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

In the title compound, C21H23ClN2O, the dihedral angle between the benzene rings is 83.2 (6)°, while the mean plane of the pyrazole ring [r.m.s. deviation = 0.043 (1) Å] makes dihedral angles of 3.4 (3) and 86.2 (1)° with the benzene rings. In the crystal, a pair of weak C-H⋯O inter-actions between the benzene ring and the propan-1-one group link the mol-ecules into an inversion dimer with an R 2 (2)(16) graph-set motif. In addition, a weak π-π stacking inter-action [centroid-centroid distance = 3.959 (4) Å] connects the dimers into a tape running along [201].

Related literature

For the biological activity of pyrazolines, see: Taylor et al. (1992 ▶); Lombardino & Otterness (1977 ▶); Manna et al. (2005 ▶); Samshuddin et al. (2012a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For a related structure, see: Narayana et al., (2014 ▶).

Experimental

Crystal data

C21H23ClN2O

M = 354.86

Triclinic,

a = 6.6042 (3) Å

b = 10.1188 (9) Å

c = 14.4806 (12) Å

α = 98.444 (7)°

β = 90.650 (6)°

γ = 106.542 (6)°

V = 916.13 (12) Å3

Z = 2

Cu Kα radiation

μ = 1.92 mm−1

T = 173 K

0.36 × 0.28 × 0.16 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.583, T max = 0.736

5565 measured reflections

3519 independent reflections

3170 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.05

3519 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO (Agilent, 2012 ▶); 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 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814013075/is5364sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013075/is5364Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013075/is5364Isup3.cml

CCDC reference: 1006823

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

C21H23ClN2O	Z = 2
Mr = 354.86	F(000) = 376
Triclinic, P1	Dx = 1.286 Mg m−3
a = 6.6042 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.1188 (9) Å	Cell parameters from 2712 reflections
c = 14.4806 (12) Å	θ = 4.6–72.1°
α = 98.444 (7)°	µ = 1.92 mm−1
β = 90.650 (6)°	T = 173 K
γ = 106.542 (6)°	Irregular, colourless
V = 916.13 (12) Å3	0.36 × 0.28 × 0.16 mm

Agilent Eos Gemini diffractometer	3519 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 16.0416 pixels mm-1	θmax = 72.2°, θmin = 4.6°
ω scans	h = −6→8
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −12→12
Tmin = 0.583, Tmax = 0.736	l = −14→17
5565 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.2126P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.31 e Å−3
3519 reflections	Δρmin = −0.27 e Å−3
230 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0079 (10)
Primary atom site location: structure-invariant direct methods

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	0.09015 (7)	0.80472 (5)	0.39149 (3)	0.04238 (19)
O1	1.2342 (2)	0.71922 (13)	0.84127 (9)	0.0348 (3)
N1	0.9973 (2)	0.77738 (13)	0.75592 (9)	0.0247 (3)
N2	0.8703 (2)	0.75374 (13)	0.67523 (9)	0.0239 (3)
C1	0.7420 (2)	0.82811 (16)	0.68834 (11)	0.0234 (3)
C2	0.7635 (2)	0.91195 (18)	0.78502 (11)	0.0272 (4)
H2A	0.6352	0.8793	0.8198	0.033*
H2B	0.7900	1.0126	0.7822	0.033*
C3	0.9569 (2)	0.88334 (16)	0.83017 (11)	0.0243 (3)
H3	0.9150	0.8405	0.8876	0.029*
C4	1.1291 (2)	0.69830 (16)	0.76809 (11)	0.0249 (3)
C5	1.1314 (3)	0.58555 (16)	0.68676 (12)	0.0280 (4)
H5A	0.9900	0.5161	0.6769	0.034*
H5B	1.1619	0.6280	0.6292	0.034*
C6	1.2960 (3)	0.51247 (19)	0.70421 (14)	0.0363 (4)
H6A	1.2959	0.4423	0.6498	0.054*
H6B	1.2625	0.4668	0.7596	0.054*
H6C	1.4361	0.5811	0.7145	0.054*
C7	1.1482 (2)	1.00998 (15)	0.85394 (10)	0.0219 (3)
C8	1.2222 (3)	1.10049 (17)	0.78993 (11)	0.0258 (3)
H8	1.1504	1.0837	0.7302	0.031*
C9	1.3995 (3)	1.21478 (17)	0.81238 (11)	0.0271 (3)
H9	1.4486	1.2740	0.7672	0.033*
C10	1.5071 (3)	1.24473 (16)	0.89944 (11)	0.0252 (3)
C11	1.4312 (3)	1.15487 (17)	0.96358 (11)	0.0278 (4)
H11	1.5005	1.1732	1.0239	0.033*
C12	1.2564 (3)	1.03921 (17)	0.94090 (11)	0.0262 (3)
H12	1.2095	0.9787	0.9856	0.031*
C13	1.7049 (3)	1.36693 (17)	0.92541 (12)	0.0297 (4)
H13	1.7213	1.3878	0.9952	0.036*
C14	1.9003 (3)	1.3267 (2)	0.89069 (16)	0.0432 (5)
H14A	1.8869	1.3024	0.8224	0.065*
H14B	1.9124	1.2463	0.9183	0.065*
H14C	2.0270	1.4056	0.9091	0.065*
C15	1.6934 (3)	1.49961 (19)	0.89028 (16)	0.0450 (5)
H15A	1.8187	1.5766	0.9146	0.067*
H15B	1.5659	1.5228	0.9119	0.067*
H15C	1.6884	1.4847	0.8218	0.067*
C16	0.5854 (2)	0.82406 (16)	0.61440 (11)	0.0245 (3)
C17	0.5637 (3)	0.73309 (19)	0.52963 (12)	0.0315 (4)
H17	0.6547	0.6753	0.5189	0.038*
C18	0.4115 (3)	0.7264 (2)	0.46142 (12)	0.0338 (4)
H18	0.3968	0.6641	0.4042	0.041*
C19	0.2804 (3)	0.81191 (18)	0.47760 (12)	0.0301 (4)
C20	0.2989 (3)	0.90336 (18)	0.56024 (12)	0.0294 (4)
H20	0.2088	0.9619	0.5702	0.035*
C21	0.4514 (2)	0.90838 (17)	0.62857 (11)	0.0272 (4)
H21	0.4644	0.9703	0.6858	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.0387 (3)	0.0443 (3)	0.0417 (3)	0.0081 (2)	−0.0167 (2)	0.0083 (2)
O1	0.0367 (7)	0.0342 (7)	0.0332 (7)	0.0118 (5)	−0.0104 (5)	0.0020 (5)
N1	0.0265 (7)	0.0227 (6)	0.0223 (6)	0.0062 (5)	−0.0045 (5)	−0.0024 (5)
N2	0.0236 (7)	0.0228 (6)	0.0230 (6)	0.0046 (5)	−0.0026 (5)	0.0009 (5)
C1	0.0214 (7)	0.0229 (7)	0.0230 (7)	0.0026 (6)	0.0013 (6)	0.0021 (6)
C2	0.0218 (8)	0.0321 (8)	0.0249 (8)	0.0072 (6)	−0.0007 (6)	−0.0033 (6)
C3	0.0251 (8)	0.0242 (7)	0.0219 (7)	0.0063 (6)	0.0014 (6)	−0.0002 (6)
C4	0.0228 (7)	0.0204 (7)	0.0287 (8)	0.0024 (6)	−0.0017 (6)	0.0032 (6)
C5	0.0273 (8)	0.0223 (7)	0.0333 (9)	0.0075 (6)	−0.0015 (6)	0.0004 (6)
C6	0.0329 (9)	0.0277 (8)	0.0497 (11)	0.0117 (7)	0.0013 (8)	0.0043 (7)
C7	0.0226 (7)	0.0218 (7)	0.0209 (7)	0.0079 (6)	0.0004 (6)	−0.0012 (5)
C8	0.0306 (8)	0.0272 (8)	0.0198 (7)	0.0101 (6)	−0.0031 (6)	0.0019 (6)
C9	0.0336 (9)	0.0234 (7)	0.0253 (8)	0.0085 (6)	0.0030 (6)	0.0066 (6)
C10	0.0262 (8)	0.0210 (7)	0.0278 (8)	0.0074 (6)	0.0019 (6)	0.0006 (6)
C11	0.0286 (8)	0.0287 (8)	0.0224 (8)	0.0043 (7)	−0.0036 (6)	0.0010 (6)
C12	0.0291 (8)	0.0271 (8)	0.0206 (7)	0.0051 (6)	0.0009 (6)	0.0040 (6)
C13	0.0317 (9)	0.0237 (8)	0.0287 (8)	0.0022 (7)	0.0000 (7)	0.0005 (6)
C14	0.0292 (9)	0.0395 (10)	0.0530 (12)	0.0027 (8)	−0.0010 (8)	−0.0028 (9)
C15	0.0456 (11)	0.0261 (9)	0.0575 (13)	0.0008 (8)	−0.0035 (9)	0.0079 (8)
C16	0.0213 (7)	0.0266 (8)	0.0234 (8)	0.0037 (6)	−0.0003 (6)	0.0036 (6)
C17	0.0333 (9)	0.0350 (9)	0.0269 (8)	0.0139 (7)	−0.0009 (7)	−0.0013 (7)
C18	0.0358 (9)	0.0380 (9)	0.0260 (8)	0.0115 (7)	−0.0040 (7)	−0.0014 (7)
C19	0.0262 (8)	0.0321 (9)	0.0296 (8)	0.0028 (7)	−0.0047 (6)	0.0085 (7)
C20	0.0251 (8)	0.0291 (8)	0.0351 (9)	0.0089 (6)	0.0004 (7)	0.0067 (7)
C21	0.0244 (8)	0.0268 (8)	0.0284 (8)	0.0056 (6)	0.0014 (6)	0.0012 (6)

Cl1—C19	1.7391 (17)	C9—C10	1.389 (2)
O1—C4	1.218 (2)	C10—C11	1.393 (2)
N1—N2	1.3812 (18)	C10—C13	1.520 (2)
N1—C3	1.4858 (19)	C11—H11	0.9500
N1—C4	1.365 (2)	C11—C12	1.386 (2)
N2—C1	1.282 (2)	C12—H12	0.9500
C1—C2	1.509 (2)	C13—H13	1.0000
C1—C16	1.468 (2)	C13—C14	1.529 (3)
C2—H2A	0.9900	C13—C15	1.525 (2)
C2—H2B	0.9900	C14—H14A	0.9800
C2—C3	1.546 (2)	C14—H14B	0.9800
C3—H3	1.0000	C14—H14C	0.9800
C3—C7	1.515 (2)	C15—H15A	0.9800
C4—C5	1.518 (2)	C15—H15B	0.9800
C5—H5A	0.9900	C15—H15C	0.9800
C5—H5B	0.9900	C16—C17	1.401 (2)
C5—C6	1.516 (2)	C16—C21	1.391 (2)
C6—H6A	0.9800	C17—H17	0.9500
C6—H6B	0.9800	C17—C18	1.382 (2)
C6—H6C	0.9800	C18—H18	0.9500
C7—C8	1.393 (2)	C18—C19	1.388 (3)
C7—C12	1.390 (2)	C19—C20	1.382 (3)
C8—H8	0.9500	C20—H20	0.9500
C8—C9	1.387 (2)	C20—C21	1.389 (2)
C9—H9	0.9500	C21—H21	0.9500
N2—N1—C3	113.63 (12)	C9—C10—C13	122.90 (14)
C4—N1—N2	121.84 (13)	C11—C10—C13	119.59 (15)
C4—N1—C3	124.15 (13)	C10—C11—H11	119.4
C1—N2—N1	108.33 (12)	C12—C11—C10	121.14 (15)
N2—C1—C2	114.20 (14)	C12—C11—H11	119.4
N2—C1—C16	120.84 (14)	C7—C12—H12	119.4
C16—C1—C2	124.92 (14)	C11—C12—C7	121.25 (14)
C1—C2—H2A	111.2	C11—C12—H12	119.4
C1—C2—H2B	111.2	C10—C13—H13	107.4
C1—C2—C3	102.65 (13)	C10—C13—C14	110.30 (14)
H2A—C2—H2B	109.2	C10—C13—C15	113.48 (15)
C3—C2—H2A	111.2	C14—C13—H13	107.4
C3—C2—H2B	111.2	C15—C13—H13	107.4
N1—C3—C2	100.81 (12)	C15—C13—C14	110.46 (16)
N1—C3—H3	109.6	C13—C14—H14A	109.5
N1—C3—C7	112.12 (12)	C13—C14—H14B	109.5
C2—C3—H3	109.6	C13—C14—H14C	109.5
C7—C3—C2	114.82 (13)	H14A—C14—H14B	109.5
C7—C3—H3	109.6	H14A—C14—H14C	109.5
O1—C4—N1	120.11 (15)	H14B—C14—H14C	109.5
O1—C4—C5	123.92 (14)	C13—C15—H15A	109.5
N1—C4—C5	115.96 (14)	C13—C15—H15B	109.5
C4—C5—H5A	109.3	C13—C15—H15C	109.5
C4—C5—H5B	109.3	H15A—C15—H15B	109.5
H5A—C5—H5B	108.0	H15A—C15—H15C	109.5
C6—C5—C4	111.61 (14)	H15B—C15—H15C	109.5
C6—C5—H5A	109.3	C17—C16—C1	120.97 (14)
C6—C5—H5B	109.3	C21—C16—C1	120.24 (14)
C5—C6—H6A	109.5	C21—C16—C17	118.76 (15)
C5—C6—H6B	109.5	C16—C17—H17	119.6
C5—C6—H6C	109.5	C18—C17—C16	120.78 (16)
H6A—C6—H6B	109.5	C18—C17—H17	119.6
H6A—C6—H6C	109.5	C17—C18—H18	120.5
H6B—C6—H6C	109.5	C17—C18—C19	119.09 (16)
C8—C7—C3	121.51 (14)	C19—C18—H18	120.5
C12—C7—C3	120.69 (14)	C18—C19—Cl1	119.18 (14)
C12—C7—C8	117.80 (14)	C20—C19—Cl1	119.38 (14)
C7—C8—H8	119.6	C20—C19—C18	121.45 (16)
C9—C8—C7	120.73 (14)	C19—C20—H20	120.5
C9—C8—H8	119.6	C19—C20—C21	118.94 (15)
C8—C9—H9	119.2	C21—C20—H20	120.5
C8—C9—C10	121.58 (14)	C16—C21—H21	119.5
C10—C9—H9	119.2	C20—C21—C16	120.97 (15)
C9—C10—C11	117.48 (15)	C20—C21—H21	119.5
Cl1—C19—C20—C21	−179.97 (12)	C3—C7—C8—C9	−179.03 (14)
O1—C4—C5—C6	−5.7 (2)	C3—C7—C12—C11	−179.83 (14)
N1—N2—C1—C2	−1.75 (18)	C4—N1—N2—C1	170.50 (14)
N1—N2—C1—C16	−179.56 (13)	C4—N1—C3—C2	−167.46 (14)
N1—C3—C7—C8	66.98 (18)	C4—N1—C3—C7	69.93 (19)
N1—C3—C7—C12	−112.81 (16)	C7—C8—C9—C10	−1.2 (2)
N1—C4—C5—C6	175.14 (14)	C8—C7—C12—C11	0.4 (2)
N2—N1—C3—C2	5.53 (16)	C8—C9—C10—C11	0.5 (2)
N2—N1—C3—C7	−117.09 (14)	C8—C9—C10—C13	178.43 (15)
N2—N1—C4—O1	−177.75 (14)	C9—C10—C11—C12	0.7 (2)
N2—N1—C4—C5	1.4 (2)	C9—C10—C13—C14	−83.6 (2)
N2—C1—C2—C3	5.09 (18)	C9—C10—C13—C15	40.9 (2)
N2—C1—C16—C17	3.7 (2)	C10—C11—C12—C7	−1.1 (3)
N2—C1—C16—C21	−178.10 (14)	C11—C10—C13—C14	94.32 (19)
C1—C2—C3—N1	−5.77 (15)	C11—C10—C13—C15	−141.14 (17)
C1—C2—C3—C7	114.94 (14)	C12—C7—C8—C9	0.8 (2)
C1—C16—C17—C18	177.91 (16)	C13—C10—C11—C12	−177.35 (15)
C1—C16—C21—C20	−178.43 (14)	C16—C1—C2—C3	−177.20 (14)
C2—C1—C16—C17	−173.90 (16)	C16—C17—C18—C19	0.4 (3)
C2—C1—C16—C21	4.3 (2)	C17—C16—C21—C20	−0.1 (2)
C2—C3—C7—C8	−47.29 (19)	C17—C18—C19—Cl1	179.47 (14)
C2—C3—C7—C12	132.92 (15)	C17—C18—C19—C20	0.0 (3)
C3—N1—N2—C1	−2.67 (17)	C18—C19—C20—C21	−0.5 (3)
C3—N1—C4—O1	−5.3 (2)	C19—C20—C21—C16	0.6 (2)
C3—N1—C4—C5	173.88 (13)	C21—C16—C17—C18	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.95	2.51	3.419 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.95	2.51	3.419 (2)	161

Symmetry code: (i) .