The title compound, C
25H
19N
3, has one half-molecule in the asymmetric unit, with the other half generated by a crystallographic twofold axis of symmetry. The dihedral angle between the two symmetry-related indole ring systems is 46.79 (2)°. The pyridine ring forms a dihedral angle of 80.56 (2)° with the plane of each indole ring system. Molecules related by a center of inversion are linked
via intermolecular C—H
π interactions to form chains along the
c axis.
Supporting information
CCDC reference: 613824
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
1,9,26-Triazahexacyclo[17.6.1.1
3,7.1
9,16.0
10,15.0
20,25]
pentacosa-3,5,7(26),10 (15),11,13,16 (27),17,19 (28),20 (25),21,23-dodecaene
top
Crystal data top
C25H19N3 | F(000) = 760 |
Mr = 361.43 | Dx = 1.339 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6564 reflections |
a = 19.9027 (7) Å | θ = 2.6–37.1° |
b = 11.3107 (3) Å | µ = 0.08 mm−1 |
c = 8.7157 (5) Å | T = 100 K |
β = 113.994 (3)° | Needle, colourless |
V = 1792.48 (13) Å3 | 0.61 × 0.18 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 2064 independent reflections |
Radiation source: fine-focus sealed tube | 1927 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans | h = −25→25 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.917, Tmax = 0.986 | l = −11→11 |
24681 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0566P)2 + 1.0129P] where P = (Fo2 + 2Fc2)/3 |
2064 reflections | (Δ/σ)max = 0.001 |
166 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | −0.11929 (4) | 0.18374 (7) | 0.06151 (10) | 0.0179 (2) | |
N2 | 0.0000 | 0.05214 (10) | 0.2500 | 0.0176 (2) | |
C1 | −0.07190 (5) | 0.27541 (9) | 0.07460 (12) | 0.0201 (2) | |
H1 | −0.0361 (7) | 0.2678 (12) | 0.0245 (16) | 0.026 (3)* | |
C2 | −0.08178 (5) | 0.36627 (8) | 0.16726 (12) | 0.0194 (2) | |
C3 | −0.13917 (5) | 0.32878 (8) | 0.21660 (12) | 0.0180 (2) | |
C4 | −0.17396 (5) | 0.38041 (9) | 0.31150 (12) | 0.0211 (2) | |
H4 | −0.1596 (7) | 0.4604 (13) | 0.3603 (17) | 0.028 (3)* | |
C5 | −0.22839 (6) | 0.31735 (9) | 0.33640 (13) | 0.0234 (2) | |
H5 | −0.2539 (7) | 0.3512 (12) | 0.4035 (17) | 0.029 (3)* | |
C6 | −0.24860 (6) | 0.20292 (10) | 0.26929 (13) | 0.0229 (2) | |
H6 | −0.2881 (8) | 0.1597 (13) | 0.2865 (18) | 0.035 (4)* | |
C7 | −0.21486 (5) | 0.14955 (9) | 0.17644 (12) | 0.0198 (2) | |
H7 | −0.2295 (7) | 0.0718 (12) | 0.1290 (16) | 0.023 (3)* | |
C8 | −0.16023 (5) | 0.21329 (8) | 0.15079 (11) | 0.0173 (2) | |
C9 | −0.11353 (5) | 0.06674 (8) | 0.00008 (12) | 0.0196 (2) | |
H9B | −0.0998 (7) | 0.0764 (11) | −0.0976 (16) | 0.020 (3)* | |
H9A | −0.1621 (7) | 0.0269 (11) | −0.0388 (15) | 0.021 (3)* | |
C10 | −0.05444 (5) | −0.00786 (8) | 0.13195 (11) | 0.0169 (2) | |
C11 | −0.05675 (5) | −0.13101 (9) | 0.12605 (12) | 0.0201 (2) | |
H11 | −0.0970 (7) | −0.1715 (12) | 0.0387 (16) | 0.025 (3)* | |
C12 | 0.0000 | −0.19247 (12) | 0.2500 | 0.0226 (3) | |
H12 | 0.0000 | −0.2786 (19) | 0.2500 | 0.032 (5)* | |
C13 | −0.03684 (6) | 0.47429 (9) | 0.21611 (14) | 0.0239 (2) | |
H13 | −0.0640 (7) | 0.5515 (12) | 0.1941 (16) | 0.025 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0175 (4) | 0.0144 (4) | 0.0190 (4) | 0.0007 (3) | 0.0045 (3) | −0.0005 (3) |
N2 | 0.0190 (5) | 0.0145 (5) | 0.0181 (5) | 0.000 | 0.0064 (4) | 0.000 |
C1 | 0.0181 (4) | 0.0169 (5) | 0.0233 (5) | 0.0004 (3) | 0.0063 (4) | 0.0011 (4) |
C2 | 0.0166 (4) | 0.0149 (5) | 0.0233 (5) | 0.0018 (3) | 0.0048 (4) | 0.0015 (3) |
C3 | 0.0161 (4) | 0.0151 (4) | 0.0182 (4) | 0.0016 (3) | 0.0024 (3) | 0.0018 (3) |
C4 | 0.0221 (5) | 0.0182 (5) | 0.0195 (4) | 0.0040 (4) | 0.0050 (4) | 0.0008 (4) |
C5 | 0.0244 (5) | 0.0246 (5) | 0.0210 (5) | 0.0058 (4) | 0.0091 (4) | 0.0032 (4) |
C6 | 0.0196 (5) | 0.0253 (5) | 0.0217 (5) | 0.0007 (4) | 0.0063 (4) | 0.0059 (4) |
C7 | 0.0185 (4) | 0.0174 (5) | 0.0183 (4) | −0.0001 (4) | 0.0021 (4) | 0.0035 (3) |
C8 | 0.0160 (4) | 0.0159 (4) | 0.0154 (4) | 0.0025 (3) | 0.0019 (3) | 0.0019 (3) |
C9 | 0.0210 (5) | 0.0151 (5) | 0.0185 (5) | 0.0001 (3) | 0.0039 (4) | −0.0028 (3) |
C10 | 0.0188 (5) | 0.0155 (4) | 0.0172 (4) | 0.0000 (3) | 0.0084 (4) | −0.0008 (3) |
C11 | 0.0214 (5) | 0.0163 (5) | 0.0219 (5) | −0.0021 (4) | 0.0081 (4) | −0.0032 (3) |
C12 | 0.0246 (7) | 0.0140 (6) | 0.0289 (7) | 0.000 | 0.0105 (6) | 0.000 |
C13 | 0.0215 (5) | 0.0136 (5) | 0.0341 (6) | 0.0010 (4) | 0.0087 (4) | −0.0001 (4) |
Geometric parameters (Å, º) top
N1—C1 | 1.3748 (13) | C6—C7 | 1.3827 (15) |
N1—C8 | 1.3773 (12) | C6—H6 | 0.988 (15) |
N1—C9 | 1.4494 (12) | C7—C8 | 1.3963 (14) |
N2—C10 | 1.3366 (11) | C7—H7 | 0.965 (14) |
N2—C10i | 1.3366 (11) | C9—C10 | 1.5221 (13) |
C1—C2 | 1.3698 (14) | C9—H9B | 1.000 (13) |
C1—H1 | 0.979 (14) | C9—H9A | 0.993 (12) |
C2—C3 | 1.4383 (13) | C10—C11 | 1.3939 (13) |
C2—C13 | 1.4711 (13) | C11—C12 | 1.3906 (12) |
C3—C4 | 1.4037 (14) | C11—H11 | 0.967 (13) |
C3—C8 | 1.4197 (13) | C12—C11i | 1.3906 (12) |
C4—C5 | 1.3858 (15) | C12—H12 | 0.97 (2) |
C4—H4 | 0.992 (14) | C13—C13i | 1.340 (2) |
C5—C6 | 1.4098 (15) | C13—H13 | 1.005 (13) |
C5—H5 | 0.993 (14) | | |
| | | |
C1—N1—C8 | 108.28 (8) | C6—C7—H7 | 121.0 (8) |
C1—N1—C9 | 124.37 (9) | C8—C7—H7 | 121.4 (8) |
C8—N1—C9 | 125.74 (8) | N1—C8—C7 | 130.04 (9) |
C10—N2—C10i | 118.97 (12) | N1—C8—C3 | 107.83 (8) |
C2—C1—N1 | 110.90 (9) | C7—C8—C3 | 122.11 (9) |
C2—C1—H1 | 129.4 (8) | N1—C9—C10 | 112.34 (8) |
N1—C1—H1 | 119.7 (8) | N1—C9—H9B | 107.8 (7) |
C1—C2—C3 | 106.07 (8) | C10—C9—H9B | 108.0 (7) |
C1—C2—C13 | 125.28 (9) | N1—C9—H9A | 109.2 (7) |
C3—C2—C13 | 128.44 (9) | C10—C9—H9A | 110.6 (7) |
C4—C3—C8 | 119.05 (9) | H9B—C9—H9A | 108.9 (10) |
C4—C3—C2 | 134.06 (9) | N2—C10—C11 | 122.69 (9) |
C8—C3—C2 | 106.88 (8) | N2—C10—C9 | 115.81 (9) |
C5—C4—C3 | 118.85 (9) | C11—C10—C9 | 121.49 (8) |
C5—C4—H4 | 120.7 (8) | C12—C11—C10 | 117.82 (9) |
C3—C4—H4 | 120.5 (8) | C12—C11—H11 | 121.7 (8) |
C4—C5—C6 | 121.12 (10) | C10—C11—H11 | 120.5 (8) |
C4—C5—H5 | 120.9 (8) | C11i—C12—C11 | 120.01 (13) |
C6—C5—H5 | 118.0 (8) | C11i—C12—H12 | 120.00 (6) |
C7—C6—C5 | 121.27 (10) | C11—C12—H12 | 120.00 (6) |
C7—C6—H6 | 118.6 (9) | C13i—C13—C2 | 123.73 (5) |
C5—C6—H6 | 120.1 (9) | C13i—C13—H13 | 119.5 (7) |
C6—C7—C8 | 117.60 (9) | C2—C13—H13 | 116.7 (7) |
| | | |
C8—N1—C1—C2 | −1.46 (11) | C6—C7—C8—N1 | −178.31 (9) |
C9—N1—C1—C2 | −167.67 (8) | C6—C7—C8—C3 | 0.05 (14) |
N1—C1—C2—C3 | 0.31 (11) | C4—C3—C8—N1 | 179.12 (8) |
N1—C1—C2—C13 | 175.40 (9) | C2—C3—C8—N1 | −1.79 (10) |
C1—C2—C3—C4 | 179.80 (10) | C4—C3—C8—C7 | 0.44 (14) |
C13—C2—C3—C4 | 4.93 (18) | C2—C3—C8—C7 | 179.53 (8) |
C1—C2—C3—C8 | 0.91 (10) | C1—N1—C9—C10 | 78.48 (12) |
C13—C2—C3—C8 | −173.97 (9) | C8—N1—C9—C10 | −85.33 (11) |
C8—C3—C4—C5 | −0.68 (14) | C10i—N2—C10—C11 | −0.33 (7) |
C2—C3—C4—C5 | −179.47 (10) | C10i—N2—C10—C9 | −178.83 (9) |
C3—C4—C5—C6 | 0.45 (15) | N1—C9—C10—N2 | −25.39 (11) |
C4—C5—C6—C7 | 0.04 (15) | N1—C9—C10—C11 | 156.09 (9) |
C5—C6—C7—C8 | −0.29 (15) | N2—C10—C11—C12 | 0.63 (13) |
C1—N1—C8—C7 | −179.47 (9) | C9—C10—C11—C12 | 179.05 (7) |
C9—N1—C8—C7 | −13.50 (16) | C10—C11—C12—C11i | −0.30 (6) |
C1—N1—C8—C3 | 2.00 (10) | C1—C2—C13—C13i | −48.0 (2) |
C9—N1—C8—C3 | 167.97 (8) | C3—C2—C13—C13i | 125.99 (15) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···Cg1ii | 1.000 (13) | 2.804 (15) | 3.7233 (11) | 153 (1) |
C9—H9B···Cg1iii | 1.000 (13) | 2.804 (15) | 3.7233 (11) | 153 (1) |
C11—H11···Cg2iii | 0.967 (13) | 2.728 (13) | 3.6732 (11) | 166 (1) |
Symmetry codes: (ii) −x, −y, −z; (iii) x, −y, z−1/2. |