organic compounds
Methyl 4-(4-chlorophenyl)-8-iodo-2-methyl-6-oxo-1,6-dihydro-4H-pyrimido[2,1-b]quinazoline-3-carboxylate
aCenter for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3-20133 Milan, Italy, and bDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa
*Correspondence e-mail: nksusa@gmail.com, katharigattav@dut.ac.za
In the title compound, C20H15ClIN3O3, the dihedral angle between the quinazolinone ring system [r.m.s. deviation = 0.047 (2) Å] and the pendant benzene ring is 82.63 (11)°. The molecular conformation is stabilized by intramolecular C—H⋯O interactions. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds into chains along the a-axis direction. Another set of chains propagating along [101] is formed due to intermolecular I⋯Cl short contacts of 3.427 (1) Å, thus giving layers parallel to (010). The layers are connected by C—H⋯π and π–π interactions, the shortest distance between the centroids of aromatic rings being 3.8143 (16) Å.
Related literature
For crystal structures of dihydropyrimidines, see: Nayak et al. (2010, 2011a,b,c); Venugopala et al. (2012). For applications of dihydropyrimidines, see: Kappe (2000). For halogen-involving interactions, see: Nayak et al. (2011b).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).
Supporting information
https://doi.org/10.1107/S1600536812050787/yk2082sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050787/yk2082Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050787/yk2082Isup3.cml
A mixture of methyl-2-chloro-4-(4-chlorophenyl)-6-methyl-1,4- dihydropyrimidine-5-carboxylate (1 mmol), 2-amino-5-iodobenzoic acid (1 mmol) and methanamine (1 mmol) in 2-propanol (5 ml) was refluxed for 12 h. The reaction completion was monitored by TLC. The reaction medium was cooled to room temperature, the product was filtered, washed with cold 2-propanol and dried to obtain the crude product. The product was purified by recrystallization using ethanol in 66% yield as a brown solid (m. p. 467 (2) K). Crystals suitable for single-crystal X-ray study were obtained from methanol and tetrahydrofuran (1:1) solvent using slow evaporation at room temperature.
All H atoms were positioned geometrically with N—H = 0.88 Å, C—H = 0.95–1.00 Å and refined using a riding model with Uiso(H) = 1.2 Ueq(C/N) except for the methyl group where Uiso(H) = 1.5 Ueq(C).
In continuation of our work on the pharmacological properties and single-crystal X-ray studies (Nayak et al., 2010, 2011a,b,c; Venugopala et al., 2012) on dihydropyrimidine derivatives, we synthesized the title compound as a potential anti-malarial agent. Here we are reporting the single-crystal structure of the title compound.
The conformation of the title molecule is stabilized by intramolecular C—H···O interactions, and the dihedral angle between the planes of the 4-chlorophenyl and iodophenyl groups is 80.3 (2)° (Fig. 1). The θ1= 166.1 (2)°; θ2= 90.5 (2)°, symmetry code: x + 1, y, z + 1, Type II (Nayak et al., 2011b)] form infinite chains orthogonal to hydrogen bond chains which lead to two-dimensional molecular assembly (Fig. 2). Further, the C—H···π [2.67 Å,Cg1 = Centroid of six membered ring C7—C12; Table 1] and π–π [Cg2···Cg2 = 3.814 (2) Å, symmetry code: –X,1-Y,-Z; Cg2 = Centroid of six membered ring N2/C13/N3/C14/C19/C20] interactions enhance the stability of three-dimensional molecular assembly.
is stabilized by N—H···O infinite hydrogen bond chains parallel to [0 1 0]. Halogen-involving short contacts I···Cl [3.427 (2) Å,For crystal structures of dihydropyrimidines, see: Nayak et al. (2010, 2011a,b,c); Venugopala et al. (2012). For applications of dihydropyrimidines, see: Kappe (2000). For halogen-involving interactions, see: Nayak et al. (2011b).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).C20H15ClIN3O3 | Z = 2 |
Mr = 507.70 | F(000) = 500 |
Triclinic, P1 | Dx = 1.836 Mg m−3 |
Hall symbol: -P 1 | Melting point: 467(2) K |
a = 7.3443 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.847 (2) Å | Cell parameters from 560 reflections |
c = 12.475 (3) Å | θ = 2.9–26.0° |
α = 106.66 (3)° | µ = 1.92 mm−1 |
β = 103.53 (2)° | T = 173 K |
γ = 92.79 (3)° | Plate, yellow |
V = 918.5 (4) Å3 | 0.25 × 0.14 × 0.12 mm |
Bruker APEXII Kappa DUO CCD diffractometer | 3602 independent reflections |
Radiation source: fine-focus sealed tube | 3147 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
0.5° φ scans and ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −9→9 |
Tmin = 0.646, Tmax = 0.803 | k = −13→13 |
7109 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0285P)2 + 0.4298P] where P = (Fo2 + 2Fc2)/3 |
3602 reflections | (Δ/σ)max = 0.003 |
255 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C20H15ClIN3O3 | γ = 92.79 (3)° |
Mr = 507.70 | V = 918.5 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3443 (15) Å | Mo Kα radiation |
b = 10.847 (2) Å | µ = 1.92 mm−1 |
c = 12.475 (3) Å | T = 173 K |
α = 106.66 (3)° | 0.25 × 0.14 × 0.12 mm |
β = 103.53 (2)° |
Bruker APEXII Kappa DUO CCD diffractometer | 3602 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3147 reflections with I > 2σ(I) |
Tmin = 0.646, Tmax = 0.803 | Rint = 0.017 |
7109 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.89 e Å−3 |
3602 reflections | Δρmin = −0.52 e Å−3 |
255 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
I1 | 1.42667 (2) | 0.047532 (17) | 1.168961 (15) | 0.02807 (8) | |
Cl1 | 0.75652 (11) | −0.07966 (7) | 0.33638 (6) | 0.03791 (19) | |
O1 | 0.6050 (3) | 0.62853 (18) | 0.61509 (16) | 0.0272 (4) | |
O2 | 0.9047 (3) | 0.59136 (19) | 0.62752 (17) | 0.0287 (4) | |
O3 | 1.2104 (2) | 0.34709 (18) | 0.86038 (16) | 0.0250 (4) | |
N1 | 0.5905 (3) | 0.4115 (2) | 0.84598 (19) | 0.0238 (5) | |
H1 | 0.4842 | 0.3915 | 0.8617 | 0.029* | |
N2 | 0.9040 (3) | 0.3772 (2) | 0.85309 (17) | 0.0184 (4) | |
N3 | 0.7400 (3) | 0.3144 (2) | 0.97648 (19) | 0.0235 (5) | |
C1 | 0.6278 (4) | 0.7087 (3) | 0.5443 (3) | 0.0312 (7) | |
H1A | 0.7308 | 0.7789 | 0.5874 | 0.047* | |
H1B | 0.5104 | 0.7457 | 0.5232 | 0.047* | |
H1C | 0.6577 | 0.6562 | 0.4738 | 0.047* | |
C2 | 0.7579 (4) | 0.5753 (2) | 0.6529 (2) | 0.0205 (6) | |
C3 | 0.7317 (3) | 0.4945 (2) | 0.7260 (2) | 0.0185 (5) | |
C4 | 0.5854 (4) | 0.4883 (2) | 0.7733 (2) | 0.0208 (5) | |
C5 | 0.4109 (4) | 0.5552 (3) | 0.7604 (3) | 0.0270 (6) | |
H5A | 0.4379 | 0.6358 | 0.7432 | 0.041* | |
H5B | 0.3712 | 0.5751 | 0.8326 | 0.041* | |
H5C | 0.3097 | 0.4983 | 0.6969 | 0.041* | |
C6 | 0.8863 (3) | 0.4093 (2) | 0.7435 (2) | 0.0182 (5) | |
H6 | 1.0084 | 0.4588 | 0.7491 | 0.022* | |
C7 | 0.8535 (3) | 0.2847 (2) | 0.6416 (2) | 0.0180 (5) | |
C8 | 0.9062 (4) | 0.2870 (3) | 0.5422 (2) | 0.0230 (6) | |
H8 | 0.9657 | 0.3653 | 0.5392 | 0.028* | |
C9 | 0.8728 (4) | 0.1763 (3) | 0.4471 (2) | 0.0268 (6) | |
H9 | 0.9064 | 0.1790 | 0.3787 | 0.032* | |
C10 | 0.7903 (4) | 0.0623 (3) | 0.4531 (2) | 0.0261 (6) | |
C11 | 0.7360 (4) | 0.0575 (3) | 0.5507 (2) | 0.0270 (6) | |
H11 | 0.6781 | −0.0213 | 0.5536 | 0.032* | |
C12 | 0.7672 (4) | 0.1693 (3) | 0.6445 (2) | 0.0231 (6) | |
H12 | 0.7290 | 0.1669 | 0.7116 | 0.028* | |
C13 | 0.7476 (4) | 0.3651 (2) | 0.8947 (2) | 0.0192 (5) | |
C14 | 0.8986 (4) | 0.2618 (2) | 1.0197 (2) | 0.0212 (6) | |
C15 | 0.8893 (4) | 0.1949 (3) | 1.0998 (2) | 0.0262 (6) | |
H15 | 0.7788 | 0.1913 | 1.1265 | 0.031* | |
C16 | 1.0389 (4) | 0.1347 (3) | 1.1397 (2) | 0.0264 (6) | |
H16 | 1.0300 | 0.0875 | 1.1921 | 0.032* | |
C17 | 1.2046 (4) | 0.1424 (3) | 1.1035 (2) | 0.0233 (6) | |
C18 | 1.2198 (4) | 0.2091 (3) | 1.0265 (2) | 0.0227 (6) | |
H18 | 1.3325 | 0.2143 | 1.0022 | 0.027* | |
C19 | 1.0655 (4) | 0.2691 (2) | 0.9845 (2) | 0.0194 (5) | |
C20 | 1.0732 (4) | 0.3341 (2) | 0.8977 (2) | 0.0194 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02738 (11) | 0.03098 (12) | 0.02945 (11) | 0.00738 (8) | 0.00520 (8) | 0.01593 (8) |
Cl1 | 0.0363 (4) | 0.0311 (4) | 0.0339 (4) | 0.0142 (3) | −0.0019 (3) | −0.0018 (3) |
O1 | 0.0242 (10) | 0.0311 (11) | 0.0342 (11) | 0.0093 (8) | 0.0084 (9) | 0.0202 (9) |
O2 | 0.0265 (11) | 0.0315 (11) | 0.0400 (12) | 0.0078 (8) | 0.0166 (9) | 0.0220 (9) |
O3 | 0.0167 (9) | 0.0348 (11) | 0.0314 (10) | 0.0061 (8) | 0.0103 (8) | 0.0185 (9) |
N1 | 0.0154 (11) | 0.0320 (13) | 0.0320 (13) | 0.0073 (9) | 0.0111 (10) | 0.0173 (10) |
N2 | 0.0153 (11) | 0.0229 (12) | 0.0202 (11) | 0.0031 (9) | 0.0065 (9) | 0.0097 (9) |
N3 | 0.0213 (12) | 0.0289 (13) | 0.0247 (12) | 0.0064 (10) | 0.0095 (10) | 0.0115 (10) |
C1 | 0.0335 (16) | 0.0341 (17) | 0.0321 (16) | 0.0071 (13) | 0.0055 (13) | 0.0215 (13) |
C2 | 0.0221 (14) | 0.0174 (13) | 0.0205 (13) | 0.0040 (11) | 0.0037 (11) | 0.0044 (11) |
C3 | 0.0159 (13) | 0.0186 (13) | 0.0205 (13) | 0.0023 (10) | 0.0037 (10) | 0.0060 (11) |
C4 | 0.0209 (14) | 0.0191 (13) | 0.0231 (13) | 0.0042 (11) | 0.0047 (11) | 0.0080 (11) |
C5 | 0.0230 (14) | 0.0303 (15) | 0.0363 (16) | 0.0118 (12) | 0.0140 (13) | 0.0168 (13) |
C6 | 0.0167 (12) | 0.0228 (14) | 0.0194 (13) | 0.0034 (10) | 0.0069 (10) | 0.0113 (11) |
C7 | 0.0121 (12) | 0.0223 (14) | 0.0220 (13) | 0.0069 (10) | 0.0039 (10) | 0.0103 (11) |
C8 | 0.0208 (14) | 0.0261 (15) | 0.0264 (14) | 0.0047 (11) | 0.0102 (11) | 0.0113 (12) |
C9 | 0.0237 (14) | 0.0353 (17) | 0.0237 (14) | 0.0103 (13) | 0.0078 (12) | 0.0100 (12) |
C10 | 0.0210 (14) | 0.0263 (15) | 0.0251 (14) | 0.0107 (12) | −0.0004 (12) | 0.0027 (12) |
C11 | 0.0242 (15) | 0.0211 (15) | 0.0360 (16) | 0.0041 (12) | 0.0032 (12) | 0.0128 (13) |
C12 | 0.0227 (14) | 0.0247 (15) | 0.0254 (14) | 0.0046 (11) | 0.0077 (12) | 0.0113 (12) |
C13 | 0.0176 (13) | 0.0205 (13) | 0.0199 (13) | 0.0040 (10) | 0.0070 (11) | 0.0046 (11) |
C14 | 0.0221 (14) | 0.0218 (14) | 0.0198 (13) | 0.0045 (11) | 0.0056 (11) | 0.0058 (11) |
C15 | 0.0260 (15) | 0.0340 (16) | 0.0237 (14) | 0.0041 (12) | 0.0122 (12) | 0.0119 (12) |
C16 | 0.0308 (15) | 0.0312 (16) | 0.0217 (14) | 0.0047 (12) | 0.0079 (12) | 0.0141 (12) |
C17 | 0.0256 (14) | 0.0240 (14) | 0.0202 (13) | 0.0057 (11) | 0.0042 (11) | 0.0075 (11) |
C18 | 0.0223 (14) | 0.0247 (14) | 0.0220 (14) | 0.0044 (11) | 0.0066 (11) | 0.0079 (11) |
C19 | 0.0183 (13) | 0.0212 (13) | 0.0192 (13) | 0.0014 (11) | 0.0052 (10) | 0.0070 (11) |
C20 | 0.0187 (13) | 0.0193 (13) | 0.0190 (13) | 0.0023 (10) | 0.0029 (11) | 0.0058 (11) |
I1—C17 | 2.099 (3) | C5—H5C | 0.9800 |
Cl1—C10 | 1.750 (3) | C6—C7 | 1.530 (4) |
O1—C2 | 1.338 (3) | C6—H6 | 1.0000 |
O1—C1 | 1.436 (3) | C7—C12 | 1.389 (4) |
O2—C2 | 1.211 (3) | C7—C8 | 1.390 (3) |
O3—C20 | 1.223 (3) | C8—C9 | 1.389 (4) |
N1—C13 | 1.363 (3) | C8—H8 | 0.9500 |
N1—C4 | 1.392 (3) | C9—C10 | 1.379 (4) |
N1—H1 | 0.8800 | C9—H9 | 0.9500 |
N2—C13 | 1.382 (3) | C10—C11 | 1.380 (4) |
N2—C20 | 1.398 (3) | C11—C12 | 1.388 (4) |
N2—C6 | 1.483 (3) | C11—H11 | 0.9500 |
N3—C13 | 1.301 (3) | C12—H12 | 0.9500 |
N3—C14 | 1.386 (3) | C14—C19 | 1.401 (4) |
C1—H1A | 0.9800 | C14—C15 | 1.404 (4) |
C1—H1B | 0.9800 | C15—C16 | 1.372 (4) |
C1—H1C | 0.9800 | C15—H15 | 0.9500 |
C2—C3 | 1.469 (3) | C16—C17 | 1.401 (4) |
C3—C4 | 1.349 (3) | C16—H16 | 0.9500 |
C3—C6 | 1.515 (3) | C17—C18 | 1.379 (4) |
C4—C5 | 1.502 (4) | C18—C19 | 1.405 (4) |
C5—H5A | 0.9800 | C18—H18 | 0.9500 |
C5—H5B | 0.9800 | C19—C20 | 1.461 (3) |
C2—O1—C1 | 115.4 (2) | C9—C8—H8 | 119.6 |
C13—N1—C4 | 125.0 (2) | C7—C8—H8 | 119.6 |
C13—N1—H1 | 117.5 | C10—C9—C8 | 119.3 (3) |
C4—N1—H1 | 117.5 | C10—C9—H9 | 120.4 |
C13—N2—C20 | 121.4 (2) | C8—C9—H9 | 120.4 |
C13—N2—C6 | 120.6 (2) | C9—C10—C11 | 121.1 (3) |
C20—N2—C6 | 116.72 (19) | C9—C10—Cl1 | 119.8 (2) |
C13—N3—C14 | 116.7 (2) | C11—C10—Cl1 | 119.1 (2) |
O1—C1—H1A | 109.5 | C10—C11—C12 | 119.1 (3) |
O1—C1—H1B | 109.5 | C10—C11—H11 | 120.4 |
H1A—C1—H1B | 109.5 | C12—C11—H11 | 120.4 |
O1—C1—H1C | 109.5 | C11—C12—C7 | 120.9 (2) |
H1A—C1—H1C | 109.5 | C11—C12—H12 | 119.5 |
H1B—C1—H1C | 109.5 | C7—C12—H12 | 119.5 |
O2—C2—O1 | 122.5 (2) | N3—C13—N1 | 118.2 (2) |
O2—C2—C3 | 123.1 (2) | N3—C13—N2 | 125.2 (2) |
O1—C2—C3 | 114.4 (2) | N1—C13—N2 | 116.6 (2) |
C4—C3—C2 | 126.5 (2) | N3—C14—C19 | 122.9 (2) |
C4—C3—C6 | 119.8 (2) | N3—C14—C15 | 118.4 (2) |
C2—C3—C6 | 113.7 (2) | C19—C14—C15 | 118.7 (2) |
C3—C4—N1 | 118.3 (2) | C16—C15—C14 | 120.4 (2) |
C3—C4—C5 | 129.1 (2) | C16—C15—H15 | 119.8 |
N1—C4—C5 | 112.6 (2) | C14—C15—H15 | 119.8 |
C4—C5—H5A | 109.5 | C15—C16—C17 | 120.3 (2) |
C4—C5—H5B | 109.5 | C15—C16—H16 | 119.8 |
H5A—C5—H5B | 109.5 | C17—C16—H16 | 119.8 |
C4—C5—H5C | 109.5 | C18—C17—C16 | 120.8 (2) |
H5A—C5—H5C | 109.5 | C18—C17—I1 | 121.37 (19) |
H5B—C5—H5C | 109.5 | C16—C17—I1 | 117.80 (19) |
N2—C6—C3 | 111.06 (19) | C17—C18—C19 | 118.7 (2) |
N2—C6—C7 | 110.0 (2) | C17—C18—H18 | 120.6 |
C3—C6—C7 | 111.7 (2) | C19—C18—H18 | 120.6 |
N2—C6—H6 | 108.0 | C14—C19—C18 | 121.0 (2) |
C3—C6—H6 | 108.0 | C14—C19—C20 | 118.9 (2) |
C7—C6—H6 | 108.0 | C18—C19—C20 | 120.0 (2) |
C12—C7—C8 | 118.8 (2) | O3—C20—N2 | 120.3 (2) |
C12—C7—C6 | 121.6 (2) | O3—C20—C19 | 125.0 (2) |
C8—C7—C6 | 119.6 (2) | N2—C20—C19 | 114.7 (2) |
C9—C8—C7 | 120.7 (3) | ||
C1—O1—C2—O2 | −1.3 (4) | C6—C7—C12—C11 | 179.1 (2) |
C1—O1—C2—C3 | 179.5 (2) | C14—N3—C13—N1 | 176.6 (2) |
O2—C2—C3—C4 | 168.5 (3) | C14—N3—C13—N2 | −4.1 (4) |
O1—C2—C3—C4 | −12.4 (4) | C4—N1—C13—N3 | 168.0 (2) |
O2—C2—C3—C6 | −13.4 (4) | C4—N1—C13—N2 | −11.4 (4) |
O1—C2—C3—C6 | 165.8 (2) | C20—N2—C13—N3 | 0.0 (4) |
C2—C3—C4—N1 | −176.2 (2) | C6—N2—C13—N3 | 166.5 (2) |
C6—C3—C4—N1 | 5.7 (4) | C20—N2—C13—N1 | 179.3 (2) |
C2—C3—C4—C5 | 3.0 (5) | C6—N2—C13—N1 | −14.2 (3) |
C6—C3—C4—C5 | −175.0 (3) | C13—N3—C14—C19 | 4.3 (4) |
C13—N1—C4—C3 | 15.7 (4) | C13—N3—C14—C15 | −173.8 (2) |
C13—N1—C4—C5 | −163.7 (2) | N3—C14—C15—C16 | 176.1 (3) |
C13—N2—C6—C3 | 31.8 (3) | C19—C14—C15—C16 | −2.0 (4) |
C20—N2—C6—C3 | −161.1 (2) | C14—C15—C16—C17 | 1.8 (4) |
C13—N2—C6—C7 | −92.5 (3) | C15—C16—C17—C18 | −0.7 (4) |
C20—N2—C6—C7 | 74.6 (3) | C15—C16—C17—I1 | 179.9 (2) |
C4—C3—C6—N2 | −27.2 (3) | C16—C17—C18—C19 | −0.1 (4) |
C2—C3—C6—N2 | 154.5 (2) | I1—C17—C18—C19 | 179.16 (19) |
C4—C3—C6—C7 | 96.0 (3) | N3—C14—C19—C18 | −176.9 (2) |
C2—C3—C6—C7 | −82.2 (3) | C15—C14—C19—C18 | 1.1 (4) |
N2—C6—C7—C12 | 27.4 (3) | N3—C14—C19—C20 | −0.5 (4) |
C3—C6—C7—C12 | −96.5 (3) | C15—C14—C19—C20 | 177.5 (2) |
N2—C6—C7—C8 | −154.5 (2) | C17—C18—C19—C14 | −0.1 (4) |
C3—C6—C7—C8 | 81.7 (3) | C17—C18—C19—C20 | −176.4 (2) |
C12—C7—C8—C9 | 0.2 (4) | C13—N2—C20—O3 | −179.2 (2) |
C6—C7—C8—C9 | −178.0 (2) | C6—N2—C20—O3 | 13.8 (3) |
C7—C8—C9—C10 | −1.5 (4) | C13—N2—C20—C19 | 3.8 (3) |
C8—C9—C10—C11 | 1.7 (4) | C6—N2—C20—C19 | −163.2 (2) |
C8—C9—C10—Cl1 | −177.3 (2) | C14—C19—C20—O3 | 179.8 (3) |
C9—C10—C11—C12 | −0.6 (4) | C18—C19—C20—O3 | −3.8 (4) |
Cl1—C10—C11—C12 | 178.3 (2) | C14—C19—C20—N2 | −3.4 (3) |
C10—C11—C12—C7 | −0.7 (4) | C18—C19—C20—N2 | 173.0 (2) |
C8—C7—C12—C11 | 0.9 (4) |
Cg1 is the centroid of the C7–C12 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.88 | 2.04 | 2.903 (3) | 167 |
C5—H5A···O1 | 0.98 | 2.22 | 2.807 (4) | 117 |
C8—H8···O2 | 0.95 | 2.49 | 3.167 (4) | 128 |
C1—H1B···Cg1ii | 0.98 | 2.67 | 3.647 (4) | 175 |
Symmetry codes: (i) x−1, y, z; (ii) −x−1, −y−1, −z−1. |
Experimental details
Crystal data | |
Chemical formula | C20H15ClIN3O3 |
Mr | 507.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 7.3443 (15), 10.847 (2), 12.475 (3) |
α, β, γ (°) | 106.66 (3), 103.53 (2), 92.79 (3) |
V (Å3) | 918.5 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.92 |
Crystal size (mm) | 0.25 × 0.14 × 0.12 |
Data collection | |
Diffractometer | Bruker APEXII Kappa DUO CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.646, 0.803 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7109, 3602, 3147 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.059, 1.09 |
No. of reflections | 3602 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.89, −0.52 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and PARST (Nardelli, 1995).
Cg1 is the centroid of the C7–C12 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.88 | 2.04 | 2.903 (3) | 167 |
C5—H5A···O1 | 0.98 | 2.22 | 2.807 (4) | 117 |
C8—H8···O2 | 0.95 | 2.49 | 3.167 (4) | 128 |
C1—H1B···Cg1ii | 0.98 | 2.67 | 3.647 (4) | 175 |
Symmetry codes: (i) x−1, y, z; (ii) −x−1, −y−1, −z−1. |
Acknowledgements
The authors thank Durban University of Technology for facilities. KNV thanks the NRF South Africa for a DST/NRF Innovation Postdoctoral Fellowship.
References
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043–1052. Web of Science CrossRef PubMed CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011b). Cryst. Growth Des. 11, 1578–1596. Web of Science CSD CrossRef CAS Google Scholar
Nayak, S. K., Venugopala, K. N., Chopra, D. & Guru Row, T. N. (2011a). CrystEngComm, 13, 591–605. Web of Science CSD CrossRef CAS Google Scholar
Nayak, S. K., Venugopala, K. N., Chopra, D., Vasu & Guru Row, T. N. (2010). CrystEngComm, 12, 1205–1216. Google Scholar
Nayak, S. K., Venugopala, K. N., Govender, T., Kruger, H. G., Maguire, G. E. M. & Row, T. N. G. (2011c). Acta Cryst. E67, o3069–o3070. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Venugopala, K. N., Nayak, S. K. & Odhav, B. (2012). Acta Cryst. E68, o2977–o2978. CSD 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.
In continuation of our work on the pharmacological properties and single-crystal X-ray studies (Nayak et al., 2010, 2011a,b,c; Venugopala et al., 2012) on dihydropyrimidine derivatives, we synthesized the title compound as a potential anti-malarial agent. Here we are reporting the single-crystal structure of the title compound.
The conformation of the title molecule is stabilized by intramolecular C—H···O interactions, and the dihedral angle between the planes of the 4-chlorophenyl and iodophenyl groups is 80.3 (2)° (Fig. 1). The crystal structure is stabilized by N—H···O infinite hydrogen bond chains parallel to [0 1 0]. Halogen-involving short contacts I···Cl [3.427 (2) Å, θ1= 166.1 (2)°; θ2= 90.5 (2)°, symmetry code: x + 1, y, z + 1, Type II (Nayak et al., 2011b)] form infinite chains orthogonal to hydrogen bond chains which lead to two-dimensional molecular assembly (Fig. 2). Further, the C—H···π [2.67 Å,Cg1 = Centroid of six membered ring C7—C12; Table 1] and π–π [Cg2···Cg2 = 3.814 (2) Å, symmetry code: –X,1-Y,-Z; Cg2 = Centroid of six membered ring N2/C13/N3/C14/C19/C20] interactions enhance the stability of three-dimensional molecular assembly.