Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300120X/na6195sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680300120X/na6195Isup2.hkl |
CCDC reference: 204704
The title compound was obtained from Key Organics Ltd and crystals were grown from ethanol solution.
All H atoms were included in the refinement, at calculated positions, as riding models, with C—H distances of 0.95 (Ar—H), 1.00 (CH), 0.99 (CH2) and 0.98 Å (CH3), while the isotropic displacement parameters were set at 1.25Ueq of the preceeding normal atom. The Rint value of 0.129 was the result of weak high-angle data.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing ellipsoids at the 50% probability level. |
C21H25NO3 | F(000) = 728 |
Mr = 339.42 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.001 (2) Å | Cell parameters from 20434 reflections |
b = 6.5492 (10) Å | θ = 2.9–27.5° |
c = 17.145 (3) Å | µ = 0.08 mm−1 |
β = 110.584 (5)° | T = 150 K |
V = 1787.1 (5) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.15 × 0.03 mm |
Bruker–Nonius KappaCCD area-detector diffractometer | 2934 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 1368 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.129 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 3.2° |
ϕ and ω scans | h = −18→20 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −7→7 |
Tmin = 0.983, Tmax = 0.998 | l = −19→20 |
8778 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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.223 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.1159P)2] where P = (Fo2 + 2Fc2)/3 |
2934 reflections | (Δ/σ)max < 0.001 |
247 parameters | Δρmax = 0.30 e Å−3 |
29 restraints | Δρmin = −0.32 e Å−3 |
C21H25NO3 | V = 1787.1 (5) Å3 |
Mr = 339.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.001 (2) Å | µ = 0.08 mm−1 |
b = 6.5492 (10) Å | T = 150 K |
c = 17.145 (3) Å | 0.20 × 0.15 × 0.03 mm |
β = 110.584 (5)° |
Bruker–Nonius KappaCCD area-detector diffractometer | 2934 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1368 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 0.998 | Rint = 0.129 |
8778 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 29 restraints |
wR(F2) = 0.223 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.30 e Å−3 |
2934 reflections | Δρmin = −0.32 e Å−3 |
247 parameters |
Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################ Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.8624 (0.0327) x + 2.8607 (0.0127) y + 10.4700 (0.0286) z = 4.1434 (0.0199) * −0.0159 (0.0025) C1 * 0.0455 (0.0024) N2 * −0.0532 (0.0027) C3 * 0.0403 (0.0028) C9 * −0.0166 (0.0027) C8 Rms deviation of fitted atoms = 0.0376 1.3752 (0.0278) x + 3.1373 (0.0091) y − 14.5166 (0.0145) z = 1.2319 (0.0115) Angle to previous plane (with approximate e.s.d.) = 62.56 (0.14) * −0.0017 (0.0028) C21 * 0.0040 (0.0028) C22 * −0.0023 (0.0028) C23 * −0.0016 (0.0028) C24 * 0.0039 (0.0027) C25 * −0.0022 (0.0027) C26 Rms deviation of fitted atoms = 0.0028 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | −0.2069 (3) | 1.1541 (7) | 0.2145 (3) | 0.0426 (11) | |
O1 | −0.19386 (19) | 0.9842 (5) | 0.24579 (19) | 0.0563 (9) | |
N2 | −0.16329 (19) | 1.2394 (5) | 0.16848 (19) | 0.0354 (9) | |
C21 | −0.0957 (3) | 1.1381 (6) | 0.1522 (2) | 0.0370 (10) | |
C22 | −0.1080 (3) | 0.9563 (6) | 0.1113 (2) | 0.0399 (11) | |
H22 | −0.1623 | 0.8960 | 0.0926 | 0.050* | |
C23 | −0.0421 (3) | 0.8575 (6) | 0.0966 (3) | 0.0393 (11) | |
H23 | −0.0505 | 0.7299 | 0.0686 | 0.049* | |
C24 | 0.0358 (3) | 0.9498 (6) | 0.1239 (2) | 0.0394 (11) | |
C25 | 0.0473 (3) | 1.1336 (6) | 0.1644 (3) | 0.0411 (11) | |
H25 | 0.1013 | 1.1956 | 0.1823 | 0.051* | |
C26 | −0.0178 (3) | 1.2307 (6) | 0.1796 (2) | 0.0399 (11) | |
H26 | −0.0092 | 1.3577 | 0.2082 | 0.050* | |
O21 | 0.10419 (17) | 0.8646 (4) | 0.11353 (18) | 0.0479 (8) | |
C27 | 0.0941 (3) | 0.6843 (7) | 0.0644 (3) | 0.0510 (12) | |
H271 | 0.0763 | 0.5714 | 0.0919 | 0.064* | |
H272 | 0.1476 | 0.6496 | 0.0581 | 0.064* | |
H273 | 0.0513 | 0.7079 | 0.0093 | 0.064* | |
C3 | −0.1976 (3) | 1.4218 (7) | 0.1317 (3) | 0.0434 (11) | |
O3 | −0.17827 (18) | 1.5097 (4) | 0.07968 (19) | 0.0518 (9) | |
C4 | −0.3450 (3) | 1.5392 (9) | 0.0946 (4) | 0.0791 (18) | |
H41 | −0.3855 | 1.6036 | 0.1169 | 0.099* | |
H42 | −0.3320 | 1.6386 | 0.0574 | 0.099* | |
C5 | −0.3833 (3) | 1.3527 (12) | 0.0465 (3) | 0.0704 (17) | |
C51A | −0.4068 (5) | 1.3958 (12) | −0.0477 (4) | 0.073 (2) | 0.70 |
H511 | −0.3603 | 1.4696 | −0.0574 | 0.091* | 0.70 |
H512 | −0.4575 | 1.4835 | −0.0673 | 0.091* | 0.70 |
C51B | −0.4308 (10) | 1.274 (3) | −0.0427 (9) | 0.076 (6) | 0.30 |
H513 | −0.4835 | 1.3523 | −0.0675 | 0.095* | 0.30 |
H514 | −0.4457 | 1.1287 | −0.0403 | 0.095* | 0.30 |
C52A | −0.4242 (5) | 1.1936 (12) | −0.0973 (5) | 0.075 (2) | 0.70 |
H523 | −0.4535 | 1.2222 | −0.1573 | 0.094* | 0.70 |
H524 | −0.4608 | 1.1049 | −0.0780 | 0.094* | 0.70 |
C52B | −0.3773 (14) | 1.295 (3) | −0.0984 (12) | 0.094 (7) | 0.30 |
H521 | −0.3344 | 1.4042 | −0.0787 | 0.118* | 0.30 |
H522 | −0.4121 | 1.3194 | −0.1575 | 0.118* | 0.30 |
C53 | −0.3383 (4) | 1.0818 (11) | −0.0842 (4) | 0.097 (2) | |
H53 | −0.2874 | 1.1382 | −0.0471 | 0.121* | |
C54 | −0.3365 (3) | 0.9123 (9) | −0.1238 (3) | 0.0637 (15) | |
C55 | −0.2582 (3) | 0.7912 (8) | −0.1072 (3) | 0.0641 (14) | |
H551 | −0.2099 | 0.8717 | −0.0729 | 0.080* | |
H552 | −0.2516 | 0.7568 | −0.1602 | 0.080* | |
H553 | −0.2618 | 0.6654 | −0.0777 | 0.080* | |
C56 | −0.4106 (3) | 0.8276 (9) | −0.1907 (4) | 0.0928 (19) | |
H561 | −0.4273 | 0.6989 | −0.1719 | 0.116* | |
H562 | −0.3962 | 0.8025 | −0.2405 | 0.116* | |
H563 | −0.4571 | 0.9252 | −0.2041 | 0.116* | |
C6 | −0.3888 (3) | 1.1894 (11) | 0.0879 (4) | 0.0758 (17) | |
H6 | −0.4113 | 1.0666 | 0.0593 | 0.095* | |
C7 | −0.3595 (3) | 1.1980 (8) | 0.1807 (3) | 0.0653 (15) | |
H71 | −0.3561 | 1.0575 | 0.2030 | 0.082* | |
H72 | −0.4009 | 1.2746 | 0.1978 | 0.082* | |
C8 | −0.2733 (3) | 1.3006 (7) | 0.2179 (3) | 0.0479 (12) | |
H8 | −0.2628 | 1.3423 | 0.2768 | 0.060* | |
C9 | −0.2638 (3) | 1.4835 (7) | 0.1672 (3) | 0.0492 (12) | |
H9 | −0.2438 | 1.6044 | 0.2046 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.042 (3) | 0.042 (3) | 0.041 (3) | 0.003 (2) | 0.011 (2) | −0.001 (2) |
O1 | 0.058 (2) | 0.053 (2) | 0.067 (2) | 0.0071 (17) | 0.0332 (18) | 0.0113 (18) |
N2 | 0.034 (2) | 0.034 (2) | 0.041 (2) | 0.0016 (16) | 0.0164 (17) | 0.0014 (17) |
C21 | 0.034 (3) | 0.038 (3) | 0.037 (2) | −0.002 (2) | 0.009 (2) | −0.001 (2) |
C22 | 0.030 (3) | 0.048 (3) | 0.040 (3) | −0.005 (2) | 0.010 (2) | −0.005 (2) |
C23 | 0.036 (3) | 0.034 (2) | 0.048 (3) | −0.002 (2) | 0.015 (2) | −0.006 (2) |
C24 | 0.038 (3) | 0.044 (3) | 0.039 (3) | 0.001 (2) | 0.016 (2) | −0.002 (2) |
C25 | 0.032 (3) | 0.044 (3) | 0.048 (3) | 0.000 (2) | 0.015 (2) | −0.001 (2) |
C26 | 0.039 (3) | 0.039 (2) | 0.040 (3) | −0.007 (2) | 0.012 (2) | −0.003 (2) |
O21 | 0.0316 (18) | 0.0525 (19) | 0.061 (2) | 0.0032 (14) | 0.0187 (15) | −0.0059 (16) |
C27 | 0.042 (3) | 0.052 (3) | 0.058 (3) | 0.009 (2) | 0.018 (2) | −0.007 (3) |
C3 | 0.042 (3) | 0.041 (3) | 0.049 (3) | −0.002 (2) | 0.016 (2) | 0.004 (2) |
O3 | 0.047 (2) | 0.0461 (18) | 0.065 (2) | 0.0022 (15) | 0.0223 (18) | 0.0094 (17) |
C4 | 0.051 (4) | 0.099 (5) | 0.098 (5) | 0.034 (3) | 0.039 (3) | 0.046 (4) |
C5 | 0.038 (3) | 0.119 (5) | 0.049 (4) | 0.020 (3) | 0.009 (3) | −0.006 (4) |
C51A | 0.059 (4) | 0.091 (4) | 0.075 (4) | 0.005 (3) | 0.030 (3) | 0.013 (4) |
C51B | 0.072 (7) | 0.073 (7) | 0.080 (7) | 0.006 (5) | 0.023 (5) | −0.006 (5) |
C52A | 0.064 (4) | 0.089 (4) | 0.064 (4) | 0.006 (4) | 0.013 (3) | −0.005 (4) |
C52B | 0.099 (8) | 0.093 (8) | 0.091 (8) | 0.000 (5) | 0.033 (5) | 0.001 (5) |
C53 | 0.115 (6) | 0.118 (5) | 0.051 (4) | 0.033 (4) | 0.021 (3) | 0.000 (4) |
C54 | 0.058 (4) | 0.079 (4) | 0.056 (3) | 0.002 (3) | 0.021 (3) | 0.010 (3) |
C55 | 0.047 (3) | 0.084 (4) | 0.061 (3) | −0.002 (3) | 0.018 (3) | 0.002 (3) |
C56 | 0.058 (4) | 0.102 (5) | 0.102 (5) | 0.003 (3) | 0.008 (4) | 0.010 (4) |
C6 | 0.031 (3) | 0.101 (5) | 0.094 (5) | −0.002 (3) | 0.021 (3) | −0.021 (4) |
C7 | 0.046 (3) | 0.072 (3) | 0.087 (4) | −0.001 (3) | 0.035 (3) | −0.003 (3) |
C8 | 0.042 (3) | 0.058 (3) | 0.046 (3) | 0.005 (2) | 0.018 (2) | −0.006 (2) |
C9 | 0.044 (3) | 0.045 (3) | 0.059 (3) | 0.008 (2) | 0.019 (3) | −0.002 (2) |
C1—O1 | 1.222 (5) | C51A—H512 | 0.99 |
C1—N2 | 1.377 (5) | C52A—C53 | 1.577 (9) |
C1—C8 | 1.498 (6) | C52A—H523 | 0.99 |
N2—C3 | 1.381 (5) | C52A—H524 | 0.99 |
N2—C21 | 1.438 (5) | C53—H53 | 0.95 |
C21—C22 | 1.359 (5) | C51B—C52B | 1.539 (16) |
C21—C26 | 1.380 (5) | C51B—H513 | 0.99 |
C22—C23 | 1.391 (5) | C51B—H514 | 0.99 |
C22—H22 | 0.95 | C52B—H521 | 0.99 |
C23—C24 | 1.379 (6) | C52B—H522 | 0.99 |
C23—H23 | 0.95 | C54—C53 | 1.307 (7) |
C24—O21 | 1.357 (5) | C54—C56 | 1.481 (7) |
C24—C25 | 1.369 (5) | C54—C55 | 1.488 (6) |
C25—C26 | 1.378 (5) | C55—H551 | 0.98 |
C25—H25 | 0.95 | C55—H552 | 0.98 |
C26—H26 | 0.95 | C55—H553 | 0.98 |
O21—C27 | 1.426 (5) | C56—H561 | 0.98 |
C27—H271 | 0.98 | C56—H562 | 0.98 |
C27—H272 | 0.98 | C56—H563 | 0.98 |
C27—H273 | 0.98 | C6—C5 | 1.305 (7) |
C3—O3 | 1.200 (5) | C6—C7 | 1.491 (7) |
C3—C9 | 1.511 (6) | C6—H6 | 0.95 |
C4—C5 | 1.489 (8) | C7—C8 | 1.532 (6) |
C4—C9 | 1.542 (7) | C7—H71 | 0.99 |
C4—H41 | 0.99 | C7—H72 | 0.99 |
C4—H42 | 0.99 | C8—C9 | 1.522 (6) |
C5—C51A | 1.548 (8) | C8—H8 | 1.00 |
C51A—C52A | 1.545 (9) | C9—H9 | 1.00 |
C51A—H511 | 0.99 | ||
O1—C1—N2 | 124.7 (4) | C54—C56—H562 | 109.5 |
O1—C1—C8 | 126.1 (4) | H561—C56—H562 | 109.5 |
N2—C1—C8 | 109.1 (4) | C54—C56—H563 | 109.5 |
C1—N2—C3 | 112.7 (3) | H561—C56—H563 | 109.5 |
C1—N2—C21 | 123.6 (3) | H562—C56—H563 | 109.5 |
C3—N2—C21 | 123.3 (3) | C5—C6—C7 | 119.2 (5) |
C22—C21—C26 | 121.1 (4) | C5—C6—H6 | 120.4 |
C22—C21—N2 | 121.0 (4) | C7—C6—H6 | 120.4 |
C26—C21—N2 | 117.9 (4) | C6—C7—C8 | 111.9 (4) |
C21—C22—C23 | 120.8 (4) | C6—C7—H71 | 109.2 |
C21—C22—H22 | 119.6 | C8—C7—H71 | 109.2 |
C23—C22—H22 | 119.6 | C6—C7—H72 | 109.2 |
C24—C23—C22 | 118.2 (4) | C8—C7—H72 | 109.2 |
C24—C23—H23 | 120.9 | H71—C7—H72 | 107.9 |
C22—C23—H23 | 120.9 | C1—C8—C9 | 104.4 (3) |
O21—C24—C25 | 116.8 (4) | C1—C8—C7 | 109.0 (4) |
O21—C24—C23 | 122.7 (4) | C9—C8—C7 | 112.6 (4) |
C25—C24—C23 | 120.4 (4) | C1—C8—H8 | 110.2 |
C24—C25—C26 | 121.4 (4) | C9—C8—H8 | 110.2 |
C24—C25—H25 | 119.3 | C7—C8—H8 | 110.2 |
C26—C25—H25 | 119.3 | C3—C9—C8 | 105.3 (3) |
C25—C26—C21 | 118.0 (4) | C3—C9—C4 | 108.7 (4) |
C25—C26—H26 | 121.0 | C8—C9—C4 | 113.7 (4) |
C21—C26—H26 | 121.0 | C3—C9—H9 | 109.7 |
C24—O21—C27 | 119.2 (3) | C8—C9—H9 | 109.7 |
O21—C27—H271 | 109.5 | C4—C9—H9 | 109.7 |
O21—C27—H272 | 109.5 | C6—C5—C4 | 118.1 (5) |
H271—C27—H272 | 109.5 | C6—C5—C51A | 132.5 (7) |
O21—C27—H273 | 109.5 | C4—C5—C51A | 109.3 (6) |
H271—C27—H273 | 109.5 | C5—C51A—C52A | 110.4 (6) |
H272—C27—H273 | 109.5 | C5—C51A—H511 | 109.6 |
O3—C3—N2 | 124.9 (4) | C52A—C51A—H511 | 109.6 |
O3—C3—C9 | 127.5 (4) | C5—C51A—H512 | 109.6 |
N2—C3—C9 | 107.6 (4) | C52A—C51A—H512 | 109.6 |
C5—C4—C9 | 110.2 (4) | H511—C51A—H512 | 108.1 |
C5—C4—H41 | 109.6 | C51A—C52A—C53 | 109.3 (6) |
C9—C4—H41 | 109.6 | C51A—C52A—H523 | 109.8 |
C5—C4—H42 | 109.6 | C53—C52A—H523 | 109.8 |
C9—C4—H42 | 109.6 | C51A—C52A—H524 | 109.8 |
H41—C4—H42 | 108.1 | C53—C52A—H524 | 109.8 |
C53—C54—C56 | 123.5 (6) | H523—C52A—H524 | 108.3 |
C53—C54—C55 | 122.4 (5) | C54—C53—C52A | 120.6 (6) |
C56—C54—C55 | 114.0 (5) | C54—C53—H53 | 119.7 |
C54—C55—H551 | 109.5 | C52A—C53—H53 | 119.7 |
C54—C55—H552 | 109.5 | C52B—C51B—H513 | 109.3 |
H551—C55—H552 | 109.5 | C52B—C51B—H514 | 109.3 |
C54—C55—H553 | 109.5 | H513—C51B—H514 | 108.0 |
H551—C55—H553 | 109.5 | C51B—C52B—H521 | 112.2 |
H552—C55—H553 | 109.5 | C51B—C52B—H522 | 112.2 |
C54—C56—H561 | 109.5 | H521—C52B—H522 | 109.8 |
O1—C1—N2—C3 | 172.3 (4) | N2—C1—C8—C9 | 0.5 (4) |
C8—C1—N2—C3 | −6.4 (4) | O1—C1—C8—C7 | −57.6 (6) |
O1—C1—N2—C21 | −0.6 (6) | N2—C1—C8—C7 | 121.1 (4) |
C8—C1—N2—C21 | −179.3 (4) | C6—C7—C8—C1 | −76.0 (5) |
C1—N2—C21—C22 | 59.6 (5) | C6—C7—C8—C9 | 39.5 (6) |
C3—N2—C21—C22 | −112.6 (4) | O3—C3—C9—C8 | 169.8 (4) |
C1—N2—C21—C26 | −120.1 (4) | N2—C3—C9—C8 | −8.6 (5) |
C3—N2—C21—C26 | 67.7 (5) | O3—C3—C9—C4 | 47.6 (6) |
C26—C21—C22—C23 | 0.6 (6) | N2—C3—C9—C4 | −130.8 (4) |
N2—C21—C22—C23 | −179.1 (3) | C1—C8—C9—C3 | 4.8 (5) |
C21—C22—C23—C24 | −0.6 (6) | C7—C8—C9—C3 | −113.3 (4) |
C22—C23—C24—O21 | 179.2 (4) | C1—C8—C9—C4 | 123.8 (4) |
C22—C23—C24—C25 | 0.1 (6) | C7—C8—C9—C4 | 5.6 (5) |
O21—C24—C25—C26 | −178.6 (3) | C5—C4—C9—C3 | 69.5 (5) |
C23—C24—C25—C26 | 0.5 (6) | C5—C4—C9—C8 | −47.4 (6) |
C24—C25—C26—C21 | −0.6 (6) | C7—C6—C5—C4 | 2.0 (7) |
C22—C21—C26—C25 | 0.0 (6) | C7—C6—C5—C51A | 179.6 (6) |
N2—C21—C26—C25 | 179.7 (3) | C9—C4—C5—C6 | 45.5 (6) |
C25—C24—O21—C27 | −173.5 (3) | C9—C4—C5—C51A | −132.7 (5) |
C23—C24—O21—C27 | 7.4 (6) | C6—C5—C51A—C52A | −12.8 (10) |
C1—N2—C3—O3 | −169.0 (4) | C4—C5—C51A—C52A | 164.9 (6) |
C21—N2—C3—O3 | 4.0 (6) | C5—C51A—C52A—C53 | −74.5 (8) |
C1—N2—C3—C9 | 9.5 (5) | C56—C54—C53—C52A | 8.3 (9) |
C21—N2—C3—C9 | −177.5 (4) | C55—C54—C53—C52A | −174.0 (6) |
C5—C6—C7—C8 | −46.6 (7) | C51A—C52A—C53—C54 | −176.2 (6) |
O1—C1—C8—C9 | −178.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O3i | 0.95 | 2.55 | 3.134 (5) | 120 |
C25—H25···O1ii | 0.95 | 2.49 | 3.340 (5) | 149 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H25NO3 |
Mr | 339.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 17.001 (2), 6.5492 (10), 17.145 (3) |
β (°) | 110.584 (5) |
V (Å3) | 1787.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.20 × 0.15 × 0.03 |
Data collection | |
Diffractometer | Bruker–Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.983, 0.998 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8778, 2934, 1368 |
Rint | 0.129 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.223, 0.94 |
No. of reflections | 2934 |
No. of parameters | 247 |
No. of restraints | 29 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.32 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O3i | 0.95 | 2.55 | 3.134 (5) | 120 |
C25—H25···O1ii | 0.95 | 2.49 | 3.340 (5) | 149 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2. |
The title compound, (I), was prepared by a Diels–Alder reaction between 1-(4-methoxyphenyl)-3-pyrroline-2,5-dione and 7-methyl-3-methyleneocta-1,6-diene. The naming of (I) has proved difficult with several variants for the main ring system being previously given. The basic unsubstituted structure (Kirfel, 1976) was named as a tetrahydrophthalimide and several other substituted analogues have been similarly named, although numbering schemes differ significantly as to which four atoms are saturated. Other names include hydroisoindoline-1,3-dione (with differing numbers of saturated C atoms), cyclohex-4-ene-1,2-dicarboximide and azabicyclo[4.3.0]non-3-ene-7,9-dione, with the first being the most popular. The structure of (I) comprises a U-shaped molecule with two disordered atoms in the pentene chain (Fig. 1). The shape is dependent on the boat conformation displayed by the hydrophthalimide group. Of 136 current structures (Cambridge Structural Database, September 2002 release; Allen, 2002) containing a phthalimide ring similar to (I), only 48 do not have any bridging across the cyclohexene ring. From the 48, 23 compounds contain an N-phenyl moiety, of which 11 compounds share a similar boat conformation to (I). This conformation is also displayed by 5-(2-methyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-5-yl)pent-2-enoic acid (Yliniemala et al., 1995) which is the nearest structural analogue to (I). In this structure, the pent-2-enoic acid chain is not disordered. In (I), the two components (A and B) of the two disordered alkane C atoms (C51 and C52) exist with unequal partial occupancies of 0.70 and 0.30, respectively, for A and B. The dihedral angle between the planar imide ring [r.m.s. deviation 0.038 (3) Å] and the phenyl ring is 62.56 (14)°. C—H···O close contacts are observed from two different aromatic C atoms to the two oxo O atoms (Table 1).