organic compounds
Dimethyl 1,4-dihydro-4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
*Correspondence e-mail: hkfun@usm.my
In the title compound, C18H21NO5, the dihydropyridine ring adopts a flattened-boat conformation and its planar part forms a dihedral angle of 84.60 (2)° with the benzene ring. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds result in the formation of zigzag layers parallel to (001). These layers are interconnected via C—H⋯π interactions.
Related literature
For the synthesis, see: Rathore et al. (2009). For general background and applications of 1,4-dihydropyridine derivatives, see: Bocker & Guengerich (1986); Cooper et al. (1992); Gaudio et al. (1994); Gordeev et al. (1996); Sunkel et al. (1992); Vo et al. (1995). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2009a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX DUO (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536810004940/ci5029sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810004940/ci5029Isup2.hkl
Dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-methoxyphenyl)-3,5-pyridine dicarboxylate was prepared according to the Hantzsch pyridine synthesis (Rathore et al., 2009). A mixture of 4-methoxybenzaldehyde (10.0 mmol), methylacetoacetate (20.0 mmol) and ammonium acetate (10.0 mmol) was heated at 353 K for 2 h (monitored by TLC). After the completion of the reaction, the mixture was cooled to room temperature and it was kept for 24 h to get a solid product. The solid formed was washed using diethyl ether. The washed solid was collected separately and the liquid kept for solidification. The purity of the crude product was checked through TLC and recrystallized using acetone and ether.
Atom H1N1 was located in a difference Fourier map and was refined freely [N–H = 0.854 (18) Å]. The remaining H atoms were positioned geometrically [C–H = 0.93–0.98 Å] and were refined using a riding model, with Uiso(H) = 1.2-1.5 Ueq(C). A rotating-group model was applied for the methyl groups. Reflection 010 was partially obscured by the beam stop and hence was omitted. In addition, the most disagreeable reflections 114, 414 amd 248 were also omitted during the refinement.
Data collection: APEX DUO (Bruker, 2009); cell
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 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. The crystal packing of the title compound, viewed approximately along the c axis, showing R12(6) ring motifs. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity. |
C18H21NO5 | Z = 2 |
Mr = 331.36 | F(000) = 352 |
Triclinic, P1 | Dx = 1.365 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4106 (3) Å | Cell parameters from 9874 reflections |
b = 9.5715 (5) Å | θ = 2.8–37.5° |
c = 11.7771 (6) Å | µ = 0.10 mm−1 |
α = 83.029 (1)° | T = 100 K |
β = 83.834 (1)° | Block, colourless |
γ = 77.424 (1)° | 0.35 × 0.34 × 0.24 mm |
V = 806.46 (7) Å3 |
Bruker SMART APEX DUO CCD area-detector diffractometer | 4664 independent reflections |
Radiation source: fine-focus sealed tube | 4319 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 30.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −10→10 |
Tmin = 0.966, Tmax = 0.976 | k = −13→13 |
19600 measured reflections | l = −15→16 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0628P)2 + 0.2437P] where P = (Fo2 + 2Fc2)/3 |
4664 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C18H21NO5 | γ = 77.424 (1)° |
Mr = 331.36 | V = 806.46 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4106 (3) Å | Mo Kα radiation |
b = 9.5715 (5) Å | µ = 0.10 mm−1 |
c = 11.7771 (6) Å | T = 100 K |
α = 83.029 (1)° | 0.35 × 0.34 × 0.24 mm |
β = 83.834 (1)° |
Bruker SMART APEX DUO CCD area-detector diffractometer | 4664 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4319 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.976 | Rint = 0.019 |
19600 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.48 e Å−3 |
4664 reflections | Δρmin = −0.22 e Å−3 |
226 parameters |
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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.19666 (9) | 0.64176 (7) | 0.02070 (6) | 0.01872 (14) | |
O2 | 0.45751 (9) | −0.03547 (8) | 0.19907 (6) | 0.02053 (15) | |
O3 | 0.76827 (9) | −0.08374 (7) | 0.16829 (6) | 0.01754 (14) | |
O4 | 0.13686 (9) | 0.26414 (7) | 0.49736 (6) | 0.01760 (14) | |
O5 | 0.29405 (9) | 0.35204 (8) | 0.61485 (6) | 0.01934 (14) | |
N1 | 0.78947 (10) | 0.17746 (8) | 0.42720 (6) | 0.01437 (14) | |
C1 | 0.22940 (12) | 0.30263 (9) | 0.19929 (7) | 0.01528 (16) | |
H1A | 0.1636 | 0.2291 | 0.2132 | 0.018* | |
C2 | 0.17064 (12) | 0.41859 (9) | 0.11955 (7) | 0.01588 (16) | |
H2A | 0.0667 | 0.4221 | 0.0806 | 0.019* | |
C3 | 0.26760 (11) | 0.52967 (9) | 0.09799 (7) | 0.01404 (16) | |
C4 | 0.42555 (12) | 0.52171 (9) | 0.15453 (8) | 0.01685 (17) | |
H4A | 0.4930 | 0.5942 | 0.1393 | 0.020* | |
C5 | 0.48191 (12) | 0.40434 (9) | 0.23414 (8) | 0.01621 (17) | |
H5A | 0.5875 | 0.3997 | 0.2718 | 0.019* | |
C6 | 0.38473 (11) | 0.29392 (9) | 0.25892 (7) | 0.01226 (15) | |
C7 | 0.44663 (11) | 0.16962 (9) | 0.34963 (7) | 0.01211 (15) | |
H7A | 0.3513 | 0.1114 | 0.3631 | 0.015* | |
C8 | 0.62773 (11) | 0.07428 (8) | 0.30836 (7) | 0.01266 (15) | |
C9 | 0.79129 (11) | 0.08547 (9) | 0.34450 (7) | 0.01310 (15) | |
C10 | 0.63106 (11) | 0.23953 (9) | 0.49133 (7) | 0.01351 (15) | |
C11 | 0.46306 (11) | 0.22785 (9) | 0.46145 (7) | 0.01275 (15) | |
C12 | 0.28140 (14) | 0.76387 (10) | 0.00644 (9) | 0.02215 (19) | |
H12A | 0.2151 | 0.8376 | −0.0455 | 0.033* | |
H12B | 0.4079 | 0.7363 | −0.0243 | 0.033* | |
H12C | 0.2782 | 0.7998 | 0.0794 | 0.033* | |
C13 | 0.60706 (12) | −0.01947 (9) | 0.22266 (7) | 0.01414 (16) | |
C14 | 0.74903 (14) | −0.16612 (11) | 0.07708 (9) | 0.02279 (19) | |
H14A | 0.8698 | −0.2091 | 0.0444 | 0.034* | |
H14B | 0.6814 | −0.1038 | 0.0188 | 0.034* | |
H14C | 0.6831 | −0.2403 | 0.1073 | 0.034* | |
C15 | 0.28484 (11) | 0.28084 (9) | 0.52454 (7) | 0.01380 (16) | |
C16 | 0.11938 (13) | 0.41561 (11) | 0.67270 (8) | 0.02036 (18) | |
H16A | 0.1416 | 0.4659 | 0.7338 | 0.031* | |
H16B | 0.0540 | 0.3414 | 0.7037 | 0.031* | |
H16C | 0.0462 | 0.4819 | 0.6191 | 0.031* | |
C17 | 0.98251 (11) | 0.00466 (9) | 0.30817 (8) | 0.01614 (16) | |
H17A | 0.9862 | −0.0969 | 0.3206 | 0.024* | |
H17B | 1.0712 | 0.0281 | 0.3526 | 0.024* | |
H17C | 1.0122 | 0.0312 | 0.2282 | 0.024* | |
C18 | 0.67039 (12) | 0.31346 (10) | 0.58865 (8) | 0.01716 (17) | |
H18A | 0.5985 | 0.4101 | 0.5848 | 0.026* | |
H18B | 0.8000 | 0.3156 | 0.5830 | 0.026* | |
H18C | 0.6379 | 0.2619 | 0.6604 | 0.026* | |
H1N1 | 0.895 (2) | 0.1892 (17) | 0.4467 (13) | 0.030 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0186 (3) | 0.0164 (3) | 0.0206 (3) | −0.0040 (2) | −0.0063 (2) | 0.0048 (2) |
O2 | 0.0147 (3) | 0.0233 (3) | 0.0262 (3) | −0.0051 (2) | −0.0037 (2) | −0.0088 (3) |
O3 | 0.0143 (3) | 0.0177 (3) | 0.0218 (3) | −0.0029 (2) | −0.0008 (2) | −0.0080 (2) |
O4 | 0.0111 (3) | 0.0237 (3) | 0.0187 (3) | −0.0042 (2) | −0.0016 (2) | −0.0036 (2) |
O5 | 0.0127 (3) | 0.0272 (3) | 0.0193 (3) | −0.0035 (2) | 0.0003 (2) | −0.0099 (3) |
N1 | 0.0095 (3) | 0.0180 (3) | 0.0168 (3) | −0.0037 (2) | −0.0026 (2) | −0.0036 (3) |
C1 | 0.0140 (4) | 0.0160 (4) | 0.0171 (4) | −0.0055 (3) | −0.0041 (3) | 0.0002 (3) |
C2 | 0.0139 (4) | 0.0177 (4) | 0.0168 (4) | −0.0039 (3) | −0.0055 (3) | 0.0001 (3) |
C3 | 0.0140 (3) | 0.0141 (3) | 0.0131 (3) | −0.0013 (3) | −0.0014 (3) | −0.0005 (3) |
C4 | 0.0166 (4) | 0.0161 (4) | 0.0192 (4) | −0.0068 (3) | −0.0043 (3) | 0.0015 (3) |
C5 | 0.0140 (4) | 0.0178 (4) | 0.0182 (4) | −0.0056 (3) | −0.0057 (3) | 0.0009 (3) |
C6 | 0.0111 (3) | 0.0132 (3) | 0.0125 (3) | −0.0021 (3) | −0.0014 (3) | −0.0017 (3) |
C7 | 0.0098 (3) | 0.0135 (3) | 0.0133 (3) | −0.0027 (3) | −0.0021 (3) | −0.0010 (3) |
C8 | 0.0117 (3) | 0.0119 (3) | 0.0144 (3) | −0.0025 (3) | −0.0016 (3) | −0.0010 (3) |
C9 | 0.0120 (3) | 0.0126 (3) | 0.0146 (3) | −0.0029 (3) | −0.0010 (3) | −0.0003 (3) |
C10 | 0.0124 (4) | 0.0148 (3) | 0.0134 (3) | −0.0028 (3) | −0.0021 (3) | −0.0006 (3) |
C11 | 0.0109 (3) | 0.0146 (3) | 0.0128 (3) | −0.0028 (3) | −0.0012 (3) | −0.0010 (3) |
C12 | 0.0258 (5) | 0.0168 (4) | 0.0238 (4) | −0.0066 (3) | −0.0043 (3) | 0.0043 (3) |
C13 | 0.0141 (4) | 0.0123 (3) | 0.0161 (4) | −0.0030 (3) | −0.0017 (3) | −0.0006 (3) |
C14 | 0.0205 (4) | 0.0232 (4) | 0.0270 (5) | −0.0042 (3) | −0.0016 (3) | −0.0131 (4) |
C15 | 0.0131 (3) | 0.0148 (3) | 0.0132 (3) | −0.0028 (3) | −0.0013 (3) | 0.0000 (3) |
C16 | 0.0149 (4) | 0.0243 (4) | 0.0218 (4) | −0.0022 (3) | 0.0021 (3) | −0.0087 (3) |
C17 | 0.0101 (3) | 0.0161 (4) | 0.0223 (4) | −0.0023 (3) | −0.0014 (3) | −0.0030 (3) |
C18 | 0.0132 (4) | 0.0221 (4) | 0.0178 (4) | −0.0038 (3) | −0.0037 (3) | −0.0059 (3) |
O1—C3 | 1.3697 (10) | C7—C8 | 1.5180 (11) |
O1—C12 | 1.4276 (11) | C7—H7A | 0.98 |
O2—C13 | 1.2163 (10) | C8—C9 | 1.3565 (11) |
O3—C13 | 1.3516 (10) | C8—C13 | 1.4698 (11) |
O3—C14 | 1.4433 (11) | C9—C17 | 1.5040 (11) |
O4—C15 | 1.2226 (10) | C10—C11 | 1.3603 (11) |
O5—C15 | 1.3461 (10) | C10—C18 | 1.5026 (11) |
O5—C16 | 1.4416 (11) | C11—C15 | 1.4637 (11) |
N1—C10 | 1.3843 (10) | C12—H12A | 0.96 |
N1—C9 | 1.3872 (11) | C12—H12B | 0.96 |
N1—H1N1 | 0.871 (16) | C12—H12C | 0.96 |
C1—C2 | 1.3885 (11) | C14—H14A | 0.96 |
C1—C6 | 1.3938 (11) | C14—H14B | 0.96 |
C1—H1A | 0.93 | C14—H14C | 0.96 |
C2—C3 | 1.3925 (12) | C16—H16A | 0.96 |
C2—H2A | 0.93 | C16—H16B | 0.96 |
C3—C4 | 1.3912 (12) | C16—H16C | 0.96 |
C4—C5 | 1.3928 (11) | C17—H17A | 0.96 |
C4—H4A | 0.93 | C17—H17B | 0.96 |
C5—C6 | 1.3901 (11) | C17—H17C | 0.96 |
C5—H5A | 0.93 | C18—H18A | 0.96 |
C6—C7 | 1.5252 (11) | C18—H18B | 0.96 |
C7—C11 | 1.5172 (11) | C18—H18C | 0.96 |
C3—O1—C12 | 116.97 (7) | C10—C11—C15 | 124.91 (8) |
C13—O3—C14 | 115.18 (7) | C10—C11—C7 | 120.70 (7) |
C15—O5—C16 | 116.31 (7) | C15—C11—C7 | 114.13 (7) |
C10—N1—C9 | 124.03 (7) | O1—C12—H12A | 109.5 |
C10—N1—H1N1 | 116.8 (10) | O1—C12—H12B | 109.5 |
C9—N1—H1N1 | 118.7 (10) | H12A—C12—H12B | 109.5 |
C2—C1—C6 | 121.53 (8) | O1—C12—H12C | 109.5 |
C2—C1—H1A | 119.2 | H12A—C12—H12C | 109.5 |
C6—C1—H1A | 119.2 | H12B—C12—H12C | 109.5 |
C1—C2—C3 | 119.85 (8) | O2—C13—O3 | 121.96 (8) |
C1—C2—H2A | 120.1 | O2—C13—C8 | 123.36 (8) |
C3—C2—H2A | 120.1 | O3—C13—C8 | 114.65 (7) |
O1—C3—C4 | 124.45 (8) | O3—C14—H14A | 109.5 |
O1—C3—C2 | 115.92 (7) | O3—C14—H14B | 109.5 |
C4—C3—C2 | 119.63 (8) | H14A—C14—H14B | 109.5 |
C3—C4—C5 | 119.49 (8) | O3—C14—H14C | 109.5 |
C3—C4—H4A | 120.3 | H14A—C14—H14C | 109.5 |
C5—C4—H4A | 120.3 | H14B—C14—H14C | 109.5 |
C6—C5—C4 | 121.82 (8) | O4—C15—O5 | 121.67 (8) |
C6—C5—H5A | 119.1 | O4—C15—C11 | 123.13 (8) |
C4—C5—H5A | 119.1 | O5—C15—C11 | 115.20 (7) |
C5—C6—C1 | 117.64 (7) | O5—C16—H16A | 109.5 |
C5—C6—C7 | 120.39 (7) | O5—C16—H16B | 109.5 |
C1—C6—C7 | 121.96 (7) | H16A—C16—H16B | 109.5 |
C11—C7—C8 | 111.44 (6) | O5—C16—H16C | 109.5 |
C11—C7—C6 | 109.82 (6) | H16A—C16—H16C | 109.5 |
C8—C7—C6 | 110.88 (6) | H16B—C16—H16C | 109.5 |
C11—C7—H7A | 108.2 | C9—C17—H17A | 109.5 |
C8—C7—H7A | 108.2 | C9—C17—H17B | 109.5 |
C6—C7—H7A | 108.2 | H17A—C17—H17B | 109.5 |
C9—C8—C13 | 125.21 (7) | C9—C17—H17C | 109.5 |
C9—C8—C7 | 120.89 (7) | H17A—C17—H17C | 109.5 |
C13—C8—C7 | 113.77 (7) | H17B—C17—H17C | 109.5 |
C8—C9—N1 | 118.88 (7) | C10—C18—H18A | 109.5 |
C8—C9—C17 | 127.61 (8) | C10—C18—H18B | 109.5 |
N1—C9—C17 | 113.47 (7) | H18A—C18—H18B | 109.5 |
C11—C10—N1 | 118.71 (7) | C10—C18—H18C | 109.5 |
C11—C10—C18 | 127.85 (8) | H18A—C18—H18C | 109.5 |
N1—C10—C18 | 113.43 (7) | H18B—C18—H18C | 109.5 |
C6—C1—C2—C3 | −0.14 (13) | C10—N1—C9—C8 | 12.37 (12) |
C12—O1—C3—C4 | −6.29 (13) | C10—N1—C9—C17 | −165.74 (7) |
C12—O1—C3—C2 | 173.39 (8) | C9—N1—C10—C11 | −10.00 (12) |
C1—C2—C3—O1 | −178.08 (8) | C9—N1—C10—C18 | 169.89 (7) |
C1—C2—C3—C4 | 1.62 (13) | N1—C10—C11—C15 | 176.50 (7) |
O1—C3—C4—C5 | 178.06 (8) | C18—C10—C11—C15 | −3.38 (14) |
C2—C3—C4—C5 | −1.60 (13) | N1—C10—C11—C7 | −9.74 (12) |
C3—C4—C5—C6 | 0.12 (14) | C18—C10—C11—C7 | 170.39 (8) |
C4—C5—C6—C1 | 1.32 (13) | C8—C7—C11—C10 | 24.10 (10) |
C4—C5—C6—C7 | −177.87 (8) | C6—C7—C11—C10 | −99.17 (9) |
C2—C1—C6—C5 | −1.31 (13) | C8—C7—C11—C15 | −161.50 (7) |
C2—C1—C6—C7 | 177.87 (8) | C6—C7—C11—C15 | 75.23 (8) |
C5—C6—C7—C11 | 53.55 (10) | C14—O3—C13—O2 | 2.95 (12) |
C1—C6—C7—C11 | −125.60 (8) | C14—O3—C13—C8 | −174.88 (7) |
C5—C6—C7—C8 | −70.05 (10) | C9—C8—C13—O2 | 173.87 (8) |
C1—C6—C7—C8 | 110.80 (9) | C7—C8—C13—O2 | −10.26 (12) |
C11—C7—C8—C9 | −21.76 (10) | C9—C8—C13—O3 | −8.34 (12) |
C6—C7—C8—C9 | 100.90 (9) | C7—C8—C13—O3 | 167.53 (7) |
C11—C7—C8—C13 | 162.17 (7) | C16—O5—C15—O4 | −4.05 (12) |
C6—C7—C8—C13 | −75.16 (8) | C16—O5—C15—C11 | 175.05 (7) |
C13—C8—C9—N1 | −179.23 (7) | C10—C11—C15—O4 | −177.44 (8) |
C7—C8—C9—N1 | 5.17 (12) | C7—C11—C15—O4 | 8.43 (11) |
C13—C8—C9—C17 | −1.42 (14) | C10—C11—C15—O5 | 3.48 (12) |
C7—C8—C9—C17 | −177.01 (8) | C7—C11—C15—O5 | −170.65 (7) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O4i | 0.87 (2) | 2.23 (2) | 3.0906 (10) | 169 (1) |
C14—H14A···O1ii | 0.96 | 2.54 | 3.4631 (13) | 162 |
C18—H18B···O4i | 0.96 | 2.56 | 3.4558 (12) | 156 |
C12—H12B···Cg1iii | 0.96 | 2.79 | 3.6549 (11) | 151 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H21NO5 |
Mr | 331.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.4106 (3), 9.5715 (5), 11.7771 (6) |
α, β, γ (°) | 83.029 (1), 83.834 (1), 77.424 (1) |
V (Å3) | 806.46 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.35 × 0.34 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.966, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19600, 4664, 4319 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.110, 1.05 |
No. of reflections | 4664 |
No. of parameters | 226 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.48, −0.22 |
Computer programs: APEX DUO (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O4i | 0.87 (2) | 2.23 (2) | 3.0906 (10) | 169 (1) |
C14—H14A···O1ii | 0.96 | 2.54 | 3.4631 (13) | 162 |
C18—H18B···O4i | 0.96 | 2.56 | 3.4558 (12) | 156 |
C12—H12B···Cg1iii | 0.96 | 2.79 | 3.6549 (11) | 151 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z; (iii) −x+1, −y+1, −z. |
Acknowledgements
HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).
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Hantzsch 1,4-dihydropyridines (1,4-DHPS) are biologically active compounds which include various vasodilator, antihypertensive, bronchodilator, heptaprotective, antitumor, antimutagenic, geroprotective and antidiabetic agents (Gaudio et al., 1994). Nifedipine, nitrendipine and nimodipine have been used commercially as calcium channel blockers (Bocker & Guengerich, 1986; Gordeev et al., 1996). For the treatment of congestive heart failure a number of DHP calcium antagonists have been introduced (Sunkel et al., 1992; Vo et al., 1995). Some DHPs have also been introduced as neuroprotectant and cognition enhancers. In addition, a number of DHPs with platelet anti-aggregatory activity have also been discovered (Cooper et al., 1992).
In the title compound (Fig. 1), the 1,4-dihydropyridine ring (C7–C11/N1) adopts a flattened-boat conformation with puckering parameter Q = 0.2368 (9) Å; Θ = 72.8 (2)° and ϕ = 186.1 (2)° (Cremer & Pople, 1975). The C8–C11 plane forms a dihedral angle of 84.60 (2)° with the C1–C6 benzene ring. Bond lengths (Allen et al., 1987) and angles are within the normal range and are comparable to those in closely related structures (Fun et al., 2009a,b).
In the crystal packing (Fig. 2), intermolecular N1—H1N1···O4 and C18—H18B···O4 hydrogen bonds (Table 1) link pairs of neighbouring molecules to form chains along the [100] direction; the chains contain R21(6) ring motifs (Bernstein et al., 1995). Intermolecular C14—H14A···O1 hydrogen bonds further interconnect these chains together to form zigzag layers parallel to the (001). The crystal structure is further stabilized by C—H···π interactions involving the C1–C6 benzene ring (centroid Cg1).