Phosphonopropionic acid as a building block in supramolecular chemistry: salts with organic diamines
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102021237/bm0061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768102021237/bm0061VIIsup8.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102021237/bm0061sup9.pdf |
CCDC references: 210873; 210874; 210875; 210876; 210877; 210878; 210879
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).
C12H12N22+·C12H10N2·2(C3H6O5P)− | F(000) = 704 |
Mr = 672.55 | Dx = 1.461 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3496 reflections |
a = 10.1600 (3) Å | θ = 2.8–27.5° |
b = 10.4061 (3) Å | µ = 0.21 mm−1 |
c = 14.5441 (5) Å | T = 150 K |
β = 96.2880 (12)° | Block, colourless |
V = 1528.44 (8) Å3 | 0.22 × 0.16 × 0.14 mm |
Z = 2 |
Kappa-CCD diffractometer | 2880 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.042 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
ϕ scans, and ω scans with κ offsets | h = −13→13 |
13452 measured reflections | k = −13→13 |
3496 independent reflections | l = −18→18 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.6401P] where P = (Fo2 + 2Fc2)/3 |
3496 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C12H12N22+·C12H10N2·2(C3H6O5P)− | V = 1528.44 (8) Å3 |
Mr = 672.55 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.1600 (3) Å | µ = 0.21 mm−1 |
b = 10.4061 (3) Å | T = 150 K |
c = 14.5441 (5) Å | 0.22 × 0.16 × 0.14 mm |
β = 96.2880 (12)° |
Kappa-CCD diffractometer | 2880 reflections with I > 2σ(I) |
13452 measured reflections | Rint = 0.042 |
3496 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
3496 reflections | Δρmin = −0.42 e Å−3 |
210 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | −0.12432 (12) | 0.46207 (14) | 0.21704 (9) | 0.0255 (3) | |
C12 | −0.18883 (15) | 0.36667 (16) | 0.16967 (11) | 0.0250 (3) | |
C13 | −0.29918 (15) | 0.38614 (16) | 0.10699 (11) | 0.0231 (3) | |
C14 | −0.34753 (14) | 0.51103 (15) | 0.09126 (10) | 0.0212 (3) | |
C15 | −0.27925 (16) | 0.60983 (16) | 0.14024 (12) | 0.0274 (4) | |
C16 | −0.16981 (16) | 0.58185 (17) | 0.20161 (12) | 0.0288 (4) | |
C17 | −0.46417 (14) | 0.54284 (15) | 0.02611 (11) | 0.0221 (3) | |
N21 | 0.62522 (12) | 0.59514 (13) | 0.79666 (9) | 0.0216 (3) | |
C22 | 0.70080 (14) | 0.68140 (16) | 0.84635 (11) | 0.0236 (3) | |
C23 | 0.81286 (15) | 0.64407 (15) | 0.90215 (11) | 0.0238 (3) | |
C24 | 0.84758 (14) | 0.51395 (15) | 0.90851 (10) | 0.0197 (3) | |
C25 | 0.76696 (15) | 0.42735 (15) | 0.85448 (11) | 0.0222 (3) | |
C26 | 0.65671 (15) | 0.47024 (15) | 0.79968 (11) | 0.0231 (3) | |
C27 | 0.96084 (14) | 0.46486 (15) | 0.97001 (11) | 0.0220 (3) | |
P1 | 0.40649 (3) | 0.59435 (4) | 0.59827 (3) | 0.01825 (12) | |
O1 | 0.07888 (11) | 0.42023 (12) | 0.34015 (9) | 0.0319 (3) | |
O2 | 0.02148 (11) | 0.60505 (11) | 0.40398 (9) | 0.0290 (3) | |
O3 | 0.45265 (10) | 0.45215 (10) | 0.61687 (8) | 0.0222 (2) | |
O4 | 0.41924 (10) | 0.66590 (11) | 0.68904 (7) | 0.0239 (3) | |
O5 | 0.48314 (10) | 0.65546 (10) | 0.52532 (8) | 0.0224 (2) | |
C1 | 0.09583 (14) | 0.51387 (16) | 0.40157 (11) | 0.0219 (3) | |
C2 | 0.22088 (15) | 0.49638 (17) | 0.46571 (12) | 0.0266 (4) | |
C3 | 0.23605 (14) | 0.58554 (16) | 0.54947 (11) | 0.0234 (3) | |
H12 | −0.1571 | 0.2814 | 0.1797 | 0.030* | |
H13 | −0.3419 | 0.3155 | 0.0749 | 0.028* | |
H15 | −0.3080 | 0.6963 | 0.1314 | 0.033* | |
H16 | −0.1246 | 0.6506 | 0.2344 | 0.035* | |
H17 | −0.4903 | 0.6304 | 0.0209 | 0.026* | |
H21 | 0.5540 | 0.6209 | 0.7616 | 0.026* | |
H22 | 0.6768 | 0.7697 | 0.8431 | 0.028* | |
H23 | 0.8663 | 0.7065 | 0.9362 | 0.029* | |
H25 | 0.7885 | 0.3385 | 0.8556 | 0.027* | |
H26 | 0.6024 | 0.4105 | 0.7636 | 0.028* | |
H27 | 0.9798 | 0.3757 | 0.9667 | 0.026* | |
H1 | 0.0138 | 0.4373 | 0.3013 | 0.048* | |
H3 | 0.4723 | 0.4191 | 0.5675 | 0.033* | |
H2A | 0.2974 | 0.5097 | 0.4301 | 0.032* | |
H2B | 0.2245 | 0.4064 | 0.4880 | 0.032* | |
H3A | 0.1812 | 0.5533 | 0.5968 | 0.028* | |
H3B | 0.2042 | 0.6725 | 0.5306 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0214 (6) | 0.0348 (8) | 0.0191 (7) | 0.0030 (6) | −0.0034 (5) | −0.0041 (6) |
C12 | 0.0239 (7) | 0.0282 (8) | 0.0218 (8) | 0.0040 (6) | −0.0016 (6) | −0.0003 (7) |
C13 | 0.0224 (7) | 0.0255 (8) | 0.0204 (8) | −0.0001 (6) | −0.0022 (6) | −0.0031 (6) |
C14 | 0.0188 (7) | 0.0274 (8) | 0.0171 (7) | 0.0015 (6) | −0.0004 (6) | −0.0021 (6) |
C15 | 0.0279 (8) | 0.0262 (8) | 0.0266 (9) | 0.0038 (7) | −0.0037 (7) | −0.0046 (7) |
C16 | 0.0271 (8) | 0.0316 (9) | 0.0259 (9) | 0.0002 (7) | −0.0059 (7) | −0.0088 (7) |
C17 | 0.0221 (7) | 0.0225 (7) | 0.0210 (8) | 0.0042 (6) | −0.0006 (6) | −0.0010 (6) |
N21 | 0.0179 (6) | 0.0267 (7) | 0.0188 (7) | 0.0017 (5) | −0.0042 (5) | 0.0022 (5) |
C22 | 0.0240 (7) | 0.0224 (8) | 0.0233 (8) | 0.0018 (6) | −0.0023 (6) | 0.0016 (6) |
C23 | 0.0228 (7) | 0.0215 (8) | 0.0256 (8) | −0.0015 (6) | −0.0042 (6) | −0.0012 (6) |
C24 | 0.0178 (7) | 0.0230 (8) | 0.0177 (7) | −0.0003 (6) | −0.0004 (6) | 0.0022 (6) |
C25 | 0.0231 (7) | 0.0208 (7) | 0.0217 (8) | 0.0000 (6) | −0.0019 (6) | 0.0008 (6) |
C26 | 0.0216 (7) | 0.0247 (8) | 0.0217 (8) | −0.0025 (6) | −0.0033 (6) | −0.0004 (6) |
C27 | 0.0193 (7) | 0.0221 (8) | 0.0237 (8) | 0.0013 (6) | −0.0023 (6) | 0.0031 (6) |
P1 | 0.01556 (19) | 0.0199 (2) | 0.0182 (2) | 0.00056 (14) | −0.00320 (14) | −0.00039 (15) |
O1 | 0.0255 (6) | 0.0379 (7) | 0.0290 (7) | 0.0072 (5) | −0.0121 (5) | −0.0113 (5) |
O2 | 0.0243 (6) | 0.0278 (6) | 0.0325 (7) | 0.0043 (5) | −0.0074 (5) | −0.0016 (5) |
O3 | 0.0259 (5) | 0.0200 (5) | 0.0200 (6) | 0.0015 (4) | −0.0009 (4) | 0.0010 (4) |
O4 | 0.0213 (5) | 0.0279 (6) | 0.0208 (6) | 0.0043 (4) | −0.0056 (4) | −0.0048 (5) |
O5 | 0.0221 (5) | 0.0191 (5) | 0.0260 (6) | −0.0009 (4) | 0.0020 (4) | 0.0007 (4) |
C1 | 0.0178 (7) | 0.0260 (8) | 0.0214 (8) | −0.0026 (6) | −0.0011 (6) | 0.0018 (6) |
C2 | 0.0197 (7) | 0.0308 (9) | 0.0272 (9) | 0.0026 (6) | −0.0069 (6) | −0.0054 (7) |
C3 | 0.0167 (7) | 0.0306 (8) | 0.0219 (8) | 0.0012 (6) | −0.0026 (6) | −0.0028 (7) |
N11—C12 | 1.338 (2) | C24—C27 | 1.470 (2) |
N11—C16 | 1.340 (2) | C25—C26 | 1.376 (2) |
C12—C13 | 1.380 (2) | C25—H25 | 0.95 |
C12—H12 | 0.95 | C26—H26 | 0.95 |
C13—C14 | 1.399 (2) | C27—C27ii | 1.333 (3) |
C13—H13 | 0.95 | C27—H27 | 0.95 |
C14—C15 | 1.392 (2) | P1—O4 | 1.5088 (11) |
C14—C17 | 1.472 (2) | P1—O5 | 1.5223 (11) |
C15—C16 | 1.379 (2) | P1—O3 | 1.5668 (11) |
C15—H15 | 0.95 | P1—C3 | 1.8005 (15) |
C16—H16 | 0.95 | O1—C1 | 1.320 (2) |
C17—C17i | 1.335 (3) | O1—H1 | 0.84 |
C17—H17 | 0.95 | O2—C1 | 1.2157 (19) |
N21—C26 | 1.338 (2) | O3—H3 | 0.84 |
N21—C22 | 1.340 (2) | C1—C2 | 1.503 (2) |
N21—H21 | 0.88 | C2—C3 | 1.526 (2) |
C22—C23 | 1.380 (2) | C2—H2A | 0.99 |
C22—H22 | 0.95 | C2—H2B | 0.99 |
C23—C24 | 1.400 (2) | C3—H3A | 0.99 |
C23—H23 | 0.95 | C3—H3B | 0.99 |
C24—C25 | 1.400 (2) | ||
C12—N11—C16 | 117.61 (14) | C26—C25—H25 | 119.8 |
N11—C12—C13 | 123.21 (15) | C24—C25—H25 | 119.8 |
N11—C12—H12 | 118.4 | N21—C26—C25 | 120.70 (14) |
C13—C12—H12 | 118.4 | N21—C26—H26 | 119.7 |
C12—C13—C14 | 119.31 (15) | C25—C26—H26 | 119.7 |
C12—C13—H13 | 120.3 | C27ii—C27—C24 | 125.38 (19) |
C14—C13—H13 | 120.3 | C27ii—C27—H27 | 117.3 |
C15—C14—C13 | 117.13 (14) | C24—C27—H27 | 117.3 |
C15—C14—C17 | 118.97 (14) | O4—P1—O5 | 113.72 (7) |
C13—C14—C17 | 123.90 (14) | O4—P1—O3 | 108.64 (6) |
C16—C15—C14 | 119.79 (15) | O5—P1—O3 | 110.40 (6) |
C16—C15—H15 | 120.1 | O4—P1—C3 | 110.89 (7) |
C14—C15—H15 | 120.1 | O5—P1—C3 | 106.85 (7) |
N11—C16—C15 | 122.95 (15) | O3—P1—C3 | 106.07 (7) |
N11—C16—H16 | 118.5 | C1—O1—H1 | 109.5 |
C15—C16—H16 | 118.5 | P1—O3—H3 | 109.5 |
C17i—C17—C14 | 124.53 (19) | O2—C1—O1 | 124.06 (14) |
C17i—C17—H17 | 117.7 | O2—C1—C2 | 124.23 (15) |
C14—C17—H17 | 117.7 | O1—C1—C2 | 111.67 (13) |
C26—N21—C22 | 120.80 (13) | C1—C2—C3 | 115.26 (13) |
C26—N21—H21 | 119.6 | C1—C2—H2A | 108.5 |
C22—N21—H21 | 119.6 | C3—C2—H2A | 108.5 |
N21—C22—C23 | 121.05 (15) | C1—C2—H2B | 108.5 |
N21—C22—H22 | 119.5 | C3—C2—H2B | 108.5 |
C23—C22—H22 | 119.5 | H2A—C2—H2B | 107.5 |
C22—C23—C24 | 119.81 (14) | C2—C3—P1 | 110.76 (10) |
C22—C23—H23 | 120.1 | C2—C3—H3A | 109.5 |
C24—C23—H23 | 120.1 | P1—C3—H3A | 109.5 |
C23—C24—C25 | 117.25 (13) | C2—C3—H3B | 109.5 |
C23—C24—C27 | 123.46 (14) | P1—C3—H3B | 109.5 |
C25—C24—C27 | 119.27 (14) | H3A—C3—H3B | 108.1 |
C26—C25—C24 | 120.37 (14) | ||
C16—N11—C12—C13 | −0.5 (2) | C22—C23—C24—C27 | −176.52 (15) |
N11—C12—C13—C14 | 0.0 (2) | C23—C24—C25—C26 | −1.6 (2) |
C12—C13—C14—C15 | 0.5 (2) | C27—C24—C25—C26 | 176.90 (14) |
C12—C13—C14—C17 | 179.99 (15) | C22—N21—C26—C25 | 0.5 (2) |
C13—C14—C15—C16 | −0.6 (2) | C24—C25—C26—N21 | 0.4 (2) |
C17—C14—C15—C16 | 179.96 (15) | C23—C24—C27—C27ii | 3.8 (3) |
C12—N11—C16—C15 | 0.4 (3) | C25—C24—C27—C27ii | −174.64 (19) |
C14—C15—C16—N11 | 0.1 (3) | O2—C1—C2—C3 | 12.9 (2) |
C15—C14—C17—C17i | 178.49 (19) | O1—C1—C2—C3 | −169.25 (14) |
C13—C14—C17—C17i | −1.0 (3) | C1—C2—C3—P1 | −160.80 (12) |
C26—N21—C22—C23 | −0.2 (2) | O4—P1—C3—C2 | −171.44 (11) |
N21—C22—C23—C24 | −1.1 (2) | O5—P1—C3—C2 | 64.13 (13) |
C22—C23—C24—C25 | 1.9 (2) | O3—P1—C3—C2 | −53.67 (13) |
Symmetry codes: (i) −x−1, −y+1, −z; (ii) −x+2, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O4 | 0.88 | 1.70 | 2.580 (2) | 177 |
O1—H1···N11 | 0.84 | 1.78 | 2.617 (2) | 176 |
O3—H3···O5iii | 0.84 | 1.66 | 2.501 (2) | 176 |
C13—H13···O5iv | 0.95 | 2.55 | 3.489 (2) | 170 |
C17—H17···O5v | 0.95 | 2.25 | 3.185 (2) | 169 |
C22—H22···O3vi | 0.95 | 2.41 | 3.292 (2) | 153 |
C23—H23···O2vii | 0.95 | 2.59 | 3.361 (2) | 138 |
Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x, y−1/2, −z+1/2; (v) x−1, −y+3/2, z−1/2; (vi) −x+1, y+1/2, −z+3/2; (vii) x+1, −y+3/2, z+1/2. |
C10H10N3+·C3H6O5P−·H2O | F(000) = 1440 |
Mr = 343.27 | Dx = 1.514 Mg m−3 |
Orthorhombic, Fmm2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2 | Cell parameters from 1703 reflections |
a = 18.7267 (11) Å | θ = 3.2–27.5° |
b = 22.6805 (11) Å | µ = 0.22 mm−1 |
c = 7.0893 (4) Å | T = 150 K |
V = 3011.0 (3) Å3 | Needle, colourless |
Z = 8 | 0.34 × 0.08 × 0.08 mm |
Kappa-CCD diffractometer | 1445 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.085 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
ϕ scans, and ω scans with κ offsets | h = −21→24 |
8696 measured reflections | k = −29→28 |
1703 independent reflections | l = −9→9 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0134P)2 + 1.5818P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.111 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.19 e Å−3 |
1703 reflections | Δρmin = −0.26 e Å−3 |
216 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
33 restraints | Extinction coefficient: 0.0030 (7) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983); 708 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.2 (2) |
C10H10N3+·C3H6O5P−·H2O | V = 3011.0 (3) Å3 |
Mr = 343.27 | Z = 8 |
Orthorhombic, Fmm2 | Mo Kα radiation |
a = 18.7267 (11) Å | µ = 0.22 mm−1 |
b = 22.6805 (11) Å | T = 150 K |
c = 7.0893 (4) Å | 0.34 × 0.08 × 0.08 mm |
Kappa-CCD diffractometer | 1445 reflections with I > 2σ(I) |
8696 measured reflections | Rint = 0.085 |
1703 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.111 | Δρmax = 0.19 e Å−3 |
S = 1.04 | Δρmin = −0.26 e Å−3 |
1703 reflections | Absolute structure: Flack (1983); 708 Friedel pairs |
216 parameters | Absolute structure parameter: −0.2 (2) |
33 restraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.14853 (14) | 0.03268 (12) | 0.4885 (5) | 0.0219 (5) | 0.50 |
O3 | 0.10568 (17) | 0.04733 (14) | 0.3037 (5) | 0.0286 (8) | 0.50 |
O4 | 0.22710 (13) | 0.04602 (11) | 0.4613 (5) | 0.0254 (7) | 0.50 |
O5 | 0.11160 (18) | 0.06517 (13) | 0.6473 (5) | 0.0268 (7) | 0.50 |
C1 | 0.0499 (2) | −0.1289 (2) | 0.5803 (12) | 0.0291 (11) | 0.50 |
C2 | 0.0608 (2) | −0.06304 (17) | 0.5606 (7) | 0.0251 (9) | 0.50 |
C3 | 0.1389 (5) | −0.0460 (4) | 0.5290 (17) | 0.024 (3) | 0.50 |
O1 | −0.01644 (14) | −0.14672 (14) | 0.6123 (6) | 0.0285 (11) | 0.50 |
O2 | 0.09813 (15) | −0.16460 (12) | 0.5694 (6) | 0.0388 (9) | 0.50 |
O6 | 0.17568 (16) | 0.04406 (13) | −0.0095 (5) | 0.0347 (7) | 0.50 |
N1 | 0.28612 (17) | 0.15719 (17) | 0.4770 (7) | 0.0267 (8) | 0.50 |
C11 | 0.35778 (17) | 0.15477 (10) | 0.5228 (6) | 0.0252 (10) | 0.50 |
N12 | 0.39386 (14) | 0.20516 (12) | 0.5483 (6) | 0.0265 (8) | 0.50 |
C13 | 0.46353 (15) | 0.20518 (11) | 0.5914 (7) | 0.0313 (10) | 0.50 |
C14 | 0.5000 | 0.15219 (10) | 0.6111 (6) | 0.0327 (10) | |
C15 | 0.46341 (16) | 0.09946 (12) | 0.5854 (7) | 0.0305 (10) | 0.50 |
C16 | 0.39126 (16) | 0.10035 (13) | 0.5398 (6) | 0.0274 (10) | 0.50 |
C21 | 0.2448 (2) | 0.20801 (16) | 0.4420 (11) | 0.0264 (16) | 0.50 |
N22 | 0.27667 (19) | 0.26023 (13) | 0.4679 (6) | 0.0272 (9) | 0.50 |
C23 | 0.2386 (2) | 0.3095 (2) | 0.4402 (12) | 0.0271 (17) | 0.50 |
C24 | 0.1683 (2) | 0.30746 (15) | 0.3777 (7) | 0.0302 (10) | 0.50 |
C25 | 0.13592 (19) | 0.25274 (13) | 0.3568 (8) | 0.0290 (10) | 0.50 |
C26 | 0.1737 (2) | 0.20111 (15) | 0.3906 (7) | 0.0277 (9) | 0.50 |
H3 | 0.1314 | 0.0405 | 0.2091 | 0.043* | 0.50 |
H2A | 0.0432 | −0.0433 | 0.6762 | 0.030* | 0.50 |
H2B | 0.0320 | −0.0485 | 0.4532 | 0.030* | 0.50 |
H3A | 0.1578 | −0.0678 | 0.4187 | 0.028* | 0.50 |
H3B | 0.1674 | −0.0574 | 0.6408 | 0.028* | 0.50 |
H11 | −0.0449 | −0.1188 | 0.5912 | 0.043* | 0.50 |
H1 | 0.2637 | 0.1232 | 0.4688 | 0.032* | 0.50 |
H12 | 0.3713 | 0.2390 | 0.5364 | 0.032* | 0.50 |
H13 | 0.4880 | 0.2415 | 0.6084 | 0.038* | 0.50 |
H14 | 0.5494 | 0.1520 | 0.6418 | 0.039* | 0.50 |
H15 | 0.4877 | 0.0629 | 0.5989 | 0.037* | 0.50 |
H16 | 0.3655 | 0.0647 | 0.5208 | 0.033* | 0.50 |
H23 | 0.2602 | 0.3467 | 0.4638 | 0.032* | 0.50 |
H24 | 0.1430 | 0.3427 | 0.3499 | 0.036* | 0.50 |
H25 | 0.0873 | 0.2506 | 0.3190 | 0.035* | 0.50 |
H26 | 0.1522 | 0.1633 | 0.3792 | 0.033* | 0.50 |
H61 | 0.1550 | 0.0500 | −0.113 | 0.030* | 0.50 |
H62 | 0.2085 | 0.0189 | −0.016 | 0.030* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0195 (7) | 0.0179 (10) | 0.0283 (13) | −0.0001 (7) | −0.0018 (8) | −0.0010 (9) |
O3 | 0.0238 (17) | 0.0311 (16) | 0.0308 (18) | 0.0021 (14) | −0.0015 (14) | 0.0032 (14) |
O4 | 0.0172 (14) | 0.0210 (13) | 0.038 (2) | −0.0004 (10) | 0.0005 (13) | 0.0014 (14) |
O5 | 0.0258 (17) | 0.0237 (16) | 0.0308 (19) | 0.0038 (14) | −0.0002 (16) | −0.0041 (14) |
C1 | 0.021 (3) | 0.028 (3) | 0.037 (3) | 0.0017 (19) | 0.002 (2) | 0.001 (3) |
C2 | 0.0185 (19) | 0.022 (2) | 0.035 (2) | 0.0046 (16) | −0.0011 (18) | 0.0007 (19) |
C3 | 0.025 (4) | 0.016 (5) | 0.030 (6) | 0.005 (3) | −0.006 (4) | −0.003 (3) |
O1 | 0.017 (3) | 0.0200 (13) | 0.0486 (19) | −0.0034 (12) | 0.0014 (14) | 0.0028 (13) |
O2 | 0.0267 (16) | 0.0198 (14) | 0.070 (3) | 0.0047 (12) | 0.0039 (17) | 0.0011 (17) |
O6 | 0.0368 (17) | 0.0387 (16) | 0.0286 (15) | 0.0160 (13) | −0.0006 (19) | 0.0014 (19) |
N1 | 0.0194 (15) | 0.0230 (16) | 0.038 (2) | −0.0038 (13) | −0.0022 (19) | 0.002 (2) |
C11 | 0.0212 (18) | 0.0257 (18) | 0.029 (3) | −0.0020 (16) | −0.0003 (17) | 0.0024 (17) |
N12 | 0.0226 (18) | 0.0224 (15) | 0.035 (2) | 0.0016 (13) | −0.0038 (14) | 0.0011 (15) |
C13 | 0.022 (2) | 0.031 (2) | 0.041 (3) | −0.0012 (17) | −0.006 (2) | 0.006 (2) |
C14 | 0.0255 (19) | 0.031 (2) | 0.042 (2) | −0.013 (11) | −0.001 (16) | 0.0030 (19) |
C15 | 0.024 (2) | 0.031 (2) | 0.037 (3) | 0.0014 (17) | −0.004 (2) | 0.003 (2) |
C16 | 0.024 (2) | 0.0259 (19) | 0.032 (3) | −0.0009 (17) | 0.0011 (16) | 0.0024 (18) |
C21 | 0.029 (3) | 0.016 (4) | 0.034 (3) | 0.001 (3) | −0.010 (3) | 0.010 (3) |
N22 | 0.0309 (19) | 0.0149 (17) | 0.036 (2) | −0.0032 (15) | −0.0025 (19) | −0.001 (2) |
C23 | 0.028 (3) | 0.016 (3) | 0.037 (3) | 0.000 (3) | 0.003 (3) | −0.008 (3) |
C24 | 0.032 (2) | 0.026 (2) | 0.033 (3) | 0.0019 (19) | −0.003 (2) | 0.0031 (19) |
C25 | 0.025 (2) | 0.028 (2) | 0.033 (3) | −0.0004 (19) | −0.008 (2) | −0.0006 (19) |
C26 | 0.025 (2) | 0.026 (2) | 0.033 (2) | −0.0056 (17) | −0.0036 (19) | 0.0030 (19) |
P1—O5 | 1.513 (3) | C11—C16 | 1.3898 (11) |
P1—O4 | 1.514 (4) | N12—C13 | 1.3401 (11) |
P1—O3 | 1.572 (5) | N12—H12 | 0.88 |
P1—C3 | 1.815 (6) | C13—C14 | 1.3894 (11) |
O3—H3 | 0.84 | C13—H13 | 0.95 |
C1—O2 | 1.216 (5) | C14—C15 | 1.3902 (11) |
C1—O1 | 1.326 (5) | C14—H14 | 0.95 |
C1—C2 | 1.513 (5) | C15—C16 | 1.3894 (11) |
C2—C3 | 1.530 (8) | C15—H15 | 0.95 |
C2—H2A | 0.99 | C16—H16 | 0.95 |
C2—H2B | 0.99 | C21—N22 | 1.3387 (11) |
C3—H3A | 0.99 | C21—C26 | 1.3892 (11) |
C3—H3B | 0.99 | N22—C23 | 1.3400 (11) |
O1—H11 | 0.84 | C23—C24 | 1.3895 (11) |
O6—H61 | 0.84 | C23—H23 | 0.95 |
O6—H62 | 0.84 | C24—C25 | 1.3895 (11) |
N1—C11 | 1.382 (4) | C24—H24 | 0.95 |
N1—C21 | 1.410 (4) | C25—C26 | 1.3891 (11) |
N1—H1 | 0.88 | C25—H25 | 0.95 |
C11—N12 | 1.3397 (11) | C26—H26 | 0.95 |
O5—P1—O4 | 116.2 (3) | C13—N12—H12 | 119.3 |
O5—P1—O3 | 106.5 (2) | N12—C13—C14 | 120.1 (3) |
O4—P1—O3 | 110.3 (3) | N12—C13—H13 | 120.0 |
O5—P1—C3 | 108.4 (5) | C14—C13—H13 | 120.0 |
O4—P1—C3 | 108.2 (4) | C13—C14—C15 | 119.3 (2) |
O3—P1—C3 | 106.8 (5) | C13—C14—H14 | 120.4 |
O2—C1—O1 | 120.2 (4) | C15—C14—H14 | 120.4 |
O2—C1—C2 | 123.4 (4) | C16—C15—C14 | 119.8 (3) |
O1—C1—C2 | 116.3 (4) | C16—C15—H15 | 120.1 |
C1—C2—C3 | 113.1 (4) | C14—C15—H15 | 120.1 |
C1—C2—H2A | 109.0 | C15—C16—C11 | 118.1 (3) |
C3—C2—H2A | 109.0 | C15—C16—H16 | 120.9 |
C1—C2—H2B | 109.0 | C11—C16—H16 | 120.9 |
C3—C2—H2B | 109.0 | N22—C21—C26 | 124.2 (4) |
H2A—C2—H2B | 107.8 | N22—C21—N1 | 117.0 (4) |
C2—C3—P1 | 111.5 (6) | C26—C21—N1 | 118.7 (3) |
C2—C3—H3A | 109.3 | C21—N22—C23 | 118.7 (4) |
P1—C3—H3A | 109.3 | N22—C23—C24 | 121.5 (4) |
C2—C3—H3B | 109.3 | N22—C23—H23 | 119.2 |
P1—C3—H3B | 109.3 | C24—C23—H23 | 119.2 |
H3A—C3—H3B | 108.0 | C23—C24—C25 | 118.5 (4) |
H61—O6—H62 | 114 | C23—C24—H24 | 120.7 |
C11—N1—C21 | 127.3 (3) | C25—C24—H24 | 120.7 |
C11—N1—H1 | 116.3 | C26—C25—C24 | 120.8 (3) |
C21—N1—H1 | 116.3 | C26—C25—H25 | 119.6 |
N12—C11—N1 | 119.2 (3) | C24—C25—H25 | 119.6 |
N12—C11—C16 | 121.2 (3) | C25—C26—C21 | 116.0 (4) |
N1—C11—C16 | 119.6 (3) | C25—C26—H26 | 122.0 |
C11—N12—C13 | 121.5 (3) | C21—C26—H26 | 122.0 |
C11—N12—H12 | 119.3 | ||
O2—C1—C2—C3 | −0.9 (11) | C14—C15—C16—C11 | −0.5 (7) |
O1—C1—C2—C3 | 178.5 (7) | N12—C11—C16—C15 | 0.4 (7) |
C1—C2—C3—P1 | 175.7 (6) | N1—C11—C16—C15 | 179.8 (4) |
O5—P1—C3—C2 | 52.4 (9) | C11—N1—C21—N22 | −4.9 (9) |
O4—P1—C3—C2 | 179.2 (5) | C11—N1—C21—C26 | 177.5 (5) |
O3—P1—C3—C2 | −62.0 (8) | C26—C21—N22—C23 | −1.1 (8) |
C21—N1—C11—N12 | 3.9 (7) | N1—C21—N22—C23 | −178.5 (8) |
C21—N1—C11—C16 | −175.5 (6) | C21—N22—C23—C24 | −2.8 (9) |
N1—C11—N12—C13 | −179.5 (4) | N22—C23—C24—C25 | 4.6 (11) |
C16—C11—N12—C13 | −0.1 (7) | C23—C24—C25—C26 | −2.5 (8) |
C11—N12—C13—C14 | −0.1 (7) | C24—C25—C26—C21 | −1.1 (8) |
N12—C13—C14—C15 | 0.1 (7) | N22—C21—C26—C25 | 3.0 (9) |
C13—C14—C15—C16 | 0.2 (7) | N1—C21—C26—C25 | −179.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O6 | 0.84 | 1.76 | 2.579 (5) | 165 |
O3—H3···O6i | 0.84 | 2.60 | 3.308 (5) | 143 |
O1—H11···O5ii | 0.84 | 1.79 | 2.580 (4) | 156 |
N1—H1···O4 | 0.88 | 1.88 | 2.755 (4) | 173 |
N12—H12···N22 | 0.88 | 1.90 | 2.589 (5) | 134 |
N12—H12···O2iii | 0.88 | 2.27 | 2.961 (4) | 135 |
O6—H61···O5iv | 0.84 | 1.92 | 2.755 (6) | 177 |
O6—H62···O4v | 0.84 | 1.91 | 2.744 (4) | 172 |
Symmetry codes: (i) x, −y, z; (ii) −x, −y, z; (iii) −x+1/2, y+1/2, z; (iv) x, y, z−1; (v) −x+1/2, −y, z−1/2. |
C4H12N22+·C3H5O5P2− | F(000) = 512 |
Mr = 240.20 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2230 reflections |
a = 10.6065 (3) Å | θ = 3.0–27.5° |
b = 7.9214 (2) Å | µ = 0.26 mm−1 |
c = 12.8892 (4) Å | T = 150 K |
β = 94.0540 (12)° | Plate, colourless |
V = 1080.22 (5) Å3 | 0.30 × 0.28 × 0.15 mm |
Z = 4 |
Kappa-CCD diffractometer | 2447 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2048 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.904, Tmax = 0.971 | k = −10→9 |
6785 measured reflections | l = −16→16 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0261P)2 + 0.5908P] where P = (Fo2 + 2Fc2)/3 |
2447 reflections | (Δ/σ)max = 0.001 |
137 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C4H12N22+·C3H5O5P2− | V = 1080.22 (5) Å3 |
Mr = 240.20 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.6065 (3) Å | µ = 0.26 mm−1 |
b = 7.9214 (2) Å | T = 150 K |
c = 12.8892 (4) Å | 0.30 × 0.28 × 0.15 mm |
β = 94.0540 (12)° |
Kappa-CCD diffractometer | 2447 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2048 reflections with I > 2σ(I) |
Tmin = 0.904, Tmax = 0.971 | Rint = 0.028 |
6785 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
2447 reflections | Δρmin = −0.39 e Å−3 |
137 parameters |
x | y | z | Uiso*/Ueq | ||
P1 | −0.14995 (3) | 0.38468 (5) | 0.30764 (3) | 0.01246 (12) | |
O1 | 0.31411 (11) | 0.55269 (17) | 0.28397 (9) | 0.0255 (3) | |
O2 | 0.18824 (11) | 0.58144 (17) | 0.13997 (9) | 0.0252 (3) | |
O3 | −0.28138 (10) | 0.41331 (14) | 0.24556 (9) | 0.0194 (3) | |
O4 | −0.11942 (10) | 0.19878 (13) | 0.29566 (9) | 0.0174 (2) | |
O5 | −0.15216 (10) | 0.44479 (15) | 0.41824 (8) | 0.0182 (3) | |
C1 | 0.20731 (15) | 0.5426 (2) | 0.23447 (12) | 0.0177 (3) | |
C2 | 0.09908 (14) | 0.4697 (2) | 0.29166 (12) | 0.0180 (3) | |
C3 | −0.03428 (14) | 0.5046 (2) | 0.24297 (12) | 0.0160 (3) | |
N11 | 0.36504 (12) | 0.51669 (18) | 0.48988 (10) | 0.0201 (3) | |
C12 | 0.44696 (16) | 0.6649 (2) | 0.51645 (13) | 0.0223 (4) | |
C13 | 0.57438 (16) | 0.6432 (2) | 0.47229 (13) | 0.0217 (4) | |
N21 | 0.42462 (12) | 0.57172 (16) | 0.07702 (10) | 0.0148 (3) | |
C22 | 0.43507 (15) | 0.6577 (2) | −0.02486 (12) | 0.0179 (3) | |
C23 | 0.55922 (16) | 0.6144 (2) | −0.06889 (12) | 0.0183 (3) | |
H3 | −0.2977 | 0.5171 | 0.2430 | 0.029* | |
H2A | 0.1051 | 0.5152 | 0.3634 | 0.022* | |
H2B | 0.1107 | 0.3459 | 0.2968 | 0.022* | |
H3A | −0.0388 | 0.4741 | 0.1683 | 0.019* | |
H3B | −0.0532 | 0.6265 | 0.2484 | 0.019* | |
H11A | 0.3489 | 0.5112 | 0.4189 | 0.024* | |
H11B | 0.2891 | 0.5297 | 0.5193 | 0.024* | |
H12A | 0.4585 | 0.6771 | 0.5930 | 0.027* | |
H12B | 0.4059 | 0.7687 | 0.4878 | 0.027* | |
H13A | 0.5636 | 0.6417 | 0.3954 | 0.026* | |
H13B | 0.6296 | 0.7398 | 0.4935 | 0.026* | |
H21A | 0.4853 | 0.6140 | 0.1246 | 0.018* | |
H21B | 0.3467 | 0.5946 | 0.1009 | 0.018* | |
H22A | 0.4292 | 0.7814 | −0.0154 | 0.021* | |
H22B | 0.3643 | 0.6218 | −0.0742 | 0.021* | |
H23A | 0.5622 | 0.6659 | −0.1387 | 0.022* | |
H23B | 0.6296 | 0.6620 | −0.0235 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0113 (2) | 0.0122 (2) | 0.0136 (2) | −0.00021 (14) | −0.00108 (14) | 0.00052 (14) |
O1 | 0.0169 (6) | 0.0408 (8) | 0.0187 (6) | −0.0066 (5) | 0.0008 (5) | 0.0033 (5) |
O2 | 0.0181 (6) | 0.0404 (8) | 0.0173 (6) | 0.0000 (5) | 0.0033 (5) | 0.0089 (5) |
O3 | 0.0149 (5) | 0.0152 (5) | 0.0266 (6) | 0.0012 (4) | −0.0079 (5) | −0.0002 (5) |
O4 | 0.0153 (5) | 0.0137 (5) | 0.0225 (6) | 0.0005 (4) | −0.0035 (4) | −0.0002 (4) |
O5 | 0.0155 (5) | 0.0240 (6) | 0.0152 (6) | −0.0009 (5) | 0.0013 (4) | −0.0026 (4) |
C1 | 0.0178 (8) | 0.0180 (8) | 0.0176 (8) | 0.0003 (6) | 0.0032 (6) | 0.0002 (6) |
C2 | 0.0152 (7) | 0.0213 (8) | 0.0177 (8) | −0.0007 (6) | 0.0020 (6) | 0.0044 (6) |
C3 | 0.0164 (7) | 0.0167 (8) | 0.0148 (7) | −0.0009 (6) | 0.0000 (6) | 0.0024 (6) |
N11 | 0.0137 (6) | 0.0317 (8) | 0.0151 (7) | −0.0014 (6) | 0.0022 (5) | −0.0025 (6) |
C12 | 0.0214 (8) | 0.0245 (9) | 0.0213 (8) | 0.0000 (7) | 0.0028 (6) | −0.0052 (7) |
C13 | 0.0211 (8) | 0.0249 (9) | 0.0193 (8) | −0.0050 (7) | 0.0026 (6) | −0.0017 (7) |
N21 | 0.0141 (6) | 0.0165 (6) | 0.0139 (6) | −0.0004 (5) | 0.0013 (5) | −0.0014 (5) |
C22 | 0.0223 (8) | 0.0171 (7) | 0.0141 (7) | 0.0023 (6) | 0.0004 (6) | 0.0017 (6) |
C23 | 0.0230 (8) | 0.0152 (8) | 0.0173 (8) | −0.0026 (6) | 0.0056 (6) | 0.0009 (6) |
P1—O5 | 1.5047 (11) | C12—C13 | 1.513 (2) |
P1—O4 | 1.5179 (11) | C12—H12A | 0.99 |
P1—O3 | 1.5739 (11) | C12—H12B | 0.99 |
P1—C3 | 1.8019 (15) | C13—N11i | 1.487 (2) |
O1—C1 | 1.2628 (19) | C13—H13A | 0.99 |
O2—C1 | 1.2587 (19) | C13—H13B | 0.99 |
O3—H3 | 0.84 | N21—C23ii | 1.489 (2) |
C1—C2 | 1.521 (2) | N21—C22 | 1.4901 (19) |
C2—C3 | 1.532 (2) | N21—H21A | 0.92 |
C2—H2A | 0.99 | N21—H21B | 0.92 |
C2—H2B | 0.99 | C22—C23 | 1.510 (2) |
C3—H3A | 0.99 | C22—H22A | 0.99 |
C3—H3B | 0.99 | C22—H22B | 0.99 |
N11—C12 | 1.486 (2) | C23—N21ii | 1.489 (2) |
N11—C13i | 1.487 (2) | C23—H23A | 0.99 |
N11—H11A | 0.92 | C23—H23B | 0.99 |
N11—H11B | 0.92 | ||
O5—P1—O4 | 114.90 (7) | N11—C12—H12A | 109.6 |
O5—P1—O3 | 111.31 (6) | C13—C12—H12A | 109.6 |
O4—P1—O3 | 106.01 (6) | N11—C12—H12B | 109.6 |
O5—P1—C3 | 109.15 (7) | C13—C12—H12B | 109.6 |
O4—P1—C3 | 107.90 (7) | H12A—C12—H12B | 108.1 |
O3—P1—C3 | 107.24 (7) | N11i—C13—C12 | 110.49 (14) |
P1—O3—H3 | 109.5 | N11i—C13—H13A | 109.6 |
O2—C1—O1 | 123.41 (15) | C12—C13—H13A | 109.6 |
O2—C1—C2 | 119.11 (14) | N11i—C13—H13B | 109.6 |
O1—C1—C2 | 117.38 (14) | C12—C13—H13B | 109.6 |
C1—C2—C3 | 116.08 (13) | H13A—C13—H13B | 108.1 |
C1—C2—H2A | 108.3 | C23ii—N21—C22 | 111.98 (12) |
C3—C2—H2A | 108.3 | C23ii—N21—H21A | 109.2 |
C1—C2—H2B | 108.3 | C22—N21—H21A | 109.2 |
C3—C2—H2B | 108.3 | C23ii—N21—H21B | 109.2 |
H2A—C2—H2B | 107.4 | C22—N21—H21B | 109.2 |
C2—C3—P1 | 110.77 (10) | H21A—N21—H21B | 107.9 |
C2—C3—H3A | 109.5 | N21—C22—C23 | 110.41 (12) |
P1—C3—H3A | 109.5 | N21—C22—H22A | 109.6 |
C2—C3—H3B | 109.5 | C23—C22—H22A | 109.6 |
P1—C3—H3B | 109.5 | N21—C22—H22B | 109.6 |
H3A—C3—H3B | 108.1 | C23—C22—H22B | 109.6 |
C12—N11—C13i | 111.44 (13) | H22A—C22—H22B | 108.1 |
C12—N11—H11A | 109.3 | N21ii—C23—C22 | 111.03 (13) |
C13i—N11—H11A | 109.3 | N21ii—C23—H23A | 109.4 |
C12—N11—H11B | 109.3 | C22—C23—H23A | 109.4 |
C13i—N11—H11B | 109.3 | N21ii—C23—H23B | 109.4 |
H11A—N11—H11B | 108.0 | C22—C23—H23B | 109.4 |
N11—C12—C13 | 110.29 (14) | H23A—C23—H23B | 108.0 |
O2—C1—C2—C3 | −20.5 (2) | O3—P1—C3—C2 | −174.17 (10) |
O1—C1—C2—C3 | 163.06 (15) | C13i—N11—C12—C13 | 56.89 (19) |
C1—C2—C3—P1 | 171.29 (11) | N11—C12—C13—N11i | −56.34 (18) |
O5—P1—C3—C2 | 65.12 (12) | C23ii—N21—C22—C23 | −55.72 (18) |
O4—P1—C3—C2 | −60.36 (12) | N21—C22—C23—N21ii | 55.18 (17) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4iii | 0.84 | 1.74 | 2.535 (2) | 157 |
N11—H11A···O1 | 0.92 | 1.78 | 2.686 (2) | 167 |
N11—H11B···O5iv | 0.92 | 1.72 | 2.640 (2) | 176 |
N21—H21A···O4v | 0.92 | 1.82 | 2.738 (2) | 172 |
N21—H21B···O1 | 0.92 | 2.43 | 2.992 (2) | 119 |
N21—H21B···O2 | 0.92 | 1.79 | 2.690 (2) | 165 |
C13—H13B···O2vi | 0.99 | 2.41 | 3.243 (2) | 142 |
C22—H22A···O5vii | 0.99 | 2.47 | 3.349 (2) | 148 |
C22—H22B···O3viii | 0.99 | 2.34 | 3.227 (2) | 149 |
Symmetry codes: (iii) −x−1/2, y+1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) −x+1/2, y+1/2, −z+1/2; (vi) x+1/2, −y+3/2, z+1/2; (vii) x+1/2, −y+3/2, z−1/2; (viii) −x, −y+1, −z. |
C6H16N22+·2(C3H6O5P−)·2(H2O) | F(000) = 488 |
Mr = 458.34 | Dx = 1.430 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2415 reflections |
a = 6.9270 (2) Å | θ = 2.9–27.5° |
b = 20.6027 (5) Å | µ = 0.26 mm−1 |
c = 8.0115 (2) Å | T = 150 K |
β = 111.4092 (10)° | Block, colourless |
V = 1064.47 (5) Å3 | 0.32 × 0.22 × 0.16 mm |
Z = 2 |
Kappa-CCD diffractometer | 1990 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
ϕ scans, and ω scans with κ offsets | h = −8→8 |
6838 measured reflections | k = −26→26 |
2415 independent reflections | l = −10→10 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.3605P] where P = (Fo2 + 2Fc2)/3 |
2415 reflections | (Δ/σ)max = 0.001 |
135 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C6H16N22+·2(C3H6O5P−)·2(H2O) | V = 1064.47 (5) Å3 |
Mr = 458.34 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.9270 (2) Å | µ = 0.26 mm−1 |
b = 20.6027 (5) Å | T = 150 K |
c = 8.0115 (2) Å | 0.32 × 0.22 × 0.16 mm |
β = 111.4092 (10)° |
Kappa-CCD diffractometer | 1990 reflections with I > 2σ(I) |
6838 measured reflections | Rint = 0.035 |
2415 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
2415 reflections | Δρmin = −0.48 e Å−3 |
135 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.29332 (6) | 0.382569 (18) | 0.06467 (5) | 0.01690 (13) | |
O1 | −0.2948 (2) | 0.22877 (6) | −0.2716 (2) | 0.0426 (4) | |
O2 | −0.03885 (19) | 0.18412 (6) | −0.04435 (18) | 0.0369 (3) | |
O3 | 0.21194 (18) | 0.42239 (5) | −0.11368 (14) | 0.0244 (3) | |
O4 | 0.19661 (16) | 0.40809 (5) | 0.19357 (14) | 0.0216 (3) | |
O5 | 0.52786 (16) | 0.38202 (5) | 0.14543 (16) | 0.0247 (3) | |
C1 | −0.1178 (2) | 0.23078 (8) | −0.1329 (2) | 0.0247 (4) | |
C2 | −0.0318 (3) | 0.29874 (8) | −0.1004 (2) | 0.0280 (4) | |
C3 | 0.2023 (2) | 0.30174 (7) | −0.0040 (2) | 0.0228 (3) | |
N11 | 0.45581 (19) | 0.43241 (6) | 0.51960 (16) | 0.0189 (3) | |
C12 | 0.6670 (2) | 0.45397 (8) | 0.5346 (2) | 0.0210 (3) | |
C13 | 0.6520 (2) | 0.51458 (8) | 0.4228 (2) | 0.0218 (3) | |
C14 | 0.4643 (3) | 0.37154 (8) | 0.6226 (2) | 0.0270 (4) | |
O6 | 0.1965 (2) | 0.54462 (7) | −0.0611 (3) | 0.0298 (6) | 0.928 (6) |
O61 | 0.154 (3) | 0.5377 (9) | −0.161 (4) | 0.025* | 0.072 (6) |
H1 | −0.3442 | 0.1911 | −0.2824 | 0.064* | |
H3 | 0.2154 | 0.4622 | −0.0898 | 0.037* | |
H2A | −0.0985 | 0.3225 | −0.0284 | 0.034* | |
H2B | −0.0689 | 0.3212 | −0.2171 | 0.034* | |
H3A | 0.2702 | 0.2849 | −0.0846 | 0.027* | |
H3B | 0.2426 | 0.2733 | 0.1029 | 0.027* | |
H11 | 0.3803 | 0.4238 | 0.3994 | 0.023* | |
H12A | 0.7359 | 0.4189 | 0.4925 | 0.025* | |
H12B | 0.7517 | 0.4632 | 0.6616 | 0.025* | |
H13A | 0.7930 | 0.5291 | 0.4358 | 0.026* | |
H13B | 0.5750 | 0.5045 | 0.2948 | 0.026* | |
H14A | 0.3232 | 0.3581 | 0.6075 | 0.040* | |
H14B | 0.5443 | 0.3792 | 0.7499 | 0.040* | |
H14C | 0.5310 | 0.3373 | 0.5780 | 0.040* | |
H61 | 0.0767 | 0.5599 | −0.1065 | 0.065* | |
H62 | 0.2756 | 0.5670 | −0.0951 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0139 (2) | 0.0155 (2) | 0.0197 (2) | 0.00018 (14) | 0.00415 (15) | 0.00017 (15) |
O1 | 0.0290 (7) | 0.0225 (7) | 0.0541 (8) | −0.0081 (5) | −0.0114 (6) | 0.0042 (6) |
O2 | 0.0297 (7) | 0.0246 (7) | 0.0443 (8) | −0.0030 (5) | −0.0008 (6) | 0.0058 (6) |
O3 | 0.0310 (6) | 0.0210 (6) | 0.0209 (6) | 0.0010 (5) | 0.0092 (5) | 0.0017 (5) |
O4 | 0.0179 (5) | 0.0264 (6) | 0.0190 (5) | 0.0007 (5) | 0.0049 (4) | −0.0025 (5) |
O5 | 0.0141 (6) | 0.0189 (6) | 0.0376 (7) | 0.0002 (4) | 0.0053 (5) | 0.0007 (5) |
C1 | 0.0191 (8) | 0.0214 (8) | 0.0300 (8) | −0.0015 (7) | 0.0046 (7) | −0.0001 (7) |
C2 | 0.0204 (8) | 0.0198 (8) | 0.0357 (9) | −0.0021 (6) | 0.0007 (7) | 0.0000 (7) |
C3 | 0.0194 (8) | 0.0180 (8) | 0.0287 (8) | −0.0004 (6) | 0.0059 (7) | −0.0008 (7) |
N11 | 0.0193 (6) | 0.0185 (6) | 0.0168 (6) | −0.0007 (5) | 0.0043 (5) | −0.0008 (5) |
C12 | 0.0166 (7) | 0.0212 (8) | 0.0237 (8) | 0.0001 (6) | 0.0054 (6) | −0.0022 (6) |
C13 | 0.0204 (8) | 0.0219 (8) | 0.0238 (8) | −0.0006 (6) | 0.0088 (6) | −0.0021 (6) |
C14 | 0.0287 (9) | 0.0206 (8) | 0.0283 (9) | −0.0017 (7) | 0.0064 (7) | 0.0045 (7) |
O6 | 0.0210 (7) | 0.0211 (7) | 0.0492 (16) | 0.0033 (5) | 0.0152 (8) | 0.0065 (7) |
P1—O5 | 1.5136 (11) | N11—C12 | 1.4911 (19) |
P1—O4 | 1.5154 (11) | N11—H11 | 0.93 |
P1—O3 | 1.5635 (11) | C12—C13 | 1.518 (2) |
P1—C3 | 1.7945 (16) | C12—H12A | 0.99 |
O1—C1 | 1.3212 (19) | C12—H12B | 0.99 |
O1—H1 | 0.84 | C13—N11i | 1.488 (2) |
O2—C1 | 1.201 (2) | C13—H13A | 0.99 |
O3—H3 | 0.84 | C13—H13B | 0.99 |
C1—C2 | 1.507 (2) | C14—H14A | 0.98 |
C2—C3 | 1.521 (2) | C14—H14B | 0.98 |
C2—H2A | 0.99 | C14—H14C | 0.98 |
C2—H2B | 0.99 | O6—O61 | 0.76 (3) |
C3—H3A | 0.99 | O6—H61 | 0.84 |
C3—H3B | 0.99 | O6—H62 | 0.84 |
N11—C13i | 1.488 (2) | O61—H61 | 0.92 |
N11—C14 | 1.490 (2) | O61—H62 | 1.02 |
O5—P1—O4 | 112.57 (6) | C14—N11—H11 | 107.8 |
O5—P1—O3 | 111.54 (7) | C12—N11—H11 | 107.8 |
O4—P1—O3 | 109.82 (6) | N11—C12—C13 | 110.10 (12) |
O5—P1—C3 | 109.05 (7) | N11—C12—H12A | 109.6 |
O4—P1—C3 | 109.73 (7) | C13—C12—H12A | 109.6 |
O3—P1—C3 | 103.74 (7) | N11—C12—H12B | 109.6 |
C1—O1—H1 | 109.5 | C13—C12—H12B | 109.6 |
P1—O3—H3 | 109.5 | H12A—C12—H12B | 108.2 |
O2—C1—O1 | 123.67 (15) | N11i—C13—C12 | 110.76 (12) |
O2—C1—C2 | 125.13 (15) | N11i—C13—H13A | 109.5 |
O1—C1—C2 | 111.20 (14) | C12—C13—H13A | 109.5 |
C1—C2—C3 | 113.98 (14) | N11i—C13—H13B | 109.5 |
C1—C2—H2A | 108.8 | C12—C13—H13B | 109.5 |
C3—C2—H2A | 108.8 | H13A—C13—H13B | 108.1 |
C1—C2—H2B | 108.8 | N11—C14—H14A | 109.5 |
C3—C2—H2B | 108.8 | N11—C14—H14B | 109.5 |
H2A—C2—H2B | 107.7 | H14A—C14—H14B | 109.5 |
C2—C3—P1 | 112.55 (11) | N11—C14—H14C | 109.5 |
C2—C3—H3A | 109.1 | H14A—C14—H14C | 109.5 |
P1—C3—H3A | 109.1 | H14B—C14—H14C | 109.5 |
C2—C3—H3B | 109.1 | O61—O6—H61 | 70.6 |
P1—C3—H3B | 109.1 | O61—O6—H62 | 79.1 |
H3A—C3—H3B | 107.8 | H61—O6—H62 | 108.5 |
C13i—N11—C14 | 111.63 (12) | O6—O61—H61 | 58.7 |
C13i—N11—C12 | 110.18 (12) | O6—O61—H62 | 53.8 |
C14—N11—C12 | 111.51 (12) | H61—O61—H62 | 88.6 |
C13i—N11—H11 | 107.8 | ||
O3—P1—C3—C2 | −56.5 (2) | P1—C3—C2—C1 | −170.4 (2) |
O4—P1—C3—C2 | 60.8 (2) | C3—C2—C1—O1 | −154.9 (2) |
O5—P1—C3—C2 | −175.5 (2) | C3—C2—C1—O2 | 25.9 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5ii | 0.84 | 1.74 | 2.562 (2) | 167 |
O3—H3···O6 | 0.84 | 1.73 | 2.562 (2) | 174 |
N11—H11···O4 | 0.93 | 1.71 | 2.622 (2) | 168 |
O6—H61···O4iii | 0.84 | 1.88 | 2.717 (2) | 176 |
O6—H62···O5iv | 0.83 | 1.88 | 2.707 (2) | 174 |
Symmetry codes: (ii) x−1, −y+1/2, z−1/2; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z. |
C10H8.82N20.72+·C3H6O5.28P0.72= | F(000) = 648 |
Mr = 1240.98 | Dx = 1.537 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3059 reflections |
a = 11.3482 (5) Å | θ = 3.3–27.5° |
b = 6.7178 (3) Å | µ = 0.23 mm−1 |
c = 17.7354 (7) Å | T = 150 K |
β = 97.4980 (18)° | Plate, colourless |
V = 1340.50 (10) Å3 | 0.22 × 0.20 × 0.08 mm |
Z = 1 |
Kappa-CCD diffractometer | 2113 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.060 |
Graphite monochromator | θmax = 27.5°, θmin = 3.3° |
ϕ scans, and ω scans with κ offsets | h = −14→14 |
13381 measured reflections | k = −8→8 |
3059 independent reflections | l = −22→23 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0557P)2 + 0.2557P] where P = (Fo2 + 2Fc2)/3 |
3059 reflections | (Δ/σ)max = 0.001 |
194 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C10H8.82N20.72+·C3H6O5.28P0.72= | V = 1340.50 (10) Å3 |
Mr = 1240.98 | Z = 1 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.3482 (5) Å | µ = 0.23 mm−1 |
b = 6.7178 (3) Å | T = 150 K |
c = 17.7354 (7) Å | 0.22 × 0.20 × 0.08 mm |
β = 97.4980 (18)° |
Kappa-CCD diffractometer | 2113 reflections with I > 2σ(I) |
13381 measured reflections | Rint = 0.060 |
3059 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.27 e Å−3 |
3059 reflections | Δρmin = −0.40 e Å−3 |
194 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N11 | −0.25452 (14) | 0.2979 (2) | 0.32676 (9) | 0.0255 (4) | |
C12 | −0.33789 (17) | 0.2537 (3) | 0.37035 (10) | 0.0233 (4) | |
C13 | −0.45783 (16) | 0.2444 (3) | 0.34295 (10) | 0.0221 (4) | |
C14 | −0.49461 (16) | 0.2853 (3) | 0.26663 (10) | 0.0195 (4) | |
C15 | −0.40681 (17) | 0.3329 (3) | 0.22137 (11) | 0.0294 (5) | |
C16 | −0.28898 (18) | 0.3364 (3) | 0.25306 (11) | 0.0320 (5) | |
N21 | −0.86140 (13) | 0.2691 (2) | 0.17454 (9) | 0.0236 (4) | |
C22 | −0.77653 (17) | 0.2587 (3) | 0.12837 (11) | 0.0234 (4) | |
C23 | −0.65690 (16) | 0.2626 (3) | 0.15610 (10) | 0.0220 (4) | |
C24 | −0.62221 (16) | 0.2792 (3) | 0.23439 (10) | 0.0195 (4) | |
C25 | −0.71148 (16) | 0.2900 (3) | 0.28117 (10) | 0.0219 (4) | |
C26 | −0.82974 (16) | 0.2843 (3) | 0.24981 (11) | 0.0231 (4) | |
P1 | 0.36541 (4) | 0.25021 (7) | 0.53910 (3) | 0.01867 (15) | |
O1 | −0.02847 (12) | 0.2992 (3) | 0.37185 (8) | 0.0377 (4) | |
O2 | −0.05061 (12) | 0.2529 (2) | 0.49404 (8) | 0.0311 (4) | |
O3 | 0.39660 (11) | 0.4400 (2) | 0.49837 (8) | 0.0275 (3) | |
O4 | 0.41748 (12) | 0.24594 (19) | 0.62307 (7) | 0.0262 (3) | |
O5 | 0.39726 (11) | 0.0642 (2) | 0.49603 (7) | 0.0266 (3) | |
C1 | 0.01158 (16) | 0.2721 (3) | 0.44412 (10) | 0.0223 (4) | |
C2 | 0.14589 (15) | 0.2672 (3) | 0.45486 (10) | 0.0220 (4) | |
C3 | 0.20659 (15) | 0.2485 (3) | 0.53604 (10) | 0.0201 (4) | |
H11 | −0.1790 | 0.3017 | 0.3458 | 0.031* | 0.22 (4) |
H12 | −0.3140 | 0.2273 | 0.4227 | 0.028* | |
H13 | −0.5143 | 0.2106 | 0.3759 | 0.027* | |
H15 | −0.4280 | 0.3627 | 0.1690 | 0.035* | |
H16 | −0.2301 | 0.3674 | 0.2214 | 0.038* | |
H21 | −0.9370 | 0.2659 | 0.1555 | 0.028* | 0.50 |
H22 | −0.7995 | 0.2483 | 0.0751 | 0.028* | |
H23 | −0.5988 | 0.2542 | 0.1222 | 0.026* | |
H25 | −0.6912 | 0.3014 | 0.3347 | 0.026* | |
H26 | −0.8898 | 0.2914 | 0.2824 | 0.028* | |
H1 | −0.1031 | 0.2950 | 0.3658 | 0.057* | 0.78 (4) |
H3 | 0.4705 | 0.4573 | 0.5054 | 0.041* | 0.50 |
H4 | 0.4919 | 0.2375 | 0.6267 | 0.039* | 0.50 |
H5 | 0.5000 | 0.0000 | 0.5000 | 0.040* | |
H2A | 0.1747 | 0.3906 | 0.4328 | 0.026* | |
H2B | 0.1716 | 0.1540 | 0.4252 | 0.026* | |
H3A | 0.1815 | 0.1230 | 0.5585 | 0.024* | |
H3B | 0.1820 | 0.3605 | 0.5667 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0174 (8) | 0.0324 (9) | 0.0257 (8) | 0.0002 (6) | −0.0010 (6) | 0.0015 (7) |
C12 | 0.0220 (9) | 0.0275 (10) | 0.0194 (9) | 0.0007 (7) | −0.0009 (7) | −0.0002 (7) |
C13 | 0.0198 (9) | 0.0280 (10) | 0.0185 (9) | −0.0006 (7) | 0.0025 (7) | 0.0013 (7) |
C14 | 0.0168 (9) | 0.0215 (9) | 0.0200 (9) | −0.0004 (7) | 0.0013 (7) | 0.0003 (7) |
C15 | 0.0210 (10) | 0.0455 (12) | 0.0212 (10) | −0.0002 (9) | 0.0013 (8) | 0.0047 (9) |
C16 | 0.0211 (10) | 0.0471 (13) | 0.0281 (11) | −0.0030 (9) | 0.0051 (8) | 0.0062 (9) |
N21 | 0.0182 (8) | 0.0283 (9) | 0.0231 (8) | 0.0006 (6) | −0.0015 (6) | 0.0010 (6) |
C22 | 0.0232 (10) | 0.0262 (10) | 0.0195 (9) | 0.0000 (7) | −0.0019 (7) | 0.0007 (7) |
C23 | 0.0206 (9) | 0.0264 (10) | 0.0188 (9) | −0.0005 (7) | 0.0022 (7) | −0.0004 (7) |
C24 | 0.0188 (9) | 0.0201 (9) | 0.0193 (9) | 0.0010 (7) | 0.0010 (7) | −0.0003 (7) |
C25 | 0.0208 (9) | 0.0266 (10) | 0.0177 (9) | 0.0000 (7) | 0.0008 (7) | −0.0007 (7) |
C26 | 0.0197 (9) | 0.0266 (10) | 0.0233 (9) | 0.0007 (7) | 0.0043 (7) | −0.0013 (7) |
P1 | 0.0126 (2) | 0.0240 (3) | 0.0191 (3) | 0.00014 (17) | 0.00073 (17) | 0.00022 (18) |
O1 | 0.0143 (7) | 0.0745 (11) | 0.0234 (7) | 0.0006 (7) | −0.0010 (5) | 0.0026 (7) |
O2 | 0.0186 (7) | 0.0502 (9) | 0.0253 (7) | −0.0003 (6) | 0.0059 (6) | 0.0023 (6) |
O3 | 0.0191 (7) | 0.0301 (8) | 0.0324 (8) | −0.0034 (5) | 0.0004 (6) | 0.0069 (6) |
O4 | 0.0184 (7) | 0.0377 (8) | 0.0211 (7) | 0.0002 (6) | −0.0025 (5) | 0.0008 (6) |
O5 | 0.0214 (7) | 0.0302 (8) | 0.0279 (8) | 0.0047 (5) | 0.0018 (6) | −0.0056 (5) |
C1 | 0.0170 (9) | 0.0281 (10) | 0.0214 (9) | 0.0004 (7) | 0.0010 (7) | −0.0021 (7) |
C2 | 0.0132 (8) | 0.0320 (10) | 0.0207 (9) | −0.0002 (7) | 0.0019 (7) | 0.0002 (8) |
C3 | 0.0143 (8) | 0.0269 (9) | 0.0189 (9) | 0.0000 (7) | 0.0016 (7) | −0.0005 (7) |
N11—C12 | 1.331 (2) | C25—C26 | 1.385 (3) |
N11—C16 | 1.340 (2) | C25—H25 | 0.95 |
N11—H11 | 0.88 | C26—H26 | 0.95 |
C12—C13 | 1.386 (3) | P1—O4 | 1.5292 (13) |
C12—H12 | 0.95 | P1—O3 | 1.5293 (13) |
C13—C14 | 1.391 (2) | P1—O5 | 1.5320 (13) |
C13—H13 | 0.95 | P1—C3 | 1.7961 (18) |
C14—C15 | 1.396 (3) | O1—C1 | 1.315 (2) |
C14—C24 | 1.486 (3) | O1—H1 | 0.84 |
C15—C16 | 1.381 (3) | O2—C1 | 1.209 (2) |
C15—H15 | 0.95 | O3—H3 | 0.84 |
C16—H16 | 0.95 | O4—H4 | 0.84 |
N21—C26 | 1.340 (2) | O5—H5 | 1.2366 |
N21—C22 | 1.345 (2) | C1—C2 | 1.511 (2) |
N21—H21 | 0.88 | C2—C3 | 1.518 (2) |
C22—C23 | 1.382 (3) | C2—H2A | 0.99 |
C22—H22 | 0.95 | C2—H2B | 0.99 |
C23—C24 | 1.397 (2) | C3—H3A | 0.99 |
C23—H23 | 0.95 | C3—H3B | 0.99 |
C24—C25 | 1.393 (3) | ||
C12—N11—C16 | 118.07 (17) | C26—C25—H25 | 119.9 |
C12—N11—H11 | 121.0 | C24—C25—H25 | 119.9 |
C16—N11—H11 | 121.0 | N21—C26—C25 | 121.47 (17) |
N11—C12—C13 | 123.12 (17) | N21—C26—H26 | 119.3 |
N11—C12—H12 | 118.4 | C25—C26—H26 | 119.3 |
C13—C12—H12 | 118.4 | O4—P1—O3 | 113.07 (8) |
C12—C13—C14 | 119.26 (17) | O4—P1—O5 | 112.58 (7) |
C12—C13—H13 | 120.4 | O3—P1—O5 | 111.11 (8) |
C14—C13—H13 | 120.4 | O4—P1—C3 | 106.74 (8) |
C13—C14—C15 | 117.31 (17) | O3—P1—C3 | 106.50 (8) |
C13—C14—C24 | 121.50 (16) | O5—P1—C3 | 106.31 (8) |
C15—C14—C24 | 121.19 (17) | C1—O1—H1 | 109.5 |
C16—C15—C14 | 119.72 (18) | P1—O3—H3 | 109.5 |
C16—C15—H15 | 120.1 | P1—O4—H4 | 109.5 |
C14—C15—H15 | 120.1 | P1—O5—H5 | 122.6 |
N11—C16—C15 | 122.51 (18) | O2—C1—O1 | 124.59 (17) |
N11—C16—H16 | 118.7 | O2—C1—C2 | 125.51 (17) |
C15—C16—H16 | 118.7 | O1—C1—C2 | 109.90 (15) |
C26—N21—C22 | 119.36 (16) | C1—C2—C3 | 116.53 (15) |
C26—N21—H21 | 120.3 | C1—C2—H2A | 108.2 |
C22—N21—H21 | 120.3 | C3—C2—H2A | 108.2 |
N21—C22—C23 | 122.03 (17) | C1—C2—H2B | 108.2 |
N21—C22—H22 | 119.0 | C3—C2—H2B | 108.2 |
C23—C22—H22 | 119.0 | H2A—C2—H2B | 107.3 |
C22—C23—C24 | 119.42 (17) | C2—C3—P1 | 110.95 (12) |
C22—C23—H23 | 120.3 | C2—C3—H3A | 109.4 |
C24—C23—H23 | 120.3 | P1—C3—H3A | 109.4 |
C25—C24—C23 | 117.62 (16) | C2—C3—H3B | 109.4 |
C25—C24—C14 | 121.15 (16) | P1—C3—H3B | 109.4 |
C23—C24—C14 | 121.23 (16) | H3A—C3—H3B | 108.0 |
C26—C25—C24 | 120.10 (17) | ||
C16—N11—C12—C13 | 0.5 (3) | C15—C14—C24—C25 | −160.98 (19) |
N11—C12—C13—C14 | −0.8 (3) | C13—C14—C24—C23 | −161.26 (17) |
C12—C13—C14—C15 | 0.4 (3) | C15—C14—C24—C23 | 18.9 (3) |
C12—C13—C14—C24 | −179.47 (16) | C23—C24—C25—C26 | 0.0 (3) |
C13—C14—C15—C16 | 0.4 (3) | C14—C24—C25—C26 | 179.91 (16) |
C24—C14—C15—C16 | −179.74 (19) | C22—N21—C26—C25 | 0.1 (3) |
C12—N11—C16—C15 | 0.4 (3) | C24—C25—C26—N21 | −0.2 (3) |
C14—C15—C16—N11 | −0.8 (3) | O2—C1—C2—C3 | −3.8 (3) |
C26—N21—C22—C23 | 0.2 (3) | O1—C1—C2—C3 | 176.69 (16) |
N21—C22—C23—C24 | −0.4 (3) | C1—C2—C3—P1 | −178.76 (12) |
C22—C23—C24—C25 | 0.3 (3) | O4—P1—C3—C2 | 176.01 (12) |
C22—C23—C24—C14 | −179.61 (16) | O3—P1—C3—C2 | 54.96 (14) |
C13—C14—C24—C25 | 18.8 (3) | O5—P1—C3—C2 | −63.60 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N11 | 0.84 | 1.77 | 2.585 (2) | 164 |
O3—H3···O3i | 0.84 | 1.67 | 2.475 (2) | 160 |
O4—H4···N21ii | 0.84 | 1.77 | 2.558 (2) | 156 |
O5—H5···O5iii | 1.24 | 1.24 | 2.473 (2) | 180 |
N11—H11···O1 | 0.88 | 1.71 | 2.585 (2) | 173 |
N21—H21···O4iv | 0.88 | 1.68 | 2.558 (2) | 177 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+3/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) x−3/2, −y+1/2, z−1/2. |
C12H14N22+·2(C3H6O5P−) | Z = 1 |
Mr = 492.35 | F(000) = 258 |
Triclinic, P1 | Dx = 1.520 Mg m−3 |
Hall symbol: -P -1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5651 (3) Å | Cell parameters from 5037 reflections |
b = 8.6472 (3) Å | θ = 2.8–27.6° |
c = 9.0077 (4) Å | µ = 0.26 mm−1 |
α = 72.6340 (14)° | T = 150 K |
β = 73.1760 (15)° | Plate, colourless |
γ = 87.386 (2)° | 0.30 × 0.14 × 0.12 mm |
V = 537.79 (4) Å3 |
Kappa-CCD diffractometer | 2457 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2163 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ scans, and ω scans with κ offsets | θmax = 27.6°, θmin = 2.8° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.930, Tmax = 0.973 | k = −11→11 |
6047 measured reflections | l = −11→11 |
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)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0237P)2 + 0.2452P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2457 reflections | Δρmax = 0.32 e Å−3 |
148 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (7) |
C12H14N22+·2(C3H6O5P−) | γ = 87.386 (2)° |
Mr = 492.35 | V = 537.79 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.5651 (3) Å | Mo Kα radiation |
b = 8.6472 (3) Å | µ = 0.26 mm−1 |
c = 9.0077 (4) Å | T = 150 K |
α = 72.6340 (14)° | 0.30 × 0.14 × 0.12 mm |
β = 73.1760 (15)° |
Kappa-CCD diffractometer | 2457 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2163 reflections with I > 2σ(I) |
Tmin = 0.930, Tmax = 0.973 | Rint = 0.035 |
6047 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.32 e Å−3 |
2457 reflections | Δρmin = −0.37 e Å−3 |
148 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | 0.37635 (17) | 0.04194 (14) | 0.85339 (16) | 0.0206 (3) | |
C12 | 0.2617 (2) | −0.04464 (17) | 0.99512 (19) | 0.0213 (3) | |
C13 | 0.2703 (2) | −0.21093 (17) | 1.04550 (18) | 0.0203 (3) | |
C14 | 0.39673 (19) | −0.28923 (16) | 0.94808 (18) | 0.0173 (3) | |
C15 | 0.5144 (2) | −0.19391 (17) | 0.80193 (19) | 0.0215 (3) | |
C16 | 0.5006 (2) | −0.02859 (18) | 0.75733 (19) | 0.0233 (3) | |
C17 | 0.40381 (19) | −0.47121 (16) | 0.9967 (2) | 0.0210 (3) | |
P1 | 0.22718 (5) | 0.39160 (4) | 0.61755 (5) | 0.01547 (13) | |
O1 | 0.18632 (15) | 0.99449 (12) | 0.57217 (14) | 0.0262 (3) | |
O2 | −0.02062 (17) | 0.83045 (13) | 0.78710 (15) | 0.0325 (3) | |
O3 | 0.30644 (14) | 0.45771 (12) | 0.42584 (13) | 0.0193 (2) | |
O4 | 0.38859 (13) | 0.35962 (11) | 0.69065 (13) | 0.0189 (2) | |
O5 | 0.09918 (14) | 0.24752 (11) | 0.66071 (14) | 0.0215 (2) | |
C1 | 0.1045 (2) | 0.85194 (16) | 0.66337 (19) | 0.0189 (3) | |
C2 | 0.1917 (2) | 0.71868 (16) | 0.59294 (19) | 0.0198 (3) | |
C3 | 0.09578 (19) | 0.55173 (15) | 0.68156 (18) | 0.0173 (3) | |
H11 | 0.3700 | 0.1481 | 0.8224 | 0.025* | |
H12 | 0.1746 | 0.0084 | 1.0608 | 0.026* | |
H13 | 0.1902 | −0.2726 | 1.1467 | 0.024* | |
H15 | 0.6035 | −0.2431 | 0.7337 | 0.026* | |
H16 | 0.5799 | 0.0365 | 0.6574 | 0.028* | |
H17A | 0.3668 | −0.5119 | 0.9178 | 0.025* | |
H17B | 0.3140 | −0.5176 | 1.1048 | 0.025* | |
H1 | 0.1425 | 1.0658 | 0.6170 | 0.039* | |
H3 | 0.3995 | 0.5199 | 0.4009 | 0.029* | |
H2A | 0.3221 | 0.7122 | 0.5947 | 0.024* | |
H2B | 0.1918 | 0.7484 | 0.4779 | 0.024* | |
H3A | −0.0265 | 0.5517 | 0.6620 | 0.021* | |
H3B | 0.0748 | 0.5298 | 0.7998 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0242 (6) | 0.0130 (5) | 0.0258 (7) | 0.0038 (5) | −0.0090 (5) | −0.0065 (5) |
C12 | 0.0184 (7) | 0.0204 (7) | 0.0263 (8) | 0.0053 (5) | −0.0047 (6) | −0.0112 (6) |
C13 | 0.0178 (7) | 0.0201 (7) | 0.0198 (7) | 0.0007 (5) | −0.0009 (6) | −0.0058 (6) |
C14 | 0.0165 (7) | 0.0151 (6) | 0.0205 (7) | 0.0015 (5) | −0.0058 (6) | −0.0051 (5) |
C15 | 0.0233 (7) | 0.0168 (7) | 0.0209 (8) | 0.0036 (5) | −0.0007 (6) | −0.0065 (6) |
C16 | 0.0248 (8) | 0.0193 (7) | 0.0208 (8) | 0.0004 (6) | −0.0010 (6) | −0.0039 (6) |
C17 | 0.0190 (7) | 0.0144 (7) | 0.0272 (8) | 0.0010 (5) | −0.0041 (6) | −0.0051 (6) |
P1 | 0.0148 (2) | 0.01102 (18) | 0.0200 (2) | 0.00057 (12) | −0.00161 (14) | −0.00699 (14) |
O1 | 0.0290 (6) | 0.0130 (5) | 0.0321 (7) | −0.0007 (4) | 0.0031 (5) | −0.0118 (4) |
O2 | 0.0374 (7) | 0.0198 (5) | 0.0320 (7) | 0.0004 (5) | 0.0079 (5) | −0.0128 (5) |
O3 | 0.0179 (5) | 0.0194 (5) | 0.0207 (6) | −0.0019 (4) | −0.0024 (4) | −0.0089 (4) |
O4 | 0.0173 (5) | 0.0149 (5) | 0.0228 (6) | 0.0018 (4) | −0.0042 (4) | −0.0049 (4) |
O5 | 0.0186 (5) | 0.0134 (5) | 0.0311 (6) | −0.0011 (4) | −0.0002 (4) | −0.0112 (4) |
C1 | 0.0190 (7) | 0.0142 (6) | 0.0243 (8) | 0.0018 (5) | −0.0042 (6) | −0.0090 (6) |
C2 | 0.0195 (7) | 0.0139 (6) | 0.0250 (8) | 0.0011 (5) | −0.0013 (6) | −0.0094 (6) |
C3 | 0.0162 (7) | 0.0133 (6) | 0.0218 (7) | 0.0010 (5) | −0.0019 (5) | −0.0079 (5) |
N11—C12 | 1.338 (2) | P1—O5 | 1.4980 (10) |
N11—C16 | 1.340 (2) | P1—O4 | 1.5254 (11) |
N11—H11 | 0.88 | P1—O3 | 1.5846 (11) |
C12—C13 | 1.377 (2) | P1—C3 | 1.8048 (14) |
C12—H12 | 0.95 | O1—C1 | 1.3222 (17) |
C13—C14 | 1.397 (2) | O1—H1 | 0.84 |
C13—H13 | 0.95 | O2—C1 | 1.2059 (19) |
C14—C15 | 1.395 (2) | O3—H3 | 0.84 |
C14—C17 | 1.5052 (18) | C1—C2 | 1.5134 (19) |
C15—C16 | 1.373 (2) | C2—C3 | 1.5234 (18) |
C15—H15 | 0.95 | C2—H2A | 0.99 |
C16—H16 | 0.95 | C2—H2B | 0.99 |
C17—C17i | 1.528 (3) | C3—H3A | 0.99 |
C17—H17A | 0.99 | C3—H3B | 0.99 |
C17—H17B | 0.99 | ||
C12—N11—C16 | 121.84 (13) | O5—P1—O4 | 114.93 (6) |
C12—N11—H11 | 119.1 | O5—P1—O3 | 108.77 (6) |
C16—N11—H11 | 119.1 | O4—P1—O3 | 108.82 (6) |
N11—C12—C13 | 119.76 (13) | O5—P1—C3 | 108.77 (6) |
N11—C12—H12 | 120.1 | O4—P1—C3 | 108.83 (6) |
C13—C12—H12 | 120.1 | O3—P1—C3 | 106.38 (6) |
C12—C13—C14 | 120.16 (14) | C1—O1—H1 | 109.5 |
C12—C13—H13 | 119.9 | P1—O3—H3 | 109.5 |
C14—C13—H13 | 119.9 | O2—C1—O1 | 124.74 (13) |
C15—C14—C13 | 118.05 (13) | O2—C1—C2 | 124.54 (13) |
C15—C14—C17 | 120.61 (13) | O1—C1—C2 | 110.71 (12) |
C13—C14—C17 | 121.32 (13) | C1—C2—C3 | 114.53 (12) |
C16—C15—C14 | 119.54 (14) | C1—C2—H2A | 108.6 |
C16—C15—H15 | 120.2 | C3—C2—H2A | 108.6 |
C14—C15—H15 | 120.2 | C1—C2—H2B | 108.6 |
N11—C16—C15 | 120.64 (14) | C3—C2—H2B | 108.6 |
N11—C16—H16 | 119.7 | H2A—C2—H2B | 107.6 |
C15—C16—H16 | 119.7 | C2—C3—P1 | 112.83 (10) |
C14—C17—C17i | 112.33 (14) | C2—C3—H3A | 109.0 |
C14—C17—H17A | 109.1 | P1—C3—H3A | 109.0 |
C17i—C17—H17A | 109.1 | C2—C3—H3B | 109.0 |
C14—C17—H17B | 109.1 | P1—C3—H3B | 109.0 |
C17i—C17—H17B | 109.1 | H3A—C3—H3B | 107.8 |
H17A—C17—H17B | 107.9 | ||
C16—N11—C12—C13 | 0.2 (2) | C15—C14—C17—C17i | 57.0 (2) |
N11—C12—C13—C14 | −0.8 (2) | C13—C14—C17—C17i | −124.38 (18) |
C12—C13—C14—C15 | 1.3 (2) | O2—C1—C2—C3 | 6.2 (2) |
C12—C13—C14—C17 | −177.40 (13) | O1—C1—C2—C3 | −174.92 (13) |
C13—C14—C15—C16 | −1.1 (2) | C1—C2—C3—P1 | −169.43 (10) |
C17—C14—C15—C16 | 177.54 (14) | O5—P1—C3—C2 | −159.26 (10) |
C12—N11—C16—C15 | −0.1 (2) | O4—P1—C3—C2 | 74.85 (12) |
C14—C15—C16—N11 | 0.5 (2) | O3—P1—C3—C2 | −42.25 (12) |
Symmetry code: (i) −x+1, −y−1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O4 | 0.88 | 1.84 | 2.692 (2) | 161 |
O1—H1···O5ii | 0.84 | 1.73 | 2.542 (2) | 163 |
O3—H3···O4iii | 0.84 | 1.79 | 2.619 (2) | 168 |
C12—H12···O2iv | 0.95 | 2.29 | 3.224 (2) | 167 |
C13—H13···O5v | 0.95 | 2.41 | 3.196 (2) | 139 |
Symmetry codes: (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+2; (v) −x, −y, −z+2. |
C6H16N22+·2(C3H6O5P−)·0.3(CH4O) | F(000) = 910 |
Mr = 429.31 | Dx = 1.377 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 4652 reflections |
a = 20.2229 (17) Å | θ = 3.8–27.5° |
b = 8.6162 (6) Å | µ = 0.26 mm−1 |
c = 11.8812 (9) Å | T = 150 K |
V = 2070.2 (3) Å3 | Plate, colourless |
Z = 4 | 0.24 × 0.10 × 0.04 mm |
Kappa-CCD diffractometer | 3521 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.125 |
Graphite monochromator | θmax = 27.5°, θmin = 3.8° |
ϕ scans, and ω scans with κ offsets | h = −26→25 |
15150 measured reflections | k = −11→11 |
4652 independent reflections | l = −15→15 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.0488P)2 + 2.3804P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.168 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.56 e Å−3 |
4652 reflections | Δρmin = −0.30 e Å−3 |
250 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.019 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2161 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.07 (15) |
C6H16N22+·2(C3H6O5P−)·0.3(CH4O) | V = 2070.2 (3) Å3 |
Mr = 429.31 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 20.2229 (17) Å | µ = 0.26 mm−1 |
b = 8.6162 (6) Å | T = 150 K |
c = 11.8812 (9) Å | 0.24 × 0.10 × 0.04 mm |
Kappa-CCD diffractometer | 3521 reflections with I > 2σ(I) |
15150 measured reflections | Rint = 0.125 |
4652 independent reflections |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.168 | Δρmax = 0.56 e Å−3 |
S = 1.03 | Δρmin = −0.30 e Å−3 |
4652 reflections | Absolute structure: Flack (1983), 2161 Friedel pairs |
250 parameters | Absolute structure parameter: 0.07 (15) |
1 restraint |
Experimental. ?e' command in the SHELXL97 input file. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.41188 (19) | 0.4517 (4) | 0.2262 (3) | 0.0389 (9) | |
N4 | 0.4030 (2) | 0.5321 (5) | 0.4606 (4) | 0.0441 (10) | |
C2 | 0.3906 (3) | 0.3365 (5) | 0.3133 (4) | 0.0403 (11) | |
C3 | 0.4224 (3) | 0.3749 (6) | 0.4246 (5) | 0.0453 (12) | |
C5 | 0.4215 (3) | 0.6522 (6) | 0.3742 (5) | 0.0437 (11) | |
C6 | 0.3931 (3) | 0.6175 (5) | 0.2601 (5) | 0.0413 (10) | |
C7 | 0.4077 (3) | 0.1733 (6) | 0.2744 (6) | 0.0537 (15) | |
C8 | 0.4172 (3) | 0.7278 (6) | 0.1727 (5) | 0.0541 (14) | |
P1 | 0.10255 (6) | 0.52993 (13) | 0.24994 (11) | 0.0361 (3) | |
O11 | 0.0993 (2) | 1.1155 (4) | 0.2527 (7) | 0.107 (2) | |
O12 | 0.20082 (18) | 1.0163 (4) | 0.2506 (4) | 0.0519 (9) | |
O13 | 0.07487 (17) | 0.5181 (4) | 0.3735 (3) | 0.0429 (8) | |
O14 | 0.04324 (17) | 0.5500 (4) | 0.1730 (3) | 0.0417 (8) | |
O15 | 0.14568 (17) | 0.3921 (4) | 0.2219 (3) | 0.0451 (9) | |
C11 | 0.1420 (3) | 0.9984 (5) | 0.2567 (6) | 0.0501 (12) | |
C12 | 0.1083 (3) | 0.8438 (5) | 0.2678 (7) | 0.0577 (16) | |
C13 | 0.1512 (2) | 0.7024 (5) | 0.2433 (5) | 0.0426 (11) | |
P2 | 0.22451 (6) | 0.38493 (12) | 0.53461 (11) | 0.0353 (3) | |
O21 | 0.21387 (17) | −0.2113 (4) | 0.5093 (3) | 0.0451 (9) | |
O22 | 0.31199 (18) | −0.1005 (4) | 0.4738 (3) | 0.0505 (9) | |
O23 | 0.23345 (16) | 0.3816 (4) | 0.6663 (3) | 0.0393 (8) | |
O24 | 0.15009 (15) | 0.3965 (4) | 0.5195 (3) | 0.0393 (7) | |
O25 | 0.26564 (16) | 0.5123 (3) | 0.4808 (3) | 0.0383 (8) | |
C21 | 0.2535 (3) | −0.0882 (5) | 0.4985 (4) | 0.0398 (10) | |
C22 | 0.2190 (2) | 0.0597 (5) | 0.5268 (5) | 0.0416 (10) | |
C23 | 0.2546 (3) | 0.2034 (5) | 0.4835 (4) | 0.0409 (11) | |
O1 | 0.0298 (6) | 0.2034 (13) | 0.5328 (12) | 0.058 (4)* | 0.337 (13) |
C1 | 0.0061 (10) | 0.043 (2) | 0.5029 (16) | 0.058 (4)* | 0.337 (13) |
H1A | 0.3922 | 0.4278 | 0.1585 | 0.047* | |
H1B | 0.4570 | 0.4456 | 0.2167 | 0.047* | |
H4A | 0.4234 | 0.5552 | 0.5277 | 0.053* | |
H4B | 0.3580 | 0.5348 | 0.4721 | 0.053* | |
H2 | 0.3416 | 0.3439 | 0.3222 | 0.048* | |
H3A | 0.4084 | 0.2983 | 0.4820 | 0.054* | |
H3B | 0.4711 | 0.3692 | 0.4173 | 0.054* | |
H5A | 0.4055 | 0.7551 | 0.3995 | 0.052* | |
H5B | 0.4703 | 0.6574 | 0.3683 | 0.052* | |
H6 | 0.3438 | 0.6250 | 0.2645 | 0.050* | |
H7A | 0.3889 | 0.1553 | 0.1996 | 0.081* | |
H7B | 0.3895 | 0.0977 | 0.3276 | 0.081* | |
H7C | 0.4559 | 0.1617 | 0.2711 | 0.081* | |
H8A | 0.4014 | 0.8326 | 0.1901 | 0.081* | |
H8B | 0.4005 | 0.6961 | 0.0988 | 0.081* | |
H8C | 0.4657 | 0.7273 | 0.1717 | 0.081* | |
H11 | 0.1195 | 1.1981 | 0.2377 | 0.160* | |
H13 | 0.1052 | 0.4892 | 0.4170 | 0.064* | |
H12A | 0.0700 | 0.8419 | 0.2159 | 0.069* | |
H12B | 0.0909 | 0.8344 | 0.3453 | 0.069* | |
H13A | 0.1875 | 0.6965 | 0.2991 | 0.051* | |
H13B | 0.1712 | 0.7123 | 0.1676 | 0.051* | |
H21 | 0.2369 | −0.2921 | 0.5152 | 0.068* | |
H23 | 0.2704 | 0.4198 | 0.6833 | 0.059* | |
H22A | 0.2145 | 0.0674 | 0.6096 | 0.050* | |
H22B | 0.1739 | 0.0571 | 0.4944 | 0.050* | |
H23A | 0.2517 | 0.2041 | 0.4004 | 0.049* | |
H23B | 0.3019 | 0.1946 | 0.5037 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.033 (2) | 0.041 (2) | 0.043 (3) | −0.0025 (16) | −0.0003 (17) | −0.0034 (17) |
N4 | 0.040 (2) | 0.049 (2) | 0.043 (2) | 0.0000 (19) | 0.0051 (18) | −0.0033 (19) |
C2 | 0.036 (2) | 0.036 (2) | 0.049 (3) | −0.009 (2) | 0.000 (2) | 0.002 (2) |
C3 | 0.035 (2) | 0.049 (3) | 0.052 (3) | −0.002 (2) | −0.002 (2) | 0.003 (2) |
C5 | 0.039 (3) | 0.038 (2) | 0.055 (3) | 0.005 (2) | 0.001 (2) | −0.006 (2) |
C6 | 0.039 (2) | 0.038 (2) | 0.046 (3) | 0.001 (2) | −0.002 (2) | −0.001 (2) |
C7 | 0.046 (3) | 0.041 (3) | 0.074 (4) | −0.003 (2) | −0.001 (3) | 0.008 (3) |
C8 | 0.057 (3) | 0.041 (3) | 0.064 (4) | −0.001 (2) | −0.003 (3) | 0.005 (3) |
P1 | 0.0335 (6) | 0.0304 (5) | 0.0443 (6) | −0.0002 (5) | 0.0020 (6) | −0.0001 (6) |
O11 | 0.051 (3) | 0.0317 (19) | 0.237 (8) | 0.0030 (18) | 0.018 (4) | 0.021 (4) |
O12 | 0.049 (2) | 0.0370 (17) | 0.070 (2) | −0.0045 (15) | 0.006 (2) | −0.002 (2) |
O13 | 0.0378 (18) | 0.050 (2) | 0.0407 (18) | 0.0076 (16) | 0.0029 (15) | 0.0097 (16) |
O14 | 0.0342 (17) | 0.0475 (18) | 0.0433 (19) | 0.0004 (14) | 0.0023 (14) | −0.0046 (15) |
O15 | 0.0403 (18) | 0.0296 (15) | 0.065 (2) | 0.0002 (13) | 0.0091 (17) | −0.0100 (15) |
C11 | 0.048 (3) | 0.028 (2) | 0.075 (4) | −0.0027 (18) | −0.001 (3) | 0.000 (3) |
C12 | 0.051 (3) | 0.0210 (18) | 0.101 (5) | −0.001 (2) | 0.010 (3) | −0.002 (3) |
C13 | 0.040 (2) | 0.032 (2) | 0.055 (3) | 0.0001 (18) | 0.003 (2) | −0.002 (2) |
P2 | 0.0343 (6) | 0.0277 (5) | 0.0439 (6) | 0.0005 (4) | 0.0003 (6) | 0.0002 (6) |
O21 | 0.0430 (19) | 0.0264 (15) | 0.066 (3) | 0.0020 (13) | 0.0047 (17) | 0.0020 (16) |
O22 | 0.0395 (19) | 0.0381 (18) | 0.074 (3) | 0.0063 (15) | 0.0078 (18) | −0.0033 (18) |
O23 | 0.0357 (18) | 0.0374 (17) | 0.0449 (18) | −0.0023 (14) | −0.0029 (14) | −0.0013 (15) |
O24 | 0.0295 (15) | 0.0428 (16) | 0.045 (2) | 0.0025 (13) | 0.0002 (14) | 0.0045 (16) |
O25 | 0.0394 (19) | 0.0268 (14) | 0.0488 (19) | −0.0017 (13) | 0.0041 (15) | 0.0015 (13) |
C21 | 0.040 (2) | 0.034 (2) | 0.046 (3) | −0.007 (2) | 0.004 (2) | −0.005 (2) |
C22 | 0.036 (2) | 0.032 (2) | 0.057 (3) | −0.0024 (18) | 0.007 (2) | −0.001 (3) |
C23 | 0.043 (3) | 0.030 (2) | 0.049 (3) | 0.001 (2) | 0.008 (2) | 0.002 (2) |
N1—C2 | 1.497 (6) | P1—C13 | 1.785 (5) |
N1—C6 | 1.532 (6) | O11—C11 | 1.329 (6) |
N1—H1A | 0.92 | O11—H11 | 0.84 |
N1—H1B | 0.92 | O12—C11 | 1.201 (6) |
N4—C3 | 1.474 (7) | O13—H13 | 0.84 |
N4—C5 | 1.505 (7) | C11—C12 | 1.503 (6) |
N4—H4A | 0.92 | C12—C13 | 1.524 (7) |
N4—H4B | 0.92 | C12—H12A | 0.99 |
C2—C3 | 1.507 (7) | C12—H12B | 0.99 |
C2—C7 | 1.520 (7) | C13—H13A | 0.99 |
C2—H2 | 1.00 | C13—H13B | 0.99 |
C3—H3A | 0.99 | P2—O25 | 1.518 (3) |
C3—H3B | 0.99 | P2—O24 | 1.519 (3) |
C5—C6 | 1.503 (7) | P2—O23 | 1.575 (3) |
C5—H5A | 0.99 | P2—C23 | 1.785 (5) |
C5—H5B | 0.99 | O21—C21 | 1.335 (5) |
C6—C8 | 1.490 (8) | O21—H21 | 0.84 |
C6—H6 | 1.00 | O22—C21 | 1.224 (6) |
C7—H7A | 0.98 | O23—H23 | 0.84 |
C7—H7B | 0.98 | C21—C22 | 1.492 (6) |
C7—H7C | 0.98 | C22—C23 | 1.522 (6) |
C8—H8A | 0.98 | C22—H22A | 0.99 |
C8—H8B | 0.98 | C22—H22B | 0.99 |
C8—H8C | 0.98 | C23—H23A | 0.99 |
P1—O15 | 1.511 (3) | C23—H23B | 0.99 |
P1—O14 | 1.518 (4) | O1—C1 | 1.50 (2) |
P1—O13 | 1.575 (4) | ||
C2—N1—C6 | 111.4 (4) | H8B—C8—H8C | 109.5 |
C2—N1—H1A | 109.3 | O15—P1—O14 | 114.4 (2) |
C6—N1—H1A | 109.3 | O15—P1—O13 | 111.1 (2) |
C2—N1—H1B | 109.3 | O14—P1—O13 | 106.8 (2) |
C6—N1—H1B | 109.3 | O15—P1—C13 | 109.1 (2) |
H1A—N1—H1B | 108.0 | O14—P1—C13 | 108.3 (2) |
C3—N4—C5 | 111.6 (4) | O13—P1—C13 | 106.9 (2) |
C3—N4—H4A | 109.3 | C11—O11—H11 | 109.5 |
C5—N4—H4A | 109.3 | P1—O13—H13 | 109.5 |
C3—N4—H4B | 109.3 | O12—C11—O11 | 123.0 (4) |
C5—N4—H4B | 109.3 | O12—C11—C12 | 124.7 (5) |
H4A—N4—H4B | 108.0 | O11—C11—C12 | 112.4 (5) |
N1—C2—C3 | 109.8 (4) | C11—C12—C13 | 115.6 (5) |
N1—C2—C7 | 109.8 (4) | C11—C12—H12A | 108.4 |
C3—C2—C7 | 111.9 (4) | C13—C12—H12A | 108.4 |
N1—C2—H2 | 108.4 | C11—C12—H12B | 108.4 |
C3—C2—H2 | 108.4 | C13—C12—H12B | 108.4 |
C7—C2—H2 | 108.4 | H12A—C12—H12B | 107.4 |
N4—C3—C2 | 110.0 (4) | C12—C13—P1 | 110.0 (4) |
N4—C3—H3A | 109.7 | C12—C13—H13A | 109.7 |
C2—C3—H3A | 109.7 | P1—C13—H13A | 109.7 |
N4—C3—H3B | 109.7 | C12—C13—H13B | 109.7 |
C2—C3—H3B | 109.7 | P1—C13—H13B | 109.7 |
H3A—C3—H3B | 108.2 | H13A—C13—H13B | 108.2 |
C6—C5—N4 | 112.5 (4) | O25—P2—O24 | 116.47 (19) |
C6—C5—H5A | 109.1 | O25—P2—O23 | 111.6 (2) |
N4—C5—H5A | 109.1 | O24—P2—O23 | 103.4 (2) |
C6—C5—H5B | 109.1 | O25—P2—C23 | 107.7 (2) |
N4—C5—H5B | 109.1 | O24—P2—C23 | 110.8 (2) |
H5A—C5—H5B | 107.8 | O23—P2—C23 | 106.4 (2) |
C8—C6—C5 | 112.1 (4) | C21—O21—H21 | 109.5 |
C8—C6—N1 | 109.3 (4) | P2—O23—H23 | 109.5 |
C5—C6—N1 | 109.1 (4) | O22—C21—O21 | 122.3 (4) |
C8—C6—H6 | 108.8 | O22—C21—C22 | 125.5 (4) |
C5—C6—H6 | 108.8 | O21—C21—C22 | 112.1 (4) |
N1—C6—H6 | 108.8 | C21—C22—C23 | 113.4 (4) |
C2—C7—H7A | 109.5 | C21—C22—H22A | 108.9 |
C2—C7—H7B | 109.5 | C23—C22—H22A | 108.9 |
H7A—C7—H7B | 109.5 | C21—C22—H22B | 108.9 |
C2—C7—H7C | 109.5 | C23—C22—H22B | 108.9 |
H7A—C7—H7C | 109.5 | H22A—C22—H22B | 107.7 |
H7B—C7—H7C | 109.5 | C22—C23—P2 | 115.9 (3) |
C6—C8—H8A | 109.5 | C22—C23—H23A | 108.3 |
C6—C8—H8B | 109.5 | P2—C23—H23A | 108.3 |
H8A—C8—H8B | 109.5 | C22—C23—H23B | 108.3 |
C6—C8—H8C | 109.5 | P2—C23—H23B | 108.3 |
H8A—C8—H8C | 109.5 | H23A—C23—H23B | 107.4 |
C6—N1—C2—C3 | −58.9 (5) | O11—C11—C12—C13 | 165.1 (7) |
C6—N1—C2—C7 | 177.8 (4) | C11—C12—C13—P1 | −175.7 (5) |
C5—N4—C3—C2 | −57.7 (5) | O15—P1—C13—C12 | 178.2 (4) |
N1—C2—C3—N4 | 59.5 (5) | O14—P1—C13—C12 | 53.2 (5) |
C7—C2—C3—N4 | −178.3 (4) | O13—P1—C13—C12 | −61.6 (5) |
C3—N4—C5—C6 | 55.8 (5) | O22—C21—C22—C23 | 20.7 (8) |
N4—C5—C6—C8 | −174.2 (4) | O21—C21—C22—C23 | −163.0 (4) |
N4—C5—C6—N1 | −53.0 (5) | C21—C22—C23—P2 | −169.4 (4) |
C2—N1—C6—C8 | 178.1 (4) | O25—P2—C23—C22 | −179.3 (4) |
C2—N1—C6—C5 | 55.2 (5) | O24—P2—C23—C22 | −50.8 (5) |
O12—C11—C12—C13 | −14.0 (11) | O23—P2—C23—C22 | 60.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O24i | 0.92 | 1.88 | 2.798 (5) | 175 |
N1—H1A···O23i | 0.92 | 2.58 | 3.084 (5) | 116 |
N1—H1B···O14ii | 0.92 | 1.82 | 2.731 (5) | 170 |
N4—H4A···O14iii | 0.92 | 1.85 | 2.752 (6) | 165 |
N4—H4B···O25 | 0.92 | 1.88 | 2.792 (5) | 171 |
O11—H11···O15iv | 0.84 | 1.76 | 2.587 (5) | 166 |
O13—H13···O24 | 0.84 | 1.72 | 2.534 (5) | 164 |
O21—H21···O25v | 0.84 | 1.83 | 2.624 (4) | 157 |
O23—H23···O15iii | 0.84 | 1.77 | 2.533 (5) | 149 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) x+1/2, −y+1, z; (iii) −x+1/2, y, z+1/2; (iv) x, y+1, z; (v) x, y−1, z. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C12H12N22+·C12H10N2·2(C3H6O5P)− | C10H10N3+·C3H6O5P−·H2O | C4H12N22+·C3H5O5P2− | C6H16N22+·2(C3H6O5P−)·2(H2O) |
Mr | 672.55 | 343.27 | 240.20 | 458.34 |
Crystal system, space group | Monoclinic, P21/c | Orthorhombic, Fmm2 | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 150 | 150 | 150 | 150 |
a, b, c (Å) | 10.1600 (3), 10.4061 (3), 14.5441 (5) | 18.7267 (11), 22.6805 (11), 7.0893 (4) | 10.6065 (3), 7.9214 (2), 12.8892 (4) | 6.9270 (2), 20.6027 (5), 8.0115 (2) |
α, β, γ (°) | 90, 96.2880 (12), 90 | 90, 90, 90 | 90, 94.0540 (12), 90 | 90, 111.4092 (10), 90 |
V (Å3) | 1528.44 (8) | 3011.0 (3) | 1080.22 (5) | 1064.47 (5) |
Z | 2 | 8 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.21 | 0.22 | 0.26 | 0.26 |
Crystal size (mm) | 0.22 × 0.16 × 0.14 | 0.34 × 0.08 × 0.08 | 0.30 × 0.28 × 0.15 | 0.32 × 0.22 × 0.16 |
Data collection | ||||
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | – | – | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | – |
Tmin, Tmax | – | – | 0.904, 0.971 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13452, 3496, 2880 | 8696, 1703, 1445 | 6785, 2447, 2048 | 6838, 2415, 1990 |
Rint | 0.042 | 0.085 | 0.028 | 0.035 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.650 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.097, 1.04 | 0.045, 0.111, 1.04 | 0.034, 0.091, 1.04 | 0.036, 0.092, 1.05 |
No. of reflections | 3496 | 1703 | 2447 | 2415 |
No. of parameters | 210 | 216 | 137 | 135 |
No. of restraints | 0 | 33 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.42 | 0.19, −0.26 | 0.29, −0.39 | 0.34, −0.48 |
Absolute structure | ? | Flack (1983); 708 Friedel pairs | ? | ? |
Absolute structure parameter | ? | −0.2 (2) | ? | ? |
(V) | (VI) | (VII) | |
Crystal data | |||
Chemical formula | C10H8.82N20.72+·C3H6O5.28P0.72= | C12H14N22+·2(C3H6O5P−) | C6H16N22+·2(C3H6O5P−)·0.3(CH4O) |
Mr | 1240.98 | 492.35 | 429.31 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 | Orthorhombic, Pca21 |
Temperature (K) | 150 | 150 | 150 |
a, b, c (Å) | 11.3482 (5), 6.7178 (3), 17.7354 (7) | 7.5651 (3), 8.6472 (3), 9.0077 (4) | 20.2229 (17), 8.6162 (6), 11.8812 (9) |
α, β, γ (°) | 90, 97.4980 (18), 90 | 72.6340 (14), 73.1760 (15), 87.386 (2) | 90, 90, 90 |
V (Å3) | 1340.50 (10) | 537.79 (4) | 2070.2 (3) |
Z | 1 | 1 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.23 | 0.26 | 0.26 |
Crystal size (mm) | 0.22 × 0.20 × 0.08 | 0.30 × 0.14 × 0.12 | 0.24 × 0.10 × 0.04 |
Data collection | |||
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | – | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | – |
Tmin, Tmax | – | 0.930, 0.973 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13381, 3059, 2113 | 6047, 2457, 2163 | 15150, 4652, 3521 |
Rint | 0.060 | 0.035 | 0.125 |
(sin θ/λ)max (Å−1) | 0.649 | 0.652 | 0.649 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.120, 1.03 | 0.032, 0.085, 1.06 | 0.064, 0.168, 1.03 |
No. of reflections | 3059 | 2457 | 4652 |
No. of parameters | 194 | 148 | 250 |
No. of restraints | 0 | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.40 | 0.32, −0.37 | 0.56, −0.30 |
Absolute structure | ? | ? | Flack (1983), 2161 Friedel pairs |
Absolute structure parameter | ? | ? | 0.07 (15) |
Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997b), PLATON (Spek, 2002), SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O4 | 0.88 | 1.70 | 2.580 (2) | 177 |
O1—H1···N11 | 0.84 | 1.78 | 2.617 (2) | 176 |
O3—H3···O5i | 0.84 | 1.66 | 2.501 (2) | 176 |
C13—H13···O5ii | 0.95 | 2.55 | 3.489 (2) | 170 |
C17—H17···O5iii | 0.95 | 2.25 | 3.185 (2) | 169 |
C22—H22···O3iv | 0.95 | 2.41 | 3.292 (2) | 153 |
C23—H23···O2v | 0.95 | 2.59 | 3.361 (2) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x−1, −y+3/2, z−1/2; (iv) −x+1, y+1/2, −z+3/2; (v) x+1, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O6 | 0.84 | 1.76 | 2.579 (5) | 165 |
O3—H3···O6i | 0.84 | 2.60 | 3.308 (5) | 143 |
O1—H11···O5ii | 0.84 | 1.79 | 2.580 (4) | 156 |
N1—H1···O4 | 0.88 | 1.88 | 2.755 (4) | 173 |
N12—H12···N22 | 0.88 | 1.90 | 2.589 (5) | 134 |
N12—H12···O2iii | 0.88 | 2.27 | 2.961 (4) | 135 |
O6—H61···O5iv | 0.84 | 1.92 | 2.755 (6) | 177 |
O6—H62···O4v | 0.84 | 1.91 | 2.744 (4) | 172 |
Symmetry codes: (i) x, −y, z; (ii) −x, −y, z; (iii) −x+1/2, y+1/2, z; (iv) x, y, z−1; (v) −x+1/2, −y, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4i | 0.84 | 1.74 | 2.535 (2) | 157 |
N11—H11A···O1 | 0.92 | 1.78 | 2.686 (2) | 167 |
N11—H11B···O5ii | 0.92 | 1.72 | 2.640 (2) | 176 |
N21—H21A···O4iii | 0.92 | 1.82 | 2.738 (2) | 172 |
N21—H21B···O1 | 0.92 | 2.43 | 2.992 (2) | 119 |
N21—H21B···O2 | 0.92 | 1.79 | 2.690 (2) | 165 |
C13—H13B···O2iv | 0.99 | 2.41 | 3.243 (2) | 142 |
C22—H22A···O5v | 0.99 | 2.47 | 3.349 (2) | 148 |
C22—H22B···O3vi | 0.99 | 2.34 | 3.227 (2) | 149 |
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) x+1/2, −y+3/2, z−1/2; (vi) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5i | 0.84 | 1.74 | 2.562 (2) | 167 |
O3—H3···O6 | 0.84 | 1.73 | 2.562 (2) | 174 |
N11—H11···O4 | 0.93 | 1.71 | 2.622 (2) | 168 |
O6—H61···O4ii | 0.84 | 1.88 | 2.717 (2) | 176 |
O6—H62···O5iii | 0.83 | 1.88 | 2.707 (2) | 174 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N11 | 0.84 | 1.77 | 2.585 (2) | 164 |
O3—H3···O3i | 0.84 | 1.67 | 2.475 (2) | 160 |
O4—H4···N21ii | 0.84 | 1.77 | 2.558 (2) | 156 |
O5—H5···O5iii | 1.24 | 1.24 | 2.473 (2) | 180 |
N11—H11···O1 | 0.88 | 1.71 | 2.585 (2) | 173 |
N21—H21···O4iv | 0.88 | 1.68 | 2.558 (2) | 177 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+3/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) x−3/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O4 | 0.88 | 1.84 | 2.692 (2) | 161 |
O1—H1···O5i | 0.84 | 1.73 | 2.542 (2) | 163 |
O3—H3···O4ii | 0.84 | 1.79 | 2.619 (2) | 168 |
C12—H12···O2iii | 0.95 | 2.29 | 3.224 (2) | 167 |
C13—H13···O5iv | 0.95 | 2.41 | 3.196 (2) | 139 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) −x, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O24i | 0.92 | 1.88 | 2.798 (5) | 175 |
N1—H1A···O23i | 0.92 | 2.58 | 3.084 (5) | 116 |
N1—H1B···O14ii | 0.92 | 1.82 | 2.731 (5) | 170 |
N4—H4A···O14iii | 0.92 | 1.85 | 2.752 (6) | 165 |
N4—H4B···O25 | 0.92 | 1.88 | 2.792 (5) | 171 |
O11—H11···O15iv | 0.84 | 1.76 | 2.587 (5) | 166 |
O13—H13···O24 | 0.84 | 1.72 | 2.534 (5) | 164 |
O21—H21···O25v | 0.84 | 1.83 | 2.624 (4) | 157 |
O23—H23···O15iii | 0.84 | 1.77 | 2.533 (5) | 149 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) x+1/2, −y+1, z; (iii) −x+1/2, y, z+1/2; (iv) x, y+1, z; (v) x, y−1, z. |
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