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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 2| February 2010| Page o363
https://doi.org/10.1107/S1600536810001066

Di­ethyl 4-(2,4-di­chloro­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

P. Palakshi Reddy,a V. Vijayakumar,a J. Suresh,b T. Narasimhamurthyc and P. L. Nilantha Lakshmand*

aOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, bDepartment of Physics, The Madura College, Madurai 625 011, India, cMaterials Research Centre, Indian Institute of Science, Bangalore 560 012, India, and dDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 22 December 2009; accepted 8 January 2010; online 16 January 2010)

In the title compound, C19H21Cl2NO4, the dihydro­pyridine ring adopts a flattened boat conformation. The dichloro­phenyl ring is oriented almost perpendicular to the planar part of the dihydro­pyridine ring [dihedral angle = 89.1 (1)°]. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal structure, mol­ecules are linked into chains along the b axis by N—H⋯O hydrogen bonds

Related literature

The dihydro­pyridine hetrocyclic ring is a common feature of various bioactive compounds such as vasodilator, anti­atherosclerotic, anti­tumor, geroprotective, hepta­protective and anti­diabetic agents, see: Salehi & Guo (2004[Salehi, H. & Guo, Q. X. (2004). Synth. Commun. 34, 4349-4357.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C19H21Cl2NO4

  • Mr = 398.27

  • Monoclinic, P 21 /c

  • a = 15.928 (7) Å

  • b = 12.266 (6) Å

  • c = 10.042 (5) Å

  • β = 103.962 (7)°

  • V = 1903.8 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 293 K

  • 0.19 × 0.16 × 0.12 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SADABS. Bruker AXS Inc., Maddison, Wisconsin, USA.]) Tmin = 0.933, Tmax = 0.937

  • 20317 measured reflections

  • 4491 independent reflections

  • 3230 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.168

  • S = 1.04

  • 4491 reflections

  • 243 parameters

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

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.85 (4) 2.46 (4) 3.298 (4) 169 (3)
C7—H7C⋯O2 0.96 2.14 2.764 (5) 122
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810001066/ci5001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001066/ci5001Isup2.hkl

checkCIF report


Comment top

1,4-Dihydropyridines are identified as an important class of drugs for a longwhile. The dihydropyridine hetrocyclic ring is a common feature of various bioactive compounds such as vasodilator, antiatherosclerotic, antitumor, geroprotective, heptaprotective and antidiabetic agents (Salehi & Guo, 2004).

The molecular structure of the title compound, with the adopted atomic numbering scheme is shown in Fig. 1. The dihydropyridine ring adopts a flattened boat conformation, with atoms N1 and C4 slightly displaced out of the C2/C3/C5/C6 plane by 0.088 (4) and 0.188 (4) Å, respectively. The puckering parameters (Cremer & Pople, 1975) are: q2 = 0.158 (3) Å, q3 = -0.039 (3) Å and φ2 = 3(1)°. The C—C and C—N bond distances of the pyridine ring agree well with expected values. The 2,4-dichlorophenyl ring at C4 is oriented at an angle of 89.1 (1)° with respect to the C2/C3/C5/C6 plane. This near perpendicular orientation of the chlorophenyl ring to the dihydropyridine ring can be ascribed to the greater steric hinderance with the two ethylcarboxylate groups at C3 and C5. Both ethylcarboxylate side chains adopt same orientation with respect to the dihydropyridine ring. An intramolecular C7—H7C···O2 hydrogen bond is observed.

In the crystal structure, the molecules are linked into chains along the b axis by N—H···O hydrogen bonds (Table 1).

Related literature top

The dihydropyridine hetrocyclic ring is a common feature of various

bioactive compounds such as vasodilator, antiatherosclerotic, antitumor,

geroprotective, heptaprotective and antidiabetic agents, see: Salehi & Guo (2004). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

Diethyl 2,6-dimethyl-1,4-dihydro-4-2(2,6-dichlorophenyl)-3,5- pyridinedicarboxylate is prepared according to Hantzsch pyridine synthesis. 2,6-Dichlororobenzaldehyde (10 mmol, 1.76 g), ethylacetoacetate (20 mmol, 2.6 ml) and ammonium acetate (10 mmol, 0.8 g) were taken in a 1:2:1 mole ratio along with ethanol as a solvent in a flask and refluxed in steam-bath until the colour of the solution changed to reddish-orange (approximately an hour) and kept in ice cold condition to get a solid product. The product was extracted using diethyl ether and then excess solvent was distilled off. The purity of the crude product was checked through TLC and recrystallized using a acetone-benzene (3:1) solution. Single crystals of the title compound suitable for X-ray diffraction analysis were grown using a acetone-benzene (3:1) solution over a period of 2 d (yield = 68%, m.p. 413 K).

Refinement top

The amino H atom was located in a difference map and was refined isotropically. The remaining H atoms were placed in calculated positions and allowed to ride on their carrier atoms, with C-H = 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C) for CH and CH2 groups and Uiso(H) = 1.5Ueq(C) for CH3 groups.

Structure description top

1,4-Dihydropyridines are identified as an important class of drugs for a longwhile. The dihydropyridine hetrocyclic ring is a common feature of various bioactive compounds such as vasodilator, antiatherosclerotic, antitumor, geroprotective, heptaprotective and antidiabetic agents (Salehi & Guo, 2004).

The molecular structure of the title compound, with the adopted atomic numbering scheme is shown in Fig. 1. The dihydropyridine ring adopts a flattened boat conformation, with atoms N1 and C4 slightly displaced out of the C2/C3/C5/C6 plane by 0.088 (4) and 0.188 (4) Å, respectively. The puckering parameters (Cremer & Pople, 1975) are: q2 = 0.158 (3) Å, q3 = -0.039 (3) Å and φ2 = 3(1)°. The C—C and C—N bond distances of the pyridine ring agree well with expected values. The 2,4-dichlorophenyl ring at C4 is oriented at an angle of 89.1 (1)° with respect to the C2/C3/C5/C6 plane. This near perpendicular orientation of the chlorophenyl ring to the dihydropyridine ring can be ascribed to the greater steric hinderance with the two ethylcarboxylate groups at C3 and C5. Both ethylcarboxylate side chains adopt same orientation with respect to the dihydropyridine ring. An intramolecular C7—H7C···O2 hydrogen bond is observed.

In the crystal structure, the molecules are linked into chains along the b axis by N—H···O hydrogen bonds (Table 1).

The dihydropyridine hetrocyclic ring is a common feature of various

bioactive compounds such as vasodilator, antiatherosclerotic, antitumor,

geroprotective, heptaprotective and antidiabetic agents, see: Salehi & Guo (2004). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Diethyl 4-(2,4-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top
Crystal data top
C19H21Cl2NO4F(000) = 832
Mr = 398.27Dx = 1.389 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 15.928 (7) Åθ = 2–28°
b = 12.266 (6) ŵ = 0.37 mm−1
c = 10.042 (5) ÅT = 293 K
β = 103.962 (7)°Block, colourless
V = 1903.8 (15) Å30.19 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		4491 independent reflections
Radiation source: fine-focus sealed tube3230 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −20→20
Tmin = 0.933, Tmax = 0.937k = −16→15
20317 measured reflectionsl = −13→13
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0754P)2 + 1.087P]
where P = (Fo2 + 2Fc2)/3
4491 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C19H21Cl2NO4V = 1903.8 (15) Å3
Mr = 398.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.928 (7) ŵ = 0.37 mm−1
b = 12.266 (6) ÅT = 293 K
c = 10.042 (5) Å0.19 × 0.16 × 0.12 mm
β = 103.962 (7)°
Data collection top
Bruker SMART APEX CCD
diffractometer		4491 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		3230 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.937Rint = 0.034
20317 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.55 e Å−3
4491 reflectionsΔρmin = −0.56 e Å−3
243 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
H10.457 (2)−0.188 (3)0.674 (4)0.077 (10)*
C20.36076 (17)−0.1934 (2)0.5152 (3)0.0498 (6)
C30.30628 (16)−0.13017 (19)0.4249 (3)0.0443 (5)
C40.30510 (14)−0.00633 (18)0.4398 (2)0.0385 (5)
H40.30470.02640.35060.046*
C50.38599 (15)0.03294 (19)0.5438 (2)0.0414 (5)
C60.43734 (15)−0.0368 (2)0.6316 (3)0.0458 (6)
C70.3671 (2)−0.3158 (2)0.5144 (4)0.0724 (9)
H7A0.3368−0.34570.57780.109*
H7B0.4268−0.33700.54110.109*
H7C0.3418−0.34260.42380.109*
C80.51522 (18)−0.0086 (3)0.7436 (3)0.0615 (7)
H8A0.54670.04930.71330.092*
H8B0.5518−0.07150.76560.092*
H8C0.49700.01450.82360.092*
C90.2429 (2)−0.1811 (2)0.3105 (3)0.0576 (7)
C100.1394 (2)−0.1567 (3)0.1037 (3)0.0834 (11)
H10A0.1663−0.21020.05620.100*
H10B0.0947−0.19290.13780.100*
C110.1024 (4)−0.0724 (5)0.0120 (5)0.146 (2)
H11A0.0756−0.01990.05930.219*
H11B0.0598−0.1027−0.06310.219*
H11C0.1468−0.0375−0.02240.219*
C120.40564 (15)0.1502 (2)0.5500 (3)0.0465 (6)
C130.3635 (2)0.3178 (2)0.4302 (4)0.0708 (9)
H13A0.35270.34070.33510.085*
H13B0.42070.34280.47730.085*
C140.2986 (2)0.3668 (3)0.4941 (4)0.0847 (11)
H14A0.24210.34110.44820.127*
H14B0.30060.44470.48660.127*
H14C0.31080.34650.58920.127*
C150.22400 (14)0.03096 (17)0.4827 (2)0.0382 (5)
C160.16297 (16)0.10357 (19)0.4097 (3)0.0442 (5)
C170.09232 (16)0.1380 (2)0.4559 (3)0.0529 (7)
H170.05310.18770.40570.064*
C180.08165 (16)0.0971 (2)0.5769 (3)0.0540 (7)
C190.13873 (18)0.0238 (2)0.6521 (3)0.0554 (7)
H190.1301−0.00400.73390.066*
C200.20941 (16)−0.0081 (2)0.6045 (3)0.0456 (6)
H200.2485−0.05740.65590.055*
N10.42086 (15)−0.14648 (18)0.6216 (3)0.0549 (6)
O10.45504 (13)0.19882 (16)0.6420 (2)0.0648 (5)
O20.2248 (3)−0.2760 (2)0.3005 (3)0.1241 (13)
O30.20393 (13)−0.11059 (17)0.2178 (2)0.0639 (5)
O40.36015 (13)0.19982 (14)0.4368 (2)0.0577 (5)
Cl10.17106 (5)0.15619 (6)0.25211 (7)0.0651 (2)
Cl2−0.00735 (5)0.13933 (8)0.63631 (10)0.0800 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0523 (14)0.0362 (12)0.0598 (16)0.0037 (11)0.0118 (12)−0.0033 (11)
C30.0485 (13)0.0359 (12)0.0476 (13)0.0012 (10)0.0099 (11)−0.0058 (10)
C40.0407 (12)0.0335 (11)0.0393 (12)0.0007 (9)0.0056 (9)0.0004 (9)
C50.0400 (12)0.0385 (12)0.0454 (13)0.0003 (10)0.0098 (10)−0.0031 (10)
C60.0406 (12)0.0461 (13)0.0486 (14)0.0025 (10)0.0066 (10)−0.0023 (11)
C70.076 (2)0.0376 (14)0.095 (2)0.0127 (14)0.0044 (18)0.0006 (15)
C80.0507 (15)0.0642 (18)0.0604 (17)0.0047 (13)−0.0048 (13)−0.0028 (14)
C90.0729 (18)0.0470 (15)0.0500 (15)−0.0009 (13)0.0093 (13)−0.0108 (12)
C100.078 (2)0.104 (3)0.0564 (19)−0.020 (2)−0.0069 (16)−0.0176 (19)
C110.149 (5)0.130 (4)0.108 (4)−0.009 (4)−0.069 (3)0.005 (3)
C120.0417 (13)0.0409 (13)0.0578 (15)−0.0012 (10)0.0135 (11)−0.0022 (11)
C130.087 (2)0.0406 (15)0.086 (2)−0.0071 (15)0.0233 (18)0.0076 (15)
C140.079 (2)0.0552 (19)0.114 (3)0.0075 (17)0.012 (2)−0.0121 (19)
C150.0391 (11)0.0308 (10)0.0412 (12)−0.0013 (9)0.0032 (9)−0.0027 (9)
C160.0448 (13)0.0369 (12)0.0470 (13)0.0020 (10)0.0034 (10)0.0019 (10)
C170.0440 (13)0.0440 (14)0.0667 (17)0.0065 (11)0.0052 (12)−0.0034 (12)
C180.0414 (13)0.0506 (15)0.0718 (18)−0.0042 (11)0.0168 (12)−0.0209 (13)
C190.0571 (16)0.0606 (17)0.0506 (15)−0.0094 (13)0.0170 (12)−0.0063 (12)
C200.0457 (13)0.0429 (13)0.0461 (13)0.0005 (10)0.0066 (10)0.0036 (10)
N10.0532 (13)0.0411 (12)0.0615 (14)0.0088 (10)−0.0033 (11)0.0063 (10)
O10.0614 (12)0.0495 (11)0.0764 (14)−0.0127 (9)0.0026 (10)−0.0115 (10)
O20.192 (3)0.0500 (14)0.095 (2)−0.0218 (17)−0.035 (2)−0.0179 (13)
O30.0652 (12)0.0620 (12)0.0538 (11)−0.0057 (10)−0.0063 (9)−0.0078 (9)
O40.0673 (12)0.0372 (9)0.0651 (12)−0.0024 (8)0.0089 (9)0.0024 (8)
Cl10.0712 (5)0.0637 (4)0.0564 (4)0.0147 (4)0.0075 (3)0.0212 (3)
Cl20.0531 (4)0.0868 (6)0.1078 (7)−0.0043 (4)0.0343 (4)−0.0335 (5)
Geometric parameters (Å, º) top
C2—C31.341 (4)C11—H11A0.96
C2—N11.376 (3)C11—H11B0.96
C2—C71.504 (4)C11—H11C0.96
C3—C91.473 (4)C12—O11.216 (3)
C3—C41.527 (3)C12—O41.338 (3)
C4—C151.527 (3)C13—O41.450 (3)
C4—C51.528 (3)C13—C141.470 (5)
C4—H40.98C13—H13A0.97
C5—C61.353 (3)C13—H13B0.97
C5—C121.470 (3)C14—H14A0.96
C6—N11.370 (3)C14—H14B0.96
C6—C81.500 (4)C14—H14C0.96
C7—H7A0.96C15—C201.384 (3)
C7—H7B0.96C15—C161.390 (3)
C7—H7C0.96C16—C171.383 (4)
C8—H8A0.96C16—Cl11.743 (3)
C8—H8B0.96C17—C181.363 (4)
C8—H8C0.96C17—H170.93
C9—O21.198 (4)C18—C191.368 (4)
C9—O31.312 (3)C18—Cl21.744 (3)
C10—C111.414 (6)C19—C201.382 (4)
C10—O31.456 (3)C19—H190.93
C10—H10A0.97C20—H200.93
C10—H10B0.97N1—H10.85 (4)
C3—C2—N1119.9 (2)C10—C11—H11C109.5
C3—C2—C7127.4 (3)H11A—C11—H11C109.5
N1—C2—C7112.7 (2)H11B—C11—H11C109.5
C2—C3—C9119.5 (2)O1—C12—O4122.7 (2)
C2—C3—C4122.0 (2)O1—C12—C5127.2 (2)
C9—C3—C4118.4 (2)O4—C12—C5110.1 (2)
C3—C4—C15110.91 (19)O4—C13—C14110.5 (3)
C3—C4—C5110.63 (19)O4—C13—H13A109.5
C15—C4—C5110.11 (19)C14—C13—H13A109.5
C3—C4—H4108.4O4—C13—H13B109.5
C15—C4—H4108.4C14—C13—H13B109.5
C5—C4—H4108.4H13A—C13—H13B108.1
C6—C5—C12120.1 (2)C13—C14—H14A109.5
C6—C5—C4121.6 (2)C13—C14—H14B109.5
C12—C5—C4118.2 (2)H14A—C14—H14B109.5
C5—C6—N1119.9 (2)C13—C14—H14C109.5
C5—C6—C8127.1 (2)H14A—C14—H14C109.5
N1—C6—C8113.0 (2)H14B—C14—H14C109.5
C2—C7—H7A109.5C20—C15—C16116.2 (2)
C2—C7—H7B109.5C20—C15—C4118.6 (2)
H7A—C7—H7B109.5C16—C15—C4125.1 (2)
C2—C7—H7C109.5C17—C16—C15122.8 (2)
H7A—C7—H7C109.5C17—C16—Cl1115.87 (19)
H7B—C7—H7C109.5C15—C16—Cl1121.4 (2)
C6—C8—H8A109.5C18—C17—C16118.3 (2)
C6—C8—H8B109.5C18—C17—H17120.9
H8A—C8—H8B109.5C16—C17—H17120.9
C6—C8—H8C109.5C17—C18—C19121.6 (2)
H8A—C8—H8C109.5C17—C18—Cl2118.8 (2)
H8B—C8—H8C109.5C19—C18—Cl2119.6 (2)
O2—C9—O3121.2 (3)C18—C19—C20118.9 (3)
O2—C9—C3125.7 (3)C18—C19—H19120.5
O3—C9—C3113.1 (2)C20—C19—H19120.5
C11—C10—O3109.4 (3)C19—C20—C15122.2 (2)
C11—C10—H10A109.8C19—C20—H20118.9
O3—C10—H10A109.8C15—C20—H20118.9
C11—C10—H10B109.8C6—N1—C2123.6 (2)
O3—C10—H10B109.8C6—N1—H1117 (2)
H10A—C10—H10B108.2C2—N1—H1118 (2)
C10—C11—H11A109.5C9—O3—C10115.2 (3)
C10—C11—H11B109.5C12—O4—C13118.3 (2)
H11A—C11—H11B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (4)2.46 (4)3.298 (4)169 (3)
C7—H7C···O20.962.142.764 (5)122
Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC19H21Cl2NO4
Mr398.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)15.928 (7), 12.266 (6), 10.042 (5)
β (°) 103.962 (7)
V (Å3)1903.8 (15)
Z4
Radiation typeMo Kα
µ (mm−1)0.37
Crystal size (mm)0.19 × 0.16 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.933, 0.937
No. of measured, independent and
observed [I > 2σ(I)] reflections		20317, 4491, 3230
Rint0.034
(sin θ/λ)max (Å−1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.168, 1.04
No. of reflections4491
No. of parameters243
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.55, −0.56

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (4)2.46 (4)3.298 (4)169 (3)
C7—H7C···O20.962.142.764 (5)122
Symmetry code: (i) −x+1, y−1/2, −z+3/2.
 

Acknowledgements

The authors acknowledge the use of the CCD facility at the Indian Institute of Science, Bangalore, set up under the IRHPA–DST programme.

References

First citationBruker (1998). SADABS. Bruker AXS Inc., Maddison, Wisconsin, USA.  Google Scholar
 First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationSalehi, H. & Guo, Q. X. (2004). Synth. Commun. 34, 4349–4357.  Web of Science CrossRef CAS 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o363
https://doi.org/10.1107/S1600536810001066
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