The crystalline forms of nine hydro­chloride salts of substituted tryptamines

The crystal structures of the hydro­chloride salts of nine substituted tryptamines, namely, 1-methyl­trypt­am­mon­ium chloride, C₁₁H₁₅N₂⁺·Cl⁻, (1), 2-methyl-1-phenyl­trypt­am­mon­ium chloride, C₁₇H₁₉N₂⁺·Cl⁻, (2), 5-meth­oxy­trypt­am­mon­ium chloride, C₁₁H₁₅N₂O⁺·Cl⁻, (3), 5-bromo­trypt­am­mon­ium chloride, C₁₀H₁₂BrN₂⁺·Cl⁻, (4), 5-chloro­trypt­am­mon­ium chloride, C₁₀H₁₂ClN₂⁺·Cl⁻, (5), 5-fluoro­trypt­am­mon­ium chloride, C₁₀H₁₂FN₂⁺·Cl⁻, (6), 5-methyl­trypt­am­mon­ium chloride, C₁₁H₁₅N₂⁺·Cl⁻, (7), 6-fluoro­trypt­am­mon­ium chloride, C₁₀H₁₂FN₂⁺·Cl⁻, (8), and 7-methyl­trypt­am­mon­ium chloride, C₁₁H₁₅N₂⁺·Cl⁻, (9), are reported. The seven tryptamines with N—H indoles, (3)–(9), show very similar structures, with N—H...Cl hydro­gen-bonding networks forming two-dimensional sheets in the crystals. These sheets are combinations of R₄²(8) and R₄²(18) rings, and C₂¹(4) and C₂¹(9) chains. Substitution at the indole N atom reduces the dimensionality of the hydro­gen-bonding network, with com­pounds (1) and (2) demonstrating one-dimensional chains that are a combination of different rings and parallel chains.

Computing details

For all structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-(1-Methyl-1H-indol-3-yl)ethan-1-aminium chloride (1)

Crystal data

C11H15N2^+·Cl^−	Dx = 1.143 Mg m^−3
Mr = 210.70	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c	Cell parameters from 9722 reflections
a = 29.3337 (13) Å	θ = 2.8–24.3°
c = 7.3922 (6) Å	µ = 0.28 mm^−1
V = 5508.6 (7) Å^3	T = 297 K
Z = 18	BLOCK, colourless
F(000) = 2016	0.31 × 0.08 × 0.07 mm

Data collection

Bruker D8 Venture CMOS diffractometer	2091 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.7°, θmin = 3.5°
Tmin = 0.706, Tmax = 0.745	h = −35→35
32453 measured reflections	k = −35→35
2315 independent reflections	l = −9→9

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)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0618P)^2 + 2.0481P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.60 e Å^−3
2315 reflections	Δρmin = −0.15 e Å^−3
140 parameters	Absolute structure: Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
4 restraints	Absolute structure parameter: 0.009 (18)

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
Cl1	0.66266 (4)	0.22246 (4)	0.63002 (12)	0.0663 (3)
N1	0.36653 (12)	0.09035 (13)	0.3658 (4)	0.0674 (8)
N2	0.56375 (11)	0.23378 (13)	0.7085 (5)	0.0597 (7)
C1	0.41758 (15)	0.12607 (16)	0.4106 (5)	0.0654 (9)
H1	0.446658	0.133421	0.339634	0.078*
C2	0.33464 (15)	0.09024 (14)	0.5008 (5)	0.0599 (8)
C3	0.28016 (16)	0.06058 (17)	0.5188 (7)	0.0777 (12)
H3	0.259385	0.035927	0.432066	0.093*
C4	0.25852 (18)	0.0692 (2)	0.6691 (9)	0.0925 (15)
H4	0.222210	0.050013	0.684537	0.111*
C5	0.28923 (18)	0.1058 (2)	0.7999 (8)	0.0896 (13)
H5	0.272972	0.110758	0.899979	0.107*
C6	0.34302 (17)	0.13482 (16)	0.7847 (6)	0.0733 (10)
H6	0.363194	0.159286	0.872790	0.088*
C7	0.36677 (14)	0.12676 (13)	0.6337 (5)	0.0552 (8)
C8	0.42012 (13)	0.14939 (13)	0.5726 (5)	0.0559 (8)
C9	0.46744 (14)	0.18920 (14)	0.6738 (6)	0.0627 (9)
H9A	0.462456	0.180773	0.801749	0.075*
H9B	0.470897	0.223619	0.658077	0.075*
C10	0.51710 (13)	0.19135 (14)	0.6123 (5)	0.0578 (8)
H10A	0.514822	0.157718	0.635309	0.069*
H10B	0.521289	0.197822	0.482993	0.069*
C11	0.3491 (2)	0.0576 (3)	0.2036 (6)	0.1052 (17)
H11A	0.379213	0.061783	0.138148	0.158*
H11B	0.329339	0.068222	0.128344	0.158*
H11C	0.327298	0.021421	0.237532	0.158*
H2A	0.5699 (17)	0.2686 (9)	0.674 (6)	0.072 (11)*
H2B	0.5633 (17)	0.2319 (16)	0.841 (2)	0.069 (13)*
H2C	0.5942 (11)	0.2285 (16)	0.688 (5)	0.068 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0543 (5)	0.0807 (6)	0.0612 (5)	0.0318 (4)	−0.0011 (4)	0.0001 (4)
N1	0.0648 (19)	0.073 (2)	0.0575 (18)	0.0287 (16)	−0.0114 (15)	−0.0049 (14)
N2	0.0478 (15)	0.0654 (18)	0.0622 (17)	0.0256 (14)	0.0003 (13)	0.0065 (14)
C1	0.0551 (19)	0.074 (2)	0.063 (2)	0.0297 (17)	−0.0014 (16)	0.0045 (18)
C2	0.0518 (17)	0.0573 (19)	0.068 (2)	0.0250 (16)	−0.0090 (17)	0.0062 (16)
C3	0.053 (2)	0.070 (2)	0.097 (3)	0.0218 (18)	−0.013 (2)	0.008 (2)
C4	0.050 (2)	0.086 (3)	0.128 (4)	0.024 (2)	0.007 (3)	0.015 (3)
C5	0.069 (3)	0.097 (3)	0.104 (3)	0.043 (3)	0.025 (3)	0.012 (3)
C6	0.068 (2)	0.068 (2)	0.084 (3)	0.034 (2)	0.008 (2)	−0.003 (2)
C7	0.0493 (17)	0.0506 (17)	0.065 (2)	0.0241 (14)	−0.0001 (15)	0.0076 (14)
C8	0.0501 (18)	0.0537 (17)	0.063 (2)	0.0251 (15)	−0.0022 (15)	0.0029 (15)
C9	0.0513 (18)	0.0559 (18)	0.076 (2)	0.0235 (16)	0.0007 (16)	−0.0062 (16)
C10	0.0494 (18)	0.0602 (19)	0.0547 (19)	0.0205 (15)	0.0011 (15)	0.0023 (15)
C11	0.097 (4)	0.126 (4)	0.067 (3)	0.037 (3)	−0.026 (2)	−0.020 (3)

Geometric parameters (Å, º)

N1—C1	1.372 (5)	C5—H5	0.9300
N1—C2	1.366 (5)	C5—C6	1.373 (7)
N1—C11	1.459 (6)	C6—H6	0.9300
N2—C10	1.491 (5)	C6—C7	1.397 (6)
N2—H2A	0.979 (14)	C7—C8	1.433 (5)
N2—H2B	0.983 (14)	C8—C9	1.493 (5)
N2—H2C	0.990 (14)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C1—C8	1.363 (5)	C9—C10	1.497 (5)
C2—C3	1.392 (5)	C10—H10A	0.9700
C2—C7	1.411 (5)	C10—H10B	0.9700
C3—H3	0.9300	C11—H11A	0.9600
C3—C4	1.364 (7)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C4—C5	1.390 (8)
C1—N1—C11	126.2 (4)	C7—C6—H6	120.8
C2—N1—C1	108.1 (3)	C2—C7—C8	107.0 (3)
C2—N1—C11	125.7 (4)	C6—C7—C2	119.0 (4)
C10—N2—H2A	111 (3)	C6—C7—C8	134.0 (4)
C10—N2—H2B	117 (3)	C1—C8—C7	105.8 (3)
C10—N2—H2C	109 (2)	C1—C8—C9	129.0 (3)
H2A—N2—H2B	108 (3)	C7—C8—C9	125.2 (3)
H2A—N2—H2C	114 (3)	C8—C9—H9A	109.1
H2B—N2—H2C	97 (3)	C8—C9—H9B	109.1
N1—C1—H1	124.4	C8—C9—C10	112.7 (3)
C8—C1—N1	111.1 (3)	H9A—C9—H9B	107.8
C8—C1—H1	124.4	C10—C9—H9A	109.1
N1—C2—C3	129.9 (4)	C10—C9—H9B	109.1
N1—C2—C7	108.1 (3)	N2—C10—C9	111.0 (3)
C3—C2—C7	122.0 (4)	N2—C10—H10A	109.4
C2—C3—H3	121.4	N2—C10—H10B	109.4
C4—C3—C2	117.2 (4)	C9—C10—H10A	109.4
C4—C3—H3	121.4	C9—C10—H10B	109.4
C3—C4—H4	119.1	H10A—C10—H10B	108.0
C3—C4—C5	121.9 (4)	N1—C11—H11A	109.5
C5—C4—H4	119.1	N1—C11—H11B	109.5
C4—C5—H5	119.3	N1—C11—H11C	109.5
C6—C5—C4	121.5 (5)	H11A—C11—H11B	109.5
C6—C5—H5	119.3	H11A—C11—H11C	109.5
C5—C6—H6	120.8	H11B—C11—H11C	109.5
C5—C6—C7	118.5 (4)
N1—C1—C8—C7	−0.2 (4)	C3—C2—C7—C8	179.3 (3)
N1—C1—C8—C9	178.3 (4)	C3—C4—C5—C6	−0.6 (8)
N1—C2—C3—C4	−179.4 (4)	C4—C5—C6—C7	−0.2 (7)
N1—C2—C7—C6	178.4 (3)	C5—C6—C7—C2	1.6 (5)
N1—C2—C7—C8	0.2 (4)	C5—C6—C7—C8	179.3 (4)
C1—N1—C2—C3	−179.3 (4)	C6—C7—C8—C1	−177.9 (4)
C1—N1—C2—C7	−0.3 (4)	C6—C7—C8—C9	3.6 (6)
C1—C8—C9—C10	−18.4 (6)	C7—C2—C3—C4	1.7 (6)
C2—N1—C1—C8	0.3 (4)	C7—C8—C9—C10	159.7 (3)
C2—C3—C4—C5	−0.2 (7)	C8—C9—C10—N2	176.5 (3)
C2—C7—C8—C1	0.0 (4)	C11—N1—C1—C8	−179.1 (4)
C2—C7—C8—C9	−178.5 (3)	C11—N1—C2—C3	0.1 (6)
C3—C2—C7—C6	−2.5 (5)	C11—N1—C2—C7	179.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cl1^i	0.97	2.79	3.737 (4)	165
N2—H2A···Cl1^ii	0.98 (1)	2.20 (2)	3.151 (3)	163 (4)
N2—H2B···Cl1^iii	0.98 (1)	2.15 (2)	3.130 (4)	176 (3)
N2—H2C···Cl1	0.99 (1)	2.15 (2)	3.135 (3)	175 (3)

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

2-(2-Methyl-1-phenyl-1H-indol-3-yl)ethan-1-aminium chloride (2)

Crystal data

C17H19N2^+·Cl^−	F(000) = 2432
Mr = 286.79	Dx = 1.224 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.3990 (6) Å	Cell parameters from 9887 reflections
b = 16.3016 (10) Å	θ = 2.7–25.3°
c = 37.091 (2) Å	µ = 0.24 mm^−1
β = 97.963 (2)°	T = 297 K
V = 6227.1 (7) Å^3	BLOCK, grey
Z = 16	0.24 × 0.20 × 0.10 mm

Data collection

Bruker D8 Venture CMOS diffractometer	8101 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.057
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.8°, θmin = 2.7°
Tmin = 0.713, Tmax = 0.745	h = −12→12
111482 measured reflections	k = −19→19
11846 independent reflections	l = −45→45

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 3.9708P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
11846 reflections	Δρmax = 0.19 e Å^−3
773 parameters	Δρmin = −0.23 e Å^−3

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
Cl1	0.79350 (7)	0.96887 (4)	0.45355 (2)	0.05329 (18)
Cl2	0.04463 (6)	0.75927 (4)	0.49628 (2)	0.05032 (17)
Cl3	0.54378 (7)	0.76291 (4)	0.49570 (2)	0.05548 (18)
Cl4	0.79783 (7)	0.52912 (4)	0.95039 (2)	0.05374 (18)
N1	0.9639 (2)	0.75981 (12)	0.67892 (5)	0.0442 (5)
N2	0.8058 (2)	0.85020 (14)	0.52439 (6)	0.0446 (5)
H2A	0.8826 (17)	0.8285 (16)	0.5150 (7)	0.065 (9)*
H2B	0.7271 (18)	0.8251 (16)	0.5108 (7)	0.071 (9)*
H2C	0.806 (3)	0.9103 (6)	0.5227 (8)	0.080 (10)*
N3	0.4492 (2)	0.76986 (12)	0.67862 (5)	0.0431 (5)
N4	0.3053 (2)	0.85178 (14)	0.52353 (5)	0.0441 (5)
H4A	0.301 (3)	0.9119 (7)	0.5218 (9)	0.088 (11)*
H4B	0.2271 (18)	0.8253 (16)	0.5102 (7)	0.075 (9)*
H4C	0.3841 (18)	0.8313 (18)	0.5145 (8)	0.080 (10)*
N5	0.5881 (2)	0.60429 (13)	0.39835 (6)	0.0471 (5)
N6	0.5326 (2)	0.87735 (15)	0.42721 (6)	0.0520 (6)
H6A	0.6155 (18)	0.9037 (18)	0.4374 (8)	0.084 (11)*
H6B	0.535 (3)	0.8211 (9)	0.4370 (8)	0.085 (11)*
H6C	0.461 (2)	0.9076 (18)	0.4360 (8)	0.093 (11)*
N7	0.5765 (2)	0.87732 (13)	0.88966 (6)	0.0483 (5)
N8	0.5324 (2)	0.61619 (15)	0.93046 (6)	0.0493 (5)
H8A	0.6168 (16)	0.5921 (17)	0.9407 (7)	0.072 (9)*
H8B	0.534 (3)	0.6744 (8)	0.9377 (8)	0.082 (10)*
H8C	0.465 (2)	0.5862 (16)	0.9413 (7)	0.079 (10)*
C1	0.9978 (2)	0.76368 (15)	0.64369 (6)	0.0425 (6)
C2	0.8767 (2)	0.82299 (14)	0.68259 (6)	0.0409 (6)
C3	0.8176 (3)	0.84603 (16)	0.71234 (7)	0.0522 (7)
H3	0.834615	0.818143	0.734356	0.063*
C4	0.7332 (3)	0.91142 (17)	0.70828 (8)	0.0606 (8)
H4	0.691712	0.927583	0.727785	0.073*
C5	0.7087 (3)	0.95382 (16)	0.67539 (7)	0.0557 (7)
H5	0.650098	0.997199	0.673191	0.067*
C6	0.7699 (3)	0.93259 (15)	0.64614 (7)	0.0484 (6)
H6	0.754394	0.962135	0.624520	0.058*
C7	0.8556 (2)	0.86597 (14)	0.64931 (6)	0.0388 (5)
C8	0.9338 (2)	0.82692 (15)	0.62527 (6)	0.0405 (6)
C9	0.9362 (2)	0.84990 (17)	0.58621 (6)	0.0469 (6)
H9A	1.008914	0.823018	0.577346	0.056*
H9B	0.948175	0.908691	0.584416	0.056*
C10	0.8121 (2)	0.82529 (15)	0.56297 (6)	0.0425 (6)
H10A	0.802875	0.766172	0.564098	0.051*
H10B	0.739613	0.849693	0.572936	0.051*
C11	0.9920 (2)	0.69574 (15)	0.70494 (7)	0.0438 (6)
C12	0.8913 (3)	0.65465 (17)	0.71758 (8)	0.0607 (8)
H12	0.805893	0.667686	0.708514	0.073*
C13	0.9170 (3)	0.5940 (2)	0.74374 (10)	0.0808 (10)
H13	0.848607	0.567237	0.752484	0.097*
C14	1.0429 (3)	0.5732 (2)	0.75685 (10)	0.0833 (11)
H14	1.059911	0.532305	0.774348	0.100*
C15	1.1429 (3)	0.6130 (2)	0.74395 (10)	0.0801 (10)
H15	1.228127	0.598641	0.752556	0.096*
C16	1.1185 (3)	0.67439 (18)	0.71828 (8)	0.0626 (8)
H16	1.187263	0.701492	0.709906	0.075*
C17	1.0925 (3)	0.70483 (17)	0.63136 (8)	0.0577 (7)
H17A	1.087756	0.707608	0.605357	0.087*
H17B	1.072067	0.650185	0.638370	0.087*
H17C	1.178705	0.718810	0.642421	0.087*
C18	0.4814 (2)	0.77325 (16)	0.64329 (6)	0.0420 (6)
C19	0.3657 (2)	0.83462 (14)	0.68293 (6)	0.0394 (6)
C20	0.3040 (3)	0.85631 (16)	0.71247 (6)	0.0467 (6)
H20	0.319835	0.827805	0.734352	0.056*
C21	0.2188 (3)	0.92138 (17)	0.70830 (7)	0.0543 (7)
H21	0.175551	0.936603	0.727587	0.065*
C22	0.1962 (3)	0.96481 (17)	0.67568 (7)	0.0547 (7)
H22	0.137999	1.008423	0.673553	0.066*
C23	0.2586 (3)	0.94427 (16)	0.64654 (7)	0.0479 (6)
H23	0.243578	0.974154	0.625011	0.057*
C24	0.3448 (2)	0.87786 (14)	0.64969 (6)	0.0385 (5)
C25	0.4203 (2)	0.83788 (15)	0.62541 (6)	0.0401 (6)
C26	0.4255 (2)	0.86152 (16)	0.58646 (6)	0.0443 (6)
H26A	0.426911	0.920811	0.584366	0.053*
H26B	0.504397	0.840166	0.578758	0.053*
C27	0.3096 (2)	0.82794 (15)	0.56233 (6)	0.0406 (6)
H27A	0.310617	0.768565	0.564065	0.049*
H27B	0.231307	0.847319	0.571057	0.049*
C28	0.4871 (2)	0.70846 (16)	0.70529 (6)	0.0434 (6)
C29	0.5444 (3)	0.73212 (18)	0.73976 (7)	0.0539 (7)
H29	0.559023	0.787379	0.745051	0.065*
C30	0.5798 (3)	0.6735 (2)	0.76621 (8)	0.0665 (9)
H30	0.617194	0.689548	0.789365	0.080*
C31	0.5601 (3)	0.5918 (2)	0.75853 (9)	0.0710 (9)
H31	0.584743	0.552560	0.776365	0.085*
C32	0.5038 (3)	0.56802 (19)	0.72444 (9)	0.0688 (9)
H32	0.491071	0.512583	0.719190	0.083*
C33	0.4656 (3)	0.62636 (17)	0.69772 (8)	0.0559 (7)
H33	0.425763	0.610071	0.674845	0.067*
C34	0.5752 (3)	0.71410 (18)	0.63037 (7)	0.0589 (7)
H34A	0.645071	0.703919	0.649610	0.088*
H34B	0.609201	0.736936	0.609791	0.088*
H34C	0.531333	0.663515	0.623428	0.088*
C35	0.6487 (2)	0.68102 (16)	0.40298 (7)	0.0453 (6)
C36	0.4873 (2)	0.60927 (16)	0.36971 (6)	0.0444 (6)
C37	0.4011 (3)	0.54984 (18)	0.35480 (7)	0.0582 (7)
H37	0.404938	0.496512	0.363792	0.070*
C38	0.3088 (3)	0.5726 (2)	0.32601 (8)	0.0681 (9)
H38	0.249163	0.534032	0.315482	0.082*
C39	0.3040 (3)	0.6526 (2)	0.31257 (8)	0.0671 (9)
H39	0.240321	0.666556	0.293406	0.080*
C40	0.3905 (3)	0.71081 (19)	0.32690 (7)	0.0596 (8)
H40	0.387208	0.763521	0.317225	0.071*
C41	0.4843 (3)	0.69032 (16)	0.35635 (6)	0.0451 (6)
C42	0.5875 (2)	0.73390 (16)	0.37777 (7)	0.0454 (6)
C43	0.6168 (3)	0.82317 (16)	0.37277 (7)	0.0530 (7)
H43A	0.617315	0.833782	0.347056	0.064*
H43B	0.703019	0.834986	0.385271	0.064*
C44	0.5207 (3)	0.88058 (16)	0.38686 (7)	0.0510 (7)
H44A	0.536188	0.936211	0.379237	0.061*
H44B	0.433145	0.865307	0.376509	0.061*
C45	0.6151 (3)	0.53317 (16)	0.42098 (7)	0.0477 (6)
C46	0.5229 (3)	0.50360 (18)	0.44069 (8)	0.0625 (8)
H46	0.443431	0.530311	0.439606	0.075*
C47	0.5468 (3)	0.43472 (19)	0.46208 (9)	0.0712 (9)
H47	0.483108	0.414738	0.475045	0.085*
C48	0.6639 (4)	0.39567 (18)	0.46432 (9)	0.0701 (9)
H48	0.680393	0.349676	0.479066	0.084*
C49	0.7564 (4)	0.4243 (2)	0.44489 (9)	0.0747 (10)
H49	0.836058	0.397669	0.446442	0.090*
C50	0.7325 (3)	0.49300 (19)	0.42274 (8)	0.0662 (8)
H50	0.795350	0.511745	0.409184	0.079*
C51	0.7620 (3)	0.69443 (18)	0.43159 (8)	0.0589 (7)
H51A	0.741587	0.674891	0.454551	0.088*
H51B	0.781686	0.751939	0.433399	0.088*
H51C	0.835754	0.665102	0.425281	0.088*
C52	0.6344 (2)	0.80036 (15)	0.89627 (7)	0.0444 (6)
C53	0.4733 (3)	0.86942 (17)	0.86181 (7)	0.0500 (7)
C54	0.3858 (3)	0.9277 (2)	0.84556 (8)	0.0646 (8)
H54	0.392942	0.982596	0.852294	0.078*
C55	0.2882 (3)	0.9010 (2)	0.81909 (8)	0.0751 (10)
H55	0.228509	0.938729	0.807885	0.090*
C56	0.2772 (3)	0.8190 (2)	0.80884 (8)	0.0703 (9)
H56	0.209670	0.802694	0.791193	0.084*
C57	0.3647 (3)	0.7616 (2)	0.82441 (7)	0.0587 (7)
H57	0.357554	0.707103	0.817053	0.070*
C58	0.4645 (3)	0.78623 (17)	0.85140 (7)	0.0489 (6)
C59	0.5687 (3)	0.74419 (16)	0.87334 (7)	0.0459 (6)
C60	0.5970 (3)	0.65432 (15)	0.87112 (7)	0.0507 (7)
H60A	0.686322	0.644406	0.881648	0.061*
H60B	0.587858	0.638157	0.845725	0.061*
C61	0.5086 (3)	0.60172 (15)	0.89056 (6)	0.0463 (6)
H61A	0.418853	0.614330	0.881444	0.056*
H61B	0.523558	0.544338	0.885607	0.056*
C62	0.6076 (3)	0.95001 (15)	0.91065 (8)	0.0495 (6)
C63	0.6052 (3)	0.94922 (18)	0.94765 (8)	0.0606 (8)
H63	0.582463	0.901640	0.959064	0.073*
C64	0.6370 (4)	1.0196 (2)	0.96776 (9)	0.0788 (10)
H64	0.634985	1.018977	0.992745	0.095*
C65	0.6713 (4)	1.0901 (2)	0.95142 (10)	0.0806 (10)
H65	0.694574	1.136719	0.965262	0.097*
C66	0.6709 (3)	1.09126 (18)	0.91442 (10)	0.0739 (9)
H66	0.691808	1.139362	0.903068	0.089*
C67	0.6397 (3)	1.02152 (17)	0.89387 (8)	0.0599 (8)
H67	0.640271	1.022637	0.868826	0.072*
C68	0.7539 (3)	0.78991 (17)	0.92304 (8)	0.0542 (7)
H68A	0.818492	0.828610	0.917844	0.081*
H68B	0.786673	0.735184	0.921333	0.081*
H68C	0.733706	0.799184	0.947184	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0600 (4)	0.0514 (4)	0.0510 (4)	0.0165 (3)	0.0170 (3)	0.0057 (3)
Cl2	0.0471 (4)	0.0551 (4)	0.0488 (4)	0.0054 (3)	0.0065 (3)	−0.0018 (3)
Cl3	0.0508 (4)	0.0580 (4)	0.0598 (4)	0.0023 (3)	0.0151 (3)	0.0067 (3)
Cl4	0.0605 (4)	0.0504 (4)	0.0519 (4)	−0.0154 (3)	0.0136 (3)	−0.0031 (3)
N1	0.0515 (13)	0.0408 (12)	0.0409 (11)	0.0035 (10)	0.0086 (10)	0.0030 (9)
N2	0.0507 (14)	0.0478 (13)	0.0363 (11)	0.0055 (11)	0.0093 (10)	0.0034 (10)
N3	0.0494 (12)	0.0471 (12)	0.0324 (10)	0.0053 (10)	0.0042 (9)	0.0060 (9)
N4	0.0491 (14)	0.0519 (14)	0.0307 (11)	0.0042 (11)	0.0034 (10)	0.0016 (10)
N5	0.0485 (13)	0.0455 (13)	0.0479 (12)	0.0006 (10)	0.0087 (10)	−0.0002 (10)
N6	0.0504 (15)	0.0542 (15)	0.0539 (14)	0.0090 (12)	0.0161 (12)	0.0058 (12)
N7	0.0515 (13)	0.0426 (12)	0.0510 (13)	0.0046 (10)	0.0079 (11)	0.0073 (10)
N8	0.0510 (14)	0.0541 (15)	0.0450 (13)	−0.0114 (12)	0.0147 (11)	−0.0051 (11)
C1	0.0421 (14)	0.0449 (14)	0.0404 (13)	−0.0067 (11)	0.0054 (11)	−0.0043 (11)
C2	0.0500 (15)	0.0358 (13)	0.0378 (13)	−0.0017 (11)	0.0087 (11)	−0.0004 (10)
C3	0.076 (2)	0.0446 (15)	0.0374 (14)	0.0019 (14)	0.0145 (13)	0.0044 (12)
C4	0.087 (2)	0.0491 (16)	0.0507 (16)	0.0067 (16)	0.0261 (15)	−0.0035 (13)
C5	0.075 (2)	0.0382 (15)	0.0562 (17)	0.0099 (13)	0.0165 (15)	−0.0015 (12)
C6	0.0608 (17)	0.0391 (14)	0.0450 (14)	−0.0010 (13)	0.0063 (13)	0.0045 (12)
C7	0.0434 (14)	0.0368 (13)	0.0356 (13)	−0.0070 (11)	0.0037 (11)	0.0004 (10)
C8	0.0400 (14)	0.0454 (14)	0.0365 (13)	−0.0078 (11)	0.0063 (11)	0.0002 (11)
C9	0.0456 (15)	0.0566 (16)	0.0405 (14)	−0.0050 (12)	0.0131 (11)	0.0014 (12)
C10	0.0510 (15)	0.0430 (14)	0.0345 (13)	−0.0017 (12)	0.0097 (11)	0.0047 (11)
C11	0.0468 (15)	0.0390 (14)	0.0449 (14)	−0.0008 (11)	0.0034 (12)	0.0037 (11)
C12	0.0475 (16)	0.0558 (17)	0.078 (2)	0.0019 (14)	0.0053 (15)	0.0176 (15)
C13	0.068 (2)	0.066 (2)	0.112 (3)	0.0036 (17)	0.024 (2)	0.042 (2)
C14	0.078 (2)	0.071 (2)	0.101 (3)	0.0159 (19)	0.011 (2)	0.045 (2)
C15	0.058 (2)	0.080 (2)	0.098 (3)	0.0093 (18)	−0.0045 (18)	0.032 (2)
C16	0.0503 (17)	0.0599 (18)	0.076 (2)	−0.0053 (14)	0.0030 (15)	0.0154 (16)
C17	0.0532 (17)	0.0584 (17)	0.0628 (18)	0.0045 (14)	0.0131 (14)	−0.0063 (14)
C18	0.0408 (14)	0.0531 (15)	0.0318 (12)	0.0005 (12)	0.0040 (10)	0.0016 (11)
C19	0.0421 (14)	0.0410 (14)	0.0345 (12)	−0.0044 (11)	0.0032 (10)	0.0002 (10)
C20	0.0575 (16)	0.0493 (15)	0.0334 (13)	−0.0025 (13)	0.0063 (12)	0.0022 (11)
C21	0.0658 (18)	0.0552 (17)	0.0437 (15)	0.0027 (14)	0.0143 (13)	−0.0090 (13)
C22	0.0626 (18)	0.0483 (16)	0.0528 (16)	0.0118 (13)	0.0061 (14)	−0.0045 (13)
C23	0.0538 (16)	0.0463 (15)	0.0419 (14)	0.0015 (13)	0.0007 (12)	0.0042 (12)
C24	0.0390 (13)	0.0414 (13)	0.0334 (12)	−0.0064 (11)	−0.0012 (10)	0.0014 (10)
C25	0.0370 (13)	0.0504 (15)	0.0319 (12)	−0.0041 (11)	0.0015 (10)	0.0026 (11)
C26	0.0400 (14)	0.0592 (16)	0.0339 (13)	−0.0027 (12)	0.0059 (11)	0.0066 (12)
C27	0.0471 (14)	0.0444 (14)	0.0304 (12)	−0.0004 (11)	0.0060 (11)	0.0025 (10)
C28	0.0403 (14)	0.0524 (16)	0.0376 (13)	0.0030 (12)	0.0059 (11)	0.0093 (11)
C29	0.0553 (17)	0.0644 (18)	0.0406 (14)	−0.0025 (14)	0.0017 (12)	0.0095 (13)
C30	0.0615 (19)	0.092 (3)	0.0454 (16)	0.0062 (18)	0.0047 (14)	0.0232 (16)
C31	0.065 (2)	0.081 (2)	0.069 (2)	0.0226 (18)	0.0191 (17)	0.0401 (19)
C32	0.072 (2)	0.0526 (18)	0.086 (2)	0.0098 (16)	0.0271 (18)	0.0168 (17)
C33	0.0586 (18)	0.0551 (18)	0.0551 (17)	0.0043 (14)	0.0110 (14)	0.0053 (14)
C34	0.0594 (18)	0.0685 (19)	0.0514 (16)	0.0172 (15)	0.0163 (14)	0.0058 (14)
C35	0.0426 (14)	0.0489 (15)	0.0464 (14)	−0.0008 (12)	0.0136 (12)	−0.0059 (12)
C36	0.0478 (15)	0.0509 (15)	0.0364 (13)	0.0002 (12)	0.0124 (12)	−0.0041 (12)
C37	0.071 (2)	0.0526 (17)	0.0514 (16)	−0.0060 (15)	0.0098 (15)	−0.0062 (13)
C38	0.071 (2)	0.081 (2)	0.0504 (17)	−0.0154 (17)	0.0023 (15)	−0.0112 (16)
C39	0.069 (2)	0.090 (2)	0.0398 (15)	−0.0019 (18)	−0.0019 (14)	−0.0013 (16)
C40	0.070 (2)	0.0670 (19)	0.0426 (15)	0.0048 (16)	0.0111 (14)	0.0064 (14)
C41	0.0512 (15)	0.0488 (15)	0.0377 (13)	0.0022 (12)	0.0147 (12)	−0.0006 (11)
C42	0.0483 (15)	0.0461 (15)	0.0448 (14)	−0.0014 (12)	0.0177 (12)	−0.0018 (12)
C43	0.0584 (17)	0.0535 (16)	0.0512 (16)	−0.0041 (14)	0.0220 (13)	0.0020 (13)
C44	0.0543 (16)	0.0453 (15)	0.0540 (16)	0.0014 (13)	0.0094 (13)	0.0085 (12)
C45	0.0563 (16)	0.0440 (15)	0.0431 (14)	0.0043 (13)	0.0077 (12)	−0.0019 (12)
C46	0.0612 (18)	0.0605 (18)	0.0679 (19)	0.0082 (15)	0.0164 (15)	0.0106 (15)
C47	0.084 (2)	0.061 (2)	0.070 (2)	−0.0013 (18)	0.0174 (18)	0.0137 (16)
C48	0.102 (3)	0.0439 (17)	0.0606 (19)	0.0067 (18)	−0.0013 (19)	0.0026 (14)
C49	0.083 (2)	0.065 (2)	0.075 (2)	0.0294 (18)	0.0058 (19)	−0.0019 (18)
C50	0.067 (2)	0.068 (2)	0.0678 (19)	0.0172 (16)	0.0231 (16)	0.0041 (16)
C51	0.0484 (16)	0.0657 (19)	0.0624 (18)	0.0013 (14)	0.0074 (14)	−0.0092 (15)
C52	0.0442 (14)	0.0406 (14)	0.0511 (15)	0.0030 (12)	0.0163 (12)	0.0115 (12)
C53	0.0565 (17)	0.0554 (17)	0.0405 (14)	0.0067 (13)	0.0158 (13)	0.0093 (12)
C54	0.074 (2)	0.066 (2)	0.0559 (18)	0.0208 (17)	0.0152 (16)	0.0120 (15)
C55	0.072 (2)	0.102 (3)	0.0517 (18)	0.025 (2)	0.0079 (16)	0.0171 (18)
C56	0.067 (2)	0.105 (3)	0.0397 (16)	0.004 (2)	0.0079 (14)	0.0027 (17)
C57	0.0648 (19)	0.074 (2)	0.0404 (15)	−0.0036 (16)	0.0167 (14)	−0.0012 (14)
C58	0.0523 (16)	0.0590 (17)	0.0388 (14)	0.0010 (13)	0.0192 (12)	0.0046 (12)
C59	0.0505 (15)	0.0454 (15)	0.0454 (14)	0.0028 (12)	0.0193 (12)	0.0079 (12)
C60	0.0618 (17)	0.0478 (15)	0.0463 (15)	0.0053 (13)	0.0202 (13)	0.0012 (12)
C61	0.0509 (15)	0.0430 (14)	0.0443 (14)	−0.0033 (12)	0.0041 (12)	−0.0034 (11)
C62	0.0498 (16)	0.0394 (14)	0.0606 (17)	0.0043 (12)	0.0123 (13)	0.0048 (13)
C63	0.073 (2)	0.0485 (17)	0.0597 (18)	−0.0018 (15)	0.0086 (15)	0.0083 (14)
C64	0.112 (3)	0.061 (2)	0.061 (2)	0.008 (2)	0.0023 (19)	0.0002 (17)
C65	0.103 (3)	0.0500 (19)	0.086 (3)	0.0021 (18)	0.002 (2)	−0.0057 (18)
C66	0.088 (2)	0.0366 (16)	0.101 (3)	−0.0023 (16)	0.026 (2)	0.0094 (17)
C67	0.0693 (19)	0.0469 (17)	0.0685 (19)	0.0043 (14)	0.0264 (15)	0.0087 (14)
C68	0.0500 (16)	0.0498 (16)	0.0640 (18)	0.0021 (13)	0.0117 (14)	0.0094 (13)

Geometric parameters (Å, º)

N1—C1	1.401 (3)	C28—C29	1.388 (3)
N1—C2	1.391 (3)	C28—C33	1.379 (4)
N1—C11	1.425 (3)	C29—H29	0.9300
N2—H2A	0.981 (10)	C29—C30	1.383 (4)
N2—H2B	0.989 (10)	C30—H30	0.9300
N2—H2C	0.982 (10)	C30—C31	1.371 (5)
N2—C10	1.480 (3)	C31—H31	0.9300
N3—C18	1.398 (3)	C31—C32	1.374 (5)
N3—C19	1.390 (3)	C32—H32	0.9300
N3—C28	1.424 (3)	C32—C33	1.391 (4)
N4—H4A	0.983 (10)	C33—H33	0.9300
N4—H4B	0.990 (10)	C34—H34A	0.9600
N4—H4C	0.986 (10)	C34—H34B	0.9600
N4—C27	1.485 (3)	C34—H34C	0.9600
N5—C35	1.400 (3)	C35—C42	1.363 (4)
N5—C36	1.388 (3)	C35—C51	1.489 (4)
N5—C45	1.436 (3)	C36—C37	1.382 (4)
N6—H6A	0.990 (10)	C36—C41	1.410 (4)
N6—H6B	0.985 (10)	C37—H37	0.9300
N6—H6C	0.989 (10)	C37—C38	1.384 (4)
N6—C44	1.485 (3)	C38—H38	0.9300
N7—C52	1.398 (3)	C38—C39	1.394 (4)
N7—C53	1.388 (3)	C39—H39	0.9300
N7—C62	1.430 (3)	C39—C40	1.364 (4)
N8—H8A	0.988 (10)	C40—H40	0.9300
N8—H8B	0.986 (10)	C40—C41	1.401 (4)
N8—H8C	0.983 (10)	C41—C42	1.432 (4)
N8—C61	1.485 (3)	C42—C43	1.504 (4)
C1—C8	1.359 (3)	C43—H43A	0.9700
C1—C17	1.491 (4)	C43—H43B	0.9700
C2—C3	1.387 (3)	C43—C44	1.514 (4)
C2—C7	1.410 (3)	C44—H44A	0.9700
C3—H3	0.9300	C44—H44B	0.9700
C3—C4	1.376 (4)	C45—C46	1.372 (4)
C4—H4	0.9300	C45—C50	1.378 (4)
C4—C5	1.395 (4)	C46—H46	0.9300
C5—H5	0.9300	C46—C47	1.378 (4)
C5—C6	1.375 (4)	C47—H47	0.9300
C6—H6	0.9300	C47—C48	1.366 (4)
C6—C7	1.400 (3)	C48—H48	0.9300
C7—C8	1.436 (3)	C48—C49	1.361 (5)
C8—C9	1.500 (3)	C49—H49	0.9300
C9—H9A	0.9700	C49—C50	1.391 (4)
C9—H9B	0.9700	C50—H50	0.9300
C9—C10	1.503 (3)	C51—H51A	0.9600
C10—H10A	0.9700	C51—H51B	0.9600
C10—H10B	0.9700	C51—H51C	0.9600
C11—C12	1.378 (4)	C52—C59	1.367 (4)
C11—C16	1.384 (4)	C52—C68	1.489 (4)
C12—H12	0.9300	C53—C54	1.393 (4)
C12—C13	1.385 (4)	C53—C58	1.410 (4)
C13—H13	0.9300	C54—H54	0.9300
C13—C14	1.375 (4)	C54—C55	1.381 (4)
C14—H14	0.9300	C55—H55	0.9300
C14—C15	1.367 (5)	C55—C56	1.390 (5)
C15—H15	0.9300	C56—H56	0.9300
C15—C16	1.380 (4)	C56—C57	1.375 (4)
C16—H16	0.9300	C57—H57	0.9300
C17—H17A	0.9600	C57—C58	1.397 (4)
C17—H17B	0.9600	C58—C59	1.435 (4)
C17—H17C	0.9600	C59—C60	1.499 (3)
C18—C25	1.355 (3)	C60—H60A	0.9700
C18—C34	1.496 (3)	C60—H60B	0.9700
C19—C20	1.390 (3)	C60—C61	1.511 (3)
C19—C24	1.410 (3)	C61—H61A	0.9700
C20—H20	0.9300	C61—H61B	0.9700
C20—C21	1.377 (4)	C62—C63	1.376 (4)
C21—H21	0.9300	C62—C67	1.384 (4)
C21—C22	1.393 (4)	C63—H63	0.9300
C22—H22	0.9300	C63—C64	1.383 (4)
C22—C23	1.376 (4)	C64—H64	0.9300
C23—H23	0.9300	C64—C65	1.370 (5)
C23—C24	1.400 (3)	C65—H65	0.9300
C24—C25	1.432 (3)	C65—C66	1.372 (5)
C25—C26	1.503 (3)	C66—H66	0.9300
C26—H26A	0.9700	C66—C67	1.382 (4)
C26—H26B	0.9700	C67—H67	0.9300
C26—C27	1.501 (3)	C68—H68A	0.9600
C27—H27A	0.9700	C68—H68B	0.9600
C27—H27B	0.9700	C68—H68C	0.9600
C1—N1—C11	127.6 (2)	C29—C30—H30	119.8
C2—N1—C1	108.05 (19)	C31—C30—C29	120.4 (3)
C2—N1—C11	123.5 (2)	C31—C30—H30	119.8
H2A—N2—H2B	109 (2)	C30—C31—H31	120.1
H2A—N2—H2C	109 (2)	C30—C31—C32	119.8 (3)
H2B—N2—H2C	113 (2)	C32—C31—H31	120.1
C10—N2—H2A	108.4 (16)	C31—C32—H32	119.8
C10—N2—H2B	107.7 (17)	C31—C32—C33	120.4 (3)
C10—N2—H2C	109.6 (18)	C33—C32—H32	119.8
C18—N3—C28	126.9 (2)	C28—C33—C32	119.8 (3)
C19—N3—C18	108.21 (19)	C28—C33—H33	120.1
C19—N3—C28	124.8 (2)	C32—C33—H33	120.1
H4A—N4—H4B	112 (3)	C18—C34—H34A	109.5
H4A—N4—H4C	111 (3)	C18—C34—H34B	109.5
H4B—N4—H4C	110 (2)	C18—C34—H34C	109.5
C27—N4—H4A	108.6 (19)	H34A—C34—H34B	109.5
C27—N4—H4B	106.4 (17)	H34A—C34—H34C	109.5
C27—N4—H4C	109.1 (18)	H34B—C34—H34C	109.5
C35—N5—C45	127.0 (2)	N5—C35—C51	121.1 (2)
C36—N5—C35	108.7 (2)	C42—C35—N5	108.8 (2)
C36—N5—C45	124.1 (2)	C42—C35—C51	130.1 (2)
H6A—N6—H6B	107 (3)	N5—C36—C41	107.5 (2)
H6A—N6—H6C	109 (3)	C37—C36—N5	130.1 (2)
H6B—N6—H6C	109 (3)	C37—C36—C41	122.3 (2)
C44—N6—H6A	108.5 (19)	C36—C37—H37	121.2
C44—N6—H6B	113.5 (19)	C36—C37—C38	117.6 (3)
C44—N6—H6C	110.6 (19)	C38—C37—H37	121.2
C52—N7—C62	126.1 (2)	C37—C38—H38	119.6
C53—N7—C52	108.5 (2)	C37—C38—C39	120.9 (3)
C53—N7—C62	125.1 (2)	C39—C38—H38	119.6
H8A—N8—H8B	107 (3)	C38—C39—H39	119.3
H8A—N8—H8C	107 (2)	C40—C39—C38	121.5 (3)
H8B—N8—H8C	111 (3)	C40—C39—H39	119.3
C61—N8—H8A	109.6 (17)	C39—C40—H40	120.4
C61—N8—H8B	114.7 (18)	C39—C40—C41	119.2 (3)
C61—N8—H8C	107.4 (18)	C41—C40—H40	120.4
N1—C1—C17	121.3 (2)	C36—C41—C42	107.0 (2)
C8—C1—N1	109.5 (2)	C40—C41—C36	118.5 (3)
C8—C1—C17	129.2 (2)	C40—C41—C42	134.6 (3)
N1—C2—C7	107.9 (2)	C35—C42—C41	108.0 (2)
C3—C2—N1	130.2 (2)	C35—C42—C43	127.9 (2)
C3—C2—C7	122.0 (2)	C41—C42—C43	124.1 (2)
C2—C3—H3	121.0	C42—C43—H43A	108.8
C4—C3—C2	118.0 (2)	C42—C43—H43B	108.8
C4—C3—H3	121.0	C42—C43—C44	113.6 (2)
C3—C4—H4	119.5	H43A—C43—H43B	107.7
C3—C4—C5	121.0 (3)	C44—C43—H43A	108.8
C5—C4—H4	119.5	C44—C43—H43B	108.8
C4—C5—H5	119.4	N6—C44—C43	111.0 (2)
C6—C5—C4	121.2 (3)	N6—C44—H44A	109.4
C6—C5—H5	119.4	N6—C44—H44B	109.4
C5—C6—H6	120.4	C43—C44—H44A	109.4
C5—C6—C7	119.2 (2)	C43—C44—H44B	109.4
C7—C6—H6	120.4	H44A—C44—H44B	108.0
C2—C7—C8	106.9 (2)	C46—C45—N5	120.0 (2)
C6—C7—C2	118.6 (2)	C46—C45—C50	119.2 (3)
C6—C7—C8	134.5 (2)	C50—C45—N5	120.8 (3)
C1—C8—C7	107.7 (2)	C45—C46—H46	119.7
C1—C8—C9	127.1 (2)	C45—C46—C47	120.6 (3)
C7—C8—C9	125.1 (2)	C47—C46—H46	119.7
C8—C9—H9A	109.4	C46—C47—H47	119.9
C8—C9—H9B	109.4	C48—C47—C46	120.2 (3)
C8—C9—C10	111.1 (2)	C48—C47—H47	119.9
H9A—C9—H9B	108.0	C47—C48—H48	120.1
C10—C9—H9A	109.4	C49—C48—C47	119.8 (3)
C10—C9—H9B	109.4	C49—C48—H48	120.1
N2—C10—C9	113.6 (2)	C48—C49—H49	119.8
N2—C10—H10A	108.8	C48—C49—C50	120.5 (3)
N2—C10—H10B	108.8	C50—C49—H49	119.8
C9—C10—H10A	108.8	C45—C50—C49	119.7 (3)
C9—C10—H10B	108.8	C45—C50—H50	120.2
H10A—C10—H10B	107.7	C49—C50—H50	120.2
C12—C11—N1	119.5 (2)	C35—C51—H51A	109.5
C12—C11—C16	119.0 (2)	C35—C51—H51B	109.5
C16—C11—N1	121.5 (2)	C35—C51—H51C	109.5
C11—C12—H12	119.9	H51A—C51—H51B	109.5
C11—C12—C13	120.2 (3)	H51A—C51—H51C	109.5
C13—C12—H12	119.9	H51B—C51—H51C	109.5
C12—C13—H13	119.8	N7—C52—C68	121.3 (2)
C14—C13—C12	120.4 (3)	C59—C52—N7	109.0 (2)
C14—C13—H13	119.8	C59—C52—C68	129.6 (2)
C13—C14—H14	120.3	N7—C53—C54	130.5 (3)
C15—C14—C13	119.5 (3)	N7—C53—C58	107.9 (2)
C15—C14—H14	120.3	C54—C53—C58	121.6 (3)
C14—C15—H15	119.7	C53—C54—H54	121.1
C14—C15—C16	120.7 (3)	C55—C54—C53	117.7 (3)
C16—C15—H15	119.7	C55—C54—H54	121.1
C11—C16—H16	119.9	C54—C55—H55	119.3
C15—C16—C11	120.2 (3)	C54—C55—C56	121.4 (3)
C15—C16—H16	119.9	C56—C55—H55	119.3
C1—C17—H17A	109.5	C55—C56—H56	119.5
C1—C17—H17B	109.5	C57—C56—C55	121.0 (3)
C1—C17—H17C	109.5	C57—C56—H56	119.5
H17A—C17—H17B	109.5	C56—C57—H57	120.4
H17A—C17—H17C	109.5	C56—C57—C58	119.3 (3)
H17B—C17—H17C	109.5	C58—C57—H57	120.4
N3—C18—C34	121.7 (2)	C53—C58—C59	106.8 (2)
C25—C18—N3	109.4 (2)	C57—C58—C53	119.1 (3)
C25—C18—C34	128.8 (2)	C57—C58—C59	134.1 (3)
N3—C19—C24	107.6 (2)	C52—C59—C58	107.8 (2)
C20—C19—N3	130.4 (2)	C52—C59—C60	127.2 (2)
C20—C19—C24	122.0 (2)	C58—C59—C60	125.0 (3)
C19—C20—H20	121.1	C59—C60—H60A	109.0
C21—C20—C19	117.9 (2)	C59—C60—H60B	109.0
C21—C20—H20	121.1	C59—C60—C61	113.0 (2)
C20—C21—H21	119.4	H60A—C60—H60B	107.8
C20—C21—C22	121.1 (2)	C61—C60—H60A	109.0
C22—C21—H21	119.4	C61—C60—H60B	109.0
C21—C22—H22	119.4	N8—C61—C60	110.9 (2)
C23—C22—C21	121.1 (3)	N8—C61—H61A	109.5
C23—C22—H22	119.4	N8—C61—H61B	109.5
C22—C23—H23	120.4	C60—C61—H61A	109.5
C22—C23—C24	119.2 (2)	C60—C61—H61B	109.5
C24—C23—H23	120.4	H61A—C61—H61B	108.0
C19—C24—C25	106.9 (2)	C63—C62—N7	120.1 (2)
C23—C24—C19	118.6 (2)	C63—C62—C67	119.7 (3)
C23—C24—C25	134.5 (2)	C67—C62—N7	120.2 (2)
C18—C25—C24	107.9 (2)	C62—C63—H63	120.2
C18—C25—C26	126.4 (2)	C62—C63—C64	119.6 (3)
C24—C25—C26	125.7 (2)	C64—C63—H63	120.2
C25—C26—H26A	109.6	C63—C64—H64	119.5
C25—C26—H26B	109.6	C65—C64—C63	121.0 (3)
H26A—C26—H26B	108.1	C65—C64—H64	119.5
C27—C26—C25	110.3 (2)	C64—C65—H65	120.4
C27—C26—H26A	109.6	C64—C65—C66	119.3 (3)
C27—C26—H26B	109.6	C66—C65—H65	120.4
N4—C27—C26	113.3 (2)	C65—C66—H66	119.7
N4—C27—H27A	108.9	C65—C66—C67	120.6 (3)
N4—C27—H27B	108.9	C67—C66—H66	119.7
C26—C27—H27A	108.9	C62—C67—H67	120.1
C26—C27—H27B	108.9	C66—C67—C62	119.9 (3)
H27A—C27—H27B	107.7	C66—C67—H67	120.1
C29—C28—N3	119.1 (2)	C52—C68—H68A	109.5
C33—C28—N3	121.3 (2)	C52—C68—H68B	109.5
C33—C28—C29	119.6 (2)	C52—C68—H68C	109.5
C28—C29—H29	120.0	H68A—C68—H68B	109.5
C30—C29—C28	120.0 (3)	H68A—C68—H68C	109.5
C30—C29—H29	120.0	H68B—C68—H68C	109.5
N1—C1—C8—C7	0.2 (3)	C24—C25—C26—C27	−80.4 (3)
N1—C1—C8—C9	−176.3 (2)	C25—C26—C27—N4	177.6 (2)
N1—C2—C3—C4	−179.3 (3)	C28—N3—C18—C25	176.1 (2)
N1—C2—C7—C6	179.5 (2)	C28—N3—C18—C34	−6.6 (4)
N1—C2—C7—C8	−0.4 (3)	C28—N3—C19—C20	1.7 (4)
N1—C11—C12—C13	−177.9 (3)	C28—N3—C19—C24	−175.6 (2)
N1—C11—C16—C15	178.9 (3)	C28—C29—C30—C31	0.8 (4)
N3—C18—C25—C24	−0.4 (3)	C29—C28—C33—C32	−1.2 (4)
N3—C18—C25—C26	−177.8 (2)	C29—C30—C31—C32	−0.6 (5)
N3—C19—C20—C21	−175.8 (2)	C30—C31—C32—C33	−0.5 (5)
N3—C19—C24—C23	177.1 (2)	C31—C32—C33—C28	1.4 (4)
N3—C19—C24—C25	−1.0 (3)	C33—C28—C29—C30	0.1 (4)
N3—C28—C29—C30	178.9 (2)	C34—C18—C25—C24	−177.5 (3)
N3—C28—C33—C32	−179.9 (2)	C34—C18—C25—C26	5.1 (4)
N5—C35—C42—C41	0.2 (3)	C35—N5—C36—C37	179.3 (3)
N5—C35—C42—C43	178.7 (2)	C35—N5—C36—C41	−0.3 (3)
N5—C36—C37—C38	179.8 (3)	C35—N5—C45—C46	114.2 (3)
N5—C36—C41—C40	179.5 (2)	C35—N5—C45—C50	−66.9 (4)
N5—C36—C41—C42	0.4 (3)	C35—C42—C43—C44	−104.1 (3)
N5—C45—C46—C47	179.0 (3)	C36—N5—C35—C42	0.0 (3)
N5—C45—C50—C49	179.9 (3)	C36—N5—C35—C51	−179.3 (2)
N7—C52—C59—C58	−0.4 (3)	C36—N5—C45—C46	−59.7 (3)
N7—C52—C59—C60	−179.8 (2)	C36—N5—C45—C50	119.2 (3)
N7—C53—C54—C55	−177.3 (3)	C36—C37—C38—C39	0.3 (4)
N7—C53—C58—C57	177.9 (2)	C36—C41—C42—C35	−0.4 (3)
N7—C53—C58—C59	−1.5 (3)	C36—C41—C42—C43	−179.0 (2)
N7—C62—C63—C64	179.2 (3)	C37—C36—C41—C40	−0.1 (4)
N7—C62—C67—C66	−179.3 (3)	C37—C36—C41—C42	−179.2 (2)
C1—N1—C2—C3	−178.3 (3)	C37—C38—C39—C40	0.8 (5)
C1—N1—C2—C7	0.5 (3)	C38—C39—C40—C41	−1.6 (5)
C1—N1—C11—C12	−119.5 (3)	C39—C40—C41—C36	1.2 (4)
C1—N1—C11—C16	61.4 (4)	C39—C40—C41—C42	−180.0 (3)
C1—C8—C9—C10	104.8 (3)	C40—C41—C42—C35	−179.3 (3)
C2—N1—C1—C8	−0.4 (3)	C40—C41—C42—C43	2.1 (5)
C2—N1—C1—C17	178.8 (2)	C41—C36—C37—C38	−0.7 (4)
C2—N1—C11—C12	48.5 (4)	C41—C42—C43—C44	74.2 (3)
C2—N1—C11—C16	−130.6 (3)	C42—C43—C44—N6	68.6 (3)
C2—C3—C4—C5	−0.7 (4)	C45—N5—C35—C42	−174.6 (2)
C2—C7—C8—C1	0.1 (3)	C45—N5—C35—C51	6.1 (4)
C2—C7—C8—C9	176.7 (2)	C45—N5—C36—C37	−5.9 (4)
C3—C2—C7—C6	−1.6 (4)	C45—N5—C36—C41	174.5 (2)
C3—C2—C7—C8	178.5 (2)	C45—C46—C47—C48	1.0 (5)
C3—C4—C5—C6	−1.1 (5)	C46—C45—C50—C49	−1.2 (4)
C4—C5—C6—C7	1.6 (4)	C46—C47—C48—C49	−1.0 (5)
C5—C6—C7—C2	−0.2 (4)	C47—C48—C49—C50	0.0 (5)
C5—C6—C7—C8	179.6 (3)	C48—C49—C50—C45	1.1 (5)
C6—C7—C8—C1	−179.7 (3)	C50—C45—C46—C47	0.1 (4)
C6—C7—C8—C9	−3.1 (4)	C51—C35—C42—C41	179.5 (3)
C7—C2—C3—C4	2.0 (4)	C51—C35—C42—C43	−2.0 (4)
C7—C8—C9—C10	−71.1 (3)	C52—N7—C53—C54	179.7 (3)
C8—C9—C10—N2	177.0 (2)	C52—N7—C53—C58	1.3 (3)
C11—N1—C1—C8	169.1 (2)	C52—N7—C62—C63	−53.9 (4)
C11—N1—C1—C17	−11.7 (4)	C52—N7—C62—C67	126.3 (3)
C11—N1—C2—C3	11.7 (4)	C52—C59—C60—C61	100.3 (3)
C11—N1—C2—C7	−169.6 (2)	C53—N7—C52—C59	−0.6 (3)
C11—C12—C13—C14	−1.2 (5)	C53—N7—C52—C68	175.7 (2)
C12—C11—C16—C15	−0.2 (5)	C53—N7—C62—C63	118.2 (3)
C12—C13—C14—C15	0.2 (6)	C53—N7—C62—C67	−61.6 (4)
C13—C14—C15—C16	0.7 (6)	C53—C54—C55—C56	−0.1 (5)
C14—C15—C16—C11	−0.7 (5)	C53—C58—C59—C52	1.2 (3)
C16—C11—C12—C13	1.2 (5)	C53—C58—C59—C60	−179.4 (2)
C17—C1—C8—C7	−178.9 (2)	C54—C53—C58—C57	−0.7 (4)
C17—C1—C8—C9	4.6 (4)	C54—C53—C58—C59	179.9 (2)
C18—N3—C19—C20	178.0 (3)	C54—C55—C56—C57	−1.0 (5)
C18—N3—C19—C24	0.8 (3)	C55—C56—C57—C58	1.2 (4)
C18—N3—C28—C29	128.2 (3)	C56—C57—C58—C53	−0.4 (4)
C18—N3—C28—C33	−53.1 (4)	C56—C57—C58—C59	178.8 (3)
C18—C25—C26—C27	96.5 (3)	C57—C58—C59—C52	−178.1 (3)
C19—N3—C18—C25	−0.2 (3)	C57—C58—C59—C60	1.3 (5)
C19—N3—C18—C34	177.1 (2)	C58—C53—C54—C55	1.0 (4)
C19—N3—C28—C29	−56.2 (3)	C58—C59—C60—C61	−79.0 (3)
C19—N3—C28—C33	122.6 (3)	C59—C60—C61—N8	−66.5 (3)
C19—C20—C21—C22	−0.8 (4)	C62—N7—C52—C59	172.6 (2)
C19—C24—C25—C18	0.9 (3)	C62—N7—C52—C68	−11.1 (4)
C19—C24—C25—C26	178.3 (2)	C62—N7—C53—C54	6.5 (4)
C20—C19—C24—C23	−0.4 (4)	C62—N7—C53—C58	−171.9 (2)
C20—C19—C24—C25	−178.5 (2)	C62—C63—C64—C65	−0.3 (5)
C20—C21—C22—C23	−0.2 (4)	C63—C62—C67—C66	0.9 (4)
C21—C22—C23—C24	0.9 (4)	C63—C64—C65—C66	1.6 (6)
C22—C23—C24—C19	−0.6 (4)	C64—C65—C66—C67	−1.7 (6)
C22—C23—C24—C25	176.9 (3)	C65—C66—C67—C62	0.5 (5)
C23—C24—C25—C18	−176.8 (3)	C67—C62—C63—C64	−1.0 (5)
C23—C24—C25—C26	0.6 (4)	C68—C52—C59—C58	−176.3 (2)
C24—C19—C20—C21	1.1 (4)	C68—C52—C59—C60	4.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2^i	0.98 (1)	2.22 (1)	3.189 (2)	171 (2)
N2—H2B···Cl3	0.99 (1)	2.16 (1)	3.127 (2)	164 (2)
N2—H2C···Cl1	0.98 (1)	2.72 (3)	3.251 (2)	114 (2)
N2—H2C···Cl4^ii	0.98 (1)	2.49 (2)	3.290 (2)	138 (2)
N4—H4A···Cl1^iii	0.98 (1)	2.41 (2)	3.251 (2)	143 (3)
N4—H4A···Cl4^iv	0.98 (1)	2.81 (3)	3.328 (2)	113 (2)
N4—H4B···Cl2	0.99 (1)	2.18 (1)	3.144 (2)	164 (2)
N4—H4C···Cl3	0.99 (1)	2.19 (1)	3.166 (2)	169 (3)
N6—H6A···Cl1	0.99 (1)	2.15 (1)	3.131 (3)	173 (3)
N6—H6B···Cl3	0.99 (1)	2.37 (2)	3.141 (2)	135 (2)
N6—H6C···Cl4^iv	0.99 (1)	2.11 (1)	3.100 (2)	175 (3)
N8—H8A···Cl4	0.99 (1)	2.13 (1)	3.101 (3)	167 (2)
N8—H8B···Cl2^v	0.99 (1)	2.42 (2)	3.164 (2)	132 (2)
N8—H8C···Cl1^vi	0.98 (1)	2.10 (1)	3.069 (2)	167 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1, −y+2, −z+1; (iv) x−1/2, −y+3/2, z−1/2; (v) x+1/2, −y+3/2, z+1/2; (vi) x−1/2, −y+3/2, z+1/2.

2-(5-Methoxy-1H-indol-3-yl)ethan-1-aminium chloride (3)

Crystal data

C11H15N2O^+·Cl^−	F(000) = 480
Mr = 226.70	Dx = 1.284 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6858 (8) Å	Cell parameters from 7221 reflections
b = 8.3613 (4) Å	θ = 2.8–25.7°
c = 9.7878 (5) Å	µ = 0.30 mm^−1
β = 102.742 (2)°	T = 297 K
V = 1172.27 (10) Å^3	PLATE, colourless
Z = 4	0.24 × 0.21 × 0.04 mm

Data collection

Bruker D8 Venture CMOS diffractometer	1842 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.040
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.8°, θmin = 2.8°
Tmin = 0.696, Tmax = 0.745	h = −17→17
21284 measured reflections	k = −10→10
2213 independent reflections	l = −11→11

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.3256P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2213 reflections	Δρmax = 0.18 e Å^−3
149 parameters	Δρmin = −0.24 e Å^−3

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
Cl1	1.05785 (3)	0.68037 (6)	0.17151 (4)	0.06006 (18)
O1	0.47751 (10)	0.34764 (18)	0.32736 (18)	0.0787 (4)
N1	0.84685 (11)	0.49024 (19)	0.52994 (17)	0.0582 (4)
H1	0.8843 (12)	0.472 (3)	0.6100 (14)	0.070*
N2	0.88157 (10)	0.45502 (19)	0.09699 (15)	0.0524 (4)
H2A	0.8912 (13)	0.391 (2)	0.0192 (15)	0.063*
H2B	0.9369 (9)	0.523 (2)	0.124 (2)	0.063*
H2C	0.8807 (13)	0.387 (2)	0.1775 (15)	0.063*
C1	0.86687 (13)	0.5749 (2)	0.4210 (2)	0.0587 (5)
H1A	0.924770	0.619371	0.420015	0.070*
C2	0.75511 (12)	0.44368 (19)	0.49469 (17)	0.0488 (4)
C3	0.70137 (14)	0.3595 (2)	0.57105 (19)	0.0594 (5)
H3	0.726792	0.323283	0.661229	0.071*
C4	0.61014 (15)	0.3321 (2)	0.5089 (2)	0.0642 (5)
H4	0.573207	0.274972	0.557763	0.077*
C5	0.57023 (13)	0.3874 (2)	0.3736 (2)	0.0566 (4)
C6	0.62208 (12)	0.47263 (19)	0.29776 (19)	0.0511 (4)
H6	0.595425	0.510265	0.208480	0.061*
C7	0.71661 (12)	0.50130 (18)	0.35907 (17)	0.0463 (4)
C8	0.78999 (12)	0.58523 (19)	0.31395 (19)	0.0521 (4)
C9	0.78512 (14)	0.6630 (2)	0.1749 (2)	0.0650 (5)
H9A	0.834975	0.741072	0.184262	0.078*
H9B	0.726330	0.719872	0.147801	0.078*
C10	0.79313 (13)	0.5464 (2)	0.05945 (19)	0.0589 (5)
H10A	0.740740	0.472971	0.044063	0.071*
H10B	0.790955	0.604680	−0.026921	0.071*
C11	0.42849 (15)	0.4152 (3)	0.2008 (3)	0.0815 (7)
H11A	0.363683	0.386920	0.185799	0.122*
H11B	0.453610	0.375347	0.124810	0.122*
H11C	0.434709	0.529493	0.205437	0.122*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0679 (3)	0.0661 (3)	0.0455 (3)	−0.0167 (2)	0.01088 (19)	−0.00668 (19)
O1	0.0608 (8)	0.0759 (10)	0.0978 (12)	−0.0097 (7)	0.0141 (8)	0.0126 (8)
N1	0.0591 (9)	0.0609 (9)	0.0522 (9)	0.0106 (7)	0.0066 (7)	−0.0130 (7)
N2	0.0563 (9)	0.0575 (9)	0.0441 (8)	−0.0062 (7)	0.0128 (6)	0.0017 (7)
C1	0.0549 (10)	0.0479 (10)	0.0748 (12)	0.0008 (8)	0.0175 (9)	−0.0145 (9)
C2	0.0592 (10)	0.0406 (8)	0.0477 (9)	0.0104 (7)	0.0140 (7)	−0.0080 (7)
C3	0.0765 (13)	0.0569 (10)	0.0477 (10)	0.0144 (9)	0.0201 (9)	0.0032 (8)
C4	0.0759 (13)	0.0557 (11)	0.0686 (12)	0.0044 (9)	0.0325 (10)	0.0111 (9)
C5	0.0562 (10)	0.0460 (9)	0.0691 (12)	0.0005 (8)	0.0172 (9)	−0.0008 (8)
C6	0.0585 (10)	0.0429 (9)	0.0514 (9)	0.0048 (7)	0.0110 (8)	0.0015 (7)
C7	0.0563 (9)	0.0343 (7)	0.0500 (9)	0.0066 (7)	0.0155 (7)	−0.0021 (6)
C8	0.0575 (10)	0.0387 (8)	0.0626 (11)	0.0037 (7)	0.0186 (8)	−0.0018 (7)
C9	0.0665 (12)	0.0475 (10)	0.0850 (14)	0.0040 (8)	0.0257 (10)	0.0186 (9)
C10	0.0541 (10)	0.0641 (11)	0.0569 (10)	−0.0061 (8)	0.0089 (8)	0.0208 (9)
C11	0.0546 (12)	0.0920 (17)	0.0941 (17)	0.0013 (11)	0.0081 (11)	−0.0013 (13)

Geometric parameters (Å, º)

O1—C5	1.378 (2)	C4—H4	0.9300
O1—C11	1.407 (3)	C4—C5	1.404 (3)
N1—H1	0.865 (9)	C5—C6	1.374 (3)
N1—C1	1.365 (3)	C6—H6	0.9300
N1—C2	1.371 (2)	C6—C7	1.406 (2)
N2—H2A	0.966 (9)	C7—C8	1.435 (2)
N2—H2B	0.978 (9)	C8—C9	1.496 (3)
N2—H2C	0.975 (9)	C9—H9A	0.9700
N2—C10	1.482 (2)	C9—H9B	0.9700
C1—H1A	0.9300	C9—C10	1.516 (3)
C1—C8	1.363 (3)	C10—H10A	0.9700
C2—C3	1.392 (3)	C10—H10B	0.9700
C2—C7	1.408 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C3—C4	1.363 (3)	C11—H11C	0.9600
C5—O1—C11	117.98 (16)	C5—C6—C7	118.07 (16)
C1—N1—H1	126.6 (15)	C7—C6—H6	121.0
C1—N1—C2	108.64 (15)	C2—C7—C8	106.54 (15)
C2—N1—H1	124.7 (15)	C6—C7—C2	119.83 (15)
H2A—N2—H2B	105.9 (16)	C6—C7—C8	133.62 (16)
H2A—N2—H2C	110.2 (16)	C1—C8—C7	106.46 (16)
H2B—N2—H2C	106.2 (16)	C1—C8—C9	126.32 (18)
C10—N2—H2A	111.2 (12)	C7—C8—C9	127.17 (17)
C10—N2—H2B	113.5 (11)	C8—C9—H9A	108.8
C10—N2—H2C	109.6 (12)	C8—C9—H9B	108.8
N1—C1—H1A	124.8	C8—C9—C10	113.74 (14)
C8—C1—N1	110.41 (17)	H9A—C9—H9B	107.7
C8—C1—H1A	124.8	C10—C9—H9A	108.8
N1—C2—C3	130.57 (17)	C10—C9—H9B	108.8
N1—C2—C7	107.94 (15)	N2—C10—C9	110.77 (15)
C3—C2—C7	121.45 (16)	N2—C10—H10A	109.5
C2—C3—H3	121.2	N2—C10—H10B	109.5
C4—C3—C2	117.62 (17)	C9—C10—H10A	109.5
C4—C3—H3	121.2	C9—C10—H10B	109.5
C3—C4—H4	119.0	H10A—C10—H10B	108.1
C3—C4—C5	122.03 (18)	O1—C11—H11A	109.5
C5—C4—H4	119.0	O1—C11—H11B	109.5
O1—C5—C4	114.04 (17)	O1—C11—H11C	109.5
C6—C5—O1	124.97 (17)	H11A—C11—H11B	109.5
C6—C5—C4	120.99 (17)	H11A—C11—H11C	109.5
C5—C6—H6	121.0	H11B—C11—H11C	109.5
O1—C5—C6—C7	−178.99 (16)	C3—C2—C7—C8	178.31 (15)
N1—C1—C8—C7	0.11 (19)	C3—C4—C5—O1	179.56 (17)
N1—C1—C8—C9	−177.51 (16)	C3—C4—C5—C6	−0.2 (3)
N1—C2—C3—C4	178.97 (17)	C4—C5—C6—C7	0.7 (3)
N1—C2—C7—C6	−178.89 (14)	C5—C6—C7—C2	−0.3 (2)
N1—C2—C7—C8	0.04 (17)	C5—C6—C7—C8	−178.90 (17)
C1—N1—C2—C3	−178.03 (17)	C6—C7—C8—C1	178.63 (17)
C1—N1—C2—C7	0.02 (18)	C6—C7—C8—C9	−3.8 (3)
C1—C8—C9—C10	98.3 (2)	C7—C2—C3—C4	1.1 (3)
C2—N1—C1—C8	−0.08 (19)	C7—C8—C9—C10	−78.8 (2)
C2—C3—C4—C5	−0.8 (3)	C8—C9—C10—N2	−57.8 (2)
C2—C7—C8—C1	−0.09 (18)	C11—O1—C5—C4	171.93 (19)
C2—C7—C8—C9	177.50 (16)	C11—O1—C5—C6	−8.4 (3)
C3—C2—C7—C6	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1^i	0.87 (1)	2.47 (1)	3.2754 (17)	154 (2)
N2—H2A···Cl1^ii	0.97 (1)	2.24 (1)	3.1640 (16)	160 (2)
N2—H2B···Cl1	0.98 (1)	2.18 (1)	3.1547 (16)	177 (2)
N2—H2C···Cl1^iii	0.98 (1)	2.32 (1)	3.2109 (15)	151 (2)

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

2-(5-Bromo-1H-indol-3-yl)ethan-1-aminium chloride (4)

Crystal data

C10H12BrN2^+·Cl^−	Dx = 1.553 Mg m^−3
Mr = 275.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9946 reflections
a = 8.6153 (6) Å	θ = 2.8–26.4°
b = 9.3766 (5) Å	µ = 3.68 mm^−1
c = 29.173 (2) Å	T = 297 K
V = 2356.7 (3) Å^3	BLOCK, colourless
Z = 8	0.28 × 0.21 × 0.12 mm
F(000) = 1104

Data collection

Bruker D8 Venture CMOS diffractometer	1900 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.4°, θmin = 2.8°
Tmin = 0.483, Tmax = 0.647	h = −10→10
55777 measured reflections	k = −11→11
2377 independent reflections	l = −36→36

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0204P)^2 + 3.943P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2377 reflections	Δρmax = 0.55 e Å^−3
143 parameters	Δρmin = −0.72 e Å^−3

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
Br1	0.37059 (7)	0.51063 (6)	0.22026 (2)	0.0986 (2)
Cl1	0.69473 (10)	0.84762 (9)	0.52412 (3)	0.0543 (2)
N1	0.4815 (4)	0.4047 (3)	0.42015 (11)	0.0627 (8)
N2	0.4588 (3)	0.8686 (3)	0.44048 (9)	0.0492 (7)
C1	0.5644 (4)	0.5258 (4)	0.43080 (12)	0.0572 (9)
H1A	0.605264	0.546327	0.459554	0.069*
C2	0.4400 (4)	0.4104 (3)	0.37477 (13)	0.0532 (8)
C3	0.3604 (5)	0.3129 (4)	0.34752 (16)	0.0706 (11)
H3	0.322143	0.228387	0.359797	0.085*
C4	0.3402 (4)	0.3448 (5)	0.30229 (17)	0.0747 (12)
H4	0.288033	0.281107	0.283332	0.090*
C5	0.3973 (4)	0.4724 (4)	0.28423 (13)	0.0609 (9)
C6	0.4755 (4)	0.5711 (4)	0.31014 (12)	0.0497 (8)
H6	0.512137	0.655563	0.297376	0.060*
C7	0.4980 (3)	0.5396 (3)	0.35663 (11)	0.0443 (7)
C8	0.5780 (3)	0.6112 (3)	0.39326 (11)	0.0458 (7)
C9	0.6549 (4)	0.7549 (4)	0.39120 (12)	0.0556 (9)
H9A	0.708940	0.763708	0.362161	0.067*
H9B	0.731794	0.760769	0.415423	0.067*
C10	0.5427 (4)	0.8785 (3)	0.39610 (11)	0.0516 (8)
H10A	0.599247	0.967805	0.394666	0.062*
H10B	0.468706	0.876794	0.371049	0.062*
H2A	0.391 (3)	0.784 (2)	0.4406 (12)	0.061 (10)*
H2B	0.395 (4)	0.955 (3)	0.4457 (14)	0.081 (13)*
H1	0.453 (4)	0.340 (3)	0.4396 (10)	0.072 (12)*
H2C	0.531 (3)	0.859 (4)	0.4665 (8)	0.069 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0972 (4)	0.1303 (5)	0.0682 (3)	0.0144 (3)	−0.0219 (3)	−0.0334 (3)
Cl1	0.0582 (5)	0.0463 (4)	0.0584 (5)	0.0021 (4)	−0.0083 (4)	0.0048 (4)
N1	0.066 (2)	0.0525 (18)	0.070 (2)	0.0140 (16)	0.0213 (17)	0.0121 (16)
N2	0.0550 (17)	0.0448 (16)	0.0479 (15)	−0.0018 (14)	−0.0019 (13)	−0.0017 (12)
C1	0.051 (2)	0.067 (2)	0.0537 (19)	0.0154 (18)	0.0051 (16)	−0.0002 (17)
C2	0.0400 (17)	0.0427 (17)	0.077 (2)	0.0065 (14)	0.0162 (17)	−0.0038 (17)
C3	0.061 (2)	0.0447 (19)	0.106 (3)	−0.0064 (17)	0.024 (2)	−0.016 (2)
C4	0.056 (2)	0.069 (3)	0.099 (3)	−0.010 (2)	0.005 (2)	−0.038 (2)
C5	0.0465 (19)	0.070 (2)	0.066 (2)	0.0043 (18)	−0.0009 (16)	−0.0228 (19)
C6	0.0397 (17)	0.0510 (18)	0.059 (2)	0.0023 (15)	0.0022 (15)	−0.0078 (15)
C7	0.0329 (15)	0.0436 (16)	0.0565 (18)	0.0040 (13)	0.0067 (14)	−0.0058 (14)
C8	0.0348 (16)	0.0533 (18)	0.0494 (17)	0.0031 (14)	0.0030 (13)	−0.0039 (14)
C9	0.0448 (18)	0.071 (2)	0.0506 (18)	−0.0159 (17)	0.0048 (15)	−0.0102 (17)
C10	0.056 (2)	0.0511 (19)	0.0475 (18)	−0.0167 (16)	−0.0013 (15)	0.0009 (15)

Geometric parameters (Å, º)

Br1—C5	1.915 (4)	C3—C4	1.364 (6)
N1—C1	1.376 (5)	C4—H4	0.9300
N1—C2	1.372 (5)	C4—C5	1.397 (6)
N1—H1	0.866 (10)	C5—C6	1.372 (5)
N2—C10	1.486 (4)	C6—H6	0.9300
N2—H2A	0.985 (10)	C6—C7	1.401 (5)
N2—H2B	0.988 (10)	C7—C8	1.438 (4)
N2—H2C	0.983 (10)	C8—C9	1.503 (5)
C1—H1A	0.9300	C9—H9A	0.9700
C1—C8	1.362 (5)	C9—H9B	0.9700
C2—C3	1.392 (5)	C9—C10	1.516 (5)
C2—C7	1.413 (4)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C1—N1—H1	125 (3)	C6—C5—C4	122.9 (4)
C2—N1—C1	108.7 (3)	C5—C6—H6	121.4
C2—N1—H1	126 (3)	C5—C6—C7	117.3 (3)
C10—N2—H2A	110 (2)	C7—C6—H6	121.4
C10—N2—H2B	111 (2)	C2—C7—C8	106.9 (3)
C10—N2—H2C	112 (2)	C6—C7—C2	119.6 (3)
H2A—N2—H2B	109 (3)	C6—C7—C8	133.4 (3)
H2A—N2—H2C	107 (3)	C1—C8—C7	106.4 (3)
H2B—N2—H2C	108 (3)	C1—C8—C9	126.7 (3)
N1—C1—H1A	124.8	C7—C8—C9	126.9 (3)
C8—C1—N1	110.4 (3)	C8—C9—H9A	108.8
C8—C1—H1A	124.8	C8—C9—H9B	108.8
N1—C2—C3	130.8 (4)	C8—C9—C10	113.6 (3)
N1—C2—C7	107.6 (3)	H9A—C9—H9B	107.7
C3—C2—C7	121.5 (4)	C10—C9—H9A	108.8
C2—C3—H3	120.9	C10—C9—H9B	108.8
C4—C3—C2	118.1 (4)	N2—C10—C9	110.2 (3)
C4—C3—H3	120.9	N2—C10—H10A	109.6
C3—C4—H4	119.7	N2—C10—H10B	109.6
C3—C4—C5	120.5 (4)	C9—C10—H10A	109.6
C5—C4—H4	119.7	C9—C10—H10B	109.6
C4—C5—Br1	119.1 (3)	H10A—C10—H10B	108.1
C6—C5—Br1	118.0 (3)
Br1—C5—C6—C7	−178.2 (2)	C3—C2—C7—C6	0.0 (5)
N1—C1—C8—C7	0.2 (4)	C3—C2—C7—C8	−177.8 (3)
N1—C1—C8—C9	177.7 (3)	C3—C4—C5—Br1	178.5 (3)
N1—C2—C3—C4	−177.5 (4)	C3—C4—C5—C6	0.1 (6)
N1—C2—C7—C6	178.3 (3)	C4—C5—C6—C7	0.3 (5)
N1—C2—C7—C8	0.5 (3)	C5—C6—C7—C2	−0.3 (4)
C1—N1—C2—C3	177.8 (3)	C5—C6—C7—C8	176.8 (3)
C1—N1—C2—C7	−0.4 (4)	C6—C7—C8—C1	−177.8 (3)
C1—C8—C9—C10	−96.2 (4)	C6—C7—C8—C9	4.8 (5)
C2—N1—C1—C8	0.1 (4)	C7—C2—C3—C4	0.4 (5)
C2—C3—C4—C5	−0.4 (6)	C7—C8—C9—C10	80.7 (4)
C2—C7—C8—C1	−0.5 (3)	C8—C9—C10—N2	59.0 (4)
C2—C7—C8—C9	−177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.99 (1)	2.33 (2)	3.217 (3)	149 (3)
N2—H2B···Cl1^ii	0.99 (1)	2.19 (2)	3.146 (3)	162 (3)
N1—H1···Cl1^iii	0.87 (1)	2.42 (2)	3.248 (3)	161 (4)
N2—H2C···Cl1	0.98 (1)	2.20 (1)	3.182 (3)	177 (3)

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1.

2-(5-Chloro-1H-indol-3-yl)ethan-1-aminium chloride (5)

Crystal data

C10H12ClN2^+·Cl^−	F(000) = 480
Mr = 231.12	Dx = 1.344 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7030 (9) Å	Cell parameters from 8111 reflections
b = 8.6058 (5) Å	θ = 2.8–26.1°
c = 9.4141 (5) Å	µ = 0.53 mm^−1
β = 106.450 (2)°	T = 297 K
V = 1142.42 (11) Å^3	BLOCK, colourless
Z = 4	0.24 × 0.20 × 0.06 mm

Data collection

Bruker D8 Venture CMOS diffractometer	1858 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.4°, θmin = 2.8°
Tmin = 0.705, Tmax = 0.745	h = −18→18
27018 measured reflections	k = −10→10
2315 independent reflections	l = −11→11

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 0.470P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2315 reflections	Δρmax = 0.24 e Å^−3
143 parameters	Δρmin = −0.29 e Å^−3

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
Cl1	0.57154 (4)	0.62245 (8)	0.28962 (8)	0.0871 (2)
Cl2	0.05392 (4)	0.69071 (6)	0.67192 (5)	0.05911 (17)
N1	0.17384 (13)	0.5231 (2)	−0.02379 (19)	0.0629 (5)
H1	0.1383 (14)	0.550 (3)	−0.1098 (15)	0.078 (7)*
N2	0.11894 (11)	0.5425 (2)	0.41331 (18)	0.0530 (4)
H2A	0.1083 (16)	0.606 (2)	0.4928 (19)	0.083 (7)*
H2B	0.0643 (12)	0.473 (2)	0.380 (3)	0.088 (8)*
H2C	0.1162 (17)	0.610 (2)	0.3285 (18)	0.085 (7)*
C1	0.14651 (14)	0.4405 (2)	0.0805 (2)	0.0614 (5)
H1A	0.085806	0.401414	0.068358	0.074*
C2	0.26777 (14)	0.5620 (2)	0.0309 (2)	0.0523 (4)
C3	0.32853 (17)	0.6399 (2)	−0.0334 (2)	0.0664 (6)
H3	0.306903	0.679081	−0.129184	0.080*
C4	0.42130 (17)	0.6577 (3)	0.0478 (3)	0.0684 (6)
H4	0.463541	0.709514	0.007169	0.082*
C5	0.45237 (14)	0.5984 (2)	0.1909 (2)	0.0577 (5)
C6	0.39404 (13)	0.5211 (2)	0.2572 (2)	0.0512 (4)
H6	0.416593	0.483029	0.353258	0.061*
C7	0.29943 (13)	0.50122 (19)	0.17551 (19)	0.0469 (4)
C8	0.22050 (13)	0.4229 (2)	0.2053 (2)	0.0517 (4)
C9	0.21945 (15)	0.3439 (2)	0.3459 (2)	0.0621 (5)
H9A	0.277834	0.285607	0.382960	0.074*
H9B	0.167247	0.270562	0.325168	0.074*
C10	0.20939 (13)	0.4554 (2)	0.4645 (2)	0.0580 (5)
H10A	0.210787	0.398137	0.553808	0.070*
H10B	0.262148	0.527768	0.487769	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0591 (3)	0.0940 (5)	0.1052 (5)	−0.0149 (3)	0.0184 (3)	0.0055 (4)
Cl2	0.0632 (3)	0.0614 (3)	0.0495 (3)	−0.0103 (2)	0.0109 (2)	−0.0060 (2)
N1	0.0657 (11)	0.0637 (11)	0.0510 (9)	0.0154 (9)	0.0028 (8)	−0.0093 (8)
N2	0.0519 (9)	0.0546 (10)	0.0528 (9)	0.0003 (8)	0.0155 (7)	0.0033 (8)
C1	0.0515 (11)	0.0528 (11)	0.0760 (13)	0.0048 (9)	0.0117 (10)	−0.0150 (10)
C2	0.0638 (12)	0.0435 (10)	0.0477 (9)	0.0111 (9)	0.0126 (9)	−0.0055 (8)
C3	0.0922 (17)	0.0589 (12)	0.0517 (11)	0.0129 (11)	0.0262 (11)	0.0072 (9)
C4	0.0796 (15)	0.0613 (13)	0.0729 (14)	−0.0012 (11)	0.0355 (12)	0.0087 (11)
C5	0.0567 (11)	0.0507 (11)	0.0667 (12)	−0.0015 (9)	0.0188 (9)	0.0013 (9)
C6	0.0548 (10)	0.0437 (10)	0.0534 (10)	0.0044 (8)	0.0127 (8)	0.0031 (8)
C7	0.0543 (10)	0.0359 (9)	0.0502 (9)	0.0068 (8)	0.0144 (8)	−0.0017 (7)
C8	0.0512 (10)	0.0388 (9)	0.0649 (11)	0.0050 (8)	0.0161 (9)	−0.0027 (8)
C9	0.0563 (11)	0.0465 (11)	0.0863 (14)	0.0033 (9)	0.0251 (10)	0.0128 (10)
C10	0.0499 (10)	0.0617 (12)	0.0607 (11)	−0.0010 (9)	0.0126 (9)	0.0182 (9)

Geometric parameters (Å, º)

Cl1—C5	1.748 (2)	C3—C4	1.370 (3)
N1—H1	0.862 (9)	C4—H4	0.9300
N1—C1	1.362 (3)	C4—C5	1.391 (3)
N1—C2	1.372 (3)	C5—C6	1.368 (3)
N2—H2A	0.977 (10)	C6—H6	0.9300
N2—H2B	0.980 (10)	C6—C7	1.396 (2)
N2—H2C	0.976 (10)	C7—C8	1.437 (3)
N2—C10	1.483 (2)	C8—C9	1.492 (3)
C1—H1A	0.9300	C9—H9A	0.9700
C1—C8	1.365 (3)	C9—H9B	0.9700
C2—C3	1.386 (3)	C9—C10	1.511 (3)
C2—C7	1.409 (2)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C1—N1—H1	126.5 (16)	C6—C5—C4	123.0 (2)
C1—N1—C2	109.14 (17)	C5—C6—H6	121.2
C2—N1—H1	124.3 (16)	C5—C6—C7	117.62 (17)
H2A—N2—H2B	107.1 (19)	C7—C6—H6	121.2
H2A—N2—H2C	108.4 (19)	C2—C7—C8	107.37 (16)
H2B—N2—H2C	105.2 (19)	C6—C7—C2	119.47 (17)
C10—N2—H2A	111.1 (14)	C6—C7—C8	133.13 (17)
C10—N2—H2B	111.8 (14)	C1—C8—C7	105.72 (18)
C10—N2—H2C	112.9 (14)	C1—C8—C9	127.46 (19)
N1—C1—H1A	124.7	C7—C8—C9	126.78 (17)
N1—C1—C8	110.64 (18)	C8—C9—H9A	108.9
C8—C1—H1A	124.7	C8—C9—H9B	108.9
N1—C2—C3	131.21 (19)	C8—C9—C10	113.20 (16)
N1—C2—C7	107.12 (17)	H9A—C9—H9B	107.8
C3—C2—C7	121.63 (19)	C10—C9—H9A	108.9
C2—C3—H3	120.9	C10—C9—H9B	108.9
C4—C3—C2	118.24 (19)	N2—C10—C9	110.32 (16)
C4—C3—H3	120.9	N2—C10—H10A	109.6
C3—C4—H4	120.0	N2—C10—H10B	109.6
C3—C4—C5	120.1 (2)	C9—C10—H10A	109.6
C5—C4—H4	120.0	C9—C10—H10B	109.6
C4—C5—Cl1	118.45 (16)	H10A—C10—H10B	108.1
C6—C5—Cl1	118.59 (16)
Cl1—C5—C6—C7	−179.08 (14)	C3—C2—C7—C6	0.7 (3)
N1—C1—C8—C7	0.2 (2)	C3—C2—C7—C8	−177.61 (17)
N1—C1—C8—C9	178.19 (18)	C3—C4—C5—Cl1	179.44 (17)
N1—C2—C3—C4	−177.8 (2)	C3—C4—C5—C6	0.0 (3)
N1—C2—C7—C6	178.70 (16)	C4—C5—C6—C7	0.3 (3)
N1—C2—C7—C8	0.39 (19)	C5—C6—C7—C2	−0.7 (3)
C1—N1—C2—C3	177.4 (2)	C5—C6—C7—C8	177.12 (19)
C1—N1—C2—C7	−0.3 (2)	C6—C7—C8—C1	−178.32 (19)
C1—C8—C9—C10	−98.3 (2)	C6—C7—C8—C9	3.6 (3)
C2—N1—C1—C8	0.1 (2)	C7—C2—C3—C4	−0.3 (3)
C2—C3—C4—C5	0.0 (3)	C7—C8—C9—C10	79.3 (2)
C2—C7—C8—C1	−0.3 (2)	C8—C9—C10—N2	60.7 (2)
C2—C7—C8—C9	−178.39 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2^i	0.86 (1)	2.40 (1)	3.2458 (18)	165 (2)
N2—H2A···Cl2	0.98 (1)	2.18 (1)	3.1282 (17)	162 (2)
N2—H2B···Cl2^ii	0.98 (1)	2.18 (1)	3.1585 (18)	175 (2)
N2—H2C···Cl2^iii	0.98 (1)	2.28 (1)	3.1811 (17)	153 (2)

Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+1; (iii) x, −y+3/2, z−1/2.

2-(5-Fluoro-1H-indol-3-yl)ethan-1-aminium chloride (6)

Crystal data

C10H12FN2^+·Cl^−	Dx = 1.324 Mg m^−3
Mr = 214.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9978 reflections
a = 8.6708 (4) Å	θ = 2.8–26.4°
b = 9.6684 (5) Å	µ = 0.33 mm^−1
c = 25.6854 (12) Å	T = 297 K
V = 2153.28 (18) Å^3	PLATE, colourless
Z = 8	0.29 × 0.20 × 0.03 mm
F(000) = 896

Data collection

Bruker D8 Venture CMOS diffractometer	1904 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.043
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.4°, θmin = 2.8°
Tmin = 0.694, Tmax = 0.745	h = −10→10
65854 measured reflections	k = −12→12
2190 independent reflections	l = −32→32

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0348P)^2 + 1.1584P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2190 reflections	Δρmax = 0.20 e Å^−3
143 parameters	Δρmin = −0.19 e Å^−3

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
Cl1	0.31363 (6)	0.14447 (5)	0.46647 (2)	0.05314 (17)
F1	0.64999 (17)	0.44187 (18)	0.79095 (5)	0.0866 (5)
N1	0.5244 (2)	0.59702 (19)	0.59246 (7)	0.0577 (5)
N2	0.5407 (2)	0.14363 (17)	0.56311 (7)	0.0480 (4)
C1	0.4366 (2)	0.4880 (2)	0.57683 (8)	0.0539 (5)
H1A	0.393075	0.478901	0.543916	0.065*
C2	0.5701 (2)	0.57566 (19)	0.64294 (8)	0.0489 (5)
C3	0.6599 (2)	0.6567 (2)	0.67575 (11)	0.0644 (6)
H3	0.699807	0.740928	0.664589	0.077*
C4	0.6878 (3)	0.6086 (3)	0.72517 (10)	0.0672 (6)
H4	0.749892	0.658979	0.747816	0.081*
C5	0.6228 (2)	0.4845 (2)	0.74111 (8)	0.0581 (5)
C6	0.5326 (2)	0.4029 (2)	0.71029 (7)	0.0485 (4)
H6	0.490343	0.320759	0.722616	0.058*
C7	0.50647 (19)	0.44837 (18)	0.65919 (7)	0.0409 (4)
C8	0.4211 (2)	0.3940 (2)	0.61609 (7)	0.0447 (4)
C9	0.3376 (2)	0.2586 (2)	0.61418 (8)	0.0548 (5)
H9A	0.269263	0.258239	0.584276	0.066*
H9B	0.274446	0.249609	0.645168	0.066*
C10	0.4442 (2)	0.1354 (2)	0.61067 (7)	0.0526 (5)
H10A	0.510083	0.132699	0.641169	0.063*
H10B	0.383771	0.051022	0.609957	0.063*
H2A	0.476 (2)	0.154 (2)	0.5320 (6)	0.077 (8)*
H2B	0.605 (2)	0.0613 (17)	0.5590 (9)	0.076 (7)*
H2C	0.609 (2)	0.2241 (16)	0.5622 (9)	0.067 (6)*
H1	0.554 (3)	0.6645 (19)	0.5727 (9)	0.085 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0559 (3)	0.0432 (3)	0.0603 (3)	0.0035 (2)	−0.0091 (2)	0.0043 (2)
F1	0.0834 (9)	0.1216 (13)	0.0549 (7)	0.0092 (9)	−0.0167 (7)	−0.0145 (8)
N1	0.0584 (10)	0.0480 (9)	0.0668 (11)	0.0101 (8)	0.0140 (9)	0.0122 (9)
N2	0.0495 (9)	0.0406 (8)	0.0538 (9)	−0.0026 (7)	−0.0015 (8)	−0.0031 (7)
C1	0.0449 (10)	0.0675 (13)	0.0493 (10)	0.0144 (10)	0.0038 (8)	0.0023 (10)
C2	0.0414 (10)	0.0392 (9)	0.0662 (12)	0.0068 (8)	0.0115 (9)	−0.0040 (9)
C3	0.0532 (12)	0.0443 (11)	0.0958 (18)	−0.0042 (9)	0.0153 (12)	−0.0179 (11)
C4	0.0520 (12)	0.0677 (14)	0.0819 (16)	−0.0046 (11)	0.0003 (11)	−0.0346 (13)
C5	0.0484 (11)	0.0736 (14)	0.0522 (11)	0.0104 (10)	−0.0038 (9)	−0.0155 (10)
C6	0.0429 (10)	0.0507 (10)	0.0519 (10)	0.0029 (8)	0.0039 (8)	−0.0047 (9)
C7	0.0326 (8)	0.0413 (9)	0.0488 (10)	0.0040 (7)	0.0053 (7)	−0.0053 (8)
C8	0.0348 (9)	0.0523 (10)	0.0470 (10)	0.0030 (8)	0.0040 (7)	−0.0049 (8)
C9	0.0412 (10)	0.0719 (14)	0.0513 (11)	−0.0116 (10)	0.0036 (8)	−0.0117 (10)
C10	0.0578 (12)	0.0513 (11)	0.0488 (10)	−0.0182 (9)	−0.0018 (9)	0.0008 (9)

Geometric parameters (Å, º)

F1—C5	1.365 (2)	C3—C4	1.373 (3)
N1—C1	1.361 (3)	C4—H4	0.9300
N1—C2	1.371 (3)	C4—C5	1.388 (3)
N1—H1	0.863 (10)	C5—C6	1.364 (3)
N2—C10	1.483 (3)	C6—H6	0.9300
N2—H2A	0.983 (10)	C6—C7	1.403 (3)
N2—H2B	0.980 (10)	C7—C8	1.432 (2)
N2—H2C	0.976 (10)	C8—C9	1.497 (3)
C1—H1A	0.9300	C9—H9A	0.9700
C1—C8	1.364 (3)	C9—H9B	0.9700
C2—C3	1.389 (3)	C9—C10	1.510 (3)
C2—C7	1.412 (3)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C1—N1—C2	108.90 (17)	C6—C5—C4	124.2 (2)
C1—N1—H1	125.1 (18)	C5—C6—H6	121.5
C2—N1—H1	125.7 (18)	C5—C6—C7	117.01 (19)
C10—N2—H2A	110.5 (14)	C7—C6—H6	121.5
C10—N2—H2B	111.6 (14)	C2—C7—C8	107.07 (16)
C10—N2—H2C	113.7 (13)	C6—C7—C2	119.13 (17)
H2A—N2—H2B	109 (2)	C6—C7—C8	133.79 (18)
H2A—N2—H2C	104.4 (19)	C1—C8—C7	106.03 (17)
H2B—N2—H2C	107.5 (19)	C1—C8—C9	127.31 (18)
N1—C1—H1A	124.7	C7—C8—C9	126.62 (17)
N1—C1—C8	110.67 (18)	C8—C9—H9A	108.9
C8—C1—H1A	124.7	C8—C9—H9B	108.9
N1—C2—C3	130.6 (2)	C8—C9—C10	113.29 (15)
N1—C2—C7	107.33 (17)	H9A—C9—H9B	107.7
C3—C2—C7	122.1 (2)	C10—C9—H9A	108.9
C2—C3—H3	121.0	C10—C9—H9B	108.9
C4—C3—C2	117.9 (2)	N2—C10—C9	110.65 (16)
C4—C3—H3	121.0	N2—C10—H10A	109.5
C3—C4—H4	120.2	N2—C10—H10B	109.5
C3—C4—C5	119.6 (2)	C9—C10—H10A	109.5
C5—C4—H4	120.2	C9—C10—H10B	109.5
F1—C5—C4	117.9 (2)	H10A—C10—H10B	108.1
C6—C5—F1	117.9 (2)
F1—C5—C6—C7	−179.84 (16)	C3—C2—C7—C6	0.9 (3)
N1—C1—C8—C7	−0.3 (2)	C3—C2—C7—C8	179.69 (17)
N1—C1—C8—C9	−178.08 (17)	C3—C4—C5—F1	−178.34 (19)
N1—C2—C3—C4	−179.9 (2)	C3—C4—C5—C6	1.1 (3)
N1—C2—C7—C6	−178.49 (16)	C4—C5—C6—C7	0.7 (3)
N1—C2—C7—C8	0.26 (19)	C5—C6—C7—C2	−1.7 (2)
C1—N1—C2—C3	−179.83 (19)	C5—C6—C7—C8	179.99 (18)
C1—N1—C2—C7	−0.5 (2)	C6—C7—C8—C1	178.53 (19)
C1—C8—C9—C10	104.4 (2)	C6—C7—C8—C9	−3.7 (3)
C2—N1—C1—C8	0.5 (2)	C7—C2—C3—C4	0.9 (3)
C2—C3—C4—C5	−1.9 (3)	C7—C8—C9—C10	−72.9 (2)
C2—C7—C8—C1	0.04 (19)	C8—C9—C10—N2	−59.8 (2)
C2—C7—C8—C9	177.80 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.98 (1)	2.19 (1)	3.1685 (18)	171 (2)
N2—H2B···Cl1^i	0.98 (1)	2.21 (1)	3.1513 (17)	161 (2)
N2—H2C···Cl1^ii	0.98 (1)	2.31 (1)	3.2208 (17)	156 (2)
N1—H1···Cl1^iii	0.86 (1)	2.40 (1)	3.2418 (18)	166 (2)

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

2-(5-Methyl-1H-indol-3-yl)ethan-1-aminium chloride (7)

Crystal data

C11H15N2^+·Cl^−	F(000) = 448
Mr = 210.70	Dx = 1.219 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9939 (10) Å	Cell parameters from 8357 reflections
b = 8.4270 (5) Å	θ = 2.8–26.3°
c = 9.5388 (6) Å	µ = 0.30 mm^−1
β = 107.774 (2)°	T = 297 K
V = 1147.73 (13) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.08 mm

Data collection

Bruker D8 Venture CMOS diffractometer	1932 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.043
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.4°, θmin = 2.8°
Tmin = 0.678, Tmax = 0.745	h = −18→18
25382 measured reflections	k = −10→10
2331 independent reflections	l = −11→11

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.148	w = 1/[σ^2(Fo^2) + (0.0593P)^2 + 0.5865P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
2331 reflections	Δρmax = 0.34 e Å^−3
144 parameters	Δρmin = −0.30 e Å^−3

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
Cl1	0.94731 (5)	0.31223 (8)	0.32342 (7)	0.0600 (2)
N1	0.83458 (17)	0.4795 (3)	1.0140 (3)	0.0644 (6)
N2	0.87951 (15)	0.4557 (3)	0.5770 (2)	0.0525 (5)
C1	0.85885 (19)	0.5618 (3)	0.9068 (3)	0.0639 (7)
H1A	0.918484	0.600426	0.916167	0.077*
C2	0.74143 (19)	0.4424 (3)	0.9623 (3)	0.0551 (6)
C3	0.6827 (2)	0.3656 (3)	1.0296 (3)	0.0674 (8)
H3	0.706056	0.325863	1.124769	0.081*
C4	0.5900 (2)	0.3506 (3)	0.9517 (4)	0.0694 (8)
H4	0.550319	0.299743	0.995598	0.083*
C5	0.5525 (2)	0.4093 (3)	0.8075 (3)	0.0607 (7)
C6	0.61139 (18)	0.4832 (3)	0.7416 (3)	0.0531 (6)
H6	0.587788	0.520787	0.645685	0.064*
C7	0.70623 (17)	0.5017 (3)	0.8182 (3)	0.0486 (5)
C8	0.78325 (17)	0.5787 (3)	0.7847 (3)	0.0529 (6)
C9	0.7813 (2)	0.6576 (3)	0.6432 (4)	0.0649 (7)
H9A	0.832443	0.733104	0.662521	0.078*
H9B	0.723199	0.716311	0.606138	0.078*
C10	0.78937 (18)	0.5433 (3)	0.5268 (3)	0.0591 (6)
H10A	0.737745	0.468549	0.505147	0.071*
H10B	0.785671	0.600959	0.437179	0.071*
C11	0.4489 (2)	0.3953 (5)	0.7267 (4)	0.0863 (10)
H11A	0.428133	0.488299	0.667696	0.130*
H11B	0.414862	0.385387	0.796788	0.130*
H11C	0.437910	0.303224	0.664492	0.130*
H1	0.875 (2)	0.456 (4)	1.098 (2)	0.092 (11)*
H2A	0.9328 (13)	0.530 (3)	0.609 (3)	0.061 (8)*
H2B	0.8874 (19)	0.385 (3)	0.499 (2)	0.068 (8)*
H2C	0.882 (2)	0.399 (3)	0.668 (2)	0.077 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0659 (4)	0.0633 (4)	0.0501 (4)	−0.0140 (3)	0.0166 (3)	−0.0069 (3)
N1	0.0668 (15)	0.0637 (14)	0.0566 (13)	0.0172 (11)	0.0097 (11)	−0.0107 (11)
N2	0.0529 (12)	0.0543 (12)	0.0526 (12)	−0.0025 (9)	0.0193 (10)	0.0019 (9)
C1	0.0578 (15)	0.0521 (14)	0.0801 (19)	0.0071 (12)	0.0186 (14)	−0.0166 (13)
C2	0.0722 (17)	0.0443 (12)	0.0511 (13)	0.0147 (11)	0.0220 (12)	−0.0046 (10)
C3	0.096 (2)	0.0579 (15)	0.0547 (15)	0.0184 (15)	0.0331 (15)	0.0071 (12)
C4	0.089 (2)	0.0590 (16)	0.0744 (18)	0.0001 (15)	0.0461 (17)	0.0067 (14)
C5	0.0647 (16)	0.0501 (14)	0.0733 (17)	−0.0013 (12)	0.0299 (13)	−0.0002 (12)
C6	0.0610 (15)	0.0444 (12)	0.0558 (14)	0.0019 (11)	0.0206 (11)	0.0026 (10)
C7	0.0574 (14)	0.0354 (11)	0.0553 (13)	0.0059 (9)	0.0204 (11)	−0.0022 (9)
C8	0.0551 (14)	0.0394 (12)	0.0675 (15)	0.0057 (10)	0.0235 (12)	−0.0028 (11)
C9	0.0612 (16)	0.0468 (14)	0.092 (2)	0.0072 (12)	0.0311 (15)	0.0162 (13)
C10	0.0513 (14)	0.0642 (15)	0.0602 (14)	−0.0024 (12)	0.0148 (11)	0.0196 (12)
C11	0.0675 (19)	0.086 (2)	0.109 (3)	−0.0149 (17)	0.0332 (18)	0.004 (2)

Geometric parameters (Å, º)

N1—C1	1.373 (4)	C5—C6	1.379 (4)
N1—C2	1.368 (4)	C5—C11	1.513 (4)
N1—H1	0.863 (10)	C6—H6	0.9300
N2—C10	1.485 (3)	C6—C7	1.395 (3)
N2—H2A	0.986 (10)	C7—C8	1.443 (3)
N2—H2B	0.987 (10)	C8—C9	1.497 (4)
N2—H2C	0.987 (10)	C9—H9A	0.9700
C1—H1A	0.9300	C9—H9B	0.9700
C1—C8	1.362 (4)	C9—C10	1.503 (4)
C2—C3	1.397 (4)	C10—H10A	0.9700
C2—C7	1.405 (3)	C10—H10B	0.9700
C3—H3	0.9300	C11—H11A	0.9600
C3—C4	1.368 (4)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C4—C5	1.407 (4)
C1—N1—H1	123 (3)	C7—C6—H6	119.9
C2—N1—C1	108.7 (2)	C2—C7—C8	106.8 (2)
C2—N1—H1	129 (3)	C6—C7—C2	119.4 (2)
C10—N2—H2A	111.0 (16)	C6—C7—C8	133.7 (2)
C10—N2—H2B	111.3 (17)	C1—C8—C7	106.1 (2)
C10—N2—H2C	108.0 (18)	C1—C8—C9	126.8 (3)
H2A—N2—H2B	110 (2)	C7—C8—C9	127.0 (2)
H2A—N2—H2C	103 (2)	C8—C9—H9A	108.9
H2B—N2—H2C	113 (2)	C8—C9—H9B	108.9
N1—C1—H1A	124.8	C8—C9—C10	113.5 (2)
C8—C1—N1	110.4 (3)	H9A—C9—H9B	107.7
C8—C1—H1A	124.8	C10—C9—H9A	108.9
N1—C2—C3	131.1 (3)	C10—C9—H9B	108.9
N1—C2—C7	108.0 (2)	N2—C10—C9	110.6 (2)
C3—C2—C7	120.9 (3)	N2—C10—H10A	109.5
C2—C3—H3	120.9	N2—C10—H10B	109.5
C4—C3—C2	118.2 (3)	C9—C10—H10A	109.5
C4—C3—H3	120.9	C9—C10—H10B	109.5
C3—C4—H4	118.8	H10A—C10—H10B	108.1
C3—C4—C5	122.4 (3)	C5—C11—H11A	109.5
C5—C4—H4	118.8	C5—C11—H11B	109.5
C4—C5—C11	120.8 (3)	C5—C11—H11C	109.5
C6—C5—C4	118.9 (3)	H11A—C11—H11B	109.5
C6—C5—C11	120.3 (3)	H11A—C11—H11C	109.5
C5—C6—H6	119.9	H11B—C11—H11C	109.5
C5—C6—C7	120.3 (2)
N1—C1—C8—C7	0.1 (3)	C3—C2—C7—C8	177.7 (2)
N1—C1—C8—C9	−178.4 (2)	C3—C4—C5—C6	0.7 (4)
N1—C2—C3—C4	177.3 (3)	C3—C4—C5—C11	−177.9 (3)
N1—C2—C7—C6	−178.2 (2)	C4—C5—C6—C7	−1.2 (4)
N1—C2—C7—C8	−0.5 (3)	C5—C6—C7—C2	0.9 (3)
C1—N1—C2—C3	−177.4 (3)	C5—C6—C7—C8	−176.2 (2)
C1—N1—C2—C7	0.5 (3)	C6—C7—C8—C1	177.6 (3)
C1—C8—C9—C10	97.2 (3)	C6—C7—C8—C9	−3.9 (4)
C2—N1—C1—C8	−0.4 (3)	C7—C2—C3—C4	−0.4 (4)
C2—C3—C4—C5	0.1 (4)	C7—C8—C9—C10	−81.0 (3)
C2—C7—C8—C1	0.2 (3)	C8—C9—C10—N2	−61.0 (3)
C2—C7—C8—C9	178.8 (2)	C11—C5—C6—C7	177.5 (3)
C3—C2—C7—C6	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1^i	0.86 (1)	2.42 (2)	3.242 (3)	159 (3)
N2—H2A···Cl1^ii	0.99 (1)	2.17 (1)	3.156 (2)	178 (2)
N2—H2B···Cl1	0.99 (1)	2.22 (2)	3.138 (2)	155 (2)
N2—H2C···Cl1^iii	0.99 (1)	2.33 (2)	3.194 (2)	146 (2)

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

2-(6-Fluoro-1H-indol-3-yl)ethan-1-aminium chloride (8)

Crystal data

C10H12FN2^+·Cl^−	Dx = 1.352 Mg m^−3
Mr = 214.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9879 reflections
a = 8.3572 (4) Å	θ = 3.0–26.4°
b = 10.3493 (5) Å	µ = 0.34 mm^−1
c = 24.3824 (13) Å	T = 297 K
V = 2108.86 (18) Å^3	BLOCK, colourless
Z = 8	0.35 × 0.24 × 0.06 mm
F(000) = 896

Data collection

Bruker D8 Venture CMOS diffractometer	1922 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.034
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 26.4°, θmin = 3.0°
Tmin = 0.688, Tmax = 0.745	h = −10→10
56982 measured reflections	k = −12→12
2154 independent reflections	l = −30→30

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0335P)^2 + 0.9531P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
2154 reflections	Δρmax = 0.18 e Å^−3
143 parameters	Δρmin = −0.20 e Å^−3

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
F1	0.76619 (16)	0.65302 (11)	0.76660 (5)	0.0666 (3)
Cl1	0.34056 (6)	0.14461 (4)	0.45568 (2)	0.04892 (16)
N1	0.51550 (18)	0.58376 (14)	0.59023 (6)	0.0450 (4)
N2	0.55308 (19)	0.14739 (14)	0.56354 (7)	0.0453 (4)
C1	0.4260 (2)	0.48113 (17)	0.57188 (7)	0.0448 (4)
H1A	0.380270	0.475272	0.537203	0.054*
C2	0.56301 (19)	0.55967 (15)	0.64312 (7)	0.0382 (4)
C3	0.6521 (2)	0.63578 (16)	0.67903 (8)	0.0450 (4)
H3	0.690583	0.716908	0.669255	0.054*
C4	0.6792 (2)	0.58324 (17)	0.72949 (8)	0.0465 (4)
C5	0.6226 (2)	0.46375 (17)	0.74649 (8)	0.0477 (4)
H5	0.645373	0.433433	0.781539	0.057*
C6	0.5323 (2)	0.39047 (17)	0.71086 (7)	0.0426 (4)
H6	0.491869	0.310813	0.721801	0.051*
C7	0.50220 (18)	0.43737 (15)	0.65801 (7)	0.0361 (3)
C8	0.41381 (19)	0.38943 (16)	0.61152 (7)	0.0386 (4)
C9	0.3279 (2)	0.26299 (18)	0.60763 (8)	0.0464 (4)
H9A	0.268716	0.260429	0.573427	0.056*
H9B	0.251125	0.257323	0.637378	0.056*
C10	0.4382 (2)	0.14666 (17)	0.61018 (8)	0.0476 (4)
H10A	0.496814	0.147725	0.644508	0.057*
H10B	0.374973	0.068094	0.609018	0.057*
H2A	0.615 (2)	0.0671 (14)	0.5630 (9)	0.073 (7)*
H2B	0.624 (2)	0.2225 (15)	0.5639 (9)	0.067 (6)*
H2C	0.495 (2)	0.150 (2)	0.5285 (6)	0.064 (6)*
H1	0.534 (2)	0.6547 (13)	0.5732 (8)	0.056 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0690 (8)	0.0553 (7)	0.0755 (8)	−0.0059 (6)	−0.0153 (7)	−0.0187 (6)
Cl1	0.0563 (3)	0.0328 (2)	0.0576 (3)	0.00211 (18)	−0.0106 (2)	0.00254 (18)
N1	0.0490 (8)	0.0361 (8)	0.0498 (8)	0.0054 (7)	0.0075 (7)	0.0085 (7)
N2	0.0481 (9)	0.0320 (7)	0.0558 (9)	−0.0011 (6)	−0.0057 (7)	−0.0025 (7)
C1	0.0403 (9)	0.0494 (10)	0.0449 (9)	0.0100 (8)	0.0015 (7)	0.0029 (8)
C2	0.0348 (8)	0.0314 (8)	0.0485 (9)	0.0058 (7)	0.0085 (7)	0.0013 (7)
C3	0.0415 (9)	0.0307 (8)	0.0627 (11)	0.0015 (7)	0.0091 (8)	−0.0042 (8)
C4	0.0409 (9)	0.0394 (9)	0.0590 (11)	0.0033 (7)	−0.0021 (8)	−0.0127 (8)
C5	0.0499 (10)	0.0461 (10)	0.0470 (9)	0.0054 (8)	−0.0047 (8)	0.0000 (8)
C6	0.0428 (9)	0.0345 (8)	0.0507 (10)	−0.0006 (7)	0.0018 (8)	0.0042 (7)
C7	0.0306 (7)	0.0324 (8)	0.0451 (9)	0.0041 (6)	0.0044 (6)	0.0002 (7)
C8	0.0325 (8)	0.0382 (8)	0.0450 (9)	0.0041 (7)	0.0014 (7)	−0.0016 (7)
C9	0.0383 (9)	0.0515 (10)	0.0493 (10)	−0.0074 (8)	−0.0021 (7)	−0.0028 (8)
C10	0.0532 (10)	0.0384 (9)	0.0512 (10)	−0.0135 (8)	−0.0076 (8)	0.0031 (8)

Geometric parameters (Å, º)

F1—C4	1.367 (2)	C3—C4	1.364 (3)
N1—C1	1.374 (2)	C4—C5	1.387 (3)
N1—C2	1.372 (2)	C5—H5	0.9300
N1—H1	0.858 (9)	C5—C6	1.378 (2)
N2—C10	1.488 (2)	C6—H6	0.9300
N2—H2A	0.980 (10)	C6—C7	1.400 (2)
N2—H2B	0.979 (10)	C7—C8	1.441 (2)
N2—H2C	0.984 (9)	C8—C9	1.496 (2)
C1—H1A	0.9300	C9—H9A	0.9700
C1—C8	1.358 (2)	C9—H9B	0.9700
C2—C3	1.394 (2)	C9—C10	1.517 (3)
C2—C7	1.411 (2)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C1—N1—H1	127.2 (14)	C6—C5—H5	120.4
C2—N1—C1	108.85 (14)	C5—C6—H6	120.4
C2—N1—H1	123.8 (14)	C5—C6—C7	119.20 (16)
C10—N2—H2A	110.4 (14)	C7—C6—H6	120.4
C10—N2—H2B	113.0 (13)	C2—C7—C8	106.91 (15)
C10—N2—H2C	110.0 (13)	C6—C7—C2	118.89 (16)
H2A—N2—H2B	110.5 (19)	C6—C7—C8	134.18 (16)
H2A—N2—H2C	106.2 (18)	C1—C8—C7	106.29 (15)
H2B—N2—H2C	106.5 (18)	C1—C8—C9	127.04 (16)
N1—C1—H1A	124.8	C7—C8—C9	126.66 (15)
C8—C1—N1	110.45 (16)	C8—C9—H9A	108.9
C8—C1—H1A	124.8	C8—C9—H9B	108.9
N1—C2—C3	129.98 (16)	C8—C9—C10	113.57 (14)
N1—C2—C7	107.49 (15)	H9A—C9—H9B	107.7
C3—C2—C7	122.52 (16)	C10—C9—H9A	108.9
C2—C3—H3	122.3	C10—C9—H9B	108.9
C4—C3—C2	115.47 (16)	N2—C10—C9	110.89 (14)
C4—C3—H3	122.3	N2—C10—H10A	109.5
F1—C4—C5	117.03 (17)	N2—C10—H10B	109.5
C3—C4—F1	118.33 (16)	C9—C10—H10A	109.5
C3—C4—C5	124.64 (17)	C9—C10—H10B	109.5
C4—C5—H5	120.4	H10A—C10—H10B	108.0
C6—C5—C4	119.26 (17)
F1—C4—C5—C6	179.07 (16)	C2—C7—C8—C9	179.76 (15)
N1—C1—C8—C7	−0.21 (19)	C3—C2—C7—C6	0.0 (2)
N1—C1—C8—C9	−179.44 (15)	C3—C2—C7—C8	178.50 (14)
N1—C2—C3—C4	179.97 (16)	C3—C4—C5—C6	0.0 (3)
N1—C2—C7—C6	−179.12 (14)	C4—C5—C6—C7	1.1 (3)
N1—C2—C7—C8	−0.64 (17)	C5—C6—C7—C2	−1.1 (2)
C1—N1—C2—C3	−178.53 (16)	C5—C6—C7—C8	−179.09 (17)
C1—N1—C2—C7	0.52 (18)	C6—C7—C8—C1	178.67 (18)
C1—C8—C9—C10	113.9 (2)	C6—C7—C8—C9	−2.1 (3)
C2—N1—C1—C8	−0.19 (19)	C7—C2—C3—C4	1.0 (2)
C2—C3—C4—F1	179.88 (14)	C7—C8—C9—C10	−65.1 (2)
C2—C3—C4—C5	−1.1 (3)	C8—C9—C10—N2	−61.51 (19)
C2—C7—C8—C1	0.53 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.98 (1)	2.27 (1)	3.1847 (15)	155 (2)
N2—H2B···Cl1^ii	0.98 (1)	2.32 (1)	3.2597 (16)	161 (2)
N2—H2C···Cl1	0.98 (1)	2.19 (1)	3.1736 (17)	173 (2)
N1—H1···Cl1^iii	0.86 (1)	2.43 (1)	3.2562 (15)	162 (2)

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

2-(7-Methyl-1H-indol-3-yl)ethan-1-aminium chloride (9)

Crystal data

C11H15N2^+·Cl^−	Dx = 1.187 Mg m^−3
Mr = 210.70	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9693 reflections
a = 9.1893 (5) Å	θ = 2.7–25.4°
b = 9.3259 (4) Å	µ = 0.29 mm^−1
c = 27.5149 (15) Å	T = 297 K
V = 2358.0 (2) Å^3	PLATE, colourless
Z = 8	0.24 × 0.16 × 0.02 mm
F(000) = 896

Data collection

Bruker D8 Venture CMOS diffractometer	1791 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.054
Absorption correction: multi-scan (SADABS; Bruker, 2018)	θmax = 25.7°, θmin = 2.7°
Tmin = 0.703, Tmax = 0.745	h = −11→11
43558 measured reflections	k = −11→11
2237 independent reflections	l = −33→33

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 1.2441P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2237 reflections	Δρmax = 0.15 e Å^−3
144 parameters	Δρmin = −0.13 e Å^−3

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
Cl1	0.12236 (5)	0.28064 (5)	0.52435 (2)	0.04928 (16)
N1	0.60463 (18)	0.7039 (2)	0.39926 (6)	0.0520 (4)
N2	0.17796 (19)	0.56121 (18)	0.46316 (6)	0.0461 (4)
C1	0.5321 (2)	0.5891 (2)	0.41812 (8)	0.0544 (5)
H1A	0.555653	0.543935	0.447203	0.065*
C2	0.5419 (2)	0.7405 (2)	0.35562 (7)	0.0424 (4)
C3	0.5765 (2)	0.8522 (2)	0.32382 (8)	0.0532 (5)
C4	0.4905 (3)	0.8629 (3)	0.28304 (8)	0.0651 (6)
H4	0.509736	0.935255	0.260691	0.078*
C5	0.3753 (3)	0.7690 (3)	0.27406 (8)	0.0653 (6)
H5	0.320769	0.779728	0.245817	0.078*
C6	0.3410 (2)	0.6617 (2)	0.30588 (7)	0.0523 (5)
H6	0.263434	0.600343	0.299700	0.063*
C7	0.4249 (2)	0.64611 (19)	0.34787 (6)	0.0406 (4)
C8	0.4205 (2)	0.5499 (2)	0.38853 (7)	0.0461 (5)
C9	0.3100 (3)	0.4358 (2)	0.39729 (8)	0.0600 (6)
H9A	0.346766	0.369865	0.421624	0.072*
H9B	0.295166	0.382234	0.367476	0.072*
C10	0.1652 (2)	0.4957 (2)	0.41425 (8)	0.0548 (5)
H10A	0.131688	0.567459	0.391300	0.066*
H10B	0.093639	0.419302	0.415195	0.066*
C11	0.6981 (3)	0.9552 (3)	0.33489 (10)	0.0836 (8)
H11A	0.710920	1.019423	0.307963	0.125*
H11B	0.786463	0.902619	0.340248	0.125*
H11C	0.674476	1.009240	0.363516	0.125*
H2A	0.183 (3)	0.4864 (19)	0.4885 (6)	0.077 (7)*
H2B	0.2651 (17)	0.619 (2)	0.4687 (8)	0.074 (7)*
H2C	0.0905 (17)	0.618 (2)	0.4711 (8)	0.075 (7)*
H1	0.6836 (16)	0.738 (2)	0.4119 (7)	0.069 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0434 (3)	0.0486 (3)	0.0558 (3)	0.0041 (2)	−0.0017 (2)	0.0021 (2)
N1	0.0370 (9)	0.0674 (12)	0.0515 (10)	0.0034 (9)	−0.0051 (8)	−0.0124 (9)
N2	0.0394 (9)	0.0425 (9)	0.0565 (11)	−0.0054 (8)	−0.0004 (8)	−0.0002 (8)
C1	0.0538 (13)	0.0624 (13)	0.0471 (11)	0.0171 (11)	−0.0001 (10)	0.0002 (10)
C2	0.0362 (10)	0.0480 (11)	0.0429 (10)	0.0037 (8)	0.0029 (8)	−0.0128 (8)
C3	0.0475 (12)	0.0543 (12)	0.0577 (13)	−0.0070 (10)	0.0098 (10)	−0.0130 (10)
C4	0.0760 (17)	0.0619 (14)	0.0573 (14)	−0.0058 (13)	0.0082 (12)	0.0075 (11)
C5	0.0698 (15)	0.0761 (16)	0.0499 (12)	−0.0029 (14)	−0.0119 (11)	0.0039 (11)
C6	0.0477 (12)	0.0586 (12)	0.0506 (12)	−0.0069 (10)	−0.0065 (10)	−0.0104 (10)
C7	0.0379 (10)	0.0405 (10)	0.0433 (10)	0.0036 (8)	0.0014 (8)	−0.0086 (8)
C8	0.0469 (11)	0.0414 (10)	0.0500 (11)	0.0083 (9)	0.0053 (9)	−0.0041 (8)
C9	0.0771 (16)	0.0406 (11)	0.0623 (13)	−0.0026 (11)	0.0084 (12)	−0.0048 (10)
C10	0.0548 (13)	0.0527 (12)	0.0570 (12)	−0.0182 (10)	−0.0045 (10)	0.0006 (10)
C11	0.0768 (18)	0.0845 (18)	0.0896 (19)	−0.0360 (15)	0.0156 (15)	−0.0175 (15)

Geometric parameters (Å, º)

N1—C1	1.364 (3)	C5—H5	0.9300
N1—C2	1.375 (2)	C5—C6	1.367 (3)
N1—H1	0.867 (10)	C6—H6	0.9300
N2—C10	1.482 (3)	C6—C7	1.396 (3)
N2—H2A	0.987 (10)	C7—C8	1.435 (3)
N2—H2B	0.978 (10)	C8—C9	1.490 (3)
N2—H2C	0.986 (10)	C9—H9A	0.9700
C1—H1A	0.9300	C9—H9B	0.9700
C1—C8	1.359 (3)	C9—C10	1.517 (3)
C2—C3	1.397 (3)	C10—H10A	0.9700
C2—C7	1.406 (3)	C10—H10B	0.9700
C3—C4	1.376 (3)	C11—H11A	0.9600
C3—C11	1.505 (3)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C4—C5	1.395 (3)
C1—N1—C2	108.80 (17)	C7—C6—H6	120.7
C1—N1—H1	123.2 (16)	C2—C7—C8	107.15 (17)
C2—N1—H1	127.6 (16)	C6—C7—C2	118.84 (18)
C10—N2—H2A	110.7 (14)	C6—C7—C8	134.01 (19)
C10—N2—H2B	115.8 (13)	C1—C8—C7	106.12 (18)
C10—N2—H2C	110.9 (13)	C1—C8—C9	127.5 (2)
H2A—N2—H2B	104.0 (18)	C7—C8—C9	126.27 (19)
H2A—N2—H2C	105.1 (18)	C8—C9—H9A	109.1
H2B—N2—H2C	109.6 (18)	C8—C9—H9B	109.1
N1—C1—H1A	124.7	C8—C9—C10	112.61 (17)
C8—C1—N1	110.61 (19)	H9A—C9—H9B	107.8
C8—C1—H1A	124.7	C10—C9—H9A	109.1
N1—C2—C3	129.54 (19)	C10—C9—H9B	109.1
N1—C2—C7	107.31 (17)	N2—C10—C9	111.20 (17)
C3—C2—C7	123.09 (18)	N2—C10—H10A	109.4
C2—C3—C11	121.2 (2)	N2—C10—H10B	109.4
C4—C3—C2	115.72 (19)	C9—C10—H10A	109.4
C4—C3—C11	123.0 (2)	C9—C10—H10B	109.4
C3—C4—H4	118.8	H10A—C10—H10B	108.0
C3—C4—C5	122.3 (2)	C3—C11—H11A	109.5
C5—C4—H4	118.8	C3—C11—H11B	109.5
C4—C5—H5	119.3	C3—C11—H11C	109.5
C6—C5—C4	121.4 (2)	H11A—C11—H11B	109.5
C6—C5—H5	119.3	H11A—C11—H11C	109.5
C5—C6—H6	120.7	H11B—C11—H11C	109.5
C5—C6—C7	118.6 (2)
N1—C1—C8—C7	0.8 (2)	C3—C2—C7—C6	1.7 (3)
N1—C1—C8—C9	−176.10 (19)	C3—C2—C7—C8	−178.09 (17)
N1—C2—C3—C4	−178.6 (2)	C3—C4—C5—C6	0.7 (4)
N1—C2—C3—C11	−0.1 (3)	C4—C5—C6—C7	−0.7 (3)
N1—C2—C7—C6	179.24 (17)	C5—C6—C7—C2	−0.5 (3)
N1—C2—C7—C8	−0.53 (19)	C5—C6—C7—C8	179.2 (2)
C1—N1—C2—C3	178.37 (19)	C6—C7—C8—C1	−179.9 (2)
C1—N1—C2—C7	1.0 (2)	C6—C7—C8—C9	−2.9 (3)
C1—C8—C9—C10	101.3 (3)	C7—C2—C3—C4	−1.6 (3)
C2—N1—C1—C8	−1.2 (2)	C7—C2—C3—C11	176.88 (19)
C2—C3—C4—C5	0.4 (3)	C7—C8—C9—C10	−75.0 (3)
C2—C7—C8—C1	−0.2 (2)	C8—C9—C10—N2	−66.7 (2)
C2—C7—C8—C9	176.80 (18)	C11—C3—C4—C5	−178.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.99 (1)	2.23 (1)	3.1531 (18)	156 (2)
N2—H2B···Cl1^i	0.98 (1)	2.38 (2)	3.2232 (17)	144 (2)
N2—H2C···Cl1^ii	0.99 (1)	2.18 (1)	3.1480 (18)	168 (2)
N1—H1···Cl1^iii	0.87 (1)	2.51 (2)	3.2762 (17)	148 (2)

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