1,9-Diazahexacyclo[17.6.1.1^3,7.1^9,16.0^10,15.0^20,25]­hexacosa-3,5,7(26),10(15),11,13,16(27),17,19(28),20(25),21,23-dodecaene

The title compound, C₂₆H₂₀N₂, has one half-mol­ecule in the asymmetric unit. The mol­ecular twofold rotational symmetry is preserved on crystallization. The dihedral angle between the two symmetry-related indole ring systems is 49.65 (4)°. The benzene ring is oriented almost perpendicular [dihedral angle 86.02 (3)°] to the planes of both indole ring systems. Mol­ecules related by a centre of inversion are linked via inter­molecular C—H...π inter­actions to form chains along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.051
• wR factor = 0.154
• Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.762     0.993
            Tmin(prime) and Tmax expected:      0.957     0.992
            RR(prime) =      0.795
            Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       6.63 su
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

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).

Dibenzo[a-4,5;a'-10,11]-3,12-diazatetracyclo[12.3.1.1^3,6.1^9,12] eicosa-6(19),7,9(20),14 (18),15,17-hexene

Crystal data

C26H20N2	F(000) = 760
Mr = 360.44	Dx = 1.294 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1440 reflections
a = 19.6434 (9) Å	θ = 2.3–21.2°
b = 11.2843 (5) Å	µ = 0.08 mm^−1
c = 9.0441 (3) Å	T = 293 K
β = 112.635 (4)°	Needle, colourless
V = 1850.32 (13) Å^3	0.57 × 0.16 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	2891 independent reflections
Radiation source: fine-focus sealed tube	1316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
Detector resolution: 8.33 pixels mm^-1	θmax = 30.8°, θmin = 2.1°
ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→15
Tmin = 0.762, Tmax = 0.993	l = −12→12
13509 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0658P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
2891 reflections	Δρmax = 0.17 e Å^−3
129 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1998), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.37824 (7)	0.30926 (11)	0.05131 (15)	0.0495 (4)
C1	0.42547 (9)	0.21631 (14)	0.0625 (2)	0.0539 (4)
H1	0.4582	0.2135	0.0107	0.065*
C2	0.41798 (9)	0.12908 (14)	0.1595 (2)	0.0532 (4)
C3	0.36182 (9)	0.16900 (14)	0.21269 (19)	0.0509 (4)
C4	0.32884 (10)	0.12107 (16)	0.3115 (2)	0.0634 (5)
H4	0.3428	0.0468	0.3579	0.076*
C5	0.27535 (11)	0.18558 (19)	0.3390 (2)	0.0713 (6)
H5	0.2525	0.1537	0.4030	0.086*
C6	0.25482 (10)	0.29821 (18)	0.2723 (2)	0.0686 (5)
H6	0.2188	0.3401	0.2935	0.082*
C7	0.28656 (9)	0.34807 (16)	0.17651 (19)	0.0572 (5)
H7	0.2730	0.4233	0.1330	0.069*
C8	0.33969 (8)	0.28272 (14)	0.14635 (18)	0.0473 (4)
C9	0.38667 (9)	0.42826 (14)	−0.0023 (2)	0.0558 (5)
H9A	0.3397	0.4692	−0.0361	0.067*
H9B	0.4004	0.4225	−0.0942	0.067*
C10	0.44456 (8)	0.49999 (13)	0.12796 (18)	0.0472 (4)
C11	0.44502 (9)	0.62272 (14)	0.1287 (2)	0.0564 (5)
H11	0.4086	0.6647	0.0483	0.068*
C12	0.5000	0.6822 (2)	0.2500	0.0634 (7)
H12	0.5000	0.7646	0.2500	0.076*
C13	0.5000	0.44210 (19)	0.2500	0.0508 (6)
H13	0.5000	0.3597	0.2500	0.061*
C14	0.46359 (9)	0.02190 (14)	0.2112 (2)	0.0685 (6)
H14	0.4398	−0.0511	0.1880	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0499 (8)	0.0388 (7)	0.0492 (8)	−0.0014 (6)	0.0072 (6)	0.0011 (6)
C1	0.0499 (9)	0.0436 (9)	0.0619 (11)	−0.0023 (8)	0.0144 (8)	−0.0062 (8)
C2	0.0485 (9)	0.0368 (9)	0.0624 (10)	−0.0033 (7)	0.0082 (8)	−0.0036 (8)
C3	0.0493 (9)	0.0431 (9)	0.0485 (9)	−0.0099 (7)	0.0058 (8)	−0.0023 (7)
C4	0.0678 (11)	0.0519 (10)	0.0603 (11)	−0.0146 (9)	0.0135 (10)	0.0006 (9)
C5	0.0727 (13)	0.0760 (14)	0.0667 (12)	−0.0172 (11)	0.0286 (10)	−0.0112 (11)
C6	0.0611 (11)	0.0699 (14)	0.0693 (12)	−0.0047 (10)	0.0188 (10)	−0.0171 (10)
C7	0.0518 (10)	0.0540 (10)	0.0541 (10)	−0.0026 (8)	0.0074 (9)	−0.0069 (8)
C8	0.0441 (9)	0.0427 (9)	0.0442 (9)	−0.0050 (7)	0.0048 (7)	−0.0027 (7)
C9	0.0600 (10)	0.0446 (9)	0.0520 (10)	0.0007 (8)	0.0096 (8)	0.0083 (8)
C10	0.0530 (9)	0.0384 (8)	0.0477 (9)	0.0018 (7)	0.0165 (8)	0.0032 (7)
C11	0.0627 (11)	0.0415 (9)	0.0598 (10)	0.0056 (8)	0.0178 (9)	0.0072 (8)
C12	0.0803 (18)	0.0313 (11)	0.0731 (17)	0.000	0.0237 (15)	0.000
C13	0.0563 (13)	0.0331 (11)	0.0512 (13)	0.000	0.0078 (11)	0.000
C14	0.0624 (10)	0.0332 (9)	0.0965 (15)	−0.0044 (8)	0.0158 (11)	−0.0024 (9)

Geometric parameters (Å, º)

N1—C1	1.378 (2)	C7—C8	1.388 (2)
N1—C8	1.379 (2)	C7—H7	0.93
N1—C9	1.459 (2)	C9—C10	1.518 (2)
C1—C2	1.363 (2)	C9—H9A	0.97
C1—H1	0.93	C9—H9B	0.97
C2—C3	1.435 (2)	C10—C13	1.3805 (18)
C2—C14	1.470 (2)	C10—C11	1.385 (2)
C3—C4	1.399 (2)	C11—C12	1.381 (2)
C3—C8	1.412 (2)	C11—H11	0.93
C4—C5	1.377 (2)	C12—C11^i	1.381 (2)
C4—H4	0.93	C12—H12	0.93
C5—C6	1.398 (3)	C13—C10^i	1.3805 (18)
C5—H5	0.93	C13—H13	0.93
C6—C7	1.368 (2)	C14—C14^i	1.329 (3)
C6—H6	0.93	C14—H14	0.93
C1—N1—C8	107.73 (13)	N1—C8—C7	129.92 (15)
C1—N1—C9	124.46 (14)	N1—C8—C3	107.99 (14)
C8—N1—C9	124.52 (14)	C7—C8—C3	122.07 (15)
C2—C1—N1	111.13 (15)	N1—C9—C10	112.33 (13)
C2—C1—H1	124.4	N1—C9—H9A	109.1
N1—C1—H1	124.4	C10—C9—H9A	109.1
C1—C2—C3	106.04 (14)	N1—C9—H9B	109.1
C1—C2—C14	126.53 (16)	C10—C9—H9B	109.1
C3—C2—C14	127.17 (15)	H9A—C9—H9B	107.9
C4—C3—C8	118.70 (16)	C13—C10—C11	117.87 (16)
C4—C3—C2	134.24 (16)	C13—C10—C9	119.53 (14)
C8—C3—C2	107.05 (14)	C11—C10—C9	122.59 (15)
C5—C4—C3	118.95 (18)	C12—C11—C10	119.43 (17)
C5—C4—H4	120.5	C12—C11—H11	120.3
C3—C4—H4	120.5	C10—C11—H11	120.3
C4—C5—C6	121.06 (19)	C11—C12—C11^i	121.9 (2)
C4—C5—H5	119.5	C11—C12—H12	119.1
C6—C5—H5	119.5	C11^i—C12—H12	119.1
C7—C6—C5	121.41 (18)	C10^i—C13—C10	123.5 (2)
C7—C6—H6	119.3	C10^i—C13—H13	118.2
C5—C6—H6	119.3	C10—C13—H13	118.2
C6—C7—C8	117.80 (17)	C14^i—C14—C2	124.63 (9)
C6—C7—H7	121.1	C14^i—C14—H14	117.7
C8—C7—H7	121.1	C2—C14—H14	117.7
C8—N1—C1—C2	1.12 (17)	C6—C7—C8—N1	177.61 (14)
C9—N1—C1—C2	161.33 (14)	C6—C7—C8—C3	−0.8 (2)
N1—C1—C2—C3	0.38 (18)	C4—C3—C8—N1	−178.58 (13)
N1—C1—C2—C14	−174.05 (14)	C2—C3—C8—N1	2.39 (16)
C1—C2—C3—C4	179.50 (17)	C4—C3—C8—C7	0.1 (2)
C14—C2—C3—C4	−6.1 (3)	C2—C3—C8—C7	−178.88 (13)
C1—C2—C3—C8	−1.69 (17)	C1—N1—C9—C10	−78.79 (19)
C14—C2—C3—C8	172.69 (15)	C8—N1—C9—C10	78.17 (17)
C8—C3—C4—C5	0.8 (2)	N1—C9—C10—C13	24.37 (19)
C2—C3—C4—C5	179.54 (16)	N1—C9—C10—C11	−156.67 (15)
C3—C4—C5—C6	−1.2 (3)	C13—C10—C11—C12	−0.2 (2)
C4—C5—C6—C7	0.5 (3)	C9—C10—C11—C12	−179.14 (12)
C5—C6—C7—C8	0.5 (2)	C10—C11—C12—C11^i	0.09 (11)
C1—N1—C8—C7	179.24 (15)	C11—C10—C13—C10^i	0.08 (11)
C9—N1—C8—C7	19.0 (2)	C9—C10—C13—C10^i	179.09 (15)
C1—N1—C8—C3	−2.17 (16)	C1—C2—C14—C14^i	57.1 (3)
C9—N1—C8—C3	−162.37 (13)	C3—C2—C14—C14^i	−116.2 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N1	0.93	2.44	2.8087 (18)	103
C13—H13···N1^i	0.93	2.44	2.8087 (18)	103
C9—H9B···Cg2^ii	0.97	2.82	3.7184 (19)	154
C9—H9B···Cg2^iii	0.97	2.82	3.7184 (19)	154
C13—H13···Cg1	0.93	2.62	3.2625 (18)	127
C13—H13···Cg1^i	0.93	2.62	3.2625 (18)	127

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