organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N,N,N′,N′-Tetra­methyl­phthalamide

aDépartement des Sciences Fondamentales, Faculté des Sciences, Université du 20 Août 1955 – Skikda, Route d'El-Hadaïk, BP 26, 21000 Skikda, Algeria, and bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université-Mentouri, 25000 Constantine, Algeria
*Correspondence e-mail: a_beghidja@yahoo.fr

(Received 2 August 2012; accepted 8 August 2012; online 15 August 2012)

The title compound, C12H16N2O2, crystallized from toluene with two independent mol­ecules in the asymmetric unit. The dihedral angles between the amide groups and the benzene ring are 60.87 (11) and 54.08 (11)° in one independent molecule and 60.13 (11) and 64.64 (11) in the other. The crystal structure features weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions.

Related literature

For related structures, see: Altamura et al. (2005[Altamura, M., Coppini, G., Cuda, F., Dapporto, P., Guerri, A., Guidi, A., Nativi, C., Paoli, P. & Rossi, P. (2005). J. Mol. Struct. 749, 20-30.]); Anderson et al. (2004[Anderson, R. J., Batsanov, A. S., Belskaia, N., Groundwater, P. W., Meth-Cohn, O. & Zaytsev, A. (2004). Tetrahedron Lett. 45, 943-946.]); Clayden et al. (2001[Clayden, J., Lai, L. W. & Helliwell, M. (2001). Tetrahedron Asymmetry, 12, 695-698.]); Comins et al. (1998[Comins, D. L., Lee, Y. S. & Boyle, P. D. (1998). Tetrahedron Lett., 39, 187-190.]); Sakamoto et al. (2004[Sakamoto, M., Kobaru, S., Mino, T. & Fujita, T. (2004). Chem. Commun. pp. 1002-1003.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16N2O2

  • Mr = 220.27

  • Monoclinic, P 21

  • a = 6.7337 (6) Å

  • b = 18.1230 (14) Å

  • c = 9.8216 (8) Å

  • β = 104.918 (3)°

  • V = 1158.18 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.56 × 0.52 × 0.33 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.925, Tmax = 0.972

  • 8205 measured reflections

  • 2739 independent reflections

  • 2414 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.124

  • S = 1.06

  • 2739 reflections

  • 297 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O3i 0.93 2.60 3.518 (3) 170
C5—H5⋯O4ii 0.93 2.58 3.141 (4) 119
C6—H6⋯O4ii 0.93 2.51 3.105 (4) 122
C18—H18⋯O2iii 0.93 2.49 3.329 (3) 150
C24—H24A⋯O2iii 0.96 2.56 3.224 (4) 127
C16—H16⋯Cg1 0.93 2.97 3.810 (4) 124
Symmetry codes: (i) x, y, z-1; (ii) x+1, y, z; (iii) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ATOMS (Dowty, 1995[Dowty, E. (1995). ATOMS. Shape Software, Kingsport, Tennessee, USA.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The molecular structure of (I) is composed of a two crystallographically independent molecules (IA and IB). A displacement ellipsoid plot of the two independent molecules of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal, and values for the two independent molecules agree with each other. The crystal structure of (I) is stabilized by intermolecular weak hydrogen-bonds type C—H···O (Fig. 2) and C—H··· π interactions, the latter interaction is observed between centroid of benzene ring (C2—C7) (IA) and hydrogen atom H16 of benzene ring (C14—C19) of the adjacent molecule (IB), with a Cg···H16 distance of 2.96 (2) Å (Fig. 1), resulting in the formation of infinite three-dimensional network reinforcing a cohesion of structure. Hydrogen-bonding parameters are listed in Table 1.

Related literature top

For related literature, see: Altamura et al. (2005); Anderson et al. (2004); Clayden et al. (2001); Comins et al. (1998); Sakamoto et al. (2004). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···.? etc. Please revise this section as indicated.

Experimental top

To a suspension of phthalic acid (1 g, 6.02 mmol) in anhydrous toluene (10 ml) trimethlphosphine (6.02 mmol) was added and the mixture kept under reflux for 45 min. The resulting cloudy solution was allowed to cool to room temperature and a saturated aqueous solution of NaHCO3 (5 ml) was added. The layers were separated and the aqueous phase was extracted with methylene chloride (4.5 ml). The organic solutions were combined together, dried over anhydrous MgSO4 and concentrated to dryness, obtaining a white solid. Colorless single crystals suitable for X-ray diffraction analysis were obtained by dissolving the corresponding compound in toluene solution and letting it for slow evaporation at room temperature (Yield: 1.30 g, 92%).

Refinement top

All non-hydrogen atoms were refined with anisotropic atomic displacement parameters. All H atoms were placed at calculated positions and treated as riding on their parent atoms with C—H = 0.93–0.96 Å, and Uiso (H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others. The absolute structure parameter is meaningless because the compound is a weak anomalous scatterer. So, the absolute structure parameter is removed from the CIF.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ATOMS (Dowty, 1995); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
Fig. 1. View of the two molecules in the asymmetric unit of (I) showing the numbering schemes; displacement ellipsoids are drawn at the 50% probability level.

Fig. 2. Partial view of the crystal structure of (I) showing the non standard hydrogen bonds.
N,N,N',N'-Tetramethylphthalamide top
Crystal data top
C12H16N2O2F(000) = 472
Mr = 220.27Dx = 1.263 Mg m3
Monoclinic, P21Melting point: 118 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.7337 (6) ÅCell parameters from 2761 reflections
b = 18.1230 (14) Åθ = 2.4–26.8°
c = 9.8216 (8) ŵ = 0.09 mm1
β = 104.918 (3)°T = 100 K
V = 1158.18 (17) Å3Needles, colourless
Z = 40.56 × 0.52 × 0.33 mm
Data collection top
Bruker APEXII
diffractometer
2739 independent reflections
Graphite monochromator2414 reflections with I > 2σ(I)
Detector resolution: 18.4 pixels mm-1Rint = 0.045
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 88
Tmin = 0.925, Tmax = 0.972k = 2320
8205 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0785P)2]
where P = (Fo2 + 2Fc2)/3
2739 reflections(Δ/σ)max < 0.001
297 parametersΔρmax = 0.32 e Å3
1 restraintΔρmin = 0.34 e Å3
Crystal data top
C12H16N2O2V = 1158.18 (17) Å3
Mr = 220.27Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.7337 (6) ŵ = 0.09 mm1
b = 18.1230 (14) ÅT = 100 K
c = 9.8216 (8) Å0.56 × 0.52 × 0.33 mm
β = 104.918 (3)°
Data collection top
Bruker APEXII
diffractometer
2739 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
2414 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.972Rint = 0.045
8205 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.124H-atom parameters constrained
S = 1.06Δρmax = 0.32 e Å3
2739 reflectionsΔρmin = 0.34 e Å3
297 parameters
Special details top

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
O10.7861 (3)0.24084 (11)0.0065 (2)0.0216 (6)
O20.8041 (3)0.28421 (11)0.3142 (2)0.0235 (6)
N10.4493 (3)0.26282 (13)0.0175 (2)0.0195 (7)
N21.0989 (4)0.21659 (13)0.3653 (2)0.0220 (7)
C10.6269 (4)0.22638 (15)0.0296 (3)0.0171 (7)
C20.6276 (4)0.16096 (14)0.1249 (3)0.0168 (7)
C30.5027 (4)0.10057 (15)0.0751 (3)0.0189 (7)
C40.5113 (4)0.03795 (16)0.1583 (3)0.0235 (8)
C50.6447 (4)0.03548 (15)0.2915 (3)0.0211 (8)
C60.7738 (4)0.09499 (15)0.3414 (3)0.0200 (7)
C70.7675 (4)0.15789 (14)0.2577 (3)0.0171 (7)
C80.8934 (4)0.22495 (16)0.3135 (3)0.0189 (7)
C90.4327 (5)0.32006 (16)0.1231 (3)0.0244 (8)
C100.2644 (4)0.25242 (16)0.0331 (3)0.0232 (8)
C111.2112 (4)0.14818 (17)0.3610 (3)0.0261 (8)
C121.2221 (5)0.27854 (19)0.4338 (3)0.0312 (9)
O30.1819 (3)0.12996 (12)0.7353 (2)0.0259 (6)
O40.0391 (4)0.02611 (13)0.5606 (2)0.0358 (7)
N30.1580 (3)0.14947 (12)0.7148 (2)0.0186 (6)
N40.2973 (4)0.05367 (13)0.6492 (3)0.0258 (8)
C130.0169 (4)0.11065 (15)0.7583 (3)0.0188 (7)
C140.0152 (4)0.04326 (15)0.8474 (3)0.0180 (7)
C150.0313 (4)0.05018 (16)0.9770 (3)0.0209 (8)
C160.0171 (5)0.01003 (17)1.0661 (3)0.0224 (8)
C170.0435 (4)0.07820 (16)1.0259 (3)0.0209 (8)
C180.0923 (4)0.08572 (14)0.8968 (3)0.0206 (7)
C190.0795 (4)0.02558 (15)0.8073 (3)0.0189 (7)
C200.1098 (5)0.03514 (15)0.6626 (3)0.0235 (8)
C210.1553 (5)0.22148 (16)0.6495 (3)0.0244 (8)
C220.3615 (4)0.12250 (17)0.7172 (3)0.0243 (8)
C230.3187 (7)0.0733 (2)0.5096 (4)0.0426 (13)
C240.4731 (5)0.06937 (18)0.7671 (3)0.0292 (9)
H30.412900.102100.014300.0230*
H40.427300.002300.124400.0280*
H50.648200.006000.347800.0250*
H60.864400.092900.430500.0240*
H9A0.560900.324400.148200.0370*
H9B0.400600.366200.085700.0370*
H9C0.325700.307500.205200.0370*
H10A0.293200.218100.110100.0350*
H10B0.155400.233500.042000.0350*
H10C0.223500.298900.064200.0350*
H11A1.137700.118600.283200.0390*
H11B1.224500.121500.447300.0390*
H11C1.345300.159400.349500.0390*
H12A1.135300.320800.431700.0470*
H12B1.325000.289800.385100.0470*
H12C1.287500.265900.529800.0470*
H150.072300.095701.004100.0250*
H160.048200.004801.152500.0270*
H170.051600.118801.085000.0250*
H180.133800.131300.870500.0250*
H21A0.019700.231400.639600.0370*
H21B0.193200.258700.707600.0370*
H21C0.251200.221700.558300.0370*
H22A0.347500.079100.774900.0360*
H22B0.438200.110700.623000.0360*
H22C0.432600.160000.755200.0360*
H23A0.221200.045800.439500.0640*
H23B0.293700.125100.494000.0640*
H23C0.455400.061800.503600.0640*
H24A0.474200.120900.790300.0440*
H24B0.463600.040500.847200.0440*
H24C0.597600.057100.741700.0440*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0140 (10)0.0250 (10)0.0271 (10)0.0016 (8)0.0076 (8)0.0017 (8)
O20.0234 (11)0.0206 (9)0.0257 (10)0.0012 (9)0.0047 (9)0.0004 (8)
N10.0116 (11)0.0236 (12)0.0242 (11)0.0015 (10)0.0063 (9)0.0041 (9)
N20.0166 (12)0.0240 (11)0.0235 (11)0.0029 (10)0.0019 (10)0.0011 (9)
C10.0128 (12)0.0197 (12)0.0185 (12)0.0004 (11)0.0033 (10)0.0047 (10)
C20.0144 (12)0.0182 (11)0.0193 (12)0.0025 (10)0.0069 (10)0.0008 (10)
C30.0087 (12)0.0237 (12)0.0245 (13)0.0005 (11)0.0044 (10)0.0019 (11)
C40.0134 (13)0.0222 (13)0.0365 (15)0.0026 (11)0.0094 (12)0.0036 (12)
C50.0181 (14)0.0188 (12)0.0290 (14)0.0027 (11)0.0106 (12)0.0048 (11)
C60.0149 (13)0.0226 (12)0.0233 (13)0.0029 (11)0.0066 (11)0.0009 (10)
C70.0117 (12)0.0188 (12)0.0215 (12)0.0017 (11)0.0057 (10)0.0017 (10)
C80.0178 (13)0.0228 (12)0.0169 (12)0.0005 (12)0.0058 (10)0.0026 (10)
C90.0179 (14)0.0258 (13)0.0273 (14)0.0004 (12)0.0020 (12)0.0050 (11)
C100.0127 (13)0.0242 (13)0.0338 (15)0.0013 (11)0.0082 (12)0.0014 (12)
C110.0122 (13)0.0331 (15)0.0310 (15)0.0020 (13)0.0017 (12)0.0005 (12)
C120.0271 (17)0.0319 (15)0.0297 (15)0.0084 (15)0.0014 (13)0.0054 (13)
O30.0141 (10)0.0294 (10)0.0368 (11)0.0012 (9)0.0111 (9)0.0060 (9)
O40.0446 (15)0.0339 (11)0.0247 (11)0.0143 (12)0.0015 (10)0.0000 (9)
N30.0120 (11)0.0202 (11)0.0231 (11)0.0032 (9)0.0036 (9)0.0016 (9)
N40.0330 (15)0.0220 (11)0.0273 (13)0.0061 (11)0.0165 (12)0.0022 (9)
C130.0145 (13)0.0218 (12)0.0203 (12)0.0007 (11)0.0047 (10)0.0033 (10)
C140.0092 (12)0.0189 (12)0.0242 (13)0.0001 (10)0.0010 (10)0.0006 (10)
C150.0127 (13)0.0236 (12)0.0265 (14)0.0004 (11)0.0052 (11)0.0040 (11)
C160.0159 (14)0.0285 (14)0.0241 (13)0.0028 (12)0.0076 (12)0.0013 (11)
C170.0112 (13)0.0239 (13)0.0261 (14)0.0042 (11)0.0020 (11)0.0025 (11)
C180.0166 (13)0.0177 (12)0.0259 (13)0.0007 (11)0.0025 (11)0.0029 (10)
C190.0109 (13)0.0204 (12)0.0239 (13)0.0003 (11)0.0019 (10)0.0011 (10)
C200.0293 (17)0.0163 (12)0.0245 (14)0.0042 (12)0.0060 (13)0.0017 (10)
C210.0225 (15)0.0248 (13)0.0277 (14)0.0064 (13)0.0098 (12)0.0050 (12)
C220.0084 (13)0.0300 (14)0.0321 (15)0.0020 (12)0.0008 (11)0.0025 (12)
C230.064 (3)0.0364 (17)0.0380 (19)0.0132 (19)0.0323 (19)0.0050 (15)
C240.0218 (16)0.0261 (14)0.0431 (17)0.0013 (13)0.0145 (14)0.0019 (13)
Geometric parameters (Å, º) top
O1—C11.241 (3)C10—H10C0.9600
O2—C81.232 (4)C10—H10B0.9600
O3—C131.240 (3)C11—H11B0.9600
O4—C201.232 (4)C11—H11C0.9600
N1—C101.467 (3)C11—H11A0.9600
N1—C11.340 (4)C12—H12B0.9600
N1—C91.451 (4)C12—H12C0.9600
N2—C111.459 (4)C12—H12A0.9600
N2—C81.354 (4)C13—C141.504 (4)
N2—C121.454 (4)C14—C151.393 (4)
N3—C131.344 (3)C14—C191.410 (4)
N3—C221.461 (4)C15—C161.387 (4)
N3—C211.456 (4)C16—C171.390 (4)
N4—C231.459 (5)C17—C181.396 (4)
N4—C241.455 (4)C18—C191.389 (4)
N4—C201.345 (4)C19—C201.497 (4)
C1—C21.510 (4)C15—H150.9300
C2—C71.400 (4)C16—H160.9300
C2—C31.390 (4)C17—H170.9300
C3—C41.391 (4)C18—H180.9300
C4—C51.384 (4)C21—H21A0.9600
C5—C61.393 (4)C21—H21B0.9600
C6—C71.400 (4)C21—H21C0.9600
C7—C81.502 (4)C22—H22A0.9600
C3—H30.9300C22—H22B0.9600
C4—H40.9300C22—H22C0.9600
C5—H50.9300C23—H23A0.9600
C6—H60.9300C23—H23B0.9600
C9—H9A0.9600C23—H23C0.9600
C9—H9B0.9600C24—H24A0.9600
C9—H9C0.9600C24—H24B0.9600
C10—H10A0.9600C24—H24C0.9600
O1···O23.218 (3)C16···H4v2.9000
O1···C83.052 (3)C17···H4v2.8700
O1···C10i3.150 (3)C17···H10Cx2.8600
O1···C22ii3.400 (4)C18···H24B2.7900
O1···C18iii3.355 (3)C18···H10Cx3.0800
O2···C24iii3.224 (4)C18···H24A3.0800
O2···C12.936 (3)C19···H24B2.5300
O2···C20iii3.322 (3)C22···H153.0200
O2···N4iii3.059 (3)C24···H182.9500
O2···C23iii3.329 (4)C24···H22Ai2.9400
O2···C18iii3.329 (3)H3···C14vii2.8800
O2···O13.218 (3)H3···O3vii2.6000
O3···C203.085 (3)H3···N12.9200
O3···C22i3.128 (3)H3···C102.9800
O4···C133.111 (4)H3···C13vii3.0100
O4···C6iv3.105 (4)H4···C16vii2.9000
O4···C5iv3.141 (4)H4···C17vii2.8700
O1···H21Bii2.8700H5···O4i2.5800
O1···H22Cii2.8300H5···H23C2.4600
O1···H9A2.3300H6···C112.7800
O1···H18iii2.6600H6···H11B2.4400
O1···H10Bi2.6000H6···O4i2.5100
O1···H15ii2.7900H6···N22.9100
O2···H12A2.3300H9A···O12.3300
O2···H24Aiii2.5600H9B···H10C2.4500
O2···H18iii2.4900H9C···H10B2.5700
O2···H21Ci2.7600H10A···H11Civ2.5200
O2···H23Biii2.7100H10A···C11iv2.9500
O3···H11Biv2.9200H10A···C22.4500
O3···H21A2.3300H10A···C32.6300
O3···H3v2.6000H10B···H9C2.5700
O3···H22Ci2.6100H10B···C13vii2.9500
O4···H6iv2.5100H10B···O1iv2.6000
O4···H23A2.3800H10C···H9B2.4500
O4···H5iv2.5800H10C···C17xi2.8600
O4···H12Avi2.8500H10C···C18xi3.0800
N4···O2vi3.059 (3)H10C···H17xi2.5300
N1···H32.9200H11A···C62.6900
N2···H62.9100H11A···C72.5400
N3···H152.9200H11B···O3i2.9200
C1···O22.936 (3)H11B···C62.9800
C3···C15vii3.593 (4)H11B···H62.4400
C3···C103.159 (4)H11B···H22Bix2.4800
C4···C16vii3.546 (4)H11C···H10Ai2.5200
C5···O4i3.141 (4)H11C···H12B2.4000
C6···C113.058 (4)H12A···O22.3300
C6···O4i3.105 (4)H12A···O4iii2.8500
C8···O13.052 (3)H12B···H11C2.4000
C8···C21i3.400 (4)H15···O1viii2.7900
C10···O1iv3.150 (3)H15···N32.9200
C10···C33.159 (4)H15···C2viii2.8500
C11···C63.058 (4)H15···C223.0200
C13···O43.111 (4)H15···H22A2.5400
C15···C3v3.593 (4)H16···C4viii3.0800
C15···C223.202 (4)H16···C5viii2.8500
C16···C4v3.546 (4)H16···C6viii3.0500
C18···O1vi3.355 (3)H17···H10Cx2.5300
C18···C243.157 (4)H18···C242.9500
C18···O2vi3.329 (3)H18···O1vi2.6600
C20···O33.085 (3)H18···O2vi2.4900
C20···O2vi3.322 (3)H18···C1vi3.0700
C21···C8iv3.400 (4)H21A···O32.3300
C22···C153.202 (4)H21A···C12iv3.0300
C22···O3iv3.128 (3)H21B···O1viii2.8700
C22···O1viii3.400 (4)H21B···H22C2.5300
C23···O2vi3.329 (4)H21C···O2iv2.7600
C24···O2vi3.224 (4)H21C···C8iv2.8200
C24···C183.157 (4)H21C···H22B2.5400
C1···H22Cii2.8800H22A···C142.4500
C1···H18iii3.0700H22A···C152.5600
C2···H15ii2.8500H22A···C24iv2.9400
C2···H10A2.4500H22A···H152.5400
C3···H10A2.6300H22A···H24Civ2.5000
C4···H16ii3.0800H22B···C11xii3.0900
C5···H16ii2.8500H22B···H11Bxii2.4800
C6···H11B2.9800H22B···H21C2.5400
C6···H16ii3.0500H22C···O1viii2.8300
C6···H11A2.6900H22C···O3iv2.6100
C7···H11A2.5400H22C···C1viii2.8800
C8···H21Ci2.8200H22C···H21B2.5300
C10···H32.9800H23A···O42.3800
C11···H22Bix3.0900H23B···O2vi2.7100
C11···H62.7800H23C···H52.4600
C11···H10Ai2.9500H23C···H24C2.2900
C12···H21Ai3.0300H24A···C183.0800
C13···H10Bv2.9500H24A···O2vi2.5600
C13···H3v3.0100H24B···C182.7900
C14···H22A2.4500H24B···C192.5300
C14···H3v2.8800H24C···H22Ai2.5000
C15···H22A2.5600H24C···H23C2.2900
C1—N1—C9119.8 (2)H12B—C12—H12C109.00
C1—N1—C10125.4 (2)N2—C12—H12A110.00
C9—N1—C10114.7 (2)N2—C12—H12B109.00
C8—N2—C11124.9 (2)N2—C12—H12C109.00
C8—N2—C12119.6 (3)H12A—C12—H12B109.00
C11—N2—C12115.6 (2)H12A—C12—H12C110.00
C13—N3—C22124.7 (2)O3—C13—N3123.2 (3)
C21—N3—C22115.2 (2)O3—C13—C14118.5 (2)
C13—N3—C21120.0 (2)N3—C13—C14118.2 (2)
C23—N4—C24116.3 (3)C13—C14—C15119.7 (2)
C20—N4—C23118.4 (3)C13—C14—C19120.5 (2)
C20—N4—C24124.2 (3)C15—C14—C19119.5 (3)
O1—C1—C2118.6 (2)C14—C15—C16120.7 (3)
O1—C1—N1123.9 (3)C15—C16—C17119.9 (3)
N1—C1—C2117.5 (2)C16—C17—C18120.0 (3)
C1—C2—C3119.7 (3)C17—C18—C19120.5 (2)
C1—C2—C7120.2 (2)C14—C19—C18119.4 (3)
C3—C2—C7119.8 (2)C14—C19—C20119.6 (2)
C2—C3—C4120.4 (3)C18—C19—C20120.6 (2)
C3—C4—C5120.0 (3)O4—C20—N4122.8 (3)
C4—C5—C6120.1 (3)O4—C20—C19118.4 (3)
C5—C6—C7120.2 (3)N4—C20—C19118.9 (3)
C6—C7—C8121.0 (3)C14—C15—H15120.00
C2—C7—C6119.4 (2)C16—C15—H15120.00
C2—C7—C8119.3 (2)C15—C16—H16120.00
N2—C8—C7118.2 (2)C17—C16—H16120.00
O2—C8—N2123.3 (3)C16—C17—H17120.00
O2—C8—C7118.5 (2)C18—C17—H17120.00
C2—C3—H3120.00C17—C18—H18120.00
C4—C3—H3120.00C19—C18—H18120.00
C3—C4—H4120.00N3—C21—H21A109.00
C5—C4—H4120.00N3—C21—H21B109.00
C6—C5—H5120.00N3—C21—H21C109.00
C4—C5—H5120.00H21A—C21—H21B110.00
C5—C6—H6120.00H21A—C21—H21C109.00
C7—C6—H6120.00H21B—C21—H21C110.00
N1—C9—H9B109.00N3—C22—H22A109.00
N1—C9—H9A109.00N3—C22—H22B109.00
H9A—C9—H9C109.00N3—C22—H22C109.00
N1—C9—H9C110.00H22A—C22—H22B109.00
H9A—C9—H9B109.00H22A—C22—H22C109.00
H9B—C9—H9C109.00H22B—C22—H22C109.00
N1—C10—H10C109.00N4—C23—H23A109.00
N1—C10—H10A109.00N4—C23—H23B109.00
N1—C10—H10B109.00N4—C23—H23C109.00
H10A—C10—H10C110.00H23A—C23—H23B110.00
H10B—C10—H10C109.00H23A—C23—H23C109.00
H10A—C10—H10B109.00H23B—C23—H23C110.00
H11A—C11—H11B109.00N4—C24—H24A109.00
H11A—C11—H11C109.00N4—C24—H24B109.00
N2—C11—H11A109.00N4—C24—H24C109.00
N2—C11—H11B110.00H24A—C24—H24B109.00
N2—C11—H11C109.00H24A—C24—H24C109.00
H11B—C11—H11C109.00H24B—C24—H24C109.00
C9—N1—C1—O13.8 (4)C3—C4—C5—C61.4 (4)
C10—N1—C1—O1173.5 (3)C4—C5—C6—C70.7 (4)
C9—N1—C1—C2172.2 (2)C5—C6—C7—C8175.2 (3)
C10—N1—C1—C210.5 (4)C5—C6—C7—C21.3 (4)
C12—N2—C8—C7173.4 (2)C6—C7—C8—N255.4 (4)
C11—N2—C8—O2177.3 (3)C2—C7—C8—O251.7 (4)
C12—N2—C8—O24.1 (4)C2—C7—C8—N2130.7 (3)
C11—N2—C8—C75.2 (4)C6—C7—C8—O2122.3 (3)
C21—N3—C13—O36.4 (4)O3—C13—C14—C1958.4 (4)
C22—N3—C13—O3168.5 (3)N3—C13—C14—C1560.6 (4)
C21—N3—C13—C14169.5 (2)N3—C13—C14—C19125.6 (3)
C22—N3—C13—C1415.7 (4)O3—C13—C14—C15115.4 (3)
C23—N4—C20—O48.3 (4)C15—C14—C19—C181.0 (4)
C23—N4—C20—C19171.2 (3)C15—C14—C19—C20174.1 (3)
C24—N4—C20—C193.6 (4)C19—C14—C15—C160.7 (4)
C24—N4—C20—O4175.9 (3)C13—C14—C19—C18174.9 (3)
O1—C1—C2—C3114.6 (3)C13—C14—C15—C16174.6 (3)
O1—C1—C2—C759.1 (4)C13—C14—C19—C2012.1 (4)
N1—C1—C2—C361.6 (4)C14—C15—C16—C170.2 (5)
N1—C1—C2—C7124.7 (3)C15—C16—C17—C180.8 (5)
C7—C2—C3—C42.0 (4)C16—C17—C18—C190.4 (4)
C1—C2—C7—C6176.4 (3)C17—C18—C19—C140.5 (4)
C1—C2—C3—C4175.8 (3)C17—C18—C19—C20173.4 (3)
C1—C2—C7—C89.5 (4)C14—C19—C20—N4119.4 (3)
C3—C2—C7—C62.7 (4)C18—C19—C20—O4111.9 (3)
C3—C2—C7—C8176.7 (3)C18—C19—C20—N467.7 (4)
C2—C3—C4—C50.0 (4)C14—C19—C20—O461.1 (4)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z1; (iii) x+1, y+1/2, z+1; (iv) x1, y, z; (v) x, y, z+1; (vi) x+1, y1/2, z+1; (vii) x, y, z1; (viii) x1, y, z+1; (ix) x+2, y, z; (x) x, y1/2, z+1; (xi) x, y+1/2, z+1; (xii) x2, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O3vii0.932.603.518 (3)170
C5—H5···O4i0.932.583.141 (4)119
C6—H6···O4i0.932.513.105 (4)122
C18—H18···O2vi0.932.493.329 (3)150
C24—H24A···O2vi0.962.563.224 (4)127
C16—H16···Cg10.932.973.810 (4)124
Symmetry codes: (i) x+1, y, z; (vi) x+1, y1/2, z+1; (vii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC12H16N2O2
Mr220.27
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)6.7337 (6), 18.1230 (14), 9.8216 (8)
β (°) 104.918 (3)
V3)1158.18 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.56 × 0.52 × 0.33
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.925, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
8205, 2739, 2414
Rint0.045
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.124, 1.06
No. of reflections2739
No. of parameters297
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.34

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ATOMS (Dowty, 1995), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···O3i0.932.603.518 (3)170
C5—H5···O4ii0.932.583.141 (4)119
C6—H6···O4ii0.932.513.105 (4)122
C18—H18···O2iii0.932.493.329 (3)150
C24—H24A···O2iii0.962.563.224 (4)127
C16—H16···Cg10.932.973.810 (4)124
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z; (iii) x+1, y1/2, z+1.
 

Acknowledgements

The authors thank the MESRS (Algeria) for financial support.

References

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