Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102178X/na6122sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680102178X/na6122Isup2.hkl |
CCDC reference: 180776
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.126
- Data-to-parameter ratio = 18.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N12 - H12B ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf-Nonius, 1989); data reduction: DATARED (Vasilev, unpublished); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).
2C7H10N3+·CO32−·H2O | F(000) = 744 |
Mr = 350.39 | Dx = 1.330 Mg m−3 |
Monoclinic, P21/c | Melting point: 417-419K with decomposition K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.527 (3) Å | Cell parameters from 22 reflections |
b = 10.648 (5) Å | θ = 17.9–19.9° |
c = 13.081 (5) Å | µ = 0.10 mm−1 |
β = 125.98 (2)° | T = 293 K |
V = 1750.1 (11) Å3 | Prismatic, colorless |
Z = 4 | 0.21 × 0.19 × 0.19 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 1.6° |
Graphite monochromator | h = −20→16 |
ω–2θ scans | k = −14→14 |
8538 measured reflections | l = 0→17 |
4209 independent reflections | 3 standard reflections every 500 reflections |
2691 reflections with I > 2σ(I) | intensity decay: 0.8 |
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0611P)2 + 0.1716P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.013 |
4209 reflections | Δρmax = 0.17 e Å−3 |
232 parameters | Δρmin = −0.21 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: none |
Experimental. Omega scan angle= 0.90 + 0.35*tanθ (degrees), hor. width of the var. aperture APT= 1.40 + 0.00*tanθ (mm), required final sigma(I)/I = 0.050, distance from center of goniometer to the aperture disk = 173 mm, vert. height ot the manually insertable slit in front of the detector = 3.0 mm. |
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 | ||
O1 | 0.16191 (9) | 0.51546 (10) | 0.36802 (11) | 0.0442 (3) | |
O2 | 0.10619 (10) | 0.60160 (10) | 0.47455 (12) | 0.0491 (3) | |
O3 | 0.14447 (10) | 0.72283 (10) | 0.36863 (12) | 0.0484 (3) | |
OW | 0.00985 (12) | 0.90127 (14) | 0.36233 (14) | 0.0545 (3) | |
HW1 | 0.0422 (18) | 0.843 (2) | 0.350 (2) | 0.072 (7)* | |
HW2 | −0.036 (2) | 0.930 (2) | 0.288 (2) | 0.078 (8)* | |
C | 0.13729 (12) | 0.61349 (14) | 0.40376 (14) | 0.0367 (3) | |
N11 | 0.16829 (12) | 0.71604 (13) | 0.17014 (14) | 0.0475 (4) | |
H11A | 0.1380 | 0.7688 | 0.1086 | 0.057* | |
H11B | 0.1529 | 0.7158 | 0.2234 | 0.057* | |
N12 | 0.26185 (11) | 0.63616 (13) | 0.10054 (13) | 0.0462 (3) | |
H12A | 0.2316 | 0.6888 | 0.0389 | 0.055* | |
H12B | 0.3076 | 0.5835 | 0.1090 | 0.055* | |
N13 | 0.28304 (11) | 0.55444 (13) | 0.27824 (13) | 0.0454 (3) | |
H13 | 0.2568 | 0.5474 | 0.3204 | 0.054* | |
C1 | 0.23782 (12) | 0.63615 (14) | 0.18260 (14) | 0.0373 (3) | |
C11 | 0.37191 (14) | 0.47852 (17) | 0.31423 (15) | 0.0468 (4) | |
C12 | 0.36770 (19) | 0.35040 (19) | 0.3270 (2) | 0.0645 (5) | |
H12 | 0.3061 | 0.3130 | 0.3091 | 0.077* | |
C13 | 0.4563 (2) | 0.2786 (3) | 0.3667 (3) | 0.0908 (9) | |
H13A | 0.4543 | 0.1923 | 0.3761 | 0.109* | |
C14 | 0.5470 (2) | 0.3325 (3) | 0.3923 (3) | 0.0956 (10) | |
H14 | 0.6060 | 0.2829 | 0.4188 | 0.115* | |
C15 | 0.55098 (11) | 0.45918 (18) | 0.37890 (14) | 0.0815 (7) | |
H15 | 0.6123 | 0.4957 | 0.3952 | 0.098* | |
C16 | 0.46401 (11) | 0.53270 (18) | 0.34120 (14) | 0.0608 (5) | |
H16 | 0.4673 | 0.6192 | 0.3339 | 0.073* | |
N21 | 0.09399 (12) | 0.14365 (13) | 0.51848 (15) | 0.0507 (4) | |
H21A | 0.0558 | 0.1326 | 0.5457 | 0.061* | |
H21B | 0.1203 | 0.0800 | 0.5053 | 0.061* | |
N22 | 0.07274 (12) | 0.35735 (13) | 0.51638 (15) | 0.0518 (4) | |
H22A | 0.0344 | 0.3479 | 0.5436 | 0.062* | |
H22B | 0.0853 | 0.4314 | 0.5019 | 0.062* | |
N23 | 0.17285 (12) | 0.27767 (13) | 0.45696 (15) | 0.0486 (4) | |
H23 | 0.1815 | 0.3535 | 0.4418 | 0.058* | |
C2 | 0.11218 (13) | 0.25852 (15) | 0.49693 (15) | 0.0412 (4) | |
C21 | 0.22410 (13) | 0.17881 (15) | 0.43814 (16) | 0.0429 (4) | |
C22 | 0.33062 (15) | 0.15534 (19) | 0.52751 (19) | 0.0556 (5) | |
H22 | 0.3697 | 0.2041 | 0.6003 | 0.067* | |
C23 | 0.37939 (18) | 0.0579 (2) | 0.5081 (3) | 0.0720 (7) | |
H23A | 0.4512 | 0.0409 | 0.5685 | 0.086* | |
C24 | 0.3223 (2) | −0.0126 (2) | 0.4008 (3) | 0.0776 (7) | |
H24 | 0.3552 | −0.0775 | 0.3882 | 0.093* | |
C25 | 0.2171 (2) | 0.0116 (2) | 0.3121 (2) | 0.0737 (6) | |
H25 | 0.1785 | −0.0366 | 0.2389 | 0.088* | |
C26 | 0.16773 (17) | 0.10721 (18) | 0.33021 (19) | 0.0578 (5) | |
H26 | 0.0959 | 0.1234 | 0.2692 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0604 (7) | 0.0319 (5) | 0.0582 (7) | −0.0003 (5) | 0.0449 (6) | −0.0025 (5) |
O2 | 0.0715 (8) | 0.0372 (6) | 0.0646 (8) | −0.0045 (5) | 0.0545 (7) | −0.0053 (5) |
O3 | 0.0716 (8) | 0.0331 (6) | 0.0599 (7) | 0.0019 (5) | 0.0494 (7) | 0.0011 (5) |
OW | 0.0649 (9) | 0.0538 (8) | 0.0551 (8) | 0.0138 (7) | 0.0410 (8) | 0.0085 (6) |
C | 0.0389 (8) | 0.0342 (8) | 0.0415 (8) | −0.0024 (6) | 0.0261 (7) | −0.0043 (6) |
N11 | 0.0570 (8) | 0.0448 (8) | 0.0504 (8) | 0.0123 (6) | 0.0369 (7) | 0.0097 (6) |
N12 | 0.0520 (8) | 0.0484 (8) | 0.0487 (8) | 0.0105 (6) | 0.0354 (7) | 0.0116 (6) |
N13 | 0.0501 (8) | 0.0501 (8) | 0.0489 (8) | 0.0119 (6) | 0.0363 (7) | 0.0134 (6) |
C1 | 0.0376 (8) | 0.0362 (8) | 0.0401 (8) | −0.0018 (6) | 0.0240 (7) | 0.0006 (6) |
C11 | 0.0496 (9) | 0.0556 (10) | 0.0415 (9) | 0.0138 (8) | 0.0303 (8) | 0.0117 (8) |
C12 | 0.0810 (14) | 0.0568 (12) | 0.0762 (14) | 0.0202 (10) | 0.0576 (13) | 0.0224 (10) |
C13 | 0.120 (2) | 0.0763 (16) | 0.1015 (19) | 0.0528 (16) | 0.0791 (18) | 0.0411 (14) |
C14 | 0.0878 (19) | 0.124 (2) | 0.0896 (18) | 0.0631 (18) | 0.0606 (16) | 0.0404 (17) |
C15 | 0.0495 (12) | 0.123 (2) | 0.0703 (14) | 0.0221 (13) | 0.0343 (11) | 0.0163 (15) |
C16 | 0.0511 (11) | 0.0747 (13) | 0.0558 (11) | 0.0072 (10) | 0.0311 (9) | 0.0071 (10) |
N21 | 0.0649 (9) | 0.0384 (7) | 0.0699 (10) | 0.0030 (7) | 0.0515 (9) | 0.0068 (7) |
N22 | 0.0665 (9) | 0.0387 (7) | 0.0742 (10) | −0.0037 (7) | 0.0548 (9) | −0.0038 (7) |
N23 | 0.0641 (9) | 0.0336 (7) | 0.0687 (10) | 0.0033 (6) | 0.0505 (8) | 0.0063 (6) |
C2 | 0.0452 (8) | 0.0393 (8) | 0.0436 (9) | −0.0019 (7) | 0.0285 (8) | 0.0012 (7) |
C21 | 0.0520 (9) | 0.0372 (8) | 0.0540 (10) | 0.0035 (7) | 0.0393 (9) | 0.0069 (7) |
C22 | 0.0536 (10) | 0.0614 (12) | 0.0600 (11) | −0.0012 (9) | 0.0379 (10) | 0.0066 (9) |
C23 | 0.0612 (13) | 0.0782 (15) | 0.0963 (17) | 0.0241 (11) | 0.0572 (13) | 0.0334 (14) |
C24 | 0.113 (2) | 0.0557 (13) | 0.108 (2) | 0.0252 (13) | 0.0897 (19) | 0.0171 (13) |
C25 | 0.1070 (19) | 0.0502 (12) | 0.0780 (15) | 0.0077 (12) | 0.0623 (15) | −0.0041 (11) |
C26 | 0.0655 (12) | 0.0500 (11) | 0.0574 (11) | 0.0040 (9) | 0.0359 (10) | 0.0020 (9) |
O1—C | 1.2900 (18) | C15—H15 | 0.9300 |
O2—C | 1.2775 (18) | C16—H16 | 0.9300 |
O3—C | 1.2804 (18) | N21—C2 | 1.322 (2) |
OW—HW1 | 0.87 (2) | N21—H21A | 0.8600 |
OW—HW2 | 0.86 (3) | N21—H21B | 0.8600 |
N11—C1 | 1.307 (2) | N22—C2 | 1.315 (2) |
N11—H11A | 0.8600 | N22—H22A | 0.8600 |
N11—H11B | 0.8600 | N22—H22B | 0.8600 |
N12—C1 | 1.328 (2) | N23—C2 | 1.335 (2) |
N12—H12A | 0.8600 | N23—C21 | 1.426 (2) |
N12—H12B | 0.8600 | N23—H23 | 0.8600 |
N13—C1 | 1.335 (2) | C21—C26 | 1.374 (3) |
N13—C11 | 1.420 (2) | C21—C22 | 1.376 (3) |
N13—H13 | 0.8600 | C22—C23 | 1.393 (3) |
C11—C12 | 1.381 (3) | C22—H22 | 0.9300 |
C11—C16 | 1.382 (2) | C23—C24 | 1.363 (4) |
C12—C13 | 1.381 (3) | C23—H23A | 0.9300 |
C12—H12 | 0.9300 | C24—C25 | 1.362 (3) |
C13—C14 | 1.368 (4) | C24—H24 | 0.9300 |
C13—H13A | 0.9300 | C25—C26 | 1.376 (3) |
C14—C15 | 1.366 (4) | C25—H25 | 0.9300 |
C14—H14 | 0.9300 | C26—H26 | 0.9300 |
C15—C16 | 1.377 (3) | ||
HW1—OW—HW2 | 103 (2) | C15—C16—H16 | 119.9 |
O2—C—O3 | 120.00 (13) | C11—C16—H16 | 119.9 |
O2—C—O1 | 120.07 (13) | C2—N21—H21A | 120.0 |
O3—C—O1 | 119.93 (13) | C2—N21—H21B | 120.0 |
C1—N11—H11A | 120.0 | H21A—N21—H21B | 120.0 |
C1—N11—H11B | 120.0 | C2—N22—H22A | 120.0 |
H11A—N11—H11B | 120.0 | C2—N22—H22B | 120.0 |
C1—N12—H12A | 120.0 | H22A—N22—H22B | 120.0 |
C1—N12—H12B | 120.0 | C2—N23—C21 | 123.29 (14) |
H12A—N12—H12B | 120.0 | C2—N23—H23 | 118.4 |
C1—N13—C11 | 123.74 (13) | C21—N23—H23 | 118.4 |
C1—N13—H13 | 118.1 | N22—C2—N21 | 121.11 (14) |
C11—N13—H13 | 118.1 | N22—C2—N23 | 118.01 (15) |
N11—C1—N12 | 120.19 (14) | N21—C2—N23 | 120.88 (15) |
N11—C1—N13 | 118.82 (14) | C26—C21—C22 | 119.63 (17) |
N12—C1—N13 | 120.98 (14) | C26—C21—N23 | 120.26 (16) |
C12—C11—C16 | 119.80 (17) | C22—C21—N23 | 120.12 (16) |
C12—C11—N13 | 119.80 (17) | C21—C22—C23 | 119.4 (2) |
C16—C11—N13 | 120.35 (16) | C21—C22—H22 | 120.3 |
C11—C12—C13 | 119.0 (2) | C23—C22—H22 | 120.3 |
C11—C12—H12 | 120.5 | C24—C23—C22 | 120.2 (2) |
C13—C12—H12 | 120.5 | C24—C23—H23A | 119.9 |
C14—C13—C12 | 120.9 (2) | C22—C23—H23A | 119.9 |
C14—C13—H13A | 119.5 | C25—C24—C23 | 120.2 (2) |
C12—C13—H13A | 119.5 | C25—C24—H24 | 119.9 |
C15—C14—C13 | 120.1 (2) | C23—C24—H24 | 119.9 |
C15—C14—H14 | 120.0 | C24—C25—C26 | 120.3 (2) |
C13—C14—H14 | 120.0 | C24—C25—H25 | 119.9 |
C14—C15—C16 | 119.89 (13) | C26—C25—H25 | 119.9 |
C14—C15—H15 | 120.1 | C21—C26—C25 | 120.3 (2) |
C16—C15—H15 | 120.1 | C21—C26—H26 | 119.9 |
C15—C16—C11 | 120.26 (10) | C25—C26—H26 | 119.9 |
C1—N13—C11—C16 | 54.4 (2) | C2—N23—C21—C26 | 79.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
OW—HW1···O3 | 0.87 (2) | 1.94 (3) | 2.7899 (19) | 165 (2) |
OW—HW2···O1i | 0.86 (3) | 2.03 (3) | 2.868 (2) | 166 (2) |
N21—H21A···OWii | 0.86 | 2.01 | 2.866 (2) | 170 |
N21—H21B···OWiii | 0.86 | 2.51 | 3.067 (2) | 123 |
N22—H22A···O2ii | 0.86 | 2.12 | 2.8830 (19) | 147 |
N22—H22B···O2 | 0.86 | 1.91 | 2.769 (2) | 175 |
N23—H23···O1 | 0.86 | 1.91 | 2.750 (2) | 164 |
N11—H11A···O2iv | 0.86 | 2.05 | 2.889 (2) | 164 |
N11—H11B···O3 | 0.86 | 1.98 | 2.831 (2) | 170 |
N12—H12A···O3iv | 0.86 | 2.03 | 2.878 (2) | 167 |
N13—H13···O1 | 0.86 | 1.94 | 2.7721 (17) | 163 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1; (iii) x, y−1, z; (iv) x, −y+3/2, z−1/2. |
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