A dimer of 7-cyano­dibenzobarrelene

Jones, P.G.; Bubenitschek, P.; Hopf, H.; Witulski, B.

doi:10.1107/S160053680300093X

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A dimer of 7-cyanodibenzobarrelene

P. G. Jones, P. Bubenitschek, H. Hopf and B. Witulski

The molecule of the title compound, 2,3-dicyanotetrabenzo-pentacyclo[8.2.2.2^4,7.0^2,9.0^3,8]hexadeca-5,11,13,15-tetraene chloroform monosolvate, C₃₄H₂₂N₂·CHCl₃, displays approximate twofold symmetry. The four-membered ring has slightly lengthened C—C bonds and a ring pucker of 11.9 (7)°. The solvent molecule is involved in a C—H

π contact.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300093X/bt6225sup1.cif Contains datablocks 4, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300093X/bt62254sup2.hkl Contains datablock 4

CCDC reference: 204692

checkCIF report

Key indicators

Single-crystal X-ray study
T = 178 K
Mean (C-C) = 0.009 Å
R factor = 0.073
wR factor = 0.222
Data-to-parameter ratio = 10.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack    0.400
         From the CIF: _refine_ls_abs_structure_Flack_su    0.200
           Alert C Flack test results are ambiguous.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               3618
         Count of symmetry unique reflns         3629
         Completeness (_total/calc)             99.70%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Heating a solution of anthracene, (1), and cyanoacetylene, (2), in a 1:4 molar ratio in benzene at 433 K results in the formation of a complex mixture of cycloadducts (Hopf & Witulski, 1995), among them the 1:2 adduct, (3), and a 2:2 adduct, (4), isolated in 4% yield, the structure of which we were unable to derive from spectroscopic data alone. The compound was therefore subjected to X-ray structure determination, the results of which are presented here, confirming structure (4).

Although several mechanisms can be proposed to account for the formation of the triply-layered product, (4), the one involving the addition of excess (1) to the intermediate (3) is particularly attractive. Indeed, when (3) and (1) are heated in toluene at 433 K (ratio 1:2), compound (4), which is formally a head-to-tail dimer of 7-cyanodibenzobarrelene, was produced in 18% yield.

Compound (4) (Fig. 1) displays no imposed symmetry, but has approximate twofold symmetry. It crystallizes with one molecule of chloroform. Molecular dimensions may be regarded as normal, e.g. the four-membered ring displays slightly lengthened C—C bonds and a ring pucker of 11.9 (7)° (Allen, 1984). The exocyclic bonds C9—C11 and C9'—C11' are also significantly lengthened (Table 1).

The crystal packing involved three contacts that might be classified as C—H···X hydrogen bonds (X = N or Cl; Table 2). A more significant interaction, however, is between the chloroform H atom and the centroid (Cent) of ring C1a'–C4a', with an H···Cent distance of 2.65 Å (non-normalized) and a C—H···Cent angle of 160°.

Experimental top

The compound was prepared according to Witulski (1992) and recrystallized from chloroform/pentane.

Computing details top

Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecule of compound (4) in the crystal. Ellipsoids represent 30% probability levels and H-atom radii are arbitrary.

2,3-dicyanotetrabenzo-pentacyclo[8.2.2.2^4,7.0^2,9.0^3,8]hexadeca- 5,11,13,15-tetraene top

Crystal data top

C₃₄H₂₂N₂·CHCl₃	D_x = 1.358 Mg m⁻³
M_r = 577.90	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 50 reflections
a = 10.626 (4) Å	θ = 10–11°
b = 16.048 (5) Å	µ = 0.35 mm⁻¹
c = 16.580 (7) Å	T = 178 K
V = 2827.3 (18) Å³	Prism, colourless
Z = 4	0.7 × 0.4 × 0.2 mm
F(000) = 1192

Data collection top

Nicolet R3 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.1°
Graphite monochromator	h = −13→0
ω scans	k = −20→0
3618 measured reflections	l = −21→0
3618 independent reflections	3 standard reflections every 147 reflections
2199 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.074	H-atom parameters constrained
wR(F²) = 0.222	w = 1/[σ²(F_o²) + (0.087P)² + 5.5143P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3618 reflections	Δρ_max = 1.08 e Å⁻³
361 parameters	Δρ_min = −0.97 e Å⁻³
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.4 (2)

Crystal data top

C₃₄H₂₂N₂·CHCl₃	V = 2827.3 (18) Å³
M_r = 577.90	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.626 (4) Å	µ = 0.35 mm⁻¹
b = 16.048 (5) Å	T = 178 K
c = 16.580 (7) Å	0.7 × 0.4 × 0.2 mm

Data collection top

Nicolet R3 diffractometer	R_int = 0.000
3618 measured reflections	3 standard reflections every 147 reflections
3618 independent reflections	intensity decay: none
2199 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.074	H-atom parameters constrained
wR(F²) = 0.222	Δρ_max = 1.08 e Å⁻³
S = 1.03	Δρ_min = −0.97 e Å⁻³
3618 reflections	Absolute structure: Flack (1983)
361 parameters	Absolute structure parameter: 0.4 (2)
0 restraints

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.

Non-bonded distances:

2.2180 (0.0085) C11 - C12' 2.2052 (0.0084) C12 - C11'

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 7.0350 (0.0319) x − 4.9508 (0.0592) y + 11.3244 (0.0484) z = 1.1259 (0.0590)

* 0.0577 (0.0031) C11 * −0.0581 (0.0031) C12 * −0.0571 (0.0031) C11' * 0.0575 (0.0031) C12'

Rms deviation of fitted atoms = 0.0576

− 7.0350 (0.0319) x − 4.9508 (0.0592) y + 11.3244 (0.0484) z = 1.1259 (0.0590)

* 0.0577 (0.0031) C11 * −0.0581 (0.0031) C12 * −0.0571 (0.0031) C11' * 0.0575 (0.0031) C12'

Rms deviation of fitted atoms = 0.0576

7.0010 (0.0320) x + 6.4591 (0.0976) y − 10.5374 (0.0670) z = 0.0375 (0.0847)

Angle to previous plane (with approximate e.s.d.) = 6.04 (0.68)

* 0.0000 (0.0001) C11 * 0.0000 (0.0000) C12 * 0.0000 (0.0000) C12'

Rms deviation of fitted atoms = 0.0000

− 6.9920 (0.0323) x − 3.4276 (0.1013) y + 11.9722 (0.0563) z = 2.3628 (0.0887)

Angle to previous plane (with approximate e.s.d.) = 11.93 (0.69)

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	U_iso*/U_eq
C1	0.2559 (6)	0.4075 (4)	0.5363 (4)	0.0381 (15)
H1	0.2043	0.4558	0.5343	0.046*
C1A	0.3474 (6)	0.3986 (4)	0.5965 (4)	0.0330 (14)
C2	0.2421 (6)	0.3441 (4)	0.4793 (4)	0.0403 (16)
H2	0.1819	0.3502	0.4374	0.048*
C3	0.3147 (7)	0.2724 (4)	0.4829 (4)	0.0381 (15)
H3	0.3027	0.2291	0.4447	0.046*
C4	0.4050 (7)	0.2645 (4)	0.5429 (4)	0.0357 (15)
H4	0.4557	0.2158	0.5452	0.043*
C4A	0.4220 (6)	0.3271 (4)	0.5995 (4)	0.0338 (14)
C5	0.4595 (7)	0.3002 (4)	0.8146 (4)	0.0431 (17)
H5	0.5150	0.2540	0.8177	0.052*
C5A	0.4495 (6)	0.3467 (4)	0.7438 (4)	0.0370 (15)
C6	0.3866 (8)	0.3230 (5)	0.8805 (4)	0.0490 (19)
H6	0.3924	0.2917	0.9290	0.059*
C7	0.3049 (8)	0.3911 (5)	0.8768 (5)	0.053 (2)
H7	0.2538	0.4047	0.9220	0.064*
C8	0.2983 (7)	0.4388 (5)	0.8070 (4)	0.0451 (17)
H8	0.2437	0.4856	0.8042	0.054*
C8A	0.3725 (6)	0.4170 (4)	0.7416 (4)	0.0354 (14)
C9	0.3745 (6)	0.4625 (4)	0.6610 (4)	0.0360 (15)
H9	0.3151	0.5108	0.6594	0.043*
C10	0.5194 (6)	0.3310 (4)	0.6657 (4)	0.0317 (14)
H10	0.5712	0.2791	0.6682	0.038*
C11	0.5158 (6)	0.4881 (4)	0.6384 (4)	0.0310 (14)
C12	0.6008 (6)	0.4091 (4)	0.6464 (4)	0.0298 (13)
H12	0.6563	0.4007	0.5984	0.036*
C13	0.5063 (6)	0.5329 (4)	0.5598 (4)	0.0322 (14)
N	0.4878 (6)	0.5696 (4)	0.5024 (4)	0.0473 (16)
C1'	0.9221 (7)	0.5354 (4)	0.8344 (4)	0.0401 (16)
H1'	0.9620	0.4853	0.8511	0.048*
C1A'	0.8479 (6)	0.5361 (4)	0.7666 (4)	0.0358 (15)
C2'	0.9389 (8)	0.6080 (5)	0.8784 (5)	0.0498 (19)
H2'	0.9920	0.6073	0.9245	0.060*
C3'	0.8804 (7)	0.6810 (5)	0.8569 (5)	0.0472 (18)
H3'	0.8927	0.7303	0.8877	0.057*
C4'	0.8023 (7)	0.6818 (4)	0.7891 (4)	0.0409 (16)
H4'	0.7601	0.7316	0.7742	0.049*
C4A'	0.7862 (6)	0.6109 (4)	0.7438 (4)	0.0324 (14)
C5'	0.9220 (6)	0.4494 (5)	0.5717 (4)	0.0436 (17)
H5'	0.9668	0.4007	0.5868	0.052*
C5A'	0.8439 (6)	0.4895 (4)	0.6268 (4)	0.0351 (15)
C6'	0.9336 (7)	0.4816 (5)	0.4940 (4)	0.0488 (19)
H6'	0.9852	0.4538	0.4558	0.059*
C7'	0.8710 (7)	0.5536 (5)	0.4717 (5)	0.052 (2)
H7'	0.8810	0.5753	0.4188	0.063*
C8'	0.7925 (7)	0.5946 (5)	0.5272 (4)	0.0446 (17)
H8'	0.7487	0.6439	0.5123	0.053*
C8A'	0.7803 (6)	0.5620 (4)	0.6039 (4)	0.0342 (14)
C9'	0.7016 (6)	0.6003 (4)	0.6705 (3)	0.0307 (13)
H9'	0.6616	0.6539	0.6536	0.037*
C10'	0.8162 (6)	0.4633 (4)	0.7121 (4)	0.0321 (14)
H10'	0.8642	0.4121	0.7275	0.039*
C11'	0.6014 (6)	0.5342 (4)	0.7015 (4)	0.0298 (13)
C12'	0.6723 (6)	0.4497 (4)	0.7187 (4)	0.0294 (13)
H12'	0.6475	0.4246	0.7716	0.035*
C13'	0.5296 (6)	0.5743 (4)	0.7671 (4)	0.0323 (14)
N'	0.4742 (6)	0.6100 (3)	0.8149 (3)	0.0373 (13)
C99	1.0913 (8)	0.6952 (5)	0.6732 (5)	0.061 (2)
H99	1.0194	0.6636	0.6973	0.073*
Cl1	1.1543 (6)	0.6361 (3)	0.6002 (2)	0.202 (3)
Cl2	1.1987 (3)	0.7139 (2)	0.74848 (17)	0.1070 (11)
Cl3	1.0313 (3)	0.78576 (15)	0.6302 (2)	0.1018 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.028 (3)	0.037 (3)	0.049 (4)	0.001 (3)	−0.002 (3)	0.000 (3)
C1A	0.030 (3)	0.032 (3)	0.037 (3)	−0.006 (3)	0.003 (3)	−0.001 (3)
C2	0.033 (3)	0.044 (4)	0.043 (4)	−0.008 (3)	0.000 (3)	0.001 (3)
C3	0.040 (4)	0.041 (4)	0.033 (3)	−0.005 (3)	−0.002 (3)	−0.002 (3)
C4	0.038 (4)	0.033 (3)	0.036 (3)	−0.002 (3)	0.006 (3)	−0.001 (3)
C4A	0.031 (3)	0.034 (3)	0.036 (3)	0.001 (3)	0.001 (3)	0.000 (3)
C5	0.049 (4)	0.042 (4)	0.038 (4)	−0.016 (3)	−0.003 (3)	0.004 (3)
C5A	0.037 (3)	0.032 (3)	0.042 (4)	−0.013 (3)	−0.003 (3)	−0.001 (3)
C6	0.061 (5)	0.049 (4)	0.037 (4)	−0.023 (4)	0.000 (4)	0.005 (3)
C7	0.065 (5)	0.050 (4)	0.045 (4)	−0.006 (4)	0.013 (4)	−0.008 (4)
C8	0.043 (4)	0.048 (4)	0.044 (4)	−0.008 (4)	0.007 (3)	−0.010 (3)
C8A	0.027 (3)	0.041 (3)	0.038 (3)	−0.006 (3)	0.003 (3)	−0.002 (3)
C9	0.034 (3)	0.031 (3)	0.043 (4)	0.004 (3)	0.003 (3)	−0.002 (3)
C10	0.033 (3)	0.025 (3)	0.037 (3)	−0.006 (3)	0.000 (3)	0.004 (3)
C11	0.033 (3)	0.024 (3)	0.036 (3)	0.003 (3)	0.000 (3)	−0.002 (3)
C12	0.027 (3)	0.029 (3)	0.033 (3)	0.001 (3)	0.000 (3)	−0.003 (3)
C13	0.028 (3)	0.034 (3)	0.035 (3)	0.000 (3)	0.005 (3)	−0.003 (3)
N	0.053 (4)	0.049 (4)	0.039 (3)	0.003 (3)	−0.007 (3)	0.006 (3)
C1'	0.043 (4)	0.041 (4)	0.037 (3)	−0.005 (3)	−0.007 (3)	0.001 (3)
C1A'	0.033 (3)	0.036 (3)	0.038 (3)	−0.004 (3)	0.003 (3)	−0.003 (3)
C2'	0.055 (5)	0.048 (4)	0.046 (4)	−0.010 (4)	−0.016 (4)	−0.009 (4)
C3'	0.038 (4)	0.050 (4)	0.054 (4)	−0.009 (3)	0.000 (4)	−0.015 (4)
C4'	0.038 (4)	0.040 (4)	0.045 (4)	−0.002 (3)	0.006 (3)	−0.004 (3)
C4A'	0.026 (3)	0.035 (3)	0.036 (3)	−0.002 (3)	0.005 (3)	0.002 (3)
C5'	0.034 (4)	0.042 (4)	0.054 (4)	0.000 (3)	0.001 (3)	−0.011 (3)
C5A'	0.033 (3)	0.038 (3)	0.035 (3)	0.001 (3)	0.000 (3)	−0.006 (3)
C6'	0.046 (4)	0.057 (5)	0.044 (4)	−0.002 (4)	0.014 (4)	−0.015 (4)
C7'	0.051 (4)	0.069 (5)	0.037 (4)	−0.008 (4)	0.005 (4)	−0.004 (4)
C8'	0.045 (4)	0.039 (4)	0.049 (4)	−0.005 (4)	0.004 (4)	0.004 (3)
C8A'	0.033 (3)	0.035 (3)	0.035 (3)	−0.001 (3)	0.002 (3)	−0.002 (3)
C9'	0.037 (3)	0.024 (3)	0.032 (3)	0.000 (3)	0.003 (3)	0.000 (2)
C10'	0.031 (3)	0.031 (3)	0.035 (3)	0.005 (3)	0.000 (3)	−0.001 (3)
C11'	0.029 (3)	0.028 (3)	0.032 (3)	0.004 (3)	0.004 (3)	0.000 (3)
C12'	0.027 (3)	0.031 (3)	0.030 (3)	−0.003 (3)	0.001 (3)	−0.002 (3)
C13'	0.031 (3)	0.033 (3)	0.034 (3)	0.006 (3)	−0.002 (3)	−0.001 (3)
N'	0.038 (3)	0.037 (3)	0.037 (3)	0.002 (3)	0.005 (3)	−0.004 (3)
C99	0.050 (5)	0.050 (5)	0.083 (6)	−0.005 (4)	−0.017 (5)	0.005 (4)
Cl1	0.375 (8)	0.146 (3)	0.086 (2)	0.175 (5)	−0.076 (4)	−0.051 (2)
Cl2	0.113 (2)	0.136 (3)	0.0724 (17)	−0.009 (2)	−0.0339 (18)	−0.0082 (18)
Cl3	0.128 (3)	0.0539 (13)	0.124 (2)	0.0301 (16)	−0.017 (2)	0.0067 (15)

Geometric parameters (Å, º) top

C1—C2	1.397 (9)	C1'—C2'	1.386 (9)
C1—C1A	1.401 (9)	C1'—H1'	0.9500
C1—H1	0.9500	C1A'—C4A'	1.419 (9)
C1A—C4A	1.396 (9)	C1A'—C10'	1.515 (9)
C1A—C9	1.509 (9)	C2'—C3'	1.374 (10)
C2—C3	1.387 (10)	C2'—H2'	0.9500
C2—H2	0.9500	C3'—C4'	1.397 (10)
C3—C4	1.388 (9)	C3'—H3'	0.9500
C3—H3	0.9500	C4'—C4A'	1.373 (9)
C4—C4A	1.386 (9)	C4'—H4'	0.9500
C4—H4	0.9500	C4A'—C9'	1.522 (8)
C4A—C10	1.510 (9)	C5'—C5A'	1.392 (9)
C5—C6	1.388 (10)	C5'—C6'	1.393 (10)
C5—C5A	1.394 (9)	C5'—H5'	0.9500
C5—H5	0.9500	C5A'—C8A'	1.397 (9)
C5A—C8A	1.395 (9)	C5A'—C10'	1.506 (9)
C5A—C10	1.514 (9)	C6'—C7'	1.383 (11)
C6—C7	1.397 (11)	C6'—H6'	0.9500
C6—H6	0.9500	C7'—C8'	1.406 (10)
C7—C8	1.390 (10)	C7'—H7'	0.9500
C7—H7	0.9500	C8'—C8A'	1.381 (9)
C8—C8A	1.386 (9)	C8'—H8'	0.9500
C8—H8	0.9500	C8A'—C9'	1.516 (8)
C8A—C9	1.522 (9)	C9'—C11'	1.589 (9)
C9—C11	1.602 (9)	C9'—H9'	1.0000
C9—H9	1.0000	C10'—C12'	1.549 (9)
C10—C12	1.557 (8)	C10'—H10'	1.0000
C10—H10	1.0000	C11'—C13'	1.476 (9)
C11—C13	1.491 (9)	C11'—C12'	1.578 (8)
C11—C12	1.563 (8)	C12'—H12'	1.0000
C11—C11'	1.571 (9)	C13'—N'	1.141 (8)
C12—C12'	1.560 (8)	C99—Cl1	1.676 (9)
C12—H12	1.0000	C99—Cl2	1.717 (9)
C13—N	1.136 (8)	C99—Cl3	1.740 (8)
C1'—C1A'	1.373 (9)	C99—H99	1.0000

C2—C1—C1A	118.8 (6)	C1'—C1A'—C4A'	119.3 (6)
C2—C1—H1	120.6	C1'—C1A'—C10'	127.6 (6)
C1A—C1—H1	120.6	C4A'—C1A'—C10'	113.0 (5)
C4A—C1A—C1	120.2 (6)	C3'—C2'—C1'	121.4 (7)
C4A—C1A—C9	115.1 (6)	C3'—C2'—H2'	119.3
C1—C1A—C9	124.7 (6)	C1'—C2'—H2'	119.3
C3—C2—C1	121.1 (6)	C2'—C3'—C4'	119.0 (7)
C3—C2—H2	119.5	C2'—C3'—H3'	120.5
C1—C2—H2	119.5	C4'—C3'—H3'	120.5
C2—C3—C4	119.5 (6)	C4A'—C4'—C3'	120.4 (7)
C2—C3—H3	120.3	C4A'—C4'—H4'	119.8
C4—C3—H3	120.3	C3'—C4'—H4'	119.8
C4A—C4—C3	120.6 (6)	C4'—C4A'—C1A'	119.8 (6)
C4A—C4—H4	119.7	C4'—C4A'—C9'	127.0 (6)
C3—C4—H4	119.7	C1A'—C4A'—C9'	113.1 (5)
C4—C4A—C1A	119.9 (6)	C5A'—C5'—C6'	119.2 (7)
C4—C4A—C10	127.7 (6)	C5A'—C5'—H5'	120.4
C1A—C4A—C10	112.4 (6)	C6'—C5'—H5'	120.4
C6—C5—C5A	118.6 (7)	C5'—C5A'—C8A'	119.7 (6)
C6—C5—H5	120.7	C5'—C5A'—C10'	127.2 (6)
C5A—C5—H5	120.7	C8A'—C5A'—C10'	113.2 (6)
C5—C5A—C8A	120.0 (7)	C7'—C6'—C5'	121.0 (7)
C5—C5A—C10	126.4 (6)	C7'—C6'—H6'	119.5
C8A—C5A—C10	113.5 (6)	C5'—C6'—H6'	119.5
C5—C6—C7	121.2 (7)	C6'—C7'—C8'	120.1 (7)
C5—C6—H6	119.4	C6'—C7'—H7'	120.0
C7—C6—H6	119.4	C8'—C7'—H7'	120.0
C8—C7—C6	119.9 (7)	C8A'—C8'—C7'	118.7 (7)
C8—C7—H7	120.0	C8A'—C8'—H8'	120.6
C6—C7—H7	120.0	C7'—C8'—H8'	120.6
C8A—C8—C7	119.0 (7)	C8'—C8A'—C5A'	121.4 (6)
C8A—C8—H8	120.5	C8'—C8A'—C9'	124.6 (6)
C7—C8—H8	120.5	C5A'—C8A'—C9'	114.0 (5)
C8—C8A—C5A	121.1 (6)	C8A'—C9'—C4A'	107.5 (5)
C8—C8A—C9	125.1 (6)	C8A'—C9'—C11'	109.5 (5)
C5A—C8A—C9	113.8 (6)	C4A'—C9'—C11'	102.2 (5)
C1A—C9—C8A	107.1 (5)	C8A'—C9'—H9'	112.3
C1A—C9—C11	100.8 (5)	C4A'—C9'—H9'	112.3
C8A—C9—C11	110.0 (5)	C11'—C9'—H9'	112.3
C1A—C9—H9	112.7	C5A'—C10'—C1A'	107.6 (5)
C8A—C9—H9	112.7	C5A'—C10'—C12'	107.3 (5)
C11—C9—H9	112.7	C1A'—C10'—C12'	106.6 (5)
C4A—C10—C5A	107.0 (5)	C5A'—C10'—H10'	111.7
C4A—C10—C12	105.4 (5)	C1A'—C10'—H10'	111.7
C5A—C10—C12	108.4 (5)	C12'—C10'—H10'	111.7
C4A—C10—H10	111.9	C13'—C11'—C11	113.4 (5)
C5A—C10—H10	111.9	C13'—C11'—C12'	119.2 (5)
C12—C10—H10	111.9	C11—C11'—C12'	89.5 (4)
C13—C11—C12	120.3 (5)	C13'—C11'—C9'	107.1 (5)
C13—C11—C11'	113.3 (5)	C11—C11'—C9'	119.1 (5)
C12—C11—C11'	89.4 (4)	C12'—C11'—C9'	108.2 (5)
C13—C11—C9	105.4 (5)	C10'—C12'—C12	119.0 (5)
C12—C11—C9	108.3 (5)	C10'—C12'—C11'	109.7 (5)
C11'—C11—C9	120.5 (5)	C12—C12'—C11'	89.3 (4)
C10—C12—C12'	116.6 (5)	C10'—C12'—H12'	112.2
C10—C12—C11	110.4 (5)	C12—C12'—H12'	112.2
C12'—C12—C11	90.5 (4)	C11'—C12'—H12'	112.2
C10—C12—H12	112.5	N'—C13'—C11'	175.5 (7)
C12'—C12—H12	112.5	Cl1—C99—Cl2	111.0 (5)
C11—C12—H12	112.5	Cl1—C99—Cl3	108.8 (5)
N—C13—C11	173.3 (7)	Cl2—C99—Cl3	113.3 (5)
C1A'—C1'—C2'	119.9 (7)	Cl1—C99—H99	107.9
C1A'—C1'—H1'	120.1	Cl2—C99—H99	107.9
C2'—C1'—H1'	120.1	Cl3—C99—H99	107.9

C2—C1—C1A—C4A	−0.6 (9)	C1'—C1A'—C4A'—C4'	0.6 (10)
C2—C1—C1A—C9	178.9 (6)	C10'—C1A'—C4A'—C4'	177.9 (6)
C1A—C1—C2—C3	1.7 (10)	C1'—C1A'—C4A'—C9'	−176.6 (6)
C1—C2—C3—C4	−1.7 (10)	C10'—C1A'—C4A'—C9'	0.6 (8)
C2—C3—C4—C4A	0.8 (10)	C6'—C5'—C5A'—C8A'	−1.1 (10)
C3—C4—C4A—C1A	0.3 (10)	C6'—C5'—C5A'—C10'	178.2 (7)
C3—C4—C4A—C10	−176.6 (6)	C5A'—C5'—C6'—C7'	1.4 (11)
C1—C1A—C4A—C4	−0.3 (9)	C5'—C6'—C7'—C8'	−1.1 (11)
C9—C1A—C4A—C4	−179.9 (6)	C6'—C7'—C8'—C8A'	0.4 (11)
C1—C1A—C4A—C10	177.0 (6)	C7'—C8'—C8A'—C5A'	−0.1 (10)
C9—C1A—C4A—C10	−2.5 (8)	C7'—C8'—C8A'—C9'	178.6 (6)
C6—C5—C5A—C8A	3.3 (10)	C5'—C5A'—C8A'—C8'	0.5 (10)
C6—C5—C5A—C10	−179.1 (6)	C10'—C5A'—C8A'—C8'	−178.9 (6)
C5A—C5—C6—C7	−0.2 (11)	C5'—C5A'—C8A'—C9'	−178.4 (6)
C5—C6—C7—C8	−1.9 (11)	C10'—C5A'—C8A'—C9'	2.2 (8)
C6—C7—C8—C8A	0.8 (11)	C8'—C8A'—C9'—C4A'	−126.5 (7)
C7—C8—C8A—C5A	2.4 (10)	C5A'—C8A'—C9'—C4A'	52.3 (7)
C7—C8—C8A—C9	179.3 (7)	C8'—C8A'—C9'—C11'	123.2 (7)
C5—C5A—C8A—C8	−4.5 (10)	C5A'—C8A'—C9'—C11'	−58.0 (7)
C10—C5A—C8A—C8	177.7 (6)	C4'—C4A'—C9'—C8A'	129.5 (7)
C5—C5A—C8A—C9	178.3 (6)	C1A'—C4A'—C9'—C8A'	−53.5 (7)
C10—C5A—C8A—C9	0.4 (8)	C4'—C4A'—C9'—C11'	−115.2 (7)
C4A—C1A—C9—C8A	−51.2 (7)	C1A'—C4A'—C9'—C11'	61.8 (6)
C1—C1A—C9—C8A	129.2 (6)	C5'—C5A'—C10'—C1A'	124.8 (7)
C4A—C1A—C9—C11	63.8 (6)	C8A'—C5A'—C10'—C1A'	−55.9 (7)
C1—C1A—C9—C11	−115.7 (6)	C5'—C5A'—C10'—C12'	−120.8 (7)
C8—C8A—C9—C1A	−125.0 (7)	C8A'—C5A'—C10'—C12'	58.5 (7)
C5A—C8A—C9—C1A	52.1 (7)	C1'—C1A'—C10'—C5A'	−129.0 (7)
C8—C8A—C9—C11	126.3 (7)	C4A'—C1A'—C10'—C5A'	54.0 (7)
C5A—C8A—C9—C11	−56.6 (7)	C1'—C1A'—C10'—C12'	116.1 (7)
C4—C4A—C10—C5A	−127.1 (7)	C4A'—C1A'—C10'—C12'	−60.9 (7)
C1A—C4A—C10—C5A	55.8 (7)	C13—C11—C11'—C13'	106.7 (6)
C4—C4A—C10—C12	117.7 (7)	C12—C11—C11'—C13'	−130.3 (5)
C1A—C4A—C10—C12	−59.4 (6)	C9—C11—C11'—C13'	−19.3 (8)
C5—C5A—C10—C4A	127.5 (7)	C13—C11—C11'—C12'	−131.4 (5)
C8A—C5A—C10—C4A	−54.9 (7)	C12—C11—C11'—C12'	−8.4 (4)
C5—C5A—C10—C12	−119.3 (7)	C9—C11—C11'—C12'	102.6 (5)
C8A—C5A—C10—C12	58.3 (7)	C13—C11—C11'—C9'	−20.7 (7)
C1A—C9—C11—C13	68.0 (6)	C12—C11—C11'—C9'	102.3 (5)
C8A—C9—C11—C13	−179.2 (5)	C9—C11—C11'—C9'	−146.7 (5)
C1A—C9—C11—C12	−62.0 (6)	C8A'—C9'—C11'—C13'	178.8 (5)
C8A—C9—C11—C12	50.9 (7)	C4A'—C9'—C11'—C13'	65.0 (6)
C1A—C9—C11—C11'	−162.4 (5)	C8A'—C9'—C11'—C11	−50.9 (7)
C8A—C9—C11—C11'	−49.6 (7)	C4A'—C9'—C11'—C11	−164.7 (5)
C4A—C10—C12—C12'	156.5 (5)	C8A'—C9'—C11'—C12'	49.1 (6)
C5A—C10—C12—C12'	42.2 (7)	C4A'—C9'—C11'—C12'	−64.7 (6)
C4A—C10—C12—C11	55.1 (6)	C5A'—C10'—C12'—C12	38.3 (7)
C5A—C10—C12—C11	−59.2 (6)	C1A'—C10'—C12'—C12	153.3 (5)
C13—C11—C12—C10	−115.9 (6)	C5A'—C10'—C12'—C11'	−62.3 (6)
C11'—C11—C12—C10	127.2 (5)	C1A'—C10'—C12'—C11'	52.8 (6)
C9—C11—C12—C10	5.2 (7)	C10—C12—C12'—C10'	126.1 (6)
C13—C11—C12—C12'	125.3 (6)	C11—C12—C12'—C10'	−120.7 (6)
C11'—C11—C12—C12'	8.5 (5)	C10—C12—C12'—C11'	−121.7 (5)
C9—C11—C12—C12'	−113.6 (5)	C11—C12—C12'—C11'	−8.4 (5)
C2'—C1'—C1A'—C4A'	−1.7 (10)	C13'—C11'—C12'—C10'	−114.1 (6)
C2'—C1'—C1A'—C10'	−178.6 (7)	C11—C11'—C12'—C10'	129.1 (5)
C1A'—C1'—C2'—C3'	1.4 (12)	C9'—C11'—C12'—C10'	8.5 (7)
C1'—C2'—C3'—C4'	0.0 (12)	C13'—C11'—C12'—C12	125.2 (6)
C2'—C3'—C4'—C4A'	−1.2 (11)	C11—C11'—C12'—C12	8.4 (4)
C3'—C4'—C4A'—C1A'	0.9 (10)	C9'—C11'—C12'—C12	−112.2 (5)
C3'—C4'—C4A'—C9'	177.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N′ⁱ	0.95	2.70	3.641 (9)	172
C6′—H6′···N′ⁱⁱ	0.95	2.59	3.455 (9)	152
C9—H9···Cl1ⁱⁱⁱ	1.00	2.82	3.776 (7)	161

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

Experimental details

Crystal data
Chemical formula	C₃₄H₂₂N₂·CHCl₃
M_r	577.90
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	178
a, b, c (Å)	10.626 (4), 16.048 (5), 16.580 (7)
V (Å³)	2827.3 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.7 × 0.4 × 0.2

Data collection
Diffractometer	Nicolet R3 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3618, 3618, 2199
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.222, 1.03
No. of reflections	3618
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.97
Absolute structure	Flack (1983)
Absolute structure parameter	0.4 (2)

Computer programs: P3 (Nicolet, 1987), P3, XDISK (Nicolet, 1987), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) top

C9—C11	1.602 (9)	C12—C12'	1.560 (8)
C11—C12	1.563 (8)	C9'—C11'	1.589 (9)
C11—C11'	1.571 (9)	C11'—C12'	1.578 (8)

C12—C11—C11'	89.4 (4)	C11—C11'—C12'	89.5 (4)
C12'—C12—C11	90.5 (4)	C12—C12'—C11'	89.3 (4)

C11'—C11—C12—C12'	8.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N'ⁱ	0.95	2.70	3.641 (9)	172
C6'—H6'···N'ⁱⁱ	0.95	2.59	3.455 (9)	152
C9—H9···Cl1ⁱⁱⁱ	1.00	2.82	3.776 (7)	161

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

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