3-(4-Methyl­piperazin-1-yl)isobenzofuran-1(3H)-one

Odabaşoğlu, M.; Büyükgüngör, O.

doi:10.1107/S1600536808008209

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o779

doi:10.1107/S1600536808008209

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3-(4-Methylpiperazin-1-yl)isobenzofuran-1(3H)-one †

Mustafa Odabaşoğlu ^a and Orhan Büyükgüngör ^b ^*

^aDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 26 March 2008; accepted 26 March 2008; online 2 April 2008)

In the molecule of the title compound, C₁₃H₁₆N₂O₂, the phthalide ring system is virtually planar, with a dihedral angle between the fused five- and six-membered rings of 1.17 (4)°. The methylpiperazine ring adopts a chair conformation. In the crystal structure, intermolecular C—H⋯O and C—H⋯N hydrogen bonds link the molecules, generating edge-fused R₃³(17) ring motifs, to form a three-dimensional network.

Related literature

For a related structure, see: Odabaşoğlu & Büyükgüngör (2006 ). For ring motif details, see: Bernstein et al. (1995 ); Etter (1990 ). For ring conformation puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₃H₁₆N₂O₂
M_r = 232.28
Monoclinic, P 2₁ /c
a = 13.1442 (7) Å
b = 6.0567 (4) Å
c = 15.7845 (10) Å
β = 104.022 (5)°
V = 1219.17 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.56 × 0.49 × 0.37 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.952, T_max = 0.969
14223 measured reflections
2394 independent reflections
1890 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.091
S = 1.04
2394 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.98	2.69	3.6135 (18)	157
C10—H10A⋯N2ⁱⁱ	0.97	2.60	3.5315 (17)	160
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808008209/hk2441sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008209/hk2441Isup2.hkl

checkCIF report

Comment top

The present work is part of a structural study of compounds of 3-substituted phthalides, and we report herein the structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings A (C2–C7) and B (C1/C2/C7/C8/O2) are, of course, planar. The dihedral angle between them is A/B = 1.17 (4)°. So, rings A and B are also nearly coplanar. Ring C (N1/N2/C9–C12) is not planar, having total puckering amplitude, Q_T, of 1.014 (3) Å. It adopts chair [ϕ = 29.44 (2)° and θ = 59.51 (3)°] conformation (Cremer & Pople, 1975).

In the crystal structure, intermolecular C—H···O and C—H···N hydrogen bonds (Table 1) link the molecules, generating edge-fused R₃³(17) (Fig. 2) ring motifs (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, in which they may be effective in the stabilization of the structure.

Related literature top

For a related structure, see: Odabaşoğlu & Büyükgüngör (2006). For ring motif details, see: Bernstein et al. (1995); Etter (1990). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and 1-methylpiperazine as starting materials (yield; 85%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol–DMF (1:1) solution at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of (I), showing the formation of R₃³(17) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, y + 1, z; (ii) 1 - x, 2 - y, 1/2 - z]. H atoms not involved in hydrogen bondings have been omitted for clarity.

3-(4-methylpiperazin-1-yl)isobenzofuran-1(3H)-one top

Crystal data top

C₁₃H₁₆N₂O₂	F(000) = 496
M_r = 232.28	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14223 reflections
a = 13.1442 (7) Å	θ = 1.3–27.2°
b = 6.0567 (4) Å	µ = 0.09 mm⁻¹
c = 15.7845 (10) Å	T = 296 K
β = 104.022 (5)°	Prism, colourless
V = 1219.17 (13) Å³	0.56 × 0.49 × 0.37 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	2394 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1890 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.035
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.6°
w–scan rotation method	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
T_min = 0.952, T_max = 0.969	l = −19→19
14223 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0465P)² + 0.1087P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2394 reflections	Δρ_max = 0.14 e Å⁻³
155 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (3)

Crystal data top

C₁₃H₁₆N₂O₂	V = 1219.17 (13) Å³
M_r = 232.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1442 (7) Å	µ = 0.09 mm⁻¹
b = 6.0567 (4) Å	T = 296 K
c = 15.7845 (10) Å	0.56 × 0.49 × 0.37 mm
β = 104.022 (5)°

Data collection top

Stoe IPDSII diffractometer	2394 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1890 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.969	R_int = 0.035
14223 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
2394 reflections	Δρ_min = −0.11 e Å⁻³
155 parameters

Special details top

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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
O1	0.90768 (9)	0.78386 (19)	0.39052 (8)	0.0726 (3)
O2	0.83029 (7)	0.45298 (17)	0.38597 (6)	0.0573 (3)
N1	0.69300 (8)	0.23856 (17)	0.42651 (7)	0.0465 (3)
N2	0.47776 (8)	0.18458 (18)	0.34023 (6)	0.0468 (3)
C1	0.87740 (10)	0.6335 (2)	0.42833 (9)	0.0536 (3)
C2	0.88098 (9)	0.6114 (2)	0.52149 (9)	0.0500 (3)
C3	0.91995 (11)	0.7553 (3)	0.59001 (11)	0.0616 (4)
H3	0.9512	0.8881	0.5810	0.074*
C4	0.91066 (11)	0.6944 (3)	0.67175 (11)	0.0678 (4)
H4	0.9355	0.7880	0.7189	0.081*
C5	0.86475 (11)	0.4955 (3)	0.68471 (10)	0.0656 (4)
H5	0.8597	0.4574	0.7406	0.079*
C6	0.82633 (10)	0.3527 (3)	0.61639 (9)	0.0582 (4)
H6	0.7954	0.2194	0.6254	0.070*
C7	0.83528 (9)	0.4141 (2)	0.53414 (9)	0.0479 (3)
C8	0.80023 (10)	0.2952 (2)	0.44870 (9)	0.0502 (3)
H8	0.8419	0.1601	0.4509	0.060*
C9	0.66011 (11)	0.0825 (2)	0.35430 (9)	0.0520 (3)
H9A	0.7084	−0.0412	0.3621	0.062*
H9B	0.6608	0.1545	0.2995	0.062*
C10	0.55130 (11)	0.0013 (2)	0.35199 (9)	0.0515 (3)
H10A	0.5293	−0.1029	0.3044	0.062*
H10B	0.5515	−0.0746	0.4061	0.062*
C11	0.51096 (10)	0.3423 (2)	0.41085 (9)	0.0485 (3)
H11A	0.5086	0.2729	0.4657	0.058*
H11B	0.4629	0.4664	0.4017	0.058*
C12	0.62040 (10)	0.4247 (2)	0.41613 (9)	0.0468 (3)
H12A	0.6219	0.5054	0.3634	0.056*
H12B	0.6417	0.5244	0.4653	0.056*
C13	0.37178 (12)	0.1092 (3)	0.33673 (11)	0.0711 (5)
H13A	0.3252	0.2336	0.3289	0.107*
H13B	0.3706	0.0351	0.3903	0.107*
H13C	0.3496	0.0089	0.2887	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0645 (7)	0.0696 (7)	0.0885 (8)	0.0008 (5)	0.0281 (6)	0.0230 (6)
O2	0.0522 (5)	0.0658 (6)	0.0575 (6)	0.0024 (5)	0.0200 (4)	0.0016 (5)
N1	0.0447 (6)	0.0395 (6)	0.0549 (6)	0.0040 (5)	0.0116 (5)	−0.0060 (5)
N2	0.0493 (6)	0.0476 (6)	0.0426 (6)	−0.0004 (5)	0.0095 (4)	−0.0034 (5)
C1	0.0395 (7)	0.0542 (8)	0.0687 (9)	0.0076 (6)	0.0164 (6)	0.0087 (7)
C2	0.0346 (6)	0.0504 (8)	0.0633 (8)	0.0055 (6)	0.0086 (6)	0.0033 (6)
C3	0.0409 (7)	0.0587 (9)	0.0816 (10)	−0.0033 (6)	0.0082 (7)	−0.0051 (8)
C4	0.0453 (8)	0.0845 (12)	0.0679 (10)	−0.0015 (8)	0.0024 (7)	−0.0171 (9)
C5	0.0471 (8)	0.0933 (12)	0.0535 (8)	0.0038 (8)	0.0066 (6)	0.0013 (8)
C6	0.0472 (8)	0.0642 (9)	0.0619 (8)	−0.0007 (7)	0.0106 (6)	0.0092 (7)
C7	0.0372 (6)	0.0490 (8)	0.0558 (8)	0.0042 (6)	0.0080 (5)	0.0032 (6)
C8	0.0479 (7)	0.0448 (7)	0.0588 (8)	0.0064 (6)	0.0148 (6)	0.0027 (6)
C9	0.0587 (8)	0.0429 (7)	0.0544 (8)	0.0107 (6)	0.0140 (6)	−0.0077 (6)
C10	0.0651 (8)	0.0407 (7)	0.0463 (7)	−0.0012 (6)	0.0087 (6)	−0.0069 (6)
C11	0.0495 (7)	0.0466 (7)	0.0514 (7)	0.0025 (6)	0.0165 (6)	−0.0073 (6)
C12	0.0477 (7)	0.0372 (7)	0.0573 (8)	0.0032 (6)	0.0159 (6)	−0.0065 (6)
C13	0.0568 (9)	0.0815 (11)	0.0733 (10)	−0.0138 (8)	0.0123 (7)	−0.0175 (9)

Geometric parameters (Å, º) top

C1—O1	1.2078 (17)	C9—C10	1.504 (2)
C1—O2	1.3512 (17)	C9—H9A	0.9700
C1—C2	1.466 (2)	C9—H9B	0.9700
C2—C7	1.3740 (19)	C10—N2	1.4537 (17)
C2—C3	1.387 (2)	C10—H10A	0.9700
C3—C4	1.375 (2)	C10—H10B	0.9700
C3—H3	0.9300	C11—N2	1.4526 (16)
C4—C5	1.384 (2)	C11—C12	1.5056 (18)
C4—H4	0.9300	C11—H11A	0.9700
C5—C6	1.379 (2)	C11—H11B	0.9700
C5—H5	0.9300	C12—N1	1.4602 (16)
C6—C7	1.3826 (19)	C12—H12A	0.9700
C6—H6	0.9300	C12—H12B	0.9700
C7—C8	1.4995 (19)	C13—N2	1.4543 (18)
C8—N1	1.4098 (17)	C13—H13A	0.9600
C8—O2	1.4966 (16)	C13—H13B	0.9600
C8—H8	0.9800	C13—H13C	0.9600
C9—N1	1.4629 (16)

C1—O2—C8	110.62 (10)	O2—C8—H8	108.8
C8—N1—C12	115.28 (10)	C7—C8—H8	108.8
C8—N1—C9	116.08 (10)	N1—C9—C10	109.26 (10)
C12—N1—C9	110.46 (10)	N1—C9—H9A	109.8
C11—N2—C10	109.72 (10)	C10—C9—H9A	109.8
C11—N2—C13	110.04 (11)	N1—C9—H9B	109.8
C10—N2—C13	111.48 (12)	C10—C9—H9B	109.8
O1—C1—O2	122.13 (14)	H9A—C9—H9B	108.3
O1—C1—C2	129.07 (15)	N2—C10—C9	110.63 (11)
O2—C1—C2	108.78 (12)	N2—C10—H10A	109.5
C7—C2—C3	121.67 (14)	C9—C10—H10A	109.5
C7—C2—C1	108.45 (12)	N2—C10—H10B	109.5
C3—C2—C1	129.87 (14)	C9—C10—H10B	109.5
C4—C3—C2	117.60 (15)	H10A—C10—H10B	108.1
C4—C3—H3	121.2	N2—C11—C12	111.45 (10)
C2—C3—H3	121.2	N2—C11—H11A	109.3
C3—C4—C5	120.85 (15)	C12—C11—H11A	109.3
C3—C4—H4	119.6	N2—C11—H11B	109.3
C5—C4—H4	119.6	C12—C11—H11B	109.3
C6—C5—C4	121.35 (14)	H11A—C11—H11B	108.0
C6—C5—H5	119.3	N1—C12—C11	109.89 (10)
C4—C5—H5	119.3	N1—C12—H12A	109.7
C5—C6—C7	117.86 (14)	C11—C12—H12A	109.7
C5—C6—H6	121.1	N1—C12—H12B	109.7
C7—C6—H6	121.1	C11—C12—H12B	109.7
C2—C7—C6	120.67 (13)	H12A—C12—H12B	108.2
C2—C7—C8	109.69 (12)	N2—C13—H13A	109.5
C6—C7—C8	129.64 (13)	N2—C13—H13B	109.5
N1—C8—O2	113.53 (10)	H13A—C13—H13B	109.5
N1—C8—C7	114.27 (11)	N2—C13—H13C	109.5
O2—C8—C7	102.45 (10)	H13A—C13—H13C	109.5
N1—C8—H8	108.8	H13B—C13—H13C	109.5

O1—C1—O2—C8	−179.48 (12)	C2—C7—C8—O2	−1.01 (13)
C2—C1—O2—C8	−0.77 (13)	C6—C7—C8—O2	178.33 (12)
O1—C1—C2—C7	178.69 (14)	N1—C8—O2—C1	124.81 (11)
O2—C1—C2—C7	0.10 (14)	C7—C8—O2—C1	1.08 (13)
O1—C1—C2—C3	−0.2 (2)	O2—C8—N1—C12	−55.67 (14)
O2—C1—C2—C3	−178.84 (13)	C7—C8—N1—C12	61.34 (15)
C7—C2—C3—C4	−0.5 (2)	O2—C8—N1—C9	75.74 (14)
C1—C2—C3—C4	178.35 (13)	C7—C8—N1—C9	−167.25 (11)
C2—C3—C4—C5	0.5 (2)	C10—C9—N1—C8	167.50 (11)
C3—C4—C5—C6	−0.4 (2)	C10—C9—N1—C12	−58.87 (14)
C4—C5—C6—C7	0.1 (2)	N1—C9—C10—N2	59.53 (14)
C3—C2—C7—C6	0.25 (19)	C9—C10—N2—C11	−58.56 (13)
C1—C2—C7—C6	−178.80 (11)	C9—C10—N2—C13	179.29 (11)
C3—C2—C7—C8	179.66 (12)	C12—C11—N2—C10	57.22 (14)
C1—C2—C7—C8	0.61 (14)	C12—C11—N2—C13	−179.77 (12)
C5—C6—C7—C2	−0.08 (19)	N2—C11—C12—N1	−56.78 (14)
C5—C6—C7—C8	−179.35 (13)	C11—C12—N1—C8	−168.52 (10)
C2—C7—C8—N1	−124.24 (12)	C11—C12—N1—C9	57.45 (14)
C6—C7—C8—N1	55.10 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.98	2.69	3.6135 (18)	157
C10—H10A···N2ⁱⁱ	0.97	2.60	3.5315 (17)	160

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂O₂
M_r	232.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.1442 (7), 6.0567 (4), 15.7845 (10)
β (°)	104.022 (5)
V (Å³)	1219.17 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.56 × 0.49 × 0.37

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.952, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	14223, 2394, 1890
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.091, 1.04
No. of reflections	2394
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.11

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.98	2.69	3.6135 (18)	156.7
C10—H10A···N2ⁱⁱ	0.97	2.60	3.5315 (17)	160.4

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2.

Footnotes

†3-Substituted phthalides. XXXVI.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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