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In the title structure, C6H10N3+·C6H2N3O7, the asymmetric unit consists of a 2-amino-4,6-dimethyl­pyrimidinium cation and a picrate (2,4,6-trinitro­phenolate) anion. In the crystal structure, inversion-symmetry-related cations are paired via N—H...N hydrogen bonds, whereas inversion-related anions are paired via weak C—H...O hydrogen bonds. The cations and anions further inter­act with each other through N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031254/lh2147sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031254/lh2147Isup2.hkl
Contains datablock I

CCDC reference: 605414

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.060
  • wR factor = 0.201
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O5 .. O2B .. 2.77 Ang.
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT156_ALERT_4_C Axial System Input Cell not Standard ........... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2-amino-4,6-dimethylpyrimidinium 2,4,6-trinitrophenolate top
Crystal data top
C6H10N3+·C6H2N3O7Z = 2
Mr = 352.28F(000) = 364
Triclinic, P1Dx = 1.556 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 9.646 (3) ÅCell parameters from 45 reflections
b = 10.990 (3) Åθ = 4.4–69.9°
c = 8.351 (3) ŵ = 1.13 mm1
α = 79.86 (3)°T = 153 K
β = 67.75 (3)°Prism, yellow
γ = 66.62 (3)°0.17 × 0.14 × 0.10 mm
V = 751.7 (5) Å3
Data collection top
Siemens AED single-crystal
diffractometer
Rint = 0.000
Radiation source: fine- focus sealed tubeθmax = 69.9°, θmin = 4.4°
Graphite monochromatorh = 811
ω–2θ scansk = 1113
2841 measured reflectionsl = 410
2841 independent reflections1 standard reflections every 100 reflections
1974 reflections with I > 2σ(I) intensity decay: none
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1398P)2]
where P = (Fo2 + 2Fc2)/3
2841 reflections(Δ/σ)max < 0.001
247 parametersΔρmax = 0.29 e Å3
12 restraintsΔρmin = 0.25 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2> σ(F2) is used only for calculating -R-factor-obs 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*/UeqOcc. (<1)
O10.2098 (2)1.02406 (18)0.0711 (2)0.0799 (7)
O2A0.2722 (6)0.7743 (3)0.1351 (7)0.0973 (16)0.688 (8)
O3A0.5037 (8)0.6355 (10)0.1286 (13)0.109 (3)0.688 (8)
O40.6767 (3)0.6695 (2)0.3186 (4)0.1124 (10)
O50.5866 (4)0.8515 (3)0.4427 (4)0.1360 (13)
O60.0950 (3)1.2313 (2)0.1202 (4)0.1240 (10)
O70.2213 (3)1.23746 (19)0.2736 (3)0.0943 (8)
N40.3923 (3)0.7441 (2)0.0941 (3)0.0771 (8)
N50.5883 (3)0.7848 (2)0.3412 (4)0.0842 (9)
N60.1985 (2)1.17761 (19)0.1840 (3)0.0659 (7)
C90.2872 (3)0.9695 (2)0.0282 (3)0.0584 (7)
C100.3878 (3)0.8291 (2)0.0247 (3)0.0594 (7)
C110.4814 (3)0.7708 (2)0.1245 (3)0.0627 (8)
C120.4827 (3)0.8454 (2)0.2406 (3)0.0644 (8)
C130.3882 (3)0.9791 (2)0.2580 (3)0.0601 (7)
C140.2935 (3)1.0374 (2)0.1582 (3)0.0564 (7)
O3B0.445 (2)0.6331 (18)0.080 (3)0.106 (5)0.312 (8)
O2B0.3769 (15)0.8021 (8)0.2409 (13)0.108 (3)0.312 (8)
N10.0035 (2)0.78322 (17)0.2287 (3)0.0597 (6)
N20.0929 (2)0.99391 (17)0.3275 (3)0.0628 (6)
N30.0821 (2)0.82206 (17)0.4380 (2)0.0558 (6)
C20.0048 (2)0.8665 (2)0.3325 (3)0.0536 (6)
C40.1664 (3)0.6923 (2)0.4423 (3)0.0603 (7)
C50.1663 (3)0.6036 (2)0.3407 (3)0.0664 (8)
C60.0807 (3)0.6509 (2)0.2321 (3)0.0646 (8)
C70.2642 (3)0.6440 (3)0.5575 (4)0.0781 (9)
C80.0773 (4)0.5666 (3)0.1131 (4)0.0892 (11)
H130.389401.029600.338500.0720*
H110.545700.679000.114600.0750*
H10.058600.815900.157800.0720*
H2A0.094401.049200.393100.0750*
H2B0.150101.023500.258500.0750*
H50.225500.511400.347800.0800*
H7A0.272200.719600.595600.1170*
H7B0.372100.583700.494300.1170*
H7C0.212900.596800.658600.1170*
H8A0.034400.581900.129700.1340*
H8B0.132600.473000.138200.1340*
H8C0.131500.589400.007000.1340*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0948 (13)0.0702 (10)0.0866 (12)0.0162 (9)0.0554 (11)0.0085 (9)
O2A0.118 (3)0.086 (2)0.116 (3)0.0278 (18)0.069 (3)0.0266 (19)
O3A0.098 (4)0.088 (3)0.131 (6)0.001 (3)0.042 (4)0.053 (3)
O40.1227 (18)0.0738 (13)0.154 (2)0.0106 (12)0.0908 (17)0.0036 (13)
O50.194 (3)0.1013 (17)0.159 (2)0.0228 (17)0.137 (2)0.0143 (16)
O60.149 (2)0.0714 (13)0.165 (2)0.0122 (13)0.112 (2)0.0288 (13)
O70.1191 (16)0.0653 (11)0.1158 (16)0.0225 (10)0.0614 (14)0.0225 (10)
N40.0859 (15)0.0681 (14)0.0846 (15)0.0243 (11)0.0344 (12)0.0168 (11)
N50.0986 (16)0.0713 (14)0.0994 (17)0.0293 (12)0.0597 (14)0.0124 (12)
N60.0720 (12)0.0577 (11)0.0685 (12)0.0211 (9)0.0263 (10)0.0040 (9)
C90.0583 (12)0.0605 (12)0.0599 (12)0.0239 (9)0.0220 (10)0.0003 (9)
C100.0628 (12)0.0584 (12)0.0612 (12)0.0246 (10)0.0205 (10)0.0071 (10)
C110.0644 (13)0.0545 (12)0.0702 (14)0.0219 (10)0.0241 (11)0.0007 (10)
C120.0701 (14)0.0612 (13)0.0706 (14)0.0257 (11)0.0350 (12)0.0065 (10)
C130.0666 (13)0.0599 (12)0.0615 (12)0.0262 (10)0.0269 (10)0.0013 (10)
C140.0571 (11)0.0531 (11)0.0589 (12)0.0199 (9)0.0196 (9)0.0024 (9)
O3B0.124 (10)0.057 (4)0.130 (9)0.017 (7)0.042 (8)0.028 (5)
O2B0.143 (7)0.092 (5)0.093 (5)0.015 (4)0.062 (5)0.028 (4)
N10.0695 (11)0.0499 (9)0.0673 (11)0.0184 (8)0.0319 (9)0.0086 (8)
N20.0768 (12)0.0473 (9)0.0717 (12)0.0137 (8)0.0391 (10)0.0092 (8)
N30.0636 (10)0.0480 (9)0.0593 (10)0.0170 (7)0.0260 (8)0.0061 (7)
C20.0588 (11)0.0481 (10)0.0561 (11)0.0189 (8)0.0204 (9)0.0063 (8)
C40.0623 (12)0.0539 (12)0.0648 (13)0.0180 (9)0.0238 (10)0.0045 (9)
C50.0773 (14)0.0463 (11)0.0764 (15)0.0136 (10)0.0336 (12)0.0086 (10)
C60.0736 (14)0.0482 (11)0.0762 (15)0.0176 (10)0.0309 (12)0.0107 (10)
C70.0936 (18)0.0622 (14)0.0876 (17)0.0157 (12)0.0534 (15)0.0032 (12)
C80.121 (2)0.0556 (14)0.111 (2)0.0193 (14)0.0666 (19)0.0197 (14)
Geometric parameters (Å, º) top
O1—C91.242 (3)C9—C141.453 (4)
O2A—N41.235 (7)C9—C101.459 (3)
O2B—N41.311 (10)C10—C111.358 (4)
O3A—N41.237 (10)C11—C121.382 (4)
O3B—N41.124 (18)C12—C131.387 (3)
O4—N51.214 (3)C13—C141.365 (4)
O5—N51.206 (4)C11—H110.9504
O6—N61.206 (4)C13—H130.9500
O7—N61.206 (3)C4—C51.401 (4)
N4—C101.456 (3)C4—C71.486 (4)
N5—C121.449 (4)C5—C61.355 (4)
N6—C141.452 (3)C6—C81.490 (4)
N1—C61.357 (3)C5—H50.9495
N1—C21.361 (3)C7—H7A0.9798
N2—C21.322 (3)C7—H7B0.9802
N3—C41.334 (3)C7—H7C0.9797
N3—C21.342 (3)C8—H8A0.9796
N1—H10.8798C8—H8B0.9797
N2—H2B0.8801C8—H8C0.9800
N2—H2A0.8796
O1···O2A2.673 (4)C2···O1i3.253 (3)
O1···O62.628 (3)C4···C113.491 (4)
O1···N62.888 (3)C5···O3Aiv3.302 (10)
O1···O2B2.632 (9)C6···O2A3.300 (6)
O1···N1i2.799 (3)C7···O4vi3.301 (4)
O1···N2i2.837 (3)C7···O2Avii3.190 (6)
O1···C2i3.253 (3)C7···O6ix3.405 (5)
O2A···N13.177 (6)C7···O2Bvii3.309 (13)
O2A···N2i3.038 (5)C8···O6i3.081 (5)
O2A···O12.673 (4)C8···O4xi3.369 (5)
O2A···C63.300 (6)C8···C8xii3.574 (6)
O2A···C7ii3.190 (6)C9···C13iii3.331 (4)
O2B···N2i3.018 (13)C9···C23.431 (4)
O2B···O5ii2.773 (12)C9···C12iii3.508 (4)
O2B···C7ii3.309 (13)C10···C23.589 (4)
O2B···O12.632 (9)C10···C13iii3.562 (4)
O3A···O7iii3.219 (10)C11···N6iii3.368 (4)
O3A···C5iv3.302 (10)C11···C14iii3.568 (4)
O3B···O3Biv2.95 (3)C11···C43.491 (4)
O4···C8v3.369 (5)C12···C14iii3.558 (4)
O4···C7vi3.301 (4)C12···C9iii3.508 (4)
O5···O2Bvii2.773 (12)C13···C10iii3.562 (4)
O5···O5viii3.150 (4)C13···C9iii3.331 (4)
O6···O12.628 (3)C14···C12iii3.558 (4)
O6···C7ix3.405 (5)C14···C11iii3.568 (4)
O6···C8i3.081 (5)C4···H2Aix3.0869
O7···O3Aiii3.219 (10)C8···H8Axii3.0467
O7···N3ix3.228 (4)H1···H2B2.2819
O1···H1i2.0150H1···H8A2.5333
O1···H2Bi2.0648H1···O6i2.6397
O2A···H7Aii2.4280H1···O1i2.0150
O2A···H8C2.7275H2A···N3ix2.2289
O2A···H2Bi2.3287H2A···H7Aix2.4310
O2B···H7Aii2.4317H2A···C4ix3.0869
O2B···H2Bi2.3017H2B···O1i2.0648
O3A···H112.3741H2B···O2Ai2.3287
O3A···H5iv2.6178H2B···H12.2819
O3B···H112.3900H2B···O2Bi2.3017
O4···H112.4439H5···H8B2.4069
O4···H8Av2.5015H5···H7B2.5830
O4···H7Cvi2.6869H5···O3Aiv2.6178
O5···H13viii2.5497H7A···O2Bvii2.4317
O5···H132.4301H7A···H2Aix2.4310
O6···H8Bx2.8560H7A···O2Avii2.4280
O6···H7Cix2.9023H7B···H7Bvi2.4486
O6···H8Ai2.7156H7B···H52.5830
O6···H1i2.6397H7C···H8Cvii2.5946
O6···H8Ci2.6536H7C···O6ix2.9023
O7···H8Bx2.5798H7C···O4vi2.6869
O7···H132.3305H8A···C8xii3.0467
N1···O1i2.799 (3)H8A···H12.5333
N1···O2A3.177 (6)H8A···O6i2.7156
N2···O2Ai3.038 (5)H8A···O4xi2.5015
N2···N3ix3.107 (3)H8B···O7xiii2.5798
N2···O1i2.837 (3)H8B···H52.4069
N2···O2Bi3.018 (13)H8B···O6xiii2.8560
N3···O7ix3.228 (4)H8C···O2A2.7275
N3···N2ix3.107 (3)H8C···O6i2.6536
N3···N6ix3.289 (3)H8C···H7Cii2.5946
N6···N3ix3.289 (3)H11···O42.4439
N6···C11iii3.368 (4)H11···O3B2.3900
N6···O12.888 (3)H11···O3A2.3741
N3···H2Aix2.2289H13···O5viii2.5497
C2···C103.589 (4)H13···O52.4301
C2···C93.431 (4)H13···O72.3305
O2A—N4—O3A122.0 (5)N6—C14—C9119.7 (2)
O2A—N4—C10117.9 (3)N6—C14—C13115.9 (2)
O3A—N4—C10119.1 (5)C10—C11—H11120.10
O2B—N4—C10115.0 (5)C12—C11—H11120.15
O3B—N4—C10120.9 (12)C12—C13—H13120.34
O2B—N4—O3B121.2 (12)C14—C13—H13120.35
O4—N5—O5122.4 (3)N1—C2—N3121.41 (19)
O4—N5—C12118.9 (3)N2—C2—N3119.7 (2)
O5—N5—C12118.7 (2)N1—C2—N2118.9 (2)
O6—N6—O7121.1 (2)N3—C4—C7117.6 (2)
O6—N6—C14119.6 (2)C5—C4—C7120.4 (2)
O7—N6—C14119.2 (2)N3—C4—C5122.0 (2)
C2—N1—C6121.5 (2)C4—C5—C6119.2 (2)
C2—N3—C4117.8 (2)N1—C6—C8118.2 (3)
C6—N1—H1119.22C5—C6—C8123.8 (2)
C2—N1—H1119.25N1—C6—C5117.9 (2)
C2—N2—H2B120.01C4—C5—H5120.45
C2—N2—H2A120.03C6—C5—H5120.34
H2A—N2—H2B119.96C4—C7—H7A109.48
O1—C9—C10123.9 (2)C4—C7—H7B109.51
O1—C9—C14124.6 (2)C4—C7—H7C109.48
C10—C9—C14111.4 (2)H7A—C7—H7B109.44
N4—C10—C9119.2 (2)H7A—C7—H7C109.48
N4—C10—C11116.6 (2)H7B—C7—H7C109.44
C9—C10—C11124.2 (2)C6—C8—H8A109.51
C10—C11—C12119.8 (2)C6—C8—H8B109.49
N5—C12—C13119.3 (2)C6—C8—H8C109.50
N5—C12—C11119.8 (2)H8A—C8—H8B109.45
C11—C12—C13120.9 (3)H8A—C8—H8C109.43
C12—C13—C14119.3 (2)H8B—C8—H8C109.45
C9—C14—C13124.3 (2)
O2A—N4—C10—C928.4 (4)C14—C9—C10—N4178.0 (2)
O2A—N4—C10—C11152.5 (4)O1—C9—C10—C11175.2 (3)
O3A—N4—C10—C9162.5 (6)O1—C9—C14—N63.1 (4)
O3A—N4—C10—C1116.6 (6)O1—C9—C10—N43.8 (4)
O4—N5—C12—C111.6 (4)C14—C9—C10—C113.0 (4)
O4—N5—C12—C13176.2 (3)O1—C9—C14—C13174.8 (3)
O5—N5—C12—C11179.5 (3)C10—C9—C14—N6178.7 (2)
O5—N5—C12—C132.8 (5)C10—C9—C14—C133.3 (4)
O6—N6—C14—C912.8 (4)N4—C10—C11—C12179.8 (3)
O6—N6—C14—C13169.1 (3)C9—C10—C11—C121.2 (4)
O7—N6—C14—C9169.5 (3)C10—C11—C12—N5177.0 (3)
O7—N6—C14—C138.6 (4)C10—C11—C12—C130.7 (4)
C6—N1—C2—N32.6 (4)N5—C12—C13—C14177.4 (3)
C2—N1—C6—C51.0 (4)C11—C12—C13—C140.3 (4)
C6—N1—C2—N2177.9 (2)C12—C13—C14—C91.9 (4)
C2—N1—C6—C8179.4 (3)C12—C13—C14—N6179.9 (2)
C2—N3—C4—C7179.1 (2)N3—C4—C5—C61.3 (4)
C2—N3—C4—C50.2 (4)C7—C4—C5—C6177.6 (3)
C4—N3—C2—N12.1 (3)C4—C5—C6—N10.9 (4)
C4—N3—C2—N2178.4 (2)C4—C5—C6—C8177.4 (3)
Symmetry codes: (i) x, y+2, z; (ii) x, y, z1; (iii) x+1, y+2, z; (iv) x+1, y+1, z; (v) x+1, y, z; (vi) x+1, y+1, z+1; (vii) x, y, z+1; (viii) x+1, y+2, z+1; (ix) x, y+2, z+1; (x) x, y+1, z; (xi) x1, y, z; (xii) x, y+1, z; (xiii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.022.799 (3)148
N2—H2A···N3ix0.882.233.107 (3)176
N2—H2B···O1i0.882.062.837 (3)146
N2—H2B···O2Ai0.882.333.038 (5)138
C7—H7A···O2Avii0.982.433.190 (6)134
C8—H8A···O4xi0.982.503.369 (5)147
C8—H8B···O7xiii0.982.583.539 (4)166
C13—H13···O5viii0.952.553.497 (4)175
Symmetry codes: (i) x, y+2, z; (vii) x, y, z+1; (viii) x+1, y+2, z+1; (ix) x, y+2, z+1; (xi) x1, y, z; (xiii) x, y1, z.
 

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