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
. 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
CCDC references: 298347; 298348
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.
Crystal data top
C10H12N5O5P | Z = 4 |
Mr = 313.22 | F(000) = 648 |
Triclinic, P1 | Dx = 1.643 Mg m−3 |
a = 8.9243 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.720 (2) Å | Cell parameters from 5624 reflections |
c = 14.295 (3) Å | θ = 1.3–4.1° |
α = 91.41 (3)° | µ = 0.25 mm−1 |
β = 100.75 (3)° | T = 115 K |
γ = 108.85 (3)° | Thin, needle, colourless |
V = 1266.2 (4) Å3 | 0.41 × 0.09 × 0.09 mm |
Data collection top
KM4CCD diffractometer | 5604 independent reflections |
Radiation source: fine-focus sealed tube | 5604 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: CCD pixels mm-1 | θmax = 28.1°, θmin = 2.6° |
CCD scans | h = −9→11 |
Absorption correction: ANALYTICAL- crysAlis Ver170.26 ? | k = −14→13 |
Tmin = 0.910, Tmax = 0.982 | l = −18→18 |
11933 measured reflections | |
Refinement top
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | Calculated w = 1/[σ2(Fo2) + (0.040P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max = 0.366 |
5604 reflections | Δρmax = 0.66 e Å−3 |
451 parameters | Δρmin = −0.49 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: 0.00000 (19) |
Crystal data top
C10H12N5O5P | γ = 108.85 (3)° |
Mr = 313.22 | V = 1266.2 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.9243 (18) Å | Mo Kα radiation |
b = 10.720 (2) Å | µ = 0.25 mm−1 |
c = 14.295 (3) Å | T = 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 = 0.982 | Rint = 0.049 |
11933 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | (Δ/σ)max = 0.366 |
5604 reflections | Δρmax = 0.66 e Å−3 |
451 parameters | Δρmin = −0.49 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
P1 | 0.258675 (17) | 0.582058 (14) | 0.349123 (11) | 0.01303 (4) | |
O14 | 0.32806 (5) | 0.49898 (4) | 0.42273 (3) | 0.01967 (12) | |
O13 | 0.28265 (5) | 0.71693 (4) | 0.39431 (3) | 0.02124 (13) | |
O11 | 0.08116 (5) | 0.50476 (4) | 0.30711 (3) | 0.01675 (12) | |
O12 | 0.35224 (5) | 0.59204 (4) | 0.26664 (3) | 0.01947 (12) | |
P2 | 0.744779 (18) | 0.580556 (14) | 0.348245 (11) | 0.01408 (4) | |
O21 | 0.58020 (5) | 0.49509 (4) | 0.29008 (3) | 0.01659 (12) | |
O22 | 0.80272 (5) | 0.51551 (5) | 0.43261 (3) | 0.02431 (14) | |
O24 | 0.86877 (5) | 0.61866 (4) | 0.28136 (3) | 0.02002 (12) | |
O23 | 0.72490 (5) | 0.71416 (4) | 0.38014 (4) | 0.02953 (14) | |
N3A | 0.43288 (6) | 0.93466 (5) | 0.33384 (4) | 0.01585 (14) | |
N3B | 0.92187 (6) | 0.94488 (5) | 0.34791 (4) | 0.01787 (14) | |
N1B | 1.06869 (6) | 1.05476 (5) | 0.23065 (4) | 0.01769 (14) | |
N7A | 0.45402 (6) | 1.26300 (5) | 0.37371 (4) | 0.01543 (14) | |
N9A | 0.34856 (6) | 1.07372 (5) | 0.43783 (4) | 0.01657 (14) | |
N9B | 0.84433 (6) | 1.09571 (5) | 0.44545 (4) | 0.01653 (14) | |
N7B | 0.95034 (6) | 1.27878 (5) | 0.38205 (4) | 0.01570 (14) | |
N1A | 0.57722 (6) | 1.04557 (5) | 0.21931 (4) | 0.01723 (14) | |
C6B | 1.06024 (7) | 1.17390 (6) | 0.25746 (4) | 0.01481 (16) | |
C4B | 0.91659 (7) | 1.06430 (6) | 0.37517 (4) | 0.01510 (16) | |
C8B | 0.86802 (7) | 1.22608 (6) | 0.44756 (4) | 0.01751 (17) | |
C5A | 0.48855 (7) | 1.16628 (5) | 0.32549 (4) | 0.01431 (16) | |
C2A | 0.51132 (7) | 0.93972 (6) | 0.26212 (4) | 0.01722 (17) | |
N6B | 1.12164 (6) | 1.27880 (5) | 0.21158 (4) | 0.01675 (14) | |
C4A | 0.42180 (7) | 1.05120 (6) | 0.36615 (4) | 0.01424 (16) | |
C6A | 0.56655 (7) | 1.16404 (6) | 0.24825 (4) | 0.01436 (16) | |
N6A | 0.62922 (6) | 1.27112 (5) | 0.20491 (4) | 0.01728 (14) | |
C5B | 0.98354 (7) | 1.17957 (5) | 0.33502 (4) | 0.01399 (16) | |
C2B | 1.00165 (7) | 0.95015 (6) | 0.27631 (5) | 0.01913 (17) | |
C8A | 0.37259 (7) | 1.20346 (6) | 0.43947 (4) | 0.01696 (17) | |
C10A | 0.68851 (7) | 1.26754 (6) | 0.11594 (5) | 0.02013 (17) | |
C10B | 1.18666 (7) | 1.27282 (6) | 0.12502 (5) | 0.01981 (17) | |
C11A | 0.55868 (7) | 1.25542 (6) | 0.03094 (5) | 0.02177 (18) | |
C12B | 1.03694 (9) | 1.35284 (7) | −0.01344 (7) | 0.0425 (3) | |
C11B | 1.06245 (7) | 1.25828 (6) | 0.03689 (5) | 0.02159 (18) | |
C12A | 0.53515 (9) | 1.35116 (7) | −0.01963 (7) | 0.0473 (3) | |
O15A | 0.43382 (7) | 1.14135 (5) | 0.00432 (5) | 0.0503 (2) | |
O15B | 0.94531 (7) | 1.14240 (6) | 0.00584 (5) | 0.0535 (2) | |
C14B | 0.84718 (10) | 1.16537 (9) | −0.07549 (7) | 0.0540 (3) | |
C13B | 0.89981 (10) | 1.28997 (10) | −0.08914 (6) | 0.0566 (3) | |
C14A | 0.33063 (10) | 1.16623 (9) | −0.07322 (6) | 0.0532 (3) | |
C13A | 0.38689 (10) | 1.28857 (10) | −0.09029 (6) | 0.0640 (3) | |
H2A | 0.5233 (7) | 0.8592 (6) | 0.2408 (4) | 0.0110 (16)* | |
H7B | 0.9870 (8) | 1.3626 (7) | 0.3705 (5) | 0.0253 (19)* | |
H8A | 0.3406 (7) | 1.2540 (6) | 0.4845 (4) | 0.0150 (17)* | |
H6A | 0.6136 (8) | 1.3398 (7) | 0.2234 (5) | 0.029 (2)* | |
H8B | 0.8343 (7) | 1.2759 (6) | 0.4905 (5) | 0.0183 (18)* | |
H6B | 1.1116 (8) | 1.3490 (7) | 0.2326 (5) | 0.0251 (19)* | |
H7A | 0.4880 (8) | 1.3483 (7) | 0.3638 (5) | 0.032 (2)* | |
H0A1 | 0.7801 (7) | 1.3546 (6) | 0.1154 (5) | 0.0205 (18)* | |
H2B | 1.0154 (8) | 0.8652 (7) | 0.2542 (5) | 0.0261 (19)* | |
H0B1 | 1.2797 (7) | 1.3561 (6) | 0.1258 (5) | 0.0212 (18)* | |
H0A2 | 0.7278 (7) | 1.1911 (6) | 0.1140 (5) | 0.0195 (18)* | |
H0B2 | 1.2253 (8) | 1.1947 (6) | 0.1258 (5) | 0.0214 (18)* | |
H23 | 0.8011 (11) | 0.7971 (9) | 0.3700 (7) | 0.069 (3)* | |
H9B | 0.7850 (10) | 1.0386 (8) | 0.4838 (6) | 0.060 (3)* | |
H12 | 0.4319 (10) | 0.5654 (8) | 0.2747 (6) | 0.055 (3)* | |
H24 | 0.9400 (10) | 0.5833 (9) | 0.2888 (7) | 0.060 (3)* | |
H14 | 0.2752 (12) | 0.4929 (10) | 0.4816 (8) | 0.089 (4)* | |
H3A | 0.3782 (10) | 0.8473 (9) | 0.3583 (7) | 0.064 (3)* | |
H13B | 0.8728 (12) | 1.3363 (10) | −0.1376 (8) | 0.092 (4)* | |
H14B | 0.7532 (18) | 1.0813 (15) | −0.1039 (11) | 0.172 (6)* | |
H14A | 0.2238 (17) | 1.0805 (14) | −0.0982 (11) | 0.158 (6)* | |
H13A | 0.3651 (14) | 1.3354 (12) | −0.1355 (9) | 0.117 (5)* | |
H12B | 1.0680 (7) | 1.3898 (6) | −0.0113 (4) | 0.0087 (16)* | |
H12A | 0.5684 (7) | 1.3891 (6) | −0.0180 (4) | 0.0115 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01350 (6) | 0.01263 (6) | 0.01499 (7) | 0.00548 (5) | 0.00555 (6) | 0.00389 (5) |
O14 | 0.02151 (19) | 0.02299 (19) | 0.0185 (2) | 0.01141 (15) | 0.00591 (17) | 0.00805 (16) |
O13 | 0.0273 (2) | 0.01304 (18) | 0.0242 (2) | 0.00408 (16) | 0.01210 (18) | 0.00252 (16) |
O11 | 0.01348 (17) | 0.01445 (17) | 0.0242 (2) | 0.00509 (14) | 0.00728 (16) | 0.00461 (16) |
O12 | 0.01777 (17) | 0.02859 (19) | 0.0192 (2) | 0.01389 (14) | 0.00916 (16) | 0.01052 (17) |
P2 | 0.01436 (6) | 0.01412 (6) | 0.01535 (7) | 0.00466 (5) | 0.00686 (6) | 0.00318 (5) |
O21 | 0.01500 (17) | 0.01529 (17) | 0.0214 (2) | 0.00665 (14) | 0.00557 (16) | 0.00247 (16) |
O22 | 0.0219 (2) | 0.0347 (2) | 0.0159 (2) | 0.00824 (17) | 0.00417 (18) | 0.00906 (18) |
O24 | 0.01831 (17) | 0.02614 (19) | 0.0237 (2) | 0.01304 (15) | 0.01243 (16) | 0.01285 (17) |
O23 | 0.0344 (2) | 0.01376 (19) | 0.0433 (3) | 0.00213 (17) | 0.02606 (19) | −0.00167 (18) |
N3A | 0.0169 (2) | 0.0127 (2) | 0.0175 (2) | 0.00391 (17) | 0.0040 (2) | 0.00284 (18) |
N3B | 0.0181 (2) | 0.0149 (2) | 0.0210 (3) | 0.00554 (17) | 0.0047 (2) | 0.00347 (19) |
N1B | 0.0183 (2) | 0.0167 (2) | 0.0194 (2) | 0.00610 (17) | 0.0064 (2) | 0.00202 (19) |
N7A | 0.0158 (2) | 0.0140 (2) | 0.0170 (2) | 0.00489 (17) | 0.00438 (19) | 0.00234 (18) |
N9A | 0.0158 (2) | 0.0175 (2) | 0.0157 (2) | 0.00429 (18) | 0.0036 (2) | 0.00273 (19) |
N9B | 0.0166 (2) | 0.0171 (2) | 0.0163 (2) | 0.00507 (18) | 0.0048 (2) | 0.00468 (19) |
N7B | 0.0158 (2) | 0.0134 (2) | 0.0180 (2) | 0.00418 (17) | 0.0046 (2) | 0.00327 (19) |
N1A | 0.0177 (2) | 0.0165 (2) | 0.0188 (2) | 0.00633 (17) | 0.0057 (2) | 0.00331 (19) |
C6B | 0.0123 (2) | 0.0160 (2) | 0.0142 (3) | 0.0031 (2) | 0.0010 (2) | 0.0016 (2) |
C4B | 0.0105 (2) | 0.0174 (2) | 0.0156 (3) | 0.0029 (2) | 0.0013 (2) | 0.0026 (2) |
C8B | 0.0151 (3) | 0.0193 (3) | 0.0174 (3) | 0.0047 (2) | 0.0032 (2) | 0.0026 (2) |
C5A | 0.0123 (2) | 0.0146 (2) | 0.0153 (3) | 0.00459 (19) | 0.0009 (2) | 0.0008 (2) |
C2A | 0.0184 (3) | 0.0155 (2) | 0.0185 (3) | 0.0070 (2) | 0.0031 (2) | 0.0011 (2) |
N6B | 0.0187 (2) | 0.0148 (2) | 0.0171 (2) | 0.00480 (17) | 0.0062 (2) | 0.00155 (19) |
C4A | 0.0110 (2) | 0.0148 (2) | 0.0150 (3) | 0.00363 (19) | −0.0008 (2) | 0.0024 (2) |
C6A | 0.0098 (2) | 0.0174 (2) | 0.0153 (3) | 0.00452 (19) | 0.0012 (2) | 0.0021 (2) |
N6A | 0.0192 (2) | 0.0166 (2) | 0.0172 (2) | 0.00573 (18) | 0.0068 (2) | 0.00307 (19) |
C5B | 0.0116 (2) | 0.0140 (2) | 0.0157 (3) | 0.00437 (19) | 0.0009 (2) | 0.0016 (2) |
C2B | 0.0207 (3) | 0.0156 (2) | 0.0217 (3) | 0.0071 (2) | 0.0040 (2) | 0.0027 (2) |
C8A | 0.0148 (3) | 0.0182 (3) | 0.0173 (3) | 0.0043 (2) | 0.0037 (2) | 0.0029 (2) |
C10A | 0.0213 (3) | 0.0217 (3) | 0.0210 (3) | 0.0078 (2) | 0.0114 (2) | 0.0080 (2) |
C10B | 0.0195 (3) | 0.0226 (3) | 0.0201 (3) | 0.0072 (2) | 0.0102 (2) | 0.0063 (2) |
C11A | 0.0250 (3) | 0.0251 (3) | 0.0200 (3) | 0.0105 (2) | 0.0121 (2) | 0.0036 (2) |
C12B | 0.0310 (4) | 0.0248 (3) | 0.0734 (6) | 0.0118 (3) | 0.0077 (4) | 0.0251 (3) |
C11B | 0.0220 (3) | 0.0277 (3) | 0.0192 (3) | 0.0100 (2) | 0.0113 (2) | 0.0021 (2) |
C12A | 0.0367 (4) | 0.0331 (3) | 0.0849 (6) | 0.0192 (3) | 0.0252 (4) | 0.0396 (3) |
O15A | 0.0471 (3) | 0.0360 (3) | 0.0597 (4) | 0.0157 (2) | −0.0112 (3) | 0.0003 (3) |
O15B | 0.0467 (3) | 0.0369 (3) | 0.0658 (4) | 0.0137 (2) | −0.0142 (3) | 0.0024 (3) |
C14B | 0.0477 (4) | 0.0687 (4) | 0.0461 (5) | 0.0385 (3) | −0.0196 (4) | −0.0238 (4) |
C13B | 0.0565 (4) | 0.1079 (5) | 0.0352 (4) | 0.0586 (3) | 0.0212 (3) | 0.0402 (4) |
C14A | 0.0526 (4) | 0.0759 (4) | 0.0373 (4) | 0.0460 (3) | −0.0163 (4) | −0.0236 (4) |
C13A | 0.0736 (4) | 0.1233 (5) | 0.0395 (4) | 0.0781 (3) | 0.0330 (3) | 0.0487 (4) |
Geometric parameters (Å, º) top
P1—O13 | 1.5020 (6) | N9B—C4B | 1.3798 (9) |
P1—O11 | 1.5262 (7) | N9B—H9B | 0.933 (9) |
P1—O12 | 1.5540 (6) | N7B—C8B | 1.3229 (9) |
P1—O14 | 1.5630 (7) | N7B—C5B | 1.3833 (9) |
O14—O12 | 2.4840 (9) | N7B—O11v | 2.6732 (11) |
O14—O11 | 2.5150 (10) | N7B—H7B | 0.883 (7) |
O14—O13 | 2.5268 (8) | N1A—C2A | 1.3210 (9) |
O14—O22i | 2.5420 (9) | N1A—C6A | 1.3639 (9) |
O14—O21 | 3.2107 (11) | C6B—N6B | 1.3293 (9) |
O14—O14i | 3.4241 (14) | C6B—C5B | 1.4171 (10) |
O14—H14 | 1.033 (11) | C4B—C5B | 1.3780 (9) |
O13—O11 | 2.5182 (13) | C8B—H8B | 0.954 (7) |
O13—O12 | 2.5196 (9) | C5A—C4A | 1.3799 (9) |
O13—N3A | 2.5499 (11) | C5A—C6A | 1.4144 (10) |
O11—O12 | 2.4797 (9) | C2A—H2A | 0.953 (7) |
O11—O24ii | 2.5449 (9) | N6B—C10B | 1.4695 (10) |
O11—N7Biii | 2.6732 (11) | N6B—H6B | 0.841 (7) |
O11—O22ii | 3.3532 (11) | C6A—N6A | 1.3280 (9) |
O12—O21 | 2.5417 (9) | N6A—C10A | 1.4699 (9) |
O12—O23 | 3.2367 (14) | N6A—H6A | 0.838 (8) |
O12—H12 | 0.838 (10) | C2B—H2B | 1.008 (8) |
P2—O22 | 1.4999 (7) | C8A—H8A | 0.970 (7) |
P2—O21 | 1.5249 (8) | C10A—C11A | 1.4851 (10) |
P2—O24 | 1.5579 (7) | C10A—O15A | 2.4690 (14) |
P2—O23 | 1.5661 (6) | C10A—H0A1 | 1.025 (6) |
O21—O23 | 2.4720 (12) | C10A—H0A2 | 0.992 (7) |
O21—O24 | 2.5151 (10) | C10B—C11B | 1.4826 (10) |
O21—O22 | 2.5160 (11) | C10B—O15B | 2.4626 (14) |
O22—O24 | 2.5331 (10) | C10B—H0B1 | 1.002 (6) |
O22—O23 | 2.5337 (9) | C10B—H0B2 | 1.003 (7) |
O22—O14i | 2.5420 (9) | C11A—C12A | 1.3187 (12) |
O22—O11iv | 3.3532 (11) | C11A—O15A | 1.3491 (9) |
O24—O23 | 2.4788 (10) | C12B—C11B | 1.3117 (11) |
O24—O11iv | 2.5449 (9) | C12B—C13B | 1.4352 (12) |
O24—H24 | 0.832 (10) | C12B—O15B | 2.1809 (11) |
O23—N3B | 2.6397 (11) | C12B—H12B | 0.400 (5) |
O23—H23 | 0.963 (9) | C11B—O15B | 1.3393 (9) |
N3A—C2A | 1.3379 (9) | C12A—C13A | 1.4545 (13) |
N3A—C4A | 1.3610 (9) | C12A—O15A | 2.1983 (11) |
N3A—H3A | 1.011 (9) | C12A—H12A | 0.416 (6) |
N3B—C2B | 1.3440 (10) | O15A—C14A | 1.3929 (12) |
N3B—C4B | 1.3469 (9) | O15A—C13A | 2.1945 (13) |
N1B—C2B | 1.3377 (9) | O15B—C14B | 1.3974 (12) |
N1B—C6B | 1.3538 (9) | O15B—C13B | 2.1967 (13) |
N7A—C8A | 1.3430 (9) | C14B—C13B | 1.2978 (14) |
N7A—C5A | 1.3768 (9) | C14B—H14B | 1.024 (13) |
N7A—H7A | 0.889 (7) | C13B—H13B | 0.904 (11) |
N9A—C8A | 1.3359 (9) | C14A—C13A | 1.2913 (14) |
N9A—C4A | 1.3692 (9) | C14A—H14A | 1.082 (12) |
N9B—C8B | 1.3429 (9) | C13A—H13A | 0.860 (13) |
| | | |
O13—P1—O11 | 112.52 (4) | P2—O23—O12 | 87.06 (4) |
O13—P1—O12 | 111.07 (4) | O21—O23—O12 | 50.74 (3) |
O11—P1—O12 | 107.23 (3) | O24—O23—O12 | 102.74 (3) |
O13—P1—O14 | 111.05 (3) | O22—O23—O12 | 104.97 (3) |
O11—P1—O14 | 109.00 (4) | N3B—O23—O12 | 122.62 (3) |
O12—P1—O14 | 105.68 (3) | P2—O23—H23 | 120.1 (6) |
P1—O14—O12 | 37.04 (2) | O21—O23—H23 | 137.2 (6) |
P1—O14—O11 | 35.02 (2) | O24—O23—H23 | 83.6 (6) |
O12—O14—O11 | 59.47 (3) | O22—O23—H23 | 124.0 (6) |
P1—O14—O13 | 33.69 (2) | N3B—O23—H23 | 2.8 (6) |
O12—O14—O13 | 60.37 (3) | O12—O23—H23 | 125.3 (6) |
O11—O14—O13 | 59.93 (3) | C2A—N3A—C4A | 116.21 (6) |
P1—O14—O22i | 109.50 (3) | C2A—N3A—O13 | 122.42 (5) |
O12—O14—O22i | 146.45 (3) | C4A—N3A—O13 | 120.97 (5) |
O11—O14—O22i | 94.15 (3) | C2A—N3A—H3A | 120.8 (6) |
O13—O14—O22i | 89.30 (3) | C4A—N3A—H3A | 122.8 (6) |
P1—O14—O21 | 88.04 (3) | O13—N3A—H3A | 2.7 (6) |
O12—O14—O21 | 51.09 (2) | C2B—N3B—C4B | 112.16 (6) |
O11—O14—O21 | 104.24 (3) | C2B—N3B—O23 | 119.03 (5) |
O13—O14—O21 | 102.87 (3) | C4B—N3B—O23 | 125.67 (5) |
O22i—O14—O21 | 161.27 (2) | C2B—N1B—C6B | 118.90 (6) |
P1—O14—O14i | 143.00 (3) | C8A—N7A—C5A | 106.47 (5) |
O12—O14—O14i | 118.83 (3) | C8A—N7A—H7A | 129.2 (5) |
O11—O14—O14i | 178.00 (2) | C5A—N7A—H7A | 124.1 (5) |
O13—O14—O14i | 118.52 (4) | C8A—N9A—C4A | 103.38 (6) |
O22i—O14—O14i | 87.04 (3) | C8B—N9B—C4B | 107.65 (6) |
O21—O14—O14i | 74.69 (2) | C8B—N9B—H9B | 124.4 (6) |
P1—O14—H14 | 109.7 (6) | C4B—N9B—H9B | 127.9 (6) |
O12—O14—H14 | 146.7 (6) | C8B—N7B—C5B | 108.27 (5) |
O11—O14—H14 | 94.4 (6) | C8B—N7B—O11v | 144.04 (5) |
O13—O14—H14 | 89.5 (6) | C5B—N7B—O11v | 107.68 (4) |
O22i—O14—H14 | 0.2 (6) | C8B—N7B—H7B | 128.8 (5) |
O21—O14—H14 | 161.0 (6) | C5B—N7B—H7B | 122.8 (5) |
O14i—O14—H14 | 86.8 (6) | O11v—N7B—H7B | 15.4 (5) |
P1—O13—O11 | 34.04 (2) | C2A—N1A—C6A | 119.12 (6) |
P1—O13—O12 | 35.14 (2) | N6B—C6B—N1B | 120.24 (6) |
O11—O13—O12 | 58.97 (3) | N6B—C6B—C5B | 122.88 (6) |
P1—O13—O14 | 35.26 (2) | N1B—C6B—C5B | 116.88 (6) |
O11—O13—O14 | 59.80 (3) | N3B—C4B—C5B | 124.80 (6) |
O12—O13—O14 | 58.97 (3) | N3B—C4B—N9B | 128.06 (6) |
P1—O13—N3A | 124.73 (3) | C5B—C4B—N9B | 107.14 (6) |
O11—O13—N3A | 131.51 (3) | N7B—C8B—N9B | 110.11 (6) |
O12—O13—N3A | 89.73 (3) | N7B—C8B—H8B | 123.6 (4) |
O14—O13—N3A | 136.37 (3) | N9B—C8B—H8B | 126.2 (4) |
P1—O11—O12 | 36.77 (2) | N7A—C5A—C4A | 105.32 (6) |
P1—O11—O14 | 35.99 (2) | N7A—C5A—C6A | 134.31 (6) |
O12—O11—O14 | 59.64 (3) | C4A—C5A—C6A | 120.32 (6) |
P1—O11—O13 | 33.43 (2) | N1A—C2A—N3A | 126.67 (6) |
O12—O11—O13 | 60.54 (3) | N1A—C2A—H2A | 116.6 (4) |
O14—O11—O13 | 60.27 (3) | N3A—C2A—H2A | 116.7 (4) |
P1—O11—O24ii | 121.32 (3) | C6B—N6B—C10B | 123.87 (6) |
O12—O11—O24ii | 125.05 (3) | C6B—N6B—H6B | 114.4 (5) |
O14—O11—O24ii | 142.57 (3) | C10B—N6B—H6B | 121.4 (5) |
O13—O11—O24ii | 88.74 (3) | N3A—C4A—N9A | 128.19 (6) |
P1—O11—N7Biii | 116.69 (4) | N3A—C4A—C5A | 120.54 (6) |
O12—O11—N7Biii | 128.57 (3) | N9A—C4A—C5A | 111.27 (6) |
O14—O11—N7Biii | 80.85 (4) | N6A—C6A—N1A | 120.06 (6) |
O13—O11—N7Biii | 127.33 (3) | N6A—C6A—C5A | 122.84 (6) |
O24ii—O11—N7Biii | 106.37 (3) | N1A—C6A—C5A | 117.09 (6) |
P1—O11—O22ii | 118.57 (3) | C6A—N6A—C10A | 123.58 (6) |
O12—O11—O22ii | 152.84 (2) | C6A—N6A—H6A | 115.7 (5) |
O14—O11—O22ii | 108.12 (3) | C10A—N6A—H6A | 119.3 (5) |
O13—O11—O22ii | 92.30 (3) | C4B—C5B—N7B | 106.83 (6) |
O24ii—O11—O22ii | 48.52 (2) | C4B—C5B—C6B | 118.72 (6) |
N7Biii—O11—O22ii | 66.09 (3) | N7B—C5B—C6B | 134.38 (6) |
P1—O12—O11 | 36.01 (2) | N1B—C2B—N3B | 128.47 (6) |
P1—O12—O14 | 37.29 (2) | N1B—C2B—H2B | 114.8 (4) |
O11—O12—O14 | 60.89 (3) | N3B—C2B—H2B | 116.7 (4) |
P1—O12—O13 | 33.80 (2) | N9A—C8A—N7A | 113.55 (6) |
O11—O12—O13 | 60.49 (3) | N9A—C8A—H8A | 125.4 (4) |
O14—O12—O13 | 60.66 (2) | N7A—C8A—H8A | 120.9 (4) |
P1—O12—O21 | 116.57 (3) | N6A—C10A—C11A | 111.07 (6) |
O11—O12—O21 | 129.38 (3) | N6A—C10A—O15A | 100.41 (5) |
O14—O12—O21 | 79.40 (3) | C11A—C10A—O15A | 27.89 (3) |
O13—O12—O21 | 125.84 (3) | N6A—C10A—H0A1 | 108.6 (4) |
P1—O12—O23 | 102.03 (3) | C11A—C10A—H0A1 | 107.7 (4) |
O11—O12—O23 | 137.44 (3) | O15A—C10A—H0A1 | 135.0 (4) |
O14—O12—O23 | 79.91 (3) | N6A—C10A—H0A2 | 108.2 (4) |
O13—O12—O23 | 87.08 (3) | C11A—C10A—H0A2 | 110.2 (3) |
O21—O12—O23 | 48.86 (2) | O15A—C10A—H0A2 | 90.8 (3) |
P1—O12—H12 | 117.8 (6) | H0A1—C10A—H0A2 | 110.9 (5) |
O11—O12—H12 | 132.8 (6) | N6B—C10B—C11B | 111.70 (6) |
O14—O12—H12 | 81.0 (6) | N6B—C10B—O15B | 102.89 (4) |
O13—O12—H12 | 124.5 (6) | C11B—C10B—O15B | 27.64 (3) |
O21—O12—H12 | 3.9 (5) | N6B—C10B—H0B1 | 109.0 (4) |
O23—O12—H12 | 45.4 (5) | C11B—C10B—H0B1 | 109.2 (4) |
O22—P2—O21 | 112.57 (4) | O15B—C10B—H0B1 | 135.3 (4) |
O22—P2—O24 | 111.85 (3) | N6B—C10B—H0B2 | 108.1 (4) |
O21—P2—O24 | 109.34 (3) | C11B—C10B—H0B2 | 109.3 (3) |
O22—P2—O23 | 111.44 (4) | O15B—C10B—H0B2 | 88.6 (3) |
O21—P2—O23 | 106.21 (4) | H0B1—C10B—H0B2 | 109.7 (6) |
O24—P2—O23 | 105.02 (4) | C12A—C11A—O15A | 110.97 (6) |
P2—O21—O23 | 37.47 (3) | C12A—C11A—C10A | 127.35 (6) |
P2—O21—O24 | 35.77 (2) | O15A—C11A—C10A | 121.11 (7) |
O23—O21—O24 | 59.60 (3) | C11B—C12B—C13B | 106.35 (7) |
P2—O21—O22 | 33.40 (2) | C11B—C12B—O15B | 35.06 (4) |
O23—O21—O22 | 61.05 (3) | C13B—C12B—O15B | 71.46 (6) |
O24—O21—O22 | 60.46 (3) | C11B—C12B—H12B | 124.8 (9) |
P2—O21—O12 | 117.87 (3) | C13B—C12B—H12B | 127.4 (9) |
O23—O21—O12 | 80.40 (3) | O15B—C12B—H12B | 159.3 (9) |
O24—O21—O12 | 125.22 (3) | C12B—C11B—O15B | 110.70 (6) |
O22—O21—O12 | 130.72 (3) | C12B—C11B—C10B | 127.30 (6) |
P2—O21—O14 | 104.89 (3) | O15B—C11B—C10B | 121.47 (7) |
O23—O21—O14 | 80.61 (3) | C11A—C12A—C13A | 105.37 (7) |
O24—O21—O14 | 138.76 (3) | C11A—C12A—O15A | 34.96 (4) |
O22—O21—O14 | 92.30 (3) | C13A—C12A—O15A | 70.52 (6) |
O12—O21—O14 | 49.51 (2) | C11A—C12A—H12A | 125.1 (9) |
P2—O22—O21 | 34.03 (2) | C13A—C12A—H12A | 128.7 (9) |
P2—O22—O24 | 34.81 (2) | O15A—C12A—H12A | 159.8 (9) |
O21—O22—O24 | 59.75 (3) | C11A—O15A—C14A | 106.30 (7) |
P2—O22—O23 | 35.12 (2) | C11A—O15A—C13A | 72.66 (5) |
O21—O22—O23 | 58.62 (3) | C14A—O15A—C13A | 33.66 (5) |
O24—O22—O23 | 58.58 (3) | C11A—O15A—C12A | 34.07 (4) |
P2—O22—O14i | 119.28 (3) | C14A—O15A—C12A | 72.33 (6) |
O21—O22—O14i | 105.58 (3) | C13A—O15A—C12A | 38.67 (4) |
O24—O22—O14i | 151.27 (3) | C11A—O15A—C10A | 31.00 (4) |
O23—O22—O14i | 92.76 (3) | C14A—O15A—C10A | 137.21 (5) |
P2—O22—O11iv | 82.78 (3) | C13A—O15A—C10A | 103.55 (4) |
O21—O22—O11iv | 96.04 (3) | C12A—O15A—C10A | 64.88 (4) |
O24—O22—O11iv | 48.83 (2) | C11B—O15B—C14B | 106.30 (7) |
O23—O22—O11iv | 104.68 (3) | C11B—O15B—C12B | 34.24 (4) |
O14i—O22—O11iv | 157.25 (2) | C14B—O15B—C12B | 72.20 (6) |
P2—O24—O23 | 37.61 (2) | C11B—O15B—C13B | 72.41 (5) |
P2—O24—O21 | 34.90 (2) | C14B—O15B—C13B | 33.93 (5) |
O23—O24—O21 | 59.34 (3) | C12B—O15B—C13B | 38.28 (4) |
P2—O24—O22 | 33.34 (2) | C11B—O15B—C10B | 30.90 (4) |
O23—O24—O22 | 60.72 (3) | C14B—O15B—C10B | 137.16 (5) |
O21—O24—O22 | 59.79 (3) | C12B—O15B—C10B | 64.97 (4) |
P2—O24—O11iv | 114.79 (3) | C13B—O15B—C10B | 103.23 (4) |
O23—O24—O11iv | 137.83 (3) | C13B—C14B—O15B | 109.13 (7) |
O21—O24—O11iv | 120.77 (3) | C13B—C14B—H14B | 139.2 (9) |
O22—O24—O11iv | 82.65 (3) | O15B—C14B—H14B | 111.6 (9) |
P2—O24—H24 | 116.6 (6) | C14B—C13B—C12B | 107.20 (9) |
O23—O24—H24 | 138.8 (7) | C14B—C13B—O15B | 36.94 (5) |
O21—O24—H24 | 122.5 (6) | C12B—C13B—O15B | 70.26 (6) |
O22—O24—H24 | 84.3 (7) | C14B—C13B—H13B | 132.4 (6) |
O11iv—O24—H24 | 1.9 (6) | C12B—C13B—H13B | 120.0 (6) |
P2—O23—O21 | 36.323 (19) | O15B—C13B—H13B | 168.1 (7) |
P2—O23—O24 | 37.37 (2) | C13A—C14A—O15A | 109.63 (7) |
O21—O23—O24 | 61.06 (3) | C13A—C14A—H14A | 138.5 (8) |
P2—O23—O22 | 33.436 (19) | O15A—C14A—H14A | 111.7 (8) |
O21—O23—O22 | 60.33 (3) | C14A—C13A—C12A | 107.52 (9) |
O24—O23—O22 | 60.70 (3) | C14A—C13A—O15A | 36.72 (5) |
P2—O23—N3B | 121.70 (3) | C12A—C13A—O15A | 70.80 (6) |
O21—O23—N3B | 136.80 (3) | C14A—C13A—H13A | 135.7 (7) |
O24—O23—N3B | 84.93 (3) | C12A—C13A—H13A | 116.1 (7) |
O22—O23—N3B | 126.66 (3) | O15A—C13A—H13A | 169.7 (8) |
| | | |
O13—P1—O14—O12 | −120.53 (4) | O12—O21—O22—O11iv | −146.86 (3) |
O11—P1—O14—O12 | 114.96 (4) | O14—O21—O22—O11iv | 178.522 (15) |
O13—P1—O14—O11 | 124.51 (4) | O22—P2—O24—O23 | −121.02 (4) |
O12—P1—O14—O11 | −114.96 (4) | O21—P2—O24—O23 | 113.60 (4) |
O11—P1—O14—O13 | −124.51 (4) | O22—P2—O24—O21 | 125.37 (4) |
O12—P1—O14—O13 | 120.53 (4) | O23—P2—O24—O21 | −113.60 (4) |
O13—P1—O14—O22i | 56.34 (4) | O21—P2—O24—O22 | −125.37 (4) |
O11—P1—O14—O22i | −68.18 (4) | O23—P2—O24—O22 | 121.02 (4) |
O12—P1—O14—O22i | 176.87 (2) | O22—P2—O24—O11iv | 16.55 (3) |
O13—P1—O14—O21 | −116.95 (3) | O21—P2—O24—O11iv | −108.83 (3) |
O11—P1—O14—O21 | 118.54 (3) | O23—P2—O24—O11iv | 137.57 (3) |
O12—P1—O14—O21 | 3.585 (19) | O23—O21—O24—P2 | 40.55 (3) |
O13—P1—O14—O14i | −55.93 (7) | O22—O21—O24—P2 | −31.24 (2) |
O11—P1—O14—O14i | 179.56 (5) | O12—O21—O24—P2 | 89.94 (4) |
O12—P1—O14—O14i | 64.61 (6) | O14—O21—O24—P2 | 23.55 (3) |
O12—P1—O13—O11 | 120.22 (4) | P2—O21—O24—O23 | −40.55 (3) |
O14—P1—O13—O11 | −122.49 (4) | O22—O21—O24—O23 | −71.78 (3) |
O11—P1—O13—O12 | −120.22 (4) | O12—O21—O24—O23 | 49.40 (3) |
O14—P1—O13—O12 | 117.29 (4) | O14—O21—O24—O23 | −16.99 (3) |
O11—P1—O13—O14 | 122.49 (4) | P2—O21—O24—O22 | 31.24 (2) |
O12—P1—O13—O14 | −117.29 (4) | O23—O21—O24—O22 | 71.78 (3) |
O11—P1—O13—N3A | −114.48 (4) | O12—O21—O24—O22 | 121.18 (4) |
O12—P1—O13—N3A | 5.74 (4) | O14—O21—O24—O22 | 54.79 (4) |
O14—P1—O13—N3A | 123.03 (4) | P2—O21—O24—O11iv | 89.98 (4) |
O12—O14—O13—P1 | 36.64 (2) | O23—O21—O24—O11iv | 130.52 (3) |
O11—O14—O13—P1 | −33.12 (3) | O22—O21—O24—O11iv | 58.74 (4) |
O22i—O14—O13—P1 | −128.31 (3) | O12—O21—O24—O11iv | 179.92 (2) |
O21—O14—O13—P1 | 66.05 (3) | O14—O21—O24—O11iv | 113.53 (4) |
O14i—O14—O13—P1 | 145.44 (4) | O21—O22—O24—P2 | 32.67 (2) |
P1—O14—O13—O11 | 33.12 (3) | O23—O22—O24—P2 | −36.83 (3) |
O12—O14—O13—O11 | 69.76 (3) | O14i—O22—O24—P2 | −32.68 (4) |
O22i—O14—O13—O11 | −95.20 (3) | O11iv—O22—O24—P2 | 164.89 (3) |
O21—O14—O13—O11 | 99.16 (3) | P2—O22—O24—O23 | 36.83 (3) |
O14i—O14—O13—O11 | 178.56 (3) | O21—O22—O24—O23 | 69.50 (3) |
P1—O14—O13—O12 | −36.64 (2) | O14i—O22—O24—O23 | 4.16 (4) |
O11—O14—O13—O12 | −69.76 (3) | O11iv—O22—O24—O23 | −158.28 (2) |
O22i—O14—O13—O12 | −164.96 (2) | P2—O22—O24—O21 | −32.67 (2) |
O21—O14—O13—O12 | 29.40 (2) | O23—O22—O24—O21 | −69.50 (3) |
O14i—O14—O13—O12 | 108.79 (4) | O14i—O22—O24—O21 | −65.35 (5) |
P1—O14—O13—N3A | −86.94 (5) | O11iv—O22—O24—O21 | 132.22 (3) |
O12—O14—O13—N3A | −50.29 (4) | P2—O22—O24—O11iv | −164.89 (3) |
O11—O14—O13—N3A | −120.05 (4) | O21—O22—O24—O11iv | −132.22 (3) |
O22i—O14—O13—N3A | 144.75 (4) | O23—O22—O24—O11iv | 158.28 (2) |
O21—O14—O13—N3A | −20.89 (4) | O14i—O22—O24—O11iv | 162.43 (4) |
O14i—O14—O13—N3A | 58.50 (5) | O22—P2—O23—O21 | −122.92 (4) |
O13—P1—O11—O12 | 122.41 (4) | O24—P2—O23—O21 | 115.79 (4) |
O14—P1—O11—O12 | −113.95 (4) | O22—P2—O23—O24 | 121.29 (4) |
O13—P1—O11—O14 | −123.64 (4) | O21—P2—O23—O24 | −115.79 (4) |
O12—P1—O11—O14 | 113.95 (4) | O21—P2—O23—O22 | 122.92 (4) |
O12—P1—O11—O13 | −122.41 (4) | O24—P2—O23—O22 | −121.29 (4) |
O14—P1—O11—O13 | 123.64 (4) | O22—P2—O23—N3B | 109.76 (4) |
O13—P1—O11—O24ii | 14.43 (4) | O21—P2—O23—N3B | −127.32 (4) |
O12—P1—O11—O24ii | −107.98 (4) | O24—P2—O23—N3B | −11.53 (4) |
O14—P1—O11—O24ii | 138.07 (3) | O22—P2—O23—O12 | −123.18 (4) |
O13—P1—O11—N7Biii | −118.05 (3) | O21—P2—O23—O12 | −0.26 (2) |
O12—P1—O11—N7Biii | 119.54 (4) | O24—P2—O23—O12 | 115.53 (3) |
O14—P1—O11—N7Biii | 5.59 (4) | O24—O21—O23—P2 | −38.65 (2) |
O13—P1—O11—O22ii | −42.11 (4) | O22—O21—O23—P2 | 32.16 (3) |
O12—P1—O11—O22ii | −164.52 (3) | O12—O21—O23—P2 | −179.67 (3) |
O14—P1—O11—O22ii | 81.53 (4) | O14—O21—O23—P2 | 130.09 (3) |
O12—O14—O11—P1 | −39.34 (3) | P2—O21—O23—O24 | 38.65 (2) |
O13—O14—O11—P1 | 31.89 (2) | O22—O21—O23—O24 | 70.81 (3) |
O22i—O14—O11—P1 | 118.67 (4) | O12—O21—O23—O24 | −141.02 (2) |
O21—O14—O11—P1 | −64.93 (4) | O14—O21—O23—O24 | 168.74 (2) |
O14i—O14—O11—P1 | −7.6 (8) | P2—O21—O23—O22 | −32.16 (3) |
P1—O14—O11—O12 | 39.34 (3) | O24—O21—O23—O22 | −70.81 (3) |
O13—O14—O11—O12 | 71.23 (3) | O12—O21—O23—O22 | 148.17 (3) |
O22i—O14—O11—O12 | 158.01 (2) | O14—O21—O23—O22 | 97.93 (3) |
O21—O14—O11—O12 | −25.59 (2) | P2—O21—O23—N3B | 81.24 (5) |
O14i—O14—O11—O12 | 31.8 (8) | O24—O21—O23—N3B | 42.59 (4) |
P1—O14—O11—O13 | −31.89 (2) | O22—O21—O23—N3B | 113.40 (4) |
O12—O14—O11—O13 | −71.23 (3) | O12—O21—O23—N3B | −98.43 (4) |
O22i—O14—O11—O13 | 86.79 (4) | O14—O21—O23—N3B | −148.67 (4) |
O21—O14—O11—O13 | −96.81 (4) | P2—O21—O23—O12 | 179.67 (3) |
O14i—O14—O11—O13 | −39.5 (8) | O24—O21—O23—O12 | 141.02 (2) |
P1—O14—O11—O24ii | −69.92 (4) | O22—O21—O23—O12 | −148.17 (3) |
O12—O14—O11—O24ii | −109.26 (4) | O14—O21—O23—O12 | −50.24 (2) |
O13—O14—O11—O24ii | −38.03 (4) | O21—O24—O23—P2 | 37.55 (3) |
O22i—O14—O11—O24ii | 48.75 (4) | O22—O24—O23—P2 | −32.68 (3) |
O21—O14—O11—O24ii | −134.85 (4) | O11iv—O24—O23—P2 | −65.83 (5) |
O14i—O14—O11—O24ii | −77.5 (8) | P2—O24—O23—O21 | −37.55 (3) |
P1—O14—O11—N7Biii | −174.95 (3) | O22—O24—O23—O21 | −70.23 (3) |
O12—O14—O11—N7Biii | 145.71 (3) | O11iv—O24—O23—O21 | −103.38 (4) |
O13—O14—O11—N7Biii | −143.06 (3) | P2—O24—O23—O22 | 32.68 (3) |
O22i—O14—O11—N7Biii | −56.28 (3) | O21—O24—O23—O22 | 70.23 (3) |
O21—O14—O11—N7Biii | 120.12 (3) | O11iv—O24—O23—O22 | −33.15 (3) |
O14i—O14—O11—N7Biii | 177.5 (8) | P2—O24—O23—N3B | 170.17 (3) |
P1—O14—O11—O22ii | −113.94 (4) | O21—O24—O23—N3B | −152.28 (3) |
O12—O14—O11—O22ii | −153.28 (2) | O22—O24—O23—N3B | 137.49 (3) |
O13—O14—O11—O22ii | −82.06 (4) | O11iv—O24—O23—N3B | 104.34 (5) |
O22i—O14—O11—O22ii | 4.73 (3) | P2—O24—O23—O12 | −67.51 (4) |
O21—O14—O11—O22ii | −178.869 (15) | O21—O24—O23—O12 | −29.96 (2) |
O14i—O14—O11—O22ii | −121.5 (8) | O22—O24—O23—O12 | −100.19 (3) |
O12—O13—O11—P1 | 35.48 (3) | O11iv—O24—O23—O12 | −133.33 (3) |
O14—O13—O11—P1 | −34.29 (3) | O21—O22—O23—P2 | −34.91 (3) |
N3A—O13—O11—P1 | 92.82 (5) | O24—O22—O23—P2 | 36.50 (3) |
P1—O13—O11—O12 | −35.48 (3) | O14i—O22—O23—P2 | −141.50 (3) |
O14—O13—O11—O12 | −69.77 (3) | O11iv—O22—O23—P2 | 53.24 (3) |
N3A—O13—O11—O12 | 57.34 (4) | P2—O22—O23—O21 | 34.91 (3) |
P1—O13—O11—O14 | 34.29 (3) | O24—O22—O23—O21 | 71.41 (3) |
O12—O13—O11—O14 | 69.77 (3) | O14i—O22—O23—O21 | −106.59 (3) |
N3A—O13—O11—O14 | 127.11 (4) | O11iv—O22—O23—O21 | 88.15 (3) |
P1—O13—O11—O24ii | −167.71 (3) | P2—O22—O23—O24 | −36.50 (3) |
O12—O13—O11—O24ii | −132.23 (3) | O21—O22—O23—O24 | −71.41 (3) |
O14—O13—O11—O24ii | 158.00 (2) | O14i—O22—O23—O24 | −178.001 (19) |
N3A—O13—O11—O24ii | −74.89 (4) | O11iv—O22—O23—O24 | 16.739 (18) |
P1—O13—O11—N7Biii | 82.55 (4) | P2—O22—O23—N3B | −93.54 (5) |
O12—O13—O11—N7Biii | 118.02 (4) | O21—O22—O23—N3B | −128.45 (4) |
O14—O13—O11—N7Biii | 48.26 (3) | O24—O22—O23—N3B | −57.04 (4) |
N3A—O13—O11—N7Biii | 175.36 (3) | O14i—O22—O23—N3B | 124.96 (4) |
P1—O13—O11—O22ii | 143.89 (3) | O11iv—O22—O23—N3B | −40.30 (4) |
O12—O13—O11—O22ii | 179.37 (2) | P2—O22—O23—O12 | 59.91 (4) |
O14—O13—O11—O22ii | 109.60 (3) | O21—O22—O23—O12 | 25.01 (2) |
N3A—O13—O11—O22ii | −123.29 (4) | O24—O22—O23—O12 | 96.41 (3) |
O13—P1—O12—O11 | −123.31 (4) | O14i—O22—O23—O12 | −81.59 (3) |
O14—P1—O12—O11 | 116.17 (3) | O11iv—O22—O23—O12 | 113.15 (3) |
O13—P1—O12—O14 | 120.52 (4) | P1—O12—O23—P2 | 115.10 (4) |
O11—P1—O12—O14 | −116.17 (3) | O11—O12—O23—P2 | 107.30 (4) |
O11—P1—O12—O13 | 123.31 (4) | O14—O12—O23—P2 | 84.89 (3) |
O14—P1—O12—O13 | −120.52 (4) | O13—O12—O23—P2 | 145.59 (3) |
O13—P1—O12—O21 | 115.46 (4) | O21—O12—O23—P2 | 0.196 (19) |
O11—P1—O12—O21 | −121.23 (3) | P1—O12—O23—O21 | 114.90 (4) |
O14—P1—O12—O21 | −5.06 (3) | O11—O12—O23—O21 | 107.11 (4) |
O13—P1—O12—O23 | 65.66 (4) | O14—O12—O23—O21 | 84.69 (3) |
O11—P1—O12—O23 | −171.02 (2) | O13—O12—O23—O21 | 145.40 (3) |
O14—P1—O12—O23 | −54.85 (3) | P1—O12—O23—O24 | 149.26 (3) |
O14—O11—O12—P1 | −38.49 (2) | O11—O12—O23—O24 | 141.47 (3) |
O13—O11—O12—P1 | 32.29 (3) | O14—O12—O23—O24 | 119.05 (3) |
O24ii—O11—O12—P1 | 97.01 (4) | O13—O12—O23—O24 | 179.76 (2) |
N7Biii—O11—O12—P1 | −83.84 (4) | O21—O12—O23—O24 | 34.36 (3) |
O22ii—O11—O12—P1 | 30.90 (5) | P1—O12—O23—O22 | 86.58 (4) |
P1—O11—O12—O14 | 38.49 (2) | O11—O12—O23—O22 | 78.79 (5) |
O13—O11—O12—O14 | 70.78 (3) | O14—O12—O23—O22 | 56.37 (3) |
O24ii—O11—O12—O14 | 135.50 (4) | O13—O12—O23—O22 | 117.08 (3) |
N7Biii—O11—O12—O14 | −45.35 (3) | O21—O12—O23—O22 | −28.32 (2) |
O22ii—O11—O12—O14 | 69.39 (5) | P1—O12—O23—N3B | −118.61 (4) |
P1—O11—O12—O13 | −32.29 (3) | O11—O12—O23—N3B | −126.41 (4) |
O14—O11—O12—O13 | −70.78 (3) | O14—O12—O23—N3B | −148.82 (3) |
O24ii—O11—O12—O13 | 64.72 (3) | O13—O12—O23—N3B | −88.11 (3) |
N7Biii—O11—O12—O13 | −116.12 (3) | O21—O12—O23—N3B | 126.49 (4) |
O22ii—O11—O12—O13 | −1.39 (5) | P1—O13—N3A—C2A | −5.95 (6) |
P1—O11—O12—O21 | 81.65 (4) | O11—O13—N3A—C2A | −48.82 (6) |
O14—O11—O12—O21 | 43.16 (3) | O12—O13—N3A—C2A | −2.65 (5) |
O13—O11—O12—O21 | 113.94 (3) | O14—O13—N3A—C2A | 38.59 (6) |
O24ii—O11—O12—O21 | 178.66 (2) | P1—O13—N3A—C4A | 166.58 (4) |
N7Biii—O11—O12—O21 | −2.18 (4) | O11—O13—N3A—C4A | 123.71 (5) |
O22ii—O11—O12—O21 | 112.55 (5) | O12—O13—N3A—C4A | 169.88 (4) |
P1—O11—O12—O23 | 13.04 (3) | O14—O13—N3A—C4A | −148.88 (4) |
O14—O11—O12—O23 | −25.45 (3) | P2—O23—N3B—C2B | 23.69 (6) |
O13—O11—O12—O23 | 45.33 (4) | O21—O23—N3B—C2B | −19.79 (7) |
O24ii—O11—O12—O23 | 110.05 (4) | O24—O23—N3B—C2B | 16.69 (5) |
N7Biii—O11—O12—O23 | −70.79 (5) | O22—O23—N3B—C2B | 63.96 (6) |
O22ii—O11—O12—O23 | 43.94 (7) | O12—O23—N3B—C2B | −85.20 (6) |
O11—O14—O12—P1 | 37.15 (2) | P2—O23—N3B—C4B | −177.98 (5) |
O13—O14—O12—P1 | −33.35 (3) | O21—O23—N3B—C4B | 138.54 (5) |
O22i—O14—O12—P1 | −5.35 (3) | O24—O23—N3B—C4B | 175.03 (5) |
O21—O14—O12—P1 | −175.39 (2) | O22—O23—N3B—C4B | −137.70 (5) |
O14i—O14—O12—P1 | −141.65 (4) | O12—O23—N3B—C4B | 73.13 (6) |
P1—O14—O12—O11 | −37.15 (2) | C2B—N1B—C6B—N6B | −178.05 (5) |
O13—O14—O12—O11 | −70.50 (4) | C2B—N1B—C6B—C5B | 1.72 (8) |
O22i—O14—O12—O11 | −42.50 (4) | C2B—N3B—C4B—C5B | 0.34 (8) |
O21—O14—O12—O11 | 147.45 (2) | O23—N3B—C4B—C5B | −159.26 (5) |
O14i—O14—O12—O11 | −178.80 (3) | C2B—N3B—C4B—N9B | 179.48 (6) |
P1—O14—O12—O13 | 33.35 (3) | O23—N3B—C4B—N9B | 19.88 (8) |
O11—O14—O12—O13 | 70.50 (4) | C8B—N9B—C4B—N3B | −179.53 (6) |
O22i—O14—O12—O13 | 28.00 (4) | C8B—N9B—C4B—C5B | −0.27 (6) |
O21—O14—O12—O13 | −142.05 (3) | C5B—N7B—C8B—N9B | −0.41 (6) |
O14i—O14—O12—O13 | −108.30 (4) | O11v—N7B—C8B—N9B | −179.14 (5) |
P1—O14—O12—O21 | 175.39 (2) | C4B—N9B—C8B—N7B | 0.43 (6) |
O11—O14—O12—O21 | −147.45 (2) | C8A—N7A—C5A—C4A | 0.67 (6) |
O13—O14—O12—O21 | 142.05 (3) | C8A—N7A—C5A—C6A | 178.24 (6) |
O22i—O14—O12—O21 | 170.05 (3) | C6A—N1A—C2A—N3A | −0.44 (9) |
O14i—O14—O12—O21 | 33.75 (3) | C4A—N3A—C2A—N1A | −0.69 (9) |
P1—O14—O12—O23 | 125.68 (3) | O13—N3A—C2A—N1A | 172.18 (5) |
O11—O14—O12—O23 | 162.83 (2) | N1B—C6B—N6B—C10B | 6.28 (8) |
O13—O14—O12—O23 | 92.33 (3) | C5B—C6B—N6B—C10B | −173.48 (5) |
O22i—O14—O12—O23 | 120.33 (4) | C2A—N3A—C4A—N9A | 179.83 (5) |
O21—O14—O12—O23 | −49.72 (2) | O13—N3A—C4A—N9A | 6.86 (8) |
O14i—O14—O12—O23 | −15.97 (3) | C2A—N3A—C4A—C5A | 0.20 (8) |
O11—O13—O12—P1 | −34.37 (3) | O13—N3A—C4A—C5A | −172.77 (4) |
O14—O13—O12—P1 | 36.78 (3) | C8A—N9A—C4A—N3A | −179.73 (6) |
N3A—O13—O12—P1 | −175.28 (3) | C8A—N9A—C4A—C5A | −0.07 (6) |
P1—O13—O12—O11 | 34.37 (3) | N7A—C5A—C4A—N3A | 179.31 (5) |
O14—O13—O12—O11 | 71.15 (3) | C6A—C5A—C4A—N3A | 1.32 (8) |
N3A—O13—O12—O11 | −140.92 (3) | N7A—C5A—C4A—N9A | −0.38 (6) |
P1—O13—O12—O14 | −36.78 (3) | C6A—C5A—C4A—N9A | −178.37 (5) |
O11—O13—O12—O14 | −71.15 (3) | C2A—N1A—C6A—N6A | −178.69 (5) |
N3A—O13—O12—O14 | 147.94 (3) | C2A—N1A—C6A—C5A | 1.93 (8) |
P1—O13—O12—O21 | −85.00 (4) | N7A—C5A—C6A—N6A | 0.97 (10) |
O11—O13—O12—O21 | −119.37 (4) | C4A—C5A—C6A—N6A | 178.25 (5) |
O14—O13—O12—O21 | −48.22 (3) | N7A—C5A—C6A—N1A | −179.66 (6) |
N3A—O13—O12—O21 | 99.72 (4) | C4A—C5A—C6A—N1A | −2.37 (8) |
P1—O13—O12—O23 | −116.84 (4) | N1A—C6A—N6A—C10A | 10.23 (8) |
O11—O13—O12—O23 | −151.21 (2) | C5A—C6A—N6A—C10A | −170.42 (5) |
O14—O13—O12—O23 | −80.06 (3) | N3B—C4B—C5B—N7B | 179.32 (5) |
N3A—O13—O12—O23 | 67.88 (3) | N9B—C4B—C5B—N7B | 0.03 (6) |
O22—P2—O21—O23 | 122.21 (4) | N3B—C4B—C5B—C6B | 1.89 (9) |
O24—P2—O21—O23 | −112.83 (4) | N9B—C4B—C5B—C6B | −177.40 (5) |
O22—P2—O21—O24 | −124.96 (4) | C8B—N7B—C5B—C4B | 0.23 (6) |
O23—P2—O21—O24 | 112.83 (4) | O11v—N7B—C5B—C4B | 179.45 (4) |
O24—P2—O21—O22 | 124.96 (4) | C8B—N7B—C5B—C6B | 177.08 (6) |
O23—P2—O21—O22 | −122.21 (4) | O11v—N7B—C5B—C6B | −3.70 (8) |
O22—P2—O21—O12 | 122.58 (4) | N6B—C6B—C5B—C4B | 176.89 (5) |
O24—P2—O21—O12 | −112.46 (4) | N1B—C6B—C5B—C4B | −2.88 (8) |
O23—P2—O21—O12 | 0.37 (3) | N6B—C6B—C5B—N7B | 0.33 (10) |
O22—P2—O21—O14 | 70.86 (4) | N1B—C6B—C5B—N7B | −179.44 (6) |
O24—P2—O21—O14 | −164.18 (2) | C6B—N1B—C2B—N3B | 0.66 (9) |
O23—P2—O21—O14 | −51.35 (3) | C4B—N3B—C2B—N1B | −1.71 (9) |
P1—O12—O21—P2 | −82.91 (4) | O23—N3B—C2B—N1B | 159.39 (5) |
O11—O12—O21—P2 | −123.47 (4) | C4A—N9A—C8A—N7A | 0.53 (6) |
O14—O12—O21—P2 | −86.02 (4) | C5A—N7A—C8A—N9A | −0.78 (7) |
O13—O12—O21—P2 | −44.62 (5) | C6A—N6A—C10A—C11A | 91.56 (8) |
O23—O12—O21—P2 | −0.23 (2) | C6A—N6A—C10A—O15A | 64.71 (7) |
P1—O12—O21—O23 | −82.68 (4) | C6B—N6B—C10B—C11B | 93.52 (8) |
O11—O12—O21—O23 | −123.24 (3) | C6B—N6B—C10B—O15B | 66.03 (7) |
O14—O12—O21—O23 | −85.80 (3) | N6A—C10A—C11A—C12A | 98.84 (10) |
O13—O12—O21—O23 | −44.39 (4) | O15A—C10A—C11A—C12A | 170.55 (14) |
P1—O12—O21—O24 | −124.30 (4) | N6A—C10A—C11A—O15A | −71.71 (9) |
O11—O12—O21—O24 | −164.86 (3) | C13B—C12B—C11B—O15B | −5.80 (10) |
O14—O12—O21—O24 | −127.41 (4) | C13B—C12B—C11B—C10B | −177.47 (8) |
O13—O12—O21—O24 | −86.01 (5) | O15B—C12B—C11B—C10B | −171.67 (12) |
O23—O12—O21—O24 | −41.62 (3) | N6B—C10B—C11B—C12B | 94.89 (9) |
P1—O12—O21—O22 | −45.17 (4) | O15B—C10B—C11B—C12B | 170.85 (14) |
O11—O12—O21—O22 | −85.73 (5) | N6B—C10B—C11B—O15B | −75.97 (9) |
O14—O12—O21—O22 | −48.29 (3) | O15A—C11A—C12A—C13A | −4.90 (10) |
O13—O12—O21—O22 | −6.88 (4) | C10A—C11A—C12A—C13A | −176.24 (8) |
O23—O12—O21—O22 | 37.51 (3) | C10A—C11A—C12A—O15A | −171.34 (13) |
P1—O12—O21—O14 | 3.118 (17) | C12A—C11A—O15A—C14A | 4.42 (10) |
O11—O12—O21—O14 | −37.45 (3) | C10A—C11A—O15A—C14A | 176.38 (7) |
O13—O12—O21—O14 | 41.40 (3) | C12A—C11A—O15A—C13A | 3.28 (7) |
O23—O12—O21—O14 | 85.80 (3) | C10A—C11A—O15A—C13A | 175.24 (8) |
P1—O14—O21—P2 | 111.37 (3) | C10A—C11A—O15A—C12A | 171.96 (12) |
O12—O14—O21—P2 | 114.15 (3) | C12A—C11A—O15A—C10A | −171.96 (12) |
O11—O14—O21—P2 | 142.71 (3) | C13A—C12A—O15A—C11A | 174.99 (11) |
O13—O14—O21—P2 | 80.89 (4) | C11A—C12A—O15A—C14A | −175.55 (10) |
O22i—O14—O21—P2 | −48.54 (7) | C13A—C12A—O15A—C14A | −0.56 (7) |
O14i—O14—O21—P2 | −35.55 (3) | C11A—C12A—O15A—C13A | −174.99 (11) |
P1—O14—O21—O23 | 82.58 (3) | C11A—C12A—O15A—C10A | 4.56 (7) |
O12—O14—O21—O23 | 85.36 (3) | C13A—C12A—O15A—C10A | 179.55 (7) |
O11—O14—O21—O23 | 113.92 (4) | N6A—C10A—O15A—C11A | 115.74 (9) |
O13—O14—O21—O23 | 52.10 (3) | N6A—C10A—O15A—C14A | 110.62 (9) |
O22i—O14—O21—O23 | −77.33 (7) | C11A—C10A—O15A—C14A | −5.11 (10) |
O14i—O14—O21—O23 | −64.34 (4) | N6A—C10A—O15A—C13A | 111.06 (6) |
P1—O14—O21—O24 | 97.39 (4) | C11A—C10A—O15A—C13A | −4.67 (7) |
O12—O14—O21—O24 | 100.16 (4) | N6A—C10A—O15A—C12A | 110.77 (6) |
O11—O14—O21—O24 | 128.72 (4) | C11A—C10A—O15A—C12A | −4.96 (7) |
O13—O14—O21—O24 | 66.90 (4) | C12B—C11B—O15B—C14B | 5.39 (10) |
O22i—O14—O21—O24 | −62.53 (8) | C10B—C11B—O15B—C14B | 177.62 (7) |
O14i—O14—O21—O24 | −49.54 (4) | C10B—C11B—O15B—C12B | 172.23 (12) |
P1—O14—O21—O22 | 142.74 (3) | C12B—C11B—O15B—C13B | 3.81 (7) |
O12—O14—O21—O22 | 145.51 (3) | C10B—C11B—O15B—C13B | 176.04 (8) |
O11—O14—O21—O22 | 174.071 (19) | C12B—C11B—O15B—C10B | −172.23 (12) |
O13—O14—O21—O22 | 112.25 (4) | C13B—C12B—O15B—C11B | 174.13 (10) |
O22i—O14—O21—O22 | −17.18 (7) | C11B—C12B—O15B—C14B | −174.56 (10) |
O14i—O14—O21—O22 | −4.186 (18) | C13B—C12B—O15B—C14B | −0.44 (7) |
P1—O14—O21—O12 | −2.774 (15) | C11B—C12B—O15B—C13B | −174.13 (10) |
O11—O14—O21—O12 | 28.56 (2) | C11B—C12B—O15B—C10B | 4.39 (7) |
O13—O14—O21—O12 | −33.26 (3) | C13B—C12B—O15B—C10B | 178.52 (7) |
O22i—O14—O21—O12 | −162.69 (6) | N6B—C10B—O15B—C11B | 112.38 (9) |
O14i—O14—O21—O12 | −149.70 (3) | N6B—C10B—O15B—C14B | 109.02 (10) |
O24—P2—O22—O21 | −123.57 (4) | C11B—C10B—O15B—C14B | −3.36 (10) |
O23—P2—O22—O21 | 119.20 (4) | N6B—C10B—O15B—C12B | 107.56 (6) |
O21—P2—O22—O24 | 123.57 (4) | C11B—C10B—O15B—C12B | −4.81 (7) |
O23—P2—O22—O24 | −117.22 (4) | N6B—C10B—O15B—C13B | 108.51 (6) |
O21—P2—O22—O23 | −119.20 (4) | C11B—C10B—O15B—C13B | −3.87 (7) |
O24—P2—O22—O23 | 117.22 (4) | C11B—O15B—C14B—C13B | −2.70 (11) |
O21—P2—O22—O14i | −73.73 (4) | C12B—O15B—C14B—C13B | 0.48 (8) |
O24—P2—O22—O14i | 162.69 (2) | C10B—O15B—C14B—C13B | −0.90 (14) |
O23—P2—O22—O14i | 45.47 (4) | O15B—C14B—C13B—C12B | −0.73 (12) |
O21—P2—O22—O11iv | 112.17 (3) | C11B—C12B—C13B—C14B | 3.98 (11) |
O24—P2—O22—O11iv | −11.41 (2) | O15B—C12B—C13B—C14B | 0.47 (7) |
O23—P2—O22—O11iv | −128.63 (3) | C11B—C12B—C13B—O15B | 3.51 (6) |
O23—O21—O22—P2 | −36.03 (3) | C11B—O15B—C13B—C14B | 177.28 (11) |
O24—O21—O22—P2 | 33.41 (3) | C12B—O15B—C13B—C14B | −179.25 (12) |
O12—O21—O22—P2 | −79.36 (4) | C10B—O15B—C13B—C14B | 179.37 (10) |
O14—O21—O22—P2 | −113.98 (4) | C11B—O15B—C13B—C12B | −3.46 (6) |
P2—O21—O22—O24 | −33.41 (3) | C14B—O15B—C13B—C12B | 179.25 (12) |
O23—O21—O22—O24 | −69.44 (3) | C10B—O15B—C13B—C12B | −1.38 (6) |
O12—O21—O22—O24 | −112.76 (3) | C11A—O15A—C14A—C13A | −1.96 (11) |
O14—O21—O22—O24 | −147.38 (2) | C12A—O15A—C14A—C13A | 0.63 (8) |
P2—O21—O22—O23 | 36.03 (3) | C10A—O15A—C14A—C13A | 0.78 (14) |
O24—O21—O22—O23 | 69.44 (3) | O15A—C14A—C13A—C12A | −0.95 (12) |
O12—O21—O22—O23 | −43.32 (3) | C11A—C12A—C13A—C14A | 3.58 (11) |
O14—O21—O22—O23 | −77.94 (3) | O15A—C12A—C13A—C14A | 0.60 (7) |
P2—O21—O22—O14i | 119.63 (4) | C11A—C12A—C13A—O15A | 2.98 (6) |
O23—O21—O22—O14i | 83.59 (4) | C11A—O15A—C13A—C14A | 178.02 (11) |
O24—O21—O22—O14i | 153.03 (3) | C12A—O15A—C13A—C14A | −179.04 (12) |
O12—O21—O22—O14i | 40.27 (4) | C10A—O15A—C13A—C14A | −179.46 (9) |
O14—O21—O22—O14i | 5.65 (2) | C11A—O15A—C13A—C12A | −2.94 (6) |
P2—O21—O22—O11iv | −67.50 (4) | C14A—O15A—C13A—C12A | 179.04 (12) |
O23—O21—O22—O11iv | −103.53 (3) | C10A—O15A—C13A—C12A | −0.42 (6) |
O24—O21—O22—O11iv | −34.09 (2) | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x−1, y−1, z; (iv) x+1, y, z; (v) x+1, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7B—H7B···O11v | 0.883 (7) | 1.837 (7) | 2.6732 (11) | 157.3 (7) |
N6A—H6A···O21vi | 0.838 (8) | 2.029 (8) | 2.8586 (10) | 170.5 (7) |
N6B—H6B···O11v | 0.841 (7) | 2.076 (8) | 2.9068 (10) | 169.4 (7) |
N7A—H7A···O21vi | 0.889 (7) | 1.958 (7) | 2.7794 (11) | 153.0 (7) |
O23—H23···N3B | 0.963 (9) | 1.679 (9) | 2.6397 (11) | 175.6 (9) |
N9B—H9B···N9Avii | 0.933 (9) | 1.940 (9) | 2.8716 (12) | 176.1 (9) |
O12—H12···O21 | 0.838 (10) | 1.707 (10) | 2.5417 (9) | 174.1 (8) |
O24—H24···O11iv | 0.832 (10) | 1.714 (10) | 2.5449 (9) | 177.2 (9) |
O14—H14···O22i | 1.033 (11) | 1.509 (11) | 2.5420 (9) | 179.6 (9) |
N3A—H3A···O13 | 1.011 (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. |
Crystal data top
C10H9N50·H3O4P | Z = 2 |
Mr = 313.22 | F(000) = 324 |
TRICLINIC, P1 | Dx = 1.608 Mg m−3 |
a = 4.4923 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.736 (2) Å | Cell parameters from 3615 reflections |
c = 14.455 (3) Å | θ = 2.2–20.1° |
α = 91.00 (3)° | µ = 0.25 mm−1 |
β = 100.92 (3)° | T = 293 K |
γ = 108.47 (3)° | THIN NEEDLE, colourlrss |
V = 647.0 (2) Å3 | 0.41 × 0.09 × 0.09 mm |
Data collection top
KM4CCD diffractometer | 5349 independent reflections |
Radiation source: fine-focus sealed tube | 3704 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
CCD scans | θmax = 40.3°, θmin = 4.2° |
Absorption correction: ANALYTICAL- crysAlis Ver170.26 ? | h = −5→8 |
Tmin = 0.915, Tmax = 0.982 | k = −17→19 |
14205 measured reflections | l = −24→25 |
Refinement top
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)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | Calculated w = 1/[σ2(Fo2) + (0.030P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3 |
S = 1.21 | (Δ/σ)max = 1.110 |
3704 reflections | Δρmax = 0.42 e Å−3 |
230 parameters | Δρmin = −0.42 e Å−3 |
6 restraints | Extinction correction: SHELXL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0051 (6) |
Crystal data top
C10H9N50·H3O4P | γ = 108.47 (3)° |
Mr = 313.22 | V = 647.0 (2) Å3 |
TRICLINIC, P1 | Z = 2 |
a = 4.4923 (9) Å | Mo Kα radiation |
b = 10.736 (2) Å | µ = 0.25 mm−1 |
c = 14.455 (3) Å | T = 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 = 0.982 | Rint = 0.042 |
14205 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 6 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.21 | (Δ/σ)max = 1.110 |
3704 reflections | Δρmax = 0.42 e Å−3 |
230 parameters | Δρmin = −0.42 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.50152 (5) | 0.41820 (2) | 0.650206 (16) | 0.03131 (6) | |
O11 | 0.84100 (14) | 0.49848 (6) | 0.69833 (5) | 0.03952 (19) | |
O14 | 0.28906 (14) | 0.39684 (7) | 0.72484 (5) | 0.04474 (19) | |
O12 | 0.37165 (17) | 0.49211 (8) | 0.57185 (5) | 0.0535 (2) | |
O13 | 0.49328 (19) | 0.28368 (7) | 0.61236 (6) | 0.0673 (3) | |
N7A | 0.89979 (18) | 0.27033 (7) | 0.37875 (5) | 0.0354 (2) | |
C5A | 0.9620 (2) | 0.17194 (8) | 0.33073 (6) | 0.0304 (2) | |
C6A | 1.1143 (2) | 0.16831 (9) | 0.25398 (6) | 0.0329 (2) | |
N6A | 1.23787 (18) | 0.27477 (8) | 0.20996 (5) | 0.0377 (2) | |
N1A | 1.13127 (19) | 0.05008 (8) | 0.22584 (6) | 0.0408 (2) | |
N3A | 0.84149 (19) | −0.06057 (8) | 0.33987 (6) | 0.0402 (2) | |
C4A | 0.8292 (2) | 0.05723 (9) | 0.37032 (6) | 0.0325 (2) | |
N9A | 0.68896 (18) | 0.08407 (8) | 0.44098 (6) | 0.0393 (2) | |
C2A | 0.9964 (2) | −0.05447 (10) | 0.26902 (8) | 0.0447 (3) | |
C8A | 0.7386 (2) | 0.21350 (10) | 0.44356 (7) | 0.0415 (3) | |
C10A | 1.3657 (2) | 0.27000 (11) | 0.12400 (7) | 0.0450 (3) | |
C11A | 1.1203 (2) | 0.25788 (11) | 0.03733 (7) | 0.0453 (3) | |
O15A | 0.8842 (3) | 0.14556 (10) | 0.00751 (8) | 0.0966 (4) | |
C14A | 0.6949 (4) | 0.16948 (19) | −0.07229 (11) | 0.1018 (6) | |
C13A | 0.8047 (4) | 0.29113 (19) | −0.08774 (11) | 0.1101 (6) | |
C12A | 1.0819 (3) | 0.35400 (12) | −0.01366 (11) | 0.0762 (5) | |
H8A | 0.671 (2) | 0.2572 (10) | 0.4879 (7) | 0.038 (3)* | |
H7A | 0.952 (2) | 0.3632 (11) | 0.3627 (8) | 0.061 (3)* | |
H6A | 1.208 (2) | 0.3477 (10) | 0.2296 (8) | 0.051 (3)* | |
H2A | 0.999 (2) | −0.1410 (10) | 0.2454 (7) | 0.041 (3)* | |
H14 | 0.143 (3) | 0.4282 (11) | 0.7195 (8) | 0.058 (3)* | |
H10A | 1.450 (2) | 0.1871 (11) | 0.1228 (7) | 0.057 (3)* | |
H10B | 1.528 (2) | 0.3468 (11) | 0.1265 (8) | 0.057 (3)* | |
H12 | 0.460 (5) | 0.481 (2) | 0.5268 (14) | 0.059 (7)* | 0.50 |
H9A | 0.573 (4) | 0.0306 (17) | 0.4720 (11) | 0.034 (5)* | 0.50 |
H3 | 0.685 (4) | −0.1663 (19) | 0.3579 (14) | 0.155 (8)* | |
H14A | 0.4887 | 0.0997 | −0.1122 | 0.105* | |
H13A | 0.7194 | 0.3454 | −0.1398 | 0.111* | |
H12A | 1.2254 | 0.4512 | −0.0100 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.03355 (9) | 0.03164 (10) | 0.03291 (11) | 0.01117 (8) | 0.01541 (8) | 0.00763 (8) |
O11 | 0.0319 (3) | 0.0347 (3) | 0.0553 (4) | 0.0121 (2) | 0.0140 (3) | 0.0103 (3) |
O14 | 0.0415 (3) | 0.0672 (4) | 0.0448 (3) | 0.0333 (2) | 0.0261 (2) | 0.0279 (3) |
O12 | 0.0564 (4) | 0.0705 (4) | 0.0384 (4) | 0.0244 (3) | 0.0128 (3) | 0.0220 (3) |
O13 | 0.0984 (5) | 0.0280 (3) | 0.0827 (5) | 0.0072 (3) | 0.0598 (4) | −0.0006 (3) |
N7A | 0.0393 (3) | 0.0333 (4) | 0.0350 (4) | 0.0111 (3) | 0.0114 (3) | 0.0070 (3) |
C5A | 0.0305 (4) | 0.0292 (4) | 0.0296 (4) | 0.0072 (3) | 0.0059 (3) | 0.0049 (3) |
C6A | 0.0313 (4) | 0.0349 (4) | 0.0301 (4) | 0.0082 (3) | 0.0050 (3) | 0.0051 (3) |
N6A | 0.0439 (4) | 0.0346 (4) | 0.0352 (4) | 0.0091 (3) | 0.0154 (3) | 0.0057 (3) |
N1A | 0.0466 (4) | 0.0359 (4) | 0.0427 (4) | 0.0133 (3) | 0.0161 (3) | 0.0047 (3) |
N3A | 0.0449 (4) | 0.0291 (4) | 0.0459 (4) | 0.0099 (3) | 0.0113 (4) | 0.0070 (3) |
C4A | 0.0314 (4) | 0.0331 (4) | 0.0311 (4) | 0.0078 (3) | 0.0058 (3) | 0.0074 (3) |
N9A | 0.0394 (4) | 0.0438 (4) | 0.0350 (4) | 0.0102 (3) | 0.0132 (3) | 0.0097 (3) |
C2A | 0.0531 (5) | 0.0343 (5) | 0.0493 (6) | 0.0150 (4) | 0.0150 (4) | 0.0060 (4) |
C8A | 0.0405 (4) | 0.0477 (5) | 0.0376 (5) | 0.0120 (4) | 0.0152 (4) | 0.0059 (4) |
C10A | 0.0454 (4) | 0.0516 (5) | 0.0420 (5) | 0.0136 (4) | 0.0218 (4) | 0.0130 (4) |
C11A | 0.0521 (5) | 0.0541 (6) | 0.0380 (5) | 0.0204 (4) | 0.0232 (4) | 0.0076 (4) |
O15A | 0.0969 (7) | 0.0757 (6) | 0.0971 (8) | 0.0207 (6) | −0.0157 (7) | 0.0065 (6) |
C14A | 0.1030 (9) | 0.1377 (12) | 0.0633 (9) | 0.0626 (8) | −0.0238 (8) | −0.0238 (9) |
C13A | 0.1290 (8) | 0.1903 (12) | 0.0632 (8) | 0.1129 (7) | 0.0348 (7) | 0.0598 (8) |
C12A | 0.0803 (8) | 0.0632 (6) | 0.0918 (9) | 0.0337 (6) | 0.0136 (7) | 0.0388 (6) |
Geometric parameters (Å, º) top
P1—O11 | 1.5155 (9) | N3A—C4A | 1.3528 (13) |
P1—O13 | 1.5222 (9) | N3A—H3 | 1.193 (19) |
P1—O12 | 1.5256 (9) | C4A—N9A | 1.3683 (14) |
P1—O14 | 1.5452 (8) | N9A—C8A | 1.3344 (14) |
P1—H12 | 1.92 (2) | N9A—H9A | 0.843 (15) |
O14—H14 | 0.818 (13) | C2A—H2A | 0.988 (10) |
O12—H12 | 0.85 (2) | C8A—H8A | 0.937 (11) |
N7A—C8A | 1.3309 (13) | C10A—C11A | 1.4772 (15) |
N7A—C5A | 1.3822 (13) | C10A—H10A | 1.074 (12) |
N7A—H7A | 0.992 (12) | C10A—H10B | 0.907 (10) |
C5A—C4A | 1.3743 (13) | C11A—C12A | 1.3150 (18) |
C5A—C6A | 1.4154 (14) | C11A—O15A | 1.3278 (14) |
C6A—N6A | 1.3329 (13) | O15A—C14A | 1.377 (2) |
C6A—N1A | 1.3555 (13) | C14A—C13A | 1.282 (3) |
N6A—C10A | 1.4708 (14) | C14A—H14A | 1.0463 |
N6A—H6A | 0.886 (12) | C13A—C12A | 1.446 (2) |
N1A—C2A | 1.3242 (14) | C13A—H13A | 1.0487 |
N3A—C2A | 1.3346 (15) | C12A—H12A | 1.0326 |
| | | |
O11—P1—O13 | 109.90 (5) | N9A—C4A—C5A | 109.15 (9) |
O11—P1—O12 | 110.41 (5) | C8A—N9A—C4A | 105.61 (9) |
O13—P1—O12 | 111.52 (5) | C8A—N9A—H9A | 125.5 (13) |
O11—P1—O14 | 108.18 (4) | C4A—N9A—H9A | 128.4 (13) |
O13—P1—O14 | 108.06 (5) | N1A—C2A—N3A | 128.28 (10) |
O12—P1—O14 | 108.67 (5) | N1A—C2A—H2A | 117.9 (6) |
O11—P1—H12 | 103.1 (6) | N3A—C2A—H2A | 113.7 (6) |
O13—P1—H12 | 92.8 (8) | N7A—C8A—N9A | 112.14 (10) |
O12—P1—H12 | 25.5 (8) | N7A—C8A—H8A | 125.5 (6) |
O14—P1—H12 | 132.9 (8) | N9A—C8A—H8A | 122.3 (6) |
P1—O14—H14 | 120.0 (8) | N6A—C10A—C11A | 111.86 (9) |
P1—O12—H12 | 103.9 (17) | N6A—C10A—H10A | 109.4 (6) |
C8A—N7A—C5A | 106.79 (8) | C11A—C10A—H10A | 108.8 (5) |
C8A—N7A—H7A | 128.1 (7) | N6A—C10A—H10B | 106.6 (7) |
C5A—N7A—H7A | 124.9 (7) | C11A—C10A—H10B | 109.2 (7) |
C4A—C5A—N7A | 106.31 (8) | H10A—C10A—H10B | 111.0 (9) |
C4A—C5A—C6A | 119.52 (9) | C12A—C11A—O15A | 111.26 (10) |
N7A—C5A—C6A | 134.15 (8) | C12A—C11A—C10A | 126.62 (10) |
N6A—C6A—N1A | 120.17 (9) | O15A—C11A—C10A | 121.75 (11) |
N6A—C6A—C5A | 122.78 (9) | C11A—O15A—C14A | 106.75 (12) |
N1A—C6A—C5A | 117.06 (8) | C13A—C14A—O15A | 109.34 (13) |
C6A—N6A—C10A | 123.30 (9) | C13A—C14A—H14A | 125.6 |
C6A—N6A—H6A | 115.5 (7) | O15A—C14A—H14A | 125.0 |
C10A—N6A—H6A | 120.4 (7) | C14A—C13A—C12A | 107.81 (14) |
C2A—N1A—C6A | 118.57 (9) | C14A—C13A—H13A | 131.0 |
C2A—N3A—C4A | 113.87 (8) | C12A—C13A—H13A | 121.2 |
C2A—N3A—H3 | 118.4 (10) | C11A—C12A—C13A | 104.61 (12) |
C4A—N3A—H3 | 126.3 (10) | C11A—C12A—H12A | 130.2 |
N3A—C4A—N9A | 128.19 (9) | C13A—C12A—H12A | 124.8 |
N3A—C4A—C5A | 122.65 (9) | | |
| | | |
C8A—N7A—C5A—C4A | 0.24 (9) | N3A—C4A—N9A—C8A | −179.47 (9) |
C8A—N7A—C5A—C6A | 178.17 (9) | C5A—C4A—N9A—C8A | −0.17 (10) |
C4A—C5A—C6A—N6A | 177.51 (8) | C6A—N1A—C2A—N3A | −0.62 (15) |
N7A—C5A—C6A—N6A | −0.20 (15) | C4A—N3A—C2A—N1A | −0.93 (15) |
C4A—C5A—C6A—N1A | −2.51 (12) | C5A—N7A—C8A—N9A | −0.37 (10) |
N7A—C5A—C6A—N1A | 179.78 (9) | C4A—N9A—C8A—N7A | 0.34 (10) |
N1A—C6A—N6A—C10A | 6.77 (13) | C6A—N6A—C10A—C11A | 92.95 (12) |
C5A—C6A—N6A—C10A | −173.25 (8) | N6A—C10A—C11A—C12A | 98.20 (15) |
N6A—C6A—N1A—C2A | −177.72 (8) | N6A—C10A—C11A—O15A | −74.12 (15) |
C5A—C6A—N1A—C2A | 2.30 (12) | C12A—C11A—O15A—C14A | 4.64 (17) |
C2A—N3A—C4A—N9A | 179.89 (9) | C10A—C11A—O15A—C14A | 178.02 (13) |
C2A—N3A—C4A—C5A | 0.67 (12) | C11A—O15A—C14A—C13A | −2.2 (2) |
N7A—C5A—C4A—N3A | 179.30 (8) | O15A—C14A—C13A—C12A | −0.7 (2) |
C6A—C5A—C4A—N3A | 1.02 (13) | O15A—C11A—C12A—C13A | −4.94 (17) |
N7A—C5A—C4A—N9A | −0.05 (9) | C10A—C11A—C12A—C13A | −177.94 (13) |
C6A—C5A—C4A—N9A | −178.33 (7) | C14A—C13A—C12A—C11A | 3.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7A—H7A···O11i | 0.992 (12) | 1.825 (11) | 2.7414 (13) | 152.2 (11) |
N6A—H6A···O11i | 0.886 (12) | 2.030 (12) | 2.9019 (13) | 168.0 (10) |
O14—H14···O11ii | 0.818 (13) | 1.734 (13) | 2.5501 (12) | 174.9 (12) |
O12—H12···O12iii | 0.85 (2) | 1.72 (2) | 2.5435 (17) | 162 (3) |
N3A—H3···O13iv | 1.193 (19) | 1.388 (19) | 2.5777 (14) | 174.4 (17) |
N9A—H9A···N9Aiv | 0.84 (2) | 2.04 (2) | 2.8837 (19) | 174 (2) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1. |
Experimental details
| (115) | (293) |
Crystal data |
Chemical formula | C10H12N5O5P | C10H9N50·H3O4P |
Mr | 313.22 | 313.22 |
Crystal system, space group | Triclinic, P1 | TRICLINIC, P1 |
Temperature (K) | 115 | 293 |
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) |
V (Å3) | 1266.2 (4) | 647.0 (2) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.25 | 0.25 |
Crystal size (mm) | 0.41 × 0.09 × 0.09 | 0.41 × 0.09 × 0.09 |
|
Data collection |
Diffractometer | KM4CCD diffractometer | KM4CCD diffractometer |
Absorption correction | ANALYTICAL- CrysAlis Ver170.26 | ANALYTICAL- CrysAlis Ver170.26 |
Tmin, Tmax | 0.910, 0.982 | 0.915, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11933, 5604, 5604 | 14205, 5349, 3704 |
Rint | 0.049 | 0.042 |
(sin θ/λ)max (Å−1) | 0.663 | 0.910 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.119, 1.22 | 0.056, 0.137, 1.21 |
No. of reflections | 5604 | 3704 |
No. of parameters | 451 | 230 |
No. of restraints | 0 | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | 0.366 | 1.110 |
Δρmax, Δρmin (e Å−3) | 0.66, −0.49 | 0.42, −0.42 |
Hydrogen-bond geometry (Å, º) for (115) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7B—H7B···O11i | 0.883 (7) | 1.837 (7) | 2.6732 (11) | 157.3 (7) |
N6A—H6A···O21ii | 0.838 (8) | 2.029 (8) | 2.8586 (10) | 170.5 (7) |
N6B—H6B···O11i | 0.841 (7) | 2.076 (8) | 2.9068 (10) | 169.4 (7) |
N7A—H7A···O21ii | 0.889 (7) | 1.958 (7) | 2.7794 (11) | 153.0 (7) |
O23—H23···N3B | 0.963 (9) | 1.679 (9) | 2.6397 (11) | 175.6 (9) |
N9B—H9B···N9Aiii | 0.933 (9) | 1.940 (9) | 2.8716 (12) | 176.1 (9) |
O12—H12···O21 | 0.838 (10) | 1.707 (10) | 2.5417 (9) | 174.1 (8) |
O24—H24···O11iv | 0.832 (10) | 1.714 (10) | 2.5449 (9) | 177.2 (9) |
O14—H14···O22v | 1.033 (11) | 1.509 (11) | 2.5420 (9) | 179.6 (9) |
N3A—H3A···O13 | 1.011 (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···A | D—H | H···A | D···A | D—H···A |
N7A—H7A···O11i | 0.992 (12) | 1.825 (11) | 2.7414 (13) | 152.2 (11) |
N6A—H6A···O11i | 0.886 (12) | 2.030 (12) | 2.9019 (13) | 168.0 (10) |
O14—H14···O11ii | 0.818 (13) | 1.734 (13) | 2.5501 (12) | 174.9 (12) |
O12—H12···O12iii | 0.85 (2) | 1.72 (2) | 2.5435 (17) | 162 (3) |
N3A—H3···O13iv | 1.193 (19) | 1.388 (19) | 2.5777 (14) | 174.4 (17) |
N9A—H9A···N9Aiv | 0.843 (15) | 2.044 (16) | 2.8837 (19) | 173.9 (15) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1. |