organic compounds
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
The 16H13N2O+·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 the shortest centroid–centroid distance being 3.5929 (8) Å. The was determined from a nonmerohedral twin {ratio of the twin components = 0.357 (1):0.643 (1) and [-100 0-10 -101]}.
of the title compound, CRelated 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
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell 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
https://doi.org/10.1107/S1600536812039864/xu5617sup1.cif
contains datablocks I, global. DOI: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
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.
The
was solved from non-merohedral twin with the 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 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).
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,
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 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).
of the title compound (Fig. 1), [(C16H13N2O+)(NCS-)] C16H12N2O, there are two independent molecules (A and B) in the 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 weakFor 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).
Data collection: CrysAlis PRO (Agilent, 2011); cell
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).C16H13N2O+·NCS−·C16H12N2O | Z = 2 |
Mr = 555.64 | F(000) = 580 |
Triclinic, P1 | Dx = 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 |
Xcalibur (Ruby, Gemini) diffractometer | 9408 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 8399 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 76.0°, θmin = 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 |
Tmin = 0.904, Tmax = 1.000 | l = −12→16 |
9408 measured reflections |
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(Fo2) + (0.0899P)2 + 0.2899P] where P = (Fo2 + 2Fc2)/3 |
9408 reflections | (Δ/σ)max = 0.001 |
374 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C16H13N2O+·NCS−·C16H12N2O | γ = 71.684 (5)° |
Mr = 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)° |
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 = 1.000 | Rint = 0.000 |
9408 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.36 e Å−3 |
9408 reflections | Δρmin = −0.30 e Å−3 |
374 parameters |
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. |
x | y | z | Uiso*/Ueq | 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* |
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) |
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) |
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 |
Mr | 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)] |
Tmin, Tmax | 0.904, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9408, 9408, 8399 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.36, −0.30 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).