Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C8H12N+·C9H10NS2, is salt formed between a dithio­carbamate and an asymmetric secondary amine. The crystal packing is stabilized by N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017648/bt2046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017648/bt2046Isup2.hkl
Contains datablock I

CCDC reference: 610701

Key indicators

  • Single-crystal X-ray study
  • T = 233 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.096
  • Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - C1 .. 7.81 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S2 - C1 .. 6.01 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C8 H12 N
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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: SHELXL97.

N-methyl(phenyl)methanaminium benzyl(methyl)carbamodithioate top
Crystal data top
C8H12N+·C9H10NS2F(000) = 680
Mr = 318.49Dx = 1.251 Mg m3
Monoclinic, P21/nMelting point: 108 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.0903 (2) ÅCell parameters from 10949 reflections
b = 15.3530 (4) Åθ = 1.0–27.0°
c = 11.3422 (3) ŵ = 0.31 mm1
β = 105.801 (2)°T = 233 K
V = 1690.70 (7) Å3Prism, colourless
Z = 40.3 × 0.25 × 0.15 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3213 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.2°, θmin = 2.3°
φ and ω scansh = 012
10817 measured reflectionsk = 1919
3742 independent reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0391P)2 + 0.5808P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3742 reflectionsΔρmax = 0.37 e Å3
199 parametersΔρmin = 0.45 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (2)
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.

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
xyzUiso*/Ueq
S20.13768 (4)0.45804 (3)0.23104 (4)0.04839 (14)
S10.09407 (5)0.30940 (3)0.05437 (4)0.05503 (16)
N10.21897 (13)0.29528 (8)0.29021 (11)0.0391 (3)
N20.16358 (14)0.47493 (9)0.08379 (12)0.0406 (3)
H2NA0.1315 (19)0.4380 (12)0.0343 (18)0.054 (5)*
H2NB0.093 (2)0.5114 (13)0.1168 (18)0.060 (5)*
C10.15524 (13)0.34995 (10)0.19994 (13)0.0362 (3)
C20.2398 (2)0.20316 (11)0.26845 (17)0.0566 (5)
H2A0.28750.17540.34510.085*
H2B0.29450.19770.21060.085*
H2C0.15120.17530.23530.085*
C30.26701 (15)0.32143 (10)0.41950 (14)0.0409 (3)
H3A0.26190.38500.42520.049*
H3B0.36360.30430.45220.049*
C40.18275 (15)0.28057 (9)0.49624 (13)0.0366 (3)
C50.24707 (17)0.24803 (11)0.61179 (14)0.0438 (4)
H50.34360.24980.64090.053*
C60.1707 (2)0.21303 (12)0.68463 (15)0.0535 (4)
H60.21560.19130.76280.064*
C70.0291 (2)0.20985 (11)0.64319 (17)0.0532 (4)
H70.02270.18590.69260.064*
C80.03597 (18)0.24219 (12)0.52845 (17)0.0533 (4)
H80.13260.24050.49970.064*
C90.04058 (16)0.27708 (11)0.45571 (15)0.0475 (4)
H90.00460.29870.37760.057*
C100.2893 (2)0.51756 (12)0.00862 (15)0.0547 (4)
H10A0.26670.55240.05460.082*
H10B0.32750.55480.06020.082*
H10C0.35640.47350.02920.082*
C110.18462 (17)0.41889 (10)0.18521 (15)0.0448 (4)
H11A0.09520.39590.23220.054*
H11B0.24280.36930.14940.054*
C120.25018 (16)0.46604 (9)0.27113 (13)0.0387 (3)
C130.39146 (17)0.46209 (12)0.25407 (16)0.0494 (4)
H130.44610.42920.18890.059*
C140.45313 (18)0.50605 (14)0.33180 (18)0.0576 (5)
H140.54920.50380.31870.069*
C150.3726 (2)0.55308 (12)0.42839 (16)0.0566 (5)
H150.41390.58340.48110.068*
C160.23196 (19)0.55588 (12)0.44796 (15)0.0511 (4)
H160.17730.58710.51500.061*
C170.17061 (16)0.51286 (11)0.36930 (14)0.0433 (3)
H170.07460.51550.38260.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0524 (3)0.0477 (2)0.0463 (2)0.01634 (17)0.01558 (18)0.00966 (17)
S10.0605 (3)0.0676 (3)0.0355 (2)0.0262 (2)0.01054 (18)0.00061 (19)
N10.0430 (7)0.0389 (6)0.0366 (6)0.0019 (5)0.0131 (5)0.0058 (5)
N20.0438 (7)0.0438 (7)0.0363 (7)0.0047 (6)0.0145 (6)0.0070 (6)
C10.0264 (6)0.0478 (8)0.0369 (7)0.0016 (6)0.0127 (5)0.0084 (6)
C20.0777 (12)0.0402 (9)0.0585 (11)0.0041 (8)0.0297 (10)0.0066 (8)
C30.0376 (7)0.0454 (8)0.0362 (7)0.0016 (6)0.0038 (6)0.0082 (6)
C40.0415 (7)0.0336 (7)0.0335 (7)0.0015 (6)0.0085 (6)0.0007 (6)
C50.0480 (8)0.0459 (8)0.0358 (8)0.0068 (7)0.0086 (6)0.0046 (6)
C60.0747 (12)0.0506 (9)0.0390 (8)0.0127 (8)0.0220 (8)0.0086 (7)
C70.0743 (12)0.0418 (9)0.0557 (10)0.0002 (8)0.0384 (9)0.0006 (7)
C80.0473 (9)0.0558 (10)0.0603 (11)0.0060 (7)0.0209 (8)0.0058 (8)
C90.0429 (8)0.0567 (10)0.0405 (8)0.0008 (7)0.0074 (7)0.0051 (7)
C100.0667 (11)0.0582 (10)0.0417 (9)0.0152 (9)0.0193 (8)0.0050 (8)
C110.0522 (9)0.0399 (8)0.0443 (8)0.0026 (7)0.0166 (7)0.0007 (7)
C120.0434 (8)0.0376 (7)0.0369 (8)0.0010 (6)0.0141 (6)0.0068 (6)
C130.0450 (8)0.0575 (10)0.0466 (9)0.0073 (7)0.0141 (7)0.0045 (8)
C140.0469 (9)0.0738 (12)0.0593 (11)0.0048 (9)0.0265 (8)0.0152 (10)
C150.0735 (12)0.0587 (10)0.0492 (10)0.0116 (9)0.0367 (9)0.0118 (8)
C160.0678 (11)0.0535 (10)0.0355 (8)0.0038 (8)0.0197 (8)0.0016 (7)
C170.0439 (8)0.0504 (9)0.0357 (7)0.0011 (7)0.0110 (6)0.0054 (7)
Geometric parameters (Å, º) top
S2—C11.7157 (16)C7—C81.381 (3)
S1—C11.7144 (15)C7—H70.9400
N1—C11.3446 (18)C8—C91.383 (2)
N1—C21.461 (2)C8—H80.9400
N1—C31.4696 (19)C9—H90.9400
N2—H2NB0.91 (2)C10—H10A0.9700
N2—H2NA0.92 (2)C10—H10B0.9700
N2—C101.475 (2)C10—H10C0.9700
N2—C111.497 (2)C11—C121.504 (2)
N2—H2NA0.92 (2)C11—H11A0.9800
N2—H2NB0.91 (2)C11—H11B0.9800
C2—H2A0.9700C12—C171.384 (2)
C2—H2B0.9700C12—C131.387 (2)
C2—H2C0.9700C13—C141.385 (3)
C3—C41.509 (2)C13—H130.9400
C3—H3A0.9800C14—C151.377 (3)
C3—H3B0.9800C14—H140.9400
C4—C91.383 (2)C15—C161.376 (3)
C4—C51.387 (2)C15—H150.9400
C5—C61.382 (2)C16—C171.384 (2)
C5—H50.9400C16—H160.9400
C6—C71.378 (3)C17—H170.9400
C6—H60.9400
C1—N1—C2122.46 (14)C6—C7—C8119.44 (15)
C1—N1—C3123.28 (13)C6—C7—H7120.3
C2—N1—C3114.18 (12)C8—C7—H7120.3
H2NB—N2—H2NA105.3 (16)C7—C8—C9120.15 (16)
H2NB—N2—C10115.1 (12)C7—C8—H8119.9
H2NA—N2—C10108.2 (11)C9—C8—H8119.9
H2NB—N2—C11107.4 (12)C8—C9—C4120.94 (15)
H2NA—N2—C11105.3 (12)C8—C9—H9119.5
C10—N2—C11114.81 (13)C4—C9—H9119.5
H2NB—N2—H2NA105.3 (16)N2—C10—H10A109.5
C10—N2—H2NA108.2 (11)N2—C10—H10B109.5
C11—N2—H2NA105.3 (12)H10A—C10—H10B109.5
H2NA—N2—H2NB105.3 (16)N2—C10—H10C109.5
C10—N2—H2NB115.1 (12)H10A—C10—H10C109.5
C11—N2—H2NB107.4 (12)H10B—C10—H10C109.5
H2NA—N2—H2NB105.3 (16)N2—C11—C12113.62 (12)
N1—C1—S1118.61 (12)N2—C11—H11A108.8
N1—C1—S2120.13 (11)C12—C11—H11A108.8
S1—C1—S2121.26 (8)N2—C11—H11B108.8
N1—C2—H2A109.5C12—C11—H11B108.8
N1—C2—H2B109.5H11A—C11—H11B107.7
H2A—C2—H2B109.5C17—C12—C13118.96 (14)
N1—C2—H2C109.5C17—C12—C11120.68 (14)
H2A—C2—H2C109.5C13—C12—C11120.35 (14)
H2B—C2—H2C109.5C14—C13—C12120.85 (16)
N1—C3—C4112.17 (12)C14—C13—H13119.6
N1—C3—H3A109.2C12—C13—H13119.6
C4—C3—H3A109.2C15—C14—C13119.45 (16)
N1—C3—H3B109.2C15—C14—H14120.3
C4—C3—H3B109.2C13—C14—H14120.3
H3A—C3—H3B107.9C16—C15—C14120.26 (16)
C9—C4—C5118.43 (14)C16—C15—H15119.9
C9—C4—C3121.38 (13)C14—C15—H15119.9
C5—C4—C3120.16 (13)C15—C16—C17120.24 (16)
C6—C5—C4120.74 (15)C15—C16—H16119.9
C6—C5—H5119.6C17—C16—H16119.9
C4—C5—H5119.6C12—C17—C16120.21 (15)
C7—C6—C5120.31 (15)C12—C17—H17119.9
C7—C6—H6119.8C16—C17—H17119.9
C5—C6—H6119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2NA···S10.917 (19)2.293 (19)3.1630 (15)158.3 (17)
N2—H2NB···S2i0.90 (2)2.38 (2)3.2131 (15)153.0 (17)
Symmetry code: (i) x, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds