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The crystal structures of the hydrochloride salts of nine substituted tryptamines, namely, 1-methyltryptammonium chloride, C
11H
15N
2+·Cl
−, (
1), 2-methyl-1-phenyltryptammonium chloride, C
17H
19N
2+·Cl
−, (
2), 5-methoxytryptammonium chloride, C
11H
15N
2O
+·Cl
−, (
3), 5-bromotryptammonium chloride, C
10H
12BrN
2+·Cl
−, (
4), 5-chlorotryptammonium chloride, C
10H
12ClN
2+·Cl
−, (
5), 5-fluorotryptammonium chloride, C
10H
12FN
2+·Cl
−, (
6), 5-methyltryptammonium chloride, C
11H
15N
2+·Cl
−, (
7), 6-fluorotryptammonium chloride, C
10H
12FN
2+·Cl
−, (
8), and 7-methyltryptammonium chloride, C
11H
15N
2+·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.
Supporting information
CCDC references: 2106056; 2106055; 2106054; 2106053; 2106052; 2106051; 2106050; 2106049; 2106048
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-1
H-indol-3-yl)ethan-1-aminium chloride (1)
top
Crystal data top
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) Å3 | T = 297 K |
Z = 18 | BLOCK, colourless |
F(000) = 2016 | 0.31 × 0.08 × 0.07 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0618P)2 + 2.0481P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···Cl1i | 0.97 | 2.79 | 3.737 (4) | 165 |
N2—H2A···Cl1ii | 0.98 (1) | 2.20 (2) | 3.151 (3) | 163 (4) |
N2—H2B···Cl1iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (2)
top
Crystal data top
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) Å3 | BLOCK, grey |
Z = 16 | 0.24 × 0.20 × 0.10 mm |
Data collection top
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 top
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0396P)2 + 3.9708P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl2i | 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···Cl4ii | 0.98 (1) | 2.49 (2) | 3.290 (2) | 138 (2) |
N4—H4A···Cl1iii | 0.98 (1) | 2.41 (2) | 3.251 (2) | 143 (3) |
N4—H4A···Cl4iv | 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···Cl4iv | 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···Cl2v | 0.99 (1) | 2.42 (2) | 3.164 (2) | 132 (2) |
N8—H8C···Cl1vi | 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-1
H-indol-3-yl)ethan-1-aminium chloride (3)
top
Crystal data top
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) Å3 | PLATE, colourless |
Z = 4 | 0.24 × 0.21 × 0.04 mm |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3256P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.87 (1) | 2.47 (1) | 3.2754 (17) | 154 (2) |
N2—H2A···Cl1ii | 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···Cl1iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (4)
top
Crystal data top
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) Å3 | BLOCK, colourless |
Z = 8 | 0.28 × 0.21 × 0.12 mm |
F(000) = 1104 | |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0204P)2 + 3.943P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1i | 0.99 (1) | 2.33 (2) | 3.217 (3) | 149 (3) |
N2—H2B···Cl1ii | 0.99 (1) | 2.19 (2) | 3.146 (3) | 162 (3) |
N1—H1···Cl1iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (5)
top
Crystal data top
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) Å3 | BLOCK, colourless |
Z = 4 | 0.24 × 0.20 × 0.06 mm |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.470P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl2i | 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···Cl2ii | 0.98 (1) | 2.18 (1) | 3.1585 (18) | 175 (2) |
N2—H2C···Cl2iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (6)
top
Crystal data top
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) Å3 | PLATE, colourless |
Z = 8 | 0.29 × 0.20 × 0.03 mm |
F(000) = 896 | |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0348P)2 + 1.1584P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···Cl1i | 0.98 (1) | 2.21 (1) | 3.1513 (17) | 161 (2) |
N2—H2C···Cl1ii | 0.98 (1) | 2.31 (1) | 3.2208 (17) | 156 (2) |
N1—H1···Cl1iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (7)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.20 × 0.08 mm |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.5865P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.86 (1) | 2.42 (2) | 3.242 (3) | 159 (3) |
N2—H2A···Cl1ii | 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···Cl1iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (8)
top
Crystal data top
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) Å3 | BLOCK, colourless |
Z = 8 | 0.35 × 0.24 × 0.06 mm |
F(000) = 896 | |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0335P)2 + 0.9531P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1i | 0.98 (1) | 2.27 (1) | 3.1847 (15) | 155 (2) |
N2—H2B···Cl1ii | 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···Cl1iii | 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-1
H-indol-3-yl)ethan-1-aminium chloride (9)
top
Crystal data top
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) Å3 | PLATE, colourless |
Z = 8 | 0.24 × 0.16 × 0.02 mm |
F(000) = 896 | |
Data collection top
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 top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.029P)2 + 1.2441P] where P = (Fo2 + 2Fc2)/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 top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···Cl1i | 0.98 (1) | 2.38 (2) | 3.2232 (17) | 144 (2) |
N2—H2C···Cl1ii | 0.99 (1) | 2.18 (1) | 3.1480 (18) | 168 (2) |
N1—H1···Cl1iii | 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. |
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