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A new type of thio­phene derivative with potential pharmacological activity, viz. 2-amino-4-(2-naphthalyl)­thio­phene-3-carbo­nitrile, C15H10N2S, has been prepared and studied by NMR and single-crystal X-ray diffraction techniques. The mol­ecule contains two different groups, naphthalene and thio­phene, which are nearly perpendicular to one another. In the crystal structure, a hydrogen bond, with a D...A distance of 3.033 (3) Å, is present between the amino substituent and the carbo­nitrile N atom of a symmetry-related mol­ecule. The crystal structure also includes one C—H...π interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013425/su6198sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013425/su6198Isup2.hkl
Contains datablock I

CCDC reference: 274651

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.042
  • wR factor = 0.070
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.716 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S - C3 .. 5.32 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.20 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.42 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97, PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

2-Amino-4-(2-naphthalyl)thiophene-3-carbonitrile top
Crystal data top
C15H10N2SF(000) = 520
Mr = 250.31Dx = 1.326 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.3075 (14) ÅCell parameters from 6485 reflections
b = 7.4751 (9) Åθ = 2–28.1°
c = 13.6676 (17) ŵ = 0.24 mm1
β = 94.046 (3)°T = 293 K
V = 1254.3 (3) Å3Prism, colourless
Z = 40.25 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
930 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
Graphite monochromatorθmax = 27.1°, θmin = 2.2°
φ and w scansh = 1614
6485 measured reflectionsk = 95
2769 independent reflectionsl = 1814
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) = 0.070H-atom parameters constrained
S = 0.72 w = 1/[σ2(Fo2) + (0.0119P)2]
where P = (Fo2 + 2Fc2)/3
2769 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
S0.70246 (6)0.19501 (9)0.31719 (6)0.0614 (3)
C50.56302 (19)0.0609 (3)0.3137 (2)0.0411 (7)
C60.4875 (2)0.2041 (4)0.34309 (18)0.0438 (7)
C150.3771 (2)0.1623 (3)0.35951 (18)0.0433 (7)
C30.6423 (2)0.1328 (3)0.2041 (2)0.0488 (8)
C70.5231 (2)0.3760 (4)0.3551 (2)0.0643 (9)
H70.59470.40380.34360.077*
N10.47201 (18)0.1678 (3)0.06844 (19)0.0690 (8)
C20.57086 (19)0.0083 (3)0.2146 (2)0.0433 (7)
C100.3082 (2)0.2991 (4)0.39250 (19)0.0507 (8)
C10.5157 (2)0.0949 (4)0.1332 (2)0.0471 (8)
N20.66814 (15)0.2151 (3)0.12138 (18)0.0729 (8)
H2A0.63880.18090.06560.087*
H2B0.71410.30200.12430.087*
C80.4534 (3)0.5121 (4)0.3846 (2)0.0784 (11)
H80.47880.62910.39070.094*
C140.3330 (2)0.0110 (3)0.34408 (19)0.0548 (8)
H140.37640.10160.32130.066*
C130.2276 (2)0.0468 (4)0.3622 (2)0.0717 (10)
H130.19950.16110.35100.086*
C40.62941 (19)0.0347 (3)0.3765 (2)0.0509 (8)
H40.63540.01670.44400.061*
C110.2003 (2)0.2547 (4)0.4124 (2)0.0736 (10)
H110.15540.34240.43610.088*
C90.3501 (2)0.4736 (4)0.4040 (2)0.0693 (10)
H90.30560.56400.42550.083*
C120.1613 (2)0.0879 (5)0.3977 (2)0.0789 (11)
H120.09000.06170.41110.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0533 (5)0.0565 (5)0.0742 (7)0.0122 (4)0.0018 (4)0.0061 (5)
C50.0327 (17)0.0366 (18)0.054 (2)0.0025 (13)0.0057 (15)0.0001 (15)
C60.0471 (18)0.0383 (18)0.047 (2)0.0007 (16)0.0078 (14)0.0013 (15)
C150.0441 (18)0.0425 (19)0.044 (2)0.0024 (16)0.0047 (14)0.0021 (14)
C30.0464 (18)0.049 (2)0.051 (2)0.0012 (15)0.0034 (16)0.0037 (16)
C70.054 (2)0.046 (2)0.093 (3)0.0027 (18)0.0129 (18)0.0062 (18)
N10.0730 (18)0.074 (2)0.060 (2)0.0273 (15)0.0027 (15)0.0067 (16)
C20.0349 (17)0.0414 (19)0.054 (2)0.0027 (14)0.0078 (16)0.0016 (16)
C100.0482 (19)0.047 (2)0.057 (2)0.0082 (18)0.0061 (15)0.0008 (16)
C10.0404 (19)0.050 (2)0.051 (3)0.0085 (15)0.0076 (16)0.0093 (17)
N20.0724 (17)0.0788 (18)0.067 (2)0.0379 (14)0.0042 (15)0.0056 (15)
C80.079 (3)0.039 (2)0.117 (3)0.001 (2)0.012 (2)0.0103 (18)
C140.050 (2)0.049 (2)0.066 (3)0.0014 (16)0.0090 (17)0.0013 (16)
C130.051 (2)0.070 (2)0.094 (3)0.0082 (18)0.008 (2)0.0020 (19)
C40.0521 (19)0.0495 (19)0.051 (2)0.0002 (15)0.0058 (16)0.0005 (15)
C110.053 (2)0.077 (3)0.092 (3)0.0159 (19)0.0156 (18)0.006 (2)
C90.069 (2)0.056 (2)0.084 (3)0.0185 (19)0.011 (2)0.0113 (18)
C120.048 (2)0.091 (3)0.099 (3)0.006 (2)0.0179 (19)0.013 (2)
Geometric parameters (Å, º) top
S—C31.730 (3)C10—C91.407 (3)
S—C41.733 (2)C10—C111.414 (3)
C5—C41.347 (3)N2—H2A0.8600
C5—C21.420 (3)N2—H2B0.8600
C5—C61.491 (3)C8—C91.349 (3)
C6—C71.364 (3)C8—H80.9300
C6—C151.428 (3)C14—C131.364 (3)
C15—C141.415 (3)C14—H140.9300
C15—C101.421 (3)C13—C121.404 (3)
C3—N21.345 (3)C13—H130.9300
C3—C21.387 (3)C4—H40.9300
C7—C81.407 (3)C11—C121.346 (3)
C7—H70.9300C11—H110.9300
N1—C11.142 (3)C9—H90.9300
C2—C11.418 (3)C12—H120.9300
C3—S—C491.61 (13)C3—N2—H2B120.0
C4—C5—C2112.4 (3)H2A—N2—H2B120.0
C4—C5—C6124.8 (3)C9—C8—C7120.2 (3)
C2—C5—C6122.8 (2)C9—C8—H8119.9
C7—C6—C15119.2 (2)C7—C8—H8119.9
C7—C6—C5120.5 (2)C13—C14—C15120.8 (3)
C15—C6—C5120.2 (2)C13—C14—H14119.6
C14—C15—C10118.4 (3)C15—C14—H14119.6
C14—C15—C6122.4 (3)C14—C13—C12120.3 (3)
C10—C15—C6119.2 (2)C14—C13—H13119.8
N2—C3—C2128.6 (3)C12—C13—H13119.8
N2—C3—S121.1 (2)C5—C4—S112.4 (2)
C2—C3—S110.3 (2)C5—C4—H4123.8
C6—C7—C8121.3 (3)S—C4—H4123.8
C6—C7—H7119.4C12—C11—C10121.2 (3)
C8—C7—H7119.4C12—C11—H11119.4
C3—C2—C1122.5 (3)C10—C11—H11119.4
C3—C2—C5113.3 (3)C8—C9—C10121.2 (3)
C1—C2—C5124.1 (3)C8—C9—H9119.4
C9—C10—C11122.5 (3)C10—C9—H9119.4
C9—C10—C15118.7 (3)C11—C12—C13120.5 (3)
C11—C10—C15118.8 (3)C11—C12—H12119.8
N1—C1—C2178.6 (3)C13—C12—H12119.8
C3—N2—H2A120.0
C4—C5—C6—C786.6 (3)C6—C5—C2—C15.6 (4)
C2—C5—C6—C794.6 (3)C14—C15—C10—C9177.3 (2)
C4—C5—C6—C1593.0 (3)C6—C15—C10—C92.6 (4)
C2—C5—C6—C1585.8 (3)C14—C15—C10—C112.6 (4)
C7—C6—C15—C14177.0 (2)C6—C15—C10—C11177.4 (3)
C5—C6—C15—C143.4 (4)C6—C7—C8—C91.7 (5)
C7—C6—C15—C103.0 (4)C10—C15—C14—C131.2 (4)
C5—C6—C15—C10176.7 (2)C6—C15—C14—C13178.8 (3)
C4—S—C3—N2179.8 (2)C15—C14—C13—C120.7 (4)
C4—S—C3—C21.06 (19)C2—C5—C4—S1.0 (3)
C15—C6—C7—C80.9 (4)C6—C5—C4—S177.96 (19)
C5—C6—C7—C8178.8 (3)C3—S—C4—C50.0 (2)
N2—C3—C2—C13.0 (4)C9—C10—C11—C12177.8 (3)
S—C3—C2—C1175.52 (19)C15—C10—C11—C122.1 (4)
N2—C3—C2—C5179.6 (2)C7—C8—C9—C102.0 (5)
S—C3—C2—C51.8 (3)C11—C10—C9—C8179.9 (3)
C4—C5—C2—C31.8 (3)C15—C10—C9—C80.1 (4)
C6—C5—C2—C3177.1 (2)C10—C11—C12—C130.2 (5)
C4—C5—C2—C1175.5 (2)C14—C13—C12—C111.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.213.033 (3)161
C4—H4···Cg3ii0.932.753.564 (3)146
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.
 

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