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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3025
https://doi.org/10.1107/S160053681204010X

2-Amino-4-methyl-4,5,6,7-tetra­hydro-1-benzo­thiophene-3-carbo­nitrile

Ashraf Y. Khan,a Nikhath Fathima,b Mallikarjun B. Kalashetti,a Noor Shahina Begumb and I. M. Khazia*

aDepartment of Chemistry, Karnatak University, Dharwad 580 003, India, and bDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: dr_imk@yahoo.com

(Received 31 August 2012; accepted 21 September 2012; online 26 September 2012)

In the title compound, C10H12N2S, the thio­phene ring is essentially planar (r.m.s. deviation = 0.0290 Å). The two C atoms of the cyclo­hexene ring (at positions 6 and 7) are disordered over two sets of sites in a 0.810 (5):0.190 (5) ratio. The cyclo­hexene rings in both the major and minor occupancy conformers adopt a half-chair conformation. In the crystal, there are two types of N—H⋯N inter­action. One of these results in centrosymmetric head-to-head dimers corresponding to an R22(12) graph-set motif and the other forms a 20-membered macrocyclic ring involving six mol­ecules.

Related literature

For biological activities of benzothio­phenes, see: Shetty et al. (2009[Shetty, N. S., Lamani, R. S. & Khazi, I. A. M. (2009). J. Chem. Sci. 121, 301-307.]). For the crystal structure of a closely related compound, see: Ziaulla et al. (2011[Ziaulla, M., Banu, A., Begum, N. S., Panchamukhi, S. I. & Khazi, I. M. (2011). Acta Cryst. E67, o699.]). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C10H12N2S

  • Mr = 192.28

  • Monoclinic, P 21 /c

  • a = 9.6771 (2) Å

  • b = 7.6364 (2) Å

  • c = 13.8156 (3) Å

  • β = 100.221 (2)°

  • V = 1004.75 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 296 K

  • 0.18 × 0.16 × 0.16 mm
Data collection

  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]) Tmin = 0.952, Tmax = 0.957

  • 8861 measured reflections

  • 2195 independent reflections

  • 1812 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.118

  • S = 1.06

  • 2195 reflections

  • 125 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯N2i 0.86 2.24 3.088 (2) 167
N1—H1B⋯N2ii 0.86 2.56 3.349 (2) 153
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681204010X/pv2585sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681204010X/pv2585Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681204010X/pv2585Isup3.cml

checkCIF report


Comment top

Tetrahydro-benzothiophenes are important class of compounds which exhibits antibacterial and antifungal activities (Shetty et al.,2009). In the title compound, the tetrahydro-benzothiophene ring is substituted with the methyl group at C8, amine at C2 and carbonitrile group at C3 positions. The thiophene ring is essentially planar (r.m.s. deviation = 0.03 Å). The atoms C6 and C7 are disordered over two sites (C6/C6' and C7/C7') with site occupancy factors 0.810 (5) and 0.190 (5) resulting in a major and a minor conformers, respectively. The cyclohexene ring in both the conformers is in the half-chair conformation with C6 and C7 atoms being deviated from the rest of the ring atoms by 0.3330 (3) and -0.3132 (3) Å for the major conformer. The C6' and C7' atoms are deviated by -0.3738 (2) and 0.3546 (2) Å for the minor conformer respectively. The methyl group of the cyclohexene ring is oriented axially which is characterized by the bond angles C6—C8—C11 = 112.50 (2)° and C10—C8—C11 = 115.02 (2)°. The crystal structure is stabilized by two types of N—H···N intermolecular interactions generating centrosymmetric head-to-head dimers corresponding to graph-set R22(12) motif (Bernstein et al., 1995) and a 20-membered macrocyclic ring involving six molecules (Fig. 2). The bond distances and angles in the title compound agree very well with the corresponding bond distances and angles reported in a closely related compound (Ziaulla et al., 2011).

Related literature top

For biological activities of benzothiophenes, see: Shetty et al. (2009). For the crystal structure of a closely related compound, see: Ziaulla et al. (2011). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

To a well stirred mixture of 2-methyl cyclohexanone (8 g, 71.4 mmole) and malononitrile (4.712 g, 71.4 mmole) in ethanol (100 ml) was added elemental sulfur (2.3 g, 72 mmole). To this cooled reaction mixture was added diethyl amine (5 ml) with vigorous stirring during 1 min. The reaction mixture was stirred at 333 K for about 1 h. The solvent was evaporated under reduced pressure. The residue was poured into crushed ice and the solid obtained was purified by column chromatography (yield = 9.3 g (68%), m.p. = 392–394 K. The crystals suitable for X-ray crystallographic analysis were grown from a solution of dichloromethane.

Refinement top

The occupancies were refined individually for the C atoms C6 and C7, the disordered atoms were grouped in Part 1 and Part 2 as Part 1: C6 and C7 with partial occupancy of 0.810 (5) and Part 2: C6' and C7' with partial occupancy 0.190 (5). In this way the occupancy disordered was modelled using the EADP command in SHELXL97. The H atoms were placed at calculated positions in the riding model approximation with N—H = 0.86° A, C—H = 0.97 and 0.96 Å for heterocyclic and methyl H atoms respectively, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(N/C).

Structure description top

Tetrahydro-benzothiophenes are important class of compounds which exhibits antibacterial and antifungal activities (Shetty et al.,2009). In the title compound, the tetrahydro-benzothiophene ring is substituted with the methyl group at C8, amine at C2 and carbonitrile group at C3 positions. The thiophene ring is essentially planar (r.m.s. deviation = 0.03 Å). The atoms C6 and C7 are disordered over two sites (C6/C6' and C7/C7') with site occupancy factors 0.810 (5) and 0.190 (5) resulting in a major and a minor conformers, respectively. The cyclohexene ring in both the conformers is in the half-chair conformation with C6 and C7 atoms being deviated from the rest of the ring atoms by 0.3330 (3) and -0.3132 (3) Å for the major conformer. The C6' and C7' atoms are deviated by -0.3738 (2) and 0.3546 (2) Å for the minor conformer respectively. The methyl group of the cyclohexene ring is oriented axially which is characterized by the bond angles C6—C8—C11 = 112.50 (2)° and C10—C8—C11 = 115.02 (2)°. The crystal structure is stabilized by two types of N—H···N intermolecular interactions generating centrosymmetric head-to-head dimers corresponding to graph-set R22(12) motif (Bernstein et al., 1995) and a 20-membered macrocyclic ring involving six molecules (Fig. 2). The bond distances and angles in the title compound agree very well with the corresponding bond distances and angles reported in a closely related compound (Ziaulla et al., 2011).

For biological activities of benzothiophenes, see: Shetty et al. (2009). For the crystal structure of a closely related compound, see: Ziaulla et al. (2011). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. C6 and C7 are disordered over sites C6/C6' and C7/C7' respectively.
[Figure 2] Fig. 2. A view of the intermolecular hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non participating in H-bonding were omitted for clarity.
2-Amino-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile top
Crystal data top
C10H12N2SF(000) = 408
Mr = 192.28Dx = 1.271 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2195 reflections
a = 9.6771 (2) Åθ = 2.1–27.0°
b = 7.6364 (2) ŵ = 0.28 mm−1
c = 13.8156 (3) ÅT = 296 K
β = 100.221 (2)°Block, yellow
V = 1004.75 (4) Å30.18 × 0.16 × 0.16 mm
Z = 4
Data collection top
Bruker SMART APEX CCD detector
diffractometer		2195 independent reflections
Radiation source: fine-focus sealed tube1812 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −12→12
Tmin = 0.952, Tmax = 0.957k = −9→9
8861 measured reflectionsl = −17→17
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) = 0.118H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1371P]
where P = (Fo2 + 2Fc2)/3
2195 reflections(Δ/σ)max < 0.001
125 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C10H12N2SV = 1004.75 (4) Å3
Mr = 192.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6771 (2) ŵ = 0.28 mm−1
b = 7.6364 (2) ÅT = 296 K
c = 13.8156 (3) Å0.18 × 0.16 × 0.16 mm
β = 100.221 (2)°
Data collection top
Bruker SMART APEX CCD detector
diffractometer		2195 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1812 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.957Rint = 0.024
8861 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.06Δρmax = 0.16 e Å−3
2195 reflectionsΔρmin = −0.25 e Å−3
125 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
S10.71234 (4)0.00203 (5)0.83213 (3)0.05244 (18)
C30.65478 (15)0.14987 (19)0.98594 (10)0.0421 (3)
C10.59583 (16)0.2640 (2)1.04856 (10)0.0472 (4)
N20.54845 (17)0.3532 (2)1.10080 (11)0.0653 (4)
C20.63578 (15)0.17225 (19)0.88557 (10)0.0439 (3)
C90.76862 (16)−0.0986 (2)0.94522 (11)0.0481 (4)
C80.73216 (16)−0.00656 (18)1.01974 (11)0.0420 (3)
N10.57113 (16)0.3034 (2)0.82953 (10)0.0650 (4)
H1A0.53450.38900.85660.078*
H1B0.56660.30140.76680.078*
C100.8661 (2)0.0583 (3)1.18824 (14)0.0791 (6)
H10A0.88370.01681.25490.119*
H10B0.82580.17341.18610.119*
H10C0.95280.06261.16370.119*
C40.76560 (17)−0.0641 (2)1.12553 (12)0.0528 (4)
H40.6773−0.05911.15090.063*0.810 (5)
C50.8427 (2)−0.2719 (2)0.95380 (14)0.0663 (5)
H5A0.9131−0.27400.91180.080*0.810 (5)
H5B0.7762−0.36550.93360.080*0.810 (5)
C70.8107 (4)−0.2568 (4)1.1298 (2)0.0708 (8)0.810 (5)
H7A0.8542−0.28571.19660.085*0.810 (5)
H7B0.7281−0.33001.11230.085*0.810 (5)
C60.9126 (4)−0.2970 (4)1.06146 (19)0.0730 (8)0.810 (5)
H6A0.9452−0.41681.07150.088*0.810 (5)
H6B0.9934−0.22021.07660.088*0.810 (5)
C4'0.76560 (17)−0.0641 (2)1.12553 (12)0.0528 (4)0.00
H4A0.6823−0.09251.15380.063*0.190 (5)
C5'0.8427 (2)−0.2719 (2)0.95380 (14)0.0663 (5)0.00
H5C0.9410−0.25570.94980.080*0.190 (5)
H5D0.8009−0.34850.90060.080*0.190 (5)
C7'0.8760 (17)−0.2149 (18)1.1356 (10)0.0708 (8)0.190 (5)
H7C0.8836−0.26971.19960.085*0.190 (5)
H7D0.9673−0.16791.12970.085*0.190 (5)
C6'0.8294 (17)−0.3534 (17)1.0531 (9)0.0730 (8)0.190 (5)
H6C0.8883−0.45671.06500.088*0.190 (5)
H6D0.7329−0.38821.05280.088*0.190 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0652 (3)0.0563 (3)0.0354 (2)0.01326 (18)0.00757 (18)−0.00553 (16)
C30.0464 (7)0.0441 (8)0.0358 (7)−0.0006 (6)0.0074 (5)−0.0036 (6)
C10.0574 (9)0.0472 (8)0.0362 (7)0.0016 (7)0.0063 (6)−0.0003 (6)
N20.0859 (11)0.0645 (9)0.0477 (8)0.0141 (8)0.0176 (7)−0.0073 (7)
C20.0486 (8)0.0458 (8)0.0369 (7)0.0041 (6)0.0062 (6)−0.0016 (6)
C90.0532 (8)0.0470 (9)0.0435 (8)0.0064 (7)0.0073 (6)0.0019 (6)
C80.0429 (7)0.0449 (8)0.0373 (8)−0.0026 (6)0.0044 (6)0.0023 (6)
N10.0891 (11)0.0662 (9)0.0391 (7)0.0320 (8)0.0095 (7)0.0061 (6)
C100.0743 (13)0.1082 (17)0.0479 (11)−0.0107 (12)−0.0082 (9)0.0044 (11)
C40.0556 (9)0.0618 (10)0.0413 (8)−0.0008 (8)0.0095 (7)0.0107 (8)
C50.0798 (12)0.0545 (10)0.0669 (12)0.0193 (9)0.0196 (9)0.0058 (9)
C70.083 (2)0.0661 (16)0.0646 (14)0.0052 (14)0.0166 (15)0.0268 (12)
C60.0775 (19)0.0668 (16)0.0730 (15)0.0256 (14)0.0090 (14)0.0181 (12)
C4'0.0556 (9)0.0618 (10)0.0413 (8)−0.0008 (8)0.0095 (7)0.0107 (8)
C5'0.0798 (12)0.0545 (10)0.0669 (12)0.0193 (9)0.0196 (9)0.0058 (9)
C7'0.083 (2)0.0661 (16)0.0646 (14)0.0052 (14)0.0166 (15)0.0268 (12)
C6'0.0775 (19)0.0668 (16)0.0730 (15)0.0256 (14)0.0090 (14)0.0181 (12)
Geometric parameters (Å, º) top
S1—C21.7256 (14)C4—C71.533 (3)
S1—C91.7397 (16)C4—H40.9800
C3—C21.3768 (19)C5—C61.533 (3)
C3—C11.417 (2)C5—H5A0.9700
C3—C81.443 (2)C5—H5B0.9700
C1—N21.146 (2)C7—C61.513 (5)
C2—N11.3499 (19)C7—H7A0.9700
C9—C81.345 (2)C7—H7B0.9700
C9—C51.500 (2)C6—H6A0.9700
C8—C41.505 (2)C6—H6B0.9700
N1—H1A0.8600C7'—C6'1.56 (2)
N1—H1B0.8600C7'—H7C0.9700
C10—C41.507 (3)C7'—H7D0.9700
C10—H10A0.9600C6'—H6C0.9700
C10—H10B0.9600C6'—H6D0.9700
C10—H10C0.9600
C2—S1—C992.20 (7)C10—C4—H4106.5
C2—C3—C1122.84 (14)C7—C4—H4106.5
C2—C3—C8113.43 (13)C9—C5—C6108.02 (16)
C1—C3—C8123.61 (13)C9—C5—H5A110.1
N2—C1—C3178.40 (17)C6—C5—H5A110.1
N1—C2—C3129.43 (14)C9—C5—H5B110.1
N1—C2—S1120.27 (11)C6—C5—H5B110.1
C3—C2—S1110.29 (11)H5A—C5—H5B108.4
C8—C9—C5125.99 (15)C6—C7—C4112.5 (2)
C8—C9—S1111.95 (12)C6—C7—H7A109.1
C5—C9—S1122.00 (12)C4—C7—H7A109.1
C9—C8—C3112.13 (14)C6—C7—H7B109.1
C9—C8—C4123.39 (14)C4—C7—H7B109.1
C3—C8—C4124.46 (14)H7A—C7—H7B107.8
C2—N1—H1A120.0C7—C6—C5110.9 (3)
C2—N1—H1B120.0C7—C6—H6A109.5
H1A—N1—H1B120.0C5—C6—H6A109.5
C4—C10—H10A109.5C7—C6—H6B109.5
C4—C10—H10B109.5C5—C6—H6B109.5
H10A—C10—H10B109.5H6A—C6—H6B108.1
C4—C10—H10C109.5C6'—C7'—H7C109.8
H10A—C10—H10C109.5C6'—C7'—H7D109.8
H10B—C10—H10C109.5H7C—C7'—H7D108.3
C8—C4—C10112.49 (15)C7'—C6'—H6C110.0
C8—C4—C7109.16 (16)C7'—C6'—H6D110.0
C10—C4—C7115.0 (2)H6C—C6'—H6D108.4
C8—C4—H4106.5
C2—C3—C1—N2158 (6)C2—C3—C8—C9−0.47 (19)
C8—C3—C1—N2−17 (6)C1—C3—C8—C9175.63 (14)
C1—C3—C2—N15.0 (3)C2—C3—C8—C4−178.94 (14)
C8—C3—C2—N1−178.86 (16)C1—C3—C8—C4−2.8 (2)
C1—C3—C2—S1−176.09 (12)C9—C8—C4—C10114.82 (19)
C8—C3—C2—S10.05 (16)C3—C8—C4—C10−66.9 (2)
C9—S1—C2—N1179.29 (14)C9—C8—C4—C7−14.1 (3)
C9—S1—C2—C30.28 (12)C3—C8—C4—C7164.16 (19)
C2—S1—C9—C8−0.56 (13)C8—C9—C5—C6−18.6 (3)
C2—S1—C9—C5176.80 (15)S1—C9—C5—C6164.40 (18)
C5—C9—C8—C3−176.56 (16)C8—C4—C7—C644.6 (3)
S1—C9—C8—C30.67 (17)C10—C4—C7—C6−82.9 (3)
C5—C9—C8—C41.9 (3)C4—C7—C6—C5−64.8 (4)
S1—C9—C8—C4179.16 (12)C9—C5—C6—C747.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.243.088 (2)167
N1—H1B···N2ii0.862.563.349 (2)153
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC10H12N2S
Mr192.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.6771 (2), 7.6364 (2), 13.8156 (3)
β (°) 100.221 (2)
V (Å3)1004.75 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.18 × 0.16 × 0.16
Data collection
DiffractometerBruker SMART APEX CCD detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.952, 0.957
No. of measured, independent and
observed [I > 2σ(I)] reflections		8861, 2195, 1812
Rint0.024
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.118, 1.06
No. of reflections2195
No. of parameters125
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.16, −0.25

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.2433.088 (2)167
N1—H1B···N2ii0.862.5583.349 (2)153
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+1/2, z−1/2.
 

Acknowledgements

IMK is grateful to the University Grants Commission (UGC), India, for financial assistance.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555–1573.  CrossRef CAS Google Scholar
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 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShetty, N. S., Lamani, R. S. & Khazi, I. A. M. (2009). J. Chem. Sci. 121, 301–307.  CrossRef CAS Google Scholar
 First citationWatkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.  Google Scholar
 First citationZiaulla, M., Banu, A., Begum, N. S., Panchamukhi, S. I. & Khazi, I. M. (2011). Acta Cryst. E67, o699.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3025
https://doi.org/10.1107/S160053681204010X
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