1,10-Phenanthrolin-1-ium 1-oxo-2,6,7-trioxa-1-phosphabicyclo­[2.2.2]octane-4-carboxyl­ate 1-oxo-2,6,7-trioxa-1-phosphabicyclo­[2.2.2]octane-4-carboxylic acid monohydrate

Wang, Z.; Zang, H.-J.; Guo, M.-L.

doi:10.1107/S1600536807032813

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1,10-Phenanthrolin-1-ium 1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxylate 1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxylic acid monohydrate

Z. Wang, H.-J. Zang and M.-L. Guo

The asymmetric unit of the title salt, C₁₂H₉N₂⁺·C₅H₆O₆P⁻·C₅H₇O₆P·H₂O, contains one 1,10-phenanthrolinium cation, one 1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxylate anion, one 1-oxo-2,6,7-trioxa-1-phospha-bicyclo[2.2.2]octane-4-carboxylic acid neutral molecule and one water molecule. In the anion, the oxygen atoms of the carboxylate group are disordered over two positions, with site occupation factors ca 0.7:0.3. In the crystal structure, intermolecular O—H

O and N—H

O hydrogen-bonding interactions result in the formation of a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032813/rz2150sup1.cif Contains datablocks I, publication_text
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032813/rz2150Isup2.hkl Contains datablock I

CCDC reference: 657701

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.053
wR factor = 0.159
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.66
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.28
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT415_ALERT_2_C Short Inter D-H..H-X       H7B    ..  H13A    ..       2.12 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         38

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Caged bicyclic phosphates are widely used as flame retardants in some polymers. As a low-toxicity and environmentally friendly flame retardant system, the phosphorus-nitrogen combination has been extensively studied. We report here the crystal structure of a new bicyclic phosphate cage compound.

The content of the asymmetric unit of the title salt is shown in Fig. 1. In the 1,10-phenanthrolinium cation, the C—N—C bond angle of 123.0 (3)° at the protonated N1 atom is significantly larger than that at the non-protonated N2 atom (116.4 (3)°). This widening is not unexpected, as analogous differences were already observed in previously reported monoprotonated phenanthrolines (Hensen et al., 1998, 2000; Guo, 2005). In the anion, the oxygen atoms O11 and O12 of the carboxylate group are positionally disordered over two position, with site occupation factors of 0.701 (15) and 0.299 (15) for the major and minor components respectively. In the crystal structure, ions and neutral molecules are linked into an extended three-dimensional network by O—H···O and N—H···O hydrogen bonding interactions (Table 1, Fig. 2).

Related literature top

For related literature, see: Guo (2005); Hensen et al. (1998, 2000).

Experimental top

The title salt was prepared by mixing ethanol solutions of 1-oxo-2,6,7-trioxa-1-phospha-bicyclo[2.2.2]octane-4-carboxylic acid (1.94 g in 10 ml) and 1,10-phenanthroline (1.8 g in 10 ml). The solution was stirred at room temperature for 10 min, after which the crystalline product was separated by filtration. The pure product (1.0 g) was heated and dissolved in water (25 ml). Single crystals suitable for X-ray analysis were obtained from this aqueous solution by slow evaporation of the solvent over a period of five days at room temperature.

Structure description top

For related literature, see: Guo (2005); Hensen et al. (1998, 2000).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Only the major component of disorder is shown.
	Fig. 2. Packing diagram of the title compound, showing hydrogen-bond interactions as dashed lines.

1,10-Phenanthrolin-1-ium 1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxylate 1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxylic acid monohydrate top

Crystal data top

C₁₂H₉N₂⁺·C₅H₆O₆P⁻·C₅H₇O₆P·H₂O	F(000) = 1216
M_r = 586.37	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2791 reflections
a = 9.2841 (18) Å	θ = 2.5–26.3°
b = 8.5863 (16) Å	µ = 0.25 mm⁻¹
c = 31.124 (6) Å	T = 294 K
β = 99.917 (5)°	Prism, colorless
V = 2444.0 (8) Å³	0.20 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area detector diffractometer	5008 independent reflections
Radiation source: fine-focus sealed tube	2956 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 26.4°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→8
T_min = 0.948, T_max = 0.972	k = −10→10
13684 measured reflections	l = −38→36

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0773P)² + 0.655P] where P = (F_o² + 2F_c²)/3
5008 reflections	(Δ/σ)_max = 0.001
371 parameters	Δρ_max = 0.35 e Å⁻³
38 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₂H₉N₂⁺·C₅H₆O₆P⁻·C₅H₇O₆P·H₂O	V = 2444.0 (8) Å³
M_r = 586.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2841 (18) Å	µ = 0.25 mm⁻¹
b = 8.5863 (16) Å	T = 294 K
c = 31.124 (6) Å	0.20 × 0.16 × 0.12 mm
β = 99.917 (5)°

Data collection top

Bruker SMART CCD area detector diffractometer	5008 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2956 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.972	R_int = 0.043
13684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	38 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
5008 reflections	Δρ_min = −0.32 e Å⁻³
371 parameters

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	U_iso*/U_eq	Occ. (<1)
P1	1.15068 (9)	0.02050 (10)	0.95898 (3)	0.0336 (2)
O1	1.2593 (2)	0.0302 (3)	0.99848 (7)	0.0451 (6)
O2	1.2147 (2)	0.0221 (3)	0.91570 (7)	0.0514 (7)
O3	1.0366 (2)	0.1551 (3)	0.95336 (7)	0.0440 (6)
O4	1.0576 (2)	−0.1324 (3)	0.95573 (7)	0.0460 (6)
O5	0.8678 (3)	−0.0305 (3)	0.81115 (7)	0.0533 (7)
O6	0.7046 (2)	−0.0035 (3)	0.85531 (7)	0.0554 (7)
H6C	0.6335	−0.0100	0.8339	0.066*
C1	1.1025 (4)	0.0206 (5)	0.87599 (10)	0.0477 (9)
H1A	1.1220	−0.0637	0.8571	0.057*
H1B	1.1055	0.1178	0.8603	0.057*
C2	0.9191 (3)	0.1378 (4)	0.91576 (10)	0.0387 (8)
H2A	0.9109	0.2321	0.8983	0.046*
H2B	0.8268	0.1210	0.9256	0.046*
C3	0.9521 (4)	−0.1485 (4)	0.91557 (10)	0.0426 (8)
H3A	0.8552	−0.1652	0.9224	0.051*
H3B	0.9772	−0.2377	0.8992	0.051*
C4	0.9527 (3)	−0.0008 (3)	0.88813 (9)	0.0308 (7)
C5	0.8348 (4)	−0.0131 (4)	0.84658 (10)	0.0370 (8)
P2	0.91080 (11)	0.49646 (13)	0.82372 (3)	0.0523 (3)
O7	1.0150 (3)	0.4764 (4)	0.86362 (9)	0.0841 (10)
O8	0.8420 (4)	0.3432 (3)	0.80474 (10)	0.0960 (11)
O9	0.7750 (3)	0.5977 (4)	0.82963 (7)	0.0649 (8)
O10	0.9709 (3)	0.5822 (4)	0.78669 (8)	0.0795 (10)
C6	0.7333 (5)	0.3608 (5)	0.76470 (14)	0.0862 (13)
H6A	0.6396	0.3205	0.7694	0.103*
H6B	0.7638	0.3021	0.7412	0.103*
C7	0.6693 (4)	0.6187 (5)	0.78974 (10)	0.0575 (10)
H7A	0.6594	0.7287	0.7828	0.069*
H7B	0.5747	0.5798	0.7940	0.069*
C8	0.8643 (4)	0.5989 (6)	0.74632 (11)	0.0712 (12)
H8A	0.8993	0.5447	0.7228	0.085*
H8B	0.8530	0.7081	0.7386	0.085*
C9	0.7185 (4)	0.5323 (4)	0.75239 (10)	0.0440 (8)
C10	0.6033 (4)	0.5554 (5)	0.71121 (11)	0.0549 (10)
O11	0.5054 (7)	0.4583 (8)	0.7037 (2)	0.0620 (19)	0.701 (15)
O12	0.6099 (9)	0.6825 (11)	0.6909 (3)	0.123 (4)	0.701 (15)
O11'	0.4766 (12)	0.5159 (19)	0.7151 (4)	0.048 (3)	0.299 (15)
O12'	0.6430 (10)	0.553 (3)	0.6759 (3)	0.075 (7)	0.299 (15)
N1	0.5028 (3)	0.8006 (3)	0.96061 (8)	0.0342 (6)
H1	0.5655	0.8589	0.9790	0.041*
N2	0.5012 (3)	0.7655 (3)	1.04740 (8)	0.0381 (7)
C11	0.5104 (4)	0.8262 (4)	0.91909 (10)	0.0386 (8)
H11	0.5743	0.9009	0.9116	0.046*
C12	0.4235 (4)	0.7417 (4)	0.88690 (10)	0.0422 (8)
H12	0.4296	0.7583	0.8577	0.051*
C13	0.3281 (4)	0.6333 (4)	0.89802 (10)	0.0399 (8)
H13	0.2697	0.5762	0.8763	0.048*
C14	0.3182 (3)	0.6079 (4)	0.94211 (9)	0.0339 (7)
C15	0.2217 (4)	0.4975 (4)	0.95668 (11)	0.0402 (8)
H15	0.1603	0.4379	0.9363	0.048*
C16	0.2182 (4)	0.4786 (4)	0.99920 (11)	0.0405 (8)
H16	0.1543	0.4060	1.0078	0.049*
C17	0.3105 (3)	0.5678 (4)	1.03176 (10)	0.0345 (7)
C18	0.3133 (4)	0.5502 (4)	1.07702 (11)	0.0410 (8)
H18	0.2517	0.4791	1.0873	0.049*
C19	0.4072 (4)	0.6385 (4)	1.10530 (10)	0.0450 (9)
H19	0.4103	0.6283	1.1352	0.054*
C20	0.4988 (4)	0.7445 (4)	1.08938 (10)	0.0437 (8)
H20	0.5617	0.8039	1.1094	0.052*
C21	0.4079 (3)	0.6769 (3)	1.01926 (9)	0.0316 (7)
C22	0.4103 (3)	0.6958 (3)	0.97354 (9)	0.0307 (7)
O13	0.3103 (4)	0.5046 (4)	0.79112 (13)	0.1197 (14)
H13A	0.3580	0.5070	0.7702	0.144*
H13B	0.2572	0.4255	0.7859	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0254 (4)	0.0425 (5)	0.0304 (4)	−0.0021 (4)	−0.0018 (3)	−0.0021 (4)
O1	0.0347 (13)	0.0596 (15)	0.0368 (13)	−0.0045 (11)	−0.0062 (10)	−0.0028 (11)
O2	0.0258 (12)	0.0915 (19)	0.0353 (13)	−0.0075 (13)	0.0008 (10)	−0.0068 (12)
O3	0.0435 (13)	0.0436 (13)	0.0386 (13)	0.0066 (11)	−0.0103 (11)	−0.0131 (10)
O4	0.0449 (13)	0.0411 (13)	0.0435 (13)	−0.0065 (11)	−0.0160 (11)	0.0080 (10)
O5	0.0522 (16)	0.0778 (18)	0.0279 (13)	−0.0068 (14)	0.0014 (11)	−0.0081 (12)
O6	0.0284 (13)	0.096 (2)	0.0361 (13)	−0.0018 (13)	−0.0098 (10)	−0.0016 (12)
C1	0.0307 (18)	0.079 (3)	0.0318 (18)	−0.0028 (18)	0.0019 (14)	−0.0056 (17)
C2	0.0358 (18)	0.0419 (19)	0.0338 (17)	0.0050 (16)	−0.0065 (14)	0.0004 (14)
C3	0.0415 (19)	0.0357 (18)	0.0437 (19)	−0.0049 (16)	−0.0126 (16)	−0.0013 (15)
C4	0.0280 (16)	0.0373 (17)	0.0253 (14)	0.0001 (14)	−0.0009 (13)	−0.0020 (13)
C5	0.0346 (19)	0.0387 (19)	0.0347 (18)	−0.0041 (15)	−0.0020 (15)	0.0002 (14)
P2	0.0441 (6)	0.0700 (7)	0.0351 (5)	−0.0119 (5)	−0.0156 (4)	0.0103 (5)
O7	0.0680 (19)	0.121 (3)	0.0496 (17)	−0.0271 (19)	−0.0275 (15)	0.0276 (16)
O8	0.114 (2)	0.0543 (17)	0.091 (2)	0.0021 (17)	−0.0649 (19)	0.0064 (15)
O9	0.0637 (18)	0.098 (2)	0.0291 (13)	−0.0002 (17)	−0.0041 (12)	−0.0061 (13)
O10	0.0362 (15)	0.152 (3)	0.0465 (15)	−0.0141 (18)	−0.0035 (12)	0.0238 (17)
C6	0.097 (3)	0.062 (2)	0.078 (2)	0.005 (2)	−0.049 (2)	−0.005 (2)
C7	0.049 (2)	0.080 (3)	0.0385 (19)	0.008 (2)	−0.0056 (17)	0.0008 (18)
C8	0.044 (2)	0.132 (3)	0.0354 (19)	0.002 (2)	−0.0004 (17)	0.020 (2)
C9	0.0395 (16)	0.0621 (18)	0.0262 (14)	0.0012 (15)	−0.0059 (13)	0.0023 (14)
C10	0.047 (2)	0.082 (3)	0.0306 (19)	0.003 (2)	−0.0077 (17)	0.0063 (19)
O11	0.057 (3)	0.054 (3)	0.061 (4)	−0.004 (3)	−0.029 (3)	−0.002 (3)
O12	0.142 (6)	0.109 (6)	0.086 (5)	−0.055 (5)	−0.069 (4)	0.050 (5)
O11'	0.039 (5)	0.058 (6)	0.043 (5)	−0.005 (4)	−0.003 (3)	−0.008 (4)
O12'	0.034 (5)	0.167 (19)	0.023 (5)	−0.007 (7)	0.004 (4)	0.017 (6)
N1	0.0300 (14)	0.0383 (15)	0.0320 (14)	−0.0016 (12)	−0.0013 (11)	−0.0033 (12)
N2	0.0384 (16)	0.0431 (16)	0.0301 (14)	−0.0013 (13)	−0.0012 (12)	−0.0031 (12)
C11	0.0359 (18)	0.0440 (19)	0.0356 (18)	−0.0008 (16)	0.0054 (15)	0.0050 (15)
C12	0.041 (2)	0.054 (2)	0.0303 (17)	0.0072 (18)	0.0030 (15)	0.0022 (15)
C13	0.0374 (18)	0.046 (2)	0.0321 (17)	0.0033 (16)	−0.0059 (15)	−0.0053 (14)
C14	0.0286 (16)	0.0368 (18)	0.0338 (17)	0.0035 (15)	−0.0022 (14)	−0.0037 (14)
C15	0.0321 (18)	0.0385 (19)	0.0459 (19)	−0.0049 (15)	−0.0049 (15)	−0.0050 (15)
C16	0.0355 (19)	0.0371 (19)	0.048 (2)	−0.0038 (15)	0.0040 (16)	0.0040 (15)
C17	0.0321 (17)	0.0329 (17)	0.0376 (18)	0.0078 (14)	0.0038 (14)	0.0015 (14)
C18	0.044 (2)	0.0394 (19)	0.0413 (19)	0.0061 (16)	0.0128 (16)	0.0061 (15)
C19	0.050 (2)	0.054 (2)	0.0322 (18)	0.0080 (19)	0.0088 (16)	0.0034 (16)
C20	0.042 (2)	0.051 (2)	0.0351 (19)	0.0040 (17)	−0.0004 (16)	−0.0075 (16)
C21	0.0294 (16)	0.0341 (17)	0.0296 (16)	0.0061 (14)	0.0003 (13)	−0.0016 (13)
C22	0.0267 (15)	0.0322 (16)	0.0312 (16)	0.0027 (14)	−0.0011 (13)	0.0002 (13)
O13	0.093 (3)	0.120 (3)	0.149 (4)	−0.018 (2)	0.029 (3)	−0.022 (2)

Geometric parameters (Å, º) top

P1—O1	1.452 (2)	C8—H8A	0.9700
P1—O3	1.557 (2)	C8—H8B	0.9700
P1—O2	1.563 (2)	C9—C10	1.535 (4)
P1—O4	1.565 (2)	C10—O12'	1.218 (8)
O2—C1	1.473 (4)	C10—O11	1.225 (6)
O3—C2	1.463 (3)	C10—O11'	1.250 (11)
O4—C3	1.455 (3)	C10—O12	1.268 (6)
O5—C5	1.204 (4)	N1—C11	1.325 (4)
O6—C5	1.286 (4)	N1—C22	1.352 (4)
O6—H6C	0.8548	N1—H1	0.8964
C1—C4	1.513 (4)	N2—C20	1.323 (4)
C1—H1A	0.9700	N2—C21	1.354 (4)
C1—H1B	0.9700	C11—C12	1.379 (4)
C2—C4	1.532 (4)	C11—H11	0.9300
C2—H2A	0.9700	C12—C13	1.369 (5)
C2—H2B	0.9700	C12—H12	0.9300
C3—C4	1.529 (4)	C13—C14	1.408 (4)
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C22	1.404 (4)
C4—C5	1.547 (4)	C14—C15	1.430 (4)
P2—O7	1.447 (3)	C15—C16	1.339 (5)
P2—O8	1.536 (3)	C15—H15	0.9300
P2—O10	1.550 (3)	C16—C17	1.431 (4)
P2—O9	1.568 (3)	C16—H16	0.9300
O8—C6	1.470 (4)	C17—C21	1.403 (4)
O9—C7	1.455 (4)	C17—C18	1.413 (4)
O10—C8	1.467 (4)	C18—C19	1.359 (5)
C6—C9	1.522 (5)	C18—H18	0.9300
C6—H6A	0.9700	C19—C20	1.393 (5)
C6—H6B	0.9700	C19—H19	0.9300
C7—C9	1.514 (5)	C20—H20	0.9300
C7—H7A	0.9700	C21—C22	1.436 (4)
C7—H7B	0.9700	O13—H13A	0.8488
C8—C9	1.511 (5)	O13—H13B	0.8393

O1—P1—O3	114.37 (13)	C9—C8—H8A	109.7
O1—P1—O2	114.69 (14)	O10—C8—H8B	109.7
O3—P1—O2	104.42 (13)	C9—C8—H8B	109.7
O1—P1—O4	113.44 (13)	H8A—C8—H8B	108.2
O3—P1—O4	104.95 (13)	C8—C9—C7	107.8 (3)
O2—P1—O4	103.81 (13)	C8—C9—C6	110.7 (4)
C1—O2—P1	113.86 (19)	C7—C9—C6	107.9 (3)
C2—O3—P1	114.43 (18)	C8—C9—C10	110.9 (3)
C3—O4—P1	114.66 (18)	C7—C9—C10	108.6 (3)
C5—O6—H6C	117.4	C6—C9—C10	110.8 (3)
O2—C1—C4	109.8 (2)	O12'—C10—O11	98.3 (8)
O2—C1—H1A	109.7	O12'—C10—O11'	121.3 (8)
C4—C1—H1A	109.7	O12'—C10—O12	61.1 (7)
O2—C1—H1B	109.7	O11—C10—O12	126.0 (4)
C4—C1—H1B	109.7	O11'—C10—O12	114.1 (7)
H1A—C1—H1B	108.2	O12'—C10—C9	118.4 (5)
O3—C2—C4	109.4 (2)	O11—C10—C9	117.4 (4)
O3—C2—H2A	109.8	O11'—C10—C9	114.6 (6)
C4—C2—H2A	109.8	O12—C10—C9	116.1 (4)
O3—C2—H2B	109.8	C11—N1—C22	123.0 (3)
C4—C2—H2B	109.8	C11—N1—H1	113.2
H2A—C2—H2B	108.2	C22—N1—H1	123.8
O4—C3—C4	109.5 (2)	C20—N2—C21	116.4 (3)
O4—C3—H3A	109.8	N1—C11—C12	119.9 (3)
C4—C3—H3A	109.8	N1—C11—H11	120.0
O4—C3—H3B	109.8	C12—C11—H11	120.0
C4—C3—H3B	109.8	C13—C12—C11	119.8 (3)
H3A—C3—H3B	108.2	C13—C12—H12	120.1
C1—C4—C3	109.4 (3)	C11—C12—H12	120.1
C1—C4—C2	109.3 (3)	C12—C13—C14	120.4 (3)
C3—C4—C2	108.1 (3)	C12—C13—H13	119.8
C1—C4—C5	110.4 (2)	C14—C13—H13	119.8
C3—C4—C5	109.9 (2)	C22—C14—C13	117.5 (3)
C2—C4—C5	109.8 (2)	C22—C14—C15	118.4 (3)
O5—C5—O6	126.8 (3)	C13—C14—C15	124.2 (3)
O5—C5—C4	121.3 (3)	C16—C15—C14	121.1 (3)
O6—C5—C4	112.0 (3)	C16—C15—H15	119.4
O7—P2—O8	113.61 (17)	C14—C15—H15	119.4
O7—P2—O10	114.93 (16)	C15—C16—C17	121.4 (3)
O8—P2—O10	107.47 (19)	C15—C16—H16	119.3
O7—P2—O9	113.40 (18)	C17—C16—H16	119.3
O8—P2—O9	103.32 (18)	C21—C17—C18	116.5 (3)
O10—P2—O9	102.94 (17)	C21—C17—C16	119.8 (3)
C6—O8—P2	114.7 (2)	C18—C17—C16	123.7 (3)
C7—O9—P2	114.0 (2)	C19—C18—C17	119.1 (3)
C8—O10—P2	114.0 (2)	C19—C18—H18	120.5
O8—C6—C9	109.4 (3)	C17—C18—H18	120.5
O8—C6—H6A	109.8	C18—C19—C20	119.8 (3)
C9—C6—H6A	109.8	C18—C19—H19	120.1
O8—C6—H6B	109.8	C20—C19—H19	120.1
C9—C6—H6B	109.8	N2—C20—C19	123.7 (3)
H6A—C6—H6B	108.2	N2—C20—H20	118.1
O9—C7—C9	110.2 (3)	C19—C20—H20	118.1
O9—C7—H7A	109.6	N2—C21—C17	124.5 (3)
C9—C7—H7A	109.6	N2—C21—C22	117.4 (3)
O9—C7—H7B	109.6	C17—C21—C22	118.1 (3)
C9—C7—H7B	109.6	N1—C22—C14	119.5 (3)
H7A—C7—H7B	108.1	N1—C22—C21	119.3 (3)
O10—C8—C9	110.0 (3)	C14—C22—C21	121.2 (3)
O10—C8—H8A	109.7	H13A—O13—H13B	103.8

O1—P1—O2—C1	−176.9 (2)	O8—C6—C9—C7	−60.0 (5)
O3—P1—O2—C1	−51.0 (3)	O8—C6—C9—C10	−178.8 (4)
O4—P1—O2—C1	58.7 (3)	C8—C9—C10—O12'	32.4 (13)
O1—P1—O3—C2	−174.5 (2)	C7—C9—C10—O12'	150.7 (13)
O2—P1—O3—C2	59.3 (2)	C6—C9—C10—O12'	−91.0 (13)
O4—P1—O3—C2	−49.6 (2)	C8—C9—C10—O11	150.2 (7)
O1—P1—O4—C3	−177.4 (2)	C7—C9—C10—O11	−91.5 (7)
O3—P1—O4—C3	57.0 (2)	C6—C9—C10—O11	26.8 (7)
O2—P1—O4—C3	−52.3 (2)	C8—C9—C10—O11'	−173.8 (10)
P1—O2—C1—C4	−6.5 (4)	C7—C9—C10—O11'	−55.5 (10)
P1—O3—C2—C4	−7.5 (3)	C6—C9—C10—O11'	62.8 (10)
P1—O4—C3—C4	−4.5 (3)	C8—C9—C10—O12	−37.3 (8)
O2—C1—C4—C3	−55.4 (3)	C7—C9—C10—O12	81.0 (8)
O2—C1—C4—C2	62.7 (3)	C6—C9—C10—O12	−160.7 (8)
O2—C1—C4—C5	−176.4 (3)	C22—N1—C11—C12	−1.3 (5)
O4—C3—C4—C1	61.9 (3)	N1—C11—C12—C13	0.9 (5)
O4—C3—C4—C2	−57.0 (3)	C11—C12—C13—C14	0.2 (5)
O4—C3—C4—C5	−176.9 (3)	C12—C13—C14—C22	−0.8 (5)
O3—C2—C4—C1	−54.9 (3)	C12—C13—C14—C15	179.9 (3)
O3—C2—C4—C3	64.1 (3)	C22—C14—C15—C16	0.4 (5)
O3—C2—C4—C5	−176.1 (2)	C13—C14—C15—C16	179.7 (3)
C1—C4—C5—O5	12.0 (4)	C14—C15—C16—C17	0.0 (5)
C3—C4—C5—O5	−108.7 (3)	C15—C16—C17—C21	−0.4 (5)
C2—C4—C5—O5	132.6 (3)	C15—C16—C17—C18	−178.7 (3)
C1—C4—C5—O6	−168.5 (3)	C21—C17—C18—C19	0.4 (4)
C3—C4—C5—O6	70.9 (3)	C16—C17—C18—C19	178.7 (3)
C2—C4—C5—O6	−47.9 (4)	C17—C18—C19—C20	0.0 (5)
O7—P2—O8—C6	178.7 (3)	C21—N2—C20—C19	0.0 (5)
O10—P2—O8—C6	−53.0 (4)	C18—C19—C20—N2	−0.3 (5)
O9—P2—O8—C6	55.4 (4)	C20—N2—C21—C17	0.5 (4)
O7—P2—O9—C7	−180.0 (3)	C20—N2—C21—C22	−179.0 (3)
O8—P2—O9—C7	−56.5 (3)	C18—C17—C21—N2	−0.7 (4)
O10—P2—O9—C7	55.2 (3)	C16—C17—C21—N2	−179.1 (3)
O7—P2—O10—C8	179.0 (3)	C18—C17—C21—C22	178.8 (3)
O8—P2—O10—C8	51.5 (3)	C16—C17—C21—C22	0.4 (4)
O9—P2—O10—C8	−57.2 (3)	C11—N1—C22—C14	0.6 (4)
P2—O8—C6—C9	0.3 (5)	C11—N1—C22—C21	−179.2 (3)
P2—O9—C7—C9	1.1 (4)	C13—C14—C22—N1	0.5 (4)
P2—O10—C8—C9	2.4 (5)	C15—C14—C22—N1	179.8 (3)
O10—C8—C9—C7	58.6 (4)	C13—C14—C22—C21	−179.7 (3)
O10—C8—C9—C6	−59.2 (5)	C15—C14—C22—C21	−0.4 (4)
O10—C8—C9—C10	177.4 (3)	N2—C21—C22—N1	−0.7 (4)
O9—C7—C9—C8	−60.6 (4)	C17—C21—C22—N1	179.8 (3)
O9—C7—C9—C6	59.0 (4)	N2—C21—C22—C14	179.5 (3)
O9—C7—C9—C10	179.2 (3)	C17—C21—C22—C14	0.0 (4)
O8—C6—C9—C8	57.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13B···O12ⁱ	0.84	2.47	2.893 (9)	112
N1—H1···O1ⁱⁱ	0.90	1.91	2.765 (3)	159
O6—H6C···O11ⁱ	0.85	1.61	2.459 (5)	173

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₅H₆O₆P⁻·C₅H₇O₆P·H₂O
M_r	586.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	9.2841 (18), 8.5863 (16), 31.124 (6)
β (°)	99.917 (5)
V (Å³)	2444.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.948, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	13684, 5008, 2956
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.159, 1.03
No. of reflections	5008
No. of parameters	371
No. of restraints	38
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.32

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13B···O12ⁱ	0.84	2.47	2.893 (9)	112.4
N1—H1···O1ⁱⁱ	0.90	1.91	2.765 (3)	158.6
O6—H6C···O11ⁱ	0.85	1.61	2.459 (5)	173.1

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, −y+1, −z+2.

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