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

Saeed, S.; Rashid, N.; Butcher, R.J.; Öztürk Yildirim, S.; Hussain, R.

doi:10.1107/S1600536812039864

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3002

https://doi.org/10.1107/S1600536812039864

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

Sohail Saeed,^a ^* Naghmana Rashid,^a Ray J. Butcher,^b Sema Öztürk Yildirim ^b,^c and Rizwan Hussain ^d

^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. π–π 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 ); 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

Crystal data

C₁₆H₁₃N₂O⁺·NCS⁻·C₁₆H₁₂N₂O
M_r = 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 )T_min = 0.904, T_max = 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
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812039864/xu5617sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039864/xu5617Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039864/xu5617Isup3.cml

checkCIF report

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.

Structure description 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).

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

	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.
	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⁻·C₁₆H₁₂N₂O	Z = 2
M_r = 555.64	F(000) = 580
Triclinic, P1	D_x = 1.378 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.2667 (4) Å	Cell parameters from 3931 reflections
b = 12.9008 (7) Å	θ = 3.3–75.5°
c = 13.5579 (8) Å	µ = 1.41 mm⁻¹
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 Source	8399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 10.5081 pixels mm^-1	θ_max = 76.0°, θ_min = 3.3°
ω scans	h = −10→10
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011) based on expressions derived from Clark & Reid (1995)]	k = −16→16
T_min = 0.904, T_max = 1.000	l = −12→16
9408 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0899P)² + 0.2899P] where P = (F_o² + 2F_c²)/3
9408 reflections	(Δ/σ)_max = 0.001
374 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₃N₂O⁺·NCS⁻·C₁₆H₁₂N₂O	γ = 71.684 (5)°
M_r = 555.64	V = 1339.45 (13) Å³
Triclinic, P1	Z = 2
a = 8.2667 (4) Å	Cu Kα radiation
b = 12.9008 (7) Å	µ = 1.41 mm⁻¹
c = 13.5579 (8) Å	T = 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)
T_min = 0.904, T_max = 1.000	R_int = 0.000
9408 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
9408 reflections	Δρ_min = −0.30 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1S	0.08493 (5)	0.80651 (3)	0.97576 (3)	0.03396 (11)
N1S	0.4395 (2)	0.68666 (11)	0.95127 (10)	0.0399 (3)
C1S	0.2927 (2)	0.73545 (11)	0.96208 (10)	0.0315 (3)
O1A	0.66272 (14)	0.64980 (8)	0.56439 (7)	0.0319 (2)
N1A	0.58653 (14)	0.61521 (8)	0.73364 (8)	0.0240 (2)
H1AA	0.5779	0.6394	0.7935	0.034 (4)*
N2A	0.44101 (14)	0.33301 (8)	0.74169 (8)	0.0245 (2)
H2AA	0.4093	0.2735	0.7445	0.029*	0.61 (3)
C1A	0.68983 (17)	0.77349 (10)	0.67251 (10)	0.0245 (3)
C2A	0.66122 (17)	0.81223 (11)	0.76696 (10)	0.0263 (3)
H2AB	0.6133	0.7745	0.8239	0.032*
C3A	0.70214 (18)	0.90814 (11)	0.78109 (11)	0.0276 (3)
C4A	0.6715 (2)	0.94936 (12)	0.87865 (12)	0.0358 (3)
H4AA	0.6243	0.9120	0.9362	0.043*
C5A	0.7098 (2)	1.04289 (13)	0.89019 (14)	0.0412 (4)
H5AA	0.6893	1.0700	0.9557	0.049*
C6A	0.7797 (2)	1.09912 (12)	0.80502 (14)	0.0401 (4)
H6AA	0.8058	1.1638	0.8138	0.048*
C7A	0.81019 (19)	1.06170 (12)	0.71064 (13)	0.0356 (3)
H7AA	0.8561	1.1009	0.6541	0.043*
C8A	0.77348 (17)	0.96363 (11)	0.69583 (11)	0.0277 (3)
C9A	0.80472 (18)	0.92153 (11)	0.59920 (11)	0.0295 (3)
H9AA	0.8545	0.9577	0.5416	0.035*
C10A	0.76400 (17)	0.82912 (10)	0.58763 (10)	0.0268 (3)
H10A	0.7856	0.8019	0.5221	0.032*
C11A	0.64576 (16)	0.67468 (10)	0.65080 (10)	0.0239 (3)
C12A	0.53898 (16)	0.52088 (10)	0.73240 (10)	0.0218 (2)
C13A	0.53009 (17)	0.47683 (10)	0.64435 (10)	0.0242 (3)
H13A	0.5583	0.5106	0.5800	0.029*
C14A	0.47968 (17)	0.38366 (10)	0.65253 (10)	0.0256 (3)
H14A	0.4721	0.3544	0.5928	0.031*
C15A	0.45085 (19)	0.37358 (11)	0.82714 (10)	0.0281 (3)
H15A	0.4240	0.3371	0.8902	0.034*
C16A	0.49897 (18)	0.46677 (11)	0.82490 (10)	0.0273 (3)
H16A	0.5050	0.4942	0.8859	0.033*
O1B	0.27783 (14)	−0.15477 (8)	0.54771 (7)	0.0330 (2)
N1B	0.21021 (14)	−0.12707 (8)	0.71690 (8)	0.0225 (2)
H1BA	0.1676	−0.1533	0.7758	0.034 (4)*
N2B	0.35165 (14)	0.15425 (8)	0.73472 (8)	0.0242 (2)
H2BB	0.3810	0.2132	0.7397	0.029*	0.39 (3)
C1B	0.16169 (16)	−0.28346 (10)	0.65252 (10)	0.0221 (2)
C2B	0.10170 (17)	−0.32263 (10)	0.74599 (10)	0.0242 (3)
H2BA	0.0943	−0.2846	0.8040	0.029*
C3B	0.05008 (17)	−0.41902 (10)	0.75834 (10)	0.0255 (3)
C4B	−0.0151 (2)	−0.45925 (13)	0.85460 (12)	0.0357 (3)
H4BA	−0.0282	−0.4202	0.9129	0.043*
C5B	−0.0597 (2)	−0.55389 (13)	0.86471 (13)	0.0401 (4)
H5BA	−0.1037	−0.5800	0.9298	0.048*
C6B	−0.0404 (2)	−0.61291 (12)	0.77879 (14)	0.0376 (4)
H6BA	−0.0690	−0.6795	0.7867	0.045*
C7B	0.01863 (19)	−0.57544 (11)	0.68477 (12)	0.0322 (3)
H7BA	0.0299	−0.6157	0.6275	0.039*
C8B	0.06374 (16)	−0.47632 (10)	0.67138 (11)	0.0257 (3)
C9B	0.12318 (18)	−0.43331 (11)	0.57536 (11)	0.0277 (3)
H9BA	0.1309	−0.4701	0.5166	0.033*
C10B	0.16984 (17)	−0.33960 (10)	0.56551 (10)	0.0255 (3)
H10B	0.2081	−0.3116	0.5001	0.031*
C11B	0.22166 (16)	−0.18353 (10)	0.63304 (9)	0.0221 (2)
C12B	0.25886 (16)	−0.03295 (10)	0.71828 (10)	0.0212 (2)
C13B	0.34762 (17)	0.01249 (10)	0.63456 (10)	0.0239 (3)
H13B	0.3773	−0.0193	0.5705	0.029*
C14B	0.39169 (17)	0.10469 (11)	0.64657 (10)	0.0259 (3)
H14B	0.4536	0.1345	0.5894	0.031*
C15B	0.26547 (18)	0.11074 (11)	0.81480 (10)	0.0273 (3)
H15B	0.2363	0.1450	0.8777	0.033*
C16B	0.21700 (18)	0.01874 (11)	0.81046 (10)	0.0267 (3)
H16B	0.1560	−0.0094	0.8692	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1S	0.0457 (2)	0.03312 (19)	0.02666 (18)	−0.02096 (15)	0.00028 (14)	−0.00364 (13)
N1S	0.0512 (9)	0.0364 (7)	0.0346 (7)	−0.0163 (6)	−0.0070 (6)	−0.0049 (5)
C1S	0.0538 (10)	0.0279 (6)	0.0200 (6)	−0.0233 (7)	−0.0048 (6)	−0.0025 (5)
O1A	0.0463 (6)	0.0275 (5)	0.0268 (5)	−0.0190 (4)	−0.0050 (4)	−0.0023 (4)
N1A	0.0306 (6)	0.0186 (5)	0.0273 (5)	−0.0111 (4)	−0.0076 (4)	−0.0040 (4)
N2A	0.0276 (5)	0.0188 (5)	0.0303 (6)	−0.0107 (4)	−0.0064 (4)	−0.0020 (4)
C1A	0.0235 (6)	0.0179 (6)	0.0335 (7)	−0.0069 (5)	−0.0073 (5)	−0.0014 (5)
C2A	0.0284 (6)	0.0225 (6)	0.0302 (7)	−0.0107 (5)	−0.0066 (5)	0.0005 (5)
C3A	0.0281 (6)	0.0230 (6)	0.0340 (7)	−0.0076 (5)	−0.0105 (5)	−0.0018 (5)
C4A	0.0432 (8)	0.0308 (7)	0.0394 (8)	−0.0149 (6)	−0.0129 (7)	−0.0057 (6)
C5A	0.0468 (9)	0.0340 (8)	0.0512 (10)	−0.0151 (7)	−0.0186 (7)	−0.0111 (7)
C6A	0.0384 (8)	0.0248 (7)	0.0664 (11)	−0.0117 (6)	−0.0223 (7)	−0.0106 (7)
C7A	0.0323 (7)	0.0240 (6)	0.0549 (9)	−0.0119 (6)	−0.0134 (7)	0.0001 (6)
C8A	0.0238 (6)	0.0228 (6)	0.0384 (7)	−0.0070 (5)	−0.0103 (5)	0.0000 (5)
C9A	0.0298 (7)	0.0243 (6)	0.0349 (7)	−0.0106 (5)	−0.0061 (6)	0.0038 (5)
C10A	0.0282 (6)	0.0224 (6)	0.0294 (7)	−0.0078 (5)	−0.0053 (5)	−0.0002 (5)
C11A	0.0233 (6)	0.0163 (5)	0.0332 (7)	−0.0068 (5)	−0.0068 (5)	−0.0010 (5)
C12A	0.0216 (6)	0.0171 (5)	0.0280 (6)	−0.0064 (4)	−0.0059 (5)	−0.0022 (5)
C13A	0.0281 (6)	0.0229 (6)	0.0255 (6)	−0.0119 (5)	−0.0065 (5)	−0.0017 (5)
C14A	0.0303 (6)	0.0230 (6)	0.0276 (6)	−0.0121 (5)	−0.0067 (5)	−0.0038 (5)
C15A	0.0361 (7)	0.0245 (6)	0.0266 (6)	−0.0132 (5)	−0.0073 (5)	0.0010 (5)
C16A	0.0363 (7)	0.0251 (6)	0.0235 (6)	−0.0122 (5)	−0.0063 (5)	−0.0032 (5)
O1B	0.0489 (6)	0.0308 (5)	0.0251 (5)	−0.0232 (4)	−0.0024 (4)	−0.0017 (4)
N1B	0.0290 (5)	0.0188 (5)	0.0229 (5)	−0.0128 (4)	−0.0041 (4)	0.0003 (4)
N2B	0.0276 (5)	0.0176 (5)	0.0303 (6)	−0.0109 (4)	−0.0051 (4)	−0.0017 (4)
C1B	0.0224 (6)	0.0181 (6)	0.0275 (6)	−0.0068 (4)	−0.0072 (5)	−0.0018 (5)
C2B	0.0292 (6)	0.0216 (6)	0.0259 (6)	−0.0110 (5)	−0.0085 (5)	−0.0018 (5)
C3B	0.0277 (6)	0.0217 (6)	0.0308 (7)	−0.0109 (5)	−0.0098 (5)	0.0025 (5)
C4B	0.0457 (8)	0.0344 (7)	0.0343 (8)	−0.0219 (6)	−0.0118 (6)	0.0063 (6)
C5B	0.0481 (9)	0.0370 (8)	0.0442 (9)	−0.0261 (7)	−0.0158 (7)	0.0148 (7)
C6B	0.0366 (8)	0.0232 (6)	0.0605 (10)	−0.0167 (6)	−0.0187 (7)	0.0096 (6)
C7B	0.0310 (7)	0.0212 (6)	0.0495 (8)	−0.0102 (5)	−0.0143 (6)	−0.0027 (6)
C8B	0.0229 (6)	0.0186 (6)	0.0376 (7)	−0.0064 (5)	−0.0098 (5)	−0.0014 (5)
C9B	0.0297 (7)	0.0238 (6)	0.0317 (7)	−0.0083 (5)	−0.0065 (5)	−0.0079 (5)
C10B	0.0288 (6)	0.0232 (6)	0.0258 (6)	−0.0088 (5)	−0.0049 (5)	−0.0040 (5)
C11B	0.0249 (6)	0.0194 (6)	0.0238 (6)	−0.0088 (5)	−0.0052 (5)	−0.0011 (5)
C12B	0.0225 (6)	0.0175 (5)	0.0259 (6)	−0.0077 (4)	−0.0072 (5)	−0.0002 (4)
C13B	0.0290 (6)	0.0223 (6)	0.0234 (6)	−0.0124 (5)	−0.0041 (5)	−0.0014 (5)
C14B	0.0287 (6)	0.0237 (6)	0.0276 (6)	−0.0128 (5)	−0.0040 (5)	0.0007 (5)
C15B	0.0320 (7)	0.0244 (6)	0.0280 (7)	−0.0133 (5)	−0.0015 (5)	−0.0059 (5)
C16B	0.0314 (7)	0.0255 (6)	0.0252 (6)	−0.0145 (5)	−0.0007 (5)	−0.0013 (5)

Geometric parameters (Å, º) top

S1S—C1S	1.6530 (17)	C16A—H16A	0.9500
N1S—C1S	1.163 (2)	O1B—C11B	1.2163 (16)
O1A—C11A	1.2141 (17)	N1B—C11B	1.3836 (16)
N1A—C11A	1.3822 (17)	N1B—C12B	1.3969 (15)
N1A—C12A	1.3941 (15)	N1B—H1BA	0.8800
N1A—H1AA	0.8800	N2B—C15B	1.3392 (17)
N2A—C14A	1.3384 (17)	N2B—C14B	1.3424 (17)
N2A—C15A	1.3476 (17)	N2B—H2BB	0.8800
N2A—H2AA	0.8800	C1B—C2B	1.3642 (18)
C1A—C2A	1.3688 (19)	C1B—C10B	1.4258 (17)
C1A—C10A	1.4201 (19)	C1B—C11B	1.5007 (17)
C1A—C11A	1.5035 (17)	C2B—C3B	1.4199 (17)
C2A—C3A	1.4220 (18)	C2B—H2BA	0.9500
C2A—H2AB	0.9500	C3B—C4B	1.413 (2)
C3A—C8A	1.413 (2)	C3B—C8B	1.4213 (19)
C3A—C4A	1.419 (2)	C4B—C5B	1.368 (2)
C4A—C5A	1.372 (2)	C4B—H4BA	0.9500
C4A—H4AA	0.9500	C5B—C6B	1.411 (2)
C5A—C6A	1.413 (3)	C5B—H5BA	0.9500
C5A—H5AA	0.9500	C6B—C7B	1.360 (2)
C6A—C7A	1.359 (2)	C6B—H6BA	0.9500
C6A—H6AA	0.9500	C7B—C8B	1.4247 (18)
C7A—C8A	1.4330 (19)	C7B—H7BA	0.9500
C7A—H7AA	0.9500	C8B—C9B	1.411 (2)
C8A—C9A	1.411 (2)	C9B—C10B	1.3659 (18)
C9A—C10A	1.3685 (19)	C9B—H9BA	0.9500
C9A—H9AA	0.9500	C10B—H10B	0.9500
C10A—H10A	0.9500	C12B—C13B	1.3943 (17)
C12A—C16A	1.3981 (18)	C12B—C16B	1.4029 (18)
C12A—C13A	1.3993 (17)	C13B—C14B	1.3828 (17)
C13A—C14A	1.3777 (17)	C13B—H13B	0.9500
C13A—H13A	0.9500	C14B—H14B	0.9500
C14A—H14A	0.9500	C15B—C16B	1.3770 (18)
C15A—C16A	1.3757 (18)	C15B—H15B	0.9500
C15A—H15A	0.9500	C16B—H16B	0.9500

N1S—C1S—S1S	178.91 (14)	C11B—N1B—C12B	127.11 (11)
C11A—N1A—C12A	126.84 (11)	C11B—N1B—H1BA	116.4
C11A—N1A—H1AA	116.6	C12B—N1B—H1BA	116.4
C12A—N1A—H1AA	116.6	C15B—N2B—C14B	117.55 (11)
C14A—N2A—C15A	119.63 (11)	C15B—N2B—H2BB	121.2
C14A—N2A—H2AA	120.2	C14B—N2B—H2BB	121.2
C15A—N2A—H2AA	120.2	C2B—C1B—C10B	119.21 (11)
C2A—C1A—C10A	119.38 (12)	C2B—C1B—C11B	124.68 (11)
C2A—C1A—C11A	124.32 (12)	C10B—C1B—C11B	116.11 (11)
C10A—C1A—C11A	116.29 (12)	C1B—C2B—C3B	121.33 (12)
C1A—C2A—C3A	121.01 (12)	C1B—C2B—H2BA	119.3
C1A—C2A—H2AB	119.5	C3B—C2B—H2BA	119.3
C3A—C2A—H2AB	119.5	C4B—C3B—C2B	121.82 (12)
C8A—C3A—C4A	119.61 (13)	C4B—C3B—C8B	119.12 (12)
C8A—C3A—C2A	119.03 (12)	C2B—C3B—C8B	119.06 (12)
C4A—C3A—C2A	121.36 (13)	C5B—C4B—C3B	120.68 (15)
C5A—C4A—C3A	120.27 (15)	C5B—C4B—H4BA	119.7
C5A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.7
C3A—C4A—H4AA	119.9	C4B—C5B—C6B	120.25 (15)
C4A—C5A—C6A	120.28 (15)	C4B—C5B—H5BA	119.9
C4A—C5A—H5AA	119.9	C6B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.9	C7B—C6B—C5B	120.65 (13)
C7A—C6A—C5A	120.78 (13)	C7B—C6B—H6BA	119.7
C7A—C6A—H6AA	119.6	C5B—C6B—H6BA	119.7
C5A—C6A—H6AA	119.6	C6B—C7B—C8B	120.55 (14)
C6A—C7A—C8A	120.49 (15)	C6B—C7B—H7BA	119.7
C6A—C7A—H7AA	119.8	C8B—C7B—H7BA	119.7
C8A—C7A—H7AA	119.8	C9B—C8B—C3B	118.65 (12)
C9A—C8A—C3A	119.19 (12)	C9B—C8B—C7B	122.67 (13)
C9A—C8A—C7A	122.24 (14)	C3B—C8B—C7B	118.68 (13)
C3A—C8A—C7A	118.57 (13)	C10B—C9B—C8B	121.09 (12)
C10A—C9A—C8A	120.63 (13)	C10B—C9B—H9BA	119.5
C10A—C9A—H9AA	119.7	C8B—C9B—H9BA	119.5
C8A—C9A—H9AA	119.7	C9B—C10B—C1B	120.62 (12)
C9A—C10A—C1A	120.75 (13)	C9B—C10B—H10B	119.7
C9A—C10A—H10A	119.6	C1B—C10B—H10B	119.7
C1A—C10A—H10A	119.6	O1B—C11B—N1B	122.34 (11)
O1A—C11A—N1A	122.82 (11)	O1B—C11B—C1B	121.19 (11)
O1A—C11A—C1A	120.67 (12)	N1B—C11B—C1B	116.47 (11)
N1A—C11A—C1A	116.51 (11)	C13B—C12B—N1B	124.48 (11)
N1A—C12A—C16A	117.80 (11)	C13B—C12B—C16B	117.79 (11)
N1A—C12A—C13A	124.03 (12)	N1B—C12B—C16B	117.72 (11)
C16A—C12A—C13A	118.16 (11)	C14B—C13B—C12B	118.76 (12)
C14A—C13A—C12A	118.88 (12)	C14B—C13B—H13B	120.6
C14A—C13A—H13A	120.6	C12B—C13B—H13B	120.6
C12A—C13A—H13A	120.6	N2B—C14B—C13B	123.50 (12)
N2A—C14A—C13A	122.28 (12)	N2B—C14B—H14B	118.3
N2A—C14A—H14A	118.9	C13B—C14B—H14B	118.3
C13A—C14A—H14A	118.9	N2B—C15B—C16B	123.19 (12)
N2A—C15A—C16A	121.34 (12)	N2B—C15B—H15B	118.4
N2A—C15A—H15A	119.3	C16B—C15B—H15B	118.4
C16A—C15A—H15A	119.3	C15B—C16B—C12B	119.21 (12)
C15A—C16A—C12A	119.70 (12)	C15B—C16B—H16B	120.4
C15A—C16A—H16A	120.1	C12B—C16B—H16B	120.4
C12A—C16A—H16A	120.1

C10A—C1A—C2A—C3A	1.0 (2)	C10B—C1B—C2B—C3B	1.06 (19)
C11A—C1A—C2A—C3A	−178.25 (12)	C11B—C1B—C2B—C3B	−178.88 (11)
C1A—C2A—C3A—C8A	0.0 (2)	C1B—C2B—C3B—C4B	−178.85 (13)
C1A—C2A—C3A—C4A	179.46 (13)	C1B—C2B—C3B—C8B	0.88 (19)
C8A—C3A—C4A—C5A	0.4 (2)	C2B—C3B—C4B—C5B	−178.25 (14)
C2A—C3A—C4A—C5A	−179.09 (14)	C8B—C3B—C4B—C5B	2.0 (2)
C3A—C4A—C5A—C6A	0.1 (2)	C3B—C4B—C5B—C6B	0.2 (2)
C4A—C5A—C6A—C7A	0.0 (2)	C4B—C5B—C6B—C7B	−1.5 (2)
C5A—C6A—C7A—C8A	−0.6 (2)	C5B—C6B—C7B—C8B	0.6 (2)
C4A—C3A—C8A—C9A	179.51 (13)	C4B—C3B—C8B—C9B	177.77 (13)
C2A—C3A—C8A—C9A	−0.98 (19)	C2B—C3B—C8B—C9B	−1.97 (18)
C4A—C3A—C8A—C7A	−1.1 (2)	C4B—C3B—C8B—C7B	−2.89 (19)
C2A—C3A—C8A—C7A	178.46 (12)	C2B—C3B—C8B—C7B	177.37 (12)
C6A—C7A—C8A—C9A	−179.41 (13)	C6B—C7B—C8B—C9B	−179.07 (13)
C6A—C7A—C8A—C3A	1.2 (2)	C6B—C7B—C8B—C3B	1.6 (2)
C3A—C8A—C9A—C10A	1.1 (2)	C3B—C8B—C9B—C10B	1.13 (19)
C7A—C8A—C9A—C10A	−178.35 (13)	C7B—C8B—C9B—C10B	−178.18 (13)
C8A—C9A—C10A—C1A	−0.1 (2)	C8B—C9B—C10B—C1B	0.8 (2)
C2A—C1A—C10A—C9A	−0.9 (2)	C2B—C1B—C10B—C9B	−1.93 (19)
C11A—C1A—C10A—C9A	178.39 (12)	C11B—C1B—C10B—C9B	178.01 (12)
C12A—N1A—C11A—O1A	0.2 (2)	C12B—N1B—C11B—O1B	−0.2 (2)
C12A—N1A—C11A—C1A	−179.59 (11)	C12B—N1B—C11B—C1B	179.44 (11)
C2A—C1A—C11A—O1A	174.42 (13)	C2B—C1B—C11B—O1B	178.11 (13)
C10A—C1A—C11A—O1A	−4.83 (18)	C10B—C1B—C11B—O1B	−1.83 (18)
C2A—C1A—C11A—N1A	−5.75 (19)	C2B—C1B—C11B—N1B	−1.58 (18)
C10A—C1A—C11A—N1A	175.00 (11)	C10B—C1B—C11B—N1B	178.48 (11)
C11A—N1A—C12A—C16A	173.68 (12)	C11B—N1B—C12B—C13B	−8.2 (2)
C11A—N1A—C12A—C13A	−5.9 (2)	C11B—N1B—C12B—C16B	172.51 (12)
N1A—C12A—C13A—C14A	−179.35 (12)	N1B—C12B—C13B—C14B	−178.54 (12)
C16A—C12A—C13A—C14A	1.12 (18)	C16B—C12B—C13B—C14B	0.80 (18)
C15A—N2A—C14A—C13A	0.1 (2)	C15B—N2B—C14B—C13B	0.5 (2)
C12A—C13A—C14A—N2A	−0.9 (2)	C12B—C13B—C14B—N2B	−0.9 (2)
C14A—N2A—C15A—C16A	0.4 (2)	C14B—N2B—C15B—C16B	0.0 (2)
N2A—C15A—C16A—C12A	−0.1 (2)	N2B—C15B—C16B—C12B	0.0 (2)
N1A—C12A—C16A—C15A	179.78 (12)	C13B—C12B—C16B—C15B	−0.39 (19)
C13A—C12A—C16A—C15A	−0.65 (19)	N1B—C12B—C16B—C15B	179.00 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₂O⁺·NCS⁻·C₁₆H₁₂N₂O
M_r	555.64
Crystal system, space group	Triclinic, 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)
V (Å³)	1339.45 (13)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.41
Crystal size (mm)	0.38 × 0.35 × 0.29

Data collection
Diffractometer	Xcalibur (Ruby, Gemini)
Absorption correction	Multi-scan [CrysAlis RED (Agilent, 2011) based on expressions derived from Clark & Reid (1995)]
T_min, T_max	0.904, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9408, 9408, 8399
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.02
No. of reflections	9408
No. of parameters	374
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···N1S	0.88	2.24	3.0576 (17)	153.6
N1B—H1BA···S1Sⁱ	0.88	2.69	3.5345 (11)	162.1
N2A—H2AA···N2B	0.88	1.77	2.6492 (15)	173.4
N2B—H2BB···N2A	0.88	1.77	2.6492 (15)	176.5

Symmetry code: (i) x, y−1, z.

Acknowledgements

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

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
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. CSD CrossRef Web of Science Google Scholar
Priya, B. S., Swamy, B. S. N. & Rangapa, K. S. (2005). Bioorg. Med. Chem. 13, 2623–2628. Web of Science CrossRef PubMed CAS Google Scholar
Saeed, S., Rashid, N., Butcher, R. J., Öztürk Yildirim, S. & Hussain, R. (2012). Acta Cryst. E68, o2762. CSD CrossRef IUCr Journals Google Scholar
Saeed, S., Rashid, N., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1194. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Toda, 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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