The title compound, C
17H
20N
2O
3, was synthesized by the substituted one-carbon unit transfer reaction of tryptamine with an imidazolidine derivative. There are intramolecular and intermolecular N—H
O hydrogen bonds in the crystal structure.
Supporting information
CCDC reference: 263713
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.111
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.494 0.973
Tmin' and Tmax expected: 0.964 0.973
RR' = 0.513
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.51
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 6.22 su
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.
Ethyl 2-acetyl-3-[2-(1
H-indol-3-yl)ethylamino]propenoate
top
Crystal data top
C17H20N2O3 | Z = 2 |
Mr = 300.35 | F(000) = 320 |
Triclinic, P1 | Dx = 1.303 Mg m−3 |
a = 8.4342 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.391 (2) Å | Cell parameters from 1672 reflections |
c = 10.360 (2) Å | θ = 2.6–26.9° |
α = 79.941 (3)° | µ = 0.09 mm−1 |
β = 71.597 (3)° | T = 183 K |
γ = 89.332 (3)° | Block, colorless |
V = 765.8 (3) Å3 | 0.40 × 0.30 × 0.30 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2636 independent reflections |
Radiation source: fine-focus sealed tube | 2154 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→8 |
Tmin = 0.494, Tmax = 0.973 | k = −10→11 |
3165 measured reflections | l = −12→12 |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0645P)2] where P = (Fo2 + 2Fc2)/3 |
2636 reflections | (Δ/σ)max < 0.001 |
201 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.06078 (13) | 0.61983 (13) | 0.36769 (12) | 0.0367 (3) | |
O2 | 0.46298 (15) | 0.82821 (13) | 0.03923 (12) | 0.0410 (3) | |
O3 | 0.60063 (15) | 0.62634 (12) | 0.06465 (12) | 0.0412 (3) | |
N1 | 0.40414 (17) | −0.04562 (14) | 0.78771 (13) | 0.0311 (3) | |
H1 | 0.4528 | −0.0584 | 0.8523 | 0.037* | |
N2 | 0.28535 (16) | 0.43809 (14) | 0.41933 (13) | 0.0306 (3) | |
H2 | 0.1776 | 0.4533 | 0.4450 | 0.037* | |
C1 | 0.25980 (19) | −0.08463 (17) | 0.64843 (15) | 0.0268 (4) | |
C2 | 0.1666 (2) | −0.16850 (19) | 0.59696 (17) | 0.0342 (4) | |
H2A | 0.1292 | −0.1273 | 0.5218 | 0.041* | |
C3 | 0.1301 (2) | −0.31164 (19) | 0.65694 (18) | 0.0383 (4) | |
H3 | 0.0666 | −0.3696 | 0.6227 | 0.046* | |
C4 | 0.1841 (2) | −0.37327 (19) | 0.76675 (18) | 0.0378 (4) | |
H4 | 0.1562 | −0.4725 | 0.8064 | 0.045* | |
C5 | 0.2772 (2) | −0.29412 (18) | 0.81940 (17) | 0.0330 (4) | |
H5 | 0.3147 | −0.3369 | 0.8940 | 0.040* | |
C6 | 0.3140 (2) | −0.14922 (17) | 0.75912 (16) | 0.0283 (4) | |
C7 | 0.31928 (19) | 0.06404 (17) | 0.61249 (15) | 0.0266 (4) | |
C8 | 0.4058 (2) | 0.08124 (17) | 0.69889 (16) | 0.0294 (4) | |
H8 | 0.4605 | 0.1694 | 0.6981 | 0.035* | |
C9 | 0.2874 (2) | 0.17564 (17) | 0.50269 (16) | 0.0296 (4) | |
H9A | 0.1662 | 0.1742 | 0.5150 | 0.036* | |
H9B | 0.3465 | 0.1510 | 0.4110 | 0.036* | |
C10 | 0.3451 (2) | 0.32607 (17) | 0.50645 (17) | 0.0313 (4) | |
H10A | 0.3046 | 0.3430 | 0.6030 | 0.038* | |
H10B | 0.4689 | 0.3330 | 0.4754 | 0.038* | |
C11 | 0.3809 (2) | 0.51711 (17) | 0.30607 (16) | 0.0289 (4) | |
H11 | 0.4937 | 0.4903 | 0.2744 | 0.035* | |
C12 | 0.3377 (2) | 0.63612 (17) | 0.22580 (16) | 0.0272 (4) | |
C13 | 0.1716 (2) | 0.69010 (18) | 0.26918 (17) | 0.0291 (4) | |
C14 | 0.1296 (2) | 0.8319 (2) | 0.19874 (19) | 0.0457 (5) | |
H14A | 0.0102 | 0.8470 | 0.2389 | 0.069* | |
H14B | 0.1557 | 0.8311 | 0.0998 | 0.069* | |
H14C | 0.1955 | 0.9105 | 0.2115 | 0.069* | |
C15 | 0.4675 (2) | 0.70816 (18) | 0.10318 (17) | 0.0302 (4) | |
C16 | 0.7388 (2) | 0.6907 (2) | −0.05471 (19) | 0.0468 (5) | |
H16A | 0.6946 | 0.7461 | −0.1253 | 0.056* | |
H16B | 0.8064 | 0.6132 | −0.0955 | 0.056* | |
C17 | 0.8469 (2) | 0.7888 (2) | −0.0164 (2) | 0.0508 (5) | |
H17A | 0.7828 | 0.8706 | 0.0158 | 0.076* | |
H17B | 0.9438 | 0.8248 | −0.0974 | 0.076* | |
H17C | 0.8853 | 0.7355 | 0.0575 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0294 (7) | 0.0336 (7) | 0.0420 (7) | 0.0007 (5) | −0.0084 (6) | 0.0010 (6) |
O2 | 0.0388 (7) | 0.0389 (8) | 0.0384 (7) | 0.0013 (6) | −0.0135 (6) | 0.0133 (6) |
O3 | 0.0342 (7) | 0.0335 (7) | 0.0431 (7) | 0.0035 (6) | 0.0022 (6) | −0.0007 (6) |
N1 | 0.0376 (8) | 0.0273 (8) | 0.0315 (8) | 0.0026 (6) | −0.0172 (6) | −0.0016 (6) |
N2 | 0.0270 (8) | 0.0252 (8) | 0.0351 (8) | 0.0009 (6) | −0.0080 (6) | 0.0031 (6) |
C1 | 0.0251 (9) | 0.0256 (9) | 0.0262 (8) | 0.0032 (7) | −0.0037 (7) | −0.0037 (7) |
C2 | 0.0339 (10) | 0.0346 (10) | 0.0352 (9) | 0.0019 (8) | −0.0127 (8) | −0.0064 (8) |
C3 | 0.0365 (10) | 0.0313 (10) | 0.0465 (11) | −0.0034 (8) | −0.0097 (9) | −0.0114 (8) |
C4 | 0.0368 (10) | 0.0235 (10) | 0.0450 (11) | 0.0017 (8) | −0.0039 (8) | −0.0023 (8) |
C5 | 0.0352 (10) | 0.0268 (10) | 0.0326 (9) | 0.0072 (8) | −0.0072 (8) | −0.0013 (7) |
C6 | 0.0269 (9) | 0.0264 (9) | 0.0284 (9) | 0.0051 (7) | −0.0044 (7) | −0.0051 (7) |
C7 | 0.0272 (9) | 0.0242 (9) | 0.0254 (8) | 0.0034 (7) | −0.0051 (7) | −0.0032 (7) |
C8 | 0.0333 (10) | 0.0226 (9) | 0.0304 (9) | 0.0011 (7) | −0.0084 (7) | −0.0028 (7) |
C9 | 0.0325 (9) | 0.0268 (9) | 0.0286 (9) | 0.0034 (7) | −0.0105 (7) | −0.0012 (7) |
C10 | 0.0338 (10) | 0.0260 (9) | 0.0326 (9) | 0.0020 (7) | −0.0126 (8) | 0.0025 (7) |
C11 | 0.0275 (9) | 0.0253 (9) | 0.0341 (9) | −0.0003 (7) | −0.0095 (7) | −0.0064 (7) |
C12 | 0.0287 (9) | 0.0224 (9) | 0.0308 (9) | 0.0004 (7) | −0.0116 (7) | −0.0013 (7) |
C13 | 0.0323 (10) | 0.0255 (9) | 0.0307 (9) | 0.0001 (7) | −0.0132 (8) | −0.0022 (7) |
C14 | 0.0404 (11) | 0.0407 (12) | 0.0475 (11) | 0.0136 (9) | −0.0092 (9) | 0.0050 (9) |
C15 | 0.0321 (10) | 0.0300 (10) | 0.0308 (9) | −0.0015 (7) | −0.0146 (7) | −0.0021 (8) |
C16 | 0.0393 (11) | 0.0458 (12) | 0.0416 (11) | 0.0013 (9) | 0.0039 (9) | −0.0038 (9) |
C17 | 0.0430 (12) | 0.0435 (12) | 0.0540 (12) | 0.0014 (9) | −0.0018 (10) | −0.0031 (10) |
Geometric parameters (Å, º) top
O1—C13 | 1.2358 (19) | C7—C9 | 1.495 (2) |
O2—C15 | 1.2105 (19) | C8—H8 | 0.9500 |
O3—C15 | 1.347 (2) | C9—C10 | 1.510 (2) |
O3—C16 | 1.448 (2) | C9—H9A | 0.9900 |
N1—C6 | 1.368 (2) | C9—H9B | 0.9900 |
N1—C8 | 1.369 (2) | C10—H10A | 0.9900 |
N1—H1 | 0.8800 | C10—H10B | 0.9900 |
N2—C11 | 1.2998 (19) | C11—C12 | 1.389 (2) |
N2—C10 | 1.4556 (19) | C11—H11 | 0.9500 |
N2—H2 | 0.8800 | C12—C13 | 1.445 (2) |
C1—C2 | 1.396 (2) | C12—C15 | 1.452 (2) |
C1—C6 | 1.405 (2) | C13—C14 | 1.498 (2) |
C1—C7 | 1.434 (2) | C14—H14A | 0.9800 |
C2—C3 | 1.373 (2) | C14—H14B | 0.9800 |
C2—H2A | 0.9500 | C14—H14C | 0.9800 |
C3—C4 | 1.389 (3) | C16—C17 | 1.487 (3) |
C3—H3 | 0.9500 | C16—H16A | 0.9900 |
C4—C5 | 1.375 (3) | C16—H16B | 0.9900 |
C4—H4 | 0.9500 | C17—H17A | 0.9800 |
C5—C6 | 1.389 (2) | C17—H17B | 0.9800 |
C5—H5 | 0.9500 | C17—H17C | 0.9800 |
C7—C8 | 1.351 (2) | | |
| | | |
C15—O3—C16 | 116.60 (13) | N2—C10—C9 | 112.55 (13) |
C6—N1—C8 | 108.48 (13) | N2—C10—H10A | 109.1 |
C6—N1—H1 | 125.8 | C9—C10—H10A | 109.1 |
C8—N1—H1 | 125.8 | N2—C10—H10B | 109.1 |
C11—N2—C10 | 124.21 (14) | C9—C10—H10B | 109.1 |
C11—N2—H2 | 117.9 | H10A—C10—H10B | 107.8 |
C10—N2—H2 | 117.9 | N2—C11—C12 | 127.75 (15) |
C2—C1—C6 | 119.13 (15) | N2—C11—H11 | 116.1 |
C2—C1—C7 | 133.74 (15) | C12—C11—H11 | 116.1 |
C6—C1—C7 | 107.13 (14) | C11—C12—C13 | 120.30 (14) |
C3—C2—C1 | 118.77 (16) | C11—C12—C15 | 117.70 (15) |
C3—C2—H2A | 120.6 | C13—C12—C15 | 121.88 (14) |
C1—C2—H2A | 120.6 | O1—C13—C12 | 120.02 (14) |
C2—C3—C4 | 121.22 (17) | O1—C13—C14 | 118.46 (15) |
C2—C3—H3 | 119.4 | C12—C13—C14 | 121.52 (15) |
C4—C3—H3 | 119.4 | C13—C14—H14A | 109.5 |
C5—C4—C3 | 121.56 (16) | C13—C14—H14B | 109.5 |
C5—C4—H4 | 119.2 | H14A—C14—H14B | 109.5 |
C3—C4—H4 | 119.2 | C13—C14—H14C | 109.5 |
C4—C5—C6 | 117.35 (16) | H14A—C14—H14C | 109.5 |
C4—C5—H5 | 121.3 | H14B—C14—H14C | 109.5 |
C6—C5—H5 | 121.3 | O2—C15—O3 | 121.37 (15) |
N1—C6—C5 | 130.51 (15) | O2—C15—C12 | 126.07 (16) |
N1—C6—C1 | 107.51 (14) | O3—C15—C12 | 112.56 (14) |
C5—C6—C1 | 121.97 (16) | O3—C16—C17 | 111.25 (16) |
C8—C7—C1 | 106.03 (14) | O3—C16—H16A | 109.4 |
C8—C7—C9 | 127.97 (15) | C17—C16—H16A | 109.4 |
C1—C7—C9 | 125.99 (14) | O3—C16—H16B | 109.4 |
C7—C8—N1 | 110.85 (15) | C17—C16—H16B | 109.4 |
C7—C8—H8 | 124.6 | H16A—C16—H16B | 108.0 |
N1—C8—H8 | 124.6 | C16—C17—H17A | 109.5 |
C7—C9—C10 | 112.27 (13) | C16—C17—H17B | 109.5 |
C7—C9—H9A | 109.1 | H17A—C17—H17B | 109.5 |
C10—C9—H9A | 109.1 | C16—C17—H17C | 109.5 |
C7—C9—H9B | 109.1 | H17A—C17—H17C | 109.5 |
C10—C9—H9B | 109.1 | H17B—C17—H17C | 109.5 |
H9A—C9—H9B | 107.9 | | |
| | | |
C6—C1—C2—C3 | 0.4 (2) | C6—N1—C8—C7 | −0.02 (19) |
C7—C1—C2—C3 | −179.90 (17) | C8—C7—C9—C10 | −7.7 (2) |
C1—C2—C3—C4 | −0.1 (3) | C1—C7—C9—C10 | 171.15 (15) |
C2—C3—C4—C5 | −0.4 (3) | C11—N2—C10—C9 | −110.86 (18) |
C3—C4—C5—C6 | 0.5 (3) | C7—C9—C10—N2 | −168.51 (13) |
C8—N1—C6—C5 | 179.64 (17) | C10—N2—C11—C12 | −172.13 (15) |
C8—N1—C6—C1 | 0.56 (18) | N2—C11—C12—C13 | 3.3 (3) |
C4—C5—C6—N1 | −179.16 (16) | N2—C11—C12—C15 | 179.56 (15) |
C4—C5—C6—C1 | −0.2 (2) | C11—C12—C13—O1 | −9.6 (2) |
C2—C1—C6—N1 | 178.92 (14) | C15—C12—C13—O1 | 174.32 (15) |
C7—C1—C6—N1 | −0.87 (18) | C11—C12—C13—C14 | 169.43 (16) |
C2—C1—C6—C5 | −0.3 (2) | C15—C12—C13—C14 | −6.7 (2) |
C7—C1—C6—C5 | 179.95 (14) | C16—O3—C15—O2 | 1.4 (2) |
C2—C1—C7—C8 | −178.90 (17) | C16—O3—C15—C12 | −178.38 (14) |
C6—C1—C7—C8 | 0.85 (17) | C11—C12—C15—O2 | −163.19 (16) |
C2—C1—C7—C9 | 2.1 (3) | C13—C12—C15—O2 | 13.0 (3) |
C6—C1—C7—C9 | −178.20 (15) | C11—C12—C15—O3 | 16.6 (2) |
C1—C7—C8—N1 | −0.52 (18) | C13—C12—C15—O3 | −167.24 (14) |
C9—C7—C8—N1 | 178.50 (15) | C15—O3—C16—C17 | 81.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.88 | 2.02 | 2.6518 (17) | 128 |
N2—H2···O1i | 0.88 | 2.32 | 3.0393 (18) | 139 |
N1—H1···O2ii | 0.88 | 2.07 | 2.8572 (17) | 149 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z+1. |