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The crystal structure of a second monoclinic polymorph of anilinium picrate (C6H8N+·C6H2N3O7) shows a three-dimensional hydrogen-bonded polymer with strong primary interspecies interactions involving the proximal phenolate and adjacent nitro group O-atom acceptors and separate anilinium H-atom donors in two cyclic R_1^2(6) associations. Other nitro-O–anilinium-H hydrogen bonds together with heteromol­ecular π–π interactions are also present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022603/bt6521sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022603/bt6521Isup2.hkl
Contains datablock I

CCDC reference: 253006

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.209
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); 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: PLATON for Windows.

anilinium 2,4,6-trinitrophenate top
Crystal data top
C6H8N+·C6H2N3O7F(000) = 664
Mr = 322.24Dx = 1.554 Mg m3
Monoclinic, P21/cMelting point: 452.1–454.5 (dec.) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 13.064 (7) ÅCell parameters from 25 reflections
b = 7.1007 (17) Åθ = 13.0–17.0°
c = 14.863 (8) ŵ = 0.13 mm1
β = 92.96 (3)°T = 298 K
V = 1376.9 (11) Å3Block, yellow–brown
Z = 40.40 × 0.34 × 0.30 mm
Data collection top
Rigaku AFC 7R
diffractometer
Rint = 0.023
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.7°
Graphite monochromatorh = 1616
ω–2θ scansk = 90
3420 measured reflectionsl = 719
3160 independent reflections3 standard reflections every 150 min
1417 reflections with I > 2σ(I) intensity decay: 0.6%
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.1P)2 + 1.0338P]
where P = (Fo2 + 2Fc2)/3
3160 reflections(Δ/σ)max = 0.023
221 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.27 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
O10.61340 (18)0.1336 (4)0.03204 (16)0.0420 (9)
O210.7103 (2)0.1255 (5)0.12369 (18)0.0621 (13)
O220.8459 (3)0.2973 (5)0.1071 (2)0.0734 (14)
O411.0813 (2)0.1194 (6)0.1366 (2)0.0738 (13)
O421.0232 (2)0.0121 (7)0.2594 (2)0.0835 (16)
O610.6681 (2)0.0615 (5)0.29062 (18)0.0566 (10)
O620.5608 (2)0.0869 (6)0.2035 (2)0.0758 (13)
N20.7816 (3)0.1928 (5)0.0776 (2)0.0473 (11)
N41.0108 (3)0.0707 (6)0.1828 (2)0.0554 (13)
N60.6466 (2)0.0278 (5)0.2216 (2)0.0407 (10)
C10.7022 (3)0.1152 (5)0.0678 (2)0.0304 (11)
C20.7925 (3)0.1445 (5)0.0176 (2)0.0349 (11)
C30.8910 (3)0.1356 (6)0.0543 (2)0.0375 (11)
C40.9065 (3)0.0822 (6)0.1434 (2)0.0390 (13)
C50.8261 (3)0.0435 (6)0.1960 (2)0.0350 (11)
C60.7272 (3)0.0636 (5)0.1603 (2)0.0313 (10)
N110.5818 (2)0.2897 (5)0.4279 (2)0.0434 (10)
C110.6347 (3)0.1973 (6)0.5058 (2)0.0370 (11)
C210.5804 (3)0.1503 (6)0.5790 (3)0.0426 (14)
C310.6333 (3)0.0723 (6)0.6534 (3)0.0458 (14)
C410.7385 (3)0.0503 (6)0.6544 (3)0.0484 (14)
C510.7914 (3)0.0986 (6)0.5800 (3)0.0459 (15)
C610.7392 (3)0.1715 (6)0.5045 (3)0.0406 (11)
H30.9475000.1654000.0191000.0460*
H50.8381000.0025000.2565000.0440*
H11A0.587 (5)0.213 (9)0.376 (4)0.090 (18)*
H11B0.614 (4)0.408 (8)0.414 (3)0.072 (17)*
H11C0.513 (5)0.301 (9)0.438 (4)0.086 (19)*
H210.5084000.1698000.5786000.0520*
H310.5969000.0344000.7042000.0570*
H410.7748000.0018000.7068000.0600*
H510.8638000.0824000.5804000.0560*
H610.7749000.2029000.4523000.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0305 (13)0.0610 (18)0.0341 (14)0.0085 (13)0.0016 (10)0.0037 (13)
O210.0572 (19)0.102 (3)0.0268 (14)0.0029 (19)0.0007 (13)0.0043 (16)
O220.074 (2)0.090 (3)0.058 (2)0.008 (2)0.0207 (17)0.0298 (19)
O410.0332 (15)0.117 (3)0.072 (2)0.0042 (18)0.0114 (15)0.003 (2)
O420.0496 (19)0.144 (4)0.055 (2)0.006 (2)0.0161 (15)0.010 (2)
O610.0520 (16)0.080 (2)0.0380 (15)0.0123 (16)0.0044 (13)0.0171 (16)
O620.0373 (16)0.142 (3)0.0495 (18)0.021 (2)0.0152 (14)0.026 (2)
N20.050 (2)0.062 (2)0.0306 (17)0.0100 (19)0.0088 (15)0.0105 (17)
N40.0360 (18)0.082 (3)0.048 (2)0.0040 (19)0.0009 (16)0.007 (2)
N60.0373 (17)0.055 (2)0.0298 (16)0.0044 (16)0.0024 (13)0.0021 (15)
C10.0339 (18)0.0296 (19)0.0277 (18)0.0013 (16)0.0011 (14)0.0032 (15)
C20.042 (2)0.040 (2)0.0230 (17)0.0045 (17)0.0033 (14)0.0016 (16)
C30.0343 (19)0.043 (2)0.036 (2)0.0006 (17)0.0095 (15)0.0005 (17)
C40.0267 (17)0.052 (3)0.038 (2)0.0016 (17)0.0021 (15)0.0044 (18)
C50.0394 (19)0.042 (2)0.0235 (16)0.0017 (18)0.0007 (14)0.0026 (16)
C60.0319 (17)0.035 (2)0.0271 (17)0.0021 (16)0.0038 (14)0.0005 (15)
N110.0332 (16)0.060 (2)0.0369 (17)0.0078 (16)0.0016 (13)0.0073 (16)
C110.0345 (19)0.037 (2)0.039 (2)0.0057 (17)0.0025 (15)0.0072 (17)
C210.0322 (19)0.051 (3)0.045 (2)0.0019 (18)0.0050 (17)0.008 (2)
C310.050 (2)0.051 (3)0.037 (2)0.004 (2)0.0071 (17)0.0020 (19)
C410.048 (2)0.046 (3)0.050 (2)0.003 (2)0.0103 (19)0.000 (2)
C510.0318 (19)0.046 (3)0.059 (3)0.0094 (18)0.0067 (18)0.009 (2)
C610.0343 (19)0.043 (2)0.045 (2)0.0038 (17)0.0076 (17)0.0079 (19)
Geometric parameters (Å, º) top
O1—C11.258 (5)C3—C41.382 (4)
O21—N21.224 (5)C4—C51.369 (5)
O22—N21.219 (5)C5—C61.379 (5)
O41—N41.227 (5)C3—H30.9504
O42—N41.215 (5)C5—H50.9504
O61—N61.226 (4)C11—C611.379 (6)
O62—N61.214 (4)C11—C211.370 (6)
N2—C21.456 (4)C21—C311.389 (6)
N4—C41.457 (5)C31—C411.382 (6)
N6—C61.450 (5)C41—C511.377 (6)
N11—C111.472 (5)C51—C611.383 (6)
N11—H11A0.95 (6)C21—H210.9505
N11—H11C0.92 (7)C31—H310.9517
N11—H11B0.97 (6)C41—H410.9549
C1—C61.444 (4)C51—H510.9525
C1—C21.443 (5)C61—H610.9521
C2—C31.373 (5)
O21—N2—O22123.7 (3)N6—C6—C5115.9 (3)
O21—N2—C2119.0 (3)C1—C6—C5123.7 (3)
O22—N2—C2117.3 (3)N6—C6—C1120.5 (3)
O41—N4—O42123.6 (4)C4—C3—H3120.59
O41—N4—C4118.2 (3)C2—C3—H3120.64
O42—N4—C4118.2 (3)C4—C5—H5120.51
O61—N6—O62122.2 (3)C6—C5—H5120.09
O61—N6—C6118.3 (3)N11—C11—C21119.5 (3)
O62—N6—C6119.5 (3)N11—C11—C61118.3 (3)
H11B—N11—H11C113 (5)C21—C11—C61122.2 (4)
H11A—N11—H11C107 (5)C11—C21—C31118.2 (4)
C11—N11—H11B111 (3)C21—C31—C41120.5 (4)
C11—N11—H11C109 (4)C31—C41—C51120.2 (4)
C11—N11—H11A109 (4)C41—C51—C61119.9 (4)
H11A—N11—H11B106 (5)C11—C61—C51119.0 (4)
C2—C1—C6112.2 (3)C11—C21—H21120.81
O1—C1—C2121.8 (3)C31—C21—H21120.98
O1—C1—C6126.0 (3)C21—C31—H31119.74
N2—C2—C1119.7 (3)C41—C31—H31119.78
N2—C2—C3116.1 (3)C31—C41—H41120.07
C1—C2—C3124.2 (3)C51—C41—H41119.73
C2—C3—C4118.8 (3)C41—C51—H51120.28
C3—C4—C5121.6 (4)C61—C51—H51119.87
N4—C4—C3119.2 (3)C11—C61—H61120.49
N4—C4—C5119.2 (3)C51—C61—H61120.46
C4—C5—C6119.4 (3)
O21—N2—C2—C134.6 (5)O1—C1—C6—N60.1 (6)
O21—N2—C2—C3147.4 (4)O1—C1—C6—C5179.3 (4)
O22—N2—C2—C1146.4 (4)C1—C2—C3—C44.9 (6)
O22—N2—C2—C331.6 (5)N2—C2—C3—C4177.2 (4)
O41—N4—C4—C34.1 (6)C2—C3—C4—N4179.5 (4)
O41—N4—C4—C5174.7 (4)C2—C3—C4—C51.9 (6)
O42—N4—C4—C3175.4 (4)N4—C4—C5—C6176.7 (4)
O42—N4—C4—C55.9 (6)C3—C4—C5—C62.0 (6)
O61—N6—C6—C1161.2 (3)C4—C5—C6—C13.1 (6)
O61—N6—C6—C518.3 (5)C4—C5—C6—N6177.4 (4)
O62—N6—C6—C119.1 (5)N11—C11—C21—C31176.7 (4)
O62—N6—C6—C5161.5 (4)C21—C11—C61—C511.1 (6)
O1—C1—C2—N21.3 (5)C61—C11—C21—C310.7 (6)
C2—C1—C6—C50.4 (5)N11—C11—C61—C51174.9 (4)
C2—C1—C6—N6179.9 (4)C11—C21—C31—C412.6 (6)
C6—C1—C2—C33.6 (5)C21—C31—C41—C512.6 (7)
O1—C1—C2—C3176.6 (4)C31—C41—C51—C610.8 (7)
C6—C1—C2—N2178.4 (3)C41—C51—C61—C111.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O610.95 (6)2.01 (6)2.881 (5)152 (6)
N11—H11B···O1i0.97 (6)2.38 (5)2.909 (5)114 (3)
N11—H11B···O21i0.97 (6)2.09 (5)3.037 (5)167 (5)
N11—H11C···O1ii0.92 (7)1.79 (7)2.704 (4)169 (6)
N11—H11C···O62ii0.92 (7)2.40 (6)2.771 (4)104 (4)
C5—H5···O22iii0.952.473.135 (5)127
C31—H31···O62iv0.952.563.394 (5)146
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x, y1/2, z+1/2; (iv) x+1, y, z+1.
 

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