Methyl (1-benzamido-2-meth­oxy-2-oxoeth­yl)trypto­phanate

Karai, O.; Aouine, Y.; Faraj, H.; Alami, A.; El Hallaoui, A.; Zouihri, H.

doi:10.1107/S2414314617015474

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171547

https://doi.org/10.1107/S2414314617015474

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Methyl (1-benzamido-2-methoxy-2-oxoethyl)tryptophanate

Oumaima Karai,^a Younas Aouine,^b Hassane Faraj,^b Anouar Alami,^b ^* Abdelilah El Hallaoui ^b and Hafid Zouihri ^c

^aFormation Doctorale Molécules Bioactives, Santé et Biotechnologies, Centre d'études Doctorales Sciences et Technologies LCO, Faculté des Sciences Dhar El Marhaz, Fès, Morocco, ^bLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and ^cLaboratoire de Chimie des Matériaux et Biotechnologie des Produits Naturels, E.Ma.Me.P.S., Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco
^*Correspondence e-mail: anouar.alami@usmba.ac.ma

Edited by J. Simpson, University of Otago, New Zealand (Received 13 October 2017; accepted 24 October 2017; online 31 October 2017)

The title molecule, C₂₂H₂₃N₃O₂, is U-shaped, with a dihedral angle of 80.76 (9)° between the indole ring system and the phenyl ring. In the crystal, N—H⋯O hydrogen bonds combine with N—H⋯π and C—H⋯π interactions to generate a three-dimensional structure.

Keywords: crystal structure; indole; benzamido; hydrogen bonds.

CCDC reference: 1573006

Structure description

The molecule of the title compound is approximately U-shaped, Fig. 1, with the indole ring system and the benzene ring linked by a complex alaninate chain and with a dihedral angle of 80.76 (9)° between them. This conformation is supported by an intramolecular C5—H5⋯Cg3 interaction (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N3/C15–C17/C22, C1–C6 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1ⁱ	0.87 (2)	2.03 (2)	2.862 (2)	162 (3)
N2—H2N⋯Cg2ⁱⁱ	0.89 (2)	2.65 (3)	3.4451 (18)	149 (2)
C5—H5⋯Cg3	0.93	2.83	3.662 (2)	149
C20—H20⋯Cg1ⁱⁱⁱ	0.93	2.83	3.684 (3)	154
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Figure 1
The structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

In the crystal, classical N3—H3N⋯O1 hydrogen bonds together with unusual intermolecular N2—H2N⋯Cg2 contacts and C20—H20⋯Cg1 interactions combine to generate a three dimensional network, Fig. 2.

Figure 2
A view of the crystal packing of the title compound along the b axis. N—H⋯O hydrogen bonds are drawn as blue dashed lines with N—H⋯π and C—H⋯π contacts shown as dotted green lines. Ring centroids are displayed as coloured spheres.

Synthesis and crystallization

To a solution of 2.6 mmol of N-protected methyl α-azidoglycinate and 3.12 mmol of di-isopropylethylamine (DIEA) in 10 ml of acetone, 2.86 mmol of 2-amino-3-(1H-indol-3-yl)propanoate was added. The reaction mixture was stirred at room temperature. The solvent was evaporated under reduced pressure. The residue was quenched with saturated aqueous solution of ammonium chloride (20 ml) and extracted with methylene chloride (3 × 20 ml). The organic layer was dried over sodium sulfate (Na₂SO₄) and the solvent was removed under reduced pressure. Single crystals of the title compound were obtained by recrystallization from chloroform (CHCl₃) solution, yield = 86% (white solid); m.p. = 174–176°C.

¹H NMR (DMSO, δ_H p.p.m.): 2.94–3.02 (m, 3H, NH—CH—CH₂– and –CH₂-indol-3-yl); 3.28 (s, 3H, –OCH₃); 3.64 (s, 3H, –OCH₃); 3.67–3.72 (t, 1H, N—CH—CH₂–, J = 6.90 Hz); 5.25–5.31 (dd, 1H, N—CH—N, J₁ = 10.17 Hz and J₂ = 7.73 Hz); 6.93–7.82 (m, 10H, 10H_arom); 9.1 (s, 1H, NHBz); 10.9 (s, 1H, NH_indole). ¹³C NMR (DMSO, δ_C p.p.m.): 29.18 (1 C, –CH₂-indol-3-yl); 51.78 and 52.65 (2 C, –OCH₃); 59.06 (1 C, –CH—CH₂-indol-3-yl); 64.18 (1 C, N—CH—N); 109.80–136.48 (14 C, C_arom); 166.61, 170.38 and 174.89 (3 C, CO). Calculated for C₂₂H₂₃N₃O₅ (%): C, 64.54; H, 5.66; N, 10.26; found (%): C 64.28, H 5.71, N 10.16. MS ESI m/z (%) = 409.60.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. With no heavy atoms in the molecule the absolute structure could not be determined reliably.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₃N₃O₅
M_r	409.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.5716 (3), 11.6875 (4), 18.1827 (6)
V (Å³)	2034.06 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.21 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005 )
No. of measured, independent and observed [I > 2σ(I)] reflections	22029, 4675, 4359
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.05
No. of reflections	4675
No. of parameters	285
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17
Absolute structure	Flack x determined using 1822 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 ).
Absolute structure parameter	0.0 (2)
Computer programs: APEX2 and SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1573006

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617015474/sj4140sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617015474/sj4140Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617015474/sj4140Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Methyl 3-(1H-indol-3-yl)-2-{[2-methoxy-2-oxo-1-(phenylformamido)ethyl]amino}propanoate top

Crystal data top

C₂₂H₂₃N₃O₅	D_x = 1.337 Mg m⁻³
M_r = 409.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 275 reflections
a = 9.5716 (3) Å	θ = 1.3–57°
b = 11.6875 (4) Å	µ = 0.10 mm⁻¹
c = 18.1827 (6) Å	T = 293 K
V = 2034.06 (12) Å³	Prism, colourless
Z = 4	0.23 × 0.21 × 0.14 mm
F(000) = 864

Data collection top

Bruker APEXII CCD diffractometer	4675 independent reflections
Radiation source: fine-focus sealed tube	4359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scan	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
	k = −15→15
22029 measured reflections	l = −23→23

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0569P)² + 0.2737P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.097	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.22 e Å⁻³
4675 reflections	Δρ_min = −0.17 e Å⁻³
285 parameters	Absolute structure: Flack x determined using 1822 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
3 restraints	Absolute structure parameter: 0.0 (2)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C7	0.71253 (18)	0.07261 (14)	0.23815 (10)	0.0313 (3)
C6	0.77399 (19)	−0.04380 (14)	0.22646 (10)	0.0309 (3)
C5	0.7366 (2)	−0.11460 (15)	0.16841 (10)	0.0361 (4)
H5	0.6644	−0.0934	0.1370	0.043*
C1	0.8802 (2)	−0.07750 (17)	0.27415 (11)	0.0393 (4)
H1	0.9056	−0.0306	0.3133	0.047*
C4	0.8070 (2)	−0.21720 (17)	0.15728 (13)	0.0464 (5)
H4	0.7830	−0.2640	0.1179	0.056*
C2	0.9483 (2)	−0.18102 (19)	0.26330 (14)	0.0486 (5)
H2	1.0180	−0.2041	0.2957	0.058*
C3	0.9124 (2)	−0.24964 (19)	0.20450 (14)	0.0510 (5)
H3	0.9596	−0.3181	0.1967	0.061*
N1	0.58969 (17)	0.09702 (13)	0.20564 (9)	0.0349 (3)
C8	0.52998 (19)	0.21167 (15)	0.21117 (10)	0.0327 (4)
H8	0.5171	0.2306	0.2632	0.039*
C9	0.6299 (2)	0.29926 (15)	0.17664 (11)	0.0365 (4)
O1	0.77431 (17)	0.14492 (12)	0.27462 (9)	0.0497 (4)
O3	0.61318 (19)	0.40054 (12)	0.20853 (9)	0.0517 (4)
O2	0.70594 (19)	0.28145 (14)	0.12588 (10)	0.0582 (4)
C10	0.6864 (3)	0.4950 (2)	0.17486 (19)	0.0675 (7)
H10A	0.6760	0.5621	0.2049	0.101*
H10B	0.6480	0.5094	0.1270	0.101*
H10C	0.7837	0.4764	0.1704	0.101*
N2	0.39521 (17)	0.21076 (14)	0.17551 (9)	0.0352 (3)
C12	0.3859 (2)	0.33133 (17)	0.06305 (11)	0.0401 (4)
C11	0.3936 (2)	0.21081 (15)	0.09530 (10)	0.0340 (4)
H11	0.4796	0.1744	0.0777	0.041*
C13	0.3913 (3)	0.4341 (2)	−0.04853 (15)	0.0638 (7)
H13A	0.4554	0.4918	−0.0320	0.096*
H13B	0.2972	0.4595	−0.0403	0.096*
H13C	0.4052	0.4205	−0.1001	0.096*
O5	0.41550 (19)	0.32938 (14)	−0.00816 (9)	0.0514 (4)
O4	0.3559 (3)	0.41515 (15)	0.09638 (11)	0.0743 (6)
N3	0.2625 (2)	−0.15885 (14)	0.13318 (10)	0.0431 (4)
C17	0.3845 (2)	−0.05961 (16)	0.04926 (10)	0.0370 (4)
C16	0.2847 (2)	0.01589 (16)	0.08328 (11)	0.0379 (4)
C14	0.2676 (2)	0.14084 (17)	0.06700 (12)	0.0413 (4)
H14A	0.1828	0.1686	0.0902	0.050*
H14B	0.2583	0.1516	0.0143	0.050*
C15	0.2145 (2)	−0.04813 (17)	0.13370 (11)	0.0422 (4)
H15	0.1441	−0.0208	0.1642	0.051*
C22	0.3673 (2)	−0.16815 (16)	0.08245 (11)	0.0381 (4)
C18	0.4861 (2)	−0.0466 (2)	−0.00585 (12)	0.0480 (5)
H18	0.4993	0.0237	−0.0288	0.058*
C21	0.4464 (3)	−0.26306 (19)	0.06147 (12)	0.0481 (5)
H21	0.4324	−0.3344	0.0829	0.058*
C19	0.5659 (3)	−0.1399 (2)	−0.02529 (14)	0.0584 (6)
H19	0.6345	−0.1318	−0.0611	0.070*
C20	0.5456 (3)	−0.2470 (2)	0.00800 (14)	0.0564 (6)
H20	0.6007	−0.3085	−0.0065	0.068*
H2N	0.343 (3)	0.2689 (19)	0.1905 (14)	0.047 (7)*
H1N	0.537 (2)	0.0475 (18)	0.1878 (12)	0.036 (6)*
H3N	0.233 (3)	−0.212 (2)	0.1624 (15)	0.070 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0333 (8)	0.0256 (7)	0.0350 (8)	−0.0013 (7)	0.0002 (7)	−0.0008 (6)
C6	0.0307 (8)	0.0247 (7)	0.0373 (8)	−0.0019 (6)	0.0032 (7)	0.0033 (6)
C5	0.0382 (9)	0.0278 (8)	0.0422 (10)	−0.0006 (7)	0.0000 (8)	0.0005 (7)
C1	0.0341 (8)	0.0367 (9)	0.0472 (10)	−0.0005 (8)	−0.0037 (8)	0.0032 (8)
C4	0.0507 (11)	0.0310 (9)	0.0574 (12)	−0.0001 (8)	0.0075 (9)	−0.0088 (8)
C2	0.0337 (9)	0.0427 (11)	0.0694 (14)	0.0071 (8)	−0.0038 (9)	0.0087 (10)
C3	0.0427 (11)	0.0310 (9)	0.0793 (15)	0.0081 (8)	0.0102 (10)	−0.0008 (10)
N1	0.0366 (8)	0.0219 (6)	0.0463 (8)	0.0003 (6)	−0.0065 (7)	−0.0013 (6)
C8	0.0366 (9)	0.0256 (8)	0.0358 (8)	0.0032 (7)	−0.0010 (7)	0.0002 (7)
C9	0.0394 (9)	0.0290 (8)	0.0411 (9)	0.0009 (7)	−0.0015 (8)	0.0024 (7)
O1	0.0485 (8)	0.0338 (7)	0.0669 (9)	0.0035 (6)	−0.0163 (7)	−0.0159 (7)
O3	0.0640 (10)	0.0268 (7)	0.0643 (9)	−0.0053 (7)	0.0080 (8)	−0.0036 (6)
O2	0.0665 (10)	0.0450 (8)	0.0630 (9)	−0.0052 (8)	0.0244 (9)	−0.0024 (7)
C10	0.0796 (18)	0.0320 (11)	0.0910 (19)	−0.0118 (11)	0.0063 (16)	0.0059 (12)
N2	0.0335 (7)	0.0330 (7)	0.0391 (8)	0.0057 (6)	0.0023 (6)	0.0022 (6)
C12	0.0409 (10)	0.0335 (9)	0.0460 (10)	0.0008 (8)	0.0002 (8)	0.0089 (8)
C11	0.0343 (8)	0.0279 (8)	0.0396 (9)	0.0044 (7)	−0.0009 (7)	0.0047 (7)
C13	0.0725 (16)	0.0576 (15)	0.0614 (14)	−0.0001 (13)	−0.0020 (13)	0.0283 (12)
O5	0.0655 (10)	0.0446 (8)	0.0442 (8)	0.0014 (7)	−0.0002 (7)	0.0135 (6)
O4	0.1215 (18)	0.0361 (8)	0.0655 (11)	0.0202 (10)	0.0198 (11)	0.0083 (8)
N3	0.0521 (10)	0.0345 (8)	0.0429 (9)	−0.0053 (7)	0.0003 (8)	0.0085 (7)
C17	0.0414 (10)	0.0336 (9)	0.0360 (9)	−0.0049 (8)	−0.0063 (8)	0.0004 (7)
C16	0.0416 (10)	0.0335 (9)	0.0386 (9)	−0.0027 (8)	−0.0074 (8)	0.0023 (7)
C14	0.0405 (10)	0.0345 (9)	0.0488 (11)	−0.0003 (8)	−0.0099 (9)	0.0080 (8)
C15	0.0457 (10)	0.0388 (9)	0.0421 (10)	−0.0012 (9)	0.0009 (9)	0.0026 (8)
C22	0.0417 (10)	0.0340 (9)	0.0386 (9)	−0.0050 (8)	−0.0091 (8)	−0.0005 (8)
C18	0.0519 (12)	0.0469 (12)	0.0451 (11)	−0.0085 (10)	0.0022 (9)	0.0012 (9)
C21	0.0572 (12)	0.0339 (10)	0.0534 (12)	−0.0001 (9)	−0.0111 (10)	−0.0056 (9)
C19	0.0559 (14)	0.0651 (15)	0.0543 (13)	−0.0040 (12)	0.0085 (11)	−0.0120 (11)
C20	0.0565 (13)	0.0512 (12)	0.0614 (13)	0.0065 (11)	−0.0012 (11)	−0.0177 (11)

Geometric parameters (Å, º) top

C7—O1	1.226 (2)	C12—O5	1.326 (3)
C7—N1	1.347 (2)	C12—C11	1.528 (2)
C7—C6	1.497 (2)	C11—C14	1.546 (3)
C6—C5	1.388 (3)	C11—H11	0.9800
C6—C1	1.393 (3)	C13—O5	1.446 (3)
C5—C4	1.391 (3)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C1—C2	1.388 (3)	C13—H13C	0.9600
C1—H1	0.9300	N3—C22	1.367 (3)
C4—C3	1.378 (3)	N3—C15	1.373 (3)
C4—H4	0.9300	N3—H3N	0.87 (2)
C2—C3	1.380 (3)	C17—C18	1.405 (3)
C2—H2	0.9300	C17—C22	1.414 (3)
C3—H3	0.9300	C17—C16	1.440 (3)
N1—C8	1.460 (2)	C16—C15	1.361 (3)
N1—H1N	0.831 (19)	C16—C14	1.499 (3)
C8—N2	1.444 (2)	C14—H14A	0.9700
C8—C9	1.535 (3)	C14—H14B	0.9700
C8—H8	0.9800	C15—H15	0.9300
C9—O2	1.194 (3)	C22—C21	1.396 (3)
C9—O3	1.328 (2)	C18—C19	1.377 (4)
O3—C10	1.444 (3)	C18—H18	0.9300
C10—H10A	0.9600	C21—C20	1.372 (4)
C10—H10B	0.9600	C21—H21	0.9300
C10—H10C	0.9600	C19—C20	1.404 (4)
N2—C11	1.459 (2)	C19—H19	0.9300
N2—H2N	0.89 (2)	C20—H20	0.9300
C12—O4	1.187 (3)

O1—C7—N1	120.83 (16)	N2—C11—C12	112.63 (16)
O1—C7—C6	120.90 (16)	N2—C11—C14	109.92 (16)
N1—C7—C6	118.24 (15)	C12—C11—C14	108.79 (15)
C5—C6—C1	119.54 (17)	N2—C11—H11	108.5
C5—C6—C7	123.24 (16)	C12—C11—H11	108.5
C1—C6—C7	117.08 (16)	C14—C11—H11	108.5
C6—C5—C4	119.97 (18)	O5—C13—H13A	109.5
C6—C5—H5	120.0	O5—C13—H13B	109.5
C4—C5—H5	120.0	H13A—C13—H13B	109.5
C2—C1—C6	120.0 (2)	O5—C13—H13C	109.5
C2—C1—H1	120.0	H13A—C13—H13C	109.5
C6—C1—H1	120.0	H13B—C13—H13C	109.5
C3—C4—C5	120.1 (2)	C12—O5—C13	116.56 (19)
C3—C4—H4	119.9	C22—N3—C15	108.96 (16)
C5—C4—H4	119.9	C22—N3—H3N	127 (2)
C3—C2—C1	120.0 (2)	C15—N3—H3N	124 (2)
C3—C2—H2	120.0	C18—C17—C22	118.80 (19)
C1—C2—H2	120.0	C18—C17—C16	134.39 (19)
C4—C3—C2	120.33 (19)	C22—C17—C16	106.81 (18)
C4—C3—H3	119.8	C15—C16—C17	106.25 (17)
C2—C3—H3	119.8	C15—C16—C14	127.9 (2)
C7—N1—C8	120.39 (15)	C17—C16—C14	125.78 (19)
C7—N1—H1N	123.4 (16)	C16—C14—C11	111.37 (16)
C8—N1—H1N	115.5 (16)	C16—C14—H14A	109.4
N2—C8—N1	108.18 (15)	C11—C14—H14A	109.4
N2—C8—C9	112.20 (15)	C16—C14—H14B	109.4
N1—C8—C9	109.88 (15)	C11—C14—H14B	109.4
N2—C8—H8	108.8	H14A—C14—H14B	108.0
N1—C8—H8	108.8	C16—C15—N3	110.40 (19)
C9—C8—H8	108.8	C16—C15—H15	124.8
O2—C9—O3	124.51 (19)	N3—C15—H15	124.8
O2—C9—C8	125.43 (18)	N3—C22—C21	130.20 (19)
O3—C9—C8	109.93 (16)	N3—C22—C17	107.58 (17)
C9—O3—C10	115.99 (19)	C21—C22—C17	122.2 (2)
O3—C10—H10A	109.5	C19—C18—C17	118.8 (2)
O3—C10—H10B	109.5	C19—C18—H18	120.6
H10A—C10—H10B	109.5	C17—C18—H18	120.6
O3—C10—H10C	109.5	C20—C21—C22	117.4 (2)
H10A—C10—H10C	109.5	C20—C21—H21	121.3
H10B—C10—H10C	109.5	C22—C21—H21	121.3
C8—N2—C11	117.27 (15)	C18—C19—C20	121.2 (2)
C8—N2—H2N	111.2 (17)	C18—C19—H19	119.4
C11—N2—H2N	107.5 (16)	C20—C19—H19	119.4
O4—C12—O5	124.37 (19)	C21—C20—C19	121.6 (2)
O4—C12—C11	125.23 (19)	C21—C20—H20	119.2
O5—C12—C11	110.40 (17)	C19—C20—H20	119.2

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N3/C15–C17/C22, C1–C6 and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.87 (2)	2.03 (2)	2.862 (2)	162 (3)
N2—H2N···Cg2ⁱⁱ	0.89 (2)	2.65 (3)	3.4451 (18)	149 (2)
C5—H5···Cg3	0.93	2.83	3.662 (2)	149
C20—H20···Cg1ⁱⁱⁱ	0.93	2.83	3.684 (3)	154

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1/2, −y−1/2, −z.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 2| Part 10| October 2017| x171547

https://doi.org/10.1107/S2414314617015474

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl (1-benzamido-2-meth­­oxy-2-oxoeth­yl)trypto­phanate

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

Methyl (1-benzamido-2-methoxy-2-oxoethyl)tryptophanate