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The crystal structure of the proton-transfer compound from the reaction of 3,5-di­nitro­salicylic acid (DNSA) with benzyl­amine (BA), viz. benzyl­ammonium 3,5-di­nitro­salicyl­ate, C7H10N+·C7H3N2O7-, shows a hydrogen-bonded polymer in which the protonated primary amine group of benzyl­amine gives a total of six inter-species interactions with O atoms of the DNSA anions. In addition, there are unusual centrosymmetric interactions between the carboxyl­ate groups of the DNSA anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012163/tk6066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012163/tk6066Isup2.hkl
Contains datablock I

CCDC reference: 193743

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.056
  • wR factor = 0.217
  • Data-to-parameter ratio = 14.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C14 H13 N3 O7 Atom count from _chemical_formula_moiety:

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
(C7H10N)+·(C7H3N2O7)Z = 2
Mr = 335.27F(000) = 348
Triclinic, P1Dx = 1.505 Mg m3
Hall symbol: -P 1Melting point = 473–475 K
a = 10.953 (15) ÅMo Kα radiation, λ = 0.71069 Å
b = 11.450 (8) ÅCell parameters from 25 reflections
c = 7.118 (4) Åθ = 12.6–17.1°
α = 94.56 (5)°µ = 0.12 mm1
β = 105.61 (7)°T = 295 K
γ = 117.61 (6)°Plate, yellow
V = 739.7 (14) Å30.30 × 0.25 × 0.20 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.027
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 3.1°
Graphite monochromatorh = 146
ω–2θ scansk = 1314
3872 measured reflectionsl = 89
3406 independent reflections3 standard reflections every 150 reflections
1708 reflections with I > 2σ(I) intensity decay: 1.2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217H atoms treated by a mixture of independent and constrained refinement
S = 0.88 w = 1/[σ2(Fo2) + (0.1P)2 + 1.0302P]
where P = (Fo2 + 2Fc2)/3
3406 reflections(Δ/σ)max < 0.001
234 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 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
xyzUiso*/Ueq
O20.7333 (3)0.8842 (2)0.3173 (4)0.0587 (9)
O310.4892 (3)0.8743 (3)0.0898 (5)0.0700 (10)
O320.3006 (3)0.6810 (3)0.0623 (5)0.0686 (11)
O510.2491 (3)0.2720 (3)0.0973 (5)0.0662 (10)
O520.4380 (3)0.2666 (3)0.2817 (5)0.0671 (10)
O710.9131 (3)0.6785 (3)0.6062 (4)0.0582 (9)
O720.9404 (3)0.8732 (3)0.5489 (5)0.0800 (13)
N30.4248 (3)0.7503 (3)0.0591 (5)0.0470 (10)
N50.3789 (3)0.3279 (3)0.2013 (5)0.0461 (10)
C10.7049 (4)0.6758 (3)0.3836 (5)0.0393 (10)
C20.6480 (4)0.7577 (3)0.2897 (5)0.0391 (10)
C30.4957 (4)0.6831 (3)0.1679 (5)0.0385 (10)
C40.4077 (4)0.5444 (3)0.1406 (5)0.0393 (10)
C50.4695 (4)0.4735 (3)0.2339 (5)0.0378 (10)
C60.6172 (4)0.5385 (3)0.3550 (5)0.0403 (11)
C70.8614 (4)0.7419 (4)0.5207 (6)0.0482 (11)
N810.2029 (4)0.8954 (4)0.1328 (6)0.0537 (12)
C110.1648 (4)0.8357 (4)0.1809 (6)0.0492 (12)
C210.2794 (5)0.8812 (4)0.3577 (6)0.0598 (12)
C310.2852 (5)0.7957 (5)0.4812 (6)0.0704 (18)
C410.1745 (6)0.6636 (5)0.4295 (7)0.0671 (17)
C510.0585 (5)0.6160 (4)0.2543 (7)0.0670 (16)
C610.0523 (4)0.7008 (4)0.1285 (6)0.0576 (14)
C710.1621 (5)0.9269 (4)0.0402 (7)0.0633 (16)
H40.3049000.4991000.0591000.0480*
H60.6604000.4888000.4185000.0510*
H720.879 (7)0.895 (6)0.452 (9)0.13 (2)*
H210.3588000.975400.398100.0730*
H310.3699000.830900.603800.0850*
H410.1787000.605500.520100.0810*
H510.0203000.521100.217500.0820*
H610.0284000.667800.002500.0710*
H7110.0653000.916000.010300.0800*
H7120.2292001.020000.110800.0800*
H8110.117 (6)0.813 (5)0.231 (7)0.078 (14)*
H8120.238 (5)0.969 (5)0.206 (6)0.071 (13)*
H8130.281 (6)0.884 (5)0.107 (7)0.080 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0516 (15)0.0362 (13)0.0712 (18)0.0158 (12)0.0050 (13)0.0245 (12)
O310.0600 (18)0.0461 (16)0.105 (2)0.0313 (14)0.0172 (16)0.0345 (16)
O320.0597 (18)0.0606 (17)0.076 (2)0.0340 (15)0.0007 (16)0.0247 (15)
O510.0488 (17)0.0415 (15)0.087 (2)0.0128 (13)0.0118 (16)0.0147 (14)
O520.0713 (19)0.0419 (15)0.091 (2)0.0328 (14)0.0212 (16)0.0268 (15)
O710.0534 (15)0.0514 (15)0.0664 (18)0.0290 (13)0.0082 (13)0.0238 (13)
O720.0494 (17)0.0471 (17)0.106 (3)0.0118 (14)0.0090 (16)0.0369 (17)
N30.0494 (18)0.0460 (17)0.0540 (19)0.0296 (15)0.0164 (15)0.0238 (14)
N50.0497 (18)0.0334 (15)0.0522 (18)0.0175 (14)0.0190 (15)0.0132 (13)
C10.0423 (18)0.0367 (17)0.0420 (18)0.0215 (15)0.0142 (15)0.0164 (14)
C20.0429 (18)0.0341 (17)0.0429 (18)0.0200 (15)0.0151 (15)0.0179 (14)
C30.0426 (18)0.0405 (18)0.0398 (18)0.0261 (15)0.0130 (15)0.0176 (14)
C40.0426 (18)0.0384 (18)0.0398 (18)0.0211 (15)0.0158 (15)0.0149 (15)
C50.0447 (18)0.0311 (16)0.0392 (18)0.0191 (15)0.0162 (15)0.0108 (13)
C60.051 (2)0.0382 (17)0.0416 (19)0.0274 (16)0.0188 (16)0.0183 (14)
C70.046 (2)0.0413 (19)0.052 (2)0.0210 (16)0.0090 (17)0.0188 (17)
N810.049 (2)0.051 (2)0.067 (2)0.0284 (17)0.0171 (18)0.0344 (18)
C110.053 (2)0.045 (2)0.054 (2)0.0288 (18)0.0165 (18)0.0150 (17)
C210.056 (2)0.053 (2)0.055 (2)0.020 (2)0.012 (2)0.0091 (19)
C310.068 (3)0.097 (4)0.049 (2)0.048 (3)0.011 (2)0.023 (2)
C410.086 (3)0.076 (3)0.067 (3)0.054 (3)0.036 (3)0.038 (2)
C510.076 (3)0.046 (2)0.070 (3)0.022 (2)0.026 (2)0.023 (2)
C610.049 (2)0.054 (2)0.061 (3)0.0217 (19)0.0120 (19)0.0216 (19)
C710.075 (3)0.043 (2)0.074 (3)0.033 (2)0.021 (2)0.021 (2)
Geometric parameters (Å, º) top
O2—C21.269 (4)C4—C51.383 (6)
O31—N31.225 (5)C5—C61.395 (6)
O32—N31.218 (5)C4—H40.97
O51—N51.222 (5)C6—H60.96
O52—N51.235 (5)C11—C711.508 (6)
O71—C71.218 (6)C11—C211.368 (7)
O72—C71.305 (6)C11—C611.393 (6)
O72—H720.96 (7)C21—C311.378 (7)
N3—C31.456 (6)C31—C411.366 (8)
N5—C51.449 (5)C41—C511.365 (8)
N81—C711.490 (7)C51—C611.384 (6)
N81—H8121.00 (5)C21—H210.97
N81—H8130.90 (7)C31—H310.97
N81—H8110.99 (5)C41—H410.97
C1—C71.498 (7)C51—H510.98
C1—C61.371 (5)C61—H610.97
C1—C21.460 (6)C71—H7110.97
C2—C31.431 (6)C71—H7120.96
C3—C41.386 (5)
O2···O312.673 (6)C2···N5iv3.449 (7)
O2···O722.483 (6)C2···O51iv3.294 (7)
O2···N32.925 (6)C3···C5iv3.456 (7)
O2···O72i3.153 (6)C3···N5iv3.295 (7)
O2···N81ii2.823 (6)C4···C6iv3.483 (7)
O31···C213.380 (8)C4···C5iv3.325 (7)
O31···N81ii3.081 (7)C4···C4iv3.590 (8)
O31···O22.673 (6)C5···C3iv3.456 (7)
O31···N813.239 (7)C5···C6iii3.305 (7)
O31···O31ii3.177 (6)C5···C4iv3.325 (7)
O32···N813.125 (7)C6···C6iii3.560 (8)
O32···C113.419 (8)C6···N5iii3.379 (7)
O51···C7iii3.247 (7)C6···C5iii3.305 (7)
O51···C2iv3.294 (7)C6···C4iv3.483 (7)
O52···N3iv3.215 (7)C7···O51iii3.247 (7)
O52···C1iii3.358 (7)C7···N81v3.379 (8)
O71···N81v2.912 (7)C11···O323.419 (8)
O72···N81v3.031 (7)C21···O313.380 (8)
O72···O2i3.153 (6)C31···N81x3.384 (8)
O72···O72i2.814 (6)C2···H722.16 (7)
O72···O22.483 (6)C2···H812ii2.96 (5)
O2···H812ii1.85 (5)C7···H811v2.57 (6)
O2···H721.57 (8)C31···H813x3.04 (5)
O31···H8132.39 (7)C61···H8113.06 (5)
O31···H813ii2.71 (6)H4···O322.3328
O31···H812ii2.51 (6)H4···O512.4368
O32···H51vi2.6803H6···O522.4372
O32···H41vii2.7841H6···O712.4778
O32···H8132.47 (6)H6···H41iii2.4263
O32···H42.3328H21···H7122.3945
O51···H712viii2.8026H31···O52iii2.7815
O51···H61vi2.7425H41···H6iii2.4263
O51···H42.4368H41···O32x2.7841
O52···H62.4372H41···O71iii2.9003
O52···H712viii2.5795H51···O32vi2.6803
O52···H31iii2.7815H61···O71ix2.7455
O71···H62.4778H61···H7112.5546
O71···H41iii2.9003H61···O51vi2.7425
O71···H811v1.96 (6)H72···O21.57 (8)
O71···H61v2.7455H72···C22.16 (7)
O72···H812v2.86 (6)H72···O72i2.47 (7)
O72···H811v2.54 (6)H72···H72i2.48 (10)
O72···H72i2.47 (7)H711···H612.5546
N3···O22.925 (6)H712···O51xi2.8026
N3···O52iv3.215 (7)H712···O52xi2.5795
N5···C2iv3.449 (7)H712···H212.3945
N5···C1iii3.319 (7)H811···O71ix1.96 (6)
N5···C3iv3.295 (7)H811···O72ix2.54 (6)
N5···C6iii3.379 (7)H811···C7ix2.57 (6)
N81···O71ix2.912 (7)H811···C613.06 (5)
N81···O323.125 (7)H812···O72ix2.86 (6)
N81···O313.239 (7)H812···O2ii1.85 (5)
N81···O72ix3.031 (7)H812···O31ii2.51 (6)
N81···C7ix3.379 (8)H812···C2ii2.96 (5)
N81···C31vii3.384 (8)H813···O312.39 (7)
N81···O2ii2.823 (6)H813···O322.47 (6)
N81···O31ii3.081 (7)H813···N32.78 (6)
N3···H8132.78 (6)H813···C31vii3.04 (5)
C1···N5iii3.319 (7)H813···O31ii2.71 (6)
C1···O52iii3.358 (7)
C7—O72—H72104 (4)O72—C7—C1116.5 (4)
O31—N3—O32120.8 (4)C3—C4—H4120
O32—N3—C3118.8 (3)C5—C4—H4121
O31—N3—C3120.4 (3)C5—C6—H6121
O51—N5—O52123.3 (3)C1—C6—H6118
O51—N5—C5119.1 (3)C21—C11—C71121.2 (4)
O52—N5—C5117.6 (4)C21—C11—C61118.6 (4)
C71—N81—H811109 (4)C61—C11—C71120.2 (4)
C71—N81—H812116 (3)C11—C21—C31121.1 (4)
H811—N81—H812108 (4)C21—C31—C41120.1 (5)
H811—N81—H813108 (5)C31—C41—C51119.9 (5)
H812—N81—H81397 (5)C41—C51—C61120.4 (4)
C71—N81—H813118 (3)C11—C61—C51119.9 (4)
C2—C1—C6121.7 (4)N81—C71—C11111.0 (4)
C6—C1—C7118.2 (4)C11—C21—H21120
C2—C1—C7120.1 (3)C31—C21—H21119
O2—C2—C3125.6 (4)C21—C31—H31119
C1—C2—C3114.6 (3)C41—C31—H31121
O2—C2—C1119.8 (4)C31—C41—H41119
C2—C3—C4123.3 (4)C51—C41—H41121
N3—C3—C4115.8 (4)C41—C51—H51120
N3—C3—C2120.9 (3)C61—C51—H51120
C3—C4—C5118.8 (4)C11—C61—H61119
N5—C5—C4119.0 (4)C51—C61—H61121
C4—C5—C6121.5 (3)N81—C71—H711109
N5—C5—C6119.5 (3)N81—C71—H712109
C1—C6—C5120.1 (4)C11—C71—H711110
O71—C7—C1122.6 (4)C11—C71—H712110
O71—C7—O72120.9 (4)H711—C71—H712107
O31—N3—C3—C4172.5 (4)C1—C2—C3—C40.3 (6)
O32—N3—C3—C2170.9 (4)O2—C2—C3—C4179.1 (4)
O31—N3—C3—C29.2 (6)C1—C2—C3—N3177.9 (3)
O32—N3—C3—C47.4 (5)N3—C3—C4—C5177.7 (4)
O51—N5—C5—C6179.0 (4)C2—C3—C4—C50.5 (6)
O51—N5—C5—C42.3 (6)C3—C4—C5—N5178.3 (4)
O52—N5—C5—C60.9 (6)C3—C4—C5—C60.4 (6)
O52—N5—C5—C4177.9 (4)C4—C5—C6—C10.1 (6)
C6—C1—C7—O710.3 (6)N5—C5—C6—C1178.6 (4)
C2—C1—C6—C50.1 (6)C61—C11—C21—C310.7 (8)
C7—C1—C2—C3177.9 (4)C71—C11—C21—C31176.7 (5)
C2—C1—C7—O720.1 (6)C21—C11—C71—N81102.2 (5)
C6—C1—C2—O2178.9 (4)C61—C11—C71—N8175.2 (6)
C6—C1—C2—C30.0 (6)C21—C11—C61—C510.2 (7)
C7—C1—C2—O23.2 (6)C71—C11—C61—C51177.3 (5)
C6—C1—C7—O72178.1 (4)C11—C21—C31—C410.9 (9)
C7—C1—C6—C5177.9 (4)C21—C31—C41—C510.5 (9)
C2—C1—C7—O71178.3 (4)C31—C41—C51—C610.0 (9)
O2—C2—C3—N31.0 (6)C41—C51—C61—C110.2 (8)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z; (v) x+1, y, z+1; (vi) x, y+1, z; (vii) x, y, z1; (viii) x, y1, z; (ix) x1, y, z1; (x) x, y, z+1; (xi) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O72—H72···O20.96 (7)1.57 (8)2.483 (6)158 (7)
O72—H72···O72i0.96 (7)2.47 (7)2.814 (6)101 (5)
N81—H811···O71ix0.99 (5)1.96 (6)2.912 (7)160 (6)
N81—H811···O72ix0.99 (5)2.54 (6)3.031 (7)110 (4)
N81—H812···O2ii1.00 (5)1.85 (5)2.823 (6)164 (5)
N81—H812···O31ii1.00 (5)2.51 (6)3.081 (7)116 (4)
N81—H813···O310.90 (7)2.39 (7)3.239 (7)158 (4)
N81—H813···O320.90 (7)2.47 (6)3.125 (7)130 (5)
C71—H712···O52xi0.962.583.530 (7)172
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z; (ix) x1, y, z1; (xi) x, y+1, z.
 

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