Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002910/ob6349sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002910/ob6349Isup2.hkl |
CCDC reference: 236070
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.059
- wR factor = 0.187
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C6 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N12 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.67
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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: SMART-W2K/NT (Bruker, 2003); cell refinement: SMART-W2K/NT; data reduction: SAINT-W2K/NT (Bruker, 2003); program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.
2C8H20N+·C12H6N2O42−·4H2O | F(000) = 628 |
Mr = 574.76 | Dx = 1.161 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3258 reflections |
a = 10.740 (2) Å | θ = 2.7–26.1° |
b = 7.5172 (15) Å | µ = 0.08 mm−1 |
c = 20.398 (4) Å | T = 297 K |
β = 93.40 (3)° | Needle, colourless |
V = 1643.9 (6) Å3 | 0.51 × 0.22 × 0.21 mm |
Z = 2 |
Bruker SMART APEX CCD area-detector diffractometer | 3924 independent reflections |
Radiation source: fine-focus sealed tube | 2868 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.366 pixels mm-1 | θmax = 28.0°, θmin = 1.9° |
φ and ω scans | h = −14→12 |
Absorption correction: empirical (using intensity measurements) (SADABS; Scheldrick, 1996) | k = −9→9 |
Tmin = 0.976, Tmax = 0.982 | l = −26→24 |
11634 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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1096P)2 + 0.1896P] where P = (Fo2 + 2Fc2)/3 |
3924 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. none |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) $1 1 - x, -0.5 + y, 0.5 - z - 7.1037 (0.0047) x - 0.8070 (0.0050) y - 14.2732 (0.0086) z = 0.0431 (0.0100) * 0.0046 (0.0011) N1_$1 * -0.0056 (0.0010) C1_$1 * 0.0023 (0.0010) C2_$1 * 0.0019 (0.0011) C3_$1 * -0.0029 (0.0012) C4_$1 * -0.0003 (0.0012) C5_$1 Rms deviation of fitted atoms = 0.0034 7.1037 (0.0047) x - 0.8070 (0.0051) y + 14.2732 (0.0087) z = 13.8799 (0.0106) Angle to previous plane (with approximate e.s.d.) = 12.3 (0.1) * 0.0046 (0.0011) N1 * -0.0056 (0.0010) C1 * 0.0023 (0.0010) C2 * 0.0019 (0.0011) C3 * -0.0029 (0.0012) C4 * -0.0003 (0.0012) C5 Rms deviation of fitted atoms = 0.0034 6.4731 (0.0233) x + 0.0356 (0.0220) y + 15.4856 (0.0365) z = 15.6782 (0.0439) Angle to previous plane (with approximate e.s.d.) = 7.9 (0.3) * 0.0000 (0.0000) O1 * 0.0000 (0.0000) C6 * 0.0000 (0.0000) O2 Rms deviation of fitted atoms = 0.0000 |
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 | 0.94168 (12) | 0.69262 (17) | 0.04085 (7) | 0.0468 (3) | |
C1 | 0.95390 (12) | 0.52034 (18) | 0.02458 (7) | 0.0361 (3) | |
C2 | 0.88453 (12) | 0.38600 (18) | 0.05172 (7) | 0.0367 (3) | |
C3 | 0.79853 (13) | 0.42740 (19) | 0.09693 (7) | 0.0388 (3) | |
C4 | 0.78513 (15) | 0.6057 (2) | 0.11323 (8) | 0.0472 (4) | |
C5 | 0.85781 (15) | 0.7313 (2) | 0.08447 (9) | 0.0513 (4) | |
C6 | 0.72243 (15) | 0.2816 (2) | 0.12765 (8) | 0.0463 (4) | |
O1 | 0.75180 (16) | 0.12661 (16) | 0.11620 (9) | 0.0865 (6) | |
O2 | 0.63897 (13) | 0.32739 (17) | 0.16271 (8) | 0.0709 (4) | |
H2 | 0.8961 | 0.2683 | 0.0394 | 0.044* | |
H4 | 0.7277 | 0.6399 | 0.1432 | 0.057* | |
H5 | 0.8479 | 0.8499 | 0.0961 | 0.062* | |
N12 | 0.24920 (13) | 0.0412 (2) | 0.12718 (7) | 0.0550 (4) | |
C11 | 0.27263 (19) | −0.0851 (3) | 0.18496 (10) | 0.0672 (5) | |
C12 | 0.1844 (3) | −0.2391 (4) | 0.18647 (14) | 0.0965 (8) | |
C13 | 0.3465 (2) | 0.1874 (3) | 0.13466 (11) | 0.0726 (6) | |
C14 | 0.3427 (3) | 0.3201 (3) | 0.07911 (15) | 0.0985 (9) | |
C15 | 0.1185 (2) | 0.1180 (4) | 0.12676 (13) | 0.0854 (7) | |
C16 | 0.0893 (3) | 0.2131 (5) | 0.18866 (18) | 0.1219 (12) | |
C17 | 0.2574 (2) | −0.0569 (3) | 0.06324 (10) | 0.0781 (6) | |
C18 | 0.3837 (3) | −0.1429 (4) | 0.05483 (14) | 0.1043 (9) | |
H11A | 0.3569 | −0.1309 | 0.1840 | 0.081* | |
H11B | 0.2676 | −0.0179 | 0.2253 | 0.081* | |
H12A | 0.1008 | −0.1957 | 0.1889 | 0.145* | |
H12B | 0.2060 | −0.3117 | 0.2242 | 0.145* | |
H12C | 0.1900 | −0.3087 | 0.1473 | 0.145* | |
H13A | 0.3351 | 0.2506 | 0.1753 | 0.087* | |
H13B | 0.4285 | 0.1330 | 0.1383 | 0.087* | |
H14A | 0.3528 | 0.2590 | 0.0384 | 0.148* | |
H14B | 0.4090 | 0.4048 | 0.0865 | 0.148* | |
H14C | 0.2640 | 0.3811 | 0.0770 | 0.148* | |
H15A | 0.1074 | 0.2004 | 0.0903 | 0.103* | |
H15B | 0.0590 | 0.0222 | 0.1192 | 0.103* | |
H16A | 0.0972 | 0.1319 | 0.2250 | 0.183* | |
H16B | 0.0055 | 0.2581 | 0.1844 | 0.183* | |
H16C | 0.1464 | 0.3102 | 0.1962 | 0.183* | |
H17A | 0.2398 | 0.0256 | 0.0273 | 0.094* | |
H17B | 0.1937 | −0.1485 | 0.0604 | 0.094* | |
H18A | 0.4477 | −0.0538 | 0.0586 | 0.156* | |
H18B | 0.3838 | −0.1979 | 0.0124 | 0.156* | |
H18C | 0.3992 | −0.2314 | 0.0883 | 0.156* | |
O3 | 0.49461 (12) | 0.59825 (19) | 0.19880 (7) | 0.0611 (4) | |
O4 | 0.63296 (15) | −0.08433 (18) | 0.20773 (8) | 0.0731 (5) | |
H3A | 0.549 (2) | 0.521 (3) | 0.1853 (10) | 0.071 (6)* | |
H3B | 0.544 (2) | 0.689 (3) | 0.2054 (12) | 0.081 (7)* | |
H4B | 0.5915 (18) | −0.010 (3) | 0.2341 (10) | 0.062 (6)* | |
H4A | 0.664 (2) | −0.016 (4) | 0.1802 (14) | 0.103 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0523 (7) | 0.0331 (6) | 0.0574 (8) | 0.0015 (5) | 0.0220 (6) | −0.0037 (5) |
C1 | 0.0371 (7) | 0.0326 (7) | 0.0391 (7) | 0.0046 (5) | 0.0076 (5) | −0.0007 (5) |
C2 | 0.0395 (7) | 0.0297 (6) | 0.0416 (7) | 0.0041 (5) | 0.0086 (5) | −0.0019 (5) |
C3 | 0.0407 (7) | 0.0345 (7) | 0.0420 (7) | 0.0033 (5) | 0.0096 (6) | −0.0006 (5) |
C4 | 0.0507 (8) | 0.0382 (8) | 0.0550 (9) | 0.0039 (6) | 0.0239 (7) | −0.0052 (6) |
C5 | 0.0577 (9) | 0.0314 (7) | 0.0675 (10) | 0.0015 (6) | 0.0267 (8) | −0.0085 (7) |
C6 | 0.0534 (9) | 0.0362 (7) | 0.0515 (9) | 0.0012 (6) | 0.0205 (7) | −0.0003 (6) |
O1 | 0.1164 (12) | 0.0333 (6) | 0.1183 (13) | 0.0030 (7) | 0.0784 (11) | 0.0021 (7) |
O2 | 0.0746 (8) | 0.0443 (7) | 0.0995 (11) | 0.0019 (6) | 0.0532 (8) | 0.0017 (6) |
N12 | 0.0548 (8) | 0.0544 (8) | 0.0541 (8) | 0.0000 (6) | −0.0123 (6) | 0.0034 (6) |
C11 | 0.0634 (11) | 0.0777 (13) | 0.0597 (11) | 0.0094 (10) | −0.0041 (9) | 0.0129 (10) |
C12 | 0.0973 (18) | 0.0944 (18) | 0.0967 (18) | −0.0118 (15) | −0.0031 (15) | 0.0356 (15) |
C13 | 0.0746 (12) | 0.0651 (12) | 0.0758 (13) | −0.0097 (10) | −0.0167 (10) | −0.0053 (10) |
C14 | 0.112 (2) | 0.0681 (15) | 0.112 (2) | −0.0314 (14) | −0.0241 (16) | 0.0173 (13) |
C15 | 0.0605 (12) | 0.1001 (18) | 0.0936 (17) | 0.0126 (11) | −0.0130 (11) | 0.0243 (14) |
C16 | 0.095 (2) | 0.147 (3) | 0.124 (2) | 0.060 (2) | 0.0126 (17) | 0.002 (2) |
C17 | 0.1071 (17) | 0.0697 (13) | 0.0558 (11) | −0.0170 (13) | −0.0098 (11) | −0.0016 (9) |
C18 | 0.145 (3) | 0.0911 (18) | 0.0790 (16) | 0.0155 (18) | 0.0279 (16) | −0.0129 (14) |
O3 | 0.0553 (7) | 0.0499 (7) | 0.0802 (9) | 0.0044 (6) | 0.0229 (6) | −0.0017 (6) |
O4 | 0.0943 (11) | 0.0396 (7) | 0.0899 (11) | −0.0045 (7) | 0.0437 (9) | 0.0013 (7) |
C1—N1 | 1.3452 (19) | C13—H13B | 0.9700 |
C1—C2 | 1.389 (2) | C14—H14A | 0.9600 |
C1—C1i | 1.482 (3) | C14—H14B | 0.9600 |
C2—C3 | 1.3788 (19) | C14—H14C | 0.9600 |
C2—H2 | 0.9300 | C15—C16 | 1.500 (4) |
C3—C4 | 1.391 (2) | C15—N12 | 1.517 (3) |
C3—C6 | 1.524 (2) | C15—H15A | 0.9700 |
C4—C5 | 1.378 (2) | C15—H15B | 0.9700 |
C4—H4 | 0.9300 | C16—H16A | 0.9600 |
C5—N1 | 1.3353 (19) | C16—H16B | 0.9600 |
C5—H5 | 0.9300 | C16—H16C | 0.9600 |
C6—O2 | 1.2286 (19) | C17—N12 | 1.506 (3) |
C6—O1 | 1.2331 (19) | C17—C18 | 1.521 (4) |
C11—C12 | 1.498 (3) | C17—H17A | 0.9700 |
C11—N12 | 1.523 (2) | C17—H17B | 0.9700 |
C11—H11A | 0.9700 | C18—H18A | 0.9600 |
C11—H11B | 0.9700 | C18—H18B | 0.9600 |
C12—H12A | 0.9600 | C18—H18C | 0.9600 |
C12—H12B | 0.9600 | O3—H3A | 0.88 (2) |
C12—H12C | 0.9600 | O3—H3B | 0.87 (3) |
C13—C14 | 1.509 (3) | O4—H4B | 0.91 (2) |
C13—N12 | 1.518 (3) | O4—H4A | 0.84 (3) |
C13—H13A | 0.9700 | ||
N1—C1—C2 | 122.62 (12) | C16—C15—N12 | 114.6 (2) |
N1—C1—C1i | 116.37 (15) | C16—C15—H15A | 108.6 |
N1—C5—C4 | 123.79 (14) | C17—C18—H18A | 109.5 |
N1—C5—H5 | 118.1 | C17—C18—H18B | 109.5 |
C1—C2—H2 | 120.0 | C17—C18—H18C | 109.5 |
C2—C1—C1i | 121.01 (15) | C17—N12—C15 | 106.45 (17) |
C2—C3—C4 | 117.41 (13) | C17—N12—C13 | 111.49 (17) |
C2—C3—C6 | 120.63 (13) | C17—N12—C11 | 110.46 (16) |
C3—C2—C1 | 119.92 (13) | C18—C17—H17A | 108.8 |
C3—C2—H2 | 120.0 | C18—C17—H17B | 108.8 |
C3—C4—H4 | 120.4 | N12—C11—H11A | 108.5 |
C4—C3—C6 | 121.95 (13) | N12—C11—H11B | 108.5 |
C4—C5—H5 | 118.1 | N12—C13—H13A | 108.6 |
C5—C4—C3 | 119.29 (13) | N12—C13—H13B | 108.6 |
C5—C4—H4 | 120.4 | N12—C17—C18 | 113.84 (19) |
C5—N1—C1 | 116.97 (13) | N12—C17—H17A | 108.8 |
O1—C6—C3 | 116.89 (13) | N12—C17—H17B | 108.8 |
O2—C6—O1 | 125.35 (15) | N12—C15—H15A | 108.6 |
O2—C6—C3 | 117.75 (13) | N12—C15—H15B | 108.6 |
C11—C12—H12A | 109.5 | H11A—C11—H11B | 107.5 |
C11—C12—H12B | 109.5 | H12A—C12—H12B | 109.5 |
C11—C12—H12C | 109.5 | H12A—C12—H12C | 109.5 |
C12—C11—N12 | 114.98 (17) | H12B—C12—H12C | 109.5 |
C12—C11—H11A | 108.5 | H13A—C13—H13B | 107.6 |
C12—C11—H11B | 108.5 | H14A—C14—H14B | 109.5 |
C13—C14—H14A | 109.5 | H14A—C14—H14C | 109.5 |
C13—C14—H14B | 109.5 | H14B—C14—H14C | 109.5 |
C13—C14—H14C | 109.5 | H15A—C15—H15B | 107.6 |
C13—N12—C11 | 107.00 (14) | H16A—C16—H16B | 109.5 |
C14—C13—N12 | 114.56 (18) | H16A—C16—H16C | 109.5 |
C14—C13—H13A | 108.6 | H16B—C16—H16C | 109.5 |
C14—C13—H13B | 108.6 | H17A—C17—H17B | 107.7 |
C15—C16—H16A | 109.5 | H18A—C18—H18B | 109.5 |
C15—C16—H16B | 109.5 | H18A—C18—H18C | 109.5 |
C15—C16—H16C | 109.5 | H18B—C18—H18C | 109.5 |
C15—N12—C13 | 110.86 (17) | H4B—O4—H4A | 105 (2) |
C15—N12—C11 | 110.62 (16) | H3A—O3—H3B | 99 (2) |
C16—C15—H15B | 108.6 | ||
N1—C1—C2—C3 | 0.4 (2) | C6—C3—C4—C5 | 179.11 (16) |
C1i—C1—C2—C3 | −179.42 (15) | C18—C17—N12—C15 | 179.7 (2) |
C1—C2—C3—C4 | 0.2 (2) | C18—C17—N12—C13 | 58.7 (3) |
C1—C2—C3—C6 | −179.46 (13) | C18—C17—N12—C11 | −60.1 (2) |
C1i—C1—N1—C5 | 179.18 (15) | C16—C15—N12—C17 | 176.7 (2) |
C2—C3—C4—C5 | −0.5 (2) | C16—C15—N12—C13 | −61.9 (3) |
C2—C3—C6—O2 | −173.14 (16) | C16—C15—N12—C11 | 56.7 (3) |
C2—C3—C6—O1 | 8.3 (2) | C14—C13—N12—C17 | 55.6 (3) |
C2—C1—N1—C5 | −0.7 (2) | C14—C13—N12—C15 | −62.9 (3) |
C3—C4—C5—N1 | 0.3 (3) | C14—C13—N12—C11 | 176.4 (2) |
C4—C3—C6—O2 | 7.2 (2) | C12—C11—N12—C17 | −58.9 (2) |
C4—C3—C6—O1 | −171.33 (18) | C12—C11—N12—C15 | 58.7 (3) |
C4—C5—N1—C1 | 0.3 (3) | C12—C11—N12—C13 | 179.6 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O1 | 0.84 (3) | 1.97 (3) | 2.813 (2) | 174 (3) |
O3—H3A···O2 | 0.88 (2) | 1.82 (2) | 2.688 (2) | 168 (2) |
O3—H3B···O4ii | 0.87 (3) | 1.95 (3) | 2.811 (2) | 169 (2) |
O4—H4B···O3iii | 0.91 (2) | 1.88 (2) | 2.776 (2) | 167 (2) |
Symmetry codes: (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+1/2. |
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