S-Methyl 3-[4-(diethyl­amino)benzyl­idene]dithio­carbazate

The title compound, C₁₃H₁₉N₃S₂, is a Schiff base prepared by the reaction of S-methyl­endithio­carbazate and and 4-(diethyl­amino)benzaldehyde. Weak inter­molecular N—H...S hydrogen bonds link the mol­ecules into dimers.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.067
• wR factor = 0.159
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C11     ..       9.07 su

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.29
           From the CIF: _diffrn_reflns_theta_full          28.29
           From the CIF: _reflns_number_total               3557
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3762
           Completeness (_total/calc)             94.55%
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C13 H19 N3 S2

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

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL, Mercury 1.3 (Bruno et al., 2002); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

(I)

Crystal data

C13H19N3S2	Z = 2
Mr = 281.43	F(000) = 300
Triclinic, P1	Dx = 1.235 Mg m^−3
a = 6.9340 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3979 (8) Å	Cell parameters from 1831 reflections
c = 13.8832 (13) Å	θ = 2.9–28.3°
α = 89.343 (2)°	µ = 0.34 mm^−1
β = 84.071 (2)°	T = 297 K
γ = 70.321 (2)°	Block, yellow
V = 756.91 (12) Å^3	0.56 × 0.24 × 0.16 mm

Data collection

Siemens SMART CCD area detector diffractometer	3557 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.9°
ω scans	h = −9→8
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	k = −9→11
Tmin = 0.833, Tmax = 0.948	l = −18→18
4816 measured reflections

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.5524P] where P = (Fo^2 + 2Fc^2)/3
3557 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
S1	0.17958 (15)	0.64367 (13)	0.05704 (5)	0.0746 (3)
S2	−0.00130 (14)	0.82107 (12)	−0.11987 (6)	0.0688 (3)
N1	0.8155 (4)	0.7684 (4)	−0.63664 (17)	0.0665 (8)
N3	0.3844 (4)	0.6587 (3)	−0.10960 (15)	0.0548 (6)
H3A	0.4934	0.6042	−0.0828	0.066*
C1	0.8418 (5)	0.6876 (4)	−0.37717 (19)	0.0502 (7)
H1A	0.9389	0.6655	−0.3329	0.060*
C2	0.9001 (5)	0.7115 (4)	−0.47246 (19)	0.0513 (7)
H2A	1.0351	0.7054	−0.4912	0.062*
C3	0.7590 (5)	0.7448 (4)	−0.54163 (19)	0.0514 (7)
C4	0.5582 (5)	0.7500 (5)	−0.5087 (2)	0.0628 (9)
H4A	0.4606	0.7703	−0.5527	0.075*
C5	0.5027 (5)	0.7260 (4)	−0.4132 (2)	0.0575 (8)
H5A	0.3685	0.7303	−0.3940	0.069*
C6	0.6419 (5)	0.6957 (3)	−0.34507 (18)	0.0459 (7)
C7	0.5880 (5)	0.6710 (4)	−0.24344 (19)	0.0500 (7)
H7A	0.6933	0.6318	−0.2036	0.060*
N2	0.4025 (4)	0.7007 (3)	−0.20630 (16)	0.0533 (6)
C9	0.2024 (5)	0.7010 (4)	−0.05788 (18)	0.0491 (7)
C10	−0.2175 (6)	0.8615 (6)	−0.0290 (3)	0.0863 (12)
H10A	−0.3421	0.9202	−0.0572	0.129*
H10B	−0.2019	0.9296	0.0227	0.129*
H10C	−0.2239	0.7561	−0.0040	0.129*
C11	0.6603 (7)	0.8332 (5)	−0.7069 (3)	0.0802 (11)
H11A	0.5297	0.9018	−0.6730	0.096*
H11B	0.7057	0.9033	−0.7537	0.096*
C12	0.6352 (8)	0.6912 (7)	−0.7565 (4)	0.1158 (18)
H12A	0.5427	0.7325	−0.8051	0.174*
H12B	0.5797	0.6274	−0.7106	0.174*
H12C	0.7665	0.6199	−0.7866	0.174*
C13	1.0225 (5)	0.7648 (4)	−0.6711 (2)	0.0618 (8)
H13A	1.0498	0.7355	−0.7397	0.074*
H13B	1.1216	0.6781	−0.6375	0.074*
C14	1.0493 (6)	0.9315 (5)	−0.6549 (3)	0.0768 (10)
H14A	1.1819	0.9283	−0.6847	0.115*
H14B	1.0396	0.9541	−0.5866	0.115*
H14C	0.9436	1.0192	−0.6831	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0697 (6)	0.0962 (7)	0.0368 (4)	−0.0046 (5)	0.0066 (4)	0.0172 (4)
S2	0.0610 (5)	0.0832 (6)	0.0492 (4)	−0.0075 (4)	−0.0067 (4)	0.0132 (4)
N1	0.0656 (18)	0.105 (2)	0.0366 (12)	−0.0393 (16)	−0.0044 (12)	0.0103 (13)
N3	0.0571 (15)	0.0673 (16)	0.0324 (11)	−0.0120 (12)	−0.0020 (10)	0.0111 (11)
C1	0.0572 (18)	0.0534 (17)	0.0411 (14)	−0.0195 (14)	−0.0080 (13)	0.0069 (12)
C2	0.0501 (17)	0.0613 (19)	0.0435 (15)	−0.0215 (14)	−0.0016 (13)	0.0074 (13)
C3	0.0608 (19)	0.0593 (18)	0.0357 (13)	−0.0239 (15)	−0.0006 (13)	0.0022 (12)
C4	0.055 (2)	0.094 (3)	0.0430 (15)	−0.0294 (18)	−0.0082 (14)	0.0122 (16)
C5	0.0493 (18)	0.077 (2)	0.0445 (15)	−0.0213 (16)	−0.0001 (13)	0.0083 (14)
C6	0.0572 (18)	0.0414 (15)	0.0356 (13)	−0.0137 (13)	0.0009 (12)	0.0035 (11)
C7	0.0593 (19)	0.0499 (17)	0.0380 (14)	−0.0154 (14)	−0.0037 (13)	0.0070 (12)
N2	0.0630 (16)	0.0558 (15)	0.0344 (11)	−0.0132 (12)	0.0015 (11)	0.0077 (10)
C9	0.0567 (18)	0.0512 (17)	0.0346 (13)	−0.0131 (14)	−0.0013 (12)	0.0032 (11)
C10	0.059 (2)	0.108 (3)	0.073 (2)	−0.006 (2)	0.0038 (18)	0.001 (2)
C11	0.092 (3)	0.102 (3)	0.056 (2)	−0.048 (2)	−0.0020 (19)	0.008 (2)
C12	0.130 (4)	0.137 (4)	0.091 (3)	−0.065 (4)	0.014 (3)	−0.033 (3)
C13	0.066 (2)	0.072 (2)	0.0406 (15)	−0.0188 (17)	0.0071 (14)	0.0015 (14)
C14	0.084 (3)	0.081 (3)	0.068 (2)	−0.033 (2)	−0.0047 (19)	0.0208 (19)

Geometric parameters (Å, º)

S1—C9	1.669 (3)	C6—C7	1.453 (4)
S2—C9	1.739 (3)	C7—N2	1.278 (4)
S2—C10	1.797 (4)	C7—H7A	0.9300
N1—C3	1.368 (3)	C10—H10A	0.9600
N1—C13	1.455 (4)	C10—H10B	0.9600
N1—C11	1.489 (5)	C10—H10C	0.9600
N3—C9	1.323 (4)	C11—C12	1.453 (6)
N3—N2	1.388 (3)	C11—H11A	0.9700
N3—H3A	0.8600	C11—H11B	0.9700
C1—C2	1.375 (4)	C12—H12A	0.9600
C1—C6	1.391 (4)	C12—H12B	0.9600
C1—H1A	0.9300	C12—H12C	0.9600
C2—C3	1.400 (4)	C13—C14	1.495 (5)
C2—H2A	0.9300	C13—H13A	0.9700
C3—C4	1.405 (4)	C13—H13B	0.9700
C4—C5	1.374 (4)	C14—H14A	0.9600
C4—H4A	0.9300	C14—H14B	0.9600
C5—C6	1.382 (4)	C14—H14C	0.9600
C5—H5A	0.9300
C9—S2—C10	102.26 (16)	S1—C9—S2	124.79 (18)
C3—N1—C13	122.3 (3)	S2—C10—H10A	109.5
C3—N1—C11	121.7 (3)	S2—C10—H10B	109.5
C13—N1—C11	115.0 (2)	H10A—C10—H10B	109.5
C9—N3—N2	121.1 (2)	S2—C10—H10C	109.5
C9—N3—H3A	119.4	H10A—C10—H10C	109.5
N2—N3—H3A	119.4	H10B—C10—H10C	109.5
C2—C1—C6	122.0 (3)	C12—C11—N1	109.3 (4)
C2—C1—H1A	119.0	C12—C11—H11A	109.8
C6—C1—H1A	119.0	N1—C11—H11A	109.8
C1—C2—C3	120.9 (3)	C12—C11—H11B	109.8
C1—C2—H2A	119.5	N1—C11—H11B	109.8
C3—C2—H2A	119.5	H11A—C11—H11B	108.3
N1—C3—C2	121.4 (3)	C11—C12—H12A	109.5
N1—C3—C4	122.0 (3)	C11—C12—H12B	109.5
C2—C3—C4	116.7 (2)	H12A—C12—H12B	109.5
C5—C4—C3	121.6 (3)	C11—C12—H12C	109.5
C5—C4—H4A	119.2	H12A—C12—H12C	109.5
C3—C4—H4A	119.2	H12B—C12—H12C	109.5
C4—C5—C6	121.4 (3)	N1—C13—C14	111.8 (3)
C4—C5—H5A	119.3	N1—C13—H13A	109.3
C6—C5—H5A	119.3	C14—C13—H13A	109.3
C5—C6—C1	117.4 (2)	N1—C13—H13B	109.3
C5—C6—C7	122.9 (3)	C14—C13—H13B	109.3
C1—C6—C7	119.7 (3)	H13A—C13—H13B	107.9
N2—C7—C6	123.0 (3)	C13—C14—H14A	109.5
N2—C7—H7A	118.5	C13—C14—H14B	109.5
C6—C7—H7A	118.5	H14A—C14—H14B	109.5
C7—N2—N3	114.1 (2)	C13—C14—H14C	109.5
N3—C9—S1	121.2 (2)	H14A—C14—H14C	109.5
N3—C9—S2	114.0 (2)	H14B—C14—H14C	109.5
C6—C1—C2—C3	−0.1 (5)	C2—C1—C6—C7	−179.5 (3)
C13—N1—C3—C2	−1.6 (5)	C5—C6—C7—N2	−11.0 (5)
C11—N1—C3—C2	−169.1 (3)	C1—C6—C7—N2	169.5 (3)
C13—N1—C3—C4	179.4 (3)	C6—C7—N2—N3	176.0 (2)
C11—N1—C3—C4	11.8 (5)	C9—N3—N2—C7	171.6 (3)
C1—C2—C3—N1	−179.9 (3)	N2—N3—C9—S1	177.4 (2)
C1—C2—C3—C4	−0.8 (4)	N2—N3—C9—S2	−3.5 (4)
N1—C3—C4—C5	179.9 (3)	C10—S2—C9—N3	−178.0 (3)
C2—C3—C4—C5	0.8 (5)	C10—S2—C9—S1	1.0 (3)
C3—C4—C5—C6	0.1 (5)	C3—N1—C11—C12	−93.6 (4)
C4—C5—C6—C1	−1.0 (5)	C13—N1—C11—C12	98.0 (4)
C4—C5—C6—C7	179.5 (3)	C3—N1—C13—C14	−83.2 (4)
C2—C1—C6—C5	1.1 (4)	C11—N1—C13—C14	85.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···S1^i	0.86	2.56	3.371 (3)	157

Symmetry code: (i) −x+1, −y+1, −z.