N′-[(Biphenyl-4-yl)methyl­ene]-2-[(3,5-di-tert-butyl-4-hydroxy­benz­yl)sulfan­yl]acetohydrazide

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

doi:10.1107/S1600536810006884

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o734

doi:10.1107/S1600536810006884

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N′-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]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 23 February 2010; accepted 23 February 2010; online 3 March 2010)

In the title compound, C₃₀H₃₆N₂O₂S, the dihedral angle between the two aromatic rings of the biphenyl residue is 31.2 (1)°. The two methylene C atoms subtend an angle of 99.9 (1)° at the S atom. In the crystal, molecules form inversion dimers linked by pairs of N—H⋯O hydrogen bonds. The hydroxyl group is shielded by the tert-butyl residues and is therefore not involved in any hydrogen bonding.

Related literature

When heated in acidified ethanol the compound gave biphenyl-4-carbaldehyde azine; see: Yehye et al. (2008 ).

Experimental

Crystal data

C₃₀H₃₆N₂O₂S
M_r = 488.67
Triclinic, $[P \overline 1]$
a = 9.1104 (11) Å
b = 10.5601 (12) Å
c = 15.5146 (18) Å
α = 104.435 (2)°
β = 102.805 (2)°
γ = 97.559 (2)°
V = 1381.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.944, T_max = 0.986
10977 measured reflections
4873 independent reflections
3404 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.04
4873 reflections
324 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.87 (1)	1.97 (1)	2.827 (2)	174 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006884/bt5202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006884/bt5202Isup2.hkl

checkCIF report

Related literature top

When heated in acidified ethanol the compound gave biphenyl-4-carbaldehyde azine; see: Yehye et al. (2008).

Experimental top

2-(3,5-Di-tert-butyl-4-hydroxybenzylthio)acetohydrazine (0.5 g, 1.54 mmol) and 4-phenylbenzaldehyde (0.28 g, 1.54 mmol) were stirred in ethanol (10 ml) for 2 h. The resulting solid was collected and recrystallized from ethanol to give the Schiff base as large prismatic crystals in 90% yield. The formulation was assumed from ¹H NMR spectral analysis.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₃₀H₃₆N₂O₂S at the the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

N'-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4- hydroxybenzyl)sulfanyl]acetohydrazide top

Crystal data top

C₃₀H₃₆N₂O₂S	Z = 2
M_r = 488.67	F(000) = 524
Triclinic, P1	D_x = 1.175 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1104 (11) Å	Cell parameters from 2001 reflections
b = 10.5601 (12) Å	θ = 2.3–21.2°
c = 15.5146 (18) Å	µ = 0.15 mm⁻¹
α = 104.435 (2)°	T = 293 K
β = 102.805 (2)°	Prism, colorless
γ = 97.559 (2)°	0.40 × 0.10 × 0.10 mm
V = 1381.7 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	4873 independent reflections
Radiation source: fine-focus sealed tube	3404 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.944, T_max = 0.986	k = −12→12
10977 measured reflections	l = −16→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0664P)² + 0.0264P] where P = (F_o² + 2F_c²)/3
4873 reflections	(Δ/σ)_max = 0.001
324 parameters	Δρ_max = 0.17 e Å⁻³
2 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₀H₃₆N₂O₂S	γ = 97.559 (2)°
M_r = 488.67	V = 1381.7 (3) Å³
Triclinic, P1	Z = 2
a = 9.1104 (11) Å	Mo Kα radiation
b = 10.5601 (12) Å	µ = 0.15 mm⁻¹
c = 15.5146 (18) Å	T = 293 K
α = 104.435 (2)°	0.40 × 0.10 × 0.10 mm
β = 102.805 (2)°

Data collection top

Bruker SMART APEX diffractometer	4873 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3404 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.986	R_int = 0.035
10977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.17 e Å⁻³
4873 reflections	Δρ_min = −0.19 e Å⁻³
324 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.76556 (7)	0.68306 (6)	0.78801 (4)	0.0490 (2)
O1	0.5035 (2)	0.7947 (2)	1.15128 (12)	0.0773 (6)
H1O	0.414 (2)	0.758 (5)	1.146 (4)	0.20 (2)*
O2	0.54723 (17)	0.65943 (15)	0.58105 (10)	0.0543 (4)
N1	0.7059 (2)	0.51789 (18)	0.55439 (12)	0.0445 (5)
H1	0.6318 (18)	0.4645 (17)	0.5098 (11)	0.048 (6)*
N2	0.8470 (2)	0.48554 (18)	0.57906 (12)	0.0449 (4)
C1	0.5274 (2)	0.7853 (2)	1.06541 (15)	0.0472 (6)
C2	0.4146 (2)	0.7092 (2)	0.98530 (15)	0.0443 (5)
C3	0.4476 (2)	0.7061 (2)	0.90205 (15)	0.0475 (6)
H3	0.3756	0.6556	0.8477	0.057*
C4	0.5832 (2)	0.7749 (2)	0.89644 (15)	0.0465 (6)
C5	0.6914 (2)	0.8472 (2)	0.97723 (15)	0.0468 (6)
H5	0.7831	0.8931	0.9736	0.056*
C6	0.6687 (2)	0.8541 (2)	1.06363 (15)	0.0428 (5)
C7	0.2608 (2)	0.6336 (2)	0.98892 (17)	0.0538 (6)
C8	0.2880 (3)	0.5279 (3)	1.0406 (2)	0.0774 (8)
H8A	0.3423	0.4667	1.0100	0.116*
H8B	0.1910	0.4801	1.0409	0.116*
H8C	0.3477	0.5711	1.1029	0.116*
C9	0.1710 (3)	0.7315 (3)	1.0355 (2)	0.0724 (8)
H9A	0.0774	0.6826	1.0394	0.109*
H9B	0.1475	0.7919	0.9997	0.109*
H9C	0.2323	0.7811	1.0964	0.109*
C10	0.1580 (3)	0.5607 (3)	0.8920 (2)	0.0779 (8)
H10A	0.2075	0.4953	0.8612	0.117*
H10B	0.1405	0.6238	0.8575	0.117*
H10C	0.0616	0.5174	0.8963	0.117*
C11	0.7924 (3)	0.9341 (2)	1.15209 (15)	0.0513 (6)
C12	0.7331 (3)	1.0494 (3)	1.20689 (19)	0.0837 (9)
H12A	0.6451	1.0141	1.2243	0.126*
H12B	0.7047	1.1066	1.1693	0.126*
H12C	0.8124	1.0995	1.2613	0.126*
C13	0.8421 (3)	0.8430 (3)	1.21158 (19)	0.0748 (8)
H13A	0.7556	0.8054	1.2292	0.112*
H13B	0.9211	0.8940	1.2659	0.112*
H13C	0.8808	0.7725	1.1768	0.112*
C14	0.9374 (3)	0.9949 (3)	1.13007 (19)	0.0720 (8)
H14A	1.0121	1.0454	1.1865	0.108*
H14B	0.9115	1.0525	1.0924	0.108*
H14C	0.9793	0.9248	1.0976	0.108*
C15	0.6138 (3)	0.7729 (3)	0.80454 (16)	0.0578 (6)
H15A	0.6433	0.8635	0.8025	0.069*
H15B	0.5212	0.7302	0.7553	0.069*
C16	0.7967 (2)	0.7190 (2)	0.68495 (14)	0.0445 (5)
H16A	0.7939	0.8118	0.6893	0.053*
H16B	0.8969	0.7036	0.6786	0.053*
C17	0.6743 (2)	0.6309 (2)	0.60228 (14)	0.0415 (5)
C18	0.8649 (3)	0.3747 (2)	0.53133 (15)	0.0486 (6)
H18	0.7843	0.3207	0.4826	0.058*
C19	1.0115 (2)	0.3318 (2)	0.55261 (15)	0.0448 (5)
C20	1.0305 (3)	0.2105 (2)	0.50071 (16)	0.0520 (6)
H20	0.9502	0.1578	0.4513	0.062*
C21	1.1672 (3)	0.1671 (2)	0.52141 (16)	0.0508 (6)
H21	1.1770	0.0852	0.4857	0.061*
C22	1.2902 (2)	0.2427 (2)	0.59426 (15)	0.0438 (5)
C23	1.2704 (3)	0.3650 (2)	0.64509 (16)	0.0539 (6)
H23	1.3511	0.4186	0.6939	0.065*
C24	1.1346 (3)	0.4084 (2)	0.62486 (16)	0.0549 (6)
H24	1.1251	0.4906	0.6602	0.066*
C25	1.4349 (3)	0.1944 (2)	0.61918 (15)	0.0470 (6)
C26	1.4334 (3)	0.0584 (3)	0.60401 (17)	0.0578 (6)
H26	1.3410	−0.0024	0.5761	0.069*
C27	1.5670 (3)	0.0121 (3)	0.62980 (19)	0.0703 (8)
H27	1.5640	−0.0788	0.6199	0.084*
C28	1.7033 (3)	0.1010 (4)	0.6700 (2)	0.0748 (8)
H28	1.7932	0.0703	0.6875	0.090*
C29	1.7081 (3)	0.2344 (3)	0.68445 (19)	0.0719 (8)
H29	1.8015	0.2940	0.7112	0.086*
C30	1.5748 (3)	0.2822 (3)	0.65969 (18)	0.0607 (7)
H30	1.5794	0.3734	0.6703	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0509 (4)	0.0565 (4)	0.0402 (3)	0.0122 (3)	0.0105 (3)	0.0156 (3)
O1	0.0721 (13)	0.1141 (16)	0.0468 (11)	−0.0004 (12)	0.0283 (10)	0.0237 (10)
O2	0.0481 (9)	0.0556 (10)	0.0505 (10)	0.0197 (8)	0.0053 (7)	0.0020 (7)
N1	0.0409 (11)	0.0479 (11)	0.0375 (11)	0.0131 (9)	0.0044 (9)	0.0024 (9)
N2	0.0435 (11)	0.0508 (11)	0.0427 (11)	0.0165 (9)	0.0120 (8)	0.0135 (9)
C1	0.0484 (13)	0.0578 (14)	0.0400 (13)	0.0093 (11)	0.0186 (11)	0.0169 (11)
C2	0.0395 (12)	0.0499 (13)	0.0463 (13)	0.0104 (10)	0.0133 (10)	0.0166 (11)
C3	0.0421 (12)	0.0549 (14)	0.0426 (13)	0.0100 (10)	0.0075 (10)	0.0119 (11)
C4	0.0441 (13)	0.0619 (15)	0.0389 (13)	0.0151 (11)	0.0156 (10)	0.0177 (11)
C5	0.0415 (12)	0.0554 (14)	0.0473 (14)	0.0050 (10)	0.0160 (11)	0.0203 (11)
C6	0.0415 (12)	0.0453 (13)	0.0432 (13)	0.0070 (10)	0.0119 (10)	0.0158 (10)
C7	0.0394 (12)	0.0612 (15)	0.0635 (16)	0.0065 (11)	0.0167 (11)	0.0220 (13)
C8	0.0623 (17)	0.0742 (19)	0.111 (2)	0.0098 (14)	0.0326 (17)	0.0471 (18)
C9	0.0513 (15)	0.086 (2)	0.090 (2)	0.0194 (14)	0.0322 (15)	0.0283 (16)
C10	0.0483 (16)	0.086 (2)	0.084 (2)	−0.0105 (14)	0.0134 (14)	0.0132 (16)
C11	0.0503 (13)	0.0509 (14)	0.0456 (13)	0.0032 (11)	0.0079 (11)	0.0093 (11)
C12	0.092 (2)	0.077 (2)	0.0620 (18)	0.0160 (17)	0.0096 (16)	−0.0065 (15)
C13	0.0641 (17)	0.088 (2)	0.0652 (18)	0.0056 (15)	−0.0033 (14)	0.0320 (16)
C14	0.0584 (16)	0.0727 (18)	0.0679 (18)	−0.0148 (14)	0.0045 (13)	0.0154 (14)
C15	0.0559 (15)	0.0806 (18)	0.0440 (14)	0.0211 (13)	0.0167 (11)	0.0238 (13)
C16	0.0409 (12)	0.0466 (13)	0.0419 (13)	0.0035 (10)	0.0127 (10)	0.0067 (10)
C17	0.0439 (13)	0.0447 (13)	0.0350 (12)	0.0099 (10)	0.0108 (10)	0.0094 (10)
C18	0.0481 (13)	0.0527 (14)	0.0438 (13)	0.0136 (11)	0.0105 (11)	0.0111 (11)
C19	0.0491 (13)	0.0489 (13)	0.0411 (13)	0.0158 (11)	0.0152 (11)	0.0151 (11)
C20	0.0504 (14)	0.0530 (14)	0.0471 (14)	0.0117 (11)	0.0086 (11)	0.0076 (11)
C21	0.0560 (15)	0.0455 (13)	0.0521 (14)	0.0184 (11)	0.0175 (12)	0.0092 (11)
C22	0.0487 (13)	0.0494 (14)	0.0409 (12)	0.0140 (10)	0.0167 (10)	0.0202 (11)
C23	0.0533 (14)	0.0534 (15)	0.0484 (14)	0.0148 (12)	0.0020 (11)	0.0108 (12)
C24	0.0650 (16)	0.0494 (14)	0.0490 (14)	0.0222 (12)	0.0106 (12)	0.0102 (11)
C25	0.0527 (14)	0.0565 (15)	0.0424 (13)	0.0185 (11)	0.0204 (11)	0.0223 (11)
C26	0.0605 (16)	0.0606 (16)	0.0577 (16)	0.0232 (12)	0.0166 (12)	0.0200 (12)
C27	0.080 (2)	0.0734 (19)	0.0688 (18)	0.0430 (17)	0.0213 (16)	0.0245 (15)
C28	0.0611 (18)	0.106 (3)	0.0719 (19)	0.0418 (18)	0.0209 (15)	0.0365 (18)
C29	0.0492 (15)	0.096 (2)	0.076 (2)	0.0150 (15)	0.0146 (14)	0.0374 (17)
C30	0.0555 (15)	0.0686 (17)	0.0667 (17)	0.0133 (13)	0.0179 (13)	0.0326 (14)

Geometric parameters (Å, º) top

S1—C16	1.804 (2)	C12—H12C	0.9600
S1—C15	1.805 (2)	C13—H13A	0.9600
O1—C1	1.379 (3)	C13—H13B	0.9600
O1—H1O	0.83 (1)	C13—H13C	0.9600
O2—C17	1.230 (2)	C14—H14A	0.9600
N1—C17	1.342 (3)	C14—H14B	0.9600
N1—N2	1.371 (2)	C14—H14C	0.9600
N1—H1	0.87 (1)	C15—H15A	0.9700
N2—C18	1.271 (3)	C15—H15B	0.9700
C1—C2	1.402 (3)	C16—C17	1.500 (3)
C1—C6	1.402 (3)	C16—H16A	0.9700
C2—C3	1.383 (3)	C16—H16B	0.9700
C2—C7	1.539 (3)	C18—C19	1.462 (3)
C3—C4	1.380 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C24	1.386 (3)
C4—C5	1.379 (3)	C19—C20	1.387 (3)
C4—C15	1.508 (3)	C20—C21	1.383 (3)
C5—C6	1.387 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.387 (3)
C6—C11	1.534 (3)	C21—H21	0.9300
C7—C10	1.530 (3)	C22—C23	1.392 (3)
C7—C9	1.540 (3)	C22—C25	1.482 (3)
C7—C8	1.543 (3)	C23—C24	1.375 (3)
C8—H8A	0.9600	C23—H23	0.9300
C8—H8B	0.9600	C24—H24	0.9300
C8—H8C	0.9600	C25—C30	1.387 (3)
C9—H9A	0.9600	C25—C26	1.394 (3)
C9—H9B	0.9600	C26—C27	1.385 (3)
C9—H9C	0.9600	C26—H26	0.9300
C10—H10A	0.9600	C27—C28	1.367 (4)
C10—H10B	0.9600	C27—H27	0.9300
C10—H10C	0.9600	C28—C29	1.363 (4)
C11—C12	1.535 (3)	C28—H28	0.9300
C11—C14	1.536 (3)	C29—C30	1.388 (3)
C11—C13	1.535 (3)	C29—H29	0.9300
C12—H12A	0.9600	C30—H30	0.9300
C12—H12B	0.9600

C16—S1—C15	99.92 (10)	C11—C13—H13C	109.5
C1—O1—H1O	110 (4)	H13A—C13—H13C	109.5
C17—N1—N2	120.93 (18)	H13B—C13—H13C	109.5
C17—N1—H1	117.2 (14)	C11—C14—H14A	109.5
N2—N1—H1	121.8 (14)	C11—C14—H14B	109.5
C18—N2—N1	116.47 (18)	H14A—C14—H14B	109.5
O1—C1—C2	120.5 (2)	C11—C14—H14C	109.5
O1—C1—C6	116.5 (2)	H14A—C14—H14C	109.5
C2—C1—C6	122.98 (19)	H14B—C14—H14C	109.5
C3—C2—C1	116.67 (19)	C4—C15—S1	109.84 (15)
C3—C2—C7	121.2 (2)	C4—C15—H15A	109.7
C1—C2—C7	122.10 (19)	S1—C15—H15A	109.7
C4—C3—C2	122.6 (2)	C4—C15—H15B	109.7
C4—C3—H3	118.7	S1—C15—H15B	109.7
C2—C3—H3	118.7	H15A—C15—H15B	108.2
C5—C4—C3	118.6 (2)	C17—C16—S1	109.61 (14)
C5—C4—C15	120.1 (2)	C17—C16—H16A	109.7
C3—C4—C15	121.4 (2)	S1—C16—H16A	109.7
C4—C5—C6	122.6 (2)	C17—C16—H16B	109.7
C4—C5—H5	118.7	S1—C16—H16B	109.7
C6—C5—H5	118.7	H16A—C16—H16B	108.2
C5—C6—C1	116.5 (2)	O2—C17—N1	121.11 (19)
C5—C6—C11	121.18 (19)	O2—C17—C16	120.80 (19)
C1—C6—C11	122.28 (19)	N1—C17—C16	118.04 (19)
C10—C7—C9	106.5 (2)	N2—C18—C19	120.3 (2)
C10—C7—C2	111.37 (19)	N2—C18—H18	119.8
C9—C7—C2	110.51 (19)	C19—C18—H18	119.8
C10—C7—C8	107.4 (2)	C24—C19—C20	117.8 (2)
C9—C7—C8	110.5 (2)	C24—C19—C18	121.9 (2)
C2—C7—C8	110.45 (19)	C20—C19—C18	120.2 (2)
C7—C8—H8A	109.5	C21—C20—C19	120.9 (2)
C7—C8—H8B	109.5	C21—C20—H20	119.5
H8A—C8—H8B	109.5	C19—C20—H20	119.5
C7—C8—H8C	109.5	C20—C21—C22	121.5 (2)
H8A—C8—H8C	109.5	C20—C21—H21	119.3
H8B—C8—H8C	109.5	C22—C21—H21	119.3
C7—C9—H9A	109.5	C21—C22—C23	117.1 (2)
C7—C9—H9B	109.5	C21—C22—C25	121.8 (2)
H9A—C9—H9B	109.5	C23—C22—C25	121.1 (2)
C7—C9—H9C	109.5	C24—C23—C22	121.6 (2)
H9A—C9—H9C	109.5	C24—C23—H23	119.2
H9B—C9—H9C	109.5	C22—C23—H23	119.2
C7—C10—H10A	109.5	C23—C24—C19	121.1 (2)
C7—C10—H10B	109.5	C23—C24—H24	119.5
H10A—C10—H10B	109.5	C19—C24—H24	119.5
C7—C10—H10C	109.5	C30—C25—C26	118.0 (2)
H10A—C10—H10C	109.5	C30—C25—C22	121.5 (2)
H10B—C10—H10C	109.5	C26—C25—C22	120.6 (2)
C12—C11—C14	107.5 (2)	C27—C26—C25	121.2 (3)
C12—C11—C6	110.4 (2)	C27—C26—H26	119.4
C14—C11—C6	111.31 (19)	C25—C26—H26	119.4
C12—C11—C13	110.4 (2)	C28—C27—C26	119.6 (3)
C14—C11—C13	106.5 (2)	C28—C27—H27	120.2
C6—C11—C13	110.45 (19)	C26—C27—H27	120.2
C11—C12—H12A	109.5	C29—C28—C27	120.3 (3)
C11—C12—H12B	109.5	C29—C28—H28	119.8
H12A—C12—H12B	109.5	C27—C28—H28	119.8
C11—C12—H12C	109.5	C28—C29—C30	120.6 (3)
H12A—C12—H12C	109.5	C28—C29—H29	119.7
H12B—C12—H12C	109.5	C30—C29—H29	119.7
C11—C13—H13A	109.5	C25—C30—C29	120.3 (3)
C11—C13—H13B	109.5	C25—C30—H30	119.9
H13A—C13—H13B	109.5	C29—C30—H30	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87 (1)	1.97 (1)	2.827 (2)	174 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₀H₃₆N₂O₂S
M_r	488.67
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1104 (11), 10.5601 (12), 15.5146 (18)
α, β, γ (°)	104.435 (2), 102.805 (2), 97.559 (2)
V (Å³)	1381.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	10977, 4873, 3404
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.04
No. of reflections	4873
No. of parameters	324
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87 (1)	1.97 (1)	2.827 (2)	174 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya (grant No. FS338/2008 A) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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. (2010). publCIF. In preparation. Google Scholar
Yehye, W. A., Ariffin, A., Rahman, N. A. & Ng, S. W. (2008). Acta Cryst. E64, o2444. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page o734

doi:10.1107/S1600536810006884

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

N′-[(Bi­phenyl-4-yl)methyl­ene]-2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]acetohydrazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]acetohydrazide