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In the title structure, C10H26N2O22+·2NO3, the ethambutol mol­ecule exists in the cationic form, having two protonated amine groups, and is charge-balanced by two nitrate anions. In the crystal structure, a two-dimensional network is formed via inter­molecular O—H...O and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026778/lh2119sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026778/lh2119Isup2.hkl
Contains datablock I

CCDC reference: 618271

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.082
  • Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT353_ALERT_3_C Long N-H Bond (0.87A) N2 - H2C ... 1.05 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O5 .. 2.63 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 2011 Count of symmetry unique reflns 2015 Completeness (_total/calc) 99.80% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: SHELXTL.

(S,S)-2,2'-(Ethane-1,2-diyldiiminio)dibutan-1-ol dinitrate top
Crystal data top
C10H26N2O22+·2NO3F(000) = 356
Mr = 330.35Dx = 1.373 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ybCell parameters from 2687 reflections
a = 8.769 (3) Åθ = 2.1–27.9°
b = 9.598 (4) ŵ = 0.12 mm1
c = 9.583 (4) ÅT = 113 K
β = 97.829 (6)°Block, colorless
V = 799.0 (5) Å30.26 × 0.24 × 0.20 mm
Z = 2
Data collection top
Bruker SMART-1000
diffractometer
2011 independent reflections
Radiation source: fine-focus sealed tube1830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 811
Tmin = 0.964, Tmax = 0.977k = 1212
7494 measured reflectionsl = 1212
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0503P)2]
where P = (Fo2 + 2Fc2)/3
2011 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.28 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
O10.31942 (18)0.47671 (16)0.20921 (14)0.0218 (3)
H1A0.339 (3)0.432 (3)0.279 (3)0.033*
O20.87421 (19)0.44956 (15)0.63053 (15)0.0214 (3)
H20.831 (3)0.482 (3)0.687 (3)0.032*
O30.61041 (18)0.59595 (15)0.99975 (14)0.0210 (3)
O40.72104 (18)0.61474 (16)0.81099 (14)0.0238 (3)
O50.6963 (2)0.41156 (16)0.90564 (16)0.0306 (4)
O60.47683 (19)0.12143 (16)0.50926 (17)0.0275 (4)
O70.4151 (2)0.33225 (14)0.56104 (16)0.0254 (4)
O80.28950 (18)0.15573 (16)0.63261 (15)0.0242 (4)
N10.4038 (2)0.38068 (18)0.06638 (16)0.0150 (3)
H1B0.469 (3)0.427 (3)0.017 (2)0.018*
H1C0.414 (3)0.285 (3)0.046 (2)0.018*
N20.6728 (2)0.35449 (18)0.40543 (17)0.0145 (3)
H2C0.580 (3)0.351 (2)0.464 (2)0.017*
H2D0.703 (3)0.439 (3)0.413 (2)0.017*
N30.6771 (2)0.53952 (19)0.90432 (18)0.0193 (4)
N40.3933 (2)0.20173 (18)0.56722 (17)0.0184 (4)
C10.2424 (2)0.4308 (2)0.01654 (19)0.0161 (4)
H10.16890.37500.06500.019*
C20.2122 (2)0.3997 (2)0.1410 (2)0.0185 (4)
H2A0.22440.29880.15750.022*
H2B0.10580.42690.17920.022*
C30.2242 (2)0.5839 (2)0.0525 (2)0.0190 (4)
H3A0.25950.59790.15410.023*
H3B0.29100.64050.00080.023*
C40.0592 (2)0.6352 (2)0.0189 (2)0.0244 (5)
H4A0.05430.73400.04380.029*
H4B0.00730.58130.07320.029*
H4C0.02410.62350.08200.029*
C50.4596 (2)0.4015 (2)0.21860 (19)0.0177 (4)
H5A0.38210.36650.27600.021*
H5B0.47590.50190.23860.021*
C60.6102 (2)0.3228 (2)0.2561 (2)0.0171 (4)
H6A0.59220.22130.24440.021*
H6B0.68480.35170.19290.021*
C70.8032 (2)0.2614 (2)0.46801 (19)0.0182 (4)
H70.76250.16400.46670.022*
C80.8419 (3)0.3046 (2)0.6217 (2)0.0204 (5)
H8A0.75400.28310.67290.024*
H8B0.93240.25150.66630.024*
C90.9373 (3)0.2622 (2)0.3826 (2)0.0234 (5)
H9A0.89960.22730.28680.028*
H9B1.01580.19550.42630.028*
C101.0157 (3)0.4026 (3)0.3682 (3)0.0323 (5)
H10A1.09990.39120.31160.039*
H10B1.05690.43750.46190.039*
H10C0.94060.46930.32190.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0311 (9)0.0196 (7)0.0157 (6)0.0029 (7)0.0067 (6)0.0013 (6)
O20.0247 (8)0.0200 (8)0.0199 (7)0.0024 (7)0.0047 (6)0.0040 (6)
O30.0248 (8)0.0184 (7)0.0213 (7)0.0014 (6)0.0081 (6)0.0016 (6)
O40.0291 (8)0.0209 (8)0.0230 (7)0.0007 (7)0.0093 (6)0.0040 (6)
O50.0424 (10)0.0134 (8)0.0379 (9)0.0046 (7)0.0121 (8)0.0011 (7)
O60.0311 (9)0.0185 (8)0.0366 (8)0.0017 (7)0.0178 (7)0.0027 (7)
O70.0374 (9)0.0124 (7)0.0288 (8)0.0034 (7)0.0129 (7)0.0014 (6)
O80.0268 (8)0.0207 (8)0.0279 (8)0.0044 (7)0.0140 (7)0.0009 (6)
N10.0175 (8)0.0131 (9)0.0140 (8)0.0005 (7)0.0012 (7)0.0005 (6)
N20.0170 (8)0.0133 (8)0.0131 (7)0.0004 (7)0.0016 (7)0.0007 (6)
N30.0209 (9)0.0170 (9)0.0198 (8)0.0008 (7)0.0022 (7)0.0003 (7)
N40.0222 (9)0.0146 (8)0.0182 (8)0.0021 (7)0.0024 (7)0.0004 (7)
C10.0156 (10)0.0170 (10)0.0153 (9)0.0007 (8)0.0009 (8)0.0002 (7)
C20.0190 (10)0.0200 (10)0.0159 (9)0.0013 (8)0.0002 (8)0.0016 (8)
C30.0192 (10)0.0175 (10)0.0197 (9)0.0033 (9)0.0003 (8)0.0022 (8)
C40.0243 (11)0.0259 (12)0.0225 (10)0.0070 (10)0.0014 (9)0.0007 (9)
C50.0208 (11)0.0187 (10)0.0129 (8)0.0018 (9)0.0001 (8)0.0020 (8)
C60.0188 (10)0.0189 (10)0.0127 (9)0.0028 (8)0.0016 (8)0.0030 (8)
C70.0195 (10)0.0142 (9)0.0196 (9)0.0038 (8)0.0017 (8)0.0003 (8)
C80.0252 (11)0.0158 (10)0.0189 (10)0.0016 (9)0.0014 (9)0.0021 (8)
C90.0220 (11)0.0252 (11)0.0226 (10)0.0075 (10)0.0012 (9)0.0018 (9)
C100.0289 (12)0.0378 (14)0.0332 (12)0.0007 (11)0.0154 (10)0.0022 (11)
Geometric parameters (Å, º) top
O1—C21.423 (3)C3—C41.521 (3)
O1—H1A0.83 (3)C3—H3A0.9900
O2—C81.420 (3)C3—H3B0.9900
O2—H20.76 (3)C4—H4A0.9800
O3—N31.272 (2)C4—H4B0.9800
O4—N31.250 (2)C4—H4C0.9800
O5—N31.239 (2)C5—C61.521 (3)
O6—N41.245 (2)C5—H5A0.9900
O7—N41.270 (2)C5—H5B0.9900
O8—N41.253 (2)C6—H6A0.9900
N1—C51.488 (2)C6—H6B0.9900
N1—C11.509 (3)C7—C91.522 (3)
N1—H1B0.90 (2)C7—C81.523 (3)
N1—H1C0.95 (3)C7—H71.0000
N2—C61.493 (2)C8—H8A0.9900
N2—C71.510 (3)C8—H8B0.9900
N2—H2C1.05 (2)C9—C101.528 (4)
N2—H2D0.85 (3)C9—H9A0.9900
C1—C31.523 (3)C9—H9B0.9900
C1—C21.526 (3)C10—H10A0.9800
C1—H11.0000C10—H10B0.9800
C2—H2A0.9900C10—H10C0.9800
C2—H2B0.9900
C2—O1—H1A109 (2)H4A—C4—H4B109.5
C8—O2—H2109 (2)C3—C4—H4C109.5
C5—N1—C1115.90 (15)H4A—C4—H4C109.5
C5—N1—H1B107.5 (15)H4B—C4—H4C109.5
C1—N1—H1B108.2 (16)N1—C5—C6108.91 (15)
C5—N1—H1C107.6 (13)N1—C5—H5A109.9
C1—N1—H1C111.0 (13)C6—C5—H5A109.9
H1B—N1—H1C106 (2)N1—C5—H5B109.9
C6—N2—C7114.83 (15)C6—C5—H5B109.9
C6—N2—H2C107.3 (12)H5A—C5—H5B108.3
C7—N2—H2C111.5 (13)N2—C6—C5108.61 (15)
C6—N2—H2D110.3 (15)N2—C6—H6A110.0
C7—N2—H2D108.6 (16)C5—C6—H6A110.0
H2C—N2—H2D104 (2)N2—C6—H6B110.0
O5—N3—O4121.66 (18)C5—C6—H6B110.0
O5—N3—O3119.33 (18)H6A—C6—H6B108.3
O4—N3—O3119.01 (18)N2—C7—C9112.46 (16)
O6—N4—O8121.09 (18)N2—C7—C8106.25 (16)
O6—N4—O7119.23 (18)C9—C7—C8115.63 (17)
O8—N4—O7119.68 (18)N2—C7—H7107.4
N1—C1—C3111.02 (16)C9—C7—H7107.4
N1—C1—C2106.25 (16)C8—C7—H7107.4
C3—C1—C2113.78 (17)O2—C8—C7109.90 (17)
N1—C1—H1108.6O2—C8—H8A109.7
C3—C1—H1108.6C7—C8—H8A109.7
C2—C1—H1108.6O2—C8—H8B109.7
O1—C2—C1108.45 (16)C7—C8—H8B109.7
O1—C2—H2A110.0H8A—C8—H8B108.2
C1—C2—H2A110.0C7—C9—C10116.31 (18)
O1—C2—H2B110.0C7—C9—H9A108.2
C1—C2—H2B110.0C10—C9—H9A108.2
H2A—C2—H2B108.4C7—C9—H9B108.2
C4—C3—C1113.00 (18)C10—C9—H9B108.2
C4—C3—H3A109.0H9A—C9—H9B107.4
C1—C3—H3A109.0C9—C10—H10A109.5
C4—C3—H3B109.0C9—C10—H10B109.5
C1—C3—H3B109.0H10A—C10—H10B109.5
H3A—C3—H3B107.8C9—C10—H10C109.5
C3—C4—H4A109.5H10A—C10—H10C109.5
C3—C4—H4B109.5H10B—C10—H10C109.5
C5—N1—C1—C355.3 (2)N1—C5—C6—N2174.91 (17)
C5—N1—C1—C2179.53 (17)C6—N2—C7—C956.3 (2)
N1—C1—C2—O162.0 (2)C6—N2—C7—C8176.23 (18)
C3—C1—C2—O160.4 (2)N2—C7—C8—O255.0 (2)
N1—C1—C3—C4173.70 (16)C9—C7—C8—O270.5 (2)
C2—C1—C3—C466.5 (2)N2—C7—C9—C1061.0 (2)
C1—N1—C5—C6169.86 (16)C8—C7—C9—C1061.3 (3)
C7—N2—C6—C5167.56 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2D···O8i0.85 (3)2.13 (3)2.939 (3)158 (2)
N2—H2D···O6i0.85 (3)2.54 (3)3.041 (2)119.0 (19)
N1—H1C···O3ii0.95 (3)1.87 (3)2.804 (2)168 (2)
N1—H1C···O4ii0.95 (3)2.53 (2)3.073 (2)116.8 (17)
N2—H2C···O71.05 (2)1.83 (2)2.880 (3)176 (2)
N2—H2C···O61.05 (2)2.44 (2)3.068 (2)117.2 (16)
N1—H1B···O3iii0.90 (2)2.06 (3)2.877 (2)149 (2)
N1—H1B···O5iii0.90 (2)2.39 (2)3.180 (3)146 (2)
O2—H2···O40.76 (3)2.07 (3)2.818 (2)166 (3)
O2—H2···O50.76 (3)2.63 (3)3.262 (2)141 (3)
O1—H1A···O7iii0.83 (3)1.99 (3)2.824 (2)173 (3)
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x, y, z1.
 

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