Multi-temperature study of potassium uridine-5′-mono­phosphate: electron density distribution and anharmonic motion modelling

Uridine, a nucleoside formed of a uracil fragment attached to a ribose ring via a β-N1-glycosidic bond, is one of the four basic components of ribonucleic acid. Here a new anhydrous structure and experimental charge density distribution analysis of a uridine-5′-monophosphate potassium salt, K(UMPH), is reported. The studied case constitutes the very first structure of a 5′-nucleotide potassium salt according to the Cambridge Structural Database. The excellent crystal quality allowed the collection of charge density data at various temperatures, i.e. 10, 100, 200 and 300 K on one single crystal. Crystal structure and charge density data were analysed thoroughly in the context of related literature-reported examples. Detailed analysis of the charge density distribution revealed elevated anharmonic motion of part of the uracil ring moiety relatively weakly interacting with the neighbouring species. The effect was manifested by alternate positive and negative residual density patterns observed for these atoms, which `disappear' at low temperature. It also occurred that the potassium cation, quite uniformly coordinated by seven O atoms from all molecular fragments of the UMPH⁻ anion, including the O atom from the ribo­furan­ose ring, can be treated as spherical in the charge density model which was supported by theoretical calculations. Apart from the predominant electrostatic interactions, four relatively strong hydrogen bond types further support the stability of the crystal structure. This results in a compact and quite uniform structure (in all directions) of the studied crystal, as opposed to similar cases with layered architecture reported in the literature.

Computing details

(KUMPH_100K)

Crystal data

C9H12KN2O9P	F(000) = 744
Mr = 362.3	Dx = 1.786 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 99520 reflections
a = 8.0630 (3) Å	θ = 2.3–59.2°
b = 10.4358 (5) Å	µ = 0.56 mm^−1
c = 16.0092 (7) Å	T = 100 K
V = 1347.08 (10) Å^3	Thick plate-like block, colourless
Z = 4	0.28 × 0.27 × 0.16 mm

Data collection

CCD detector diffractometer	18693 independent reflections
Radiation source: TXS rotating anode	17743 reflections with I > 3σ(I)
Multilayer optics monochromator	Rint = 0.026
ω–scans	θmax = 59.2°, θmin = 2.3°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −19→19
Tmin = 0.862, Tmax = 0.890	k = −23→23
142735 measured reflections	l = −37→35

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.011	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.014	(Δ/σ)max = 0.003
S = 0.84	Δρmax = 0.08 e Å^−3
17743 reflections	Δρmin = −0.08 e Å^−3
642 parameters	Absolute structure: Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.
12 restraints	Absolute structure parameter: −0.002 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
K1	0.210497	0.402523	0.669702	0.009241
P1	0.135498 (1)	0.323701	0.460472	0.006616
O1	0.17789 (2)	0.20192 (2)	0.403550 (10)	0.009810 (10)
O5	0.38856 (2)	0.01781 (2)	0.323025 (1)	0.008426 (1)
O7	0.23819 (3)	−0.13729 (2)	0.178810 (10)	0.011680 (10)
O4	0.04700 (2)	0.25991 (2)	0.536150 (10)	0.010441 (1)
O8	0.37054 (2)	−0.36713 (2)	0.338190 (10)	0.012680 (10)
O2	0.29472 (2)	0.38059 (2)	0.493640 (10)	0.009157 (1)
O6	−0.01817 (2)	0.05342 (2)	0.230770 (10)	0.012098 (1)
N1	0.32946 (2)	−0.17099 (2)	0.397610 (10)	0.008681 (1)
O9	0.25051 (9)	−0.35210 (10)	0.61569 (9)	0.02007 (3)
O3	0.02734 (3)	0.41406 (2)	0.412670 (10)	0.011990 (10)
C3	0.11235 (2)	0.00951 (2)	0.281370 (10)	0.008376 (1)
N2	0.31473 (2)	−0.35674 (2)	0.477750 (10)	0.011260 (10)
C1	0.24777 (2)	0.22254 (2)	0.322560 (10)	0.009250 (10)
C2	0.26657 (2)	0.09473 (2)	0.279950 (1)	0.007820 (1)
C6	0.34051 (2)	−0.30331 (2)	0.400690 (10)	0.009100 (10)
C7	0.27446 (8)	−0.29200 (6)	0.55048 (4)	0.01348 (2)
C5	0.34886 (2)	−0.11354 (2)	0.314270 (10)	0.007899 (1)
C4	0.18828 (2)	−0.12200 (2)	0.262700 (10)	0.008689 (1)
C9	0.29290 (7)	−0.09960 (6)	0.46702 (4)	0.01288 (2)
C8	0.26480 (10)	−0.15485 (7)	0.54200 (4)	0.01743 (2)
H3	0.0670 (10)	0.0050 (8)	0.3460 (2)	0.02187
H1A	0.3669 (4)	0.2714 (6)	0.3282 (6)	0.02725
H1B	0.1628 (7)	0.2797 (6)	0.2848 (4)	0.02756
H2	0.3090 (9)	0.1138 (7)	0.2160 (2)	0.02225
H5	0.4512 (6)	−0.1635 (6)	0.2829 (4)	0.02058
H4	0.1079 (6)	−0.2016 (4)	0.2820 (5)	0.02057
H9	0.2910 (10)	0.0034 (2)	0.4588 (7)	0.02428
H8	0.2320 (10)	−0.0975 (6)	0.5959 (3)	0.02394
H11	−0.0543 (5)	0.2056 (5)	0.5233 (5)	0.02260
H13	0.1418 (5)	−0.1246 (8)	0.1435 (3)	0.01968
H10	0.3160 (10)	−0.45544 (8)	0.4775 (6)	0.02343
H12	−0.0180 (10)	0.0091 (6)	0.1775 (2)	0.02131

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.009656 (1)	0.009400 (10)	0.008670 (10)	0.000076 (1)	−0.000645 (1)	0.001347 (1)
P1	0.007550 (10)	0.006750 (10)	0.005550 (10)	0.000250 (10)	−0.000691 (1)	−0.000387 (1)
O1	0.01461 (5)	0.00746 (6)	0.00734 (5)	−0.00095 (3)	0.00188 (4)	−0.00125 (4)
O5	0.00855 (3)	0.00821 (5)	0.00852 (5)	−0.00109 (3)	−0.00122 (4)	0.00059 (3)
O7	0.01465 (6)	0.01328 (7)	0.00712 (6)	0.00305 (4)	−0.00169 (4)	−0.00321 (3)
O4	0.01057 (4)	0.01373 (6)	0.00702 (5)	−0.00290 (5)	0.00084 (4)	−0.00009 (4)
O8	0.01951 (7)	0.00929 (7)	0.00924 (6)	0.00158 (4)	0.00070 (4)	−0.00230 (5)
O2	0.00856 (4)	0.00790 (5)	0.01101 (5)	−0.00062 (4)	−0.00139 (4)	−0.00060 (3)
O6	0.01005 (4)	0.01479 (6)	0.01146 (6)	0.00300 (5)	−0.00282 (4)	−0.00340 (5)
N1	0.01295 (4)	0.00708 (5)	0.00601 (4)	−0.00023 (3)	−0.000017 (3)	−0.00040 (3)
O9	0.0389 (2)	0.01198 (8)	0.00929 (7)	−0.00436 (7)	0.00362 (7)	0.00274 (6)
O3	0.01327 (5)	0.01226 (7)	0.01045 (6)	0.00335 (5)	−0.00385 (5)	0.00097 (4)
C3	0.00817 (4)	0.00952 (5)	0.00745 (5)	0.00022 (3)	−0.00029 (3)	−0.00167 (3)
N2	0.01780 (6)	0.00755 (5)	0.00842 (5)	−0.00123 (4)	−0.00015 (4)	0.00052 (4)
C1	0.01292 (5)	0.00773 (5)	0.00711 (5)	−0.00051 (4)	0.00072 (4)	−0.00020 (3)
C2	0.00926 (4)	0.00811 (5)	0.00609 (4)	−0.00004 (4)	0.00008 (3)	−0.00030 (3)
C6	0.01253 (5)	0.00732 (5)	0.00745 (5)	−0.00006 (4)	−0.00062 (4)	−0.00062 (3)
C7	0.02370 (9)	0.00908 (6)	0.00765 (5)	−0.00333 (5)	0.00097 (5)	0.00087 (4)
C5	0.00918 (4)	0.00815 (5)	0.00637 (4)	0.00027 (4)	−0.00022 (3)	−0.00038 (3)
C4	0.00988 (4)	0.00860 (5)	0.00759 (5)	−0.00042 (4)	−0.00098 (3)	−0.00156 (3)
C9	0.02429 (8)	0.00749 (5)	0.00687 (5)	−0.00146 (6)	0.00215 (5)	−0.00067 (4)
C8	0.03600 (10)	0.00906 (6)	0.00724 (6)	−0.00291 (6)	0.00438 (6)	−0.00059 (4)
H3	0.0265	0.0245	0.0146	0.0001	0.0030	0.0003
H1A	0.0283	0.0275	0.0259	−0.0086	0.0015	−0.0050
H1B	0.0359	0.0258	0.0211	0.0074	−0.0041	0.0018
H2	0.0291	0.0233	0.0144	−0.0026	0.0025	0.0011
H5	0.0194	0.0224	0.0199	0.0018	0.0024	−0.0031
H4	0.0212	0.0184	0.0220	−0.0051	0.0015	0.0023
H9	0.0357	0.0142	0.0230	−0.0002	0.0018	0.0006
H8	0.0344	0.0204	0.0169	0.0021	0.0043	−0.0050
H11	0.0250	0.0231	0.0197	−0.0032	−0.0013	−0.0004
H13	0.0171	0.0247	0.0173	0.0009	−0.0032	0.0005
H10	0.0366	0.0146	0.0191	0.0005	0.0024	−0.0010
H12	0.0253	0.0222	0.0164	0.0034	−0.0017	−0.0037

Geometric parameters (Å, º)

P1—O1	1.6007 (2)	C3—C2	1.5290 (3)
P1—O4	1.5557 (2)	C3—C4	1.5322 (3)
P1—O3	1.4952 (2)	C3—H3	1.0980 (8)
P1—O2	1.5108 (2)	N2—C6	1.3698 (3)
O1—C1	1.4300 (3)	N2—C7	1.3847 (7)
O5—C5	1.4145 (3)	N2—H10	1.0300 (8)
O5—C2	1.4448 (3)	C1—C2	1.5057 (3)
O7—C4	1.4111 (3)	C1—H1A	1.0910 (9)
O7—H13	0.9700 (9)	C1—H1B	1.0910 (9)
O4—H11	1.0150 (9)	C2—H2	1.0980 (8)
O8—C6	1.2261 (3)	C7—C8	1.4398 (10)
O6—C3	1.4049 (3)	C5—C4	1.5381 (3)
O6—H12	0.9699 (9)	C5—H5	1.0981 (9)
N1—C6	1.3846 (3)	C4—H4	1.0979 (9)
N1—C5	1.4711 (3)	C9—C8	1.3508 (9)
N1—C9	1.3698 (6)	C9—H9	1.0830 (8)
O9—C7	1.2330 (10)	C8—H8	1.0831 (9)
P1—O1—C1	118.75 (2)	O9—C7—N2	120.00 (10)
P1—O4—H11	116.7 (5)	O9—C7—C8	125.20 (10)
O1—P1—O4	101.630 (10)	C3—O6—H12	110.4 (5)
O1—P1—O3	109.500 (10)	C3—C2—C1	115.250 (10)
O1—P1—O2	109.305 (10)	C3—C2—H2	111.9 (4)
O1—C1—C2	108.49 (2)	C3—C4—C5	100.380 (10)
O1—C1—H1A	110.0 (5)	C3—C4—H4	112.8 (3)
O1—C1—H1B	109.7 (4)	N2—C7—C8	114.74 (5)
O5—C5—N1	109.21 (2)	C1—C2—H2	107.1 (4)
O5—C5—C4	107.42 (2)	C2—O5—C5	109.70 (2)
O5—C5—H5	109.6 (4)	C2—C3—C4	101.14 (2)
O5—C2—C3	102.910 (10)	C2—C3—H3	108.1 (4)
O5—C2—C1	110.150 (10)	C2—C1—H1A	111.3 (4)
O5—C2—H2	109.5 (4)	C2—C1—H1B	107.2 (4)
O7—C4—C5	106.10 (2)	C6—N1—C5	115.58 (2)
O7—C4—C3	113.63 (2)	C6—N1—C9	121.83 (4)
O7—C4—H4	110.5 (4)	C6—N2—C7	126.46 (4)
O4—P1—O3	113.640 (10)	C6—N2—H10	113.8 (5)
O4—P1—O2	106.510 (10)	C7—N2—H10	119.5 (5)
O8—C6—N1	121.70 (2)	C7—C8—C9	119.93 (7)
O8—C6—N2	122.94 (2)	C7—C8—H8	119.2 (4)
O2—P1—O3	115.320 (10)	C5—N1—C9	122.47 (3)
O6—C3—C2	114.26 (2)	C5—C4—H4	112.9 (4)
O6—C3—C4	118.62 (2)	C4—O7—H13	108.1 (4)
O6—C3—H3	107.9 (4)	C4—C5—H5	111.1 (4)
N1—C6—N2	115.35 (2)	C4—C3—H3	106.2 (4)
N1—C5—C4	111.96 (2)	C9—C8—H8	120.9 (4)
N1—C5—H5	107.6 (4)	C8—C9—H9	122.0 (6)
N1—C9—C8	121.65 (5)	H1A—C1—H1B	110.0 (6)
N1—C9—H9	116.4 (6)
P1—O1—C1—C2	−176.690 (10)	O3—P1—O1—C1	53.660 (10)
P1—O1—C1—H1A	61.4 (4)	O3—P1—O4—H11	60.6 (4)
P1—O1—C1—H1B	−59.8 (4)	C3—C2—O5—C5	26.470 (10)
O1—P1—O4—H11	−56.9 (4)	C3—C2—C1—H1A	170.7 (2)
O1—C1—C2—O5	−66.330 (10)	C3—C2—C1—H1B	−68.9 (4)
O1—C1—C2—C3	49.52 (2)	C3—C4—O7—H13	−58.7 (5)
O1—C1—C2—H2	174.7 (2)	C3—C4—C5—H5	−144.8 (4)
O5—C5—N1—C6	−161.180 (10)	N2—C6—N1—C5	−177.10 (2)
O5—C5—N1—C9	22.62 (3)	N2—C6—N1—C9	−0.87 (3)
O5—C5—C4—O7	93.520 (10)	N2—C7—C8—C9	0.50 (6)
O5—C5—C4—C3	−24.970 (10)	N2—C7—C8—H8	178.90 (10)
O5—C5—C4—H4	−145.3 (4)	C1—C2—O5—C5	149.860 (10)
O5—C2—C3—O6	−169.81 (2)	C1—C2—C3—C4	−161.110 (10)
O5—C2—C3—C4	−41.190 (10)	C1—C2—C3—H3	−49.8 (4)
O5—C2—C3—H3	70.1 (4)	C2—O5—C5—C4	−0.750 (10)
O5—C2—C1—H1A	54.8 (4)	C2—O5—C5—H5	120.0 (4)
O5—C2—C1—H1B	175.20 (10)	C2—C3—O6—H12	98.0 (5)
O7—C4—C5—N1	−146.590 (10)	C2—C3—C4—C5	39.490 (10)
O7—C4—C5—H5	−26.3 (4)	C2—C3—C4—H4	159.9 (3)
O7—C4—C3—O6	52.43 (2)	C6—N1—C5—C4	79.990 (10)
O7—C4—C3—C2	−73.340 (10)	C6—N1—C5—H5	−42.3 (4)
O7—C4—C3—H3	174.0 (3)	C6—N1—C9—C8	−0.39 (5)
O4—P1—O1—C1	174.140 (10)	C6—N1—C9—H9	178.0 (3)
O8—C6—N1—C5	2.55 (2)	C6—N2—C7—C8	−1.95 (5)
O8—C6—N1—C9	178.77 (4)	C7—C8—C9—H9	−177.80 (10)
O8—C6—N2—C7	−177.51 (4)	C5—O5—C2—H2	−92.6 (4)
O8—C6—N2—H10	−3.7 (5)	C5—N1—C9—C8	175.58 (5)
O2—P1—O1—C1	−73.550 (10)	C5—N1—C9—H9	−6.0 (6)
O2—P1—O4—H11	−171.3 (3)	C5—C4—O7—H13	−168.0 (2)
O6—C3—C2—C1	70.27 (2)	C5—C4—C3—H3	−73.2 (4)
O6—C3—C2—H2	−52.4 (4)	C4—C5—N1—C9	−96.21 (3)
O6—C3—C4—C5	165.25 (2)	C4—C3—O6—H12	−21.2 (5)
O6—C3—C4—H4	−74.3 (4)	C4—C3—C2—H2	76.3 (4)
N1—C6—N2—C7	2.13 (3)	C9—N1—C5—H5	141.5 (4)
N1—C6—N2—H10	175.90 (10)	C8—C7—N2—H10	−175.4 (2)
N1—C5—O5—C2	−122.37 (2)	H3—C3—O6—H12	−141.8 (6)
N1—C5—C4—C3	94.920 (10)	H3—C3—C2—H2	−172.5 (6)
N1—C5—C4—H4	−25.4 (4)	H3—C3—C4—H4	47.2 (6)
N1—C9—C8—C7	0.57 (5)	H1A—C1—C2—H2	−64.2 (6)
N1—C9—C8—H8	−177.80 (10)	H1B—C1—C2—H2	56.2 (6)
O9—C7—N2—C6	178.23 (9)	H5—C5—C4—H4	94.9 (5)
O9—C7—N2—H10	4.7 (5)	H4—C4—O7—H13	69.3 (6)
O9—C7—C8—C9	−179.69 (10)	H9—C9—C8—H8	3.9 (6)
O9—C7—C8—H8	−1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···P1^i	1.0150 (9)	2.534 (4)	3.4312 (2)	147.2 (3)
O4—H11···O1^i	1.0150 (9)	2.640 (6)	3.1540 (3)	111.3 (4)
O4—H11···O2^i	1.0150 (9)	1.5379 (9)	2.5524 (3)	177.70 (10)
N2—H10···O2^ii	1.0300 (8)	1.739 (2)	2.7577 (3)	169.5 (3)
O7—H13···O3^iii	0.9700 (9)	1.6830 (10)	2.6487 (3)	173.4 (2)
O6—H12···O3^iii	0.9699 (9)	1.7530 (10)	2.7191 (3)	173.4 (2)
C3—H3···O1	1.0980 (8)	2.423 (8)	2.8525 (3)	101.5 (4)
C5—H5···O8	1.0981 (9)	2.393 (8)	2.6797 (3)	92.7 (5)
C9—H9···O1	1.0830 (8)	2.430 (5)	3.4343 (7)	153.6 (4)
C9—H9···O5	1.0830 (8)	2.320 (10)	2.7221 (6)	100.0 (7)
O7—H13···O6	0.9700 (9)	2.659 (7)	2.9875 (3)	100.2 (5)
O6—H12···O7	0.9699 (9)	2.567 (9)	2.9875 (3)	106.3 (6)
C1—H1A···O4^iv	1.0910 (9)	2.633 (8)	3.3123 (3)	119.7 (5)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.

(KUMPH_10K_neutrons)

Crystal data

C9H12KN2O9P	Z = 4
Mr = 362.3	F(000) = 378.772
Orthorhombic, P212121	Dx = 1.793 Mg m^−3
Hall symbol: P 2ac 2ab	Neutron radiation, λ = 0.2-1.0 Å
a = 8.0754 (16) Å	µ = 0.57 mm^−1
b = 10.387 (2) Å	T = 10 K
c = 16.000 (3) Å	Thick plate-like block, colourless
V = 1342.1 (4) Å^3	2 × 1 × 1 mm

Data collection

11 neutron detectors diffractometer	13558 reflections with I > 3σ(I)
Radiation source: ISIS neutron spallation source	Rint = 0
Not applicable to TOF Laue technique monochromator	θmax = 77.8°, θmin = 1.9°
π–scans, time–of–flight Laue	h = −19→21
13658 measured reflections	k = −28→23
13658 independent reflections	l = −44→42

Refinement

Refinement on F	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.081	Weighting scheme based on measured s.u.'s w = 1/(σ^2(F) + 0.0001F^2)
wR(F^2) = 0.089	(Δ/σ)max = 0.010
S = 2.74	Δρmax = 4.90 e Å^−3
13658 reflections	Δρmin = −4.13 e Å^−3
318 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 10.0 (3)
0 constraints	Absolute structure: 2639 of Friedel pairs used in the refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
K1	0.2084 (5)	0.4023 (4)	0.6706 (2)	0.0040 (10)
P1	0.1337 (3)	0.3244 (3)	0.46151 (16)	0.0024 (7)
O1	0.1756 (3)	0.2033 (2)	0.40397 (14)	0.0047 (6)
O5	0.3865 (3)	0.0196 (3)	0.32260 (15)	0.0044 (6)
O7	0.2380 (3)	−0.1367 (3)	0.17847 (14)	0.0055 (6)
O4	0.0452 (3)	0.2591 (3)	0.53676 (14)	0.0043 (6)
O8	0.3710 (3)	−0.3665 (3)	0.33931 (14)	0.0053 (6)
O2	0.2930 (3)	0.3809 (2)	0.49535 (14)	0.0037 (6)
O6	−0.0196 (3)	0.0546 (3)	0.23014 (15)	0.0053 (7)
N1	0.32642 (19)	−0.16967 (15)	0.39779 (9)	0.0040 (4)
O9	0.2420 (3)	−0.3497 (3)	0.61633 (15)	0.0075 (7)
O3	0.0264 (3)	0.4160 (2)	0.41421 (15)	0.0046 (6)
C3	0.1115 (3)	0.0110 (2)	0.28098 (13)	0.0037 (5)
N2	0.31148 (19)	−0.35534 (16)	0.47887 (9)	0.0050 (4)
C1	0.2455 (3)	0.2248 (2)	0.32262 (12)	0.0038 (5)
C2	0.2649 (3)	0.0972 (2)	0.27993 (12)	0.0034 (5)
C6	0.3387 (3)	−0.3021 (2)	0.40155 (12)	0.0035 (5)
C7	0.2664 (3)	−0.2900 (2)	0.55124 (12)	0.0043 (5)
C5	0.3471 (3)	−0.1123 (2)	0.31418 (12)	0.0034 (5)
C4	0.1876 (3)	−0.1211 (2)	0.26208 (12)	0.0040 (5)
C9	0.2854 (3)	−0.0979 (2)	0.46652 (12)	0.0046 (6)
C8	0.2543 (3)	−0.1523 (2)	0.54159 (13)	0.0070 (6)
H3	0.0658 (5)	0.0073 (5)	0.3457 (3)	0.0149 (13)
H1a	0.3661 (6)	0.2737 (5)	0.3291 (3)	0.0192 (14)
H1b	0.1644 (6)	0.2861 (5)	0.2846 (3)	0.0191 (14)
H2	0.3067 (6)	0.1143 (5)	0.2156 (3)	0.0154 (13)
H5	0.4484 (6)	−0.1644 (5)	0.2839 (3)	0.0136 (12)
H4	0.1076 (6)	−0.2014 (5)	0.2826 (3)	0.0160 (13)
H9	0.2820 (6)	0.0054 (5)	0.4565 (3)	0.0196 (14)
H8	0.2231 (7)	−0.0929 (5)	0.5947 (3)	0.0227 (15)
H11	−0.0538 (6)	0.2039 (5)	0.5224 (3)	0.0173 (14)
H13	0.1429 (6)	−0.1235 (5)	0.1401 (3)	0.0171 (14)
H10	0.3138 (7)	−0.4549 (5)	0.4815 (3)	0.0163 (13)
H12	−0.0226 (6)	0.0121 (5)	0.1754 (3)	0.0195 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.0056 (17)	0.0045 (18)	0.0021 (14)	−0.0001 (12)	0.0007 (12)	0.0007 (13)
P1	0.0036 (11)	0.0008 (12)	0.0029 (10)	−0.0003 (8)	0.0005 (8)	0.0001 (9)
O1	0.0075 (10)	0.0032 (11)	0.0034 (9)	−0.0010 (9)	0.0005 (8)	−0.0014 (8)
O5	0.0046 (10)	0.0035 (12)	0.0052 (10)	−0.0024 (9)	−0.0008 (8)	0.0009 (9)
O7	0.0084 (11)	0.0068 (12)	0.0014 (8)	0.0029 (9)	−0.0002 (8)	−0.0021 (8)
O4	0.0063 (10)	0.0035 (12)	0.0032 (9)	−0.0016 (8)	0.0007 (8)	0.0006 (8)
O8	0.0099 (11)	0.0040 (13)	0.0022 (9)	0.0001 (9)	0.0012 (8)	−0.0005 (8)
O2	0.0038 (11)	0.0036 (12)	0.0036 (9)	−0.0002 (8)	−0.0003 (7)	−0.0016 (8)
O6	0.0045 (11)	0.0062 (13)	0.0051 (10)	0.0022 (8)	−0.0025 (8)	−0.0005 (9)
N1	0.0066 (7)	0.0026 (7)	0.0028 (6)	0.0003 (5)	−0.0009 (5)	−0.0001 (5)
O9	0.0153 (12)	0.0033 (12)	0.0039 (9)	−0.0006 (10)	0.0027 (9)	0.0009 (8)
O3	0.0049 (11)	0.0048 (12)	0.0042 (10)	0.0024 (9)	−0.0026 (8)	−0.0001 (8)
C3	0.0035 (9)	0.0043 (10)	0.0034 (8)	0.0006 (7)	0.0008 (7)	−0.0007 (8)
N2	0.0094 (7)	0.0028 (8)	0.0026 (6)	−0.0003 (6)	0.0006 (5)	0.0002 (5)
C1	0.0054 (9)	0.0026 (9)	0.0035 (7)	−0.0012 (7)	0.0000 (7)	−0.0008 (7)
C2	0.0046 (9)	0.0035 (10)	0.0021 (7)	0.0006 (7)	0.0001 (7)	−0.0009 (7)
C6	0.0052 (9)	0.0029 (10)	0.0023 (8)	0.0001 (7)	0.0002 (7)	−0.0004 (7)
C7	0.0069 (9)	0.0037 (11)	0.0024 (8)	−0.0014 (8)	0.0002 (7)	0.0006 (7)
C5	0.0048 (9)	0.0037 (11)	0.0017 (8)	−0.0010 (7)	0.0002 (6)	−0.0011 (7)
C4	0.0043 (9)	0.0048 (10)	0.0030 (8)	0.0002 (8)	0.0003 (7)	0.0001 (7)
C9	0.0088 (10)	0.0028 (11)	0.0021 (8)	0.0005 (7)	0.0013 (7)	−0.0002 (7)
C8	0.0124 (10)	0.0056 (11)	0.0031 (8)	0.0001 (8)	0.0013 (8)	0.0006 (7)
H3	0.016 (2)	0.019 (3)	0.0090 (19)	0.0028 (19)	0.0028 (15)	−0.0013 (17)
H1a	0.019 (2)	0.016 (3)	0.023 (2)	−0.0080 (19)	0.0055 (18)	−0.007 (2)
H1b	0.025 (2)	0.020 (3)	0.0123 (19)	0.009 (2)	−0.0019 (18)	0.0037 (18)
H2	0.018 (2)	0.019 (3)	0.0092 (18)	0.0001 (19)	0.0029 (16)	0.0024 (17)
H5	0.016 (2)	0.010 (2)	0.015 (2)	0.0030 (16)	0.0035 (17)	−0.0020 (17)
H4	0.019 (2)	0.013 (3)	0.017 (2)	−0.0071 (18)	0.0004 (18)	0.0043 (18)
H9	0.036 (3)	0.008 (2)	0.015 (2)	0.002 (2)	0.0020 (19)	0.0042 (17)
H8	0.042 (3)	0.015 (3)	0.011 (2)	0.005 (2)	0.008 (2)	−0.0059 (18)
H11	0.017 (2)	0.016 (3)	0.019 (2)	−0.0037 (18)	0.0032 (18)	−0.0003 (19)
H13	0.021 (2)	0.020 (3)	0.0108 (19)	0.000 (2)	−0.0059 (16)	−0.0031 (18)
H10	0.027 (3)	0.010 (2)	0.0129 (19)	0.000 (2)	0.0045 (19)	0.0014 (16)
H12	0.021 (2)	0.026 (3)	0.011 (2)	0.003 (2)	−0.0050 (18)	−0.004 (2)

(KUMPH_10K)

Crystal data

C9H12KN2O9P	F(000) = 744
Mr = 362.3	Dx = 1.789 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 66342 reflections
a = 8.0778 (2) Å	θ = 2.3–58.1°
b = 10.4023 (3) Å	µ = 0.57 mm^−1
c = 16.0137 (4) Å	T = 10 K
V = 1345.59 (6) Å^3	Thick plate-like block, colourless
Z = 4	0.28 × 0.27 × 0.16 mm

Data collection

CCD detector diffractometer	18408 independent reflections
Radiation source: TXS rotating anode	17834 reflections with I > 3σ(I)
Multilayer optics monochromator	Rint = 0.041
ω–scans	θmax = 58.4°, θmin = 2.3°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −18→18
Tmin = 0.808, Tmax = 1.127	k = −24→24
80683 measured reflections	l = −37→38

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.015	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.018	(Δ/σ)max = 0.010
S = 0.84	Δρmax = 0.15 e Å^−3
17834 reflections	Δρmin = −0.16 e Å^−3
602 parameters	Absolute structure: Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.
12 restraints	Absolute structure parameter: 0.005 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
K1	0.208935 (1)	0.402503	0.670567	0.005009
P1	0.134122 (1)	0.324496 (1)	0.461400	0.003258
O1	0.17634 (2)	0.20297 (2)	0.403800 (10)	0.005440 (10)
O5	0.38718 (2)	0.01911 (2)	0.322780 (10)	0.004753 (1)
O7	0.23792 (3)	−0.13640 (2)	0.178350 (10)	0.006520 (10)
O4	0.04510 (3)	0.25963 (2)	0.536680 (10)	0.005920 (10)
O8	0.37083 (3)	−0.36704 (2)	0.339210 (10)	0.00691 (2)
O2	0.29338 (3)	0.38090 (2)	0.495060 (10)	0.005290 (10)
O6	−0.01911 (3)	0.05459 (2)	0.230170 (10)	0.006790 (10)
N1	0.32704 (2)	−0.16991 (2)	0.397740 (10)	0.004710 (10)
O9	0.24315 (3)	−0.35032 (3)	0.61635 (2)	0.00930 (2)
O3	0.02650 (3)	0.41598 (2)	0.413860 (10)	0.006520 (10)
C3	0.11119 (3)	0.01071 (2)	0.280950 (10)	0.004690 (10)
N2	0.31207 (3)	−0.35569 (2)	0.478570 (10)	0.006000 (10)
C1	0.24608 (3)	0.22437 (2)	0.322780 (10)	0.005340 (10)
C2	0.26519 (2)	0.09636 (2)	0.279790 (10)	0.004370 (10)
C6	0.33892 (3)	−0.30259 (2)	0.401340 (10)	0.004880 (10)
C7	0.26810 (3)	−0.29029 (2)	0.550960 (10)	0.006280 (10)
C5	0.34744 (3)	−0.11270 (2)	0.314250 (10)	0.004300 (10)
C4	0.18749 (3)	−0.12127 (2)	0.262260 (10)	0.004770 (10)
C9	0.28671 (3)	−0.09789 (2)	0.466690 (10)	0.006540 (10)
C8	0.25612 (4)	−0.15255 (2)	0.541720 (10)	0.00804 (2)
H3	0.0650 (10)	0.0070 (10)	0.3451 (2)	0.01709
H1A	0.3678 (5)	0.2705 (7)	0.3282 (8)	0.02122
H1B	0.1637 (8)	0.2847 (6)	0.2844 (4)	0.02141
H2	0.3100 (10)	0.1152 (10)	0.2165 (2)	0.01714
H5	0.4474 (7)	−0.1664 (7)	0.2833 (5)	0.01643
H4	0.1090 (7)	−0.2006 (5)	0.2821 (7)	0.01652
H9	0.283 (2)	0.0041 (2)	0.4568 (9)	0.01963
H8	0.2250 (10)	−0.0945 (7)	0.5947 (3)	0.01964
H11	−0.0522 (6)	0.2020 (6)	0.5226 (7)	0.01723
H13	0.1389 (5)	−0.1250 (10)	0.1427 (4)	0.01591
H10	0.313 (2)	−0.45573 (9)	0.4800 (9)	0.01888
H12	−0.0160 (10)	0.0111 (6)	0.1765 (2)	0.01670

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.004490 (10)	0.005130 (10)	0.005400 (10)	0.000071 (1)	−0.000272 (1)	0.000510 (1)
P1	0.00285 (2)	0.00341 (2)	0.003520 (10)	0.000110 (10)	−0.000280 (10)	−0.000190 (10)
O1	0.00745 (6)	0.00392 (5)	0.00496 (5)	−0.00013 (3)	0.00123 (4)	−0.00097 (5)
O5	0.00413 (5)	0.00411 (5)	0.00601 (5)	−0.00043 (3)	−0.00089 (4)	0.00043 (4)
O7	0.00744 (7)	0.00736 (6)	0.00477 (6)	0.00139 (4)	−0.00081 (5)	−0.00141 (4)
O4	0.00537 (5)	0.00752 (5)	0.00487 (6)	−0.00165 (5)	0.00080 (4)	0.00023 (4)
O8	0.01001 (8)	0.00510 (6)	0.00562 (6)	0.00077 (4)	0.00072 (4)	−0.00115 (5)
O2	0.00399 (5)	0.00468 (5)	0.00721 (5)	−0.00066 (4)	−0.00089 (4)	−0.00041 (4)
O6	0.00492 (5)	0.00812 (5)	0.00732 (6)	0.00169 (5)	−0.00163 (4)	−0.00147 (5)
N1	0.00662 (6)	0.00356 (5)	0.00396 (5)	0.00014 (3)	0.00013 (3)	0.000003 (4)
O9	0.01555 (9)	0.00651 (7)	0.00584 (6)	−0.00130 (5)	0.00183 (5)	0.00153 (6)
O3	0.00649 (6)	0.00627 (6)	0.00681 (5)	0.00180 (5)	−0.00197 (5)	0.00096 (4)
C3	0.00396 (6)	0.00510 (5)	0.00502 (5)	0.00021 (4)	−0.00024 (4)	−0.00067 (4)
N2	0.00900 (7)	0.00396 (5)	0.00505 (5)	−0.00024 (4)	0.00045 (4)	0.00027 (5)
C1	0.00655 (6)	0.00425 (5)	0.00522 (5)	−0.00006 (4)	0.00054 (4)	−0.00026 (4)
C2	0.00451 (5)	0.00429 (5)	0.00432 (5)	−0.000013 (4)	−0.00005 (3)	−0.00019 (4)
C6	0.00607 (6)	0.00402 (5)	0.00454 (5)	0.00005 (4)	−0.00005 (4)	−0.00017 (4)
C7	0.00910 (7)	0.00489 (5)	0.00484 (5)	−0.00103 (4)	0.00055 (4)	0.00052 (5)
C5	0.00433 (6)	0.00425 (5)	0.00432 (5)	0.00024 (4)	−0.00010 (4)	−0.00006 (4)
C4	0.00472 (6)	0.00461 (5)	0.00497 (5)	−0.00024 (4)	−0.00059 (4)	−0.00050 (4)
C9	0.01052 (7)	0.00440 (5)	0.00468 (5)	−0.00019 (5)	0.00095 (4)	−0.00021 (5)
C8	0.01424 (9)	0.00495 (6)	0.00492 (6)	−0.00050 (5)	0.00185 (5)	−0.00016 (5)
H3	0.0195	0.0201	0.0117	0.0001	0.0031	0.0004
H1A	0.0172	0.0234	0.0231	−0.0066	0.0012	−0.0046
H1B	0.0255	0.0209	0.0178	0.0077	−0.0039	0.0021
H2	0.0209	0.0190	0.0116	−0.0013	0.0030	0.0013
H5	0.0143	0.0172	0.0178	0.0030	0.0029	−0.0026
H4	0.0162	0.0141	0.0193	−0.0047	0.0015	0.0024
H9	0.0286	0.0100	0.0202	0.0007	0.0019	0.0013
H8	0.0284	0.0164	0.0142	0.0023	0.0039	−0.0046
H11	0.0171	0.0180	0.0165	−0.0042	−0.0008	−0.0002
H13	0.0126	0.0206	0.0145	0.0011	−0.0030	0.0004
H10	0.0290	0.0103	0.0173	0.0004	0.0030	−0.0002
H12	0.0190	0.0178	0.0133	0.0030	−0.0017	−0.0036

Geometric parameters (Å, º)

P1—O1	1.6017 (2)	C3—C2	1.5303 (3)
P1—O4	1.5575 (2)	C3—C4	1.5343 (3)
P1—O3	1.4970 (2)	C3—H3	1.0950 (8)
P1—O2	1.5132 (2)	N2—C6	1.3716 (3)
O1—C1	1.4318 (3)	N2—C7	1.3903 (3)
O5—C5	1.4149 (3)	N2—H10	1.0410 (8)
O5—C2	1.4459 (3)	C1—C2	1.5069 (3)
O7—C4	1.4129 (3)	C1—H1A	1.0970 (8)
O7—H13	0.9900 (8)	C1—H1B	1.1020 (8)
O4—H11	1.0140 (8)	C2—H2	1.0930 (8)
O8—C6	1.2272 (3)	C7—C8	1.4437 (3)
O6—C3	1.4062 (3)	C5—C4	1.5396 (3)
O6—H12	0.9710 (8)	C5—H5	1.1000 (8)
N1—C6	1.3847 (3)	C4—H4	1.0880 (8)
N1—C5	1.4728 (3)	C9—C8	1.3521 (3)
N1—C9	1.3735 (3)	C9—H9	1.0730 (8)
O9—C7	1.2358 (3)	C8—H8	1.0711 (8)
P1—O1—C1	118.88 (2)	O9—C7—N2	120.06 (3)
P1—O4—H11	116.2 (6)	O9—C7—C8	125.27 (2)
O1—P1—O4	101.660 (10)	C3—O6—H12	110.1 (6)
O1—P1—O3	109.420 (10)	C3—C2—C1	115.19 (2)
O1—P1—O2	109.280 (10)	C3—C2—H2	112.5 (4)
O1—C1—C2	108.48 (2)	C3—C4—C5	100.360 (10)
O1—C1—H1A	110.4 (7)	C3—C4—H4	112.8 (4)
O1—C1—H1B	110.9 (4)	N2—C7—C8	114.67 (2)
O5—C5—N1	109.23 (2)	C1—C2—H2	107.4 (5)
O5—C5—C4	107.38 (2)	C2—O5—C5	109.75 (2)
O5—C5—H5	111.7 (4)	C2—C3—C4	101.07 (2)
O5—C2—C3	102.98 (2)	C2—C3—H3	108.1 (5)
O5—C2—C1	110.08 (2)	C2—C1—H1A	109.3 (5)
O5—C2—H2	108.5 (6)	C2—C1—H1B	108.0 (4)
O7—C4—C5	106.19 (2)	C6—N1—C5	115.64 (2)
O7—C4—C3	113.64 (2)	C6—N1—C9	121.78 (2)
O7—C4—H4	111.2 (6)	C6—N2—C7	126.52 (2)
O4—P1—O3	113.640 (10)	C6—N2—H10	114.9 (8)
O4—P1—O2	106.540 (10)	C7—N2—H10	118.3 (8)
O8—C6—N1	121.69 (2)	C7—C8—C9	119.74 (2)
O8—C6—N2	122.97 (2)	C7—C8—H8	119.6 (4)
O2—P1—O3	115.37 (2)	C5—N1—C9	122.41 (2)
O6—C3—C2	114.36 (2)	C5—C4—H4	112.0 (5)
O6—C3—C4	118.58 (2)	C4—O7—H13	107.5 (4)
O6—C3—H3	107.3 (6)	C4—C5—H5	110.1 (4)
N1—C6—N2	115.34 (2)	C4—C3—H3	106.8 (6)
N1—C5—C4	111.94 (2)	C9—C8—H8	120.6 (4)
N1—C5—H5	106.6 (5)	C8—C9—H9	122.8 (8)
N1—C9—C8	121.89 (2)	H1A—C1—H1B	109.6 (7)
N1—C9—H9	115.4 (8)
P1—O1—C1—C2	−176.910 (10)	O3—P1—O1—C1	53.460 (10)
P1—O1—C1—H1A	63.3 (5)	O3—P1—O4—H11	63.7 (5)
P1—O1—C1—H1B	−58.4 (4)	C3—C2—O5—C5	26.12 (2)
O1—P1—O4—H11	−53.8 (5)	C3—C2—C1—H1A	170.1 (3)
O1—C1—C2—O5	−66.27 (2)	C3—C2—C1—H1B	−70.7 (4)
O1—C1—C2—C3	49.60 (2)	C3—C4—O7—H13	−59.5 (7)
O1—C1—C2—H2	175.8 (2)	C3—C4—C5—H5	−147.1 (5)
O5—C5—N1—C6	−160.77 (2)	N2—C6—N1—C5	−177.06 (2)
O5—C5—N1—C9	23.88 (2)	N2—C6—N1—C9	−1.67 (2)
O5—C5—C4—O7	93.20 (2)	N2—C7—C8—C9	0.09 (2)
O5—C5—C4—C3	−25.33 (2)	N2—C7—C8—H8	−178.8 (2)
O5—C5—C4—H4	−145.2 (5)	C1—C2—O5—C5	149.44 (2)
O5—C2—C3—O6	−169.62 (2)	C1—C2—C3—C4	−160.90 (2)
O5—C2—C3—C4	−41.04 (2)	C1—C2—C3—H3	−48.9 (6)
O5—C2—C3—H3	70.9 (6)	C2—O5—C5—C4	−0.29 (2)
O5—C2—C1—H1A	54.2 (5)	C2—O5—C5—H5	120.4 (5)
O5—C2—C1—H1B	173.4 (2)	C2—C3—O6—H12	96.7 (6)
O7—C4—C5—N1	−146.93 (2)	C2—C3—C4—C5	39.60 (2)
O7—C4—C5—H5	−28.6 (5)	C2—C3—C4—H4	159.0 (4)
O7—C4—C3—O6	52.49 (2)	C6—N1—C5—C4	80.45 (2)
O7—C4—C3—C2	−73.32 (2)	C6—N1—C5—H5	−39.9 (4)
O7—C4—C3—H3	173.7 (3)	C6—N1—C9—C8	−0.13 (2)
O4—P1—O1—C1	173.91 (2)	C6—N1—C9—H9	179.2 (4)
O8—C6—N1—C5	2.73 (2)	C6—N2—C7—C8	−2.14 (2)
O8—C6—N1—C9	178.12 (3)	C7—C8—C9—H9	−178.3 (2)
O8—C6—N2—C7	−176.88 (2)	C5—O5—C2—H2	−93.3 (5)
O8—C6—N2—H10	−3.8 (7)	C5—N1—C9—C8	174.94 (2)
O2—P1—O1—C1	−73.740 (10)	C5—N1—C9—H9	−5.7 (7)
O2—P1—O4—H11	−168.2 (3)	C5—C4—O7—H13	−168.9 (3)
O6—C3—C2—C1	70.52 (2)	C5—C4—C3—H3	−73.4 (5)
O6—C3—C2—H2	−53.0 (5)	C4—C5—N1—C9	−94.90 (2)
O6—C3—C4—C5	165.41 (2)	C4—C3—O6—H12	−22.4 (5)
O6—C3—C4—H4	−75.2 (5)	C4—C3—C2—H2	75.5 (6)
N1—C6—N2—C7	2.91 (2)	C9—N1—C5—H5	144.7 (4)
N1—C6—N2—H10	176.0 (2)	C8—C7—N2—H10	−175.1 (3)
N1—C5—O5—C2	−121.88 (2)	H3—C3—O6—H12	−143.3 (7)
N1—C5—C4—C3	94.54 (2)	H3—C3—C2—H2	−172.5 (8)
N1—C5—C4—H4	−25.4 (6)	H3—C3—C4—H4	46.0 (8)
N1—C9—C8—C7	0.95 (2)	H1A—C1—C2—H2	−63.7 (8)
N1—C9—C8—H8	179.85 (8)	H1B—C1—C2—H2	55.6 (7)
O9—C7—N2—C6	178.04 (2)	H5—C5—C4—H4	93.0 (6)
O9—C7—N2—H10	5.1 (7)	H4—C4—O7—H13	69.0 (8)
O9—C7—C8—C9	179.91 (3)	H9—C9—C8—H8	0.6 (8)
O9—C7—C8—H8	1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···P1^i	1.0140 (8)	2.562 (5)	3.4333 (2)	143.9 (4)
O4—H11···O1^i	1.0140 (8)	2.679 (8)	3.1517 (3)	108.6 (5)
O4—H11···O2^i	1.0140 (8)	1.5420 (10)	2.5553 (3)	176.50 (10)
N2—H10···O2^ii	1.0410 (8)	1.724 (2)	2.7569 (3)	171.0 (4)
O7—H13···O3^iii	0.9900 (8)	1.669 (2)	2.6532 (3)	172.3 (3)
O6—H12···O3^iii	0.9710 (8)	1.755 (2)	2.7207 (3)	172.3 (2)
C3—H3···O1	1.0950 (8)	2.420 (10)	2.8543 (3)	101.9 (6)
C5—H5···O8	1.1000 (8)	2.353 (9)	2.6823 (3)	94.9 (6)
C9—H9···O1	1.0730 (8)	2.396 (5)	3.4064 (3)	156.5 (5)
C9—H9···O5	1.0730 (8)	2.310 (10)	2.7296 (3)	101.1 (9)
O7—H13···O6	0.9900 (8)	2.658 (10)	2.9910 (3)	99.9 (6)
O6—H12···O7	0.9710 (8)	2.560 (10)	2.9910 (3)	106.7 (7)
C1—H1A···O4^iv	1.0970 (8)	2.610 (10)	3.3056 (3)	120.2 (6)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.

(KUMPH_200K)

Crystal data

C9H12KN2O9P	F(000) = 744
Mr = 362.3	Dx = 1.772 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 52158 reflections
a = 8.0670 (2) Å	θ = 2.3–58.7°
b = 10.4871 (3) Å	µ = 0.56 mm^−1
c = 16.0561 (4) Å	T = 200 K
V = 1358.34 (6) Å^3	Thick plate-like block, colourless
Z = 4	0.28 × 0.27 × 0.16 mm

Data collection

CCD detector diffractometer	19248 independent reflections
Radiation source: TXS rotating anode	15846 reflections with I > 3σ(I)
Multilayer optics monochromator	Rint = 0.029
ω–scans	θmax = 59.3°, θmin = 2.3°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −19→18
Tmin = 0.860, Tmax = 0.890	k = −23→25
97227 measured reflections	l = −21→38

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.017	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.019	(Δ/σ)max = 0.010
S = 0.89	Δρmax = 0.13 e Å^−3
15846 reflections	Δρmin = −0.13 e Å^−3
642 parameters	Absolute structure: Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.
12 restraints	Absolute structure parameter: −0.002 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
K1	0.212198 (1)	0.402589 (1)	0.668447	0.016965
P1	0.137140 (10)	0.322435 (1)	0.459060	0.011988
O1	0.17962 (4)	0.20055 (4)	0.40307 (2)	0.01720 (3)
O5	0.38975 (3)	0.01593 (3)	0.323350 (10)	0.01452 (2)
O7	0.23825 (7)	−0.13860 (3)	0.17956 (2)	0.02099 (3)
O4	0.04971 (5)	0.26010 (4)	0.53522 (2)	0.01842 (2)
O8	0.36953 (5)	−0.36702 (5)	0.33670 (3)	0.02265 (4)
O2	0.29617 (5)	0.37989 (4)	0.49164 (2)	0.01595 (2)
O6	−0.01680 (5)	0.05165 (4)	0.23160 (3)	0.02138 (2)
N1	0.33234 (4)	−0.17255 (3)	0.39738 (2)	0.01506 (2)
O9	0.2589 (2)	−0.3548 (3)	0.6146 (2)	0.03800 (10)
O3	0.02840 (6)	0.41148 (6)	0.41109 (2)	0.02141 (3)
C3	0.11375 (4)	0.00783 (3)	0.28200 (2)	0.01435 (2)
N2	0.31774 (5)	−0.35813 (3)	0.47644 (2)	0.01986 (3)
C1	0.24963 (4)	0.21974 (3)	0.32228 (2)	0.01596 (2)
C2	0.26789 (4)	0.09229 (3)	0.280250 (10)	0.01325 (2)
C6	0.34199 (4)	−0.30417 (3)	0.39967 (2)	0.01583 (2)
C7	0.2819 (2)	−0.29430 (10)	0.54954 (6)	0.02471 (4)
C5	0.35017 (4)	−0.11467 (3)	0.314330 (10)	0.01354 (2)
C4	0.18922 (4)	−0.12311 (3)	0.26335 (2)	0.01507 (2)
C9	0.30110 (10)	−0.10249 (10)	0.46731 (5)	0.02371 (4)
C8	0.2758 (2)	−0.15820 (10)	0.54194 (7)	0.03289 (7)
H3	0.0680 (10)	0.0050 (10)	0.3465 (2)	0.02994
H1A	0.3705 (5)	0.2656 (7)	0.3280 (6)	0.03722
H1B	0.1654 (8)	0.2767 (7)	0.2843 (4)	0.03783
H2	0.3050 (10)	0.1090 (10)	0.2154 (2)	0.03065
H5	0.4513 (7)	−0.1646 (8)	0.2822 (5)	0.02739
H4	0.1096 (8)	−0.2015 (5)	0.2846 (6)	0.02734
H9	0.296 (2)	−0.0001 (2)	0.4587 (9)	0.03210
H8	0.2460 (10)	−0.0973 (7)	0.5943 (3)	0.03130
H11	−0.0507 (6)	0.2056 (6)	0.5216 (6)	0.03202
H13	0.1393 (5)	−0.1300 (10)	0.1457 (4)	0.02593
H10	0.315 (2)	−0.45632 (10)	0.4757 (8)	0.03084
H12	−0.019 (2)	0.0052 (6)	0.1794 (2)	0.02908

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.01796 (2)	0.01711 (2)	0.01583 (2)	−0.00008 (2)	−0.001350 (10)	0.002750 (10)
P1	0.01388 (2)	0.01204 (2)	0.01005 (2)	0.00053 (2)	−0.00143 (2)	−0.000760 (10)
O1	0.02640 (10)	0.01248 (9)	0.01270 (8)	−0.00195 (8)	0.00331 (8)	−0.00192 (7)
O5	0.01462 (8)	0.01445 (9)	0.01450 (7)	−0.00192 (7)	−0.00203 (7)	0.00103 (5)
O7	0.0268 (2)	0.0237 (2)	0.01243 (9)	0.00622 (10)	−0.00375 (9)	−0.00645 (6)
O4	0.01870 (10)	0.02460 (10)	0.01196 (9)	−0.00530 (10)	0.00135 (7)	−0.00067 (7)
O8	0.0356 (2)	0.01570 (10)	0.01660 (10)	0.00266 (10)	0.00088 (9)	−0.00418 (9)
O2	0.01491 (9)	0.01323 (9)	0.01971 (9)	−0.00107 (10)	−0.00270 (8)	−0.00103 (7)
O6	0.01760 (10)	0.02640 (10)	0.02020 (10)	0.00560 (10)	−0.00532 (9)	−0.00630 (10)
N1	0.02270 (10)	0.01218 (8)	0.01036 (6)	−0.00075 (7)	−0.00032 (5)	−0.00072 (6)
O9	0.0761 (6)	0.0214 (2)	0.01640 (10)	−0.0094 (2)	0.0062 (2)	0.00490 (10)
O3	0.02380 (10)	0.02200 (10)	0.01840 (10)	0.00620 (10)	−0.00743 (10)	0.00146 (9)
C3	0.01409 (9)	0.01655 (9)	0.01241 (7)	0.00041 (8)	−0.00039 (6)	−0.00306 (6)
N2	0.0319 (2)	0.01263 (9)	0.01505 (9)	−0.00256 (9)	−0.00092 (8)	0.00091 (7)
C1	0.02280 (10)	0.01300 (9)	0.01207 (7)	−0.00102 (8)	0.00129 (7)	0.00016 (6)
C2	0.01592 (9)	0.01407 (8)	0.00976 (6)	0.000003 (8)	0.00022 (5)	−0.00034 (5)
C6	0.02210 (10)	0.01247 (8)	0.01289 (7)	−0.00023 (8)	−0.00136 (6)	−0.00121 (6)
C7	0.0447 (2)	0.01630 (10)	0.01310 (9)	−0.00730 (10)	0.00140 (10)	0.00157 (7)
C5	0.01594 (9)	0.01404 (9)	0.01065 (6)	0.00059 (8)	−0.00023 (6)	−0.00086 (5)
C4	0.01738 (10)	0.01464 (8)	0.01318 (7)	−0.00075 (9)	−0.00199 (6)	−0.00302 (6)
C9	0.0468 (2)	0.01274 (9)	0.01161 (8)	−0.00350 (10)	0.00424 (9)	−0.00139 (6)
C8	0.0707 (4)	0.01610 (10)	0.01192 (9)	−0.0073 (2)	0.00780 (10)	−0.00161 (8)
H3	0.0370	0.0316	0.0212	0.0004	0.0029	0.0000
H1A	0.0445	0.0351	0.0320	−0.0110	0.0014	−0.0057
H1B	0.0532	0.0324	0.0278	0.0071	−0.0045	0.0016
H2	0.0415	0.0301	0.0203	−0.0044	0.0016	0.0007
H5	0.0274	0.0300	0.0247	0.0000	0.0013	−0.0040
H4	0.0289	0.0254	0.0277	−0.0055	0.0015	0.0026
H9	0.0462	0.0211	0.0289	−0.0014	0.0017	0.0000
H8	0.0446	0.0266	0.0227	0.0015	0.0038	−0.0061
H11	0.0385	0.0310	0.0266	−0.0014	−0.0019	−0.0011
H13	0.0231	0.0313	0.0235	−0.0003	−0.0035	0.0007
H10	0.0478	0.0215	0.0232	0.0001	0.0016	−0.0019
H12	0.0348	0.0291	0.0233	0.0042	−0.0020	−0.0038

Geometric parameters (Å, º)

P1—O1	1.5998 (4)	C3—C2	1.5269 (4)
P1—O4	1.5557 (4)	C3—C4	1.5316 (4)
P1—O3	1.4949 (4)	C3—H3	1.0980 (9)
P1—O2	1.5108 (4)	N2—C6	1.3704 (5)
O1—C1	1.4290 (4)	N2—C7	1.3820 (10)
O5—C5	1.4139 (5)	N2—H10	1.0300 (9)
O5—C2	1.4445 (4)	C1—C2	1.5045 (4)
O7—C4	1.4117 (5)	C1—H1B	1.0910 (9)
O7—H13	0.9700 (9)	C1—H1A	1.0910 (9)
O4—H11	1.0150 (9)	C2—H2	1.0980 (9)
O8—C6	1.2271 (5)	C7—C8	1.433 (2)
O6—C3	1.4055 (5)	C5—C4	1.5374 (4)
O6—H12	0.9699 (9)	C5—H5	1.0980 (9)
N1—C6	1.3830 (4)	C4—H4	1.0980 (9)
N1—C5	1.4721 (4)	C9—C8	1.3490 (10)
N1—C9	1.3652 (9)	C9—H9	1.0829 (9)
O9—C7	1.236 (3)	C8—H8	1.0830 (9)
P1—O1—C1	118.83 (3)	O9—C7—N2	120.0 (2)
P1—O4—H11	115.4 (5)	O9—C7—C8	125.3 (2)
O1—P1—O4	101.72 (2)	C3—O6—H12	110.5 (7)
O1—P1—O3	109.59 (2)	C3—C2—C1	115.30 (2)
O1—P1—O2	109.35 (2)	C3—C2—H2	109.4 (5)
O1—C1—C2	108.71 (3)	C3—C4—C5	100.37 (2)
O1—C1—H1B	109.7 (4)	C3—C4—H4	112.2 (4)
O1—C1—H1A	109.8 (5)	N2—C7—C8	114.67 (8)
O5—C5—N1	109.19 (3)	C1—C2—H2	108.2 (6)
O5—C5—C4	107.52 (3)	C2—O5—C5	109.53 (3)
O5—C5—H5	110.0 (5)	C2—C3—C4	101.11 (3)
O5—C2—C3	102.93 (3)	C2—C3—H3	107.8 (5)
O5—C2—C1	110.13 (2)	C2—C1—H1B	107.3 (4)
O5—C2—H2	110.8 (6)	C2—C1—H1A	110.0 (4)
O7—C4—C5	106.10 (3)	C6—N1—C5	115.47 (3)
O7—C4—C3	113.64 (3)	C6—N1—C9	121.72 (6)
O7—C4—H4	111.9 (5)	C6—N2—C7	126.43 (6)
O4—P1—O3	113.67 (2)	C6—N2—H10	113.9 (7)
O4—P1—O2	106.28 (2)	C7—N2—H10	119.4 (7)
O8—C6—N1	121.63 (3)	C7—C8—C9	120.10 (10)
O8—C6—N2	123.04 (4)	C7—C8—H8	121.9 (5)
O2—P1—O3	115.31 (3)	C5—N1—C9	122.75 (5)
O6—C3—C2	114.20 (3)	C5—C4—H4	111.9 (5)
O6—C3—C4	118.58 (3)	C4—O7—H13	107.0 (4)
O6—C3—H3	107.7 (5)	C4—C5—H5	110.5 (4)
N1—C6—N2	115.34 (3)	C4—C3—H3	106.9 (6)
N1—C5—C4	112.09 (3)	C9—C8—H8	117.9 (5)
N1—C5—H5	107.6 (5)	C8—C9—H9	122.5 (8)
N1—C9—C8	121.70 (8)	H1A—C1—H1B	111.2 (7)
N1—C9—H9	115.8 (8)
P1—O1—C1—C2	−176.42 (2)	O3—P1—O1—C1	53.98 (2)
P1—O1—C1—H1B	−59.4 (4)	O3—P1—O4—H11	61.1 (4)
P1—O1—C1—H1A	63.2 (5)	C3—C2—O5—C5	26.95 (3)
O1—P1—O4—H11	−56.6 (4)	C3—C2—C1—H1B	−69.2 (4)
O1—C1—C2—O5	−66.52 (2)	C3—C2—C1—H1A	169.7 (3)
O1—C1—C2—C3	49.39 (3)	C3—C4—O7—H13	−61.4 (6)
O1—C1—C2—H2	172.2 (3)	C3—C4—C5—H5	−144.7 (5)
O5—C5—N1—C6	−161.82 (2)	N2—C6—N1—C5	−177.12 (3)
O5—C5—N1—C9	20.95 (5)	N2—C6—N1—C9	0.15 (5)
O5—C5—C4—O7	93.90 (2)	N2—C7—C8—C9	1.15 (9)
O5—C5—C4—C3	−24.59 (3)	N2—C7—C8—H8	178.7 (2)
O5—C5—C4—H4	−143.8 (4)	C1—C2—O5—C5	150.40 (2)
O5—C2—C3—O6	−169.96 (3)	C1—C2—C3—C4	−161.38 (2)
O5—C2—C3—C4	−41.43 (2)	C1—C2—C3—H3	−49.5 (6)
O5—C2—C3—H3	70.5 (6)	C2—O5—C5—C4	−1.27 (2)
O5—C2—C1—H1B	174.9 (2)	C2—O5—C5—H5	119.1 (5)
O5—C2—C1—H1A	53.8 (5)	C2—C3—O6—H12	100.1 (7)
O7—C4—C5—N1	−146.09 (3)	C2—C3—C4—C5	39.39 (2)
O7—C4—C5—H5	−26.2 (5)	C2—C3—C4—H4	158.3 (4)
O7—C4—C3—O6	52.21 (3)	C6—N1—C5—C4	79.15 (2)
O7—C4—C3—C2	−73.44 (3)	C6—N1—C5—H5	−42.5 (5)
O7—C4—C3—H3	173.9 (3)	C6—N1—C9—C8	−0.96 (7)
O4—P1—O1—C1	174.57 (3)	C6—N1—C9—H9	180.0 (4)
O8—C6—N1—C5	2.50 (3)	C6—N2—C7—C8	−2.09 (7)
O8—C6—N1—C9	179.76 (6)	C7—C8—C9—H9	179.2 (2)
O8—C6—N2—C7	−178.14 (7)	C5—O5—C2—H2	−90.0 (5)
O8—C6—N2—H10	−4.6 (6)	C5—N1—C9—C8	176.11 (8)
O2—P1—O1—C1	−73.32 (2)	C5—N1—C9—H9	−2.9 (8)
O2—P1—O4—H11	−171.0 (3)	C5—C4—O7—H13	−170.8 (3)
O6—C3—C2—C1	70.10 (3)	C5—C4—C3—H3	−73.2 (5)
O6—C3—C2—H2	−52.0 (6)	C4—C5—N1—C9	−98.08 (5)
O6—C3—C4—C5	165.03 (3)	C4—C3—O6—H12	−18.9 (6)
O6—C3—C4—H4	−76.0 (4)	C4—C3—C2—H2	76.5 (6)
N1—C6—N2—C7	1.47 (5)	C9—N1—C5—H5	140.3 (4)
N1—C6—N2—H10	175.0 (2)	C8—C7—N2—H10	−175.3 (3)
N1—C5—O5—C2	−123.10 (3)	H3—C3—O6—H12	−140.3 (7)
N1—C5—C4—C3	95.42 (2)	H3—C3—C2—H2	−171.6 (8)
N1—C5—C4—H4	−23.8 (5)	H3—C3—C4—H4	45.7 (7)
N1—C9—C8—C7	0.25 (8)	H1A—C1—C2—H2	−67.5 (7)
N1—C9—C8—H8	−177.4 (2)	H1B—C1—C2—H2	53.6 (7)
O9—C7—N2—C6	178.3 (2)	H5—C5—C4—H4	96.1 (6)
O9—C7—N2—H10	5.1 (7)	H4—C4—O7—H13	67.0 (7)
O9—C7—C8—C9	−179.2 (2)	H9—C9—C8—H8	1.6 (8)
O9—C7—C8—H8	−1.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···P1^i	1.0150 (9)	2.555 (5)	3.4401 (5)	145.6 (4)
O4—H11···O1^i	1.0150 (9)	2.677 (7)	3.1726 (5)	110.1 (5)
O4—H11···O2^i	1.0150 (9)	1.5410 (10)	2.5543 (6)	175.4 (2)
N2—H10···O2^ii	1.0300 (9)	1.744 (2)	2.7637 (5)	170.0 (3)
O7—H13···O3^iii	0.9700 (9)	1.688 (2)	2.6498 (7)	170.5 (3)
O6—H12···O3^iii	0.9699 (9)	1.7550 (10)	2.7236 (6)	175.90 (10)
C3—H3···O1	1.0980 (9)	2.418 (10)	2.8541 (4)	101.9 (6)
C5—H5···O8	1.0980 (9)	2.389 (9)	2.6752 (6)	92.7 (6)
C9—H9···O1	1.0829 (9)	2.472 (6)	3.4820 (10)	154.7 (6)
C9—H9···O5	1.0829 (9)	2.31 (2)	2.7196 (10)	100.4 (10)
O7—H13···O6	0.9700 (9)	2.667 (9)	2.9854 (7)	99.6 (6)
O6—H12···O7	0.9699 (9)	2.570 (10)	2.9854 (7)	106.0 (8)
C1—H1A···O4^iv	1.0910 (9)	2.643 (9)	3.3376 (5)	120.9 (5)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.

(KUMPH_300K)

Crystal data

C9H12KN2O9P	F(000) = 744
Mr = 362.3	Dx = 1.76 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9713 reflections
a = 8.0835 (2) Å	θ = 2.3–51.7°
b = 10.5221 (3) Å	µ = 0.56 mm^−1
c = 16.0738 (4) Å	T = 300 K
V = 1367.16 (6) Å^3	Thick plate-like block, colourless
Z = 4	0.28 × 0.27 × 0.16 mm

Data collection

CCD detector diffractometer	18254 independent reflections
Radiation source: TXS rotating anode	12221 reflections with I > 3σ(I)
Multilayer optics monochromator	Rint = 0.029
ω–scans	θmax = 58.7°, θmin = 2.3°
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38	h = −17→17
Tmin = 0.847, Tmax = 0.929	k = −12→24
89436 measured reflections	l = −32→37

Refinement

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.019	Weighting scheme based on measured s.u.'s
wR(F^2) = 0.022	(Δ/σ)max = 0.005
S = 1.04	Δρmax = 0.13 e Å^−3
12221 reflections	Δρmin = −0.13 e Å^−3
642 parameters	Absolute structure: Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.
13 restraints	Absolute structure parameter: 0.001 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
K1	0.212830 (10)	0.402964 (1)	0.667627 (1)	0.026544 (1)
P1	0.137890 (10)	0.321474 (1)	0.458144 (1)	0.018679 (1)
O1	0.18053 (7)	0.19961 (6)	0.40262 (4)	0.02633 (6)
O5	0.38964 (5)	0.01481 (5)	0.32351 (2)	0.02214 (3)
O7	0.23770 (10)	−0.13943 (5)	0.18006 (5)	0.03237 (7)
O4	0.05114 (9)	0.25958 (6)	0.53473 (5)	0.02824 (5)
O8	0.36851 (8)	−0.36700 (8)	0.33585 (6)	0.03457 (10)
O2	0.29627 (9)	0.37921 (6)	0.49049 (3)	0.02470 (4)
O6	−0.01597 (10)	0.05081 (7)	0.23194 (6)	0.03273 (5)
N1	0.33345 (6)	−0.17339 (4)	0.39715 (3)	0.02275 (4)
O9	0.2639 (3)	−0.3556 (7)	0.6121 (4)	0.0582 (3)
O3	0.02950 (10)	0.40990 (10)	0.41030 (4)	0.03294 (6)
C3	0.11452 (6)	0.00686 (4)	0.28229 (3)	0.02165 (4)
N2	0.31903 (8)	−0.35889 (6)	0.47549 (5)	0.03028 (7)
C1	0.25033 (7)	0.21821 (4)	0.32204 (3)	0.02416 (4)
C2	0.26823 (6)	0.09084 (4)	0.28042 (3)	0.02016 (3)
C6	0.34243 (7)	−0.30460 (4)	0.39899 (3)	0.02399 (4)
C7	0.2856 (2)	−0.2956 (2)	0.54860 (10)	0.03675 (8)
C5	0.35014 (7)	−0.11528 (4)	0.31434 (3)	0.02068 (4)
C4	0.18932 (7)	−0.12368 (4)	0.26370 (3)	0.02292 (4)
C9	0.3047 (2)	−0.1038 (2)	0.46740 (10)	0.03530 (9)
C8	0.2817 (3)	−0.1606 (2)	0.54140 (10)	0.0493 (2)
H3	0.0700 (10)	0.0020 (10)	0.3468 (2)	0.03953
H1A	0.3699 (5)	0.2655 (8)	0.3276 (8)	0.04910
H1B	0.1706 (10)	0.2770 (8)	0.2831 (5)	0.05007
H2	0.307 (2)	0.1060 (10)	0.2157 (2)	0.04074
H5	0.4517 (8)	−0.1655 (9)	0.2831 (6)	0.03575
H4	0.1082 (9)	−0.2002 (6)	0.2859 (7)	0.03564
H9	0.298 (2)	−0.0017 (3)	0.4600 (10)	0.04139
H8	0.259 (2)	−0.0979 (8)	0.5937 (4)	0.04006
H11	−0.0474 (7)	0.2042 (7)	0.5200 (8)	0.04325
H13	0.1392 (6)	−0.1280 (10)	0.1464 (5)	0.03393
H10	0.318 (2)	−0.45680 (10)	0.4751 (10)	0.03967
H12	−0.020 (2)	0.0028 (7)	0.1804 (3)	0.03864

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.02850 (4)	0.02646 (3)	0.02467 (4)	−0.00019 (3)	−0.00209 (3)	0.00438 (3)
P1	0.02183 (4)	0.01847 (3)	0.01574 (4)	0.00083 (3)	−0.00223 (3)	−0.00122 (2)
O1	0.0407 (3)	0.0184 (2)	0.0198 (2)	−0.00270 (10)	0.0049 (2)	−0.00290 (10)
O5	0.0226 (2)	0.0215 (2)	0.0223 (2)	−0.00300 (10)	−0.0029 (2)	0.00160 (9)
O7	0.0424 (4)	0.0355 (3)	0.0192 (2)	0.0093 (2)	−0.0057 (2)	−0.01000 (10)
O4	0.0288 (2)	0.0376 (2)	0.0183 (2)	−0.0085 (2)	0.0020 (2)	−0.00090 (10)
O8	0.0555 (5)	0.0231 (3)	0.0251 (3)	0.00400 (10)	0.0011 (2)	−0.0064 (2)
O2	0.0238 (2)	0.0196 (2)	0.0306 (2)	−0.00150 (10)	−0.0042 (2)	−0.00150 (10)
O6	0.0276 (2)	0.0398 (2)	0.0307 (2)	0.0090 (3)	−0.0088 (2)	−0.0094 (2)
N1	0.0340 (2)	0.01800 (10)	0.01630 (10)	−0.00105 (10)	−0.00070 (10)	−0.00130 (10)
O9	0.1170 (10)	0.0320 (5)	0.0260 (5)	−0.0143 (3)	0.0082 (4)	0.0077 (4)
O3	0.0373 (3)	0.0337 (3)	0.0278 (3)	0.0096 (3)	−0.0115 (3)	0.0019 (2)
C3	0.0215 (2)	0.02480 (10)	0.01860 (10)	0.00070 (10)	−0.00060 (10)	−0.00460 (10)
N2	0.0485 (4)	0.0191 (2)	0.0232 (2)	−0.00390 (10)	−0.0017 (2)	0.00160 (10)
C1	0.0350 (2)	0.01910 (10)	0.01850 (10)	−0.00140 (10)	0.00230 (10)	0.00040 (10)
C2	0.0246 (2)	0.02090 (10)	0.01490 (10)	0.00008 (11)	0.00040 (10)	−0.00048 (9)
C6	0.0338 (2)	0.01850 (10)	0.0197 (2)	−0.00020 (10)	−0.00190 (10)	−0.00190 (10)
C7	0.0659 (5)	0.0247 (2)	0.0197 (2)	−0.0103 (2)	0.0014 (2)	0.00280 (10)
C5	0.0249 (2)	0.02050 (10)	0.01660 (10)	0.00090 (10)	−0.00040 (10)	−0.00149 (9)
C4	0.0266 (2)	0.02200 (10)	0.0201 (2)	−0.00080 (10)	−0.00320 (10)	−0.00480 (10)
C9	0.0691 (5)	0.0191 (2)	0.0177 (2)	−0.0056 (2)	0.0055 (2)	−0.00220 (10)
C8	0.1053 (9)	0.0246 (2)	0.0179 (2)	−0.0112 (3)	0.0109 (3)	−0.0026 (2)
H3	0.0493	0.0400	0.0293	0.0006	0.0024	0.0001
H1A	0.0645	0.0432	0.0397	−0.0140	0.0014	−0.0064
H1B	0.0744	0.0399	0.0359	0.0067	−0.0051	0.0017
H2	0.0562	0.0380	0.0280	−0.0065	0.0008	0.0003
H5	0.0369	0.0389	0.0314	−0.0017	0.0000	−0.0048
H4	0.0381	0.0338	0.0350	−0.0060	0.0014	0.0028
H9	0.0584	0.0292	0.0366	−0.0010	0.0017	−0.0006
H8	0.0560	0.0338	0.0304	0.0011	0.0040	−0.0072
H11	0.0544	0.0399	0.0354	0.0007	−0.0025	−0.0017
H13	0.0320	0.0386	0.0311	−0.0007	−0.0043	0.0013
H10	0.0609	0.0297	0.0285	0.0005	0.0006	−0.0029
H12	0.0466	0.0374	0.0319	0.0052	−0.0027	−0.0038

Geometric parameters (Å, º)

P1—O1	1.5998 (6)	C3—C2	1.5250 (7)
P1—O4	1.5592 (8)	C3—C4	1.5302 (6)
P1—O3	1.4915 (8)	C3—H3	1.0980 (10)
P1—O2	1.5094 (8)	N2—C6	1.3690 (9)
O1—C1	1.4263 (9)	N2—C7	1.377 (2)
O5—C5	1.4133 (7)	N2—H10	1.0300 (10)
O5—C2	1.4433 (7)	C1—C2	1.5050 (6)
O7—C4	1.4099 (9)	C1—H1A	1.0910 (10)
O7—H13	0.9700 (10)	C1—H1B	1.0910 (10)
O4—H11	1.0150 (10)	C2—H2	1.0980 (10)
O8—C6	1.2271 (9)	C7—C8	1.425 (3)
O6—C3	1.4080 (10)	C5—C4	1.5363 (7)
O6—H12	0.9700 (10)	C5—H5	1.0980 (10)
N1—C6	1.3828 (6)	C4—H4	1.0980 (10)
N1—C5	1.4710 (6)	C9—C8	1.345 (2)
N1—C9	1.365 (2)	C9—H9	1.0830 (10)
O9—C7	1.213 (6)	C8—H8	1.0830 (10)
P1—O1—C1	118.81 (6)	O9—C7—N2	119.6 (5)
P1—O4—H11	114.2 (7)	O9—C7—C8	125.7 (5)
O1—P1—O4	101.69 (3)	C3—O6—H12	110.1 (9)
O1—P1—O3	109.80 (4)	C3—C2—C1	115.40 (4)
O1—P1—O2	109.39 (3)	C3—C2—H2	109.6 (6)
O1—C1—C2	108.64 (5)	C3—C4—C5	100.33 (3)
O1—C1—H1A	109.8 (7)	C3—C4—H4	111.0 (5)
O1—C1—H1B	111.4 (5)	N2—C7—C8	114.7 (2)
O5—C5—N1	109.20 (4)	C1—C2—H2	108.4 (7)
O5—C5—C4	107.59 (4)	C2—O5—C5	109.46 (5)
O5—C5—H5	110.1 (5)	C2—C3—C4	101.21 (4)
O5—C2—C3	102.91 (4)	C2—C3—H3	108.1 (6)
O5—C2—C1	110.22 (4)	C2—C1—H1A	110.9 (5)
O5—C2—H2	110.2 (8)	C2—C1—H1B	107.8 (5)
O7—C4—C5	106.08 (6)	C6—N1—C5	115.43 (4)
O7—C4—C3	113.66 (5)	C6—N1—C9	121.77 (9)
O7—C4—H4	112.9 (6)	C6—N2—C7	126.30 (10)
O4—P1—O3	113.79 (4)	C6—N2—H10	114.4 (9)
O4—P1—O2	106.12 (4)	C7—N2—H10	119.1 (9)
O8—C6—N1	121.71 (6)	C7—C8—C9	120.7 (2)
O8—C6—N2	122.91 (7)	C7—C8—H8	123.2 (6)
O2—P1—O3	115.14 (6)	C5—N1—C9	122.75 (10)
O6—C3—C2	114.13 (4)	C5—C4—H4	112.0 (5)
O6—C3—C4	118.60 (6)	C4—O7—H13	106.8 (6)
O6—C3—H3	108.4 (7)	C4—C5—H5	111.3 (5)
N1—C6—N2	115.38 (5)	C4—C3—H3	105.7 (6)
N1—C5—C4	112.20 (5)	C9—C8—H8	116.1 (6)
N1—C5—H5	106.4 (6)	C8—C9—H9	122.0 (10)
N1—C9—C8	121.20 (10)	H1A—C1—H1B	108.2 (8)
N1—C9—H9	117.0 (10)
P1—O1—C1—C2	−176.24 (4)	O3—P1—O1—C1	54.00 (4)
P1—O1—C1—H1A	62.3 (5)	O3—P1—O4—H11	62.3 (6)
P1—O1—C1—H1B	−57.6 (5)	C3—C2—O5—C5	27.17 (4)
O1—P1—O4—H11	−55.7 (6)	C3—C2—C1—H1A	170.2 (3)
O1—C1—C2—O5	−66.58 (4)	C3—C2—C1—H1B	−71.5 (5)
O1—C1—C2—C3	49.42 (4)	C3—C4—O7—H13	−59.7 (7)
O1—C1—C2—H2	172.7 (4)	C3—C4—C5—H5	−145.0 (6)
O5—C5—N1—C6	−162.12 (4)	N2—C6—N1—C5	−177.02 (6)
O5—C5—N1—C9	20.29 (9)	N2—C6—N1—C9	0.60 (9)
O5—C5—C4—O7	94.19 (4)	N2—C7—C8—C9	1.8 (2)
O5—C5—C4—C3	−24.31 (4)	N2—C7—C8—H8	−179.0 (4)
O5—C5—C4—H4	−142.2 (5)	C1—C2—O5—C5	150.77 (4)
O5—C2—C3—O6	−170.09 (4)	C1—C2—C3—C4	−161.61 (4)
O5—C2—C3—C4	−41.52 (3)	C1—C2—C3—H3	−50.9 (6)
O5—C2—C3—H3	69.2 (7)	C2—O5—C5—C4	−1.58 (4)
O5—C2—C1—H1A	54.2 (6)	C2—O5—C5—H5	119.8 (6)
O5—C2—C1—H1B	172.5 (3)	C2—C3—O6—H12	101.4 (9)
O7—C4—C5—N1	−145.68 (4)	C2—C3—C4—C5	39.26 (4)
O7—C4—C5—H5	−26.5 (6)	C2—C3—C4—H4	157.9 (5)
O7—C4—C3—O6	52.12 (6)	C6—N1—C5—C4	78.69 (3)
O7—C4—C3—C2	−73.52 (5)	C6—N1—C5—H5	−43.2 (5)
O7—C4—C3—H3	173.9 (4)	C6—N1—C9—C8	−0.90 (10)
O4—P1—O1—C1	174.81 (4)	C6—N1—C9—H9	−179.2 (4)
O8—C6—N1—C5	2.49 (6)	C6—N2—C7—C8	−2.20 (10)
O8—C6—N1—C9	−179.90 (10)	C7—C8—C9—H9	177.8 (2)
O8—C6—N2—C7	−178.50 (10)	C5—O5—C2—H2	−89.6 (7)
O8—C6—N2—H10	−3.7 (8)	C5—N1—C9—C8	176.50 (10)
O2—P1—O1—C1	−73.27 (3)	C5—N1—C9—H9	−2.0 (10)
O2—P1—O4—H11	−170.1 (3)	C5—C4—O7—H13	−169.0 (3)
O6—C3—C2—C1	69.82 (5)	C5—C4—C3—H3	−73.3 (6)
O6—C3—C2—H2	−52.9 (8)	C4—C5—N1—C9	−98.90 (8)
O6—C3—C4—C5	164.91 (4)	C4—C3—O6—H12	−17.7 (7)
O6—C3—C4—H4	−76.5 (5)	C4—C3—C2—H2	75.7 (8)
N1—C6—N2—C7	1.00 (10)	C9—N1—C5—H5	139.2 (5)
N1—C6—N2—H10	175.8 (2)	C8—C7—N2—H10	−176.7 (3)
N1—C5—O5—C2	−123.60 (4)	H3—C3—O6—H12	−138.1 (8)
N1—C5—C4—C3	95.82 (4)	H3—C3—C2—H2	−174.0 (10)
N1—C5—C4—H4	−22.1 (6)	H3—C3—C4—H4	45.3 (8)
N1—C9—C8—C7	−0.4 (2)	H1A—C1—C2—H2	−66.5 (9)
N1—C9—C8—H8	−179.7 (2)	H1B—C1—C2—H2	51.8 (10)
O9—C7—N2—C6	178.4 (4)	H5—C5—C4—H4	97.1 (7)
O9—C7—N2—H10	3.9 (9)	H4—C4—O7—H13	67.9 (8)
O9—C7—C8—C9	−178.9 (4)	H9—C9—C8—H8	−1.0 (10)
O9—C7—C8—H8	0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···P1^i	1.0150 (10)	2.582 (6)	3.4496 (8)	143.3 (5)
O4—H11···O2^i	1.0150 (10)	1.548 (2)	2.5580 (10)	172.7 (3)
N2—H10···O2^ii	1.0300 (10)	1.752 (3)	2.7724 (9)	170.1 (4)
O7—H13···O3^iii	0.9700 (10)	1.688 (2)	2.654 (2)	173.4 (3)
O6—H12···O3^iii	0.9700 (10)	1.758 (2)	2.7270 (10)	177.40 (10)
C3—H3···O1	1.0980 (10)	2.430 (10)	2.8530 (7)	100.9 (6)
C5—H5···O8	1.0980 (10)	2.380 (10)	2.6752 (9)	93.1 (8)
C9—H9···O1	1.0830 (10)	2.497 (8)	3.505 (2)	154.4 (7)
C9—H9···O5	1.0830 (10)	2.32 (2)	2.716 (2)	99.0 (10)
O7—H13···O6	0.9700 (10)	2.650 (10)	2.9850 (10)	100.8 (7)
O6—H12···O7	0.9700 (10)	2.56 (2)	2.9850 (10)	106.0 (10)
C1—H1A···O4^iv	1.0910 (10)	2.670 (10)	3.3568 (9)	120.7 (7)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1.