19031 (17)	0.38040 (14)	0.2862 (3)	0.0629 (5)
H6	1.2004	0.3363	0.2318	0.075*
C7	1.2401 (2)	0.44801 (18)	0.2487 (3)	0.0776 (7)
H7	1.2830	0.4484	0.1695	0.093*
C8	1.2262 (2)	0.51358 (16)	0.3277 (4)	0.0820 (8)
H8	1.2583	0.5585	0.3012	0.098*
C9	1.1646 (2)	0.51239 (14)	0.4457 (4)	0.0803 (8)
H9	1.1556	0.5567	0.4999	0.096*
C10	1.11504 (17)	0.44554 (12)	0.4858 (3)	0.0647 (6)
H10	1.0745	0.4455	0.5675	0.078*
C11	0.86035 (15)	0.22509 (11)	0.6259 (2)	0.0488 (4)
H11A	0.8471	0.2703	0.6836	0.059*
H11B	0.8810	0.1847	0.6991	0.059*
C12	0.75498 (14)	0.20293 (10)	0.5253 (2)	0.0439 (4)
C13	0.70381 (16)	0.25233 (12)	0.4155 (2)	0.0563 (5)
H13	0.7353	0.2993	0.4014	0.068*
C14	0.60599 (16)	0.23267 (14)	0.3261 (3)	0.0630 (6)
H14	0.5739	0.2667	0.2525	0.076*
C15	0.55480 (15)	0.16391 (13)	0.3434 (2)	0.0550 (5)
C16	0.60596 (16)	0.11511 (12)	0.4557 (3)	0.0581 (5)
H16	0.5734	0.0688	0.4718	0.070*
C17	0.70455 (15)	0.13405 (11)	0.5443 (2)	0.0525 (5)
H17	0.7371	0.0999	0.6174	0.063*
C18	0.44732 (18)	0.14091 (16)	0.2427 (3)	0.0751 (7)
C19	0.4710 (3)	0.0946 (3)	0.1148 (6)	0.185 (3)
H19A	0.4903	0.0443	0.1506	0.277*
H19B	0.5309	0.1165	0.0709	0.277*
H19C	0.4076	0.0924	0.0383	0.277*
C20	0.3864 (3)	0.2129 (3)	0.1715 (6)	0.151 (2)
H20A	0.4274	0.2350	0.0975	0.227*
H20B	0.3794	0.2490	0.2513	0.227*
H20C	0.3150	0.1988	0.1219	0.227*
C21	0.3666 (3)	0.1096 (3)	0.3438 (5)	0.148 (2)
H21A	0.2932	0.1199	0.2967	0.222*
H21B	0.3792	0.1334	0.4429	0.222*
H21C	0.3767	0.0558	0.3553	0.222*

	U11	U22	U33	U12	U13	U23
O1	0.0727 (10)	0.0507 (8)	0.0822 (11)	0.0079 (7)	0.0261 (8)	0.0001 (7)
O2	0.0514 (8)	0.0513 (8)	0.0893 (11)	0.0027 (6)	0.0172 (8)	0.0011 (7)
N1	0.0354 (7)	0.0495 (8)	0.0459 (8)	−0.0024 (6)	−0.0012 (6)	−0.0039 (6)
N2	0.0380 (8)	0.0489 (8)	0.0510 (9)	−0.0027 (6)	−0.0009 (6)	−0.0040 (6)
C1	0.0404 (10)	0.0509 (10)	0.0596 (11)	0.0039 (8)	−0.0021 (8)	−0.0019 (8)
C2	0.0369 (9)	0.0495 (10)	0.0517 (10)	0.0034 (7)	−0.0025 (8)	−0.0008 (8)
C3	0.0362 (9)	0.0543 (11)	0.0551 (11)	0.0057 (7)	0.0024 (8)	0.0004 (8)
C4	0.0322 (8)	0.0537 (10)	0.0466 (9)	0.0018 (7)	−0.0045 (7)	0.0006 (7)
C5	0.0321 (9)	0.0558 (10)	0.0563 (11)	0.0025 (7)	−0.0055 (8)	0.0072 (8)
C6	0.0485 (11)	0.0788 (14)	0.0604 (12)	−0.0038 (10)	0.0045 (9)	0.0025 (10)
C7	0.0564 (13)	0.102 (2)	0.0754 (16)	−0.0117 (12)	0.0110 (11)	0.0205 (14)
C8	0.0559 (14)	0.0742 (17)	0.114 (2)	−0.0116 (11)	0.0055 (14)	0.0295 (15)
C9	0.0598 (14)	0.0591 (13)	0.123 (2)	−0.0048 (10)	0.0163 (14)	0.0034 (13)
C10	0.0493 (11)	0.0559 (12)	0.0906 (16)	−0.0013 (9)	0.0159 (11)	−0.0021 (11)
C11	0.0436 (10)	0.0590 (11)	0.0434 (9)	−0.0048 (8)	0.0043 (8)	−0.0049 (8)
C12	0.0363 (9)	0.0530 (10)	0.0430 (9)	−0.0008 (7)	0.0076 (7)	−0.0061 (7)
C13	0.0421 (10)	0.0633 (12)	0.0634 (12)	−0.0089 (8)	0.0069 (9)	0.0134 (9)
C14	0.0412 (10)	0.0838 (15)	0.0624 (13)	−0.0037 (9)	0.0016 (9)	0.0231 (11)
C15	0.0344 (9)	0.0760 (13)	0.0546 (11)	−0.0022 (8)	0.0062 (8)	−0.0029 (9)
C16	0.0435 (10)	0.0521 (11)	0.0772 (14)	−0.0076 (8)	0.0029 (9)	−0.0051 (9)
C17	0.0455 (10)	0.0488 (10)	0.0611 (12)	0.0011 (8)	−0.0004 (9)	0.0014 (8)
C18	0.0397 (11)	0.1038 (19)	0.0782 (16)	−0.0116 (11)	−0.0042 (10)	−0.0058 (13)
C19	0.072 (2)	0.270 (7)	0.196 (5)	0.018 (3)	−0.036 (3)	−0.159 (5)
C20	0.077 (2)	0.157 (4)	0.195 (5)	0.009 (2)	−0.067 (3)	−0.013 (3)
C21	0.0644 (19)	0.220 (5)	0.151 (4)	−0.052 (3)	−0.013 (2)	0.029 (3)

O1—C1	1.308 (2)	C11—H11B	0.9700
O1—H1	0.8200	C12—C17	1.385 (3)
O2—C1	1.233 (3)	C12—C13	1.385 (3)
N1—N2	1.346 (2)	C13—C14	1.390 (3)
N1—C2	1.369 (2)	C13—H13	0.9300
N1—C11	1.473 (2)	C14—C15	1.385 (3)
N2—C4	1.352 (2)	C14—H14	0.9300
C1—C2	1.470 (3)	C15—C16	1.393 (3)
C2—C3	1.386 (3)	C15—C18	1.544 (3)
C3—C4	1.403 (3)	C16—C17	1.391 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.477 (3)	C17—H17	0.9300
C5—C6	1.389 (3)	C18—C19	1.451 (5)
C5—C10	1.395 (3)	C18—C21	1.525 (5)
C6—C7	1.401 (4)	C18—C20	1.561 (5)
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.372 (4)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—C9	1.367 (4)	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C10	1.395 (3)	C20—H20C	0.9600
C9—H9	0.9300	C21—H21A	0.9600
C10—H10	0.9300	C21—H21B	0.9600
C11—C12	1.519 (2)	C21—H21C	0.9600
C11—H11A	0.9700
C1—O1—H1	109.5	C17—C12—C11	121.19 (16)
N2—N1—C2	111.20 (15)	C13—C12—C11	120.99 (17)
N2—N1—C11	118.80 (15)	C12—C13—C14	120.89 (18)
C2—N1—C11	129.99 (16)	C12—C13—H13	119.6
N1—N2—C4	106.21 (14)	C14—C13—H13	119.6
O2—C1—O1	124.52 (19)	C15—C14—C13	122.00 (19)
O2—C1—C2	122.64 (18)	C15—C14—H14	119.0
O1—C1—C2	112.81 (18)	C13—C14—H14	119.0
N1—C2—C3	106.92 (16)	C14—C15—C16	116.70 (17)
N1—C2—C1	123.70 (17)	C14—C15—C18	122.4 (2)
C3—C2—C1	129.20 (17)	C16—C15—C18	120.9 (2)
C2—C3—C4	105.44 (17)	C17—C16—C15	121.59 (19)
C2—C3—H3	127.3	C17—C16—H16	119.2
C4—C3—H3	127.3	C15—C16—H16	119.2
N2—C4—C3	110.23 (16)	C12—C17—C16	121.04 (18)
N2—C4—C5	120.35 (16)	C12—C17—H17	119.5
C3—C4—C5	129.42 (18)	C16—C17—H17	119.5
C6—C5—C10	118.23 (19)	C19—C18—C21	117.7 (4)
C6—C5—C4	121.08 (19)	C19—C18—C15	110.1 (2)
C10—C5—C4	120.68 (18)	C21—C18—C15	109.8 (2)
C5—C6—C7	120.4 (2)	C19—C18—C20	106.5 (4)
C5—C6—H6	119.8	C21—C18—C20	102.2 (3)
C7—C6—H6	119.8	C15—C18—C20	110.2 (2)
C8—C7—C6	120.6 (2)	C18—C19—H19A	109.5
C8—C7—H7	119.7	C18—C19—H19B	109.5
C6—C7—H7	119.7	H19A—C19—H19B	109.5
C9—C8—C7	119.5 (2)	C18—C19—H19C	109.5
C9—C8—H8	120.2	H19A—C19—H19C	109.5
C7—C8—H8	120.2	H19B—C19—H19C	109.5
C8—C9—C10	120.9 (3)	C18—C20—H20A	109.5
C8—C9—H9	119.6	C18—C20—H20B	109.5
C10—C9—H9	119.6	H20A—C20—H20B	109.5
C5—C10—C9	120.4 (2)	C18—C20—H20C	109.5
C5—C10—H10	119.8	H20A—C20—H20C	109.5
C9—C10—H10	119.8	H20B—C20—H20C	109.5
N1—C11—C12	113.64 (14)	C18—C21—H21A	109.5
N1—C11—H11A	108.8	C18—C21—H21B	109.5
C12—C11—H11A	108.8	H21A—C21—H21B	109.5
N1—C11—H11B	108.8	C18—C21—H21C	109.5
C12—C11—H11B	108.8	H21A—C21—H21C	109.5
H11A—C11—H11B	107.7	H21B—C21—H21C	109.5
C17—C12—C13	117.77 (16)
C2—N1—N2—C4	−0.45 (18)	C7—C8—C9—C10	−0.6 (4)
C11—N1—N2—C4	179.05 (14)	C6—C5—C10—C9	2.2 (3)
N2—N1—C2—C3	−0.09 (19)	C4—C5—C10—C9	−177.19 (19)
C11—N1—C2—C3	−179.51 (16)	C8—C9—C10—C5	−1.1 (4)
N2—N1—C2—C1	175.41 (15)	N2—N1—C11—C12	106.44 (18)
C11—N1—C2—C1	−4.0 (3)	C2—N1—C11—C12	−74.2 (2)
O2—C1—C2—N1	−4.8 (3)	N1—C11—C12—C17	120.67 (19)
O1—C1—C2—N1	177.14 (16)	N1—C11—C12—C13	−62.0 (2)
O2—C1—C2—C3	169.67 (19)	C17—C12—C13—C14	−1.0 (3)
O1—C1—C2—C3	−8.4 (3)	C11—C12—C13—C14	−178.41 (19)
N1—C2—C3—C4	0.56 (19)	C12—C13—C14—C15	0.8 (3)
C1—C2—C3—C4	−174.60 (17)	C13—C14—C15—C16	0.3 (3)
N1—N2—C4—C3	0.81 (19)	C13—C14—C15—C18	−178.8 (2)
N1—N2—C4—C5	−179.17 (14)	C14—C15—C16—C17	−1.0 (3)
C2—C3—C4—N2	−0.87 (19)	C18—C15—C16—C17	178.0 (2)
C2—C3—C4—C5	179.11 (16)	C13—C12—C17—C16	0.2 (3)
N2—C4—C5—C6	−160.76 (17)	C11—C12—C17—C16	177.62 (18)
C3—C4—C5—C6	19.3 (3)	C15—C16—C17—C12	0.8 (3)
N2—C4—C5—C10	18.6 (3)	C14—C15—C18—C19	95.8 (4)
C3—C4—C5—C10	−161.36 (19)	C16—C15—C18—C19	−83.2 (4)
C10—C5—C6—C7	−1.7 (3)	C14—C15—C18—C21	−133.1 (3)
C4—C5—C6—C7	177.74 (18)	C16—C15—C18—C21	47.9 (4)
C5—C6—C7—C8	0.0 (4)	C14—C15—C18—C20	−21.3 (4)
C6—C7—C8—C9	1.1 (4)	C16—C15—C18—C20	159.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.82	2.641 (2)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.82	2.641 (2)	178

Symmetry code: (i) .