Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017088/dn6153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017088/dn6153Isup2.hkl |
CCDC reference: 248828
Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1996) and Materials Studio (Accelrys, 2001); software used to prepare material for publication: SHELXL97.
C6H10N3O2+·C4H5O6− | F(000) = 640 |
Mr = 305.25 | Dx = 1.604 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2110 reflections |
a = 5.0207 (9) Å | θ = 2.6–22.4° |
b = 12.109 (2) Å | µ = 0.14 mm−1 |
c = 20.797 (4) Å | T = 295 K |
V = 1264.4 (4) Å3 | Needle, colourless |
Z = 4 | 0.40 × 0.10 × 0.05 mm |
Siemens SMART APEX CCD diffractometer | 1334 independent reflections |
Radiation source: fine-focus sealed tube | 1117 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 67 pixels mm-1 | θmax = 25.1°, θmin = 2.0° |
Thin–slice ω scans | h = −3→5 |
Absorption correction: multi-scan (Blessing, 1995) | k = −13→14 |
Tmin = 0.941, Tmax = 0.998 | l = −23→24 |
6322 measured reflections |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.019P)2] where P = (Fo2 + 2Fc2)/3 |
1334 reflections | (Δ/σ)max < 0.001 |
194 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Experimental. The data was collected at room temperature using a Bruker AXS SMART– APEX CCD area-detector (Mo Kα radiation). Intensities were integrated from a series of exposures. Each exposure covered 0.3° in ω, with an exposure time of 60 s and the total data set was more than a hemisphere. The SAINT software containing SADABS was used to integrate and correct the data. |
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. MERG 3 inserted in instruction file to merg all friedel pairs prior to least squares refinement. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5828 (5) | 0.03063 (19) | 0.32085 (11) | 0.0274 (6) | |
C2 | 0.7235 (5) | −0.0158 (2) | 0.27282 (12) | 0.0349 (6) | |
H2 | 0.7054 | −0.0011 | 0.2291 | 0.042* | |
C3 | 0.8663 (6) | −0.0862 (2) | 0.36268 (13) | 0.0392 (7) | |
H3 | 0.9616 | −0.1279 | 0.3924 | 0.047* | |
C4 | 0.3684 (5) | 0.11467 (18) | 0.32007 (11) | 0.0305 (6) | |
H4A | 0.2245 | 0.0889 | 0.3473 | 0.037* | |
H4B | 0.2993 | 0.1198 | 0.2766 | 0.037* | |
C5 | 0.4473 (5) | 0.23026 (19) | 0.34208 (11) | 0.0300 (6) | |
H5 | 0.3076 | 0.2810 | 0.3276 | 0.036* | |
C6 | 0.7087 (5) | 0.27209 (19) | 0.31508 (12) | 0.0277 (6) | |
C7 | 0.5204 (6) | 0.19402 (19) | 0.11514 (12) | 0.0327 (6) | |
C8 | 0.3547 (5) | 0.14123 (18) | 0.06330 (10) | 0.0283 (6) | |
H8 | 0.1704 | 0.1670 | 0.0671 | 0.034* | |
C9 | 0.3612 (5) | 0.01531 (19) | 0.07077 (10) | 0.0291 (6) | |
H9 | 0.2422 | −0.0032 | 0.1066 | 0.035* | |
C10 | 0.2460 (5) | −0.0390 (2) | 0.01085 (12) | 0.0322 (6) | |
N1 | 0.8983 (4) | −0.08880 (16) | 0.30024 (10) | 0.0391 (6) | |
H1 | 1.0103 | −0.1295 | 0.2798 | 0.047* | |
N2 | 0.6779 (4) | −0.01512 (16) | 0.37654 (9) | 0.0340 (5) | |
H2A | 0.6226 | 0.0003 | 0.4146 | 0.041* | |
N3 | 0.4589 (5) | 0.23784 (18) | 0.41277 (10) | 0.0473 (6) | |
H3A | 0.6164 | 0.2136 | 0.4265 | 0.071* | |
H3B | 0.3302 | 0.1966 | 0.4298 | 0.071* | |
H3C | 0.4371 | 0.3078 | 0.4247 | 0.071* | |
O1 | 0.8800 (4) | 0.30273 (15) | 0.35291 (8) | 0.0439 (5) | |
O2 | 0.7275 (4) | 0.27511 (14) | 0.25462 (8) | 0.0434 (5) | |
O3 | 0.4282 (4) | 0.17651 (15) | 0.17279 (8) | 0.0435 (5) | |
H3D | 0.5209 | 0.2092 | 0.1991 | 0.065* | |
O4 | 0.7156 (4) | 0.24775 (16) | 0.10423 (8) | 0.0536 (6) | |
O5 | 0.4566 (4) | 0.17257 (15) | 0.00294 (8) | 0.0384 (5) | |
H5A | 0.3427 | 0.2071 | −0.0169 | 0.058* | |
O6 | 0.6163 (3) | −0.02466 (14) | 0.08717 (8) | 0.0338 (4) | |
H6 | 0.7191 | −0.0140 | 0.0572 | 0.051* | |
O7 | 0.0131 (3) | −0.01179 (16) | −0.00399 (8) | 0.0452 (5) | |
O8 | 0.3848 (4) | −0.10665 (14) | −0.01880 (8) | 0.0423 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0313 (14) | 0.0219 (12) | 0.0289 (13) | −0.0060 (12) | −0.0007 (12) | 0.0008 (11) |
C2 | 0.0423 (16) | 0.0323 (14) | 0.0300 (14) | −0.0013 (13) | 0.0023 (12) | −0.0029 (12) |
C3 | 0.0422 (17) | 0.0275 (15) | 0.0478 (18) | 0.0047 (14) | 0.0036 (14) | 0.0050 (13) |
C4 | 0.0281 (13) | 0.0302 (14) | 0.0331 (13) | −0.0056 (12) | 0.0033 (12) | 0.0029 (11) |
C5 | 0.0260 (14) | 0.0236 (13) | 0.0406 (15) | 0.0016 (11) | 0.0052 (11) | 0.0024 (11) |
C6 | 0.0256 (14) | 0.0219 (13) | 0.0356 (15) | 0.0028 (11) | 0.0028 (12) | −0.0020 (11) |
C7 | 0.0413 (17) | 0.0256 (13) | 0.0312 (14) | 0.0049 (13) | 0.0035 (12) | 0.0033 (11) |
C8 | 0.0278 (13) | 0.0292 (13) | 0.0278 (13) | 0.0022 (12) | 0.0011 (11) | 0.0053 (10) |
C9 | 0.0268 (13) | 0.0315 (13) | 0.0291 (14) | −0.0013 (12) | −0.0039 (11) | 0.0084 (11) |
C10 | 0.0322 (15) | 0.0343 (15) | 0.0302 (14) | −0.0095 (14) | −0.0024 (12) | 0.0063 (11) |
N1 | 0.0430 (14) | 0.0272 (12) | 0.0472 (14) | 0.0037 (11) | 0.0128 (12) | −0.0085 (10) |
N2 | 0.0404 (13) | 0.0296 (12) | 0.0320 (12) | 0.0031 (11) | 0.0068 (10) | 0.0014 (10) |
N3 | 0.0606 (16) | 0.0350 (12) | 0.0464 (13) | −0.0170 (12) | 0.0243 (12) | −0.0134 (11) |
O1 | 0.0270 (10) | 0.0598 (13) | 0.0449 (11) | −0.0062 (10) | 0.0019 (9) | −0.0118 (9) |
O2 | 0.0496 (12) | 0.0468 (11) | 0.0338 (11) | −0.0166 (10) | 0.0075 (9) | 0.0027 (9) |
O3 | 0.0484 (13) | 0.0534 (12) | 0.0286 (10) | −0.0140 (10) | 0.0017 (9) | −0.0017 (9) |
O4 | 0.0618 (14) | 0.0597 (13) | 0.0394 (12) | −0.0325 (13) | 0.0091 (10) | −0.0031 (9) |
O5 | 0.0476 (12) | 0.0371 (11) | 0.0306 (10) | 0.0039 (9) | 0.0015 (8) | 0.0111 (8) |
O6 | 0.0314 (10) | 0.0316 (9) | 0.0384 (10) | 0.0020 (9) | −0.0088 (8) | 0.0029 (9) |
O7 | 0.0317 (10) | 0.0667 (14) | 0.0371 (11) | 0.0016 (10) | −0.0108 (8) | −0.0007 (9) |
O8 | 0.0436 (11) | 0.0371 (10) | 0.0460 (11) | 0.0021 (10) | −0.0093 (9) | −0.0120 (9) |
C1—C2 | 1.347 (3) | C7—O3 | 1.303 (3) |
C1—N2 | 1.370 (3) | C7—C8 | 1.504 (3) |
C1—C4 | 1.481 (3) | C8—O5 | 1.408 (3) |
C2—N1 | 1.370 (3) | C8—C9 | 1.533 (3) |
C2—H2 | 0.9300 | C8—H8 | 0.9800 |
C3—N1 | 1.309 (3) | C9—O6 | 1.411 (3) |
C3—N2 | 1.311 (3) | C9—C10 | 1.523 (3) |
C3—H3 | 0.9300 | C9—H9 | 0.9800 |
C4—C5 | 1.525 (3) | C10—O8 | 1.240 (3) |
C4—H4A | 0.9700 | C10—O7 | 1.253 (3) |
C4—H4B | 0.9700 | N1—H1 | 0.8600 |
C5—N3 | 1.474 (3) | N2—H2A | 0.8600 |
C5—C6 | 1.515 (3) | N3—H3A | 0.8900 |
C5—H5 | 0.9800 | N3—H3B | 0.8900 |
C6—O1 | 1.223 (3) | N3—H3C | 0.8900 |
C6—O2 | 1.261 (3) | O3—H3D | 0.8200 |
C6—O2 | 1.261 (3) | O5—H5A | 0.8200 |
C7—O4 | 1.198 (3) | O6—H6 | 0.8200 |
C2—C1—N2 | 106.0 (2) | O5—C8—C9 | 110.54 (18) |
C2—C1—C4 | 131.3 (2) | C7—C8—C9 | 109.78 (19) |
N2—C1—C4 | 122.7 (2) | O5—C8—H8 | 109.2 |
C1—C2—N1 | 107.3 (2) | C7—C8—H8 | 109.2 |
C1—C2—H2 | 126.4 | C9—C8—H8 | 109.2 |
N1—C2—H2 | 126.4 | O6—C9—C10 | 113.2 (2) |
N1—C3—N2 | 108.8 (2) | O6—C9—C8 | 112.63 (19) |
N1—C3—H3 | 125.6 | C10—C9—C8 | 109.76 (18) |
N2—C3—H3 | 125.6 | O6—C9—H9 | 106.9 |
C1—C4—C5 | 116.0 (2) | C10—C9—H9 | 106.9 |
C1—C4—H4A | 108.3 | C8—C9—H9 | 106.9 |
C5—C4—H4A | 108.3 | O8—C10—O7 | 125.1 (2) |
C1—C4—H4B | 108.3 | O8—C10—C9 | 118.6 (2) |
C5—C4—H4B | 108.3 | O7—C10—C9 | 116.3 (2) |
H4A—C4—H4B | 107.4 | C3—N1—C2 | 108.6 (2) |
N3—C5—C6 | 108.3 (2) | C3—N1—H1 | 125.7 |
N3—C5—C4 | 111.51 (19) | C2—N1—H1 | 125.7 |
C6—C5—C4 | 114.9 (2) | C3—N2—C1 | 109.3 (2) |
N3—C5—H5 | 107.2 | C3—N2—H2A | 125.3 |
C6—C5—H5 | 107.2 | C1—N2—H2A | 125.3 |
C4—C5—H5 | 107.2 | C5—N3—H3A | 109.5 |
O1—C6—O2 | 125.4 (2) | C5—N3—H3B | 109.5 |
O1—C6—O2 | 125.4 (2) | H3A—N3—H3B | 109.5 |
O1—C6—C5 | 118.2 (2) | C5—N3—H3C | 109.5 |
O2—C6—C5 | 116.4 (2) | H3A—N3—H3C | 109.5 |
O2—C6—C5 | 116.4 (2) | H3B—N3—H3C | 109.5 |
O4—C7—O3 | 123.6 (2) | C7—O3—H3D | 109.5 |
O4—C7—C8 | 123.2 (2) | C8—O5—H5A | 109.5 |
O3—C7—C8 | 113.2 (2) | C9—O6—H6 | 109.5 |
O5—C8—C7 | 108.9 (2) | ||
N2—C1—C2—N1 | 0.4 (3) | O5—C8—C9—O6 | 79.5 (2) |
C4—C1—C2—N1 | 179.9 (2) | C7—C8—C9—O6 | −40.6 (3) |
C2—C1—C4—C5 | −105.5 (3) | O5—C8—C9—C10 | −47.6 (3) |
N2—C1—C4—C5 | 73.9 (3) | C7—C8—C9—C10 | −167.7 (2) |
C1—C4—C5—N3 | −79.1 (3) | O6—C9—C10—O8 | −3.2 (3) |
C1—C4—C5—C6 | 44.6 (3) | C8—C9—C10—O8 | 123.6 (2) |
N3—C5—C6—O1 | 0.7 (3) | O6—C9—C10—O7 | 175.8 (2) |
C4—C5—C6—O1 | −124.7 (2) | C8—C9—C10—O7 | −57.3 (3) |
N3—C5—C6—O2 | −177.35 (19) | N2—C3—N1—C2 | 0.3 (3) |
C4—C5—C6—O2 | 57.2 (3) | C1—C2—N1—C3 | −0.4 (3) |
N3—C5—C6—O2 | −177.35 (19) | N1—C3—N2—C1 | 0.0 (3) |
C4—C5—C6—O2 | 57.2 (3) | C2—C1—N2—C3 | −0.3 (3) |
O4—C7—C8—O5 | −4.2 (3) | C4—C1—N2—C3 | −179.8 (2) |
O3—C7—C8—O5 | 175.00 (19) | O1—C6—O2—O2 | 0.0 (4) |
O4—C7—C8—C9 | 116.9 (2) | C5—C6—O2—O2 | 0.0 (3) |
O3—C7—C8—C9 | −63.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 1.89 | 2.747 (3) | 173 |
N2—H2A···O7ii | 0.86 | 1.83 | 2.683 (3) | 171 |
N3—H3B···O8ii | 0.89 | 1.87 | 2.743 (3) | 167 |
N3—H3C···O6iii | 0.89 | 2.06 | 2.901 (3) | 157 |
N3—H3C···O8iii | 0.89 | 2.39 | 3.004 (3) | 127 |
O5—H5A···O4iv | 0.82 | 2.00 | 2.713 (2) | 145 |
O5—H5A···O5iv | 0.82 | 2.44 | 3.136 (2) | 143 |
O6—H6···O7v | 0.82 | 1.95 | 2.754 (2) | 167 |
O3—H3D···O2 | 0.82 | 1.75 | 2.565 (2) | 178 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1/2, −y, z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1/2, −y+1/2, −z; (v) x+1, y, z. |