N-(2-Nitro­phenyl­sulfon­yl)-N-(4-nitro­phenyl­sulfon­yl)methyl­amine

Lu, H.

doi:10.1107/S1600536808027499

organic compounds

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Volume 64| Part 10| October 2008| Page o1885

doi:10.1107/S1600536808027499

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N-(2-Nitrophenylsulfonyl)-N-(4-nitrophenylsulfonyl)methylamine

Haiyan Lu ^a ^*

^aThe Graduate School of the Chinese Academy of Sciences, Beijing 100049, People's Republic of China
^*Correspondence e-mail: haiyan_lu2008@yahoo.cn

(Received 22 July 2008; accepted 27 August 2008; online 6 September 2008)

In the crystal structure of the title compound, C₁₃H₁₁N₃O₈S₂, molecules are linked by intermolecular C—H⋯O hydrogen bonds into zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic π–π stacking interactions [centroid–centroid distance = 3.749 (3) Å] involving adjacent 4-nitrobenzene rings. Intramolecular C—H⋯O hydrogen bonds are also present.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 ); Curtis & Pavkovic (1983 ). For details of the biological activities of sulfonamide compounds, see: Kamoshita et al. (1987 ). For details of the application of sulfonimade catalysts, see: Zhang et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₈S₂
M_r = 401.37
Monoclinic, P 2₁ /c
a = 13.517 (3) Å
b = 9.994 (2) Å
c = 11.990 (2) Å
β = 95.26 (3)°
V = 1613.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 153 (2) K
0.58 × 0.47 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi 1995 ) T_min = 0.750, T_max = 0.897
15376 measured reflections
3683 independent reflections
3540 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.094
S = 1.13
3683 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O7	0.95	2.53	2.902 (2)	104
C4—H4A⋯O5	0.95	2.38	2.803 (2)	106
C13—H13A⋯O7	0.98	2.54	2.978 (2)	107
C13—H13C⋯O1	0.98	2.34	2.972 (2)	122
C1—H1A⋯O6ⁱ	0.95	2.51	3.369 (2)	150
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); 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: 10.1107/S1600536808027499/rz2239sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027499/rz2239Isup2.hkl

checkCIF report

Comment top

Molecules containing the sulfonimide group have been recently of interest for their applications as herbicides (Kamoshita et al., 1987) and catalysts (Zhang et al., 2007). In the present paper, the crystal structure of a new compound containing two sulfonimide groups is reported.

In the molecule of the title compound (Fig. 1) all bond lengths are normal (Allen et al., 1987) and in a good agreement with those reported previously for similar compounds (Henschel et al., 1996; Curtis & Pavkovic, 1983). The molecular conformation is stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal structure, molecules are linked by intermolecular C—H···O hydrogen bonding interactions (Fig. 2) forming zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic π-π stacking interactions occurring between adjacent the 4-nitrobenzene rings with a centroid-centroid distance of 3.749 (3) Å.

Related literature top

For the crystal structures of related compounds, see: Henschel et al. (1996); Curtis & Pavkovic (1983). For details of the biological activities of sulfonimide compounds, see: Kamoshita et al. (1987). For details of the application of sulfonimides catalysts, see: Zhang et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of 4-nitro-benzene-1-sulfonyl chloride (10 mmol, 2.21 g) in anhydrous CH₂Cl₂ (10 mL) was dropwise added over a period of 10 min to a solution of 2-nitro-N-methyl-benzenesulfonamide (10 mmol, 2.16 g) and EtN(i-Pr)₂ (3 mmol) in CH₂Cl₂ (10 mL) at 273K. The mixture was stirred at room temperature for 4 h. The organic phase was washed with 2N HCl twice and dried over anhydrous Na₂SO₄. The solvent was removed and the residue was purified by flash chromatography (2:1 cyclohexane/dichloromethane) to give the title compound as a white solid (2.81 mg, 70% yield). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethanol/dichloromethane solution (1:1 v/v) at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the b axis, showing the chains of molecules formed by intermolecular hydrogen bonds (dashed lines).

N-(2-Nitrophenylsulfonyl)-N-(4-nitrophenylsulfonyl)methylamine top

Crystal data top

C₁₃H₁₁N₃O₈S₂	F(000) = 824
M_r = 401.37	D_x = 1.653 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10014 reflections
a = 13.517 (3) Å	θ = 6.2–55.0°
b = 9.994 (2) Å	µ = 0.38 mm⁻¹
c = 11.990 (2) Å	T = 153 K
β = 95.26 (3)°	Block, colourless
V = 1613.0 (6) Å³	0.58 × 0.47 × 0.29 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3683 independent reflections
Radiation source: Rotating Anode	3540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω oscillation scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	h = −17→17
T_min = 0.750, T_max = 0.897	k = −12→12
15376 measured reflections	l = −15→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0558P)² + 0.7411P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
3683 reflections	Δρ_max = 0.49 e Å⁻³
236 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2001), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0231 (18)

Crystal data top

C₁₃H₁₁N₃O₈S₂	V = 1613.0 (6) Å³
M_r = 401.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.517 (3) Å	µ = 0.38 mm⁻¹
b = 9.994 (2) Å	T = 153 K
c = 11.990 (2) Å	0.58 × 0.47 × 0.29 mm
β = 95.26 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3683 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	3540 reflections with I > 2σ(I)
T_min = 0.750, T_max = 0.897	R_int = 0.017
15376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.13	Δρ_max = 0.49 e Å⁻³
3683 reflections	Δρ_min = −0.41 e Å⁻³
236 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.15312 (2)	0.15728 (3)	0.41897 (3)	0.01644 (11)
S2	0.35222 (2)	0.06267 (3)	0.48921 (3)	0.01728 (11)
O8	0.20741 (8)	0.19778 (11)	0.32804 (8)	0.0220 (2)
O7	0.06390 (8)	0.08053 (11)	0.39952 (9)	0.0241 (2)
O3	0.13493 (10)	0.70583 (13)	0.72576 (12)	0.0399 (3)
O6	0.39404 (8)	−0.02832 (12)	0.57283 (9)	0.0261 (2)
O5	0.38943 (8)	0.19667 (11)	0.48792 (9)	0.0255 (2)
O4	−0.01529 (9)	0.63329 (11)	0.73325 (9)	0.0271 (2)
N3	0.23085 (9)	0.06608 (12)	0.50391 (10)	0.0187 (2)
C7	0.12748 (10)	0.29709 (13)	0.50127 (11)	0.0161 (3)
O2	0.34613 (11)	−0.36035 (12)	0.39097 (13)	0.0401 (3)
C8	0.04276 (10)	0.29488 (13)	0.55885 (11)	0.0173 (3)
H8B	−0.0011	0.2205	0.5523	0.021*
N1	0.31903 (10)	−0.24388 (12)	0.39825 (11)	0.0241 (3)
C6	0.36282 (10)	−0.14363 (14)	0.32761 (12)	0.0199 (3)
C11	0.17430 (11)	0.51236 (14)	0.57559 (13)	0.0215 (3)
H11A	0.2180	0.5870	0.5826	0.026*
C12	0.19373 (10)	0.40442 (15)	0.50825 (12)	0.0209 (3)
H12A	0.2509	0.4036	0.4677	0.025*
C4	0.40219 (10)	0.08068 (15)	0.27685 (13)	0.0218 (3)
H4A	0.4043	0.1739	0.2922	0.026*
C10	0.08951 (10)	0.50856 (13)	0.63249 (11)	0.0177 (3)
C5	0.36741 (10)	−0.00693 (14)	0.35469 (11)	0.0174 (3)
O1	0.25661 (11)	−0.20743 (12)	0.45856 (12)	0.0375 (3)
C9	0.02324 (10)	0.40325 (14)	0.62611 (11)	0.0181 (3)
H9A	−0.0340	0.4048	0.6665	0.022*
C3	0.43385 (11)	0.03367 (18)	0.17699 (13)	0.0269 (3)
H3A	0.4561	0.0949	0.1241	0.032*
N2	0.06833 (10)	0.62403 (12)	0.70259 (10)	0.0227 (3)
C2	0.43303 (12)	−0.10224 (18)	0.15451 (13)	0.0286 (3)
H2A	0.4578	−0.1345	0.0879	0.034*
C13	0.19287 (12)	0.00944 (17)	0.60575 (13)	0.0268 (3)
H13A	0.1205	0.0196	0.6011	0.040*
H13B	0.2229	0.0569	0.6719	0.040*
H13C	0.2100	−0.0857	0.6117	0.040*
C1	0.39611 (11)	−0.19141 (16)	0.22913 (13)	0.0258 (3)
H1A	0.3937	−0.2844	0.2129	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01570 (18)	0.01769 (18)	0.01585 (18)	0.00236 (11)	0.00106 (12)	−0.00261 (11)
S2	0.01591 (17)	0.01766 (18)	0.01801 (18)	0.00156 (11)	0.00017 (12)	−0.00121 (11)
O8	0.0226 (5)	0.0266 (5)	0.0172 (5)	0.0065 (4)	0.0044 (4)	0.0012 (4)
O7	0.0198 (5)	0.0260 (5)	0.0260 (5)	−0.0025 (4)	0.0002 (4)	−0.0080 (4)
O3	0.0363 (7)	0.0304 (6)	0.0522 (8)	−0.0013 (5)	−0.0003 (6)	−0.0206 (6)
O6	0.0242 (5)	0.0314 (6)	0.0221 (5)	0.0076 (4)	−0.0012 (4)	0.0041 (4)
O5	0.0255 (5)	0.0213 (5)	0.0295 (6)	−0.0048 (4)	0.0017 (4)	−0.0063 (4)
O4	0.0322 (6)	0.0265 (5)	0.0234 (5)	0.0113 (4)	0.0059 (4)	−0.0020 (4)
N3	0.0179 (5)	0.0196 (6)	0.0193 (6)	0.0046 (4)	0.0050 (4)	0.0025 (4)
C7	0.0167 (6)	0.0158 (6)	0.0156 (6)	0.0036 (5)	0.0007 (5)	−0.0003 (5)
O2	0.0495 (8)	0.0169 (5)	0.0556 (8)	0.0060 (5)	0.0141 (6)	0.0020 (5)
C8	0.0185 (6)	0.0170 (6)	0.0167 (6)	0.0008 (5)	0.0020 (5)	0.0019 (5)
N1	0.0279 (6)	0.0172 (6)	0.0270 (6)	−0.0001 (5)	0.0015 (5)	−0.0007 (5)
C6	0.0175 (6)	0.0200 (7)	0.0220 (7)	0.0020 (5)	0.0012 (5)	−0.0002 (5)
C11	0.0195 (6)	0.0173 (6)	0.0276 (7)	−0.0006 (5)	0.0010 (5)	−0.0013 (5)
C12	0.0167 (6)	0.0207 (7)	0.0260 (7)	0.0005 (5)	0.0054 (5)	−0.0011 (5)
C4	0.0162 (6)	0.0240 (7)	0.0253 (7)	−0.0002 (5)	0.0032 (5)	0.0026 (5)
C10	0.0215 (6)	0.0158 (6)	0.0154 (6)	0.0060 (5)	−0.0017 (5)	−0.0004 (5)
C5	0.0135 (6)	0.0193 (6)	0.0193 (6)	0.0021 (5)	0.0018 (5)	−0.0010 (5)
O1	0.0488 (7)	0.0227 (6)	0.0449 (7)	−0.0002 (5)	0.0257 (6)	0.0008 (5)
C9	0.0200 (6)	0.0196 (6)	0.0152 (6)	0.0038 (5)	0.0034 (5)	0.0025 (5)
C3	0.0198 (7)	0.0379 (8)	0.0233 (7)	−0.0007 (6)	0.0046 (6)	0.0046 (6)
N2	0.0296 (6)	0.0184 (6)	0.0192 (6)	0.0071 (5)	−0.0021 (5)	−0.0021 (5)
C2	0.0227 (7)	0.0422 (9)	0.0214 (7)	0.0056 (6)	0.0044 (6)	−0.0045 (6)
C13	0.0280 (7)	0.0300 (8)	0.0237 (7)	0.0051 (6)	0.0097 (6)	0.0079 (6)
C1	0.0237 (7)	0.0272 (7)	0.0263 (7)	0.0051 (6)	0.0005 (6)	−0.0076 (6)

Geometric parameters (Å, º) top

S1—O8	1.4275 (11)	C6—C5	1.4044 (19)
S1—O7	1.4304 (11)	C11—C12	1.387 (2)
S1—N3	1.6660 (13)	C11—C10	1.387 (2)
S1—C7	1.7633 (14)	C11—H11A	0.9500
S2—O6	1.4310 (11)	C12—H12A	0.9500
S2—O5	1.4312 (11)	C4—C3	1.390 (2)
S2—N3	1.6665 (13)	C4—C5	1.393 (2)
S2—C5	1.7855 (14)	C4—H4A	0.9500
O3—N2	1.2289 (19)	C10—C9	1.380 (2)
O4—N2	1.2236 (18)	C10—N2	1.4712 (17)
N3—C13	1.4799 (18)	C9—H9A	0.9500
C7—C8	1.3905 (19)	C3—C2	1.385 (2)
C7—C12	1.3950 (19)	C3—H3A	0.9500
O2—N1	1.2258 (17)	C2—C1	1.388 (2)
C8—C9	1.3901 (19)	C2—H2A	0.9500
C8—H8B	0.9500	C13—H13A	0.9800
N1—O1	1.2164 (18)	C13—H13B	0.9800
N1—C6	1.4709 (19)	C13—H13C	0.9800
C6—C1	1.387 (2)	C1—H1A	0.9500

O8—S1—O7	120.82 (7)	C7—C12—H12A	120.7
O8—S1—N3	106.41 (6)	C3—C4—C5	120.96 (14)
O7—S1—N3	106.34 (7)	C3—C4—H4A	119.5
O8—S1—C7	110.12 (7)	C5—C4—H4A	119.5
O7—S1—C7	108.07 (7)	C9—C10—C11	123.72 (13)
N3—S1—C7	103.69 (6)	C9—C10—N2	118.08 (13)
O6—S2—O5	119.05 (7)	C11—C10—N2	118.20 (13)
O6—S2—N3	105.57 (7)	C4—C5—C6	117.85 (13)
O5—S2—N3	109.41 (6)	C4—C5—S2	115.74 (11)
O6—S2—C5	108.34 (7)	C6—C5—S2	125.56 (11)
O5—S2—C5	106.57 (7)	C10—C9—C8	118.02 (13)
N3—S2—C5	107.42 (7)	C10—C9—H9A	121.0
C13—N3—S1	117.82 (10)	C8—C9—H9A	121.0
C13—N3—S2	119.92 (10)	C2—C3—C4	120.11 (15)
S1—N3—S2	121.22 (7)	C2—C3—H3A	119.9
C8—C7—C12	122.40 (12)	C4—C3—H3A	119.9
C8—C7—S1	118.58 (10)	O4—N2—O3	124.02 (13)
C12—C7—S1	119.00 (10)	O4—N2—C10	117.68 (12)
C9—C8—C7	118.98 (13)	O3—N2—C10	118.30 (13)
C9—C8—H8B	120.5	C3—C2—C1	120.10 (14)
C7—C8—H8B	120.5	C3—C2—H2A	120.0
O1—N1—O2	123.70 (14)	C1—C2—H2A	120.0
O1—N1—C6	118.43 (12)	N3—C13—H13A	109.5
O2—N1—C6	117.85 (13)	N3—C13—H13B	109.5
C1—C6—C5	121.40 (14)	H13A—C13—H13B	109.5
C1—C6—N1	115.78 (13)	N3—C13—H13C	109.5
C5—C6—N1	122.76 (13)	H13A—C13—H13C	109.5
C12—C11—C10	118.30 (13)	H13B—C13—H13C	109.5
C12—C11—H11A	120.8	C6—C1—C2	119.47 (15)
C10—C11—H11A	120.8	C6—C1—H1A	120.3
C11—C12—C7	118.57 (13)	C2—C1—H1A	120.3
C11—C12—H12A	120.7

O8—S1—N3—C13	−179.35 (11)	C12—C11—C10—C9	0.1 (2)
O7—S1—N3—C13	−49.34 (12)	C12—C11—C10—N2	−179.14 (12)
C7—S1—N3—C13	64.50 (12)	C3—C4—C5—C6	−1.7 (2)
O8—S1—N3—S2	12.32 (10)	C3—C4—C5—S2	168.34 (11)
O7—S1—N3—S2	142.33 (8)	C1—C6—C5—C4	3.0 (2)
C7—S1—N3—S2	−103.84 (9)	N1—C6—C5—C4	−174.28 (13)
O6—S2—N3—C13	13.90 (13)	C1—C6—C5—S2	−165.97 (11)
O5—S2—N3—C13	−115.35 (12)	N1—C6—C5—S2	16.74 (19)
C5—S2—N3—C13	129.34 (12)	O6—S2—C5—C4	−134.24 (11)
O6—S2—N3—S1	−178.01 (8)	O5—S2—C5—C4	−5.02 (12)
O5—S2—N3—S1	52.74 (10)	N3—S2—C5—C4	112.16 (11)
C5—S2—N3—S1	−62.56 (10)	O6—S2—C5—C6	34.94 (14)
O8—S1—C7—C8	151.35 (11)	O5—S2—C5—C6	164.17 (12)
O7—S1—C7—C8	17.44 (13)	N3—S2—C5—C6	−78.65 (13)
N3—S1—C7—C8	−95.14 (12)	C11—C10—C9—C8	0.0 (2)
O8—S1—C7—C12	−30.00 (13)	N2—C10—C9—C8	179.28 (11)
O7—S1—C7—C12	−163.91 (11)	C7—C8—C9—C10	−0.02 (19)
N3—S1—C7—C12	83.51 (12)	C5—C4—C3—C2	−1.3 (2)
C12—C7—C8—C9	−0.2 (2)	C9—C10—N2—O4	−14.29 (18)
S1—C7—C8—C9	178.44 (10)	C11—C10—N2—O4	164.99 (13)
O1—N1—C6—C1	−152.05 (15)	C9—C10—N2—O3	166.50 (14)
O2—N1—C6—C1	26.4 (2)	C11—C10—N2—O3	−14.22 (19)
O1—N1—C6—C5	25.4 (2)	C4—C3—C2—C1	3.1 (2)
O2—N1—C6—C5	−156.21 (15)	C5—C6—C1—C2	−1.3 (2)
C10—C11—C12—C7	−0.3 (2)	N1—C6—C1—C2	176.21 (13)
C8—C7—C12—C11	0.3 (2)	C3—C2—C1—C6	−1.8 (2)
S1—C7—C12—C11	−178.29 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O7	0.95	2.53	2.902 (2)	104
C4—H4A···O5	0.95	2.38	2.803 (2)	106
C13—H13A···O7	0.98	2.54	2.978 (2)	107
C13—H13C···O1	0.98	2.34	2.972 (2)	122
C1—H1A···O6ⁱ	0.95	2.51	3.369 (2)	150

Symmetry code: (i) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₈S₂
M_r	401.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	13.517 (3), 9.994 (2), 11.990 (2)
β (°)	95.26 (3)
V (Å³)	1613.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.58 × 0.47 × 0.29

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi 1995)
T_min, T_max	0.750, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	15376, 3683, 3540
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.094, 1.13
No. of reflections	3683
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O7	0.95	2.53	2.902 (2)	103.7
C4—H4A···O5	0.95	2.38	2.803 (2)	106.3
C13—H13A···O7	0.98	2.54	2.978 (2)	106.9
C13—H13C···O1	0.98	2.34	2.972 (2)	121.8
C1—H1A···O6ⁱ	0.95	2.51	3.369 (2)	149.7

Symmetry code: (i) x, −y−1/2, z−1/2.

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
Curtis, V. A. & Pavkovic, S. F. (1983). Acta Cryst. C39, 1077–1078. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315. CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent. US 4 670 046. Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Takyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem. 265, 9–14. Web of Science CrossRef CAS Google Scholar

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Volume 64| Part 10| October 2008| Page o1885

doi:10.1107/S1600536808027499

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