1,1-Di­methyl­hydrazinium chloride

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.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](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

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Computing details

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).

(I)

Crystal data

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) Å^3	0.3 × 0.12 × 0.12 mm
Z = 8

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0392P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···Cl2^i	0.91 (2)	2.47 (2)	3.3513 (16)	163.4 (16)
N2—H3···Cl2^ii	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···Cl1^iii	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···Cl2^i	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···Cl1^iv	0.95 (2)	2.82 (2)	3.732 (2)	160.2 (16)
C2—H2B···Cl2^ii	0.97 (2)	2.88 (2)	3.721 (2)	146.4 (15)
C4—H4B···Cl2^v	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.