Bis[4-(2-hydroxy­ethyl­amino)phen­yl] sulfone

Chen, G.-F.; Ma, G.-C.; Hu, J.; Zhang, W.-Q.

doi:10.1107/S1600536807063805

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o174

https://doi.org/10.1107/S1600536807063805

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Bis[4-(2-hydroxyethylamino)phenyl] sulfone

Guo-Feng Chen,^a,^b Guo-Chun Ma,^a Jing Hu ^a and Wen-Qin Zhang ^a ^*

^aDepartment of Chemistry, Tianjin University, Tianjin 300072, People's Republic of China, and ^bDepartment of Chemistry, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, People's Republic of China
^*Correspondence e-mail: chenguofeng@mail.hbu.edu.cn

(Received 12 November 2007; accepted 27 November 2007; online 6 December 2007)

The title compound, C₁₆H₂₀N₂O₄S, exhibits a V-shape structure with a dihedral angle of 77.5 (11)° formed by the two benzenel rings. The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds as well as π–π [3.738 (3) Å] and C—H⋯π interactions.

Related literature

For related literature, see: Shahsafi et al. (1987 ).

Experimental

Crystal data

C₁₆H₂₀N₂O₄S
M_r = 336.40
Monoclinic, C 2/c
a = 25.643 (17) Å
b = 8.118 (6) Å
c = 15.340 (11) Å
β = 102.989 (12)°
V = 3112 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 294 (2) K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.966
7793 measured reflections
2742 independent reflections
1982 reflections with I > 2σ
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.110
S = 1.03
2742 reflections
218 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3	0.93	2.59	2.919 (3)	101
C10—H10⋯O2	0.93	2.57	2.915 (3)	102
C7—H7⋯O3	0.93	2.47	2.854 (3)	105
O1—H1⋯O3ⁱ	0.82	1.87	2.683 (3)	175
O1—H1⋯S1ⁱ	0.82	2.88	3.638 (2)	154
O4—H4⋯O2ⁱⁱ	0.82	2.13	2.945 (3)	177
N1—H1C⋯O4ⁱⁱⁱ	0.892 (10)	2.185 (11)	3.066 (3)	169 (2)
N2—H2C⋯O1^iv	0.895 (10)	2.027 (11)	2.917 (3)	172 (2)
C10—H10⋯Cg2	0.93	2.97	3.762(4)	144
Symmetry codes: (i) $[-x, y+1, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[-x+{1\over2}, y+{1\over2}, -z+{1\over2}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807063805/bx2122sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063805/bx2122Isup2.hkl

checkCIF report

Comment top

The derivatives of diphenyl sulphone are used as precursors in the organic synthesis. Several derivatives of aminosulphones have been shown to possess strong tuberculostatic, antileprotic and anticonvulsant activities (Shahsafi, et al., 1987). The crystal structure determination of the title compound, (I), was carried out in order to elucidate its molecular conformation.

The V-shape structure of the molecule is supported by the two phenyl rings with a dihedral angle of 77.5 (11)°.

The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds (Table 1) as well as weak π-π and C—H..π interactions.

Related literature top

For related literature, see: Shahsafi et al. (1987).

Experimental top

The title compound, (I), was synthesized by the reaction of 4,4'-dichlorodiphenyl sulfone (5.74 g, 0.02 mol) with 2-aminoethanol (9.76 g, 0.16 mol). The mixture was refluxed for 6 h and cooled to room temperature. After dilution with water, it was filtered off, washed thoroughly with water, and recrystallized from dimethylformamide and water (4:1 v/v) to give the product as fine white needles (5.5 g, yield 81.8%). The pure product (0.1 g) was dissolved in 15 ml dimethylformamide and water (4:1 v/v). Single crystals were obtained from this solution by slow evaporation over a period of 7 days at room temperature (m.p. 464–466 K).

Structure description top

The V-shape structure of the molecule is supported by the two phenyl rings with a dihedral angle of 77.5 (11)°.

The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds (Table 1) as well as weak π-π and C—H..π interactions.

For related literature, see: Shahsafi et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. A view of the structure of (I), showing the atom-numbering Scheme; displacement ellipsoids were drawn at the 30% probability level.

Bis[4-(2-hydroxyethylamino)phenyl] sulfone top

Crystal data top

C₁₆H₂₀N₂O₄S	F(000) = 1424
M_r = 336.40	D_x = 1.436 Mg m⁻³
Monoclinic, C2/c	Melting point: 465(1) K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.643 (17) Å	Cell parameters from 2679 reflections
b = 8.118 (6) Å	θ = 2.6–26.4°
c = 15.340 (11) Å	µ = 0.23 mm⁻¹
β = 102.989 (12)°	T = 294 K
V = 3112 (4) Å³	Needle, colorless
Z = 8	0.20 × 0.18 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2742 independent reflections
Radiation source: fine-focus sealed tube	1982 reflections with I > 2σ
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→30
T_min = 0.953, T_max = 0.966	k = −9→9
7793 measured reflections	l = −15→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.055P)² + 1.5895P] where P = (F_o² + 2F_c²)/3
2742 reflections	(Δ/σ)_max = 0.005
218 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₆H₂₀N₂O₄S	V = 3112 (4) Å³
M_r = 336.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.643 (17) Å	µ = 0.23 mm⁻¹
b = 8.118 (6) Å	T = 294 K
c = 15.340 (11) Å	0.20 × 0.18 × 0.16 mm
β = 102.989 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2742 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1982 reflections with I > 2σ
T_min = 0.953, T_max = 0.966	R_int = 0.033
7793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.22 e Å⁻³
2742 reflections	Δρ_min = −0.35 e Å⁻³
218 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	0.13804 (2)	0.13061 (7)	0.27577 (4)	0.0437 (2)
O1	−0.11464 (7)	0.7991 (2)	0.07807 (12)	0.0614 (5)
H1	−0.1153	0.8496	0.1241	0.092*
O2	0.16477 (7)	0.1933 (2)	0.36085 (10)	0.0575 (5)
O3	0.11181 (7)	−0.0265 (2)	0.27233 (11)	0.0551 (5)
O4	0.37876 (7)	−0.1123 (3)	0.00979 (13)	0.0656 (5)
H4	0.3659	−0.1633	0.0460	0.098*
N1	−0.02318 (8)	0.5964 (3)	0.09390 (13)	0.0496 (5)
N2	0.29293 (8)	0.0802 (3)	0.05074 (14)	0.0479 (5)
C1	−0.06999 (11)	0.8469 (3)	0.04713 (18)	0.0605 (7)
H1A	−0.0667	0.9659	0.0504	0.073*
H1B	−0.0749	0.8150	−0.0151	0.073*
C2	−0.01965 (10)	0.7710 (3)	0.09995 (18)	0.0541 (7)
H2A	0.0106	0.8089	0.0771	0.065*
H2B	−0.0140	0.8045	0.1621	0.065*
C3	0.01441 (8)	0.4931 (3)	0.13841 (14)	0.0395 (5)
C4	0.06235 (9)	0.5465 (3)	0.19253 (16)	0.0455 (6)
H4A	0.0692	0.6588	0.1996	0.055*
C5	0.09948 (9)	0.4366 (3)	0.23534 (16)	0.0452 (6)
H5	0.1314	0.4743	0.2712	0.054*
C6	0.09002 (8)	0.2708 (3)	0.22587 (14)	0.0370 (5)
C7	0.04241 (9)	0.2161 (3)	0.17295 (15)	0.0436 (6)
H7	0.0358	0.1036	0.1664	0.052*
C8	0.00543 (9)	0.3235 (3)	0.13085 (15)	0.0449 (6)
H8	−0.0267	0.2844	0.0961	0.054*
C9	0.18453 (8)	0.1155 (3)	0.21042 (14)	0.0380 (5)
C10	0.23154 (9)	0.2043 (3)	0.23028 (15)	0.0441 (6)
H10	0.2389	0.2729	0.2801	0.053*
C11	0.26711 (9)	0.1918 (3)	0.17704 (16)	0.0450 (6)
H11	0.2989	0.2510	0.1914	0.054*
C12	0.25677 (9)	0.0920 (3)	0.10144 (14)	0.0378 (5)
C13	0.20852 (8)	0.0063 (3)	0.08150 (15)	0.0407 (5)
H13	0.2002	−0.0593	0.0305	0.049*
C14	0.17353 (9)	0.0173 (3)	0.13568 (15)	0.0424 (6)
H14	0.1418	−0.0423	0.1221	0.051*
C15	0.28658 (9)	−0.0244 (3)	−0.02587 (15)	0.0465 (6)
H15A	0.2595	0.0214	−0.0743	0.056*
H15B	0.2745	−0.1321	−0.0115	0.056*
C16	0.33752 (10)	−0.0418 (4)	−0.05525 (17)	0.0554 (7)
H16A	0.3313	−0.1096	−0.1087	0.066*
H16B	0.3489	0.0661	−0.0709	0.066*
H1C	−0.0542 (6)	0.548 (3)	0.0693 (15)	0.053 (7)*
H2C	0.3197 (7)	0.153 (2)	0.0623 (15)	0.049 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0429 (3)	0.0529 (4)	0.0352 (3)	0.0069 (3)	0.0084 (2)	0.0087 (3)
O1	0.0496 (10)	0.0687 (12)	0.0647 (12)	0.0064 (9)	0.0100 (9)	−0.0226 (10)
O2	0.0570 (10)	0.0800 (13)	0.0318 (9)	0.0134 (10)	0.0023 (8)	0.0028 (8)
O3	0.0590 (10)	0.0523 (10)	0.0570 (11)	−0.0009 (9)	0.0190 (9)	0.0179 (8)
O4	0.0422 (10)	0.0902 (15)	0.0653 (12)	0.0090 (10)	0.0144 (9)	0.0052 (11)
N1	0.0434 (12)	0.0531 (13)	0.0481 (12)	0.0080 (11)	0.0016 (10)	−0.0008 (10)
N2	0.0427 (11)	0.0510 (12)	0.0521 (12)	−0.0059 (10)	0.0150 (10)	−0.0089 (10)
C1	0.0681 (18)	0.0621 (17)	0.0520 (16)	0.0196 (15)	0.0147 (14)	0.0100 (14)
C2	0.0517 (15)	0.0544 (16)	0.0578 (16)	0.0082 (13)	0.0157 (12)	0.0068 (13)
C3	0.0367 (12)	0.0505 (14)	0.0329 (12)	0.0077 (11)	0.0113 (10)	0.0001 (10)
C4	0.0424 (13)	0.0445 (14)	0.0500 (14)	0.0024 (11)	0.0111 (11)	0.0014 (11)
C5	0.0362 (12)	0.0540 (15)	0.0442 (13)	−0.0014 (11)	0.0064 (10)	0.0011 (11)
C6	0.0331 (11)	0.0470 (13)	0.0325 (11)	0.0049 (10)	0.0103 (9)	0.0036 (10)
C7	0.0421 (13)	0.0457 (14)	0.0436 (13)	0.0019 (12)	0.0110 (11)	−0.0027 (11)
C8	0.0359 (12)	0.0553 (15)	0.0413 (13)	0.0018 (11)	0.0043 (10)	−0.0075 (11)
C9	0.0347 (11)	0.0411 (12)	0.0361 (12)	0.0082 (10)	0.0034 (9)	0.0048 (10)
C10	0.0430 (13)	0.0439 (14)	0.0426 (13)	0.0038 (11)	0.0040 (10)	−0.0037 (11)
C11	0.0371 (12)	0.0441 (13)	0.0518 (15)	−0.0028 (11)	0.0060 (11)	−0.0040 (12)
C12	0.0361 (11)	0.0375 (12)	0.0386 (12)	0.0050 (10)	0.0059 (10)	0.0038 (10)
C13	0.0358 (12)	0.0420 (13)	0.0414 (13)	0.0036 (10)	0.0024 (10)	−0.0050 (11)
C14	0.0316 (11)	0.0459 (13)	0.0472 (13)	0.0030 (10)	0.0034 (10)	0.0023 (11)
C15	0.0424 (13)	0.0533 (15)	0.0428 (13)	0.0017 (11)	0.0073 (11)	−0.0014 (11)
C16	0.0544 (15)	0.0697 (18)	0.0444 (14)	−0.0022 (14)	0.0158 (12)	−0.0033 (13)

Geometric parameters (Å, º) top

S1—O2	1.4249 (18)	C4—H4A	0.9300
S1—O3	1.4371 (19)	C5—C6	1.370 (3)
S1—C6	1.724 (2)	C5—H5	0.9300
S1—C9	1.726 (2)	C6—C7	1.379 (3)
O1—C1	1.390 (3)	C7—C8	1.342 (3)
O1—H1	0.8200	C7—H7	0.9300
O4—C16	1.402 (3)	C8—H8	0.9300
O4—H4	0.8200	C9—C14	1.373 (3)
N1—C3	1.343 (3)	C9—C10	1.379 (3)
N1—C2	1.422 (3)	C10—C11	1.358 (3)
N1—H1C	0.892 (10)	C10—H10	0.9300
N2—C12	1.341 (3)	C11—C12	1.390 (3)
N2—C15	1.429 (3)	C11—H11	0.9300
N2—H2C	0.895 (10)	C12—C13	1.393 (3)
C1—C2	1.494 (4)	C13—C14	1.356 (3)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.481 (3)
C2—H2B	0.9700	C15—H15A	0.9700
C3—C4	1.389 (3)	C15—H15B	0.9700
C3—C8	1.396 (3)	C16—H16A	0.9700
C4—C5	1.361 (3)	C16—H16B	0.9700

O2—S1—O3	118.39 (11)	C7—C6—S1	119.89 (18)
O2—S1—C6	108.63 (11)	C8—C7—C6	120.7 (2)
O3—S1—C6	106.71 (11)	C8—C7—H7	119.7
O2—S1—C9	107.72 (11)	C6—C7—H7	119.7
O3—S1—C9	107.12 (11)	C7—C8—C3	121.0 (2)
C6—S1—C9	107.85 (11)	C7—C8—H8	119.5
C1—O1—H1	109.5	C3—C8—H8	119.5
C16—O4—H4	109.5	C14—C9—C10	119.6 (2)
C3—N1—C2	124.2 (2)	C14—C9—S1	119.16 (18)
C3—N1—H1C	114.2 (16)	C10—C9—S1	121.22 (18)
C2—N1—H1C	120.3 (16)	C11—C10—C9	120.0 (2)
C12—N2—C15	123.6 (2)	C11—C10—H10	120.0
C12—N2—H2C	115.9 (15)	C9—C10—H10	120.0
C15—N2—H2C	119.8 (15)	C10—C11—C12	121.2 (2)
O1—C1—C2	112.2 (2)	C10—C11—H11	119.4
O1—C1—H1A	109.2	C12—C11—H11	119.4
C2—C1—H1A	109.2	N2—C12—C11	119.9 (2)
O1—C1—H1B	109.2	N2—C12—C13	122.2 (2)
C2—C1—H1B	109.2	C11—C12—C13	117.9 (2)
H1A—C1—H1B	107.9	C14—C13—C12	120.7 (2)
N1—C2—C1	109.9 (2)	C14—C13—H13	119.7
N1—C2—H2A	109.7	C12—C13—H13	119.7
C1—C2—H2A	109.7	C13—C14—C9	120.7 (2)
N1—C2—H2B	109.7	C13—C14—H14	119.7
C1—C2—H2B	109.7	C9—C14—H14	119.7
H2A—C2—H2B	108.2	N2—C15—C16	111.2 (2)
N1—C3—C4	123.1 (2)	N2—C15—H15A	109.4
N1—C3—C8	119.2 (2)	C16—C15—H15A	109.4
C4—C3—C8	117.7 (2)	N2—C15—H15B	109.4
C5—C4—C3	120.9 (2)	C16—C15—H15B	109.4
C5—C4—H4A	119.6	H15A—C15—H15B	108.0
C3—C4—H4A	119.6	O4—C16—C15	113.5 (2)
C4—C5—C6	120.3 (2)	O4—C16—H16A	108.9
C4—C5—H5	119.8	C15—C16—H16A	108.9
C6—C5—H5	119.8	O4—C16—H16B	108.9
C5—C6—C7	119.4 (2)	C15—C16—H16B	108.9
C5—C6—S1	120.64 (18)	H16A—C16—H16B	107.7

C3—N1—C2—C1	−175.9 (2)	O2—S1—C9—C14	161.83 (17)
O1—C1—C2—N1	60.4 (3)	O3—S1—C9—C14	33.5 (2)
C2—N1—C3—C4	−3.1 (3)	C6—S1—C9—C14	−81.1 (2)
C2—N1—C3—C8	176.8 (2)	O2—S1—C9—C10	−20.3 (2)
N1—C3—C4—C5	−179.1 (2)	O3—S1—C9—C10	−148.70 (18)
C8—C3—C4—C5	1.0 (3)	C6—S1—C9—C10	96.8 (2)
C3—C4—C5—C6	−0.2 (3)	C14—C9—C10—C11	−1.3 (3)
C4—C5—C6—C7	−0.4 (3)	S1—C9—C10—C11	−179.14 (18)
C4—C5—C6—S1	177.07 (17)	C9—C10—C11—C12	0.9 (3)
O2—S1—C6—C5	37.3 (2)	C15—N2—C12—C11	177.4 (2)
O3—S1—C6—C5	166.02 (17)	C15—N2—C12—C13	−2.2 (3)
C9—S1—C6—C5	−79.2 (2)	C10—C11—C12—N2	−179.1 (2)
O2—S1—C6—C7	−145.26 (17)	C10—C11—C12—C13	0.5 (3)
O3—S1—C6—C7	−16.6 (2)	N2—C12—C13—C14	178.0 (2)
C9—S1—C6—C7	98.25 (19)	C11—C12—C13—C14	−1.6 (3)
C5—C6—C7—C8	0.0 (3)	C12—C13—C14—C9	1.2 (3)
S1—C6—C7—C8	−177.44 (17)	C10—C9—C14—C13	0.3 (3)
C6—C7—C8—C3	0.9 (3)	S1—C9—C14—C13	178.15 (17)
N1—C3—C8—C7	178.8 (2)	C12—N2—C15—C16	−166.6 (2)
C4—C3—C8—C7	−1.4 (3)	N2—C15—C16—O4	61.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.59	2.919 (3)	101
C10—H10···O2	0.93	2.57	2.915 (3)	102
C7—H7···O3	0.93	2.47	2.854 (3)	105
O1—H1···O3ⁱ	0.82	1.87	2.683 (3)	175
O1—H1···S1ⁱ	0.82	2.88	3.638 (2)	154
O4—H4···O2ⁱⁱ	0.82	2.13	2.945 (3)	177
N1—H1C···O4ⁱⁱⁱ	0.89 (1)	2.19 (1)	3.066 (3)	169 (2)
N2—H2C···O1^iv	0.90 (1)	2.03 (1)	2.917 (3)	172 (2)
C10—H10···Cg2^v	0.93	2.97	3.762 (4)	144

Symmetry codes: (i) −x, y+1, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₂O₄S
M_r	336.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	25.643 (17), 8.118 (6), 15.340 (11)
β (°)	102.989 (12)
V (Å³)	3112 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.966
No. of measured, independent and observed (I > 2σ) reflections	7793, 2742, 1982
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 1.03
No. of reflections	2742
No. of parameters	218
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)	0.22, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.59	2.919 (3)	101.2
C10—H10···O2	0.93	2.57	2.915 (3)	102.2
C7—H7···O3	0.93	2.47	2.854 (3)	104.5
O1—H1···O3ⁱ	0.82	1.87	2.683 (3)	175.3
O1—H1···S1ⁱ	0.82	2.88	3.638 (2)	154.2
O4—H4···O2ⁱⁱ	0.82	2.13	2.945 (3)	176.8
N1—H1C···O4ⁱⁱⁱ	0.892 (10)	2.185 (11)	3.066 (3)	169 (2)
N2—H2C···O1^iv	0.895 (10)	2.027 (11)	2.917 (3)	172 (2)
C10—H10···Cg2^v	0.93	2.97	3.762 (4)	144.00

Symmetry codes: (i) −x, y+1, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) −x+1/2, y+1/2, −z+1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shahsafi, M. A., Meshkatalsadat, M. H. & Parekh, H. (1987). Indian J. Chem. 26B, 803–807. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar

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Volume 64| Part 1| January 2008| Page o174

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