2-Hy­droxy-N-(4-meth­oxy­benz­yl)-4-nitro­anilinium chloride

Boulcina, R.; Fantazi, B.; Bouacida, S.; Roisnel, T.; Debache, A.

doi:10.1107/S1600536811029552

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o2164-o2165

doi:10.1107/S1600536811029552

Open

access

2-Hydroxy-N-(4-methoxybenzyl)-4-nitroanilinium chloride

Raouf Boulcina,^a Boubakeur Fantazi,^b Sofiane Bouacida,^b ^*‡ Thierry Roisnel ^c and Abdelmadjid Debache ^a

^aLaboratoire des Produits Naturels d'origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 28 June 2011; accepted 21 July 2011; online 30 July 2011)

The crystal structure of the title compound, C₁₄H₁₅N₂O₄⁺·Cl⁻, can be described as being composed of layers containing both cations and anions that are staggered along [010]. Two types of the hydrogen bonds are observed, viz. cation–anion and cation–cation. The chloride anions are acceptors of the strong hydrogen bonds donated by the secondary amine and the hydroxy groups. The packing is also stabilized by weak C—H⋯O intermolecular hydrogen bonds. An intramolecular N—H⋯O interaction also occurs.

Related literature

For the preparation of amines, see: Apodaca & Xiao (2001 ); Baxter & Reitz (2002 ); Salvatore et al. (2002 ); Sato et al. (2004 ). For applications of amines, see: Bergeron et al. (1997 ); Seayad et al. (2002 ). For background to hydrogen bonding, see: Desiraju (2003 ); Dorn et al. (2005 ) and for hydrogen-bond motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₄H₁₅N₂O₄⁺·Cl⁻
M_r = 310.73
Monoclinic, C 2/c
a = 32.1166 (9) Å
b = 7.4888 (2) Å
c = 13.0907 (4) Å
β = 108.655 (2)°
V = 2983.09 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.18 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.784, T_max = 0.984
11129 measured reflections
3359 independent reflections
2290 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.079
S = 1.35
3359 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1	0.84	2.16	2.9950 (13)	174
N10—H10A⋯O1	0.92	2.22	2.652 (2)	108
N10—H10A⋯Cl1ⁱ	0.92	2.30	3.1082 (17)	146
N10—H10B⋯Cl1ⁱⁱ	0.92	2.23	3.0518 (15)	149
C8—H8⋯O5ⁱⁱ	0.93	2.58	3.273 (2)	132
C14—H14⋯O6ⁱⁱⁱ	0.93	2.48	3.388 (3)	165
Symmetry codes: (i) $[-x, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029552/fb2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029552/fb2237Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029552/fb2237Isup3.cml

checkCIF report

Comment top

Amines are one of the most important classes of biologically active compounds of natural origin. They are also widely used in the chemical industry as basic intermediates for preparation of e.g. fine chemicals, pharmaceuticals and agrochemicals (Seayad et al., 2002).

Due to their biological properties, amines have played important role in chemotherapeutic treatment of different diseases (Bergeron et al., 1997).

Alkylation of the secondary amines with alkyl halides is the most straightforward method for the synthesis of the tertiary amines (Salvatore et al., 2002). Reductive amination of aldehydes andketones is a powerful tool for the synthesis of amines. This approach is extensively used for rapid access to diverse sets of amines (Sato et al., 2004; Baxter et al., 2002; Apodaca et al., 2001).

The synthetic route we envisioned for preparation of the title compounds consists of a one-step reductive amination of aromatic aldehydes with primary amine at acid conditions (pH = 4-5). We found that this could be efficiently conducted in methanol at room temperature using the excess of reductive agent (NaBH₃CN). Under these conditions 2-(4-methoxybenzylamino)-5-nitrophenol was cleanly obtained in very good chemical yield (85%).

Fig. 1 shows the title molecule. The two benzene rings contain the interplanar angle equal to 35.35 (6)°. In the crystal packing, the important role play the hydrogen bonds. In the title structure, two types of hydrogen bonds are present, interconnecting the cations with the anions as well as mutually the cations. The chloride anions are involved as acceptors in the strong hydrogen bonds (Desiraju, 2003; Dorn et al. 2005) with the secondary amine and the hydroxy group stemming from the cation (Tab. 1), i.e. in [O—H···Cl^- and N—H···Cl^-] hydrogen bonds interactions.

The layers staggered along the b axis can be discerned in the crystal structure (Fig. 2). Each layer contains dimers composed of the cations and Cl^-. These dimers are situated about the crystallographic two-fold axes. The dimers form the motifs R²₄(14) (Etter et al., 1990) with a pair of chains O1-H1···Cl1···H10a-N10-C1-C9 (Fig. 3). Moreover, the dimers are interconnected with those in the adjacent layer by another pair of the hydrogen bonds Cl1···H10b-N10-H10a with the graph set motif R²₄(8) (Fig. 3). The latter motifs are situated about the crystallographic inversion centres. The packing is also stabilized by weak N—H···O (intramolecular) and C—H···O (intermolecular) interactions (Fig. 4, Tab. 1). Fig. 5 shows the projection of the structure along the a axis.

Related literature top

For the preparation of amines, see: Apodaca & Xiao (2001); Baxter & Reitz (2002); Salvatore et al. (2002); Sato et al. (2004). For applications of amines, see: Bergeron et al. (1997); Seayad et al. (2002). For background to hydrogen bonding, see: Desiraju (2003); Dorn et al. (2005) and for hydrogen-bond motifs, see: Etter et al. (1990).

Experimental top

To the solution of 4-methoxybenzaldehyde (2 mmol) in dry methanol (10 ml) 5-nitro-2-aminophenol (2 mmol) was added and acidified by concentrated HCl until pH = 6. After vigorous stirring for 2 h at room temperature, NaBH₃CN (6 mmol) was added. On completion of the reaction, as indicated by thin layer chromatography (ethyl acetate/hexane: 1/3 as eluent), the excess of the hydride was carefully destroyed by slow addition of 20 ml of cold water. The mixture was left for several hours and the resulting precipitate was filtered off, washed with water, then with ethanol and with hexane. 2-(4-methoxybenzylamino)-5-nitrophenol was identified by IR, ¹H and ¹³C NMR spectroscopies. Colourless prismatic crystals (0.06×0.12×0.18 mm) of the title structure were obtained by slow crystallization from the aqueous solution with pH = 5.5.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The title molecule (Farrugia, 1997) with the atomic labelling scheme. The displacement parameters are drawn at the 50% probability level.
	Fig. 2. The packing of the title structure viewed down the c axis (Brandenburg & Berndt, 2001). Cl is shown in green, N in blue and C in grey.
	Fig. 3. A section of the title structure showing the hydrogen bonds N—H···Cl and O—H···Cl as dashed lines (Brandenburg & Berndt, 2001). Cl is shown in green, N in blue and C in grey.
	Fig. 4. A section of the title structure showing intermolecular hydrogen bond N—H···O and weak C—H···O interactions as dashed lines (Brandenburg & Berndt, 2001). Cl is shown in green, N in blue and C in grey.
	Fig. 5. The packing of the title structure viewed down the a axis (Brandenburg & Berndt, 2001). Cl is shown in green, N in blue and C in grey.

2-Hydroxy-N-(4-methoxybenzyl)-4-nitroanilinium chloride top

Crystal data top

C₁₄H₁₅N₂O₄⁺·Cl⁻	F(000) = 1296
M_r = 310.73	D_x = 1.384 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1996 reflections
a = 32.1166 (9) Å	θ = 2.7–25.9°
b = 7.4888 (2) Å	µ = 0.27 mm⁻¹
c = 13.0907 (4) Å	T = 100 K
β = 108.655 (2)°	Prism, colourless
V = 2983.09 (15) Å³	0.18 × 0.12 × 0.06 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	2290 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −41→36
T_min = 0.784, T_max = 0.984	k = −9→8
11129 measured reflections	l = −16→13
3359 independent 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.079	H-atom parameters constrained
S = 1.35	w = 1/[σ²(F_o²) + (0.010P)²] where P = (F_o² + 2F_c²)/3
3359 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³
59 constraints

Crystal data top

C₁₄H₁₅N₂O₄⁺·Cl⁻	V = 2983.09 (15) Å³
M_r = 310.73	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.1166 (9) Å	µ = 0.27 mm⁻¹
b = 7.4888 (2) Å	T = 100 K
c = 13.0907 (4) Å	0.18 × 0.12 × 0.06 mm
β = 108.655 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3359 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	2290 reflections with I > 2σ(I)
T_min = 0.784, T_max = 0.984	R_int = 0.049
11129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.35	Δρ_max = 0.32 e Å⁻³
3359 reflections	Δρ_min = −0.25 e Å⁻³
191 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.05089 (4)	0.24108 (16)	0.25570 (10)	0.0282 (4)
H1	0.0481	0.2513	0.317	0.042*
O5	0.19661 (4)	0.3946 (2)	0.52794 (12)	0.0450 (4)
O6	0.23649 (5)	0.4782 (2)	0.43081 (12)	0.0596 (5)
O18	0.16637 (4)	0.13654 (17)	−0.26241 (11)	0.0333 (4)
N4	0.20173 (6)	0.4259 (2)	0.44038 (15)	0.0365 (5)
N10	0.05796 (5)	0.31371 (19)	0.06366 (12)	0.0219 (4)
H10A	0.0329	0.3166	0.0834	0.026*
H10B	0.0562	0.4062	0.0162	0.026*
C1	0.09069 (6)	0.3047 (2)	0.25869 (16)	0.0223 (5)
C2	0.12573 (6)	0.3321 (2)	0.35182 (16)	0.0250 (5)
H2	0.1233	0.3074	0.4194	0.03*
C3	0.16445 (6)	0.3973 (3)	0.34105 (16)	0.0259 (5)
C7	0.16978 (6)	0.4387 (3)	0.24313 (16)	0.0289 (5)
H7	0.1963	0.4833	0.2395	0.035*
C8	0.13458 (6)	0.4118 (2)	0.15093 (16)	0.0247 (5)
H8	0.1369	0.439	0.0837	0.03*
C9	0.09576 (6)	0.3441 (2)	0.15932 (15)	0.0207 (5)
C11	0.05879 (6)	0.1389 (2)	0.00555 (16)	0.0273 (5)
H11A	0.068	0.044	0.0584	0.033*
H11B	0.0293	0.1116	−0.0407	0.033*
C12	0.08902 (6)	0.1425 (2)	−0.06154 (16)	0.0232 (5)
C13	0.13234 (6)	0.0854 (2)	−0.02110 (16)	0.0267 (5)
H13	0.1432	0.0459	0.0499	0.032*
C14	0.15987 (6)	0.0858 (2)	−0.08398 (16)	0.0264 (5)
H14	0.1891	0.0507	−0.0548	0.032*
C15	0.14329 (6)	0.1393 (2)	−0.19111 (16)	0.0236 (5)
C16	0.10009 (6)	0.1979 (2)	−0.23310 (15)	0.0245 (5)
H16	0.089	0.2353	−0.3045	0.029*
C17	0.07379 (6)	0.2001 (2)	−0.16807 (16)	0.0248 (5)
H17	0.045	0.2412	−0.1962	0.03*
C19	0.21172 (6)	0.0849 (3)	−0.22251 (18)	0.0447 (6)
H19A	0.2139	−0.0351	−0.1955	0.067*
H19B	0.2273	0.1641	−0.1654	0.067*
H19C	0.2243	0.0912	−0.2799	0.067*
Cl1	0.042616 (15)	0.30709 (6)	0.47404 (4)	0.02477 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0289 (8)	0.0383 (9)	0.0212 (8)	−0.0058 (6)	0.0133 (7)	0.0010 (6)
O5	0.0345 (9)	0.0751 (12)	0.0242 (9)	0.0038 (8)	0.0079 (7)	−0.0032 (8)
O6	0.0226 (9)	0.1194 (16)	0.0372 (10)	−0.0117 (9)	0.0102 (8)	−0.0126 (10)
O18	0.0293 (8)	0.0455 (10)	0.0306 (9)	0.0039 (7)	0.0174 (7)	−0.0011 (7)
N4	0.0260 (11)	0.0543 (13)	0.0292 (12)	0.0056 (9)	0.0087 (9)	−0.0083 (10)
N10	0.0229 (9)	0.0259 (10)	0.0201 (9)	−0.0018 (7)	0.0112 (7)	−0.0006 (8)
C1	0.0221 (11)	0.0214 (11)	0.0265 (12)	0.0034 (9)	0.0120 (9)	0.0004 (9)
C2	0.0275 (12)	0.0290 (13)	0.0200 (11)	0.0072 (9)	0.0096 (9)	0.0017 (9)
C3	0.0215 (11)	0.0328 (13)	0.0230 (12)	0.0054 (9)	0.0066 (9)	−0.0049 (10)
C7	0.0209 (11)	0.0378 (14)	0.0309 (13)	0.0003 (9)	0.0125 (10)	−0.0048 (10)
C8	0.0268 (11)	0.0309 (13)	0.0211 (11)	0.0013 (9)	0.0140 (9)	−0.0004 (9)
C9	0.0205 (10)	0.0206 (12)	0.0212 (11)	0.0015 (8)	0.0072 (9)	−0.0018 (9)
C11	0.0337 (12)	0.0237 (12)	0.0263 (12)	−0.0035 (9)	0.0121 (10)	−0.0044 (9)
C12	0.0285 (12)	0.0216 (12)	0.0217 (11)	−0.0027 (9)	0.0112 (9)	−0.0035 (9)
C13	0.0321 (12)	0.0284 (13)	0.0192 (11)	0.0032 (10)	0.0073 (9)	−0.0007 (9)
C14	0.0220 (11)	0.0317 (13)	0.0246 (12)	0.0039 (9)	0.0060 (9)	−0.0026 (10)
C15	0.0254 (11)	0.0257 (12)	0.0228 (12)	−0.0031 (9)	0.0120 (9)	−0.0046 (9)
C16	0.0276 (11)	0.0276 (12)	0.0171 (11)	0.0006 (9)	0.0053 (9)	0.0017 (9)
C17	0.0214 (11)	0.0267 (12)	0.0253 (12)	−0.0014 (9)	0.0064 (9)	−0.0019 (10)
C19	0.0297 (13)	0.0644 (17)	0.0467 (16)	0.0054 (12)	0.0218 (12)	−0.0007 (13)
Cl1	0.0245 (3)	0.0286 (3)	0.0224 (3)	0.0021 (2)	0.0091 (2)	−0.0001 (2)

Geometric parameters (Å, º) top

O1—C1	1.353 (2)	C8—C9	1.382 (2)
O1—H1	0.84	C8—H8	0.93
O5—N4	1.231 (2)	C11—C12	1.503 (2)
O6—N4	1.2268 (19)	C11—H11A	0.97
O18—C15	1.365 (2)	C11—H11B	0.97
O18—C19	1.434 (2)	C12—C13	1.389 (2)
N4—C3	1.475 (2)	C12—C17	1.390 (3)
N10—C9	1.456 (2)	C13—C14	1.387 (2)
N10—C11	1.519 (2)	C13—H13	0.93
N10—H10A	0.9201	C14—C15	1.390 (3)
N10—H10B	0.9201	C14—H14	0.93
C1—C2	1.385 (2)	C15—C16	1.390 (2)
C1—C9	1.393 (2)	C16—C17	1.378 (2)
C2—C3	1.385 (2)	C16—H16	0.93
C2—H2	0.93	C17—H17	0.93
C3—C7	1.381 (3)	C19—H19A	0.96
C7—C8	1.379 (2)	C19—H19B	0.96
C7—H7	0.93	C19—H19C	0.96

C1—O1—H1	109.3	C12—C11—H11A	108.9
C15—O18—C19	117.73 (15)	N10—C11—H11A	108.9
O6—N4—O5	123.56 (18)	C12—C11—H11B	108.9
O6—N4—C3	117.71 (18)	N10—C11—H11B	108.9
O5—N4—C3	118.73 (17)	H11A—C11—H11B	107.7
C9—N10—C11	114.97 (13)	C13—C12—C17	117.77 (18)
C9—N10—H10A	108.5	C13—C12—C11	121.83 (18)
C11—N10—H10A	108.5	C17—C12—C11	120.38 (17)
C9—N10—H10B	108.5	C14—C13—C12	121.61 (18)
C11—N10—H10B	108.5	C14—C13—H13	119.2
H10A—N10—H10B	107.5	C12—C13—H13	119.2
O1—C1—C2	124.88 (17)	C13—C14—C15	119.21 (18)
O1—C1—C9	116.05 (17)	C13—C14—H14	120.4
C2—C1—C9	119.07 (17)	C15—C14—H14	120.4
C3—C2—C1	117.78 (18)	O18—C15—C16	115.21 (17)
C3—C2—H2	121.1	O18—C15—C14	124.67 (17)
C1—C2—H2	121.1	C16—C15—C14	120.11 (18)
C7—C3—C2	123.74 (19)	C17—C16—C15	119.42 (18)
C7—C3—N4	118.62 (17)	C17—C16—H16	120.3
C2—C3—N4	117.63 (18)	C15—C16—H16	120.3
C3—C7—C8	117.97 (18)	C16—C17—C12	121.83 (18)
C3—C7—H7	121	C16—C17—H17	119.1
C8—C7—H7	121	C12—C17—H17	119.1
C9—C8—C7	119.44 (18)	O18—C19—H19A	109.5
C9—C8—H8	120.3	O18—C19—H19B	109.5
C7—C8—H8	120.3	H19A—C19—H19B	109.5
C8—C9—C1	121.97 (18)	O18—C19—H19C	109.5
C8—C9—N10	120.92 (17)	H19A—C19—H19C	109.5
C1—C9—N10	117.10 (16)	H19B—C19—H19C	109.5
C12—C11—N10	113.27 (14)

O1—C1—C2—C3	179.67 (17)	C11—N10—C9—C8	82.5 (2)
C9—C1—C2—C3	−0.2 (3)	C11—N10—C9—C1	−98.47 (19)
C1—C2—C3—C7	0.9 (3)	C9—N10—C11—C12	−77.3 (2)
C1—C2—C3—N4	−179.87 (16)	N10—C11—C12—C13	93.1 (2)
O6—N4—C3—C7	−3.1 (3)	N10—C11—C12—C17	−88.4 (2)
O5—N4—C3—C7	177.68 (18)	C17—C12—C13—C14	0.3 (3)
O6—N4—C3—C2	177.70 (18)	C11—C12—C13—C14	178.75 (17)
O5—N4—C3—C2	−1.6 (3)	C12—C13—C14—C15	−2.1 (3)
C2—C3—C7—C8	−0.6 (3)	C19—O18—C15—C16	177.25 (17)
N4—C3—C7—C8	−179.78 (17)	C19—O18—C15—C14	−3.9 (3)
C3—C7—C8—C9	−0.5 (3)	C13—C14—C15—O18	−176.41 (17)
C7—C8—C9—C1	1.2 (3)	C13—C14—C15—C16	2.4 (3)
C7—C8—C9—N10	−179.87 (16)	O18—C15—C16—C17	178.03 (16)
O1—C1—C9—C8	179.28 (16)	C14—C15—C16—C17	−0.9 (3)
C2—C1—C9—C8	−0.8 (3)	C15—C16—C17—C12	−1.0 (3)
O1—C1—C9—N10	0.3 (2)	C13—C12—C17—C16	1.3 (3)
C2—C1—C9—N10	−179.82 (15)	C11—C12—C17—C16	−177.19 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.84	2.16	2.9950 (13)	174
N10—H10A···O1	0.92	2.22	2.652 (2)	108
N10—H10A···Cl1ⁱ	0.92	2.30	3.1082 (17)	146
N10—H10B···Cl1ⁱⁱ	0.92	2.23	3.0518 (15)	149
C8—H8···O5ⁱⁱ	0.93	2.58	3.273 (2)	132
C14—H14···O6ⁱⁱⁱ	0.93	2.48	3.388 (3)	165

Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₂O₄⁺·Cl⁻
M_r	310.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	32.1166 (9), 7.4888 (2), 13.0907 (4)
β (°)	108.655 (2)
V (Å³)	2983.09 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.18 × 0.12 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.784, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11129, 3359, 2290
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.079, 1.35
No. of reflections	3359
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.84	2.16	2.9950 (13)	174
N10—H10A···O1	0.92	2.22	2.652 (2)	108
N10—H10A···Cl1ⁱ	0.92	2.30	3.1082 (17)	146
N10—H10B···Cl1ⁱⁱ	0.92	2.23	3.0518 (15)	149
C8—H8···O5ⁱⁱ	0.93	2.58	3.273 (2)	132
C14—H14···O6ⁱⁱⁱ	0.93	2.48	3.388 (3)	165

Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Footnotes

‡Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, Oum El Bouaghi 04000, Algeria

Acknowledgements

We are grateful to all personnel of the PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance.

References

Apodaca, R. & Xiao, W. (2001). Org. Lett. 3, 1745–1748. Web of Science CrossRef PubMed CAS Google Scholar
Baxter, E. W. & Reitz, A. B. (2002). Org. React. 59, 1–714. CAS Google Scholar
Bergeron, R. J., Feng, Y., Weimer, W. R., McManis, J. S., Dimova, H., Porter, C., Raisler, B. & Phanstiel, O. (1997). J. Med. Chem. 40, 1475–1494. CrossRef CAS PubMed Web of Science Google Scholar
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Desiraju, G. R. (2003). Crystal Design: Structure and Function Perspectives in Supramolecular Chemistry, Vol. 7, edited by G. R. Desiraju, pp. 5–7. John Wiley & Sons Ltd. Google Scholar
Dorn, T., Janiak, C. & Abu-Shandi, K. (2005). CrystEngComm, 7, 633–641. Web of Science CSD CrossRef CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Salvatore, R. N., Nagle, A. S. & Jung, K. W. (2002). J. Org. Chem. 67, 674–683. Web of Science CrossRef PubMed CAS Google Scholar
Sato, S., Sakamoto, T., Miyazawa, E. & Kikugawa, Y. (2004). Tetrahedron, 60, 7899–7906. Web of Science CrossRef CAS Google Scholar
Seayad, A., Ahmed, M., Klein, H., Jackstell, R., Gross, T. & Beller, M. (2002). Science, 297, 1676–1678. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar