Dimethyl-ammonium 4-nitro-phenolate-4-nitro-phenol (1/1).

The title compound, C(2)H(8)N(+)·C(6)H(4)NO(3) (-)·C(6)H(5)NO(3), was synthesized from dimethyl-amine and 4-nitro-phenol in an overall yield of 85%. The dihdral angles between the nphenyl rings and their attached nitro groups are 5.7 (6) and 2.5 (7)°. In the crystal, there are strong hydrogen bonds between the ammonium group and the nitro-phenol and nitro-phenolate O atoms, and between the nitro-phenol and nitro-phenolate O atoms, forming a chain along the b-axis direction.

Related literature

For background to dialectric behaviour, see: Horiuchi et al. (2007 ▶); Kumai et al. (2006 ▶).

Experimental

Crystal data

C2H8N+·C6H4NO3 −·C6H5NO3

M = 323.31

Monoclinic,

a = 6.3185 (10) Å

b = 16.8867 (10) Å

c = 15.1015 (14) Å

β = 101.928 (10)°

V = 1576.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.960, T max = 0.977

15857 measured reflections

3617 independent reflections

1474 reflections with I > 2σ(I)

R int = 0.134

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.212

S = 1.00

3617 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008317/ez2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008317/ez2184Isup2.hkl

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

C2H8N+·C6H4NO3−·C6H5NO3	F(000) = 680
Mr = 323.31	Dx = 1.362 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 0 reflections
a = 6.3185 (10) Å	θ = 2.7–27.3°
b = 16.8867 (10) Å	µ = 0.11 mm−1
c = 15.1015 (14) Å	T = 293 K
β = 101.928 (10)°	Prism, yellow
V = 1576.5 (3) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	3617 independent reflections
Radiation source: fine-focus sealed tube	1474 reflections with I > 2σ(I)
graphite	Rint = 0.134
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −21→21
Tmin = 0.960, Tmax = 0.977	l = −19→19
15857 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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0781P)2] where P = (Fo2 + 2Fc2)/3
3617 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
C1	0.1166 (5)	0.16858 (18)	0.2568 (2)	0.0476 (8)
C2	−0.0163 (5)	0.13397 (19)	0.3106 (2)	0.0551 (9)
H2	−0.1503	0.1564	0.3115	0.066*
C3	0.0485 (6)	0.0682 (2)	0.3612 (2)	0.0622 (10)
H3A	−0.0433	0.0451	0.3946	0.075*
C4	0.2496 (6)	0.03589 (19)	0.3631 (2)	0.0541 (9)
C5	0.3856 (6)	0.06954 (19)	0.3122 (2)	0.0566 (9)
H5	0.5208	0.0474	0.3131	0.068*
C6	0.3216 (5)	0.13475 (19)	0.2612 (2)	0.0530 (9)
H6	0.4154	0.1575	0.2284	0.064*
C7	0.1727 (5)	0.15350 (19)	0.7572 (2)	0.0492 (9)
C8	−0.0224 (5)	0.1312 (2)	0.7775 (2)	0.0563 (9)
H8	−0.1464	0.1606	0.7553	0.068*
C9	−0.0337 (6)	0.0659 (2)	0.8302 (2)	0.0575 (9)
H9	−0.1655	0.0506	0.8431	0.069*
C10	0.1485 (6)	0.02359 (19)	0.8637 (2)	0.0499 (9)
C11	0.3448 (6)	0.0449 (2)	0.8463 (3)	0.0668 (11)
H11	0.4683	0.0156	0.8696	0.080*
C12	0.3560 (6)	0.1109 (2)	0.7933 (3)	0.0642 (11)
H12	0.4888	0.1267	0.7819	0.077*
C13	−0.0771 (7)	0.2605 (2)	−0.0167 (3)	0.0913 (14)
H13A	−0.0713	0.2802	−0.0758	0.137*
H13B	−0.1768	0.2918	0.0085	0.137*
H13C	−0.1244	0.2064	−0.0214	0.137*
C14	0.3086 (7)	0.2208 (2)	0.0111 (3)	0.0861 (13)
H14A	0.2750	0.1653	0.0100	0.129*
H14B	0.4451	0.2299	0.0514	0.129*
H14C	0.3168	0.2379	−0.0488	0.129*
N1	0.3125 (7)	−0.03649 (18)	0.4114 (2)	0.0694 (9)
N2	0.1366 (7)	−0.04734 (19)	0.9189 (2)	0.0692 (9)
N3	0.1396 (5)	0.26538 (15)	0.0422 (2)	0.0671 (9)
H3B	0.1793	0.3166	0.0478	0.081*
H3C	0.1310	0.2477	0.0976	0.081*
O1	0.0540 (4)	0.23037 (12)	0.20599 (14)	0.0553 (7)
O2	0.1749 (4)	0.21762 (15)	0.70479 (17)	0.0650 (8)
O3	0.4907 (5)	−0.06544 (16)	0.4107 (2)	0.0896 (10)
O4	0.1846 (5)	−0.06924 (15)	0.45180 (19)	0.0896 (10)
O5	0.3015 (6)	−0.08400 (18)	0.9483 (2)	0.1126 (12)
O6	−0.0419 (5)	−0.06671 (15)	0.93146 (17)	0.0791 (9)
H1	0.313 (7)	0.233 (2)	0.704 (3)	0.104 (16)*

	U11	U22	U33	U12	U13	U23
C1	0.057 (2)	0.0400 (19)	0.045 (2)	−0.0029 (17)	0.0077 (17)	−0.0043 (16)
C2	0.061 (2)	0.048 (2)	0.060 (2)	0.0018 (18)	0.0225 (19)	−0.0010 (18)
C3	0.074 (3)	0.051 (2)	0.067 (3)	−0.007 (2)	0.028 (2)	0.0028 (19)
C4	0.069 (2)	0.0402 (19)	0.053 (2)	0.0022 (18)	0.011 (2)	0.0003 (17)
C5	0.060 (2)	0.046 (2)	0.064 (2)	0.0070 (18)	0.012 (2)	−0.0058 (19)
C6	0.053 (2)	0.045 (2)	0.063 (2)	−0.0023 (17)	0.0166 (19)	0.0012 (18)
C7	0.052 (2)	0.0426 (19)	0.055 (2)	−0.0042 (17)	0.0154 (18)	−0.0032 (17)
C8	0.046 (2)	0.053 (2)	0.067 (2)	0.0017 (17)	0.0077 (19)	0.0025 (19)
C9	0.051 (2)	0.058 (2)	0.065 (2)	−0.0081 (19)	0.014 (2)	−0.002 (2)
C10	0.057 (2)	0.046 (2)	0.048 (2)	−0.0057 (18)	0.0156 (18)	0.0008 (16)
C11	0.055 (2)	0.061 (2)	0.087 (3)	0.0125 (19)	0.020 (2)	0.011 (2)
C12	0.054 (2)	0.057 (2)	0.086 (3)	0.0044 (19)	0.024 (2)	0.014 (2)
C13	0.099 (4)	0.077 (3)	0.088 (3)	−0.004 (2)	−0.004 (3)	0.014 (2)
C14	0.098 (3)	0.087 (3)	0.083 (3)	−0.012 (3)	0.041 (3)	−0.013 (2)
N1	0.102 (3)	0.046 (2)	0.059 (2)	0.003 (2)	0.013 (2)	0.0026 (16)
N2	0.089 (3)	0.055 (2)	0.065 (2)	−0.014 (2)	0.018 (2)	−0.0048 (17)
N3	0.102 (3)	0.0431 (17)	0.0586 (19)	−0.0083 (17)	0.022 (2)	0.0005 (15)
O1	0.0664 (16)	0.0450 (13)	0.0580 (15)	0.0080 (12)	0.0205 (12)	0.0035 (12)
O2	0.0596 (18)	0.0565 (16)	0.0798 (18)	−0.0041 (13)	0.0167 (15)	0.0149 (13)
O3	0.095 (2)	0.0640 (18)	0.110 (2)	0.0230 (17)	0.022 (2)	0.0174 (16)
O4	0.132 (3)	0.0583 (17)	0.087 (2)	0.0032 (17)	0.044 (2)	0.0174 (15)
O5	0.102 (3)	0.084 (2)	0.148 (3)	0.0146 (19)	0.018 (2)	0.054 (2)
O6	0.098 (2)	0.0679 (18)	0.078 (2)	−0.0276 (16)	0.0314 (17)	0.0043 (14)

C1—O1	1.307 (3)	C10—N2	1.471 (4)
C1—C6	1.405 (4)	C11—C12	1.382 (4)
C1—C2	1.410 (4)	C11—H11	0.9300
C2—C3	1.362 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—N3	1.473 (5)
C3—C4	1.378 (5)	C13—H13A	0.9600
C3—H3A	0.9300	C13—H13B	0.9600
C4—C5	1.387 (4)	C13—H13C	0.9600
C4—N1	1.436 (4)	C14—N3	1.462 (4)
C5—C6	1.357 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O2	1.343 (4)	N1—O3	1.229 (4)
C7—C12	1.376 (4)	N1—O4	1.239 (4)
C7—C8	1.382 (4)	N2—O5	1.214 (4)
C8—C9	1.371 (4)	N2—O6	1.226 (4)
C8—H8	0.9300	N3—H3B	0.9000
C9—C10	1.360 (4)	N3—H3C	0.9000
C9—H9	0.9300	O2—H1	0.91 (4)
C10—C11	1.368 (4)
O1—C1—C6	121.1 (3)	C10—C11—H11	120.6
O1—C1—C2	121.7 (3)	C12—C11—H11	120.6
C6—C1—C2	117.2 (3)	C7—C12—C11	120.7 (3)
C3—C2—C1	121.0 (3)	C7—C12—H12	119.7
C3—C2—H2	119.5	C11—C12—H12	119.7
C1—C2—H2	119.5	N3—C13—H13A	109.5
C2—C3—C4	120.2 (3)	N3—C13—H13B	109.5
C2—C3—H3A	119.9	H13A—C13—H13B	109.5
C4—C3—H3A	119.9	N3—C13—H13C	109.5
C3—C4—C5	120.0 (3)	H13A—C13—H13C	109.5
C3—C4—N1	120.3 (3)	H13B—C13—H13C	109.5
C5—C4—N1	119.4 (3)	N3—C14—H14A	109.5
C6—C5—C4	120.1 (3)	N3—C14—H14B	109.5
C6—C5—H5	120.0	H14A—C14—H14B	109.5
C4—C5—H5	120.0	N3—C14—H14C	109.5
C5—C6—C1	121.3 (3)	H14A—C14—H14C	109.5
C5—C6—H6	119.3	H14B—C14—H14C	109.5
C1—C6—H6	119.3	O3—N1—O4	121.2 (3)
O2—C7—C12	122.9 (3)	O3—N1—C4	119.5 (4)
O2—C7—C8	117.9 (3)	O4—N1—C4	119.3 (4)
C12—C7—C8	119.1 (3)	O5—N2—O6	123.7 (3)
C9—C8—C7	120.2 (3)	O5—N2—C10	118.8 (4)
C9—C8—H8	119.9	O6—N2—C10	117.5 (4)
C7—C8—H8	119.9	C14—N3—C13	115.2 (3)
C10—C9—C8	119.8 (3)	C14—N3—H3B	108.5
C10—C9—H9	120.1	C13—N3—H3B	108.5
C8—C9—H9	120.1	C14—N3—H3C	108.5
C9—C10—C11	121.4 (3)	C13—N3—H3C	108.5
C9—C10—N2	120.0 (3)	H3B—N3—H3C	107.5
C11—C10—N2	118.6 (3)	C7—O2—H1	111 (3)
C10—C11—C12	118.7 (3)
O1—C1—C2—C3	178.1 (3)	C8—C9—C10—N2	−178.9 (3)
C6—C1—C2—C3	−3.0 (5)	C9—C10—C11—C12	−0.2 (5)
C1—C2—C3—C4	2.3 (5)	N2—C10—C11—C12	179.1 (3)
C2—C3—C4—C5	−1.0 (5)	O2—C7—C12—C11	−179.5 (3)
C2—C3—C4—N1	−175.7 (3)	C8—C7—C12—C11	2.4 (5)
C3—C4—C5—C6	0.6 (5)	C10—C11—C12—C7	−1.2 (5)
N1—C4—C5—C6	175.3 (3)	C3—C4—N1—O3	178.4 (3)
C4—C5—C6—C1	−1.4 (5)	C5—C4—N1—O3	3.7 (5)
O1—C1—C6—C5	−178.5 (3)	C3—C4—N1—O4	−0.5 (5)
C2—C1—C6—C5	2.6 (5)	C5—C4—N1—O4	−175.2 (3)
O2—C7—C8—C9	179.5 (3)	C9—C10—N2—O5	−179.8 (4)
C12—C7—C8—C9	−2.3 (5)	C11—C10—N2—O5	1.0 (5)
C7—C8—C9—C10	0.9 (5)	C9—C10—N2—O6	1.4 (5)
C8—C9—C10—C11	0.3 (5)	C11—C10—N2—O6	−177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O4i	0.90	2.11	3.000 (4)	170
N3—H3C···O1	0.90	1.82	2.704 (4)	165
O2—H1···O1ii	0.91 (4)	1.64 (4)	2.548 (3)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O4i	0.90	2.11	3.000 (4)	170
N3—H3C⋯O1	0.90	1.82	2.704 (4)	165
O2—H1⋯O1ii	0.91 (4)	1.64 (4)	2.548 (3)	175 (4)

Symmetry codes: (i) ; (ii) .