N,N′-Bis[2-(dimethyl­amino)eth­yl]dithio­oxamide

In the title compound, C₁₀H₂₂N₄S₂, mol­ecules lie across crystallographic inversion centres. Weak N—H...N and N—H...S hydrogen-bonding inter­actions are observed in the mol­ecular structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.038
• wR factor = 0.116
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        N2'
PLAT301_ALERT_3_B Main Residue  Disorder .........................      38.00 Perc.

Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

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Computing details

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.

N,N'-Bis[2-(dimethylamino)ethyl]dithiooxamide

Crystal data

C10H22N4S2	F(000) = 284
Mr = 262.44	Dx = 1.122 Mg m^−3
Monoclinic, P21/c	Melting point: 365 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.964 (2) Å	Cell parameters from 1018 reflections
b = 7.2840 (16) Å	θ = 3.4–20.3°
c = 11.462 (3) Å	µ = 0.33 mm^−1
β = 110.917 (3)°	T = 293 K
V = 777.1 (3) Å^3	Block, orange
Z = 2	0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1828 independent reflections
Radiation source: fine-focus sealed tube	979 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 27.9°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.902, Tmax = 0.943	k = −9→6
4992 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.0516P] where P = (Fo^2 + 2Fc^2)/3
1828 reflections	(Δ/σ)max = 0.002
123 parameters	Δρmax = 0.16 e Å^−3
36 restraints	Δρmin = −0.11 e Å^−3

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.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.34853 (6)	0.22246 (8)	0.44569 (6)	0.1048 (3)
N1	0.58653 (15)	0.1209 (2)	0.41561 (13)	0.0850 (5)
H1A	0.6623	0.0441	0.4400	0.102*	0.666 (4)
H1B	0.6476	0.0323	0.4115	0.102*	0.334 (4)
C1	0.48805 (17)	0.0890 (2)	0.46279 (14)	0.0692 (5)
N2	0.8349 (6)	0.1618 (11)	0.3602 (6)	0.089 (2)	0.666 (4)
C2	0.5908 (6)	0.2657 (7)	0.3278 (6)	0.0913 (19)	0.666 (4)
H2A	0.6161	0.3817	0.3719	0.110*	0.666 (4)
H2B	0.4965	0.2789	0.2635	0.110*	0.666 (4)
C3	0.6981 (4)	0.2201 (5)	0.2691 (3)	0.0956 (11)	0.666 (4)
H3A	0.6601	0.1228	0.2084	0.115*	0.666 (4)
H3B	0.7134	0.3270	0.2249	0.115*	0.666 (4)
C4	0.9230 (4)	0.0740 (6)	0.2986 (4)	0.1237 (15)	0.666 (4)
H4A	1.0120	0.0343	0.3603	0.186*	0.666 (4)
H4B	0.9424	0.1599	0.2431	0.186*	0.666 (4)
H4C	0.8728	−0.0302	0.2519	0.186*	0.666 (4)
C5	0.9123 (6)	0.3131 (7)	0.4366 (4)	0.1323 (19)	0.666 (4)
H5A	1.0034	0.2704	0.4931	0.198*	0.666 (4)
H5B	0.8574	0.3619	0.4833	0.198*	0.666 (4)
H5C	0.9273	0.4073	0.3840	0.198*	0.666 (4)
N2'	0.8247 (10)	0.1946 (19)	0.3609 (11)	0.077 (4)	0.334 (4)
C2'	0.5945 (11)	0.3100 (13)	0.3685 (13)	0.098 (4)	0.334 (4)
H2'A	0.5599	0.3980	0.4147	0.118*	0.334 (4)
H2'B	0.5338	0.3182	0.2810	0.118*	0.334 (4)
C3'	0.7503 (6)	0.3553 (8)	0.3838 (6)	0.087 (2)	0.334 (4)
H3'A	0.7510	0.4520	0.3258	0.104*	0.334 (4)
H3'B	0.8009	0.4000	0.4679	0.104*	0.334 (4)
C4'	0.7820 (10)	0.1586 (13)	0.2265 (7)	0.138 (3)	0.334 (4)
H4'A	0.6822	0.1255	0.1932	0.207*	0.334 (4)
H4'B	0.8387	0.0598	0.2132	0.207*	0.334 (4)
H4'C	0.7971	0.2670	0.1851	0.207*	0.334 (4)
C5'	0.9798 (7)	0.2200 (14)	0.4172 (9)	0.132 (3)	0.334 (4)
H5'A	1.0277	0.1159	0.3984	0.198*	0.334 (4)
H5'B	1.0069	0.2317	0.5060	0.198*	0.334 (4)
H5'C	1.0069	0.3291	0.3840	0.198*	0.334 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0879 (4)	0.0858 (4)	0.1471 (6)	0.0242 (3)	0.0499 (4)	0.0344 (3)
N1	0.0762 (9)	0.0827 (10)	0.1000 (11)	0.0090 (8)	0.0362 (8)	0.0303 (8)
C1	0.0647 (9)	0.0629 (10)	0.0766 (11)	−0.0026 (8)	0.0212 (8)	0.0063 (7)
N2	0.087 (4)	0.096 (4)	0.085 (4)	−0.017 (2)	0.033 (3)	−0.011 (2)
C2	0.093 (3)	0.090 (3)	0.097 (4)	0.015 (2)	0.043 (2)	0.032 (3)
C3	0.111 (3)	0.093 (2)	0.087 (2)	−0.0183 (19)	0.042 (2)	0.0084 (17)
C4	0.114 (3)	0.143 (3)	0.130 (3)	−0.013 (3)	0.064 (3)	−0.021 (3)
C5	0.150 (5)	0.141 (4)	0.111 (3)	−0.061 (4)	0.052 (3)	−0.041 (3)
N2'	0.079 (7)	0.070 (5)	0.097 (9)	−0.020 (4)	0.049 (7)	0.001 (4)
C2'	0.121 (7)	0.091 (6)	0.110 (9)	−0.001 (5)	0.073 (6)	0.032 (6)
C3'	0.095 (5)	0.068 (4)	0.105 (4)	−0.009 (3)	0.046 (4)	0.011 (3)
C4'	0.149 (7)	0.143 (6)	0.135 (6)	−0.011 (5)	0.068 (5)	−0.027 (5)
C5'	0.098 (5)	0.133 (7)	0.173 (8)	−0.007 (5)	0.057 (5)	0.025 (6)

Geometric parameters (Å, º)

S1—C1	1.6496 (17)	C5—H5A	0.96
N1—C1	1.2993 (19)	C5—H5B	0.96
N1—C2	1.469 (4)	C5—H5C	0.96
N1—C2'	1.492 (7)	N2'—C5'	1.458 (9)
N1—H1A	0.90	N2'—C3'	1.459 (9)
N1—H1B	0.90	N2'—C4'	1.468 (9)
C1—C1^i	1.524 (3)	C2'—C3'	1.535 (9)
N2—C5	1.447 (6)	C2'—H2'A	0.97
N2—C3	1.453 (6)	C2'—H2'B	0.97
N2—C4	1.456 (6)	C3'—H3'A	0.97
C2—C3	1.491 (6)	C3'—H3'B	0.97
C2—H2A	0.97	C4'—H4'A	0.96
C2—H2B	0.97	C4'—H4'B	0.96
C3—H3A	0.97	C4'—H4'C	0.96
C3—H3B	0.97	C5'—H5'A	0.96
C4—H4A	0.96	C5'—H5'B	0.96
C4—H4B	0.96	C5'—H5'C	0.96
C4—H4C	0.96
C1—N1—C2	128.6 (2)	C5'—N2'—C4'	110.6 (8)
C1—N1—C2'	117.5 (5)	C3'—N2'—C4'	110.9 (9)
C1—N1—H1A	115.7	N1—C2'—C3'	109.8 (7)
C2—N1—H1A	115.7	N1—C2'—H2'A	109.7
C2'—N1—H1A	122.6	C3'—C2'—H2'A	109.7
C1—N1—H1B	121.3	N1—C2'—H2'B	109.7
C2—N1—H1B	107.1	C3'—C2'—H2'B	109.7
C2'—N1—H1B	121.3	H2'A—C2'—H2'B	108.2
N1—C1—C1^i	113.26 (18)	N2'—C3'—C2'	111.4 (7)
N1—C1—S1	125.09 (13)	N2'—C3'—H3'A	109.3
C1^i—C1—S1	121.65 (17)	C2'—C3'—H3'A	109.3
C5—N2—C3	111.9 (6)	N2'—C3'—H3'B	109.3
C5—N2—C4	110.2 (5)	C2'—C3'—H3'B	109.3
C3—N2—C4	110.7 (5)	H3'A—C3'—H3'B	108.0
N1—C2—C3	110.5 (3)	N2'—C4'—H4'A	109.5
N1—C2—H2A	109.6	N2'—C4'—H4'B	109.5
C3—C2—H2A	109.6	H4'A—C4'—H4'B	109.5
N1—C2—H2B	109.6	N2'—C4'—H4'C	109.5
C3—C2—H2B	109.6	H4'A—C4'—H4'C	109.5
H2A—C2—H2B	108.1	H4'B—C4'—H4'C	109.5
N2—C3—C2	112.4 (4)	N2'—C5'—H5'A	109.5
N2—C3—H3A	109.1	N2'—C5'—H5'B	109.5
C2—C3—H3A	109.1	H5'A—C5'—H5'B	109.5
N2—C3—H3B	109.1	N2'—C5'—H5'C	109.5
C2—C3—H3B	109.1	H5'A—C5'—H5'C	109.5
H3A—C3—H3B	107.9	H5'B—C5'—H5'C	109.5
C5'—N2'—C3'	110.2 (8)
C2—N1—C1—C1^i	172.4 (4)	C4—N2—C3—C2	165.2 (5)
C2'—N1—C1—C1^i	−165.3 (6)	N1—C2—C3—N2	−47.4 (6)
C2—N1—C1—S1	−7.2 (4)	C1—N1—C2'—C3'	149.3 (6)
C2'—N1—C1—S1	15.1 (7)	C2—N1—C2'—C3'	−84.1 (16)
C1—N1—C2—C3	−163.0 (3)	C5'—N2'—C3'—C2'	−160.0 (9)
C2'—N1—C2—C3	131.3 (18)	C4'—N2'—C3'—C2'	77.3 (11)
C5—N2—C3—C2	−71.5 (7)	N1—C2'—C3'—N2'	36.6 (12)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1^i	0.90	2.37	2.910 (2)	119
N1—H1B···N2	0.90	2.35	2.782 (7)	110

Symmetry code: (i) −x+1, −y, −z+1.