2-[(3-Propyl­sulfanyl-5-p-tolyl-4H-1,2,4-triazol-4-yl)imino­meth­yl]phenol

Wang, W.; Liu, Q.; Xu, C.; Wu, W.; Gao, Y.

doi:10.1107/S1600536811029849

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2236

doi:10.1107/S1600536811029849

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2-[(3-Propylsulfanyl-5-p-tolyl-4H-1,2,4-triazol-4-yl)iminomethyl]phenol

Wei Wang,^a,^b Qing-lei Liu,^a Chao Xu,^b Wen-peng Wu ^b and Yan Gao ^b ^*

^aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China
^*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 5 July 2011; accepted 23 July 2011; online 2 August 2011)

In the title molecule, C₁₉H₂₀N₄OS, the two benzene rings form dihedral angles of 16.2 (1) and 12.0 (1)°, respectively, with the central triazole ring. In the crystal, intermolecular O—H⋯N hydrogen bonds link molecules into chains in the [010] direction.

Related literature

For standard values of the bond lengths, see: Allen et al. (1987 ). For the crystal structure of a related compound, see: Wang et al. (2011 ).

Experimental

Crystal data

C₁₉H₂₀N₄OS
M_r = 352.45
Monoclinic, C 2/c
a = 22.682 (2) Å
b = 18.1736 (15) Å
c = 9.1557 (8) Å
β = 109.678 (7)°
V = 3553.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.962, T_max = 0.977
16201 measured reflections
3499 independent reflections
3206 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.122
S = 1.14
3499 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.95 (3)	1.71 (3)	2.658 (2)	175 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029849/cv5131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029849/cv5131Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029849/cv5131Isup3.cml

checkCIF report

Comment top

In continuation of structural study of Mannich bases derivatives synthesized by reactions of the amino heterocycles and aromatic aldehydes in our group (Wang et al., 2011), we present here the crystal structure of the title compound, (I).

In (I) (Fig.1), all the bond lengths and angles are normal (Allen et al., 1987). The C5 atom in the triazole ring deviates form the normal C_sp² hybridization state having the bond angles of 108.4 (2)° (N2—C5—N3) and 127.6 (2)° (N3—C5—C6), respectively. Rings C6—C11 and C14—C19 are inclined with repect to the 1,2,4-triazole ring at 16.2 (2)° and 12.0 (2)°, respectively. Two benzene rings form a dihedral angle of 18.0 (2)°.

In the crystal structure, intermolecular O—H···N hydrogen bonds (Table 1) link the adjacent molecules into chains in [010].

Related literature top

For standard values of the bond lengths, see: Allen et al. (1987). For the crystal structure of a related compound, see: Wang et al. (2011).

Experimental top

The title compound was synthesized by the reaction of salicylic aldehyde (2.0 mmol) and 4-amino-3-propylthio-5-p-tolyl-1,2,4-triazole (2.0 mmol) by refluxing in ethanol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as colourless solid in 89% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

2-[(3-Propylsulfanyl-5-p-tolyl-4H-1,2,4-triazol-4- yl)iminomethyl]phenol top

Crystal data top

C₁₉H₂₀N₄OS	F(000) = 1488
M_r = 352.45	D_x = 1.318 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5676 reflections
a = 22.682 (2) Å	θ = 1.9–27.9°
b = 18.1736 (15) Å	µ = 0.20 mm⁻¹
c = 9.1557 (8) Å	T = 113 K
β = 109.678 (7)°	Prism, colourless
V = 3553.7 (5) Å³	0.20 × 0.16 × 0.12 mm
Z = 8

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3499 independent reflections
Radiation source: rotating anode	3206 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.061
Detector resolution: 14.22 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ϕ and ω scans	h = −27→27
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −21→22
T_min = 0.962, T_max = 0.977	l = −11→11
16201 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0382P)² + 4.5494P] where P = (F_o² + 2F_c²)/3
3499 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₂₀N₄OS	V = 3553.7 (5) Å³
M_r = 352.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.682 (2) Å	µ = 0.20 mm⁻¹
b = 18.1736 (15) Å	T = 113 K
c = 9.1557 (8) Å	0.20 × 0.16 × 0.12 mm
β = 109.678 (7)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3499 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3206 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.977	R_int = 0.061
16201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.28 e Å⁻³
3499 reflections	Δρ_min = −0.24 e Å⁻³
232 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.

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.

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

	x	y	z	U_iso*/U_eq
S1	0.28535 (3)	0.18666 (3)	0.66027 (7)	0.02339 (18)
O1	0.22719 (7)	0.34890 (9)	0.84176 (19)	0.0231 (4)
H1	0.2327 (15)	0.3982 (19)	0.816 (4)	0.065 (11)*
N1	0.28721 (9)	0.03831 (11)	0.6965 (2)	0.0231 (5)
N2	0.25373 (9)	−0.01562 (11)	0.7421 (2)	0.0234 (5)
N3	0.21532 (9)	0.09105 (10)	0.7742 (2)	0.0190 (4)
N4	0.17143 (9)	0.14097 (10)	0.7951 (2)	0.0206 (4)
C1	0.43083 (12)	0.09850 (16)	0.5327 (3)	0.0357 (7)
H1A	0.4081	0.0552	0.4785	0.053*
H1B	0.4737	0.0844	0.5946	0.053*
H1C	0.4320	0.1359	0.4566	0.053*
C2	0.39763 (11)	0.12982 (14)	0.6392 (3)	0.0257 (6)
H2A	0.3961	0.0919	0.7156	0.031*
H2B	0.4215	0.1725	0.6969	0.031*
C3	0.33133 (11)	0.15388 (13)	0.5455 (3)	0.0240 (5)
H3A	0.3092	0.1118	0.4819	0.029*
H3B	0.3337	0.1935	0.4735	0.029*
C4	0.26334 (10)	0.10185 (12)	0.7148 (3)	0.0194 (5)
C5	0.21029 (11)	0.01597 (12)	0.7866 (3)	0.0196 (5)
C6	0.16446 (11)	−0.02466 (13)	0.8370 (3)	0.0227 (5)
C7	0.12894 (12)	0.00694 (14)	0.9178 (3)	0.0268 (6)
H7	0.1336	0.0578	0.9433	0.032*
C8	0.08665 (12)	−0.03538 (15)	0.9615 (3)	0.0312 (6)
H8	0.0623	−0.0126	1.0152	0.037*
C9	0.07908 (11)	−0.11011 (14)	0.9288 (3)	0.0299 (6)
C10	0.11503 (12)	−0.14132 (14)	0.8479 (3)	0.0321 (6)
H10	0.1106	−0.1923	0.8234	0.038*
C11	0.15695 (11)	−0.09988 (13)	0.8024 (3)	0.0277 (6)
H11	0.1808	−0.1226	0.7473	0.033*
C12	0.03444 (13)	−0.15614 (17)	0.9807 (3)	0.0410 (7)
H12A	0.0174	−0.1957	0.9055	0.061*
H12B	0.0001	−0.1251	0.9875	0.061*
H12C	0.0568	−0.1775	1.0827	0.061*
C13	0.19299 (11)	0.20586 (13)	0.8382 (3)	0.0207 (5)
H13	0.2355	0.2165	0.8521	0.025*
C14	0.15332 (11)	0.26319 (13)	0.8662 (3)	0.0199 (5)
C15	0.09753 (11)	0.24755 (14)	0.8943 (3)	0.0256 (5)
H15	0.0839	0.1980	0.8929	0.031*
C16	0.06239 (12)	0.30375 (14)	0.9239 (3)	0.0300 (6)
H16	0.0247	0.2930	0.9434	0.036*
C17	0.08210 (12)	0.37635 (14)	0.9251 (3)	0.0283 (6)
H17	0.0574	0.4149	0.9448	0.034*
C18	0.13694 (11)	0.39332 (13)	0.8982 (3)	0.0228 (5)
H18	0.1501	0.4430	0.8997	0.027*
C19	0.17279 (11)	0.33639 (13)	0.8688 (3)	0.0200 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0284 (3)	0.0148 (3)	0.0310 (3)	−0.0006 (2)	0.0153 (3)	0.0012 (2)
O1	0.0262 (9)	0.0155 (9)	0.0319 (9)	0.0002 (7)	0.0153 (8)	0.0028 (7)
N1	0.0248 (11)	0.0157 (10)	0.0317 (11)	0.0003 (8)	0.0134 (9)	0.0030 (9)
N2	0.0256 (11)	0.0168 (10)	0.0300 (11)	−0.0006 (8)	0.0121 (9)	0.0008 (9)
N3	0.0205 (10)	0.0145 (10)	0.0235 (10)	0.0028 (8)	0.0093 (8)	−0.0001 (8)
N4	0.0222 (10)	0.0164 (10)	0.0252 (10)	0.0028 (8)	0.0108 (8)	0.0001 (8)
C1	0.0310 (15)	0.0409 (17)	0.0403 (16)	0.0033 (12)	0.0189 (13)	−0.0005 (13)
C2	0.0261 (13)	0.0246 (13)	0.0277 (13)	−0.0015 (10)	0.0108 (11)	−0.0009 (11)
C3	0.0277 (13)	0.0195 (13)	0.0274 (12)	−0.0009 (10)	0.0126 (11)	0.0021 (10)
C4	0.0210 (12)	0.0156 (12)	0.0218 (11)	−0.0009 (9)	0.0073 (10)	0.0002 (9)
C5	0.0219 (12)	0.0136 (11)	0.0229 (11)	0.0015 (9)	0.0070 (10)	0.0000 (9)
C6	0.0227 (12)	0.0188 (12)	0.0262 (12)	0.0002 (10)	0.0075 (10)	0.0069 (10)
C7	0.0330 (14)	0.0230 (13)	0.0274 (13)	0.0010 (11)	0.0140 (11)	0.0038 (11)
C8	0.0301 (14)	0.0366 (15)	0.0298 (13)	0.0002 (12)	0.0139 (11)	0.0059 (12)
C9	0.0250 (14)	0.0299 (15)	0.0322 (14)	−0.0059 (11)	0.0063 (11)	0.0107 (12)
C10	0.0265 (14)	0.0203 (13)	0.0462 (16)	−0.0027 (11)	0.0079 (12)	0.0056 (12)
C11	0.0250 (13)	0.0200 (13)	0.0377 (14)	0.0004 (10)	0.0099 (11)	0.0037 (11)
C12	0.0327 (16)	0.0453 (18)	0.0445 (17)	−0.0104 (13)	0.0125 (13)	0.0141 (14)
C13	0.0235 (12)	0.0190 (12)	0.0201 (11)	0.0002 (10)	0.0081 (10)	0.0014 (9)
C14	0.0238 (12)	0.0179 (12)	0.0186 (11)	0.0010 (9)	0.0079 (9)	0.0005 (9)
C15	0.0279 (13)	0.0201 (13)	0.0322 (13)	−0.0020 (10)	0.0145 (11)	−0.0018 (11)
C16	0.0297 (14)	0.0246 (14)	0.0428 (15)	−0.0012 (11)	0.0217 (12)	−0.0028 (12)
C17	0.0306 (14)	0.0240 (13)	0.0340 (14)	0.0053 (11)	0.0159 (12)	−0.0007 (11)
C18	0.0283 (13)	0.0169 (12)	0.0251 (12)	−0.0004 (10)	0.0115 (10)	0.0002 (10)
C19	0.0239 (12)	0.0199 (12)	0.0177 (11)	−0.0005 (10)	0.0088 (9)	0.0007 (10)

Geometric parameters (Å, º) top

S1—C4	1.744 (2)	C7—H7	0.9500
S1—C3	1.812 (2)	C8—C9	1.389 (4)
O1—C19	1.357 (3)	C8—H8	0.9500
O1—H1	0.95 (3)	C9—C10	1.394 (4)
N1—C4	1.310 (3)	C9—C12	1.508 (3)
N1—N2	1.388 (3)	C10—C11	1.382 (3)
N2—C5	1.318 (3)	C10—H10	0.9500
N3—C5	1.377 (3)	C11—H11	0.9500
N3—C4	1.386 (3)	C12—H12A	0.9800
N3—N4	1.407 (3)	C12—H12B	0.9800
N4—C13	1.287 (3)	C12—H12C	0.9800
C1—C2	1.529 (3)	C13—C14	1.455 (3)
C1—H1A	0.9800	C13—H13	0.9500
C1—H1B	0.9800	C14—C19	1.399 (3)
C1—H1C	0.9800	C14—C15	1.403 (3)
C2—C3	1.523 (3)	C15—C16	1.377 (3)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—C17	1.392 (3)
C3—H3A	0.9900	C16—H16	0.9500
C3—H3B	0.9900	C17—C18	1.382 (3)
C5—C6	1.470 (3)	C17—H17	0.9500
C6—C7	1.388 (3)	C18—C19	1.397 (3)
C6—C11	1.401 (3)	C18—H18	0.9500
C7—C8	1.390 (3)

C4—S1—C3	98.71 (11)	C9—C8—H8	119.1
C19—O1—H1	114 (2)	C7—C8—H8	119.1
C4—N1—N2	107.00 (19)	C8—C9—C10	117.4 (2)
C5—N2—N1	109.10 (19)	C8—C9—C12	121.5 (3)
C5—N3—C4	105.69 (18)	C10—C9—C12	121.1 (2)
C5—N3—N4	123.09 (18)	C11—C10—C9	121.6 (2)
C4—N3—N4	130.37 (19)	C11—C10—H10	119.2
C13—N4—N3	114.81 (19)	C9—C10—H10	119.2
C2—C1—H1A	109.5	C10—C11—C6	120.5 (2)
C2—C1—H1B	109.5	C10—C11—H11	119.8
H1A—C1—H1B	109.5	C6—C11—H11	119.8
C2—C1—H1C	109.5	C9—C12—H12A	109.5
H1A—C1—H1C	109.5	C9—C12—H12B	109.5
H1B—C1—H1C	109.5	H12A—C12—H12B	109.5
C3—C2—C1	110.6 (2)	C9—C12—H12C	109.5
C3—C2—H2A	109.5	H12A—C12—H12C	109.5
C1—C2—H2A	109.5	H12B—C12—H12C	109.5
C3—C2—H2B	109.5	N4—C13—C14	121.1 (2)
C1—C2—H2B	109.5	N4—C13—H13	119.4
H2A—C2—H2B	108.1	C14—C13—H13	119.4
C2—C3—S1	114.79 (17)	C19—C14—C15	119.3 (2)
C2—C3—H3A	108.6	C19—C14—C13	118.3 (2)
S1—C3—H3A	108.6	C15—C14—C13	122.5 (2)
C2—C3—H3B	108.6	C16—C15—C14	120.2 (2)
S1—C3—H3B	108.6	C16—C15—H15	119.9
H3A—C3—H3B	107.5	C14—C15—H15	119.9
N1—C4—N3	109.80 (19)	C15—C16—C17	119.9 (2)
N1—C4—S1	124.89 (18)	C15—C16—H16	120.0
N3—C4—S1	125.18 (17)	C17—C16—H16	120.0
N2—C5—N3	108.4 (2)	C18—C17—C16	121.1 (2)
N2—C5—C6	124.0 (2)	C18—C17—H17	119.5
N3—C5—C6	127.6 (2)	C16—C17—H17	119.5
C7—C6—C11	118.4 (2)	C17—C18—C19	119.1 (2)
C7—C6—C5	123.9 (2)	C17—C18—H18	120.4
C11—C6—C5	117.7 (2)	C19—C18—H18	120.4
C6—C7—C8	120.4 (2)	O1—C19—C18	122.4 (2)
C6—C7—H7	119.8	O1—C19—C14	117.2 (2)
C8—C7—H7	119.8	C18—C19—C14	120.4 (2)
C9—C8—C7	121.8 (2)

C4—N1—N2—C5	0.2 (3)	C5—C6—C7—C8	−179.9 (2)
C5—N3—N4—C13	154.6 (2)	C6—C7—C8—C9	1.0 (4)
C4—N3—N4—C13	−37.5 (3)	C7—C8—C9—C10	−0.9 (4)
C1—C2—C3—S1	176.26 (18)	C7—C8—C9—C12	178.2 (2)
C4—S1—C3—C2	−80.05 (19)	C8—C9—C10—C11	0.4 (4)
N2—N1—C4—N3	1.0 (3)	C12—C9—C10—C11	−178.8 (2)
N2—N1—C4—S1	−175.07 (16)	C9—C10—C11—C6	0.0 (4)
C5—N3—C4—N1	−1.8 (2)	C7—C6—C11—C10	0.0 (4)
N4—N3—C4—N1	−171.2 (2)	C5—C6—C11—C10	179.4 (2)
C5—N3—C4—S1	174.29 (17)	N3—N4—C13—C14	−179.28 (19)
N4—N3—C4—S1	4.8 (3)	N4—C13—C14—C19	−161.9 (2)
C3—S1—C4—N1	11.7 (2)	N4—C13—C14—C15	19.7 (3)
C3—S1—C4—N3	−163.77 (19)	C19—C14—C15—C16	0.1 (4)
N1—N2—C5—N3	−1.3 (3)	C13—C14—C15—C16	178.4 (2)
N1—N2—C5—C6	177.6 (2)	C14—C15—C16—C17	0.3 (4)
C4—N3—C5—N2	1.9 (2)	C15—C16—C17—C18	−0.5 (4)
N4—N3—C5—N2	172.28 (19)	C16—C17—C18—C19	0.3 (4)
C4—N3—C5—C6	−177.0 (2)	C17—C18—C19—O1	−179.8 (2)
N4—N3—C5—C6	−6.6 (4)	C17—C18—C19—C14	0.2 (3)
N2—C5—C6—C7	164.0 (2)	C15—C14—C19—O1	179.7 (2)
N3—C5—C6—C7	−17.3 (4)	C13—C14—C19—O1	1.2 (3)
N2—C5—C6—C11	−15.3 (3)	C15—C14—C19—C18	−0.3 (3)
N3—C5—C6—C11	163.4 (2)	C13—C14—C19—C18	−178.7 (2)
C11—C6—C7—C8	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.95 (3)	2.58 (3)	3.464 (3)	155 (3)
O1—H1···N2ⁱ	0.95 (3)	1.71 (3)	2.658 (2)	175 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₄OS
M_r	352.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	22.682 (2), 18.1736 (15), 9.1557 (8)
β (°)	109.678 (7)
V (Å³)	3553.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.962, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	16201, 3499, 3206
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.122, 1.14
No. of reflections	3499
No. of parameters	232
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.95 (3)	1.71 (3)	2.658 (2)	175 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011). Acta Cryst. E67, o269. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2236

doi:10.1107/S1600536811029849

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