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

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ISSN: 2056-9890

4-(Naphthalene-2-carboxamido)­pyridin-1-ium thio­cyanate–N-(pyridin-4-yl)naphthalene-2-carboxamide (1/1)

aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
*Correspondence e-mail: sohail262001@yahoo.com

(Received 1 September 2012; accepted 19 September 2012; online 26 September 2012)

The asymmetric unit of the title compound, C16H13N2O+·NCS·C16H12N2O, contains two N-(pyridin-4-yl)naphthalene-2-carboxamide mol­ecules, both are partially protonated in the pyridine moiety, i.e. the H atom attached to the pyridine N atom is partially occupied with an occupancy factor of 0.61 (3) and 0.39 (3), respectively. In the crystal, protonated and neutral N-(pyridin-4-yl)naphthalene-2-carboxamide mol­ecules are linked by N—H⋯N hydrogen bonding; the thio­cyanate counter-ion links with both protonated and neutral N-(pyridin-4-yl)naphthalene-2-carboxamide mol­ecules via N—H⋯S and N—H⋯N hydrogen bonding. The dihedral angles between the pyridine ring and naphthalene ring systems are 11.33 (6) and 9.51 (6)°, respectively. ππ stacking is observed in the crystal structure, the shortest centroid–centroid distance being 3.5929 (8) Å. The crystal structure was determined from a nonmerohedral twin {ratio of the twin components = 0.357 (1):0.643 (1) and twin law [-100 0-10 -101]}.

Related literature

For background to the biological activity of N-substituted benzamides and their applications in synthesis, see: Saeed et al. (2011[Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1194.]); Priya et al. (2005[Priya, B. S., Swamy, B. S. N. & Rangapa, K. S. (2005). Bioorg. Med. Chem. 13, 2623-2628.]). For related structures and use in mol­ecular recognition, see: Toda et al. (1987[Toda, F., Kai, A., Tagami, Y. & Mak, T. C. W. (1987). Chem. Lett. pp. 1393-1396.]); Saeed et al. (2011[Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1194.], 2012[Saeed, S., Rashid, N., Butcher, R. J., Öztürk Yildirim, S. & Hussain, R. (2012). Acta Cryst. E68, o2762.]). For bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13N2O+·NCS·C16H12N2O

  • Mr = 555.64

  • Triclinic, [P \overline 1]

  • a = 8.2667 (4) Å

  • b = 12.9008 (7) Å

  • c = 13.5579 (8) Å

  • α = 84.047 (5)°

  • β = 77.566 (5)°

  • γ = 71.684 (5)°

  • V = 1339.45 (13) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 1.41 mm−1

  • T = 123 K

  • 0.38 × 0.35 × 0.29 mm

Data collection
  • Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.])Tmin = 0.904, Tmax = 1.000

  • 9408 measured reflections

  • 9408 independent reflections

  • 8399 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.137

  • S = 1.02

  • 9408 reflections

  • 374 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 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
N1A—H1AA⋯N1S 0.88 2.24 3.0576 (17) 154
N1B—H1BA⋯S1Si 0.88 2.69 3.5345 (11) 162
N2A—H2AA⋯N2B 0.88 1.77 2.6492 (15) 173
N2B—H2BB⋯N2A 0.88 1.77 2.6492 (15) 177
Symmetry code: (i) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Amides are known to play a pivital role in molecular recognition, being important components in supramolecular chemical anion sensors technology (Saeed et al., 2011, 2012). Moreover, amides have also been reported as antimicrobial agents (Priya et al., 2005). A compound with the same basic skeleton as the title compound has been used in host–guest chemistry to form numerous highly crystalline adducts with a variety of common organic solvents (Toda et al., 1987). The structure of the title compound has been determined to explore the effect of substituents on the structure of the title compound.

The crystal structure of the title compound (Fig. 1), [(C16H13N2O+)(NCS-)] C16H12N2O, there are two independent molecules (A and B) in the asymmetric unit of which one is protonated (A). In both A and B the naphthyl and pyridine rings are planar with a mean deviation from the least- squares plane defined by naphthyl ring carbon atoms (C1—C10) and C1A of -0.018 (1) Å and 0.0268 (1) Å for the C1B. All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The dihedral angles between the naphthyl and pyridine ring systems is 11.33 (6) and 9.51 (6)° in molecules A and B, respectively. In the crystal, N—H···N and N—H···S intra- and intermolecular hydrogen bonds are observed (Table 1) as well as weak π - π stacking interactions [Cg1···Cg4 (x,1 + y,z] = 3.615 (1) Å, Cg2···Cg3 (x,-1 + y,z] = 3.593 (1) Å, Cg2···Cg5 (x,-1 + y,z] = 3.735 (1) Å and Cg3···Cg4 (1 + x,1 + y,y] = 3.686 (1) Å where Cg1(N2A/C12A—C16A), Cg2(N2B/C12B—C16B), Cg3(C1A—C3A/C8A—C10A), Cg4(C1B—C3B/C8B—C10B) and Cg5(C3A—C8A) are the centroids of the pyridinium and naphthalene rings](Fig. 2).

Related literature top

For background to the biological activity of N-substituted benzamides and their applications in synthesis, see: Saeed et al. (2011); Priya et al. (2005). For related structures and use in molecular recognition, see: Toda et al. (1987); Saeed et al. (2011, 2012). For bond lengths, see: Allen et al. (1987).

Experimental top

A solution of naphthalene 2-carbonyl chloride (0.01 mol) in anhydrous acetone (80 ml) was added dropwise to a suspension of dry sodium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 45 min. After cooling to room temperature, a solution of 4-aminopyridine (0.01 mol) in anhydrous acetone (25 ml) was added and the resulting mixture refluxed for 2 h. Hydrochloric acid (0.1 N, 400 ml) was added, and the solution was filtered.

Refinement top

The crystal structure was solved from non-merohedral twin with the twin law in the reciprocal matrix of -1, 0, 0: 0, -1, 0: -1, 0, 1 and the twin component ratio of 0.357 (1)/0.643 (1). In the refinement the HKLF 5 reflection file format in SHELXL was used.

H atoms attached to C atoms were positioned with idealized geometry and were refined isotropic with Ueq(H) set to 1.2 times of the Ueq(C) using a riding model with C—H = 0.95 Å. H atoms attached to N atoms were positioned with idealized geometry and were refined isotropically with Ueq(H) set to 1.2 times of Ueq(N) using a riding model with N—H = 0.88 Å. The H atom attached to the pyridine-N atom is disordered over two sites in a ratio of 0.61 (3):0.39 (3).

Structure description top

Amides are known to play a pivital role in molecular recognition, being important components in supramolecular chemical anion sensors technology (Saeed et al., 2011, 2012). Moreover, amides have also been reported as antimicrobial agents (Priya et al., 2005). A compound with the same basic skeleton as the title compound has been used in host–guest chemistry to form numerous highly crystalline adducts with a variety of common organic solvents (Toda et al., 1987). The structure of the title compound has been determined to explore the effect of substituents on the structure of the title compound.

The crystal structure of the title compound (Fig. 1), [(C16H13N2O+)(NCS-)] C16H12N2O, there are two independent molecules (A and B) in the asymmetric unit of which one is protonated (A). In both A and B the naphthyl and pyridine rings are planar with a mean deviation from the least- squares plane defined by naphthyl ring carbon atoms (C1—C10) and C1A of -0.018 (1) Å and 0.0268 (1) Å for the C1B. All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The dihedral angles between the naphthyl and pyridine ring systems is 11.33 (6) and 9.51 (6)° in molecules A and B, respectively. In the crystal, N—H···N and N—H···S intra- and intermolecular hydrogen bonds are observed (Table 1) as well as weak π - π stacking interactions [Cg1···Cg4 (x,1 + y,z] = 3.615 (1) Å, Cg2···Cg3 (x,-1 + y,z] = 3.593 (1) Å, Cg2···Cg5 (x,-1 + y,z] = 3.735 (1) Å and Cg3···Cg4 (1 + x,1 + y,y] = 3.686 (1) Å where Cg1(N2A/C12A—C16A), Cg2(N2B/C12B—C16B), Cg3(C1A—C3A/C8A—C10A), Cg4(C1B—C3B/C8B—C10B) and Cg5(C3A—C8A) are the centroids of the pyridinium and naphthalene rings](Fig. 2).

For background to the biological activity of N-substituted benzamides and their applications in synthesis, see: Saeed et al. (2011); Priya et al. (2005). For related structures and use in molecular recognition, see: Toda et al. (1987); Saeed et al. (2011, 2012). For bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. The dashed line denotes the hydrogen bond between the neutral and protonated moieties.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed down c axis. The dashed lines denote hydrogen bonds.
4-(Naphthalene-2-carboxamido)pyridin-1-ium thiocyanate– N-(pyridin-4-yl)naphthalene-2-carboxamide (1/1) top
Crystal data top
C16H13N2O+·NCS·C16H12N2OZ = 2
Mr = 555.64F(000) = 580
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 8.2667 (4) ÅCell parameters from 3931 reflections
b = 12.9008 (7) Åθ = 3.3–75.5°
c = 13.5579 (8) ŵ = 1.41 mm1
α = 84.047 (5)°T = 123 K
β = 77.566 (5)°Prism, colorless
γ = 71.684 (5)°0.38 × 0.35 × 0.29 mm
V = 1339.45 (13) Å3
Data collection top
Xcalibur (Ruby, Gemini)
diffractometer
9408 independent reflections
Radiation source: Enhance (Cu) X-ray Source8399 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 10.5081 pixels mm-1θmax = 76.0°, θmin = 3.3°
ω scansh = 1010
Absorption correction: multi-scan
[CrysAlis RED (Agilent, 2011) based on expressions derived from Clark & Reid (1995)]
k = 1616
Tmin = 0.904, Tmax = 1.000l = 1216
9408 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0899P)2 + 0.2899P]
where P = (Fo2 + 2Fc2)/3
9408 reflections(Δ/σ)max = 0.001
374 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C16H13N2O+·NCS·C16H12N2Oγ = 71.684 (5)°
Mr = 555.64V = 1339.45 (13) Å3
Triclinic, P1Z = 2
a = 8.2667 (4) ÅCu Kα radiation
b = 12.9008 (7) ŵ = 1.41 mm1
c = 13.5579 (8) ÅT = 123 K
α = 84.047 (5)°0.38 × 0.35 × 0.29 mm
β = 77.566 (5)°
Data collection top
Xcalibur (Ruby, Gemini)
diffractometer
9408 independent reflections
Absorption correction: multi-scan
[CrysAlis RED (Agilent, 2011) based on expressions derived from Clark & Reid (1995)]
8399 reflections with I > 2σ(I)
Tmin = 0.904, Tmax = 1.000Rint = 0.000
9408 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.02Δρmax = 0.36 e Å3
9408 reflectionsΔρmin = 0.30 e Å3
374 parameters
Special details top

Experimental. CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid, 1995).

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*/UeqOcc. (<1)
S1S0.08493 (5)0.80651 (3)0.97576 (3)0.03396 (11)
N1S0.4395 (2)0.68666 (11)0.95127 (10)0.0399 (3)
C1S0.2927 (2)0.73545 (11)0.96208 (10)0.0315 (3)
O1A0.66272 (14)0.64980 (8)0.56439 (7)0.0319 (2)
N1A0.58653 (14)0.61521 (8)0.73364 (8)0.0240 (2)
H1AA0.57790.63940.79350.034 (4)*
N2A0.44101 (14)0.33301 (8)0.74169 (8)0.0245 (2)
H2AA0.40930.27350.74450.029*0.61 (3)
C1A0.68983 (17)0.77349 (10)0.67251 (10)0.0245 (3)
C2A0.66122 (17)0.81223 (11)0.76696 (10)0.0263 (3)
H2AB0.61330.77450.82390.032*
C3A0.70214 (18)0.90814 (11)0.78109 (11)0.0276 (3)
C4A0.6715 (2)0.94936 (12)0.87865 (12)0.0358 (3)
H4AA0.62430.91200.93620.043*
C5A0.7098 (2)1.04289 (13)0.89019 (14)0.0412 (4)
H5AA0.68931.07000.95570.049*
C6A0.7797 (2)1.09912 (12)0.80502 (14)0.0401 (4)
H6AA0.80581.16380.81380.048*
C7A0.81019 (19)1.06170 (12)0.71064 (13)0.0356 (3)
H7AA0.85611.10090.65410.043*
C8A0.77348 (17)0.96363 (11)0.69583 (11)0.0277 (3)
C9A0.80472 (18)0.92153 (11)0.59920 (11)0.0295 (3)
H9AA0.85450.95770.54160.035*
C10A0.76400 (17)0.82912 (10)0.58763 (10)0.0268 (3)
H10A0.78560.80190.52210.032*
C11A0.64576 (16)0.67468 (10)0.65080 (10)0.0239 (3)
C12A0.53898 (16)0.52088 (10)0.73240 (10)0.0218 (2)
C13A0.53009 (17)0.47683 (10)0.64435 (10)0.0242 (3)
H13A0.55830.51060.58000.029*
C14A0.47968 (17)0.38366 (10)0.65253 (10)0.0256 (3)
H14A0.47210.35440.59280.031*
C15A0.45085 (19)0.37358 (11)0.82714 (10)0.0281 (3)
H15A0.42400.33710.89020.034*
C16A0.49897 (18)0.46677 (11)0.82490 (10)0.0273 (3)
H16A0.50500.49420.88590.033*
O1B0.27783 (14)0.15477 (8)0.54771 (7)0.0330 (2)
N1B0.21021 (14)0.12707 (8)0.71690 (8)0.0225 (2)
H1BA0.16760.15330.77580.034 (4)*
N2B0.35165 (14)0.15425 (8)0.73472 (8)0.0242 (2)
H2BB0.38100.21320.73970.029*0.39 (3)
C1B0.16169 (16)0.28346 (10)0.65252 (10)0.0221 (2)
C2B0.10170 (17)0.32263 (10)0.74599 (10)0.0242 (3)
H2BA0.09430.28460.80400.029*
C3B0.05008 (17)0.41902 (10)0.75834 (10)0.0255 (3)
C4B0.0151 (2)0.45925 (13)0.85460 (12)0.0357 (3)
H4BA0.02820.42020.91290.043*
C5B0.0597 (2)0.55389 (13)0.86471 (13)0.0401 (4)
H5BA0.10370.58000.92980.048*
C6B0.0404 (2)0.61291 (12)0.77879 (14)0.0376 (4)
H6BA0.06900.67950.78670.045*
C7B0.01863 (19)0.57544 (11)0.68477 (12)0.0322 (3)
H7BA0.02990.61570.62750.039*
C8B0.06374 (16)0.47632 (10)0.67138 (11)0.0257 (3)
C9B0.12318 (18)0.43331 (11)0.57536 (11)0.0277 (3)
H9BA0.13090.47010.51660.033*
C10B0.16984 (17)0.33960 (10)0.56551 (10)0.0255 (3)
H10B0.20810.31160.50010.031*
C11B0.22166 (16)0.18353 (10)0.63304 (9)0.0221 (2)
C12B0.25886 (16)0.03295 (10)0.71828 (10)0.0212 (2)
C13B0.34762 (17)0.01249 (10)0.63456 (10)0.0239 (3)
H13B0.37730.01930.57050.029*
C14B0.39169 (17)0.10469 (11)0.64657 (10)0.0259 (3)
H14B0.45360.13450.58940.031*
C15B0.26547 (18)0.11074 (11)0.81480 (10)0.0273 (3)
H15B0.23630.14500.87770.033*
C16B0.21700 (18)0.01874 (11)0.81046 (10)0.0267 (3)
H16B0.15600.00940.86920.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1S0.0457 (2)0.03312 (19)0.02666 (18)0.02096 (15)0.00028 (14)0.00364 (13)
N1S0.0512 (9)0.0364 (7)0.0346 (7)0.0163 (6)0.0070 (6)0.0049 (5)
C1S0.0538 (10)0.0279 (6)0.0200 (6)0.0233 (7)0.0048 (6)0.0025 (5)
O1A0.0463 (6)0.0275 (5)0.0268 (5)0.0190 (4)0.0050 (4)0.0023 (4)
N1A0.0306 (6)0.0186 (5)0.0273 (5)0.0111 (4)0.0076 (4)0.0040 (4)
N2A0.0276 (5)0.0188 (5)0.0303 (6)0.0107 (4)0.0064 (4)0.0020 (4)
C1A0.0235 (6)0.0179 (6)0.0335 (7)0.0069 (5)0.0073 (5)0.0014 (5)
C2A0.0284 (6)0.0225 (6)0.0302 (7)0.0107 (5)0.0066 (5)0.0005 (5)
C3A0.0281 (6)0.0230 (6)0.0340 (7)0.0076 (5)0.0105 (5)0.0018 (5)
C4A0.0432 (8)0.0308 (7)0.0394 (8)0.0149 (6)0.0129 (7)0.0057 (6)
C5A0.0468 (9)0.0340 (8)0.0512 (10)0.0151 (7)0.0186 (7)0.0111 (7)
C6A0.0384 (8)0.0248 (7)0.0664 (11)0.0117 (6)0.0223 (7)0.0106 (7)
C7A0.0323 (7)0.0240 (6)0.0549 (9)0.0119 (6)0.0134 (7)0.0001 (6)
C8A0.0238 (6)0.0228 (6)0.0384 (7)0.0070 (5)0.0103 (5)0.0000 (5)
C9A0.0298 (7)0.0243 (6)0.0349 (7)0.0106 (5)0.0061 (6)0.0038 (5)
C10A0.0282 (6)0.0224 (6)0.0294 (7)0.0078 (5)0.0053 (5)0.0002 (5)
C11A0.0233 (6)0.0163 (5)0.0332 (7)0.0068 (5)0.0068 (5)0.0010 (5)
C12A0.0216 (6)0.0171 (5)0.0280 (6)0.0064 (4)0.0059 (5)0.0022 (5)
C13A0.0281 (6)0.0229 (6)0.0255 (6)0.0119 (5)0.0065 (5)0.0017 (5)
C14A0.0303 (6)0.0230 (6)0.0276 (6)0.0121 (5)0.0067 (5)0.0038 (5)
C15A0.0361 (7)0.0245 (6)0.0266 (6)0.0132 (5)0.0073 (5)0.0010 (5)
C16A0.0363 (7)0.0251 (6)0.0235 (6)0.0122 (5)0.0063 (5)0.0032 (5)
O1B0.0489 (6)0.0308 (5)0.0251 (5)0.0232 (4)0.0024 (4)0.0017 (4)
N1B0.0290 (5)0.0188 (5)0.0229 (5)0.0128 (4)0.0041 (4)0.0003 (4)
N2B0.0276 (5)0.0176 (5)0.0303 (6)0.0109 (4)0.0051 (4)0.0017 (4)
C1B0.0224 (6)0.0181 (6)0.0275 (6)0.0068 (4)0.0072 (5)0.0018 (5)
C2B0.0292 (6)0.0216 (6)0.0259 (6)0.0110 (5)0.0085 (5)0.0018 (5)
C3B0.0277 (6)0.0217 (6)0.0308 (7)0.0109 (5)0.0098 (5)0.0025 (5)
C4B0.0457 (8)0.0344 (7)0.0343 (8)0.0219 (6)0.0118 (6)0.0063 (6)
C5B0.0481 (9)0.0370 (8)0.0442 (9)0.0261 (7)0.0158 (7)0.0148 (7)
C6B0.0366 (8)0.0232 (6)0.0605 (10)0.0167 (6)0.0187 (7)0.0096 (6)
C7B0.0310 (7)0.0212 (6)0.0495 (8)0.0102 (5)0.0143 (6)0.0027 (6)
C8B0.0229 (6)0.0186 (6)0.0376 (7)0.0064 (5)0.0098 (5)0.0014 (5)
C9B0.0297 (7)0.0238 (6)0.0317 (7)0.0083 (5)0.0065 (5)0.0079 (5)
C10B0.0288 (6)0.0232 (6)0.0258 (6)0.0088 (5)0.0049 (5)0.0040 (5)
C11B0.0249 (6)0.0194 (6)0.0238 (6)0.0088 (5)0.0052 (5)0.0011 (5)
C12B0.0225 (6)0.0175 (5)0.0259 (6)0.0077 (4)0.0072 (5)0.0002 (4)
C13B0.0290 (6)0.0223 (6)0.0234 (6)0.0124 (5)0.0041 (5)0.0014 (5)
C14B0.0287 (6)0.0237 (6)0.0276 (6)0.0128 (5)0.0040 (5)0.0007 (5)
C15B0.0320 (7)0.0244 (6)0.0280 (7)0.0133 (5)0.0015 (5)0.0059 (5)
C16B0.0314 (7)0.0255 (6)0.0252 (6)0.0145 (5)0.0007 (5)0.0013 (5)
Geometric parameters (Å, º) top
S1S—C1S1.6530 (17)C16A—H16A0.9500
N1S—C1S1.163 (2)O1B—C11B1.2163 (16)
O1A—C11A1.2141 (17)N1B—C11B1.3836 (16)
N1A—C11A1.3822 (17)N1B—C12B1.3969 (15)
N1A—C12A1.3941 (15)N1B—H1BA0.8800
N1A—H1AA0.8800N2B—C15B1.3392 (17)
N2A—C14A1.3384 (17)N2B—C14B1.3424 (17)
N2A—C15A1.3476 (17)N2B—H2BB0.8800
N2A—H2AA0.8800C1B—C2B1.3642 (18)
C1A—C2A1.3688 (19)C1B—C10B1.4258 (17)
C1A—C10A1.4201 (19)C1B—C11B1.5007 (17)
C1A—C11A1.5035 (17)C2B—C3B1.4199 (17)
C2A—C3A1.4220 (18)C2B—H2BA0.9500
C2A—H2AB0.9500C3B—C4B1.413 (2)
C3A—C8A1.413 (2)C3B—C8B1.4213 (19)
C3A—C4A1.419 (2)C4B—C5B1.368 (2)
C4A—C5A1.372 (2)C4B—H4BA0.9500
C4A—H4AA0.9500C5B—C6B1.411 (2)
C5A—C6A1.413 (3)C5B—H5BA0.9500
C5A—H5AA0.9500C6B—C7B1.360 (2)
C6A—C7A1.359 (2)C6B—H6BA0.9500
C6A—H6AA0.9500C7B—C8B1.4247 (18)
C7A—C8A1.4330 (19)C7B—H7BA0.9500
C7A—H7AA0.9500C8B—C9B1.411 (2)
C8A—C9A1.411 (2)C9B—C10B1.3659 (18)
C9A—C10A1.3685 (19)C9B—H9BA0.9500
C9A—H9AA0.9500C10B—H10B0.9500
C10A—H10A0.9500C12B—C13B1.3943 (17)
C12A—C16A1.3981 (18)C12B—C16B1.4029 (18)
C12A—C13A1.3993 (17)C13B—C14B1.3828 (17)
C13A—C14A1.3777 (17)C13B—H13B0.9500
C13A—H13A0.9500C14B—H14B0.9500
C14A—H14A0.9500C15B—C16B1.3770 (18)
C15A—C16A1.3757 (18)C15B—H15B0.9500
C15A—H15A0.9500C16B—H16B0.9500
N1S—C1S—S1S178.91 (14)C11B—N1B—C12B127.11 (11)
C11A—N1A—C12A126.84 (11)C11B—N1B—H1BA116.4
C11A—N1A—H1AA116.6C12B—N1B—H1BA116.4
C12A—N1A—H1AA116.6C15B—N2B—C14B117.55 (11)
C14A—N2A—C15A119.63 (11)C15B—N2B—H2BB121.2
C14A—N2A—H2AA120.2C14B—N2B—H2BB121.2
C15A—N2A—H2AA120.2C2B—C1B—C10B119.21 (11)
C2A—C1A—C10A119.38 (12)C2B—C1B—C11B124.68 (11)
C2A—C1A—C11A124.32 (12)C10B—C1B—C11B116.11 (11)
C10A—C1A—C11A116.29 (12)C1B—C2B—C3B121.33 (12)
C1A—C2A—C3A121.01 (12)C1B—C2B—H2BA119.3
C1A—C2A—H2AB119.5C3B—C2B—H2BA119.3
C3A—C2A—H2AB119.5C4B—C3B—C2B121.82 (12)
C8A—C3A—C4A119.61 (13)C4B—C3B—C8B119.12 (12)
C8A—C3A—C2A119.03 (12)C2B—C3B—C8B119.06 (12)
C4A—C3A—C2A121.36 (13)C5B—C4B—C3B120.68 (15)
C5A—C4A—C3A120.27 (15)C5B—C4B—H4BA119.7
C5A—C4A—H4AA119.9C3B—C4B—H4BA119.7
C3A—C4A—H4AA119.9C4B—C5B—C6B120.25 (15)
C4A—C5A—C6A120.28 (15)C4B—C5B—H5BA119.9
C4A—C5A—H5AA119.9C6B—C5B—H5BA119.9
C6A—C5A—H5AA119.9C7B—C6B—C5B120.65 (13)
C7A—C6A—C5A120.78 (13)C7B—C6B—H6BA119.7
C7A—C6A—H6AA119.6C5B—C6B—H6BA119.7
C5A—C6A—H6AA119.6C6B—C7B—C8B120.55 (14)
C6A—C7A—C8A120.49 (15)C6B—C7B—H7BA119.7
C6A—C7A—H7AA119.8C8B—C7B—H7BA119.7
C8A—C7A—H7AA119.8C9B—C8B—C3B118.65 (12)
C9A—C8A—C3A119.19 (12)C9B—C8B—C7B122.67 (13)
C9A—C8A—C7A122.24 (14)C3B—C8B—C7B118.68 (13)
C3A—C8A—C7A118.57 (13)C10B—C9B—C8B121.09 (12)
C10A—C9A—C8A120.63 (13)C10B—C9B—H9BA119.5
C10A—C9A—H9AA119.7C8B—C9B—H9BA119.5
C8A—C9A—H9AA119.7C9B—C10B—C1B120.62 (12)
C9A—C10A—C1A120.75 (13)C9B—C10B—H10B119.7
C9A—C10A—H10A119.6C1B—C10B—H10B119.7
C1A—C10A—H10A119.6O1B—C11B—N1B122.34 (11)
O1A—C11A—N1A122.82 (11)O1B—C11B—C1B121.19 (11)
O1A—C11A—C1A120.67 (12)N1B—C11B—C1B116.47 (11)
N1A—C11A—C1A116.51 (11)C13B—C12B—N1B124.48 (11)
N1A—C12A—C16A117.80 (11)C13B—C12B—C16B117.79 (11)
N1A—C12A—C13A124.03 (12)N1B—C12B—C16B117.72 (11)
C16A—C12A—C13A118.16 (11)C14B—C13B—C12B118.76 (12)
C14A—C13A—C12A118.88 (12)C14B—C13B—H13B120.6
C14A—C13A—H13A120.6C12B—C13B—H13B120.6
C12A—C13A—H13A120.6N2B—C14B—C13B123.50 (12)
N2A—C14A—C13A122.28 (12)N2B—C14B—H14B118.3
N2A—C14A—H14A118.9C13B—C14B—H14B118.3
C13A—C14A—H14A118.9N2B—C15B—C16B123.19 (12)
N2A—C15A—C16A121.34 (12)N2B—C15B—H15B118.4
N2A—C15A—H15A119.3C16B—C15B—H15B118.4
C16A—C15A—H15A119.3C15B—C16B—C12B119.21 (12)
C15A—C16A—C12A119.70 (12)C15B—C16B—H16B120.4
C15A—C16A—H16A120.1C12B—C16B—H16B120.4
C12A—C16A—H16A120.1
C10A—C1A—C2A—C3A1.0 (2)C10B—C1B—C2B—C3B1.06 (19)
C11A—C1A—C2A—C3A178.25 (12)C11B—C1B—C2B—C3B178.88 (11)
C1A—C2A—C3A—C8A0.0 (2)C1B—C2B—C3B—C4B178.85 (13)
C1A—C2A—C3A—C4A179.46 (13)C1B—C2B—C3B—C8B0.88 (19)
C8A—C3A—C4A—C5A0.4 (2)C2B—C3B—C4B—C5B178.25 (14)
C2A—C3A—C4A—C5A179.09 (14)C8B—C3B—C4B—C5B2.0 (2)
C3A—C4A—C5A—C6A0.1 (2)C3B—C4B—C5B—C6B0.2 (2)
C4A—C5A—C6A—C7A0.0 (2)C4B—C5B—C6B—C7B1.5 (2)
C5A—C6A—C7A—C8A0.6 (2)C5B—C6B—C7B—C8B0.6 (2)
C4A—C3A—C8A—C9A179.51 (13)C4B—C3B—C8B—C9B177.77 (13)
C2A—C3A—C8A—C9A0.98 (19)C2B—C3B—C8B—C9B1.97 (18)
C4A—C3A—C8A—C7A1.1 (2)C4B—C3B—C8B—C7B2.89 (19)
C2A—C3A—C8A—C7A178.46 (12)C2B—C3B—C8B—C7B177.37 (12)
C6A—C7A—C8A—C9A179.41 (13)C6B—C7B—C8B—C9B179.07 (13)
C6A—C7A—C8A—C3A1.2 (2)C6B—C7B—C8B—C3B1.6 (2)
C3A—C8A—C9A—C10A1.1 (2)C3B—C8B—C9B—C10B1.13 (19)
C7A—C8A—C9A—C10A178.35 (13)C7B—C8B—C9B—C10B178.18 (13)
C8A—C9A—C10A—C1A0.1 (2)C8B—C9B—C10B—C1B0.8 (2)
C2A—C1A—C10A—C9A0.9 (2)C2B—C1B—C10B—C9B1.93 (19)
C11A—C1A—C10A—C9A178.39 (12)C11B—C1B—C10B—C9B178.01 (12)
C12A—N1A—C11A—O1A0.2 (2)C12B—N1B—C11B—O1B0.2 (2)
C12A—N1A—C11A—C1A179.59 (11)C12B—N1B—C11B—C1B179.44 (11)
C2A—C1A—C11A—O1A174.42 (13)C2B—C1B—C11B—O1B178.11 (13)
C10A—C1A—C11A—O1A4.83 (18)C10B—C1B—C11B—O1B1.83 (18)
C2A—C1A—C11A—N1A5.75 (19)C2B—C1B—C11B—N1B1.58 (18)
C10A—C1A—C11A—N1A175.00 (11)C10B—C1B—C11B—N1B178.48 (11)
C11A—N1A—C12A—C16A173.68 (12)C11B—N1B—C12B—C13B8.2 (2)
C11A—N1A—C12A—C13A5.9 (2)C11B—N1B—C12B—C16B172.51 (12)
N1A—C12A—C13A—C14A179.35 (12)N1B—C12B—C13B—C14B178.54 (12)
C16A—C12A—C13A—C14A1.12 (18)C16B—C12B—C13B—C14B0.80 (18)
C15A—N2A—C14A—C13A0.1 (2)C15B—N2B—C14B—C13B0.5 (2)
C12A—C13A—C14A—N2A0.9 (2)C12B—C13B—C14B—N2B0.9 (2)
C14A—N2A—C15A—C16A0.4 (2)C14B—N2B—C15B—C16B0.0 (2)
N2A—C15A—C16A—C12A0.1 (2)N2B—C15B—C16B—C12B0.0 (2)
N1A—C12A—C16A—C15A179.78 (12)C13B—C12B—C16B—C15B0.39 (19)
C13A—C12A—C16A—C15A0.65 (19)N1B—C12B—C16B—C15B179.00 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···N1S0.882.243.0576 (17)154
N1B—H1BA···S1Si0.882.693.5345 (11)162
N2A—H2AA···N2B0.881.772.6492 (15)173
N2B—H2BB···N2A0.881.772.6492 (15)177
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC16H13N2O+·NCS·C16H12N2O
Mr555.64
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)8.2667 (4), 12.9008 (7), 13.5579 (8)
α, β, γ (°)84.047 (5), 77.566 (5), 71.684 (5)
V3)1339.45 (13)
Z2
Radiation typeCu Kα
µ (mm1)1.41
Crystal size (mm)0.38 × 0.35 × 0.29
Data collection
DiffractometerXcalibur (Ruby, Gemini)
Absorption correctionMulti-scan
[CrysAlis RED (Agilent, 2011) based on expressions derived from Clark & Reid (1995)]
Tmin, Tmax0.904, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
9408, 9408, 8399
Rint0.000
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.137, 1.02
No. of reflections9408
No. of parameters374
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.30

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···N1S0.882.243.0576 (17)153.6
N1B—H1BA···S1Si0.882.693.5345 (11)162.1
N2A—H2AA···N2B0.881.772.6492 (15)173.4
N2B—H2BB···N2A0.881.772.6492 (15)176.5
Symmetry code: (i) x, y1, z.
 

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE–0619278) for funds to purchase an X-ray diffractometer.

References

First citationAgilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.  Google Scholar
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First citationSaeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1194.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationToda, F., Kai, A., Tagami, Y. & Mak, T. C. W. (1987). Chem. Lett. pp. 1393–1396.  CrossRef Web of Science Google Scholar

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