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ISSN: 2056-9890

N-Cyclo­hexyl-4-[(2-nitro­anilino)­meth­yl]thio­phene-2-sulfonamide

aBioengineering College, Xihua University, Chengdu, Sichuan 610039, People's Republic of China, and bSichuan Academy of Medical Sciences and, Sichuan Provincial People's Hospital, Chengdu, Sichuan 610072, People's Republic of China
*Correspondence e-mail: shijianyoude@126.com

(Received 16 August 2011; accepted 20 September 2011; online 30 September 2011)

In the title compound, C17H21N3O4S2, an intra­molecular N—H⋯O hydrogen bond involving the proximate amine and nitro groups is observed. In the crystal, inter­molecular N—H⋯O hydrogen bonds involving the amine and SO2 groups occur. One of the notro O atoms is disordered over two conformations with occupancies of 0.578 (12) and 0.422 (12).

Related literature

For uses of thio­phene-2-sulfonamides, see: Cuberes Altisen et al. (2007[Cuberes Altisen, R., Frigola Constansa, J. & Gutierrez Silva, B. (2007). US Patent Appl. US 20070066587 A1 20070322. ]); Santhakumar & Tomaszewski (2006[Santhakumar, V. & Tomaszewski, M. (2006). PCT Int. Appl. WO 2006052189 A1 20060518.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21N3O4S2

  • Mr = 395.49

  • Monoclinic, P 21 /c

  • a = 7.4201 (2) Å

  • b = 27.8329 (7) Å

  • c = 10.1790 (3) Å

  • β = 118.440 (3)°

  • V = 1848.50 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 145 K

  • 0.38 × 0.25 × 0.15 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Oxford, England.]) Tmin = 0.970, Tmax = 1.0

  • 8048 measured reflections

  • 3772 independent reflections

  • 3104 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.129

  • S = 1.01

  • 3772 reflections

  • 225 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.02 e Å−3

  • Δρmin = −0.68 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.88 2.27 2.956 (3) 134
N2—H2⋯O2ii 0.81 (3) 2.36 (3) 2.979 (3) 135 (3)
N2—H2⋯O3 0.81 (3) 2.01 (3) 2.620 (4) 132 (3)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Oxford, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

N-Cyclohexyl-4-((2-nitrophenylamino)methyl)thiophene-2-sulfonamide is potentially useful in the treatment of a condition mediated by the CB2 receptor (Cuberes Altisen, et al., 2007). In the title compound, C17H21N3O4S2, there is an intramolecular N-H···O between the amine and nitro groups as well as N-H···O intermolecular hydrogen bonds involving the amine and SO2 moieties. O4 is disordered over two conformations with occupancies of 0.578 (12) and 0.422 (12).

Related literature top

For uses of thiophene-2-sulfonamides, see: Cuberes Altisen et al. (2007); Santhakumar & Tomaszewski (2006).

Experimental top

A mixture of 4-((2-nitrophenylamino)methyl)thiophene-2-sulfonyl chloride (3.22 g, 0.01 mol), trimethylamine (0.885 g, 0.015 mol) and cyclohexanamine (0.99 g, 0.01 mol) in THF (150 mL) was heated to reflux for 3 h, then the solvent removed and the residue separated by silica gel column to obtain the target compound. Single crystals were obtained from the powder in CH2Cl2 and methanol after 3 days.

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distances of 0.95 to 1.00 Å [Uiso(H) = 1.2Ueq(C)]. The H atoms attached to N were idealized with N–H distances of 0.88 Å. H2 atom located by difference fouraer map.

Structure description top

N-Cyclohexyl-4-((2-nitrophenylamino)methyl)thiophene-2-sulfonamide is potentially useful in the treatment of a condition mediated by the CB2 receptor (Cuberes Altisen, et al., 2007). In the title compound, C17H21N3O4S2, there is an intramolecular N-H···O between the amine and nitro groups as well as N-H···O intermolecular hydrogen bonds involving the amine and SO2 moieties. O4 is disordered over two conformations with occupancies of 0.578 (12) and 0.422 (12).

For uses of thiophene-2-sulfonamides, see: Cuberes Altisen et al. (2007); Santhakumar & Tomaszewski (2006).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound. The intramolecular N-H···O hydrogen bond is shown by dashed lines.
N-Cyclohexyl-4-[(2-nitroanilino)methyl]thiophene-2-sulfonamide top
Crystal data top
C17H21N3O4S2F(000) = 832
Mr = 395.49Dx = 1.421 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 3479 reflections
a = 7.4201 (2) Åθ = 2.9–29.1°
b = 27.8329 (7) ŵ = 0.32 mm1
c = 10.1790 (3) ÅT = 145 K
β = 118.440 (3)°Block, yellow
V = 1848.50 (10) Å30.38 × 0.25 × 0.15 mm
Z = 4
Data collection top
Agilent Xcalibur Eos
diffractometer
3772 independent reflections
Radiation source: fine-focus sealed tube3104 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.0874 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = 99
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 3134
Tmin = 0.970, Tmax = 1.0l = 1210
8048 measured reflections
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0385P)2 + 3.9868P]
where P = (Fo2 + 2Fc2)/3
3772 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 1.02 e Å3
1 restraintΔρmin = 0.68 e Å3
Crystal data top
C17H21N3O4S2V = 1848.50 (10) Å3
Mr = 395.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.4201 (2) ŵ = 0.32 mm1
b = 27.8329 (7) ÅT = 145 K
c = 10.1790 (3) Å0.38 × 0.25 × 0.15 mm
β = 118.440 (3)°
Data collection top
Agilent Xcalibur Eos
diffractometer
3772 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
3104 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 1.0Rint = 0.021
8048 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 1.02 e Å3
3772 reflectionsΔρmin = 0.68 e Å3
225 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*/UeqOcc. (<1)
S10.35683 (10)0.25100 (2)0.68116 (8)0.02193 (18)
S20.04835 (11)0.23017 (3)0.69685 (8)0.02609 (19)
O10.4402 (3)0.24711 (8)0.7824 (2)0.0303 (5)
O20.3343 (3)0.29724 (7)0.6291 (2)0.0321 (5)
O30.8016 (4)0.10467 (11)1.0716 (4)0.0578 (8)
O40.8590 (14)0.0450 (3)0.9436 (13)0.060 (2)0.578 (12)
O4A0.9294 (19)0.0474 (5)1.0238 (16)0.060 (2)0.422 (12)
N10.4979 (4)0.21961 (8)0.5357 (3)0.0237 (5)
H10.55430.23320.44690.028*
N20.4249 (4)0.11205 (9)1.0276 (3)0.0284 (6)
H20.538 (5)0.1238 (12)1.068 (4)0.029 (9)*
N30.7563 (6)0.06859 (12)0.9914 (5)0.0608 (11)
C10.5341 (5)0.16781 (10)0.5495 (3)0.0259 (6)
H1A0.50330.16170.65500.031*
C20.3928 (5)0.13607 (11)0.5162 (3)0.0331 (7)
H2B0.24810.14380.58670.040*
H2A0.41640.14250.41350.040*
C30.4336 (6)0.08302 (12)0.5313 (4)0.0461 (9)
H3A0.34670.06290.50380.055*
H3B0.39610.07600.63660.055*
C40.6567 (7)0.07034 (13)0.4319 (4)0.0552 (11)
H4B0.67990.03640.44910.066*
H4A0.68980.07370.32590.066*
C50.7976 (6)0.10240 (14)0.4624 (4)0.0510 (10)
H5B0.77660.09600.56450.061*
H5A0.94190.09470.39080.061*
C60.7576 (5)0.15573 (12)0.4483 (4)0.0348 (7)
H6A0.79380.16300.34340.042*
H6B0.84490.17570.47570.042*
C70.1161 (4)0.22402 (10)0.7707 (3)0.0204 (6)
C80.2109 (4)0.18895 (11)0.8212 (3)0.0249 (6)
H80.33580.17920.82460.030*
C90.1434 (4)0.17152 (10)0.9146 (3)0.0212 (6)
C100.0482 (4)0.19163 (10)0.8847 (3)0.0210 (6)
H100.12040.18350.93760.025*
C110.2639 (4)0.13708 (11)1.0413 (3)0.0256 (6)
H11B0.32550.15521.13650.031*
H11A0.16850.11311.04590.031*
C120.3906 (5)0.07546 (11)0.9310 (4)0.0316 (7)
C130.1906 (8)0.05721 (14)0.8436 (5)0.0589 (6)
H130.07940.07240.84850.071*
C140.1522 (8)0.01803 (13)0.7514 (5)0.0589 (6)
H140.01600.00640.69510.071*
C150.3109 (8)0.00463 (14)0.7402 (5)0.0589 (6)
H150.28330.03190.67740.071*
C160.5047 (8)0.01209 (13)0.8186 (5)0.0589 (6)
H160.61290.00340.81030.071*
C170.5473 (6)0.05249 (12)0.9128 (5)0.0450 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0235 (3)0.0198 (3)0.0232 (4)0.0021 (3)0.0117 (3)0.0014 (3)
S20.0281 (4)0.0275 (4)0.0287 (4)0.0020 (3)0.0183 (3)0.0070 (3)
O10.0291 (11)0.0366 (12)0.0302 (11)0.0012 (9)0.0182 (9)0.0082 (9)
O20.0316 (12)0.0192 (10)0.0380 (12)0.0023 (9)0.0106 (10)0.0031 (9)
O30.0391 (15)0.0464 (17)0.096 (2)0.0100 (13)0.0383 (16)0.0169 (16)
O40.050 (5)0.057 (2)0.095 (6)0.017 (3)0.052 (5)0.011 (5)
O4A0.050 (5)0.057 (2)0.095 (6)0.017 (3)0.052 (5)0.011 (5)
N10.0280 (12)0.0215 (12)0.0181 (12)0.0003 (10)0.0082 (10)0.0022 (9)
N20.0227 (13)0.0229 (13)0.0393 (15)0.0004 (11)0.0145 (12)0.0007 (11)
N30.065 (2)0.0361 (19)0.119 (3)0.0221 (17)0.075 (2)0.036 (2)
C10.0364 (16)0.0231 (15)0.0187 (14)0.0042 (12)0.0135 (13)0.0003 (11)
C20.0482 (19)0.0268 (16)0.0243 (15)0.0024 (14)0.0171 (15)0.0002 (13)
C30.073 (3)0.0254 (18)0.0374 (19)0.0041 (17)0.0239 (19)0.0005 (15)
C40.092 (3)0.0248 (18)0.039 (2)0.017 (2)0.024 (2)0.0056 (15)
C50.065 (3)0.043 (2)0.039 (2)0.027 (2)0.0201 (19)0.0041 (17)
C60.0415 (18)0.0339 (18)0.0296 (17)0.0096 (15)0.0176 (15)0.0042 (14)
C70.0225 (13)0.0200 (14)0.0219 (14)0.0017 (11)0.0132 (11)0.0028 (11)
C80.0219 (14)0.0269 (15)0.0289 (15)0.0006 (12)0.0144 (12)0.0016 (12)
C90.0224 (13)0.0218 (14)0.0197 (13)0.0038 (11)0.0104 (11)0.0029 (11)
C100.0234 (14)0.0227 (14)0.0193 (13)0.0034 (11)0.0122 (11)0.0018 (11)
C110.0239 (14)0.0281 (16)0.0248 (15)0.0008 (12)0.0117 (12)0.0022 (12)
C120.0455 (18)0.0206 (15)0.0385 (18)0.0004 (14)0.0281 (15)0.0079 (13)
C130.1099 (19)0.0302 (10)0.0576 (13)0.0114 (11)0.0569 (14)0.0012 (9)
C140.1099 (19)0.0302 (10)0.0576 (13)0.0114 (11)0.0569 (14)0.0012 (9)
C150.1099 (19)0.0302 (10)0.0576 (13)0.0114 (11)0.0569 (14)0.0012 (9)
C160.1099 (19)0.0302 (10)0.0576 (13)0.0114 (11)0.0569 (14)0.0012 (9)
C170.075 (3)0.0216 (16)0.068 (3)0.0064 (17)0.058 (2)0.0131 (16)
Geometric parameters (Å, º) top
S1—O11.436 (2)C4—H4A0.9900
S1—O21.431 (2)C4—C51.515 (6)
S1—N11.605 (2)C5—H5B0.9900
S1—C71.742 (3)C5—H5A0.9900
S2—C71.720 (3)C5—C61.534 (5)
S2—C81.708 (3)C6—H6A0.9900
O3—N31.235 (5)C6—H6B0.9900
O4—N31.265 (9)C7—C101.362 (4)
O4A—N31.305 (12)C8—H80.9500
N1—H10.8800C8—C91.358 (4)
N1—C11.485 (4)C9—C101.420 (4)
N2—H20.81 (3)C9—C111.511 (4)
N2—C111.446 (4)C10—H100.9500
N2—C121.353 (4)C11—H11B0.9900
N3—C171.437 (6)C11—H11A0.9900
C1—H1A1.0000C12—C131.412 (6)
C1—C21.528 (4)C12—C171.414 (5)
C1—C61.515 (4)C13—H130.9500
C2—H2B0.9900C13—C141.377 (5)
C2—H2A0.9900C14—H140.9500
C2—C31.530 (4)C14—C151.387 (6)
C3—H3A0.9900C15—H150.9500
C3—H3B0.9900C15—C161.353 (6)
C3—C41.514 (6)C16—H160.9500
C4—H4B0.9900C16—C171.412 (5)
S1—N1—H1119.7C4—C5—C6111.5 (3)
S2—C7—S1119.50 (16)H4B—C4—H4A108.0
S2—C8—H8123.4C5—C4—H4B109.3
O1—S1—N1107.83 (13)C5—C4—H4A109.3
O1—S1—C7106.07 (13)C5—C6—H6A109.6
O2—S1—O1119.95 (13)C5—C6—H6B109.6
O2—S1—N1106.73 (13)H5B—C5—H5A108.0
O2—S1—C7108.05 (13)C6—C1—H1A108.0
O3—N3—O4130.6 (6)C6—C1—C2111.4 (3)
O3—N3—O4A106.0 (7)C6—C5—H5B109.3
O3—N3—C17120.2 (3)C6—C5—H5A109.3
O4—N3—O4A33.1 (5)H6A—C6—H6B108.1
O4—N3—C17108.2 (6)C7—C10—C9111.7 (2)
O4A—N3—C17132.2 (7)C7—C10—H10124.1
N1—S1—C7107.69 (13)C8—S2—C790.39 (14)
N1—C1—H1A108.0C8—C9—C10112.0 (3)
N1—C1—C2111.5 (2)C8—C9—C11124.0 (3)
N1—C1—C6109.9 (2)C9—C8—S2113.2 (2)
N2—C11—C9113.8 (2)C9—C8—H8123.4
N2—C11—H11B108.8C9—C10—H10124.1
N2—C11—H11A108.8C9—C11—H11B108.8
N2—C12—C13120.4 (3)C9—C11—H11A108.8
N2—C12—C17123.6 (3)C10—C7—S1127.0 (2)
C1—N1—S1120.60 (19)C10—C7—S2112.8 (2)
C1—N1—H1119.7C10—C9—C11123.9 (2)
C1—C2—H2B109.6C11—N2—H2117 (2)
C1—C2—H2A109.6H11B—C11—H11A107.7
C1—C2—C3110.3 (3)C12—N2—H2118 (2)
C1—C6—C5110.4 (3)C12—N2—C11123.7 (3)
C1—C6—H6A109.6C12—C13—H13119.0
C1—C6—H6B109.6C12—C17—N3121.5 (3)
C2—C1—H1A108.0C13—C12—C17115.9 (3)
C2—C3—H3A109.4C13—C14—H14119.7
C2—C3—H3B109.4C13—C14—C15120.5 (5)
H2B—C2—H2A108.1C14—C13—C12121.9 (4)
C3—C2—H2B109.6C14—C13—H13119.0
C3—C2—H2A109.6C14—C15—H15120.0
C3—C4—H4B109.3C15—C14—H14119.7
C3—C4—H4A109.3C15—C16—H16119.8
C3—C4—C5111.6 (3)C15—C16—C17120.4 (4)
H3A—C3—H3B108.0C16—C15—C14120.0 (4)
C4—C3—C2111.3 (3)C16—C15—H15120.0
C4—C3—H3A109.4C16—C17—N3117.3 (4)
C4—C3—H3B109.4C16—C17—C12121.1 (4)
C4—C5—H5B109.3C17—C16—H16119.8
C4—C5—H5A109.3
S1—N1—C1—C298.5 (3)C1—C2—C3—C455.9 (4)
S1—N1—C1—C6137.5 (2)C2—C1—C6—C556.5 (3)
S1—C7—C10—C9170.7 (2)C2—C3—C4—C555.4 (4)
S2—C7—C10—C90.7 (3)C3—C4—C5—C655.0 (4)
S2—C8—C9—C100.6 (3)C4—C5—C6—C155.3 (4)
S2—C8—C9—C11176.0 (2)C6—C1—C2—C356.9 (3)
O1—S1—N1—C156.2 (2)C7—S1—N1—C157.9 (2)
O1—S1—C7—S2169.60 (16)C7—S2—C8—C90.2 (2)
O1—S1—C7—C1021.0 (3)C8—S2—C7—S1171.17 (18)
O2—S1—N1—C1173.7 (2)C8—S2—C7—C100.3 (2)
O2—S1—C7—S239.8 (2)C8—C9—C10—C70.9 (3)
O2—S1—C7—C10150.8 (3)C8—C9—C11—N218.9 (4)
O3—N3—C17—C123.6 (5)C10—C9—C11—N2165.0 (3)
O3—N3—C17—C16177.7 (3)C11—N2—C12—C134.6 (5)
O4—N3—C17—C12173.6 (5)C11—N2—C12—C17177.0 (3)
O4—N3—C17—C167.6 (6)C11—C9—C10—C7175.7 (3)
O4A—N3—C17—C12159.5 (9)C12—N2—C11—C975.0 (4)
O4A—N3—C17—C1619.2 (10)C12—C13—C14—C150.8 (6)
N1—S1—C7—S275.17 (19)C13—C12—C17—N3177.9 (3)
N1—S1—C7—C1094.3 (3)C13—C12—C17—C163.4 (5)
N1—C1—C2—C3180.0 (2)C13—C14—C15—C160.9 (6)
N1—C1—C6—C5179.5 (3)C14—C15—C16—C170.3 (6)
N2—C12—C13—C14175.7 (3)C15—C16—C17—N3179.3 (3)
N2—C12—C17—N33.6 (5)C15—C16—C17—C121.9 (5)
N2—C12—C17—C16175.1 (3)C17—C12—C13—C142.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.272.956 (3)134
N2—H2···O2ii0.81 (3)2.36 (3)2.979 (3)135 (3)
N2—H2···O30.81 (3)2.01 (3)2.620 (4)132 (3)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H21N3O4S2
Mr395.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)145
a, b, c (Å)7.4201 (2), 27.8329 (7), 10.1790 (3)
β (°) 118.440 (3)
V3)1848.50 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.38 × 0.25 × 0.15
Data collection
DiffractometerAgilent Xcalibur Eos
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.970, 1.0
No. of measured, independent and
observed [I > 2σ(I)] reflections
8048, 3772, 3104
Rint0.021
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.129, 1.01
No. of reflections3772
No. of parameters225
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.02, 0.68

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.272.956 (3)134.3
N2—H2···O2ii0.81 (3)2.36 (3)2.979 (3)135 (3)
N2—H2···O30.81 (3)2.01 (3)2.620 (4)132 (3)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2.
 

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection. This work was supported by the Research Fund of the Key Laboratory of TCM Biotechnology, Xihua University.

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies, Oxford, England.  Google Scholar
First citationCuberes Altisen, R., Frigola Constansa, J. & Gutierrez Silva, B. (2007). US Patent Appl. US 20070066587 A1 20070322.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSanthakumar, V. & Tomaszewski, M. (2006). PCT Int. Appl. WO 2006052189 A1 20060518.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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