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The title compound, C10H26N2O22+·C2O22−·5H2O, is the oxalate salt of the drug ethambutol. Both the ethambutol cation and the oxalate anion lie about a crystallographic twofold axis which bis­ects the central C—C bonds of both ions. The O atom of one solvent water mol­ecule also lies on a twofold axis. The crystal structure is stabilized by inter­molecular O—H...N and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037652/lh2181sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037652/lh2181Isup2.hkl
Contains datablock I

CCDC reference: 624914

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.071
  • Data-to-parameter ratio = 9.8

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C6 - C6_b ... 1.55 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C .. O2 .. 2.62 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.87 From the CIF: _reflns_number_total 1376 Count of symmetry unique reflns 1377 Completeness (_total/calc) 99.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

(S,S)—N,N'-Bis(2-hydroxy-2-butyl)ethylenediammonium oxalate pentahydrate top
Crystal data top
C10H26N2O22+·C2O42·5H2OF(000) = 840
Mr = 384.43Dx = 1.269 Mg m3
Orthorhombic, C2221Mo Kα radiation, λ = 0.71070 Å
Hall symbol: C 2c 2Cell parameters from 3399 reflections
a = 8.2104 (15) Åθ = 2.6–27.9°
b = 10.3092 (19) ŵ = 0.11 mm1
c = 23.771 (5) ÅT = 113 K
V = 2012.0 (7) Å3Block, colorless
Z = 40.16 × 0.14 × 0.06 mm
Data collection top
Rigaku Saturn
diffractometer
1376 independent reflections
Radiation source: rotating anode1314 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.041
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 3.2°
ω scansh = 1010
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1313
Tmin = 0.976, Tmax = 0.993l = 3128
12718 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0427P)2 + 0.473P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1376 reflectionsΔρmax = 0.24 e Å3
141 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0137 (13)
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
C10.47733 (19)0.39226 (15)0.71864 (6)0.0160 (3)
H1A0.49450.30450.70280.019*
H1B0.36070.41460.71430.019*
N10.57936 (16)0.48853 (13)0.68705 (5)0.0132 (3)
H1C0.596 (2)0.5586 (18)0.7095 (8)0.016*
H1D0.678 (3)0.4530 (18)0.6815 (8)0.016*
C20.51068 (19)0.53964 (14)0.63270 (6)0.0153 (3)
H20.40050.57700.64050.018*
C30.6226 (2)0.64947 (15)0.61306 (7)0.0186 (3)
H3A0.64750.70650.64550.022*
H3B0.72650.61190.59960.022*
C40.5481 (3)0.73060 (19)0.56624 (8)0.0314 (4)
H4A0.44870.77260.58000.047*
H4B0.52130.67450.53430.047*
H4C0.62620.79700.55430.047*
C50.4916 (2)0.43040 (16)0.59033 (7)0.0184 (3)
H5A0.42080.36170.60610.022*
H5B0.43990.46380.55560.022*
O10.64811 (14)0.37821 (11)0.57756 (5)0.0191 (3)
H10.638 (3)0.301 (2)0.5686 (9)0.029*
C60.58360 (17)0.78537 (14)0.76520 (6)0.0135 (3)
O20.66772 (13)0.68395 (10)0.76030 (4)0.0174 (3)
O30.62101 (13)0.88511 (11)0.79193 (5)0.0207 (3)
O40.8605 (2)0.50000.50000.0191 (3)
H40.799 (3)0.461 (2)0.5207 (9)0.029*
O50.08000 (19)0.58252 (15)0.67537 (5)0.0340 (4)
H5C0.152 (3)0.618 (2)0.7015 (11)0.051*
H5D0.029 (4)0.521 (3)0.6901 (11)0.051*
O60.11366 (17)0.62337 (12)0.56322 (5)0.0253 (3)
H6A0.092 (3)0.604 (2)0.5984 (11)0.038*
H6B0.044 (3)0.584 (2)0.5424 (10)0.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0180 (7)0.0145 (7)0.0156 (7)0.0024 (6)0.0003 (6)0.0006 (5)
N10.0126 (6)0.0143 (6)0.0128 (5)0.0016 (5)0.0013 (5)0.0015 (5)
C20.0146 (7)0.0193 (7)0.0121 (6)0.0033 (6)0.0010 (5)0.0008 (6)
C30.0208 (8)0.0187 (7)0.0163 (7)0.0005 (6)0.0000 (6)0.0004 (6)
C40.0352 (10)0.0342 (10)0.0248 (9)0.0018 (8)0.0024 (8)0.0139 (7)
C50.0156 (7)0.0257 (8)0.0139 (7)0.0012 (6)0.0010 (6)0.0028 (6)
O10.0189 (5)0.0174 (5)0.0209 (5)0.0011 (5)0.0035 (4)0.0038 (4)
C60.0130 (7)0.0142 (6)0.0134 (6)0.0013 (6)0.0006 (6)0.0015 (5)
O20.0160 (5)0.0158 (5)0.0204 (6)0.0031 (4)0.0041 (4)0.0022 (4)
O30.0161 (5)0.0171 (5)0.0288 (6)0.0003 (5)0.0050 (5)0.0070 (4)
O40.0193 (8)0.0213 (8)0.0168 (7)0.0000.0000.0041 (6)
O50.0382 (8)0.0416 (8)0.0223 (6)0.0238 (7)0.0090 (6)0.0091 (5)
O60.0320 (7)0.0226 (6)0.0213 (6)0.0075 (6)0.0043 (5)0.0017 (5)
Geometric parameters (Å, º) top
C1—C1i1.537 (3)C4—H4B0.9800
C1—H1A0.9900C4—H4C0.9800
C1—H1B0.9900C5—H5A0.9900
N1—C11.5003 (19)C5—H5B0.9900
N1—C21.5049 (19)O1—C51.426 (2)
N1—H1C0.908 (19)O1—H10.82 (2)
N1—H1D0.89 (2)C6—C6i1.551 (3)
C2—C51.519 (2)O2—C61.2584 (17)
C2—C31.531 (2)O3—C61.2472 (18)
C2—H21.0000O4—H40.81 (2)
C3—C41.521 (2)O5—H5C0.93 (3)
C3—H3A0.9900O5—H5D0.84 (3)
C3—H3B0.9900O6—H6A0.88 (3)
C4—H4A0.9800O6—H6B0.86 (3)
N1—C1—C1i110.51 (12)C4—C3—H3B109.0
C1—N1—C2116.88 (12)C2—C3—H3B109.0
C1—N1—H1C108.4 (12)H3A—C3—H3B107.8
C2—N1—H1C106.4 (11)C3—C4—H4A109.5
C1—N1—H1D107.8 (12)C3—C4—H4B109.5
C2—N1—H1D110.7 (12)H4A—C4—H4B109.5
H1C—N1—H1D106.1 (17)C3—C4—H4C109.5
N1—C1—H1A109.5H4A—C4—H4C109.5
C1i—C1—H1A109.5H4B—C4—H4C109.5
N1—C1—H1B109.5O1—C5—C2109.13 (13)
C1i—C1—H1B109.5O1—C5—H5A109.9
H1A—C1—H1B108.1C2—C5—H5A109.9
N1—C2—C3107.19 (12)O1—C5—H5B109.9
N1—C2—C5110.39 (12)C2—C5—H5B109.9
C5—C2—C3114.09 (13)H5A—C5—H5B108.3
N1—C2—H2108.3C5—O1—H1108.9 (17)
C5—C2—H2108.3O3—C6—O2126.66 (13)
C3—C2—H2108.3O3—C6—C6i117.08 (10)
C4—C3—C2112.84 (14)O2—C6—C6i116.26 (9)
C4—C3—H3A109.0H5C—O5—H5D110 (2)
C2—C3—H3A109.0H6A—O6—H6B108 (2)
C2—N1—C1—C1i156.35 (12)C5—C2—C3—C470.74 (18)
C1—N1—C2—C563.45 (16)N1—C2—C5—O163.06 (16)
C1—N1—C2—C3171.74 (12)C3—C2—C5—O157.72 (16)
N1—C2—C3—C4166.73 (13)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O10.81 (2)2.02 (2)2.8314 (16)174 (2)
N1—H1C···O20.908 (19)1.86 (2)2.7599 (17)168.3 (17)
N1—H1C···O2i0.908 (19)2.622 (19)3.1210 (17)115.4 (15)
N1—H1D···O3ii0.89 (2)1.90 (2)2.7273 (17)152.1 (17)
O5—H5C···O2i0.93 (3)1.87 (3)2.7789 (18)166 (2)
O5—H5D···O3iii0.84 (3)1.91 (3)2.7330 (18)166 (3)
O6—H6A···O50.88 (3)1.85 (3)2.7132 (18)169 (2)
O1—H1···O6iv0.82 (2)1.85 (2)2.6643 (17)169 (2)
O6—H6B···O4v0.86 (3)2.01 (3)2.8630 (18)173 (2)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+3/2, y1/2, z+3/2; (iii) x+1/2, y1/2, z+3/2; (iv) x+1/2, y1/2, z; (v) x1, y, z.
 

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