Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021803/na6173sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021803/na6173Isup2.hkl |
CCDC reference: 169989
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.102
- Data-to-parameter ratio = 13.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_353 Alert C Long N-H Bond (0.87A) N(2) - H(2B) = 1.04 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C4H12N22+·2C4H3O4− | F(000) = 672 |
Mr = 318.28 | Dx = 1.490 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.735 (2) Å | Cell parameters from 22 reflections |
b = 11.603 (2) Å | θ = 4.0–12.6° |
c = 11.843 (2) Å | µ = 0.13 mm−1 |
β = 105.87 (1)° | T = 293 K |
V = 1418.9 (4) Å3 | Prism, colorless |
Z = 4 | 0.46 × 0.30 × 0.20 mm |
Siemens P4 diffractometer | Rint = 0.028 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 2.3° |
Graphite monochromator | h = 0→13 |
ω scans | k = 0→14 |
2775 measured reflections | l = −14→13 |
2631 independent reflections | 3 standard reflections every 97 reflections |
1500 reflections with I > 2σ(I) | intensity decay: 1.3% |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0698P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
2631 reflections | Δρmax = 0.14 e Å−3 |
200 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0156 (16) |
Experimental. Data collection were performed with a scan width of Δω = (1.0 + 0.30 tan θ)o and a scan rate of less than 16°min-1 inω. |
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 | 1.01707 (16) | 0.90544 (15) | 0.70442 (14) | 0.0504 (5) | |
O2 | 0.83884 (16) | 0.81417 (14) | 0.70825 (14) | 0.0461 (5) | |
O3 | 0.68105 (16) | 0.89171 (15) | 0.99624 (16) | 0.0548 (5) | |
O4 | 0.69656 (15) | 0.80606 (15) | 0.83507 (14) | 0.0482 (5) | |
O5 | 1.07921 (15) | 0.71574 (15) | −0.07079 (14) | 0.0493 (5) | |
O6 | 1.09071 (16) | 0.63470 (15) | −0.23602 (15) | 0.0529 (5) | |
O7 | 0.93714 (16) | 0.70797 (14) | 0.05629 (14) | 0.0476 (5) | |
O8 | 0.76236 (17) | 0.61331 (16) | 0.06466 (14) | 0.0524 (5) | |
N1 | 0.98012 (17) | 0.76114 (16) | 0.50401 (15) | 0.0354 (5) | |
N2 | 0.80103 (17) | 0.72217 (16) | 0.27844 (15) | 0.0362 (5) | |
C1 | 0.9245 (2) | 0.8922 (2) | 0.7458 (2) | 0.0383 (6) | |
C2 | 0.9124 (2) | 0.9718 (2) | 0.84063 (19) | 0.0414 (6) | |
H2 | 0.9691 | 1.0341 | 0.8538 | 0.050* | |
C3 | 0.8331 (2) | 0.9680 (2) | 0.9098 (2) | 0.0402 (6) | |
H3 | 0.8435 | 1.0281 | 0.9636 | 0.048* | |
C4 | 0.7306 (2) | 0.8833 (2) | 0.9148 (2) | 0.0397 (6) | |
C5 | 1.0403 (2) | 0.6429 (2) | −0.1548 (2) | 0.0398 (6) | |
C6 | 0.9308 (2) | 0.5653 (2) | −0.1553 (2) | 0.0433 (6) | |
H6 | 0.9135 | 0.5102 | −0.2147 | 0.052* | |
C7 | 0.8529 (2) | 0.5609 (2) | −0.0853 (2) | 0.0436 (6) | |
H7 | 0.7899 | 0.5037 | −0.1043 | 0.052* | |
C8 | 0.8496 (2) | 0.6319 (2) | 0.0180 (2) | 0.0385 (6) | |
C9 | 0.9382 (2) | 0.8570 (2) | 0.4191 (2) | 0.0417 (6) | |
H9A | 1.0078 | 0.9127 | 0.4294 | 0.050* | |
H9B | 0.8642 | 0.8956 | 0.4340 | 0.050* | |
C10 | 0.9025 (2) | 0.8124 (2) | 0.29493 (19) | 0.0393 (6) | |
H10A | 0.8710 | 0.8755 | 0.2409 | 0.047* | |
H10B | 0.9787 | 0.7805 | 0.2775 | 0.047* | |
C11 | 0.8422 (2) | 0.6266 (2) | 0.36360 (18) | 0.0410 (6) | |
H11A | 0.9162 | 0.5876 | 0.3489 | 0.049* | |
H11B | 0.7724 | 0.5711 | 0.3531 | 0.049* | |
C12 | 0.8781 (2) | 0.6714 (2) | 0.48857 (19) | 0.0388 (6) | |
H12A | 0.8021 | 0.7038 | 0.5059 | 0.047* | |
H12B | 0.9094 | 0.6083 | 0.5427 | 0.047* | |
H2' | 1.0128 | 0.7165 | −0.0007 | 0.080* | |
H1' | 0.7626 | 0.8049 | 0.7663 | 0.080* | |
H1A | 1.0576 | 0.7292 | 0.5008 | 0.080* | |
H2B | 0.7933 | 0.6886 | 0.1958 | 0.080* | |
H2A | 0.7219 | 0.7587 | 0.2816 | 0.080* | |
H1B | 0.9951 | 0.7949 | 0.5823 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0585 (12) | 0.0542 (11) | 0.0475 (11) | −0.0025 (10) | 0.0295 (10) | 0.0016 (9) |
O2 | 0.0465 (10) | 0.0500 (11) | 0.0414 (10) | −0.0044 (9) | 0.0116 (8) | −0.0120 (8) |
O3 | 0.0515 (11) | 0.0524 (11) | 0.0741 (13) | −0.0057 (9) | 0.0400 (10) | −0.0088 (10) |
O4 | 0.0391 (10) | 0.0529 (11) | 0.0531 (11) | −0.0110 (9) | 0.0137 (8) | −0.0082 (9) |
O5 | 0.0410 (10) | 0.0585 (12) | 0.0484 (10) | −0.0161 (9) | 0.0124 (8) | −0.0099 (9) |
O6 | 0.0466 (11) | 0.0613 (12) | 0.0582 (12) | −0.0006 (9) | 0.0267 (10) | −0.0037 (9) |
O7 | 0.0476 (10) | 0.0535 (11) | 0.0412 (10) | −0.0093 (9) | 0.0116 (8) | −0.0143 (8) |
O8 | 0.0540 (11) | 0.0684 (13) | 0.0404 (10) | −0.0087 (10) | 0.0226 (9) | −0.0029 (9) |
N1 | 0.0326 (10) | 0.0403 (11) | 0.0333 (10) | −0.0009 (9) | 0.0090 (8) | −0.0046 (9) |
N2 | 0.0312 (10) | 0.0445 (12) | 0.0331 (11) | 0.0002 (9) | 0.0089 (8) | −0.0043 (9) |
C1 | 0.0435 (15) | 0.0407 (14) | 0.0305 (13) | 0.0049 (12) | 0.0097 (11) | 0.0073 (11) |
C2 | 0.0393 (14) | 0.0429 (15) | 0.0423 (14) | −0.0064 (12) | 0.0119 (12) | −0.0066 (12) |
C3 | 0.0376 (14) | 0.0411 (15) | 0.0428 (14) | −0.0049 (12) | 0.0123 (12) | −0.0083 (12) |
C4 | 0.0324 (13) | 0.0388 (14) | 0.0489 (15) | 0.0050 (12) | 0.0128 (12) | 0.0032 (12) |
C5 | 0.0342 (13) | 0.0390 (14) | 0.0461 (15) | 0.0045 (12) | 0.0105 (12) | 0.0030 (13) |
C6 | 0.0461 (16) | 0.0458 (15) | 0.0386 (14) | −0.0078 (13) | 0.0124 (12) | −0.0108 (12) |
C7 | 0.0433 (15) | 0.0454 (15) | 0.0420 (14) | −0.0150 (13) | 0.0117 (12) | −0.0097 (12) |
C8 | 0.0390 (14) | 0.0423 (14) | 0.0326 (13) | −0.0008 (13) | 0.0070 (11) | 0.0014 (11) |
C9 | 0.0437 (15) | 0.0336 (13) | 0.0477 (15) | −0.0041 (12) | 0.0123 (12) | −0.0005 (12) |
C10 | 0.0393 (14) | 0.0403 (14) | 0.0399 (14) | −0.0005 (12) | 0.0136 (11) | 0.0066 (11) |
C11 | 0.0414 (15) | 0.0366 (14) | 0.0425 (14) | −0.0064 (12) | 0.0073 (12) | −0.0013 (12) |
C12 | 0.0423 (14) | 0.0381 (14) | 0.0370 (13) | −0.0021 (11) | 0.0123 (11) | 0.0046 (11) |
O2—H1' | 1.21 | C1—C2 | 1.486 (3) |
O7—H2' | 1.19 | C2—C3 | 1.334 (3) |
O4—H1' | 1.22 | C2—H2 | 0.9300 |
O5—H2' | 1.23 | C3—C4 | 1.489 (3) |
O1—C1 | 1.232 (3) | C3—H3 | 0.9300 |
O3—C4 | 1.226 (3) | C5—C6 | 1.479 (3) |
O6—C5 | 1.230 (3) | C6—C7 | 1.330 (3) |
O8—C8 | 1.230 (3) | C6—H6 | 0.9300 |
O2—C1 | 1.281 (3) | C7—C8 | 1.484 (3) |
O4—C4 | 1.281 (3) | C7—H7 | 0.9300 |
O5—C5 | 1.285 (3) | C9—C10 | 1.506 (3) |
O7—C8 | 1.279 (3) | C9—H9A | 0.9700 |
N1—C9 | 1.484 (3) | C9—H9B | 0.9700 |
N1—C12 | 1.486 (3) | C10—H10A | 0.9700 |
N1—H1A | 0.92 | C10—H10B | 0.9700 |
N1—H1B | 0.98 | C11—C12 | 1.516 (3) |
N2—C11 | 1.483 (3) | C11—H11A | 0.9700 |
N2—C10 | 1.485 (3) | C11—H11B | 0.9700 |
N2—H2B | 1.04 | C12—H12A | 0.9700 |
N2—H2A | 0.96 | C12—H12B | 0.9700 |
C1—O2—H1' | 113.50 | C3—C2—H2 | 114.9 |
C4—O4—H1' | 113.59 | C1—C2—H2 | 114.9 |
C5—O5—H2' | 113.57 | C2—C3—H3 | 114.8 |
C8—O7—H2' | 113.86 | C4—C3—H3 | 114.8 |
C9—N1—C12 | 111.42 (17) | C7—C6—H6 | 114.6 |
C9—N1—H1A | 112.53 | C5—C6—H6 | 114.6 |
C12—N1—H1A | 110.90 | C6—C7—H7 | 114.6 |
C9—N1—H1B | 106.44 | C8—C7—H7 | 114.6 |
C12—N1—H1B | 108.77 | N1—C9—C10 | 110.69 (18) |
H1A—N1—H1B | 106.50 | N1—C9—H9A | 109.5 |
C11—N2—C10 | 111.49 (17) | C10—C9—H9A | 109.5 |
C11—N2—H2B | 107.06 | N1—C9—H9B | 109.5 |
C10—N2—H2B | 104.83 | C10—C9—H9B | 109.5 |
C11—N2—H2A | 113.98 | H9A—C9—H9B | 108.1 |
C10—N2—H2A | 108.00 | N2—C10—C9 | 110.64 (18) |
H2B—N2—H2A | 111.11 | N2—C10—H10A | 109.5 |
O1—C1—O2 | 122.0 (2) | C9—C10—H10A | 109.5 |
O1—C1—C2 | 118.0 (2) | N2—C10—H10B | 109.5 |
O2—C1—C2 | 119.9 (2) | C9—C10—H10B | 109.5 |
O8—C8—O7 | 122.6 (2) | H10A—C10—H10B | 108.1 |
O8—C8—C7 | 117.8 (2) | N2—C11—C12 | 110.90 (18) |
O7—C8—C7 | 119.7 (2) | N2—C11—H11A | 109.5 |
O3—C4—O4 | 122.5 (2) | C12—C11—H11A | 109.5 |
O3—C4—C3 | 117.6 (2) | N2—C11—H11B | 109.5 |
O4—C4—C3 | 119.8 (2) | C12—C11—H11B | 109.5 |
O6—C5—O5 | 122.4 (2) | H11A—C11—H11B | 108.0 |
O6—C5—C6 | 117.9 (2) | N1—C12—C11 | 110.00 (18) |
O5—C5—C6 | 119.6 (2) | N1—C12—H12A | 109.7 |
C3—C2—C1 | 130.2 (2) | C11—C12—H12A | 109.7 |
C6—C7—C8 | 130.8 (2) | N1—C12—H12B | 109.7 |
C2—C3—C4 | 130.5 (2) | C11—C12—H12B | 109.7 |
C7—C6—C5 | 130.9 (2) | H12A—C12—H12B | 108.2 |
O1—C1—C2—C3 | −170.5 (2) | C6—C7—C8—O8 | 176.5 (3) |
O2—C1—C2—C3 | 10.7 (4) | C6—C7—C8—O7 | −4.5 (4) |
C1—C2—C3—C4 | −0.1 (4) | C12—N1—C9—C10 | −57.2 (2) |
C2—C3—C4—O3 | 171.6 (3) | C11—N2—C10—C9 | −56.1 (2) |
C2—C3—C4—O4 | −9.1 (4) | N1—C9—C10—N2 | 56.1 (2) |
O6—C5—C6—C7 | −174.2 (3) | C10—N2—C11—C12 | 56.3 (2) |
O5—C5—C6—C7 | 5.8 (4) | C9—N1—C12—C11 | 56.8 (2) |
C5—C6—C7—C8 | −0.5 (5) | N2—C11—C12—N1 | −56.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1′···O4 | 1.21 | 1.22 | 2.419 (2) | 171 |
O7—H2′···O5 | 1.19 | 1.23 | 2.420 (2) | 171 |
N1—H1B···O1 | 0.98 | 1.90 | 2.842 (2) | 161 |
N2—H2B···O8 | 1.04 | 1.73 | 2.757 (2) | 169 |
N1—H1A···O3i | 0.92 | 1.94 | 2.813 (3) | 157 |
N2—H2A···O6ii | 0.96 | 1.84 | 2.770 (3) | 162 |
C10—H10B···O4i | 0.97 | 2.46 | 3.356 (3) | 153 |
C12—H12A···O5ii | 0.97 | 2.50 | 3.357 (3) | 148 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2. |
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