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The organic moiety of the title compound, C11H18NO5P·2H2O, is zwitterionic. The crystal packing is stabilized by N—H...O and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025742/hb6242sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025742/hb6242Isup2.hkl
Contains datablock I

CCDC reference: 283917

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.112
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

Ethyl [(2-hydroxyethylammonio)(2-hydroxyphenyl)methyl]phosphonate dihydrate top
Crystal data top
C11H18NO5P·2H2OF(000) = 664
Mr = 311.27Dx = 1.414 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1375 reflections
a = 7.356 (2) Åθ = 1.8–27.5°
b = 8.707 (5) ŵ = 0.22 mm1
c = 23.417 (8) ÅT = 298 K
β = 102.80 (3)°Block, colorless
V = 1462.6 (11) Å30.20 × 0.15 × 0.15 mm
Z = 4
Data collection top
SMART 1K CCD area-detector
diffractometer
2498 independent reflections
Radiation source: fine-focus sealed tube1718 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 81
Tmin = 0.958, Tmax = 0.968k = 99
5972 measured reflectionsl = 2426
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: difmap (water O-H) and geom (others)
wR(F2) = 0.112H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0442P)2 + 0.189P]
where P = (Fo2 + 2Fc2)/3
2498 reflections(Δ/σ)max = 0.001
184 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.25 e Å3
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*/Ueq
C10.3069 (4)0.0952 (3)0.12570 (11)0.0229 (6)
C20.3755 (4)0.0109 (3)0.17683 (12)0.0260 (7)
O10.3413 (3)0.0666 (2)0.22735 (8)0.0376 (6)
H10.38820.00960.25450.056*
C30.4750 (4)0.1236 (3)0.17452 (14)0.0324 (7)
H30.52260.17810.20870.039*
C40.5036 (4)0.1770 (4)0.12161 (15)0.0380 (8)
H40.56760.26850.12020.046*
C50.4372 (4)0.0945 (4)0.07081 (14)0.0389 (8)
H50.45720.12980.03520.047*
C60.3402 (4)0.0417 (3)0.07324 (13)0.0330 (7)
H60.29700.09770.03910.040*
C70.2019 (4)0.2429 (3)0.13007 (11)0.0228 (6)
H70.16920.24210.16840.027*
N10.0221 (3)0.2529 (3)0.08500 (9)0.0251 (5)
H1A0.02830.34610.08750.030*
H1B0.04750.24510.04920.030*
C80.1193 (4)0.1330 (4)0.09051 (13)0.0331 (7)
H8A0.07360.03250.08260.040*
H8B0.23430.15240.06190.040*
C90.1565 (5)0.1353 (4)0.15099 (14)0.0388 (8)
H9A0.27490.08590.15060.047*
H9B0.05950.07880.17760.047*
O20.1608 (3)0.2898 (3)0.17073 (11)0.0439 (6)
H20.26920.31590.16860.066*
P10.34197 (10)0.41641 (8)0.12755 (3)0.0221 (2)
O30.5035 (3)0.4073 (2)0.17859 (8)0.0310 (5)
O40.3787 (3)0.4357 (2)0.06832 (8)0.0348 (5)
O50.1997 (3)0.5486 (2)0.13578 (8)0.0285 (5)
C100.1590 (4)0.5813 (4)0.19294 (12)0.0333 (7)
H10A0.26690.62760.21860.040*
H10B0.12950.48680.21090.040*
C110.0019 (6)0.6882 (5)0.18447 (15)0.0579 (11)
H11A0.02800.78100.16640.087*
H11B0.02900.71180.22180.087*
H11C0.10870.64080.15970.087*
O60.7417 (3)0.4872 (3)0.04613 (9)0.0496 (7)
H610.64480.47030.05720.074*
H620.71950.48970.01040.074*
O70.9750 (4)0.7445 (3)0.03541 (9)0.0496 (7)
H710.89880.68310.04310.074*
H721.07750.72900.05690.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0170 (14)0.0241 (15)0.0264 (15)0.0007 (13)0.0020 (13)0.0005 (12)
C20.0216 (15)0.0289 (16)0.0264 (16)0.0036 (14)0.0027 (13)0.0041 (12)
O10.0446 (14)0.0428 (13)0.0253 (11)0.0114 (11)0.0075 (10)0.0095 (9)
C30.0257 (16)0.0277 (17)0.0425 (19)0.0009 (14)0.0050 (14)0.0073 (13)
C40.0254 (17)0.0250 (17)0.061 (2)0.0025 (14)0.0047 (17)0.0044 (14)
C50.0358 (18)0.0391 (19)0.0416 (19)0.0012 (17)0.0080 (16)0.0134 (15)
C60.0301 (17)0.0369 (18)0.0305 (17)0.0020 (15)0.0036 (14)0.0006 (13)
C70.0206 (15)0.0262 (15)0.0206 (14)0.0030 (13)0.0023 (12)0.0007 (12)
N10.0201 (13)0.0299 (13)0.0240 (12)0.0023 (11)0.0018 (10)0.0004 (10)
C80.0200 (15)0.0354 (17)0.0417 (19)0.0063 (15)0.0024 (14)0.0046 (13)
C90.0294 (17)0.0409 (19)0.048 (2)0.0080 (16)0.0128 (16)0.0058 (15)
O20.0271 (12)0.0506 (15)0.0570 (15)0.0022 (11)0.0161 (12)0.0117 (11)
P10.0195 (4)0.0250 (4)0.0220 (4)0.0017 (3)0.0051 (3)0.0006 (3)
O30.0234 (11)0.0372 (12)0.0303 (11)0.0005 (10)0.0015 (9)0.0097 (9)
O40.0409 (13)0.0399 (13)0.0271 (11)0.0062 (11)0.0149 (10)0.0024 (9)
O50.0306 (12)0.0267 (11)0.0286 (11)0.0044 (9)0.0072 (9)0.0001 (8)
C100.0345 (18)0.0369 (17)0.0303 (16)0.0048 (15)0.0110 (14)0.0039 (14)
C110.054 (3)0.079 (3)0.041 (2)0.033 (2)0.0115 (19)0.0059 (18)
O60.0370 (14)0.0734 (17)0.0393 (14)0.0078 (13)0.0101 (11)0.0190 (12)
O70.0531 (16)0.0599 (16)0.0333 (12)0.0032 (14)0.0041 (12)0.0098 (11)
Geometric parameters (Å, º) top
C1—C61.385 (4)C8—H8A0.9700
C1—C21.400 (4)C8—H8B0.9700
C1—C71.515 (4)C9—O21.425 (4)
C2—O11.353 (3)C9—H9A0.9700
C2—C31.388 (4)C9—H9B0.9700
O1—H10.8200O2—H20.8200
C3—C41.382 (4)P1—O41.480 (2)
C3—H30.9300P1—O31.489 (2)
C4—C51.383 (4)P1—O51.596 (2)
C4—H40.9300O5—C101.463 (3)
C5—C61.391 (4)C10—C111.484 (4)
C5—H50.9300C10—H10A0.9700
C6—H60.9300C10—H10B0.9700
C7—N11.501 (4)C11—H11A0.9600
P1—C71.837 (3)C11—H11B0.9600
C7—H70.9800C11—H11C0.9600
N1—C81.499 (4)O6—H610.8244
N1—H1A0.9000O6—H620.8164
N1—H1B0.9000O7—H710.8230
C8—C91.501 (4)O7—H720.8201
C6—C1—C2118.8 (3)C9—C8—H8A109.6
C6—C1—C7122.6 (2)N1—C8—H8B109.6
C2—C1—C7118.7 (2)C9—C8—H8B109.6
O1—C2—C3122.6 (2)H8A—C8—H8B108.1
O1—C2—C1117.3 (3)O2—C9—C8109.9 (3)
C3—C2—C1120.2 (3)O2—C9—H9A109.7
C2—O1—H1109.5C8—C9—H9A109.7
C4—C3—C2120.3 (3)O2—C9—H9B109.7
C4—C3—H3119.8C8—C9—H9B109.7
C2—C3—H3119.8H9A—C9—H9B108.2
C3—C4—C5120.1 (3)C9—O2—H2109.5
C3—C4—H4120.0O4—P1—O3118.65 (13)
C5—C4—H4120.0O4—P1—O5106.98 (12)
C4—C5—C6119.6 (3)O3—P1—O5111.70 (11)
C4—C5—H5120.2O4—P1—C7110.08 (12)
C6—C5—H5120.2O3—P1—C7106.48 (12)
C1—C6—C5121.0 (3)O5—P1—C7101.64 (12)
C1—C6—H6119.5C10—O5—P1121.56 (17)
C5—C6—H6119.5O5—C10—C11108.6 (2)
N1—C7—C1112.6 (2)O5—C10—H10A110.0
N1—C7—P1110.05 (18)C11—C10—H10A110.0
C1—C7—P1113.44 (19)O5—C10—H10B110.0
N1—C7—H7106.8C11—C10—H10B110.0
C1—C7—H7106.8H10A—C10—H10B108.4
P1—C7—H7106.8C10—C11—H11A109.5
C8—N1—C7114.8 (2)C10—C11—H11B109.5
C8—N1—H1A108.6H11A—C11—H11B109.5
C7—N1—H1A108.6C10—C11—H11C109.5
C8—N1—H1B108.6H11A—C11—H11C109.5
C7—N1—H1B108.6H11B—C11—H11C109.5
H1A—N1—H1B107.5H61—O6—H62109.8
N1—C8—C9110.3 (2)H71—O7—H72109.7
N1—C8—H8A109.6
C6—C1—C2—O1179.7 (3)C1—C7—N1—C863.6 (3)
C7—C1—C2—O10.8 (4)P1—C7—N1—C8168.72 (18)
C6—C1—C2—C30.0 (4)C7—N1—C8—C954.7 (3)
C7—C1—C2—C3179.0 (3)N1—C8—C9—O239.4 (3)
O1—C2—C3—C4178.9 (3)N1—C7—P1—O458.0 (2)
C1—C2—C3—C41.4 (4)C1—C7—P1—O469.2 (2)
C2—C3—C4—C51.6 (5)N1—C7—P1—O3172.22 (17)
C3—C4—C5—C60.6 (5)C1—C7—P1—O360.6 (2)
C2—C1—C6—C51.1 (4)N1—C7—P1—O555.2 (2)
C7—C1—C6—C5180.0 (3)C1—C7—P1—O5177.62 (18)
C4—C5—C6—C10.8 (5)O4—P1—O5—C10168.8 (2)
C6—C1—C7—N149.0 (4)O3—P1—O5—C1037.4 (2)
C2—C1—C7—N1132.0 (3)C7—P1—O5—C1075.8 (2)
C6—C1—C7—P176.8 (3)P1—O5—C10—C11169.6 (2)
C2—C1—C7—P1102.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O50.902.523.010 (3)115
N1—H1A···O6i0.902.142.901 (3)142
N1—H1B···O7ii0.901.952.825 (3)162
O1—H1···O3iii0.821.822.639 (3)172
O2—H2···O3i0.821.912.716 (3)167
O6—H61···O40.822.052.866 (3)169
O6—H62···O4ii0.821.942.714 (3)159
O7—H72···O5iv0.822.443.073 (3)135
O7—H71···O60.822.072.867 (4)163
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x+1, y1/2, z+1/2; (iv) x+1, y, z.
 

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