N-(4-Methyl-benz-yl)-3-nitro-anilinium chloride.

The cation of the title compound, C(14)H(15)N(2)O(2) (+)·Cl(-), comprises two almost ideally planar systems, 3-nitro-phenyl (r.m.s. deviation = 0.0117 Å) and 4-methyl-phenyl (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 mol-ecules via N-H⋯Cl hydrogen bonds and consolidated by C-H⋯Cl and C-H⋯O inter-actions. Within these chains, fused R(2) (1)(6) and R(3) (2)(10) ring motifs are formed. Parallel chains are further linked into a two-dimensional network parallel to (100) via C-H⋯O inter-actions.

Related literature

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

Crystal data

C14H15N2O2 +·Cl−

M = 278.73

Monoclinic,

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 ▶) T min = 0.852, T max = 0.964

8156 measured reflections

4075 independent reflections

2357 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 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

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026281/su2452sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026281/su2452Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026281/su2452Isup3.cml

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

C14H15N2O2+·Cl−	F(000) = 584
Mr = 278.73	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3055 reflections
a = 14.2586 (7) Å	θ = 4.5–32.5°
b = 13.1416 (8) Å	µ = 0.27 mm−1
c = 7.7524 (3) Å	T = 296 K
β = 105.215 (5)°	Block, light-yellow
V = 1401.73 (13) Å3	0.56 × 0.46 × 0.14 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Saphire-3 CCD detector	4075 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 16.3426 pixels mm-1	θmax = 30.0°, θmin = 4.6°
CCD scans	h = −20→19
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −18→9
Tmin = 0.852, Tmax = 0.964	l = −10→6
8156 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H 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 reflections	Δρmax = 0.31 e Å−3
181 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (14)

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.

	x	y	z	Uiso*/Ueq
O1	0.57567 (10)	0.63507 (13)	0.82246 (19)	0.0791 (6)
O2	0.68831 (9)	0.61154 (13)	1.0638 (2)	0.0867 (6)
N1	0.26475 (8)	0.65004 (11)	1.00157 (16)	0.0369 (4)
N2	0.60377 (10)	0.62354 (11)	0.9829 (2)	0.0541 (5)
C1	0.36701 (10)	0.63347 (11)	1.09502 (17)	0.0347 (4)
C2	0.43444 (10)	0.63446 (11)	0.99596 (18)	0.0372 (4)
C3	0.53073 (10)	0.62306 (12)	1.08717 (19)	0.0404 (5)
C4	0.56150 (12)	0.61009 (14)	1.2695 (2)	0.0543 (6)
C5	0.49261 (13)	0.61086 (15)	1.3644 (2)	0.0588 (6)
C6	0.39530 (12)	0.62219 (13)	1.27825 (19)	0.0478 (5)
C7	0.19176 (11)	0.58625 (15)	1.0622 (2)	0.0502 (5)
C8	0.09152 (11)	0.60310 (14)	0.94307 (19)	0.0445 (5)
C9	0.05107 (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)
C13	0.03705 (12)	0.68605 (16)	0.9664 (2)	0.0613 (7)
C14	−0.20099 (14)	0.64248 (19)	0.6153 (3)	0.0808 (9)
Cl1	0.24918 (3)	0.62691 (3)	0.59416 (4)	0.0470 (1)
H1N	0.2565 (11)	0.6433 (12)	0.887 (2)	0.042 (4)*
H2	0.41570	0.64250	0.87250	0.0450*
H2N	0.2519 (14)	0.7188 (17)	1.020 (3)	0.073 (6)*
H4	0.62700	0.60110	1.32670	0.0650*
H5	0.51170	0.60370	1.48800	0.0710*
H6	0.34910	0.62220	1.34350	0.0570*
H7A	0.20890	0.51490	1.05980	0.0600*
H7B	0.19290	0.60400	1.18420	0.0600*
H9	0.08720	0.47860	0.78960	0.0630*
H10	−0.06890	0.50060	0.61550	0.0680*
H12	−0.09160	0.75670	0.87460	0.0820*
H13	0.06320	0.73340	1.05520	0.0740*
H14A	−0.22840	0.70300	0.65160	0.1210*
H14B	−0.23900	0.58460	0.63070	0.1210*
H14C	−0.20110	0.64820	0.49180	0.1210*

	U11	U22	U33	U12	U13	U23
O1	0.0592 (8)	0.1205 (14)	0.0652 (9)	0.0020 (8)	0.0300 (7)	−0.0021 (8)
O2	0.0341 (7)	0.1123 (14)	0.1114 (11)	0.0022 (8)	0.0153 (7)	−0.0063 (9)
N1	0.0342 (6)	0.0468 (9)	0.0297 (6)	0.0033 (6)	0.0083 (4)	0.0001 (5)
N2	0.0361 (7)	0.0534 (10)	0.0733 (10)	−0.0024 (7)	0.0154 (6)	−0.0096 (7)
C1	0.0341 (7)	0.0351 (8)	0.0327 (6)	0.0023 (6)	0.0047 (5)	−0.0007 (5)
C2	0.0364 (7)	0.0408 (9)	0.0327 (6)	0.0023 (7)	0.0061 (5)	0.0000 (6)
C3	0.0332 (7)	0.0370 (9)	0.0488 (8)	−0.0025 (7)	0.0067 (6)	−0.0047 (6)
C4	0.0399 (8)	0.0597 (12)	0.0518 (9)	0.0045 (8)	−0.0084 (7)	−0.0010 (8)
C5	0.0613 (11)	0.0724 (14)	0.0332 (7)	0.0026 (10)	−0.0044 (7)	0.0023 (7)
C6	0.0505 (8)	0.0602 (11)	0.0318 (7)	0.0014 (8)	0.0092 (6)	−0.0001 (7)
C7	0.0408 (8)	0.0648 (12)	0.0462 (8)	−0.0038 (8)	0.0138 (6)	0.0082 (7)
C8	0.0359 (7)	0.0576 (11)	0.0420 (8)	−0.0031 (7)	0.0137 (6)	0.0004 (7)
C9	0.0479 (9)	0.0566 (11)	0.0576 (9)	0.0014 (9)	0.0204 (7)	−0.0054 (8)
C10	0.0496 (10)	0.0692 (13)	0.0498 (9)	−0.0136 (10)	0.0121 (7)	−0.0114 (8)
C11	0.0398 (8)	0.0686 (13)	0.0520 (9)	−0.0047 (9)	0.0088 (7)	0.0064 (8)
C12	0.0465 (10)	0.0709 (15)	0.0858 (13)	0.0099 (10)	0.0153 (9)	−0.0137 (11)
C13	0.0468 (10)	0.0702 (14)	0.0646 (11)	−0.0019 (10)	0.0106 (8)	−0.0207 (9)
C14	0.0413 (10)	0.104 (2)	0.0879 (14)	−0.0025 (11)	0.0006 (9)	0.0170 (12)
Cl1	0.0535 (2)	0.0530 (3)	0.0344 (2)	−0.0059 (2)	0.0116 (1)	−0.0013 (2)

O1—N2	1.212 (2)	C10—C11	1.370 (3)
O2—N2	1.214 (2)	C11—C12	1.382 (3)
N1—C1	1.464 (2)	C11—C14	1.512 (3)
N1—C7	1.505 (2)	C12—C13	1.384 (3)
N2—C3	1.477 (2)	C2—H2	0.9300
N1—H2N	0.94 (2)	C4—H4	0.9300
N1—H1N	0.87 (2)	C5—H5	0.9300
C1—C2	1.379 (2)	C6—H6	0.9300
C1—C6	1.379 (2)	C7—H7A	0.9700
C2—C3	1.378 (2)	C7—H7B	0.9700
C3—C4	1.376 (2)	C9—H9	0.9300
C4—C5	1.373 (2)	C10—H10	0.9300
C5—C6	1.381 (2)	C12—H12	0.9300
C7—C8	1.501 (2)	C13—H13	0.9300
C8—C13	1.378 (3)	C14—H14A	0.9600
C8—C9	1.383 (2)	C14—H14B	0.9600
C9—C10	1.381 (2)	C14—H14C	0.9600
Cl1···C2	3.5173 (14)	C6···H7B	2.8000
Cl1···C6i	3.6084 (17)	C6···H7A	3.0900
Cl1···N1	3.1224 (13)	C7···H6	2.7300
Cl1···N1ii	3.0398 (15)	C13···H2N	3.01 (2)
Cl1···C1ii	3.5683 (15)	C14···H12ii	3.0300
Cl1···H6i	2.6900	C14···H4x	2.9000
Cl1···H2	2.7700	H1N···Cl1	2.255 (15)
Cl1···H7Bi	3.0800	H1N···H2	2.3000
Cl1···H1N	2.255 (15)	H2···O1	2.4100
Cl1···H10iii	3.1400	H2···H1N	2.3000
Cl1···H2Nii	2.11 (2)	H2···Cl1	2.7700
O1···C4ii	3.374 (3)	H2N···C13	3.01 (2)
O2···C7iv	3.393 (2)	H2N···Cl1vi	2.11 (2)
O1···H5i	2.5500	H4···O2	2.4200
O1···H2	2.4100	H4···H14Cxi	2.5300
O2···H7Aiv	2.5600	H4···C14xi	2.9000
O2···H4	2.4200	H5···O1viii	2.5500
O2···H14Av	2.7200	H5···C5vii	3.0500
N1···Cl1	3.1224 (13)	H6···C7	2.7300
N1···Cl1vi	3.0398 (15)	H6···H7B	2.2600
N2···C2iv	3.445 (2)	H6···Cl1viii	2.6900
C1···Cl1vi	3.5683 (15)	H7A···C6	3.0900
C2···C6ii	3.591 (2)	H7A···H9	2.3900
C2···N2iv	3.445 (2)	H7A···O2iv	2.5600
C2···C3iv	3.505 (2)	H7B···H6	2.2600
C2···Cl1	3.5173 (14)	H7B···Cl1viii	3.0800
C3···C3iv	3.526 (2)	H7B···C6	2.8000
C3···C2iv	3.505 (2)	H7B···H13	2.5200
C4···O1vi	3.374 (3)	H9···H7A	2.3900
C5···C5vii	3.567 (3)	H10···Cl1iii	3.1400
C6···C2vi	3.591 (2)	H12···H14Cvi	2.3600
C6···Cl1viii	3.6084 (17)	H12···H14A	2.3500
C7···O2iv	3.393 (2)	H12···C14vi	3.0300
C7···C10ix	3.595 (2)	H13···H7B	2.5200
C8···C10ix	3.591 (2)	H14A···O2xii	2.7200
C10···C8ix	3.591 (2)	H14A···H12	2.3500
C10···C7ix	3.595 (2)	H14C···H4x	2.5300
C5···H5vii	3.0500	H14C···H12ii	2.3600
C1—N1—C7	116.3 (1)	C8—C13—C12	120.56 (17)
O1—N2—O2	124.2 (2)	C1—C2—H2	121.00
O1—N2—C3	118.1 (1)	C3—C2—H2	121.00
O2—N2—C3	117.6 (1)	C3—C4—H4	121.00
C1—N1—H2N	106.0 (13)	C5—C4—H4	121.00
C7—N1—H1N	110.1 (11)	C4—C5—H5	120.00
C7—N1—H2N	108.0 (13)	C6—C5—H5	120.00
H1N—N1—H2N	105.9 (17)	C1—C6—H6	120.00
C1—N1—H1N	109.9 (11)	C5—C6—H6	120.00
N1—C1—C2	118.2 (1)	N1—C7—H7A	110.00
N1—C1—C6	120.7 (1)	N1—C7—H7B	110.00
C2—C1—C6	121.09 (14)	C8—C7—H7A	110.00
C1—C2—C3	117.37 (13)	C8—C7—H7B	110.00
N2—C3—C4	118.8 (1)	H7A—C7—H7B	108.00
N2—C3—C2	118.0 (1)	C8—C9—H9	120.00
C2—C3—C4	123.15 (14)	C10—C9—H9	120.00
C3—C4—C5	117.99 (15)	C9—C10—H10	119.00
C4—C5—C6	120.72 (14)	C11—C10—H10	119.00
C1—C6—C5	119.67 (15)	C11—C12—H12	120.00
N1—C7—C8	110.5 (1)	C13—C12—H12	120.00
C7—C8—C13	120.98 (15)	C8—C13—H13	120.00
C9—C8—C13	118.50 (15)	C12—C13—H13	120.00
C7—C8—C9	120.52 (16)	C11—C14—H14A	109.00
C8—C9—C10	120.38 (17)	C11—C14—H14B	109.00
C9—C10—C11	121.48 (16)	C11—C14—H14C	109.00
C10—C11—C12	118.05 (16)	H14A—C14—H14B	109.00
C12—C11—C14	120.85 (18)	H14A—C14—H14C	109.00
C10—C11—C14	121.10 (17)	H14B—C14—H14C	109.00
C11—C12—C13	120.99 (19)
C7—N1—C1—C2	140.58 (14)	C3—C4—C5—C6	1.3 (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—C2	0.8 (2)	N1—C7—C8—C9	99.82 (19)
O1—N2—C3—C4	−179.97 (17)	C7—C8—C9—C10	177.41 (16)
O2—N2—C3—C2	−178.65 (16)	C13—C8—C9—C10	−1.4 (3)
O2—N2—C3—C4	0.6 (2)	C7—C8—C13—C12	−178.34 (17)
C2—C1—C6—C5	−0.5 (2)	C9—C8—C13—C12	0.5 (3)
N1—C1—C2—C3	177.31 (13)	C8—C9—C10—C11	0.5 (3)
N1—C1—C6—C5	−177.32 (15)	C9—C10—C11—C14	−178.80 (17)
C6—C1—C2—C3	0.4 (2)	C9—C10—C11—C12	1.3 (3)
C1—C2—C3—C4	0.6 (2)	C14—C11—C12—C13	177.86 (18)
C1—C2—C3—N2	179.76 (13)	C10—C11—C12—C13	−2.3 (3)
N2—C3—C4—C5	179.37 (16)	C11—C12—C13—C8	1.4 (3)
C2—C3—C4—C5	−1.5 (3)

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···Cl1vi	0.94 (2)	2.11 (2)	3.040 (2)	169 (2)
C2—H2···Cl1	0.93	2.77	3.517 (1)	139
C5—H5···O1viii	0.93	2.55	3.451 (2)	164
C6—H6···Cl1viii	0.93	2.69	3.608 (2)	167
C7—H7A···O2iv	0.97	2.56	3.393 (2)	144

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) ; (ii) ; (iii) .