Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032515/ez2085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032515/ez2085Isup2.hkl |
CCDC reference: 659073
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.138
- Data-to-parameter ratio = 17.3
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 ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT731_ALERT_1_C Bond Calc 0.89(2), Rep 0.888(9) ...... 2.22 su-Ra N1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(2), Rep 0.888(9) ...... 2.22 su-Ra N1 -H1 1.555 1.555
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 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: Cotta-Ramusino & Varì (1999); Goldmann & Stoltefuss (1991); Hofmann & Cimiraglia (1990); Sun et al. (2006); Yiu & Knaus (1999).
The title compound was prepared by dissolving 2,6-dimethyl-4-(m-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid mono-methyl ester (332 mg, 1 mmol) and 2-methoxy-ethanol (76 mg, 1 mmol) in 10 ml CH2Cl2. Dicyclohexyl-carbodiimide (206 mg, 1 mmol) was added dropwise to the solution at 278 K. The reaction mixture was stirred at 276–279 K for a further 6 h. The solvent was removed by vacuum evaporation. The desired product was purified by chromatography on a silica gel column (eluted by ethyl acetate and petroleum, 1:6) at room temperature. The product (350 mg) was obtained in a yield of 90%. Suitable crystals were obtained by slow evaporation of a solution in ethyl acetate and petroleum (1:6).
The H atom bonded to N1 was located in a difference map and its positional parameters were refined freely [Uiso(H) = 1.2Ueq(N)]. All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.97 A ° and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C).
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 title compound, (I), is a nefidipine analog. The molecular structure of (I) is shown in Fig. 1. The dihydropyridine rings display an envelope conformation, with atom C4 displaced from the mean planes formed by the other atoms in the same ring by 0.170 (1) A°. The dihedral angle between the benzene ring and the N1/C2/C3/C5/C6 plane is 85.50 (0)°. This is similar to the situation found in nefidipine (Hofmann & Cimiraglia, 1990; Cotta-Ramusino & Varì, 1999) and the structure of 3-(2-acetoxyethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylate (Sun et al., 2006).
For related literature, see: Cotta-Ramusino & Varì (1999); Goldmann & Stoltefuss (1991); Hofmann & Cimiraglia (1990); Sun et al. (2006); Yiu & Knaus (1999).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. A view of the title compound (I) showing atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C19H22N2O7 | Dx = 1.365 Mg m−3 |
Mr = 390.39 | Melting point = 413–414 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.575 (3) Å | Cell parameters from 2365 reflections |
b = 9.909 (2) Å | θ = 2.5–33.6° |
c = 14.522 (3) Å | µ = 0.11 mm−1 |
β = 115.11 (3)° | T = 293 K |
V = 1899.1 (7) Å3 | Block, yellow |
Z = 4 | 0.10 × 0.08 × 0.06 mm |
F(000) = 824 |
Bruker P4 diffractometer | 4505 independent reflections |
Radiation source: fine-focus sealed tube | 3156 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 27.9°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick 1996) | h = −19→15 |
Tmin = 0.990, Tmax = 0.994 | k = −13→13 |
14339 measured reflections | l = −15→19 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0636P)2 + 0.0976P] where P = (Fo2 + 2Fc2)/3 |
4505 reflections | (Δ/σ)max = 0.001 |
261 parameters | Δρmax = 0.30 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C19H22N2O7 | V = 1899.1 (7) Å3 |
Mr = 390.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.575 (3) Å | µ = 0.11 mm−1 |
b = 9.909 (2) Å | T = 293 K |
c = 14.522 (3) Å | 0.10 × 0.08 × 0.06 mm |
β = 115.11 (3)° |
Bruker P4 diffractometer | 4505 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick 1996) | 3156 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.994 | Rint = 0.055 |
14339 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 1 restraint |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.30 e Å−3 |
4505 reflections | Δρmin = −0.23 e Å−3 |
261 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 | 0.60094 (10) | 0.61768 (13) | 1.13994 (9) | 0.0270 (3) | |
O2 | 0.49017 (10) | 0.70189 (13) | 1.19424 (9) | 0.0269 (3) | |
O3 | 0.24981 (11) | 1.05799 (13) | 1.00474 (10) | 0.0335 (4) | |
O4 | 0.20420 (10) | 1.08548 (14) | 0.83810 (10) | 0.0310 (3) | |
O5 | 0.12560 (11) | 1.32144 (15) | 0.70977 (11) | 0.0383 (4) | |
O6 | 0.14553 (13) | 0.79275 (18) | 1.19824 (13) | 0.0520 (5) | |
O7 | 0.04605 (11) | 0.62697 (15) | 1.12708 (12) | 0.0414 (4) | |
N1 | 0.45194 (12) | 0.83737 (15) | 0.86965 (11) | 0.0229 (3) | |
N2 | 0.11639 (12) | 0.70158 (17) | 1.13617 (12) | 0.0286 (4) | |
C1 | 0.58383 (15) | 0.67373 (19) | 0.94922 (14) | 0.0260 (4) | |
H1A | 0.6474 | 0.6993 | 1.0033 | 0.039* | |
H1B | 0.5866 | 0.6874 | 0.8850 | 0.039* | |
H1C | 0.5707 | 0.5803 | 0.9564 | 0.039* | |
C2 | 0.50064 (13) | 0.75855 (17) | 0.95394 (13) | 0.0197 (4) | |
C3 | 0.47090 (13) | 0.76349 (17) | 1.03097 (13) | 0.0192 (4) | |
C4 | 0.37869 (13) | 0.84412 (17) | 1.02140 (13) | 0.0194 (4) | |
H4 | 0.3980 | 0.8990 | 1.0829 | 0.023* | |
C5 | 0.34163 (14) | 0.93896 (17) | 0.93035 (13) | 0.0203 (4) | |
C6 | 0.37773 (13) | 0.93152 (17) | 0.85898 (13) | 0.0204 (4) | |
C7 | 0.35141 (16) | 1.01866 (19) | 0.76676 (13) | 0.0276 (4) | |
H7A | 0.3090 | 1.0918 | 0.7686 | 0.041* | |
H7B | 0.3159 | 0.9658 | 0.7066 | 0.041* | |
H7C | 0.4124 | 1.0541 | 0.7660 | 0.041* | |
C8 | 0.51996 (13) | 0.69282 (17) | 1.12730 (13) | 0.0199 (4) | |
C9 | 0.64973 (16) | 0.5507 (2) | 1.23687 (14) | 0.0329 (5) | |
H9A | 0.6656 | 0.6156 | 1.2905 | 0.049* | |
H9B | 0.7110 | 0.5085 | 1.2420 | 0.049* | |
H9C | 0.6051 | 0.4834 | 1.2426 | 0.049* | |
C10 | 0.29293 (13) | 0.75040 (17) | 1.01454 (12) | 0.0189 (4) | |
C11 | 0.26034 (14) | 0.64731 (18) | 0.94289 (14) | 0.0241 (4) | |
H11 | 0.2917 | 0.6357 | 0.8995 | 0.029* | |
C12 | 0.18251 (14) | 0.56185 (19) | 0.93470 (15) | 0.0281 (4) | |
H12 | 0.1619 | 0.4938 | 0.8860 | 0.034* | |
C13 | 0.13505 (14) | 0.57720 (19) | 0.99865 (14) | 0.0256 (4) | |
H13 | 0.0833 | 0.5193 | 0.9947 | 0.031* | |
C14 | 0.16678 (13) | 0.68103 (17) | 1.06860 (13) | 0.0209 (4) | |
C15 | 0.24447 (14) | 0.76776 (17) | 1.07778 (13) | 0.0213 (4) | |
H15 | 0.2639 | 0.8368 | 1.1257 | 0.026* | |
C16 | 0.26331 (14) | 1.03323 (17) | 0.92952 (13) | 0.0231 (4) | |
C17 | 0.12072 (16) | 1.1692 (2) | 0.83370 (16) | 0.0344 (5) | |
H17A | 0.1461 | 1.2441 | 0.8808 | 0.041* | |
H17B | 0.0748 | 1.1168 | 0.8521 | 0.041* | |
C18 | 0.06682 (15) | 1.2205 (2) | 0.72745 (16) | 0.0322 (5) | |
H18A | 0.0553 | 1.1469 | 0.6798 | 0.039* | |
H18B | 0.0015 | 1.2573 | 0.7173 | 0.039* | |
C19 | 0.08013 (19) | 1.3655 (3) | 0.60699 (18) | 0.0504 (6) | |
H19A | 0.0761 | 1.2913 | 0.5630 | 0.076* | |
H19B | 0.1203 | 1.4363 | 0.5976 | 0.076* | |
H19C | 0.0132 | 1.3988 | 0.5910 | 0.076* | |
H1 | 0.4693 (16) | 0.831 (2) | 0.8182 (12) | 0.037 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0301 (7) | 0.0354 (7) | 0.0173 (6) | 0.0075 (6) | 0.0117 (6) | 0.0043 (5) |
O2 | 0.0290 (8) | 0.0382 (8) | 0.0180 (6) | −0.0013 (6) | 0.0145 (6) | 0.0023 (6) |
O3 | 0.0477 (9) | 0.0309 (7) | 0.0308 (8) | 0.0091 (6) | 0.0253 (7) | 0.0010 (6) |
O4 | 0.0328 (8) | 0.0357 (8) | 0.0289 (7) | 0.0114 (6) | 0.0173 (6) | 0.0050 (6) |
O5 | 0.0365 (9) | 0.0461 (9) | 0.0307 (8) | −0.0077 (7) | 0.0127 (7) | 0.0093 (7) |
O6 | 0.0572 (11) | 0.0653 (11) | 0.0551 (10) | −0.0319 (9) | 0.0446 (9) | −0.0335 (9) |
O7 | 0.0369 (9) | 0.0500 (9) | 0.0501 (10) | −0.0192 (7) | 0.0310 (8) | −0.0092 (7) |
N1 | 0.0303 (9) | 0.0276 (8) | 0.0172 (8) | 0.0016 (7) | 0.0163 (7) | 0.0019 (6) |
N2 | 0.0255 (9) | 0.0358 (9) | 0.0289 (9) | −0.0054 (7) | 0.0158 (8) | −0.0021 (7) |
C1 | 0.0294 (10) | 0.0331 (10) | 0.0215 (9) | 0.0004 (8) | 0.0165 (8) | 0.0011 (8) |
C2 | 0.0220 (9) | 0.0228 (9) | 0.0165 (8) | −0.0032 (7) | 0.0103 (8) | −0.0015 (7) |
C3 | 0.0234 (10) | 0.0216 (9) | 0.0161 (8) | −0.0031 (7) | 0.0116 (7) | −0.0011 (7) |
C4 | 0.0248 (10) | 0.0215 (9) | 0.0156 (8) | −0.0037 (7) | 0.0122 (8) | −0.0028 (7) |
C5 | 0.0245 (10) | 0.0209 (8) | 0.0186 (9) | −0.0032 (7) | 0.0123 (8) | −0.0016 (7) |
C6 | 0.0244 (10) | 0.0206 (9) | 0.0185 (9) | −0.0043 (7) | 0.0115 (8) | −0.0016 (7) |
C7 | 0.0361 (11) | 0.0282 (10) | 0.0225 (9) | −0.0014 (8) | 0.0165 (9) | 0.0017 (8) |
C8 | 0.0224 (9) | 0.0229 (9) | 0.0162 (8) | −0.0056 (7) | 0.0099 (8) | −0.0024 (7) |
C9 | 0.0338 (11) | 0.0441 (12) | 0.0204 (10) | 0.0068 (9) | 0.0112 (9) | 0.0092 (8) |
C10 | 0.0206 (9) | 0.0215 (8) | 0.0155 (8) | 0.0005 (7) | 0.0085 (7) | 0.0014 (7) |
C11 | 0.0261 (10) | 0.0274 (10) | 0.0225 (9) | −0.0015 (8) | 0.0138 (8) | −0.0048 (7) |
C12 | 0.0278 (11) | 0.0255 (10) | 0.0302 (10) | −0.0056 (8) | 0.0117 (9) | −0.0087 (8) |
C13 | 0.0214 (10) | 0.0259 (10) | 0.0287 (10) | −0.0038 (8) | 0.0098 (8) | 0.0010 (8) |
C14 | 0.0202 (9) | 0.0243 (9) | 0.0212 (9) | 0.0003 (7) | 0.0116 (8) | 0.0021 (7) |
C15 | 0.0251 (10) | 0.0222 (9) | 0.0179 (9) | −0.0022 (7) | 0.0105 (8) | −0.0016 (7) |
C16 | 0.0303 (10) | 0.0194 (9) | 0.0239 (10) | −0.0027 (8) | 0.0155 (8) | −0.0013 (7) |
C17 | 0.0346 (12) | 0.0359 (11) | 0.0424 (12) | 0.0119 (9) | 0.0256 (10) | 0.0085 (9) |
C18 | 0.0274 (11) | 0.0340 (11) | 0.0386 (12) | 0.0017 (9) | 0.0172 (10) | 0.0024 (9) |
C19 | 0.0452 (14) | 0.0649 (16) | 0.0367 (13) | −0.0055 (12) | 0.0132 (11) | 0.0147 (12) |
O1—C8 | 1.341 (2) | C6—C7 | 1.500 (2) |
O1—C9 | 1.441 (2) | C7—H7A | 0.9600 |
O2—C8 | 1.225 (2) | C7—H7B | 0.9600 |
O3—C16 | 1.214 (2) | C7—H7C | 0.9600 |
O4—C16 | 1.342 (2) | C9—H9A | 0.9600 |
O4—C17 | 1.452 (2) | C9—H9B | 0.9600 |
O5—C18 | 1.410 (2) | C9—H9C | 0.9600 |
O5—C19 | 1.421 (3) | C10—C15 | 1.386 (2) |
O6—N2 | 1.218 (2) | C10—C11 | 1.390 (2) |
O7—N2 | 1.225 (2) | C11—C12 | 1.380 (3) |
N1—C2 | 1.369 (2) | C11—H11 | 0.9300 |
N1—C6 | 1.386 (2) | C12—C13 | 1.382 (3) |
N1—H1 | 0.888 (9) | C12—H12 | 0.9300 |
N2—C14 | 1.468 (2) | C13—C14 | 1.380 (3) |
C1—C2 | 1.501 (2) | C13—H13 | 0.9300 |
C1—H1A | 0.9600 | C14—C15 | 1.382 (2) |
C1—H1B | 0.9600 | C15—H15 | 0.9300 |
C1—H1C | 0.9600 | C17—C18 | 1.492 (3) |
C2—C3 | 1.361 (2) | C17—H17A | 0.9700 |
C3—C8 | 1.452 (2) | C17—H17B | 0.9700 |
C3—C4 | 1.518 (2) | C18—H18A | 0.9700 |
C4—C5 | 1.522 (2) | C18—H18B | 0.9700 |
C4—C10 | 1.526 (2) | C19—H19A | 0.9600 |
C4—H4 | 0.9800 | C19—H19B | 0.9600 |
C5—C6 | 1.349 (2) | C19—H19C | 0.9600 |
C5—C16 | 1.471 (3) | ||
C8—O1—C9 | 115.48 (14) | H9A—C9—H9B | 109.5 |
C16—O4—C17 | 115.99 (14) | O1—C9—H9C | 109.5 |
C18—O5—C19 | 111.16 (16) | H9A—C9—H9C | 109.5 |
C2—N1—C6 | 124.58 (14) | H9B—C9—H9C | 109.5 |
C2—N1—H1 | 119.0 (14) | C15—C10—C11 | 118.60 (16) |
C6—N1—H1 | 116.4 (14) | C15—C10—C4 | 120.98 (15) |
O6—N2—O7 | 122.71 (16) | C11—C10—C4 | 120.41 (15) |
O6—N2—C14 | 118.76 (15) | C12—C11—C10 | 121.52 (17) |
O7—N2—C14 | 118.52 (16) | C12—C11—H11 | 119.2 |
C2—C1—H1A | 109.5 | C10—C11—H11 | 119.2 |
C2—C1—H1B | 109.5 | C11—C12—C13 | 120.16 (17) |
H1A—C1—H1B | 109.5 | C11—C12—H12 | 119.9 |
C2—C1—H1C | 109.5 | C13—C12—H12 | 119.9 |
H1A—C1—H1C | 109.5 | C14—C13—C12 | 118.01 (17) |
H1B—C1—H1C | 109.5 | C14—C13—H13 | 121.0 |
C3—C2—N1 | 119.28 (16) | C12—C13—H13 | 121.0 |
C3—C2—C1 | 127.08 (16) | C13—C14—C15 | 122.64 (16) |
N1—C2—C1 | 113.64 (14) | C13—C14—N2 | 119.26 (16) |
C2—C3—C8 | 125.15 (16) | C15—C14—N2 | 118.10 (16) |
C2—C3—C4 | 121.45 (15) | C14—C15—C10 | 119.06 (16) |
C8—C3—C4 | 113.38 (14) | C14—C15—H15 | 120.5 |
C3—C4—C5 | 112.24 (14) | C10—C15—H15 | 120.5 |
C3—C4—C10 | 110.75 (14) | O3—C16—O4 | 122.05 (17) |
C5—C4—C10 | 109.88 (14) | O3—C16—C5 | 122.84 (16) |
C3—C4—H4 | 107.9 | O4—C16—C5 | 115.03 (15) |
C5—C4—H4 | 107.9 | O4—C17—C18 | 107.68 (15) |
C10—C4—H4 | 107.9 | O4—C17—H17A | 110.2 |
C6—C5—C16 | 125.65 (16) | C18—C17—H17A | 110.2 |
C6—C5—C4 | 121.55 (16) | O4—C17—H17B | 110.2 |
C16—C5—C4 | 112.79 (14) | C18—C17—H17B | 110.2 |
C5—C6—N1 | 119.42 (15) | H17A—C17—H17B | 108.5 |
C5—C6—C7 | 128.25 (17) | O5—C18—C17 | 109.62 (17) |
N1—C6—C7 | 112.27 (15) | O5—C18—H18A | 109.7 |
C6—C7—H7A | 109.5 | C17—C18—H18A | 109.7 |
C6—C7—H7B | 109.5 | O5—C18—H18B | 109.7 |
H7A—C7—H7B | 109.5 | C17—C18—H18B | 109.7 |
C6—C7—H7C | 109.5 | H18A—C18—H18B | 108.2 |
H7A—C7—H7C | 109.5 | O5—C19—H19A | 109.5 |
H7B—C7—H7C | 109.5 | O5—C19—H19B | 109.5 |
O2—C8—O1 | 121.34 (16) | H19A—C19—H19B | 109.5 |
O2—C8—C3 | 122.25 (16) | O5—C19—H19C | 109.5 |
O1—C8—C3 | 116.40 (14) | H19A—C19—H19C | 109.5 |
O1—C9—H9A | 109.5 | H19B—C19—H19C | 109.5 |
O1—C9—H9B | 109.5 | ||
C6—N1—C2—C3 | 5.0 (3) | C5—C4—C10—C15 | −106.64 (18) |
C6—N1—C2—C1 | −175.04 (16) | C3—C4—C10—C11 | −52.6 (2) |
N1—C2—C3—C8 | −175.56 (16) | C5—C4—C10—C11 | 72.0 (2) |
C1—C2—C3—C8 | 4.5 (3) | C15—C10—C11—C12 | −0.9 (3) |
N1—C2—C3—C4 | 5.9 (2) | C4—C10—C11—C12 | −179.55 (16) |
C1—C2—C3—C4 | −174.06 (17) | C10—C11—C12—C13 | −0.2 (3) |
C2—C3—C4—C5 | −12.9 (2) | C11—C12—C13—C14 | 1.1 (3) |
C8—C3—C4—C5 | 168.40 (14) | C12—C13—C14—C15 | −1.0 (3) |
C2—C3—C4—C10 | 110.34 (18) | C12—C13—C14—N2 | 178.76 (17) |
C8—C3—C4—C10 | −68.37 (18) | O6—N2—C14—C13 | 179.37 (19) |
C3—C4—C5—C6 | 10.6 (2) | O7—N2—C14—C13 | −1.3 (3) |
C10—C4—C5—C6 | −113.10 (18) | O6—N2—C14—C15 | −0.8 (3) |
C3—C4—C5—C16 | −170.61 (14) | O7—N2—C14—C15 | 178.47 (17) |
C10—C4—C5—C16 | 65.68 (18) | C13—C14—C15—C10 | −0.1 (3) |
C16—C5—C6—N1 | 179.96 (16) | N2—C14—C15—C10 | −179.84 (15) |
C4—C5—C6—N1 | −1.4 (3) | C11—C10—C15—C14 | 1.0 (3) |
C16—C5—C6—C7 | 3.0 (3) | C4—C10—C15—C14 | 179.64 (16) |
C4—C5—C6—C7 | −178.38 (17) | C17—O4—C16—O3 | −2.3 (3) |
C2—N1—C6—C5 | −7.3 (3) | C17—O4—C16—C5 | 174.69 (16) |
C2—N1—C6—C7 | 170.09 (16) | C6—C5—C16—O3 | −162.51 (18) |
C9—O1—C8—O2 | −0.5 (2) | C4—C5—C16—O3 | 18.8 (2) |
C9—O1—C8—C3 | 178.75 (15) | C6—C5—C16—O4 | 20.5 (3) |
C2—C3—C8—O2 | 179.45 (17) | C4—C5—C16—O4 | −158.19 (15) |
C4—C3—C8—O2 | −1.9 (2) | C16—O4—C17—C18 | 178.25 (16) |
C2—C3—C8—O1 | 0.2 (3) | C19—O5—C18—C17 | 175.64 (18) |
C4—C3—C8—O1 | 178.86 (14) | O4—C17—C18—O5 | −73.8 (2) |
C3—C4—C10—C15 | 128.79 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.89 (1) | 1.97 (1) | 2.8556 (19) | 171 (2) |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H22N2O7 |
Mr | 390.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.575 (3), 9.909 (2), 14.522 (3) |
β (°) | 115.11 (3) |
V (Å3) | 1899.1 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.10 × 0.08 × 0.06 |
Data collection | |
Diffractometer | Bruker P4 |
Absorption correction | Multi-scan (SADABS; Sheldrick 1996) |
Tmin, Tmax | 0.990, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14339, 4505, 3156 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.138, 1.06 |
No. of reflections | 4505 |
No. of parameters | 261 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.23 |
Computer programs: SMART (Bruker, 1997), SMART, SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.888 (9) | 1.974 (10) | 2.8556 (19) | 171 (2) |
Symmetry code: (i) x, −y+3/2, z−1/2. |
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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 title compound, (I), is a nefidipine analog. The molecular structure of (I) is shown in Fig. 1. The dihydropyridine rings display an envelope conformation, with atom C4 displaced from the mean planes formed by the other atoms in the same ring by 0.170 (1) A°. The dihedral angle between the benzene ring and the N1/C2/C3/C5/C6 plane is 85.50 (0)°. This is similar to the situation found in nefidipine (Hofmann & Cimiraglia, 1990; Cotta-Ramusino & Varì, 1999) and the structure of 3-(2-acetoxyethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylate (Sun et al., 2006).