The reaction of 1,1-dimethylhydrazine with a solution of HCl in Et2O affords the anhydrous salt Me2N(H)NH2+·Cl-. The crystal structure, determined by X-ray analysis, consists of two independent [Me2N(H)NH2]+ cations and two Cl- anions, which are connected via hydrogen bonds.
Supporting information
CCDC reference: 274579
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (N-C) = 0.002 Å
- R factor = 0.027
- wR factor = 0.062
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. CL2 .. 2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B .. CL2 .. 2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. CL2 .. 2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. CL2 .. 2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. CL2 .. 2.87 Ang.
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C2 H9 Cl1 N2
Atom count from _chemical_formula_moiety:C2 H9 N2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
0 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: EXPOSE in IPDS Software (Stoe & Cie, 1999); cell refinement: CELL in IPDS Software; data reduction: INTEGRATE in IPDS Software; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C2H9N2+·Cl− | F(000) = 416 |
Mr = 96.56 | Dx = 1.195 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8000 reflections |
a = 9.7305 (9) Å | θ = 2.8–26° |
b = 10.5319 (10) Å | µ = 0.56 mm−1 |
c = 10.4759 (10) Å | T = 193 K |
β = 90.475 (11)° | Needle, light orange |
V = 1073.54 (18) Å3 | 0.3 × 0.12 × 0.12 mm |
Z = 8 | |
Data collection top
Stoe IPDS diffractometer | 1623 reflections with I > 2σ(I) |
ω scans | Rint = 0.041 |
Absorption correction: multi-scan (Blessing, 1995) | θmax = 26°, θmin = 2.7° |
Tmin = 0.853, Tmax = 0.949 | h = −11→11 |
10258 measured reflections | k = −12→12 |
2077 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0392P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.062 | (Δ/σ)max = 0.001 |
S = 0.95 | Δρmax = 0.31 e Å−3 |
2077 reflections | Δρmin = −0.17 e Å−3 |
163 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.6671 (2) | 0.00656 (19) | 0.84566 (17) | 0.0376 (4) | |
C2 | 0.7287 (2) | 0.21319 (17) | 0.93808 (18) | 0.0393 (4) | |
C3 | 0.6365 (2) | 0.04944 (19) | 0.33371 (17) | 0.0374 (4) | |
C4 | 0.8257 (2) | 0.19980 (18) | 0.37108 (18) | 0.0393 (4) | |
N1 | 0.77420 (15) | 0.08222 (12) | 0.91098 (11) | 0.0257 (3) | |
N2 | 0.81135 (15) | 0.02060 (15) | 1.03065 (12) | 0.0307 (3) | |
N3 | 0.72961 (14) | 0.10851 (12) | 0.42932 (11) | 0.0255 (3) | |
N4 | 0.79526 (16) | 0.00937 (14) | 0.50273 (13) | 0.0333 (3) | |
Cl1 | 1.00781 (4) | 0.13637 (4) | 0.71945 (3) | 0.03479 (13) | |
Cl2 | 0.56072 (4) | 0.26381 (3) | 0.61525 (3) | 0.02948 (12) | |
H1 | 0.843 (2) | 0.0885 (16) | 0.8641 (16) | 0.032 (5)* | |
H1A | 0.646 (2) | 0.0507 (19) | 0.7702 (19) | 0.048 (5)* | |
H1B | 0.701 (2) | −0.078 (2) | 0.8323 (17) | 0.040 (5)* | |
H1C | 0.591 (2) | 0.0021 (19) | 0.9024 (19) | 0.049 (6)* | |
H2 | 0.847 (2) | −0.056 (2) | 1.0081 (18) | 0.050 (6)* | |
H2A | 0.699 (2) | 0.2511 (18) | 0.8614 (18) | 0.041 (5)* | |
H2B | 0.807 (2) | 0.2574 (19) | 0.9737 (18) | 0.051 (6)* | |
H2C | 0.656 (2) | 0.2016 (18) | 0.9996 (18) | 0.043 (5)* | |
H3 | 0.878 (2) | 0.0730 (19) | 1.0611 (17) | 0.041 (5)* | |
H3A | 0.695 (2) | 0.0055 (19) | 0.2733 (18) | 0.044 (5)* | |
H3B | 0.577 (2) | −0.008 (2) | 0.3776 (18) | 0.050 (6)* | |
H3C | 0.584 (2) | 0.117 (2) | 0.2975 (18) | 0.049 (6)* | |
H4 | 0.6779 (19) | 0.1505 (17) | 0.4848 (16) | 0.033 (5)* | |
H4A | 0.879 (2) | 0.235 (2) | 0.4381 (19) | 0.050 (6)* | |
H4B | 0.883 (2) | 0.155 (2) | 0.316 (2) | 0.061 (6)* | |
H4C | 0.771 (2) | 0.261 (2) | 0.3247 (18) | 0.052 (6)* | |
H5 | 0.848 (2) | 0.0502 (19) | 0.5584 (19) | 0.044 (5)* | |
H6 | 0.850 (2) | −0.0268 (19) | 0.4479 (19) | 0.048 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0373 (11) | 0.0421 (11) | 0.0333 (8) | −0.0065 (8) | −0.0088 (8) | 0.0004 (8) |
C2 | 0.0454 (12) | 0.0318 (10) | 0.0406 (9) | 0.0079 (8) | −0.0063 (9) | −0.0012 (7) |
C3 | 0.0380 (11) | 0.0386 (10) | 0.0354 (8) | −0.0043 (9) | −0.0072 (8) | −0.0019 (8) |
C4 | 0.0388 (11) | 0.0359 (10) | 0.0433 (9) | −0.0083 (8) | 0.0112 (9) | 0.0044 (8) |
N1 | 0.0250 (8) | 0.0304 (7) | 0.0218 (6) | −0.0005 (6) | 0.0027 (5) | 0.0006 (5) |
N2 | 0.0349 (9) | 0.0329 (8) | 0.0241 (6) | 0.0018 (7) | −0.0033 (6) | 0.0017 (5) |
N3 | 0.0270 (7) | 0.0244 (6) | 0.0250 (6) | −0.0003 (5) | 0.0054 (5) | −0.0029 (5) |
N4 | 0.0390 (9) | 0.0328 (7) | 0.0282 (7) | 0.0030 (7) | −0.0022 (7) | 0.0001 (6) |
Cl1 | 0.0342 (2) | 0.0429 (2) | 0.02733 (18) | −0.00617 (17) | 0.00485 (15) | −0.00714 (15) |
Cl2 | 0.0331 (2) | 0.0306 (2) | 0.02483 (17) | 0.00653 (16) | 0.00486 (14) | 0.00109 (14) |
Geometric parameters (Å, º) top
C1—N1 | 1.476 (2) | C4—N3 | 1.476 (2) |
C1—H1A | 0.94 (2) | C4—H4A | 0.95 (2) |
C1—H1B | 0.96 (2) | C4—H4B | 0.93 (2) |
C1—H1C | 0.96 (2) | C4—H4C | 0.97 (2) |
C2—N1 | 1.477 (2) | N1—N2 | 1.4546 (17) |
C2—H2A | 0.941 (19) | N1—H1 | 0.83 (2) |
C2—H2B | 0.97 (2) | N2—H2 | 0.91 (2) |
C2—H2C | 0.97 (2) | N2—H3 | 0.91 (2) |
C3—N3 | 1.482 (2) | N3—N4 | 1.4428 (18) |
C3—H3A | 0.97 (2) | N3—H4 | 0.890 (19) |
C3—H3B | 0.96 (2) | N4—H5 | 0.89 (2) |
C3—H3C | 0.95 (2) | N4—H6 | 0.87 (2) |
| | | |
N1—C1—H1A | 105.9 (12) | N3—C4—H4C | 107.3 (13) |
N1—C1—H1B | 109.1 (11) | H4A—C4—H4C | 114.0 (17) |
H1A—C1—H1B | 114.3 (16) | H4B—C4—H4C | 110.9 (17) |
N1—C1—H1C | 106.8 (12) | N2—N1—C1 | 109.16 (13) |
H1A—C1—H1C | 112.3 (18) | N2—N1—C2 | 108.89 (12) |
H1B—C1—H1C | 108.3 (17) | C1—N1—C2 | 112.43 (15) |
N1—C2—H2A | 108.9 (12) | N2—N1—H1 | 110.4 (12) |
N1—C2—H2B | 106.7 (12) | C1—N1—H1 | 109.6 (12) |
H2A—C2—H2B | 111.3 (17) | C2—N1—H1 | 106.3 (12) |
N1—C2—H2C | 103.4 (11) | N1—N2—H2 | 105.3 (12) |
H2A—C2—H2C | 113.5 (17) | N1—N2—H3 | 101.7 (11) |
H2B—C2—H2C | 112.5 (16) | H2—N2—H3 | 110.7 (19) |
N3—C3—H3A | 106.5 (11) | N4—N3—C4 | 114.37 (14) |
N3—C3—H3B | 108.1 (11) | N4—N3—C3 | 108.78 (13) |
H3A—C3—H3B | 111.5 (17) | C4—N3—C3 | 112.31 (13) |
N3—C3—H3C | 106.2 (12) | N4—N3—H4 | 105.2 (11) |
H3A—C3—H3C | 114.3 (16) | C4—N3—H4 | 108.1 (12) |
H3B—C3—H3C | 109.8 (17) | C3—N3—H4 | 107.7 (11) |
N3—C4—H4A | 107.3 (12) | N3—N4—H5 | 104.6 (13) |
N3—C4—H4B | 108.0 (14) | N3—N4—H6 | 103.6 (13) |
H4A—C4—H4B | 109.1 (19) | H5—N4—H6 | 107.0 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.83 (2) | 2.27 (2) | 3.0975 (15) | 169.3 (16) |
N2—H2···Cl2i | 0.91 (2) | 2.47 (2) | 3.3513 (16) | 163.4 (16) |
N2—H3···Cl2ii | 0.91 (2) | 2.53 (2) | 3.4342 (16) | 171.6 (15) |
N3—H4···Cl2 | 0.890 (19) | 2.149 (19) | 3.0369 (14) | 175.9 (16) |
N4—H5···Cl1 | 0.89 (2) | 2.46 (2) | 3.3382 (15) | 172.5 (17) |
N4—H6···Cl1iii | 0.87 (2) | 2.52 (2) | 3.3940 (16) | 175.8 (18) |
C1—H1A···Cl2 | 0.94 (2) | 2.89 (2) | 3.768 (2) | 156.8 (16) |
C1—H1B···Cl2i | 0.96 (2) | 2.90 (2) | 3.701 (2) | 141.1 (14) |
C2—H2A···Cl2 | 0.941 (19) | 2.900 (18) | 3.7817 (19) | 156.4 (15) |
C3—H3C···Cl1iv | 0.95 (2) | 2.82 (2) | 3.732 (2) | 160.2 (16) |
C2—H2B···Cl2ii | 0.97 (2) | 2.88 (2) | 3.721 (2) | 146.4 (15) |
C4—H4B···Cl2v | 0.93 (2) | 2.87 (2) | 3.5585 (19) | 132.0 (17) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+2, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x+1/2, −y+1/2, z−1/2. |