organic compounds
3-(4-Methylpiperazin-1-yl)isobenzofuran-1(3H)-one†
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
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 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
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell 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
10.1107/S1600536808008209/hk2441sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008209/hk2441Isup2.hkl
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.
H atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: X-AREA (Stoe & Cie, 2002); cell
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).C13H16N2O2 | F(000) = 496 |
Mr = 232.28 | Dx = 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 |
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 | Rint = 0.035 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
w–scan rotation method | h = −16→16 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −7→7 |
Tmin = 0.952, Tmax = 0.969 | l = −19→19 |
14223 measured reflections |
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(Fo2) + (0.0465P)2 + 0.1087P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2394 reflections | Δρmax = 0.14 e Å−3 |
155 parameters | Δρmin = −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) |
C13H16N2O2 | V = 1219.17 (13) Å3 |
Mr = 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)° |
Stoe IPDSII diffractometer | 2394 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1890 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.969 | Rint = 0.035 |
14223 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.14 e Å−3 |
2394 reflections | Δρmin = −0.11 e Å−3 |
155 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.952, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14223, 2394, 1890 |
Rint | 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 |
Δρmax, Δρmin (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).
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 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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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, QT, 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.