Dichlorido[(R,R)-N,N,N-tribenzyl-cyclo-hexane-1,2-diamine-κN,N]copper(II).

In the title compound, [CuCl(2)(C(27)H(32)N(2))], which bears a chiral diamine ligand, viz (R,R)-N,N,N''- tribenzyl-cyclo-hexane-1,2-diamine, the Cu(II) ion is ligated by two N and two Cl atoms in a distorted square-planar geometry. The coordination of the ligands to the Cu(II) ion results in the formation of a five-membered heterocyclic ring and a chiral center at the monosubstituted nitro-gen in an (S)-configuration. The catalytic capacity of the complex for the asymmetric nitro-aldol reaction is promising (49% ee).

Related literature

For the synthesis of N,N,N′′-tribenzyl-(R,R)-1,2-diamino­cyclo­hexane, see: Tye et al. (2002 ▶); Boyd et al. (2005 ▶). For related structures, see: Alexakis et al. (2001 ▶); Tye et al. (2002 ▶); Boyd et al. (2005 ▶, 2006 ▶); Arjan et al. (2005 ▶); Brethon et al. (2004 ▶); Jones & Mahon (2008 ▶); Evans & Seidel (2005 ▶); Evans et al. (2007 ▶); Roh et al. (2004 ▶); Nguyen & Jeong (2008a ▶,b ▶).

Experimental

Crystal data

[CuCl2(C27H32N2)]

M = 519.00

Orthorhombic,

a = 10.5806 (7) Å

b = 15.4409 (8) Å

c = 16.2579 (12) Å

V = 2656.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.04 mm−1

T = 295 K

0.40 × 0.40 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: analytical (ABSCALC; McArdle & Daly, 1999 ▶) T min = 0.660, T max = 0.666

5793 measured reflections

4931 independent reflections

3885 reflections with I > 2σ(I)

R int = 0.019

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.06

4931 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: −0.017 (13)

Data collection: CAD4 (Enraf–Nonius, 1989 ▶); cell refinement: CAD4; data reduction: XCAD (McArdle, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014054/rk2198sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014054/rk2198Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuCl2(C27H32N2)]	F(000) = 1084
Mr = 519.00	Dx = 1.298 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.5806 (7) Å	θ = 10–13°
b = 15.4409 (8) Å	µ = 1.04 mm−1
c = 16.2579 (12) Å	T = 295 K
V = 2656.1 (3) Å3	Block, blue
Z = 4	0.40 × 0.40 × 0.40 mm

Enraf–Nonius CAD-4 diffractometer	3885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 25.5°, θmin = 1.8°
ω/2θ scans	h = −12→12
Absorption correction: analytical (ABSCALC; McArdle & Daly, 1999)	k = −18→18
Tmin = 0.660, Tmax = 0.666	l = −19→19
5793 measured reflections	3 standard reflections every 60 min
4931 independent reflections	intensity decay: none

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0488P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4931 reflections	Δρmax = 0.33 e Å−3
292 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.017 (13)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
Cu	0.03338 (3)	0.43742 (2)	0.76295 (2)	0.03853 (10)
Cl1	−0.03484 (8)	0.33981 (5)	0.85529 (5)	0.05231 (19)
Cl2	−0.10262 (9)	0.40812 (6)	0.66326 (6)	0.0609 (2)
N1	0.0744 (2)	0.56146 (15)	0.72591 (14)	0.0361 (5)
N2	0.2032 (2)	0.43863 (17)	0.81961 (17)	0.0403 (5)
H2	0.193 (3)	0.438 (2)	0.871 (2)	0.048*
C1	0.1701 (3)	0.59164 (18)	0.78886 (17)	0.0352 (6)
H1	0.1234	0.5982	0.8406	0.042*
C2	0.2323 (3)	0.67928 (19)	0.7726 (2)	0.0476 (7)
H2A	0.2862	0.6755	0.7245	0.057*
H2B	0.1679	0.7226	0.7621	0.057*
C3	0.3099 (4)	0.7054 (2)	0.8468 (2)	0.0561 (9)
H3A	0.3490	0.7612	0.8368	0.067*
H3B	0.2552	0.7108	0.8944	0.067*
C4	0.4109 (3)	0.6388 (2)	0.8639 (2)	0.0602 (9)
H4A	0.4581	0.6556	0.9125	0.072*
H4B	0.4692	0.6366	0.8179	0.072*
C5	0.3532 (3)	0.5492 (2)	0.8772 (2)	0.0489 (8)
H5A	0.3028	0.5498	0.9271	0.059*
H5B	0.4204	0.5072	0.8845	0.059*
C6	0.2699 (3)	0.52161 (18)	0.8048 (2)	0.0373 (7)
H6	0.3229	0.5156	0.7557	0.045*
C7	−0.0463 (3)	0.61569 (18)	0.73180 (19)	0.0433 (7)
H7A	−0.0267	0.6739	0.7135	0.052*
H7B	−0.1075	0.5919	0.6936	0.052*
C8	−0.1073 (3)	0.62181 (19)	0.8143 (2)	0.0428 (7)
C9	−0.1934 (3)	0.5605 (2)	0.8410 (2)	0.0544 (8)
H9	−0.2095	0.5122	0.8085	0.065*
C10	−0.2553 (3)	0.5697 (3)	0.9143 (3)	0.0645 (10)
H10	−0.3108	0.5267	0.9317	0.077*
C11	−0.2371 (4)	0.6404 (3)	0.9621 (2)	0.0628 (10)
H11	−0.2812	0.6469	1.0112	0.075*
C12	−0.1515 (4)	0.7031 (3)	0.9366 (2)	0.0609 (10)
H12	−0.1373	0.7517	0.9692	0.073*
C13	−0.0880 (4)	0.6938 (2)	0.8638 (2)	0.0530 (9)
H13	−0.0312	0.7364	0.8473	0.064*
C14	0.1132 (3)	0.5719 (2)	0.63786 (17)	0.0465 (7)
H14A	0.1232	0.6333	0.6273	0.056*
H14B	0.0438	0.5518	0.6038	0.056*
C15	0.2318 (3)	0.5269 (2)	0.60886 (19)	0.0502 (8)
C16	0.2368 (4)	0.4375 (3)	0.59948 (19)	0.0564 (8)
H16	0.1669	0.4039	0.6127	0.068*
C17	0.3453 (4)	0.3988 (3)	0.5705 (3)	0.0759 (12)
H17	0.3495	0.3388	0.5664	0.091*
C18	0.4472 (5)	0.4482 (4)	0.5478 (3)	0.1003 (17)
H18	0.5202	0.4216	0.5284	0.120*
C19	0.4416 (5)	0.5367 (4)	0.5536 (3)	0.0976 (17)
H19	0.5098	0.5703	0.5368	0.117*
C20	0.3350 (4)	0.5754 (3)	0.5844 (2)	0.0744 (12)
H20	0.3320	0.6354	0.5888	0.089*
C21	0.2727 (3)	0.3570 (2)	0.7986 (2)	0.0551 (9)
H21A	0.2184	0.3082	0.8114	0.066*
H21B	0.2874	0.3562	0.7397	0.066*
C22	0.3962 (3)	0.34379 (19)	0.8410 (2)	0.0432 (7)
C23	0.4030 (4)	0.3147 (3)	0.9210 (2)	0.0631 (10)
H23	0.3292	0.3016	0.9495	0.076*
C24	0.5196 (5)	0.3048 (2)	0.9596 (2)	0.0737 (12)
H24	0.5238	0.2849	1.0135	0.088*
C25	0.6279 (4)	0.3247 (3)	0.9178 (3)	0.0705 (12)
H25	0.7056	0.3197	0.9440	0.085*
C26	0.6229 (3)	0.3515 (2)	0.8387 (3)	0.0621 (10)
H26	0.6970	0.3628	0.8099	0.075*
C27	0.5094 (3)	0.3617 (2)	0.8020 (2)	0.0517 (8)
H27	0.5073	0.3816	0.7480	0.062*

	U11	U22	U33	U12	U13	U23
Cu	0.03398 (17)	0.03603 (16)	0.04556 (19)	0.00039 (16)	−0.00646 (17)	−0.00163 (15)
Cl1	0.0463 (4)	0.0478 (4)	0.0629 (5)	−0.0078 (4)	−0.0052 (4)	0.0079 (3)
Cl2	0.0622 (5)	0.0594 (5)	0.0612 (5)	−0.0084 (4)	−0.0245 (4)	−0.0054 (4)
N1	0.0349 (11)	0.0387 (11)	0.0348 (12)	0.0045 (10)	−0.0041 (9)	−0.0005 (11)
N2	0.0347 (12)	0.0368 (12)	0.0494 (14)	0.0047 (12)	−0.0050 (11)	−0.0005 (13)
C1	0.0369 (15)	0.0370 (15)	0.0317 (15)	0.0021 (12)	−0.0037 (12)	−0.0027 (11)
C2	0.0491 (17)	0.0375 (15)	0.0563 (19)	−0.0031 (13)	−0.0058 (16)	−0.0004 (15)
C3	0.060 (2)	0.0404 (18)	0.068 (2)	−0.0031 (16)	−0.0085 (19)	−0.0075 (16)
C4	0.0491 (19)	0.056 (2)	0.075 (2)	−0.0027 (17)	−0.0152 (18)	−0.0130 (18)
C5	0.0405 (17)	0.046 (2)	0.060 (2)	0.0053 (14)	−0.0171 (15)	−0.0075 (15)
C6	0.0308 (15)	0.0376 (15)	0.0435 (17)	0.0020 (13)	−0.0003 (13)	−0.0048 (13)
C7	0.0416 (16)	0.0432 (15)	0.0452 (15)	0.0113 (13)	−0.0069 (16)	0.0001 (13)
C8	0.0360 (16)	0.0383 (16)	0.0540 (19)	0.0081 (14)	−0.0024 (15)	0.0009 (14)
C9	0.0398 (17)	0.0482 (18)	0.075 (2)	−0.0005 (17)	−0.0008 (17)	−0.0117 (19)
C10	0.0439 (19)	0.062 (2)	0.087 (3)	−0.0029 (19)	0.0155 (18)	0.007 (2)
C11	0.058 (2)	0.071 (3)	0.060 (2)	0.016 (2)	0.0131 (18)	0.004 (2)
C12	0.070 (2)	0.055 (2)	0.057 (2)	0.0071 (19)	0.0078 (19)	−0.0099 (17)
C13	0.061 (2)	0.0385 (17)	0.059 (2)	0.0054 (15)	0.0057 (17)	0.0001 (15)
C14	0.0547 (18)	0.0492 (18)	0.0357 (15)	0.0029 (17)	0.0005 (14)	0.0012 (14)
C15	0.061 (2)	0.058 (2)	0.0313 (16)	−0.0050 (17)	0.0085 (15)	−0.0060 (14)
C16	0.065 (2)	0.061 (2)	0.0434 (18)	−0.002 (2)	0.0110 (15)	−0.0125 (18)
C17	0.081 (3)	0.075 (3)	0.072 (3)	0.008 (2)	0.012 (2)	−0.027 (2)
C18	0.075 (3)	0.127 (4)	0.099 (3)	0.005 (3)	0.036 (3)	−0.035 (3)
C19	0.082 (3)	0.115 (4)	0.096 (3)	−0.022 (3)	0.047 (3)	−0.017 (3)
C20	0.085 (3)	0.076 (3)	0.062 (2)	−0.015 (2)	0.029 (2)	−0.006 (2)
C21	0.0438 (19)	0.0413 (18)	0.080 (2)	0.0136 (15)	−0.0093 (18)	−0.0090 (17)
C22	0.0367 (16)	0.0350 (15)	0.058 (2)	0.0057 (13)	0.0038 (15)	0.0010 (14)
C23	0.059 (2)	0.061 (2)	0.070 (3)	0.0144 (19)	0.020 (2)	0.0199 (19)
C24	0.096 (3)	0.071 (3)	0.055 (2)	0.030 (3)	−0.005 (2)	0.0129 (18)
C25	0.054 (2)	0.071 (3)	0.086 (3)	0.019 (2)	−0.017 (2)	−0.008 (2)
C26	0.0404 (19)	0.050 (2)	0.096 (3)	0.0027 (16)	0.008 (2)	−0.001 (2)
C27	0.046 (2)	0.0439 (17)	0.065 (2)	0.0104 (14)	0.0076 (16)	0.0028 (15)

Cu—N2	2.019 (2)	C10—H10	0.9300
Cu—N1	2.054 (2)	C11—C12	1.389 (5)
Cu—Cl2	2.2141 (9)	C11—H11	0.9300
Cu—Cl1	2.2463 (8)	C12—C13	1.369 (5)
N1—C14	1.498 (4)	C12—H12	0.9300
N1—C1	1.513 (3)	C13—H13	0.9300
N1—C7	1.530 (3)	C14—C15	1.511 (5)
N2—C6	1.482 (4)	C14—H14A	0.9700
N2—C21	1.499 (4)	C14—H14B	0.9700
N2—H2	0.85 (3)	C15—C20	1.383 (5)
C1—C2	1.528 (4)	C15—C16	1.389 (5)
C1—C6	1.533 (4)	C16—C17	1.377 (5)
C1—H1	0.9800	C16—H16	0.9300
C2—C3	1.513 (5)	C17—C18	1.371 (6)
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—C19	1.371 (7)
C3—C4	1.509 (5)	C18—H18	0.9300
C3—H3A	0.9700	C19—C20	1.371 (6)
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.528 (5)	C20—H20	0.9300
C4—H4A	0.9700	C21—C22	1.492 (5)
C4—H4B	0.9700	C21—H21A	0.9700
C5—C6	1.531 (4)	C21—H21B	0.9700
C5—H5A	0.9700	C22—C23	1.379 (5)
C5—H5B	0.9700	C22—C27	1.383 (4)
C6—H6	0.9800	C23—C24	1.392 (6)
C7—C8	1.492 (4)	C23—H23	0.9300
C7—H7A	0.9700	C24—C25	1.366 (6)
C7—H7B	0.9700	C24—H24	0.9300
C8—C9	1.383 (5)	C25—C26	1.352 (6)
C8—C13	1.388 (5)	C25—H25	0.9300
C9—C10	1.368 (5)	C26—C27	1.350 (5)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.354 (6)	C27—H27	0.9300
N2—Cu—N1	86.39 (10)	C10—C9—C8	121.2 (4)
N2—Cu—Cl2	156.09 (8)	C10—C9—H9	119.4
N1—Cu—Cl2	96.50 (7)	C8—C9—H9	119.4
N2—Cu—Cl1	89.27 (8)	C11—C10—C9	121.1 (4)
N1—Cu—Cl1	152.80 (7)	C11—C10—H10	119.5
Cl2—Cu—Cl1	98.24 (4)	C9—C10—H10	119.5
C14—N1—C1	115.5 (2)	C10—C11—C12	118.9 (4)
C14—N1—C7	103.3 (2)	C10—C11—H11	120.5
C1—N1—C7	110.3 (2)	C12—C11—H11	120.5
C14—N1—Cu	115.99 (19)	C13—C12—C11	120.4 (4)
C1—N1—Cu	103.32 (16)	C13—C12—H12	119.8
C7—N1—Cu	108.40 (17)	C11—C12—H12	119.8
C6—N2—C21	117.2 (2)	C12—C13—C8	120.9 (3)
C6—N2—Cu	110.95 (18)	C12—C13—H13	119.6
C21—N2—Cu	108.9 (2)	C8—C13—H13	119.6
C6—N2—H2	103 (2)	N1—C14—C15	118.5 (3)
C21—N2—H2	106 (2)	N1—C14—H14A	107.7
Cu—N2—H2	110 (2)	C15—C14—H14A	107.7
N1—C1—C2	116.4 (2)	N1—C14—H14B	107.7
N1—C1—C6	111.0 (2)	C15—C14—H14B	107.7
C2—C1—C6	111.0 (2)	H14A—C14—H14B	107.1
N1—C1—H1	105.9	C20—C15—C16	118.5 (3)
C2—C1—H1	105.9	C20—C15—C14	119.8 (3)
C6—C1—H1	105.9	C16—C15—C14	121.5 (3)
C3—C2—C1	109.4 (3)	C17—C16—C15	120.0 (4)
C3—C2—H2A	109.8	C17—C16—H16	120.0
C1—C2—H2A	109.8	C15—C16—H16	120.0
C3—C2—H2B	109.8	C18—C17—C16	120.4 (4)
C1—C2—H2B	109.8	C18—C17—H17	119.8
H2A—C2—H2B	108.2	C16—C17—H17	119.8
C4—C3—C2	110.5 (3)	C19—C18—C17	120.1 (5)
C4—C3—H3A	109.6	C19—C18—H18	119.9
C2—C3—H3A	109.6	C17—C18—H18	119.9
C4—C3—H3B	109.6	C18—C19—C20	119.7 (5)
C2—C3—H3B	109.6	C18—C19—H19	120.2
H3A—C3—H3B	108.1	C20—C19—H19	120.2
C3—C4—C5	111.1 (3)	C19—C20—C15	121.2 (4)
C3—C4—H4A	109.4	C19—C20—H20	119.4
C5—C4—H4A	109.4	C15—C20—H20	119.4
C3—C4—H4B	109.4	C22—C21—N2	116.0 (3)
C5—C4—H4B	109.4	C22—C21—H21A	108.3
H4A—C4—H4B	108.0	N2—C21—H21A	108.3
C4—C5—C6	111.9 (3)	C22—C21—H21B	108.3
C4—C5—H5A	109.2	N2—C21—H21B	108.3
C6—C5—H5A	109.2	H21A—C21—H21B	107.4
C4—C5—H5B	109.2	C23—C22—C27	116.9 (3)
C6—C5—H5B	109.2	C23—C22—C21	121.8 (3)
H5A—C5—H5B	107.9	C27—C22—C21	121.3 (3)
N2—C6—C5	112.9 (3)	C22—C23—C24	120.5 (4)
N2—C6—C1	108.0 (2)	C22—C23—H23	119.8
C5—C6—C1	109.3 (2)	C24—C23—H23	119.8
N2—C6—H6	108.8	C25—C24—C23	119.6 (3)
C5—C6—H6	108.8	C25—C24—H24	120.2
C1—C6—H6	108.8	C23—C24—H24	120.2
C8—C7—N1	116.9 (2)	C26—C25—C24	120.6 (4)
C8—C7—H7A	108.1	C26—C25—H25	119.7
N1—C7—H7A	108.1	C24—C25—H25	119.7
C8—C7—H7B	108.1	C27—C26—C25	119.4 (4)
N1—C7—H7B	108.1	C27—C26—H26	120.3
H7A—C7—H7B	107.3	C25—C26—H26	120.3
C9—C8—C13	117.6 (3)	C26—C27—C22	123.0 (3)
C9—C8—C7	121.6 (3)	C26—C27—H27	118.5
C13—C8—C7	120.6 (3)	C22—C27—H27	118.5
N2—Cu—N1—C14	104.1 (2)	C1—N1—C7—C8	−53.7 (3)
Cl2—Cu—N1—C14	−52.04 (19)	Cu—N1—C7—C8	58.8 (3)
Cl1—Cu—N1—C14	−174.54 (15)	N1—C7—C8—C9	−86.8 (3)
N2—Cu—N1—C1	−23.25 (17)	N1—C7—C8—C13	99.2 (3)
Cl2—Cu—N1—C1	−179.41 (15)	C13—C8—C9—C10	−1.4 (5)
Cl1—Cu—N1—C1	58.1 (2)	C7—C8—C9—C10	−175.5 (3)
N2—Cu—N1—C7	−140.32 (18)	C8—C9—C10—C11	2.0 (6)
Cl2—Cu—N1—C7	63.51 (17)	C9—C10—C11—C12	−1.7 (6)
Cl1—Cu—N1—C7	−59.0 (2)	C10—C11—C12—C13	0.8 (6)
N1—Cu—N2—C6	−1.8 (2)	C11—C12—C13—C8	−0.3 (6)
Cl2—Cu—N2—C6	96.1 (3)	C9—C8—C13—C12	0.5 (5)
Cl1—Cu—N2—C6	−154.94 (19)	C7—C8—C13—C12	174.8 (3)
N1—Cu—N2—C21	−132.2 (2)	C1—N1—C14—C15	59.0 (4)
Cl2—Cu—N2—C21	−34.3 (3)	C7—N1—C14—C15	179.6 (3)
Cl1—Cu—N2—C21	74.7 (2)	Cu—N1—C14—C15	−62.0 (3)
C14—N1—C1—C2	45.3 (3)	N1—C14—C15—C20	−114.2 (4)
C7—N1—C1—C2	−71.3 (3)	N1—C14—C15—C16	71.3 (4)
Cu—N1—C1—C2	173.0 (2)	C20—C15—C16—C17	3.5 (5)
C14—N1—C1—C6	−82.8 (3)	C14—C15—C16—C17	178.0 (3)
C7—N1—C1—C6	160.6 (2)	C15—C16—C17—C18	−2.5 (6)
Cu—N1—C1—C6	44.9 (2)	C16—C17—C18—C19	−0.1 (8)
N1—C1—C2—C3	171.8 (3)	C17—C18—C19—C20	1.7 (8)
C6—C1—C2—C3	−60.1 (3)	C18—C19—C20—C15	−0.7 (8)
C1—C2—C3—C4	59.6 (4)	C16—C15—C20—C19	−1.9 (6)
C2—C3—C4—C5	−57.4 (4)	C14—C15—C20—C19	−176.5 (4)
C3—C4—C5—C6	55.2 (4)	C6—N2—C21—C22	57.9 (4)
C21—N2—C6—C5	−86.4 (3)	Cu—N2—C21—C22	−175.2 (3)
Cu—N2—C6—C5	147.6 (2)	N2—C21—C22—C23	78.9 (4)
C21—N2—C6—C1	152.6 (3)	N2—C21—C22—C27	−100.0 (4)
Cu—N2—C6—C1	26.6 (3)	C27—C22—C23—C24	0.3 (5)
C4—C5—C6—N2	−174.6 (3)	C21—C22—C23—C24	−178.6 (3)
C4—C5—C6—C1	−54.3 (4)	C22—C23—C24—C25	0.4 (6)
N1—C1—C6—N2	−48.7 (3)	C23—C24—C25—C26	−1.8 (6)
C2—C1—C6—N2	−179.7 (2)	C24—C25—C26—C27	2.4 (6)
N1—C1—C6—C5	−171.9 (2)	C25—C26—C27—C22	−1.7 (6)
C2—C1—C6—C5	57.1 (3)	C23—C22—C27—C26	0.3 (5)
C14—N1—C7—C8	−177.7 (3)	C21—C22—C27—C26	179.2 (3)