1-{3-(4-Chloro-phen-yl)-5-[4-(propan-2-yl)phen-yl]-4,5-di-hydro-1H-pyrazol-1-yl}butan-1-one.

In the title compound, C22H25ClN2O, the pyrazole ring exhibits an envelope conformation with the methine C atom as the flap. The benzene rings are twisted by 3.3 (5) and 84.6 (5)° from the pyrazole mean plane, and are inclined to each other by 81.4 (4)°. In the crystal, pairs of weak C-H⋯O hydrogen bonds form centrosymmetric dimers with an R 2 (2)(16) graph-set motif. C-H⋯π inter-actions link the dimers into columns propagating in [100].

Related literature

For the biological activity of pyrazolines, see: Samshuddin et al. (2012a ▶,b ▶). For related structures, see: Baktır et al. (2011 ▶); Jasinski et al. (2010 ▶); Fun et al. (2012a ▶,b ▶); Samshuddin et al. (2010 ▶, 2012c ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For a related structure, see: Narayana et al., (2014 ▶).

Experimental

Crystal data

C22H25ClN2O

M = 368.89

Triclinic,

a = 6.8148 (6) Å

b = 11.1115 (9) Å

c = 13.8239 (15) Å

α = 70.935 (9)°

β = 81.420 (8)°

γ = 75.829 (7)°

V = 956.52 (17) Å3

Z = 2

Cu Kα radiation

μ = 1.86 mm−1

T = 173 K

0.48 × 0.24 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.777, T max = 1.000

6121 measured reflections

3624 independent reflections

3104 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.134

S = 1.03

3624 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814013063/cv5461sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013063/cv5461Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013063/cv5461Isup3.cml

CCDC reference: 1006822

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H25ClN2O	Z = 2
Mr = 368.89	F(000) = 392
Triclinic, P1	Dx = 1.281 Mg m−3
a = 6.8148 (6) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.1115 (9) Å	Cell parameters from 2535 reflections
c = 13.8239 (15) Å	θ = 4.6–71.4°
α = 70.935 (9)°	µ = 1.86 mm−1
β = 81.420 (8)°	T = 173 K
γ = 75.829 (7)°	Prism, colourless
V = 956.52 (17) Å3	0.48 × 0.24 × 0.12 mm

Agilent Eos Gemini diffractometer	3624 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.0416 pixels mm-1	θmax = 71.3°, θmin = 3.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −13→10
Tmin = 0.777, Tmax = 1.000	l = −16→16
6121 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0787P)2 + 0.1856P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3624 reflections	Δρmax = 0.36 e Å−3
238 parameters	Δρmin = −0.29 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
Cl1	1.42326 (7)	0.34338 (5)	0.49295 (4)	0.04081 (18)
O1	0.25099 (19)	0.72366 (12)	0.02504 (10)	0.0295 (3)
N1	0.4990 (2)	0.67625 (14)	0.12995 (11)	0.0225 (3)
N2	0.6268 (2)	0.58597 (14)	0.20187 (11)	0.0213 (3)
C1	0.3613 (2)	0.64081 (16)	0.08821 (13)	0.0216 (3)
C2	0.5284 (3)	0.81112 (16)	0.10752 (13)	0.0229 (4)
H2	0.5346	0.8553	0.0318	0.027*
C3	0.7387 (3)	0.78265 (17)	0.14768 (13)	0.0249 (4)
H3A	0.8467	0.7902	0.0909	0.030*
H3B	0.7440	0.8420	0.1868	0.030*
C4	0.7574 (2)	0.64368 (16)	0.21642 (13)	0.0214 (3)
C5	0.9147 (2)	0.57270 (17)	0.28833 (12)	0.0218 (3)
C6	0.9295 (3)	0.43990 (18)	0.33925 (15)	0.0297 (4)
H6	0.8325	0.3970	0.3298	0.036*
C7	1.0828 (3)	0.37023 (19)	0.40300 (15)	0.0337 (4)
H7	1.0922	0.2799	0.4370	0.040*
C8	1.2233 (3)	0.43392 (19)	0.41678 (13)	0.0276 (4)
C9	1.2096 (3)	0.56538 (19)	0.37002 (14)	0.0285 (4)
H9	1.3048	0.6081	0.3816	0.034*
C10	1.0544 (3)	0.63514 (18)	0.30554 (14)	0.0258 (4)
H10	1.0437	0.7259	0.2731	0.031*
C11	0.3582 (3)	0.88801 (16)	0.16102 (13)	0.0221 (3)
C12	0.3619 (3)	0.88196 (18)	0.26294 (14)	0.0285 (4)
H12	0.4768	0.8312	0.2994	0.034*
C13	0.2016 (3)	0.94830 (18)	0.31206 (14)	0.0306 (4)
H13	0.2081	0.9421	0.3817	0.037*
C14	0.0295 (3)	1.02465 (17)	0.26082 (14)	0.0259 (4)
C15	0.0259 (3)	1.03183 (16)	0.15890 (14)	0.0254 (4)
H15	−0.0885	1.0833	0.1222	0.030*
C16	0.1878 (3)	0.96452 (16)	0.10962 (13)	0.0237 (4)
H16	0.1820	0.9709	0.0398	0.028*
C17	−0.1436 (3)	1.09614 (19)	0.31842 (15)	0.0314 (4)
H17	−0.0822	1.1473	0.3488	0.038*
C18	−0.3049 (4)	1.1923 (3)	0.25140 (19)	0.0543 (7)
H18A	−0.2410	1.2535	0.1947	0.081*
H18B	−0.4025	1.2404	0.2924	0.081*
H18C	−0.3755	1.1453	0.2237	0.081*
C19	−0.2392 (4)	1.0005 (3)	0.40755 (19)	0.0535 (6)
H19A	−0.2975	0.9461	0.3812	0.080*
H19B	−0.3464	1.0487	0.4447	0.080*
H19C	−0.1352	0.9450	0.4542	0.080*
C20	0.3585 (2)	0.49736 (16)	0.12252 (13)	0.0222 (4)
H20A	0.3351	0.4671	0.1982	0.027*
H20B	0.4928	0.4484	0.1035	0.027*
C21	0.1959 (3)	0.46751 (17)	0.07518 (13)	0.0245 (4)
H21A	0.2187	0.4978	−0.0005	0.029*
H21B	0.0612	0.5156	0.0945	0.029*
C22	0.1971 (3)	0.3223 (2)	0.11055 (16)	0.0347 (4)
H22A	0.0947	0.3061	0.0762	0.052*
H22B	0.1660	0.2932	0.1850	0.052*
H22C	0.3314	0.2742	0.0931	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0383 (3)	0.0454 (3)	0.0359 (3)	−0.0011 (2)	−0.0233 (2)	−0.0053 (2)
O1	0.0329 (7)	0.0260 (6)	0.0298 (7)	−0.0028 (5)	−0.0177 (5)	−0.0045 (5)
N1	0.0239 (7)	0.0197 (7)	0.0240 (7)	−0.0018 (6)	−0.0114 (6)	−0.0046 (6)
N2	0.0219 (7)	0.0210 (7)	0.0206 (7)	−0.0006 (5)	−0.0085 (5)	−0.0055 (5)
C1	0.0216 (8)	0.0246 (9)	0.0204 (8)	−0.0033 (6)	−0.0054 (6)	−0.0086 (6)
C2	0.0263 (8)	0.0212 (8)	0.0216 (8)	−0.0063 (7)	−0.0085 (6)	−0.0032 (6)
C3	0.0231 (8)	0.0243 (9)	0.0276 (9)	−0.0054 (7)	−0.0070 (7)	−0.0058 (7)
C4	0.0203 (8)	0.0237 (8)	0.0211 (8)	−0.0036 (6)	−0.0035 (6)	−0.0082 (6)
C5	0.0201 (8)	0.0269 (9)	0.0192 (8)	−0.0026 (6)	−0.0046 (6)	−0.0084 (7)
C6	0.0297 (9)	0.0288 (9)	0.0325 (10)	−0.0099 (7)	−0.0110 (7)	−0.0054 (8)
C7	0.0385 (10)	0.0272 (10)	0.0329 (10)	−0.0058 (8)	−0.0148 (8)	−0.0012 (8)
C8	0.0260 (9)	0.0373 (10)	0.0187 (8)	−0.0017 (7)	−0.0096 (7)	−0.0077 (7)
C9	0.0262 (9)	0.0375 (10)	0.0265 (9)	−0.0091 (7)	−0.0086 (7)	−0.0113 (8)
C10	0.0278 (9)	0.0257 (9)	0.0262 (9)	−0.0056 (7)	−0.0071 (7)	−0.0086 (7)
C11	0.0251 (8)	0.0171 (8)	0.0242 (8)	−0.0050 (6)	−0.0075 (6)	−0.0035 (6)
C12	0.0322 (9)	0.0251 (9)	0.0261 (9)	0.0016 (7)	−0.0163 (7)	−0.0042 (7)
C13	0.0390 (10)	0.0309 (10)	0.0228 (9)	−0.0016 (8)	−0.0118 (7)	−0.0092 (7)
C14	0.0318 (9)	0.0199 (8)	0.0258 (9)	−0.0051 (7)	−0.0058 (7)	−0.0055 (7)
C15	0.0271 (9)	0.0199 (8)	0.0281 (9)	−0.0027 (6)	−0.0116 (7)	−0.0033 (7)
C16	0.0309 (9)	0.0214 (8)	0.0193 (8)	−0.0058 (7)	−0.0098 (7)	−0.0030 (6)
C17	0.0348 (10)	0.0280 (9)	0.0312 (10)	−0.0023 (8)	−0.0064 (8)	−0.0101 (8)
C18	0.0466 (13)	0.0582 (15)	0.0393 (12)	0.0204 (11)	−0.0043 (10)	−0.0122 (11)
C19	0.0593 (15)	0.0477 (14)	0.0426 (13)	−0.0076 (11)	0.0094 (11)	−0.0075 (11)
C20	0.0224 (8)	0.0237 (9)	0.0221 (8)	−0.0034 (6)	−0.0069 (6)	−0.0078 (7)
C21	0.0241 (8)	0.0279 (9)	0.0251 (9)	−0.0063 (7)	−0.0055 (7)	−0.0108 (7)
C22	0.0393 (11)	0.0331 (10)	0.0386 (11)	−0.0137 (8)	−0.0063 (8)	−0.0141 (8)

Cl1—C8	1.7443 (17)	C12—C13	1.382 (3)
O1—C1	1.228 (2)	C13—H13	0.9500
N1—N2	1.3903 (18)	C13—C14	1.402 (2)
N1—C1	1.363 (2)	C14—C15	1.388 (2)
N1—C2	1.486 (2)	C14—C17	1.527 (2)
N2—C4	1.289 (2)	C15—H15	0.9500
C1—C20	1.511 (2)	C15—C16	1.395 (3)
C2—H2	1.0000	C16—H16	0.9500
C2—C3	1.537 (2)	C17—H17	1.0000
C2—C11	1.515 (2)	C17—C18	1.513 (3)
C3—H3A	0.9900	C17—C19	1.522 (3)
C3—H3B	0.9900	C18—H18A	0.9800
C3—C4	1.512 (2)	C18—H18B	0.9800
C4—C5	1.467 (2)	C18—H18C	0.9800
C5—C6	1.397 (3)	C19—H19A	0.9800
C5—C10	1.394 (2)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800
C6—C7	1.378 (3)	C20—H20A	0.9900
C7—H7	0.9500	C20—H20B	0.9900
C7—C8	1.388 (3)	C20—C21	1.518 (2)
C8—C9	1.376 (3)	C21—H21A	0.9900
C9—H9	0.9500	C21—H21B	0.9900
C9—C10	1.394 (2)	C21—C22	1.524 (3)
C10—H10	0.9500	C22—H22A	0.9800
C11—C12	1.392 (2)	C22—H22B	0.9800
C11—C16	1.394 (2)	C22—H22C	0.9800
C12—H12	0.9500
N2—N1—C2	112.45 (13)	C12—C13—C14	121.12 (17)
C1—N1—N2	121.93 (14)	C14—C13—H13	119.4
C1—N1—C2	125.61 (14)	C13—C14—C17	119.15 (16)
C4—N2—N1	107.90 (14)	C15—C14—C13	117.76 (16)
O1—C1—N1	119.87 (16)	C15—C14—C17	123.09 (16)
O1—C1—C20	123.77 (15)	C14—C15—H15	119.5
N1—C1—C20	116.35 (14)	C14—C15—C16	120.95 (16)
N1—C2—H2	110.2	C16—C15—H15	119.5
N1—C2—C3	100.23 (13)	C11—C16—C15	121.13 (16)
N1—C2—C11	110.45 (14)	C11—C16—H16	119.4
C3—C2—H2	110.2	C15—C16—H16	119.4
C11—C2—H2	110.2	C14—C17—H17	106.8
C11—C2—C3	115.22 (14)	C18—C17—C14	114.41 (17)
C2—C3—H3A	111.4	C18—C17—H17	106.8
C2—C3—H3B	111.4	C18—C17—C19	110.51 (19)
H3A—C3—H3B	109.2	C19—C17—C14	111.04 (16)
C4—C3—C2	101.99 (13)	C19—C17—H17	106.8
C4—C3—H3A	111.4	C17—C18—H18A	109.5
C4—C3—H3B	111.4	C17—C18—H18B	109.5
N2—C4—C3	113.43 (14)	C17—C18—H18C	109.5
N2—C4—C5	120.71 (15)	H18A—C18—H18B	109.5
C5—C4—C3	125.71 (15)	H18A—C18—H18C	109.5
C6—C5—C4	120.24 (15)	H18B—C18—H18C	109.5
C10—C5—C4	120.94 (16)	C17—C19—H19A	109.5
C10—C5—C6	118.80 (16)	C17—C19—H19B	109.5
C5—C6—H6	119.5	C17—C19—H19C	109.5
C7—C6—C5	120.99 (17)	H19A—C19—H19B	109.5
C7—C6—H6	119.5	H19A—C19—H19C	109.5
C6—C7—H7	120.5	H19B—C19—H19C	109.5
C6—C7—C8	119.10 (17)	C1—C20—H20A	109.0
C8—C7—H7	120.5	C1—C20—H20B	109.0
C7—C8—Cl1	118.71 (15)	C1—C20—C21	112.72 (14)
C9—C8—Cl1	119.96 (14)	H20A—C20—H20B	107.8
C9—C8—C7	121.32 (16)	C21—C20—H20A	109.0
C8—C9—H9	120.4	C21—C20—H20B	109.0
C8—C9—C10	119.24 (17)	C20—C21—H21A	109.3
C10—C9—H9	120.4	C20—C21—H21B	109.3
C5—C10—H10	119.8	C20—C21—C22	111.64 (15)
C9—C10—C5	120.49 (17)	H21A—C21—H21B	108.0
C9—C10—H10	119.8	C22—C21—H21A	109.3
C12—C11—C2	121.95 (15)	C22—C21—H21B	109.3
C12—C11—C16	117.72 (16)	C21—C22—H22A	109.5
C16—C11—C2	120.30 (15)	C21—C22—H22B	109.5
C11—C12—H12	119.3	C21—C22—H22C	109.5
C13—C12—C11	121.31 (16)	H22A—C22—H22B	109.5
C13—C12—H12	119.3	H22A—C22—H22C	109.5
C12—C13—H13	119.4	H22B—C22—H22C	109.5
Cl1—C8—C9—C10	177.00 (14)	C3—C2—C11—C16	153.55 (15)
O1—C1—C20—C21	−3.4 (2)	C3—C4—C5—C6	−172.73 (17)
N1—N2—C4—C3	−3.92 (19)	C3—C4—C5—C10	5.9 (3)
N1—N2—C4—C5	−179.60 (13)	C4—C5—C6—C7	176.61 (17)
N1—C1—C20—C21	177.93 (14)	C4—C5—C10—C9	−176.72 (15)
N1—C2—C3—C4	−18.43 (16)	C5—C6—C7—C8	0.3 (3)
N1—C2—C11—C12	84.01 (19)	C6—C5—C10—C9	1.9 (3)
N1—C2—C11—C16	−93.79 (18)	C6—C7—C8—Cl1	−177.13 (15)
N2—N1—C1—O1	179.87 (15)	C6—C7—C8—C9	1.5 (3)
N2—N1—C1—C20	−1.4 (2)	C7—C8—C9—C10	−1.6 (3)
N2—N1—C2—C3	18.47 (17)	C8—C9—C10—C5	−0.1 (3)
N2—N1—C2—C11	−103.49 (15)	C10—C5—C6—C7	−2.0 (3)
N2—C4—C5—C6	2.4 (2)	C11—C2—C3—C4	100.09 (16)
N2—C4—C5—C10	−179.00 (15)	C11—C12—C13—C14	−0.3 (3)
C1—N1—N2—C4	171.21 (15)	C12—C11—C16—C15	−0.5 (2)
C1—N1—C2—C3	−162.79 (16)	C12—C13—C14—C15	−0.3 (3)
C1—N1—C2—C11	75.2 (2)	C12—C13—C14—C17	−179.98 (18)
C1—C20—C21—C22	179.69 (15)	C13—C14—C15—C16	0.4 (3)
C2—N1—N2—C4	−10.00 (19)	C13—C14—C17—C18	170.5 (2)
C2—N1—C1—O1	1.3 (3)	C13—C14—C17—C19	−63.6 (2)
C2—N1—C1—C20	180.00 (15)	C14—C15—C16—C11	0.0 (3)
C2—C3—C4—N2	15.17 (19)	C15—C14—C17—C18	−9.2 (3)
C2—C3—C4—C5	−169.40 (15)	C15—C14—C17—C19	116.7 (2)
C2—C11—C12—C13	−177.21 (17)	C16—C11—C12—C13	0.6 (3)
C2—C11—C16—C15	177.37 (15)	C17—C14—C15—C16	−179.92 (16)
C3—C2—C11—C12	−28.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.95	2.57	3.437 (2)	151
C20—H20A···Cgii	0.99	2.67	3.5079 (19)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.95	2.57	3.437 (2)	151
C20—H20A⋯Cg ii	0.99	2.67	3.5079 (19)	143

Symmetry codes: (i) ; (ii) .