Download citation
Download citation
link to html
The crystal structure of kinetin dihydrogenphosphate has been determined at 115 and 293 K. Kinetin dihydrogenphos­phate undergoes a polymorphic phase transition at 291.1 K. In both phases the crystal belongs to the triclinic system with the symmetry described by the space group P\bar 1. In the low-temperature phase, the unit cell is doubled along the a axis. There is a dynamic equilibrium between different tautomeric forms of the adenine residue, determined by the distribution of H atoms within the network of hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810502673X/gp5001sup1.cif
Contains datablocks 115, 293, paper

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810502673X/gp500115sup2.hkl
Contains datablock 15

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810502673X/gp5001115sup3.hkl
Contains datablock 115

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S010876810502673X/gp5001293sup4.fcf
Contains datablock 293

CCDC references: 298347; 298348

Computing details top

Data collection: CRYSaLIS PROCEDURE for 293. Cell refinement: CRYSaLIS PROCEDURE for 293. Data reduction: CRYSaLIS PROCEDURE for 293. For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: DIAMOND 2 for 293.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(115) top
Crystal data top
C10H12N5O5PZ = 4
Mr = 313.22F(000) = 648
Triclinic, P1Dx = 1.643 Mg m3
a = 8.9243 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.720 (2) ÅCell parameters from 5624 reflections
c = 14.295 (3) Åθ = 1.3–4.1°
α = 91.41 (3)°µ = 0.25 mm1
β = 100.75 (3)°T = 115 K
γ = 108.85 (3)°Thin, needle, colourless
V = 1266.2 (4) Å30.41 × 0.09 × 0.09 mm
Data collection top
KM4CCD
diffractometer
5604 independent reflections
Radiation source: fine-focus sealed tube5604 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: CCD pixels mm-1θmax = 28.1°, θmin = 2.6°
CCD scansh = 911
Absorption correction: ANALYTICAL- crysAlis Ver170.26
?
k = 1413
Tmin = 0.910, Tmax = 0.982l = 1818
11933 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119Calculated w = 1/[σ2(Fo2) + (0.040P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
S = 1.22(Δ/σ)max = 0.366
5604 reflectionsΔρmax = 0.66 e Å3
451 parametersΔρmin = 0.49 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00000 (19)
Crystal data top
C10H12N5O5Pγ = 108.85 (3)°
Mr = 313.22V = 1266.2 (4) Å3
Triclinic, P1Z = 4
a = 8.9243 (18) ÅMo Kα radiation
b = 10.720 (2) ŵ = 0.25 mm1
c = 14.295 (3) ÅT = 115 K
α = 91.41 (3)°0.41 × 0.09 × 0.09 mm
β = 100.75 (3)°
Data collection top
KM4CCD
diffractometer
5604 independent reflections
Absorption correction: ANALYTICAL- crysAlis Ver170.26
?
5604 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.982Rint = 0.049
11933 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.22(Δ/σ)max = 0.366
5604 reflectionsΔρmax = 0.66 e Å3
451 parametersΔρmin = 0.49 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.258675 (17)0.582058 (14)0.349123 (11)0.01303 (4)
O140.32806 (5)0.49898 (4)0.42273 (3)0.01967 (12)
O130.28265 (5)0.71693 (4)0.39431 (3)0.02124 (13)
O110.08116 (5)0.50476 (4)0.30711 (3)0.01675 (12)
O120.35224 (5)0.59204 (4)0.26664 (3)0.01947 (12)
P20.744779 (18)0.580556 (14)0.348245 (11)0.01408 (4)
O210.58020 (5)0.49509 (4)0.29008 (3)0.01659 (12)
O220.80272 (5)0.51551 (5)0.43261 (3)0.02431 (14)
O240.86877 (5)0.61866 (4)0.28136 (3)0.02002 (12)
O230.72490 (5)0.71416 (4)0.38014 (4)0.02953 (14)
N3A0.43288 (6)0.93466 (5)0.33384 (4)0.01585 (14)
N3B0.92187 (6)0.94488 (5)0.34791 (4)0.01787 (14)
N1B1.06869 (6)1.05476 (5)0.23065 (4)0.01769 (14)
N7A0.45402 (6)1.26300 (5)0.37371 (4)0.01543 (14)
N9A0.34856 (6)1.07372 (5)0.43783 (4)0.01657 (14)
N9B0.84433 (6)1.09571 (5)0.44545 (4)0.01653 (14)
N7B0.95034 (6)1.27878 (5)0.38205 (4)0.01570 (14)
N1A0.57722 (6)1.04557 (5)0.21931 (4)0.01723 (14)
C6B1.06024 (7)1.17390 (6)0.25746 (4)0.01481 (16)
C4B0.91659 (7)1.06430 (6)0.37517 (4)0.01510 (16)
C8B0.86802 (7)1.22608 (6)0.44756 (4)0.01751 (17)
C5A0.48855 (7)1.16628 (5)0.32549 (4)0.01431 (16)
C2A0.51132 (7)0.93972 (6)0.26212 (4)0.01722 (17)
N6B1.12164 (6)1.27880 (5)0.21158 (4)0.01675 (14)
C4A0.42180 (7)1.05120 (6)0.36615 (4)0.01424 (16)
C6A0.56655 (7)1.16404 (6)0.24825 (4)0.01436 (16)
N6A0.62922 (6)1.27112 (5)0.20491 (4)0.01728 (14)
C5B0.98354 (7)1.17957 (5)0.33502 (4)0.01399 (16)
C2B1.00165 (7)0.95015 (6)0.27631 (5)0.01913 (17)
C8A0.37259 (7)1.20346 (6)0.43947 (4)0.01696 (17)
C10A0.68851 (7)1.26754 (6)0.11594 (5)0.02013 (17)
C10B1.18666 (7)1.27282 (6)0.12502 (5)0.01981 (17)
C11A0.55868 (7)1.25542 (6)0.03094 (5)0.02177 (18)
C12B1.03694 (9)1.35284 (7)0.01344 (7)0.0425 (3)
C11B1.06245 (7)1.25828 (6)0.03689 (5)0.02159 (18)
C12A0.53515 (9)1.35116 (7)0.01963 (7)0.0473 (3)
O15A0.43382 (7)1.14135 (5)0.00432 (5)0.0503 (2)
O15B0.94531 (7)1.14240 (6)0.00584 (5)0.0535 (2)
C14B0.84718 (10)1.16537 (9)0.07549 (7)0.0540 (3)
C13B0.89981 (10)1.28997 (10)0.08914 (6)0.0566 (3)
C14A0.33063 (10)1.16623 (9)0.07322 (6)0.0532 (3)
C13A0.38689 (10)1.28857 (10)0.09029 (6)0.0640 (3)
H2A0.5233 (7)0.8592 (6)0.2408 (4)0.0110 (16)*
H7B0.9870 (8)1.3626 (7)0.3705 (5)0.0253 (19)*
H8A0.3406 (7)1.2540 (6)0.4845 (4)0.0150 (17)*
H6A0.6136 (8)1.3398 (7)0.2234 (5)0.029 (2)*
H8B0.8343 (7)1.2759 (6)0.4905 (5)0.0183 (18)*
H6B1.1116 (8)1.3490 (7)0.2326 (5)0.0251 (19)*
H7A0.4880 (8)1.3483 (7)0.3638 (5)0.032 (2)*
H0A10.7801 (7)1.3546 (6)0.1154 (5)0.0205 (18)*
H2B1.0154 (8)0.8652 (7)0.2542 (5)0.0261 (19)*
H0B11.2797 (7)1.3561 (6)0.1258 (5)0.0212 (18)*
H0A20.7278 (7)1.1911 (6)0.1140 (5)0.0195 (18)*
H0B21.2253 (8)1.1947 (6)0.1258 (5)0.0214 (18)*
H230.8011 (11)0.7971 (9)0.3700 (7)0.069 (3)*
H9B0.7850 (10)1.0386 (8)0.4838 (6)0.060 (3)*
H120.4319 (10)0.5654 (8)0.2747 (6)0.055 (3)*
H240.9400 (10)0.5833 (9)0.2888 (7)0.060 (3)*
H140.2752 (12)0.4929 (10)0.4816 (8)0.089 (4)*
H3A0.3782 (10)0.8473 (9)0.3583 (7)0.064 (3)*
H13B0.8728 (12)1.3363 (10)0.1376 (8)0.092 (4)*
H14B0.7532 (18)1.0813 (15)0.1039 (11)0.172 (6)*
H14A0.2238 (17)1.0805 (14)0.0982 (11)0.158 (6)*
H13A0.3651 (14)1.3354 (12)0.1355 (9)0.117 (5)*
H12B1.0680 (7)1.3898 (6)0.0113 (4)0.0087 (16)*
H12A0.5684 (7)1.3891 (6)0.0180 (4)0.0115 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01350 (6)0.01263 (6)0.01499 (7)0.00548 (5)0.00555 (6)0.00389 (5)
O140.02151 (19)0.02299 (19)0.0185 (2)0.01141 (15)0.00591 (17)0.00805 (16)
O130.0273 (2)0.01304 (18)0.0242 (2)0.00408 (16)0.01210 (18)0.00252 (16)
O110.01348 (17)0.01445 (17)0.0242 (2)0.00509 (14)0.00728 (16)0.00461 (16)
O120.01777 (17)0.02859 (19)0.0192 (2)0.01389 (14)0.00916 (16)0.01052 (17)
P20.01436 (6)0.01412 (6)0.01535 (7)0.00466 (5)0.00686 (6)0.00318 (5)
O210.01500 (17)0.01529 (17)0.0214 (2)0.00665 (14)0.00557 (16)0.00247 (16)
O220.0219 (2)0.0347 (2)0.0159 (2)0.00824 (17)0.00417 (18)0.00906 (18)
O240.01831 (17)0.02614 (19)0.0237 (2)0.01304 (15)0.01243 (16)0.01285 (17)
O230.0344 (2)0.01376 (19)0.0433 (3)0.00213 (17)0.02606 (19)0.00167 (18)
N3A0.0169 (2)0.0127 (2)0.0175 (2)0.00391 (17)0.0040 (2)0.00284 (18)
N3B0.0181 (2)0.0149 (2)0.0210 (3)0.00554 (17)0.0047 (2)0.00347 (19)
N1B0.0183 (2)0.0167 (2)0.0194 (2)0.00610 (17)0.0064 (2)0.00202 (19)
N7A0.0158 (2)0.0140 (2)0.0170 (2)0.00489 (17)0.00438 (19)0.00234 (18)
N9A0.0158 (2)0.0175 (2)0.0157 (2)0.00429 (18)0.0036 (2)0.00273 (19)
N9B0.0166 (2)0.0171 (2)0.0163 (2)0.00507 (18)0.0048 (2)0.00468 (19)
N7B0.0158 (2)0.0134 (2)0.0180 (2)0.00418 (17)0.0046 (2)0.00327 (19)
N1A0.0177 (2)0.0165 (2)0.0188 (2)0.00633 (17)0.0057 (2)0.00331 (19)
C6B0.0123 (2)0.0160 (2)0.0142 (3)0.0031 (2)0.0010 (2)0.0016 (2)
C4B0.0105 (2)0.0174 (2)0.0156 (3)0.0029 (2)0.0013 (2)0.0026 (2)
C8B0.0151 (3)0.0193 (3)0.0174 (3)0.0047 (2)0.0032 (2)0.0026 (2)
C5A0.0123 (2)0.0146 (2)0.0153 (3)0.00459 (19)0.0009 (2)0.0008 (2)
C2A0.0184 (3)0.0155 (2)0.0185 (3)0.0070 (2)0.0031 (2)0.0011 (2)
N6B0.0187 (2)0.0148 (2)0.0171 (2)0.00480 (17)0.0062 (2)0.00155 (19)
C4A0.0110 (2)0.0148 (2)0.0150 (3)0.00363 (19)0.0008 (2)0.0024 (2)
C6A0.0098 (2)0.0174 (2)0.0153 (3)0.00452 (19)0.0012 (2)0.0021 (2)
N6A0.0192 (2)0.0166 (2)0.0172 (2)0.00573 (18)0.0068 (2)0.00307 (19)
C5B0.0116 (2)0.0140 (2)0.0157 (3)0.00437 (19)0.0009 (2)0.0016 (2)
C2B0.0207 (3)0.0156 (2)0.0217 (3)0.0071 (2)0.0040 (2)0.0027 (2)
C8A0.0148 (3)0.0182 (3)0.0173 (3)0.0043 (2)0.0037 (2)0.0029 (2)
C10A0.0213 (3)0.0217 (3)0.0210 (3)0.0078 (2)0.0114 (2)0.0080 (2)
C10B0.0195 (3)0.0226 (3)0.0201 (3)0.0072 (2)0.0102 (2)0.0063 (2)
C11A0.0250 (3)0.0251 (3)0.0200 (3)0.0105 (2)0.0121 (2)0.0036 (2)
C12B0.0310 (4)0.0248 (3)0.0734 (6)0.0118 (3)0.0077 (4)0.0251 (3)
C11B0.0220 (3)0.0277 (3)0.0192 (3)0.0100 (2)0.0113 (2)0.0021 (2)
C12A0.0367 (4)0.0331 (3)0.0849 (6)0.0192 (3)0.0252 (4)0.0396 (3)
O15A0.0471 (3)0.0360 (3)0.0597 (4)0.0157 (2)0.0112 (3)0.0003 (3)
O15B0.0467 (3)0.0369 (3)0.0658 (4)0.0137 (2)0.0142 (3)0.0024 (3)
C14B0.0477 (4)0.0687 (4)0.0461 (5)0.0385 (3)0.0196 (4)0.0238 (4)
C13B0.0565 (4)0.1079 (5)0.0352 (4)0.0586 (3)0.0212 (3)0.0402 (4)
C14A0.0526 (4)0.0759 (4)0.0373 (4)0.0460 (3)0.0163 (4)0.0236 (4)
C13A0.0736 (4)0.1233 (5)0.0395 (4)0.0781 (3)0.0330 (3)0.0487 (4)
Geometric parameters (Å, º) top
P1—O131.5020 (6)N9B—C4B1.3798 (9)
P1—O111.5262 (7)N9B—H9B0.933 (9)
P1—O121.5540 (6)N7B—C8B1.3229 (9)
P1—O141.5630 (7)N7B—C5B1.3833 (9)
O14—O122.4840 (9)N7B—O11v2.6732 (11)
O14—O112.5150 (10)N7B—H7B0.883 (7)
O14—O132.5268 (8)N1A—C2A1.3210 (9)
O14—O22i2.5420 (9)N1A—C6A1.3639 (9)
O14—O213.2107 (11)C6B—N6B1.3293 (9)
O14—O14i3.4241 (14)C6B—C5B1.4171 (10)
O14—H141.033 (11)C4B—C5B1.3780 (9)
O13—O112.5182 (13)C8B—H8B0.954 (7)
O13—O122.5196 (9)C5A—C4A1.3799 (9)
O13—N3A2.5499 (11)C5A—C6A1.4144 (10)
O11—O122.4797 (9)C2A—H2A0.953 (7)
O11—O24ii2.5449 (9)N6B—C10B1.4695 (10)
O11—N7Biii2.6732 (11)N6B—H6B0.841 (7)
O11—O22ii3.3532 (11)C6A—N6A1.3280 (9)
O12—O212.5417 (9)N6A—C10A1.4699 (9)
O12—O233.2367 (14)N6A—H6A0.838 (8)
O12—H120.838 (10)C2B—H2B1.008 (8)
P2—O221.4999 (7)C8A—H8A0.970 (7)
P2—O211.5249 (8)C10A—C11A1.4851 (10)
P2—O241.5579 (7)C10A—O15A2.4690 (14)
P2—O231.5661 (6)C10A—H0A11.025 (6)
O21—O232.4720 (12)C10A—H0A20.992 (7)
O21—O242.5151 (10)C10B—C11B1.4826 (10)
O21—O222.5160 (11)C10B—O15B2.4626 (14)
O22—O242.5331 (10)C10B—H0B11.002 (6)
O22—O232.5337 (9)C10B—H0B21.003 (7)
O22—O14i2.5420 (9)C11A—C12A1.3187 (12)
O22—O11iv3.3532 (11)C11A—O15A1.3491 (9)
O24—O232.4788 (10)C12B—C11B1.3117 (11)
O24—O11iv2.5449 (9)C12B—C13B1.4352 (12)
O24—H240.832 (10)C12B—O15B2.1809 (11)
O23—N3B2.6397 (11)C12B—H12B0.400 (5)
O23—H230.963 (9)C11B—O15B1.3393 (9)
N3A—C2A1.3379 (9)C12A—C13A1.4545 (13)
N3A—C4A1.3610 (9)C12A—O15A2.1983 (11)
N3A—H3A1.011 (9)C12A—H12A0.416 (6)
N3B—C2B1.3440 (10)O15A—C14A1.3929 (12)
N3B—C4B1.3469 (9)O15A—C13A2.1945 (13)
N1B—C2B1.3377 (9)O15B—C14B1.3974 (12)
N1B—C6B1.3538 (9)O15B—C13B2.1967 (13)
N7A—C8A1.3430 (9)C14B—C13B1.2978 (14)
N7A—C5A1.3768 (9)C14B—H14B1.024 (13)
N7A—H7A0.889 (7)C13B—H13B0.904 (11)
N9A—C8A1.3359 (9)C14A—C13A1.2913 (14)
N9A—C4A1.3692 (9)C14A—H14A1.082 (12)
N9B—C8B1.3429 (9)C13A—H13A0.860 (13)
O13—P1—O11112.52 (4)P2—O23—O1287.06 (4)
O13—P1—O12111.07 (4)O21—O23—O1250.74 (3)
O11—P1—O12107.23 (3)O24—O23—O12102.74 (3)
O13—P1—O14111.05 (3)O22—O23—O12104.97 (3)
O11—P1—O14109.00 (4)N3B—O23—O12122.62 (3)
O12—P1—O14105.68 (3)P2—O23—H23120.1 (6)
P1—O14—O1237.04 (2)O21—O23—H23137.2 (6)
P1—O14—O1135.02 (2)O24—O23—H2383.6 (6)
O12—O14—O1159.47 (3)O22—O23—H23124.0 (6)
P1—O14—O1333.69 (2)N3B—O23—H232.8 (6)
O12—O14—O1360.37 (3)O12—O23—H23125.3 (6)
O11—O14—O1359.93 (3)C2A—N3A—C4A116.21 (6)
P1—O14—O22i109.50 (3)C2A—N3A—O13122.42 (5)
O12—O14—O22i146.45 (3)C4A—N3A—O13120.97 (5)
O11—O14—O22i94.15 (3)C2A—N3A—H3A120.8 (6)
O13—O14—O22i89.30 (3)C4A—N3A—H3A122.8 (6)
P1—O14—O2188.04 (3)O13—N3A—H3A2.7 (6)
O12—O14—O2151.09 (2)C2B—N3B—C4B112.16 (6)
O11—O14—O21104.24 (3)C2B—N3B—O23119.03 (5)
O13—O14—O21102.87 (3)C4B—N3B—O23125.67 (5)
O22i—O14—O21161.27 (2)C2B—N1B—C6B118.90 (6)
P1—O14—O14i143.00 (3)C8A—N7A—C5A106.47 (5)
O12—O14—O14i118.83 (3)C8A—N7A—H7A129.2 (5)
O11—O14—O14i178.00 (2)C5A—N7A—H7A124.1 (5)
O13—O14—O14i118.52 (4)C8A—N9A—C4A103.38 (6)
O22i—O14—O14i87.04 (3)C8B—N9B—C4B107.65 (6)
O21—O14—O14i74.69 (2)C8B—N9B—H9B124.4 (6)
P1—O14—H14109.7 (6)C4B—N9B—H9B127.9 (6)
O12—O14—H14146.7 (6)C8B—N7B—C5B108.27 (5)
O11—O14—H1494.4 (6)C8B—N7B—O11v144.04 (5)
O13—O14—H1489.5 (6)C5B—N7B—O11v107.68 (4)
O22i—O14—H140.2 (6)C8B—N7B—H7B128.8 (5)
O21—O14—H14161.0 (6)C5B—N7B—H7B122.8 (5)
O14i—O14—H1486.8 (6)O11v—N7B—H7B15.4 (5)
P1—O13—O1134.04 (2)C2A—N1A—C6A119.12 (6)
P1—O13—O1235.14 (2)N6B—C6B—N1B120.24 (6)
O11—O13—O1258.97 (3)N6B—C6B—C5B122.88 (6)
P1—O13—O1435.26 (2)N1B—C6B—C5B116.88 (6)
O11—O13—O1459.80 (3)N3B—C4B—C5B124.80 (6)
O12—O13—O1458.97 (3)N3B—C4B—N9B128.06 (6)
P1—O13—N3A124.73 (3)C5B—C4B—N9B107.14 (6)
O11—O13—N3A131.51 (3)N7B—C8B—N9B110.11 (6)
O12—O13—N3A89.73 (3)N7B—C8B—H8B123.6 (4)
O14—O13—N3A136.37 (3)N9B—C8B—H8B126.2 (4)
P1—O11—O1236.77 (2)N7A—C5A—C4A105.32 (6)
P1—O11—O1435.99 (2)N7A—C5A—C6A134.31 (6)
O12—O11—O1459.64 (3)C4A—C5A—C6A120.32 (6)
P1—O11—O1333.43 (2)N1A—C2A—N3A126.67 (6)
O12—O11—O1360.54 (3)N1A—C2A—H2A116.6 (4)
O14—O11—O1360.27 (3)N3A—C2A—H2A116.7 (4)
P1—O11—O24ii121.32 (3)C6B—N6B—C10B123.87 (6)
O12—O11—O24ii125.05 (3)C6B—N6B—H6B114.4 (5)
O14—O11—O24ii142.57 (3)C10B—N6B—H6B121.4 (5)
O13—O11—O24ii88.74 (3)N3A—C4A—N9A128.19 (6)
P1—O11—N7Biii116.69 (4)N3A—C4A—C5A120.54 (6)
O12—O11—N7Biii128.57 (3)N9A—C4A—C5A111.27 (6)
O14—O11—N7Biii80.85 (4)N6A—C6A—N1A120.06 (6)
O13—O11—N7Biii127.33 (3)N6A—C6A—C5A122.84 (6)
O24ii—O11—N7Biii106.37 (3)N1A—C6A—C5A117.09 (6)
P1—O11—O22ii118.57 (3)C6A—N6A—C10A123.58 (6)
O12—O11—O22ii152.84 (2)C6A—N6A—H6A115.7 (5)
O14—O11—O22ii108.12 (3)C10A—N6A—H6A119.3 (5)
O13—O11—O22ii92.30 (3)C4B—C5B—N7B106.83 (6)
O24ii—O11—O22ii48.52 (2)C4B—C5B—C6B118.72 (6)
N7Biii—O11—O22ii66.09 (3)N7B—C5B—C6B134.38 (6)
P1—O12—O1136.01 (2)N1B—C2B—N3B128.47 (6)
P1—O12—O1437.29 (2)N1B—C2B—H2B114.8 (4)
O11—O12—O1460.89 (3)N3B—C2B—H2B116.7 (4)
P1—O12—O1333.80 (2)N9A—C8A—N7A113.55 (6)
O11—O12—O1360.49 (3)N9A—C8A—H8A125.4 (4)
O14—O12—O1360.66 (2)N7A—C8A—H8A120.9 (4)
P1—O12—O21116.57 (3)N6A—C10A—C11A111.07 (6)
O11—O12—O21129.38 (3)N6A—C10A—O15A100.41 (5)
O14—O12—O2179.40 (3)C11A—C10A—O15A27.89 (3)
O13—O12—O21125.84 (3)N6A—C10A—H0A1108.6 (4)
P1—O12—O23102.03 (3)C11A—C10A—H0A1107.7 (4)
O11—O12—O23137.44 (3)O15A—C10A—H0A1135.0 (4)
O14—O12—O2379.91 (3)N6A—C10A—H0A2108.2 (4)
O13—O12—O2387.08 (3)C11A—C10A—H0A2110.2 (3)
O21—O12—O2348.86 (2)O15A—C10A—H0A290.8 (3)
P1—O12—H12117.8 (6)H0A1—C10A—H0A2110.9 (5)
O11—O12—H12132.8 (6)N6B—C10B—C11B111.70 (6)
O14—O12—H1281.0 (6)N6B—C10B—O15B102.89 (4)
O13—O12—H12124.5 (6)C11B—C10B—O15B27.64 (3)
O21—O12—H123.9 (5)N6B—C10B—H0B1109.0 (4)
O23—O12—H1245.4 (5)C11B—C10B—H0B1109.2 (4)
O22—P2—O21112.57 (4)O15B—C10B—H0B1135.3 (4)
O22—P2—O24111.85 (3)N6B—C10B—H0B2108.1 (4)
O21—P2—O24109.34 (3)C11B—C10B—H0B2109.3 (3)
O22—P2—O23111.44 (4)O15B—C10B—H0B288.6 (3)
O21—P2—O23106.21 (4)H0B1—C10B—H0B2109.7 (6)
O24—P2—O23105.02 (4)C12A—C11A—O15A110.97 (6)
P2—O21—O2337.47 (3)C12A—C11A—C10A127.35 (6)
P2—O21—O2435.77 (2)O15A—C11A—C10A121.11 (7)
O23—O21—O2459.60 (3)C11B—C12B—C13B106.35 (7)
P2—O21—O2233.40 (2)C11B—C12B—O15B35.06 (4)
O23—O21—O2261.05 (3)C13B—C12B—O15B71.46 (6)
O24—O21—O2260.46 (3)C11B—C12B—H12B124.8 (9)
P2—O21—O12117.87 (3)C13B—C12B—H12B127.4 (9)
O23—O21—O1280.40 (3)O15B—C12B—H12B159.3 (9)
O24—O21—O12125.22 (3)C12B—C11B—O15B110.70 (6)
O22—O21—O12130.72 (3)C12B—C11B—C10B127.30 (6)
P2—O21—O14104.89 (3)O15B—C11B—C10B121.47 (7)
O23—O21—O1480.61 (3)C11A—C12A—C13A105.37 (7)
O24—O21—O14138.76 (3)C11A—C12A—O15A34.96 (4)
O22—O21—O1492.30 (3)C13A—C12A—O15A70.52 (6)
O12—O21—O1449.51 (2)C11A—C12A—H12A125.1 (9)
P2—O22—O2134.03 (2)C13A—C12A—H12A128.7 (9)
P2—O22—O2434.81 (2)O15A—C12A—H12A159.8 (9)
O21—O22—O2459.75 (3)C11A—O15A—C14A106.30 (7)
P2—O22—O2335.12 (2)C11A—O15A—C13A72.66 (5)
O21—O22—O2358.62 (3)C14A—O15A—C13A33.66 (5)
O24—O22—O2358.58 (3)C11A—O15A—C12A34.07 (4)
P2—O22—O14i119.28 (3)C14A—O15A—C12A72.33 (6)
O21—O22—O14i105.58 (3)C13A—O15A—C12A38.67 (4)
O24—O22—O14i151.27 (3)C11A—O15A—C10A31.00 (4)
O23—O22—O14i92.76 (3)C14A—O15A—C10A137.21 (5)
P2—O22—O11iv82.78 (3)C13A—O15A—C10A103.55 (4)
O21—O22—O11iv96.04 (3)C12A—O15A—C10A64.88 (4)
O24—O22—O11iv48.83 (2)C11B—O15B—C14B106.30 (7)
O23—O22—O11iv104.68 (3)C11B—O15B—C12B34.24 (4)
O14i—O22—O11iv157.25 (2)C14B—O15B—C12B72.20 (6)
P2—O24—O2337.61 (2)C11B—O15B—C13B72.41 (5)
P2—O24—O2134.90 (2)C14B—O15B—C13B33.93 (5)
O23—O24—O2159.34 (3)C12B—O15B—C13B38.28 (4)
P2—O24—O2233.34 (2)C11B—O15B—C10B30.90 (4)
O23—O24—O2260.72 (3)C14B—O15B—C10B137.16 (5)
O21—O24—O2259.79 (3)C12B—O15B—C10B64.97 (4)
P2—O24—O11iv114.79 (3)C13B—O15B—C10B103.23 (4)
O23—O24—O11iv137.83 (3)C13B—C14B—O15B109.13 (7)
O21—O24—O11iv120.77 (3)C13B—C14B—H14B139.2 (9)
O22—O24—O11iv82.65 (3)O15B—C14B—H14B111.6 (9)
P2—O24—H24116.6 (6)C14B—C13B—C12B107.20 (9)
O23—O24—H24138.8 (7)C14B—C13B—O15B36.94 (5)
O21—O24—H24122.5 (6)C12B—C13B—O15B70.26 (6)
O22—O24—H2484.3 (7)C14B—C13B—H13B132.4 (6)
O11iv—O24—H241.9 (6)C12B—C13B—H13B120.0 (6)
P2—O23—O2136.323 (19)O15B—C13B—H13B168.1 (7)
P2—O23—O2437.37 (2)C13A—C14A—O15A109.63 (7)
O21—O23—O2461.06 (3)C13A—C14A—H14A138.5 (8)
P2—O23—O2233.436 (19)O15A—C14A—H14A111.7 (8)
O21—O23—O2260.33 (3)C14A—C13A—C12A107.52 (9)
O24—O23—O2260.70 (3)C14A—C13A—O15A36.72 (5)
P2—O23—N3B121.70 (3)C12A—C13A—O15A70.80 (6)
O21—O23—N3B136.80 (3)C14A—C13A—H13A135.7 (7)
O24—O23—N3B84.93 (3)C12A—C13A—H13A116.1 (7)
O22—O23—N3B126.66 (3)O15A—C13A—H13A169.7 (8)
O13—P1—O14—O12120.53 (4)O12—O21—O22—O11iv146.86 (3)
O11—P1—O14—O12114.96 (4)O14—O21—O22—O11iv178.522 (15)
O13—P1—O14—O11124.51 (4)O22—P2—O24—O23121.02 (4)
O12—P1—O14—O11114.96 (4)O21—P2—O24—O23113.60 (4)
O11—P1—O14—O13124.51 (4)O22—P2—O24—O21125.37 (4)
O12—P1—O14—O13120.53 (4)O23—P2—O24—O21113.60 (4)
O13—P1—O14—O22i56.34 (4)O21—P2—O24—O22125.37 (4)
O11—P1—O14—O22i68.18 (4)O23—P2—O24—O22121.02 (4)
O12—P1—O14—O22i176.87 (2)O22—P2—O24—O11iv16.55 (3)
O13—P1—O14—O21116.95 (3)O21—P2—O24—O11iv108.83 (3)
O11—P1—O14—O21118.54 (3)O23—P2—O24—O11iv137.57 (3)
O12—P1—O14—O213.585 (19)O23—O21—O24—P240.55 (3)
O13—P1—O14—O14i55.93 (7)O22—O21—O24—P231.24 (2)
O11—P1—O14—O14i179.56 (5)O12—O21—O24—P289.94 (4)
O12—P1—O14—O14i64.61 (6)O14—O21—O24—P223.55 (3)
O12—P1—O13—O11120.22 (4)P2—O21—O24—O2340.55 (3)
O14—P1—O13—O11122.49 (4)O22—O21—O24—O2371.78 (3)
O11—P1—O13—O12120.22 (4)O12—O21—O24—O2349.40 (3)
O14—P1—O13—O12117.29 (4)O14—O21—O24—O2316.99 (3)
O11—P1—O13—O14122.49 (4)P2—O21—O24—O2231.24 (2)
O12—P1—O13—O14117.29 (4)O23—O21—O24—O2271.78 (3)
O11—P1—O13—N3A114.48 (4)O12—O21—O24—O22121.18 (4)
O12—P1—O13—N3A5.74 (4)O14—O21—O24—O2254.79 (4)
O14—P1—O13—N3A123.03 (4)P2—O21—O24—O11iv89.98 (4)
O12—O14—O13—P136.64 (2)O23—O21—O24—O11iv130.52 (3)
O11—O14—O13—P133.12 (3)O22—O21—O24—O11iv58.74 (4)
O22i—O14—O13—P1128.31 (3)O12—O21—O24—O11iv179.92 (2)
O21—O14—O13—P166.05 (3)O14—O21—O24—O11iv113.53 (4)
O14i—O14—O13—P1145.44 (4)O21—O22—O24—P232.67 (2)
P1—O14—O13—O1133.12 (3)O23—O22—O24—P236.83 (3)
O12—O14—O13—O1169.76 (3)O14i—O22—O24—P232.68 (4)
O22i—O14—O13—O1195.20 (3)O11iv—O22—O24—P2164.89 (3)
O21—O14—O13—O1199.16 (3)P2—O22—O24—O2336.83 (3)
O14i—O14—O13—O11178.56 (3)O21—O22—O24—O2369.50 (3)
P1—O14—O13—O1236.64 (2)O14i—O22—O24—O234.16 (4)
O11—O14—O13—O1269.76 (3)O11iv—O22—O24—O23158.28 (2)
O22i—O14—O13—O12164.96 (2)P2—O22—O24—O2132.67 (2)
O21—O14—O13—O1229.40 (2)O23—O22—O24—O2169.50 (3)
O14i—O14—O13—O12108.79 (4)O14i—O22—O24—O2165.35 (5)
P1—O14—O13—N3A86.94 (5)O11iv—O22—O24—O21132.22 (3)
O12—O14—O13—N3A50.29 (4)P2—O22—O24—O11iv164.89 (3)
O11—O14—O13—N3A120.05 (4)O21—O22—O24—O11iv132.22 (3)
O22i—O14—O13—N3A144.75 (4)O23—O22—O24—O11iv158.28 (2)
O21—O14—O13—N3A20.89 (4)O14i—O22—O24—O11iv162.43 (4)
O14i—O14—O13—N3A58.50 (5)O22—P2—O23—O21122.92 (4)
O13—P1—O11—O12122.41 (4)O24—P2—O23—O21115.79 (4)
O14—P1—O11—O12113.95 (4)O22—P2—O23—O24121.29 (4)
O13—P1—O11—O14123.64 (4)O21—P2—O23—O24115.79 (4)
O12—P1—O11—O14113.95 (4)O21—P2—O23—O22122.92 (4)
O12—P1—O11—O13122.41 (4)O24—P2—O23—O22121.29 (4)
O14—P1—O11—O13123.64 (4)O22—P2—O23—N3B109.76 (4)
O13—P1—O11—O24ii14.43 (4)O21—P2—O23—N3B127.32 (4)
O12—P1—O11—O24ii107.98 (4)O24—P2—O23—N3B11.53 (4)
O14—P1—O11—O24ii138.07 (3)O22—P2—O23—O12123.18 (4)
O13—P1—O11—N7Biii118.05 (3)O21—P2—O23—O120.26 (2)
O12—P1—O11—N7Biii119.54 (4)O24—P2—O23—O12115.53 (3)
O14—P1—O11—N7Biii5.59 (4)O24—O21—O23—P238.65 (2)
O13—P1—O11—O22ii42.11 (4)O22—O21—O23—P232.16 (3)
O12—P1—O11—O22ii164.52 (3)O12—O21—O23—P2179.67 (3)
O14—P1—O11—O22ii81.53 (4)O14—O21—O23—P2130.09 (3)
O12—O14—O11—P139.34 (3)P2—O21—O23—O2438.65 (2)
O13—O14—O11—P131.89 (2)O22—O21—O23—O2470.81 (3)
O22i—O14—O11—P1118.67 (4)O12—O21—O23—O24141.02 (2)
O21—O14—O11—P164.93 (4)O14—O21—O23—O24168.74 (2)
O14i—O14—O11—P17.6 (8)P2—O21—O23—O2232.16 (3)
P1—O14—O11—O1239.34 (3)O24—O21—O23—O2270.81 (3)
O13—O14—O11—O1271.23 (3)O12—O21—O23—O22148.17 (3)
O22i—O14—O11—O12158.01 (2)O14—O21—O23—O2297.93 (3)
O21—O14—O11—O1225.59 (2)P2—O21—O23—N3B81.24 (5)
O14i—O14—O11—O1231.8 (8)O24—O21—O23—N3B42.59 (4)
P1—O14—O11—O1331.89 (2)O22—O21—O23—N3B113.40 (4)
O12—O14—O11—O1371.23 (3)O12—O21—O23—N3B98.43 (4)
O22i—O14—O11—O1386.79 (4)O14—O21—O23—N3B148.67 (4)
O21—O14—O11—O1396.81 (4)P2—O21—O23—O12179.67 (3)
O14i—O14—O11—O1339.5 (8)O24—O21—O23—O12141.02 (2)
P1—O14—O11—O24ii69.92 (4)O22—O21—O23—O12148.17 (3)
O12—O14—O11—O24ii109.26 (4)O14—O21—O23—O1250.24 (2)
O13—O14—O11—O24ii38.03 (4)O21—O24—O23—P237.55 (3)
O22i—O14—O11—O24ii48.75 (4)O22—O24—O23—P232.68 (3)
O21—O14—O11—O24ii134.85 (4)O11iv—O24—O23—P265.83 (5)
O14i—O14—O11—O24ii77.5 (8)P2—O24—O23—O2137.55 (3)
P1—O14—O11—N7Biii174.95 (3)O22—O24—O23—O2170.23 (3)
O12—O14—O11—N7Biii145.71 (3)O11iv—O24—O23—O21103.38 (4)
O13—O14—O11—N7Biii143.06 (3)P2—O24—O23—O2232.68 (3)
O22i—O14—O11—N7Biii56.28 (3)O21—O24—O23—O2270.23 (3)
O21—O14—O11—N7Biii120.12 (3)O11iv—O24—O23—O2233.15 (3)
O14i—O14—O11—N7Biii177.5 (8)P2—O24—O23—N3B170.17 (3)
P1—O14—O11—O22ii113.94 (4)O21—O24—O23—N3B152.28 (3)
O12—O14—O11—O22ii153.28 (2)O22—O24—O23—N3B137.49 (3)
O13—O14—O11—O22ii82.06 (4)O11iv—O24—O23—N3B104.34 (5)
O22i—O14—O11—O22ii4.73 (3)P2—O24—O23—O1267.51 (4)
O21—O14—O11—O22ii178.869 (15)O21—O24—O23—O1229.96 (2)
O14i—O14—O11—O22ii121.5 (8)O22—O24—O23—O12100.19 (3)
O12—O13—O11—P135.48 (3)O11iv—O24—O23—O12133.33 (3)
O14—O13—O11—P134.29 (3)O21—O22—O23—P234.91 (3)
N3A—O13—O11—P192.82 (5)O24—O22—O23—P236.50 (3)
P1—O13—O11—O1235.48 (3)O14i—O22—O23—P2141.50 (3)
O14—O13—O11—O1269.77 (3)O11iv—O22—O23—P253.24 (3)
N3A—O13—O11—O1257.34 (4)P2—O22—O23—O2134.91 (3)
P1—O13—O11—O1434.29 (3)O24—O22—O23—O2171.41 (3)
O12—O13—O11—O1469.77 (3)O14i—O22—O23—O21106.59 (3)
N3A—O13—O11—O14127.11 (4)O11iv—O22—O23—O2188.15 (3)
P1—O13—O11—O24ii167.71 (3)P2—O22—O23—O2436.50 (3)
O12—O13—O11—O24ii132.23 (3)O21—O22—O23—O2471.41 (3)
O14—O13—O11—O24ii158.00 (2)O14i—O22—O23—O24178.001 (19)
N3A—O13—O11—O24ii74.89 (4)O11iv—O22—O23—O2416.739 (18)
P1—O13—O11—N7Biii82.55 (4)P2—O22—O23—N3B93.54 (5)
O12—O13—O11—N7Biii118.02 (4)O21—O22—O23—N3B128.45 (4)
O14—O13—O11—N7Biii48.26 (3)O24—O22—O23—N3B57.04 (4)
N3A—O13—O11—N7Biii175.36 (3)O14i—O22—O23—N3B124.96 (4)
P1—O13—O11—O22ii143.89 (3)O11iv—O22—O23—N3B40.30 (4)
O12—O13—O11—O22ii179.37 (2)P2—O22—O23—O1259.91 (4)
O14—O13—O11—O22ii109.60 (3)O21—O22—O23—O1225.01 (2)
N3A—O13—O11—O22ii123.29 (4)O24—O22—O23—O1296.41 (3)
O13—P1—O12—O11123.31 (4)O14i—O22—O23—O1281.59 (3)
O14—P1—O12—O11116.17 (3)O11iv—O22—O23—O12113.15 (3)
O13—P1—O12—O14120.52 (4)P1—O12—O23—P2115.10 (4)
O11—P1—O12—O14116.17 (3)O11—O12—O23—P2107.30 (4)
O11—P1—O12—O13123.31 (4)O14—O12—O23—P284.89 (3)
O14—P1—O12—O13120.52 (4)O13—O12—O23—P2145.59 (3)
O13—P1—O12—O21115.46 (4)O21—O12—O23—P20.196 (19)
O11—P1—O12—O21121.23 (3)P1—O12—O23—O21114.90 (4)
O14—P1—O12—O215.06 (3)O11—O12—O23—O21107.11 (4)
O13—P1—O12—O2365.66 (4)O14—O12—O23—O2184.69 (3)
O11—P1—O12—O23171.02 (2)O13—O12—O23—O21145.40 (3)
O14—P1—O12—O2354.85 (3)P1—O12—O23—O24149.26 (3)
O14—O11—O12—P138.49 (2)O11—O12—O23—O24141.47 (3)
O13—O11—O12—P132.29 (3)O14—O12—O23—O24119.05 (3)
O24ii—O11—O12—P197.01 (4)O13—O12—O23—O24179.76 (2)
N7Biii—O11—O12—P183.84 (4)O21—O12—O23—O2434.36 (3)
O22ii—O11—O12—P130.90 (5)P1—O12—O23—O2286.58 (4)
P1—O11—O12—O1438.49 (2)O11—O12—O23—O2278.79 (5)
O13—O11—O12—O1470.78 (3)O14—O12—O23—O2256.37 (3)
O24ii—O11—O12—O14135.50 (4)O13—O12—O23—O22117.08 (3)
N7Biii—O11—O12—O1445.35 (3)O21—O12—O23—O2228.32 (2)
O22ii—O11—O12—O1469.39 (5)P1—O12—O23—N3B118.61 (4)
P1—O11—O12—O1332.29 (3)O11—O12—O23—N3B126.41 (4)
O14—O11—O12—O1370.78 (3)O14—O12—O23—N3B148.82 (3)
O24ii—O11—O12—O1364.72 (3)O13—O12—O23—N3B88.11 (3)
N7Biii—O11—O12—O13116.12 (3)O21—O12—O23—N3B126.49 (4)
O22ii—O11—O12—O131.39 (5)P1—O13—N3A—C2A5.95 (6)
P1—O11—O12—O2181.65 (4)O11—O13—N3A—C2A48.82 (6)
O14—O11—O12—O2143.16 (3)O12—O13—N3A—C2A2.65 (5)
O13—O11—O12—O21113.94 (3)O14—O13—N3A—C2A38.59 (6)
O24ii—O11—O12—O21178.66 (2)P1—O13—N3A—C4A166.58 (4)
N7Biii—O11—O12—O212.18 (4)O11—O13—N3A—C4A123.71 (5)
O22ii—O11—O12—O21112.55 (5)O12—O13—N3A—C4A169.88 (4)
P1—O11—O12—O2313.04 (3)O14—O13—N3A—C4A148.88 (4)
O14—O11—O12—O2325.45 (3)P2—O23—N3B—C2B23.69 (6)
O13—O11—O12—O2345.33 (4)O21—O23—N3B—C2B19.79 (7)
O24ii—O11—O12—O23110.05 (4)O24—O23—N3B—C2B16.69 (5)
N7Biii—O11—O12—O2370.79 (5)O22—O23—N3B—C2B63.96 (6)
O22ii—O11—O12—O2343.94 (7)O12—O23—N3B—C2B85.20 (6)
O11—O14—O12—P137.15 (2)P2—O23—N3B—C4B177.98 (5)
O13—O14—O12—P133.35 (3)O21—O23—N3B—C4B138.54 (5)
O22i—O14—O12—P15.35 (3)O24—O23—N3B—C4B175.03 (5)
O21—O14—O12—P1175.39 (2)O22—O23—N3B—C4B137.70 (5)
O14i—O14—O12—P1141.65 (4)O12—O23—N3B—C4B73.13 (6)
P1—O14—O12—O1137.15 (2)C2B—N1B—C6B—N6B178.05 (5)
O13—O14—O12—O1170.50 (4)C2B—N1B—C6B—C5B1.72 (8)
O22i—O14—O12—O1142.50 (4)C2B—N3B—C4B—C5B0.34 (8)
O21—O14—O12—O11147.45 (2)O23—N3B—C4B—C5B159.26 (5)
O14i—O14—O12—O11178.80 (3)C2B—N3B—C4B—N9B179.48 (6)
P1—O14—O12—O1333.35 (3)O23—N3B—C4B—N9B19.88 (8)
O11—O14—O12—O1370.50 (4)C8B—N9B—C4B—N3B179.53 (6)
O22i—O14—O12—O1328.00 (4)C8B—N9B—C4B—C5B0.27 (6)
O21—O14—O12—O13142.05 (3)C5B—N7B—C8B—N9B0.41 (6)
O14i—O14—O12—O13108.30 (4)O11v—N7B—C8B—N9B179.14 (5)
P1—O14—O12—O21175.39 (2)C4B—N9B—C8B—N7B0.43 (6)
O11—O14—O12—O21147.45 (2)C8A—N7A—C5A—C4A0.67 (6)
O13—O14—O12—O21142.05 (3)C8A—N7A—C5A—C6A178.24 (6)
O22i—O14—O12—O21170.05 (3)C6A—N1A—C2A—N3A0.44 (9)
O14i—O14—O12—O2133.75 (3)C4A—N3A—C2A—N1A0.69 (9)
P1—O14—O12—O23125.68 (3)O13—N3A—C2A—N1A172.18 (5)
O11—O14—O12—O23162.83 (2)N1B—C6B—N6B—C10B6.28 (8)
O13—O14—O12—O2392.33 (3)C5B—C6B—N6B—C10B173.48 (5)
O22i—O14—O12—O23120.33 (4)C2A—N3A—C4A—N9A179.83 (5)
O21—O14—O12—O2349.72 (2)O13—N3A—C4A—N9A6.86 (8)
O14i—O14—O12—O2315.97 (3)C2A—N3A—C4A—C5A0.20 (8)
O11—O13—O12—P134.37 (3)O13—N3A—C4A—C5A172.77 (4)
O14—O13—O12—P136.78 (3)C8A—N9A—C4A—N3A179.73 (6)
N3A—O13—O12—P1175.28 (3)C8A—N9A—C4A—C5A0.07 (6)
P1—O13—O12—O1134.37 (3)N7A—C5A—C4A—N3A179.31 (5)
O14—O13—O12—O1171.15 (3)C6A—C5A—C4A—N3A1.32 (8)
N3A—O13—O12—O11140.92 (3)N7A—C5A—C4A—N9A0.38 (6)
P1—O13—O12—O1436.78 (3)C6A—C5A—C4A—N9A178.37 (5)
O11—O13—O12—O1471.15 (3)C2A—N1A—C6A—N6A178.69 (5)
N3A—O13—O12—O14147.94 (3)C2A—N1A—C6A—C5A1.93 (8)
P1—O13—O12—O2185.00 (4)N7A—C5A—C6A—N6A0.97 (10)
O11—O13—O12—O21119.37 (4)C4A—C5A—C6A—N6A178.25 (5)
O14—O13—O12—O2148.22 (3)N7A—C5A—C6A—N1A179.66 (6)
N3A—O13—O12—O2199.72 (4)C4A—C5A—C6A—N1A2.37 (8)
P1—O13—O12—O23116.84 (4)N1A—C6A—N6A—C10A10.23 (8)
O11—O13—O12—O23151.21 (2)C5A—C6A—N6A—C10A170.42 (5)
O14—O13—O12—O2380.06 (3)N3B—C4B—C5B—N7B179.32 (5)
N3A—O13—O12—O2367.88 (3)N9B—C4B—C5B—N7B0.03 (6)
O22—P2—O21—O23122.21 (4)N3B—C4B—C5B—C6B1.89 (9)
O24—P2—O21—O23112.83 (4)N9B—C4B—C5B—C6B177.40 (5)
O22—P2—O21—O24124.96 (4)C8B—N7B—C5B—C4B0.23 (6)
O23—P2—O21—O24112.83 (4)O11v—N7B—C5B—C4B179.45 (4)
O24—P2—O21—O22124.96 (4)C8B—N7B—C5B—C6B177.08 (6)
O23—P2—O21—O22122.21 (4)O11v—N7B—C5B—C6B3.70 (8)
O22—P2—O21—O12122.58 (4)N6B—C6B—C5B—C4B176.89 (5)
O24—P2—O21—O12112.46 (4)N1B—C6B—C5B—C4B2.88 (8)
O23—P2—O21—O120.37 (3)N6B—C6B—C5B—N7B0.33 (10)
O22—P2—O21—O1470.86 (4)N1B—C6B—C5B—N7B179.44 (6)
O24—P2—O21—O14164.18 (2)C6B—N1B—C2B—N3B0.66 (9)
O23—P2—O21—O1451.35 (3)C4B—N3B—C2B—N1B1.71 (9)
P1—O12—O21—P282.91 (4)O23—N3B—C2B—N1B159.39 (5)
O11—O12—O21—P2123.47 (4)C4A—N9A—C8A—N7A0.53 (6)
O14—O12—O21—P286.02 (4)C5A—N7A—C8A—N9A0.78 (7)
O13—O12—O21—P244.62 (5)C6A—N6A—C10A—C11A91.56 (8)
O23—O12—O21—P20.23 (2)C6A—N6A—C10A—O15A64.71 (7)
P1—O12—O21—O2382.68 (4)C6B—N6B—C10B—C11B93.52 (8)
O11—O12—O21—O23123.24 (3)C6B—N6B—C10B—O15B66.03 (7)
O14—O12—O21—O2385.80 (3)N6A—C10A—C11A—C12A98.84 (10)
O13—O12—O21—O2344.39 (4)O15A—C10A—C11A—C12A170.55 (14)
P1—O12—O21—O24124.30 (4)N6A—C10A—C11A—O15A71.71 (9)
O11—O12—O21—O24164.86 (3)C13B—C12B—C11B—O15B5.80 (10)
O14—O12—O21—O24127.41 (4)C13B—C12B—C11B—C10B177.47 (8)
O13—O12—O21—O2486.01 (5)O15B—C12B—C11B—C10B171.67 (12)
O23—O12—O21—O2441.62 (3)N6B—C10B—C11B—C12B94.89 (9)
P1—O12—O21—O2245.17 (4)O15B—C10B—C11B—C12B170.85 (14)
O11—O12—O21—O2285.73 (5)N6B—C10B—C11B—O15B75.97 (9)
O14—O12—O21—O2248.29 (3)O15A—C11A—C12A—C13A4.90 (10)
O13—O12—O21—O226.88 (4)C10A—C11A—C12A—C13A176.24 (8)
O23—O12—O21—O2237.51 (3)C10A—C11A—C12A—O15A171.34 (13)
P1—O12—O21—O143.118 (17)C12A—C11A—O15A—C14A4.42 (10)
O11—O12—O21—O1437.45 (3)C10A—C11A—O15A—C14A176.38 (7)
O13—O12—O21—O1441.40 (3)C12A—C11A—O15A—C13A3.28 (7)
O23—O12—O21—O1485.80 (3)C10A—C11A—O15A—C13A175.24 (8)
P1—O14—O21—P2111.37 (3)C10A—C11A—O15A—C12A171.96 (12)
O12—O14—O21—P2114.15 (3)C12A—C11A—O15A—C10A171.96 (12)
O11—O14—O21—P2142.71 (3)C13A—C12A—O15A—C11A174.99 (11)
O13—O14—O21—P280.89 (4)C11A—C12A—O15A—C14A175.55 (10)
O22i—O14—O21—P248.54 (7)C13A—C12A—O15A—C14A0.56 (7)
O14i—O14—O21—P235.55 (3)C11A—C12A—O15A—C13A174.99 (11)
P1—O14—O21—O2382.58 (3)C11A—C12A—O15A—C10A4.56 (7)
O12—O14—O21—O2385.36 (3)C13A—C12A—O15A—C10A179.55 (7)
O11—O14—O21—O23113.92 (4)N6A—C10A—O15A—C11A115.74 (9)
O13—O14—O21—O2352.10 (3)N6A—C10A—O15A—C14A110.62 (9)
O22i—O14—O21—O2377.33 (7)C11A—C10A—O15A—C14A5.11 (10)
O14i—O14—O21—O2364.34 (4)N6A—C10A—O15A—C13A111.06 (6)
P1—O14—O21—O2497.39 (4)C11A—C10A—O15A—C13A4.67 (7)
O12—O14—O21—O24100.16 (4)N6A—C10A—O15A—C12A110.77 (6)
O11—O14—O21—O24128.72 (4)C11A—C10A—O15A—C12A4.96 (7)
O13—O14—O21—O2466.90 (4)C12B—C11B—O15B—C14B5.39 (10)
O22i—O14—O21—O2462.53 (8)C10B—C11B—O15B—C14B177.62 (7)
O14i—O14—O21—O2449.54 (4)C10B—C11B—O15B—C12B172.23 (12)
P1—O14—O21—O22142.74 (3)C12B—C11B—O15B—C13B3.81 (7)
O12—O14—O21—O22145.51 (3)C10B—C11B—O15B—C13B176.04 (8)
O11—O14—O21—O22174.071 (19)C12B—C11B—O15B—C10B172.23 (12)
O13—O14—O21—O22112.25 (4)C13B—C12B—O15B—C11B174.13 (10)
O22i—O14—O21—O2217.18 (7)C11B—C12B—O15B—C14B174.56 (10)
O14i—O14—O21—O224.186 (18)C13B—C12B—O15B—C14B0.44 (7)
P1—O14—O21—O122.774 (15)C11B—C12B—O15B—C13B174.13 (10)
O11—O14—O21—O1228.56 (2)C11B—C12B—O15B—C10B4.39 (7)
O13—O14—O21—O1233.26 (3)C13B—C12B—O15B—C10B178.52 (7)
O22i—O14—O21—O12162.69 (6)N6B—C10B—O15B—C11B112.38 (9)
O14i—O14—O21—O12149.70 (3)N6B—C10B—O15B—C14B109.02 (10)
O24—P2—O22—O21123.57 (4)C11B—C10B—O15B—C14B3.36 (10)
O23—P2—O22—O21119.20 (4)N6B—C10B—O15B—C12B107.56 (6)
O21—P2—O22—O24123.57 (4)C11B—C10B—O15B—C12B4.81 (7)
O23—P2—O22—O24117.22 (4)N6B—C10B—O15B—C13B108.51 (6)
O21—P2—O22—O23119.20 (4)C11B—C10B—O15B—C13B3.87 (7)
O24—P2—O22—O23117.22 (4)C11B—O15B—C14B—C13B2.70 (11)
O21—P2—O22—O14i73.73 (4)C12B—O15B—C14B—C13B0.48 (8)
O24—P2—O22—O14i162.69 (2)C10B—O15B—C14B—C13B0.90 (14)
O23—P2—O22—O14i45.47 (4)O15B—C14B—C13B—C12B0.73 (12)
O21—P2—O22—O11iv112.17 (3)C11B—C12B—C13B—C14B3.98 (11)
O24—P2—O22—O11iv11.41 (2)O15B—C12B—C13B—C14B0.47 (7)
O23—P2—O22—O11iv128.63 (3)C11B—C12B—C13B—O15B3.51 (6)
O23—O21—O22—P236.03 (3)C11B—O15B—C13B—C14B177.28 (11)
O24—O21—O22—P233.41 (3)C12B—O15B—C13B—C14B179.25 (12)
O12—O21—O22—P279.36 (4)C10B—O15B—C13B—C14B179.37 (10)
O14—O21—O22—P2113.98 (4)C11B—O15B—C13B—C12B3.46 (6)
P2—O21—O22—O2433.41 (3)C14B—O15B—C13B—C12B179.25 (12)
O23—O21—O22—O2469.44 (3)C10B—O15B—C13B—C12B1.38 (6)
O12—O21—O22—O24112.76 (3)C11A—O15A—C14A—C13A1.96 (11)
O14—O21—O22—O24147.38 (2)C12A—O15A—C14A—C13A0.63 (8)
P2—O21—O22—O2336.03 (3)C10A—O15A—C14A—C13A0.78 (14)
O24—O21—O22—O2369.44 (3)O15A—C14A—C13A—C12A0.95 (12)
O12—O21—O22—O2343.32 (3)C11A—C12A—C13A—C14A3.58 (11)
O14—O21—O22—O2377.94 (3)O15A—C12A—C13A—C14A0.60 (7)
P2—O21—O22—O14i119.63 (4)C11A—C12A—C13A—O15A2.98 (6)
O23—O21—O22—O14i83.59 (4)C11A—O15A—C13A—C14A178.02 (11)
O24—O21—O22—O14i153.03 (3)C12A—O15A—C13A—C14A179.04 (12)
O12—O21—O22—O14i40.27 (4)C10A—O15A—C13A—C14A179.46 (9)
O14—O21—O22—O14i5.65 (2)C11A—O15A—C13A—C12A2.94 (6)
P2—O21—O22—O11iv67.50 (4)C14A—O15A—C13A—C12A179.04 (12)
O23—O21—O22—O11iv103.53 (3)C10A—O15A—C13A—C12A0.42 (6)
O24—O21—O22—O11iv34.09 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x1, y1, z; (iv) x+1, y, z; (v) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7B—H7B···O11v0.883 (7)1.837 (7)2.6732 (11)157.3 (7)
N6A—H6A···O21vi0.838 (8)2.029 (8)2.8586 (10)170.5 (7)
N6B—H6B···O11v0.841 (7)2.076 (8)2.9068 (10)169.4 (7)
N7A—H7A···O21vi0.889 (7)1.958 (7)2.7794 (11)153.0 (7)
O23—H23···N3B0.963 (9)1.679 (9)2.6397 (11)175.6 (9)
N9B—H9B···N9Avii0.933 (9)1.940 (9)2.8716 (12)176.1 (9)
O12—H12···O210.838 (10)1.707 (10)2.5417 (9)174.1 (8)
O24—H24···O11iv0.832 (10)1.714 (10)2.5449 (9)177.2 (9)
O14—H14···O22i1.033 (11)1.509 (11)2.5420 (9)179.6 (9)
N3A—H3A···O131.011 (9)1.541 (9)2.5499 (11)175.5 (9)
Symmetry codes: (i) x+1, y+1, z+1; (iv) x+1, y, z; (v) x+1, y+1, z; (vi) x, y+1, z; (vii) x+1, y+2, z+1.
(293) top
Crystal data top
C10H9N50·H3O4PZ = 2
Mr = 313.22F(000) = 324
TRICLINIC, P1Dx = 1.608 Mg m3
a = 4.4923 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.736 (2) ÅCell parameters from 3615 reflections
c = 14.455 (3) Åθ = 2.2–20.1°
α = 91.00 (3)°µ = 0.25 mm1
β = 100.92 (3)°T = 293 K
γ = 108.47 (3)°THIN NEEDLE, colourlrss
V = 647.0 (2) Å30.41 × 0.09 × 0.09 mm
Data collection top
KM4CCD
diffractometer
5349 independent reflections
Radiation source: fine-focus sealed tube3704 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
CCD scansθmax = 40.3°, θmin = 4.2°
Absorption correction: ANALYTICAL- crysAlis Ver170.26
?
h = 58
Tmin = 0.915, Tmax = 0.982k = 1719
14205 measured reflectionsl = 2425
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137Calculated w = 1/[σ2(Fo2) + (0.030P)2 + 0.1P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 1.110
3704 reflectionsΔρmax = 0.42 e Å3
230 parametersΔρmin = 0.42 e Å3
6 restraintsExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (6)
Crystal data top
C10H9N50·H3O4Pγ = 108.47 (3)°
Mr = 313.22V = 647.0 (2) Å3
TRICLINIC, P1Z = 2
a = 4.4923 (9) ÅMo Kα radiation
b = 10.736 (2) ŵ = 0.25 mm1
c = 14.455 (3) ÅT = 293 K
α = 91.00 (3)°0.41 × 0.09 × 0.09 mm
β = 100.92 (3)°
Data collection top
KM4CCD
diffractometer
5349 independent reflections
Absorption correction: ANALYTICAL- crysAlis Ver170.26
?
3704 reflections with I > 2σ(I)
Tmin = 0.915, Tmax = 0.982Rint = 0.042
14205 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0566 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.21(Δ/σ)max = 1.110
3704 reflectionsΔρmax = 0.42 e Å3
230 parametersΔρmin = 0.42 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.50152 (5)0.41820 (2)0.650206 (16)0.03131 (6)
O110.84100 (14)0.49848 (6)0.69833 (5)0.03952 (19)
O140.28906 (14)0.39684 (7)0.72484 (5)0.04474 (19)
O120.37165 (17)0.49211 (8)0.57185 (5)0.0535 (2)
O130.49328 (19)0.28368 (7)0.61236 (6)0.0673 (3)
N7A0.89979 (18)0.27033 (7)0.37875 (5)0.0354 (2)
C5A0.9620 (2)0.17194 (8)0.33073 (6)0.0304 (2)
C6A1.1143 (2)0.16831 (9)0.25398 (6)0.0329 (2)
N6A1.23787 (18)0.27477 (8)0.20996 (5)0.0377 (2)
N1A1.13127 (19)0.05008 (8)0.22584 (6)0.0408 (2)
N3A0.84149 (19)0.06057 (8)0.33987 (6)0.0402 (2)
C4A0.8292 (2)0.05723 (9)0.37032 (6)0.0325 (2)
N9A0.68896 (18)0.08407 (8)0.44098 (6)0.0393 (2)
C2A0.9964 (2)0.05447 (10)0.26902 (8)0.0447 (3)
C8A0.7386 (2)0.21350 (10)0.44356 (7)0.0415 (3)
C10A1.3657 (2)0.27000 (11)0.12400 (7)0.0450 (3)
C11A1.1203 (2)0.25788 (11)0.03733 (7)0.0453 (3)
O15A0.8842 (3)0.14556 (10)0.00751 (8)0.0966 (4)
C14A0.6949 (4)0.16948 (19)0.07229 (11)0.1018 (6)
C13A0.8047 (4)0.29113 (19)0.08774 (11)0.1101 (6)
C12A1.0819 (3)0.35400 (12)0.01366 (11)0.0762 (5)
H8A0.671 (2)0.2572 (10)0.4879 (7)0.038 (3)*
H7A0.952 (2)0.3632 (11)0.3627 (8)0.061 (3)*
H6A1.208 (2)0.3477 (10)0.2296 (8)0.051 (3)*
H2A0.999 (2)0.1410 (10)0.2454 (7)0.041 (3)*
H140.143 (3)0.4282 (11)0.7195 (8)0.058 (3)*
H10A1.450 (2)0.1871 (11)0.1228 (7)0.057 (3)*
H10B1.528 (2)0.3468 (11)0.1265 (8)0.057 (3)*
H120.460 (5)0.481 (2)0.5268 (14)0.059 (7)*0.50
H9A0.573 (4)0.0306 (17)0.4720 (11)0.034 (5)*0.50
H30.685 (4)0.1663 (19)0.3579 (14)0.155 (8)*
H14A0.48870.09970.11220.105*
H13A0.71940.34540.13980.111*
H12A1.22540.45120.01000.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.03355 (9)0.03164 (10)0.03291 (11)0.01117 (8)0.01541 (8)0.00763 (8)
O110.0319 (3)0.0347 (3)0.0553 (4)0.0121 (2)0.0140 (3)0.0103 (3)
O140.0415 (3)0.0672 (4)0.0448 (3)0.0333 (2)0.0261 (2)0.0279 (3)
O120.0564 (4)0.0705 (4)0.0384 (4)0.0244 (3)0.0128 (3)0.0220 (3)
O130.0984 (5)0.0280 (3)0.0827 (5)0.0072 (3)0.0598 (4)0.0006 (3)
N7A0.0393 (3)0.0333 (4)0.0350 (4)0.0111 (3)0.0114 (3)0.0070 (3)
C5A0.0305 (4)0.0292 (4)0.0296 (4)0.0072 (3)0.0059 (3)0.0049 (3)
C6A0.0313 (4)0.0349 (4)0.0301 (4)0.0082 (3)0.0050 (3)0.0051 (3)
N6A0.0439 (4)0.0346 (4)0.0352 (4)0.0091 (3)0.0154 (3)0.0057 (3)
N1A0.0466 (4)0.0359 (4)0.0427 (4)0.0133 (3)0.0161 (3)0.0047 (3)
N3A0.0449 (4)0.0291 (4)0.0459 (4)0.0099 (3)0.0113 (4)0.0070 (3)
C4A0.0314 (4)0.0331 (4)0.0311 (4)0.0078 (3)0.0058 (3)0.0074 (3)
N9A0.0394 (4)0.0438 (4)0.0350 (4)0.0102 (3)0.0132 (3)0.0097 (3)
C2A0.0531 (5)0.0343 (5)0.0493 (6)0.0150 (4)0.0150 (4)0.0060 (4)
C8A0.0405 (4)0.0477 (5)0.0376 (5)0.0120 (4)0.0152 (4)0.0059 (4)
C10A0.0454 (4)0.0516 (5)0.0420 (5)0.0136 (4)0.0218 (4)0.0130 (4)
C11A0.0521 (5)0.0541 (6)0.0380 (5)0.0204 (4)0.0232 (4)0.0076 (4)
O15A0.0969 (7)0.0757 (6)0.0971 (8)0.0207 (6)0.0157 (7)0.0065 (6)
C14A0.1030 (9)0.1377 (12)0.0633 (9)0.0626 (8)0.0238 (8)0.0238 (9)
C13A0.1290 (8)0.1903 (12)0.0632 (8)0.1129 (7)0.0348 (7)0.0598 (8)
C12A0.0803 (8)0.0632 (6)0.0918 (9)0.0337 (6)0.0136 (7)0.0388 (6)
Geometric parameters (Å, º) top
P1—O111.5155 (9)N3A—C4A1.3528 (13)
P1—O131.5222 (9)N3A—H31.193 (19)
P1—O121.5256 (9)C4A—N9A1.3683 (14)
P1—O141.5452 (8)N9A—C8A1.3344 (14)
P1—H121.92 (2)N9A—H9A0.843 (15)
O14—H140.818 (13)C2A—H2A0.988 (10)
O12—H120.85 (2)C8A—H8A0.937 (11)
N7A—C8A1.3309 (13)C10A—C11A1.4772 (15)
N7A—C5A1.3822 (13)C10A—H10A1.074 (12)
N7A—H7A0.992 (12)C10A—H10B0.907 (10)
C5A—C4A1.3743 (13)C11A—C12A1.3150 (18)
C5A—C6A1.4154 (14)C11A—O15A1.3278 (14)
C6A—N6A1.3329 (13)O15A—C14A1.377 (2)
C6A—N1A1.3555 (13)C14A—C13A1.282 (3)
N6A—C10A1.4708 (14)C14A—H14A1.0463
N6A—H6A0.886 (12)C13A—C12A1.446 (2)
N1A—C2A1.3242 (14)C13A—H13A1.0487
N3A—C2A1.3346 (15)C12A—H12A1.0326
O11—P1—O13109.90 (5)N9A—C4A—C5A109.15 (9)
O11—P1—O12110.41 (5)C8A—N9A—C4A105.61 (9)
O13—P1—O12111.52 (5)C8A—N9A—H9A125.5 (13)
O11—P1—O14108.18 (4)C4A—N9A—H9A128.4 (13)
O13—P1—O14108.06 (5)N1A—C2A—N3A128.28 (10)
O12—P1—O14108.67 (5)N1A—C2A—H2A117.9 (6)
O11—P1—H12103.1 (6)N3A—C2A—H2A113.7 (6)
O13—P1—H1292.8 (8)N7A—C8A—N9A112.14 (10)
O12—P1—H1225.5 (8)N7A—C8A—H8A125.5 (6)
O14—P1—H12132.9 (8)N9A—C8A—H8A122.3 (6)
P1—O14—H14120.0 (8)N6A—C10A—C11A111.86 (9)
P1—O12—H12103.9 (17)N6A—C10A—H10A109.4 (6)
C8A—N7A—C5A106.79 (8)C11A—C10A—H10A108.8 (5)
C8A—N7A—H7A128.1 (7)N6A—C10A—H10B106.6 (7)
C5A—N7A—H7A124.9 (7)C11A—C10A—H10B109.2 (7)
C4A—C5A—N7A106.31 (8)H10A—C10A—H10B111.0 (9)
C4A—C5A—C6A119.52 (9)C12A—C11A—O15A111.26 (10)
N7A—C5A—C6A134.15 (8)C12A—C11A—C10A126.62 (10)
N6A—C6A—N1A120.17 (9)O15A—C11A—C10A121.75 (11)
N6A—C6A—C5A122.78 (9)C11A—O15A—C14A106.75 (12)
N1A—C6A—C5A117.06 (8)C13A—C14A—O15A109.34 (13)
C6A—N6A—C10A123.30 (9)C13A—C14A—H14A125.6
C6A—N6A—H6A115.5 (7)O15A—C14A—H14A125.0
C10A—N6A—H6A120.4 (7)C14A—C13A—C12A107.81 (14)
C2A—N1A—C6A118.57 (9)C14A—C13A—H13A131.0
C2A—N3A—C4A113.87 (8)C12A—C13A—H13A121.2
C2A—N3A—H3118.4 (10)C11A—C12A—C13A104.61 (12)
C4A—N3A—H3126.3 (10)C11A—C12A—H12A130.2
N3A—C4A—N9A128.19 (9)C13A—C12A—H12A124.8
N3A—C4A—C5A122.65 (9)
C8A—N7A—C5A—C4A0.24 (9)N3A—C4A—N9A—C8A179.47 (9)
C8A—N7A—C5A—C6A178.17 (9)C5A—C4A—N9A—C8A0.17 (10)
C4A—C5A—C6A—N6A177.51 (8)C6A—N1A—C2A—N3A0.62 (15)
N7A—C5A—C6A—N6A0.20 (15)C4A—N3A—C2A—N1A0.93 (15)
C4A—C5A—C6A—N1A2.51 (12)C5A—N7A—C8A—N9A0.37 (10)
N7A—C5A—C6A—N1A179.78 (9)C4A—N9A—C8A—N7A0.34 (10)
N1A—C6A—N6A—C10A6.77 (13)C6A—N6A—C10A—C11A92.95 (12)
C5A—C6A—N6A—C10A173.25 (8)N6A—C10A—C11A—C12A98.20 (15)
N6A—C6A—N1A—C2A177.72 (8)N6A—C10A—C11A—O15A74.12 (15)
C5A—C6A—N1A—C2A2.30 (12)C12A—C11A—O15A—C14A4.64 (17)
C2A—N3A—C4A—N9A179.89 (9)C10A—C11A—O15A—C14A178.02 (13)
C2A—N3A—C4A—C5A0.67 (12)C11A—O15A—C14A—C13A2.2 (2)
N7A—C5A—C4A—N3A179.30 (8)O15A—C14A—C13A—C12A0.7 (2)
C6A—C5A—C4A—N3A1.02 (13)O15A—C11A—C12A—C13A4.94 (17)
N7A—C5A—C4A—N9A0.05 (9)C10A—C11A—C12A—C13A177.94 (13)
C6A—C5A—C4A—N9A178.33 (7)C14A—C13A—C12A—C11A3.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7A—H7A···O11i0.992 (12)1.825 (11)2.7414 (13)152.2 (11)
N6A—H6A···O11i0.886 (12)2.030 (12)2.9019 (13)168.0 (10)
O14—H14···O11ii0.818 (13)1.734 (13)2.5501 (12)174.9 (12)
O12—H12···O12iii0.85 (2)1.72 (2)2.5435 (17)162 (3)
N3A—H3···O13iv1.193 (19)1.388 (19)2.5777 (14)174.4 (17)
N9A—H9A···N9Aiv0.84 (2)2.04 (2)2.8837 (19)174 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1.

Experimental details

(115)(293)
Crystal data
Chemical formulaC10H12N5O5PC10H9N50·H3O4P
Mr313.22313.22
Crystal system, space groupTriclinic, P1TRICLINIC, P1
Temperature (K)115293
a, b, c (Å)8.9243 (18), 10.720 (2), 14.295 (3)4.4923 (9), 10.736 (2), 14.455 (3)
α, β, γ (°)91.41 (3), 100.75 (3), 108.85 (3)91.00 (3), 100.92 (3), 108.47 (3)
V3)1266.2 (4)647.0 (2)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.250.25
Crystal size (mm)0.41 × 0.09 × 0.090.41 × 0.09 × 0.09
Data collection
DiffractometerKM4CCD
diffractometer
KM4CCD
diffractometer
Absorption correctionANALYTICAL- CrysAlis Ver170.26ANALYTICAL- CrysAlis Ver170.26
Tmin, Tmax0.910, 0.9820.915, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
11933, 5604, 5604 14205, 5349, 3704
Rint0.0490.042
(sin θ/λ)max1)0.6630.910
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.119, 1.22 0.056, 0.137, 1.21
No. of reflections56043704
No. of parameters451230
No. of restraints06
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max0.3661.110
Δρmax, Δρmin (e Å3)0.66, 0.490.42, 0.42

Computer programs: CRYSaLIS PROCEDURE, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), DIAMOND 2.

Hydrogen-bond geometry (Å, º) for (115) top
D—H···AD—HH···AD···AD—H···A
N7B—H7B···O11i0.883 (7)1.837 (7)2.6732 (11)157.3 (7)
N6A—H6A···O21ii0.838 (8)2.029 (8)2.8586 (10)170.5 (7)
N6B—H6B···O11i0.841 (7)2.076 (8)2.9068 (10)169.4 (7)
N7A—H7A···O21ii0.889 (7)1.958 (7)2.7794 (11)153.0 (7)
O23—H23···N3B0.963 (9)1.679 (9)2.6397 (11)175.6 (9)
N9B—H9B···N9Aiii0.933 (9)1.940 (9)2.8716 (12)176.1 (9)
O12—H12···O210.838 (10)1.707 (10)2.5417 (9)174.1 (8)
O24—H24···O11iv0.832 (10)1.714 (10)2.5449 (9)177.2 (9)
O14—H14···O22v1.033 (11)1.509 (11)2.5420 (9)179.6 (9)
N3A—H3A···O131.011 (9)1.541 (9)2.5499 (11)175.5 (9)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z; (iii) x+1, y+2, z+1; (iv) x+1, y, z; (v) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (293) top
D—H···AD—HH···AD···AD—H···A
N7A—H7A···O11i0.992 (12)1.825 (11)2.7414 (13)152.2 (11)
N6A—H6A···O11i0.886 (12)2.030 (12)2.9019 (13)168.0 (10)
O14—H14···O11ii0.818 (13)1.734 (13)2.5501 (12)174.9 (12)
O12—H12···O12iii0.85 (2)1.72 (2)2.5435 (17)162 (3)
N3A—H3···O13iv1.193 (19)1.388 (19)2.5777 (14)174.4 (17)
N9A—H9A···N9Aiv0.843 (15)2.044 (16)2.8837 (19)173.9 (15)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1.
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds