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ISSN: 2056-9890

2-Amino-N-(4-methyl­phenyl­sulfon­yl)-N-phenyl­benzene­sulfonamide

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

(Received 20 February 2008; accepted 18 March 2008; online 29 March 2008)

In the title mol­ecule, C19H18N2O4S2, the phenyl ring makes dihedral angles of 33.99 (2) and 43.70 (3)° with the two methyl-substituted benzene rings. Inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers. The crystal packing exhibits weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996[Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313-1315.]). For details of the biological activities of sulfon­amide-containing compounds, see: Kamoshita et al. (1987[Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent 4 670 046.]). For related literature, see: Allen et al. (1987[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.]); Zhang et al. (2007[Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem. 265, 9-14.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18N2O4S2

  • Mr = 402.47

  • Monoclinic, P 21 /c

  • a = 14.6245 (3) Å

  • b = 10.0454 (2) Å

  • c = 13.4735 (4) Å

  • β = 107.478 (2)°

  • V = 1887.99 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 293 (2) K

  • 0.52 × 0.32 × 0.25 mm

Data collection
  • Rigaku R-AXIS RAPID IP area-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.855, Tmax = 0.926

  • 17437 measured reflections

  • 4312 independent reflections

  • 3531 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.121

  • S = 1.07

  • 4312 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2B⋯O3i 0.86 2.20 3.062 (2) 176
C19—H19A⋯O1ii 0.96 2.57 3.517 (3) 169
C19—H19C⋯O4iii 0.96 2.58 3.538 (3) 174
N2—H2C⋯O2 0.86 2.23 2.893 (2) 133
Symmetry codes: (i) -x, -y+1, -z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as 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 normal (Allen et al., 1987) and in a good agreement with those reported previously (Henschel et al., 1996). The phenyl ring (C7—C12) makes the dihedral angles of 33.99 (2) and 43.70 (3)°, respectively, with two benzene rings (C1—C6/N1 and C13—C19). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the crystal structures of related compounds, see: Henschel et al. (1996). For details of the biological activities of sulfonimide-containing compounds, see: Kamoshita et al. (1987). For related literature, see: Allen et al. (1987); Zhang et al. (2007).

Experimental top

A solution of methylsulfonyl chloride (1 mmol) was dissolved in anhydrous CH2Cl2 (10 ml), and dropwise added over a period of 10 min to a solution of 2-amino-N-methyl-benzenesulfonamide (1 mmol) and DMAP2 (3 mmol) in CH2Cl2 (10 ml) at 273 K. The mixture was stirred for 4 h at room temperature. The organic phase was washed with 2 N HCl twice, and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography (1:1 cyclohexane:dichloromethane) to give (I) as a white solid (294 mg, 73%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and dichloromethane at room temperature.

Refinement top

H atoms were positioned geometrically with C—H = 0.93 or 0.96 Å, N—H=0.86 Å, and refined using a riding model, with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C, N).

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
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.
2-Amino-N-(4-methylphenylsulfonyl)-N-phenylbenzenesulfonamide top
Crystal data top
C19H18N2O4S2F(000) = 840
Mr = 402.47Dx = 1.416 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2652 reflections
a = 14.6245 (3) Åθ = 2.6–25.6°
b = 10.0454 (2) ŵ = 0.31 mm1
c = 13.4735 (4) ÅT = 293 K
β = 107.478 (2)°Platelet, yellow
V = 1887.99 (7) Å30.52 × 0.32 × 0.25 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4312 independent reflections
Radiation source: Rotating Anode3531 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω oscillation scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(ABSCOR; Higashi 1995)
h = 1818
Tmin = 0.855, Tmax = 0.927k = 1313
17437 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0647P)2 + 0.3731P]
where P = (Fo2 + 2Fc2)/3
4312 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C19H18N2O4S2V = 1887.99 (7) Å3
Mr = 402.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.6245 (3) ŵ = 0.31 mm1
b = 10.0454 (2) ÅT = 293 K
c = 13.4735 (4) Å0.52 × 0.32 × 0.25 mm
β = 107.478 (2)°
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
4312 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi 1995)
3531 reflections with I > 2σ(I)
Tmin = 0.855, Tmax = 0.927Rint = 0.038
17437 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.07Δρmax = 0.40 e Å3
4312 reflectionsΔρmin = 0.26 e Å3
245 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
xyzUiso*/Ueq
S10.18008 (3)0.28081 (5)0.24068 (4)0.04085 (14)
S20.24948 (3)0.51762 (5)0.14469 (3)0.04136 (14)
O10.24248 (10)0.20876 (14)0.32523 (12)0.0550 (4)
O20.16312 (11)0.23184 (16)0.13781 (11)0.0573 (4)
O30.18520 (10)0.46901 (19)0.05005 (10)0.0595 (4)
O40.24789 (12)0.65454 (14)0.17142 (12)0.0571 (4)
N10.22958 (11)0.43445 (16)0.24350 (11)0.0386 (3)
N20.00565 (13)0.3985 (2)0.09409 (13)0.0651 (6)
H2B0.05420.43710.05150.078*
H2C0.04150.37270.07310.078*
C10.00348 (13)0.3782 (2)0.19378 (15)0.0431 (4)
C20.08053 (14)0.4204 (2)0.22702 (18)0.0541 (5)
H2D0.13320.45990.17940.065*
C30.08033 (17)0.4052 (3)0.3272 (2)0.0667 (6)
H3B0.13260.43460.34690.080*
C40.00295 (18)0.3463 (3)0.4010 (2)0.0691 (7)
H4B0.00340.33700.46960.083*
C50.07352 (16)0.3022 (2)0.37162 (16)0.0540 (5)
H5A0.12510.26180.42020.065*
C60.07447 (12)0.31772 (19)0.26886 (14)0.0399 (4)
C70.25885 (13)0.49745 (18)0.34475 (13)0.0375 (4)
C80.19747 (14)0.5849 (2)0.37156 (16)0.0459 (4)
H8A0.13930.60760.32340.055*
C90.22318 (18)0.6384 (2)0.47042 (19)0.0586 (6)
H9A0.18210.69700.48940.070*
C100.3098 (2)0.6048 (3)0.54093 (18)0.0650 (6)
H10A0.32680.64060.60770.078*
C110.37175 (19)0.5185 (3)0.51344 (18)0.0640 (6)
H11A0.43020.49690.56150.077*
C120.34685 (14)0.4643 (2)0.41479 (15)0.0497 (5)
H12A0.38830.40660.39560.060*
C130.36661 (12)0.47731 (19)0.14622 (13)0.0384 (4)
C140.44113 (15)0.5618 (2)0.19508 (16)0.0514 (5)
H14A0.43010.63700.23010.062*
C150.53243 (15)0.5326 (2)0.19103 (18)0.0562 (5)
H15A0.58290.58900.22390.067*
C160.55032 (14)0.4216 (2)0.13933 (16)0.0494 (5)
C170.47460 (17)0.3389 (2)0.09216 (19)0.0590 (6)
H17A0.48600.26350.05760.071*
C180.38235 (15)0.3642 (2)0.09434 (18)0.0523 (5)
H18A0.33220.30710.06200.063*
C190.64941 (17)0.3926 (3)0.1334 (2)0.0718 (7)
H19A0.68500.47420.14020.108*
H19B0.64510.35210.06760.108*
H19C0.68150.33310.18870.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0370 (2)0.0369 (2)0.0459 (3)0.00456 (18)0.00835 (18)0.00020 (18)
S20.0365 (2)0.0506 (3)0.0373 (2)0.00913 (19)0.01168 (18)0.00992 (19)
O10.0466 (8)0.0449 (8)0.0664 (9)0.0112 (6)0.0064 (7)0.0118 (7)
O20.0573 (9)0.0564 (9)0.0567 (8)0.0020 (7)0.0148 (7)0.0172 (7)
O30.0401 (7)0.0969 (12)0.0360 (7)0.0060 (8)0.0031 (6)0.0088 (7)
O40.0668 (10)0.0444 (8)0.0697 (9)0.0160 (7)0.0354 (8)0.0182 (7)
N10.0390 (8)0.0422 (8)0.0361 (7)0.0013 (6)0.0133 (6)0.0008 (6)
N20.0426 (9)0.1027 (17)0.0438 (9)0.0165 (10)0.0037 (7)0.0140 (10)
C10.0340 (8)0.0449 (10)0.0468 (10)0.0028 (8)0.0067 (7)0.0042 (8)
C20.0347 (9)0.0589 (13)0.0679 (13)0.0040 (9)0.0145 (9)0.0136 (11)
C30.0513 (12)0.0765 (16)0.0834 (16)0.0059 (12)0.0371 (12)0.0146 (14)
C40.0654 (15)0.0889 (19)0.0633 (14)0.0073 (14)0.0350 (12)0.0226 (13)
C50.0492 (11)0.0615 (13)0.0510 (11)0.0031 (10)0.0147 (9)0.0201 (10)
C60.0326 (8)0.0389 (9)0.0460 (9)0.0015 (7)0.0085 (7)0.0053 (8)
C70.0395 (9)0.0388 (9)0.0352 (8)0.0038 (7)0.0128 (7)0.0001 (7)
C80.0444 (10)0.0430 (10)0.0532 (11)0.0009 (8)0.0189 (8)0.0003 (8)
C90.0690 (14)0.0522 (12)0.0646 (13)0.0004 (11)0.0353 (11)0.0124 (10)
C100.0861 (18)0.0632 (14)0.0464 (12)0.0049 (13)0.0208 (11)0.0143 (10)
C110.0643 (14)0.0713 (15)0.0459 (11)0.0031 (12)0.0005 (10)0.0055 (11)
C120.0429 (10)0.0574 (12)0.0459 (10)0.0052 (9)0.0089 (8)0.0034 (9)
C130.0341 (8)0.0462 (10)0.0355 (8)0.0042 (7)0.0116 (7)0.0048 (7)
C140.0454 (11)0.0551 (12)0.0541 (11)0.0023 (9)0.0157 (9)0.0107 (10)
C150.0390 (10)0.0646 (14)0.0620 (13)0.0083 (10)0.0104 (9)0.0056 (11)
C160.0384 (10)0.0553 (12)0.0573 (12)0.0063 (9)0.0189 (9)0.0121 (9)
C170.0546 (12)0.0540 (12)0.0748 (15)0.0035 (10)0.0291 (11)0.0118 (11)
C180.0416 (10)0.0533 (12)0.0627 (12)0.0037 (9)0.0168 (9)0.0106 (10)
C190.0484 (12)0.0763 (17)0.100 (2)0.0100 (12)0.0359 (13)0.0127 (15)
Geometric parameters (Å, º) top
S1—O21.4206 (15)C8—C91.379 (3)
S1—O11.4248 (14)C8—H8A0.9300
S1—N11.7002 (16)C9—C101.378 (3)
S1—C61.7378 (19)C9—H9A0.9300
S2—O41.4237 (16)C10—C111.382 (4)
S2—O31.4241 (15)C10—H10A0.9300
S2—N11.6698 (15)C11—C121.380 (3)
S2—C131.7543 (18)C11—H11A0.9300
N1—C71.447 (2)C12—H12A0.9300
N2—C11.349 (3)C13—C141.382 (3)
N2—H2B0.8600C13—C181.389 (3)
N2—H2C0.8600C14—C151.384 (3)
C1—C21.398 (3)C14—H14A0.9300
C1—C61.414 (2)C15—C161.380 (3)
C2—C31.357 (3)C15—H15A0.9300
C2—H2D0.9300C16—C171.377 (3)
C3—C41.394 (3)C16—C191.504 (3)
C3—H3B0.9300C17—C181.382 (3)
C4—C51.367 (3)C17—H17A0.9300
C4—H4B0.9300C18—H18A0.9300
C5—C61.397 (3)C19—H19A0.9600
C5—H5A0.9300C19—H19B0.9600
C7—C81.380 (3)C19—H19C0.9600
C7—C121.389 (3)
O2—S1—O1119.11 (10)C9—C8—C7119.4 (2)
O2—S1—N1106.54 (9)C9—C8—H8A120.3
O1—S1—N1106.09 (8)C7—C8—H8A120.3
O2—S1—C6112.39 (9)C10—C9—C8119.9 (2)
O1—S1—C6109.36 (9)C10—C9—H9A120.1
N1—S1—C6101.64 (8)C8—C9—H9A120.1
O4—S2—O3120.08 (10)C9—C10—C11120.6 (2)
O4—S2—N1105.17 (8)C9—C10—H10A119.7
O3—S2—N1108.43 (9)C11—C10—H10A119.7
O4—S2—C13108.07 (9)C12—C11—C10120.1 (2)
O3—S2—C13108.12 (9)C12—C11—H11A120.0
N1—S2—C13106.17 (8)C10—C11—H11A120.0
C7—N1—S2117.37 (12)C11—C12—C7118.8 (2)
C7—N1—S1114.93 (11)C11—C12—H12A120.6
S2—N1—S1127.69 (9)C7—C12—H12A120.6
C1—N2—H2B120.0C14—C13—C18121.05 (18)
C1—N2—H2C120.0C14—C13—S2119.43 (15)
H2B—N2—H2C120.0C18—C13—S2119.45 (15)
N2—C1—C2119.54 (18)C13—C14—C15118.9 (2)
N2—C1—C6123.36 (18)C13—C14—H14A120.6
C2—C1—C6117.10 (18)C15—C14—H14A120.6
C3—C2—C1121.5 (2)C16—C15—C14121.5 (2)
C3—C2—H2D119.2C16—C15—H15A119.3
C1—C2—H2D119.2C14—C15—H15A119.3
C2—C3—C4121.1 (2)C17—C16—C15118.16 (19)
C2—C3—H3B119.5C17—C16—C19120.9 (2)
C4—C3—H3B119.5C15—C16—C19121.0 (2)
C5—C4—C3119.3 (2)C16—C17—C18122.3 (2)
C5—C4—H4B120.3C16—C17—H17A118.9
C3—C4—H4B120.3C18—C17—H17A118.9
C4—C5—C6120.2 (2)C17—C18—C13118.12 (19)
C4—C5—H5A119.9C17—C18—H18A120.9
C6—C5—H5A119.9C13—C18—H18A120.9
C5—C6—C1120.73 (18)C16—C19—H19A109.5
C5—C6—S1117.82 (14)C16—C19—H19B109.5
C1—C6—S1120.92 (14)H19A—C19—H19B109.5
C8—C7—C12121.20 (18)C16—C19—H19C109.5
C8—C7—N1119.59 (16)H19A—C19—H19C109.5
C12—C7—N1119.15 (17)H19B—C19—H19C109.5
O4—S2—N1—C727.73 (15)S2—N1—C7—C885.99 (19)
O3—S2—N1—C7157.36 (13)S1—N1—C7—C895.07 (18)
C13—S2—N1—C786.67 (14)S2—N1—C7—C1296.67 (19)
O4—S2—N1—S1153.48 (12)S1—N1—C7—C1282.28 (19)
O3—S2—N1—S123.85 (15)C12—C7—C8—C91.3 (3)
C13—S2—N1—S192.12 (13)N1—C7—C8—C9176.02 (18)
O2—S1—N1—C7175.64 (13)C7—C8—C9—C100.4 (3)
O1—S1—N1—C747.78 (15)C8—C9—C10—C110.4 (4)
C6—S1—N1—C766.53 (14)C9—C10—C11—C120.4 (4)
O2—S1—N1—S23.18 (14)C10—C11—C12—C70.4 (4)
O1—S1—N1—S2131.04 (12)C8—C7—C12—C111.2 (3)
C6—S1—N1—S2114.65 (12)N1—C7—C12—C11176.1 (2)
N2—C1—C2—C3178.3 (2)O4—S2—C13—C1416.10 (18)
C6—C1—C2—C30.6 (3)O3—S2—C13—C14147.52 (16)
C1—C2—C3—C40.2 (4)N1—S2—C13—C1496.30 (17)
C2—C3—C4—C50.6 (4)O4—S2—C13—C18161.03 (16)
C3—C4—C5—C60.8 (4)O3—S2—C13—C1829.62 (19)
C4—C5—C6—C10.4 (3)N1—S2—C13—C1886.56 (17)
C4—C5—C6—S1171.3 (2)C18—C13—C14—C150.5 (3)
N2—C1—C6—C5178.5 (2)S2—C13—C14—C15176.61 (17)
C2—C1—C6—C50.3 (3)C13—C14—C15—C160.1 (3)
N2—C1—C6—S17.1 (3)C14—C15—C16—C170.6 (3)
C2—C1—C6—S1171.74 (16)C14—C15—C16—C19178.6 (2)
O2—S1—C6—C5148.79 (17)C15—C16—C17—C180.6 (4)
O1—S1—C6—C514.18 (19)C19—C16—C17—C18178.7 (2)
N1—S1—C6—C597.68 (17)C16—C17—C18—C130.0 (4)
O2—S1—C6—C139.51 (19)C14—C13—C18—C170.5 (3)
O1—S1—C6—C1174.13 (15)S2—C13—C18—C17176.55 (17)
N1—S1—C6—C174.01 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O3i0.862.203.062 (2)176
C19—H19A···O1ii0.962.573.517 (3)169
C19—H19C···O4iii0.962.583.538 (3)174
N2—H2C···O20.862.232.893 (2)133
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H18N2O4S2
Mr402.47
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.6245 (3), 10.0454 (2), 13.4735 (4)
β (°) 107.478 (2)
V3)1887.99 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.52 × 0.32 × 0.25
Data collection
DiffractometerRigaku R-AXIS RAPID IP area-detector
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi 1995)
Tmin, Tmax0.855, 0.927
No. of measured, independent and
observed [I > 2σ(I)] reflections
17437, 4312, 3531
Rint0.038
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.121, 1.07
No. of reflections4312
No. of parameters245
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.26

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O3i0.862.203.062 (2)175.6
C19—H19A···O1ii0.962.573.517 (3)169.3
C19—H19C···O4iii0.962.583.538 (3)173.6
N2—H2C···O20.862.232.893 (2)133.3
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2.
 

References

First citationAllen, 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
First citationHenschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315.  CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationKamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent 4 670 046.  Google Scholar
First citationRigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, 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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