2-[(3,5-Di-tert-butyl-4-hydroxy­benz­yl)­sulfan­yl]-N′-isopropyl­ideneaceto­hydrazide

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

doi:10.1107/S1600536809007843

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o730

doi:10.1107/S1600536809007843

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2-[(3,5-Di-tert-butyl-4-hydroxybenzyl)sulfanyl]-N′-isopropylideneacetohydrazide

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

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

(Received 25 February 2009; accepted 4 March 2009; online 11 March 2009)

The title compound, C₂₀H₃₂N₂O₂S, the condensation product of a thioacetohydrazine and acetone, has a two-coordinate S atom and the angle at this atom is 100.7 (1)°. The (CH₃)C=N—NH—C(O)– substituent engages in N—H⋯O hydrogen-bonding interactions with the substituent of an adjacent molecule across a center of inversion, generating a dimeric structure.

Related literature

There are several structural studies of (CH₃)C=N–NH–C(O)–X compounds; for N-acetyl-N′-isopropylidenehydrazine, see: Khusainova et al. (2004 ). For the synthesis of the thioacetohydrazine reactant, see: MacLeay & Meyers (1989 ); Myers & MacLeay (1989 ).

Experimental

Crystal data

C₂₀H₃₂N₂O₂S
M_r = 364.54
Monoclinic, C 2/c
a = 30.8643 (10) Å
b = 10.0128 (3) Å
c = 13.9596 (5) Å
β = 96.227 (2)°
V = 4288.6 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.984
14652 measured reflections
4886 independent reflections
3240 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.05
4886 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 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	2.10	2.940 (2)	159
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536809007843/tk2379sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007843/tk2379Isup2.hkl

checkCIF report

Related literature top

There are several structural studies of (CH₃)C=N–NH–C(O)–X compounds; for N-acetyl-N'-isopropylidenehydrazine, see: Khusainova et al. (2004). For the synthesis of the thioacetohydrazine reactant, see: MacLeay & Meyers (1989); Myers & MacLeay (1989).

Experimental top

2-(3,5-Di-tert-butyl-4-hydroxybenzylthio)acetohydrazine (0.5 g, 1.54 mmol) and acetone (10 ml) were heated for 6 h; several drops of acetic acid were added to the reaction. The solvent was removed and the product recrystallized from hexane.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 C₂₀H₃₂N₂O₂S at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

2-[(3,5-Di-tert-butyl-4-hydroxybenzyl)sulfanyl]-N'- isopropylideneacetohydrazide top

Crystal data top

C₂₀H₃₂N₂O₂S	F(000) = 1584
M_r = 364.54	D_x = 1.129 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1963 reflections
a = 30.8643 (10) Å	θ = 2.6–26.3°
b = 10.0128 (3) Å	µ = 0.17 mm⁻¹
c = 13.9596 (5) Å	T = 100 K
β = 96.227 (2)°	Block, colorless
V = 4288.6 (2) Å³	0.25 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	4886 independent reflections
Radiation source: fine-focus sealed tube	3240 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −39→40
T_min = 0.960, T_max = 0.984	k = −13→13
14652 measured reflections	l = −18→14

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-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0627P)² + 0.8959P] where P = (F_o² + 2F_c²)/3
4886 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₃₂N₂O₂S	V = 4288.6 (2) Å³
M_r = 364.54	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.8643 (10) Å	µ = 0.17 mm⁻¹
b = 10.0128 (3) Å	T = 100 K
c = 13.9596 (5) Å	0.25 × 0.15 × 0.10 mm
β = 96.227 (2)°

Data collection top

Bruker SMART APEX diffractometer	4886 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3240 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.984	R_int = 0.052
14652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
4886 reflections	Δρ_min = −0.28 e Å⁻³
237 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.394869 (18)	0.18708 (5)	0.52819 (4)	0.02810 (16)
O1	0.32415 (5)	0.04431 (14)	0.08151 (10)	0.0287 (4)
H1O	0.3479	0.0304	0.0591	0.066 (10)*
O2	0.45752 (5)	0.41852 (14)	0.43360 (10)	0.0284 (4)
N1	0.49822 (5)	0.32105 (16)	0.55791 (12)	0.0228 (4)
H1	0.5109	0.3970	0.5762	0.033 (6)*
N2	0.51037 (5)	0.20268 (16)	0.60634 (12)	0.0233 (4)
C1	0.34695 (6)	0.22530 (19)	0.35011 (14)	0.0212 (4)
C2	0.31851 (6)	0.11801 (18)	0.33503 (15)	0.0208 (4)
H2	0.3045	0.0851	0.3876	0.025*
C3	0.30992 (6)	0.05737 (18)	0.24556 (15)	0.0205 (4)
C4	0.33196 (6)	0.10754 (18)	0.17019 (14)	0.0207 (4)
C5	0.35919 (6)	0.21967 (19)	0.18074 (14)	0.0206 (4)
C6	0.36638 (6)	0.27540 (19)	0.27299 (14)	0.0213 (4)
H6	0.3853	0.3502	0.2830	0.026*
C7	0.27708 (7)	−0.0579 (2)	0.22932 (15)	0.0257 (5)
C8	0.25474 (7)	−0.0877 (2)	0.31963 (16)	0.0326 (5)
H8A	0.2394	−0.0077	0.3383	0.049*
H8B	0.2767	−0.1138	0.3723	0.049*
H8C	0.2338	−0.1606	0.3061	0.049*
C9	0.30019 (9)	−0.1865 (2)	0.2033 (2)	0.0425 (6)
H9A	0.2790	−0.2594	0.1946	0.064*
H9B	0.3229	−0.2093	0.2554	0.064*
H9C	0.3135	−0.1729	0.1435	0.064*
C10	0.24093 (7)	−0.0210 (2)	0.14912 (17)	0.0360 (6)
H10A	0.2260	0.0600	0.1674	0.054*
H10B	0.2199	−0.0945	0.1398	0.054*
H10C	0.2538	−0.0049	0.0890	0.054*
C11	0.38057 (7)	0.2813 (2)	0.09618 (16)	0.0284 (5)
C12	0.40558 (9)	0.4089 (2)	0.12623 (17)	0.0404 (6)
H12A	0.4293	0.3879	0.1764	0.061*
H12B	0.3858	0.4734	0.1513	0.061*
H12C	0.4177	0.4472	0.0703	0.061*
C13	0.34528 (10)	0.3206 (3)	0.01478 (18)	0.0480 (7)
H13A	0.3255	0.3861	0.0390	0.072*
H13B	0.3287	0.2410	−0.0078	0.072*
H13C	0.3591	0.3596	−0.0387	0.072*
C14	0.41348 (10)	0.1852 (2)	0.0594 (2)	0.0544 (8)
H14A	0.4342	0.1558	0.1135	0.082*
H14B	0.4292	0.2307	0.0116	0.082*
H14C	0.3981	0.1075	0.0297	0.082*
C15	0.35698 (7)	0.2863 (2)	0.44856 (14)	0.0242 (5)
H15A	0.3295	0.2968	0.4783	0.029*
H15B	0.3695	0.3764	0.4417	0.029*
C16	0.44235 (7)	0.18946 (19)	0.46239 (16)	0.0258 (5)
H16A	0.4615	0.1128	0.4823	0.031*
H16B	0.4332	0.1816	0.3924	0.031*
C17	0.46677 (6)	0.3174 (2)	0.48258 (14)	0.0221 (4)
C18	0.54119 (7)	0.2084 (2)	0.67522 (15)	0.0252 (5)
C19	0.55491 (8)	0.0790 (2)	0.72261 (16)	0.0328 (5)
H19A	0.5361	0.0070	0.6946	0.049*
H19B	0.5524	0.0852	0.7919	0.049*
H19C	0.5852	0.0600	0.7124	0.049*
C20	0.56467 (8)	0.3315 (2)	0.71190 (17)	0.0376 (6)
H20A	0.5435	0.4023	0.7203	0.056*
H20B	0.5844	0.3607	0.6655	0.056*
H20C	0.5816	0.3124	0.7739	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0292 (3)	0.0299 (3)	0.0231 (3)	−0.0090 (2)	−0.0063 (2)	0.0075 (2)
O1	0.0321 (9)	0.0280 (8)	0.0264 (9)	−0.0086 (7)	0.0057 (7)	−0.0100 (6)
O2	0.0270 (8)	0.0279 (8)	0.0286 (9)	−0.0029 (6)	−0.0044 (7)	0.0037 (6)
N1	0.0219 (9)	0.0237 (8)	0.0219 (9)	−0.0034 (7)	−0.0018 (7)	−0.0016 (7)
N2	0.0237 (9)	0.0257 (9)	0.0203 (9)	0.0017 (7)	0.0019 (7)	0.0006 (7)
C1	0.0188 (10)	0.0232 (9)	0.0207 (11)	0.0016 (8)	−0.0024 (8)	0.0014 (8)
C2	0.0174 (10)	0.0224 (9)	0.0223 (11)	0.0006 (8)	0.0009 (8)	0.0044 (8)
C3	0.0170 (10)	0.0193 (9)	0.0243 (11)	0.0003 (8)	−0.0015 (8)	0.0014 (8)
C4	0.0200 (10)	0.0199 (9)	0.0214 (11)	−0.0004 (8)	−0.0012 (8)	−0.0024 (8)
C5	0.0208 (10)	0.0201 (9)	0.0208 (11)	0.0006 (8)	0.0015 (8)	0.0007 (8)
C6	0.0190 (10)	0.0193 (9)	0.0244 (11)	−0.0026 (8)	−0.0031 (8)	0.0013 (8)
C7	0.0237 (11)	0.0250 (10)	0.0282 (12)	−0.0071 (9)	0.0023 (9)	−0.0018 (9)
C8	0.0303 (12)	0.0305 (11)	0.0373 (14)	−0.0113 (10)	0.0048 (10)	0.0031 (10)
C9	0.0496 (16)	0.0223 (11)	0.0580 (18)	−0.0087 (11)	0.0172 (13)	−0.0045 (11)
C10	0.0269 (12)	0.0433 (13)	0.0359 (14)	−0.0155 (11)	−0.0046 (10)	−0.0016 (11)
C11	0.0367 (13)	0.0260 (11)	0.0232 (12)	−0.0095 (9)	0.0066 (10)	0.0000 (9)
C12	0.0553 (16)	0.0360 (13)	0.0310 (14)	−0.0208 (12)	0.0096 (12)	0.0026 (10)
C13	0.0673 (19)	0.0478 (15)	0.0261 (14)	−0.0202 (14)	−0.0072 (13)	0.0108 (11)
C14	0.0605 (18)	0.0398 (14)	0.071 (2)	−0.0102 (13)	0.0424 (16)	−0.0037 (14)
C15	0.0231 (11)	0.0274 (10)	0.0214 (11)	−0.0001 (9)	−0.0013 (9)	0.0000 (8)
C16	0.0252 (11)	0.0233 (10)	0.0270 (12)	0.0028 (9)	−0.0065 (9)	−0.0036 (9)
C17	0.0181 (10)	0.0275 (10)	0.0207 (11)	−0.0004 (8)	0.0024 (8)	−0.0024 (9)
C18	0.0276 (11)	0.0279 (11)	0.0199 (11)	0.0001 (9)	0.0018 (9)	−0.0020 (8)
C19	0.0395 (13)	0.0323 (12)	0.0253 (13)	0.0048 (10)	−0.0031 (10)	−0.0029 (9)
C20	0.0441 (14)	0.0353 (12)	0.0294 (13)	−0.0072 (11)	−0.0145 (11)	0.0031 (10)

Geometric parameters (Å, º) top

S1—C16	1.812 (2)	C10—H10A	0.9800
S1—C15	1.819 (2)	C10—H10B	0.9800
O1—C4	1.388 (2)	C10—H10C	0.9800
O1—H1O	0.8400	C11—C14	1.528 (3)
O2—C17	1.237 (2)	C11—C12	1.527 (3)
N1—C17	1.352 (2)	C11—C13	1.537 (3)
N1—N2	1.396 (2)	C12—H12A	0.9800
N1—H1	0.8800	C12—H12B	0.9800
N2—C18	1.278 (3)	C12—H12C	0.9800
C1—C6	1.382 (3)	C13—H13A	0.9800
C1—C2	1.389 (3)	C13—H13B	0.9800
C1—C15	1.505 (3)	C13—H13C	0.9800
C2—C3	1.388 (3)	C14—H14A	0.9800
C2—H2	0.9500	C14—H14B	0.9800
C3—C4	1.406 (3)	C14—H14C	0.9800
C3—C7	1.536 (3)	C15—H15A	0.9900
C4—C5	1.401 (3)	C15—H15B	0.9900
C5—C6	1.399 (3)	C16—C17	1.498 (3)
C5—C11	1.542 (3)	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C7—C8	1.531 (3)	C18—C20	1.493 (3)
C7—C9	1.535 (3)	C18—C19	1.495 (3)
C7—C10	1.537 (3)	C19—H19A	0.9800
C8—H8A	0.9800	C19—H19B	0.9800
C8—H8B	0.9800	C19—H19C	0.9800
C8—H8C	0.9800	C20—H20A	0.9800
C9—H9A	0.9800	C20—H20B	0.9800
C9—H9B	0.9800	C20—H20C	0.9800
C9—H9C	0.9800

C16—S1—C15	100.65 (10)	C14—C11—C5	111.09 (18)
C4—O1—H1O	109.5	C12—C11—C5	111.70 (17)
C17—N1—N2	119.11 (16)	C13—C11—C5	109.91 (19)
C17—N1—H1	120.4	C11—C12—H12A	109.5
N2—N1—H1	120.4	C11—C12—H12B	109.5
C18—N2—N1	117.74 (17)	H12A—C12—H12B	109.5
C6—C1—C2	118.89 (18)	C11—C12—H12C	109.5
C6—C1—C15	120.02 (18)	H12A—C12—H12C	109.5
C2—C1—C15	121.09 (18)	H12B—C12—H12C	109.5
C3—C2—C1	122.04 (19)	C11—C13—H13A	109.5
C3—C2—H2	119.0	C11—C13—H13B	109.5
C1—C2—H2	119.0	H13A—C13—H13B	109.5
C2—C3—C4	117.15 (17)	C11—C13—H13C	109.5
C2—C3—C7	121.32 (18)	H13A—C13—H13C	109.5
C4—C3—C7	121.52 (17)	H13B—C13—H13C	109.5
O1—C4—C5	120.24 (17)	C11—C14—H14A	109.5
O1—C4—C3	116.94 (17)	C11—C14—H14B	109.5
C5—C4—C3	122.76 (18)	H14A—C14—H14B	109.5
C6—C5—C4	116.74 (18)	C11—C14—H14C	109.5
C6—C5—C11	120.44 (17)	H14A—C14—H14C	109.5
C4—C5—C11	122.82 (17)	H14B—C14—H14C	109.5
C1—C6—C5	122.24 (18)	C1—C15—S1	113.01 (14)
C1—C6—H6	118.9	C1—C15—H15A	109.0
C5—C6—H6	118.9	S1—C15—H15A	109.0
C8—C7—C9	107.06 (18)	C1—C15—H15B	109.0
C8—C7—C3	111.95 (17)	S1—C15—H15B	109.0
C9—C7—C3	110.44 (17)	H15A—C15—H15B	107.8
C8—C7—C10	106.88 (18)	C17—C16—S1	109.51 (14)
C9—C7—C10	110.41 (19)	C17—C16—H16A	109.8
C3—C7—C10	110.01 (17)	S1—C16—H16A	109.8
C7—C8—H8A	109.5	C17—C16—H16B	109.8
C7—C8—H8B	109.5	S1—C16—H16B	109.8
H8A—C8—H8B	109.5	H16A—C16—H16B	108.2
C7—C8—H8C	109.5	O2—C17—N1	120.74 (18)
H8A—C8—H8C	109.5	O2—C17—C16	120.97 (18)
H8B—C8—H8C	109.5	N1—C17—C16	118.26 (18)
C7—C9—H9A	109.5	N2—C18—C20	126.07 (19)
C7—C9—H9B	109.5	N2—C18—C19	116.51 (19)
H9A—C9—H9B	109.5	C20—C18—C19	117.41 (19)
C7—C9—H9C	109.5	C18—C19—H19A	109.5
H9A—C9—H9C	109.5	C18—C19—H19B	109.5
H9B—C9—H9C	109.5	H19A—C19—H19B	109.5
C7—C10—H10A	109.5	C18—C19—H19C	109.5
C7—C10—H10B	109.5	H19A—C19—H19C	109.5
H10A—C10—H10B	109.5	H19B—C19—H19C	109.5
C7—C10—H10C	109.5	C18—C20—H20A	109.5
H10A—C10—H10C	109.5	C18—C20—H20B	109.5
H10B—C10—H10C	109.5	H20A—C20—H20B	109.5
C14—C11—C12	106.5 (2)	C18—C20—H20C	109.5
C14—C11—C13	110.9 (2)	H20A—C20—H20C	109.5
C12—C11—C13	106.61 (18)	H20B—C20—H20C	109.5

C17—N1—N2—C18	177.73 (18)	C4—C3—C7—C9	65.2 (3)
C6—C1—C2—C3	1.8 (3)	C2—C3—C7—C10	122.0 (2)
C15—C1—C2—C3	−177.81 (18)	C4—C3—C7—C10	−56.9 (2)
C1—C2—C3—C4	1.2 (3)	C6—C5—C11—C14	114.5 (2)
C1—C2—C3—C7	−177.73 (18)	C4—C5—C11—C14	−65.8 (3)
C2—C3—C4—O1	178.34 (17)	C6—C5—C11—C12	−4.3 (3)
C7—C3—C4—O1	−2.8 (3)	C4—C5—C11—C12	175.47 (19)
C2—C3—C4—C5	−4.5 (3)	C6—C5—C11—C13	−122.4 (2)
C7—C3—C4—C5	174.38 (18)	C4—C5—C11—C13	57.3 (3)
O1—C4—C5—C6	−178.28 (17)	C6—C1—C15—S1	−102.63 (19)
C3—C4—C5—C6	4.7 (3)	C2—C1—C15—S1	77.0 (2)
O1—C4—C5—C11	1.9 (3)	C16—S1—C15—C1	61.45 (16)
C3—C4—C5—C11	−175.14 (19)	C15—S1—C16—C17	81.49 (15)
C2—C1—C6—C5	−1.6 (3)	N2—N1—C17—O2	−174.54 (18)
C15—C1—C6—C5	178.00 (18)	N2—N1—C17—C16	7.7 (3)
C4—C5—C6—C1	−1.5 (3)	S1—C16—C17—O2	−87.7 (2)
C11—C5—C6—C1	178.29 (18)	S1—C16—C17—N1	89.99 (19)
C2—C3—C7—C8	3.3 (3)	N1—N2—C18—C20	2.5 (3)
C4—C3—C7—C8	−175.55 (18)	N1—N2—C18—C19	−177.17 (17)
C2—C3—C7—C9	−115.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.10	2.940 (2)	159

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₃₂N₂O₂S
M_r	364.54
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	30.8643 (10), 10.0128 (3), 13.9596 (5)
β (°)	96.227 (2)
V (Å³)	4288.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.25 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	14652, 4886, 3240
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.05
No. of reflections	4886
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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	2.10	2.940 (2)	159

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 (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khusainova, N. G., Mostovaya, O. M., Azancheev, N. M., Litvinov, I. A., Krivolapov, B. D. & Cherkasov, R. A. (2004). Mendeleev Commun. 14, 212–214. Web of Science CSD CrossRef Google Scholar
MacLeay, R. E. & Meyers, T. D. (1989). Eur. Patent EP 303986 A2 19890222. Google Scholar
Myers, T. D. & MacLeay, R. E. (1989). Eur. Patent EP 306729 A1 19890315. 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 4| April 2009| Page o730

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