4-[1-Acetyl-3-(4-methoxy-phen-yl)-2-pyrazolin-5-yl]phenol.

In the title compound, C(18)H(18)N(2)O(3), the dihedral angle formed by the benzene rings is 71.75 (4)°. In the crystal structure, centrosymmetrically related mol-ecules are linked into dimers by inter-molecular O-H⋯O hydrogen bonds and π-π stacking inter-actions with centroid-centroid distances of 3.5511 (6) Å.

Related literature

For the biological activity of 2-pyrazoline derivatives, see: Grimm et al. (2009 ▶). For the synthesis and crystal structure of 2-pyrazoline derivatives, see: Chen et al. (2009 ▶); Li et al. (2008 ▶); Humaira et al. (2008 ▶); Shoman et al. (2009 ▶).

Experimental

Crystal data

C18H18N2O3

M = 310.34

Monoclinic,

a = 8.7037 (17) Å

b = 15.673 (3) Å

c = 11.096 (2) Å

β = 100.31 (3)°

V = 1489.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.28 × 0.25 × 0.23 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.974, T max = 0.978

12107 measured reflections

3542 independent reflections

2857 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.07

3542 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043785/rz2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043785/rz2374Isup2.hkl

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

C18H18N2O3	F(000) = 656
Mr = 310.34	Dx = 1.384 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4953 reflections
a = 8.7037 (17) Å	θ = 1.9–27.9°
b = 15.673 (3) Å	µ = 0.10 mm−1
c = 11.096 (2) Å	T = 113 K
β = 100.31 (3)°	Block, colourless
V = 1489.2 (5) Å3	0.28 × 0.25 × 0.23 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3542 independent reflections
Radiation source: rotating anode	2857 reflections with I > 2σ(I)
confocal	Rint = 0.035
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω and φ scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −20→20
Tmin = 0.974, Tmax = 0.978	l = −10→14
12107 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.155P] where P = (Fo2 + 2Fc2)/3
3542 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 > 2σ(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	0.94883 (10)	0.38855 (6)	0.70894 (7)	0.0229 (2)
H1	1.0433	0.3749	0.7160	0.034*
O2	0.75176 (10)	0.66339 (5)	0.27990 (7)	0.0225 (2)
O3	−0.11026 (10)	0.27148 (5)	−0.04411 (8)	0.0231 (2)
N1	0.58975 (11)	0.55520 (6)	0.21083 (8)	0.0167 (2)
N2	0.43790 (11)	0.52531 (6)	0.17203 (8)	0.0171 (2)
C1	0.89186 (13)	0.40973 (7)	0.59032 (10)	0.0168 (2)
C2	0.75202 (13)	0.45422 (7)	0.56538 (10)	0.0182 (2)
H2	0.6974	0.4675	0.6298	0.022*
C3	0.69165 (13)	0.47942 (7)	0.44593 (10)	0.0168 (2)
H3	0.5958	0.5099	0.4295	0.020*
C4	0.77000 (13)	0.46058 (7)	0.35034 (9)	0.0151 (2)
C5	0.90875 (13)	0.41512 (7)	0.37684 (10)	0.0163 (2)
H5	0.9631	0.4015	0.3123	0.020*
C6	0.97009 (13)	0.38908 (7)	0.49508 (10)	0.0164 (2)
H6	1.0646	0.3574	0.5111	0.020*
C7	0.70776 (13)	0.48686 (7)	0.21887 (10)	0.0159 (2)
H7	0.7957	0.5053	0.1780	0.019*
C8	0.61163 (13)	0.41600 (7)	0.14272 (10)	0.0171 (2)
H8A	0.6386	0.4113	0.0600	0.021*
H8B	0.6277	0.3600	0.1843	0.021*
C9	0.44632 (13)	0.44749 (7)	0.13665 (9)	0.0160 (2)
C10	0.61741 (14)	0.63762 (7)	0.24368 (9)	0.0179 (2)
C11	0.47757 (15)	0.69509 (8)	0.23326 (11)	0.0233 (3)
H11A	0.5121	0.7537	0.2534	0.035*
H11B	0.4107	0.6759	0.2903	0.035*
H11C	0.4186	0.6931	0.1493	0.035*
C12	0.30403 (13)	0.39938 (7)	0.09013 (9)	0.0163 (2)
C13	0.31003 (14)	0.31987 (7)	0.03532 (10)	0.0183 (2)
H13	0.4088	0.2956	0.0306	0.022*
C14	0.17471 (14)	0.27499 (7)	−0.01279 (10)	0.0191 (2)
H14	0.1812	0.2213	−0.0512	0.023*
C15	0.03036 (13)	0.30954 (7)	−0.00400 (10)	0.0180 (2)
C16	0.02255 (14)	0.38880 (7)	0.05220 (10)	0.0205 (3)
H16	−0.0763	0.4123	0.0584	0.025*
C17	0.15651 (14)	0.43316 (8)	0.09871 (10)	0.0199 (2)
H17	0.1494	0.4869	0.1369	0.024*
C18	−0.11105 (16)	0.19636 (9)	−0.11600 (13)	0.0320 (3)
H18A	−0.0643	0.2087	−0.1881	0.048*
H18B	−0.2188	0.1769	−0.1424	0.048*
H18C	−0.0506	0.1516	−0.0671	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (5)	0.0314 (5)	0.0155 (4)	0.0013 (4)	0.0014 (3)	0.0053 (3)
O2	0.0226 (5)	0.0219 (4)	0.0217 (4)	−0.0016 (3)	0.0006 (3)	0.0008 (3)
O3	0.0177 (4)	0.0242 (4)	0.0269 (4)	−0.0011 (3)	0.0027 (3)	−0.0048 (3)
N1	0.0146 (5)	0.0173 (5)	0.0179 (4)	0.0021 (4)	0.0021 (4)	0.0011 (3)
N2	0.0161 (5)	0.0191 (5)	0.0158 (4)	0.0003 (4)	0.0021 (4)	0.0015 (4)
C1	0.0174 (6)	0.0167 (5)	0.0158 (5)	−0.0046 (4)	0.0017 (4)	0.0015 (4)
C2	0.0174 (6)	0.0216 (6)	0.0165 (5)	−0.0023 (4)	0.0058 (4)	−0.0007 (4)
C3	0.0133 (5)	0.0182 (5)	0.0190 (5)	0.0000 (4)	0.0035 (4)	−0.0002 (4)
C4	0.0156 (5)	0.0144 (5)	0.0150 (5)	−0.0021 (4)	0.0022 (4)	0.0001 (4)
C5	0.0174 (6)	0.0155 (5)	0.0168 (5)	−0.0007 (4)	0.0054 (4)	−0.0013 (4)
C6	0.0141 (6)	0.0147 (5)	0.0201 (5)	−0.0002 (4)	0.0020 (4)	0.0008 (4)
C7	0.0154 (5)	0.0172 (5)	0.0155 (5)	0.0033 (4)	0.0040 (4)	0.0002 (4)
C8	0.0170 (6)	0.0193 (5)	0.0148 (5)	0.0024 (4)	0.0023 (4)	−0.0011 (4)
C9	0.0177 (6)	0.0187 (5)	0.0118 (5)	0.0037 (4)	0.0030 (4)	0.0018 (4)
C10	0.0229 (6)	0.0177 (5)	0.0134 (5)	0.0007 (5)	0.0037 (4)	0.0021 (4)
C11	0.0261 (6)	0.0176 (5)	0.0260 (6)	0.0033 (5)	0.0046 (5)	−0.0011 (5)
C12	0.0176 (6)	0.0186 (5)	0.0128 (5)	0.0017 (4)	0.0027 (4)	0.0022 (4)
C13	0.0174 (6)	0.0196 (5)	0.0184 (5)	0.0042 (4)	0.0043 (4)	0.0007 (4)
C14	0.0216 (6)	0.0171 (5)	0.0183 (5)	0.0021 (4)	0.0030 (4)	−0.0009 (4)
C15	0.0179 (6)	0.0212 (6)	0.0146 (5)	0.0003 (4)	0.0019 (4)	0.0029 (4)
C16	0.0177 (6)	0.0230 (6)	0.0212 (5)	0.0041 (5)	0.0047 (4)	−0.0009 (4)
C17	0.0210 (6)	0.0202 (5)	0.0188 (5)	0.0041 (5)	0.0040 (4)	−0.0017 (4)
C18	0.0253 (7)	0.0251 (6)	0.0435 (8)	−0.0009 (5)	0.0008 (6)	−0.0114 (6)

O1—C1	1.3619 (13)	C8—C9	1.5112 (15)
O1—H1	0.8400	C8—H8A	0.9900
O2—C10	1.2345 (15)	C8—H8B	0.9900
O3—C15	1.3626 (14)	C9—C12	1.4628 (16)
O3—C18	1.4216 (15)	C10—C11	1.5018 (16)
N1—C10	1.3521 (15)	C11—H11A	0.9800
N1—N2	1.3957 (13)	C11—H11B	0.9800
N1—C7	1.4757 (14)	C11—H11C	0.9800
N2—C9	1.2873 (14)	C12—C13	1.3917 (15)
C1—C2	1.3870 (16)	C12—C17	1.4077 (16)
C1—C6	1.3939 (15)	C13—C14	1.3935 (16)
C2—C3	1.3927 (16)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.3875 (16)
C3—C4	1.3915 (15)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.3970 (16)
C4—C5	1.3876 (16)	C16—C17	1.3762 (17)
C4—C7	1.5193 (15)	C16—H16	0.9500
C5—C6	1.3865 (15)	C17—H17	0.9500
C5—H5	0.9500	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.5474 (16)	C18—H18C	0.9800
C7—H7	1.0000
C1—O1—H1	109.5	N2—C9—C12	120.34 (10)
C15—O3—C18	117.37 (9)	N2—C9—C8	113.68 (10)
C10—N1—N2	121.13 (9)	C12—C9—C8	125.91 (10)
C10—N1—C7	126.07 (10)	O2—C10—N1	120.86 (10)
N2—N1—C7	112.67 (9)	O2—C10—C11	122.43 (10)
C9—N2—N1	108.04 (9)	N1—C10—C11	116.71 (10)
O1—C1—C2	118.04 (10)	C10—C11—H11A	109.5
O1—C1—C6	122.24 (10)	C10—C11—H11B	109.5
C2—C1—C6	119.72 (10)	H11A—C11—H11B	109.5
C1—C2—C3	120.04 (10)	C10—C11—H11C	109.5
C1—C2—H2	120.0	H11A—C11—H11C	109.5
C3—C2—H2	120.0	H11B—C11—H11C	109.5
C4—C3—C2	120.82 (10)	C13—C12—C17	118.18 (11)
C4—C3—H3	119.6	C13—C12—C9	121.34 (10)
C2—C3—H3	119.6	C17—C12—C9	120.47 (10)
C5—C4—C3	118.30 (10)	C12—C13—C14	121.61 (10)
C5—C4—C7	119.33 (9)	C12—C13—H13	119.2
C3—C4—C7	122.36 (10)	C14—C13—H13	119.2
C6—C5—C4	121.65 (10)	C15—C14—C13	119.34 (10)
C6—C5—H5	119.2	C15—C14—H14	120.3
C4—C5—H5	119.2	C13—C14—H14	120.3
C5—C6—C1	119.44 (10)	O3—C15—C14	125.30 (11)
C5—C6—H6	120.3	O3—C15—C16	114.99 (10)
C1—C6—H6	120.3	C14—C15—C16	119.69 (11)
N1—C7—C4	112.31 (9)	C17—C16—C15	120.73 (11)
N1—C7—C8	100.69 (9)	C17—C16—H16	119.6
C4—C7—C8	113.25 (9)	C15—C16—H16	119.6
N1—C7—H7	110.1	C16—C17—C12	120.42 (11)
C4—C7—H7	110.1	C16—C17—H17	119.8
C8—C7—H7	110.1	C12—C17—H17	119.8
C9—C8—C7	101.97 (9)	O3—C18—H18A	109.5
C9—C8—H8A	111.4	O3—C18—H18B	109.5
C7—C8—H8A	111.4	H18A—C18—H18B	109.5
C9—C8—H8B	111.4	O3—C18—H18C	109.5
C7—C8—H8B	111.4	H18A—C18—H18C	109.5
H8A—C8—H8B	109.2	H18B—C18—H18C	109.5
C10—N1—N2—C9	174.49 (9)	N1—N2—C9—C8	−2.58 (12)
C7—N1—N2—C9	−9.40 (11)	C7—C8—C9—N2	12.40 (12)
O1—C1—C2—C3	178.11 (10)	C7—C8—C9—C12	−170.70 (9)
C6—C1—C2—C3	−1.14 (16)	N2—N1—C10—O2	178.76 (9)
C1—C2—C3—C4	−0.03 (17)	C7—N1—C10—O2	3.20 (16)
C2—C3—C4—C5	0.80 (16)	N2—N1—C10—C11	−1.45 (14)
C2—C3—C4—C7	179.90 (10)	C7—N1—C10—C11	−177.02 (9)
C3—C4—C5—C6	−0.41 (16)	N2—C9—C12—C13	170.72 (10)
C7—C4—C5—C6	−179.55 (10)	C8—C9—C12—C13	−5.99 (16)
C4—C5—C6—C1	−0.73 (16)	N2—C9—C12—C17	−8.61 (15)
O1—C1—C6—C5	−177.70 (10)	C8—C9—C12—C17	174.68 (10)
C2—C1—C6—C5	1.51 (16)	C17—C12—C13—C14	1.49 (16)
C10—N1—C7—C4	71.36 (13)	C9—C12—C13—C14	−177.86 (10)
N2—N1—C7—C4	−104.52 (10)	C12—C13—C14—C15	−1.19 (16)
C10—N1—C7—C8	−167.87 (10)	C18—O3—C15—C14	−9.49 (16)
N2—N1—C7—C8	16.25 (10)	C18—O3—C15—C16	171.96 (10)
C5—C4—C7—N1	−162.58 (9)	C13—C14—C15—O3	−178.16 (10)
C3—C4—C7—N1	18.32 (15)	C13—C14—C15—C16	0.33 (16)
C5—C4—C7—C8	84.19 (12)	O3—C15—C16—C17	178.82 (10)
C3—C4—C7—C8	−94.91 (12)	C14—C15—C16—C17	0.18 (17)
N1—C7—C8—C9	−15.77 (10)	C15—C16—C17—C12	0.15 (17)
C4—C7—C8—C9	104.33 (10)	C13—C12—C17—C16	−0.96 (16)
N1—N2—C9—C12	−179.67 (8)	C9—C12—C17—C16	178.39 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.87	2.7117 (13)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.87	2.7117 (13)	175

Symmetry code: (i) .