N (4 Methyl 1 piperazinyl)­phthal­imide

organic papers

o306

Structure Reports Online

ISSN 1600-5368

N

-(4-Methyl-1-piperazinyl)phthalimide

Ming-Lin Guo

College of Materials and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China

Correspondence e-mail: [email protected]

Key indicators Single-crystal X-ray study T= 293 K

Mean(C±C) = 0.003 AÊ Rfactor = 0.041 wRfactor = 0.114

Data-to-parameter ratio = 12.2

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

The title compound, C13H15N3O2, (I), crystallizes in the

monoclinic space group P21/m. The phthalimide rings lie in

crystallographic mirror planes. Molecules are associated into columns parallel to theb-axis direction, and linked together along the a-axis direction by a two-dimensional network of hydrogen bonds involving CÐH O interactions. The molecular packing in the crystal is stabilized by the weak intermolecular CÐH O hydrogen bonds and van der Waals forces.

Experimental

The title compound was prepared by the reaction of phthalic anhy-dride (6.4 g) with 1-amino-4-methylpiperazine (5.0 g) under micro-wave irradiation for 10 min. The resulting product was heated and dissolved in ethanol (60 ml). The homogeneous solution was allowed to stand at room temperature for 12 h, after which 7.0 g of the colorless crystalline product was separated by ®ltration. PureN -(4-methyl-1-piperazinyl)phthalimide (1.5 g) was dissolved in ethanol (20 ml). A single crystal was obtained by evaporation for 10 h at room temperature.

Crystal data C13H15N3O2

Mr= 245.28 Monoclinic,P21=m a= 8.364 (3) AÊ

b= 6.816 (3) AÊ

c= 10.972 (5) AÊ

= 101.980 (6)

V= 611.9 (4) AÊ3

Z= 2

Dx= 1.331 Mg mÿ3 MoKradiation Cell parameters from 853

re¯ections

= 2.8±26.4 = 0.09 mmÿ1

T= 293 (2) K Prism, colorless 0.240.220.16 mm Data collection

Bruker SMART CCD area-detector diffractometer

'and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996)

Tmin= 0.976,Tmax= 0.985

3540 measured re¯ections

1372 independent re¯ections 1064 re¯ections withI> 2(I)

Rint= 0.021 max= 26.4

h=ÿ10!10

k=ÿ8!8

l=ÿ8!13 Re®nement

Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.041}

wR(F2_{) = 0.114}

S= 1.08 1372 re¯ections 112 parameters

H atoms treated by a mixture of independent and constrained re®nement

w= 1/[2_(F

o2) + (0.0616P)2 + 0.071P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.22 e AÊÿ3

min=ÿ0.14 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.30 (2)

Table 1

Hydrogen-bonding geometry (AÊ,_).

DÐH A DÐH H A D A DÐH A

C5ÐH5 O1ii _{0.93 2.36 3.249 (3) 161}

C5ÐH5 O1iii _{0.93 2.36 3.249 (3) 161} Symmetry code: (ii) 1‡x;y;z; (iii) 1‡x;1

2ÿy;z.

H atoms were treated as riding, with CÐH distances of 0.93± 0.97 AÊ. For the H atoms attached to atom C13, Uiso(H) =

1.5Ueq(C13); all otherUiso(H) values were re®ned.

Data collection:SMART(Bruker, 1997); cell re®nement:SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure:SHELXTL (Sheldrick, 2001); program(s) used to re®ne structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.

References

Bruker (1997).SMART(Version 5.051) andSAINT(Version 5.A06). Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996).SADABS. University of GoÈttingen, Germany. Sheldrick, G. M. (2001).SHELXTL.Version 6.12. Bruker AXS Inc., Madison,

Wisconsin, USA.

Figure 2

Packing diagram showing CÐH O interactions, viewed down thebaxis.

Figure 1

The molecular structure of (I), showing 30% probability displacement ellipsoids. [Symmetry code: (i)x,1

supporting information

sup-1

Acta Cryst. (2004). E60, o306–o307

supporting information

Acta Cryst. (2004). E60, o306–o307 [https://doi.org/10.1107/S1600536804001825]

N

-(4-Methyl-1-piperazinyl)phthalimide

Ming-Lin Guo

N-(4-methyl-1-piperazinyl)phthalimide

Crystal data

C13H15N3O2 Mr = 245.28

Monoclinic, P21/m Hall symbol: -P 2yb a = 8.364 (3) Å b = 6.816 (3) Å c = 10.972 (5) Å β = 101.980 (6)° V = 611.9 (4) Å3 Z = 2

F(000) = 260 Dx = 1.331 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 853 reflections θ = 2.8–26.4°

µ = 0.09 mm−1 T = 293 K Prism, colorless 0.24 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.976, Tmax = 0.985

3540 measured reflections 1372 independent reflections 1064 reflections with I > 2σ(I) Rint = 0.021

θmax = 26.4°, θmin = 1.9° h = −10→10

k = −8→8 l = −8→13

Refinement

Refinement on F2 Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.041} wR(F2_{) = 0.114} S = 1.08 1372 reflections 112 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(Fo2_{) + (0.0616P)}2 _{+ 0.071P]}

where P = (Fo2 _{+ 2Fc}2_)/3 (Δ/σ)max < 0.001

Δρmax = 0.22 e Å−3 Δρmin = −0.14 e Å−3

Special details

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 F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2₎

x y z Uiso*/Ueq

O1 0.09160 (17) 0.2500 0.53563 (13) 0.0658 (5) O2 0.33863 (19) 0.2500 0.20035 (13) 0.0656 (5) N1 0.17519 (19) 0.2500 0.34678 (14) 0.0454 (4) N2 0.01766 (19) 0.2500 0.26989 (15) 0.0459 (4) N3 −0.2218 (2) 0.2500 0.04513 (14) 0.0498 (5) C1 0.1975 (2) 0.2500 0.47739 (17) 0.0430 (5) C2 0.3774 (2) 0.2500 0.52412 (17) 0.0387 (4) C3 0.4669 (2) 0.2500 0.64501 (18) 0.0447 (5) H3 0.4158 0.2500 0.7126 0.052 (6)* C4 0.6360 (2) 0.2500 0.6615 (2) 0.0481 (5) H4 0.6997 0.2500 0.7418 0.050 (6)* C5 0.7113 (2) 0.2500 0.5608 (2) 0.0502 (5) H5 0.8248 0.2500 0.5744 0.068 (7)* C6 0.6206 (2) 0.2500 0.4402 (2) 0.0494 (5) H6 0.6717 0.2500 0.3725 0.052 (6)* C7 0.4526 (2) 0.2500 0.42321 (17) 0.0408 (4) C8 0.3241 (2) 0.2500 0.30737 (18) 0.0460 (5) C9 −0.01328 (18) 0.0716 (2) 0.19382 (14) 0.0547 (4) H9A 0.0051 −0.0435 0.2469 0.066 (5)* H9B 0.0604 0.0657 0.1363 0.071 (5)* C10 −0.18826 (17) 0.0754 (2) 0.12258 (13) 0.0537 (4) H10A −0.2094 −0.0404 0.0704 0.066 (5)* H10B −0.2610 0.0722 0.1808 0.061 (4)* C13 −0.3922 (3) 0.2500 −0.0222 (2) 0.0652 (7) H13A −0.4127 0.3650 −0.0736 0.098* H13B −0.4629 0.2500 0.0364 0.098*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

supporting information

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Acta Cryst. (2004). E60, o306–o307

C1 0.0373 (10) 0.0501 (11) 0.0408 (10) 0.000 0.0064 (8) 0.000 C2 0.0348 (9) 0.0368 (9) 0.0439 (10) 0.000 0.0069 (7) 0.000 C3 0.0399 (10) 0.0487 (11) 0.0440 (10) 0.000 0.0055 (8) 0.000 C4 0.0385 (10) 0.0460 (11) 0.0546 (12) 0.000 −0.0023 (9) 0.000 C5 0.0316 (9) 0.0453 (11) 0.0722 (14) 0.000 0.0075 (9) 0.000 C6 0.0443 (11) 0.0484 (11) 0.0598 (12) 0.000 0.0210 (9) 0.000 C7 0.0404 (10) 0.0367 (9) 0.0463 (10) 0.000 0.0110 (8) 0.000 C8 0.0473 (11) 0.0475 (11) 0.0446 (10) 0.000 0.0129 (8) 0.000 C9 0.0558 (9) 0.0478 (9) 0.0548 (9) 0.0010 (6) −0.0021 (7) −0.0021 (7) C10 0.0545 (9) 0.0551 (9) 0.0469 (8) −0.0060 (7) 0.0003 (6) −0.0043 (7) C13 0.0515 (13) 0.0928 (18) 0.0454 (11) 0.000 −0.0033 (10) 0.000

Geometric parameters (Å, º)

O1—C1 1.195 (2) C4—C5 1.381 (3) O2—C8 1.205 (2) C4—H4 0.9300 N1—C8 1.401 (2) C5—C6 1.382 (3) N1—C1 1.406 (2) C5—H5 0.9300 N1—N2 1.409 (2) C6—C7 1.379 (3) N2—C9i _{1.4672 (17) C6—H6 0.9299} N2—C9 1.4672 (17) C7—C8 1.484 (3) N3—C10i _{1.4554 (18) C9—C10 1.5095 (19)} N3—C10 1.4554 (18) C9—H9A 0.9699 N3—C13 1.463 (3) C9—H9B 0.9700 C1—C2 1.486 (2) C10—H10A 0.9699 C2—C3 1.381 (3) C10—H10B 0.9699 C2—C7 1.382 (3) C13—H13A 0.9599 C3—C4 1.388 (3) C13—H13B 0.9600 C3—H3 0.9300

C5—C4—C3 121.15 (19) N3—C10—H10B 109.4 C5—C4—H4 119.4 C9—C10—H10B 109.4 C3—C4—H4 119.4 H10A—C10—H10B 108.0 C4—C5—C6 121.04 (18) N3—C13—H13A 109.5 C4—C5—H5 119.5 N3—C13—H13B 109.5 C6—C5—H5 119.5 H13A—C13—H13B 109.5

C8—N1—N2—C9i _{−63.29 (11) C5—C6—C7—C8 180.0} C1—N1—N2—C9i _{116.71 (11) C3—C2—C7—C6 0.0} C8—N1—N2—C9 63.29 (11) C1—C2—C7—C6 180.0 C1—N1—N2—C9 −116.71 (11) C3—C2—C7—C8 180.0 C8—N1—C1—O1 180.0 C1—C2—C7—C8 0.0 N2—N1—C1—O1 0.0 C1—N1—C8—O2 180.0 C8—N1—C1—C2 0.0 N2—N1—C8—O2 0.0 N2—N1—C1—C2 180.0 C1—N1—C8—C7 0.0 O1—C1—C2—C3 0.0 N2—N1—C8—C7 180.0 N1—C1—C2—C3 180.0 C6—C7—C8—O2 0.0 O1—C1—C2—C7 180.0 C2—C7—C8—O2 180.0 N1—C1—C2—C7 0.0 C6—C7—C8—N1 180.0 C7—C2—C3—C4 0.0 C2—C7—C8—N1 0.0

C1—C2—C3—C4 180.0 N1—N2—C9—C10 175.38 (12) C2—C3—C4—C5 0.0 C9i_{—N2—C9—C10 −58.1 (2)} C3—C4—C5—C6 0.0 C10i_{—N3—C10—C9 −58.3 (2)} C4—C5—C6—C7 0.0 C13—N3—C10—C9 −179.75 (14) C5—C6—C7—C2 0.0 N2—C9—C10—N3 57.70 (17)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

C5—H5···O1ii _{0.93 2.36 3.249 (3) 161} C5—H5···O1iii _{0.93 2.36 3.249 (3) 161}