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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2112.
Published online 2009 August 8. doi:  10.1107/S1600536809030645
PMCID: PMC2970103

2-(3,5-Di-tert-butyl-4-hydroxy­benzyl­sulfan­yl)-N′-(3-methoxy­benzyl­idene)acetohydrazide

Abstract

The title compound, C25H34N2O3S, is a derivative of N′-benzyl­ideneacetohydrazide having substituents on the acetyl and benzylidenyl parts, and displays a planar Ccarbon­yl—NH—NCanis­yl fragment [torsion angle = 174.9 (3)°]. The –NH– unit forms an N—H(...)O hydrogen bond with the carbonyl O atom of an inversion-related mol­ecule.

Related literature

For N-(benzyl­idene)acetohydrazide, see: Litvinov et al. (1991 [triangle]).

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Object name is e-65-o2112-scheme1.jpg

Experimental

Crystal data

  • C25H34N2O3S
  • M r = 442.60
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2112-efi1.jpg
  • a = 5.9952 (2) Å
  • b = 10.3199 (3) Å
  • c = 20.6141 (7) Å
  • α = 97.279 (2)°
  • β = 95.916 (2)°
  • γ = 99.981 (2)°
  • V = 1235.72 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 223 K
  • 0.35 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.947, T max = 0.984
  • 8285 measured reflections
  • 4294 independent reflections
  • 2577 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.075
  • wR(F 2) = 0.219
  • S = 1.06
  • 4294 reflections
  • 287 parameters
  • H-atom parameters constrained
  • Δρmax = 0.61 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030645/xu2573sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030645/xu2573Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-(3,5-Di-tert-butyl-4-hydroxybenzylthio)acetohydrazine (0.5 g, 1.54 mmol) and 3-methoxybenzaldehyde (0.21 g, 1.54 mmol) were heated in toluene (10 ml) for 4 h in the presence of p-toluene sulphonic acid as catalyst. The cool mixture was poured onto ice; the resulting solid was collected, dried and recrystallized from toluene in 70% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The imino H-atom was similarly treated (N–H 0.88 Å).; the hydroxy H-atom was placed in a position such that all H···H contacts exceeded 2.0 Å (O–H 0.84 Å).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C25H34N2O3S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C25H34N2O3SZ = 2
Mr = 442.60F(000) = 476
Triclinic, P1Dx = 1.190 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9952 (2) ÅCell parameters from 1620 reflections
b = 10.3199 (3) Åθ = 2.6–21.7°
c = 20.6141 (7) ŵ = 0.16 mm1
α = 97.279 (2)°T = 223 K
β = 95.916 (2)°Prism, colorless
γ = 99.981 (2)°0.35 × 0.10 × 0.10 mm
V = 1235.72 (7) Å3

Data collection

Bruker SMART APEX diffractometer4294 independent reflections
Radiation source: fine-focus sealed tube2577 reflections with I > 2σ(I)
graphiteRint = 0.035
ω scansθmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.947, Tmax = 0.984k = −12→12
8285 measured reflectionsl = −24→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.1218P)2] where P = (Fo2 + 2Fc2)/3
4294 reflections(Δ/σ)max = 0.001
287 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = −0.27 e Å3

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 (Å2)

xyzUiso*/Ueq
S10.75715 (19)0.78337 (10)0.36105 (5)0.0691 (4)
O10.1621 (4)0.5619 (2)0.06464 (11)0.0613 (8)
H1O0.25380.50930.06050.092*
O20.4442 (5)0.5039 (2)0.40994 (12)0.0635 (8)
O31.6583 (5)0.8943 (3)0.72616 (13)0.0731 (9)
N10.7590 (5)0.5928 (3)0.48032 (14)0.0545 (8)
H10.69260.56600.51370.065*
N20.9784 (5)0.6642 (3)0.49141 (14)0.0531 (8)
C10.2353 (5)0.6087 (3)0.13041 (16)0.0433 (8)
C20.1613 (5)0.5357 (3)0.17936 (15)0.0400 (8)
C30.2413 (6)0.5907 (3)0.24438 (16)0.0435 (8)
H30.19650.54250.27810.052*
C40.3841 (6)0.7132 (3)0.26141 (15)0.0424 (8)
C50.4527 (6)0.7824 (3)0.21091 (16)0.0454 (9)
H50.55170.86540.22210.054*
C60.3814 (5)0.7343 (3)0.14524 (16)0.0432 (9)
C7−0.0028 (6)0.3992 (3)0.16267 (18)0.0495 (9)
C8−0.0615 (7)0.3430 (4)0.22584 (19)0.0628 (11)
H8A0.07780.33300.25160.094*
H8B−0.16230.25700.21410.094*
H8C−0.13670.40360.25170.094*
C90.1096 (7)0.2961 (4)0.1244 (2)0.0632 (11)
H9A0.15370.32750.08430.095*
H9B0.00230.21240.11320.095*
H9C0.24400.28340.15150.095*
C10−0.2303 (7)0.4132 (4)0.1249 (2)0.0725 (13)
H10A−0.20180.44750.08420.109*
H10B−0.30190.47410.15180.109*
H10C−0.33070.32680.11470.109*
C110.4605 (6)0.8127 (4)0.09063 (17)0.0538 (10)
C120.2542 (7)0.8470 (4)0.04992 (19)0.0673 (12)
H12A0.15210.76560.02910.101*
H12B0.30700.89820.01630.101*
H12C0.17350.89890.07870.101*
C130.6181 (8)0.9471 (4)0.1203 (2)0.0835 (15)
H13A0.75360.93060.14540.125*
H13B0.53720.99880.14900.125*
H13C0.66210.99590.08490.125*
C140.5967 (7)0.7360 (5)0.0464 (2)0.0770 (14)
H14A0.73160.72100.07240.115*
H14B0.64240.78700.01190.115*
H14C0.50300.65110.02660.115*
C150.4592 (7)0.7738 (3)0.33293 (17)0.0567 (10)
H15A0.36800.72110.36070.068*
H15B0.42530.86370.33920.068*
C160.7607 (7)0.6107 (4)0.36385 (18)0.0634 (11)
H16A0.68440.55810.32200.076*
H16B0.91910.59760.36930.076*
C170.6438 (7)0.5632 (3)0.41904 (18)0.0519 (9)
C181.0622 (6)0.6942 (3)0.55202 (18)0.0484 (9)
H180.97390.66580.58450.058*
C191.2932 (6)0.7721 (3)0.57209 (17)0.0456 (9)
C201.4309 (7)0.8176 (4)0.52624 (19)0.0574 (10)
H201.37570.80050.48100.069*
C211.6485 (8)0.8877 (4)0.5475 (2)0.0653 (11)
H211.74180.91770.51640.078*
C221.7322 (7)0.9150 (3)0.6137 (2)0.0547 (10)
H221.88150.96260.62760.066*
C231.5954 (7)0.8718 (3)0.65910 (18)0.0519 (9)
C241.3768 (6)0.8000 (3)0.63807 (17)0.0475 (9)
H241.28430.76980.66930.057*
C251.8769 (8)0.9736 (5)0.7502 (2)0.0793 (14)
H25A1.90130.98190.79790.119*
H25B1.88431.06120.73720.119*
H25C1.99400.93190.73180.119*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0859 (8)0.0701 (7)0.0346 (6)−0.0270 (6)−0.0044 (5)0.0117 (4)
O10.0721 (17)0.0705 (17)0.0310 (14)−0.0100 (14)−0.0009 (12)0.0066 (11)
O20.085 (2)0.0483 (15)0.0520 (17)0.0036 (14)−0.0108 (14)0.0139 (12)
O30.082 (2)0.0767 (19)0.0480 (17)−0.0086 (16)−0.0075 (14)0.0083 (13)
N10.070 (2)0.0470 (17)0.0455 (19)0.0155 (16)−0.0058 (16)0.0090 (13)
N20.063 (2)0.0553 (18)0.0430 (19)0.0242 (16)−0.0048 (15)0.0065 (14)
C10.0435 (19)0.054 (2)0.0297 (18)0.0018 (16)0.0059 (14)0.0076 (15)
C20.0431 (18)0.0427 (19)0.0349 (19)0.0042 (15)0.0099 (15)0.0092 (14)
C30.055 (2)0.0402 (19)0.038 (2)0.0082 (16)0.0128 (16)0.0129 (15)
C40.059 (2)0.0423 (19)0.0268 (18)0.0117 (16)0.0039 (15)0.0062 (14)
C50.055 (2)0.0417 (18)0.0359 (19)−0.0017 (16)−0.0001 (15)0.0112 (14)
C60.0425 (19)0.050 (2)0.0348 (19)−0.0036 (16)0.0046 (15)0.0146 (15)
C70.050 (2)0.048 (2)0.048 (2)−0.0032 (17)0.0141 (17)0.0076 (16)
C80.080 (3)0.049 (2)0.060 (3)−0.002 (2)0.026 (2)0.0144 (18)
C90.070 (3)0.051 (2)0.064 (3)−0.003 (2)0.019 (2)−0.0008 (19)
C100.052 (2)0.072 (3)0.087 (3)−0.010 (2)0.005 (2)0.019 (2)
C110.058 (2)0.063 (2)0.034 (2)−0.0093 (19)−0.0006 (17)0.0154 (17)
C120.072 (3)0.078 (3)0.049 (2)−0.004 (2)0.000 (2)0.033 (2)
C130.097 (3)0.080 (3)0.056 (3)−0.039 (3)−0.006 (2)0.031 (2)
C140.064 (3)0.111 (4)0.054 (3)−0.007 (3)0.019 (2)0.027 (2)
C150.091 (3)0.0354 (19)0.043 (2)0.0132 (19)0.004 (2)0.0085 (15)
C160.064 (2)0.086 (3)0.039 (2)0.027 (2)0.0017 (18)−0.0077 (19)
C170.070 (3)0.042 (2)0.043 (2)0.0183 (19)−0.0060 (19)0.0027 (16)
C180.061 (2)0.0413 (19)0.046 (2)0.0183 (17)0.0036 (18)0.0109 (16)
C190.059 (2)0.0429 (19)0.040 (2)0.0186 (17)0.0070 (17)0.0114 (15)
C200.073 (3)0.063 (2)0.043 (2)0.025 (2)0.0118 (19)0.0108 (18)
C210.081 (3)0.068 (3)0.059 (3)0.028 (2)0.030 (2)0.023 (2)
C220.055 (2)0.045 (2)0.068 (3)0.0146 (18)0.015 (2)0.0109 (18)
C230.063 (2)0.041 (2)0.051 (2)0.0108 (18)0.0031 (19)0.0114 (17)
C240.060 (2)0.0440 (19)0.040 (2)0.0101 (17)0.0085 (17)0.0112 (15)
C250.073 (3)0.080 (3)0.073 (3)0.002 (2)−0.019 (2)0.005 (2)

Geometric parameters (Å, °)

S1—C161.794 (4)C10—H10C0.9700
S1—C151.802 (4)C11—C141.524 (6)
O1—C11.379 (4)C11—C121.540 (5)
O1—H1O0.8400C11—C131.549 (5)
O2—C171.230 (4)C12—H12A0.9700
O3—C231.374 (4)C12—H12B0.9700
O3—C251.423 (5)C12—H12C0.9700
N1—C171.347 (4)C13—H13A0.9700
N1—N21.373 (4)C13—H13B0.9700
N1—H10.8800C13—H13C0.9700
N2—C181.276 (4)C14—H14A0.9700
C1—C21.397 (4)C14—H14B0.9700
C1—C61.411 (4)C14—H14C0.9700
C2—C31.389 (4)C15—H15A0.9800
C2—C71.548 (4)C15—H15B0.9800
C3—C41.380 (4)C16—C171.487 (5)
C3—H30.9400C16—H16A0.9800
C4—C51.392 (4)C16—H16B0.9800
C4—C151.516 (5)C18—C191.465 (5)
C5—C61.378 (5)C18—H180.9400
C5—H50.9400C19—C241.376 (5)
C6—C111.534 (4)C19—C201.391 (5)
C7—C101.538 (5)C20—C211.375 (6)
C7—C91.534 (5)C20—H200.9400
C7—C81.540 (5)C21—C221.382 (5)
C8—H8A0.9700C21—H210.9400
C8—H8B0.9700C22—C231.373 (5)
C8—H8C0.9700C22—H220.9400
C9—H9A0.9700C23—C241.385 (5)
C9—H9B0.9700C24—H240.9400
C9—H9C0.9700C25—H25A0.9700
C10—H10A0.9700C25—H25B0.9700
C10—H10B0.9700C25—H25C0.9700
C16—S1—C15100.04 (17)C11—C12—H12C109.5
C1—O1—H1O95.8H12A—C12—H12C109.5
C23—O3—C25117.4 (3)H12B—C12—H12C109.5
C17—N1—N2120.9 (3)C11—C13—H13A109.5
C17—N1—H1119.6C11—C13—H13B109.5
N2—N1—H1119.6H13A—C13—H13B109.5
C18—N2—N1114.8 (3)C11—C13—H13C109.5
O1—C1—C2120.9 (3)H13A—C13—H13C109.5
O1—C1—C6116.7 (3)H13B—C13—H13C109.5
C2—C1—C6122.4 (3)C11—C14—H14A109.5
C3—C2—C1117.1 (3)C11—C14—H14B109.5
C3—C2—C7120.8 (3)H14A—C14—H14B109.5
C1—C2—C7122.0 (3)C11—C14—H14C109.5
C4—C3—C2122.6 (3)H14A—C14—H14C109.5
C4—C3—H3118.7H14B—C14—H14C109.5
C2—C3—H3118.7C4—C15—S1115.0 (3)
C3—C4—C5118.1 (3)C4—C15—H15A108.5
C3—C4—C15121.4 (3)S1—C15—H15A108.5
C5—C4—C15120.4 (3)C4—C15—H15B108.5
C6—C5—C4122.7 (3)S1—C15—H15B108.5
C6—C5—H5118.7H15A—C15—H15B107.5
C4—C5—H5118.7C17—C16—S1111.4 (3)
C5—C6—C1117.0 (3)C17—C16—H16A109.4
C5—C6—C11121.5 (3)S1—C16—H16A109.4
C1—C6—C11121.5 (3)C17—C16—H16B109.4
C10—C7—C9111.7 (3)S1—C16—H16B109.4
C10—C7—C8106.5 (3)H16A—C16—H16B108.0
C9—C7—C8105.8 (3)O2—C17—N1120.4 (4)
C10—C7—C2110.6 (3)O2—C17—C16121.4 (3)
C9—C7—C2110.9 (3)N1—C17—C16118.1 (4)
C8—C7—C2111.1 (3)N2—C18—C19121.4 (3)
C7—C8—H8A109.5N2—C18—H18119.3
C7—C8—H8B109.5C19—C18—H18119.3
H8A—C8—H8B109.5C24—C19—C20119.1 (3)
C7—C8—H8C109.5C24—C19—C18119.1 (3)
H8A—C8—H8C109.5C20—C19—C18121.8 (3)
H8B—C8—H8C109.5C21—C20—C19119.6 (4)
C7—C9—H9A109.5C21—C20—H20120.2
C7—C9—H9B109.5C19—C20—H20120.2
H9A—C9—H9B109.5C20—C21—C22121.1 (4)
C7—C9—H9C109.5C20—C21—H21119.4
H9A—C9—H9C109.5C22—C21—H21119.4
H9B—C9—H9C109.5C23—C22—C21119.4 (4)
C7—C10—H10A109.5C23—C22—H22120.3
C7—C10—H10B109.5C21—C22—H22120.3
H10A—C10—H10B109.5C22—C23—O3124.7 (3)
C7—C10—H10C109.5C22—C23—C24119.8 (4)
H10A—C10—H10C109.5O3—C23—C24115.5 (3)
H10B—C10—H10C109.5C19—C24—C23121.0 (3)
C14—C11—C6111.2 (3)C19—C24—H24119.5
C14—C11—C12110.8 (3)C23—C24—H24119.5
C6—C11—C12110.4 (3)O3—C25—H25A109.5
C14—C11—C13107.0 (3)O3—C25—H25B109.5
C6—C11—C13111.0 (3)H25A—C25—H25B109.5
C12—C11—C13106.3 (3)O3—C25—H25C109.5
C11—C12—H12A109.5H25A—C25—H25C109.5
C11—C12—H12B109.5H25B—C25—H25C109.5
H12A—C12—H12B109.5
C17—N1—N2—C18174.9 (3)C1—C6—C11—C1262.1 (5)
O1—C1—C2—C3−179.3 (3)C5—C6—C11—C13−1.3 (5)
C6—C1—C2—C3−1.2 (5)C1—C6—C11—C13179.7 (4)
O1—C1—C2—C70.7 (5)C3—C4—C15—S1111.0 (3)
C6—C1—C2—C7178.8 (3)C5—C4—C15—S1−71.0 (4)
C1—C2—C3—C41.3 (5)C16—S1—C15—C4−71.7 (3)
C7—C2—C3—C4−178.7 (3)C15—S1—C16—C17−71.2 (3)
C2—C3—C4—C5−1.2 (5)N2—N1—C17—O2−177.0 (3)
C2—C3—C4—C15176.9 (3)N2—N1—C17—C16−0.3 (5)
C3—C4—C5—C60.9 (5)S1—C16—C17—O297.8 (4)
C15—C4—C5—C6−177.2 (3)S1—C16—C17—N1−78.9 (4)
C4—C5—C6—C1−0.8 (5)N1—N2—C18—C19−179.0 (3)
C4—C5—C6—C11−179.8 (3)N2—C18—C19—C24−179.0 (3)
O1—C1—C6—C5179.1 (3)N2—C18—C19—C200.5 (5)
C2—C1—C6—C51.0 (5)C24—C19—C20—C210.9 (5)
O1—C1—C6—C11−1.8 (5)C18—C19—C20—C21−178.5 (3)
C2—C1—C6—C11−180.0 (3)C19—C20—C21—C22−0.6 (6)
C3—C2—C7—C10119.7 (4)C20—C21—C22—C23−0.3 (6)
C1—C2—C7—C10−60.3 (5)C21—C22—C23—O3−179.1 (3)
C3—C2—C7—C9−115.8 (4)C21—C22—C23—C241.0 (5)
C1—C2—C7—C964.3 (4)C25—O3—C23—C223.3 (5)
C3—C2—C7—C81.6 (5)C25—O3—C23—C24−176.8 (4)
C1—C2—C7—C8−178.4 (3)C20—C19—C24—C23−0.3 (5)
C5—C6—C11—C14117.7 (4)C18—C19—C24—C23179.2 (3)
C1—C6—C11—C14−61.3 (4)C22—C23—C24—C19−0.7 (5)
C5—C6—C11—C12−118.9 (4)O3—C23—C24—C19179.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.882.002.884 (4)176

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2573).

References

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  • Westrip, S. P. (2009). publCIF In preparation.

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