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The asymmetric unit of the title compound, C
7H
11N
2+·Br
−·H
2O, consists of one crystallographically independent 1-ethyl-2,3-dimethylimidazolidinium cation, one bromide anion and one water molecule, all of them located in general positions. In the crystal structure, the bromide anions and the water molecules are connected
via O—H
Br hydrogen bonding to form dimers which are located on centres of inversion. In addition, the cations are connected to the water molecules
via weak C—H
O hydrogen bonding.
Supporting information
CCDC reference: 274594
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.054
- wR factor = 0.168
- Data-to-parameter ratio = 23.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: IPDS1 Software (Stoe & Cie, 1996); cell refinement: IPDS1 Software; data reduction: IPDS1 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
1-Ethyl-2,3-dimethylimidazolium bromide monohydrate
top
Crystal data top
C7H13N2+·Br−·H2O | F(000) = 456 |
Mr = 223.12 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/n | Melting point: not measured K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.388 (2) Å | Cell parameters from 1493 reflections |
b = 9.2652 (15) Å | θ = 0–23.2° |
c = 15.117 (4) Å | µ = 3.99 mm−1 |
β = 100.37 (3)° | T = 293 K |
V = 1017.9 (4) Å3 | Shapeless, colorless |
Z = 4 | 0.5 × 0.3 × 0.2 mm |
Data collection top
Stoe IPDS-I diffractometer | 2454 independent reflections |
Radiation source: fine-focus sealed tube | 1550 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
Detector resolution: not measured pixels mm-1 | θmax = 28.1°, θmin = 2.6° |
phi scan | h = −9→9 |
Absorption correction: numerical [X-RED (Stoe & Cie, 2002) and X-SHAPE (Stoe & Cie, 1999)] | k = −12→12 |
Tmin = 0.251, Tmax = 0.455 | l = −19→19 |
11811 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.099P)2] where P = (Fo2 + 2Fc2)/3 |
2454 reflections | (Δ/σ)max < 0.001 |
103 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Special details top
Experimental. A suitable single-crystal was carefully selected under a polarizing microscope
and mounted in a glass capillary. The scattering intensities were collected
with an imaging plate diffractometer (Stoe IPDS-I) equipped with a fine
focus sealed tube X-ray source (Mo Kα, λ = 0.71073 Å) operating at 50 kV
and 30 mA. Intensity data for [C7H13N2]+ [Br]- * H2O were
collected at 293 K by φ scans in 125 frames (0 < φ < 250° exposure time of
6 min) in the 2Θ range 3.8–56.30°·Structure solution and refinement
were carried out using the program SHELXL97 (Sheldrick, 1997). A
numerical absorption correction (X-RED, Stoe & Cie, 2001) was applied
after optimization of the crystal shape (X-SHAPE, Stoe & Cie, 1999)).
The final difference maps were free of any chemically significant features.
The refinement was based on F2 for ALL reflections. |
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 | |
N1 | −0.1176 (5) | 0.6340 (4) | 0.0891 (2) | 0.0395 (7) | |
N3 | −0.1079 (5) | 0.4236 (4) | 0.1491 (3) | 0.0423 (8) | |
C2 | −0.0063 (6) | 0.5296 (4) | 0.1246 (3) | 0.0375 (8) | |
C4 | −0.2917 (6) | 0.4638 (5) | 0.1298 (3) | 0.0497 (11) | |
H4 | −0.3933 | 0.4083 | 0.1411 | 0.060* | |
C5 | −0.2997 (6) | 0.5935 (5) | 0.0926 (4) | 0.0500 (11) | |
H5 | −0.4075 | 0.6486 | 0.0722 | 0.060* | |
C6 | −0.0690 (7) | 0.7749 (5) | 0.0555 (3) | 0.0469 (10) | |
H6A | −0.1637 | 0.8031 | 0.0034 | 0.056* | |
H6B | 0.0500 | 0.7666 | 0.0346 | 0.056* | |
C7 | −0.0544 (10) | 0.8899 (5) | 0.1260 (5) | 0.0692 (16) | |
H7A | −0.0214 | 0.9817 | 0.1009 | 0.104* | |
H7B | 0.0406 | 0.8632 | 0.1774 | 0.104* | |
H7C | −0.1729 | 0.9001 | 0.1459 | 0.104* | |
C8 | −0.0401 (7) | 0.2914 (5) | 0.1977 (4) | 0.0559 (12) | |
H8A | −0.1449 | 0.2319 | 0.2069 | 0.084* | |
H8B | 0.0336 | 0.3169 | 0.2561 | 0.084* | |
H8C | 0.0360 | 0.2371 | 0.1625 | 0.084* | |
C9 | 0.1973 (6) | 0.5293 (5) | 0.1358 (3) | 0.0496 (11) | |
H9A | 0.2365 | 0.6033 | 0.0969 | 0.074* | |
H9B | 0.2393 | 0.4344 | 0.1192 | 0.074* | |
H9C | 0.2507 | 0.5501 | 0.1986 | 0.074* | |
Br1 | 0.06073 (8) | 0.63194 (6) | 0.34915 (4) | 0.0590 (2) | |
O1 | 0.3656 (6) | 0.8309 (4) | 0.0284 (3) | 0.0654 (10) | |
H1 | 0.3837 | 0.9011 | 0.0619 | 0.098* | |
H2 | 0.3920 | 0.8502 | −0.0206 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0445 (18) | 0.0335 (16) | 0.0399 (17) | −0.0042 (15) | 0.0058 (14) | 0.0011 (14) |
N3 | 0.048 (2) | 0.0314 (16) | 0.048 (2) | −0.0034 (15) | 0.0111 (16) | −0.0040 (15) |
C2 | 0.039 (2) | 0.037 (2) | 0.036 (2) | 0.0001 (17) | 0.0064 (16) | −0.0056 (16) |
C4 | 0.033 (2) | 0.050 (3) | 0.066 (3) | −0.0093 (19) | 0.0092 (19) | −0.004 (2) |
C5 | 0.033 (2) | 0.050 (3) | 0.066 (3) | −0.0012 (19) | 0.0046 (19) | −0.004 (2) |
C6 | 0.050 (2) | 0.043 (2) | 0.046 (2) | −0.004 (2) | 0.0054 (19) | 0.0109 (19) |
C7 | 0.098 (5) | 0.035 (2) | 0.076 (4) | −0.010 (3) | 0.018 (3) | 0.000 (2) |
C8 | 0.066 (3) | 0.036 (2) | 0.067 (3) | 0.004 (2) | 0.014 (3) | 0.010 (2) |
C9 | 0.035 (2) | 0.055 (3) | 0.061 (3) | 0.001 (2) | 0.0123 (19) | −0.005 (2) |
Br1 | 0.0657 (4) | 0.0578 (3) | 0.0544 (3) | 0.0051 (2) | 0.0130 (2) | −0.0019 (2) |
O1 | 0.075 (2) | 0.0496 (19) | 0.080 (3) | −0.0085 (18) | 0.036 (2) | 0.0044 (18) |
Geometric parameters (Å, º) top
N1—C2 | 1.319 (5) | C6—H6B | 0.9900 |
N1—C5 | 1.406 (6) | C7—H7A | 0.9800 |
N1—C6 | 1.468 (5) | C7—H7B | 0.9800 |
N3—C2 | 1.329 (6) | C7—H7C | 0.9800 |
N3—C4 | 1.387 (6) | C8—H8A | 0.9800 |
N3—C8 | 1.470 (6) | C8—H8B | 0.9800 |
C2—C9 | 1.484 (6) | C8—H8C | 0.9800 |
C4—C5 | 1.324 (7) | C9—H9A | 0.9800 |
C4—H4 | 0.9500 | C9—H9B | 0.9800 |
C5—H5 | 0.9500 | C9—H9C | 0.9800 |
C6—C7 | 1.498 (7) | O1—H1 | 0.8201 |
C6—H6A | 0.9900 | O1—H2 | 0.8200 |
| | | |
C2—N1—C5 | 108.6 (4) | H6A—C6—H6B | 107.9 |
C2—N1—C6 | 128.2 (4) | C6—C7—H7A | 109.5 |
C5—N1—C6 | 123.0 (4) | C6—C7—H7B | 109.5 |
C2—N3—C4 | 108.9 (4) | H7A—C7—H7B | 109.5 |
C2—N3—C8 | 126.7 (4) | C6—C7—H7C | 109.5 |
C4—N3—C8 | 124.2 (4) | H7A—C7—H7C | 109.5 |
N1—C2—N3 | 108.2 (4) | H7B—C7—H7C | 109.5 |
N1—C2—C9 | 126.3 (4) | N3—C8—H8A | 109.5 |
N3—C2—C9 | 125.4 (4) | N3—C8—H8B | 109.5 |
C5—C4—N3 | 107.5 (4) | H8A—C8—H8B | 109.5 |
C5—C4—H4 | 126.3 | N3—C8—H8C | 109.5 |
N3—C4—H4 | 126.3 | H8A—C8—H8C | 109.5 |
C4—C5—N1 | 106.8 (4) | H8B—C8—H8C | 109.5 |
C4—C5—H5 | 126.6 | C2—C9—H9A | 109.5 |
N1—C5—H5 | 126.6 | C2—C9—H9B | 109.5 |
N1—C6—C7 | 112.2 (4) | H9A—C9—H9B | 109.5 |
N1—C6—H6A | 109.2 | C2—C9—H9C | 109.5 |
C7—C6—H6A | 109.2 | H9A—C9—H9C | 109.5 |
N1—C6—H6B | 109.2 | H9B—C9—H9C | 109.5 |
C7—C6—H6B | 109.2 | H1—O1—H2 | 110.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.95 | 2.39 | 3.321 (6) | 168 |
O1—H1···Br1ii | 0.82 | 2.52 | 3.337 (4) | 174 |
O1—H2···Br1iii | 0.82 | 2.52 | 3.309 (4) | 163 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z−1/2. |
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