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The structure of the title compound, [HN(C2H4OH)3]+·H2PO4 or C6H16NO3+·H2PO4, contains two distinct di­hydrogenphosphate anions and two triethano­l­ammonium cations in the asymmetric unit. The H2PO4 units are linked in a polymeric chain by strong P—OH...O—P hydrogen bonds along the [010] direction, while the (H2PO4) and [HN(C2H4OH)3]+ ions are connected by O—H...O hydrogen bonds to yield sheet-like entities. The triethano­lammonium cation shows a tripodal conformation and the ammonium H atom forms an intramolecular trifurcated hydrogen bond with the O atoms of the three ethanol groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011188/cv6195sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011188/cv6195Isup2.hkl
Contains datablock I

CCDC reference: 217435

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 96%
  • R factor = 0.037
  • wR factor = 0.084
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C6 H18 N1 O7 P1 Atom count from the _atom_site data: C6 H17.187 N1 O7 P1 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C6 H18 N O7 P TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 24.00 24.00 0.00 H 72.00 68.75 3.25 N 4.00 4.00 0.00 O 28.00 28.00 0.00 P 4.00 4.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional? REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.08 From the CIF: _reflns_number_total 4714 Count of symmetry unique reflns 3496 Completeness (_total/calc) 134.84% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1218 Fraction of Friedel pairs measured 0.348 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure

Comment top

Open-framework metal phosphates are generally synthesized under hydrothermal conditions in the presence of amine. The main role of the amine is to behave as a structure-directing agent and also a ligand to metal. Simple amine phosphates formed in the preparation of metal phosphates act as intermediates and sometimes occur as unexpected stable side products (Oliver et al., 1998; Neeraj et al., 1999). In the present study, we report the structure of triethanolammonium dihydrogenphosphate, (I).

The structure of (I) composed of two distinct dihydrogenphosphate anions and two triethanolammonium cations (Fig. 1). The N2-centered triethanolammonium cation is partially disordered over two positions [major component atoms C7, C9 and C11 with occupancy = 0.729 (4) and dav(N—C) = 1.501 (3) Å; minor component atoms C7a, C9a and C11a with occupancy = 0.271 (4) and dav(N—C) = 1.495 (9) Å]. The triethanolammonium cation exibits a tripodal conformation, in which the ammonium H atom forms an intramolecular trifurcated hydrogen bond with the O atoms of the three ethanol groups. Similar trifurcated intramolecular hydrogen bonds were observed in triethanolammonium bromide (Yilmaz et al., 1996). The bond geometry within the cation is comparable to those of other triethanolammonium salts with bromide (Yilmaz et al., 1996), hexachloroplatinate (Yilmaz et al., 1997), chloride and hydrogensulfide (Mootz et al., 1990).

The crystal structure contains an extensive network of O—H···O hydrogen bonds. The H2PO4 units are linked in a polymeric chain by triple hydrogen bonds involving the OH and P=O groups along the [010] direction (Fig. 2). The (H2PO4) and [HN(C2H4OH)3]+ ions are also connected by O—H···O hydrogen bonds to yield sheet-like entities (Fig. 3). Within the sheet the H2PO4 anions are hydrogen bonded in pairs and bridged by the O—HT···OP (T = triethanolammonium, P = phosphate) type hydrogen bonds involving the ammonium ions. There is no hydrogen bonding between the neighboring sheets, which are held together by van der Waals interactions.

Experimental top

1.153 ml H3PO4 (17 mmol) (aqueous 85% wt) was added dropwise to a solution of triethanolamine (1.33 ml, 10 mmol) in 20 ml me thanol and stirred for 30 min at the room temperature. The resulting solution was kept at 343 K for a day. X-ray quality crystals were formed when the solution was cooled to room temperature. Colourless transparent crystals of the title compound were washed with metanol and dried in air.

Refinement top

Water, hydroxyl and amine H atoms were found in difference maps and were refined by riding in their as-found positions. H atoms bonded to C atoms were placed in calculated positions 0.97 Å from their parent atoms and modelled by riding.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ATOMS (Shape Software, 1999); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of (I) (50% displacement ellipsoids). H atoms are drawn as small spheres of arbitrary radii and H bonds are indicated by dashed lines. Only the major orientation (atoms C7, C9 and C11) of the N2-centred molecule is shown; all C—H H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Details of the dihydrogen phosphate chain in (I), with hydrogen bonds indicated by dashed lines. Note how the P1 and P2 moieties are linked by alternating double and single hydrogen bonds. The symmetry codes are as in Table 2.
[Figure 3] Fig. 3. [010] projection of (I), showing the sheet-like arrangement of [HN(C2H4OH)3]+ and (H2PO4) groups. Colour key: [H2PO4] tetrahedra yellow, O atoms red, C atoms blue, N atoms purple, H atoms grey. The H···O portions of the hydrogen bonds are highlighted in green. C—H hydrogen atoms have been omitted for clarity.
Triethanolammonium dihydrogenphosphate top
Crystal data top
C6H16NO3+·H2PO4F(000) = 528
Mr = 247.18Dx = 1.507 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 14.1354 (7) ÅCell parameters from 3525 reflections
b = 5.5364 (3) Åθ = 2.6–28.1°
c = 15.5323 (7) ŵ = 0.27 mm1
β = 116.354 (1)°T = 293 K
V = 1089.21 (9) Å3Blade, colourless
Z = 40.45 × 0.12 × 0.04 mm
Data collection top
Bruker SMART1000 CCD
diffractometer
4714 independent reflections
Radiation source: fine-focus sealed tube3779 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 30.1°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1919
Tmin = 0.885, Tmax = 0.989k = 57
9297 measured reflectionsl = 2121
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom (C-H) and difmap (O-H and N-H)
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0442P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
4714 reflectionsΔρmax = 0.27 e Å3
284 parametersΔρmin = 0.28 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.18 (8)
Crystal data top
C6H16NO3+·H2PO4V = 1089.21 (9) Å3
Mr = 247.18Z = 4
Monoclinic, P21Mo Kα radiation
a = 14.1354 (7) ŵ = 0.27 mm1
b = 5.5364 (3) ÅT = 293 K
c = 15.5323 (7) Å0.45 × 0.12 × 0.04 mm
β = 116.354 (1)°
Data collection top
Bruker SMART1000 CCD
diffractometer
4714 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
3779 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.989Rint = 0.025
9297 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.084Δρmax = 0.27 e Å3
S = 0.98Δρmin = 0.28 e Å3
4714 reflectionsAbsolute structure: Flack (1983)
284 parametersAbsolute structure parameter: 0.18 (8)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.31964 (4)0.61894 (11)0.19862 (4)0.02914 (14)
O10.39078 (13)0.6776 (4)0.15381 (12)0.0444 (5)
O20.20379 (12)0.6632 (3)0.13789 (11)0.0361 (4)
O30.34045 (13)0.3471 (3)0.22959 (13)0.0435 (4)
H10.30510.28880.25480.052*
O40.35691 (12)0.7616 (4)0.29626 (11)0.0392 (4)
H20.31190.87840.28830.047*
P20.11319 (4)0.03585 (11)0.26504 (4)0.02875 (13)
O50.06599 (13)0.0792 (4)0.33259 (12)0.0462 (5)
O60.22771 (11)0.1089 (3)0.30189 (11)0.0351 (4)
O70.09954 (13)0.2409 (3)0.23909 (12)0.0351 (4)
H30.13690.26330.21250.042*
O80.05059 (13)0.1729 (4)0.16759 (12)0.0430 (5)
H40.00440.10290.12740.052*
N10.31374 (13)0.5765 (4)0.57448 (12)0.0302 (4)
H50.30880.41600.58440.036*
C10.33789 (19)0.5967 (5)0.48965 (17)0.0372 (6)
H60.27270.59020.43060.045*
H70.37180.75030.49170.045*
C20.40896 (18)0.3947 (5)0.49126 (17)0.0366 (5)
H80.42170.40450.43490.044*
H90.47630.40910.54780.044*
C30.2107 (2)0.6867 (6)0.5578 (2)0.0464 (7)
H100.20920.85360.53830.056*
H110.20450.68560.61760.056*
C40.11798 (19)0.5546 (6)0.48212 (18)0.0455 (7)
H120.05290.61210.48160.055*
H130.11470.58410.41930.055*
C50.4043 (2)0.6722 (6)0.66384 (17)0.0476 (7)
H140.39740.84580.66720.057*
H150.47030.63920.66110.057*
C60.4060 (2)0.5565 (7)0.75234 (17)0.0532 (9)
H160.46820.60990.80850.064*
H170.34430.60720.75960.064*
O90.36237 (14)0.1699 (4)0.49249 (13)0.0452 (5)
H180.31210.15570.43200.054*
O100.12986 (14)0.3044 (4)0.50272 (13)0.0491 (5)
H190.10830.23540.44910.059*
O110.40698 (14)0.3044 (4)0.74634 (13)0.0499 (5)
H200.47500.26820.77710.060*
N20.77358 (13)0.6721 (4)0.09932 (13)0.0287 (4)
H210.79050.83180.10730.034*
C70.8556 (2)0.5487 (7)0.0803 (2)0.0346 (8)0.729 (4)
H220.83050.38850.05530.041*0.729 (4)
H230.91860.52960.14060.041*0.729 (4)
C7A0.7996 (7)0.5685 (18)0.0243 (7)0.035 (2)*0.271 (4)
C80.8844 (2)0.6789 (6)0.01109 (19)0.0449 (7)
H240.95180.61970.01740.054*
H250.83160.64720.05400.054*
C90.6647 (2)0.6513 (6)0.0138 (2)0.0326 (8)0.729 (4)
H260.67210.65830.04540.039*0.729 (4)
H270.63390.49640.01600.039*0.729 (4)
C9A0.6690 (6)0.6448 (18)0.0876 (6)0.033 (2)*0.271 (4)
C100.59535 (18)0.8423 (6)0.01397 (19)0.0445 (7)
H280.53050.83680.04540.053*
H290.57750.81760.06680.053*
C110.7711 (2)0.5870 (7)0.1893 (2)0.0385 (9)0.729 (4)
H300.77880.41270.19400.046*0.729 (4)
H310.70370.62810.18790.046*0.729 (4)
C11A0.8546 (7)0.569 (2)0.2008 (7)0.041 (2)*0.271 (4)
C120.8604 (2)0.7047 (7)0.27677 (19)0.0502 (8)
H320.85060.67380.33380.060*
H330.92760.63620.28670.060*
O120.89125 (13)0.9323 (4)0.02875 (12)0.0397 (4)
H340.85721.01700.01580.048*
O130.64238 (14)1.0691 (4)0.02313 (12)0.0433 (5)
H350.62601.10100.04110.052*
O140.86032 (14)0.9570 (4)0.26128 (14)0.0499 (5)
H360.92511.00070.29090.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0308 (3)0.0271 (3)0.0288 (3)0.0023 (3)0.0127 (2)0.0009 (3)
O10.0465 (9)0.0522 (13)0.0391 (9)0.0169 (9)0.0232 (8)0.0076 (9)
O20.0363 (8)0.0370 (11)0.0296 (8)0.0011 (8)0.0097 (6)0.0044 (7)
O30.0434 (9)0.0282 (11)0.0644 (12)0.0026 (8)0.0290 (9)0.0069 (9)
O40.0363 (8)0.0429 (12)0.0299 (8)0.0078 (8)0.0069 (7)0.0050 (8)
P20.0294 (2)0.0292 (3)0.0270 (3)0.0041 (3)0.0120 (2)0.0037 (3)
O50.0450 (9)0.0563 (14)0.0458 (9)0.0140 (9)0.0280 (8)0.0183 (9)
O60.0316 (7)0.0318 (9)0.0391 (8)0.0055 (8)0.0133 (6)0.0030 (8)
O70.0387 (9)0.0268 (10)0.0436 (9)0.0060 (8)0.0217 (7)0.0047 (8)
O80.0450 (9)0.0369 (12)0.0359 (9)0.0014 (9)0.0078 (7)0.0009 (8)
N10.0342 (9)0.0227 (11)0.0298 (9)0.0001 (8)0.0107 (7)0.0006 (8)
C10.0459 (12)0.0313 (14)0.0360 (11)0.0010 (12)0.0197 (10)0.0067 (11)
C20.0351 (11)0.0381 (14)0.0361 (12)0.0005 (12)0.0155 (10)0.0027 (11)
C30.0443 (14)0.0411 (16)0.0529 (15)0.0091 (13)0.0207 (12)0.0025 (13)
C40.0366 (12)0.055 (2)0.0421 (14)0.0069 (14)0.0150 (11)0.0013 (14)
C50.0457 (14)0.0424 (18)0.0405 (14)0.0076 (13)0.0062 (11)0.0119 (13)
C60.0467 (14)0.075 (3)0.0307 (13)0.0113 (17)0.0106 (11)0.0107 (15)
O90.0520 (10)0.0313 (11)0.0428 (9)0.0029 (9)0.0123 (8)0.0002 (8)
O100.0566 (11)0.0531 (14)0.0347 (9)0.0145 (11)0.0177 (8)0.0060 (9)
O110.0387 (9)0.0624 (15)0.0483 (11)0.0070 (10)0.0192 (8)0.0112 (11)
N20.0298 (8)0.0251 (11)0.0336 (9)0.0020 (8)0.0161 (7)0.0012 (8)
C70.0347 (15)0.0308 (18)0.0432 (18)0.0104 (15)0.0217 (14)0.0056 (15)
C80.0461 (14)0.0498 (19)0.0483 (15)0.0062 (14)0.0295 (12)0.0009 (14)
C90.0282 (14)0.0269 (19)0.0372 (17)0.0049 (14)0.0095 (12)0.0091 (14)
C100.0299 (11)0.057 (2)0.0416 (14)0.0006 (13)0.0110 (10)0.0043 (14)
C110.0373 (16)0.043 (2)0.0401 (17)0.0012 (17)0.0215 (14)0.0082 (17)
C120.0454 (15)0.071 (2)0.0329 (13)0.0002 (15)0.0159 (11)0.0083 (14)
O120.0391 (9)0.0427 (12)0.0300 (8)0.0048 (8)0.0088 (7)0.0087 (8)
O130.0526 (10)0.0373 (12)0.0380 (9)0.0044 (9)0.0184 (8)0.0018 (8)
O140.0377 (9)0.0608 (15)0.0508 (11)0.0054 (10)0.0193 (8)0.0100 (10)
Geometric parameters (Å, º) top
P1—O11.4907 (17)C6—H170.9700
P1—O21.5034 (16)O9—H180.8945
P1—O31.567 (2)O10—H190.8405
P1—O41.5787 (17)O11—H200.8856
O3—H10.8250N2—C9A1.414 (8)
O4—H20.8768N2—C71.484 (3)
P2—O51.4915 (16)N2—C7A1.484 (9)
P2—O61.5129 (15)N2—C111.491 (3)
P2—O81.5688 (18)N2—C91.527 (3)
P2—O71.5740 (17)N2—C11A1.587 (10)
O7—H30.8117N2—H210.9100
O8—H40.7768C7—C81.493 (4)
N1—C31.492 (3)C7—H220.9700
N1—C11.505 (3)C7—H230.9700
N1—C51.506 (3)C8—O121.425 (4)
N1—H50.9100C8—H240.9700
C1—C21.496 (4)C8—H250.9700
C1—H60.9700C9—C101.443 (4)
C1—H70.9700C9—H260.9700
C2—O91.412 (3)C9—H270.9700
C2—H80.9700C10—O131.398 (4)
C2—H90.9700C10—H280.9700
C3—C41.506 (4)C10—H290.9700
C3—H100.9700C11—C121.530 (4)
C3—H110.9700C11—H300.9700
C4—O101.414 (4)C11—H310.9700
C4—H120.9700C12—O141.418 (4)
C4—H130.9700C12—H320.9700
C5—C61.507 (4)C12—H330.9700
C5—H140.9700O12—H340.7968
C5—H150.9700O13—H350.9347
C6—O111.399 (4)O14—H360.8568
C6—H160.9700
O1—P1—O2116.37 (10)C4—O10—H19105.5
O1—P1—O3106.18 (11)C6—O11—H20103.3
O2—P1—O3110.66 (10)C9A—N2—C7142.1 (4)
O1—P1—O4109.45 (10)C9A—N2—C7A117.8 (5)
O2—P1—O4109.10 (9)C9A—N2—C1168.2 (4)
O3—P1—O4104.39 (10)C7—N2—C11112.8 (2)
P1—O3—H1116.8C7A—N2—C11137.0 (4)
P1—O4—H2108.7C7—N2—C9111.5 (2)
O5—P2—O6115.37 (9)C7A—N2—C978.1 (4)
O5—P2—O8111.35 (11)C11—N2—C9111.0 (2)
O6—P2—O8106.63 (10)C9A—N2—C11A110.0 (5)
O5—P2—O7107.12 (11)C7—N2—C11A75.4 (4)
O6—P2—O7110.24 (10)C7A—N2—C11A108.6 (5)
O8—P2—O7105.73 (10)C9—N2—C11A147.3 (4)
P2—O7—H3104.2C9A—N2—H21108.5
P2—O8—H4116.5C7—N2—H21107.1
C3—N1—C1113.68 (19)C7A—N2—H21109.9
C3—N1—C5112.4 (2)C11—N2—H21107.1
C1—N1—C5110.54 (19)C9—N2—H21107.1
C3—N1—H5106.6C11A—N2—H21100.6
C1—N1—H5106.6N2—C7—C8114.1 (3)
C5—N1—H5106.6N2—C7—H22108.7
C2—C1—N1110.0 (2)C8—C7—H22108.7
C2—C1—H6109.7N2—C7—H23108.7
N1—C1—H6109.7C8—C7—H23108.7
C2—C1—H7109.7H22—C7—H23107.6
N1—C1—H7109.7O12—C8—C7110.7 (2)
H6—C1—H7108.2O12—C8—H24109.5
O9—C2—C1110.2 (2)C7—C8—H24109.5
O9—C2—H8109.6O12—C8—H25109.5
C1—C2—H8109.6C7—C8—H25109.5
O9—C2—H9109.6H24—C8—H25108.1
C1—C2—H9109.6C10—C9—N2111.5 (2)
H8—C2—H9108.1C10—C9—H26109.3
N1—C3—C4112.4 (2)N2—C9—H26109.3
N1—C3—H10109.1C10—C9—H27109.3
C4—C3—H10109.1N2—C9—H27109.3
N1—C3—H11109.1H26—C9—H27108.0
C4—C3—H11109.1O13—C10—C9111.4 (2)
H10—C3—H11107.9O13—C10—H28109.3
O10—C4—C3108.9 (2)C9—C10—H28109.3
O10—C4—H12109.9O13—C10—H29109.3
C3—C4—H12109.9C9—C10—H29109.3
O10—C4—H13109.9H28—C10—H29108.0
C3—C4—H13109.9N2—C11—C12110.1 (2)
H12—C4—H13108.3N2—C11—H30109.6
N1—C5—C6110.8 (2)C12—C11—H30109.6
N1—C5—H14109.5N2—C11—H31109.6
C6—C5—H14109.5C12—C11—H31109.6
N1—C5—H15109.5H30—C11—H31108.2
C6—C5—H15109.5O14—C12—C11109.3 (2)
H14—C5—H15108.1O14—C12—H32109.8
O11—C6—C5111.1 (2)C11—C12—H32109.8
O11—C6—H16109.4O14—C12—H33109.8
C5—C6—H16109.4C11—C12—H33109.8
O11—C6—H17109.4H32—C12—H33108.3
C5—C6—H17109.4C8—O12—H34116.7
H16—C6—H17108.0C10—O13—H35100.3
C2—O9—H18102.8C12—O14—H36105.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O60.821.852.670 (2)170
O4—H2···O6i0.881.822.680 (2)166
O7—H3···O2ii0.811.842.642 (2)171
O8—H4···O12iii0.781.902.681 (2)180
N1—H5···O90.912.332.818 (3)113
N1—H5···O100.912.352.774 (3)108
N1—H5···O110.912.352.830 (3)113
O9—H18···O60.891.852.738 (2)170
O10—H19···O50.841.852.690 (2)178
O11—H20···O1iv0.891.792.671 (2)175
N2—H21···O140.912.252.754 (3)114
N2—H21···O120.912.322.768 (2)110
N2—H21···O130.912.322.779 (3)111
O12—H34···O2v0.801.882.655 (2)163
O13—H35···O1v0.931.712.644 (2)173
O14—H36···O5vi0.861.852.698 (2)169
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x1, y1, z; (iv) x+1, y1/2, z+1; (v) x+1, y+1/2, z; (vi) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC6H16NO3+·H2PO4
Mr247.18
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)14.1354 (7), 5.5364 (3), 15.5323 (7)
β (°) 116.354 (1)
V3)1089.21 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.45 × 0.12 × 0.04
Data collection
DiffractometerBruker SMART1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.885, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
9297, 4714, 3779
Rint0.025
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.084, 0.98
No. of reflections4714
No. of parameters284
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.28
Absolute structureFlack (1983)
Absolute structure parameter0.18 (8)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and ATOMS (Shape Software, 1999), SHELXL97.

Selected bond lengths (Å) top
P1—O11.4907 (17)C3—C41.506 (4)
P1—O21.5034 (16)C4—O101.414 (4)
P1—O31.567 (2)C5—C61.507 (4)
P1—O41.5787 (17)C6—O111.399 (4)
P2—O51.4915 (16)N2—C71.484 (3)
P2—O61.5129 (15)N2—C111.491 (3)
P2—O81.5688 (18)N2—C91.527 (3)
P2—O71.5740 (17)C7—C81.493 (4)
N1—C31.492 (3)C8—O121.425 (4)
N1—C11.505 (3)C9—C101.443 (4)
N1—C51.506 (3)C10—O131.398 (4)
C1—C21.496 (4)C11—C121.530 (4)
C2—O91.412 (3)C12—O141.418 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1···O60.821.852.670 (2)170
O4—H2···O6i0.881.822.680 (2)166
O7—H3···O2ii0.811.842.642 (2)171
O8—H4···O12iii0.781.902.681 (2)180
N1—H5···O90.912.332.818 (3)113
N1—H5···O100.912.352.774 (3)108
N1—H5···O110.912.352.830 (3)113
O9—H18···O60.891.852.738 (2)170
O10—H19···O50.841.852.690 (2)178
O11—H20···O1iv0.891.792.671 (2)175
N2—H21···O140.912.252.754 (3)114
N2—H21···O120.912.322.768 (2)110
N2—H21···O130.912.322.779 (3)111
O12—H34···O2v0.801.882.655 (2)163
O13—H35···O1v0.931.712.644 (2)173
O14—H36···O5vi0.861.852.698 (2)169
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x1, y1, z; (iv) x+1, y1/2, z+1; (v) x+1, y+1/2, z; (vi) x+1, y+1, z.
 

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