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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2152
https://doi.org/10.1107/S1600536812026281

N-(4-Methyl­benz­yl)-3-nitro­anilinium chloride

Marijana Đaković,a* Tomislav Portadab and Dora Ugrinovskic

aDepartment of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia, bDepartment of Organic Chemistry and Biochemistry, Ruder Bošković Institute, PO Box 180, HR-10000 Zagreb, Croatia, and c5th High School, Klaićeva 1, HR-10000 Zagreb, Croatia
*Correspondence e-mail: mdjakovic@chem.pmf.hr

(Received 8 June 2012; accepted 10 June 2012; online 20 June 2012)

The cation of the title compound, C14H15N2O2+·Cl−, comprises two almost ideally planar systems, 3-nitro­phenyl (r.m.s. deviation = 0.0117 Å) and 4-methyl­phenyl (r.m.s. deviation = 0.238 Å), separated by the central C—N bond, and with their mean planes inclined to one another by 61.36 (5)°. In the crystal, hydrogen-bonded chains running along [001] are generated by connecting neighbouring mol­ecules via N—H⋯Cl hydrogen bonds and consolidated by C—H⋯Cl and C—H⋯O inter­actions. Within these chains, fused R21(6) and R32(10) ring motifs are formed. Parallel chains are further linked into a two-dimensional network parallel to (100) via C—H⋯O inter­actions.

Related literature

For the crystal structure of the free base, N-(4-methyl­benz­yl)-3-nitro­aniline, see: Đaković et al. (2012[Đaković, M., Portada, T. & Klačić, T. (2012). Acta Cryst. E68, o1967.]). For the crystal structures of hydro­chloride salts of similar N-benzyl­anilines, see: Dai et al. (2010[Dai, J. & Zheng, W.-N. (2010). Acta Cryst. E66, o517.]); Albrecht et al. (2010[Albrecht, M., Müller, M., Valkonen, A. & Rissanen, K. (2010). CrystEngComm, 12, 3698-3702.]); Boulcina et al. (2011[Boulcina, R., Fantazi, B., Bouacida, S., Roisnel, T. & Debache, A. (2011). Acta Cryst. E67, o2164-o2165.]). For graph-set theory, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]); Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C14H15N2O2+·Cl−

  • Mr = 278.73

  • Monoclinic, P 21 /c

  • a = 14.2586 (7) Å

  • b = 13.1416 (8) Å

  • c = 7.7524 (3) Å

  • β = 105.215 (5)°

  • V = 1401.73 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 296 K

  • 0.56 × 0.46 × 0.14 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Saphire-3 CCD detector

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.852, Tmax = 0.964

  • 8156 measured reflections

  • 4075 independent reflections

  • 2357 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.113

  • S = 0.88

  • 4075 reflections

  • 181 parameters

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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯Cl1 0.87 (2) 2.26 (2) 3.122 (1) 175 (2)
N1—H2N⋯Cl1i 0.94 (2) 2.11 (2) 3.040 (2) 169 (2)
C2—H2⋯Cl1 0.93 2.77 3.517 (1) 139
C5—H5⋯O1ii 0.93 2.55 3.451 (2) 164
C6—H6⋯Cl1ii 0.93 2.69 3.608 (2) 167
C7—H7A⋯O2iii 0.97 2.56 3.393 (2) 144
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) x, y, z+1; (iii) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026281/su2452sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026281/su2452Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812026281/su2452Isup3.cml

checkCIF report


Comment top

The title compound, N-(4-methylbenzyl)-3-nitroanilinium chloride, was prepared in a continuation of our laboratory work with high school students, in the scope of which we have recently reported the structure of the free base, N-(4-methylbenzyl)-3-nitroaniline (Đaković et al., 2012).

As expected, the protonation of the nitrogen atom N1 in the title compound (Fig. 1), significantly influences its overall geometry in comparison with the recently reported structure of its free base mentioned above. In the latter the N-methyl-3-nitroaniline system is nearly ideally planar, while in the title cation only the 3-nitroaniline unit retains its almost ideally planar geometry (r.m.s. deviation of the atoms C1–C6/N1/N2/O1/O2 from their mean plane being 0.0117 Å, with atom N1 deviating from the plane by 0.041 (2) Å). Furthermore, atom C7 is pushed out of the plane by 0.840 (2) Å as a result of the changes in hybridization (sp2 to sp3) after protonation of atom N1. This feature is also reflected in the pronounced differences of the torsion angle C2—C1—N1—C7, that is 140.6 (2) ° for the title cation, and 0.8 (3) ° for the free base. Therefore, contrary to the bent conformation of the free base molecule, the cation of the title compound comprises two almost planar systems, 3-nitrophenyl (r.m.s. deviation = 0.0117 Å) and 4-methylphenyl (r.m.s. deviation = 0.238 Å), that are separated by the central C—N bond, with a dihedral angle of 61.36 (5) °.

In the crystal, neighbouring molecules are linked by N—H···Cl hydrogen bonds and C—H···Cl and C—H···O interactions generating one-dimensional chains running in the [0 0 1] direction (Fig. 2). Within these chains fused R12(6) and R23(10) ring motifs (Etter, 1990; Bernstein et al., 1995) are formed via the C—H···Cl and C—H···O interactions. Parallel chains are further linked into a two-dimensional network via C—H···O interactions (Fig. 3).

Related literature top

For the crystal structure of the free base, N-(4-methylbenzyl)-3-nitroaniline, see: Đaković et al. (2012). For the crystal structures of hydrochloride salts of similar N-benzylanilines, see: Dai et al. (2010); Albrecht et al. (2010); Boulcina et al. (2011). For graph-set theory, see: Etter (1990); Bernstein et al. (1995).

Experimental top

The title compound was prepared by dissolving of N-(4-methylbenzyl)-3-nitroaniline, obtained as previously reported (Đaković et al., 2012), in a methanolic solution of hydrogen chloride, 3% wt. Light-yellow block-like crystals, suitable for the X-ray diffraction analysis, were obtained by slow evaporation over 3–4 days.

Refinement top

The amine H atoms were located in a difference Fourier map and freely refined, giving N—H distances of 0.87 (2) and 0.94 (2) Å. The C-bound H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms: C—H = 0.93, 0.96 and 0.97 A for aromatic, methyl and methylene H atoms, respectively, with Uiso(H) = k ×Ueq(C), where k = 1.5 for methyl H atoms and = 1.2 for other H atoms.

Structure description top

The title compound, N-(4-methylbenzyl)-3-nitroanilinium chloride, was prepared in a continuation of our laboratory work with high school students, in the scope of which we have recently reported the structure of the free base, N-(4-methylbenzyl)-3-nitroaniline (Đaković et al., 2012).

As expected, the protonation of the nitrogen atom N1 in the title compound (Fig. 1), significantly influences its overall geometry in comparison with the recently reported structure of its free base mentioned above. In the latter the N-methyl-3-nitroaniline system is nearly ideally planar, while in the title cation only the 3-nitroaniline unit retains its almost ideally planar geometry (r.m.s. deviation of the atoms C1–C6/N1/N2/O1/O2 from their mean plane being 0.0117 Å, with atom N1 deviating from the plane by 0.041 (2) Å). Furthermore, atom C7 is pushed out of the plane by 0.840 (2) Å as a result of the changes in hybridization (sp2 to sp3) after protonation of atom N1. This feature is also reflected in the pronounced differences of the torsion angle C2—C1—N1—C7, that is 140.6 (2) ° for the title cation, and 0.8 (3) ° for the free base. Therefore, contrary to the bent conformation of the free base molecule, the cation of the title compound comprises two almost planar systems, 3-nitrophenyl (r.m.s. deviation = 0.0117 Å) and 4-methylphenyl (r.m.s. deviation = 0.238 Å), that are separated by the central C—N bond, with a dihedral angle of 61.36 (5) °.

In the crystal, neighbouring molecules are linked by N—H···Cl hydrogen bonds and C—H···Cl and C—H···O interactions generating one-dimensional chains running in the [0 0 1] direction (Fig. 2). Within these chains fused R12(6) and R23(10) ring motifs (Etter, 1990; Bernstein et al., 1995) are formed via the C—H···Cl and C—H···O interactions. Parallel chains are further linked into a two-dimensional network via C—H···O interactions (Fig. 3).

For the crystal structure of the free base, N-(4-methylbenzyl)-3-nitroaniline, see: Đaković et al. (2012). For the crystal structures of hydrochloride salts of similar N-benzylanilines, see: Dai et al. (2010); Albrecht et al. (2010); Boulcina et al. (2011). For graph-set theory, see: Etter (1990); Bernstein et al. (1995).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial view of the crystal packing of the title compound showing the infinite one-dimensional wavy chains running in direction [0 0 1] constructed via N—H···Cl hydrogen bonds and C—H···Cl and C—H···O interactions (dashed cyan lines) involving the chloride ions and the 3-nitrophenyl system. The atoms involved in the fused R12(6) and R23(10) ring motifs are shown as balls (see Table 1 for details).
[Figure 3] Fig. 3. The crystal packing of the title compound viewed along the c axis. The N—H···Cl hydrogen bonds and the C—H···Cl and C—H···O interactions are shown as dashed cyan lines (see Table 1 for details).
N-(4-Methylbenzyl)-3-nitroanilinium chloride top
Crystal data top
C14H15N2O2+·Cl−F(000) = 584
Mr = 278.73Dx = 1.321 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3055 reflections
a = 14.2586 (7) Åθ = 4.5–32.5°
b = 13.1416 (8) ŵ = 0.27 mm−1
c = 7.7524 (3) ÅT = 296 K
β = 105.215 (5)°Block, light-yellow
V = 1401.73 (13) Å30.56 × 0.46 × 0.14 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Saphire-3 CCD detector		4075 independent reflections
Radiation source: Enhance (Mo) X-ray Source2357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 16.3426 pixels mm-1θmax = 30.0°, θmin = 4.6°
CCD scansh = −20→19
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −18→9
Tmin = 0.852, Tmax = 0.964l = −10→6
8156 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.065P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.001
4075 reflectionsΔρmax = 0.31 e Å−3
181 parametersΔρmin = −0.20 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0056 (14)
Crystal data top
C14H15N2O2+·Cl−V = 1401.73 (13) Å3
Mr = 278.73Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.2586 (7) ŵ = 0.27 mm−1
b = 13.1416 (8) ÅT = 296 K
c = 7.7524 (3) Å0.56 × 0.46 × 0.14 mm
β = 105.215 (5)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Saphire-3 CCD detector		4075 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		2357 reflections with I > 2σ(I)
Tmin = 0.852, Tmax = 0.964Rint = 0.024
8156 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 0.88Δρmax = 0.31 e Å−3
4075 reflectionsΔρmin = −0.20 e Å−3
181 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
O10.57567 (10)0.63507 (13)0.82246 (19)0.0791 (6)
O20.68831 (9)0.61154 (13)1.0638 (2)0.0867 (6)
N10.26475 (8)0.65004 (11)1.00157 (16)0.0369 (4)
N20.60377 (10)0.62354 (11)0.9829 (2)0.0541 (5)
C10.36701 (10)0.63347 (11)1.09502 (17)0.0347 (4)
C20.43444 (10)0.63446 (11)0.99596 (18)0.0372 (4)
C30.53073 (10)0.62306 (12)1.08717 (19)0.0404 (5)
C40.56150 (12)0.61009 (14)1.2695 (2)0.0543 (6)
C50.49261 (13)0.61086 (15)1.3644 (2)0.0588 (6)
C60.39530 (12)0.62219 (13)1.27825 (19)0.0478 (5)
C70.19176 (11)0.58625 (15)1.0622 (2)0.0502 (5)
C80.09152 (11)0.60310 (14)0.94307 (19)0.0445 (5)
C90.05107 (12)0.53434 (15)0.8091 (2)0.0528 (6)
C10−0.04264 (12)0.54790 (15)0.7043 (2)0.0564 (6)
C11−0.09779 (12)0.62937 (15)0.7283 (2)0.0541 (6)
C12−0.05627 (13)0.69956 (17)0.8588 (3)0.0681 (7)
C130.03705 (12)0.68605 (16)0.9664 (2)0.0613 (7)
C14−0.20099 (14)0.64248 (19)0.6153 (3)0.0808 (9)
Cl10.24918 (3)0.62691 (3)0.59416 (4)0.0470 (1)
H1N0.2565 (11)0.6433 (12)0.887 (2)0.042 (4)*
H20.415700.642500.872500.0450*
H2N0.2519 (14)0.7188 (17)1.020 (3)0.073 (6)*
H40.627000.601101.326700.0650*
H50.511700.603701.488000.0710*
H60.349100.622201.343500.0570*
H7A0.208900.514901.059800.0600*
H7B0.192900.604001.184200.0600*
H90.087200.478600.789600.0630*
H10−0.068900.500600.615500.0680*
H12−0.091600.756700.874600.0820*
H130.063200.733401.055200.0740*
H14A−0.228400.703000.651600.1210*
H14B−0.239000.584600.630700.1210*
H14C−0.201100.648200.491800.1210*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0592 (8)0.1205 (14)0.0652 (9)0.0020 (8)0.0300 (7)−0.0021 (8)
O20.0341 (7)0.1123 (14)0.1114 (11)0.0022 (8)0.0153 (7)−0.0063 (9)
N10.0342 (6)0.0468 (9)0.0297 (6)0.0033 (6)0.0083 (4)0.0001 (5)
N20.0361 (7)0.0534 (10)0.0733 (10)−0.0024 (7)0.0154 (6)−0.0096 (7)
C10.0341 (7)0.0351 (8)0.0327 (6)0.0023 (6)0.0047 (5)−0.0007 (5)
C20.0364 (7)0.0408 (9)0.0327 (6)0.0023 (7)0.0061 (5)0.0000 (6)
C30.0332 (7)0.0370 (9)0.0488 (8)−0.0025 (7)0.0067 (6)−0.0047 (6)
C40.0399 (8)0.0597 (12)0.0518 (9)0.0045 (8)−0.0084 (7)−0.0010 (8)
C50.0613 (11)0.0724 (14)0.0332 (7)0.0026 (10)−0.0044 (7)0.0023 (7)
C60.0505 (8)0.0602 (11)0.0318 (7)0.0014 (8)0.0092 (6)−0.0001 (7)
C70.0408 (8)0.0648 (12)0.0462 (8)−0.0038 (8)0.0138 (6)0.0082 (7)
C80.0359 (7)0.0576 (11)0.0420 (8)−0.0031 (7)0.0137 (6)0.0004 (7)
C90.0479 (9)0.0566 (11)0.0576 (9)0.0014 (9)0.0204 (7)−0.0054 (8)
C100.0496 (10)0.0692 (13)0.0498 (9)−0.0136 (10)0.0121 (7)−0.0114 (8)
C110.0398 (8)0.0686 (13)0.0520 (9)−0.0047 (9)0.0088 (7)0.0064 (8)
C120.0465 (10)0.0709 (15)0.0858 (13)0.0099 (10)0.0153 (9)−0.0137 (11)
C130.0468 (10)0.0702 (14)0.0646 (11)−0.0019 (10)0.0106 (8)−0.0207 (9)
C140.0413 (10)0.104 (2)0.0879 (14)−0.0025 (11)0.0006 (9)0.0170 (12)
Cl10.0535 (2)0.0530 (3)0.0344 (2)−0.0059 (2)0.0116 (1)−0.0013 (2)
Geometric parameters (Å, º) top
O1—N21.212 (2)C10—C111.370 (3)
O2—N21.214 (2)C11—C121.382 (3)
N1—C11.464 (2)C11—C141.512 (3)
N1—C71.505 (2)C12—C131.384 (3)
N2—C31.477 (2)C2—H20.9300
N1—H2N0.94 (2)C4—H40.9300
N1—H1N0.87 (2)C5—H50.9300
C1—C21.379 (2)C6—H60.9300
C1—C61.379 (2)C7—H7A0.9700
C2—C31.378 (2)C7—H7B0.9700
C3—C41.376 (2)C9—H90.9300
C4—C51.373 (2)C10—H100.9300
C5—C61.381 (2)C12—H120.9300
C7—C81.501 (2)C13—H130.9300
C8—C131.378 (3)C14—H14A0.9600
C8—C91.383 (2)C14—H14B0.9600
C9—C101.381 (2)C14—H14C0.9600
Cl1···C23.5173 (14)C6···H7B2.8000
Cl1···C6i3.6084 (17)C6···H7A3.0900
Cl1···N13.1224 (13)C7···H62.7300
Cl1···N1ii3.0398 (15)C13···H2N3.01 (2)
Cl1···C1ii3.5683 (15)C14···H12ii3.0300
Cl1···H6i2.6900C14···H4x2.9000
Cl1···H22.7700H1N···Cl12.255 (15)
Cl1···H7Bi3.0800H1N···H22.3000
Cl1···H1N2.255 (15)H2···O12.4100
Cl1···H10iii3.1400H2···H1N2.3000
Cl1···H2Nii2.11 (2)H2···Cl12.7700
O1···C4ii3.374 (3)H2N···C133.01 (2)
O2···C7iv3.393 (2)H2N···Cl1vi2.11 (2)
O1···H5i2.5500H4···O22.4200
O1···H22.4100H4···H14Cxi2.5300
O2···H7Aiv2.5600H4···C14xi2.9000
O2···H42.4200H5···O1viii2.5500
O2···H14Av2.7200H5···C5vii3.0500
N1···Cl13.1224 (13)H6···C72.7300
N1···Cl1vi3.0398 (15)H6···H7B2.2600
N2···C2iv3.445 (2)H6···Cl1viii2.6900
C1···Cl1vi3.5683 (15)H7A···C63.0900
C2···C6ii3.591 (2)H7A···H92.3900
C2···N2iv3.445 (2)H7A···O2iv2.5600
C2···C3iv3.505 (2)H7B···H62.2600
C2···Cl13.5173 (14)H7B···Cl1viii3.0800
C3···C3iv3.526 (2)H7B···C62.8000
C3···C2iv3.505 (2)H7B···H132.5200
C4···O1vi3.374 (3)H9···H7A2.3900
C5···C5vii3.567 (3)H10···Cl1iii3.1400
C6···C2vi3.591 (2)H12···H14Cvi2.3600
C6···Cl1viii3.6084 (17)H12···H14A2.3500
C7···O2iv3.393 (2)H12···C14vi3.0300
C7···C10ix3.595 (2)H13···H7B2.5200
C8···C10ix3.591 (2)H14A···O2xii2.7200
C10···C8ix3.591 (2)H14A···H122.3500
C10···C7ix3.595 (2)H14C···H4x2.5300
C5···H5vii3.0500H14C···H12ii2.3600
C1—N1—C7116.3 (1)C8—C13—C12120.56 (17)
O1—N2—O2124.2 (2)C1—C2—H2121.00
O1—N2—C3118.1 (1)C3—C2—H2121.00
O2—N2—C3117.6 (1)C3—C4—H4121.00
C1—N1—H2N106.0 (13)C5—C4—H4121.00
C7—N1—H1N110.1 (11)C4—C5—H5120.00
C7—N1—H2N108.0 (13)C6—C5—H5120.00
H1N—N1—H2N105.9 (17)C1—C6—H6120.00
C1—N1—H1N109.9 (11)C5—C6—H6120.00
N1—C1—C2118.2 (1)N1—C7—H7A110.00
N1—C1—C6120.7 (1)N1—C7—H7B110.00
C2—C1—C6121.09 (14)C8—C7—H7A110.00
C1—C2—C3117.37 (13)C8—C7—H7B110.00
N2—C3—C4118.8 (1)H7A—C7—H7B108.00
N2—C3—C2118.0 (1)C8—C9—H9120.00
C2—C3—C4123.15 (14)C10—C9—H9120.00
C3—C4—C5117.99 (15)C9—C10—H10119.00
C4—C5—C6120.72 (14)C11—C10—H10119.00
C1—C6—C5119.67 (15)C11—C12—H12120.00
N1—C7—C8110.5 (1)C13—C12—H12120.00
C7—C8—C13120.98 (15)C8—C13—H13120.00
C9—C8—C13118.50 (15)C12—C13—H13120.00
C7—C8—C9120.52 (16)C11—C14—H14A109.00
C8—C9—C10120.38 (17)C11—C14—H14B109.00
C9—C10—C11121.48 (16)C11—C14—H14C109.00
C10—C11—C12118.05 (16)H14A—C14—H14B109.00
C12—C11—C14120.85 (18)H14A—C14—H14C109.00
C10—C11—C14121.10 (17)H14B—C14—H14C109.00
C11—C12—C13120.99 (19)
C7—N1—C1—C2140.58 (14)C3—C4—C5—C61.3 (3)
C7—N1—C1—C6−42.5 (2)C4—C5—C6—C1−0.4 (3)
C1—N1—C7—C8−174.06 (13)N1—C7—C8—C13−81.38 (19)
O1—N2—C3—C20.8 (2)N1—C7—C8—C999.82 (19)
O1—N2—C3—C4−179.97 (17)C7—C8—C9—C10177.41 (16)
O2—N2—C3—C2−178.65 (16)C13—C8—C9—C10−1.4 (3)
O2—N2—C3—C40.6 (2)C7—C8—C13—C12−178.34 (17)
C2—C1—C6—C5−0.5 (2)C9—C8—C13—C120.5 (3)
N1—C1—C2—C3177.31 (13)C8—C9—C10—C110.5 (3)
N1—C1—C6—C5−177.32 (15)C9—C10—C11—C14−178.80 (17)
C6—C1—C2—C30.4 (2)C9—C10—C11—C121.3 (3)
C1—C2—C3—C40.6 (2)C14—C11—C12—C13177.86 (18)
C1—C2—C3—N2179.76 (13)C10—C11—C12—C13−2.3 (3)
N2—C3—C4—C5179.37 (16)C11—C12—C13—C81.4 (3)
C2—C3—C4—C5−1.5 (3)
Symmetry codes: (i) x, y, z−1; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+2; (v) x+1, −y+3/2, z+1/2; (vi) x, −y+3/2, z+1/2; (vii) −x+1, −y+1, −z+3; (viii) x, y, z+1; (ix) −x, −y+1, −z+2; (x) x−1, y, z−1; (xi) x+1, y, z+1; (xii) x−1, −y+3/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl10.87 (2)2.26 (2)3.122 (1)175 (2)
N1—H2N···Cl1vi0.94 (2)2.11 (2)3.040 (2)169 (2)
C2—H2···Cl10.932.773.517 (1)139
C5—H5···O1viii0.932.553.451 (2)164
C6—H6···Cl1viii0.932.693.608 (2)167
C7—H7A···O2iv0.972.563.393 (2)144
Symmetry codes: (iv) −x+1, −y+1, −z+2; (vi) x, −y+3/2, z+1/2; (viii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC14H15N2O2+·Cl−
Mr278.73
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.2586 (7), 13.1416 (8), 7.7524 (3)
β (°) 105.215 (5)
V (Å3)1401.73 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.56 × 0.46 × 0.14
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Saphire-3 CCD detector
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.852, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections		8156, 4075, 2357
Rint0.024
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.113, 0.88
No. of reflections4075
No. of parameters181
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.31, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl10.87 (2)2.26 (2)3.122 (1)175 (2)
N1—H2N···Cl1i0.94 (2)2.11 (2)3.040 (2)169 (2)
C2—H2···Cl10.932.773.517 (1)139
C5—H5···O1ii0.932.553.451 (2)164
C6—H6···Cl1ii0.932.693.608 (2)167
C7—H7A···O2iii0.972.563.393 (2)144
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+2.
 

Acknowledgements

This research was supported by the Ministry of Science, Education and Sports of the Republic of Croatia, Zagreb (grant Nos. 119–1193079–1332 and 098–0982904–2912) and the 5th High School, Zagreb, Croatia.

References

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2152
https://doi.org/10.1107/S1600536812026281
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