Ethyl 2-acetyl-3-[2-(1H-indol-3-yl)­ethyl­amino]­propenoate

The title compound, C₁₇H₂₀N₂O₃, 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.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](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

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Computing details

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-(1H-indol-3-yl)ethylamino]propenoate

Crystal data

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) Å^3	0.40 × 0.30 × 0.30 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0645P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.88	2.32	3.0393 (18)	139
N1—H1···O2^ii	0.88	2.07	2.8572 (17)	149

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z+1.