2-Nitroso-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine

The title compound, C₂₄H₁₉N₃O, crystallizes in the centrosymmetric space group P2₁/a with one mol­ecule in the asymmetric unit. The tetra­hydro­pyridine ring has a boat conformation. The dihedral angle between the fused pyridine rings is 16.2 (1)°. The equatorial and axial orientations of the two phenyl groups with respect to the tetra­hydro­pyridine ring are confirmed. The nitroso group is coplanar with the attached C—N—C group. The interplanar angle formed between the fused tetra­hydro­pyridine and benzene planes is 13.4 (1)°. The crystal packing is stabilized by an intermolecular C—H...O hydrogen bond, which forms a C(9) graph-set chain running along the [001] direction.

S1. Comment

Nitrosamines are known to exhibit carcinogenic properties (Magee et al., 1976; Ferguson, 1975). Ever since the first demonstration of carcinogenicity in N-nitroso compounds (Magee & Barnes, 1956), there have been extensive biochemical and physicochemical studies on their structure-activity relationships (Lijinsky, 1984; Magee et al., 1976). However, there is little information on the detailed geometries of N-nitroso compounds, although several solution NMR spectroscopic investigations have been carried out (Fraser & Grindley, 1975; Forrest et al., 1974; Ellis et al., 1974; Priya et al., 1992). Certain N-nitrosoureas are used as antitumour agents or antibiotics (Sapse et al., 1988).

1,6-Naphthyridines have extensive pharmacological properties. These derivatives have antiinflammatory (Di Braccio et al., 1997), antibacterial (Hong et al., 1997), antitumour (Chen et al.., 1997), cardiotonic (Mohan & Mishra, 1997), and anticonvulsant and insecticidal (Damon & Nadelson, 1981) properties. They exhibit unique photophysical, photochemical and optical properties due to the charge-transfer interaction between the donor and acceptor substituents. They can behave as nonlinear optical materials, which have various applications in the field of telecommunications (Murugan, 1997). In addition, 1,6-naphthyridine derivatives are also used as novel potent adenosine 3',5'-cyclic phosphate phosphodiesterase III inhibitors (Singh et al., 1995).

We have undertaken the synthesis and structural analysis of a series of cyclic nitrosamines (Senthilkumar et al., 1992, 1995; Ravinderan et al., 1992; Priya et al., 1992). The 1,6-naphthyridine system is known (Reed et al., 1988; Vinick, 1989), but only a few structural data have been reported to date (Balogh et al., 1986; Goméz de Andérez et al., 1992; Govindasamy et al., 2000). Against this background, and in order to obtain detailed information about stereochemical and conformational changes induced by the substituents on the title compound, (I), in the solid state, its X-ray structure determination has been carried out and the results are presented here. \sch

Fig. 1 shows a view of (I) with the atom-numbering scheme. The N2—N3 and N3═O bond lengths and the N2—N3—O bond angle are comparable with the previously reported values of 1.331 (2) Å, 1.231 (2) Å and 115.3 (1)°, respectively (Priya et al., 1992). The N2—N3 bond exhibits partial double-bond character, which leads to restricted rotation about the bond, as also found from solution NMR studies (Cooney & Brownstein, 1974). The N—C distances in (I) agree well with the literature values (Allen et al., 1987).

The nitroso group of (I) has a coplanar orientation with respect to atoms C2 and C3, as is evident from the C3—N2—N3—O and C2—N2—N3—O torsion angles, respectively. The C11—C1—C2—C19 torsion angle shows that the phenyl ring attached at C2 is equatorially disposed in the naphthyridine system. The C11—C12—C3—C13 torsion angle shows that the phenyl group attached at C3 is axially oriented in the naphthyridine system. A similar effect has also been observed by Lavaanya et al. (2001). The dihedral angle between the fused pyridine rings is 16.2 (1)°. The interplanar angle formed between the fused tetrahydropyridine and benzo planes is 13.4 (1)°. The angle between the planes of the C13—C18 and C19—C24 phenyl rings is 88.9 (1)°.

The substitution of a methyl or nitroso group at the N2 position has been shown to exert a large influence on the conformation of the ring and the orientation of the ring substituents (Vierhapper, 1980; Baliah & Natarajan, 1989). The tetrahydropyridine ring of (I) has a boat conformation, with a total puckering amplitude (Cremer & Pople, 1975) of Q_T = 0.520 (2) Å and with values of the lowest displacement asymmetry parameters (Nardelli, 1983) of Δ_S(C1) = 0.015 (1) and Δ_S(N2—C2) = 0.019 (1).

In addition to van der Waals interactions, the crystal packing of (I) is stabilized by an C—H···O intermolecular hydrogen bond, with C5—H5 0.93, H5—Oⁱ 2.47 and C5···Oⁱ 3.179 (3) Å, and C5—H5···Oⁱ 133° [symmetry code: (i) x + 1/2, 3/2 − y, 1 + z]. This intermolecular hydrogen bond forms a C(9) (Bernstein et al., 1995) graph-set chain, O—N3—N2—C3—C12—C4—C10—C5—H5, running along the [001] direction (Fig. 2).

S2. Experimental

The title compound was obtained by the nitrosation of the corresponding amine with NaNO₂/HCl in ethanol. Diffraction quality crystals of (I) were obtained by recrystallization from ethanol. The parent amine, 1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine, was obtained by the action of NaN₃/H₂SO₄ on 2,4,6,8-tetraphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one (Sivakumar, 2000) as a non-crystalline product.

S3. Refinement

All H atoms were geometrically fixed and allowed to ride on their parent atoms, with C—H distances in the range 0.86–0.96 Å, and U_iso = 1.5_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELX97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I), with the hydrogen-bonding scheme shown as dashed lines

2-Nitroso-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine

Crystal data

C24H19N3O	F(000) = 768
Mr = 365.42	Dx = 1.290 Mg m^−3
Monoclinic, P21/a	Cu Kα radiation, λ = 1.54180 Å
a = 9.713 (6) Å	Cell parameters from 25 reflections
b = 19.265 (8) Å	θ = 4.4–68.0°
c = 10.450 (2) Å	µ = 0.64 mm^−1
β = 105.74 (3)°	T = 293 K
V = 1882.1 (14) Å^3	Plate, pale yellow
Z = 4	0.2 × 0.2 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.052
Radiation source: fine-focus sealed tube	θmax = 68.0°, θmin = 4.4°
Graphite monochromator	h = −11→11
non–profiled w/2θ scans	k = 0→23
3876 measured reflections	l = −12→12
3435 independent reflections	3 standard reflections every 100 reflections
2660 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1135P)^2 + 0.167P] where P = (Fo^2 + 2Fc^2)/3
3435 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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
O	−0.2538 (2)	0.74971 (9)	−0.15540 (15)	0.0822 (5)
N1	0.26428 (18)	0.85872 (8)	0.22203 (15)	0.0560 (4)
N2	−0.14707 (17)	0.81452 (8)	0.00869 (15)	0.0519 (4)
N3	−0.2456 (2)	0.76712 (9)	−0.04006 (17)	0.0672 (5)
C1	0.0730 (2)	0.88174 (11)	0.02359 (18)	0.0566 (5)
H1A	0.1525	0.8831	−0.0160	0.068*
H1B	0.0397	0.9290	0.0268	0.068*
C2	−0.0481 (2)	0.83912 (9)	−0.06702 (18)	0.0510 (4)
H2	−0.0053	0.7982	−0.0967	0.061*
C3	−0.1325 (2)	0.83110 (10)	0.15039 (18)	0.0536 (5)
H3	−0.1762	0.7925	0.1863	0.064*
C4	0.0682 (2)	0.81396 (10)	0.3577 (2)	0.0571 (5)
H4	0.0027	0.7977	0.4010	0.069*
C5	0.2679 (3)	0.80539 (12)	0.5640 (2)	0.0682 (6)
H5	0.2064	0.7903	0.6126	0.082*
C6	0.4089 (3)	0.81350 (11)	0.6254 (2)	0.0716 (6)
H6	0.4427	0.8043	0.7159	0.086*
C7	0.5048 (3)	0.83554 (11)	0.5549 (2)	0.0681 (6)
H7	0.6014	0.8407	0.5983	0.082*
C8	0.4556 (2)	0.84951 (11)	0.4216 (2)	0.0636 (5)
H8	0.5194	0.8643	0.3751	0.076*
C9	0.3103 (2)	0.84176 (9)	0.35445 (19)	0.0538 (5)
C10	0.2133 (2)	0.81961 (9)	0.42672 (19)	0.0561 (5)
C11	0.1265 (2)	0.85525 (10)	0.16292 (18)	0.0518 (4)
C12	0.0236 (2)	0.83237 (9)	0.22719 (18)	0.0515 (4)
C13	−0.2166 (2)	0.89604 (10)	0.16495 (17)	0.0532 (5)
C14	−0.3646 (2)	0.89194 (13)	0.1294 (2)	0.0685 (6)
H14	−0.4091	0.8505	0.0961	0.082*
C15	−0.4473 (3)	0.94873 (15)	0.1426 (3)	0.0781 (7)
H15	−0.5466	0.9454	0.1186	0.094*
C16	−0.3817 (3)	1.00969 (14)	0.1911 (3)	0.0796 (7)
H16	−0.4367	1.0480	0.2001	0.095*
C17	−0.2354 (3)	1.01483 (13)	0.2266 (2)	0.0729 (6)
H17	−0.1918	1.0567	0.2588	0.087*
C18	−0.1518 (2)	0.95774 (11)	0.2149 (2)	0.0613 (5)
H18	−0.0526	0.9612	0.2406	0.074*
C19	−0.12092 (19)	0.88110 (9)	−0.18879 (17)	0.0487 (4)
C20	−0.0778 (2)	0.87241 (11)	−0.30400 (19)	0.0610 (5)
H20	−0.0128	0.8377	−0.3084	0.073*
C21	−0.1313 (3)	0.91526 (13)	−0.4122 (2)	0.0713 (6)
H21	−0.1010	0.9093	−0.4887	0.086*
C22	−0.2287 (3)	0.96660 (12)	−0.4083 (2)	0.0689 (6)
H22	−0.2635	0.9955	−0.4813	0.083*
C23	−0.2742 (2)	0.97476 (11)	−0.2953 (2)	0.0634 (5)
H23	−0.3417	1.0085	−0.2925	0.076*
C24	−0.2195 (2)	0.93276 (10)	−0.18588 (19)	0.0558 (5)
H24	−0.2492	0.9393	−0.1093	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0965 (13)	0.0837 (11)	0.0689 (10)	−0.0292 (9)	0.0266 (9)	−0.0193 (8)
N1	0.0563 (10)	0.0551 (9)	0.0562 (9)	−0.0051 (7)	0.0148 (7)	0.0006 (7)
N2	0.0516 (9)	0.0517 (8)	0.0536 (8)	−0.0102 (7)	0.0163 (7)	−0.0031 (6)
N3	0.0756 (12)	0.0641 (10)	0.0609 (10)	−0.0189 (9)	0.0168 (9)	−0.0077 (8)
C1	0.0520 (11)	0.0630 (11)	0.0554 (10)	−0.0091 (9)	0.0156 (9)	0.0051 (8)
C2	0.0517 (11)	0.0504 (9)	0.0540 (10)	−0.0011 (8)	0.0196 (8)	−0.0020 (7)
C3	0.0583 (12)	0.0568 (10)	0.0494 (10)	−0.0075 (8)	0.0207 (8)	0.0039 (8)
C4	0.0651 (12)	0.0527 (10)	0.0556 (10)	−0.0024 (9)	0.0196 (9)	0.0070 (8)
C5	0.0779 (15)	0.0669 (13)	0.0562 (11)	0.0001 (11)	0.0121 (10)	0.0109 (9)
C6	0.0878 (17)	0.0592 (12)	0.0579 (12)	−0.0039 (11)	0.0029 (11)	0.0046 (9)
C7	0.0636 (13)	0.0549 (11)	0.0753 (13)	0.0004 (9)	0.0005 (11)	0.0001 (9)
C8	0.0603 (13)	0.0588 (11)	0.0673 (12)	−0.0019 (9)	0.0097 (10)	0.0008 (9)
C9	0.0573 (11)	0.0432 (9)	0.0585 (10)	−0.0005 (8)	0.0117 (9)	−0.0008 (7)
C10	0.0635 (12)	0.0467 (9)	0.0563 (11)	−0.0020 (8)	0.0134 (9)	0.0048 (8)
C11	0.0541 (11)	0.0490 (9)	0.0534 (10)	−0.0029 (8)	0.0167 (8)	0.0003 (7)
C12	0.0549 (11)	0.0479 (9)	0.0521 (10)	−0.0045 (8)	0.0153 (8)	0.0012 (7)
C13	0.0539 (11)	0.0636 (11)	0.0475 (9)	−0.0037 (8)	0.0231 (8)	0.0041 (8)
C14	0.0547 (12)	0.0814 (14)	0.0752 (13)	−0.0093 (10)	0.0274 (10)	−0.0064 (11)
C15	0.0491 (12)	0.1019 (18)	0.0882 (16)	0.0055 (12)	0.0269 (11)	−0.0037 (14)
C16	0.0764 (16)	0.0807 (16)	0.0917 (16)	0.0113 (13)	0.0399 (13)	−0.0009 (13)
C17	0.0743 (15)	0.0663 (13)	0.0873 (15)	0.0003 (11)	0.0376 (13)	−0.0034 (11)
C18	0.0534 (11)	0.0657 (12)	0.0686 (12)	−0.0046 (9)	0.0228 (9)	−0.0019 (9)
C19	0.0461 (10)	0.0514 (9)	0.0494 (9)	−0.0049 (7)	0.0144 (8)	−0.0027 (7)
C20	0.0687 (13)	0.0633 (11)	0.0575 (11)	−0.0006 (10)	0.0281 (10)	−0.0051 (9)
C21	0.0887 (17)	0.0784 (14)	0.0544 (11)	−0.0057 (12)	0.0322 (11)	0.0018 (10)
C22	0.0809 (15)	0.0644 (12)	0.0605 (12)	−0.0058 (11)	0.0176 (11)	0.0099 (10)
C23	0.0666 (13)	0.0534 (11)	0.0700 (12)	0.0066 (9)	0.0180 (10)	0.0060 (9)
C24	0.0574 (11)	0.0573 (11)	0.0556 (10)	0.0024 (8)	0.0204 (9)	−0.0024 (8)

Geometric parameters (Å, º)

O—N3	1.233 (2)	C8—H8	0.9300
N1—C11	1.315 (3)	C9—C10	1.423 (3)
N1—C9	1.373 (2)	C11—C12	1.417 (3)
N2—N3	1.321 (2)	C13—C18	1.380 (3)
N2—C2	1.479 (2)	C13—C14	1.386 (3)
N2—C3	1.484 (2)	C14—C15	1.386 (3)
C1—C11	1.497 (3)	C14—H14	0.9300
C1—C2	1.533 (3)	C15—C16	1.366 (4)
C1—H1A	0.9700	C15—H15	0.9300
C1—H1B	0.9700	C16—C17	1.372 (4)
C2—C19	1.512 (3)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.392 (3)
C3—C12	1.511 (3)	C17—H17	0.9300
C3—C13	1.524 (3)	C18—H18	0.9300
C3—H3	0.9800	C19—C24	1.387 (3)
C4—C12	1.361 (3)	C19—C20	1.388 (2)
C4—C10	1.402 (3)	C20—C21	1.383 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.355 (4)	C21—C22	1.377 (3)
C5—C10	1.414 (3)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.377 (3)
C6—C7	1.401 (4)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.384 (3)
C7—C8	1.371 (3)	C23—H23	0.9300
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.404 (3)
C11—N1—C9	118.22 (17)	C5—C10—C9	118.4 (2)
N3—N2—C2	121.6 (2)	N1—C11—C12	123.51 (17)
N3—N2—C3	113.4 (2)	N1—C11—C1	118.72 (17)
C2—N2—C3	124.43 (15)	C12—C11—C1	117.60 (18)
O—N3—N2	114.4 (2)	C4—C12—C11	118.81 (19)
C11—C1—C2	115.09 (16)	C4—C12—C3	121.92 (18)
C11—C1—H1A	108.5	C11—C12—C3	119.25 (17)
C2—C1—H1A	108.5	C18—C13—C14	118.97 (19)
C11—C1—H1B	108.5	C18—C13—C3	122.89 (18)
C2—C1—H1B	108.5	C14—C13—C3	118.12 (18)
H1A—C1—H1B	107.5	C13—C14—C15	121.0 (2)
N2—C2—C19	113.48 (16)	C13—C14—H14	119.5
N2—C2—C1	110.02 (15)	C15—C14—H14	119.5
C19—C2—C1	109.79 (15)	C16—C15—C14	119.4 (2)
N2—C2—H2	107.8	C16—C15—H15	120.3
C19—C2—H2	107.8	C14—C15—H15	120.3
C1—C2—H2	107.8	C15—C16—C17	120.5 (2)
N2—C3—C12	110.1 (2)	C15—C16—H16	119.8
N2—C3—C13	111.6 (2)	C17—C16—H16	119.8
C12—C3—C13	114.93 (16)	C16—C17—C18	120.3 (2)
N2—C3—H3	106.6	C16—C17—H17	119.8
C12—C3—H3	106.6	C18—C17—H17	119.8
C13—C3—H3	106.6	C13—C18—C17	119.8 (2)
C12—C4—C10	119.84 (19)	C13—C18—H18	120.1
C12—C4—H4	120.1	C17—C18—H18	120.1
C10—C4—H4	120.1	C24—C19—C20	118.55 (18)
C6—C5—C10	120.8 (2)	C24—C19—C2	122.24 (16)
C6—C5—H5	119.6	C20—C19—C2	118.91 (17)
C10—C5—H5	119.6	C21—C20—C19	120.2 (2)
C5—C6—C7	121.1 (2)	C21—C20—H20	119.9
C5—C6—H6	119.5	C19—C20—H20	119.9
C7—C6—H6	119.5	C22—C21—C20	120.86 (19)
C8—C7—C6	119.7 (2)	C22—C21—H21	119.6
C8—C7—H7	120.1	C20—C21—H21	119.6
C6—C7—H7	120.1	C23—C22—C21	119.3 (2)
C7—C8—C9	120.9 (2)	C23—C22—H22	120.3
C7—C8—H8	119.6	C21—C22—H22	120.3
C9—C8—H8	119.6	C22—C23—C24	120.1 (2)
N1—C9—C8	119.12 (19)	C22—C23—H23	120.0
N1—C9—C10	121.65 (18)	C24—C23—H23	120.0
C8—C9—C10	119.16 (18)	C23—C24—C19	120.94 (18)
C4—C10—C5	123.7 (2)	C23—C24—H24	119.5
C4—C10—C9	117.89 (18)	C19—C24—H24	119.5
C2—N2—N3—O	−5.0 (3)	N1—C11—C12—C4	1.1 (3)
C3—N2—N3—O	−176.1 (2)	C1—C11—C12—C4	−174.12 (17)
N3—N2—C2—C19	68.4 (2)	N1—C11—C12—C3	179.35 (17)
C3—N2—C2—C19	−121.55 (19)	C1—C11—C12—C3	4.1 (3)
N3—N2—C2—C1	−168.15 (18)	N2—C3—C12—C4	−148.61 (17)
C3—N2—C2—C1	1.9 (2)	C13—C3—C12—C4	84.4 (2)
C11—C1—C2—N2	38.0 (2)	N2—C3—C12—C11	33.2 (2)
C11—C1—C2—C19	163.6 (2)	C13—C3—C12—C11	−93.8 (2)
N3—N2—C3—C12	133.87 (17)	N2—C3—C13—C18	−110.5 (2)
C2—N2—C3—C12	−36.9 (2)	C12—C3—C13—C18	15.8 (2)
N3—N2—C3—C13	−97.3 (2)	N2—C3—C13—C14	71.2 (2)
C2—N2—C3—C13	92.0 (2)	C12—C3—C13—C14	−162.57 (17)
C10—C5—C6—C7	−0.6 (4)	C18—C13—C14—C15	0.4 (3)
C5—C6—C7—C8	0.3 (3)	C3—C13—C14—C15	178.8 (2)
C6—C7—C8—C9	−0.2 (3)	C13—C14—C15—C16	0.2 (4)
C11—N1—C9—C8	−175.84 (17)	C14—C15—C16—C17	−0.1 (4)
C11—N1—C9—C10	1.2 (3)	C15—C16—C17—C18	−0.6 (4)
C7—C8—C9—N1	177.61 (18)	C14—C13—C18—C17	−1.0 (3)
C7—C8—C9—C10	0.5 (3)	C3—C13—C18—C17	−179.34 (18)
C12—C4—C10—C5	176.35 (19)	C16—C17—C18—C13	1.2 (3)
C12—C4—C10—C9	−2.8 (3)	N2—C2—C19—C24	45.2 (2)
C6—C5—C10—C4	−178.4 (2)	C1—C2—C19—C24	−78.4 (2)
C6—C5—C10—C9	0.8 (3)	N2—C2—C19—C20	−141.18 (17)
N1—C9—C10—C4	1.4 (3)	C1—C2—C19—C20	95.2 (2)
C8—C9—C10—C4	178.49 (18)	C24—C19—C20—C21	0.9 (3)
N1—C9—C10—C5	−177.79 (18)	C2—C19—C20—C21	−173.01 (19)
C8—C9—C10—C5	−0.7 (3)	C19—C20—C21—C22	−0.7 (3)
C9—N1—C11—C12	−2.5 (3)	C20—C21—C22—C23	−0.6 (4)
C9—N1—C11—C1	172.66 (16)	C21—C22—C23—C24	1.5 (3)
C2—C1—C11—N1	142.07 (18)	C22—C23—C24—C19	−1.3 (3)
C2—C1—C11—C12	−42.5 (2)	C20—C19—C24—C23	0.1 (3)
C10—C4—C12—C11	1.7 (3)	C2—C19—C24—C23	173.79 (18)
C10—C4—C12—C3	−176.49 (17)