N-Methyl-N-propyl­tryptamine (MPT)

The title compound {systematic name: [2-(1H-indol-3-yl)eth­yl](meth­yl)propyl­amine}, C₁₄H₂₀N₂, has a single mol­ecule in the asymmetric unit. The mol­ecules in the unit cell are held together in infinite one-dimensional chains along [010] through N—H...N hydrogen bonds between indole H atoms and tri­alkyl­amine N atoms.

checkCIF/PLATON results

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Datablock: I


Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a) and publCIF (Westrip, 2010); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

[2-(1H-Indol-3-yl)ethyl](methyl)propylamine

Crystal data

C14H20N2	Dx = 1.123 Mg m^−3
Mr = 216.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9106 reflections
a = 13.5715 (11) Å	θ = 3.0–25.3°
b = 12.4352 (10) Å	µ = 0.07 mm^−1
c = 15.1627 (12) Å	T = 200 K
V = 2558.9 (4) Å^3	Block, colourless
Z = 8	0.28 × 0.20 × 0.13 mm
F(000) = 944

Data collection

Bruker D8 Venture CMOS diffractometer	1942 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.048
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 25.4°, θmin = 3.0°
Tmin = 0.713, Tmax = 0.745	h = −16→16
47431 measured reflections	k = −14→15
2350 independent reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 0.843P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.17 e Å^−3
2350 reflections	Δρmin = −0.16 e Å^−3
152 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0279 (16)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.15123 (8)	0.54678 (9)	0.71757 (7)	0.0342 (3)
N2	0.47825 (7)	0.22356 (7)	0.76631 (7)	0.0281 (3)
C1	0.20625 (9)	0.48945 (10)	0.77718 (8)	0.0329 (3)
H1A	0.2086	0.5040	0.8387	0.040*
C2	0.16536 (9)	0.50319 (10)	0.63560 (8)	0.0299 (3)
C3	0.12410 (10)	0.53092 (11)	0.55460 (9)	0.0380 (3)
H3	0.0802	0.5901	0.5494	0.046*
C4	0.14904 (10)	0.46983 (12)	0.48231 (9)	0.0438 (4)
H4	0.1221	0.4873	0.4263	0.053*
C7	0.23153 (8)	0.41566 (9)	0.64465 (8)	0.0291 (3)
C5	0.21333 (10)	0.38242 (12)	0.48980 (9)	0.0427 (4)
H5	0.2288	0.3413	0.4389	0.051*
C6	0.25456 (10)	0.35491 (11)	0.56941 (9)	0.0368 (3)
H6	0.2982	0.2954	0.5735	0.044*
C8	0.25697 (9)	0.40901 (9)	0.73654 (8)	0.0299 (3)
C9	0.32024 (9)	0.32514 (10)	0.77938 (9)	0.0347 (3)
H9A	0.2902	0.2536	0.7696	0.042*
H9B	0.3217	0.3382	0.8438	0.042*
C10	0.42572 (9)	0.32375 (10)	0.74460 (9)	0.0334 (3)
H10A	0.4245	0.3328	0.6797	0.040*
H10B	0.4622	0.3854	0.7699	0.040*
C11	0.50645 (10)	0.22182 (10)	0.85999 (8)	0.0341 (3)
H11A	0.4465	0.2323	0.8962	0.041*
H11B	0.5511	0.2832	0.8716	0.041*
C12	0.55691 (12)	0.11938 (12)	0.88919 (10)	0.0473 (4)
H12A	0.6211	0.1130	0.8585	0.057*
H12B	0.5159	0.0570	0.8719	0.057*
C13	0.57384 (14)	0.11646 (13)	0.98776 (10)	0.0574 (4)
H13A	0.6089	0.0503	1.0034	0.086*
H13B	0.5103	0.1184	1.0183	0.086*
H13C	0.6133	0.1789	1.0054	0.086*
C14	0.56449 (10)	0.21237 (11)	0.70873 (9)	0.0402 (3)
H14A	0.5432	0.2125	0.6470	0.060*
H14B	0.5982	0.1446	0.7219	0.060*
H14C	0.6097	0.2726	0.7189	0.060*
H1	0.1103 (12)	0.6027 (13)	0.7328 (10)	0.055 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0332 (6)	0.0297 (6)	0.0396 (6)	0.0077 (5)	−0.0033 (5)	−0.0054 (5)
N2	0.0232 (5)	0.0262 (5)	0.0350 (6)	−0.0004 (4)	−0.0003 (4)	−0.0002 (4)
C1	0.0321 (6)	0.0317 (7)	0.0350 (7)	0.0017 (5)	−0.0026 (5)	−0.0024 (5)
C2	0.0248 (6)	0.0282 (6)	0.0365 (7)	−0.0018 (5)	0.0000 (5)	−0.0019 (5)
C3	0.0322 (7)	0.0386 (7)	0.0434 (8)	0.0002 (6)	−0.0045 (6)	0.0023 (6)
C4	0.0412 (8)	0.0546 (9)	0.0356 (8)	−0.0068 (7)	−0.0034 (6)	0.0001 (6)
C7	0.0231 (6)	0.0255 (6)	0.0386 (7)	−0.0031 (5)	0.0019 (5)	−0.0019 (5)
C5	0.0422 (8)	0.0479 (8)	0.0380 (8)	−0.0059 (6)	0.0052 (6)	−0.0103 (6)
C6	0.0320 (7)	0.0335 (7)	0.0448 (8)	−0.0010 (5)	0.0055 (6)	−0.0074 (6)
C8	0.0252 (6)	0.0263 (6)	0.0383 (7)	−0.0011 (5)	0.0005 (5)	0.0000 (5)
C9	0.0298 (7)	0.0302 (7)	0.0442 (8)	0.0033 (5)	0.0023 (6)	0.0047 (5)
C10	0.0273 (6)	0.0286 (6)	0.0441 (7)	−0.0015 (5)	−0.0006 (5)	0.0065 (5)
C11	0.0339 (7)	0.0307 (7)	0.0377 (7)	−0.0007 (5)	−0.0048 (5)	−0.0025 (5)
C12	0.0545 (9)	0.0413 (8)	0.0462 (8)	0.0095 (7)	−0.0089 (7)	0.0019 (6)
C13	0.0701 (11)	0.0508 (9)	0.0514 (9)	−0.0043 (8)	−0.0200 (8)	0.0090 (7)
C14	0.0288 (7)	0.0439 (8)	0.0478 (8)	0.0014 (6)	0.0060 (6)	0.0007 (6)

Geometric parameters (Å, º)

N1—C1	1.3722 (16)	C8—C9	1.4991 (17)
N1—C2	1.3695 (16)	C9—H9A	0.9900
N1—H1	0.920 (17)	C9—H9B	0.9900
N2—C10	1.4727 (15)	C9—C10	1.5257 (17)
N2—C11	1.4712 (15)	C10—H10A	0.9900
N2—C14	1.4668 (16)	C10—H10B	0.9900
C1—H1A	0.9500	C11—H11A	0.9900
C1—C8	1.3618 (17)	C11—H11B	0.9900
C2—C3	1.3932 (18)	C11—C12	1.5126 (18)
C2—C7	1.4177 (17)	C12—H12A	0.9900
C3—H3	0.9500	C12—H12B	0.9900
C3—C4	1.3759 (19)	C12—C13	1.513 (2)
C4—H4	0.9500	C13—H13A	0.9800
C4—C5	1.398 (2)	C13—H13B	0.9800
C7—C6	1.4035 (17)	C13—H13C	0.9800
C7—C8	1.4377 (18)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C5—C6	1.374 (2)	C14—H14C	0.9800
C6—H6	0.9500
C1—N1—H1	123.8 (10)	H9A—C9—H9B	107.7
C2—N1—C1	108.42 (10)	C10—C9—H9A	108.9
C2—N1—H1	127.7 (10)	C10—C9—H9B	108.9
C11—N2—C10	110.74 (10)	N2—C10—C9	112.74 (10)
C14—N2—C10	109.48 (10)	N2—C10—H10A	109.0
C14—N2—C11	111.45 (10)	N2—C10—H10B	109.0
N1—C1—H1A	124.5	C9—C10—H10A	109.0
C8—C1—N1	111.01 (11)	C9—C10—H10B	109.0
C8—C1—H1A	124.5	H10A—C10—H10B	107.8
N1—C2—C3	130.23 (12)	N2—C11—H11A	108.7
N1—C2—C7	107.74 (11)	N2—C11—H11B	108.7
C3—C2—C7	122.01 (12)	N2—C11—C12	114.38 (10)
C2—C3—H3	121.1	H11A—C11—H11B	107.6
C4—C3—C2	117.83 (13)	C12—C11—H11A	108.7
C4—C3—H3	121.1	C12—C11—H11B	108.7
C3—C4—H4	119.4	C11—C12—H12A	109.2
C3—C4—C5	121.19 (13)	C11—C12—H12B	109.2
C5—C4—H4	119.4	C11—C12—C13	112.22 (12)
C2—C7—C8	106.87 (10)	H12A—C12—H12B	107.9
C6—C7—C2	118.39 (11)	C13—C12—H12A	109.2
C6—C7—C8	134.69 (12)	C13—C12—H12B	109.2
C4—C5—H5	119.4	C12—C13—H13A	109.5
C6—C5—C4	121.27 (13)	C12—C13—H13B	109.5
C6—C5—H5	119.4	C12—C13—H13C	109.5
C7—C6—H6	120.3	H13A—C13—H13B	109.5
C5—C6—C7	119.31 (12)	H13A—C13—H13C	109.5
C5—C6—H6	120.3	H13B—C13—H13C	109.5
C1—C8—C7	105.96 (10)	N2—C14—H14A	109.5
C1—C8—C9	127.19 (12)	N2—C14—H14B	109.5
C7—C8—C9	126.70 (11)	N2—C14—H14C	109.5
C8—C9—H9A	108.9	H14A—C14—H14B	109.5
C8—C9—H9B	108.9	H14A—C14—H14C	109.5
C8—C9—C10	113.30 (10)	H14B—C14—H14C	109.5
N1—C1—C8—C7	−0.41 (14)	C3—C2—C7—C6	−0.82 (18)
N1—C1—C8—C9	−176.10 (11)	C3—C2—C7—C8	−178.57 (11)
N1—C2—C3—C4	−177.51 (13)	C3—C4—C5—C6	−0.5 (2)
N1—C2—C7—C6	177.50 (11)	C4—C5—C6—C7	0.1 (2)
N1—C2—C7—C8	−0.25 (13)	C7—C2—C3—C4	0.40 (19)
N2—C11—C12—C13	−173.49 (12)	C7—C8—C9—C10	62.03 (17)
C1—N1—C2—C3	178.13 (13)	C6—C7—C8—C1	−176.81 (13)
C1—N1—C2—C7	0.00 (14)	C6—C7—C8—C9	−1.1 (2)
C1—C8—C9—C10	−123.14 (14)	C8—C7—C6—C5	177.52 (13)
C2—N1—C1—C8	0.27 (14)	C8—C9—C10—N2	−162.95 (10)
C2—C3—C4—C5	0.3 (2)	C10—N2—C11—C12	177.40 (11)
C2—C7—C6—C5	0.56 (18)	C11—N2—C10—C9	−74.78 (13)
C2—C7—C8—C1	0.40 (13)	C14—N2—C10—C9	161.94 (11)
C2—C7—C8—C9	176.12 (11)	C14—N2—C11—C12	−60.47 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.920 (17)	1.990 (17)	2.9097 (15)	179.8 (16)

Symmetry code: (i) −x+1/2, y+1/2, z.