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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 66| Part 12| December 2010| Page o3219
https://doi.org/10.1107/S160053681004688X

8-Chloro-5,5-di­methyl-5,6-di­hydro­tetra­zolo[1,5-c]quinazoline

Hoong-Kun Fun,a*‡ Chin Sing Yeap,a§ J. Gowda,b A. M. A. Khaderb and Balakrishna Kallurayab

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 11 November 2010; accepted 12 November 2010; online 20 November 2010)

In the title compound, C10H10ClN5, the tetra­zole ring and the phenyl ring make a dihedral angle of 7.7 (2)°. The hexa­hydro­pyrimidine ring adopts a screw-boat conformation. In the crystal, inter­molecular bifurcated N—H⋯(N,N) hydrogen bonds link the mol­ecules into [001] chains.

Related literature

For applications of tetra­zole derivatives, see: Upadhayaya et al. (2004[Upadhayaya, R. S., Jain, S., Sinha, N., Kishore, N., Chandra, R. & Arora, S. K. (2004). Eur. J. Med. Chem. 39, 575-592.]); Poonian et al. (1976[Poonian, M. S., Nowoswiat, E. F., Blount, J. F. & Kramer, M. J. (1976). J. Med. Chem. 19, 1017-1020.]); Ismail et al. (2006[Ismail, M. A. H., Barker, S., Alou El Ella, D. A., Abouzid, K. A. M., Toubar, R. A. & Todd, M. H. (2006). J. Med. Chem. 46, 1526-1535.]); Mulwad & Kewat (2008[Mulwad, V. V. & Kewat, V. P. (2008). Indian J. Het. Chem. 17, 205-208.]); Uchida et al. (1989[Uchida, M., Komatsu, M., Morita, S., Kanbe, T., Yamasaki, K. & Nakagawa, K. (1989). Chem. Pharm. Bull. 37, 958-961.]). For ring conformations, see: Boeyens (1978[Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C10H10ClN5

  • Mr = 235.68

  • Monoclinic, P 21 /c

  • a = 6.8324 (16) Å

  • b = 21.532 (5) Å

  • c = 9.4337 (16) Å

  • β = 130.823 (11)°

  • V = 1050.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 100 K

  • 0.16 × 0.11 × 0.05 mm
Data collection

  • Bruker APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.948, Tmax = 0.982

  • 9660 measured reflections

  • 2412 independent reflections

  • 1777 reflections with I > 2σ(I)

  • Rint = 0.066
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.137

  • S = 1.12

  • 2412 reflections

  • 151 parameters

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

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N5—H1N5⋯N1i 0.85 (4) 2.35 (4) 3.190 (3) 173 (6)
N5—H1N5⋯N2i 0.85 (4) 2.57 (4) 3.326 (3) 150 (4)
Symmetry code: (i) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681004688X/hb5733sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004688X/hb5733Isup2.hkl

checkCIF report


Comment top

A number of tetrazole derivatives were reported as to be antifungal agents (Upadhayaya et al., 2004), antiviral agents (Poonian et al., 1976), angiotensin II AT1 receptor antagonists (Ismail et al., 2006), antibacterial agents (Mulwad & Kewat, 2008) and anti-ulcer agents (Uchida et al., 1989). On the basis of these considerations, our particular attention was directed to synthesize some tetrazole derivatives.

The title compound is a three fused-ring structure (Fig. 1). The tetrazole ring and the phenyl ring make dihedral angle of 7.7 (2)°. The hexahydropyrimidine ring adopts a screw-boat conformation, with puckering amplitude Q = 0.308 (3) Å, θ = 61.8 (6)°, φ = 270.4 (7)° (Boeyens, 1978). In the crystal structure, intermolecular bifurcated N5—H1N5···N1 and N5—H1N5···N2 hydrogen bonds link the molecules into chains along c axis (Fig. 2, Table 1).

Related literature top

For applications of tetrazole derivatives, see: Upadhayaya et al. (2004); Poonian et al. (1976); Ismail et al. (2006); Mulwad & Kewat (2008); Uchida et al. (1989). For ring conformations, see: Boeyens (1978). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of 2-amino-4-chlorobenzonitrile (4.2 mmol) in N,N-dimethylformamide was added ammonium chloride (3 eq) and sodium azide (3 eq). The resulting reaction mixture was refluxed for 12 h. The completion of reaction was checked by TLC (100% EA). The reaction mixture was poured into ice-water after cooling to RT and acidified to give tetrazoles as a white mass. The resulting compound was then condensed with acetone to get the title compound: colourless plates were obtained by crystallization from acetone under slow evaporation (Mp. 501 K).

Refinement top

The N-bound hydrogen atom was located from difference Fourier map and refined freely. The rest of hydrogen atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and refined using a riding model [Uiso(H) = 1.2 or 1.5Ueq]. A rotating-group model were applied for methyl groups.

Structure description top

A number of tetrazole derivatives were reported as to be antifungal agents (Upadhayaya et al., 2004), antiviral agents (Poonian et al., 1976), angiotensin II AT1 receptor antagonists (Ismail et al., 2006), antibacterial agents (Mulwad & Kewat, 2008) and anti-ulcer agents (Uchida et al., 1989). On the basis of these considerations, our particular attention was directed to synthesize some tetrazole derivatives.

The title compound is a three fused-ring structure (Fig. 1). The tetrazole ring and the phenyl ring make dihedral angle of 7.7 (2)°. The hexahydropyrimidine ring adopts a screw-boat conformation, with puckering amplitude Q = 0.308 (3) Å, θ = 61.8 (6)°, φ = 270.4 (7)° (Boeyens, 1978). In the crystal structure, intermolecular bifurcated N5—H1N5···N1 and N5—H1N5···N2 hydrogen bonds link the molecules into chains along c axis (Fig. 2, Table 1).

For applications of tetrazole derivatives, see: Upadhayaya et al. (2004); Poonian et al. (1976); Ismail et al. (2006); Mulwad & Kewat (2008); Uchida et al. (1989). For ring conformations, see: Boeyens (1978). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing of title compound, viewed down b axis, showing the molecules are linked into chains along c axis. Intermolecular hydrogen bonds are shown as dashed lines.
8-Chloro-5,5-dimethyl-5,6-dihydrotetrazolo[1,5-c]quinazoline top
Crystal data top
C10H10ClN5F(000) = 488
Mr = 235.68Dx = 1.491 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1888 reflections
a = 6.8324 (16) Åθ = 3.0–29.9°
b = 21.532 (5) ŵ = 0.34 mm−1
c = 9.4337 (16) ÅT = 100 K
β = 130.823 (11)°Plate, colourless
V = 1050.2 (4) Å30.16 × 0.11 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII DUO CCD
diffractometer		2412 independent reflections
Radiation source: fine-focus sealed tube1777 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
φ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −8→8
Tmin = 0.948, Tmax = 0.982k = −27→27
9660 measured reflectionsl = −12→12
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0361P)2 + 1.9098P]
where P = (Fo2 + 2Fc2)/3
2412 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C10H10ClN5V = 1050.2 (4) Å3
Mr = 235.68Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.8324 (16) ŵ = 0.34 mm−1
b = 21.532 (5) ÅT = 100 K
c = 9.4337 (16) Å0.16 × 0.11 × 0.05 mm
β = 130.823 (11)°
Data collection top
Bruker APEXII DUO CCD
diffractometer		2412 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		1777 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.982Rint = 0.066
9660 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.61 e Å−3
2412 reflectionsΔρmin = −0.31 e Å−3
151 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl10.68351 (15)0.62515 (4)0.46138 (11)0.0285 (2)
N10.0252 (5)0.85800 (13)−0.2050 (3)0.0225 (6)
N20.0079 (5)0.92121 (14)−0.2261 (3)0.0276 (6)
N30.1672 (5)0.94937 (13)−0.0661 (3)0.0248 (6)
N40.2938 (4)0.90385 (12)0.0634 (3)0.0192 (5)
N50.6368 (5)0.85848 (12)0.3484 (3)0.0210 (6)
C10.2056 (5)0.84885 (14)−0.0218 (4)0.0190 (6)
C20.3106 (5)0.79248 (14)0.0880 (4)0.0185 (6)
C30.2129 (6)0.73316 (15)0.0145 (4)0.0216 (7)
H3A0.07040.7285−0.11220.026*
C40.3259 (6)0.68153 (15)0.1280 (4)0.0234 (7)
H4A0.26130.64200.07970.028*
C50.5397 (6)0.69013 (15)0.3174 (4)0.0213 (6)
C60.6402 (6)0.74777 (15)0.3947 (4)0.0209 (6)
H6A0.78160.75180.52180.025*
C70.5276 (5)0.80012 (14)0.2800 (4)0.0176 (6)
C80.4845 (5)0.91539 (14)0.2689 (4)0.0189 (6)
C90.6573 (6)0.96910 (15)0.3100 (4)0.0271 (7)
H9A0.73580.96080.25690.041*
H9B0.78960.97420.44310.041*
H9C0.55611.00640.25610.041*
C100.3352 (6)0.92761 (16)0.3348 (4)0.0254 (7)
H10A0.22940.89230.30650.038*
H10B0.22750.96350.27180.038*
H10C0.45490.93470.46750.038*
H1N50.751 (8)0.8595 (18)0.467 (6)0.039 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0280 (4)0.0248 (4)0.0334 (4)0.0052 (3)0.0204 (3)0.0085 (4)
N10.0187 (12)0.0307 (16)0.0131 (12)0.0000 (10)0.0082 (10)0.0003 (11)
N20.0240 (13)0.0355 (17)0.0148 (12)0.0021 (12)0.0089 (11)0.0035 (12)
N30.0251 (13)0.0289 (15)0.0147 (12)0.0052 (11)0.0106 (11)0.0061 (11)
N40.0191 (12)0.0225 (14)0.0107 (11)0.0023 (10)0.0074 (10)0.0021 (10)
N50.0173 (12)0.0213 (14)0.0104 (12)−0.0010 (10)0.0029 (10)−0.0017 (10)
C10.0154 (13)0.0267 (16)0.0135 (13)−0.0013 (12)0.0088 (11)−0.0040 (12)
C20.0167 (13)0.0237 (17)0.0151 (13)0.0009 (12)0.0104 (11)−0.0009 (12)
C30.0182 (14)0.0282 (18)0.0166 (14)−0.0047 (12)0.0105 (12)−0.0053 (13)
C40.0237 (15)0.0227 (17)0.0253 (16)−0.0048 (13)0.0166 (13)−0.0063 (13)
C50.0214 (14)0.0236 (17)0.0257 (15)0.0044 (12)0.0184 (13)0.0044 (13)
C60.0178 (14)0.0259 (17)0.0165 (14)0.0015 (12)0.0101 (12)0.0001 (12)
C70.0162 (13)0.0204 (16)0.0171 (13)−0.0006 (11)0.0113 (11)−0.0016 (12)
C80.0174 (13)0.0207 (16)0.0135 (13)−0.0005 (12)0.0079 (11)0.0006 (12)
C90.0288 (16)0.0279 (18)0.0178 (14)−0.0080 (14)0.0122 (13)−0.0009 (13)
C100.0240 (15)0.0300 (19)0.0195 (15)0.0002 (13)0.0130 (13)−0.0006 (13)
Geometric parameters (Å, º) top
Cl1—C51.739 (3)C3—H3A0.9300
N1—C11.326 (4)C4—C51.396 (4)
N1—N21.369 (4)C4—H4A0.9300
N2—N31.297 (4)C5—C61.374 (4)
N3—N41.349 (3)C6—C71.394 (4)
N4—C11.334 (4)C6—H6A0.9300
N4—C81.489 (3)C8—C91.511 (4)
N5—C71.386 (4)C8—C101.525 (4)
N5—C81.458 (4)C9—H9A0.9600
N5—H1N50.85 (4)C9—H9B0.9600
C1—C21.445 (4)C9—H9C0.9600
C2—C31.397 (4)C10—H10A0.9600
C2—C71.413 (4)C10—H10B0.9600
C3—C41.378 (4)C10—H10C0.9600
C1—N1—N2104.8 (2)C5—C6—C7119.2 (3)
N3—N2—N1111.6 (2)C5—C6—H6A120.4
N2—N3—N4105.5 (3)C7—C6—H6A120.4
C1—N4—N3109.3 (2)N5—C7—C6121.0 (3)
C1—N4—C8126.8 (2)N5—C7—C2119.8 (3)
N3—N4—C8123.7 (2)C6—C7—C2119.0 (3)
C7—N5—C8122.4 (2)N5—C8—N4104.6 (2)
C7—N5—H1N5113 (3)N5—C8—C9109.6 (2)
C8—N5—H1N5113 (3)N4—C8—C9109.5 (2)
N1—C1—N4108.8 (3)N5—C8—C10112.2 (2)
N1—C1—C2131.4 (3)N4—C8—C10108.1 (2)
N4—C1—C2119.8 (2)C9—C8—C10112.4 (3)
C3—C2—C7120.2 (3)C8—C9—H9A109.5
C3—C2—C1124.0 (3)C8—C9—H9B109.5
C7—C2—C1115.7 (3)H9A—C9—H9B109.5
C4—C3—C2120.6 (3)C8—C9—H9C109.5
C4—C3—H3A119.7H9A—C9—H9C109.5
C2—C3—H3A119.7H9B—C9—H9C109.5
C3—C4—C5118.3 (3)C8—C10—H10A109.5
C3—C4—H4A120.9C8—C10—H10B109.5
C5—C4—H4A120.9H10A—C10—H10B109.5
C6—C5—C4122.7 (3)C8—C10—H10C109.5
C6—C5—Cl1118.8 (2)H10A—C10—H10C109.5
C4—C5—Cl1118.5 (2)H10B—C10—H10C109.5
C1—N1—N2—N3−0.1 (3)C4—C5—C6—C7−0.8 (4)
N1—N2—N3—N40.4 (3)Cl1—C5—C6—C7179.5 (2)
N2—N3—N4—C1−0.7 (3)C8—N5—C7—C6−153.7 (3)
N2—N3—N4—C8−175.8 (2)C8—N5—C7—C231.3 (4)
N2—N1—C1—N4−0.3 (3)C5—C6—C7—N5−174.1 (3)
N2—N1—C1—C2179.9 (3)C5—C6—C7—C21.0 (4)
N3—N4—C1—N10.6 (3)C3—C2—C7—N5174.4 (3)
C8—N4—C1—N1175.6 (2)C1—C2—C7—N5−4.6 (4)
N3—N4—C1—C2−179.6 (2)C3—C2—C7—C6−0.7 (4)
C8—N4—C1—C2−4.6 (4)C1—C2—C7—C6−179.7 (2)
N1—C1—C2—C3−7.2 (5)C7—N5—C8—N4−38.5 (3)
N4—C1—C2—C3173.0 (3)C7—N5—C8—C9−155.9 (3)
N1—C1—C2—C7171.7 (3)C7—N5—C8—C1078.4 (3)
N4—C1—C2—C7−8.0 (4)C1—N4—C8—N525.7 (4)
C7—C2—C3—C40.2 (4)N3—N4—C8—N5−159.9 (2)
C1—C2—C3—C4179.2 (3)C1—N4—C8—C9143.2 (3)
C2—C3—C4—C5−0.1 (4)N3—N4—C8—C9−42.5 (4)
C3—C4—C5—C60.4 (4)C1—N4—C8—C10−94.0 (3)
C3—C4—C5—Cl1−179.9 (2)N3—N4—C8—C1080.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H1N5···N1i0.85 (4)2.35 (4)3.190 (3)173 (6)
N5—H1N5···N2i0.85 (4)2.57 (4)3.326 (3)150 (4)
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC10H10ClN5
Mr235.68
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)6.8324 (16), 21.532 (5), 9.4337 (16)
β (°) 130.823 (11)
V (Å3)1050.2 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.34
Crystal size (mm)0.16 × 0.11 × 0.05
Data collection
DiffractometerBruker APEXII DUO CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.948, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections		9660, 2412, 1777
Rint0.066
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.137, 1.12
No. of reflections2412
No. of parameters151
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.61, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), SHELXTL and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H1N5···N1i0.85 (4)2.35 (4)3.190 (3)173 (6)
N5—H1N5···N2i0.85 (4)2.57 (4)3.326 (3)150 (4)
Symmetry code: (i) x+1, y, z+1.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

First citationBoeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320.  CrossRef Web of Science Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationIsmail, M. A. H., Barker, S., Alou El Ella, D. A., Abouzid, K. A. M., Toubar, R. A. & Todd, M. H. (2006). J. Med. Chem. 46, 1526–1535.  Web of Science CrossRef Google Scholar
 First citationMulwad, V. V. & Kewat, V. P. (2008). Indian J. Het. Chem. 17, 205–208.  CAS Google Scholar
 First citationPoonian, M. S., Nowoswiat, E. F., Blount, J. F. & Kramer, M. J. (1976). J. Med. Chem. 19, 1017–1020.  CSD CrossRef CAS PubMed Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationUchida, M., Komatsu, M., Morita, S., Kanbe, T., Yamasaki, K. & Nakagawa, K. (1989). Chem. Pharm. Bull. 37, 958–961.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationUpadhayaya, R. S., Jain, S., Sinha, N., Kishore, N., Chandra, R. & Arora, S. K. (2004). Eur. J. Med. Chem. 39, 575–592.  Web of Science CrossRef Google Scholar

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3219
https://doi.org/10.1107/S160053681004688X
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