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ISSN: 2056-9890

3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-di­hydro­phenanthrene-2,4-dicarbo­nitrile

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 16 August 2011; accepted 17 August 2011; online 27 August 2011)

In the title compound, C23H15N3O2, significant deviations from planarity are evidenced in the values of the dihedral angles formed between the amino-benzene ring and the benzene rings of the 1,3-benzodioxole [65.38 (12)°] and 1,2-dihydro­naphthalene [26.27 (14)°] residues; the dioxole ring has an envelope conformation with the methyl­ene-C being the flap atom. The amino-H atoms form hydrogen bonds to one of the dioxole-O atoms and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ([\overline{1}] 0 2) plane.

Related literature

For background to the biological activity of related compounds, see: Aly et al. (1991[Aly, A. S., El-Ezabawy, S. R. & Abdel-Fattah, A. M. (1991). Egypt. J. Pharm. Sci. 32, 827-834.]); Al-Saadi et al. (2005[Al-Saadi, S. M., Rostom, S. A. F. & Faid Allah, H. M. (2005). Alexandria J. Pharm. Sci. 19, 15-21.]); Rostom et al. (2011[Rostom, S. A. F., Faidallah, S. M. & Al Saadi, M. S. (2011). Med. Chem. Res. DOI: 10.1007/s00044-010-9469-0.]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H15N3O2

  • Mr = 365.38

  • Monoclinic, P 21 /c

  • a = 8.9280 (6) Å

  • b = 22.4518 (13) Å

  • c = 8.9473 (6) Å

  • β = 109.058 (7)°

  • V = 1695.18 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.25 × 0.25 × 0.05 mm

Data collection
  • Agilent Technologies SuperNova Dual diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.776, Tmax = 1.000

  • 9604 measured reflections

  • 3775 independent reflections

  • 2570 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.167

  • S = 1.02

  • 3775 reflections

  • 261 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H1⋯O1i 0.88 (1) 2.40 (2) 3.231 (3) 157 (3)
N2—H2⋯N1ii 0.88 (1) 2.37 (2) 3.188 (3) 156 (3)
Symmetry codes: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+3, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The study of the title compound (I) was motivated by recent reports of the biological activity of related compounds (Aly et al., 1991; Al-Saadi et al., 2005; Rostom et al., 2011).

With respect to the amino-benzene ring, the benzene rings of the 1,3-benzodioxole and 1,2-dihydronaphthalene residues form dihedral angles of 65.38 (12) and 26.27 (14) °, respectively, indicating non-planarity in the molecule. The five-membered dioxole ring has an envelope conformation with the methylene-C23 atom being the flap atom. The Cremer & Pople (1975) parameters defining the five-membered ring are q2 = 0.182 (3) Å and ϕ2 = 324.8 (9) Å. In the 1,2-dihydronaphthalene residue, the cyclohexa-1,3-diene ring has a distorted half-chair conformation as defined by the following parameters (Cremer & Pople, 1975): q2 = 0.503 (3) Å, ϕ2 = 265.5 (3) °, q3 = -0.189 (3) Å, and puckering amplitude Q = 0.537 (3) Å.

In the crystal structure, supramolecular arrays with zigzag topology and running parallel to the (1 0 2) plane are formed through N—H···O(dioxole) and NH···N(cyano) hydrogen bonding Table 1 and Fig. 2.

Related literature top

For background to the biological activity of related compounds, see: Aly et al. (1991); Al-Saadi et al. (2005); Rostom et al. (2011). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of the piperonaldehyde (1.5 g,10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool and the precipitate that formed was filtered, washed with water, dried and recrystallized from DMF; M.pt.: 549–551 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.99 Å, Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The amino-H atoms were located in a difference Fourier map, and subsequently refined freely. The maximum and minimum residual electron density peaks of 0.65 and 0.30 e Å-3, respectively, were located 0.92 Å and 0.65 Å from the H19 and C23 atoms, respectively.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Supramolecular array in (I) viewed towards the (1 0 2) plane. The N—H···O and N—H···.N hydrogen bonds are shown as orange and blue dashed lines, respectively.
3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-dihydrophenanthrene-2,4- dicarbonitrile top
Crystal data top
C23H15N3O2F(000) = 760
Mr = 365.38Dx = 1.432 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2779 reflections
a = 8.9280 (6) Åθ = 2.4–29.3°
b = 22.4518 (13) ŵ = 0.09 mm1
c = 8.9473 (6) ÅT = 100 K
β = 109.058 (7)°Plate, orange
V = 1695.18 (19) Å30.25 × 0.25 × 0.05 mm
Z = 4
Data collection top
Agilent Technologies SuperNova Dual
diffractometer with Atlas detector
3775 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2570 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.042
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.6°
ω scanh = 911
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 2924
Tmin = 0.776, Tmax = 1.000l = 1111
9604 measured reflections
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0527P)2 + 2.2435P]
where P = (Fo2 + 2Fc2)/3
3775 reflections(Δ/σ)max < 0.001
261 parametersΔρmax = 0.65 e Å3
2 restraintsΔρmin = 0.30 e Å3
Crystal data top
C23H15N3O2V = 1695.18 (19) Å3
Mr = 365.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.9280 (6) ŵ = 0.09 mm1
b = 22.4518 (13) ÅT = 100 K
c = 8.9473 (6) Å0.25 × 0.25 × 0.05 mm
β = 109.058 (7)°
Data collection top
Agilent Technologies SuperNova Dual
diffractometer with Atlas detector
3775 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
2570 reflections with I > 2σ(I)
Tmin = 0.776, Tmax = 1.000Rint = 0.042
9604 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0652 restraints
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.65 e Å3
3775 reflectionsΔρmin = 0.30 e Å3
261 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4763 (2)0.18869 (9)0.8357 (2)0.0314 (5)
O20.4316 (2)0.28084 (9)0.9262 (2)0.0331 (5)
N11.3481 (3)0.53871 (11)0.9128 (3)0.0338 (6)
N21.3145 (3)0.40625 (12)1.0585 (3)0.0336 (6)
H11.344 (4)0.3728 (9)1.112 (4)0.052 (11)*
H21.389 (3)0.4315 (12)1.058 (4)0.046 (10)*
N31.1365 (3)0.27041 (11)1.0990 (3)0.0334 (6)
C10.8958 (3)0.37338 (12)0.8347 (3)0.0258 (6)
C20.8496 (3)0.42563 (13)0.7482 (3)0.0272 (6)
C30.6849 (3)0.43271 (14)0.6300 (4)0.0342 (7)
H3A0.62050.45870.67460.041*
H3B0.63230.39340.60650.041*
C40.6975 (3)0.46015 (13)0.4790 (3)0.0306 (7)
H4A0.75610.43290.43100.037*
H4B0.59020.46630.40210.037*
C50.7827 (3)0.51885 (12)0.5167 (3)0.0270 (6)
C60.7385 (3)0.56661 (13)0.4116 (4)0.0297 (6)
H60.65410.56180.31480.036*
C70.8153 (3)0.62062 (13)0.4460 (4)0.0343 (7)
H70.78740.65230.37170.041*
C80.9328 (4)0.62819 (13)0.5890 (4)0.0360 (7)
H80.98380.66570.61450.043*
C90.9777 (3)0.58157 (13)0.6968 (4)0.0312 (7)
H91.05710.58790.79620.037*
C100.9068 (3)0.52541 (12)0.6600 (3)0.0263 (6)
C110.9590 (3)0.47229 (12)0.7635 (3)0.0261 (6)
C121.1138 (3)0.46557 (12)0.8686 (3)0.0240 (6)
C131.1643 (3)0.41274 (12)0.9576 (3)0.0259 (6)
C141.0515 (3)0.36702 (12)0.9370 (3)0.0243 (6)
C151.2379 (3)0.50862 (12)0.8885 (3)0.0268 (6)
C161.0980 (3)0.31309 (13)1.0264 (3)0.0271 (6)
C170.7828 (3)0.32335 (13)0.8240 (3)0.0260 (6)
C180.8070 (3)0.26822 (13)0.7666 (3)0.0304 (6)
H180.89250.26350.72650.037*
C190.7098 (3)0.21922 (14)0.7657 (3)0.0315 (7)
H190.72700.18140.72640.038*
C200.5905 (3)0.22874 (13)0.8238 (3)0.0274 (6)
C210.5615 (3)0.28346 (13)0.8782 (3)0.0273 (6)
C220.6548 (3)0.33250 (13)0.8791 (3)0.0278 (6)
H220.63350.37030.91510.033*
C230.3996 (4)0.21835 (13)0.9305 (4)0.0326 (7)
H23A0.44030.20351.04050.039*
H23B0.28400.21100.88890.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0306 (11)0.0281 (11)0.0333 (11)0.0128 (9)0.0074 (8)0.0032 (9)
O20.0300 (11)0.0322 (12)0.0402 (12)0.0058 (9)0.0157 (9)0.0018 (9)
N10.0301 (13)0.0236 (13)0.0451 (15)0.0017 (11)0.0086 (11)0.0032 (11)
N20.0231 (12)0.0274 (15)0.0453 (15)0.0042 (11)0.0046 (11)0.0105 (12)
N30.0318 (13)0.0273 (14)0.0369 (14)0.0058 (11)0.0051 (11)0.0039 (12)
C10.0254 (14)0.0258 (15)0.0292 (14)0.0026 (11)0.0131 (11)0.0030 (12)
C20.0226 (13)0.0283 (16)0.0325 (15)0.0007 (11)0.0115 (11)0.0044 (12)
C30.0238 (14)0.0345 (18)0.0443 (18)0.0021 (13)0.0112 (13)0.0090 (14)
C40.0269 (14)0.0267 (16)0.0378 (16)0.0010 (12)0.0100 (12)0.0064 (13)
C50.0237 (14)0.0248 (15)0.0378 (16)0.0040 (11)0.0171 (12)0.0048 (12)
C60.0289 (15)0.0259 (16)0.0384 (16)0.0069 (12)0.0166 (12)0.0063 (13)
C70.0349 (16)0.0234 (16)0.0483 (19)0.0092 (13)0.0187 (14)0.0068 (14)
C80.0350 (16)0.0185 (15)0.057 (2)0.0030 (12)0.0178 (15)0.0002 (14)
C90.0273 (14)0.0246 (16)0.0434 (17)0.0053 (12)0.0141 (13)0.0003 (13)
C100.0219 (13)0.0221 (15)0.0397 (16)0.0035 (11)0.0165 (12)0.0021 (12)
C110.0257 (14)0.0245 (15)0.0313 (15)0.0018 (11)0.0134 (11)0.0017 (12)
C120.0232 (13)0.0193 (14)0.0339 (15)0.0005 (11)0.0151 (11)0.0012 (12)
C130.0256 (14)0.0218 (15)0.0317 (15)0.0014 (11)0.0112 (11)0.0008 (12)
C140.0252 (14)0.0209 (14)0.0288 (14)0.0014 (11)0.0114 (11)0.0024 (11)
C150.0271 (14)0.0217 (15)0.0317 (15)0.0023 (12)0.0096 (11)0.0023 (12)
C160.0211 (13)0.0292 (16)0.0306 (15)0.0066 (12)0.0081 (11)0.0009 (13)
C170.0257 (14)0.0275 (15)0.0240 (14)0.0042 (12)0.0071 (11)0.0043 (12)
C180.0275 (14)0.0352 (17)0.0271 (15)0.0003 (13)0.0070 (11)0.0019 (13)
C190.0290 (15)0.0331 (17)0.0272 (15)0.0010 (13)0.0022 (12)0.0021 (13)
C200.0294 (14)0.0259 (15)0.0210 (13)0.0054 (12)0.0002 (11)0.0015 (11)
C210.0251 (14)0.0363 (17)0.0213 (13)0.0030 (12)0.0088 (11)0.0035 (12)
C220.0315 (15)0.0250 (15)0.0279 (14)0.0057 (12)0.0109 (11)0.0025 (12)
C230.0349 (16)0.0278 (17)0.0344 (16)0.0083 (13)0.0104 (13)0.0011 (13)
Geometric parameters (Å, º) top
O1—C201.389 (3)C7—C81.374 (4)
O1—C231.418 (3)C7—H70.9500
O2—C211.364 (3)C8—C91.391 (4)
O2—C231.435 (3)C8—H80.9500
N1—C151.154 (4)C9—C101.401 (4)
N2—C131.358 (4)C9—H90.9500
N2—H10.883 (10)C10—C111.488 (4)
N2—H20.877 (10)C11—C121.403 (4)
N3—C161.145 (4)C12—C131.418 (4)
C1—C21.392 (4)C12—C151.437 (4)
C1—C141.400 (4)C13—C141.407 (4)
C1—C171.492 (4)C14—C161.436 (4)
C2—C111.409 (4)C17—C181.384 (4)
C2—C31.513 (4)C17—C221.399 (4)
C3—C41.522 (4)C18—C191.400 (4)
C3—H3A0.9900C18—H180.9500
C3—H3B0.9900C19—C201.346 (4)
C4—C51.504 (4)C19—H190.9500
C4—H4A0.9900C20—C211.376 (4)
C4—H4B0.9900C21—C221.379 (4)
C5—C61.396 (4)C22—H220.9500
C5—C101.402 (4)C23—H23A0.9900
C6—C71.378 (4)C23—H23B0.9900
C6—H60.9500
C20—O1—C23104.5 (2)C5—C10—C11118.6 (2)
C21—O2—C23104.3 (2)C12—C11—C2119.0 (2)
C13—N2—H1120 (2)C12—C11—C10122.9 (2)
C13—N2—H2121 (2)C2—C11—C10118.0 (2)
H1—N2—H2117 (3)C11—C12—C13122.0 (2)
C2—C1—C14120.1 (2)C11—C12—C15124.2 (2)
C2—C1—C17121.8 (2)C13—C12—C15113.7 (2)
C14—C1—C17118.1 (2)N2—C13—C14121.2 (3)
C1—C2—C11120.2 (3)N2—C13—C12121.8 (2)
C1—C2—C3121.4 (2)C14—C13—C12117.0 (2)
C11—C2—C3118.3 (2)C1—C14—C13121.8 (3)
C2—C3—C4109.1 (2)C1—C14—C16119.7 (2)
C2—C3—H3A109.9C13—C14—C16118.5 (2)
C4—C3—H3A109.9N1—C15—C12173.0 (3)
C2—C3—H3B109.9N3—C16—C14179.2 (3)
C4—C3—H3B109.9C18—C17—C22120.4 (3)
H3A—C3—H3B108.3C18—C17—C1120.9 (2)
C5—C4—C3109.5 (2)C22—C17—C1118.7 (3)
C5—C4—H4A109.8C17—C18—C19122.3 (3)
C3—C4—H4A109.8C17—C18—H18118.9
C5—C4—H4B109.8C19—C18—H18118.9
C3—C4—H4B109.8C20—C19—C18116.1 (3)
H4A—C4—H4B108.2C20—C19—H19121.9
C6—C5—C10120.1 (3)C18—C19—H19121.9
C6—C5—C4120.7 (3)C19—C20—C21122.8 (3)
C10—C5—C4119.2 (2)C19—C20—O1128.3 (3)
C7—C6—C5121.0 (3)C21—C20—O1108.9 (2)
C7—C6—H6119.5O2—C21—C20110.5 (2)
C5—C6—H6119.5O2—C21—C22127.4 (3)
C8—C7—C6119.3 (3)C20—C21—C22122.1 (2)
C8—C7—H7120.3C21—C22—C17116.2 (3)
C6—C7—H7120.3C21—C22—H22121.9
C7—C8—C9120.8 (3)C17—C22—H22121.9
C7—C8—H8119.6O1—C23—O2107.7 (2)
C9—C8—H8119.6O1—C23—H23A110.2
C8—C9—C10120.6 (3)O2—C23—H23A110.2
C8—C9—H9119.7O1—C23—H23B110.2
C10—C9—H9119.7O2—C23—H23B110.2
C9—C10—C5118.1 (3)H23A—C23—H23B108.5
C9—C10—C11123.3 (3)
C14—C1—C2—C110.1 (4)C11—C12—C13—C140.5 (4)
C17—C1—C2—C11178.9 (2)C15—C12—C13—C14176.4 (2)
C14—C1—C2—C3176.7 (3)C2—C1—C14—C130.9 (4)
C17—C1—C2—C34.3 (4)C17—C1—C14—C13178.1 (2)
C1—C2—C3—C4135.0 (3)C2—C1—C14—C16179.7 (3)
C11—C2—C3—C441.8 (4)C17—C1—C14—C160.7 (4)
C2—C3—C4—C557.5 (3)N2—C13—C14—C1179.3 (3)
C3—C4—C5—C6143.6 (3)C12—C13—C14—C10.6 (4)
C3—C4—C5—C1035.8 (3)N2—C13—C14—C160.5 (4)
C10—C5—C6—C70.1 (4)C12—C13—C14—C16179.4 (2)
C4—C5—C6—C7179.5 (2)C2—C1—C17—C18117.0 (3)
C5—C6—C7—C82.8 (4)C14—C1—C17—C1864.0 (4)
C6—C7—C8—C91.9 (4)C2—C1—C17—C2265.5 (4)
C7—C8—C9—C101.7 (4)C14—C1—C17—C22113.5 (3)
C8—C9—C10—C54.2 (4)C22—C17—C18—C192.1 (4)
C8—C9—C10—C11174.4 (3)C1—C17—C18—C19175.3 (3)
C6—C5—C10—C93.4 (4)C17—C18—C19—C200.1 (4)
C4—C5—C10—C9176.1 (2)C18—C19—C20—C211.5 (4)
C6—C5—C10—C11175.3 (2)C18—C19—C20—O1179.3 (2)
C4—C5—C10—C115.2 (4)C23—O1—C20—C19169.6 (3)
C1—C2—C11—C121.0 (4)C23—O1—C20—C2112.3 (3)
C3—C2—C11—C12177.8 (3)C23—O2—C21—C2011.9 (3)
C1—C2—C11—C10175.7 (2)C23—O2—C21—C22168.8 (3)
C3—C2—C11—C101.1 (4)C19—C20—C21—O2178.4 (2)
C9—C10—C11—C1226.2 (4)O1—C20—C21—O20.2 (3)
C5—C10—C11—C12152.4 (3)C19—C20—C21—C221.0 (4)
C9—C10—C11—C2157.2 (3)O1—C20—C21—C22179.2 (2)
C5—C10—C11—C224.2 (4)O2—C21—C22—C17179.7 (3)
C2—C11—C12—C131.3 (4)C20—C21—C22—C171.0 (4)
C10—C11—C12—C13175.2 (2)C18—C17—C22—C212.5 (4)
C2—C11—C12—C15176.7 (3)C1—C17—C22—C21174.9 (2)
C10—C11—C12—C150.2 (4)C20—O1—C23—O219.6 (3)
C11—C12—C13—N2179.6 (3)C21—O2—C23—O119.5 (3)
C15—C12—C13—N23.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O1i0.88 (1)2.40 (2)3.231 (3)157 (3)
N2—H2···N1ii0.88 (1)2.37 (2)3.188 (3)156 (3)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+3, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC23H15N3O2
Mr365.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.9280 (6), 22.4518 (13), 8.9473 (6)
β (°) 109.058 (7)
V3)1695.18 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.25 × 0.05
Data collection
DiffractometerAgilent Technologies SuperNova Dual
diffractometer with Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.776, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
9604, 3775, 2570
Rint0.042
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.167, 1.02
No. of reflections3775
No. of parameters261
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.65, 0.30

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O1i0.883 (10)2.400 (17)3.231 (3)157 (3)
N2—H2···N1ii0.877 (10)2.369 (17)3.188 (3)156 (3)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+3, y+1, z+2.
 

Footnotes

Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

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First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
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First citationRostom, S. A. F., Faidallah, S. M. & Al Saadi, M. S. (2011). Med. Chem. Res. DOI: 10.1007/s00044-010-9469-0.  Google Scholar
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First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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