Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009346/tk6100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009346/tk6100Isup2.hkl |
CCDC reference: 214647
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.062
- wR factor = 0.168
- Data-to-parameter ratio = 12.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.808 1.000 Tmin' and Tmax expected: 0.972 0.993 RR' = 0.825 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
N-Butyl-4-aminophthalimide (12 mmol) and triethylamine (12 mmol) in dry chloroform (30 ml) were placed in a 50 ml flask equipped with an N2 inlet adaptor and a rubber septum, and the mixture was cooled to 263 K with stirring. Triphosgene (4 mmol) in chloroform was added dropwise and the resulting mixture was stirred at 273 K for 3 h and at 293 K for an additional 2 h. The solvent was then evaporated in vacuo to give (2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindole-5-yl)carbamic chloride, (II). (II) was soluted in dry ethanol (20 ml) and stirring at room temperature for 2 h. After evaporation of the surplus ethanol, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the title compound, (I). M.p. 413–415 K; IR (KBr): 3340 (N—H), 3080, 2951 (C—H), 1730, 1697 (C═O) cm−1; 1H NMR (CDCl3, p.p.m.): 0.92 (3H, t), 1.27–1.43 (5H, m), 1.62 (2H, s), 3.63 (2H, t), 4.24 (2H, m), 6.98 (1H, s), 7.72 (2H, m), 7.85 (1H, s). (I) (50 mg) was dissolved in ethyl acetate (15 ml) and the solution was kept at room temperature for 4 d to give colorless single crystals.
All H atoms were included in the riding-model approximation with Uiso = 1.2Ueq for CH2 and 1.5Ueq for CH3. The terminal ethyl groups in the carbamate residues were found to be disorderd. There are two components of the disorder, each with unequal partial occupancies of 0.77 and 0.23 in the first molecule, and 0.52 and 0.48 in the second. The distances C14—C15, C14'—C15', C29—C30 and C29'—C30' were fixed at 1.54 Å and C14—O4, C14'—O4', C29—O8 and C29'—O8' were fixed at 1.45 Å.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Fig. 1. Unit-cell contents of (I) showing H-bonding interactions and the atomic numbering scheme. |
C15H18N2O4 | Z = 4 |
Mr = 290.31 | F(000) = 616 |
Triclinic, P1 | Dx = 1.275 Mg m−3 |
a = 6.933 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.210 (4) Å | Cell parameters from 936 reflections |
c = 15.913 (5) Å | θ = 2.8–23.1° |
α = 99.657 (6)° | µ = 0.09 mm−1 |
β = 101.373 (6)° | T = 293 K |
γ = 91.120 (6)° | Plate, colorless |
V = 1512.8 (8) Å3 | 0.30 × 0.20 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 5277 independent reflections |
Radiation source: fine-focus sealed tube | 2549 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 25.1°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −7→8 |
Tmin = 0.808, Tmax = 1.000 | k = −11→16 |
7713 measured reflections | l = −18→18 |
Refinement on F2 | 144 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.062 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.168 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.30 e Å−3 |
5277 reflections | Δρmin = −0.31 e Å−3 |
418 parameters |
C15H18N2O4 | γ = 91.120 (6)° |
Mr = 290.31 | V = 1512.8 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.933 (2) Å | Mo Kα radiation |
b = 14.210 (4) Å | µ = 0.09 mm−1 |
c = 15.913 (5) Å | T = 293 K |
α = 99.657 (6)° | 0.30 × 0.20 × 0.08 mm |
β = 101.373 (6)° |
Bruker SMART CCD area-detector diffractometer | 5277 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2549 reflections with I > 2σ(I) |
Tmin = 0.808, Tmax = 1.000 | Rint = 0.035 |
7713 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 144 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.30 e Å−3 |
5277 reflections | Δρmin = −0.31 e Å−3 |
418 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 | Occ. (<1) | |
O1 | 0.2078 (4) | 0.74190 (18) | 0.65282 (16) | 0.0753 (8) | |
O2 | 0.2449 (4) | 1.05357 (18) | 0.61838 (18) | 0.0852 (9) | |
O3 | 0.2613 (5) | 0.7533 (2) | 0.19331 (17) | 0.0892 (10) | |
O4 | 0.2792 (4) | 0.59472 (19) | 0.18682 (15) | 0.0713 (8) | |
O5 | 0.3010 (4) | 0.18798 (17) | 0.36444 (16) | 0.0729 (8) | |
O6 | 0.2679 (4) | 0.51277 (17) | 0.40089 (17) | 0.0765 (8) | |
O7 | 0.2139 (4) | 0.3674 (2) | 0.82189 (17) | 0.0822 (9) | |
O8 | 0.2318 (4) | 0.2111 (2) | 0.83008 (16) | 0.0833 (9) | |
N1 | 0.2251 (5) | 0.9050 (2) | 0.65709 (19) | 0.0633 (9) | |
N2 | 0.2604 (4) | 0.6823 (2) | 0.31219 (18) | 0.0569 (8) | |
H2C | 0.2591 | 0.6266 | 0.3266 | 0.068* | |
N3 | 0.2910 (4) | 0.3499 (2) | 0.36153 (18) | 0.0564 (8) | |
N4 | 0.2387 (4) | 0.2537 (2) | 0.70447 (18) | 0.0594 (8) | |
H4C | 0.2457 | 0.1929 | 0.6904 | 0.071* | |
C1 | 0.7594 (9) | 0.9999 (4) | 0.8653 (4) | 0.141 (2) | |
H1A | 0.8555 | 1.0434 | 0.8544 | 0.211* | |
H1B | 0.8082 | 0.9368 | 0.8609 | 0.211* | |
H1C | 0.7348 | 1.0202 | 0.9227 | 0.211* | |
C2 | 0.5683 (8) | 0.9986 (3) | 0.7983 (3) | 0.0958 (15) | |
H2A | 0.5217 | 1.0628 | 0.8023 | 0.115* | |
H2B | 0.5951 | 0.9796 | 0.7405 | 0.115* | |
C3 | 0.4107 (8) | 0.9328 (3) | 0.8102 (3) | 0.0899 (15) | |
H3A | 0.3917 | 0.9489 | 0.8696 | 0.108* | |
H3B | 0.4545 | 0.8680 | 0.8022 | 0.108* | |
C4 | 0.2146 (7) | 0.9352 (3) | 0.7488 (3) | 0.0796 (13) | |
H4A | 0.1183 | 0.8938 | 0.7635 | 0.096* | |
H4B | 0.1699 | 0.9998 | 0.7567 | 0.096* | |
C5 | 0.2223 (5) | 0.8104 (3) | 0.6169 (2) | 0.0568 (10) | |
C6 | 0.2372 (5) | 0.8119 (2) | 0.5262 (2) | 0.0479 (9) | |
C7 | 0.2408 (5) | 0.7379 (2) | 0.4594 (2) | 0.0505 (9) | |
H7A | 0.2338 | 0.6748 | 0.4676 | 0.061* | |
C8 | 0.2551 (5) | 0.7598 (2) | 0.3785 (2) | 0.0494 (9) | |
C9 | 0.2647 (5) | 0.8548 (3) | 0.3670 (2) | 0.0625 (11) | |
H9A | 0.2731 | 0.8686 | 0.3127 | 0.075* | |
C10 | 0.2618 (6) | 0.9289 (3) | 0.4355 (2) | 0.0652 (11) | |
H10A | 0.2688 | 0.9922 | 0.4277 | 0.078* | |
C11 | 0.2482 (5) | 0.9068 (2) | 0.5154 (2) | 0.0541 (9) | |
C12 | 0.2405 (6) | 0.9670 (3) | 0.5997 (3) | 0.0627 (10) | |
C13 | 0.2672 (6) | 0.6844 (3) | 0.2283 (2) | 0.0631 (10) | |
C14 | 0.336 (5) | 0.5752 (16) | 0.1028 (12) | 0.089 (10) | 0.23 (2) |
H14A | 0.4720 | 0.5575 | 0.1093 | 0.107* | 0.23 (2) |
H14B | 0.3214 | 0.6308 | 0.0745 | 0.107* | 0.23 (2) |
C15 | 0.196 (5) | 0.492 (3) | 0.050 (2) | 0.102 (10) | 0.23 (2) |
H15A | 0.2039 | 0.4849 | −0.0105 | 0.153* | 0.23 (2) |
H15B | 0.0634 | 0.5044 | 0.0558 | 0.153* | 0.23 (2) |
H15C | 0.2329 | 0.4338 | 0.0708 | 0.153* | 0.23 (2) |
C14' | 0.2600 (18) | 0.5866 (4) | 0.0916 (3) | 0.072 (2) | 0.77 (2) |
H14C | 0.3558 | 0.6298 | 0.0786 | 0.087* | 0.77 (2) |
H14D | 0.1291 | 0.6022 | 0.0649 | 0.087* | 0.77 (2) |
C15' | 0.297 (2) | 0.4850 (5) | 0.0585 (6) | 0.091 (3) | 0.77 (2) |
H15D | 0.2866 | 0.4759 | −0.0034 | 0.137* | 0.77 (2) |
H15E | 0.2006 | 0.4433 | 0.0718 | 0.137* | 0.77 (2) |
H15F | 0.4262 | 0.4706 | 0.0859 | 0.137* | 0.77 (2) |
C16 | −0.2171 (9) | 0.3378 (5) | 0.1388 (4) | 0.144 (2) | |
H16A | −0.3198 | 0.3817 | 0.1427 | 0.216* | |
H16B | −0.2603 | 0.2768 | 0.1489 | 0.216* | |
H16C | −0.1868 | 0.3306 | 0.0818 | 0.216* | |
C17 | −0.0326 (7) | 0.3764 (3) | 0.2074 (3) | 0.0890 (14) | |
H17A | 0.0078 | 0.4389 | 0.1978 | 0.107* | |
H17B | −0.0648 | 0.3844 | 0.2647 | 0.107* | |
C18 | 0.1357 (7) | 0.3124 (3) | 0.2052 (3) | 0.0805 (13) | |
H18A | 0.1677 | 0.3050 | 0.1479 | 0.097* | |
H18B | 0.0938 | 0.2498 | 0.2139 | 0.097* | |
C19 | 0.3203 (6) | 0.3477 (3) | 0.2728 (2) | 0.0711 (12) | |
H19A | 0.4260 | 0.3062 | 0.2627 | 0.085* | |
H19B | 0.3599 | 0.4115 | 0.2662 | 0.085* | |
C20 | 0.2861 (5) | 0.2690 (3) | 0.3999 (2) | 0.0550 (9) | |
C21 | 0.2629 (5) | 0.3043 (2) | 0.4906 (2) | 0.0468 (9) | |
C22 | 0.2584 (5) | 0.2547 (2) | 0.5569 (2) | 0.0500 (9) | |
H22A | 0.2670 | 0.1886 | 0.5486 | 0.060* | |
C23 | 0.2406 (5) | 0.3068 (2) | 0.6378 (2) | 0.0492 (9) | |
C24 | 0.2264 (5) | 0.4055 (2) | 0.6486 (2) | 0.0571 (10) | |
H24A | 0.2129 | 0.4393 | 0.7023 | 0.069* | |
C25 | 0.2320 (5) | 0.4540 (2) | 0.5804 (2) | 0.0585 (10) | |
H25A | 0.2235 | 0.5201 | 0.5879 | 0.070* | |
C26 | 0.2503 (5) | 0.4026 (2) | 0.5012 (2) | 0.0512 (9) | |
C27 | 0.2696 (5) | 0.4326 (3) | 0.4189 (2) | 0.0567 (10) | |
C28 | 0.2273 (6) | 0.2862 (3) | 0.7881 (2) | 0.0635 (10) | |
C29 | 0.1836 (18) | 0.2220 (11) | 0.9163 (6) | 0.085 (5) | 0.528 (18) |
H29A | 0.0765 | 0.1777 | 0.9176 | 0.102* | 0.528 (18) |
H29B | 0.1504 | 0.2868 | 0.9363 | 0.102* | 0.528 (18) |
C30 | 0.381 (2) | 0.1972 (14) | 0.9700 (8) | 0.123 (5) | 0.528 (18) |
H30A | 0.3736 | 0.2049 | 1.0303 | 0.185* | 0.528 (18) |
H30B | 0.4855 | 0.2390 | 0.9633 | 0.185* | 0.528 (18) |
H30C | 0.4076 | 0.1321 | 0.9496 | 0.185* | 0.528 (18) |
C29' | 0.254 (3) | 0.2426 (8) | 0.9266 (5) | 0.072 (4) | 0.472 (18) |
H29C | 0.1383 | 0.2749 | 0.9395 | 0.087* | 0.472 (18) |
H29D | 0.3687 | 0.2861 | 0.9495 | 0.087* | 0.472 (18) |
C30' | 0.276 (3) | 0.1531 (8) | 0.9663 (8) | 0.099 (5) | 0.472 (18) |
H30D | 0.2793 | 0.1691 | 1.0276 | 0.148* | 0.472 (18) |
H30E | 0.3968 | 0.1249 | 0.9572 | 0.148* | 0.472 (18) |
H30F | 0.1670 | 0.1085 | 0.9393 | 0.148* | 0.472 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.112 (2) | 0.0555 (16) | 0.0669 (18) | −0.0036 (15) | 0.0308 (16) | 0.0200 (14) |
O2 | 0.129 (3) | 0.0428 (16) | 0.087 (2) | 0.0120 (16) | 0.0293 (18) | 0.0103 (14) |
O3 | 0.140 (3) | 0.0706 (19) | 0.0563 (17) | −0.0100 (18) | 0.0121 (17) | 0.0207 (15) |
O4 | 0.093 (2) | 0.0732 (19) | 0.0501 (16) | 0.0037 (15) | 0.0216 (14) | 0.0082 (14) |
O5 | 0.109 (2) | 0.0485 (16) | 0.0622 (17) | 0.0231 (14) | 0.0222 (15) | 0.0050 (13) |
O6 | 0.107 (2) | 0.0474 (16) | 0.0833 (19) | 0.0077 (14) | 0.0313 (16) | 0.0212 (14) |
O7 | 0.114 (2) | 0.0688 (19) | 0.0608 (18) | 0.0134 (16) | 0.0187 (16) | −0.0005 (15) |
O8 | 0.127 (3) | 0.0767 (19) | 0.0534 (17) | 0.0236 (17) | 0.0289 (17) | 0.0169 (15) |
N1 | 0.087 (2) | 0.0477 (19) | 0.061 (2) | 0.0043 (16) | 0.0295 (18) | 0.0095 (16) |
N2 | 0.071 (2) | 0.0537 (18) | 0.0481 (19) | −0.0008 (15) | 0.0146 (16) | 0.0138 (15) |
N3 | 0.069 (2) | 0.0499 (18) | 0.0546 (19) | 0.0116 (15) | 0.0197 (16) | 0.0126 (15) |
N4 | 0.080 (2) | 0.0517 (18) | 0.0458 (19) | 0.0110 (16) | 0.0107 (16) | 0.0067 (15) |
C1 | 0.128 (5) | 0.140 (5) | 0.147 (5) | 0.012 (4) | 0.013 (4) | 0.021 (4) |
C2 | 0.122 (4) | 0.081 (3) | 0.090 (3) | −0.007 (3) | 0.037 (3) | 0.013 (3) |
C3 | 0.141 (5) | 0.071 (3) | 0.062 (3) | −0.001 (3) | 0.033 (3) | 0.010 (2) |
C4 | 0.119 (4) | 0.062 (3) | 0.069 (3) | 0.010 (2) | 0.048 (3) | 0.010 (2) |
C5 | 0.063 (3) | 0.050 (2) | 0.062 (2) | 0.0004 (18) | 0.019 (2) | 0.015 (2) |
C6 | 0.050 (2) | 0.041 (2) | 0.054 (2) | 0.0016 (16) | 0.0102 (17) | 0.0116 (17) |
C7 | 0.049 (2) | 0.043 (2) | 0.061 (2) | 0.0022 (16) | 0.0084 (18) | 0.0152 (18) |
C8 | 0.048 (2) | 0.051 (2) | 0.048 (2) | 0.0013 (16) | 0.0046 (17) | 0.0128 (18) |
C9 | 0.077 (3) | 0.059 (2) | 0.054 (2) | −0.005 (2) | 0.010 (2) | 0.020 (2) |
C10 | 0.083 (3) | 0.049 (2) | 0.065 (3) | 0.0005 (19) | 0.009 (2) | 0.022 (2) |
C11 | 0.060 (3) | 0.045 (2) | 0.057 (2) | 0.0045 (17) | 0.0098 (19) | 0.0112 (18) |
C12 | 0.071 (3) | 0.050 (2) | 0.070 (3) | 0.006 (2) | 0.018 (2) | 0.014 (2) |
C13 | 0.068 (3) | 0.063 (3) | 0.056 (3) | −0.006 (2) | 0.003 (2) | 0.012 (2) |
C14 | 0.092 (13) | 0.096 (12) | 0.078 (12) | −0.001 (9) | 0.007 (8) | 0.025 (8) |
C15 | 0.106 (14) | 0.105 (13) | 0.092 (12) | 0.010 (9) | 0.018 (9) | 0.014 (9) |
C14' | 0.082 (5) | 0.084 (4) | 0.050 (4) | 0.001 (4) | 0.010 (3) | 0.011 (3) |
C15' | 0.109 (7) | 0.097 (5) | 0.071 (4) | 0.019 (5) | 0.036 (5) | 0.004 (3) |
C16 | 0.130 (5) | 0.183 (5) | 0.121 (4) | −0.010 (4) | −0.010 (4) | 0.074 (4) |
C17 | 0.102 (4) | 0.095 (3) | 0.080 (3) | 0.009 (3) | 0.023 (3) | 0.039 (3) |
C18 | 0.123 (4) | 0.067 (3) | 0.059 (3) | 0.011 (3) | 0.029 (3) | 0.019 (2) |
C19 | 0.084 (3) | 0.073 (3) | 0.066 (3) | 0.017 (2) | 0.032 (2) | 0.019 (2) |
C20 | 0.057 (3) | 0.051 (2) | 0.058 (2) | 0.0140 (18) | 0.0106 (19) | 0.011 (2) |
C21 | 0.046 (2) | 0.044 (2) | 0.049 (2) | 0.0096 (16) | 0.0065 (17) | 0.0060 (17) |
C22 | 0.055 (2) | 0.0401 (18) | 0.051 (2) | 0.0089 (16) | 0.0022 (18) | 0.0044 (17) |
C23 | 0.048 (2) | 0.047 (2) | 0.051 (2) | 0.0073 (16) | 0.0044 (17) | 0.0082 (18) |
C24 | 0.065 (3) | 0.051 (2) | 0.052 (2) | 0.0103 (18) | 0.0106 (19) | −0.0006 (18) |
C25 | 0.069 (3) | 0.0368 (19) | 0.067 (3) | 0.0105 (17) | 0.012 (2) | 0.0035 (19) |
C26 | 0.050 (2) | 0.044 (2) | 0.060 (2) | 0.0067 (16) | 0.0114 (18) | 0.0081 (18) |
C27 | 0.059 (3) | 0.046 (2) | 0.067 (3) | 0.0092 (18) | 0.015 (2) | 0.012 (2) |
C28 | 0.069 (3) | 0.067 (3) | 0.055 (3) | 0.016 (2) | 0.010 (2) | 0.012 (2) |
C29 | 0.094 (8) | 0.087 (7) | 0.067 (6) | −0.001 (6) | 0.013 (5) | −0.002 (5) |
C30 | 0.132 (9) | 0.146 (9) | 0.089 (7) | 0.002 (7) | 0.019 (6) | 0.020 (6) |
C29' | 0.081 (8) | 0.088 (7) | 0.050 (6) | 0.011 (6) | 0.014 (5) | 0.017 (5) |
C30' | 0.134 (10) | 0.097 (7) | 0.071 (6) | 0.000 (6) | 0.028 (6) | 0.023 (6) |
O1—C5 | 1.220 (4) | C14—C15 | 1.535 (10) |
O2—C12 | 1.214 (4) | C14—H14A | 0.9700 |
O3—C13 | 1.202 (4) | C14—H14B | 0.9700 |
O4—C13 | 1.346 (4) | C15—H15A | 0.9600 |
O4—C14 | 1.453 (9) | C15—H15B | 0.9600 |
O4—C14' | 1.479 (5) | C15—H15C | 0.9600 |
O5—C20 | 1.211 (4) | C14'—C15' | 1.497 (7) |
O6—C27 | 1.220 (4) | C14'—H14C | 0.9700 |
O7—C28 | 1.201 (4) | C14'—H14D | 0.9700 |
O8—C28 | 1.349 (4) | C15'—H15D | 0.9600 |
O8—C29 | 1.459 (7) | C15'—H15E | 0.9600 |
O8—C29' | 1.502 (7) | C15'—H15F | 0.9600 |
N1—C5 | 1.386 (4) | C16—C17 | 1.533 (6) |
N1—C12 | 1.389 (4) | C16—H16A | 0.9600 |
N1—C4 | 1.467 (5) | C16—H16B | 0.9600 |
N2—C13 | 1.350 (4) | C16—H16C | 0.9600 |
N2—C8 | 1.398 (4) | C17—C18 | 1.496 (6) |
N2—H2C | 0.8600 | C17—H17A | 0.9700 |
N3—C27 | 1.392 (4) | C17—H17B | 0.9700 |
N3—C20 | 1.392 (4) | C18—C19 | 1.515 (6) |
N3—C19 | 1.462 (4) | C18—H18A | 0.9700 |
N4—C28 | 1.352 (4) | C18—H18B | 0.9700 |
N4—C23 | 1.402 (4) | C19—H19A | 0.9700 |
N4—H4C | 0.8600 | C19—H19B | 0.9700 |
C1—C2 | 1.526 (7) | C20—C21 | 1.488 (5) |
C1—H1A | 0.9600 | C21—C22 | 1.368 (4) |
C1—H1B | 0.9600 | C21—C26 | 1.385 (4) |
C1—H1C | 0.9600 | C22—C23 | 1.403 (4) |
C2—C3 | 1.485 (6) | C22—H22A | 0.9300 |
C2—H2A | 0.9700 | C23—C24 | 1.392 (4) |
C2—H2B | 0.9700 | C24—C25 | 1.388 (5) |
C3—C4 | 1.515 (6) | C24—H24A | 0.9300 |
C3—H3A | 0.9700 | C25—C26 | 1.376 (5) |
C3—H3B | 0.9700 | C25—H25A | 0.9300 |
C4—H4A | 0.9700 | C26—C27 | 1.473 (5) |
C4—H4B | 0.9700 | C29—C30 | 1.546 (9) |
C5—C6 | 1.471 (5) | C29—H29A | 0.9700 |
C6—C7 | 1.368 (4) | C29—H29B | 0.9700 |
C6—C11 | 1.391 (4) | C30—H30A | 0.9600 |
C7—C8 | 1.396 (4) | C30—H30B | 0.9600 |
C7—H7A | 0.9300 | C30—H30C | 0.9600 |
C8—C9 | 1.393 (5) | C29'—C30' | 1.509 (9) |
C9—C10 | 1.386 (5) | C29'—H29C | 0.9700 |
C9—H9A | 0.9300 | C29'—H29D | 0.9700 |
C10—C11 | 1.381 (5) | C30'—H30D | 0.9600 |
C10—H10A | 0.9300 | C30'—H30E | 0.9600 |
C11—C12 | 1.475 (5) | C30'—H30F | 0.9600 |
C13—O4—C14 | 122.0 (10) | O4—C14'—H14D | 110.5 |
C13—O4—C14' | 113.8 (4) | C15'—C14'—H14D | 110.5 |
C14—O4—C14' | 22.0 (13) | H14C—C14'—H14D | 108.7 |
C28—O8—C29 | 120.5 (6) | C14'—C15'—H15D | 109.5 |
C28—O8—C29' | 111.8 (5) | C14'—C15'—H15E | 109.5 |
C29—O8—C29' | 21.1 (8) | H15D—C15'—H15E | 109.5 |
C5—N1—C12 | 111.4 (3) | C14'—C15'—H15F | 109.5 |
C5—N1—C4 | 124.1 (3) | H15D—C15'—H15F | 109.5 |
C12—N1—C4 | 124.5 (3) | H15E—C15'—H15F | 109.5 |
C13—N2—C8 | 127.7 (3) | C17—C16—H16A | 109.5 |
C13—N2—H2C | 116.2 | C17—C16—H16B | 109.5 |
C8—N2—H2C | 116.2 | H16A—C16—H16B | 109.5 |
C27—N3—C20 | 111.5 (3) | C17—C16—H16C | 109.5 |
C27—N3—C19 | 124.6 (3) | H16A—C16—H16C | 109.5 |
C20—N3—C19 | 123.8 (3) | H16B—C16—H16C | 109.5 |
C28—N4—C23 | 128.0 (3) | C18—C17—C16 | 112.9 (4) |
C28—N4—H4C | 116.0 | C18—C17—H17A | 109.0 |
C23—N4—H4C | 116.0 | C16—C17—H17A | 109.0 |
C2—C1—H1A | 109.5 | C18—C17—H17B | 109.0 |
C2—C1—H1B | 109.5 | C16—C17—H17B | 109.0 |
H1A—C1—H1B | 109.5 | H17A—C17—H17B | 107.8 |
C2—C1—H1C | 109.5 | C17—C18—C19 | 114.5 (4) |
H1A—C1—H1C | 109.5 | C17—C18—H18A | 108.6 |
H1B—C1—H1C | 109.5 | C19—C18—H18A | 108.6 |
C3—C2—C1 | 113.2 (4) | C17—C18—H18B | 108.6 |
C3—C2—H2A | 108.9 | C19—C18—H18B | 108.6 |
C1—C2—H2A | 108.9 | H18A—C18—H18B | 107.6 |
C3—C2—H2B | 108.9 | N3—C19—C18 | 112.2 (3) |
C1—C2—H2B | 108.9 | N3—C19—H19A | 109.2 |
H2A—C2—H2B | 107.8 | C18—C19—H19A | 109.2 |
C2—C3—C4 | 114.4 (4) | N3—C19—H19B | 109.2 |
C2—C3—H3A | 108.7 | C18—C19—H19B | 109.2 |
C4—C3—H3A | 108.7 | H19A—C19—H19B | 107.9 |
C2—C3—H3B | 108.7 | O5—C20—N3 | 125.1 (3) |
C4—C3—H3B | 108.7 | O5—C20—C21 | 129.1 (3) |
H3A—C3—H3B | 107.6 | N3—C20—C21 | 105.8 (3) |
N1—C4—C3 | 112.8 (3) | C22—C21—C26 | 122.3 (3) |
N1—C4—H4A | 109.0 | C22—C21—C20 | 129.6 (3) |
C3—C4—H4A | 109.0 | C26—C21—C20 | 108.1 (3) |
N1—C4—H4B | 109.0 | C21—C22—C23 | 117.7 (3) |
C3—C4—H4B | 109.0 | C21—C22—H22A | 121.1 |
H4A—C4—H4B | 107.8 | C23—C22—H22A | 121.1 |
O1—C5—N1 | 124.4 (3) | C24—C23—N4 | 123.6 (3) |
O1—C5—C6 | 129.1 (3) | C24—C23—C22 | 120.2 (3) |
N1—C5—C6 | 106.5 (3) | N4—C23—C22 | 116.2 (3) |
C7—C6—C11 | 121.9 (3) | C25—C24—C23 | 120.9 (3) |
C7—C6—C5 | 130.1 (3) | C25—C24—H24A | 119.6 |
C11—C6—C5 | 108.0 (3) | C23—C24—H24A | 119.6 |
C6—C7—C8 | 118.2 (3) | C26—C25—C24 | 118.7 (3) |
C6—C7—H7A | 120.9 | C26—C25—H25A | 120.7 |
C8—C7—H7A | 120.9 | C24—C25—H25A | 120.7 |
C9—C8—C7 | 120.3 (3) | C25—C26—C21 | 120.2 (3) |
C9—C8—N2 | 123.4 (3) | C25—C26—C27 | 131.8 (3) |
C7—C8—N2 | 116.4 (3) | C21—C26—C27 | 107.9 (3) |
C10—C9—C8 | 120.8 (3) | O6—C27—N3 | 124.3 (3) |
C10—C9—H9A | 119.6 | O6—C27—C26 | 129.1 (3) |
C8—C9—H9A | 119.6 | N3—C27—C26 | 106.6 (3) |
C11—C10—C9 | 118.7 (3) | O7—C28—O8 | 123.7 (3) |
C11—C10—H10A | 120.7 | O7—C28—N4 | 127.7 (3) |
C9—C10—H10A | 120.7 | O8—C28—N4 | 108.5 (3) |
C10—C11—C6 | 120.1 (3) | O8—C29—C30 | 100.2 (8) |
C10—C11—C12 | 132.3 (3) | O8—C29—H29A | 111.7 |
C6—C11—C12 | 107.6 (3) | C30—C29—H29A | 111.7 |
O2—C12—N1 | 124.6 (4) | O8—C29—H29B | 111.7 |
O2—C12—C11 | 128.9 (4) | C30—C29—H29B | 111.7 |
N1—C12—C11 | 106.5 (3) | H29A—C29—H29B | 109.5 |
O3—C13—O4 | 123.5 (3) | C29—C30—H30A | 109.5 |
O3—C13—N2 | 127.5 (4) | C29—C30—H30B | 109.5 |
O4—C13—N2 | 109.1 (3) | H30A—C30—H30B | 109.5 |
O4—C14—C15 | 105 (2) | C29—C30—H30C | 109.5 |
O4—C14—H14A | 110.7 | H30A—C30—H30C | 109.5 |
C15—C14—H14A | 110.7 | H30B—C30—H30C | 109.5 |
O4—C14—H14B | 110.7 | O8—C29'—C30' | 106.4 (8) |
C15—C14—H14B | 110.7 | O8—C29'—H29C | 110.4 |
H14A—C14—H14B | 108.8 | C30'—C29'—H29C | 110.4 |
C14—C15—H15A | 109.5 | O8—C29'—H29D | 110.4 |
C14—C15—H15B | 109.5 | C30'—C29'—H29D | 110.4 |
H15A—C15—H15B | 109.5 | H29C—C29'—H29D | 108.6 |
C14—C15—H15C | 109.5 | C29'—C30'—H30D | 109.5 |
H15A—C15—H15C | 109.5 | C29'—C30'—H30E | 109.5 |
H15B—C15—H15C | 109.5 | H30D—C30'—H30E | 109.5 |
O4—C14'—C15' | 106.0 (6) | C29'—C30'—H30F | 109.5 |
O4—C14'—H14C | 110.5 | H30D—C30'—H30F | 109.5 |
C15'—C14'—H14C | 110.5 | H30E—C30'—H30F | 109.5 |
C1—C2—C3—C4 | 175.8 (4) | C16—C17—C18—C19 | −179.4 (4) |
C5—N1—C4—C3 | 79.9 (5) | C27—N3—C19—C18 | −104.9 (4) |
C12—N1—C4—C3 | −99.6 (4) | C20—N3—C19—C18 | 76.9 (4) |
C2—C3—C4—N1 | 62.6 (5) | C17—C18—C19—N3 | 65.3 (4) |
C12—N1—C5—O1 | −179.2 (4) | C27—N3—C20—O5 | 179.8 (3) |
C4—N1—C5—O1 | 1.2 (6) | C19—N3—C20—O5 | −1.7 (6) |
C12—N1—C5—C6 | 0.0 (4) | C27—N3—C20—C21 | −1.0 (4) |
C4—N1—C5—C6 | −179.5 (3) | C19—N3—C20—C21 | 177.4 (3) |
O1—C5—C6—C7 | −0.8 (7) | O5—C20—C21—C22 | 2.2 (6) |
N1—C5—C6—C7 | −180.0 (3) | N3—C20—C21—C22 | −176.9 (3) |
O1—C5—C6—C11 | 179.2 (4) | O5—C20—C21—C26 | −179.5 (4) |
N1—C5—C6—C11 | −0.1 (4) | N3—C20—C21—C26 | 1.4 (4) |
C11—C6—C7—C8 | −0.2 (5) | C26—C21—C22—C23 | 0.0 (5) |
C5—C6—C7—C8 | 179.7 (3) | C20—C21—C22—C23 | 178.1 (3) |
C6—C7—C8—C9 | −0.3 (5) | C28—N4—C23—C24 | −1.3 (6) |
C6—C7—C8—N2 | 179.4 (3) | C28—N4—C23—C22 | 178.5 (3) |
C13—N2—C8—C9 | −2.8 (6) | C21—C22—C23—C24 | 0.5 (5) |
C13—N2—C8—C7 | 177.6 (3) | C21—C22—C23—N4 | −179.3 (3) |
C7—C8—C9—C10 | 0.6 (5) | N4—C23—C24—C25 | 179.1 (3) |
N2—C8—C9—C10 | −179.0 (3) | C22—C23—C24—C25 | −0.8 (5) |
C8—C9—C10—C11 | −0.3 (6) | C23—C24—C25—C26 | 0.5 (5) |
C9—C10—C11—C6 | −0.1 (6) | C24—C25—C26—C21 | 0.0 (5) |
C9—C10—C11—C12 | −179.6 (4) | C24—C25—C26—C27 | −176.8 (4) |
C7—C6—C11—C10 | 0.4 (5) | C22—C21—C26—C25 | −0.2 (5) |
C5—C6—C11—C10 | −179.5 (3) | C20—C21—C26—C25 | −178.7 (3) |
C7—C6—C11—C12 | 180.0 (3) | C22—C21—C26—C27 | 177.2 (3) |
C5—C6—C11—C12 | 0.0 (4) | C20—C21—C26—C27 | −1.3 (4) |
C5—N1—C12—O2 | 179.6 (4) | C20—N3—C27—O6 | −179.6 (3) |
C4—N1—C12—O2 | −0.8 (6) | C19—N3—C27—O6 | 1.9 (6) |
C5—N1—C12—C11 | 0.0 (4) | C20—N3—C27—C26 | 0.3 (4) |
C4—N1—C12—C11 | 179.6 (4) | C19—N3—C27—C26 | −178.1 (3) |
C10—C11—C12—O2 | −0.2 (7) | C25—C26—C27—O6 | −2.4 (7) |
C6—C11—C12—O2 | −179.6 (4) | C21—C26—C27—O6 | −179.5 (4) |
C10—C11—C12—N1 | 179.4 (4) | C25—C26—C27—N3 | 177.7 (4) |
C6—C11—C12—N1 | 0.0 (4) | C21—C26—C27—N3 | 0.6 (4) |
C14—O4—C13—O3 | 16.0 (17) | C29—O8—C28—O7 | 11.5 (8) |
C14'—O4—C13—O3 | −7.1 (7) | C29'—O8—C28—O7 | −10.0 (10) |
C14—O4—C13—N2 | −164.8 (16) | C29—O8—C28—N4 | −168.1 (7) |
C14'—O4—C13—N2 | 172.1 (6) | C29'—O8—C28—N4 | 170.5 (9) |
C8—N2—C13—O3 | −3.6 (7) | C23—N4—C28—O7 | 1.0 (7) |
C8—N2—C13—O4 | 177.3 (3) | C23—N4—C28—O8 | −179.5 (3) |
C13—O4—C14—C15 | −138 (2) | C28—O8—C29—C30 | −118.3 (12) |
C14'—O4—C14—C15 | −64 (3) | C29'—O8—C29—C30 | −47.6 (18) |
C13—O4—C14'—C15' | 174.6 (9) | C28—O8—C29'—C30' | −174.7 (14) |
C14—O4—C14'—C15' | 57 (3) | C29—O8—C29'—C30' | 66 (2) |
Experimental details
Crystal data | |
Chemical formula | C15H18N2O4 |
Mr | 290.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.933 (2), 14.210 (4), 15.913 (5) |
α, β, γ (°) | 99.657 (6), 101.373 (6), 91.120 (6) |
V (Å3) | 1512.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.808, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7713, 5277, 2549 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.168, 1.03 |
No. of reflections | 5277 |
No. of parameters | 418 |
No. of restraints | 144 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.31 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
O1—C5 | 1.220 (4) | N1—C5 | 1.386 (4) |
O4—C13 | 1.346 (4) | N2—C13 | 1.350 (4) |
O5—C20 | 1.211 (4) | N3—C27 | 1.392 (4) |
O8—C28 | 1.349 (4) | N4—C28 | 1.352 (4) |
C13—O4—C14 | 122.0 (10) | C27—N3—C20 | 111.5 (3) |
C28—O8—C29 | 120.5 (6) | C28—N4—C23 | 128.0 (3) |
C5—N1—C12 | 111.4 (3) | O1—C5—C6 | 129.1 (3) |
C13—N2—C8 | 127.7 (3) | O5—C20—C21 | 129.1 (3) |
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Organic carbamates are valuable synthetic intermediates, and are ubiquitously found in a variety of biologically active compounds (Vauthey et al., 2000). Functionalization of the carbamate moiety offers an attractive method for the generation of derivatives which may constitute interesting medicinal and biological properties (Folkmann et al., 1990). We are interested in phthalimide derivatives and a search of the literature revealed that some phthalimide derivatives had cytotoxicity (Hall et al., 1995) and anti-HIV activity (Van Derpoorten et al., 1997). It was assumed that compounds having both phthalimide and carbamate residues in one molecule may possess some attractive biological activities. In this connection, the structure of the title compound, ethyl N-(2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)carbamate, (I), is reported.
There are two independent molecules of (I) comprising the asymmetric unit and all molecules are connected into a chain via N—H···O contacts: H···O 2.15 Å, N···O 2.985 (16) Å and N—H···O 163° for N2—H···O6; H···O 2.11 Å, N···O 2.947 (16) Å and N—H···O 163° for N4—H···O2i [symmetry code: (i) x, −1 + y, z] (Fig. 1 and Table 1). This arrangement is similar to that found for phthalimide (Zakaria et al., 2002). The phthalimide group is planar, with the mean deviation from the least-squares plane being 0.005 (3) Å [0.015 (4) Å for the second independent molecule]. This observation is diferent from the related N-(3-iodopropyl)phthalimide moiety which is not exactly planar (Chandramohan et al., 2000). The carbamate moiety is effectively planar, as reflected in the mean deviation of the atoms from this plane of 0.002 (3) Å [0.001 (3) Å], in good agreement with the corresponding data for ethyl N-(3-oxobutanoyl)carbamate (Golden et al., 2002). The dihedral angle between the mean planes of the phthalimide and carbamate moieties is 5.7 (3) and 5.9 (3)°, respectively. The n-butyl moieties (C1/C2/C3/C4 and C16/C17/C18/C19) and phthalimide groups are folded towards each other, making an dihedral angle of 106.4 (2)° [101.7 (2)°], which is somewhat different from the corresponding angles found in the N-(3-iodopropyl)phthalimide structure of 76.6 (2)° (Chandramohan et al., 2000).