N-(2-Amino­phenyl­sulfonyl)-N-(2-nitro­phenyl­sulfonyl)methylamine

Li, X.-Y.; Song, Z.-W.

doi:10.1107/S1600536808028092

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1906

doi:10.1107/S1600536808028092

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N-(2-Aminophenylsulfonyl)-N-(2-nitrophenylsulfonyl)methylamine

Xu-Yun Li ^a and Zu-Wei Song ^a ^*

^aCollege of Science, Qingdao Agricultural University, Qingdao 266109, People's Republic of China
^*Correspondence e-mail: songzuwei2008@yahoo.cn

(Received 22 July 2008; accepted 3 September 2008; online 13 September 2008)

In the title molecule, C₁₃H₁₃N₃O₆S₂, the two benzene rings form a dihedral angle of 28.59 (7)°. The crystal sructure exhibits weak intermolecular N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds and π–π interactions [centroid-to-centroid distance = 3.899 (3) Å].

Related literature

For applications of sulfonimide-containing compounds, see: Kamoshita et al. (1987 ); Zhang et al. (2007 ). For the crystal structure of a related compound, see: Henschel et al. (1996 ).

Experimental

Crystal data

C₁₃H₁₃N₃O₆S₂
M_r = 371.38
Orthorhombic, P b c a
a = 13.844 (3) Å
b = 12.942 (2) Å
c = 16.645 (3) Å
V = 2982.2 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 153 (2) K
0.60 × 0.56 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.733, T_max = 0.969
34829 measured reflections
2630 independent reflections
2428 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.087
S = 1.08
2630 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3C⋯O1ⁱⁱ	0.88	2.52	3.366 (2)	160
C12—H12A⋯O2ⁱⁱ	0.95	2.59	3.508 (3)	162
C9—H9A⋯N3ⁱⁱⁱ	0.95	2.59	3.372 (3)	140
Symmetry codes: (ii) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536808028092/cv2436sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028092/cv2436Isup2.hkl

checkCIF report

Comment top

Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987) or catalysts (Zhang et al., 2007). Herein we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are in a good agreement with those reported previously for related compounds (Henschel et al., 1996). Two benzene rings (C1–C6 and C8–C13) form a dihedral angle of 28.59 (7)°.

The crystal packing exhibits π–π interactions (Table 1) and weak intermolecular N—H···O, C—H···N and C—H···O hydrogen bonds (Table 2).

Related literature top

For useful applications of sulfonimide-containing compounds, see: Kamoshita et al. (1987); Zhang et al. (2007). For the crystal structure of a related compound, see: Henschel et al. (1996). Cg1 and Cg2 are the centroids of atoms C1–C6 and C8–C13, respectively.

Experimental top

A solution of 2-aminobenzene-1-sulfonyl chloride (10 mmol) 1.92 g dissolved in anhydrous CH₂Cl₂ (10 ml), and dropwise added over a period of 10 min to a solution of 2-nitro-N-methyl-benzenesulfonamide (10 mmol) 2.16g and EtN(i-Pr)₂ (3 mmol) in CH₂Cl₂ (10 ml) at 273 K. The mixture was stirred at r.t. 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 (3:1 Cyclohexane:Dichloromethane) to give 1 as a white solid (3.52 mg, 95 %). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and Dichloromethane 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 (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing diagram.

N-(2-Aminophenylsulfonyl)-N-(2-nitrophenylsulfonyl)methylamine top

Crystal data top

C₁₃H₁₃N₃O₆S₂	F(000) = 1536
M_r = 371.38	D_x = 1.654 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 37072 reflections
a = 13.844 (3) Å	θ = 6.3–55.1°
b = 12.942 (2) Å	µ = 0.40 mm⁻¹
c = 16.645 (3) Å	T = 153 K
V = 2982.2 (10) Å³	Platelet, yellow
Z = 8	0.60 × 0.56 × 0.08 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	2630 independent reflections
Radiation source: Rotating anode	2428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω oscillation scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
T_min = 0.733, T_max = 0.969	k = −15→15
34829 measured reflections	l = −19→18

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0473P)² + 2.1978P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2630 reflections	Δρ_max = 0.42 e Å⁻³
218 parameters	Δρ_min = −0.39 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: 0.0018 (3)

Crystal data top

C₁₃H₁₃N₃O₆S₂	V = 2982.2 (10) Å³
M_r = 371.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.844 (3) Å	µ = 0.40 mm⁻¹
b = 12.942 (2) Å	T = 153 K
c = 16.645 (3) Å	0.60 × 0.56 × 0.08 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	2630 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2428 reflections with I > 2σ(I)
T_min = 0.733, T_max = 0.969	R_int = 0.027
34829 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.08	Δρ_max = 0.42 e Å⁻³
2630 reflections	Δρ_min = −0.39 e Å⁻³
218 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	0.22770 (3)	0.20009 (3)	0.06984 (2)	0.01845 (14)
S2	0.43344 (3)	0.22433 (4)	0.04145 (2)	0.01991 (15)
O1	0.49675 (13)	0.12116 (13)	−0.20069 (10)	0.0487 (5)
O2	0.40368 (12)	0.08365 (11)	−0.10127 (9)	0.0364 (4)
O3	0.51339 (9)	0.15580 (11)	0.03241 (8)	0.0281 (3)
O4	0.43340 (9)	0.29881 (11)	0.10485 (8)	0.0275 (3)
O5	0.16079 (10)	0.12669 (11)	0.03769 (8)	0.0288 (3)
O6	0.23132 (9)	0.30186 (10)	0.03747 (8)	0.0243 (3)
N1	0.44722 (12)	0.14579 (12)	−0.14329 (9)	0.0266 (4)
N2	0.33660 (11)	0.14908 (11)	0.05243 (9)	0.0214 (3)
N3	0.14942 (13)	0.03260 (13)	0.19054 (11)	0.0366 (4)
H3B	0.1590	0.0188	0.1394	0.044*
H3C	0.1251	−0.0150	0.2224	0.044*
C1	0.43468 (12)	0.25628 (14)	−0.12717 (11)	0.0211 (4)
C2	0.43337 (13)	0.31966 (16)	−0.19394 (11)	0.0268 (4)
H2A	0.4441	0.2917	−0.2460	0.032*
C3	0.41632 (14)	0.42395 (16)	−0.18432 (12)	0.0301 (5)
H3D	0.4138	0.4678	−0.2300	0.036*
C4	0.40295 (14)	0.46490 (15)	−0.10843 (12)	0.0298 (4)
H4B	0.3924	0.5370	−0.1020	0.036*
C5	0.40499 (13)	0.40078 (15)	−0.04174 (11)	0.0238 (4)
H5B	0.3961	0.4295	0.0102	0.029*
C6	0.41971 (12)	0.29552 (14)	−0.04974 (11)	0.0186 (4)
C7	0.34860 (16)	0.03595 (15)	0.06305 (13)	0.0347 (5)
H7A	0.4155	0.0166	0.0511	0.052*
H7B	0.3049	−0.0006	0.0264	0.052*
H7C	0.3333	0.0171	0.1186	0.052*
C8	0.21121 (13)	0.20842 (14)	0.17402 (11)	0.0211 (4)
C9	0.23455 (13)	0.30465 (15)	0.20835 (12)	0.0255 (4)
H9A	0.2607	0.3580	0.1758	0.031*
C10	0.21958 (14)	0.32160 (18)	0.28892 (12)	0.0328 (5)
H10A	0.2351	0.3864	0.3125	0.039*
C11	0.18139 (14)	0.24220 (19)	0.33523 (12)	0.0359 (5)
H11A	0.1707	0.2536	0.3909	0.043*
C12	0.15875 (14)	0.14838 (18)	0.30301 (12)	0.0340 (5)
H12A	0.1334	0.0957	0.3367	0.041*
C13	0.17225 (13)	0.12809 (15)	0.22050 (12)	0.0272 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0183 (2)	0.0203 (2)	0.0167 (2)	0.00124 (16)	0.00013 (16)	−0.00004 (16)
S2	0.0185 (2)	0.0241 (3)	0.0171 (2)	0.00214 (16)	−0.00052 (16)	−0.00013 (17)
O1	0.0593 (11)	0.0436 (10)	0.0431 (9)	0.0052 (8)	0.0250 (8)	−0.0135 (7)
O2	0.0501 (9)	0.0231 (7)	0.0360 (8)	−0.0032 (7)	0.0085 (7)	−0.0021 (6)
O3	0.0214 (7)	0.0326 (8)	0.0304 (7)	0.0080 (6)	0.0002 (5)	0.0034 (6)
O4	0.0305 (7)	0.0326 (8)	0.0195 (7)	−0.0013 (6)	−0.0024 (5)	−0.0053 (5)
O5	0.0265 (7)	0.0303 (7)	0.0297 (7)	−0.0043 (6)	−0.0045 (5)	−0.0064 (6)
O6	0.0249 (7)	0.0236 (7)	0.0246 (7)	0.0045 (5)	0.0016 (5)	0.0051 (5)
N1	0.0301 (8)	0.0271 (9)	0.0226 (8)	0.0023 (7)	0.0029 (7)	−0.0057 (7)
N2	0.0223 (8)	0.0175 (8)	0.0243 (7)	0.0030 (6)	0.0058 (6)	0.0015 (6)
N3	0.0400 (10)	0.0259 (9)	0.0438 (10)	0.0013 (8)	0.0158 (8)	0.0048 (8)
C1	0.0195 (9)	0.0215 (9)	0.0222 (9)	−0.0018 (7)	0.0022 (7)	−0.0026 (7)
C2	0.0257 (10)	0.0352 (11)	0.0194 (9)	−0.0058 (8)	0.0032 (7)	0.0002 (8)
C3	0.0301 (10)	0.0315 (11)	0.0287 (10)	−0.0056 (8)	0.0013 (8)	0.0107 (8)
C4	0.0310 (10)	0.0213 (10)	0.0371 (11)	−0.0013 (8)	0.0021 (9)	0.0041 (8)
C5	0.0235 (9)	0.0227 (9)	0.0251 (9)	−0.0004 (7)	0.0024 (7)	−0.0027 (7)
C6	0.0163 (8)	0.0220 (9)	0.0176 (9)	−0.0013 (7)	0.0014 (7)	0.0004 (7)
C7	0.0367 (11)	0.0204 (10)	0.0470 (12)	0.0061 (9)	0.0130 (10)	0.0079 (9)
C8	0.0174 (8)	0.0287 (10)	0.0171 (9)	0.0045 (7)	0.0010 (7)	0.0007 (7)
C9	0.0194 (9)	0.0316 (11)	0.0256 (10)	0.0026 (8)	0.0009 (7)	−0.0022 (8)
C10	0.0245 (10)	0.0453 (12)	0.0285 (10)	0.0031 (9)	−0.0014 (8)	−0.0121 (9)
C11	0.0248 (10)	0.0614 (15)	0.0215 (10)	0.0066 (10)	0.0013 (8)	0.0007 (10)
C12	0.0254 (10)	0.0476 (13)	0.0289 (10)	0.0092 (9)	0.0078 (8)	0.0112 (9)
C13	0.0205 (9)	0.0299 (10)	0.0311 (10)	0.0062 (8)	0.0045 (8)	0.0078 (8)

Geometric parameters (Å, º) top

S1—O6	1.4239 (13)	C3—C4	1.382 (3)
S1—O5	1.4307 (13)	C3—H3D	0.9500
S1—N2	1.6711 (15)	C4—C5	1.386 (3)
S1—C8	1.7523 (18)	C4—H4B	0.9500
S2—O3	1.4263 (13)	C5—C6	1.384 (3)
S2—O4	1.4291 (14)	C5—H5B	0.9500
S2—N2	1.6671 (15)	C7—H7A	0.9800
S2—C6	1.7859 (18)	C7—H7B	0.9800
O1—N1	1.218 (2)	C7—H7C	0.9800
O2—N1	1.224 (2)	C8—C13	1.404 (3)
N1—C1	1.465 (2)	C8—C9	1.408 (3)
N2—C7	1.484 (2)	C9—C10	1.375 (3)
N3—C13	1.370 (3)	C9—H9A	0.9500
N3—H3B	0.8800	C10—C11	1.389 (3)
N3—H3C	0.8800	C10—H10A	0.9500
C1—C2	1.381 (3)	C11—C12	1.364 (3)
C1—C6	1.401 (2)	C11—H11A	0.9500
C2—C3	1.380 (3)	C12—C13	1.411 (3)
C2—H2A	0.9500	C12—H12A	0.9500

Cg1···Cg2ⁱ	3.899 (3)

O6—S1—O5	119.70 (8)	C5—C4—H4B	120.0
O6—S1—N2	105.55 (8)	C6—C5—C4	121.02 (18)
O5—S1—N2	104.89 (8)	C6—C5—H5B	119.5
O6—S1—C8	108.79 (8)	C4—C5—H5B	119.5
O5—S1—C8	109.06 (8)	C5—C6—C1	117.86 (17)
N2—S1—C8	108.27 (8)	C5—C6—S2	116.22 (14)
O3—S2—O4	119.85 (8)	C1—C6—S2	125.40 (14)
O3—S2—N2	105.80 (8)	N2—C7—H7A	109.5
O4—S2—N2	108.22 (8)	N2—C7—H7B	109.5
O3—S2—C6	108.28 (8)	H7A—C7—H7B	109.5
O4—S2—C6	106.24 (8)	N2—C7—H7C	109.5
N2—S2—C6	107.99 (8)	H7A—C7—H7C	109.5
O1—N1—O2	123.58 (17)	H7B—C7—H7C	109.5
O1—N1—C1	117.75 (16)	C13—C8—C9	121.31 (17)
O2—N1—C1	118.56 (15)	C13—C8—S1	123.36 (15)
C7—N2—S2	119.96 (13)	C9—C8—S1	115.23 (14)
C7—N2—S1	118.04 (12)	C10—C9—C8	120.18 (19)
S2—N2—S1	120.91 (9)	C10—C9—H9A	119.9
C13—N3—H3B	120.0	C8—C9—H9A	119.9
C13—N3—H3C	120.0	C9—C10—C11	118.7 (2)
H3B—N3—H3C	120.0	C9—C10—H10A	120.6
C2—C1—C6	121.53 (18)	C11—C10—H10A	120.6
C2—C1—N1	115.70 (16)	C12—C11—C10	121.86 (19)
C6—C1—N1	122.68 (16)	C12—C11—H11A	119.1
C3—C2—C1	119.33 (18)	C10—C11—H11A	119.1
C3—C2—H2A	120.3	C11—C12—C13	121.21 (19)
C1—C2—H2A	120.3	C11—C12—H12A	119.4
C2—C3—C4	120.27 (18)	C13—C12—H12A	119.4
C2—C3—H3D	119.9	N3—C13—C8	123.80 (18)
C4—C3—H3D	119.9	N3—C13—C12	119.46 (18)
C3—C4—C5	119.96 (19)	C8—C13—C12	116.72 (19)
C3—C4—H4B	120.0

O3—S2—N2—C7	8.83 (17)	C2—C1—C6—S2	−172.37 (14)
O4—S2—N2—C7	−120.79 (15)	N1—C1—C6—S2	11.1 (2)
C6—S2—N2—C7	124.60 (15)	O3—S2—C6—C5	−134.60 (14)
O3—S2—N2—S1	176.65 (10)	O4—S2—C6—C5	−4.64 (16)
O4—S2—N2—S1	47.02 (12)	N2—S2—C6—C5	111.28 (15)
C6—S2—N2—S1	−67.59 (12)	O3—S2—C6—C1	36.88 (18)
O6—S1—N2—C7	−166.74 (14)	O4—S2—C6—C1	166.83 (15)
O5—S1—N2—C7	−39.44 (16)	N2—S2—C6—C1	−77.25 (16)
C8—S1—N2—C7	76.90 (16)	O6—S1—C8—C13	157.41 (15)
O6—S1—N2—S2	25.21 (12)	O5—S1—C8—C13	25.25 (18)
O5—S1—N2—S2	152.52 (10)	N2—S1—C8—C13	−88.35 (16)
C8—S1—N2—S2	−91.14 (11)	O6—S1—C8—C9	−18.95 (16)
O1—N1—C1—C2	32.8 (2)	O5—S1—C8—C9	−151.11 (13)
O2—N1—C1—C2	−143.45 (18)	N2—S1—C8—C9	95.29 (14)
O1—N1—C1—C6	−150.48 (18)	C13—C8—C9—C10	0.1 (3)
O2—N1—C1—C6	33.2 (3)	S1—C8—C9—C10	176.58 (15)
C6—C1—C2—C3	−0.4 (3)	C8—C9—C10—C11	0.1 (3)
N1—C1—C2—C3	176.31 (17)	C9—C10—C11—C12	0.2 (3)
C1—C2—C3—C4	1.5 (3)	C10—C11—C12—C13	−0.7 (3)
C2—C3—C4—C5	−1.1 (3)	C9—C8—C13—N3	−179.11 (17)
C3—C4—C5—C6	−0.4 (3)	S1—C8—C13—N3	4.8 (3)
C4—C5—C6—C1	1.4 (3)	C9—C8—C13—C12	−0.6 (3)
C4—C5—C6—S2	173.57 (15)	S1—C8—C13—C12	−176.77 (14)
C2—C1—C6—C5	−1.0 (3)	C11—C12—C13—N3	179.44 (19)
N1—C1—C6—C5	−177.53 (16)	C11—C12—C13—C8	0.9 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···O1ⁱⁱ	0.88	2.52	3.366 (2)	160
C12—H12A···O2ⁱⁱ	0.95	2.59	3.508 (3)	162
C9—H9A···N3ⁱⁱⁱ	0.95	2.59	3.372 (3)	140

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃N₃O₆S₂
M_r	371.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	153
a, b, c (Å)	13.844 (3), 12.942 (2), 16.645 (3)
V (Å³)	2982.2 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.60 × 0.56 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.733, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	34829, 2630, 2428
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.08
No. of reflections	2630
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.39

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

Selected interatomic distances (Å) top

Cg1···Cg2ⁱ

3.899 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···O1ⁱⁱ	0.88	2.52	3.366 (2)	160.4
C12—H12A···O2ⁱⁱ	0.95	2.59	3.508 (3)	162.0
C9—H9A···N3ⁱⁱⁱ	0.95	2.59	3.372 (3)	139.7

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

References

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 o1906

doi:10.1107/S1600536808028092

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