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

Yehye, W.A.; Ariffin, A.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536809030645

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2112

doi:10.1107/S1600536809030645

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

Wagee A. Yehye,^a Azhar Ariffin,^a Noorsaadah Abdul Rahman ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 30 July 2009; accepted 1 August 2009; online 8 August 2009)

The title compound, C₂₅H₃₄N₂O₃S, is a derivative of N′-benzylideneacetohydrazide having substituents on the acetyl and benzylidenyl parts, and displays a planar C_carbonyl—NH—NC_anisyl 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 ).

Experimental

Crystal data

C₂₅H₃₄N₂O₃S
M_r = 442.60
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.075
wR(F²) = 0.219
S = 1.06
4294 reflections
287 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88	2.00	2.884 (4)	176
Symmetry code: (i) -x+1, -y+1, -z+1.

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

Supporting information

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

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

checkCIF report

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

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

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

Crystal data top

C₂₅H₃₄N₂O₃S	Z = 2
M_r = 442.60	F(000) = 476
Triclinic, P1	D_x = 1.190 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9952 (2) Å	Cell parameters from 1620 reflections
b = 10.3199 (3) Å	θ = 2.6–21.7°
c = 20.6141 (7) Å	µ = 0.16 mm⁻¹
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 top

Bruker SMART APEX diffractometer	4294 independent reflections
Radiation source: fine-focus sealed tube	2577 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 25.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.947, T_max = 0.984	k = −12→12
8285 measured reflections	l = −24→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.219	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1218P)²] where P = (F_o² + 2F_c²)/3
4294 reflections	(Δ/σ)_max = 0.001
287 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₅H₃₄N₂O₃S	γ = 99.981 (2)°
M_r = 442.60	V = 1235.72 (7) Å³
Triclinic, P1	Z = 2
a = 5.9952 (2) Å	Mo Kα radiation
b = 10.3199 (3) Å	µ = 0.16 mm⁻¹
c = 20.6141 (7) Å	T = 223 K
α = 97.279 (2)°	0.35 × 0.10 × 0.10 mm
β = 95.916 (2)°

Data collection top

Bruker SMART APEX diffractometer	4294 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2577 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.984	R_int = 0.035
8285 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.219	H-atom parameters constrained
S = 1.06	Δρ_max = 0.61 e Å⁻³
4294 reflections	Δρ_min = −0.27 e Å⁻³
287 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.75715 (19)	0.78337 (10)	0.36105 (5)	0.0691 (4)
O1	0.1621 (4)	0.5619 (2)	0.06464 (11)	0.0613 (8)
H1O	0.2538	0.5093	0.0605	0.092*
O2	0.4442 (5)	0.5039 (2)	0.40994 (12)	0.0635 (8)
O3	1.6583 (5)	0.8943 (3)	0.72616 (13)	0.0731 (9)
N1	0.7590 (5)	0.5928 (3)	0.48032 (14)	0.0545 (8)
H1	0.6926	0.5660	0.5137	0.065*
N2	0.9784 (5)	0.6642 (3)	0.49141 (14)	0.0531 (8)
C1	0.2353 (5)	0.6087 (3)	0.13041 (16)	0.0433 (8)
C2	0.1613 (5)	0.5357 (3)	0.17936 (15)	0.0400 (8)
C3	0.2413 (6)	0.5907 (3)	0.24438 (16)	0.0435 (8)
H3	0.1965	0.5425	0.2781	0.052*
C4	0.3841 (6)	0.7132 (3)	0.26141 (15)	0.0424 (8)
C5	0.4527 (6)	0.7824 (3)	0.21091 (16)	0.0454 (9)
H5	0.5517	0.8654	0.2221	0.054*
C6	0.3814 (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)
H8A	0.0778	0.3330	0.2516	0.094*
H8B	−0.1623	0.2570	0.2141	0.094*
H8C	−0.1367	0.4036	0.2517	0.094*
C9	0.1096 (7)	0.2961 (4)	0.1244 (2)	0.0632 (11)
H9A	0.1537	0.3275	0.0843	0.095*
H9B	0.0023	0.2124	0.1132	0.095*
H9C	0.2440	0.2834	0.1515	0.095*
C10	−0.2303 (7)	0.4132 (4)	0.1249 (2)	0.0725 (13)
H10A	−0.2018	0.4475	0.0842	0.109*
H10B	−0.3019	0.4741	0.1518	0.109*
H10C	−0.3307	0.3268	0.1147	0.109*
C11	0.4605 (6)	0.8127 (4)	0.09063 (17)	0.0538 (10)
C12	0.2542 (7)	0.8470 (4)	0.04992 (19)	0.0673 (12)
H12A	0.1521	0.7656	0.0291	0.101*
H12B	0.3070	0.8982	0.0163	0.101*
H12C	0.1735	0.8989	0.0787	0.101*
C13	0.6181 (8)	0.9471 (4)	0.1203 (2)	0.0835 (15)
H13A	0.7536	0.9306	0.1454	0.125*
H13B	0.5372	0.9988	0.1490	0.125*
H13C	0.6621	0.9959	0.0849	0.125*
C14	0.5967 (7)	0.7360 (5)	0.0464 (2)	0.0770 (14)
H14A	0.7316	0.7210	0.0724	0.115*
H14B	0.6424	0.7870	0.0119	0.115*
H14C	0.5030	0.6511	0.0266	0.115*
C15	0.4592 (7)	0.7738 (3)	0.33293 (17)	0.0567 (10)
H15A	0.3680	0.7211	0.3607	0.068*
H15B	0.4253	0.8637	0.3392	0.068*
C16	0.7607 (7)	0.6107 (4)	0.36385 (18)	0.0634 (11)
H16A	0.6844	0.5581	0.3220	0.076*
H16B	0.9191	0.5976	0.3693	0.076*
C17	0.6438 (7)	0.5632 (3)	0.41904 (18)	0.0519 (9)
C18	1.0622 (6)	0.6942 (3)	0.55202 (18)	0.0484 (9)
H18	0.9739	0.6658	0.5845	0.058*
C19	1.2932 (6)	0.7721 (3)	0.57209 (17)	0.0456 (9)
C20	1.4309 (7)	0.8176 (4)	0.52624 (19)	0.0574 (10)
H20	1.3757	0.8005	0.4810	0.069*
C21	1.6485 (8)	0.8877 (4)	0.5475 (2)	0.0653 (11)
H21	1.7418	0.9177	0.5164	0.078*
C22	1.7322 (7)	0.9150 (3)	0.6137 (2)	0.0547 (10)
H22	1.8815	0.9626	0.6276	0.066*
C23	1.5954 (7)	0.8718 (3)	0.65910 (18)	0.0519 (9)
C24	1.3768 (6)	0.8000 (3)	0.63807 (17)	0.0475 (9)
H24	1.2843	0.7698	0.6693	0.057*
C25	1.8769 (8)	0.9736 (5)	0.7502 (2)	0.0793 (14)
H25A	1.9013	0.9819	0.7979	0.119*
H25B	1.8843	1.0612	0.7372	0.119*
H25C	1.9940	0.9319	0.7318	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0859 (8)	0.0701 (7)	0.0346 (6)	−0.0270 (6)	−0.0044 (5)	0.0117 (4)
O1	0.0721 (17)	0.0705 (17)	0.0310 (14)	−0.0100 (14)	−0.0009 (12)	0.0066 (11)
O2	0.085 (2)	0.0483 (15)	0.0520 (17)	0.0036 (14)	−0.0108 (14)	0.0139 (12)
O3	0.082 (2)	0.0767 (19)	0.0480 (17)	−0.0086 (16)	−0.0075 (14)	0.0083 (13)
N1	0.070 (2)	0.0470 (17)	0.0455 (19)	0.0155 (16)	−0.0058 (16)	0.0090 (13)
N2	0.063 (2)	0.0553 (18)	0.0430 (19)	0.0242 (16)	−0.0048 (15)	0.0065 (14)
C1	0.0435 (19)	0.054 (2)	0.0297 (18)	0.0018 (16)	0.0059 (14)	0.0076 (15)
C2	0.0431 (18)	0.0427 (19)	0.0349 (19)	0.0042 (15)	0.0099 (15)	0.0092 (14)
C3	0.055 (2)	0.0402 (19)	0.038 (2)	0.0082 (16)	0.0128 (16)	0.0129 (15)
C4	0.059 (2)	0.0423 (19)	0.0268 (18)	0.0117 (16)	0.0039 (15)	0.0062 (14)
C5	0.055 (2)	0.0417 (18)	0.0359 (19)	−0.0017 (16)	−0.0001 (15)	0.0112 (14)
C6	0.0425 (19)	0.050 (2)	0.0348 (19)	−0.0036 (16)	0.0046 (15)	0.0146 (15)
C7	0.050 (2)	0.048 (2)	0.048 (2)	−0.0032 (17)	0.0141 (17)	0.0076 (16)
C8	0.080 (3)	0.049 (2)	0.060 (3)	−0.002 (2)	0.026 (2)	0.0144 (18)
C9	0.070 (3)	0.051 (2)	0.064 (3)	−0.003 (2)	0.019 (2)	−0.0008 (19)
C10	0.052 (2)	0.072 (3)	0.087 (3)	−0.010 (2)	0.005 (2)	0.019 (2)
C11	0.058 (2)	0.063 (2)	0.034 (2)	−0.0093 (19)	−0.0006 (17)	0.0154 (17)
C12	0.072 (3)	0.078 (3)	0.049 (2)	−0.004 (2)	0.000 (2)	0.033 (2)
C13	0.097 (3)	0.080 (3)	0.056 (3)	−0.039 (3)	−0.006 (2)	0.031 (2)
C14	0.064 (3)	0.111 (4)	0.054 (3)	−0.007 (3)	0.019 (2)	0.027 (2)
C15	0.091 (3)	0.0354 (19)	0.043 (2)	0.0132 (19)	0.004 (2)	0.0085 (15)
C16	0.064 (2)	0.086 (3)	0.039 (2)	0.027 (2)	0.0017 (18)	−0.0077 (19)
C17	0.070 (3)	0.042 (2)	0.043 (2)	0.0183 (19)	−0.0060 (19)	0.0027 (16)
C18	0.061 (2)	0.0413 (19)	0.046 (2)	0.0183 (17)	0.0036 (18)	0.0109 (16)
C19	0.059 (2)	0.0429 (19)	0.040 (2)	0.0186 (17)	0.0070 (17)	0.0114 (15)
C20	0.073 (3)	0.063 (2)	0.043 (2)	0.025 (2)	0.0118 (19)	0.0108 (18)
C21	0.081 (3)	0.068 (3)	0.059 (3)	0.028 (2)	0.030 (2)	0.023 (2)
C22	0.055 (2)	0.045 (2)	0.068 (3)	0.0146 (18)	0.015 (2)	0.0109 (18)
C23	0.063 (2)	0.041 (2)	0.051 (2)	0.0108 (18)	0.0031 (19)	0.0114 (17)
C24	0.060 (2)	0.0440 (19)	0.040 (2)	0.0101 (17)	0.0085 (17)	0.0112 (15)
C25	0.073 (3)	0.080 (3)	0.073 (3)	0.002 (2)	−0.019 (2)	0.005 (2)

Geometric parameters (Å, º) top

S1—C16	1.794 (4)	C10—H10C	0.9700
S1—C15	1.802 (4)	C11—C14	1.524 (6)
O1—C1	1.379 (4)	C11—C12	1.540 (5)
O1—H1O	0.8400	C11—C13	1.549 (5)
O2—C17	1.230 (4)	C12—H12A	0.9700
O3—C23	1.374 (4)	C12—H12B	0.9700
O3—C25	1.423 (5)	C12—H12C	0.9700
N1—C17	1.347 (4)	C13—H13A	0.9700
N1—N2	1.373 (4)	C13—H13B	0.9700
N1—H1	0.8800	C13—H13C	0.9700
N2—C18	1.276 (4)	C14—H14A	0.9700
C1—C2	1.397 (4)	C14—H14B	0.9700
C1—C6	1.411 (4)	C14—H14C	0.9700
C2—C3	1.389 (4)	C15—H15A	0.9800
C2—C7	1.548 (4)	C15—H15B	0.9800
C3—C4	1.380 (4)	C16—C17	1.487 (5)
C3—H3	0.9400	C16—H16A	0.9800
C4—C5	1.392 (4)	C16—H16B	0.9800
C4—C15	1.516 (5)	C18—C19	1.465 (5)
C5—C6	1.378 (5)	C18—H18	0.9400
C5—H5	0.9400	C19—C24	1.376 (5)
C6—C11	1.534 (4)	C19—C20	1.391 (5)
C7—C10	1.538 (5)	C20—C21	1.375 (6)
C7—C9	1.534 (5)	C20—H20	0.9400
C7—C8	1.540 (5)	C21—C22	1.382 (5)
C8—H8A	0.9700	C21—H21	0.9400
C8—H8B	0.9700	C22—C23	1.373 (5)
C8—H8C	0.9700	C22—H22	0.9400
C9—H9A	0.9700	C23—C24	1.385 (5)
C9—H9B	0.9700	C24—H24	0.9400
C9—H9C	0.9700	C25—H25A	0.9700
C10—H10A	0.9700	C25—H25B	0.9700
C10—H10B	0.9700	C25—H25C	0.9700

C16—S1—C15	100.04 (17)	C11—C12—H12C	109.5
C1—O1—H1O	95.8	H12A—C12—H12C	109.5
C23—O3—C25	117.4 (3)	H12B—C12—H12C	109.5
C17—N1—N2	120.9 (3)	C11—C13—H13A	109.5
C17—N1—H1	119.6	C11—C13—H13B	109.5
N2—N1—H1	119.6	H13A—C13—H13B	109.5
C18—N2—N1	114.8 (3)	C11—C13—H13C	109.5
O1—C1—C2	120.9 (3)	H13A—C13—H13C	109.5
O1—C1—C6	116.7 (3)	H13B—C13—H13C	109.5
C2—C1—C6	122.4 (3)	C11—C14—H14A	109.5
C3—C2—C1	117.1 (3)	C11—C14—H14B	109.5
C3—C2—C7	120.8 (3)	H14A—C14—H14B	109.5
C1—C2—C7	122.0 (3)	C11—C14—H14C	109.5
C4—C3—C2	122.6 (3)	H14A—C14—H14C	109.5
C4—C3—H3	118.7	H14B—C14—H14C	109.5
C2—C3—H3	118.7	C4—C15—S1	115.0 (3)
C3—C4—C5	118.1 (3)	C4—C15—H15A	108.5
C3—C4—C15	121.4 (3)	S1—C15—H15A	108.5
C5—C4—C15	120.4 (3)	C4—C15—H15B	108.5
C6—C5—C4	122.7 (3)	S1—C15—H15B	108.5
C6—C5—H5	118.7	H15A—C15—H15B	107.5
C4—C5—H5	118.7	C17—C16—S1	111.4 (3)
C5—C6—C1	117.0 (3)	C17—C16—H16A	109.4
C5—C6—C11	121.5 (3)	S1—C16—H16A	109.4
C1—C6—C11	121.5 (3)	C17—C16—H16B	109.4
C10—C7—C9	111.7 (3)	S1—C16—H16B	109.4
C10—C7—C8	106.5 (3)	H16A—C16—H16B	108.0
C9—C7—C8	105.8 (3)	O2—C17—N1	120.4 (4)
C10—C7—C2	110.6 (3)	O2—C17—C16	121.4 (3)
C9—C7—C2	110.9 (3)	N1—C17—C16	118.1 (4)
C8—C7—C2	111.1 (3)	N2—C18—C19	121.4 (3)
C7—C8—H8A	109.5	N2—C18—H18	119.3
C7—C8—H8B	109.5	C19—C18—H18	119.3
H8A—C8—H8B	109.5	C24—C19—C20	119.1 (3)
C7—C8—H8C	109.5	C24—C19—C18	119.1 (3)
H8A—C8—H8C	109.5	C20—C19—C18	121.8 (3)
H8B—C8—H8C	109.5	C21—C20—C19	119.6 (4)
C7—C9—H9A	109.5	C21—C20—H20	120.2
C7—C9—H9B	109.5	C19—C20—H20	120.2
H9A—C9—H9B	109.5	C20—C21—C22	121.1 (4)
C7—C9—H9C	109.5	C20—C21—H21	119.4
H9A—C9—H9C	109.5	C22—C21—H21	119.4
H9B—C9—H9C	109.5	C23—C22—C21	119.4 (4)
C7—C10—H10A	109.5	C23—C22—H22	120.3
C7—C10—H10B	109.5	C21—C22—H22	120.3
H10A—C10—H10B	109.5	C22—C23—O3	124.7 (3)
C7—C10—H10C	109.5	C22—C23—C24	119.8 (4)
H10A—C10—H10C	109.5	O3—C23—C24	115.5 (3)
H10B—C10—H10C	109.5	C19—C24—C23	121.0 (3)
C14—C11—C6	111.2 (3)	C19—C24—H24	119.5
C14—C11—C12	110.8 (3)	C23—C24—H24	119.5
C6—C11—C12	110.4 (3)	O3—C25—H25A	109.5
C14—C11—C13	107.0 (3)	O3—C25—H25B	109.5
C6—C11—C13	111.0 (3)	H25A—C25—H25B	109.5
C12—C11—C13	106.3 (3)	O3—C25—H25C	109.5
C11—C12—H12A	109.5	H25A—C25—H25C	109.5
C11—C12—H12B	109.5	H25B—C25—H25C	109.5
H12A—C12—H12B	109.5

C17—N1—N2—C18	174.9 (3)	C1—C6—C11—C12	62.1 (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—C13	179.7 (4)
O1—C1—C2—C7	0.7 (5)	C3—C4—C15—S1	111.0 (3)
C6—C1—C2—C7	178.8 (3)	C5—C4—C15—S1	−71.0 (4)
C1—C2—C3—C4	1.3 (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—C15	176.9 (3)	N2—N1—C17—C16	−0.3 (5)
C3—C4—C5—C6	0.9 (5)	S1—C16—C17—O2	97.8 (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—C5	179.1 (3)	N2—C18—C19—C20	0.5 (5)
C2—C1—C6—C5	1.0 (5)	C24—C19—C20—C21	0.9 (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—C10	119.7 (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—C24	1.0 (5)
C1—C2—C7—C9	64.3 (4)	C25—O3—C23—C22	3.3 (5)
C3—C2—C7—C8	1.6 (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—C14	117.7 (4)	C18—C19—C24—C23	179.2 (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—C19	179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.00	2.884 (4)	176

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₄N₂O₃S
M_r	442.60
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	5.9952 (2), 10.3199 (3), 20.6141 (7)
α, β, γ (°)	97.279 (2), 95.916 (2), 99.981 (2)
V (Å³)	1235.72 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.35 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8285, 4294, 2577
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.219, 1.06
No. of reflections	4294
No. of parameters	287
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.27

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.00	2.884 (4)	176

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Litvinov, I. A., Kataeva, O. N., Ermolaeva, L. V., Vagina, G. A., Troepol'skaya, T. V. & Naumov, V. A. (1991). Russ. Chem. Bull. 40, 62–67. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 9| September 2009| Page o2112

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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