(S,S)-N,N′-Bis(2-hydr­oxy-2-but­yl)ethyl­enediammonium oxalate penta­hydrate

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.

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

No syntax errors found



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

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

Crystal data

C10H26N2O2^2+·C2O4^2^−·5H2O	F(000) = 840
Mr = 384.43	Dx = 1.269 Mg m^−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: C 2c 2	Cell parameters from 3399 reflections
a = 8.2104 (15) Å	θ = 2.6–27.9°
b = 10.3092 (19) Å	µ = 0.11 mm^−1
c = 23.771 (5) Å	T = 113 K
V = 2012.0 (7) Å^3	Block, colorless
Z = 4	0.16 × 0.14 × 0.06 mm

Data collection

Rigaku Saturn diffractometer	1376 independent reflections
Radiation source: rotating anode	1314 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.041
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (Jacobson, 1998)	k = −13→13
Tmin = 0.976, Tmax = 0.993	l = −31→28
12718 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 0.473P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1376 reflections	Δρmax = 0.24 e Å^−3
141 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0137 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.47733 (19)	0.39226 (15)	0.71864 (6)	0.0160 (3)
H1A	0.4945	0.3045	0.7028	0.019*
H1B	0.3607	0.4146	0.7143	0.019*
N1	0.57936 (16)	0.48853 (13)	0.68705 (5)	0.0132 (3)
H1C	0.596 (2)	0.5586 (18)	0.7095 (8)	0.016*
H1D	0.678 (3)	0.4530 (18)	0.6815 (8)	0.016*
C2	0.51068 (19)	0.53964 (14)	0.63270 (6)	0.0153 (3)
H2	0.4005	0.5770	0.6405	0.018*
C3	0.6226 (2)	0.64947 (15)	0.61306 (7)	0.0186 (3)
H3A	0.6475	0.7065	0.6455	0.022*
H3B	0.7265	0.6119	0.5996	0.022*
C4	0.5481 (3)	0.73060 (19)	0.56624 (8)	0.0314 (4)
H4A	0.4487	0.7726	0.5800	0.047*
H4B	0.5213	0.6745	0.5343	0.047*
H4C	0.6262	0.7970	0.5543	0.047*
C5	0.4916 (2)	0.43040 (16)	0.59033 (7)	0.0184 (3)
H5A	0.4208	0.3617	0.6061	0.022*
H5B	0.4399	0.4638	0.5556	0.022*
O1	0.64811 (14)	0.37821 (11)	0.57756 (5)	0.0191 (3)
H1	0.638 (3)	0.301 (2)	0.5686 (9)	0.029*
C6	0.58360 (17)	0.78537 (14)	0.76520 (6)	0.0135 (3)
O2	0.66772 (13)	0.68395 (10)	0.76030 (4)	0.0174 (3)
O3	0.62101 (13)	0.88511 (11)	0.79193 (5)	0.0207 (3)
O4	0.8605 (2)	0.5000	0.5000	0.0191 (3)
H4	0.799 (3)	0.461 (2)	0.5207 (9)	0.029*
O5	0.08000 (19)	0.58252 (15)	0.67537 (5)	0.0340 (4)
H5C	0.152 (3)	0.618 (2)	0.7015 (11)	0.051*
H5D	0.029 (4)	0.521 (3)	0.6901 (11)	0.051*
O6	0.11366 (17)	0.62337 (12)	0.56322 (5)	0.0253 (3)
H6A	0.092 (3)	0.604 (2)	0.5984 (11)	0.038*
H6B	0.044 (3)	0.584 (2)	0.5424 (10)	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0180 (7)	0.0145 (7)	0.0156 (7)	−0.0024 (6)	0.0003 (6)	−0.0006 (5)
N1	0.0126 (6)	0.0143 (6)	0.0128 (5)	0.0016 (5)	−0.0013 (5)	−0.0015 (5)
C2	0.0146 (7)	0.0193 (7)	0.0121 (6)	0.0033 (6)	−0.0010 (5)	0.0008 (6)
C3	0.0208 (8)	0.0187 (7)	0.0163 (7)	−0.0005 (6)	0.0000 (6)	0.0004 (6)
C4	0.0352 (10)	0.0342 (10)	0.0248 (9)	−0.0018 (8)	−0.0024 (8)	0.0139 (7)
C5	0.0156 (7)	0.0257 (8)	0.0139 (7)	−0.0012 (6)	−0.0010 (6)	−0.0028 (6)
O1	0.0189 (5)	0.0174 (5)	0.0209 (5)	−0.0011 (5)	0.0035 (4)	−0.0038 (4)
C6	0.0130 (7)	0.0142 (6)	0.0134 (6)	−0.0013 (6)	0.0006 (6)	0.0015 (5)
O2	0.0160 (5)	0.0158 (5)	0.0204 (6)	0.0031 (4)	−0.0041 (4)	−0.0022 (4)
O3	0.0161 (5)	0.0171 (5)	0.0288 (6)	0.0003 (5)	−0.0050 (5)	−0.0070 (4)
O4	0.0193 (8)	0.0213 (8)	0.0168 (7)	0.000	0.000	0.0041 (6)
O5	0.0382 (8)	0.0416 (8)	0.0223 (6)	−0.0238 (7)	−0.0090 (6)	0.0091 (5)
O6	0.0320 (7)	0.0226 (6)	0.0213 (6)	−0.0075 (6)	−0.0043 (5)	0.0017 (5)

Geometric parameters (Å, º)

C1—C1^i	1.537 (3)	C4—H4B	0.9800
C1—H1A	0.9900	C4—H4C	0.9800
C1—H1B	0.9900	C5—H5A	0.9900
N1—C1	1.5003 (19)	C5—H5B	0.9900
N1—C2	1.5049 (19)	O1—C5	1.426 (2)
N1—H1C	0.908 (19)	O1—H1	0.82 (2)
N1—H1D	0.89 (2)	C6—C6^i	1.551 (3)
C2—C5	1.519 (2)	O2—C6	1.2584 (17)
C2—C3	1.531 (2)	O3—C6	1.2472 (18)
C2—H2	1.0000	O4—H4	0.81 (2)
C3—C4	1.521 (2)	O5—H5C	0.93 (3)
C3—H3A	0.9900	O5—H5D	0.84 (3)
C3—H3B	0.9900	O6—H6A	0.88 (3)
C4—H4A	0.9800	O6—H6B	0.86 (3)
N1—C1—C1^i	110.51 (12)	C4—C3—H3B	109.0
C1—N1—C2	116.88 (12)	C2—C3—H3B	109.0
C1—N1—H1C	108.4 (12)	H3A—C3—H3B	107.8
C2—N1—H1C	106.4 (11)	C3—C4—H4A	109.5
C1—N1—H1D	107.8 (12)	C3—C4—H4B	109.5
C2—N1—H1D	110.7 (12)	H4A—C4—H4B	109.5
H1C—N1—H1D	106.1 (17)	C3—C4—H4C	109.5
N1—C1—H1A	109.5	H4A—C4—H4C	109.5
C1^i—C1—H1A	109.5	H4B—C4—H4C	109.5
N1—C1—H1B	109.5	O1—C5—C2	109.13 (13)
C1^i—C1—H1B	109.5	O1—C5—H5A	109.9
H1A—C1—H1B	108.1	C2—C5—H5A	109.9
N1—C2—C3	107.19 (12)	O1—C5—H5B	109.9
N1—C2—C5	110.39 (12)	C2—C5—H5B	109.9
C5—C2—C3	114.09 (13)	H5A—C5—H5B	108.3
N1—C2—H2	108.3	C5—O1—H1	108.9 (17)
C5—C2—H2	108.3	O3—C6—O2	126.66 (13)
C3—C2—H2	108.3	O3—C6—C6^i	117.08 (10)
C4—C3—C2	112.84 (14)	O2—C6—C6^i	116.26 (9)
C4—C3—H3A	109.0	H5C—O5—H5D	110 (2)
C2—C3—H3A	109.0	H6A—O6—H6B	108 (2)
C2—N1—C1—C1^i	−156.35 (12)	C5—C2—C3—C4	70.74 (18)
C1—N1—C2—C5	−63.45 (16)	N1—C2—C5—O1	−63.06 (16)
C1—N1—C2—C3	171.74 (12)	C3—C2—C5—O1	57.72 (16)
N1—C2—C3—C4	−166.73 (13)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1	0.81 (2)	2.02 (2)	2.8314 (16)	174 (2)
N1—H1C···O2	0.908 (19)	1.86 (2)	2.7599 (17)	168.3 (17)
N1—H1C···O2^i	0.908 (19)	2.622 (19)	3.1210 (17)	115.4 (15)
N1—H1D···O3^ii	0.89 (2)	1.90 (2)	2.7273 (17)	152.1 (17)
O5—H5C···O2^i	0.93 (3)	1.87 (3)	2.7789 (18)	166 (2)
O5—H5D···O3^iii	0.84 (3)	1.91 (3)	2.7330 (18)	166 (3)
O6—H6A···O5	0.88 (3)	1.85 (3)	2.7132 (18)	169 (2)
O1—H1···O6^iv	0.82 (2)	1.85 (2)	2.6643 (17)	169 (2)
O6—H6B···O4^v	0.86 (3)	2.01 (3)	2.8630 (18)	173 (2)

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