1-[(2S)-1-Chloro-3-phenyl­propan-2-yl]-2,4,5-triphenyl-1H-imidazole

Abstract

In the title compound, C₃₀H₂₅ClN₂, the chiral center maintains the S configuration of the stating l-phenyl­alaninol. The two phenyl groups closest to the substituted N atom adopt an almost perpendicular orientation relative to the central imidazole ring, with dihedral angles of 88.9 (4) and 84.7 (3)°. The third phenyl group is nearly coplanar with it, making a dihedral angle of 11.0 (5)°.

Related literature  

For the synthesis and applications of chiral ionic liquids, see: Ding et al. (2005 ▶); Bwambok et al. (2008 ▶); Mao et al. (2010 ▶).

Experimental  

Crystal data  

• C₃₀H₂₅ClN₂

• M _r = 448.97

• Orthorhombic,

• a = 9.6123 (4) Å

• b = 9.9437 (3) Å

• c = 24.9677 (7) Å

• V = 2386.47 (14) ų

• Z = 4

• Cu Kα radiation

• μ = 1.56 mm⁻¹

• T = 291 K

• 0.21 × 0.20 × 0.06 mm

Data collection  

• Agilent Xcalibur Eos Gemini diffractometer

• Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.657, T _max = 1.000

• 9379 measured reflections

• 4256 independent reflections

• 3235 reflections with I > 2σ(I)

• R _int = 0.044

Refinement  

• R[F ² > 2σ(F ²)] = 0.045

• wR(F ²) = 0.098

• S = 1.02

• 4256 reflections

• 298 parameters

• H-atom parameters constrained

• Δρ_max = 0.14 e Å⁻³

• Δρ_min = −0.15 e Å⁻³

• Absolute structure: Flack (1983 ▶), 1816 Friedel pairs

• Flack parameter: 0.01 (2)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812009609/ld2044Isup3.cml

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

supplementary crystallographic information

Comment

Current interest in the stereoselective synthesis and catalysis, chiral recognization and separation in ionic liquids has motivated the synthesis of novel chiral ionic liquids. (Ding & Armstrong, 2005; Bwambok et al., 2008). Our group is interested in the preparation and application of chiral imidazolium derivatives from natural precursors (Mao et al., 2010). During the study, we observed that condensation of l-phenylalaninol, dibenzoyl, arylaldehyde and ammonium acetate afforded multi-aryl substituted imidazole alcohol derivatives carrying a chiral functionality. The following reaction with SOCl₂ produced the title compound smoothly.

The molecular structure of the title compound is shown in Figure 1. As it is expected, the imidazole core (N1, C8, C7, N2, C24) is essentially planar. featuring an average deviation of less than 0.6 (3) °. The dihedral angles formed by the three aryl substituents and the central imidazole ring are 88.9 (4) (N2—C24—C25—C26), 11.0 (5) (C5—C6—C7—C8) and 95.3 (3) ° (C7—C8—C9—C14).

Due to the presence of muti aryl groups on the imidazole ring, the basicity of the N2 of the imidazole is reduced and its quaternization by the produced chloro- substituted derivative is suppressed successfully.

Experimental

SOCl₂ (40 ml) was added slowly at room temperature into a three-neck flask containing 2-(4,5-Diphenyl-2-p-tolyl-imidazol-1-yl)-3-phenyl-propan-1-ol (4.45 g, 0.01 mol) and Na₂CO₃ (1.06 g, 0.01 mol). The solids were slowly dissolved upon addition of SOCl₂. After complete addition, the mixture was kept at 50 °C for 5 h and then at 70 °C for 2 h. The excessive SOCl₂ was removed and the residue was washed with H₂O and filtered to afford the crude product. Crystallization from EtOH afforded colorless crystals of the title compound.

Refinement

A suitable crystal was selected and mounted on a Xcalibur, Eos, Gemini diffractometer.The crystal was kept at 291.15 K during data collection. Using Olex2 (Dolomanov et al., 2009), the structure was solved with the SHELXS (Sheldrick, 2008) structure solution program using Direct Methods and refined with the SHELXL (Sheldrick, 2008) refinement package using Least Squares minimization.

Figures

Fig. 1.

The molecular structure of the title compound showing 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.

Crystal data

C30H25ClN2	Dx = 1.250 Mg m−3
Mr = 448.97	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121	Cell parameters from 2343 reflections
a = 9.6123 (4) Å	θ = 3.5–66.9°
b = 9.9437 (3) Å	µ = 1.56 mm−1
c = 24.9677 (7) Å	T = 291 K
V = 2386.47 (14) Å3	Prismatic, colorless
Z = 4	0.21 × 0.20 × 0.06 mm
F(000) = 944

Data collection

Agilent Xcalibur Eos Gemini diffractometer	4256 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3235 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 16.2312 pixels mm-1	θmax = 67.0°, θmin = 3.5°
ω scans	h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.657, Tmax = 1.000	l = −29→29
9379 measured reflections

Refinement

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0291P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4256 reflections	Δρmax = 0.14 e Å−3
298 parameters	Δρmin = −0.15 e Å−3
0 restraints	Absolute structure: Flack (1983), 1816 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (2)

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
Cl1	0.02166 (10)	0.49291 (10)	0.54575 (3)	0.0805 (3)
N1	0.2271 (2)	0.64694 (19)	0.67166 (8)	0.0430 (5)
N2	0.2501 (3)	0.80764 (18)	0.73267 (8)	0.0433 (5)
C1	0.2662 (3)	0.7993 (3)	0.84491 (10)	0.0525 (7)
H1	0.2457	0.8782	0.8266	0.063*
C2	0.2834 (4)	0.8033 (3)	0.90011 (11)	0.0619 (8)
H2	0.2755	0.8844	0.9184	0.074*
C3	0.3121 (4)	0.6867 (3)	0.92756 (10)	0.0617 (8)
H3	0.3223	0.6884	0.9646	0.074*
C4	0.3255 (4)	0.5675 (3)	0.90000 (11)	0.0626 (8)
H4	0.3461	0.4887	0.9185	0.075*
C5	0.3085 (3)	0.5641 (3)	0.84478 (11)	0.0545 (8)
H5	0.3171	0.4830	0.8266	0.065*
C6	0.2790 (3)	0.6806 (2)	0.81663 (9)	0.0415 (5)
C7	0.2604 (3)	0.6838 (2)	0.75749 (9)	0.0395 (5)
C8	0.2469 (3)	0.5829 (2)	0.72076 (9)	0.0382 (5)
C9	0.2431 (3)	0.4337 (2)	0.72724 (9)	0.0394 (6)
C10	0.1175 (3)	0.3689 (3)	0.73505 (11)	0.0477 (6)
H10	0.0357	0.4187	0.7364	0.057*
C11	0.1120 (3)	0.2302 (3)	0.74093 (12)	0.0564 (8)
H11	0.0269	0.1877	0.7461	0.068*
C12	0.2317 (4)	0.1558 (2)	0.73909 (12)	0.0574 (8)
H12	0.2280	0.0628	0.7425	0.069*
C13	0.3575 (3)	0.2192 (3)	0.73211 (12)	0.0556 (7)
H13	0.4388	0.1686	0.7312	0.067*
C14	0.3644 (3)	0.3580 (3)	0.72642 (11)	0.0494 (7)
H14	0.4501	0.4000	0.7221	0.059*
C15	0.5054 (4)	0.6007 (3)	0.53636 (12)	0.0726 (10)
H15	0.4501	0.5715	0.5081	0.087*
C16	0.6292 (5)	0.6662 (4)	0.52570 (16)	0.0907 (13)
H16	0.6567	0.6799	0.4904	0.109*
C17	0.7110 (4)	0.7106 (3)	0.56644 (17)	0.0845 (12)
H17	0.7943	0.7544	0.5590	0.101*
C18	0.6708 (4)	0.6909 (3)	0.61861 (16)	0.0719 (9)
H18	0.7260	0.7218	0.6466	0.086*
C19	0.5479 (3)	0.6250 (3)	0.62902 (12)	0.0611 (8)
H19	0.5210	0.6114	0.6644	0.073*
C20	0.4629 (3)	0.5783 (3)	0.58816 (10)	0.0521 (7)
C21	0.3307 (3)	0.5022 (3)	0.59933 (10)	0.0539 (7)
H21A	0.3494	0.4355	0.6267	0.065*
H21B	0.3036	0.4546	0.5671	0.065*
C22	0.2082 (3)	0.5894 (3)	0.61769 (10)	0.0482 (7)
H22	0.2023	0.6653	0.5927	0.058*
C23	0.0692 (3)	0.5147 (3)	0.61442 (10)	0.0612 (8)
H23A	−0.0023	0.5657	0.6329	0.073*
H23B	0.0773	0.4277	0.6317	0.073*
C24	0.2292 (3)	0.7824 (2)	0.68147 (10)	0.0414 (5)
C25	0.2084 (3)	0.8899 (2)	0.64130 (10)	0.0449 (6)
C26	0.3191 (4)	0.9466 (3)	0.61519 (14)	0.0750 (10)
H26	0.4076	0.9104	0.6197	0.090*
C27	0.3010 (5)	1.0571 (4)	0.58219 (16)	0.0921 (13)
H27	0.3770	1.0946	0.5646	0.111*
C28	0.1709 (4)	1.1112 (3)	0.57538 (13)	0.0762 (11)
H28	0.1585	1.1856	0.5533	0.091*
C29	0.0601 (4)	1.0555 (4)	0.60104 (14)	0.0781 (11)
H29	−0.0283	1.0919	0.5965	0.094*
C30	0.0785 (3)	0.9450 (3)	0.63390 (12)	0.0640 (8)
H30	0.0021	0.9074	0.6512	0.077*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0822 (6)	0.1023 (6)	0.0571 (3)	−0.0076 (6)	−0.0157 (4)	−0.0137 (5)
N1	0.0504 (13)	0.0381 (10)	0.0404 (10)	0.0030 (10)	0.0030 (10)	−0.0012 (9)
N2	0.0537 (13)	0.0320 (9)	0.0441 (10)	−0.0012 (11)	−0.0006 (11)	−0.0012 (9)
C1	0.0667 (19)	0.0384 (12)	0.0524 (13)	−0.0001 (16)	−0.0016 (15)	−0.0048 (12)
C2	0.081 (2)	0.0531 (15)	0.0520 (14)	−0.0010 (18)	−0.0013 (16)	−0.0120 (13)
C3	0.077 (2)	0.0647 (18)	0.0431 (13)	−0.0035 (18)	−0.0066 (14)	−0.0035 (14)
C4	0.082 (2)	0.0540 (15)	0.0517 (14)	0.0087 (17)	−0.0078 (15)	0.0070 (14)
C5	0.074 (2)	0.0402 (13)	0.0491 (13)	0.0059 (15)	−0.0017 (14)	−0.0030 (12)
C6	0.0432 (13)	0.0391 (12)	0.0422 (11)	−0.0024 (12)	−0.0001 (11)	0.0001 (10)
C7	0.0406 (14)	0.0329 (10)	0.0449 (12)	0.0006 (12)	−0.0001 (12)	0.0004 (10)
C8	0.0367 (13)	0.0345 (11)	0.0435 (12)	0.0020 (11)	0.0045 (12)	0.0006 (10)
C9	0.0466 (15)	0.0331 (10)	0.0384 (11)	0.0026 (12)	0.0011 (12)	−0.0022 (9)
C10	0.0459 (15)	0.0394 (14)	0.0579 (14)	0.0057 (13)	0.0043 (14)	0.0019 (13)
C11	0.0532 (17)	0.0477 (16)	0.0683 (18)	−0.0100 (14)	−0.0030 (16)	0.0052 (15)
C12	0.079 (2)	0.0311 (11)	0.0618 (15)	−0.0025 (15)	−0.0026 (18)	0.0010 (12)
C13	0.0596 (18)	0.0421 (16)	0.0650 (17)	0.0192 (15)	0.0023 (16)	0.0022 (14)
C14	0.0441 (15)	0.0445 (15)	0.0596 (15)	0.0011 (13)	0.0062 (14)	0.0021 (13)
C15	0.092 (3)	0.073 (2)	0.0528 (16)	0.011 (2)	0.0135 (18)	0.0050 (15)
C16	0.108 (3)	0.092 (3)	0.072 (2)	0.008 (3)	0.034 (2)	0.023 (2)
C17	0.079 (3)	0.0602 (19)	0.114 (3)	0.001 (2)	0.036 (3)	0.014 (2)
C18	0.070 (2)	0.0579 (17)	0.087 (2)	−0.0023 (18)	0.0098 (19)	0.0003 (18)
C19	0.070 (2)	0.0577 (16)	0.0555 (15)	0.0019 (17)	0.0098 (16)	0.0060 (15)
C20	0.0629 (19)	0.0471 (15)	0.0464 (13)	0.0125 (15)	0.0084 (14)	0.0004 (12)
C21	0.0678 (19)	0.0488 (14)	0.0451 (12)	0.0048 (17)	0.0049 (13)	−0.0073 (13)
C22	0.0606 (18)	0.0424 (13)	0.0417 (12)	−0.0012 (14)	0.0010 (13)	−0.0041 (11)
C23	0.0660 (19)	0.076 (2)	0.0416 (12)	−0.0059 (19)	−0.0029 (13)	−0.0096 (15)
C24	0.0453 (14)	0.0342 (11)	0.0448 (12)	0.0020 (13)	0.0022 (12)	0.0003 (10)
C25	0.0547 (16)	0.0388 (12)	0.0412 (12)	−0.0009 (13)	0.0015 (12)	0.0020 (11)
C26	0.063 (2)	0.073 (2)	0.089 (2)	0.0052 (18)	0.0099 (19)	0.0319 (19)
C27	0.090 (3)	0.088 (3)	0.098 (3)	−0.010 (2)	0.015 (2)	0.048 (2)
C28	0.107 (3)	0.0606 (19)	0.0615 (18)	0.012 (2)	−0.003 (2)	0.0232 (16)
C29	0.084 (3)	0.079 (2)	0.0713 (19)	0.030 (2)	−0.004 (2)	0.0219 (18)
C30	0.0601 (19)	0.0696 (19)	0.0623 (16)	0.0061 (16)	0.0063 (16)	0.0164 (16)

Geometric parameters (Å, º)

Cl1—C23	1.788 (2)	C15—H15	0.9300
N1—C8	1.395 (3)	C15—C16	1.383 (6)
N1—C22	1.475 (3)	C15—C20	1.374 (4)
N1—C24	1.370 (3)	C16—H16	0.9300
N2—C7	1.382 (3)	C16—C17	1.360 (6)
N2—C24	1.318 (3)	C17—H17	0.9300
C1—H1	0.9300	C17—C18	1.373 (5)
C1—C2	1.389 (4)	C18—H18	0.9300
C1—C6	1.380 (3)	C18—C19	1.376 (5)
C2—H2	0.9300	C19—H19	0.9300
C2—C3	1.374 (4)	C19—C20	1.387 (4)
C3—H3	0.9300	C20—C21	1.506 (4)
C3—C4	1.377 (4)	C21—H21A	0.9700
C4—H4	0.9300	C21—H21B	0.9700
C4—C5	1.389 (4)	C21—C22	1.532 (4)
C5—H5	0.9300	C22—H22	0.9800
C5—C6	1.384 (3)	C22—C23	1.531 (4)
C6—C7	1.488 (3)	C23—H23A	0.9700
C7—C8	1.366 (3)	C23—H23B	0.9700
C8—C9	1.492 (3)	C24—C25	1.479 (3)
C9—C10	1.383 (4)	C25—C26	1.370 (4)
C9—C14	1.388 (4)	C25—C30	1.376 (4)
C10—H10	0.9300	C26—H26	0.9300
C10—C11	1.388 (4)	C26—C27	1.384 (4)
C11—H11	0.9300	C27—H27	0.9300
C11—C12	1.369 (4)	C27—C28	1.372 (5)
C12—H12	0.9300	C28—H28	0.9300
C12—C13	1.374 (5)	C28—C29	1.361 (5)
C13—H13	0.9300	C29—H29	0.9300
C13—C14	1.389 (4)	C29—C30	1.383 (4)
C14—H14	0.9300	C30—H30	0.9300
C8—N1—C22	130.0 (2)	C16—C17—H17	120.0
C24—N1—C8	106.9 (2)	C16—C17—C18	120.0 (4)
C24—N1—C22	123.1 (2)	C18—C17—H17	120.0
C24—N2—C7	106.05 (19)	C17—C18—H18	120.3
C2—C1—H1	119.3	C17—C18—C19	119.3 (4)
C6—C1—H1	119.3	C19—C18—H18	120.3
C6—C1—C2	121.4 (3)	C18—C19—H19	119.1
C1—C2—H2	120.2	C18—C19—C20	121.7 (3)
C3—C2—C1	119.6 (3)	C20—C19—H19	119.1
C3—C2—H2	120.2	C15—C20—C19	117.6 (3)
C2—C3—H3	120.1	C15—C20—C21	120.4 (3)
C2—C3—C4	119.7 (3)	C19—C20—C21	121.9 (2)
C4—C3—H3	120.1	C20—C21—H21A	108.6
C3—C4—H4	119.8	C20—C21—H21B	108.6
C3—C4—C5	120.4 (3)	C20—C21—C22	114.8 (2)
C5—C4—H4	119.8	H21A—C21—H21B	107.5
C4—C5—H5	119.7	C22—C21—H21A	108.6
C6—C5—C4	120.6 (3)	C22—C21—H21B	108.6
C6—C5—H5	119.7	N1—C22—C21	113.4 (2)
C1—C6—C5	118.3 (2)	N1—C22—H22	106.8
C1—C6—C7	118.6 (2)	N1—C22—C23	110.2 (2)
C5—C6—C7	123.1 (2)	C21—C22—H22	106.8
N2—C7—C6	118.23 (19)	C23—C22—C21	112.3 (2)
C8—C7—N2	110.3 (2)	C23—C22—H22	106.8
C8—C7—C6	131.4 (2)	Cl1—C23—H23A	109.8
N1—C8—C9	123.1 (2)	Cl1—C23—H23B	109.8
C7—C8—N1	105.5 (2)	C22—C23—Cl1	109.44 (19)
C7—C8—C9	131.3 (2)	C22—C23—H23A	109.8
C10—C9—C8	120.0 (3)	C22—C23—H23B	109.8
C10—C9—C14	118.8 (2)	H23A—C23—H23B	108.2
C14—C9—C8	121.2 (3)	N1—C24—C25	126.0 (2)
C9—C10—H10	119.6	N2—C24—N1	111.3 (2)
C9—C10—C11	120.8 (3)	N2—C24—C25	122.8 (2)
C11—C10—H10	119.6	C26—C25—C24	121.0 (3)
C10—C11—H11	120.0	C26—C25—C30	118.5 (3)
C12—C11—C10	120.1 (3)	C30—C25—C24	120.1 (3)
C12—C11—H11	120.0	C25—C26—H26	119.6
C11—C12—H12	120.1	C25—C26—C27	120.8 (3)
C11—C12—C13	119.8 (2)	C27—C26—H26	119.6
C13—C12—H12	120.1	C26—C27—H27	120.0
C12—C13—H13	119.6	C28—C27—C26	120.0 (4)
C12—C13—C14	120.7 (3)	C28—C27—H27	120.0
C14—C13—H13	119.6	C27—C28—H28	120.2
C9—C14—C13	119.8 (3)	C29—C28—C27	119.7 (3)
C9—C14—H14	120.1	C29—C28—H28	120.2
C13—C14—H14	120.1	C28—C29—H29	119.9
C16—C15—H15	119.6	C28—C29—C30	120.2 (3)
C20—C15—H15	119.6	C30—C29—H29	119.9
C20—C15—C16	120.9 (4)	C25—C30—C29	120.8 (3)
C15—C16—H16	119.8	C25—C30—H30	119.6
C17—C16—C15	120.5 (3)	C29—C30—H30	119.6
C17—C16—H16	119.8
N1—C8—C9—C10	−85.7 (3)	C10—C11—C12—C13	0.9 (5)
N1—C8—C9—C14	95.3 (3)	C11—C12—C13—C14	−0.6 (5)
N1—C22—C23—Cl1	161.61 (19)	C12—C13—C14—C9	−0.6 (4)
N1—C24—C25—C26	−92.4 (4)	C14—C9—C10—C11	−1.2 (4)
N1—C24—C25—C30	94.9 (4)	C15—C16—C17—C18	−0.2 (6)
N2—C7—C8—N1	−0.2 (3)	C15—C20—C21—C22	−105.2 (3)
N2—C7—C8—C9	−176.5 (3)	C16—C15—C20—C19	0.7 (5)
N2—C24—C25—C26	88.9 (4)	C16—C15—C20—C21	−177.6 (3)
N2—C24—C25—C30	−83.8 (4)	C16—C17—C18—C19	0.6 (5)
C1—C2—C3—C4	1.0 (5)	C17—C18—C19—C20	−0.3 (5)
C1—C6—C7—N2	8.6 (4)	C18—C19—C20—C15	−0.3 (5)
C1—C6—C7—C8	−169.1 (3)	C18—C19—C20—C21	178.0 (3)
C2—C1—C6—C5	0.5 (5)	C19—C20—C21—C22	76.5 (3)
C2—C1—C6—C7	−179.5 (3)	C20—C15—C16—C17	−0.5 (6)
C2—C3—C4—C5	−0.8 (6)	C20—C21—C22—N1	−69.1 (3)
C3—C4—C5—C6	0.5 (5)	C20—C21—C22—C23	165.1 (2)
C4—C5—C6—C1	−0.3 (5)	C21—C22—C23—Cl1	−70.9 (3)
C4—C5—C6—C7	179.6 (3)	C22—N1—C8—C7	179.2 (3)
C5—C6—C7—N2	−171.3 (3)	C22—N1—C8—C9	−4.1 (5)
C5—C6—C7—C8	11.0 (5)	C22—N1—C24—N2	−178.8 (2)
C6—C1—C2—C3	−0.8 (5)	C22—N1—C24—C25	2.4 (5)
C6—C7—C8—N1	177.7 (3)	C24—N1—C8—C7	−0.3 (3)
C6—C7—C8—C9	1.3 (5)	C24—N1—C8—C9	176.5 (3)
C7—N2—C24—N1	−0.7 (3)	C24—N1—C22—C21	119.7 (3)
C7—N2—C24—C25	178.1 (3)	C24—N1—C22—C23	−113.4 (3)
C7—C8—C9—C10	90.2 (4)	C24—N2—C7—C6	−177.7 (2)
C7—C8—C9—C14	−88.8 (4)	C24—N2—C7—C8	0.5 (3)
C8—N1—C22—C21	−59.6 (4)	C24—C25—C26—C27	−172.7 (3)
C8—N1—C22—C23	67.3 (4)	C24—C25—C30—C29	172.6 (3)
C8—N1—C24—N2	0.6 (3)	C25—C26—C27—C28	0.1 (6)
C8—N1—C24—C25	−178.2 (3)	C26—C25—C30—C29	−0.3 (5)
C8—C9—C10—C11	179.7 (3)	C26—C27—C28—C29	−0.2 (6)
C8—C9—C14—C13	−179.5 (2)	C27—C28—C29—C30	0.1 (6)
C9—C10—C11—C12	0.0 (5)	C28—C29—C30—C25	0.2 (5)
C10—C9—C14—C13	1.5 (4)	C30—C25—C26—C27	0.1 (5)