2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl-idene]indan-1,3-dione.

In the title compound, C(21)H(16)N(2)O(2), the five-membered heterocyclic ring makes a dihedral angle of 47.06 (6)° with the attached benzene ring, whereas the indan-1,3-dione ring system and the benzene ring are oriented at a dihedral angle of 21.92 (7)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(22) loops. Aromatic π-π stacking inter-actions [centroid-centroid distances = 3.8325 (12)-3.8600 (12) Å] also occur.

Related literature

For background to donor–acceptor chromophores, see: Asiri et al. (2006 ▶); Asiri & Khan (2009 ▶); Koyuncu et al. (2010 ▶); Kulhanek et al. (2011 ▶); Wang et al. (2011 ▶). For related structures, see: Belyakov et al. (2008 ▶); Fun et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H16N2O2

M = 328.36

Monoclinic,

a = 14.6655 (3) Å

b = 7.8902 (2) Å

c = 28.6651 (7) Å

β = 98.251 (1)°

V = 3282.61 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.26 × 0.23 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.985

12302 measured reflections

2970 independent reflections

2106 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.01

2970 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049488/hb6509sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049488/hb6509Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049488/hb6509Isup3.cml

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

C21H16N2O2	F(000) = 1376
Mr = 328.36	Dx = 1.329 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2106 reflections
a = 14.6655 (3) Å	θ = 1.4–25.3°
b = 7.8902 (2) Å	µ = 0.09 mm−1
c = 28.6651 (7) Å	T = 296 K
β = 98.251 (1)°	Prism, yellow
V = 3282.61 (13) Å3	0.26 × 0.23 × 0.21 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2970 independent reflections
Radiation source: fine-focus sealed tube	2106 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 8.00 pixels mm-1	θmax = 25.3°, θmin = 1.4°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→9
Tmin = 0.975, Tmax = 0.985	l = −34→34
12302 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.9126P] where P = (Fo2 + 2Fc2)/3
2970 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.07106 (8)	0.30881 (19)	0.11877 (4)	0.0564 (5)
O2	0.23637 (9)	0.04176 (19)	0.00898 (4)	0.0608 (5)
N1	0.34865 (9)	0.1867 (2)	0.23313 (5)	0.0473 (5)
N2	0.25797 (9)	0.1475 (2)	0.23590 (5)	0.0439 (5)
C1	0.17883 (11)	0.1490 (2)	0.07845 (6)	0.0419 (6)
C2	0.09301 (11)	0.2414 (3)	0.08361 (6)	0.0423 (6)
C3	0.03786 (11)	0.2486 (2)	0.03591 (6)	0.0403 (6)
C4	−0.04905 (12)	0.3164 (3)	0.02282 (6)	0.0475 (6)
C5	−0.08681 (13)	0.3072 (3)	−0.02408 (7)	0.0537 (7)
C6	−0.03758 (14)	0.2345 (3)	−0.05695 (7)	0.0557 (7)
C7	0.04935 (13)	0.1681 (3)	−0.04398 (6)	0.0519 (7)
C8	0.08677 (11)	0.1748 (2)	0.00319 (6)	0.0414 (6)
C9	0.17632 (12)	0.1113 (3)	0.02737 (6)	0.0450 (6)
C10	0.25407 (11)	0.1176 (2)	0.11037 (6)	0.0441 (6)
C11	0.26939 (11)	0.1368 (2)	0.16062 (6)	0.0418 (6)
C12	0.35529 (11)	0.1768 (2)	0.18786 (6)	0.0441 (6)
C13	0.44513 (12)	0.2131 (3)	0.17115 (7)	0.0616 (8)
C14	0.20881 (11)	0.1150 (2)	0.19334 (6)	0.0418 (6)
C15	0.11558 (11)	0.0380 (3)	0.18802 (6)	0.0559 (7)
C16	0.22738 (12)	0.1517 (2)	0.28101 (6)	0.0440 (6)
C17	0.14828 (13)	0.2378 (3)	0.28667 (7)	0.0577 (8)
C18	0.12018 (16)	0.2438 (3)	0.33060 (9)	0.0709 (9)
C19	0.17138 (19)	0.1645 (3)	0.36842 (8)	0.0743 (10)
C20	0.25092 (17)	0.0804 (3)	0.36263 (7)	0.0682 (9)
C21	0.27950 (13)	0.0733 (3)	0.31885 (6)	0.0536 (7)
H4	−0.08104	0.36672	0.04493	0.0570*
H5	−0.14557	0.34996	−0.03377	0.0644*
H6	−0.06392	0.23049	−0.08844	0.0668*
H7	0.08189	0.12017	−0.06624	0.0623*
H10	0.30449	0.07647	0.09756	0.0529*
H13A	0.49379	0.20906	0.19738	0.0924*
H13B	0.44309	0.32379	0.15712	0.0924*
H13C	0.45628	0.12989	0.14820	0.0924*
H15A	0.07018	0.12581	0.18772	0.0838*
H15B	0.11146	−0.03737	0.21392	0.0838*
H15C	0.10477	−0.02420	0.15897	0.0838*
H17	0.11393	0.29166	0.26111	0.0693*
H18	0.06657	0.30145	0.33466	0.0850*
H19	0.15205	0.16794	0.39792	0.0891*
H20	0.28568	0.02796	0.38831	0.0818*
H21	0.33335	0.01622	0.31488	0.0643*

	U11	U22	U33	U12	U13	U23
O1	0.0561 (8)	0.0723 (10)	0.0421 (7)	0.0083 (7)	0.0117 (6)	−0.0049 (7)
O2	0.0533 (8)	0.0730 (11)	0.0585 (8)	0.0118 (7)	0.0158 (6)	−0.0066 (7)
N1	0.0349 (8)	0.0581 (11)	0.0483 (9)	−0.0067 (7)	0.0035 (6)	−0.0007 (8)
N2	0.0348 (8)	0.0530 (10)	0.0433 (8)	−0.0046 (7)	0.0032 (6)	0.0014 (7)
C1	0.0384 (9)	0.0464 (11)	0.0407 (9)	−0.0030 (8)	0.0053 (7)	0.0007 (9)
C2	0.0416 (10)	0.0472 (12)	0.0390 (10)	−0.0033 (8)	0.0087 (8)	0.0025 (9)
C3	0.0412 (10)	0.0400 (11)	0.0402 (10)	−0.0041 (8)	0.0076 (7)	0.0044 (8)
C4	0.0455 (10)	0.0516 (13)	0.0465 (10)	0.0007 (9)	0.0106 (8)	0.0068 (9)
C5	0.0453 (11)	0.0605 (14)	0.0532 (12)	0.0008 (10)	−0.0001 (9)	0.0100 (10)
C6	0.0595 (12)	0.0637 (15)	0.0407 (10)	−0.0042 (11)	−0.0038 (9)	0.0023 (10)
C7	0.0575 (12)	0.0560 (14)	0.0424 (10)	−0.0013 (10)	0.0076 (9)	−0.0030 (9)
C8	0.0417 (10)	0.0424 (12)	0.0402 (10)	−0.0053 (8)	0.0062 (7)	0.0013 (8)
C9	0.0428 (10)	0.0458 (12)	0.0476 (10)	−0.0032 (9)	0.0103 (8)	−0.0001 (9)
C10	0.0392 (10)	0.0460 (12)	0.0474 (10)	−0.0028 (8)	0.0073 (8)	−0.0007 (9)
C11	0.0359 (9)	0.0448 (12)	0.0436 (10)	−0.0005 (8)	0.0020 (7)	0.0018 (8)
C12	0.0369 (9)	0.0488 (12)	0.0463 (10)	−0.0027 (8)	0.0045 (7)	0.0022 (9)
C13	0.0403 (10)	0.0857 (17)	0.0585 (12)	−0.0126 (11)	0.0060 (9)	0.0028 (11)
C14	0.0341 (9)	0.0442 (12)	0.0456 (10)	−0.0015 (8)	0.0006 (7)	0.0042 (9)
C15	0.0423 (10)	0.0678 (15)	0.0557 (11)	−0.0129 (10)	0.0009 (8)	0.0091 (11)
C16	0.0419 (10)	0.0437 (12)	0.0471 (10)	−0.0080 (9)	0.0089 (8)	−0.0040 (9)
C17	0.0499 (12)	0.0578 (14)	0.0670 (13)	−0.0009 (10)	0.0136 (10)	0.0003 (11)
C18	0.0641 (14)	0.0630 (16)	0.0935 (18)	−0.0102 (12)	0.0383 (13)	−0.0158 (14)
C19	0.1054 (19)	0.0613 (16)	0.0645 (15)	−0.0224 (14)	0.0406 (14)	−0.0123 (13)
C20	0.0982 (18)	0.0600 (16)	0.0470 (12)	−0.0066 (13)	0.0127 (11)	−0.0033 (11)
C21	0.0598 (12)	0.0527 (13)	0.0483 (11)	0.0012 (10)	0.0073 (9)	−0.0045 (10)

O1—C2	1.223 (2)	C16—C17	1.374 (3)
O2—C9	1.220 (2)	C16—C21	1.380 (3)
N1—N2	1.3787 (19)	C17—C18	1.381 (3)
N1—C12	1.318 (2)	C18—C19	1.377 (3)
N2—C14	1.350 (2)	C19—C20	1.373 (4)
N2—C16	1.429 (2)	C20—C21	1.380 (3)
C1—C2	1.480 (2)	C4—H4	0.9300
C1—C9	1.489 (2)	C5—H5	0.9300
C1—C10	1.351 (2)	C6—H6	0.9300
C2—C3	1.487 (2)	C7—H7	0.9300
C3—C4	1.384 (2)	C10—H10	0.9300
C3—C8	1.388 (2)	C13—H13A	0.9600
C4—C5	1.381 (3)	C13—H13B	0.9600
C5—C6	1.390 (3)	C13—H13C	0.9600
C6—C7	1.379 (3)	C15—H15A	0.9600
C7—C8	1.385 (2)	C15—H15B	0.9600
C8—C9	1.482 (2)	C15—H15C	0.9600
C10—C11	1.434 (2)	C17—H17	0.9300
C11—C12	1.419 (2)	C18—H18	0.9300
C11—C14	1.392 (2)	C19—H19	0.9300
C12—C13	1.493 (2)	C20—H20	0.9300
C14—C15	1.484 (2)	C21—H21	0.9300
N2—N1—C12	104.58 (13)	C17—C18—C19	120.1 (2)
N1—N2—C14	112.65 (13)	C18—C19—C20	120.1 (2)
N1—N2—C16	118.54 (13)	C19—C20—C21	120.3 (2)
C14—N2—C16	128.77 (14)	C16—C21—C20	119.35 (19)
C2—C1—C9	107.17 (14)	C3—C4—H4	121.00
C2—C1—C10	130.24 (16)	C5—C4—H4	121.00
C9—C1—C10	122.11 (15)	C4—C5—H5	120.00
O1—C2—C1	128.67 (16)	C6—C5—H5	120.00
O1—C2—C3	124.66 (16)	C5—C6—H6	119.00
C1—C2—C3	106.57 (14)	C7—C6—H6	119.00
C2—C3—C4	128.51 (16)	C6—C7—H7	121.00
C2—C3—C8	109.87 (14)	C8—C7—H7	121.00
C4—C3—C8	121.62 (16)	C1—C10—H10	115.00
C3—C4—C5	117.97 (17)	C11—C10—H10	115.00
C4—C5—C6	120.46 (18)	C12—C13—H13A	109.00
C5—C6—C7	121.59 (18)	C12—C13—H13B	109.00
C6—C7—C8	118.03 (17)	C12—C13—H13C	109.00
C3—C8—C7	120.32 (16)	H13A—C13—H13B	109.00
C3—C8—C9	109.58 (15)	H13A—C13—H13C	109.00
C7—C8—C9	130.10 (16)	H13B—C13—H13C	109.00
O2—C9—C1	126.67 (16)	C14—C15—H15A	109.00
O2—C9—C8	126.62 (16)	C14—C15—H15B	109.00
C1—C9—C8	106.71 (15)	C14—C15—H15C	109.00
C1—C10—C11	130.99 (16)	H15A—C15—H15B	109.00
C10—C11—C12	125.10 (15)	H15A—C15—H15C	109.00
C10—C11—C14	129.85 (15)	H15B—C15—H15C	109.00
C12—C11—C14	105.00 (15)	C16—C17—H17	120.00
N1—C12—C11	111.71 (14)	C18—C17—H17	120.00
N1—C12—C13	119.87 (15)	C17—C18—H18	120.00
C11—C12—C13	128.37 (16)	C19—C18—H18	120.00
N2—C14—C11	106.01 (14)	C18—C19—H19	120.00
N2—C14—C15	122.38 (15)	C20—C19—H19	120.00
C11—C14—C15	130.47 (15)	C19—C20—H20	120.00
N2—C16—C17	119.90 (16)	C21—C20—H20	120.00
N2—C16—C21	119.37 (16)	C16—C21—H21	120.00
C17—C16—C21	120.70 (17)	C20—C21—H21	120.00
C16—C17—C18	119.49 (19)
C12—N1—N2—C14	−0.43 (19)	C4—C3—C8—C7	0.4 (3)
C12—N1—N2—C16	−178.29 (15)	C4—C3—C8—C9	−179.10 (18)
N2—N1—C12—C11	1.86 (19)	C3—C4—C5—C6	−1.2 (3)
N2—N1—C12—C13	179.52 (16)	C4—C5—C6—C7	0.7 (4)
N1—N2—C14—C11	−1.14 (19)	C5—C6—C7—C8	0.3 (3)
N1—N2—C14—C15	167.82 (16)	C6—C7—C8—C3	−0.8 (3)
C16—N2—C14—C11	176.44 (16)	C6—C7—C8—C9	178.5 (2)
C16—N2—C14—C15	−14.6 (3)	C3—C8—C9—O2	−179.0 (2)
N1—N2—C16—C17	130.59 (19)	C3—C8—C9—C1	1.0 (2)
N1—N2—C16—C21	−47.4 (2)	C7—C8—C9—O2	1.7 (4)
C14—N2—C16—C17	−46.9 (3)	C7—C8—C9—C1	−178.41 (19)
C14—N2—C16—C21	135.2 (2)	C1—C10—C11—C12	−148.87 (18)
C9—C1—C2—O1	−173.0 (2)	C1—C10—C11—C14	34.2 (3)
C9—C1—C2—C3	3.3 (2)	C10—C11—C12—N1	179.86 (16)
C10—C1—C2—O1	−0.9 (4)	C10—C11—C12—C13	2.4 (3)
C10—C1—C2—C3	175.33 (17)	C14—C11—C12—N1	−2.57 (19)
C2—C1—C9—O2	177.3 (2)	C14—C11—C12—C13	−180.00 (19)
C2—C1—C9—C8	−2.7 (2)	C10—C11—C14—N2	179.55 (16)
C10—C1—C9—O2	4.5 (3)	C10—C11—C14—C15	11.8 (3)
C10—C1—C9—C8	−175.48 (16)	C12—C11—C14—N2	2.13 (18)
C2—C1—C10—C11	12.2 (3)	C12—C11—C14—C15	−165.60 (18)
C9—C1—C10—C11	−176.81 (18)	N2—C16—C17—C18	−178.80 (19)
O1—C2—C3—C4	−6.1 (3)	C21—C16—C17—C18	−0.9 (3)
O1—C2—C3—C8	173.65 (19)	N2—C16—C21—C20	178.66 (19)
C1—C2—C3—C4	177.46 (18)	C17—C16—C21—C20	0.7 (3)
C1—C2—C3—C8	−2.8 (2)	C16—C17—C18—C19	0.2 (3)
C2—C3—C4—C5	−179.6 (2)	C17—C18—C19—C20	0.5 (4)
C8—C3—C4—C5	0.7 (3)	C18—C19—C20—C21	−0.7 (4)
C2—C3—C8—C7	−179.42 (18)	C19—C20—C21—C16	0.1 (3)
C2—C3—C8—C9	1.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1i	0.93	2.58	3.377 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1i	0.93	2.58	3.377 (3)	145

Symmetry code: (i) .