Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028188/om2126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028188/om2126Isup2.hkl |
CCDC reference: 655598
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.111
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C16 .. 2.92 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O7 .. C9 .. 2.97 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O8 .. C21 .. 3.01 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C4 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Goldmann & Stoltefuss (1991); Hofmann & Cimiraglia (1990); Ramusino & Varì (1999); Sun et al. (2006); Yiu & Knaus (1999).
The title compound was prepared from 2,6-dimethyl-4- (m-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid mono-methyl ester and 2-(2–2ydroxy-ethyl)-isoindole-1,3-dione in CH2Cl2. 2,6-Dimethyl-4- (m-nitro-phenyl)-1,4-dihydro-pyridine- 3,5-dicarboxylic acid mono-methyl ester (332 mg, 1 mmol) and 2-methyl-propan-1-ol (191 mg, 1 mmol) were dissolved in 20 ml CH2Cl2, dicyclohexylcarbodiimide (206 mg,1 mmol) and added to the solution at 278 K. The reaction mixture was stirred at 276–279 K for a further 5 h. The solvent was removed by vacuum evaporation. The product was purified by chromatography on silica gel column (eluted by ethyl acetate and petroleum ether, 1:4) at room temperature. The product (455 mg) was obtained in a yield of 90%. Suitable crystals were obtained by slow evaporation of a solution in ethyl acetate and petroleum ether (1:4).
All H atoms were positioned geometrically and refined using a riding model, with C—H 0.97 Å, and Uiso(H) = 1.2Ueq(C) except for the H atom on N1 which was located in a Fourier map and freely refined.
4-Aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters of the nefidipine type have become almost indispensable for the treatment of cardiovascular diseases since they first appeared on the market in 1975 (Yiu & Knaus, 1999; Goldmann & Stoltefuss, 1991). The compound, 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine- 3,5-dicarboxylic acid 3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl) -ethyl] ester 5-methyl ester, is a nefidipine analog. It can also be used as an intermediate for preparation of 2,6- dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-amino-ethyl) ester 5-methyl ester. Fig.1 shows the structure of the title compound. The dihydropyridine ring has a flattened boat conformation. This compares well with the structure of 3-(2-acetoxyethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylateand nefidipine (Sun et al., 2006; Hofmann & Cimiraglia, 1990; Ramusino & Varì, 1999). The atoms C4 and N1 are displaced from the mean planes formed by the other atoms in the same ring by 0.281 (1) Å and 0.125 (1) Å, respectively. The dihedral angle between the benzene ring and the C3/C2/C6/C5 plane is 88.02 (1)°.
For related literature, see: Goldmann & Stoltefuss (1991); Hofmann & Cimiraglia (1990); Ramusino & Varì (1999); Sun et al. (2006); Yiu & Knaus (1999).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. A view of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. |
C26H23N3O8 | Dx = 1.474 Mg m−3 |
Mr = 505.47 | Melting point = 243–244 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7713 (16) Å | Cell parameters from 2343 reflections |
b = 16.372 (3) Å | θ = 2.3–22.5° |
c = 17.945 (4) Å | µ = 0.11 mm−1 |
β = 95.43 (3)° | T = 293 K |
V = 2273.0 (8) Å3 | Block, yellow |
Z = 4 | 0.10 × 0.08 × 0.04 mm |
F(000) = 1056 |
Rigaku Saturn diffractometer | 4009 independent reflections |
Radiation source: rotating anode | 3635 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.035 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −17→19 |
Tmin = 0.989, Tmax = 0.996 | l = −16→21 |
13760 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.7911P] where P = (Fo2 + 2Fc2)/3 |
4009 reflections | (Δ/σ)max = 0.001 |
341 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C26H23N3O8 | V = 2273.0 (8) Å3 |
Mr = 505.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.7713 (16) Å | µ = 0.11 mm−1 |
b = 16.372 (3) Å | T = 293 K |
c = 17.945 (4) Å | 0.10 × 0.08 × 0.04 mm |
β = 95.43 (3)° |
Rigaku Saturn diffractometer | 4009 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 3635 reflections with I > 2σ(I) |
Tmin = 0.989, Tmax = 0.996 | Rint = 0.035 |
13760 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.20 e Å−3 |
4009 reflections | Δρmin = −0.23 e Å−3 |
341 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.49383 (17) | 0.38716 (8) | 0.52148 (7) | 0.0286 (3) | |
O2 | 0.21767 (16) | 0.34959 (8) | 0.49192 (7) | 0.0249 (3) | |
O3 | −0.22762 (16) | 0.13687 (9) | 0.55571 (8) | 0.0320 (3) | |
O4 | −0.15986 (17) | 0.02564 (8) | 0.61640 (8) | 0.0305 (3) | |
O5 | 0.01803 (15) | 0.14288 (7) | 0.32204 (7) | 0.0216 (3) | |
O6 | 0.19557 (14) | 0.08248 (7) | 0.24663 (7) | 0.0201 (3) | |
O7 | 0.48119 (16) | −0.02815 (8) | 0.13320 (7) | 0.0243 (3) | |
O8 | 0.06068 (15) | −0.14941 (8) | 0.25700 (8) | 0.0277 (3) | |
N1 | 0.61576 (19) | 0.19920 (9) | 0.36933 (8) | 0.0202 (3) | |
N2 | −0.12398 (18) | 0.08343 (9) | 0.57705 (8) | 0.0230 (3) | |
N3 | 0.23954 (17) | −0.07506 (9) | 0.18687 (8) | 0.0194 (3) | |
C1 | 0.7467 (2) | 0.31005 (11) | 0.44434 (10) | 0.0221 (4) | |
H1A | 0.7234 | 0.3671 | 0.4363 | 0.033* | |
H1B | 0.8402 | 0.2937 | 0.4163 | 0.033* | |
H1C | 0.7779 | 0.3004 | 0.4966 | 0.033* | |
C2 | 0.5881 (2) | 0.26132 (10) | 0.41896 (10) | 0.0186 (4) | |
C3 | 0.4268 (2) | 0.27317 (10) | 0.43928 (9) | 0.0182 (4) | |
C4 | 0.2811 (2) | 0.21423 (10) | 0.41495 (9) | 0.0180 (4) | |
H4 | 0.1758 | 0.2463 | 0.4024 | 0.022* | |
C5 | 0.3193 (2) | 0.16685 (10) | 0.34544 (9) | 0.0178 (4) | |
C6 | 0.4839 (2) | 0.15767 (10) | 0.32777 (10) | 0.0188 (4) | |
C7 | 0.5472 (2) | 0.10637 (11) | 0.26678 (10) | 0.0240 (4) | |
H7A | 0.5237 | 0.0499 | 0.2760 | 0.036* | |
H7B | 0.6694 | 0.1140 | 0.2658 | 0.036* | |
H7C | 0.4889 | 0.1223 | 0.2195 | 0.036* | |
C8 | 0.3901 (2) | 0.34176 (11) | 0.48782 (10) | 0.0200 (4) | |
C9 | 0.1646 (3) | 0.41683 (12) | 0.53670 (11) | 0.0307 (5) | |
H9A | 0.2016 | 0.4069 | 0.5885 | 0.046* | |
H9B | 0.0410 | 0.4217 | 0.5304 | 0.046* | |
H9C | 0.2159 | 0.4665 | 0.5210 | 0.046* | |
C10 | 0.2465 (2) | 0.15458 (10) | 0.47756 (9) | 0.0177 (4) | |
C11 | 0.0819 (2) | 0.14706 (10) | 0.50058 (10) | 0.0192 (4) | |
H11 | −0.0075 | 0.1803 | 0.4802 | 0.023* | |
C12 | 0.0524 (2) | 0.08944 (10) | 0.55433 (9) | 0.0190 (4) | |
C13 | 0.1800 (2) | 0.03819 (11) | 0.58675 (10) | 0.0214 (4) | |
H13 | 0.1560 | −0.0009 | 0.6219 | 0.026* | |
C14 | 0.3446 (2) | 0.04740 (11) | 0.56474 (10) | 0.0234 (4) | |
H14 | 0.4343 | 0.0150 | 0.5862 | 0.028* | |
C15 | 0.3767 (2) | 0.10468 (11) | 0.51081 (10) | 0.0214 (4) | |
H15 | 0.4882 | 0.1098 | 0.4965 | 0.026* | |
C16 | 0.1640 (2) | 0.13082 (10) | 0.30507 (9) | 0.0178 (4) | |
C17 | 0.0471 (2) | 0.03969 (11) | 0.21084 (10) | 0.0222 (4) | |
H17A | −0.0353 | 0.0782 | 0.1868 | 0.027* | |
H17B | −0.0098 | 0.0087 | 0.2475 | 0.027* | |
C18 | 0.1126 (2) | −0.01691 (11) | 0.15341 (10) | 0.0222 (4) | |
H18A | 0.0159 | −0.0466 | 0.1283 | 0.027* | |
H18B | 0.1647 | 0.0152 | 0.1161 | 0.027* | |
C19 | 0.4159 (2) | −0.07257 (10) | 0.17660 (10) | 0.0186 (4) | |
C20 | 0.4994 (2) | −0.13393 (10) | 0.22918 (9) | 0.0184 (4) | |
C21 | 0.6719 (2) | −0.15324 (11) | 0.24496 (10) | 0.0210 (4) | |
H21 | 0.7568 | −0.1284 | 0.2196 | 0.025* | |
C22 | 0.7138 (2) | −0.21128 (11) | 0.30038 (10) | 0.0233 (4) | |
H22 | 0.8288 | −0.2256 | 0.3125 | 0.028* | |
C23 | 0.5864 (2) | −0.24808 (11) | 0.33774 (10) | 0.0243 (4) | |
H23 | 0.6180 | −0.2868 | 0.3744 | 0.029* | |
C24 | 0.4130 (2) | −0.22880 (11) | 0.32195 (10) | 0.0221 (4) | |
H24 | 0.3279 | −0.2537 | 0.3471 | 0.027* | |
C25 | 0.3725 (2) | −0.17085 (10) | 0.26712 (10) | 0.0184 (4) | |
C26 | 0.2036 (2) | −0.13412 (11) | 0.23925 (10) | 0.0199 (4) | |
H1 | 0.724 (3) | 0.1938 (13) | 0.3578 (12) | 0.033 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0341 (7) | 0.0245 (7) | 0.0270 (7) | −0.0051 (6) | 0.0015 (6) | −0.0079 (6) |
O2 | 0.0263 (7) | 0.0240 (7) | 0.0240 (7) | 0.0073 (5) | −0.0005 (5) | −0.0078 (5) |
O3 | 0.0210 (7) | 0.0389 (8) | 0.0365 (8) | 0.0058 (6) | 0.0051 (6) | 0.0092 (6) |
O4 | 0.0312 (7) | 0.0294 (8) | 0.0316 (8) | −0.0078 (6) | 0.0074 (6) | 0.0046 (6) |
O5 | 0.0185 (6) | 0.0236 (7) | 0.0225 (7) | 0.0010 (5) | 0.0012 (5) | −0.0010 (5) |
O6 | 0.0184 (6) | 0.0217 (7) | 0.0198 (6) | −0.0013 (5) | −0.0012 (5) | −0.0047 (5) |
O7 | 0.0299 (7) | 0.0231 (7) | 0.0203 (7) | −0.0034 (5) | 0.0044 (5) | 0.0018 (5) |
O8 | 0.0160 (6) | 0.0292 (7) | 0.0385 (8) | −0.0026 (5) | 0.0060 (6) | −0.0016 (6) |
N1 | 0.0177 (8) | 0.0205 (8) | 0.0222 (8) | 0.0002 (6) | 0.0014 (6) | −0.0012 (6) |
N2 | 0.0218 (8) | 0.0253 (8) | 0.0220 (8) | −0.0035 (7) | 0.0028 (6) | −0.0005 (7) |
N3 | 0.0183 (7) | 0.0198 (8) | 0.0198 (8) | 0.0012 (6) | 0.0003 (6) | −0.0015 (6) |
C1 | 0.0204 (9) | 0.0210 (9) | 0.0242 (10) | −0.0019 (7) | −0.0010 (7) | 0.0017 (8) |
C2 | 0.0234 (9) | 0.0168 (9) | 0.0150 (8) | −0.0005 (7) | −0.0007 (7) | 0.0024 (7) |
C3 | 0.0227 (9) | 0.0167 (9) | 0.0147 (9) | 0.0000 (7) | −0.0009 (7) | 0.0016 (7) |
C4 | 0.0182 (8) | 0.0175 (9) | 0.0180 (9) | 0.0017 (7) | 0.0007 (7) | −0.0021 (7) |
C5 | 0.0202 (9) | 0.0152 (8) | 0.0175 (9) | −0.0002 (7) | −0.0008 (7) | −0.0003 (7) |
C6 | 0.0212 (9) | 0.0168 (9) | 0.0182 (9) | 0.0001 (7) | 0.0001 (7) | 0.0007 (7) |
C7 | 0.0209 (9) | 0.0276 (10) | 0.0238 (10) | −0.0013 (8) | 0.0034 (8) | −0.0063 (8) |
C8 | 0.0249 (9) | 0.0184 (9) | 0.0163 (9) | 0.0004 (7) | 0.0011 (7) | 0.0025 (7) |
C9 | 0.0371 (11) | 0.0297 (11) | 0.0249 (10) | 0.0143 (9) | 0.0012 (9) | −0.0087 (8) |
C10 | 0.0204 (9) | 0.0170 (9) | 0.0156 (9) | −0.0002 (7) | 0.0005 (7) | −0.0049 (7) |
C11 | 0.0201 (9) | 0.0185 (9) | 0.0188 (9) | 0.0015 (7) | 0.0004 (7) | −0.0037 (7) |
C12 | 0.0182 (8) | 0.0206 (9) | 0.0185 (9) | −0.0012 (7) | 0.0030 (7) | −0.0046 (7) |
C13 | 0.0263 (9) | 0.0184 (9) | 0.0200 (9) | 0.0019 (7) | 0.0043 (8) | 0.0007 (7) |
C14 | 0.0231 (9) | 0.0231 (10) | 0.0237 (10) | 0.0074 (7) | 0.0002 (8) | 0.0035 (8) |
C15 | 0.0187 (9) | 0.0241 (10) | 0.0216 (9) | 0.0016 (7) | 0.0021 (7) | −0.0007 (7) |
C16 | 0.0228 (9) | 0.0159 (9) | 0.0146 (9) | 0.0008 (7) | 0.0008 (7) | 0.0015 (7) |
C17 | 0.0176 (9) | 0.0226 (9) | 0.0251 (10) | 0.0016 (7) | −0.0046 (7) | −0.0036 (8) |
C18 | 0.0226 (9) | 0.0216 (9) | 0.0206 (9) | 0.0040 (7) | −0.0069 (7) | −0.0031 (7) |
C19 | 0.0208 (9) | 0.0186 (9) | 0.0165 (9) | −0.0027 (7) | 0.0017 (7) | −0.0044 (7) |
C20 | 0.0205 (9) | 0.0184 (9) | 0.0164 (9) | 0.0001 (7) | 0.0019 (7) | −0.0022 (7) |
C21 | 0.0190 (9) | 0.0226 (9) | 0.0217 (9) | −0.0016 (7) | 0.0034 (7) | −0.0020 (7) |
C22 | 0.0199 (9) | 0.0263 (10) | 0.0229 (10) | 0.0036 (7) | −0.0017 (7) | −0.0039 (8) |
C23 | 0.0318 (10) | 0.0204 (9) | 0.0200 (10) | 0.0048 (8) | −0.0013 (8) | 0.0004 (7) |
C24 | 0.0265 (9) | 0.0191 (9) | 0.0215 (9) | −0.0017 (7) | 0.0064 (8) | 0.0006 (7) |
C25 | 0.0189 (9) | 0.0168 (9) | 0.0197 (9) | −0.0013 (7) | 0.0036 (7) | −0.0034 (7) |
C26 | 0.0189 (9) | 0.0195 (9) | 0.0213 (9) | −0.0012 (7) | 0.0017 (7) | −0.0059 (7) |
O1—C8 | 1.215 (2) | C7—H7C | 0.9600 |
O2—C8 | 1.355 (2) | C9—H9A | 0.9600 |
O2—C9 | 1.446 (2) | C9—H9B | 0.9600 |
O3—N2 | 1.226 (2) | C9—H9C | 0.9600 |
O4—N2 | 1.228 (2) | C10—C11 | 1.387 (2) |
O5—C16 | 1.218 (2) | C10—C15 | 1.391 (2) |
O6—C16 | 1.355 (2) | C11—C12 | 1.384 (2) |
O6—C17 | 1.447 (2) | C11—H11 | 0.9300 |
O7—C19 | 1.211 (2) | C12—C13 | 1.385 (2) |
O8—C26 | 1.210 (2) | C13—C14 | 1.382 (3) |
N1—C2 | 1.382 (2) | C13—H13 | 0.9300 |
N1—C6 | 1.387 (2) | C14—C15 | 1.387 (3) |
N1—H1 | 0.89 (2) | C14—H14 | 0.9300 |
N2—C12 | 1.470 (2) | C15—H15 | 0.9300 |
N3—C26 | 1.395 (2) | C17—C18 | 1.510 (2) |
N3—C19 | 1.401 (2) | C17—H17A | 0.9700 |
N3—C18 | 1.459 (2) | C17—H17B | 0.9700 |
C1—C2 | 1.502 (2) | C18—H18A | 0.9700 |
C1—H1A | 0.9600 | C18—H18B | 0.9700 |
C1—H1B | 0.9600 | C19—C20 | 1.485 (2) |
C1—H1C | 0.9600 | C20—C21 | 1.380 (2) |
C2—C3 | 1.353 (2) | C20—C25 | 1.389 (2) |
C3—C8 | 1.466 (2) | C21—C22 | 1.392 (3) |
C3—C4 | 1.520 (2) | C21—H21 | 0.9300 |
C4—C5 | 1.522 (2) | C22—C23 | 1.385 (3) |
C4—C10 | 1.532 (2) | C22—H22 | 0.9300 |
C4—H4 | 0.9800 | C23—C24 | 1.387 (3) |
C5—C6 | 1.355 (2) | C23—H23 | 0.9300 |
C5—C16 | 1.471 (2) | C24—C25 | 1.382 (3) |
C6—C7 | 1.499 (2) | C24—H24 | 0.9300 |
C7—H7A | 0.9600 | C25—C26 | 1.487 (2) |
C7—H7B | 0.9600 | ||
C8—O2—C9 | 115.98 (14) | C12—C11—H11 | 120.4 |
C16—O6—C17 | 115.54 (13) | C10—C11—H11 | 120.4 |
C2—N1—C6 | 123.74 (15) | C11—C12—C13 | 123.15 (16) |
C2—N1—H1 | 115.5 (14) | C11—C12—N2 | 117.34 (15) |
C6—N1—H1 | 119.5 (14) | C13—C12—N2 | 119.51 (15) |
O3—N2—O4 | 123.44 (15) | C14—C13—C12 | 117.33 (16) |
O3—N2—C12 | 117.91 (14) | C14—C13—H13 | 121.3 |
O4—N2—C12 | 118.64 (15) | C12—C13—H13 | 121.3 |
C26—N3—C19 | 111.71 (14) | C13—C14—C15 | 120.40 (16) |
C26—N3—C18 | 123.98 (14) | C13—C14—H14 | 119.8 |
C19—N3—C18 | 123.96 (14) | C15—C14—H14 | 119.8 |
C2—C1—H1A | 109.5 | C14—C15—C10 | 121.64 (16) |
C2—C1—H1B | 109.5 | C14—C15—H15 | 119.2 |
H1A—C1—H1B | 109.5 | C10—C15—H15 | 119.2 |
C2—C1—H1C | 109.5 | O5—C16—O6 | 121.97 (15) |
H1A—C1—H1C | 109.5 | O5—C16—C5 | 123.50 (15) |
H1B—C1—H1C | 109.5 | O6—C16—C5 | 114.53 (14) |
C3—C2—N1 | 118.93 (16) | O6—C17—C18 | 107.07 (14) |
C3—C2—C1 | 126.66 (16) | O6—C17—H17A | 110.3 |
N1—C2—C1 | 114.41 (15) | C18—C17—H17A | 110.3 |
C2—C3—C8 | 120.51 (16) | O6—C17—H17B | 110.3 |
C2—C3—C4 | 121.06 (15) | C18—C17—H17B | 110.3 |
C8—C3—C4 | 118.39 (14) | H17A—C17—H17B | 108.6 |
C3—C4—C5 | 111.17 (14) | N3—C18—C17 | 112.23 (14) |
C3—C4—C10 | 111.82 (14) | N3—C18—H18A | 109.2 |
C5—C4—C10 | 109.73 (14) | C17—C18—H18A | 109.2 |
C3—C4—H4 | 108.0 | N3—C18—H18B | 109.2 |
C5—C4—H4 | 108.0 | C17—C18—H18B | 109.2 |
C10—C4—H4 | 108.0 | H18A—C18—H18B | 107.9 |
C6—C5—C16 | 126.09 (16) | O7—C19—N3 | 125.22 (16) |
C6—C5—C4 | 120.68 (15) | O7—C19—C20 | 129.07 (16) |
C16—C5—C4 | 113.16 (14) | N3—C19—C20 | 105.71 (14) |
C5—C6—N1 | 119.05 (16) | C21—C20—C25 | 121.37 (17) |
C5—C6—C7 | 127.96 (16) | C21—C20—C19 | 130.00 (16) |
N1—C6—C7 | 112.99 (15) | C25—C20—C19 | 108.56 (15) |
C6—C7—H7A | 109.5 | C20—C21—C22 | 117.36 (16) |
C6—C7—H7B | 109.5 | C20—C21—H21 | 121.3 |
H7A—C7—H7B | 109.5 | C22—C21—H21 | 121.3 |
C6—C7—H7C | 109.5 | C23—C22—C21 | 120.92 (17) |
H7A—C7—H7C | 109.5 | C23—C22—H22 | 119.5 |
H7B—C7—H7C | 109.5 | C21—C22—H22 | 119.5 |
O1—C8—O2 | 121.89 (16) | C22—C23—C24 | 121.82 (17) |
O1—C8—C3 | 127.38 (16) | C22—C23—H23 | 119.1 |
O2—C8—C3 | 110.73 (15) | C24—C23—H23 | 119.1 |
O2—C9—H9A | 109.5 | C25—C24—C23 | 116.93 (16) |
O2—C9—H9B | 109.5 | C25—C24—H24 | 121.5 |
H9A—C9—H9B | 109.5 | C23—C24—H24 | 121.5 |
O2—C9—H9C | 109.5 | C24—C25—C20 | 121.60 (16) |
H9A—C9—H9C | 109.5 | C24—C25—C26 | 130.64 (16) |
H9B—C9—H9C | 109.5 | C20—C25—C26 | 107.72 (15) |
C11—C10—C15 | 118.33 (16) | O8—C26—N3 | 124.62 (16) |
C11—C10—C4 | 120.40 (15) | O8—C26—C25 | 129.12 (17) |
C15—C10—C4 | 121.23 (15) | N3—C26—C25 | 106.26 (14) |
C12—C11—C10 | 119.11 (16) | ||
C6—N1—C2—C3 | 12.7 (3) | C13—C14—C15—C10 | 0.3 (3) |
C6—N1—C2—C1 | −166.72 (15) | C11—C10—C15—C14 | 1.2 (3) |
N1—C2—C3—C8 | −175.91 (15) | C4—C10—C15—C14 | −176.51 (16) |
C1—C2—C3—C8 | 3.5 (3) | C17—O6—C16—O5 | −6.1 (2) |
N1—C2—C3—C4 | 6.4 (2) | C17—O6—C16—C5 | 173.91 (14) |
C1—C2—C3—C4 | −174.24 (16) | C6—C5—C16—O5 | −177.82 (17) |
C2—C3—C4—C5 | −22.4 (2) | C4—C5—C16—O5 | 5.4 (2) |
C8—C3—C4—C5 | 159.82 (14) | C6—C5—C16—O6 | 2.1 (2) |
C2—C3—C4—C10 | 100.59 (18) | C4—C5—C16—O6 | −174.63 (14) |
C8—C3—C4—C10 | −77.15 (19) | C16—O6—C17—C18 | −174.08 (14) |
C3—C4—C5—C6 | 22.5 (2) | C26—N3—C18—C17 | 63.0 (2) |
C10—C4—C5—C6 | −101.67 (18) | C19—N3—C18—C17 | −109.65 (18) |
C3—C4—C5—C16 | −160.50 (14) | O6—C17—C18—N3 | 58.87 (19) |
C10—C4—C5—C16 | 75.28 (17) | C26—N3—C19—O7 | 178.32 (16) |
C16—C5—C6—N1 | 176.72 (15) | C18—N3—C19—O7 | −8.2 (3) |
C4—C5—C6—N1 | −6.7 (2) | C26—N3—C19—C20 | −1.94 (18) |
C16—C5—C6—C7 | −3.4 (3) | C18—N3—C19—C20 | 171.54 (15) |
C4—C5—C6—C7 | 173.12 (16) | O7—C19—C20—C21 | 3.7 (3) |
C2—N1—C6—C5 | −12.5 (3) | N3—C19—C20—C21 | −176.02 (17) |
C2—N1—C6—C7 | 167.58 (16) | O7—C19—C20—C25 | −179.33 (17) |
C9—O2—C8—O1 | 2.0 (2) | N3—C19—C20—C25 | 0.94 (18) |
C9—O2—C8—C3 | −178.35 (14) | C25—C20—C21—C22 | 0.1 (3) |
C2—C3—C8—O1 | −9.6 (3) | C19—C20—C21—C22 | 176.70 (17) |
C4—C3—C8—O1 | 168.13 (17) | C20—C21—C22—C23 | 0.2 (3) |
C2—C3—C8—O2 | 170.75 (15) | C21—C22—C23—C24 | −0.2 (3) |
C4—C3—C8—O2 | −11.5 (2) | C22—C23—C24—C25 | −0.1 (3) |
C3—C4—C10—C11 | 125.58 (17) | C23—C24—C25—C20 | 0.4 (3) |
C5—C4—C10—C11 | −110.58 (17) | C23—C24—C25—C26 | −177.07 (17) |
C3—C4—C10—C15 | −56.8 (2) | C21—C20—C25—C24 | −0.4 (3) |
C5—C4—C10—C15 | 67.1 (2) | C19—C20—C25—C24 | −177.65 (16) |
C15—C10—C11—C12 | −1.3 (2) | C21—C20—C25—C26 | 177.59 (16) |
C4—C10—C11—C12 | 176.42 (15) | C19—C20—C25—C26 | 0.32 (19) |
C10—C11—C12—C13 | 0.0 (3) | C19—N3—C26—O8 | −178.54 (16) |
C10—C11—C12—N2 | −179.92 (15) | C18—N3—C26—O8 | 8.0 (3) |
O3—N2—C12—C11 | −10.4 (2) | C19—N3—C26—C25 | 2.14 (18) |
O4—N2—C12—C11 | 169.81 (15) | C18—N3—C26—C25 | −171.34 (14) |
O3—N2—C12—C13 | 169.71 (16) | C24—C25—C26—O8 | −3.0 (3) |
O4—N2—C12—C13 | −10.1 (2) | C20—C25—C26—O8 | 179.25 (18) |
C11—C12—C13—C14 | 1.5 (3) | C24—C25—C26—N3 | 176.26 (17) |
N2—C12—C13—C14 | −178.62 (15) | C20—C25—C26—N3 | −1.47 (18) |
C12—C13—C14—C15 | −1.6 (3) |
Experimental details
Crystal data | |
Chemical formula | C26H23N3O8 |
Mr | 505.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.7713 (16), 16.372 (3), 17.945 (4) |
β (°) | 95.43 (3) |
V (Å3) | 2273.0 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.10 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.989, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13760, 4009, 3635 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.111, 1.10 |
No. of reflections | 4009 |
No. of parameters | 341 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.23 |
Computer programs: CrystalClear (Rigaku, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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4-Aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters of the nefidipine type have become almost indispensable for the treatment of cardiovascular diseases since they first appeared on the market in 1975 (Yiu & Knaus, 1999; Goldmann & Stoltefuss, 1991). The compound, 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine- 3,5-dicarboxylic acid 3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl) -ethyl] ester 5-methyl ester, is a nefidipine analog. It can also be used as an intermediate for preparation of 2,6- dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-amino-ethyl) ester 5-methyl ester. Fig.1 shows the structure of the title compound. The dihydropyridine ring has a flattened boat conformation. This compares well with the structure of 3-(2-acetoxyethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylateand nefidipine (Sun et al., 2006; Hofmann & Cimiraglia, 1990; Ramusino & Varì, 1999). The atoms C4 and N1 are displaced from the mean planes formed by the other atoms in the same ring by 0.281 (1) Å and 0.125 (1) Å, respectively. The dihedral angle between the benzene ring and the C3/C2/C6/C5 plane is 88.02 (1)°.