N-(1-Phenyl­ethyl)­indole-2-carbox­amide di­methyl­form­amide solvate

In the title compound, C₁₇H₁₆N₂O·C₃H₇NO, containing indolyl and amide groups, the indolyl and phenyl rings are not coplanar, and form a dihedral angle of 88.4 (2)°. There are two intermolecular hydrogen bonds through the indole N and carbonyl O atom of the mol­ecule, as well as through the amide N atom of the mol­ecule and carbonyl O atom of the di­methyl­form­amide solvent mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.109
• Data-to-parameter ratio = 18.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1995); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(2-ethylbenzene)-2-indolecarboxamide

Crystal data

C17H16N2O·C3H7NO	Z = 2
Mr = 337.41	F(000) = 360
Triclinic, P1	Dx = 1.185 Mg m^−3
a = 7.8166 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1683 (18) Å	Cell parameters from 3267 reflections
c = 11.5769 (18) Å	θ = 1–27.5°
α = 73.310 (3)°	µ = 0.08 mm^−1
β = 85.990 (4)°	T = 294 K
γ = 77.571 (4)°	Prism, colorless
V = 945.3 (3) Å^3	0.14 × 0.12 × 0.10 mm

Data collection

Bruker CCD area-detector diffractometer	4309 independent reflections
Radiation source: fine-focus sealed tube	1395 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.989, Tmax = 0.992	k = −14→12
6524 measured reflections	l = −12→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
4309 reflections	Δρmax = 0.33 e Å^−3
229 parameters	Δρmin = −0.15 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	0.4064 (2)	0.12937 (16)	0.36007 (13)	0.0751 (5)
N1	0.4773 (2)	0.13575 (18)	0.58901 (16)	0.0637 (6)
H1A	0.5026	0.0601	0.5799	0.076*
N2	0.2952 (2)	0.34100 (18)	0.30145 (16)	0.0644 (6)
H2A	0.2734	0.4117	0.3206	0.077*
C1	0.3700 (3)	0.2330 (3)	0.3831 (2)	0.0601 (7)
C2	0.4071 (3)	0.2454 (2)	0.5016 (2)	0.0591 (6)
C3	0.3860 (3)	0.3452 (2)	0.5494 (2)	0.0733 (8)
H3	0.3425	0.4304	0.5093	0.088*
C4	0.4416 (3)	0.2977 (2)	0.6709 (2)	0.0693 (7)
C5	0.4503 (4)	0.3508 (3)	0.7655 (3)	0.0951 (9)
H5A	0.4156	0.4385	0.7535	0.114*
C6	0.5101 (4)	0.2731 (3)	0.8759 (3)	0.0923 (9)
H6A	0.5133	0.3082	0.9393	0.111*
C7	0.5656 (3)	0.1430 (3)	0.8938 (2)	0.0826 (8)
H7A	0.6069	0.0927	0.9694	0.099*
C8	0.5624 (3)	0.0848 (3)	0.8042 (2)	0.0744 (8)
H8A	0.5992	−0.0029	0.8172	0.089*
C9	0.5004 (3)	0.1660 (2)	0.6925 (2)	0.0604 (7)
C10	0.2499 (3)	0.3412 (2)	0.1808 (2)	0.0646 (7)
H10A	0.3447	0.2829	0.1526	0.078*
C11	0.2387 (3)	0.4746 (2)	0.0937 (2)	0.0928 (9)
H11A	0.3488	0.5001	0.0919	0.139*
H11B	0.1480	0.5340	0.1203	0.139*
H11C	0.2122	0.4734	0.0144	0.139*
C12	0.0814 (3)	0.2942 (2)	0.1814 (2)	0.0599 (7)
C13	−0.0565 (4)	0.3227 (3)	0.2544 (3)	0.0888 (9)
H13A	−0.0476	0.3714	0.3060	0.107*
C14	−0.2089 (4)	0.2804 (3)	0.2527 (3)	0.1034 (10)
H14A	−0.3017	0.3009	0.3030	0.124*
C15	−0.2258 (4)	0.2086 (3)	0.1780 (3)	0.1000 (10)
H15A	−0.3279	0.1784	0.1787	0.120*
C16	−0.0895 (5)	0.1820 (3)	0.1022 (3)	0.0911 (9)
H16A	−0.0999	0.1356	0.0488	0.109*
C17	0.0634 (3)	0.2241 (2)	0.1052 (2)	0.0743 (8)
H17A	0.1560	0.2044	0.0544	0.089*
O2	0.1169 (3)	0.5758 (2)	0.3463 (2)	0.1396 (10)
N3	0.0307 (3)	0.7836 (3)	0.3432 (2)	0.0930 (7)
C18	0.1043 (5)	0.6641 (4)	0.3899 (3)	0.1364 (15)
H18A	0.1529	0.6442	0.4659	0.164*
C19	−0.0380 (4)	0.8215 (3)	0.2241 (3)	0.1293 (12)
H19A	−0.0195	0.7486	0.1931	0.194*
H19B	0.0206	0.8848	0.1729	0.194*
H19C	−0.1612	0.8566	0.2261	0.194*
C20	0.0215 (4)	0.8834 (3)	0.4010 (3)	0.1367 (13)
H20A	0.0792	0.8482	0.4775	0.205*
H20B	−0.0989	0.9198	0.4132	0.205*
H20C	0.0782	0.9484	0.3509	0.205*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1053 (14)	0.0515 (12)	0.0658 (11)	−0.0032 (10)	−0.0197 (9)	−0.0173 (9)
N1	0.0745 (14)	0.0565 (14)	0.0588 (14)	−0.0025 (11)	−0.0122 (11)	−0.0194 (12)
N2	0.0761 (14)	0.0548 (14)	0.0584 (14)	−0.0048 (11)	−0.0170 (11)	−0.0120 (11)
C1	0.0562 (16)	0.0631 (19)	0.0573 (17)	−0.0091 (15)	−0.0072 (13)	−0.0116 (15)
C2	0.0680 (17)	0.0490 (17)	0.0550 (16)	−0.0030 (14)	−0.0096 (13)	−0.0105 (14)
C3	0.096 (2)	0.0468 (17)	0.0717 (19)	−0.0025 (15)	−0.0129 (16)	−0.0136 (14)
C4	0.089 (2)	0.0589 (19)	0.0643 (19)	−0.0116 (16)	−0.0041 (15)	−0.0253 (15)
C5	0.141 (3)	0.066 (2)	0.085 (2)	−0.0176 (19)	−0.009 (2)	−0.0327 (19)
C6	0.134 (3)	0.091 (2)	0.066 (2)	−0.038 (2)	−0.0001 (19)	−0.0335 (19)
C7	0.106 (2)	0.092 (2)	0.0579 (18)	−0.0376 (19)	−0.0125 (16)	−0.0174 (17)
C8	0.088 (2)	0.0699 (19)	0.0638 (18)	−0.0158 (15)	−0.0146 (15)	−0.0142 (16)
C9	0.0715 (17)	0.0621 (19)	0.0514 (17)	−0.0160 (15)	−0.0050 (14)	−0.0189 (14)
C10	0.0711 (18)	0.0638 (18)	0.0541 (16)	−0.0101 (15)	−0.0072 (14)	−0.0099 (14)
C11	0.115 (2)	0.084 (2)	0.0707 (19)	−0.0328 (18)	−0.0176 (16)	0.0047 (16)
C12	0.0596 (18)	0.0576 (18)	0.0550 (16)	−0.0045 (14)	−0.0104 (14)	−0.0072 (13)
C13	0.070 (2)	0.104 (3)	0.099 (2)	−0.0167 (19)	0.0032 (19)	−0.0403 (19)
C14	0.072 (2)	0.125 (3)	0.108 (3)	−0.015 (2)	0.0082 (19)	−0.032 (2)
C15	0.077 (2)	0.112 (3)	0.102 (3)	−0.027 (2)	−0.017 (2)	−0.006 (2)
C16	0.101 (2)	0.094 (3)	0.084 (2)	−0.028 (2)	−0.021 (2)	−0.0236 (18)
C17	0.075 (2)	0.076 (2)	0.0709 (19)	−0.0125 (16)	−0.0127 (15)	−0.0179 (16)
O2	0.188 (2)	0.0866 (18)	0.1176 (19)	0.0339 (17)	0.0033 (16)	−0.0342 (15)
N3	0.0979 (19)	0.082 (2)	0.0843 (19)	0.0042 (16)	0.0081 (16)	−0.0178 (16)
C18	0.166 (4)	0.102 (3)	0.099 (3)	0.041 (3)	0.001 (2)	−0.011 (2)
C19	0.124 (3)	0.127 (3)	0.119 (3)	−0.021 (2)	−0.008 (2)	−0.008 (2)
C20	0.159 (3)	0.119 (3)	0.134 (3)	−0.006 (3)	0.008 (2)	−0.057 (3)

Geometric parameters (Å, º)

O1—C1	1.232 (2)	C11—H11B	0.9600
N1—C9	1.368 (2)	C11—H11C	0.9600
N1—C2	1.379 (3)	C12—C13	1.363 (3)
N1—H1A	0.8600	C12—C17	1.368 (3)
N2—C1	1.345 (3)	C13—C14	1.377 (3)
N2—C10	1.464 (2)	C13—H13A	0.9300
N2—H2A	0.8600	C14—C15	1.366 (3)
C1—C2	1.472 (3)	C14—H14A	0.9300
C2—C3	1.357 (3)	C15—C16	1.370 (4)
C3—C4	1.416 (3)	C15—H15A	0.9300
C3—H3	0.9300	C16—C17	1.381 (3)
C4—C9	1.397 (3)	C16—H16A	0.9300
C4—C5	1.399 (3)	C17—H17A	0.9300
C5—C6	1.369 (3)	O2—C18	1.214 (4)
C5—H5A	0.9300	N3—C18	1.304 (4)
C6—C7	1.382 (3)	N3—C19	1.428 (3)
C6—H6A	0.9300	N3—C20	1.443 (3)
C7—C8	1.377 (3)	C18—H18A	0.9300
C7—H7A	0.9300	C19—H19A	0.9600
C8—C9	1.398 (3)	C19—H19B	0.9600
C8—H8A	0.9300	C19—H19C	0.9600
C10—C12	1.518 (3)	C20—H20A	0.9600
C10—C11	1.528 (3)	C20—H20B	0.9600
C10—H10A	0.9800	C20—H20C	0.9600
C11—H11A	0.9600
C9—N1—C2	109.4 (2)	H11A—C11—H11B	109.5
C9—N1—H1A	125.3	C10—C11—H11C	109.5
C2—N1—H1A	125.3	H11A—C11—H11C	109.5
C1—N2—C10	121.7 (2)	H11B—C11—H11C	109.5
C1—N2—H2A	119.2	C13—C12—C17	118.3 (2)
C10—N2—H2A	119.2	C13—C12—C10	121.6 (2)
O1—C1—N2	122.0 (2)	C17—C12—C10	120.1 (2)
O1—C1—C2	121.6 (2)	C12—C13—C14	120.7 (3)
N2—C1—C2	116.4 (2)	C12—C13—H13A	119.6
C3—C2—N1	108.1 (2)	C14—C13—H13A	119.6
C3—C2—C1	134.0 (2)	C15—C14—C13	121.0 (3)
N1—C2—C1	117.9 (2)	C15—C14—H14A	119.5
C2—C3—C4	108.3 (2)	C13—C14—H14A	119.5
C2—C3—H3	125.8	C14—C15—C16	118.8 (3)
C4—C3—H3	125.8	C14—C15—H15A	120.6
C9—C4—C5	117.9 (2)	C16—C15—H15A	120.6
C9—C4—C3	106.5 (2)	C15—C16—C17	119.8 (3)
C5—C4—C3	135.6 (3)	C15—C16—H16A	120.1
C6—C5—C4	119.7 (3)	C17—C16—H16A	120.1
C6—C5—H5A	120.1	C12—C17—C16	121.4 (3)
C4—C5—H5A	120.1	C12—C17—H17A	119.3
C5—C6—C7	120.5 (2)	C16—C17—H17A	119.3
C5—C6—H6A	119.7	C18—N3—C19	118.7 (3)
C7—C6—H6A	119.7	C18—N3—C20	124.5 (3)
C8—C7—C6	122.7 (3)	C19—N3—C20	116.7 (3)
C8—C7—H7A	118.7	O2—C18—N3	127.9 (4)
C6—C7—H7A	118.7	O2—C18—H18A	116.1
C7—C8—C9	115.7 (3)	N3—C18—H18A	116.1
C7—C8—H8A	122.1	N3—C19—H19A	109.5
C9—C8—H8A	122.1	N3—C19—H19B	109.5
N1—C9—C8	128.9 (2)	H19A—C19—H19B	109.5
N1—C9—C4	107.6 (2)	N3—C19—H19C	109.5
C8—C9—C4	123.4 (2)	H19A—C19—H19C	109.5
N2—C10—C12	112.03 (19)	H19B—C19—H19C	109.5
N2—C10—C11	109.96 (19)	N3—C20—H20A	109.5
C12—C10—C11	111.19 (19)	N3—C20—H20B	109.5
N2—C10—H10A	107.8	H20A—C20—H20B	109.5
C12—C10—H10A	107.8	N3—C20—H20C	109.5
C11—C10—H10A	107.8	H20A—C20—H20C	109.5
C10—C11—H11A	109.5	H20B—C20—H20C	109.5
C10—C11—H11B	109.5
C10—N2—C1—O1	1.1 (3)	C5—C4—C9—N1	179.2 (2)
C10—N2—C1—C2	−179.31 (19)	C3—C4—C9—N1	−1.3 (3)
C9—N1—C2—C3	0.1 (3)	C5—C4—C9—C8	1.8 (4)
C9—N1—C2—C1	−179.2 (2)	C3—C4—C9—C8	−178.6 (2)
O1—C1—C2—C3	177.9 (3)	C1—N2—C10—C12	78.7 (3)
N2—C1—C2—C3	−1.7 (4)	C1—N2—C10—C11	−157.2 (2)
O1—C1—C2—N1	−2.9 (3)	N2—C10—C12—C13	37.0 (3)
N2—C1—C2—N1	177.5 (2)	C11—C10—C12—C13	−86.5 (3)
N1—C2—C3—C4	−0.9 (3)	N2—C10—C12—C17	−144.7 (2)
C1—C2—C3—C4	178.3 (2)	C11—C10—C12—C17	91.8 (3)
C2—C3—C4—C9	1.4 (3)	C17—C12—C13—C14	1.0 (4)
C2—C3—C4—C5	−179.2 (3)	C10—C12—C13—C14	179.3 (2)
C9—C4—C5—C6	−2.0 (4)	C12—C13—C14—C15	0.1 (5)
C3—C4—C5—C6	178.6 (3)	C13—C14—C15—C16	−1.6 (5)
C4—C5—C6—C7	1.5 (4)	C14—C15—C16—C17	2.1 (5)
C5—C6—C7—C8	−0.7 (5)	C13—C12—C17—C16	−0.5 (4)
C6—C7—C8—C9	0.5 (4)	C10—C12—C17—C16	−178.8 (2)
C2—N1—C9—C8	177.8 (2)	C15—C16—C17—C12	−1.0 (4)
C2—N1—C9—C4	0.7 (3)	C19—N3—C18—O2	−3.4 (6)
C7—C8—C9—N1	−177.8 (2)	C20—N3—C18—O2	−179.8 (4)
C7—C8—C9—C4	−1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.01	2.803 (2)	153
N2—H2A···O2	0.86	2.06	2.863 (3)	155

Symmetry code: (i) −x+1, −y, −z+1.