The title compound, C
10H
26N
2O
22+·C
2O
22−·5H
2O, 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
CCDC reference: 624914
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (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
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−·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) Å3 | Block, colorless |
Z = 4 | 0.16 × 0.14 × 0.06 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H 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 reflections | Δρmax = 0.24 e Å−3 |
141 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
C1—C1i | 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—C6i | 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—C1i | 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 |
C1i—C1—H1A | 109.5 | H4B—C4—H4C | 109.5 |
N1—C1—H1B | 109.5 | O1—C5—C2 | 109.13 (13) |
C1i—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—C6i | 117.08 (10) |
C4—C3—C2 | 112.84 (14) | O2—C6—C6i | 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—C1i | −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) top
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···O2i | 0.908 (19) | 2.622 (19) | 3.1210 (17) | 115.4 (15) |
N1—H1D···O3ii | 0.89 (2) | 1.90 (2) | 2.7273 (17) | 152.1 (17) |
O5—H5C···O2i | 0.93 (3) | 1.87 (3) | 2.7789 (18) | 166 (2) |
O5—H5D···O3iii | 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···O6iv | 0.82 (2) | 1.85 (2) | 2.6643 (17) | 169 (2) |
O6—H6B···O4v | 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. |