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ISSN: 2056-9890

3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbo­nitrile

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fAnalytical Sciences, Manchester Metropolitan University, Manchester M1 5GD, England
*Correspondence e-mail: akkurt@erciyes.edu.tr, shaabankamel@yahoo.com

(Received 13 February 2013; accepted 14 February 2013; online 20 February 2013)

In the title compound, C20H14N2O, the phenyl ring is almost normal to the naphthalene ring system with a dihedral angle of 86.72 (9)°. The 4H-pyran ring fused with the naphthalene ring system has a boat conformation. In the crystal, mol­ecules are linked into a helical supra­molecular chain along the b axis via N—H⋯N hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯π inter­actions.

Related literature

For biological and industrial applications of chromene compounds, see, for example: Ellis & Lockhart (2007[Ellis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1-1196. London: Wiley-VCH.]); Horton et al. (2003[Horton, D. A., Boume, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H14N2O

  • Mr = 298.33

  • Monoclinic, P 21

  • a = 9.4059 (8) Å

  • b = 6.5009 (5) Å

  • c = 12.4919 (10) Å

  • β = 105.914 (9)°

  • V = 734.57 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 123 K

  • 0.30 × 0.12 × 0.07 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.955, Tmax = 1.000

  • 3674 measured reflections

  • 2780 independent reflections

  • 2477 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.091

  • S = 1.06

  • 2780 reflections

  • 217 parameters

  • 49 restraints

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

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4/C5/C10–C13 and C5–C10 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯N2i 0.90 (3) 2.16 (2) 2.978 (3) 150 (2)
N1—H2N⋯N2ii 0.87 (3) 2.33 (3) 3.138 (3) 154 (2)
C7—H7⋯Cg3iii 0.95 2.84 3.561 (2) 133
C12—H12⋯Cg2iv 0.95 2.68 3.446 (2) 139
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z]; (ii) x, y-1, z; (iii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iv) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Chromenes are components of many natural products (Ellis & Lockhart, 2007) and incorporated in numerous medicinal drugs as significant chromophores. They have shown to display anti-viral, anti-tumoral, anti-anaphylactic, spasmolytic, diuretic and clotting activity (Horton et al., 2003). Furthermore, they can be used as photo-active materials, biodegradable agrochemicals and pigments. As a part of our structural investigations on functionalized chromenes and compounds containing the benzopyran fragment, the single-crystal X-ray diffraction study on the title compound was carried out.

In the title compound (I), Fig. 1, the C14–C19 phenyl ring and the C4–C13 naphthalene ring system is essentially planar with the maximum deviations of -0.004 (2) Å for C16 and 0.015 (2) Å for C4, respectively. They make a dihedral angle of 86.72 (9)° with each other.

The 4H-pyran ring (O1/C1–C4/C13) in (I) is puckered with the puckering parameters (Cremer & Pople, 1975) of QT = 0.211 (2) Å, θ = 96.2 (5)° and ϕ = 348.9 (6)°. The N1–C1–O1–C13 and N1–C1–C2–C20 torsion angles are -165.54 (17) and -2.6 (3)°, respectively.

In the crystal structure, molecules are linked into a helical supramolecular chain along the b axis via N—H···N hydrogen bonds (Table 1). Three distinct molecules are linked by three such connections involving two acceptors to generate a R32(10) ring motif (Fig. 2; Bernstein et al., 1995). Chains are consolidated into a three-dimensional architecture by C—H···π interactions.

Related literature top

For biological and industrial applications of chromene compounds, see, for example: Ellis & Lockhart (2007); Horton et al. (2003). For puckering parameters, see: Cremer & Pople (1975). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

Benzylidenepropanedinitrile (1.54 g; 10 mmol) was dissolved in ethanol (50 ml), followed by addition of naphthalen-2-ol (1.44 g; 10 mmol) and a catalytic amount of TEA. The mixture was stirred and refluxed for 2 h at 350 K. The solid product was deposited on cooling at room temperature and collected by filtration. The crude product was washed by cold ethanol, dried under vacuum and recrystallized from ethanol to give high quality crystals (M.pt: 563 K) suitable for X-ray analysis in an excellent yield (91%).

Refinement top

All non-hydrogen atoms were refined with anisotropic thermal parameter, however the carbon atoms of the C14–C19 phenyl ring were refined to approximate isotropic behaviour with the "ISOR and DELU" instruction. The H atoms of the NH2 group were located by difference synthesis and were refined isotropically. The other H atoms were positioned geometrically, with C—H = 0.95 Å and C—H = 1.00 Å for aromatic and methine H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the labelling of the non-H atoms and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the N—H···N hydrogen bonds, having R32(10) ring motifs, forming chains along the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity.
3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile top
Crystal data top
C20H14N2OF(000) = 312
Mr = 298.33Dx = 1.349 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1797 reflections
a = 9.4059 (8) Åθ = 3.1–28.7°
b = 6.5009 (5) ŵ = 0.09 mm1
c = 12.4919 (10) ÅT = 123 K
β = 105.914 (9)°Rod, colourless
V = 734.57 (11) Å30.30 × 0.12 × 0.07 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
2780 independent reflections
Radiation source: fine-focus sealed tube2477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 16.0727 pixels mm-1θmax = 28.8°, θmin = 3.2°
ω scansh = 1210
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 78
Tmin = 0.955, Tmax = 1.000l = 1616
3674 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0342P)2 + 0.0595P]
where P = (Fo2 + 2Fc2)/3
2780 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.22 e Å3
49 restraintsΔρmin = 0.18 e Å3
Crystal data top
C20H14N2OV = 734.57 (11) Å3
Mr = 298.33Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.4059 (8) ŵ = 0.09 mm1
b = 6.5009 (5) ÅT = 123 K
c = 12.4919 (10) Å0.30 × 0.12 × 0.07 mm
β = 105.914 (9)°
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
2780 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
2477 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 1.000Rint = 0.019
3674 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04249 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.22 e Å3
2780 reflectionsΔρmin = 0.18 e Å3
217 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
O10.91532 (15)0.1653 (2)0.28251 (11)0.0225 (4)
N11.0215 (2)0.2373 (3)0.14856 (16)0.0243 (6)
N20.9541 (2)0.7742 (3)0.08334 (15)0.0294 (6)
C10.9372 (2)0.3114 (3)0.21116 (15)0.0192 (6)
C20.8832 (2)0.5038 (3)0.21023 (16)0.0188 (6)
C30.7813 (2)0.5686 (3)0.28021 (16)0.0173 (6)
C40.7940 (2)0.4143 (3)0.37246 (15)0.0166 (6)
C50.7408 (2)0.4592 (3)0.46701 (16)0.0178 (6)
C60.6672 (2)0.6459 (4)0.47667 (16)0.0207 (6)
C70.6185 (2)0.6844 (4)0.56872 (17)0.0252 (7)
C80.6400 (2)0.5410 (3)0.65490 (17)0.0273 (7)
C90.7100 (2)0.3578 (4)0.64841 (17)0.0246 (7)
C100.7613 (2)0.3129 (3)0.55449 (16)0.0197 (6)
C110.8330 (2)0.1247 (3)0.54667 (16)0.0213 (6)
C120.8812 (2)0.0815 (3)0.45537 (16)0.0197 (6)
C130.8601 (2)0.2280 (3)0.37026 (16)0.0183 (6)
C140.6240 (2)0.6022 (3)0.20788 (15)0.0201 (6)
C150.5843 (2)0.7921 (4)0.15674 (16)0.0275 (7)
C160.4429 (3)0.8218 (4)0.08696 (18)0.0357 (8)
C170.3403 (3)0.6645 (5)0.06874 (18)0.0398 (9)
C180.3793 (3)0.4760 (5)0.11953 (19)0.0368 (8)
C190.5205 (2)0.4453 (4)0.18836 (17)0.0271 (7)
C200.9215 (2)0.6514 (4)0.13967 (16)0.0209 (6)
H1N1.024 (3)0.297 (4)0.084 (2)0.038 (7)*
H2N1.032 (3)0.104 (5)0.146 (2)0.043 (8)*
H30.818200.703400.315600.0210*
H60.651400.745200.418800.0250*
H70.569500.810300.573900.0300*
H80.606200.570300.718300.0330*
H90.723900.260700.707200.0290*
H110.847800.027300.605400.0260*
H120.928200.045800.449700.0240*
H150.654000.901400.169600.0330*
H160.416600.951000.051600.0430*
H170.243500.685700.021500.0480*
H180.309100.367400.107200.0440*
H190.546700.315100.222600.0330*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0282 (8)0.0207 (8)0.0215 (7)0.0020 (7)0.0116 (6)0.0011 (7)
N10.0270 (10)0.0260 (12)0.0227 (9)0.0022 (8)0.0118 (8)0.0002 (9)
N20.0353 (11)0.0279 (11)0.0302 (10)0.0016 (9)0.0179 (9)0.0030 (9)
C10.0177 (10)0.0237 (12)0.0151 (9)0.0048 (9)0.0028 (8)0.0008 (9)
C20.0183 (10)0.0216 (11)0.0169 (9)0.0027 (8)0.0054 (8)0.0008 (9)
C30.0177 (10)0.0169 (11)0.0179 (9)0.0023 (8)0.0059 (7)0.0017 (9)
C40.0142 (10)0.0180 (11)0.0161 (9)0.0032 (8)0.0019 (7)0.0004 (9)
C50.0126 (9)0.0225 (11)0.0178 (9)0.0037 (8)0.0034 (8)0.0000 (9)
C60.0187 (10)0.0226 (11)0.0209 (9)0.0015 (9)0.0057 (8)0.0018 (10)
C70.0224 (11)0.0260 (13)0.0292 (11)0.0004 (9)0.0105 (9)0.0024 (10)
C80.0269 (12)0.0371 (15)0.0207 (10)0.0030 (10)0.0114 (9)0.0025 (10)
C90.0242 (11)0.0305 (13)0.0192 (10)0.0030 (10)0.0063 (8)0.0029 (10)
C100.0169 (10)0.0248 (12)0.0164 (9)0.0023 (9)0.0030 (8)0.0003 (9)
C110.0218 (11)0.0224 (12)0.0178 (10)0.0025 (9)0.0020 (8)0.0026 (10)
C120.0174 (10)0.0180 (11)0.0217 (10)0.0002 (9)0.0019 (8)0.0013 (10)
C130.0185 (10)0.0211 (12)0.0152 (9)0.0033 (8)0.0047 (8)0.0034 (9)
C140.0212 (10)0.0269 (12)0.0131 (9)0.0041 (9)0.0061 (8)0.0011 (9)
C150.0292 (12)0.0301 (13)0.0238 (10)0.0070 (10)0.0085 (9)0.0055 (11)
C160.0358 (13)0.0479 (16)0.0227 (11)0.0204 (12)0.0069 (10)0.0096 (12)
C170.0227 (12)0.073 (2)0.0219 (11)0.0134 (13)0.0033 (9)0.0024 (14)
C180.0208 (11)0.0592 (17)0.0291 (12)0.0029 (12)0.0046 (9)0.0022 (13)
C190.0231 (11)0.0346 (14)0.0226 (10)0.0019 (10)0.0044 (9)0.0003 (11)
C200.0223 (10)0.0235 (11)0.0181 (9)0.0019 (9)0.0077 (8)0.0035 (10)
Geometric parameters (Å, º) top
O1—C11.356 (2)C11—C121.367 (3)
O1—C131.396 (2)C12—C131.400 (3)
N1—C11.346 (3)C14—C191.385 (3)
N2—C201.160 (3)C14—C151.393 (3)
N1—H1N0.90 (3)C15—C161.389 (3)
N1—H2N0.87 (3)C16—C171.381 (4)
C1—C21.349 (3)C17—C181.382 (4)
C2—C201.415 (3)C18—C191.385 (3)
C2—C31.523 (3)C3—H31.0000
C3—C41.508 (3)C6—H60.9500
C3—C141.523 (3)C7—H70.9500
C4—C131.365 (3)C8—H80.9500
C4—C51.433 (3)C9—H90.9500
C5—C101.421 (3)C11—H110.9500
C5—C61.419 (3)C12—H120.9500
C6—C71.372 (3)C15—H150.9500
C7—C81.396 (3)C16—H160.9500
C8—C91.374 (3)C17—H170.9500
C9—C101.416 (3)C18—H180.9500
C10—C111.413 (3)C19—H190.9500
C1—O1—C13117.88 (15)C15—C14—C19119.01 (18)
H1N—N1—H2N111 (2)C14—C15—C16120.1 (2)
C1—N1—H1N122.0 (17)C15—C16—C17120.4 (2)
C1—N1—H2N117.8 (18)C16—C17—C18119.7 (2)
O1—C1—C2122.03 (17)C17—C18—C19120.1 (3)
O1—C1—N1110.54 (17)C14—C19—C18120.8 (2)
N1—C1—C2127.39 (19)N2—C20—C2178.9 (2)
C1—C2—C3123.11 (17)C2—C3—H3107.00
C1—C2—C20118.34 (19)C4—C3—H3107.00
C3—C2—C20118.54 (18)C14—C3—H3107.00
C2—C3—C14111.16 (16)C5—C6—H6120.00
C4—C3—C14114.16 (16)C7—C6—H6120.00
C2—C3—C4108.92 (16)C6—C7—H7120.00
C3—C4—C13121.06 (17)C8—C7—H7120.00
C3—C4—C5121.46 (17)C7—C8—H8120.00
C5—C4—C13117.46 (17)C9—C8—H8120.00
C4—C5—C6122.21 (18)C8—C9—H9120.00
C4—C5—C10119.53 (17)C10—C9—H9120.00
C6—C5—C10118.26 (18)C10—C11—H11120.00
C5—C6—C7120.7 (2)C12—C11—H11120.00
C6—C7—C8120.9 (2)C11—C12—H12121.00
C7—C8—C9120.24 (19)C13—C12—H12121.00
C8—C9—C10120.4 (2)C14—C15—H15120.00
C5—C10—C9119.60 (19)C16—C15—H15120.00
C5—C10—C11119.53 (17)C15—C16—H16120.00
C9—C10—C11120.88 (19)C17—C16—H16120.00
C10—C11—C12120.61 (18)C16—C17—H17120.00
C11—C12—C13118.90 (18)C18—C17—H17120.00
O1—C13—C12113.06 (16)C17—C18—H18120.00
O1—C13—C4122.98 (17)C19—C18—H18120.00
C4—C13—C12123.96 (18)C14—C19—H19120.00
C3—C14—C15119.59 (17)C18—C19—H19120.00
C3—C14—C19121.37 (18)
C13—O1—C1—N1165.54 (17)C5—C4—C13—O1179.45 (17)
C13—O1—C1—C212.3 (3)C5—C4—C13—C121.3 (3)
C1—O1—C13—C416.6 (3)C4—C5—C6—C7179.59 (19)
C1—O1—C13—C12162.72 (17)C10—C5—C6—C70.6 (3)
O1—C1—C2—C36.1 (3)C4—C5—C10—C9179.43 (18)
O1—C1—C2—C20174.79 (17)C4—C5—C10—C110.4 (3)
N1—C1—C2—C3176.45 (19)C6—C5—C10—C90.8 (3)
N1—C1—C2—C202.6 (3)C6—C5—C10—C11179.40 (18)
C1—C2—C3—C418.5 (3)C5—C6—C7—C80.1 (3)
C1—C2—C3—C14108.1 (2)C6—C7—C8—C90.3 (3)
C20—C2—C3—C4162.42 (17)C7—C8—C9—C100.2 (3)
C20—C2—C3—C1471.0 (2)C8—C9—C10—C50.4 (3)
C2—C3—C4—C5164.30 (17)C8—C9—C10—C11179.78 (19)
C2—C3—C4—C1314.1 (3)C5—C10—C11—C120.7 (3)
C14—C3—C4—C570.8 (2)C9—C10—C11—C12179.46 (19)
C14—C3—C4—C13110.8 (2)C10—C11—C12—C130.8 (3)
C2—C3—C14—C1585.4 (2)C11—C12—C13—O1179.53 (17)
C2—C3—C14—C1992.2 (2)C11—C12—C13—C40.2 (3)
C4—C3—C14—C15150.88 (18)C3—C14—C15—C16177.37 (19)
C4—C3—C14—C1931.5 (3)C19—C14—C15—C160.3 (3)
C3—C4—C5—C63.1 (3)C3—C14—C19—C18177.9 (2)
C3—C4—C5—C10177.07 (18)C15—C14—C19—C180.3 (3)
C13—C4—C5—C6178.44 (19)C14—C15—C16—C170.7 (3)
C13—C4—C5—C101.4 (3)C15—C16—C17—C180.6 (4)
C3—C4—C13—O12.1 (3)C16—C17—C18—C190.1 (4)
C3—C4—C13—C12177.14 (18)C17—C18—C19—C140.4 (4)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C4/C5/C10–C13 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···N2i0.90 (3)2.16 (2)2.978 (3)150 (2)
N1—H2N···N2ii0.87 (3)2.33 (3)3.138 (3)154 (2)
C7—H7···Cg3iii0.952.843.561 (2)133
C12—H12···Cg2iv0.952.683.446 (2)139
Symmetry codes: (i) x+2, y1/2, z; (ii) x, y1, z; (iii) x+1, y+1/2, z+1; (iv) x+2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC20H14N2O
Mr298.33
Crystal system, space groupMonoclinic, P21
Temperature (K)123
a, b, c (Å)9.4059 (8), 6.5009 (5), 12.4919 (10)
β (°) 105.914 (9)
V3)734.57 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.12 × 0.07
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.955, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
3674, 2780, 2477
Rint0.019
(sin θ/λ)max1)0.678
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.091, 1.06
No. of reflections2780
No. of parameters217
No. of restraints49
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C4/C5/C10–C13 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N···N2i0.90 (3)2.16 (2)2.978 (3)150 (2)
N1—H2N···N2ii0.87 (3)2.33 (3)3.138 (3)154 (2)
C7—H7···Cg3iii0.952.843.561 (2)133
C12—H12···Cg2iv0.952.683.446 (2)139
Symmetry codes: (i) x+2, y1/2, z; (ii) x, y1, z; (iii) x+1, y+1/2, z+1; (iv) x+2, y1/2, z+1.
 

Acknowledgements

Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for supporting this study.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationEllis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1–1196. London: Wiley-VCH.
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationHorton, D. A., Boume, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893–930.  Web of Science CrossRef PubMed CAS
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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