2-Hy-droxy-N-(4-meth-oxy-benz-yl)-4-nitro-anilinium chloride.

The crystal structure of the title compound, C(14)H(15)N(2)O(4) (+)·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 hy-droxy groups. The packing is also stabilized by weak C-H⋯O inter-molecular hydrogen bonds. An intra-molecular N-H⋯O inter-action 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 n class="Chemical">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 = 310.73

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.079

S = 1.35

3359 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAIn class="Chemical">NT; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029552/fb2237sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811029552/fb2237Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H15N2O4+·Cl−	F(000) = 1296
Mr = 310.73	Dx = 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

Bruker APEXII CCD area-detector diffractometer	2290 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −41→36
Tmin = 0.784, Tmax = 0.984	k = −9→8
11129 measured reflections	l = −16→13
3359 independent 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.079	H-atom parameters constrained
S = 1.35	w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3
3359 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.25 e Å−3
59 constraints

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
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)

	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)

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)

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

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) ; (ii) ; (iii) .