Bufotenidinium iodide

The title compound, 5-hy­droxy-N,N,N-tri­methyl­tryptammonium (5-HTQ) iodide {systematic name: [2-(5-hy­droxy-1H-indol-3-yl)eth­yl]tri­methyl­aza­nium iodide}, C₁₃H₁₉N₂O⁺·I⁻, has a single tryptammonium cation and one iodide anion in the asymmetric unit. The ions are held together by N—H...I and O—H...I hydrogen bonds in infinite chains along [100].

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.013
• wR factor = 0.032
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z > Si, NonCentro ....     Please Do !
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         47 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         34 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT019_ALERT_1_G _diffrn_measured_fraction_theta_full/*_max < 1.0      0.997 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              I
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

[2-(5-Hydroxy-1H-indol-3-yl)ethyl]trimethylazanium iodide

Crystal data

C13H19N2O^+·I^−	Dx = 1.567 Mg m^−3
Mr = 346.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9674 reflections
a = 8.9944 (4) Å	θ = 2.7–26.4°
b = 11.3250 (6) Å	µ = 2.17 mm^−1
c = 14.4042 (7) Å	T = 297 K
V = 1467.23 (12) Å^3	BLOCK, colourless
Z = 4	0.25 × 0.19 × 0.18 mm
F(000) = 688

Data collection

Bruker D8 Venture CMOS diffractometer	2866 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.4°, θmin = 2.9°
Tmin = 0.672, Tmax = 0.745	h = −11→10
45268 measured reflections	k = −14→14
2937 independent reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.013	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.032	w = 1/[σ^2(Fo^2) + (0.0105P)^2 + 0.4198P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
2937 reflections	Δρmax = 0.42 e Å^−3
165 parameters	Δρmin = −0.37 e Å^−3
2 restraints

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.

Refinement. The H atoms bonded to C were positioned geometrically and refined using a riding model with C—H = 0.97 Å and U_iso(H) = 1.2Ueq(C) for CH₂ and C—H = 0.93 Å and U_iso(H) = 1.2Ueq(C) for CH and with C—H = 0.96 Å and U_iso(H) = 1.5Ueq(C) for CH₃. The H atoms bonded to O and N were refined isotropically with a distance restraint of 0.86 (1) Å for O—H and N—H.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	1.27678 (2)	0.68783 (2)	0.80214 (2)	0.04918 (6)
O1	0.9362 (3)	0.5938 (3)	0.71675 (17)	0.0750 (7)
N1	0.6590 (3)	0.6055 (2)	0.37895 (16)	0.0498 (5)
N2	0.2789 (2)	0.30817 (18)	0.61774 (13)	0.0391 (4)
C1	0.5215 (3)	0.5666 (2)	0.40501 (19)	0.0485 (6)
H1B	0.441446	0.556178	0.364948	0.058*
C2	0.7484 (3)	0.61161 (18)	0.45606 (16)	0.0406 (6)
C3	0.8962 (3)	0.6469 (2)	0.4660 (2)	0.0497 (7)
H3	0.950871	0.673197	0.415302	0.060*
C4	0.9584 (3)	0.6418 (2)	0.5530 (2)	0.0507 (7)
H4	1.056532	0.665360	0.561501	0.061*
C5	0.8756 (3)	0.6014 (2)	0.6292 (2)	0.0479 (6)
C6	0.7298 (3)	0.5668 (2)	0.62022 (16)	0.0429 (5)
H6	0.676325	0.540356	0.671410	0.052*
C7	0.6637 (3)	0.57222 (19)	0.53238 (16)	0.0364 (5)
C8	0.5182 (3)	0.5451 (2)	0.49817 (17)	0.0391 (5)
C9	0.3882 (3)	0.5012 (2)	0.55239 (19)	0.0447 (6)
H9A	0.296470	0.525310	0.522426	0.054*
H9B	0.389880	0.534545	0.614414	0.054*
C10	0.3953 (3)	0.3676 (2)	0.55785 (17)	0.0358 (5)
H10A	0.386906	0.336400	0.495364	0.043*
H10B	0.492611	0.345643	0.581186	0.043*
C11	0.3074 (4)	0.3325 (3)	0.71866 (17)	0.0547 (7)
H11A	0.406203	0.307458	0.734450	0.082*
H11B	0.236688	0.290083	0.755761	0.082*
H11C	0.297675	0.415645	0.730285	0.082*
C12	0.2907 (3)	0.1772 (2)	0.6019 (2)	0.0566 (6)
H12A	0.388997	0.151050	0.617656	0.085*
H12B	0.271215	0.160013	0.537743	0.085*
H12C	0.219355	0.136997	0.640060	0.085*
C13	0.1260 (3)	0.3483 (3)	0.5916 (2)	0.0599 (8)
H13A	0.113955	0.429832	0.608060	0.090*
H13B	0.053621	0.301558	0.624009	0.090*
H13C	0.112305	0.339099	0.525871	0.090*
H1A	0.686 (4)	0.629 (3)	0.3256 (13)	0.070 (10)*
H1	1.021 (2)	0.625 (3)	0.713 (3)	0.093 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04798 (9)	0.05760 (10)	0.04197 (8)	−0.00650 (8)	−0.00644 (7)	0.00349 (8)
O1	0.0540 (13)	0.118 (2)	0.0527 (13)	−0.0119 (14)	−0.0117 (10)	−0.0055 (13)
N1	0.0669 (15)	0.0466 (12)	0.0357 (11)	−0.0056 (11)	0.0020 (11)	0.0092 (9)
N2	0.0353 (8)	0.0375 (9)	0.0444 (9)	−0.0029 (11)	0.0023 (8)	−0.0056 (8)
C1	0.0556 (15)	0.0419 (13)	0.0480 (14)	0.0001 (12)	−0.0082 (12)	0.0017 (12)
C2	0.0484 (17)	0.0282 (10)	0.0450 (13)	−0.0017 (10)	0.0060 (11)	0.0012 (9)
C3	0.0529 (16)	0.0398 (13)	0.0564 (16)	−0.0067 (12)	0.0170 (14)	0.0026 (12)
C4	0.0401 (14)	0.0433 (13)	0.0688 (18)	−0.0059 (11)	0.0041 (13)	−0.0079 (13)
C5	0.0463 (15)	0.0500 (15)	0.0473 (14)	−0.0004 (12)	−0.0031 (12)	−0.0097 (11)
C6	0.0443 (12)	0.0455 (12)	0.0389 (11)	−0.0029 (12)	0.0044 (11)	−0.0020 (9)
C7	0.0432 (12)	0.0263 (10)	0.0396 (12)	−0.0014 (9)	0.0050 (10)	−0.0021 (9)
C8	0.0441 (13)	0.0288 (11)	0.0442 (13)	−0.0010 (10)	−0.0002 (11)	−0.0021 (10)
C9	0.0402 (13)	0.0375 (13)	0.0564 (16)	0.0024 (11)	0.0048 (12)	−0.0018 (12)
C10	0.0325 (11)	0.0365 (11)	0.0385 (12)	−0.0011 (9)	0.0010 (9)	−0.0048 (9)
C11	0.0672 (19)	0.0554 (16)	0.0414 (13)	−0.0034 (13)	0.0083 (11)	−0.0036 (11)
C12	0.0596 (15)	0.0380 (12)	0.0721 (17)	−0.0109 (14)	0.0107 (14)	−0.0071 (13)
C13	0.0313 (12)	0.069 (2)	0.080 (2)	−0.0019 (12)	0.0037 (14)	0.0006 (16)

Geometric parameters (Å, º)

O1—C5	1.377 (4)	C6—H6	0.9300
O1—H1	0.847 (13)	C6—C7	1.399 (3)
N1—C1	1.366 (4)	C7—C8	1.432 (3)
N1—C2	1.373 (3)	C8—C9	1.492 (4)
N1—H1A	0.849 (13)	C9—H9A	0.9700
N2—C10	1.515 (3)	C9—H9B	0.9700
N2—C11	1.502 (3)	C9—C10	1.516 (3)
N2—C12	1.504 (3)	C10—H10A	0.9700
N2—C13	1.496 (3)	C10—H10B	0.9700
C1—H1B	0.9300	C11—H11A	0.9600
C1—C8	1.364 (4)	C11—H11B	0.9600
C2—C3	1.395 (4)	C11—H11C	0.9600
C2—C7	1.410 (3)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C3—C4	1.373 (4)	C12—H12C	0.9600
C4—H4	0.9300	C13—H13A	0.9600
C4—C5	1.403 (4)	C13—H13B	0.9600
C5—C6	1.374 (4)	C13—H13C	0.9600
C5—O1—H1	106 (3)	C1—C8—C9	126.2 (3)
C1—N1—C2	108.9 (2)	C7—C8—C9	127.4 (2)
C1—N1—H1A	128 (2)	C8—C9—H9A	109.9
C2—N1—H1A	123 (2)	C8—C9—H9B	109.9
C11—N2—C10	110.56 (19)	C8—C9—C10	109.0 (2)
C11—N2—C12	108.4 (2)	H9A—C9—H9B	108.3
C12—N2—C10	107.63 (18)	C10—C9—H9A	109.9
C13—N2—C10	110.9 (2)	C10—C9—H9B	109.9
C13—N2—C11	110.2 (2)	N2—C10—C9	116.3 (2)
C13—N2—C12	109.0 (2)	N2—C10—H10A	108.2
N1—C1—H1B	124.8	N2—C10—H10B	108.2
C8—C1—N1	110.3 (2)	C9—C10—H10A	108.2
C8—C1—H1B	124.8	C9—C10—H10B	108.2
N1—C2—C3	131.0 (2)	H10A—C10—H10B	107.4
N1—C2—C7	107.4 (2)	N2—C11—H11A	109.5
C3—C2—C7	121.7 (2)	N2—C11—H11B	109.5
C2—C3—H3	121.0	N2—C11—H11C	109.5
C4—C3—C2	118.1 (3)	H11A—C11—H11B	109.5
C4—C3—H3	121.0	H11A—C11—H11C	109.5
C3—C4—H4	119.7	H11B—C11—H11C	109.5
C3—C4—C5	120.7 (3)	N2—C12—H12A	109.5
C5—C4—H4	119.7	N2—C12—H12B	109.5
O1—C5—C4	121.7 (3)	N2—C12—H12C	109.5
C6—C5—O1	116.5 (3)	H12A—C12—H12B	109.5
C6—C5—C4	121.8 (3)	H12A—C12—H12C	109.5
C5—C6—H6	120.7	H12B—C12—H12C	109.5
C5—C6—C7	118.5 (2)	N2—C13—H13A	109.5
C7—C6—H6	120.7	N2—C13—H13B	109.5
C2—C7—C8	107.1 (2)	N2—C13—H13C	109.5
C6—C7—C2	119.3 (2)	H13A—C13—H13B	109.5
C6—C7—C8	133.6 (2)	H13A—C13—H13C	109.5
C1—C8—C7	106.3 (2)	H13B—C13—H13C	109.5
O1—C5—C6—C7	−179.6 (2)	C3—C2—C7—C8	179.1 (2)
N1—C1—C8—C7	−0.1 (3)	C3—C4—C5—O1	179.0 (3)
N1—C1—C8—C9	−179.7 (2)	C3—C4—C5—C6	−0.7 (4)
N1—C2—C3—C4	−178.8 (3)	C4—C5—C6—C7	0.1 (4)
N1—C2—C7—C6	178.5 (2)	C5—C6—C7—C2	0.6 (3)
N1—C2—C7—C8	−1.5 (3)	C5—C6—C7—C8	−179.4 (3)
C1—N1—C2—C3	−179.3 (3)	C6—C7—C8—C1	−179.0 (3)
C1—N1—C2—C7	1.5 (3)	C6—C7—C8—C9	0.6 (4)
C1—C8—C9—C10	92.6 (3)	C7—C2—C3—C4	0.4 (4)
C2—N1—C1—C8	−0.8 (3)	C7—C8—C9—C10	−86.9 (3)
C2—C3—C4—C5	0.4 (4)	C8—C9—C10—N2	174.8 (2)
C2—C7—C8—C1	1.0 (3)	C11—N2—C10—C9	−70.4 (3)
C2—C7—C8—C9	−179.4 (2)	C12—N2—C10—C9	171.4 (2)
C3—C2—C7—C6	−0.9 (3)	C13—N2—C10—C9	52.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···I1^i	0.85 (1)	2.89 (2)	3.662 (2)	152 (3)
O1—H1···I1	0.85 (1)	2.72 (3)	3.468 (2)	147 (4)

Symmetry code: (i) x−1/2, −y+3/2, −z+1.