Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101009313/av1077sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009313/av1077Isup2.hkl |
CCDC reference: 173370
The title compound was prepared by known synthetic methods (Hantzsch, 1882) and recrystallized from an ethanol solution. Slow evaporation of an ethanol solution yielded yellow plate-like crystals.
The hydrogen atoms H1, H3, H6, H11, H13, H14, and H15 were located on the difference Fourier map and refined isotropically. The positions of the methyl H atoms were calculated geometrically and fixed (C···H 0.96 Å). Their isotropic displacement parameters were fixed at 1.5U(eq).
Data collection: Syntex P21 software; cell refinement: Syntex P21 software; data reduction: XP21 (Pavelčík, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXS97.
Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probablity level. |
C20H23N3O7 | Z = 2 |
Mr = 417.41 | F(000) = 440 |
Triclinic, P1 | Dx = 1.337 Mg m−3 Dm = 1.34 (1) Mg m−3 Dm measured by flotation in bromoform-hexane |
a = 9.563 (4) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.703 (4) Å | Cell parameters from 25 reflections |
c = 12.031 (6) Å | θ = 8.2–21.4° |
α = 93.99 (4)° | µ = 0.10 mm−1 |
β = 105.09 (4)° | T = 293 K |
γ = 103.66 (4)° | Plate, yellow |
V = 1037.1 (8) Å3 | 0.35 × 0.30 × 0.10 mm |
Syntex P21 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.8° |
Graphite monochromator | h = 0→9 |
θ/2θ scans | k = −11→11 |
3527 measured reflections | l = −14→13 |
3527 independent reflections | 2 standard reflections every 100 min |
1209 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0112P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.78 | (Δ/σ)max = 0.002 |
3527 reflections | Δρmax = 0.14 e Å−3 |
304 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0088 (6) |
C20H23N3O7 | γ = 103.66 (4)° |
Mr = 417.41 | V = 1037.1 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.563 (4) Å | Mo Kα radiation |
b = 9.703 (4) Å | µ = 0.10 mm−1 |
c = 12.031 (6) Å | T = 293 K |
α = 93.99 (4)° | 0.35 × 0.30 × 0.10 mm |
β = 105.09 (4)° |
Syntex P21 diffractometer | Rint = 0.000 |
3527 measured reflections | 2 standard reflections every 100 min |
3527 independent reflections | intensity decay: none |
1209 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.78 | Δρmax = 0.14 e Å−3 |
3527 reflections | Δρmin = −0.14 e Å−3 |
304 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.6623 (2) | 0.3899 (2) | 0.99646 (18) | 0.0689 (7) | |
O2 | 0.3579 (2) | −0.1862 (2) | 0.64941 (18) | 0.0682 (7) | |
O3 | 0.5089 (2) | 0.0319 (2) | 0.69399 (18) | 0.0748 (8) | |
O4 | −0.1738 (4) | −0.4542 (3) | 0.4137 (3) | 0.1242 (14) | |
O5 | −0.3094 (4) | −0.3256 (3) | 0.3356 (2) | 0.1639 (17) | |
O6 | −0.0330 (3) | −0.2902 (2) | 0.98875 (18) | 0.0801 (9) | |
O7 | −0.0179 (2) | −0.3802 (2) | 0.81775 (17) | 0.0577 (7) | |
N1 | 0.3086 (3) | 0.0690 (3) | 0.9697 (2) | 0.0488 (8) | |
H1 | 0.348 (3) | 0.145 (3) | 1.0284 (19) | 0.049 (10)* | |
N2 | 0.5408 (3) | 0.2771 (3) | 0.9928 (2) | 0.0530 (8) | |
N3 | −0.2118 (4) | −0.3433 (4) | 0.4129 (3) | 0.0954 (14) | |
C1 | 0.3793 (3) | 0.0662 (3) | 0.8842 (3) | 0.0403 (9) | |
C2 | 0.3280 (3) | −0.0438 (3) | 0.7976 (3) | 0.0367 (8) | |
C3 | 0.1838 (3) | −0.1580 (4) | 0.7874 (3) | 0.0417 (9) | |
H3 | 0.209 (2) | −0.245 (2) | 0.7624 (17) | 0.018 (8)* | |
C4 | 0.1427 (3) | −0.1573 (3) | 0.8999 (3) | 0.0388 (9) | |
C5 | 0.2011 (3) | −0.0458 (4) | 0.9832 (3) | 0.0410 (9) | |
C6 | 0.5079 (4) | 0.1884 (4) | 0.9001 (3) | 0.0512 (10) | |
H6 | 0.561 (3) | 0.202 (3) | 0.8324 (19) | 0.063 (10)* | |
C7 | 0.6918 (3) | 0.4913 (3) | 1.0985 (2) | 0.0720 (11) | |
H7A | 0.7759 | 0.5701 | 1.1017 | 0.108* | |
H7B | 0.7143 | 0.4453 | 1.1666 | 0.108* | |
H7C | 0.6050 | 0.5261 | 1.0952 | 0.108* | |
C8 | 0.4098 (4) | −0.0570 (4) | 0.7115 (3) | 0.0477 (9) | |
C9 | 0.4334 (4) | −0.2175 (3) | 0.5645 (3) | 0.0938 (13) | |
H9A | 0.3867 | −0.3134 | 0.5252 | 0.141* | |
H9B | 0.5372 | −0.2087 | 0.6031 | 0.141* | |
H9C | 0.4264 | −0.1512 | 0.5090 | 0.141* | |
C10 | 0.0574 (3) | −0.1398 (4) | 0.6882 (2) | 0.0373 (8) | |
C11 | −0.0145 (4) | −0.2463 (4) | 0.5944 (3) | 0.0464 (10) | |
H11 | 0.024 (3) | −0.323 (3) | 0.592 (2) | 0.041 (10)* | |
C12 | −0.1339 (4) | −0.2294 (4) | 0.5107 (3) | 0.0526 (10) | |
C13 | −0.1847 (4) | −0.1109 (5) | 0.5149 (3) | 0.0598 (12) | |
H13 | −0.268 (3) | −0.107 (3) | 0.455 (2) | 0.068 (12)* | |
C14 | −0.1134 (5) | −0.0036 (5) | 0.6053 (3) | 0.0614 (12) | |
H14 | −0.145 (3) | 0.078 (3) | 0.616 (2) | 0.056 (11)* | |
C15 | 0.0070 (4) | −0.0188 (4) | 0.6912 (3) | 0.0486 (10) | |
H15 | 0.049 (3) | 0.060 (2) | 0.7479 (18) | 0.034 (9)* | |
C16 | 0.0239 (4) | −0.2786 (4) | 0.9096 (3) | 0.0496 (10) | |
C17 | −0.1482 (4) | −0.5021 (4) | 0.8082 (4) | 0.0655 (12) | |
H17 | −0.137 (3) | −0.535 (3) | 0.894 (2) | 0.106 (13)* | |
C18 | −0.1316 (4) | −0.6212 (3) | 0.7323 (3) | 0.0929 (14) | |
H18A | −0.0417 | −0.6475 | 0.7691 | 0.139* | |
H18B | −0.1256 | −0.5908 | 0.6590 | 0.139* | |
H18C | −0.2168 | −0.7022 | 0.7196 | 0.139* | |
C19 | −0.2868 (4) | −0.4518 (4) | 0.7581 (3) | 0.1017 (14) | |
H19A | −0.2906 | −0.3756 | 0.8116 | 0.153* | |
H19B | −0.3746 | −0.5301 | 0.7455 | 0.153* | |
H19C | −0.2830 | −0.4180 | 0.6856 | 0.153* | |
C20 | 0.1670 (3) | −0.0251 (3) | 1.0975 (2) | 0.0609 (10) | |
H20A | 0.2276 | 0.0660 | 1.1403 | 0.091* | |
H20B | 0.1889 | −0.1000 | 1.1416 | 0.091* | |
H20C | 0.0628 | −0.0280 | 1.0836 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0657 (18) | 0.0562 (16) | 0.0752 (18) | −0.0050 (15) | 0.0257 (14) | −0.0020 (14) |
O2 | 0.0645 (17) | 0.0674 (18) | 0.0753 (17) | 0.0049 (14) | 0.0420 (14) | −0.0139 (14) |
O3 | 0.0652 (18) | 0.075 (2) | 0.0792 (18) | −0.0077 (15) | 0.0392 (15) | −0.0028 (14) |
O4 | 0.152 (3) | 0.091 (3) | 0.088 (2) | 0.016 (2) | −0.012 (2) | −0.029 (2) |
O5 | 0.145 (3) | 0.174 (3) | 0.103 (3) | 0.041 (3) | −0.068 (2) | −0.043 (2) |
O6 | 0.089 (2) | 0.084 (2) | 0.0693 (18) | −0.0022 (15) | 0.0475 (16) | 0.0172 (15) |
O7 | 0.0575 (17) | 0.0540 (17) | 0.0557 (16) | −0.0005 (14) | 0.0181 (13) | 0.0135 (13) |
N1 | 0.044 (2) | 0.048 (2) | 0.052 (2) | 0.0080 (18) | 0.0163 (17) | −0.0036 (17) |
N2 | 0.0379 (18) | 0.047 (2) | 0.068 (2) | 0.0044 (16) | 0.0090 (16) | 0.0164 (17) |
N3 | 0.087 (3) | 0.097 (4) | 0.063 (3) | −0.006 (3) | −0.012 (2) | −0.016 (3) |
C1 | 0.034 (2) | 0.046 (3) | 0.047 (2) | 0.0143 (19) | 0.0177 (19) | 0.0182 (19) |
C2 | 0.037 (2) | 0.036 (2) | 0.037 (2) | 0.0102 (18) | 0.0091 (18) | 0.0066 (17) |
C3 | 0.038 (2) | 0.046 (3) | 0.042 (2) | 0.012 (2) | 0.0106 (18) | 0.0087 (19) |
C4 | 0.031 (2) | 0.047 (2) | 0.037 (2) | 0.0094 (19) | 0.0065 (18) | 0.0080 (19) |
C5 | 0.034 (2) | 0.056 (3) | 0.038 (2) | 0.018 (2) | 0.0112 (19) | 0.021 (2) |
C6 | 0.044 (3) | 0.057 (3) | 0.050 (3) | 0.008 (2) | 0.016 (2) | 0.005 (2) |
C7 | 0.074 (3) | 0.051 (2) | 0.076 (3) | 0.011 (2) | 0.002 (2) | 0.000 (2) |
C8 | 0.036 (2) | 0.056 (3) | 0.048 (2) | 0.013 (2) | 0.0061 (19) | 0.005 (2) |
C9 | 0.094 (3) | 0.107 (3) | 0.091 (3) | 0.019 (2) | 0.062 (3) | −0.023 (2) |
C10 | 0.032 (2) | 0.041 (2) | 0.039 (2) | 0.0060 (19) | 0.0126 (17) | 0.0130 (18) |
C11 | 0.042 (3) | 0.053 (3) | 0.045 (2) | 0.010 (2) | 0.013 (2) | 0.013 (2) |
C12 | 0.043 (3) | 0.060 (3) | 0.048 (3) | 0.001 (2) | 0.011 (2) | 0.011 (2) |
C13 | 0.047 (3) | 0.095 (4) | 0.043 (3) | 0.023 (3) | 0.015 (2) | 0.021 (3) |
C14 | 0.071 (3) | 0.069 (3) | 0.063 (3) | 0.044 (3) | 0.026 (3) | 0.022 (3) |
C15 | 0.054 (3) | 0.055 (3) | 0.045 (3) | 0.018 (2) | 0.022 (2) | 0.016 (2) |
C16 | 0.047 (3) | 0.060 (3) | 0.044 (3) | 0.016 (2) | 0.012 (2) | 0.016 (2) |
C17 | 0.053 (3) | 0.051 (3) | 0.083 (3) | −0.006 (2) | 0.018 (2) | 0.028 (2) |
C18 | 0.109 (3) | 0.060 (3) | 0.092 (3) | −0.004 (3) | 0.026 (3) | −0.003 (2) |
C19 | 0.054 (3) | 0.106 (3) | 0.128 (3) | −0.002 (3) | 0.014 (3) | 0.033 (3) |
C20 | 0.055 (2) | 0.089 (3) | 0.044 (2) | 0.022 (2) | 0.0177 (19) | 0.0146 (19) |
O1—N2 | 1.384 (3) | C7—H7B | 0.9600 |
O1—C7 | 1.440 (3) | C7—H7C | 0.9600 |
O2—C8 | 1.326 (3) | C9—H9A | 0.9600 |
O2—C9 | 1.450 (3) | C9—H9B | 0.9600 |
O3—C8 | 1.196 (3) | C9—H9C | 0.9600 |
O4—N3 | 1.214 (4) | C10—C15 | 1.372 (4) |
O5—N3 | 1.189 (4) | C10—C11 | 1.383 (4) |
O6—C16 | 1.214 (3) | C11—C12 | 1.363 (4) |
O7—C16 | 1.336 (3) | C11—H11 | 0.91 (2) |
O7—C17 | 1.474 (4) | C12—C13 | 1.352 (4) |
N1—C1 | 1.372 (4) | C13—C14 | 1.361 (5) |
N1—C5 | 1.376 (3) | C13—H13 | 0.93 (2) |
N1—H1 | 0.91 (2) | C14—C15 | 1.377 (4) |
N2—C6 | 1.280 (3) | C14—H14 | 0.92 (2) |
N3—C12 | 1.461 (4) | C15—H15 | 0.92 (2) |
C1—C2 | 1.341 (3) | C17—C18 | 1.486 (4) |
C1—C6 | 1.453 (4) | C17—C19 | 1.512 (4) |
C2—C8 | 1.467 (4) | C17—H17 | 1.09 (3) |
C2—C3 | 1.521 (4) | C18—H18A | 0.9600 |
C3—C4 | 1.505 (4) | C18—H18B | 0.9600 |
C3—C10 | 1.515 (4) | C18—H18C | 0.9600 |
C3—H3 | 0.980 (19) | C19—H19A | 0.9600 |
C4—C5 | 1.326 (4) | C19—H19B | 0.9600 |
C4—C16 | 1.465 (4) | C19—H19C | 0.9600 |
C5—C20 | 1.505 (3) | C20—H20A | 0.9600 |
C6—H6 | 1.07 (2) | C20—H20B | 0.9600 |
C7—H7A | 0.9600 | C20—H20C | 0.9600 |
N2—O1—C7 | 108.9 (2) | C15—C10—C11 | 118.0 (3) |
C8—O2—C9 | 116.8 (3) | C15—C10—C3 | 120.7 (3) |
C16—O7—C17 | 117.9 (3) | C11—C10—C3 | 121.3 (3) |
C1—N1—C5 | 123.6 (3) | C12—C11—C10 | 119.4 (4) |
C1—N1—H1 | 117.3 (17) | C12—C11—H11 | 124.2 (16) |
C5—N1—H1 | 118.0 (16) | C10—C11—H11 | 116.4 (16) |
C6—N2—O1 | 110.1 (3) | C13—C12—C11 | 122.5 (4) |
O5—N3—O4 | 122.0 (4) | C13—C12—N3 | 118.2 (4) |
O5—N3—C12 | 119.8 (4) | C11—C12—N3 | 119.3 (4) |
O4—N3—C12 | 118.2 (4) | C12—C13—C14 | 119.0 (4) |
C2—C1—N1 | 119.6 (3) | C12—C13—H13 | 117.6 (18) |
C2—C1—C6 | 126.6 (3) | C14—C13—H13 | 123.4 (18) |
N1—C1—C6 | 113.7 (3) | C13—C14—C15 | 119.5 (4) |
C1—C2—C8 | 120.9 (3) | C13—C14—H14 | 123.5 (17) |
C1—C2—C3 | 120.4 (3) | C15—C14—H14 | 116.8 (17) |
C8—C2—C3 | 118.8 (3) | C10—C15—C14 | 121.6 (4) |
C4—C3—C10 | 111.4 (3) | C10—C15—H15 | 125.0 (16) |
C4—C3—C2 | 111.7 (3) | C14—C15—H15 | 113.4 (16) |
C10—C3—C2 | 110.3 (3) | O6—C16—O7 | 122.1 (3) |
C4—C3—H3 | 114.9 (13) | O6—C16—C4 | 126.5 (3) |
C10—C3—H3 | 106.3 (12) | O7—C16—C4 | 111.4 (3) |
C2—C3—H3 | 101.7 (13) | O7—C17—C18 | 106.0 (3) |
C5—C4—C16 | 120.7 (3) | O7—C17—C19 | 106.6 (3) |
C5—C4—C3 | 121.6 (3) | C18—C17—C19 | 113.9 (3) |
C16—C4—C3 | 117.3 (3) | O7—C17—H17 | 107.7 (16) |
C4—C5—N1 | 119.4 (3) | C18—C17—H17 | 106.8 (16) |
C4—C5—C20 | 128.3 (3) | C19—C17—H17 | 115.4 (17) |
N1—C5—C20 | 112.3 (3) | C17—C18—H18A | 109.5 |
N2—C6—C1 | 115.7 (3) | C17—C18—H18B | 109.5 |
N2—C6—H6 | 125.5 (14) | H18A—C18—H18B | 109.5 |
C1—C6—H6 | 118.7 (14) | C17—C18—H18C | 109.5 |
O1—C7—H7A | 109.5 | H18A—C18—H18C | 109.5 |
O1—C7—H7B | 109.5 | H18B—C18—H18C | 109.5 |
H7A—C7—H7B | 109.5 | C17—C19—H19A | 109.5 |
O1—C7—H7C | 109.5 | C17—C19—H19B | 109.5 |
H7A—C7—H7C | 109.5 | H19A—C19—H19B | 109.5 |
H7B—C7—H7C | 109.5 | C17—C19—H19C | 109.5 |
O3—C8—O2 | 121.5 (3) | H19A—C19—H19C | 109.5 |
O3—C8—C2 | 127.9 (3) | H19B—C19—H19C | 109.5 |
O2—C8—C2 | 110.6 (3) | C5—C20—H20A | 109.5 |
O2—C9—H9A | 109.5 | C5—C20—H20B | 109.5 |
O2—C9—H9B | 109.5 | H20A—C20—H20B | 109.5 |
H9A—C9—H9B | 109.5 | C5—C20—H20C | 109.5 |
O2—C9—H9C | 109.5 | H20A—C20—H20C | 109.5 |
H9A—C9—H9C | 109.5 | H20B—C20—H20C | 109.5 |
H9B—C9—H9C | 109.5 | ||
C7—O1—N2—C6 | 177.1 (3) | C1—C2—C8—O2 | 167.1 (3) |
C5—N1—C1—C2 | 10.7 (5) | C3—C2—C8—O2 | −12.6 (4) |
C5—N1—C1—C6 | −168.7 (3) | C4—C3—C10—C15 | 60.9 (4) |
N1—C1—C2—C8 | −173.9 (3) | C2—C3—C10—C15 | −63.8 (4) |
C6—C1—C2—C8 | 5.4 (5) | C4—C3—C10—C11 | −116.5 (3) |
N1—C1—C2—C3 | 5.8 (4) | C2—C3—C10—C11 | 118.8 (3) |
C6—C1—C2—C3 | −174.9 (3) | C15—C10—C11—C12 | −1.7 (4) |
C1—C2—C3—C4 | −18.6 (4) | C3—C10—C11—C12 | 175.8 (3) |
C8—C2—C3—C4 | 161.0 (3) | C10—C11—C12—C13 | 0.7 (5) |
C1—C2—C3—C10 | 105.9 (3) | C10—C11—C12—N3 | −178.8 (3) |
C8—C2—C3—C10 | −74.4 (4) | O5—N3—C12—C13 | 5.5 (6) |
C10—C3—C4—C5 | −106.1 (3) | O4—N3—C12—C13 | −174.3 (4) |
C2—C3—C4—C5 | 17.8 (4) | O5—N3—C12—C11 | −175.0 (4) |
C10—C3—C4—C16 | 67.7 (4) | O4—N3—C12—C11 | 5.2 (6) |
C2—C3—C4—C16 | −168.4 (3) | C11—C12—C13—C14 | 0.6 (5) |
C16—C4—C5—N1 | −177.5 (3) | N3—C12—C13—C14 | −179.9 (3) |
C3—C4—C5—N1 | −3.9 (5) | C12—C13—C14—C15 | −1.0 (5) |
C16—C4—C5—C20 | 3.2 (5) | C11—C10—C15—C14 | 1.3 (5) |
C3—C4—C5—C20 | 176.9 (3) | C3—C10—C15—C14 | −176.2 (3) |
C1—N1—C5—C4 | −11.8 (4) | C13—C14—C15—C10 | 0.0 (5) |
C1—N1—C5—C20 | 167.6 (3) | C17—O7—C16—O6 | 6.5 (5) |
O1—N2—C6—C1 | −178.6 (2) | C17—O7—C16—C4 | −173.3 (3) |
C2—C1—C6—N2 | −176.5 (3) | C5—C4—C16—O6 | 1.0 (5) |
N1—C1—C6—N2 | 2.9 (4) | C3—C4—C16—O6 | −173.0 (3) |
C9—O2—C8—O3 | 3.8 (5) | C5—C4—C16—O7 | −179.2 (3) |
C9—O2—C8—C2 | −176.9 (3) | C3—C4—C16—O7 | 6.9 (4) |
C1—C2—C8—O3 | −13.8 (5) | C16—O7—C17—C18 | −157.2 (3) |
C3—C2—C8—O3 | 166.6 (3) | C16—O7—C17—C19 | 81.1 (4) |
Experimental details
Crystal data | |
Chemical formula | C20H23N3O7 |
Mr | 417.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.563 (4), 9.703 (4), 12.031 (6) |
α, β, γ (°) | 93.99 (4), 105.09 (4), 103.66 (4) |
V (Å3) | 1037.1 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.35 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Syntex P21 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3527, 3527, 1209 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.068, 0.78 |
No. of reflections | 3527 |
No. of parameters | 304 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.14 |
Computer programs: Syntex P21 software, XP21 (Pavelčík, 1987), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXS97.
O1—N2 | 1.384 (3) | C1—C2 | 1.341 (3) |
O3—C8 | 1.196 (3) | C2—C3 | 1.521 (4) |
O6—C16 | 1.214 (3) | C3—C4 | 1.505 (4) |
N1—C1 | 1.372 (4) | C3—C10 | 1.515 (4) |
N1—C5 | 1.376 (3) | C4—C5 | 1.326 (4) |
N3—C12 | 1.461 (4) | ||
N2—O1—C7 | 108.9 (2) | C4—C3—C2 | 111.7 (3) |
C1—N1—C5 | 123.6 (3) | C15—C10—C3 | 120.7 (3) |
O5—N3—O4 | 122.0 (4) | C13—C12—C11 | 122.5 (4) |
C4—C3—C10 | 111.4 (3) | O6—C16—O7 | 122.1 (3) |
C5—N1—C1—C2 | 10.7 (5) | C4—C3—C10—C15 | 60.9 (4) |
C1—C2—C3—C4 | −18.6 (4) | C2—C3—C10—C15 | −63.8 (4) |
C2—C3—C4—C5 | 17.8 (4) | O4—N3—C12—C11 | 5.2 (6) |
C1—N1—C5—C4 | −11.8 (4) | C5—C4—C16—O6 | 1.0 (5) |
C1—C2—C8—O3 | −13.8 (5) | C5—C4—C16—O7 | −179.2 (3) |
C1—C2—C8—O2 | 167.1 (3) |
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Many derivatives of 1,4-dihydropyridine (DHP) exhibit high affinity for calcium channel receptors and may act as agonists or antagonists, depending on the nature of the derivative, the physiological state of the channel and, in some cases, the side of the membrane containing the channel receptor to which the compound is added (Kokubun & Reuter, 1984). Amongst these 1,4-DHP is Nifedipine [2,6-dimethyl-3,5-dicarbomethoxy-4-(2-nitrophenyl)-1,4-dihydro- pyridine], which is one of the most potent of the calcium antagonists and is a powerful negative ionotropic and smooth-muscle relaxant species (Triggle et al., 1980). We have studied the crystal structure of methyl isopropyl 2-methoxyimino- -methyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-tricarboxylate, (I). \sch
The structure of (I) consists of discrete molecules. The 1,4-DHP ring exibits a boat conformation. The N1 and C3 atoms lie 0.110 (3) and 0.228 (3) Å, respectively, from the least-squares plane defined by the remaining four atoms of the DHP ring. The orientation of the 3-nitrophenyl ring relative to the 1,4-DHP ring, characterized by the torsion angle C2—C3—C10—C15, is -63.8 (4)°. Similar orientation of the phenyl ring is preferred in all the investigated phenyl-substituted derivatives (Mehdi & Ravikumar, 1992). It is probable that in this way the steric strain, which is imposed by the phenyl substitutent and the groups at the 3 and 5 positions, is minimized (Fossheim, 1986). The nitro-group is twisted 5.0 (3)° from the plane of the phenyl ring system. Langs & Triggle (1985) have observed that the majority of 1,4-DHP analogs have one of the ester groups at C3 and C5 of the 1,4-DHP ring in the cis conformation and the other in the trans conformation. A small number of very active antagonists are found to have cis,cis geometry. In the present compound both carbonyl groups are twisted in the same cis,cis direction. One ester group is slightly oriented out of the plane 1,4-DHP and the second ester group is coplanar with the 1,4-DHP ring (Table 1).