N-[(3,5-Dimethyl-pyrazol-1-yl)meth-yl]phthalimide.

The title compound {systematic name: 2-[(3,5-dimenthylpyrazol-1-yl)meth-yl]isoindole-1,3-dione}, C(14)H(13)N(3)O(2), was prepared by reaction of N-(bromo-meth-yl)phthalimide and 3,5-dimethyl-pyrazole in chloro-form solution. The mol-ecular structure and packing are stabilized by intra-molecular C-H⋯O hydrogen-bonding and C-H⋯π inter-actions.

Related literature

For related literature, see: Jian et al. (2003 ▶, 2004 ▶); Barszcz et al. (2004 ▶).

Experimental

Crystal data

C14H13N3O2

M = 255.27

Monoclinic,

a = 12.285 (2) Å

b = 8.4576 (15) Å

c = 15.6162 (19) Å

β = 127.566 (8)°

V = 1286.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

8080 measured reflections

3090 independent reflections

1464 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.178

S = 0.98

3090 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802518X/at2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802518X/at2593Isup2.hkl

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

C14H13N3O2	F000 = 536
Mr = 255.27	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1464 reflections
a = 12.285 (2) Å	θ = 2.1–28.2º
b = 8.4576 (15) Å	µ = 0.09 mm−1
c = 15.6162 (19) Å	T = 293 (2) K
β = 127.566 (8)º	Block, yellow
V = 1286.1 (3) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1464 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Monochromator: graphite	θmax = 28.2º
T = 293(2) K	θmin = 2.1º
φ and ω scans	h = −16→13
Absorption correction: none	k = −10→11
8080 measured reflections	l = −19→20
3090 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	w = 1/[σ2(Fo2) + (0.0831P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.178	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.33 e Å−3
3090 reflections	Δρmin = −0.21 e Å−3
173 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (6)
Secondary atom site location: difference Fourier map

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	0.66997 (19)	−0.2663 (2)	−0.13413 (14)	0.0613 (6)
O2	0.38437 (19)	−0.1191 (2)	−0.05358 (15)	0.0610 (6)
N1	0.50763 (19)	−0.1704 (2)	−0.11721 (15)	0.0443 (5)
N2	0.3078 (2)	−0.1271 (2)	−0.30016 (15)	0.0481 (6)
N3	0.3112 (2)	−0.2458 (2)	−0.35815 (16)	0.0508 (6)
C1	0.1467 (3)	0.0376 (4)	−0.2904 (2)	0.0729 (9)
H1A	0.2309	0.0833	−0.2297	0.109*
H1B	0.0965	−0.0058	−0.2672	0.109*
H1C	0.0925	0.1178	−0.3439	0.109*
C2	0.1782 (3)	−0.0900 (3)	−0.3378 (2)	0.0520 (7)
C3	0.0937 (3)	−0.1884 (3)	−0.4239 (2)	0.0575 (7)
H3B	−0.0016	−0.1922	−0.4669	0.069*
C4	0.1783 (3)	−0.2813 (3)	−0.4344 (2)	0.0524 (7)
C5	0.1404 (3)	−0.4075 (4)	−0.5153 (2)	0.0737 (9)
H5A	0.2223	−0.4502	−0.5013	0.111*
H5B	0.0833	−0.3632	−0.5867	0.111*
H5C	0.0914	−0.4901	−0.5099	0.111*
C6	0.4354 (2)	−0.0637 (3)	−0.20848 (18)	0.0486 (6)
H6A	0.4176	0.0345	−0.1870	0.058*
H6B	0.4937	−0.0397	−0.2292	0.058*
C7	0.6197 (2)	−0.2631 (3)	−0.0875 (2)	0.0442 (6)
C8	0.6612 (2)	−0.3498 (3)	0.01092 (18)	0.0460 (6)
C9	0.7624 (3)	−0.4605 (3)	0.0711 (2)	0.0611 (8)
H9A	0.8183	−0.4937	0.0531	0.073*
C10	0.7773 (3)	−0.5210 (4)	0.1611 (2)	0.0708 (9)
H10A	0.8446	−0.5966	0.2038	0.085*
C11	0.6954 (3)	−0.4717 (4)	0.1882 (2)	0.0685 (9)
H11A	0.7098	−0.5121	0.2498	0.082*
C12	0.5915 (3)	−0.3625 (3)	0.12510 (19)	0.0561 (7)
H12A	0.5342	−0.3306	0.1420	0.067*
C13	0.5765 (2)	−0.3033 (3)	0.03664 (18)	0.0439 (6)
C14	0.4762 (3)	−0.1880 (3)	−0.04554 (19)	0.0454 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0654 (12)	0.0772 (13)	0.0586 (11)	0.0047 (10)	0.0467 (11)	−0.0022 (9)
O2	0.0650 (12)	0.0651 (12)	0.0718 (12)	0.0080 (10)	0.0515 (11)	0.0043 (10)
N1	0.0474 (12)	0.0503 (12)	0.0403 (11)	0.0032 (10)	0.0294 (10)	0.0019 (9)
N2	0.0492 (12)	0.0535 (13)	0.0422 (11)	0.0021 (10)	0.0282 (10)	0.0022 (10)
N3	0.0583 (14)	0.0535 (13)	0.0446 (12)	0.0000 (11)	0.0333 (12)	−0.0004 (10)
C1	0.0560 (18)	0.082 (2)	0.073 (2)	0.0076 (16)	0.0352 (16)	−0.0100 (17)
C2	0.0488 (15)	0.0574 (16)	0.0486 (14)	0.0033 (13)	0.0290 (13)	0.0018 (13)
C3	0.0465 (15)	0.0656 (18)	0.0539 (16)	0.0002 (14)	0.0272 (14)	−0.0010 (14)
C4	0.0558 (16)	0.0550 (16)	0.0448 (14)	−0.0043 (13)	0.0298 (14)	0.0034 (12)
C5	0.075 (2)	0.075 (2)	0.0697 (18)	−0.0117 (17)	0.0434 (17)	−0.0163 (17)
C6	0.0504 (15)	0.0524 (15)	0.0419 (14)	−0.0034 (12)	0.0276 (13)	−0.0003 (12)
C7	0.0455 (14)	0.0481 (14)	0.0425 (13)	−0.0036 (11)	0.0287 (12)	−0.0064 (11)
C8	0.0428 (14)	0.0493 (15)	0.0407 (13)	−0.0045 (12)	0.0227 (12)	−0.0046 (12)
C9	0.0532 (17)	0.0645 (18)	0.0576 (17)	0.0062 (14)	0.0297 (14)	0.0038 (15)
C10	0.0634 (19)	0.064 (2)	0.0615 (19)	0.0063 (15)	0.0261 (16)	0.0135 (15)
C11	0.078 (2)	0.072 (2)	0.0461 (16)	−0.0097 (17)	0.0329 (16)	0.0050 (15)
C12	0.0666 (18)	0.0576 (17)	0.0447 (14)	−0.0142 (14)	0.0343 (14)	−0.0067 (13)
C13	0.0479 (14)	0.0455 (14)	0.0375 (13)	−0.0073 (11)	0.0256 (12)	−0.0054 (11)
C14	0.0471 (14)	0.0521 (15)	0.0413 (13)	−0.0039 (12)	0.0292 (12)	−0.0051 (12)

O1—O1	0.000 (5)	C5—H5A	0.9600
O1—C7	1.208 (3)	C5—H5B	0.9600
O2—C14	1.206 (3)	C5—H5C	0.9600
N1—C7	1.396 (3)	C6—H6A	0.9700
N1—C14	1.397 (3)	C6—H6B	0.9700
N1—C6	1.446 (3)	C7—O1	1.208 (3)
N2—C2	1.355 (3)	C7—C8	1.485 (3)
N2—N3	1.369 (3)	C8—C9	1.372 (3)
N2—C6	1.435 (3)	C8—C13	1.382 (3)
N3—C4	1.343 (3)	C9—C10	1.399 (4)
C1—C2	1.487 (4)	C9—H9A	0.9300
C1—H1A	0.9600	C10—C11	1.373 (4)
C1—H1B	0.9600	C10—H10A	0.9300
C1—H1C	0.9600	C11—C12	1.385 (4)
C2—C3	1.370 (4)	C11—H11A	0.9300
C3—C4	1.390 (4)	C12—C13	1.372 (3)
C3—H3B	0.9300	C12—H12A	0.9300
C4—C5	1.495 (4)	C13—C14	1.479 (4)
O1—O1—C7	0(10)	N1—C6—H6A	109.0
C7—N1—C14	111.9 (2)	N2—C6—H6B	109.0
C7—N1—C6	124.48 (19)	N1—C6—H6B	109.0
C14—N1—C6	123.6 (2)	H6A—C6—H6B	107.8
C2—N2—N3	112.6 (2)	O1—C7—O1	0.00 (8)
C2—N2—C6	128.8 (2)	O1—C7—N1	125.1 (2)
N3—N2—C6	118.6 (2)	O1—C7—N1	125.1 (2)
C4—N3—N2	103.8 (2)	O1—C7—C8	129.3 (2)
C2—C1—H1A	109.5	O1—C7—C8	129.3 (2)
C2—C1—H1B	109.5	N1—C7—C8	105.5 (2)
H1A—C1—H1B	109.5	C9—C8—C13	121.6 (2)
C2—C1—H1C	109.5	C9—C8—C7	129.9 (2)
H1A—C1—H1C	109.5	C13—C8—C7	108.5 (2)
H1B—C1—H1C	109.5	C8—C9—C10	116.5 (3)
N2—C2—C3	105.8 (2)	C8—C9—H9A	121.7
N2—C2—C1	123.1 (2)	C10—C9—H9A	121.7
C3—C2—C1	131.1 (2)	C11—C10—C9	121.8 (3)
C2—C3—C4	106.6 (2)	C11—C10—H10A	119.1
C2—C3—H3B	126.7	C9—C10—H10A	119.1
C4—C3—H3B	126.7	C10—C11—C12	120.9 (3)
N3—C4—C3	111.2 (2)	C10—C11—H11A	119.5
N3—C4—C5	119.5 (2)	C12—C11—H11A	119.5
C3—C4—C5	129.3 (2)	C13—C12—C11	117.4 (3)
C4—C5—H5A	109.5	C13—C12—H12A	121.3
C4—C5—H5B	109.5	C11—C12—H12A	121.3
H5A—C5—H5B	109.5	C12—C13—C8	121.7 (3)
C4—C5—H5C	109.5	C12—C13—C14	130.1 (2)
H5A—C5—H5C	109.5	C8—C13—C14	108.2 (2)
H5B—C5—H5C	109.5	O2—C14—N1	124.3 (2)
N2—C6—N1	112.99 (19)	O2—C14—C13	129.8 (2)
N2—C6—H6A	109.0	N1—C14—C13	105.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O1	0.97	2.58	2.917 (3)	101
C11—H11A···Cg2i	0.93	2.96	3.723 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O1	0.97	2.58	2.917 (3)	101
C11—H11A⋯Cg2i	0.93	2.96	3.723 (3)	140

Symmetry code: (i) . Cg2 is the centroid of atoms N2,N3,C2–C4.