14-(2,3-Dichloro­phen­yl)-9,10-dimethyl­benzimidazo[1,2-a]benzo[f][1,8]naphthyridine-6-carbonitrile

Tarasov, A.V.; Volovnenko, T.A.; Zubatyuk, R.I.; Shishkin, O.V.; Volovenko, Y.M.

doi:10.1107/S1600536809008447

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o792

doi:10.1107/S1600536809008447

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14-(2,3-Dichlorophenyl)-9,10-dimethylbenzimidazo[1,2-a]benzo[f][1,8]naphthyridine-6-carbonitrile

Andrii V. Tarasov,^a ^* Tatyana A. Volovnenko,^a Roman I. Zubatyuk,^b Oleg V. Shishkin ^b and Yulian M. Volovenko ^a

^aNational Taras Shevchenko University, Department of Chemistry, 64 Volodymyrska Str., Kyiv 01601, Ukraine, and ^bSTC "Institute for Single Crystals", National Academy of Science of Ukraine, 60 Lenina Ave., Kharkiv 61001, Ukraine
^*Correspondence e-mail: antaran@gala.net

(Received 3 March 2009; accepted 7 March 2009; online 19 March 2009)

In the title compound, C₂₇H₁₆Cl₂N₄, the benzimidazo[1,2-a]benzo[f][1,8]naphthyridine system is nearly planar (r.m.s. deviation for all non-H atoms = 0.033 Å). The dichlorophenyl substituent is rotated by −67.5 (2)° from this plane. In the crystal structure, molecules form stacks along the crystallographic (100) direction due to π–π stacking interactions with a centroid–centroid distance of 3.4283 (9) Å.

Related literature

For the synthesis of the title compound and a series of similar compounds, see: Volovnenko et al. (2006 ). For 1,2-fused benzimidazo heterocycles and their fluorescence properties, see: Gokhale & Seshadri (1987 ); Rajagopal & Seshadri (1991 ). For the biological properties of isoquinoline derivatives, see: Shamma (1972 ); Kametami & Fukomoto (1981 ); Bijan & Basu (1965 ); Neumeyer & Weinhard (1970 ).

Experimental

Crystal data

C₂₇H₁₆Cl₂N₄
M_r = 467.34
Triclinic, $[P \overline 1]$
a = 8.5588 (8) Å
b = 11.0751 (13) Å
c = 12.2332 (11) Å
α = 76.985 (9)°
β = 75.986 (8)°
γ = 85.438 (9)°
V = 1095.77 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.6 × 0.1 × 0.1 mm

Data collection

Oxford-Diffraction Xcalibur-3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.82, T_max = 0.97
20237 measured reflections
4290 independent reflections
2405 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.072
S = 1.01
4290 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008447/sj2589sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008447/sj2589Isup2.hkl

checkCIF report

Comment top

In the past few decades 1,2-fused benzimidazo heterocycles have attracted attention because of their fluorescent properties (Gokhale & Seshadri, 1987; Rajagopal & Seshadri 1991). On the other hand isoquinoline derivatives exhibit a wide range of biological effects and are of great interest to synthetic as well as pharmaceutical organic chemists (Shamma, 1972; Kametami & Fukomoto, 1981; Bijan & Basu, 1965; Neumeyer & Weinhard, 1970).

In a previous paper (Volovnenko et al., 2006) we have described the synthesis of a series of 14-arylbenzimidazo[1,2-a]benzo[f]-1,8-naphthyridine-6-carbonitriles. We report herein the crystal structure of the title compound, which is the derivative of the new heterocyclic system, benzimidazo[1,2-a]benzo[f]-1,8-naphthyridine.

The molecular structure of the title compound is illustrated in Fig. 1. The benzimidazo[1,2-a]benzo[f]-1,8-naphthyridine system is nearly planar (RMS deviation of the non-hydrogen atoms from mean plane is 0.033 Å). Benzene ring is rotated with respect to this plane (the C5—C6—C7—C23 torsion angle is -67.5 (2)°). This rotation results in the loss of conjugation between π systems of the heterocycle and benzene ring. In crystal molecules form stacked chains along the a axis (Fig. 2) due to stacking interactions between the π systems of the pentacyclic fragments. The distance between the parallel planes is 3.4186 (8) Å.

Related literature top

For the synthesis of the title compound and a series of similar compounds, see: Volovnenko et al. (2006). For 1,2-fused benzimidazo heterocycles and their fluorescence properties, see: Gokhale & Seshadri (1987); Rajagopal & Seshadri (1991). For the biological properties of isoquinoline derivatives, see: Shamma (1972); Kametami & Fukomoto (1981); Bijan & Basu (1965); Neumeyer & Weinhard (1970).

Experimental top

The title compound was synthesized by the reaction of 3-chloro-1-(2,3-dichlorophenyl)isoquinoline-4-carbaldehyde (1 mmol) with (5,6-dimethyl-1H-benzimidazol-2-yl)acetonitrile (1 mmol) in dimethylformamide (3–4 ml). After refluxing for 3 h, the reaction mixture was left to stand for overnight. The resulting crude solid was filtered, washed twice with acetone (10 ml) and dried. Yield: 65%. Crystals suitable for X-ray analysis were obtained by slow crystallization from hot dimethylformamide.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Crystal packing of the title compound showing stacks along the a axis. Hydrogen atoms are not shown.

14-(2,3-Dichlorophenyl)-9,10-dimethylbenzimidazo[1,2- a]benzo[f][1,8]naphthyridine-6-carbonitrile top

Crystal data top

C₂₇H₁₆Cl₂N₄	Z = 2
M_r = 467.34	F(000) = 480
Triclinic, P1	D_x = 1.416 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.5588 (8) Å	Cell parameters from 6294 reflections
b = 11.0751 (13) Å	θ = 2.7–28.6°
c = 12.2332 (11) Å	µ = 0.32 mm⁻¹
α = 76.985 (9)°	T = 293 K
β = 75.986 (8)°	Prism, pale orange
γ = 85.438 (9)°	0.6 × 0.1 × 0.1 mm
V = 1095.77 (19) Å³

Data collection top

Oxford-Diffraction Xcalibur-3 diffractometer	4290 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1827 pixels mm^-1	θ_max = 26.0°, θ_min = 2.7°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −13→13
T_min = 0.82, T_max = 0.97	l = −15→15
20237 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.03P)²] where P = (F_o² + 2F_c²)/3
4290 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₇H₁₆Cl₂N₄	γ = 85.438 (9)°
M_r = 467.34	V = 1095.77 (19) Å³
Triclinic, P1	Z = 2
a = 8.5588 (8) Å	Mo Kα radiation
b = 11.0751 (13) Å	µ = 0.32 mm⁻¹
c = 12.2332 (11) Å	T = 293 K
α = 76.985 (9)°	0.6 × 0.1 × 0.1 mm
β = 75.986 (8)°

Data collection top

Oxford-Diffraction Xcalibur-3 diffractometer	4290 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2405 reflections with I > 2σ(I)
T_min = 0.82, T_max = 0.97	R_int = 0.034
20237 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
4290 reflections	Δρ_min = −0.24 e Å⁻³
300 parameters

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	U_iso*/U_eq
Cl1	0.53369 (8)	0.08996 (5)	0.11087 (4)	0.07512 (19)
Cl2	0.55737 (9)	0.26410 (6)	−0.13175 (4)	0.0980 (2)
N1	0.24410 (16)	0.07841 (12)	0.33502 (10)	0.0416 (4)
N2	0.15186 (16)	−0.10485 (12)	0.46081 (10)	0.0380 (3)
N3	0.05348 (17)	−0.29056 (13)	0.56580 (11)	0.0445 (4)
N4	0.1445 (2)	−0.31290 (16)	0.85388 (14)	0.0799 (6)
C1	0.4249 (2)	0.22794 (16)	0.09828 (14)	0.0478 (5)
C2	0.4347 (2)	0.30496 (19)	−0.01113 (14)	0.0553 (5)
C3	0.3485 (2)	0.41496 (19)	−0.02191 (16)	0.0599 (6)
H3A	0.3550	0.4660	−0.0944	0.072*
C4	0.2526 (2)	0.45022 (18)	0.07372 (17)	0.0637 (6)
H4A	0.1933	0.5244	0.0653	0.076*
C5	0.2435 (2)	0.37670 (17)	0.18209 (15)	0.0575 (5)
H5A	0.1802	0.4023	0.2465	0.069*
C6	0.3291 (2)	0.26398 (16)	0.19503 (13)	0.0439 (4)
C7	0.3168 (2)	0.18469 (15)	0.31350 (13)	0.0411 (4)
C8	0.22786 (19)	0.00654 (15)	0.44182 (13)	0.0373 (4)
C9	0.1249 (2)	−0.19032 (15)	0.56664 (13)	0.0388 (4)
C10	0.0316 (2)	−0.27288 (15)	0.45439 (13)	0.0402 (4)
C11	0.0918 (2)	−0.15919 (15)	0.38690 (13)	0.0388 (4)
C12	0.0814 (2)	−0.12061 (16)	0.27243 (14)	0.0469 (5)
H12A	0.1221	−0.0450	0.2283	0.056*
C13	0.0089 (2)	−0.19800 (17)	0.22635 (14)	0.0506 (5)
C14	−0.0526 (2)	−0.31292 (16)	0.29292 (15)	0.0471 (5)
C15	−0.0407 (2)	−0.34975 (16)	0.40614 (14)	0.0457 (4)
H15A	−0.0808	−0.4256	0.4501	0.055*
C16	−0.1334 (2)	−0.39560 (17)	0.24225 (15)	0.0624 (6)
H16A	−0.1458	−0.4763	0.2922	0.094*
H16B	−0.0686	−0.4025	0.1679	0.094*
H16C	−0.2374	−0.3607	0.2343	0.094*
C17	−0.0053 (3)	−0.1566 (2)	0.10197 (16)	0.0844 (7)
H17A	0.0436	−0.0775	0.0691	0.127*
H17B	−0.1170	−0.1497	0.0995	0.127*
H17C	0.0485	−0.2164	0.0588	0.127*
C18	0.1780 (2)	−0.15844 (16)	0.65802 (13)	0.0421 (4)
C19	0.1568 (2)	−0.24516 (17)	0.76740 (15)	0.0527 (5)
C20	0.2535 (2)	−0.05020 (16)	0.64046 (13)	0.0431 (4)
H20A	0.2882	−0.0312	0.7009	0.052*
C21	0.28103 (19)	0.03485 (15)	0.53223 (13)	0.0375 (4)
C22	0.36455 (19)	0.14875 (15)	0.50764 (13)	0.0392 (4)
C23	0.3824 (2)	0.22500 (15)	0.39544 (13)	0.0396 (4)
C24	0.4691 (2)	0.33565 (16)	0.36838 (15)	0.0491 (5)
H24A	0.4811	0.3866	0.2954	0.059*
C25	0.5350 (2)	0.36845 (17)	0.44770 (15)	0.0534 (5)
H25A	0.5927	0.4409	0.4284	0.064*
C26	0.5162 (2)	0.29336 (17)	0.55808 (16)	0.0530 (5)
H26A	0.5612	0.3166	0.6120	0.064*
C27	0.4328 (2)	0.18652 (16)	0.58793 (14)	0.0462 (5)
H27A	0.4208	0.1381	0.6620	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1038 (5)	0.0659 (4)	0.0530 (3)	0.0237 (3)	−0.0178 (3)	−0.0166 (3)
Cl2	0.1300 (6)	0.1142 (5)	0.0412 (3)	0.0138 (5)	−0.0102 (3)	−0.0149 (3)
N1	0.0466 (9)	0.0348 (8)	0.0384 (8)	−0.0005 (7)	−0.0089 (7)	0.0011 (7)
N2	0.0416 (9)	0.0340 (8)	0.0337 (8)	0.0004 (7)	−0.0077 (6)	0.0009 (6)
N3	0.0464 (9)	0.0416 (9)	0.0402 (9)	−0.0028 (8)	−0.0085 (7)	0.0013 (7)
N4	0.1199 (17)	0.0661 (12)	0.0471 (10)	−0.0184 (12)	−0.0227 (10)	0.0103 (9)
C1	0.0549 (13)	0.0468 (11)	0.0441 (11)	−0.0044 (10)	−0.0180 (9)	−0.0066 (9)
C2	0.0628 (14)	0.0632 (13)	0.0401 (11)	−0.0086 (11)	−0.0163 (10)	−0.0043 (10)
C3	0.0633 (15)	0.0666 (15)	0.0446 (12)	−0.0157 (12)	−0.0172 (11)	0.0085 (10)
C4	0.0627 (15)	0.0506 (12)	0.0649 (14)	0.0010 (11)	−0.0148 (11)	0.0131 (10)
C5	0.0586 (14)	0.0491 (12)	0.0512 (12)	0.0007 (10)	−0.0083 (10)	0.0114 (10)
C6	0.0466 (12)	0.0427 (11)	0.0392 (10)	−0.0091 (9)	−0.0111 (9)	0.0019 (8)
C7	0.0421 (11)	0.0370 (10)	0.0383 (10)	0.0007 (9)	−0.0047 (8)	−0.0015 (8)
C8	0.0360 (10)	0.0325 (10)	0.0373 (10)	0.0022 (8)	−0.0036 (8)	−0.0011 (8)
C9	0.0392 (11)	0.0362 (10)	0.0341 (10)	0.0024 (9)	−0.0040 (8)	0.0012 (8)
C10	0.0399 (11)	0.0368 (10)	0.0381 (10)	0.0028 (9)	−0.0071 (8)	0.0004 (8)
C11	0.0380 (11)	0.0387 (10)	0.0375 (10)	0.0033 (8)	−0.0085 (8)	−0.0054 (8)
C12	0.0576 (13)	0.0360 (10)	0.0430 (11)	−0.0020 (9)	−0.0112 (9)	−0.0003 (9)
C13	0.0597 (13)	0.0474 (12)	0.0431 (11)	0.0017 (10)	−0.0130 (10)	−0.0062 (9)
C14	0.0433 (11)	0.0476 (11)	0.0505 (11)	0.0035 (9)	−0.0107 (9)	−0.0125 (9)
C15	0.0464 (12)	0.0358 (10)	0.0512 (11)	−0.0033 (9)	−0.0095 (9)	−0.0027 (9)
C16	0.0685 (15)	0.0579 (13)	0.0648 (13)	−0.0059 (11)	−0.0189 (11)	−0.0160 (10)
C17	0.133 (2)	0.0714 (15)	0.0532 (13)	−0.0218 (15)	−0.0388 (14)	0.0033 (11)
C18	0.0460 (12)	0.0394 (11)	0.0356 (10)	0.0031 (9)	−0.0074 (8)	−0.0010 (8)
C19	0.0657 (14)	0.0483 (12)	0.0418 (11)	−0.0077 (10)	−0.0122 (10)	−0.0025 (10)
C20	0.0480 (12)	0.0437 (11)	0.0365 (10)	0.0034 (9)	−0.0109 (8)	−0.0064 (8)
C21	0.0366 (11)	0.0365 (10)	0.0357 (9)	0.0051 (8)	−0.0062 (8)	−0.0041 (8)
C22	0.0352 (11)	0.0384 (10)	0.0408 (10)	0.0061 (9)	−0.0049 (8)	−0.0083 (8)
C23	0.0396 (11)	0.0338 (10)	0.0401 (10)	0.0024 (8)	−0.0035 (8)	−0.0043 (8)
C24	0.0539 (13)	0.0398 (11)	0.0470 (11)	−0.0029 (10)	−0.0032 (9)	−0.0041 (9)
C25	0.0542 (13)	0.0448 (11)	0.0598 (13)	−0.0071 (10)	−0.0039 (10)	−0.0161 (10)
C26	0.0537 (13)	0.0525 (12)	0.0561 (12)	0.0000 (10)	−0.0118 (10)	−0.0195 (10)
C27	0.0501 (12)	0.0441 (11)	0.0436 (10)	0.0043 (10)	−0.0108 (9)	−0.0094 (9)

Geometric parameters (Å, º) top

Cl1—C1	1.7214 (18)	C12—H12A	0.9300
Cl2—C2	1.7201 (19)	C13—C14	1.411 (2)
N1—C7	1.319 (2)	C13—C17	1.519 (2)
N1—C8	1.3495 (19)	C14—C15	1.379 (2)
N2—C8	1.3873 (19)	C14—C16	1.505 (2)
N2—C11	1.4009 (19)	C15—H15A	0.9300
N2—C9	1.4013 (19)	C16—H16A	0.9600
N3—C9	1.3123 (19)	C16—H16B	0.9600
N3—C10	1.3886 (19)	C16—H16C	0.9600
N4—C19	1.138 (2)	C17—H17A	0.9600
C1—C6	1.387 (2)	C17—H17B	0.9600
C1—C2	1.403 (2)	C17—H17C	0.9600
C2—C3	1.370 (3)	C18—C20	1.357 (2)
C3—C4	1.373 (2)	C18—C19	1.441 (2)
C3—H3A	0.9300	C20—C21	1.421 (2)
C4—C5	1.378 (2)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.436 (2)
C5—C6	1.393 (2)	C22—C27	1.408 (2)
C5—H5A	0.9300	C22—C23	1.420 (2)
C6—C7	1.500 (2)	C23—C24	1.416 (2)
C7—C23	1.426 (2)	C24—C25	1.360 (2)
C8—C21	1.397 (2)	C24—H24A	0.9300
C9—C18	1.425 (2)	C25—C26	1.397 (2)
C10—C15	1.394 (2)	C25—H25A	0.9300
C10—C11	1.401 (2)	C26—C27	1.363 (2)
C11—C12	1.392 (2)	C26—H26A	0.9300
C12—C13	1.382 (2)	C27—H27A	0.9300

C7—N1—C8	117.45 (14)	C15—C14—C16	119.31 (16)
C8—N2—C11	131.25 (13)	C13—C14—C16	120.72 (16)
C8—N2—C9	123.19 (13)	C14—C15—C10	119.72 (16)
C11—N2—C9	105.54 (13)	C14—C15—H15A	120.1
C9—N3—C10	104.64 (13)	C10—C15—H15A	120.1
C6—C1—C2	119.87 (16)	C14—C16—H16A	109.5
C6—C1—Cl1	120.71 (13)	C14—C16—H16B	109.5
C2—C1—Cl1	119.42 (14)	H16A—C16—H16B	109.5
C3—C2—C1	119.80 (17)	C14—C16—H16C	109.5
C3—C2—Cl2	119.59 (15)	H16A—C16—H16C	109.5
C1—C2—Cl2	120.60 (15)	H16B—C16—H16C	109.5
C2—C3—C4	120.37 (17)	C13—C17—H17A	109.5
C2—C3—H3A	119.8	C13—C17—H17B	109.5
C4—C3—H3A	119.8	H17A—C17—H17B	109.5
C3—C4—C5	120.64 (18)	C13—C17—H17C	109.5
C3—C4—H4A	119.7	H17A—C17—H17C	109.5
C5—C4—H4A	119.7	H17B—C17—H17C	109.5
C4—C5—C6	119.98 (18)	C20—C18—C9	120.27 (14)
C4—C5—H5A	120.0	C20—C18—C19	120.64 (15)
C6—C5—H5A	120.0	C9—C18—C19	119.04 (15)
C1—C6—C5	119.33 (15)	N4—C19—C18	178.0 (2)
C1—C6—C7	121.37 (15)	C18—C20—C21	121.74 (15)
C5—C6—C7	119.29 (15)	C18—C20—H20A	119.1
N1—C7—C23	123.58 (14)	C21—C20—H20A	119.1
N1—C7—C6	116.15 (14)	C8—C21—C20	119.06 (15)
C23—C7—C6	120.27 (15)	C8—C21—C22	116.76 (14)
N1—C8—N2	115.72 (14)	C20—C21—C22	124.16 (14)
N1—C8—C21	125.72 (15)	C27—C22—C23	118.74 (16)
N2—C8—C21	118.56 (13)	C27—C22—C21	123.32 (15)
N3—C9—N2	113.47 (14)	C23—C22—C21	117.92 (14)
N3—C9—C18	129.35 (14)	C24—C23—C22	118.74 (15)
N2—C9—C18	117.18 (15)	C24—C23—C7	122.71 (15)
N3—C10—C15	129.18 (15)	C22—C23—C7	118.51 (16)
N3—C10—C11	111.38 (15)	C25—C24—C23	120.91 (16)
C15—C10—C11	119.44 (15)	C25—C24—H24A	119.5
C12—C11—C10	121.67 (16)	C23—C24—H24A	119.5
C12—C11—N2	133.34 (16)	C24—C25—C26	120.03 (17)
C10—C11—N2	104.97 (13)	C24—C25—H25A	120.0
C13—C12—C11	117.98 (16)	C26—C25—H25A	120.0
C13—C12—H12A	121.0	C27—C26—C25	120.95 (17)
C11—C12—H12A	121.0	C27—C26—H26A	119.5
C12—C13—C14	121.22 (15)	C25—C26—H26A	119.5
C12—C13—C17	118.67 (17)	C26—C27—C22	120.63 (16)
C14—C13—C17	120.11 (17)	C26—C27—H27A	119.7
C15—C14—C13	119.97 (17)	C22—C27—H27A	119.7

C6—C1—C2—C3	−0.6 (3)	N2—C11—C12—C13	−178.08 (17)
Cl1—C1—C2—C3	180.00 (14)	C11—C12—C13—C14	−0.2 (3)
C6—C1—C2—Cl2	178.11 (14)	C11—C12—C13—C17	179.24 (17)
Cl1—C1—C2—Cl2	−1.3 (2)	C12—C13—C14—C15	0.0 (3)
C1—C2—C3—C4	0.1 (3)	C17—C13—C14—C15	−179.43 (18)
Cl2—C2—C3—C4	−178.65 (15)	C12—C13—C14—C16	179.13 (16)
C2—C3—C4—C5	1.0 (3)	C17—C13—C14—C16	−0.3 (3)
C3—C4—C5—C6	−1.5 (3)	C13—C14—C15—C10	0.2 (3)
C2—C1—C6—C5	0.1 (3)	C16—C14—C15—C10	−178.96 (15)
Cl1—C1—C6—C5	179.47 (14)	N3—C10—C15—C14	178.80 (16)
C2—C1—C6—C7	−179.36 (16)	C11—C10—C15—C14	−0.2 (2)
Cl1—C1—C6—C7	0.0 (2)	N3—C9—C18—C20	178.47 (16)
C4—C5—C6—C1	1.0 (3)	N2—C9—C18—C20	−1.0 (2)
C4—C5—C6—C7	−179.58 (17)	N3—C9—C18—C19	1.2 (3)
C8—N1—C7—C23	1.9 (2)	N2—C9—C18—C19	−178.29 (15)
C8—N1—C7—C6	−178.42 (14)	C9—C18—C20—C21	0.5 (2)
C1—C6—C7—N1	−67.7 (2)	C19—C18—C20—C21	177.75 (15)
C5—C6—C7—N1	112.84 (18)	N1—C8—C21—C20	179.41 (15)
C1—C6—C7—C23	111.97 (19)	N2—C8—C21—C20	−0.9 (2)
C5—C6—C7—C23	−67.5 (2)	N1—C8—C21—C22	−2.0 (2)
C7—N1—C8—N2	−179.53 (14)	N2—C8—C21—C22	177.66 (13)
C7—N1—C8—C21	0.2 (2)	C18—C20—C21—C8	0.4 (2)
C11—N2—C8—N1	2.2 (2)	C18—C20—C21—C22	−177.98 (15)
C9—N2—C8—N1	−179.90 (14)	C8—C21—C22—C27	−176.46 (15)
C11—N2—C8—C21	−177.54 (15)	C20—C21—C22—C27	2.0 (2)
C9—N2—C8—C21	0.4 (2)	C8—C21—C22—C23	1.8 (2)
C10—N3—C9—N2	0.31 (18)	C20—C21—C22—C23	−179.73 (15)
C10—N3—C9—C18	−179.18 (16)	C27—C22—C23—C24	0.4 (2)
C8—N2—C9—N3	−178.98 (14)	C21—C22—C23—C24	−177.92 (14)
C11—N2—C9—N3	−0.62 (18)	C27—C22—C23—C7	178.34 (15)
C8—N2—C9—C18	0.6 (2)	C21—C22—C23—C7	0.0 (2)
C11—N2—C9—C18	178.94 (14)	N1—C7—C23—C24	175.85 (15)
C9—N3—C10—C15	−178.96 (17)	C6—C7—C23—C24	−3.8 (2)
C9—N3—C10—C11	0.12 (18)	N1—C7—C23—C22	−2.0 (2)
N3—C10—C11—C12	−179.17 (15)	C6—C7—C23—C22	178.35 (15)
C15—C10—C11—C12	0.0 (2)	C22—C23—C24—C25	0.4 (2)
N3—C10—C11—N2	−0.49 (17)	C7—C23—C24—C25	−177.44 (16)
C15—C10—C11—N2	178.69 (14)	C23—C24—C25—C26	−0.7 (3)
C8—N2—C11—C12	−2.7 (3)	C24—C25—C26—C27	0.3 (3)
C9—N2—C11—C12	179.09 (18)	C25—C26—C27—C22	0.5 (3)
C8—N2—C11—C10	178.81 (15)	C23—C22—C27—C26	−0.9 (2)
C9—N2—C11—C10	0.63 (16)	C21—C22—C27—C26	177.38 (15)
C10—C11—C12—C13	0.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₇H₁₆Cl₂N₄
M_r	467.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5588 (8), 11.0751 (13), 12.2332 (11)
α, β, γ (°)	76.985 (9), 75.986 (8), 85.438 (9)
V (Å³)	1095.77 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.6 × 0.1 × 0.1

Data collection
Diffractometer	Oxford-Diffraction Xcalibur-3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.82, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	20237, 4290, 2405
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.072, 1.01
No. of reflections	4290
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2009).

References

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