Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000619/cv6445sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000619/cv6445Isup2.hkl |
CCDC reference: 263680
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.094
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KM-4 CCD Software (Kuma, 2002); cell refinement: KM-4 CCD Software; data reduction: KM-4 CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
C3H7N6+·C7H5O2−·2H2O | F(000) = 1200 |
Mr = 284.29 | Dx = 1.408 Mg m−3 Dm = 1.40 Mg m−3 Dm measured by floatation in chloroform/dichloromethane |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2015 reflections |
a = 21.473 (4) Å | θ = 3.3–28.0° |
b = 10.229 (2) Å | µ = 0.11 mm−1 |
c = 12.353 (2) Å | T = 293 K |
β = 98.68 (2)° | Parallelepiped, colourless |
V = 2682.2 (9) Å3 | 0.45 × 0.42 × 0.24 mm |
Z = 8 |
Kuma KM-4 with CCD area detector diffractometer | 3218 independent reflections |
Radiation source: fine-focus sealed tube | 2015 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1 | θmax = 28.0°, θmin = 3.3° |
ω scans | h = −27→28 |
Absorption correction: analytical face-indexed (SHEXLTL; Sheldrick, 1990) | k = −10→13 |
Tmin = 0.948, Tmax = 0.970 | l = −16→16 |
15755 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0485P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3218 reflections | Δρmax = 0.15 e Å−3 |
218 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (4) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.07871 (4) | 0.14473 (10) | 0.02443 (8) | 0.0375 (2) | |
H1 | 0.1218 (7) | 0.1275 (12) | 0.0428 (11) | 0.053 (4)* | |
C8 | 0.04734 (5) | 0.17745 (11) | 0.10744 (9) | 0.0367 (3) | |
N2 | −0.01535 (4) | 0.15308 (10) | −0.10060 (7) | 0.0382 (2) | |
C9 | −0.04351 (5) | 0.18184 (11) | −0.01272 (9) | 0.0351 (3) | |
N3 | −0.01454 (4) | 0.19669 (10) | 0.09140 (7) | 0.0386 (3) | |
C10 | 0.04681 (5) | 0.13589 (11) | −0.07936 (9) | 0.0359 (3) | |
N4 | 0.07999 (5) | 0.18976 (12) | 0.20628 (9) | 0.0527 (3) | |
H14 | 0.1224 (7) | 0.1806 (13) | 0.2164 (12) | 0.063* | |
H24 | 0.0605 (7) | 0.2046 (13) | 0.2623 (13) | 0.063* | |
N5 | −0.10553 (4) | 0.19750 (11) | −0.03021 (9) | 0.0456 (3) | |
H15 | −0.1265 (6) | 0.1847 (12) | −0.0971 (12) | 0.055* | |
H25 | −0.1250 (6) | 0.2118 (12) | 0.0299 (11) | 0.055* | |
N6 | 0.07955 (5) | 0.10815 (12) | −0.15816 (9) | 0.0476 (3) | |
H16 | 0.1204 (7) | 0.0991 (12) | −0.1367 (11) | 0.057* | |
H26 | 0.0598 (6) | 0.1100 (13) | −0.2225 (11) | 0.057* | |
O1 | 0.21418 (4) | 0.07803 (10) | −0.08167 (7) | 0.0551 (3) | |
O2 | 0.20091 (4) | 0.10212 (9) | 0.09112 (7) | 0.0551 (3) | |
C7 | 0.23530 (5) | 0.08657 (12) | 0.01863 (10) | 0.0401 (3) | |
C1 | 0.30504 (5) | 0.07146 (11) | 0.05510 (10) | 0.0391 (3) | |
C2 | 0.32952 (6) | 0.08193 (13) | 0.16450 (11) | 0.0525 (3) | |
H2 | 0.3030 | 0.1005 | 0.2154 | 0.063* | |
C3 | 0.39319 (6) | 0.06511 (16) | 0.19898 (12) | 0.0663 (4) | |
H3 | 0.4095 | 0.0731 | 0.2728 | 0.080* | |
C4 | 0.43246 (6) | 0.03655 (15) | 0.12424 (13) | 0.0619 (4) | |
H4 | 0.4752 | 0.0230 | 0.1477 | 0.074* | |
C5 | 0.40896 (6) | 0.02813 (15) | 0.01601 (13) | 0.0617 (4) | |
H5 | 0.4358 | 0.0105 | −0.0346 | 0.074* | |
C6 | 0.34508 (6) | 0.04571 (13) | −0.01930 (11) | 0.0527 (4) | |
H6 | 0.3293 | 0.0401 | −0.0935 | 0.063* | |
O3 | 0.28925 (5) | 0.35907 (10) | 0.29767 (8) | 0.0566 (3) | |
H1O3 | 0.2800 (8) | 0.3668 (15) | 0.2282 (15) | 0.085* | |
H2O3 | 0.2884 (8) | 0.4404 (16) | 0.3208 (14) | 0.085* | |
O4 | 0.19330 (5) | 0.19624 (14) | 0.36369 (9) | 0.0625 (3) | |
H1O4 | 0.2115 (9) | 0.1203 (18) | 0.3770 (16) | 0.098 (7)* | |
H2O4 | 0.2232 (8) | 0.2455 (16) | 0.3475 (13) | 0.080 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0245 (5) | 0.0503 (6) | 0.0378 (5) | 0.0032 (4) | 0.0053 (4) | 0.0036 (4) |
C8 | 0.0306 (6) | 0.0448 (7) | 0.0348 (6) | −0.0002 (5) | 0.0048 (5) | 0.0045 (5) |
N2 | 0.0285 (5) | 0.0517 (6) | 0.0346 (5) | −0.0001 (4) | 0.0056 (4) | 0.0000 (4) |
C9 | 0.0284 (5) | 0.0404 (7) | 0.0366 (6) | −0.0003 (5) | 0.0056 (5) | 0.0027 (5) |
N3 | 0.0281 (5) | 0.0526 (6) | 0.0350 (5) | 0.0028 (4) | 0.0045 (4) | 0.0007 (4) |
C10 | 0.0323 (6) | 0.0406 (7) | 0.0353 (6) | −0.0015 (5) | 0.0069 (5) | 0.0021 (5) |
N4 | 0.0312 (5) | 0.0884 (9) | 0.0373 (6) | 0.0027 (5) | 0.0013 (5) | −0.0020 (6) |
N5 | 0.0275 (5) | 0.0710 (8) | 0.0380 (6) | 0.0042 (5) | 0.0045 (4) | −0.0052 (5) |
N6 | 0.0311 (5) | 0.0731 (8) | 0.0396 (6) | 0.0021 (5) | 0.0084 (5) | −0.0021 (6) |
O1 | 0.0381 (5) | 0.0834 (7) | 0.0429 (5) | 0.0014 (4) | 0.0035 (4) | 0.0058 (5) |
O2 | 0.0323 (4) | 0.0867 (7) | 0.0473 (5) | 0.0100 (4) | 0.0094 (4) | 0.0027 (5) |
C7 | 0.0315 (6) | 0.0465 (7) | 0.0424 (7) | 0.0002 (5) | 0.0057 (5) | 0.0051 (5) |
C1 | 0.0322 (6) | 0.0397 (7) | 0.0457 (7) | 0.0005 (5) | 0.0068 (5) | 0.0015 (5) |
C2 | 0.0371 (7) | 0.0734 (9) | 0.0472 (8) | 0.0035 (6) | 0.0068 (6) | −0.0020 (7) |
C3 | 0.0412 (8) | 0.1015 (12) | 0.0530 (9) | 0.0001 (7) | −0.0038 (7) | −0.0012 (8) |
C4 | 0.0309 (7) | 0.0772 (10) | 0.0758 (11) | 0.0028 (6) | 0.0021 (7) | −0.0010 (8) |
C5 | 0.0369 (7) | 0.0806 (11) | 0.0707 (10) | 0.0038 (7) | 0.0182 (7) | −0.0108 (8) |
C6 | 0.0396 (7) | 0.0720 (10) | 0.0480 (8) | 0.0011 (6) | 0.0111 (6) | −0.0053 (7) |
O3 | 0.0547 (6) | 0.0744 (7) | 0.0405 (5) | 0.0050 (5) | 0.0062 (4) | −0.0008 (5) |
O4 | 0.0422 (6) | 0.0800 (8) | 0.0660 (7) | −0.0033 (6) | 0.0109 (5) | 0.0095 (6) |
N1—C8 | 1.3512 (14) | O2—C7 | 1.2537 (14) |
N1—C10 | 1.3625 (15) | C7—C1 | 1.5054 (16) |
N1—H1 | 0.935 (14) | C1—C6 | 1.3754 (17) |
C8—N4 | 1.3190 (15) | C1—C2 | 1.3783 (17) |
C8—N3 | 1.3282 (13) | C2—C3 | 1.3801 (18) |
N2—C10 | 1.3324 (14) | C2—H2 | 0.9300 |
N2—C9 | 1.3524 (14) | C3—C4 | 1.372 (2) |
C9—N5 | 1.3262 (14) | C3—H3 | 0.9300 |
C9—N3 | 1.3502 (14) | C4—C5 | 1.359 (2) |
C10—N6 | 1.3149 (15) | C4—H4 | 0.9300 |
N4—H14 | 0.906 (14) | C5—C6 | 1.3871 (18) |
N4—H24 | 0.874 (15) | C5—H5 | 0.9300 |
N5—H15 | 0.889 (14) | C6—H6 | 0.9300 |
N5—H25 | 0.916 (14) | O3—H1O3 | 0.854 (17) |
N6—H16 | 0.883 (14) | O3—H2O3 | 0.881 (16) |
N6—H26 | 0.842 (13) | O4—H1O4 | 0.874 (18) |
O1—C7 | 1.2565 (14) | O4—H2O4 | 0.863 (18) |
C8—N1—C10 | 119.54 (10) | O2—C7—O1 | 123.32 (11) |
C8—N1—H1 | 116.8 (8) | O2—C7—C1 | 117.76 (10) |
C10—N1—H1 | 123.6 (8) | O1—C7—C1 | 118.86 (11) |
N4—C8—N3 | 120.26 (11) | C6—C1—C2 | 119.07 (11) |
N4—C8—N1 | 118.03 (10) | C6—C1—C7 | 120.90 (11) |
N3—C8—N1 | 121.71 (10) | C2—C1—C7 | 120.02 (11) |
C10—N2—C9 | 115.26 (10) | C1—C2—C3 | 120.42 (13) |
N5—C9—N3 | 116.65 (10) | C1—C2—H2 | 119.8 |
N5—C9—N2 | 117.08 (11) | C3—C2—H2 | 119.8 |
N3—C9—N2 | 126.27 (10) | C4—C3—C2 | 119.97 (13) |
C8—N3—C9 | 115.60 (10) | C4—C3—H3 | 120.0 |
N6—C10—N2 | 120.95 (11) | C2—C3—H3 | 120.0 |
N6—C10—N1 | 117.51 (10) | C5—C4—C3 | 120.06 (13) |
N2—C10—N1 | 121.54 (10) | C5—C4—H4 | 120.0 |
C8—N4—H14 | 120.1 (9) | C3—C4—H4 | 120.0 |
C8—N4—H24 | 119.9 (9) | C4—C5—C6 | 120.27 (13) |
H14—N4—H24 | 120.0 (13) | C4—C5—H5 | 119.9 |
C9—N5—H15 | 119.3 (9) | C6—C5—H5 | 119.9 |
C9—N5—H25 | 117.2 (8) | C1—C6—C5 | 120.19 (12) |
H15—N5—H25 | 123.1 (11) | C1—C6—H6 | 119.9 |
C10—N6—H16 | 114.8 (9) | C5—C6—H6 | 119.9 |
C10—N6—H26 | 116.4 (10) | H1O3—O3—H2O3 | 103.1 (15) |
H16—N6—H26 | 128.4 (14) | H1O4—O4—H2O4 | 103.7 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.935 (14) | 1.733 (14) | 2.6649 (13) | 173.6 (12) |
N4—H14···O4 | 0.906 (14) | 2.194 (14) | 2.8771 (15) | 131.7 (12) |
N4—H24···N3i | 0.874 (15) | 2.187 (16) | 3.0473 (16) | 167.7 (13) |
N5—H15···O3ii | 0.889 (14) | 2.110 (13) | 2.9173 (16) | 150.6 (12) |
N5—H25···O4i | 0.916 (14) | 2.119 (14) | 2.9923 (16) | 158.9 (11) |
N6—H16···O1 | 0.883 (14) | 2.037 (15) | 2.9191 (15) | 178.0 (13) |
N6—H26···N2iii | 0.842 (13) | 2.292 (14) | 3.1228 (16) | 169.0 (12) |
O3—H1O3···O1iv | 0.854 (17) | 1.918 (18) | 2.7349 (14) | 159.5 (16) |
O3—H2O3···O2v | 0.881 (16) | 1.974 (16) | 2.8329 (14) | 164.6 (16) |
O4—H1O4···O1vi | 0.874 (18) | 2.091 (19) | 2.9045 (18) | 154.7 (17) |
O4—H2O4···O3 | 0.863 (18) | 2.001 (18) | 2.8621 (16) | 175.5 (15) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, y, −z−1/2; (iv) −x+1/2, −y+1/2, −z; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, −y, z+1/2. |