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In the crystal structure of the title salt, C10H16NO2+·C7H3N2O6, the cations adopt a dimer structure, through a head-to-tail hydrogen-bond between the di­methoxy and the ammonium groups. The cations are further connected to the anions by N—H...O hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007304/bt6143sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007304/bt6143Isup2.hkl
Contains datablock I

CCDC reference: 185811

Key indicators

  • Single-crystal X-ray study
  • T = 250 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.125
  • Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 75.00 From the CIF: _reflns_number_total 3362 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3803 Completeness (_total/calc) 88.40% Alert B: < 90% complete (theta max?)
Author response: Please see _publ_section_exptl_refinement

Yellow Alert Alert Level C:
PLAT_353 Alert C Long N-H Bond (0.87A) N(9) - H(9A) = 1.01 Ang.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Solid-state photoreactivities of some donor–acceptor crystals have been investigated by one of the authors (YI) (Ito et al., 1998). The structure of the title compound, (I), has been determined to study the packing mode of the molecules in the crystal.

The title crystal consists of ammonium cations and carboxylate anions (Fig. 1 and Table 1). In Fig. 1, the benzene rings of the cation (C14–C19) and that of the anion (C23–C28) are nearly parallel, and the dihedral angle is 18.52 (6)°. One of the nitro groups (N10) of the anion is above the benzene ring of the cation, and methoxy O2 atom of the cation is below the centre of the benzene ring of the anion. A close contact is observed for C14···O6, 3.205 (3) Å. The cations adopt a dimer structure through a head-to-tail hydrogen-bond between the dimethoxy and ammonium groups (Fig. 2 and Table 2). The cations are further connected to the anions by N—H···O hydrogen bonds involving the carboxylate moiety, forming a three-dimensional network.

Experimental top

Crystals of (I) were grown by slow evaporation from a methanol solution of a mixture of 2-(3,4-dimethoxyphenyl)ethylamine and 3,5-dinitrobenzoic acid (1:1)

Refinement top

The relatively low completeness of data collection (0.884 for θmax = 75°) is a result of the blind region of the low-temperature apparatus. The discrimination of the COO- against the NO2 groups was based on the displacement parameters of the C and N atoms. This assignment is rationalized by the longer C—O distances, 1.243 (2) and 1.245 (2) Å, than the nitro N—O distances, 1.214 (2)–1.220 (2) Å. It is reasonable that the carboxylato O atoms (O3 and O4) are both hydrogen-bond acceptors of the ammonium N—H bonds. The ammonium H atoms were located from difference syntheses and refined isotropically. The N—H bond lengths are 0.88 (2)–1.01 (2) Å. The other H atoms were positioned geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The projection of the crystal structure of (I) along a.
(I) top
Crystal data top
C10H16NO2+·C7H3N2O6Z = 2
Mr = 393.35F(000) = 412
Triclinic, P1Dx = 1.418 Mg m3
a = 10.0546 (9) ÅCu Kα radiation, λ = 1.5418 Å
b = 10.9344 (13) ÅCell parameters from 25 reflections
c = 9.0112 (14) Åθ = 25.2–29.4°
α = 106.451 (10)°µ = 0.98 mm1
β = 101.240 (9)°T = 250 K
γ = 94.890 (8)°Block, yellow
V = 921.5 (2) Å30.5 × 0.4 × 0.4 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.063
θ–2θ scansθmax = 75.0°, θmin = 2.5°
Absorption correction: integration
(Coppens et al., 1965)
h = 120
Tmin = 0.582, Tmax = 0.741k = 1313
4022 measured reflectionsl = 1111
3362 independent reflections3 standard reflections every 150 reflections
3229 reflections with I > 2σ(I) intensity decay: 1.0%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0606P)2 + 0.3459P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044(Δ/σ)max = 0.001
wR(F2) = 0.125Δρmax = 0.22 e Å3
S = 1.11Δρmin = 0.25 e Å3
3362 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
266 parametersExtinction coefficient: 0.0042 (7)
H atoms treated by a mixture of independent and constrained refinement
Crystal data top
C10H16NO2+·C7H3N2O6γ = 94.890 (8)°
Mr = 393.35V = 921.5 (2) Å3
Triclinic, P1Z = 2
a = 10.0546 (9) ÅCu Kα radiation
b = 10.9344 (13) ŵ = 0.98 mm1
c = 9.0112 (14) ÅT = 250 K
α = 106.451 (10)°0.5 × 0.4 × 0.4 mm
β = 101.240 (9)°
Data collection top
Rigaku AFC-7R
diffractometer
3229 reflections with I > 2σ(I)
Absorption correction: integration
(Coppens et al., 1965)
Rint = 0.063
Tmin = 0.582, Tmax = 0.7413 standard reflections every 150 reflections
4022 measured reflections intensity decay: 1.0%
3362 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044266 parameters
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.22 e Å3
3362 reflectionsΔρmin = 0.25 e Å3
Special details top

Refinement. Refinement was based on F2 against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F2, and conventional R-factor (R) was calculated on F, with F set to zero for negative F2. The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4623 (1)0.8037 (1)0.4684 (1)0.0435 (3)
O20.2562 (1)0.8307 (1)0.2682 (1)0.0489 (3)
O30.2269 (1)0.4623 (1)0.0237 (1)0.0562 (4)
O40.3043 (1)0.5755 (2)0.2288 (2)0.0663 (4)
O50.0273 (2)0.8190 (2)0.7185 (2)0.0721 (4)
O60.2259 (2)0.7610 (2)0.7702 (2)0.0637 (4)
O70.3885 (1)0.4924 (2)0.3193 (2)0.0641 (4)
O80.2317 (2)0.3369 (2)0.1685 (2)0.0702 (4)
N90.5257 (1)1.3139 (1)0.8672 (2)0.0420 (3)
N100.1160 (2)0.7554 (1)0.6806 (2)0.0462 (4)
N110.2688 (2)0.4435 (2)0.2643 (2)0.0470 (4)
C120.5666 (2)0.7712 (2)0.5762 (2)0.0499 (4)
C130.1408 (2)0.8378 (2)0.1529 (2)0.0627 (6)
C140.4144 (2)0.9718 (2)0.6864 (2)0.0404 (4)
C150.3864 (2)0.8955 (1)0.5301 (2)0.0356 (3)
C160.2725 (2)0.9086 (2)0.4207 (2)0.0378 (3)
C170.1878 (2)0.9965 (2)0.4723 (2)0.0445 (4)
C180.2181 (2)1.0732 (2)0.6301 (2)0.0463 (4)
C190.3305 (2)1.0631 (2)0.7383 (2)0.0424 (4)
C200.3617 (2)1.1486 (2)0.9092 (2)0.0553 (5)
C210.5020 (2)1.2319 (2)0.9674 (2)0.0509 (4)
C220.2133 (2)0.5296 (2)0.1642 (2)0.0412 (4)
C230.0695 (2)0.5569 (1)0.2705 (2)0.0346 (3)
C240.0415 (2)0.6436 (2)0.4225 (2)0.0362 (3)
C250.0887 (2)0.6651 (1)0.5181 (2)0.0364 (3)
C260.1936 (2)0.6023 (2)0.4697 (2)0.0387 (4)
C270.1618 (2)0.5163 (2)0.3185 (2)0.0369 (3)
C280.0335 (2)0.4923 (2)0.2173 (2)0.0362 (3)
H9A0.449 (2)1.366 (2)0.849 (2)0.06064 (7)*
H9B0.538 (2)1.269 (2)0.774 (2)0.04285 (6)*
H9C0.612 (2)1.372 (2)0.918 (3)0.06175 (8)*
H12A0.63420.84460.63090.0599*
H12B0.52720.74330.65110.0599*
H12C0.60800.70370.51910.0599*
H13A0.14540.92250.14470.0755*
H13B0.13990.77810.05300.0755*
H13C0.05890.81700.18490.0755*
H140.49150.96220.75980.0484*
H170.10901.00470.40000.0534*
H180.15971.13400.66410.0555*
H20A0.29411.20420.91950.0664*
H20B0.35611.09500.97490.0664*
H21A0.50941.28581.07270.0611*
H21B0.57041.17690.96740.0611*
H240.11140.68790.46040.0434*
H260.28270.61770.53690.0464*
H280.01620.43270.11340.0433*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0509 (7)0.0421 (6)0.0372 (6)0.0214 (5)0.0092 (5)0.0082 (5)
O20.0501 (7)0.0540 (7)0.0336 (6)0.0173 (6)0.0036 (5)0.0006 (5)
O30.0414 (7)0.0750 (9)0.0392 (7)0.0012 (6)0.0027 (5)0.0075 (6)
O40.0384 (7)0.083 (1)0.0647 (9)0.0252 (7)0.0023 (6)0.0034 (7)
O50.082 (1)0.0706 (10)0.0495 (8)0.0257 (8)0.0147 (7)0.0073 (7)
O60.0628 (9)0.0746 (9)0.0370 (7)0.0004 (7)0.0068 (6)0.0065 (6)
O70.0357 (7)0.0718 (9)0.091 (1)0.0185 (6)0.0177 (7)0.0293 (8)
O80.0677 (9)0.0612 (9)0.0731 (10)0.0268 (7)0.0217 (8)0.0018 (8)
N90.0357 (7)0.0467 (8)0.0328 (7)0.0115 (6)0.0041 (5)0.0036 (6)
N100.0559 (9)0.0434 (8)0.0337 (7)0.0015 (7)0.0067 (6)0.0072 (6)
N110.0452 (9)0.0502 (9)0.0518 (8)0.0199 (7)0.0168 (7)0.0179 (7)
C120.0481 (10)0.0499 (10)0.052 (1)0.0181 (8)0.0057 (8)0.0165 (8)
C130.059 (1)0.076 (1)0.0395 (9)0.019 (1)0.0029 (8)0.0041 (9)
C140.0421 (9)0.0436 (9)0.0339 (8)0.0070 (7)0.0086 (6)0.0094 (7)
C150.0402 (8)0.0322 (7)0.0359 (8)0.0090 (6)0.0128 (6)0.0089 (6)
C160.0408 (8)0.0359 (8)0.0346 (8)0.0070 (6)0.0100 (6)0.0065 (6)
C170.0394 (9)0.0450 (9)0.0461 (9)0.0123 (7)0.0080 (7)0.0089 (7)
C180.0433 (9)0.0428 (9)0.0511 (10)0.0125 (7)0.0187 (7)0.0046 (7)
C190.0455 (9)0.0411 (9)0.0373 (8)0.0033 (7)0.0156 (7)0.0035 (7)
C200.060 (1)0.059 (1)0.0406 (9)0.0054 (9)0.0203 (8)0.0005 (8)
C210.054 (1)0.058 (1)0.0302 (8)0.0120 (8)0.0050 (7)0.0005 (7)
C220.0356 (8)0.0446 (9)0.0410 (9)0.0071 (7)0.0018 (7)0.0138 (7)
C230.0336 (8)0.0361 (8)0.0338 (8)0.0065 (6)0.0058 (6)0.0112 (6)
C240.0365 (8)0.0355 (8)0.0377 (8)0.0097 (6)0.0104 (6)0.0105 (6)
C250.0415 (8)0.0354 (8)0.0298 (7)0.0036 (6)0.0059 (6)0.0082 (6)
C260.0324 (8)0.0435 (9)0.0391 (8)0.0034 (6)0.0029 (6)0.0150 (7)
C270.0340 (8)0.0401 (8)0.0399 (8)0.0109 (6)0.0112 (6)0.0139 (7)
C280.0390 (8)0.0361 (8)0.0316 (7)0.0063 (6)0.0078 (6)0.0073 (6)
Geometric parameters (Å, º) top
O1—C121.426 (2)C14—H140.950
O1—C151.370 (2)C15—C161.404 (2)
O2—C131.422 (2)C16—C171.381 (3)
O2—C161.367 (2)C17—C181.389 (2)
O3—C221.245 (2)C17—H170.950
O4—C221.243 (2)C18—C191.376 (3)
O5—N101.219 (2)C18—H180.950
O6—N101.220 (2)C19—C201.513 (2)
O7—N111.220 (2)C20—C211.522 (3)
O8—N111.214 (2)C20—H20A0.950
N9—C211.478 (3)C20—H20B0.950
N9—H9A1.01 (2)C21—H21A0.950
N9—H9B0.88 (2)C21—H21B0.951
N9—H9C0.97 (2)C22—C231.524 (2)
N10—C251.474 (2)C23—C241.387 (2)
N11—C271.469 (2)C23—C281.388 (2)
C12—H12A0.950C24—C251.380 (2)
C12—H12B0.951C24—H240.950
C12—H12C0.951C25—C261.381 (2)
C13—H13A0.948C26—C271.377 (2)
C13—H13B0.948C26—H260.951
C13—H13C0.954C27—C281.384 (2)
C14—C151.378 (2)C28—H280.951
C14—C191.400 (3)
C12—O1—C15118.0 (1)C17—C18—H18119.1
C13—O2—C16117.7 (1)C19—C18—H18119.2
C21—N9—H9A113 (1)C14—C19—C18118.4 (1)
C21—N9—H9B112 (2)C14—C19—C20121.2 (2)
C21—N9—H9C109 (2)C18—C19—C20120.5 (2)
H9A—N9—H9B108 (2)C19—C20—C21115.0 (2)
H9A—N9—H9C109 (2)C19—C20—H20A108.0
H9B—N9—H9C105 (2)C19—C20—H20B108.1
O5—N10—O6123.7 (1)C21—C20—H20A108.1
O5—N10—C25118.3 (1)C21—C20—H20B108.1
O6—N10—C25117.9 (1)H20A—C20—H20B109.5
O7—N11—O8124.1 (2)N9—C21—C20112.9 (1)
O7—N11—C27118.5 (1)N9—C21—H21A108.6
O8—N11—C27117.4 (1)N9—C21—H21B108.6
O1—C12—H12A109.6C20—C21—H21A108.6
O1—C12—H12B109.5C20—C21—H21B108.6
O1—C12—H12C109.6H21A—C21—H21B109.4
H12A—C12—H12B109.3O3—C22—O4127.4 (1)
H12A—C12—H12C109.4O3—C22—C23116.5 (1)
H12B—C12—H12C109.3O4—C22—C23116.1 (1)
O2—C13—H13A109.7C22—C23—C24120.3 (1)
O2—C13—H13B109.6C22—C23—C28120.2 (1)
O2—C13—H13C109.2C24—C23—C28119.6 (1)
H13A—C13—H13B109.8C23—C24—C25119.4 (1)
H13A—C13—H13C109.3C23—C24—H24120.3
H13B—C13—H13C109.2C25—C24—H24120.3
C15—C14—C19120.8 (1)N10—C25—C24118.8 (1)
C15—C14—H14119.6N10—C25—C26118.5 (1)
C19—C14—H14119.6C24—C25—C26122.7 (1)
O1—C15—C14125.0 (1)C25—C26—C27116.3 (1)
O1—C15—C16115.0 (1)C25—C26—H26121.9
C14—C15—C16120.1 (2)C27—C26—H26121.9
O2—C16—C15115.3 (1)N11—C27—C26118.1 (1)
O2—C16—C17125.4 (1)N11—C27—C28118.5 (1)
C15—C16—C17119.3 (1)C26—C27—C28123.3 (2)
C16—C17—C18119.8 (2)C23—C28—C27118.7 (1)
C16—C17—H17120.1C23—C28—H28120.7
C18—C17—H17120.1C27—C28—H28120.6
C17—C18—C19121.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9A···O4i1.01 (2)1.74 (2)2.733 (2)165 (2)
N9—H9B···O1ii0.88 (2)2.10 (2)2.963 (2)164 (2)
N9—H9B···O2ii0.88 (2)2.47 (2)3.056 (2)125 (2)
N9—H9C···O3iii0.97 (2)1.76 (2)2.731 (2)172 (2)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC10H16NO2+·C7H3N2O6
Mr393.35
Crystal system, space groupTriclinic, P1
Temperature (K)250
a, b, c (Å)10.0546 (9), 10.9344 (13), 9.0112 (14)
α, β, γ (°)106.451 (10), 101.240 (9), 94.890 (8)
V3)921.5 (2)
Z2
Radiation typeCu Kα
µ (mm1)0.98
Crystal size (mm)0.5 × 0.4 × 0.4
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionIntegration
(Coppens et al., 1965)
Tmin, Tmax0.582, 0.741
No. of measured, independent and
observed [I > 2σ(I)] reflections
4022, 3362, 3229
Rint0.063
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.125, 1.11
No. of reflections3362
No. of parameters266
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.25

Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), WinAFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top
O3—C221.245 (2)O6—N101.220 (2)
O4—C221.243 (2)O7—N111.220 (2)
O5—N101.219 (2)O8—N111.214 (2)
O5—N10—O6123.7 (1)O3—C22—O4127.4 (1)
O7—N11—O8124.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N9—H9A···O4i1.01 (2)1.74 (2)2.733 (2)165 (2)
N9—H9B···O1ii0.88 (2)2.10 (2)2.963 (2)164 (2)
N9—H9B···O2ii0.88 (2)2.47 (2)3.056 (2)125 (2)
N9—H9C···O3iii0.97 (2)1.76 (2)2.731 (2)172 (2)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1.
 

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