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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
CCDC reference: 193743
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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:
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.
Crystal data top
(C7H10N)+·(C7H3N2O7)− | Z = 2 |
Mr = 335.27 | F(000) = 348 |
Triclinic, P1 | Dx = 1.505 Mg m−3 |
Hall symbol: -P 1 | Melting point = 473–475 K |
a = 10.953 (15) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 11.450 (8) Å | Cell parameters from 25 reflections |
c = 7.118 (4) Å | θ = 12.6–17.1° |
α = 94.56 (5)° | µ = 0.12 mm−1 |
β = 105.61 (7)° | T = 295 K |
γ = 117.61 (6)° | Plate, yellow |
V = 739.7 (14) Å3 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.027 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 3.1° |
Graphite monochromator | h = −14→6 |
ω–2θ scans | k = −13→14 |
3872 measured reflections | l = −8→9 |
3406 independent reflections | 3 standard reflections every 150 reflections |
1708 reflections with I > 2σ(I) | intensity decay: 1.2% |
Refinement top
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.217 | H 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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O2 | 0.7333 (3) | 0.8842 (2) | 0.3173 (4) | 0.0587 (9) | |
O31 | 0.4892 (3) | 0.8743 (3) | 0.0898 (5) | 0.0700 (10) | |
O32 | 0.3006 (3) | 0.6810 (3) | −0.0623 (5) | 0.0686 (11) | |
O51 | 0.2491 (3) | 0.2720 (3) | 0.0973 (5) | 0.0662 (10) | |
O52 | 0.4380 (3) | 0.2666 (3) | 0.2817 (5) | 0.0671 (10) | |
O71 | 0.9131 (3) | 0.6785 (3) | 0.6062 (4) | 0.0582 (9) | |
O72 | 0.9404 (3) | 0.8732 (3) | 0.5489 (5) | 0.0800 (13) | |
N3 | 0.4248 (3) | 0.7503 (3) | 0.0591 (5) | 0.0470 (10) | |
N5 | 0.3789 (3) | 0.3279 (3) | 0.2013 (5) | 0.0461 (10) | |
C1 | 0.7049 (4) | 0.6758 (3) | 0.3836 (5) | 0.0393 (10) | |
C2 | 0.6480 (4) | 0.7577 (3) | 0.2897 (5) | 0.0391 (10) | |
C3 | 0.4957 (4) | 0.6831 (3) | 0.1679 (5) | 0.0385 (10) | |
C4 | 0.4077 (4) | 0.5444 (3) | 0.1406 (5) | 0.0393 (10) | |
C5 | 0.4695 (4) | 0.4735 (3) | 0.2339 (5) | 0.0378 (10) | |
C6 | 0.6172 (4) | 0.5385 (3) | 0.3550 (5) | 0.0403 (11) | |
C7 | 0.8614 (4) | 0.7419 (4) | 0.5207 (6) | 0.0482 (11) | |
N81 | 0.2029 (4) | 0.8954 (4) | −0.1328 (6) | 0.0537 (12) | |
C11 | 0.1648 (4) | 0.8357 (4) | 0.1809 (6) | 0.0492 (12) | |
C21 | 0.2794 (5) | 0.8812 (4) | 0.3577 (6) | 0.0598 (12) | |
C31 | 0.2852 (5) | 0.7957 (5) | 0.4812 (6) | 0.0704 (18) | |
C41 | 0.1745 (6) | 0.6636 (5) | 0.4295 (7) | 0.0671 (17) | |
C51 | 0.0585 (5) | 0.6160 (4) | 0.2543 (7) | 0.0670 (16) | |
C61 | 0.0523 (4) | 0.7008 (4) | 0.1285 (6) | 0.0576 (14) | |
C71 | 0.1621 (5) | 0.9269 (4) | 0.0402 (7) | 0.0633 (16) | |
H4 | 0.304900 | 0.499100 | 0.059100 | 0.0480* | |
H6 | 0.660400 | 0.488800 | 0.418500 | 0.0510* | |
H72 | 0.879 (7) | 0.895 (6) | 0.452 (9) | 0.13 (2)* | |
H21 | 0.358800 | 0.97540 | 0.39810 | 0.0730* | |
H31 | 0.369900 | 0.83090 | 0.60380 | 0.0850* | |
H41 | 0.178700 | 0.60550 | 0.52010 | 0.0810* | |
H51 | −0.020300 | 0.52110 | 0.21750 | 0.0820* | |
H61 | −0.028400 | 0.66780 | 0.00250 | 0.0710* | |
H711 | 0.065300 | 0.91600 | −0.01030 | 0.0800* | |
H712 | 0.229200 | 1.02000 | 0.11080 | 0.0800* | |
H811 | 0.117 (6) | 0.813 (5) | −0.231 (7) | 0.078 (14)* | |
H812 | 0.238 (5) | 0.969 (5) | −0.206 (6) | 0.071 (13)* | |
H813 | 0.281 (6) | 0.884 (5) | −0.107 (7) | 0.080 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0516 (15) | 0.0362 (13) | 0.0712 (18) | 0.0158 (12) | 0.0050 (13) | 0.0245 (12) |
O31 | 0.0600 (18) | 0.0461 (16) | 0.105 (2) | 0.0313 (14) | 0.0172 (16) | 0.0345 (16) |
O32 | 0.0597 (18) | 0.0606 (17) | 0.076 (2) | 0.0340 (15) | 0.0007 (16) | 0.0247 (15) |
O51 | 0.0488 (17) | 0.0415 (15) | 0.087 (2) | 0.0128 (13) | 0.0118 (16) | 0.0147 (14) |
O52 | 0.0713 (19) | 0.0419 (15) | 0.091 (2) | 0.0328 (14) | 0.0212 (16) | 0.0268 (15) |
O71 | 0.0534 (15) | 0.0514 (15) | 0.0664 (18) | 0.0290 (13) | 0.0082 (13) | 0.0238 (13) |
O72 | 0.0494 (17) | 0.0471 (17) | 0.106 (3) | 0.0118 (14) | −0.0090 (16) | 0.0369 (17) |
N3 | 0.0494 (18) | 0.0460 (17) | 0.0540 (19) | 0.0296 (15) | 0.0164 (15) | 0.0238 (14) |
N5 | 0.0497 (18) | 0.0334 (15) | 0.0522 (18) | 0.0175 (14) | 0.0190 (15) | 0.0132 (13) |
C1 | 0.0423 (18) | 0.0367 (17) | 0.0420 (18) | 0.0215 (15) | 0.0142 (15) | 0.0164 (14) |
C2 | 0.0429 (18) | 0.0341 (17) | 0.0429 (18) | 0.0200 (15) | 0.0151 (15) | 0.0179 (14) |
C3 | 0.0426 (18) | 0.0405 (18) | 0.0398 (18) | 0.0261 (15) | 0.0130 (15) | 0.0176 (14) |
C4 | 0.0426 (18) | 0.0384 (18) | 0.0398 (18) | 0.0211 (15) | 0.0158 (15) | 0.0149 (15) |
C5 | 0.0447 (18) | 0.0311 (16) | 0.0392 (18) | 0.0191 (15) | 0.0162 (15) | 0.0108 (13) |
C6 | 0.051 (2) | 0.0382 (17) | 0.0416 (19) | 0.0274 (16) | 0.0188 (16) | 0.0183 (14) |
C7 | 0.046 (2) | 0.0413 (19) | 0.052 (2) | 0.0210 (16) | 0.0090 (17) | 0.0188 (17) |
N81 | 0.049 (2) | 0.051 (2) | 0.067 (2) | 0.0284 (17) | 0.0171 (18) | 0.0344 (18) |
C11 | 0.053 (2) | 0.045 (2) | 0.054 (2) | 0.0288 (18) | 0.0165 (18) | 0.0150 (17) |
C21 | 0.056 (2) | 0.053 (2) | 0.055 (2) | 0.020 (2) | 0.012 (2) | 0.0091 (19) |
C31 | 0.068 (3) | 0.097 (4) | 0.049 (2) | 0.048 (3) | 0.011 (2) | 0.023 (2) |
C41 | 0.086 (3) | 0.076 (3) | 0.067 (3) | 0.054 (3) | 0.036 (3) | 0.038 (2) |
C51 | 0.076 (3) | 0.046 (2) | 0.070 (3) | 0.022 (2) | 0.026 (2) | 0.023 (2) |
C61 | 0.049 (2) | 0.054 (2) | 0.061 (3) | 0.0217 (19) | 0.0120 (19) | 0.0216 (19) |
C71 | 0.075 (3) | 0.043 (2) | 0.074 (3) | 0.033 (2) | 0.021 (2) | 0.021 (2) |
Geometric parameters (Å, º) top
O2—C2 | 1.269 (4) | C4—C5 | 1.383 (6) |
O31—N3 | 1.225 (5) | C5—C6 | 1.395 (6) |
O32—N3 | 1.218 (5) | C4—H4 | 0.97 |
O51—N5 | 1.222 (5) | C6—H6 | 0.96 |
O52—N5 | 1.235 (5) | C11—C71 | 1.508 (6) |
O71—C7 | 1.218 (6) | C11—C21 | 1.368 (7) |
O72—C7 | 1.305 (6) | C11—C61 | 1.393 (6) |
O72—H72 | 0.96 (7) | C21—C31 | 1.378 (7) |
N3—C3 | 1.456 (6) | C31—C41 | 1.366 (8) |
N5—C5 | 1.449 (5) | C41—C51 | 1.365 (8) |
N81—C71 | 1.490 (7) | C51—C61 | 1.384 (6) |
N81—H812 | 1.00 (5) | C21—H21 | 0.97 |
N81—H813 | 0.90 (7) | C31—H31 | 0.97 |
N81—H811 | 0.99 (5) | C41—H41 | 0.97 |
C1—C7 | 1.498 (7) | C51—H51 | 0.98 |
C1—C6 | 1.371 (5) | C61—H61 | 0.97 |
C1—C2 | 1.460 (6) | C71—H711 | 0.97 |
C2—C3 | 1.431 (6) | C71—H712 | 0.96 |
C3—C4 | 1.386 (5) | | |
| | | |
O2···O31 | 2.673 (6) | C2···N5iv | 3.449 (7) |
O2···O72 | 2.483 (6) | C2···O51iv | 3.294 (7) |
O2···N3 | 2.925 (6) | C3···C5iv | 3.456 (7) |
O2···O72i | 3.153 (6) | C3···N5iv | 3.295 (7) |
O2···N81ii | 2.823 (6) | C4···C6iv | 3.483 (7) |
O31···C21 | 3.380 (8) | C4···C5iv | 3.325 (7) |
O31···N81ii | 3.081 (7) | C4···C4iv | 3.590 (8) |
O31···O2 | 2.673 (6) | C5···C3iv | 3.456 (7) |
O31···N81 | 3.239 (7) | C5···C6iii | 3.305 (7) |
O31···O31ii | 3.177 (6) | C5···C4iv | 3.325 (7) |
O32···N81 | 3.125 (7) | C6···C6iii | 3.560 (8) |
O32···C11 | 3.419 (8) | C6···N5iii | 3.379 (7) |
O51···C7iii | 3.247 (7) | C6···C5iii | 3.305 (7) |
O51···C2iv | 3.294 (7) | C6···C4iv | 3.483 (7) |
O52···N3iv | 3.215 (7) | C7···O51iii | 3.247 (7) |
O52···C1iii | 3.358 (7) | C7···N81v | 3.379 (8) |
O71···N81v | 2.912 (7) | C11···O32 | 3.419 (8) |
O72···N81v | 3.031 (7) | C21···O31 | 3.380 (8) |
O72···O2i | 3.153 (6) | C31···N81x | 3.384 (8) |
O72···O72i | 2.814 (6) | C2···H72 | 2.16 (7) |
O72···O2 | 2.483 (6) | C2···H812ii | 2.96 (5) |
O2···H812ii | 1.85 (5) | C7···H811v | 2.57 (6) |
O2···H72 | 1.57 (8) | C31···H813x | 3.04 (5) |
O31···H813 | 2.39 (7) | C61···H811 | 3.06 (5) |
O31···H813ii | 2.71 (6) | H4···O32 | 2.3328 |
O31···H812ii | 2.51 (6) | H4···O51 | 2.4368 |
O32···H51vi | 2.6803 | H6···O52 | 2.4372 |
O32···H41vii | 2.7841 | H6···O71 | 2.4778 |
O32···H813 | 2.47 (6) | H6···H41iii | 2.4263 |
O32···H4 | 2.3328 | H21···H712 | 2.3945 |
O51···H712viii | 2.8026 | H31···O52iii | 2.7815 |
O51···H61vi | 2.7425 | H41···H6iii | 2.4263 |
O51···H4 | 2.4368 | H41···O32x | 2.7841 |
O52···H6 | 2.4372 | H41···O71iii | 2.9003 |
O52···H712viii | 2.5795 | H51···O32vi | 2.6803 |
O52···H31iii | 2.7815 | H61···O71ix | 2.7455 |
O71···H6 | 2.4778 | H61···H711 | 2.5546 |
O71···H41iii | 2.9003 | H61···O51vi | 2.7425 |
O71···H811v | 1.96 (6) | H72···O2 | 1.57 (8) |
O71···H61v | 2.7455 | H72···C2 | 2.16 (7) |
O72···H812v | 2.86 (6) | H72···O72i | 2.47 (7) |
O72···H811v | 2.54 (6) | H72···H72i | 2.48 (10) |
O72···H72i | 2.47 (7) | H711···H61 | 2.5546 |
N3···O2 | 2.925 (6) | H712···O51xi | 2.8026 |
N3···O52iv | 3.215 (7) | H712···O52xi | 2.5795 |
N5···C2iv | 3.449 (7) | H712···H21 | 2.3945 |
N5···C1iii | 3.319 (7) | H811···O71ix | 1.96 (6) |
N5···C3iv | 3.295 (7) | H811···O72ix | 2.54 (6) |
N5···C6iii | 3.379 (7) | H811···C7ix | 2.57 (6) |
N81···O71ix | 2.912 (7) | H811···C61 | 3.06 (5) |
N81···O32 | 3.125 (7) | H812···O72ix | 2.86 (6) |
N81···O31 | 3.239 (7) | H812···O2ii | 1.85 (5) |
N81···O72ix | 3.031 (7) | H812···O31ii | 2.51 (6) |
N81···C7ix | 3.379 (8) | H812···C2ii | 2.96 (5) |
N81···C31vii | 3.384 (8) | H813···O31 | 2.39 (7) |
N81···O2ii | 2.823 (6) | H813···O32 | 2.47 (6) |
N81···O31ii | 3.081 (7) | H813···N3 | 2.78 (6) |
N3···H813 | 2.78 (6) | H813···C31vii | 3.04 (5) |
C1···N5iii | 3.319 (7) | H813···O31ii | 2.71 (6) |
C1···O52iii | 3.358 (7) | | |
| | | |
C7—O72—H72 | 104 (4) | O72—C7—C1 | 116.5 (4) |
O31—N3—O32 | 120.8 (4) | C3—C4—H4 | 120 |
O32—N3—C3 | 118.8 (3) | C5—C4—H4 | 121 |
O31—N3—C3 | 120.4 (3) | C5—C6—H6 | 121 |
O51—N5—O52 | 123.3 (3) | C1—C6—H6 | 118 |
O51—N5—C5 | 119.1 (3) | C21—C11—C71 | 121.2 (4) |
O52—N5—C5 | 117.6 (4) | C21—C11—C61 | 118.6 (4) |
C71—N81—H811 | 109 (4) | C61—C11—C71 | 120.2 (4) |
C71—N81—H812 | 116 (3) | C11—C21—C31 | 121.1 (4) |
H811—N81—H812 | 108 (4) | C21—C31—C41 | 120.1 (5) |
H811—N81—H813 | 108 (5) | C31—C41—C51 | 119.9 (5) |
H812—N81—H813 | 97 (5) | C41—C51—C61 | 120.4 (4) |
C71—N81—H813 | 118 (3) | C11—C61—C51 | 119.9 (4) |
C2—C1—C6 | 121.7 (4) | N81—C71—C11 | 111.0 (4) |
C6—C1—C7 | 118.2 (4) | C11—C21—H21 | 120 |
C2—C1—C7 | 120.1 (3) | C31—C21—H21 | 119 |
O2—C2—C3 | 125.6 (4) | C21—C31—H31 | 119 |
C1—C2—C3 | 114.6 (3) | C41—C31—H31 | 121 |
O2—C2—C1 | 119.8 (4) | C31—C41—H41 | 119 |
C2—C3—C4 | 123.3 (4) | C51—C41—H41 | 121 |
N3—C3—C4 | 115.8 (4) | C41—C51—H51 | 120 |
N3—C3—C2 | 120.9 (3) | C61—C51—H51 | 120 |
C3—C4—C5 | 118.8 (4) | C11—C61—H61 | 119 |
N5—C5—C4 | 119.0 (4) | C51—C61—H61 | 121 |
C4—C5—C6 | 121.5 (3) | N81—C71—H711 | 109 |
N5—C5—C6 | 119.5 (3) | N81—C71—H712 | 109 |
C1—C6—C5 | 120.1 (4) | C11—C71—H711 | 110 |
O71—C7—C1 | 122.6 (4) | C11—C71—H712 | 110 |
O71—C7—O72 | 120.9 (4) | H711—C71—H712 | 107 |
| | | |
O31—N3—C3—C4 | 172.5 (4) | C1—C2—C3—C4 | 0.3 (6) |
O32—N3—C3—C2 | 170.9 (4) | O2—C2—C3—C4 | 179.1 (4) |
O31—N3—C3—C2 | −9.2 (6) | C1—C2—C3—N3 | −177.9 (3) |
O32—N3—C3—C4 | −7.4 (5) | N3—C3—C4—C5 | 177.7 (4) |
O51—N5—C5—C6 | 179.0 (4) | C2—C3—C4—C5 | −0.5 (6) |
O51—N5—C5—C4 | −2.3 (6) | C3—C4—C5—N5 | −178.3 (4) |
O52—N5—C5—C6 | −0.9 (6) | C3—C4—C5—C6 | 0.4 (6) |
O52—N5—C5—C4 | 177.9 (4) | C4—C5—C6—C1 | −0.1 (6) |
C6—C1—C7—O71 | 0.3 (6) | N5—C5—C6—C1 | 178.6 (4) |
C2—C1—C6—C5 | −0.1 (6) | C61—C11—C21—C31 | 0.7 (8) |
C7—C1—C2—C3 | −177.9 (4) | C71—C11—C21—C31 | −176.7 (5) |
C2—C1—C7—O72 | −0.1 (6) | C21—C11—C71—N81 | 102.2 (5) |
C6—C1—C2—O2 | −178.9 (4) | C61—C11—C71—N81 | −75.2 (6) |
C6—C1—C2—C3 | 0.0 (6) | C21—C11—C61—C51 | −0.2 (7) |
C7—C1—C2—O2 | 3.2 (6) | C71—C11—C61—C51 | 177.3 (5) |
C6—C1—C7—O72 | −178.1 (4) | C11—C21—C31—C41 | −0.9 (9) |
C7—C1—C6—C5 | 177.9 (4) | C21—C31—C41—C51 | 0.5 (9) |
C2—C1—C7—O71 | 178.3 (4) | C31—C41—C51—C61 | 0.0 (9) |
O2—C2—C3—N3 | 1.0 (6) | C41—C51—C61—C11 | −0.2 (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, z−1; (viii) x, y−1, z; (ix) x−1, y, z−1; (x) x, y, z+1; (xi) x, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O72—H72···O2 | 0.96 (7) | 1.57 (8) | 2.483 (6) | 158 (7) |
O72—H72···O72i | 0.96 (7) | 2.47 (7) | 2.814 (6) | 101 (5) |
N81—H811···O71ix | 0.99 (5) | 1.96 (6) | 2.912 (7) | 160 (6) |
N81—H811···O72ix | 0.99 (5) | 2.54 (6) | 3.031 (7) | 110 (4) |
N81—H812···O2ii | 1.00 (5) | 1.85 (5) | 2.823 (6) | 164 (5) |
N81—H812···O31ii | 1.00 (5) | 2.51 (6) | 3.081 (7) | 116 (4) |
N81—H813···O31 | 0.90 (7) | 2.39 (7) | 3.239 (7) | 158 (4) |
N81—H813···O32 | 0.90 (7) | 2.47 (6) | 3.125 (7) | 130 (5) |
C71—H712···O52xi | 0.96 | 2.58 | 3.530 (7) | 172 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z; (ix) x−1, y, z−1; (xi) x, y+1, z. |
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