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In hexakis(m-toluidinium) cyclo­hexaphosphate, 6C7H10N+·­P6O186-, the atomic arrangement is typical of a layer structure. Layers including the centrosymmetric P6O18 ring anions develop around the (100) planes at x = {1 \over 2}. The hydrogen-bond distribution is described.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199015280/gs1058sup1.cif
Contains datablocks global, I

sft

Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108270199015280/gs1058Isup2.sft
Supplementary material

CCDC reference: 143257

Comment top

The title compound, (I), has been isolated as part of an investigation into salts formed between toluidine and cyclohexaphosphoric acid. According to the relative position of the methyl group with respect to the amine function, we can separate three phases with different crystal structures. Two of these have already been studied: (o-CH3C6H4NH3)6P6O18·2H2O (Laarafa et al., 1997) and (p-CH3C6H4NH3)6P6O18·8H2O (Ben Nasr & Rzaigui, 1999). We report in this contribution the crystal structure of m-toluidine and cyclohexaphosphoric acid salt. \sch

The main geometrical features such as intramolecular bond distances and angles are reported in Table 1. A view of the asymmetric unit is shown in Fig. 1. The atomic arrangement is typical of a layer structure. Layers including the P6O18 ring anions develop around the (100) planes at x = 1/2. Between these layers, separated by a distance of 14.622 (3) Å, organic cations establish hydrogen bonds (Table 2) to interconnect the different P6O18 anions (Fig. 2). The N(1)H3 groups perform the internal P6O18 ring cohesion through hydrogen bonds involving external oxygen atoms of each PO4 tetrahedron. The two other groups, N(2)H3 and N(3)H3, are linked to three different P6O18 rings and so contribute to the intralayer cohesion of this compound. Inside such a layer, the phosphoric ring develops around the inversion centre located at (1/2, 0, 1/2) and thus presents a -1 internal symmetry. The main geometrical features of this ring are reported in Table 1. This atomic arrangement is the third type of structure obtained with toluidine and cyclohexaphosphoric acid in aqueous solution. It is worth noticing that according to the relative position of the methyl group on the phenyl ring the toluidine cyclohexaphosphate crystallizes with different degrees of hydration: the meta isomer gives an anhydrous compound, whereas the ortho and para isomers lead to di- and octahydrate salts respectively, giving additional hydrogen bonds inside the anionic layers.

Experimental top

The title compound was prepared according to the following reaction: H6P6O18 + 6(m-CH3C6H4NH2) ——> (m-CH3C6H4NH3)6P6O18. An aqueous solution of cyclohexaphosphoric acid was first obtained by passing a solution of Li6P6O18 through an ion-exchange resin in its H-state (Amberlite IR 120). The lithium salt was prepared according to the process described by Schulke & Kayser (1985), using "purum p.a. Fluka chemical reagents". This solution was then added drop by drop to distilled p-toluidine (purum p.a. Fluka) under continuous stirring until the solution exhibited a light greenish aspect. The so-obtained solution was slowly evaporated until the formation of large prismatic crystals of (m-CH3C6H4NH3)6P6O18.

Refinement top

All H atoms were found by difference Fourier synthesis and fixed at their positions with common isotropic displacement parameters (Uiso = 0.08 Å2).

Computing details top

Data collection: CAD4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD4 Operations Manual (Enraf-Nonius, 1977); data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN for Windows; molecular graphics: MOLVIEW (Cense, 1990); software used to prepare material for publication: TEXSAN for Windows.

Figures top
[Figure 1] Fig. 1. Labelled drawing of the asymmetric unities. Displacement ellipsoids are plotted at the 50% probability level.
[Figure 2] Fig. 2. The atomic arrangement of (I) in projection along the c axis. The phosphoric anion is given in a tetrahedral representation. All constituents of the organic molecules are represented: the small empty circles are H atoms, the larger empty ones are C atoms and the hatched circles represent N atoms.
(I) top
Crystal data top
6C7H10N+·O18P66Z = 1
Mr = 1122.81F(000) = 588.00
Triclinic, P1Dx = 1.408 Mg m3
a = 14.622 (3) ÅMo Kα radiation, λ = 0.7107 Å
b = 10.656 (4) ÅCell parameters from 25 reflections
c = 9.216 (4) Åθ = 10.0–13.0°
α = 112.72 (3)°µ = 0.28 mm1
β = 91.29 (3)°T = 296 K
γ = 89.68 (3)°Prism, colourless
V = 1324.2 (8) Å30.40 × 0.29 × 0.16 mm
Data collection top
CAD4
diffractometer
Rint = 0.019
Radiation source: X-ray tubeθmax = 25.0°, θmin = 3.5°
Graphite monochromatorh = 1717
ω–2θ scansk = 1212
9286 measured reflectionsl = 1010
4643 independent reflections2 standard reflections every 400 reflections
3185 reflections with I > 3.00σ(I) intensity decay: 4.2%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.035H-atom parameters not refined
wR(F2) = 0.050Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00123|Fo|2]
S = 1.28(Δ/σ)max = 0.040
3185 reflectionsΔρmax = 0.33 e Å3
325 parametersΔρmin = 0.45 e Å3
Crystal data top
6C7H10N+·O18P66γ = 89.68 (3)°
Mr = 1122.81V = 1324.2 (8) Å3
Triclinic, P1Z = 1
a = 14.622 (3) ÅMo Kα radiation
b = 10.656 (4) ŵ = 0.28 mm1
c = 9.216 (4) ÅT = 296 K
α = 112.72 (3)°0.40 × 0.29 × 0.16 mm
β = 91.29 (3)°
Data collection top
CAD4
diffractometer
Rint = 0.019
9286 measured reflections2 standard reflections every 400 reflections
4643 independent reflections intensity decay: 4.2%
3185 reflections with I > 3.00σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.050H-atom parameters not refined
S = 1.28Δρmax = 0.33 e Å3
3185 reflectionsΔρmin = 0.45 e Å3
325 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.52332 (4)0.72456 (5)0.30379 (6)0.0273 (2)
P20.54036 (4)0.82818 (5)0.64975 (7)0.0269 (2)
P30.61895 (4)1.10173 (5)0.74688 (7)0.0291 (2)
O10.50612 (11)0.5785 (2)0.2584 (2)0.0442 (5)
O20.58288 (12)0.7653 (2)0.2020 (2)0.0394 (5)
O30.57042 (11)0.7855 (2)0.4725 (2)0.0464 (5)
O40.44352 (11)0.7892 (2)0.6536 (2)0.0359 (4)
O50.61148 (12)0.7810 (2)0.7298 (2)0.0515 (6)
O60.54059 (11)0.9880 (2)0.7084 (2)0.0435 (5)
O70.70021 (11)1.0452 (2)0.6536 (2)0.0397 (5)
O80.57060 (11)1.1972 (2)0.6686 (2)0.0398 (5)
O90.6257 (1)1.1730 (2)0.9164 (2)0.0598 (6)
N10.32595 (13)0.9947 (2)0.6556 (2)0.0354 (5)
N20.63273 (12)0.3671 (2)0.2048 (2)0.0315 (5)
N30.37931 (12)0.3783 (2)0.1084 (2)0.0311 (5)
C10.2498 (2)1.0170 (2)0.7615 (3)0.0313 (6)
C20.1644 (2)1.0410 (2)0.7135 (3)0.0386 (7)
C30.0917 (2)1.0685 (3)0.8174 (3)0.0452 (7)
C40.1095 (2)1.0705 (3)0.9656 (4)0.0517 (8)
C50.1953 (2)1.0455 (3)1.0120 (3)0.0496 (8)
C60.2669 (2)1.0179 (3)0.9090 (3)0.0411 (7)
C70.0017 (2)1.0934 (4)0.7665 (5)0.0759 (12)
C80.7265 (2)0.4120 (2)0.2555 (3)0.0314 (6)
C90.7414 (2)0.5292 (2)0.3861 (3)0.0393 (7)
C100.8294 (2)0.5739 (3)0.4361 (3)0.0481 (8)
C110.9016 (2)0.4964 (4)0.3515 (4)0.0604 (9)
C120.8856 (2)0.3796 (4)0.2214 (4)0.0639 (10)
C130.7973 (2)0.3358 (3)0.1705 (3)0.0476 (7)
C140.8456 (3)0.7027 (4)0.5785 (4)0.0777 (11)
C150.2881 (1)0.4366 (2)0.1237 (3)0.0285 (6)
C160.2668 (2)0.5439 (2)0.2594 (3)0.0348 (6)
C170.1808 (2)0.5993 (3)0.2792 (3)0.0408 (7)
C180.1162 (2)0.5425 (3)0.1599 (4)0.0532 (8)
C190.1380 (2)0.4346 (3)0.0240 (4)0.0586 (9)
C200.2246 (2)0.3804 (3)0.0038 (3)0.0454 (7)
C210.1585 (2)0.7199 (3)0.4262 (4)0.0583 (9)
H10.36471.06360.69180.080*
H20.35990.92910.65010.080*
H30.30550.98230.55660.080*
H40.32291.00270.93800.080*
H50.20401.04711.11320.080*
H60.05901.09341.04320.080*
H70.15601.04400.60980.080*
H80.04351.13070.84030.080*
H90.02881.00700.72720.080*
H100.00081.13070.70430.080*
H110.62750.30850.09860.080*
H120.59260.43890.22260.080*
H130.60760.31940.25480.080*
H140.78520.25580.08320.080*
H150.93380.32520.15720.080*
H160.96290.52410.38200.080*
H170.68630.58070.43910.080*
H180.90340.73020.57820.080*
H190.85620.68490.64510.080*
H200.80030.76630.59440.080*
H210.38290.32390.15560.080*
H220.42010.45160.15980.080*
H230.38960.33100.00060.080*
H240.23960.31090.09280.080*
H250.09460.39780.06740.080*
H260.05310.57630.17660.080*
H270.30910.58400.33650.080*
H280.20110.72560.51720.080*
H290.17180.80550.41290.080*
H300.09740.72410.45110.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0340 (3)0.0208 (3)0.0253 (3)0.0005 (2)0.0028 (2)0.0068 (2)
P20.0343 (3)0.0223 (3)0.0260 (3)0.0015 (2)0.0024 (2)0.0112 (2)
P30.0379 (3)0.0244 (3)0.0238 (3)0.0015 (2)0.0024 (2)0.0081 (2)
O10.0412 (9)0.0216 (8)0.0642 (12)0.0027 (7)0.0055 (8)0.0107 (8)
O20.0496 (10)0.0351 (9)0.0327 (9)0.0032 (7)0.0149 (8)0.0115 (7)
O30.0389 (9)0.0648 (12)0.0255 (9)0.0132 (8)0.0028 (7)0.0063 (8)
O40.0376 (9)0.0346 (9)0.0399 (9)0.0021 (7)0.0077 (7)0.0189 (7)
O50.0498 (11)0.0601 (12)0.0638 (13)0.0076 (9)0.0028 (9)0.0453 (11)
O60.0387 (9)0.0233 (8)0.0641 (12)0.0013 (7)0.0058 (8)0.0117 (8)
O70.0354 (9)0.0388 (9)0.0456 (10)0.0047 (7)0.0000 (7)0.0170 (8)
O80.0445 (10)0.0419 (10)0.0438 (10)0.0127 (8)0.0162 (8)0.0279 (8)
O90.079 (1)0.0635 (13)0.0260 (10)0.0061 (11)0.0079 (9)0.0054 (9)
N10.0364 (11)0.0328 (10)0.0352 (11)0.0036 (8)0.0060 (9)0.0108 (9)
N20.0350 (10)0.0282 (9)0.0321 (10)0.0030 (8)0.0017 (8)0.0127 (8)
N30.0331 (10)0.0301 (10)0.0314 (10)0.0010 (8)0.0003 (8)0.0134 (8)
C10.0332 (12)0.0257 (11)0.0327 (12)0.0010 (9)0.0046 (9)0.0084 (9)
C20.0408 (13)0.0333 (12)0.0362 (13)0.0010 (10)0.0001 (11)0.0074 (10)
C30.0360 (13)0.0364 (13)0.056 (2)0.0009 (10)0.0039 (12)0.0092 (12)
C40.052 (2)0.049 (2)0.051 (2)0.0013 (13)0.0185 (13)0.0147 (13)
C50.062 (2)0.051 (2)0.036 (1)0.0010 (13)0.0100 (13)0.0165 (12)
C60.045 (1)0.042 (1)0.036 (1)0.0028 (11)0.0033 (11)0.0160 (11)
C70.045 (2)0.088 (3)0.094 (3)0.007 (2)0.002 (2)0.034 (2)
C80.0329 (12)0.0307 (11)0.0325 (12)0.0020 (9)0.0001 (9)0.0144 (10)
C90.042 (1)0.0332 (12)0.039 (1)0.0005 (10)0.0001 (11)0.0101 (11)
C100.048 (2)0.046 (2)0.046 (2)0.0124 (12)0.0064 (12)0.0129 (12)
C110.040 (2)0.075 (2)0.061 (2)0.013 (1)0.0033 (13)0.020 (2)
C120.039 (2)0.074 (2)0.067 (2)0.006 (1)0.009 (1)0.013 (2)
C130.046 (2)0.046 (2)0.043 (2)0.0032 (12)0.0074 (12)0.0070 (12)
C140.076 (2)0.064 (2)0.069 (2)0.018 (2)0.023 (2)0.001 (2)
C150.0320 (12)0.0239 (10)0.0315 (12)0.0019 (9)0.0016 (9)0.0130 (9)
C160.0377 (13)0.0328 (12)0.0318 (12)0.0042 (10)0.0028 (10)0.0102 (10)
C170.041 (1)0.0338 (12)0.046 (2)0.0025 (10)0.0058 (11)0.0135 (11)
C180.036 (1)0.044 (2)0.074 (2)0.0077 (12)0.0049 (13)0.018 (2)
C190.045 (2)0.052 (2)0.065 (2)0.0004 (13)0.024 (1)0.009 (2)
C200.050 (2)0.0329 (13)0.044 (2)0.0021 (11)0.0133 (12)0.0051 (11)
C210.059 (2)0.045 (2)0.057 (2)0.0100 (13)0.012 (1)0.004 (1)
Geometric parameters (Å, º) top
P1—O11.469 (2)C4—C51.375 (5)
P1—O21.477 (2)C4—H52.00
P1—O31.578 (2)C4—H61.00
P1—O8i1.577 (2)C5—C61.383 (4)
P2—O31.589 (2)C5—H41.99
P2—O41.483 (2)C5—H50.93
P2—O51.458 (2)C6—H40.89
P2—O61.576 (2)C7—H80.89
P3—O61.604 (2)C7—H90.94
P3—O71.467 (2)C7—H100.81
P3—O81.609 (2)C8—C91.373 (4)
P3—O91.451 (2)C8—C131.371 (4)
O1—H121.88C9—C101.380 (4)
O1—H221.80C9—H171.00
O2—H11.86C10—C111.390 (5)
O2—H231.80C10—C141.504 (5)
O4—H21.93C10—H181.98
O4—H131.84C10—H191.86
O5—H211.81C11—C121.371 (5)
O7—H31.84C11—H160.95
O9—H111.74C12—C131.384 (5)
N1—C11.454 (3)C12—H150.97
N1—H10.88C13—H140.93
N1—H20.84C14—H180.90
N1—H30.91C14—H190.72
N2—C81.461 (3)C14—H200.92
N2—H110.94C15—C161.370 (4)
N2—H120.93C15—C201.375 (4)
N2—H130.89C15—H211.92
N3—C151.455 (3)C15—H221.95
N3—H210.85C15—H231.96
N3—H220.95C16—C171.372 (4)
N3—H230.94C16—H270.91
C1—C21.371 (4)C17—C181.383 (4)
C1—C61.372 (4)C17—C211.505 (4)
C1—H11.95C17—H271.96
C1—H21.96C18—C191.376 (5)
C1—H31.97C18—H260.98
C1—H41.98C19—C201.375 (4)
C2—C31.400 (4)C19—H251.00
C2—H70.97C20—H240.94
C3—C41.377 (5)C21—H281.02
C3—C71.489 (4)C21—H290.99
C3—H91.94C21—H300.92
C3—H101.95
O1···N32.748 (3)O4···N12.771 (3)
O1···N22.807 (3)O5···N3iii2.657 (3)
O2···N1i2.721 (3)O7···N1i2.733 (3)
O2···N3ii2.741 (3)O9···N2iv2.664 (3)
O4···N2iii2.735 (3)
O1—P1—O2117.50 (12)C5—C4—H524.1
O1—P1—O3109.84 (13)C5—C4—H6118.8
O1—P1—O8i109.48 (11)H5—C4—H694.7
O2—P1—O3105.23 (11)C4—C5—C6120.0 (3)
O2—P1—O8i111.29 (10)C4—C5—H4142.5
O3—P1—O8i102.33 (11)C4—C5—H5118.9
O3—P2—O4109.77 (11)C6—C5—H422.5
O3—P2—O5107.09 (12)C6—C5—H5121.1
O3—P2—O6101.21 (12)H4—C5—H598.6
O4—P2—O5120.20 (11)C1—C6—C5118.3 (3)
O4—P2—O6105.54 (10)C1—C6—H4120.8
O5—P2—O6111.40 (13)C5—C6—H4120.9
O6—P3—O7110.61 (11)C3—C7—H8118.4
O6—P3—O898.70 (11)C3—C7—H9103.6
O6—P3—O9107.92 (13)C3—C7—H10112.6
O7—P3—O8105.95 (11)H8—C7—H994.7
O7—P3—O9121.22 (13)H8—C7—H10111.5
O8—P3—O9110.11 (13)H9—C7—H10114.6
P1—O1—H12127.9N2—C8—C9119.3 (2)
P1—O1—H22140.1N2—C8—C13118.8 (2)
H12—O1—H2289.3C9—C8—C13121.9 (3)
P1—O2—H1112.3C8—C9—C10120.3 (3)
P1—O2—H23128.0C8—C9—H17117.0
H1i—O2i—H23i119.7C10—C9—H17122.6
P1—O3—P2137.20 (13)C9—C10—C11118.1 (3)
P2—O4—H2112.1C9—C10—C14120.3 (3)
P2—O4—H13130.0C9—C10—H18144.1
H2—O4—H13111.6C9—C10—H19121.4
P2—O5—H21136.6C11—C10—C14121.6 (3)
P2—O6—P3134.46 (12)C11—C10—H1897.1
P3—O7—H3117.3C11—C10—H19115.8
P1i—O8—P3133.27 (12)C14—C10—H1825.3
P3—O9—H11158.8C14—C10—H1921.5
C1—N1—H1110.3H18—C10—H1934.9
C1—N1—H2114.5C10—C11—C12120.9 (3)
C1—N1—H3110.8C10—C11—H16120.5
H1—N1—H2101.5C12—C11—H16118.6
H1—N1—H3110.5C11—C12—C13120.9 (3)
H2—N1—H3108.8C11—C12—H15123.3
C8—N2—H11113.3C13—C12—H15115.8
C8—N2—H12112.7C8—C13—C12117.9 (3)
C8—N2—H13114.5C8—C13—H14120.0
H11—N2—H12108.5C12—C13—H14122.0
H11—N2—H13103.3C10—C14—H18108.8
H12—N2—H13103.6C10—C14—H19108.6
C15—N3—H21110.1C10—C14—H20113.9
C15—N3—H22106.5H18—C14—H1990.7
C15—N3—H23107.6H18—C14—H20117.4
H21—N3—H22108.1H19—C14—H20115.1
H21—N3—H23109.9N3—C15—C16119.1 (2)
H22—N3—H23114.6N3—C15—C20119.3 (2)
N1—C1—C2119.3 (2)N3—C15—H2124.5
N1—C1—C6118.4 (2)N3—C15—H2227.8
N1—C1—H125.2N3—C15—H2327.3
N1—C1—H223.0C16—C15—C20121.6 (2)
N1—C1—H325.6C16—C15—H21112.6
N1—C1—H495.8C16—C15—H2295.7
C2—C1—C6122.2 (2)C16—C15—H23143.8
C2—C1—H1125.3C20—C15—H21119.4
C2—C1—H2133.8C20—C15—H22140.3
C2—C1—H394.1C20—C15—H2393.8
C2—C1—H4144.9H21—C15—H2244.2
C6—C1—H1106.4H21—C15—H2344.4
C6—C1—H2101.8H22—C15—H2348.0
C6—C1—H3143.6C15—C16—C17120.6 (3)
C6—C1—H422.7C15—C16—H27121.9
H1—C1—H240.0C17—C16—H27117.4
H1—C1—H344.2C16—C17—C18118.2 (3)
H1—C1—H485.8C16—C17—C21120.5 (3)
H2—C1—H342.6C16—C17—H2724.2
H2—C1—H479.9C18—C17—C21121.3 (3)
H3—C1—H4121.0C18—C17—H27142.4
C1—C2—C3119.6 (3)C21—C17—H2796.3
C1—C2—H7119.4C17—C18—C19120.9 (3)
C3—C2—H7120.9C17—C18—H26118.8
C2—C3—C4117.9 (3)C19—C18—H26120.2
C2—C3—C7120.2 (3)C18—C19—C20120.7 (3)
C2—C3—H9117.2C18—C19—H25122.2
C2—C3—H10100.6C20—C19—H25116.8
C4—C3—C7121.8 (3)C15—C20—C19118.0 (3)
C4—C3—H9116.7C15—C20—H24122.3
C4—C3—H10139.8C19—C20—H24119.6
C7—C3—H928.0C17—C21—H28111.2
C7—C3—H1022.6C17—C21—H29110.5
H9—C3—H1044.6C17—C21—H30113.1
C3—C4—C5122.0 (3)H28—C21—H29102.5
C3—C4—H5146.0H28—C21—H30113.1
C3—C4—H6119.3H29—C21—H30105.8
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.881.862.721 (3)164
N1—H2···O40.881.932.771 (3)175
N1—H3···O7i0.911.842.733 (3)164
N2—H11···O9v0.941.742.664 (3)168
N2—H12···O10.931.882.807 (3)177
N2—H13···O4iii0.891.842.735 (3)176
N3—H21···O5iii0.851.812.657 (3)176
N3—H22···O10.951.802.748 (3)174
N3—H23···O2ii0.941.802.741 (3)176
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z; (iii) x+1, y+1, z+1; (v) x, y1, z1.

Experimental details

Crystal data
Chemical formula6C7H10N+·O18P66
Mr1122.81
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)14.622 (3), 10.656 (4), 9.216 (4)
α, β, γ (°)112.72 (3), 91.29 (3), 89.68 (3)
V3)1324.2 (8)
Z1
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.40 × 0.29 × 0.16
Data collection
DiffractometerCAD4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 3.00σ(I)] reflections
9286, 4643, 3185
Rint0.019
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.050, 1.28
No. of reflections3185
No. of parameters325
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.33, 0.45

Computer programs: CAD4 Operations Manual (Enraf-Nonius, 1977), TEXSAN for Windows (Molecular Structure Corporation, 1997), SIR92 (Altomare et al., 1993), TEXSAN for Windows, MOLVIEW (Cense, 1990).

Selected geometric parameters (Å, º) top
P1—O11.469 (2)C3—C41.377 (5)
P1—O21.477 (2)C3—C71.489 (4)
P1—O31.578 (2)C4—C51.375 (5)
P1—O8i1.577 (2)C5—C61.383 (4)
P2—O31.589 (2)C8—C91.373 (4)
P2—O41.483 (2)C8—C131.371 (4)
P2—O51.458 (2)C9—C101.380 (4)
P2—O61.576 (2)C10—C111.390 (5)
P3—O61.604 (2)C10—C141.504 (5)
P3—O71.467 (2)C11—C121.371 (5)
P3—O81.609 (2)C12—C131.384 (5)
P3—O91.451 (2)C15—C161.370 (4)
N1—C11.454 (3)C15—C201.375 (4)
N2—C81.461 (3)C16—C171.372 (4)
N3—C151.455 (3)C17—C181.383 (4)
C1—C21.371 (4)C17—C211.505 (4)
C1—C61.372 (4)C18—C191.376 (5)
C2—C31.400 (4)C19—C201.375 (4)
O1—P1—O2117.50 (12)O5—P2—O6111.40 (13)
O1—P1—O3109.84 (13)O6—P3—O7110.61 (11)
O1—P1—O8i109.48 (11)O6—P3—O898.70 (11)
O2—P1—O3105.23 (11)O6—P3—O9107.92 (13)
O2—P1—O8i111.29 (10)O7—P3—O8105.95 (11)
O3—P1—O8i102.33 (11)O7—P3—O9121.22 (13)
O3—P2—O4109.77 (11)O8—P3—O9110.11 (13)
O3—P2—O5107.09 (12)P1—O3—P2137.20 (13)
O3—P2—O6101.21 (12)P2—O6—P3134.46 (12)
O4—P2—O5120.20 (11)P1i—O8—P3133.27 (12)
O4—P2—O6105.54 (10)
Symmetry code: (i) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.881.862.721 (3)164
N1—H2···O40.881.932.771 (3)175
N1—H3···O7i0.911.842.733 (3)164
N2—H11···O9ii0.941.742.664 (3)168
N2—H12···O10.931.882.807 (3)177
N2—H13···O4iii0.891.842.735 (3)176
N3—H21···O5iii0.851.812.657 (3)176
N3—H22···O10.951.802.748 (3)174
N3—H23···O2iv0.941.802.741 (3)176
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y1, z1; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z.
 

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