1-(4-Isopropyl-phen-yl)-5-(4-methoxy-phen-yl)pyrazolidin-3-one.

In the mol-ecule of the title compound, C(19)H(22)N(2)O(2), the pyrazolidinone ring has an envelope conformation, with the C atom attached to the 4-methoxy-phenyl ring displaced by 0.354 (3) Å from the plane of the other ring atoms. The 4-iso-propyl-phenyl ring is oriented with respect to the 4-meth-oxy-phenyl ring at a dihedral angle of 88.94 (3)°. Intra-molecular C-H⋯N hydrogen bonds result in the formation of two planar five-membered rings, which are oriented with respect to the adjacent 4-isopropyl-phenyl and 4-meth-oxy-phenyl rings at dihedral angles of 4.05 (3) and 0.50 (3)°, respectively. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background, see: Menozzi et al. (1990 ▶); Brooks et al. (1990 ▶); Greenwood et al. (1995 ▶).

Experimental

Crystal data

C19H22N2O2

M = 310.39

Monoclinic,

a = 14.737 (3) Å

b = 7.1490 (14) Å

c = 17.493 (4) Å

β = 112.03 (3)°

V = 1708.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 294 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.969, T max = 0.984

3472 measured reflections

3340 independent reflections

1835 reflections with I > 2σ(I)

R int = 0.052

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.163

S = 1.06

3340 reflections

202 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.78 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009823/hk2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009823/hk2451Isup2.hkl

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

C19H22N2O2	F000 = 664
Mr = 310.39	Dx = 1.207 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.737 (3) Å	θ = 9–13º
b = 7.1490 (14) Å	µ = 0.08 mm−1
c = 17.493 (4) Å	T = 294 (2) K
β = 112.03 (3)º	Block, colorless
V = 1708.4 (7) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.052
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.6º
T = 294(2) K	h = −18→16
ω/2θ scans	k = 0→8
Absorption correction: ψ scan(North et al., 1968)	l = 0→21
Tmin = 0.969, Tmax = 0.984	3 standard reflections
3472 measured reflections	every 120 min
3340 independent reflections	intensity decay: none
1835 reflections with I > 2σ(I)

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)] = 0.078	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.008P)2 + 3.2P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3340 reflections	Δρmax = 0.38 e Å−3
202 parameters	Δρmin = −0.78 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.52570 (18)	0.7545 (4)	1.04046 (16)	0.0569 (7)
N1	0.2835 (2)	0.9106 (4)	0.97974 (18)	0.0486 (8)
N2	0.3849 (2)	0.9266 (4)	0.99532 (18)	0.0508 (8)
H2A	0.4104	1.0278	0.9859	0.061*
C1	0.0956 (5)	1.2768 (9)	1.2266 (4)	0.117 (2)
H1A	0.0772	1.3608	1.2611	0.176*
H1B	0.1383	1.1821	1.2601	0.176*
H1C	0.0380	1.2191	1.1876	0.176*
O2	0.0840 (2)	0.3384 (4)	0.67816 (16)	0.0656 (8)
C2	0.0897 (4)	1.5470 (7)	1.1350 (3)	0.091
H2B	0.0705	1.6238	1.1714	0.136*
H2C	0.0323	1.5035	1.0906	0.136*
H2D	0.1294	1.6189	1.1131	0.136*
C3	0.1471 (4)	1.3827 (7)	1.1817 (3)	0.0881 (16)
H3A	0.2057	1.4352	1.2244	0.106*
C4	0.1840 (3)	1.2577 (6)	1.1290 (3)	0.0657 (11)
C5	0.1216 (3)	1.1481 (7)	1.0656 (3)	0.0792 (14)
H5A	0.0549	1.1507	1.0548	0.095*
C6	0.1557 (3)	1.0349 (6)	1.0180 (3)	0.0684 (12)
H6A	0.1116	0.9649	0.9754	0.082*
C7	0.2539 (3)	1.0251 (5)	1.0332 (2)	0.0467 (9)
C8	0.3165 (3)	1.1359 (5)	1.0951 (2)	0.0538 (10)
H8A	0.3831	1.1348	1.1053	0.065*
C9	0.2817 (3)	1.2487 (6)	1.1424 (3)	0.0626 (11)
H9A	0.3257	1.3203	1.1843	0.075*
C10	0.2671 (3)	0.7054 (5)	0.9853 (2)	0.0485 (9)
H10A	0.2251	0.6878	1.0169	0.058*
C11	0.3691 (3)	0.6265 (5)	1.0361 (2)	0.0522 (10)
H11A	0.3780	0.6123	1.0936	0.063*
H11B	0.3792	0.5064	1.0147	0.063*
C12	0.4378 (3)	0.7731 (5)	1.0257 (2)	0.0473 (9)
C13	0.2185 (3)	0.6143 (5)	0.9026 (2)	0.0489 (9)
C14	0.1919 (3)	0.7046 (6)	0.8282 (2)	0.0556 (10)
H14A	0.2044	0.8320	0.8274	0.067*
C15	0.1471 (3)	0.6114 (6)	0.7545 (2)	0.0583 (11)
H15A	0.1289	0.6768	0.7050	0.070*
C16	0.1289 (3)	0.4205 (6)	0.7537 (2)	0.0544 (10)
C17	0.1560 (3)	0.3291 (6)	0.8282 (2)	0.0691 (12)
H17A	0.1439	0.2017	0.8292	0.083*
C18	0.2002 (3)	0.4224 (5)	0.9003 (2)	0.0636 (12)
H18A	0.2188	0.3565	0.9497	0.076*
C19	0.0726 (3)	0.1427 (6)	0.6765 (3)	0.0721 (13)
H19A	0.0399	0.1019	0.6206	0.108*
H19B	0.0344	0.1084	0.7083	0.108*
H19C	0.1358	0.0845	0.6996	0.108*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (16)	0.0490 (16)	0.0681 (17)	0.0004 (13)	0.0174 (13)	0.0023 (13)
N1	0.0495 (18)	0.0428 (17)	0.0569 (19)	−0.0016 (15)	0.0238 (15)	0.0036 (15)
N2	0.0493 (18)	0.0411 (17)	0.068 (2)	−0.0024 (15)	0.0287 (16)	0.0015 (16)
C1	0.158 (6)	0.112 (5)	0.131 (5)	0.002 (4)	0.110 (5)	−0.012 (4)
O2	0.0709 (19)	0.0627 (19)	0.0500 (16)	−0.0031 (15)	0.0077 (14)	−0.0046 (14)
C2	0.091	0.091	0.091	0.000	0.034	0.000
C3	0.098 (4)	0.083 (4)	0.105 (4)	0.008 (3)	0.064 (3)	−0.003 (3)
C4	0.071 (3)	0.059 (3)	0.078 (3)	−0.003 (2)	0.042 (2)	−0.006 (2)
C5	0.051 (2)	0.092 (4)	0.105 (4)	0.001 (3)	0.040 (3)	−0.009 (3)
C6	0.054 (2)	0.068 (3)	0.089 (3)	−0.016 (2)	0.034 (2)	−0.020 (3)
C7	0.047 (2)	0.042 (2)	0.053 (2)	−0.0051 (17)	0.0211 (18)	−0.0005 (18)
C8	0.051 (2)	0.055 (2)	0.055 (2)	−0.0008 (19)	0.0204 (19)	0.011 (2)
C9	0.074 (3)	0.057 (3)	0.061 (3)	−0.007 (2)	0.029 (2)	−0.008 (2)
C10	0.051 (2)	0.044 (2)	0.055 (2)	−0.0040 (18)	0.0254 (18)	−0.0009 (18)
C11	0.063 (2)	0.041 (2)	0.046 (2)	−0.0069 (19)	0.0129 (18)	−0.0012 (17)
C12	0.056 (2)	0.044 (2)	0.042 (2)	−0.0043 (19)	0.0191 (17)	−0.0029 (17)
C13	0.047 (2)	0.045 (2)	0.050 (2)	−0.0016 (18)	0.0125 (17)	0.0050 (18)
C14	0.057 (2)	0.045 (2)	0.058 (2)	−0.0012 (19)	0.014 (2)	0.0083 (19)
C15	0.065 (3)	0.056 (3)	0.046 (2)	0.001 (2)	0.0116 (19)	0.008 (2)
C16	0.045 (2)	0.061 (3)	0.049 (2)	−0.0008 (19)	0.0084 (17)	0.000 (2)
C17	0.089 (3)	0.046 (2)	0.057 (3)	−0.012 (2)	0.010 (2)	0.001 (2)
C18	0.090 (3)	0.042 (2)	0.049 (2)	−0.008 (2)	0.014 (2)	0.0026 (19)
C19	0.075 (3)	0.069 (3)	0.067 (3)	−0.017 (3)	0.020 (2)	−0.017 (2)

O1—C12	1.229 (4)	C7—C8	1.379 (5)
N1—N2	1.418 (4)	C8—C9	1.383 (5)
N1—C7	1.429 (4)	C8—H8A	0.9300
N1—C10	1.496 (4)	C9—H9A	0.9300
N2—C12	1.336 (4)	C10—C13	1.501 (5)
N2—H2A	0.8600	C10—C11	1.538 (5)
C1—C3	1.488 (6)	C10—H10A	0.9800
C1—H1A	0.9600	C11—C12	1.515 (5)
C1—H1B	0.9600	C11—H11A	0.9700
C1—H1C	0.9600	C11—H11B	0.9700
O2—C16	1.368 (4)	C13—C14	1.372 (5)
O2—C19	1.407 (5)	C13—C18	1.396 (5)
C2—C3	1.498 (6)	C14—C15	1.380 (5)
C2—H2B	0.9600	C14—H14A	0.9300
C2—H2C	0.9600	C15—C16	1.390 (5)
C2—H2D	0.9600	C15—H15A	0.9300
C3—C4	1.524 (6)	C16—C17	1.378 (5)
C3—H3A	0.9800	C17—C18	1.358 (5)
C4—C9	1.370 (5)	C17—H17A	0.9300
C4—C5	1.386 (6)	C18—H18A	0.9300
C5—C6	1.384 (6)	C19—H19A	0.9600
C5—H5A	0.9300	C19—H19B	0.9600
C6—C7	1.372 (5)	C19—H19C	0.9600
C6—H6A	0.9300
N2—N1—C7	112.7 (3)	C4—C9—H9A	119.1
N2—N1—C10	104.5 (3)	C8—C9—H9A	119.1
C7—N1—C10	115.0 (3)	N1—C10—C13	113.1 (3)
C12—N2—N1	115.2 (3)	N1—C10—C11	104.5 (3)
C12—N2—H2A	122.4	C13—C10—C11	114.0 (3)
N1—N2—H2A	122.4	N1—C10—H10A	108.3
C3—C1—H1A	109.5	C13—C10—H10A	108.3
C3—C1—H1B	109.5	C11—C10—H10A	108.3
H1A—C1—H1B	109.5	C12—C11—C10	103.3 (3)
C3—C1—H1C	109.5	C12—C11—H11A	111.1
H1A—C1—H1C	109.5	C10—C11—H11A	111.1
H1B—C1—H1C	109.5	C12—C11—H11B	111.1
C16—O2—C19	117.2 (3)	C10—C11—H11B	111.1
C3—C2—H2B	109.5	H11A—C11—H11B	109.1
C3—C2—H2C	109.5	O1—C12—N2	125.8 (3)
H2B—C2—H2C	109.5	O1—C12—C11	126.8 (3)
C3—C2—H2D	109.5	N2—C12—C11	107.4 (3)
H2B—C2—H2D	109.5	C14—C13—C18	116.9 (4)
H2C—C2—H2D	109.5	C14—C13—C10	125.0 (3)
C1—C3—C2	113.1 (4)	C18—C13—C10	118.1 (3)
C1—C3—C4	112.9 (4)	C13—C14—C15	121.7 (4)
C2—C3—C4	112.7 (4)	C13—C14—H14A	119.1
C1—C3—H3A	105.8	C15—C14—H14A	119.1
C2—C3—H3A	105.8	C14—C15—C16	120.4 (4)
C4—C3—H3A	105.8	C14—C15—H15A	119.8
C9—C4—C5	116.7 (4)	C16—C15—H15A	119.8
C9—C4—C3	121.0 (4)	O2—C16—C17	125.1 (4)
C5—C4—C3	122.4 (4)	O2—C16—C15	116.9 (4)
C6—C5—C4	122.0 (4)	C17—C16—C15	118.0 (4)
C6—C5—H5A	119.0	C18—C17—C16	121.0 (4)
C4—C5—H5A	119.0	C18—C17—H17A	119.5
C7—C6—C5	120.5 (4)	C16—C17—H17A	119.5
C7—C6—H6A	119.8	C17—C18—C13	122.0 (4)
C5—C6—H6A	119.8	C17—C18—H18A	119.0
C6—C7—C8	118.0 (4)	C13—C18—H18A	119.0
C6—C7—N1	117.5 (3)	O2—C19—H19A	109.5
C8—C7—N1	124.4 (3)	O2—C19—H19B	109.5
C7—C8—C9	121.0 (4)	H19A—C19—H19B	109.5
C7—C8—H8A	119.5	O2—C19—H19C	109.5
C9—C8—H8A	119.5	H19A—C19—H19C	109.5
C4—C9—C8	121.7 (4)	H19B—C19—H19C	109.5
C7—N1—N2—C12	112.7 (3)	C7—N1—C10—C11	−103.1 (3)
C10—N1—N2—C12	−12.9 (4)	N1—C10—C11—C12	−21.7 (4)
C1—C3—C4—C9	−120.1 (5)	C13—C10—C11—C12	102.3 (3)
C2—C3—C4—C9	110.2 (5)	N1—N2—C12—O1	176.9 (3)
C1—C3—C4—C5	59.8 (7)	N1—N2—C12—C11	−1.5 (4)
C2—C3—C4—C5	−69.8 (6)	C10—C11—C12—O1	−163.7 (4)
C9—C4—C5—C6	0.0 (7)	C10—C11—C12—N2	14.7 (4)
C3—C4—C5—C6	−180.0 (4)	N1—C10—C13—C14	0.7 (5)
C4—C5—C6—C7	1.2 (8)	C11—C10—C13—C14	−118.5 (4)
C5—C6—C7—C8	−2.2 (6)	N1—C10—C13—C18	179.5 (4)
C5—C6—C7—N1	−177.8 (4)	C11—C10—C13—C18	60.3 (5)
N2—N1—C7—C6	173.6 (3)	C18—C13—C14—C15	1.4 (6)
C10—N1—C7—C6	−66.8 (5)	C10—C13—C14—C15	−179.8 (4)
N2—N1—C7—C8	−1.8 (5)	C13—C14—C15—C16	−1.0 (6)
C10—N1—C7—C8	117.9 (4)	C19—O2—C16—C17	−5.9 (6)
C6—C7—C8—C9	2.1 (6)	C19—O2—C16—C15	174.9 (4)
N1—C7—C8—C9	177.4 (4)	C14—C15—C16—O2	179.8 (3)
C5—C4—C9—C8	0.0 (7)	C14—C15—C16—C17	0.6 (6)
C3—C4—C9—C8	179.9 (4)	O2—C16—C17—C18	−179.9 (4)
C7—C8—C9—C4	−1.1 (6)	C15—C16—C17—C18	−0.7 (7)
N2—N1—C10—C13	−103.6 (3)	C16—C17—C18—C13	1.2 (7)
C7—N1—C10—C13	132.3 (3)	C14—C13—C18—C17	−1.5 (7)
N2—N1—C10—C11	21.0 (4)	C10—C13—C18—C17	179.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	1.96	2.819 (4)	175
C8—H8A···N2	0.93	2.44	2.761 (5)	100
C14—H14A···N1	0.93	2.54	2.887 (5)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	1.96	2.819 (4)	175
C8—H8A⋯N2	0.93	2.44	2.761 (5)	100
C14—H14A⋯N1	0.93	2.54	2.887 (5)	102

Symmetry code: (i) .