Literature DB >> 21581442

Benzyl N'-benzhydrylidene-hydrazine-carbodithio-ate.

Bing-Xiang Zhang1.   

Abstract

In the title mol-ecule, C(21)H(18)N(2)S(2), the C=N-N angle of 117.6 (2)° is significantly smaller than the ideal value of 120° expected for sp(2)-hybridized N atoms. This is probably a consequence of repulsion between the nitro-gen lone pairs and the adjacent N atom, as suggested in Zheng, Qiu, Lin & Liu [Acta Cryst. (2006), E62, o1913-o1914]. The two neighbouring benzene rings form a dihedral angle of 75.95 (3)° with each other, while subtending dihedral angles of 84.18 (3) and 8.44 (2)° with the third ring in the structure.

Entities:  

Year:  2008        PMID： 21581442      PMCID： PMC2959849          DOI： 10.1107/S1600536808039408

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature on ligands derived from S-benzyl­dithio­carbazate (SBDTC), see: Ali et al. (2002 ▶, 2008 ▶); Crouse et al. (2004 ▶); Tarafder et al. (2001 ▶, 2008 ▶); Zheng et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H18N2S2 M = 362.49 Monoclinic, a = 20.2903 (14) Å b = 9.0951 (6) Å c = 10.5818 (7) Å β = 103.9240 (10)° V = 1895.4 (2) Å3 Z = 4 Mo Kα radiation μ = 0.29 mm−1 T = 295 (2) K 0.12 × 0.10 × 0.06 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.967, T max = 0.983 9776 measured reflections 3363 independent reflections 2191 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.116 S = 1.05 3363 reflections 214 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039408/bg2222sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039408/bg2222Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H18N2S2F000 = 760
Mr = 362.49Dx = 1.270 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1615 reflections
a = 20.2903 (14) Åθ = 3.0–22.7º
b = 9.0951 (6) ŵ = 0.29 mm−1
c = 10.5818 (7) ÅT = 295 (2) K
β = 103.9240 (10)ºBlock, yellow
V = 1895.4 (2) Å30.12 × 0.10 × 0.06 mm
Z = 4
Bruker APEX2 CCD area-detector diffractometer3363 independent reflections
Radiation source: fine-focus sealed tube2191 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 295(2) Kθmax = 25.1º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −24→24
Tmin = 0.967, Tmax = 0.983k = −10→10
9776 measured reflectionsl = −11→12
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.116  w = 1/[σ2(Fo2) + (0.0462P)2 + 0.2919P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3363 reflectionsΔρmax = 0.22 e Å−3
214 parametersΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
S10.29194 (4)0.73862 (8)0.23650 (8)0.0593 (2)
S20.15831 (4)0.59677 (8)0.10325 (8)0.0636 (3)
N10.17341 (11)0.8548 (2)0.2139 (2)0.0539 (6)
H10.12990.86300.19090.065*
N20.21181 (11)0.9673 (2)0.2809 (2)0.0508 (6)
C10.39011 (8)0.5783 (2)0.1752 (2)0.0578 (8)
C20.41212 (13)0.6495 (2)0.0766 (2)0.0836 (10)
H20.38070.69090.00700.100*
C30.48112 (15)0.6589 (3)0.0820 (3)0.1024 (13)
H30.49580.70650.01600.123*
C40.52811 (9)0.5971 (3)0.1861 (3)0.1042 (14)
H40.57430.60340.18970.125*
C50.50611 (11)0.5259 (3)0.2847 (3)0.1084 (14)
H50.53760.48450.35430.130*
C60.43711 (12)0.5165 (3)0.2793 (2)0.0868 (11)
H60.42240.46890.34520.104*
C70.31560 (14)0.5689 (3)0.1698 (4)0.0709 (9)
H7A0.30650.48570.22040.085*
H7B0.28980.55660.08050.085*
C80.20349 (13)0.7318 (3)0.1840 (2)0.0475 (7)
C90.18138 (13)1.0901 (3)0.2909 (2)0.0450 (6)
C100.22361 (13)1.2075 (3)0.3651 (2)0.0449 (6)
C110.29263 (14)1.1870 (3)0.4165 (3)0.0603 (8)
H110.31291.09970.40000.072*
C120.33158 (15)1.2931 (3)0.4912 (3)0.0714 (9)
H120.37771.27700.52560.086*
C130.30214 (17)1.4240 (3)0.5153 (3)0.0718 (9)
H130.32841.49590.56640.086*
C140.23479 (16)1.4474 (3)0.4641 (3)0.0664 (8)
H140.21531.53620.47920.080*
C150.19518 (15)1.3404 (3)0.3898 (3)0.0554 (7)
H150.14911.35740.35590.067*
C160.10755 (13)1.1135 (3)0.2328 (2)0.0437 (6)
C170.05888 (14)1.0439 (3)0.2829 (3)0.0564 (7)
H170.07230.98290.35500.068*
C18−0.00925 (15)1.0638 (3)0.2275 (3)0.0653 (8)
H18−0.04141.01760.26340.078*
C19−0.02962 (16)1.1503 (3)0.1210 (3)0.0664 (9)
H19−0.07571.16320.08390.080*
C200.01760 (16)1.2191 (3)0.0678 (3)0.0670 (8)
H200.00351.2776−0.00580.080*
C210.08623 (15)1.2016 (3)0.1237 (3)0.0569 (7)
H210.11811.24910.08800.068*
U11U22U33U12U13U23
S10.0445 (4)0.0491 (4)0.0788 (6)0.0040 (3)0.0042 (4)−0.0127 (4)
S20.0521 (5)0.0564 (5)0.0746 (6)−0.0006 (4)0.0000 (4)−0.0137 (4)
N10.0414 (13)0.0488 (13)0.0692 (16)0.0060 (11)0.0091 (12)−0.0080 (12)
N20.0458 (14)0.0466 (13)0.0590 (15)0.0028 (11)0.0109 (11)−0.0066 (12)
C10.0502 (18)0.0447 (16)0.075 (2)0.0061 (14)0.0092 (16)−0.0101 (16)
C20.079 (3)0.085 (2)0.083 (3)0.004 (2)0.012 (2)0.005 (2)
C30.092 (3)0.112 (3)0.113 (3)−0.017 (3)0.043 (3)−0.008 (3)
C40.056 (2)0.103 (3)0.157 (4)−0.003 (2)0.032 (3)−0.015 (3)
C50.055 (2)0.116 (3)0.142 (4)0.008 (2)0.000 (2)0.022 (3)
C60.057 (2)0.096 (3)0.105 (3)0.004 (2)0.013 (2)0.022 (2)
C70.0489 (18)0.0562 (18)0.106 (3)0.0071 (15)0.0148 (17)−0.0217 (19)
C80.0460 (16)0.0449 (15)0.0490 (16)0.0064 (13)0.0061 (13)0.0026 (13)
C90.0434 (15)0.0456 (15)0.0471 (16)0.0044 (13)0.0131 (13)0.0009 (13)
C100.0455 (16)0.0438 (14)0.0474 (16)−0.0001 (13)0.0149 (13)0.0013 (13)
C110.0478 (18)0.0486 (16)0.085 (2)−0.0010 (14)0.0170 (16)−0.0034 (17)
C120.0443 (18)0.069 (2)0.096 (3)−0.0064 (16)0.0091 (17)−0.006 (2)
C130.068 (2)0.066 (2)0.081 (2)−0.0139 (18)0.0166 (19)−0.0177 (18)
C140.065 (2)0.0560 (18)0.078 (2)0.0044 (16)0.0167 (18)−0.0150 (17)
C150.0504 (17)0.0555 (17)0.0610 (19)0.0064 (14)0.0148 (15)−0.0089 (15)
C160.0435 (16)0.0386 (14)0.0478 (16)0.0057 (12)0.0087 (13)−0.0025 (13)
C170.0494 (18)0.0600 (18)0.0606 (18)0.0050 (14)0.0145 (15)0.0111 (15)
C180.0477 (19)0.075 (2)0.074 (2)−0.0001 (16)0.0154 (16)0.0044 (19)
C190.0477 (19)0.065 (2)0.078 (2)0.0080 (16)−0.0017 (17)−0.0048 (18)
C200.067 (2)0.066 (2)0.060 (2)0.0142 (17)−0.0012 (17)0.0090 (17)
C210.0591 (19)0.0528 (16)0.0591 (18)0.0061 (15)0.0148 (15)0.0070 (15)
S1—C81.747 (3)C10—C111.388 (4)
S1—C71.810 (3)C10—C151.391 (3)
S2—C81.643 (3)C11—C121.371 (4)
N1—C81.348 (3)C11—H110.9300
N1—N21.375 (3)C12—C131.383 (4)
N1—H10.8600C12—H120.9300
N2—C91.293 (3)C13—C141.360 (4)
C1—C21.3900C13—H130.9300
C1—C61.3900C14—C151.381 (4)
C1—C71.501 (3)C14—H140.9300
C2—C31.3900C15—H150.9300
C2—H20.9300C16—C171.381 (4)
C3—C41.3900C16—C211.386 (3)
C3—H30.9300C17—C181.377 (4)
C4—C51.3900C17—H170.9300
C4—H40.9300C18—C191.355 (4)
C5—C61.3900C18—H180.9300
C5—H50.9300C19—C201.373 (4)
C6—H60.9300C19—H190.9300
C7—H7A0.9700C20—C211.385 (4)
C7—H7B0.9700C20—H200.9300
C9—C101.472 (3)C21—H210.9300
C9—C161.491 (3)
C8—S1—C7101.19 (13)C11—C10—C9121.0 (2)
C8—N1—N2120.4 (2)C15—C10—C9121.1 (2)
C8—N1—H1119.8C12—C11—C10121.3 (3)
N2—N1—H1119.8C12—C11—H11119.4
C9—N2—N1117.6 (2)C10—C11—H11119.4
C2—C1—C6120.0C11—C12—C13119.8 (3)
C2—C1—C7120.0 (2)C11—C12—H12120.1
C6—C1—C7120.0 (2)C13—C12—H12120.1
C3—C2—C1120.0C14—C13—C12119.9 (3)
C3—C2—H2120.0C14—C13—H13120.0
C1—C2—H2120.0C12—C13—H13120.0
C2—C3—C4120.0C13—C14—C15120.5 (3)
C2—C3—H3120.0C13—C14—H14119.7
C4—C3—H3120.0C15—C14—H14119.7
C5—C4—C3120.0C14—C15—C10120.6 (3)
C5—C4—H4120.0C14—C15—H15119.7
C3—C4—H4120.0C10—C15—H15119.7
C4—C5—C6120.0C17—C16—C21118.4 (3)
C4—C5—H5120.0C17—C16—C9121.1 (2)
C6—C5—H5120.0C21—C16—C9120.5 (2)
C5—C6—C1120.0C18—C17—C16120.9 (3)
C5—C6—H6120.0C18—C17—H17119.5
C1—C6—H6120.0C16—C17—H17119.5
C1—C7—S1107.18 (18)C19—C18—C17120.2 (3)
C1—C7—H7A110.3C19—C18—H18119.9
S1—C7—H7A110.3C17—C18—H18119.9
C1—C7—H7B110.3C18—C19—C20120.1 (3)
S1—C7—H7B110.3C18—C19—H19119.9
H7A—C7—H7B108.5C20—C19—H19119.9
N1—C8—S2121.0 (2)C19—C20—C21120.1 (3)
N1—C8—S1112.58 (19)C19—C20—H20119.9
S2—C8—S1126.42 (15)C21—C20—H20119.9
N2—C9—C10116.3 (2)C20—C21—C16120.2 (3)
N2—C9—C16122.8 (2)C20—C21—H21119.9
C10—C9—C16120.9 (2)C16—C21—H21119.9
C11—C10—C15117.9 (3)
C8—N1—N2—C9170.5 (2)C16—C9—C10—C153.9 (4)
C6—C1—C2—C30.0C15—C10—C11—C121.1 (4)
C7—C1—C2—C3179.7 (2)C9—C10—C11—C12−176.6 (3)
C1—C2—C3—C40.0C10—C11—C12—C13−0.7 (5)
C2—C3—C4—C50.0C11—C12—C13—C14−0.4 (5)
C3—C4—C5—C60.0C12—C13—C14—C151.0 (5)
C4—C5—C6—C10.0C13—C14—C15—C10−0.6 (5)
C2—C1—C6—C50.0C11—C10—C15—C14−0.5 (4)
C7—C1—C6—C5−179.7 (2)C9—C10—C15—C14177.3 (2)
C2—C1—C7—S1−83.8 (2)N2—C9—C16—C1770.2 (3)
C6—C1—C7—S195.8 (2)C10—C9—C16—C17−109.1 (3)
C8—S1—C7—C1164.8 (2)N2—C9—C16—C21−107.4 (3)
N2—N1—C8—S2−179.69 (18)C10—C9—C16—C2173.4 (3)
N2—N1—C8—S1−1.2 (3)C21—C16—C17—C18−1.2 (4)
C7—S1—C8—N1−175.2 (2)C9—C16—C17—C18−178.8 (3)
C7—S1—C8—S23.2 (2)C16—C17—C18—C191.1 (4)
N1—N2—C9—C10179.0 (2)C17—C18—C19—C20−0.1 (5)
N1—N2—C9—C16−0.3 (4)C18—C19—C20—C21−0.7 (4)
N2—C9—C10—C112.3 (4)C19—C20—C21—C160.6 (4)
C16—C9—C10—C11−178.4 (2)C17—C16—C21—C200.3 (4)
N2—C9—C10—C15−175.4 (2)C9—C16—C21—C20178.0 (2)
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
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Authors:  Mohammad Akbar Ali; Aminul Huq Mirza; Raymond J Butcher; M T H Tarafder; Tan Boon Keat; A Manaf Ali
Journal:  J Inorg Biochem       Date:  2002-11-25       Impact factor: 4.155

3.  Bis[benzyl N'-(3-phenyl-prop-2-enyl-idene)hydrazinecarbodithio-ato-κN',S]copper(II).

Authors:  M T H Tarafder; M Toihidul Islam; M A A A A Islam; Suchada Chantrapromma; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-01-25
  3 in total

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