Crystal structure of (4Z)-4-[(2E)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-yl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

In the title compound, C23H18N2O2, the pyrazole ring subtends dihedral angles of 2.01 (13) and 1.55 (10)° with the pendant benzene ring and the naphthalene ring system, respectively. The mol-ecule is almost planar (r.m.s. deviation for the 27 non-H atoms = 0.025 Å) and intra-molecular O-H⋯O and C-H⋯O hydrogen bonds both close S(6) loops. In the crystal, very weak aromatic π-π stacking inter-actions between the benzene and the pyrazole rings, with centroid-centroid distances of 3.8913 (14) and 3.9285 (15) Å, are observed.

Related literature

For related structures, see: Chaudhry et al. (2012 ▸); Holzer et al. (1999 ▸); Malik et al. (2009 ▸).

Experimental

Crystal data

C23H18N2O2

M = 354.39

Monoclinic,

a = 6.7067 (8) Å

b = 17.525 (2) Å

c = 15.784 (2) Å

β = 101.152 (6)°

V = 1820.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.968, T max = 0.986

13979 measured reflections

3574 independent reflections

1855 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.140

S = 0.99

3574 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500866X/hb7418sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500866X/hb7418Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901500866X/hb7418Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901500866X/hb7418fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S205698901500866X/hb7418fig2.tif

The partial packing, showing π–π inter­actions.

CCDC reference: 1062997

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

C23H18N2O2	F(000) = 744
Mr = 354.39	Dx = 1.293 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7067 (8) Å	Cell parameters from 1855 reflections
b = 17.525 (2) Å	θ = 2.6–26.0°
c = 15.784 (2) Å	µ = 0.08 mm−1
β = 101.152 (6)°	T = 296 K
V = 1820.1 (4) Å3	Needle, purple
Z = 4	0.40 × 0.16 × 0.14 mm

Bruker Kappa APEXII CCD diffractometer	3574 independent reflections
Radiation source: fine-focus sealed tube	1855 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 7.80 pixels mm-1	θmax = 26.0°, θmin = 2.6°
ω scans	h = −8→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
Tmin = 0.968, Tmax = 0.986	l = −19→19
13979 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3
3574 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.16 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 > 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	0.1673 (2)	0.54343 (9)	0.17724 (11)	0.0684 (5)
O2	0.4599 (3)	0.49546 (9)	0.10912 (11)	0.0672 (5)
H2A	0.3651	0.5215	0.1186	0.101*
N1	0.1223 (3)	0.46669 (10)	0.29460 (12)	0.0527 (5)
N2	0.2155 (3)	0.40098 (11)	0.33743 (12)	0.0593 (6)
C1	−0.0446 (3)	0.49941 (13)	0.32414 (15)	0.0510 (6)
C2	−0.1094 (4)	0.46827 (15)	0.39423 (17)	0.0714 (8)
H2	−0.0430	0.4260	0.4221	0.086*
C3	−0.2734 (4)	0.49985 (18)	0.42332 (19)	0.0851 (9)
H3	−0.3152	0.4788	0.4711	0.102*
C4	−0.3740 (4)	0.56112 (17)	0.3831 (2)	0.0800 (8)
H4	−0.4843	0.5818	0.4028	0.096*
C5	−0.3108 (4)	0.59203 (15)	0.3130 (2)	0.0764 (8)
H5	−0.3794	0.6339	0.2851	0.092*
C6	−0.1459 (4)	0.56188 (14)	0.28280 (16)	0.0639 (7)
H6	−0.1040	0.5835	0.2353	0.077*
C7	0.2133 (3)	0.48753 (12)	0.22764 (15)	0.0508 (6)
C8	0.3725 (3)	0.43280 (12)	0.22720 (14)	0.0462 (6)
C9	0.3620 (3)	0.38203 (12)	0.29714 (15)	0.0533 (6)
C10	0.4899 (4)	0.31336 (14)	0.32827 (16)	0.0743 (8)
H10A	0.4788	0.2767	0.2824	0.111*
H10B	0.4434	0.2910	0.3764	0.111*
H10C	0.6293	0.3286	0.3458	0.111*
C11	0.4960 (3)	0.43911 (13)	0.16670 (15)	0.0503 (6)
C12	0.6639 (3)	0.38941 (12)	0.15888 (15)	0.0535 (6)
H12	0.6932	0.3489	0.1974	0.064*
C13	0.7796 (3)	0.39858 (13)	0.09910 (15)	0.0532 (6)
H13	0.7481	0.4397	0.0617	0.064*
C14	0.9479 (3)	0.35123 (12)	0.08677 (15)	0.0490 (6)
C15	1.0124 (4)	0.28705 (13)	0.13931 (16)	0.0590 (7)
H15	0.9461	0.2750	0.1841	0.071*
C16	1.1694 (4)	0.24273 (13)	0.12549 (17)	0.0607 (7)
H16	1.2071	0.2005	0.1606	0.073*
C17	1.2762 (3)	0.25934 (13)	0.05903 (16)	0.0519 (6)
C18	1.4400 (4)	0.21453 (14)	0.04322 (18)	0.0667 (7)
H18	1.4792	0.1716	0.0771	0.080*
C19	1.5422 (4)	0.23311 (16)	−0.02099 (19)	0.0730 (8)
H19	1.6492	0.2028	−0.0308	0.088*
C20	1.4857 (4)	0.29768 (17)	−0.07192 (18)	0.0735 (8)
H20	1.5571	0.3104	−0.1149	0.088*
C21	1.3268 (4)	0.34231 (15)	−0.05928 (16)	0.0632 (7)
H21	1.2905	0.3849	−0.0939	0.076*
C22	1.2170 (3)	0.32398 (13)	0.00630 (14)	0.0491 (6)
C23	1.0518 (3)	0.36872 (13)	0.02178 (14)	0.0518 (6)
H23	1.0121	0.4111	−0.0128	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0733 (12)	0.0593 (11)	0.0730 (12)	0.0127 (9)	0.0152 (9)	0.0219 (9)
O2	0.0714 (14)	0.0630 (12)	0.0694 (12)	0.0042 (9)	0.0190 (9)	0.0172 (10)
N1	0.0513 (13)	0.0557 (12)	0.0505 (12)	0.0075 (10)	0.0082 (10)	0.0075 (10)
N2	0.0575 (14)	0.0632 (13)	0.0577 (13)	0.0130 (11)	0.0125 (10)	0.0150 (11)
C1	0.0440 (16)	0.0540 (15)	0.0523 (15)	0.0045 (12)	0.0028 (11)	−0.0076 (12)
C2	0.066 (2)	0.0815 (19)	0.0692 (19)	0.0154 (16)	0.0189 (15)	0.0112 (16)
C3	0.079 (2)	0.103 (2)	0.079 (2)	0.0145 (19)	0.0293 (17)	0.0075 (18)
C4	0.067 (2)	0.086 (2)	0.089 (2)	0.0127 (18)	0.0177 (17)	−0.0186 (19)
C5	0.073 (2)	0.0635 (18)	0.088 (2)	0.0187 (15)	0.0044 (16)	−0.0115 (17)
C6	0.0651 (18)	0.0612 (16)	0.0645 (17)	0.0099 (14)	0.0105 (13)	−0.0034 (14)
C7	0.0488 (16)	0.0475 (14)	0.0535 (15)	−0.0038 (12)	0.0029 (12)	0.0040 (12)
C8	0.0389 (14)	0.0490 (14)	0.0491 (14)	−0.0021 (12)	0.0051 (11)	0.0045 (11)
C9	0.0494 (16)	0.0521 (14)	0.0568 (15)	0.0034 (12)	0.0065 (12)	0.0079 (13)
C10	0.0706 (19)	0.0756 (18)	0.0787 (19)	0.0235 (15)	0.0194 (14)	0.0298 (15)
C11	0.0480 (16)	0.0451 (14)	0.0533 (15)	−0.0085 (12)	−0.0013 (12)	0.0003 (12)
C12	0.0501 (16)	0.0504 (14)	0.0584 (16)	−0.0051 (13)	0.0064 (12)	0.0034 (12)
C13	0.0521 (16)	0.0483 (14)	0.0581 (16)	−0.0096 (12)	0.0081 (12)	0.0002 (12)
C14	0.0445 (15)	0.0464 (14)	0.0552 (15)	−0.0089 (12)	0.0076 (12)	−0.0017 (12)
C15	0.0578 (17)	0.0536 (15)	0.0682 (17)	−0.0082 (13)	0.0185 (13)	0.0080 (13)
C16	0.0576 (17)	0.0504 (15)	0.0726 (18)	−0.0062 (14)	0.0088 (13)	0.0127 (13)
C17	0.0431 (15)	0.0480 (14)	0.0632 (17)	−0.0093 (12)	0.0070 (12)	−0.0082 (12)
C18	0.0623 (19)	0.0541 (16)	0.082 (2)	−0.0060 (14)	0.0104 (15)	−0.0042 (14)
C19	0.0643 (19)	0.0697 (19)	0.087 (2)	−0.0030 (15)	0.0187 (16)	−0.0200 (17)
C20	0.070 (2)	0.089 (2)	0.0660 (19)	−0.0130 (17)	0.0261 (15)	−0.0147 (17)
C21	0.0609 (18)	0.0693 (17)	0.0593 (17)	−0.0065 (15)	0.0113 (13)	−0.0028 (14)
C22	0.0466 (16)	0.0519 (15)	0.0475 (14)	−0.0113 (13)	0.0057 (11)	−0.0056 (12)
C23	0.0496 (16)	0.0482 (14)	0.0554 (16)	−0.0064 (12)	0.0042 (12)	0.0039 (12)

O1—C7	1.262 (2)	C10—H10C	0.9600
O2—C11	1.332 (2)	C11—C12	1.447 (3)
O2—H2A	0.8200	C12—C13	1.342 (3)
N1—C7	1.368 (3)	C12—H12	0.9300
N1—C1	1.415 (3)	C13—C14	1.444 (3)
N1—N2	1.418 (2)	C13—H13	0.9300
N2—C9	1.312 (3)	C14—C23	1.381 (3)
C1—C2	1.377 (3)	C14—C15	1.414 (3)
C1—C6	1.383 (3)	C15—C16	1.360 (3)
C2—C3	1.387 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.410 (3)
C3—C4	1.359 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.412 (3)
C4—C5	1.371 (4)	C17—C22	1.416 (3)
C4—H4	0.9300	C18—C19	1.368 (3)
C5—C6	1.390 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.397 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.436 (3)	C20—C21	1.368 (3)
C8—C11	1.385 (3)	C20—H20	0.9300
C8—C9	1.430 (3)	C21—C22	1.418 (3)
C9—C10	1.504 (3)	C21—H21	0.9300
C10—H10A	0.9600	C22—C23	1.417 (3)
C10—H10B	0.9600	C23—H23	0.9300
C11—O2—H2A	109.5	O2—C11—C12	115.5 (2)
C7—N1—C1	130.2 (2)	C8—C11—C12	126.1 (2)
C7—N1—N2	111.32 (18)	C13—C12—C11	123.6 (2)
C1—N1—N2	118.43 (19)	C13—C12—H12	118.2
C9—N2—N1	106.08 (18)	C11—C12—H12	118.2
C2—C1—C6	119.4 (2)	C12—C13—C14	126.8 (2)
C2—C1—N1	119.8 (2)	C12—C13—H13	116.6
C6—C1—N1	120.8 (2)	C14—C13—H13	116.6
C1—C2—C3	120.1 (3)	C23—C14—C15	118.1 (2)
C1—C2—H2	119.9	C23—C14—C13	119.5 (2)
C3—C2—H2	119.9	C15—C14—C13	122.4 (2)
C4—C3—C2	121.0 (3)	C16—C15—C14	121.2 (2)
C4—C3—H3	119.5	C16—C15—H15	119.4
C2—C3—H3	119.5	C14—C15—H15	119.4
C3—C4—C5	119.1 (3)	C15—C16—C17	121.5 (2)
C3—C4—H4	120.4	C15—C16—H16	119.3
C5—C4—H4	120.4	C17—C16—H16	119.3
C4—C5—C6	121.1 (3)	C16—C17—C18	122.8 (2)
C4—C5—H5	119.4	C16—C17—C22	118.5 (2)
C6—C5—H5	119.4	C18—C17—C22	118.7 (2)
C1—C6—C5	119.3 (3)	C19—C18—C17	121.1 (3)
C1—C6—H6	120.3	C19—C18—H18	119.4
C5—C6—H6	120.3	C17—C18—H18	119.4
O1—C7—N1	127.1 (2)	C18—C19—C20	120.0 (3)
O1—C7—C8	127.3 (2)	C18—C19—H19	120.0
N1—C7—C8	105.57 (19)	C20—C19—H19	120.0
C11—C8—C9	135.0 (2)	C21—C20—C19	120.8 (3)
C11—C8—C7	119.6 (2)	C21—C20—H20	119.6
C9—C8—C7	105.3 (2)	C19—C20—H20	119.6
N2—C9—C8	111.71 (19)	C20—C21—C22	120.4 (2)
N2—C9—C10	118.5 (2)	C20—C21—H21	119.8
C8—C9—C10	129.8 (2)	C22—C21—H21	119.8
C9—C10—H10A	109.5	C17—C22—C23	118.8 (2)
C9—C10—H10B	109.5	C17—C22—C21	118.9 (2)
H10A—C10—H10B	109.5	C23—C22—C21	122.3 (2)
C9—C10—H10C	109.5	C14—C23—C22	121.9 (2)
H10A—C10—H10C	109.5	C14—C23—H23	119.0
H10B—C10—H10C	109.5	C22—C23—H23	119.0
O2—C11—C8	118.4 (2)
C7—N1—N2—C9	0.1 (2)	C7—C8—C11—O2	−1.4 (3)
C1—N1—N2—C9	179.18 (19)	C9—C8—C11—C12	0.3 (4)
C7—N1—C1—C2	−179.6 (2)	C7—C8—C11—C12	178.99 (19)
N2—N1—C1—C2	1.5 (3)	O2—C11—C12—C13	0.8 (3)
C7—N1—C1—C6	1.2 (4)	C8—C11—C12—C13	−179.6 (2)
N2—N1—C1—C6	−177.66 (19)	C11—C12—C13—C14	−179.44 (19)
C6—C1—C2—C3	−0.6 (4)	C12—C13—C14—C23	−180.0 (2)
N1—C1—C2—C3	−179.7 (2)	C12—C13—C14—C15	−0.2 (4)
C1—C2—C3—C4	0.7 (4)	C23—C14—C15—C16	−1.3 (3)
C2—C3—C4—C5	−0.3 (4)	C13—C14—C15—C16	179.0 (2)
C3—C4—C5—C6	−0.2 (4)	C14—C15—C16—C17	0.8 (4)
C2—C1—C6—C5	0.1 (3)	C15—C16—C17—C18	179.8 (2)
N1—C1—C6—C5	179.3 (2)	C15—C16—C17—C22	0.2 (3)
C4—C5—C6—C1	0.3 (4)	C16—C17—C18—C19	−178.9 (2)
C1—N1—C7—O1	1.4 (4)	C22—C17—C18—C19	0.7 (3)
N2—N1—C7—O1	−179.63 (19)	C17—C18—C19—C20	0.4 (4)
C1—N1—C7—C8	−178.9 (2)	C18—C19—C20—C21	−1.0 (4)
N2—N1—C7—C8	0.0 (2)	C19—C20—C21—C22	0.4 (4)
O1—C7—C8—C11	0.5 (3)	C16—C17—C22—C23	−0.7 (3)
N1—C7—C8—C11	−179.13 (19)	C18—C17—C22—C23	179.63 (19)
O1—C7—C8—C9	179.5 (2)	C16—C17—C22—C21	178.4 (2)
N1—C7—C8—C9	−0.1 (2)	C18—C17—C22—C21	−1.3 (3)
N1—N2—C9—C8	−0.2 (2)	C20—C21—C22—C17	0.7 (3)
N1—N2—C9—C10	−179.94 (18)	C20—C21—C22—C23	179.8 (2)
C11—C8—C9—N2	179.0 (2)	C15—C14—C23—C22	0.7 (3)
C7—C8—C9—N2	0.2 (3)	C13—C14—C23—C22	−179.51 (18)
C11—C8—C9—C10	−1.3 (4)	C17—C22—C23—C14	0.2 (3)
C7—C8—C9—C10	179.9 (2)	C21—C22—C23—C14	−178.8 (2)
C9—C8—C11—O2	179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.80	2.555 (2)	153
C6—H6···O1	0.93	2.30	2.940 (3)	126

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2AO1	0.82	1.80	2.555(2)	153
C6H6O1	0.93	2.30	2.940(3)	126