2-Amino-4-(4-methoxy­phen­yl)-4H-benzo[h]chromene-3-carbonitrile

Gu, X.-F.; Guo, C.; Zhang, D.-M.; Tang, Q.-G.

doi:10.1107/S160053680502982X

2-Amino-4-(4-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile

X.-F. Gu, C. Guo, D.-M. Zhang and Q.-G. Tang

The title compound, C₂₁H₁₆N₂O₂, was synthesized by the reaction of 1-naphthol with malononitrile and 4-methoxybenzaldehyde in ethanol under microwave irradiation. A weak intramolecular C—H

π interaction is found.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502982X/ac6199sup1.cif Contains datablocks g, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680502982X/ac6199Isup2.hkl Contains datablock I

CCDC reference: 287431

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.202
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       6.31 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N1  -C9  -C10 -C11    18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N1  -C9  -C10 -C8      2.00  5.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Benzopyrans and their derivatives are important in natural and synthetic organic chemistry owing to their biological and pharmacological properties (Morianka & Takahashi, 1977), such as antisterility (Brooks, 1998) and anticancer activities (Hyana & Saimoto, 1987). In addition, polyfunctionalized benzopyrans constitute the structural unit of a number of natural products and, because of the inherent reactivity of the inbuilt pyran ring, these are versatile synthons (Hatakeyama et al., 1988). We report here the crystal structure of the title compound, (I).

The molecular structure of (I), shown in Fig. 1, exhibits weak intramolecular C—H···π interactions (Fig.2, Table 2), which generate a three-dimensional network.

Experimental top

Compound (I) was prepared by the reaction of 1-naphthol (5 mmol) with malononitrile (5 mmol) and 4-methoxybenzaldehyde (5 mmol) in ethanol (4 ml) using piperidine as catalyst under microwave irradiation. Pure compound (I) was obtained by recrystallization from ethanol (m.p. 464–466 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m.): 8.23 (d, 1H), 7.88 (d, 1H), 7.55–7.65 (m, 3H), 7.16 (d, 2H), 7.08–7.10 (m, 3H), 6.87 (d, 2H), 4.84 (s, 1H), 3.71(s, 3H).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I).

Fig. 2. The C—H···π interactions in (I), shown as dashed lines.

2-amino-4-(4-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile top

Crystal data top

C₂₁H₁₆N₂O₂	Z = 2
M_r = 328.36	F(000) = 344
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4140 (13) Å	Cell parameters from 25 reflections
b = 10.643 (2) Å	θ = 10–12°
c = 13.308 (3) Å	µ = 0.08 mm⁻¹
α = 108.59 (3)°	T = 293 K
β = 96.11 (3)°	Block, colourless
γ = 96.95 (3)°	0.4 × 0.4 × 0.2 mm
V = 844.5 (3) Å³

Data collection top

Nonius CAD4 diffractometer	R_int = 0.018
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 1.6°
Graphite monochromator	h = 0→7
ω/2θ scans	k = −12→12
3594 measured reflections	l = −15→15
3287 independent reflections	3 standard reflections every 200 reflections
2023 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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.202	w = 1/[σ²(F_o²) + (0.130P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3287 reflections	Δρ_max = 0.22 e Å⁻³
235 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (10)

Crystal data top

C₂₁H₁₆N₂O₂	γ = 96.95 (3)°
M_r = 328.36	V = 844.5 (3) Å³
Triclinic, P1	Z = 2
a = 6.4140 (13) Å	Mo Kα radiation
b = 10.643 (2) Å	µ = 0.08 mm⁻¹
c = 13.308 (3) Å	T = 293 K
α = 108.59 (3)°	0.4 × 0.4 × 0.2 mm
β = 96.11 (3)°

Data collection top

Nonius CAD4 diffractometer	R_int = 0.018
3594 measured reflections	3 standard reflections every 200 reflections
3287 independent reflections	intensity decay: none
2023 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.202	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
3287 reflections	Δρ_min = −0.20 e Å⁻³
235 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
O1	0.3695 (3)	0.29973 (17)	0.88148 (15)	0.0798 (6)
O2	0.3768 (2)	0.96617 (15)	0.76767 (12)	0.0596 (5)
N1	1.0298 (3)	0.8649 (2)	0.90388 (17)	0.0732 (6)
N2	0.6335 (4)	1.0832 (2)	0.90233 (19)	0.0730 (7)
C1	0.1913 (6)	0.2915 (3)	0.9340 (3)	0.0948 (10)
H1A	0.1838	0.2138	0.9562	0.142*
H1B	0.0644	0.2843	0.8858	0.142*
H1C	0.2044	0.3708	0.9958	0.142*
C2	0.4087 (4)	0.4050 (2)	0.84362 (18)	0.0575 (6)
C3	0.5833 (4)	0.4082 (2)	0.7921 (2)	0.0662 (7)
H3A	0.6680	0.3418	0.7854	0.079*
C4	0.6333 (4)	0.5090 (2)	0.75041 (18)	0.0596 (6)
H4A	0.7515	0.5095	0.7156	0.072*
C5	0.5112 (3)	0.6098 (2)	0.75921 (16)	0.0489 (5)
C6	0.3385 (4)	0.6054 (2)	0.8116 (2)	0.0641 (7)
H6A	0.2543	0.6721	0.8188	0.077*
C7	0.2859 (4)	0.5047 (2)	0.8542 (2)	0.0663 (7)
H7A	0.1686	0.5045	0.8896	0.080*
C8	0.5679 (3)	0.7229 (2)	0.71396 (17)	0.0522 (5)
H8A	0.6749	0.6973	0.6672	0.063*
C9	0.8644 (3)	0.8632 (2)	0.85951 (17)	0.0552 (6)
C10	0.6619 (3)	0.8549 (2)	0.80195 (17)	0.0511 (5)
C11	0.5645 (3)	0.9638 (2)	0.82482 (18)	0.0518 (6)
C12	0.2888 (3)	0.8560 (2)	0.67716 (17)	0.0500 (5)
C13	0.0966 (3)	0.8720 (2)	0.62116 (17)	0.0515 (6)
C14	0.0004 (4)	0.9869 (3)	0.6559 (2)	0.0654 (7)
H14A	0.0648	1.0587	0.7165	0.079*
C15	−0.1895 (4)	0.9931 (3)	0.6002 (2)	0.0802 (8)
H15A	−0.2534	1.0689	0.6241	0.096*
C16	−0.2875 (4)	0.8869 (4)	0.5082 (2)	0.0853 (9)
H16A	−0.4164	0.8923	0.4719	0.102*
C17	−0.1960 (4)	0.7764 (3)	0.4717 (2)	0.0747 (8)
H17A	−0.2616	0.7068	0.4098	0.090*
C18	−0.0010 (4)	0.7655 (3)	0.52681 (18)	0.0601 (6)
C19	0.0974 (4)	0.6512 (3)	0.49201 (19)	0.0688 (7)
H19A	0.0391	0.5827	0.4281	0.083*
C20	0.2775 (4)	0.6397 (3)	0.55075 (19)	0.0671 (7)
H20A	0.3371	0.5621	0.5268	0.081*
C21	0.3760 (3)	0.7425 (2)	0.64717 (17)	0.0520 (5)
H2	0.545 (5)	1.150 (3)	0.907 (2)	0.085 (8)*
H1	0.736 (4)	1.093 (3)	0.957 (2)	0.075 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0924 (14)	0.0657 (11)	0.0920 (13)	0.0153 (9)	0.0074 (11)	0.0424 (10)
O2	0.0426 (8)	0.0589 (9)	0.0726 (10)	0.0102 (7)	−0.0128 (7)	0.0216 (8)
N1	0.0501 (12)	0.0875 (15)	0.0769 (14)	0.0247 (10)	−0.0083 (10)	0.0216 (11)
N2	0.0623 (13)	0.0573 (13)	0.0858 (15)	0.0123 (10)	−0.0251 (12)	0.0164 (11)
C1	0.109 (2)	0.086 (2)	0.101 (2)	0.0000 (17)	0.0209 (19)	0.0514 (18)
C2	0.0616 (14)	0.0521 (13)	0.0582 (13)	0.0104 (10)	−0.0039 (11)	0.0214 (10)
C3	0.0668 (15)	0.0629 (14)	0.0730 (15)	0.0296 (12)	0.0022 (12)	0.0245 (12)
C4	0.0497 (13)	0.0691 (15)	0.0632 (13)	0.0242 (11)	0.0089 (10)	0.0211 (11)
C5	0.0405 (11)	0.0539 (12)	0.0522 (12)	0.0138 (9)	0.0019 (9)	0.0170 (9)
C6	0.0600 (14)	0.0611 (14)	0.0860 (16)	0.0296 (11)	0.0237 (13)	0.0340 (12)
C7	0.0616 (15)	0.0667 (15)	0.0806 (16)	0.0169 (12)	0.0223 (12)	0.0325 (13)
C8	0.0390 (11)	0.0617 (13)	0.0571 (12)	0.0113 (9)	0.0057 (9)	0.0211 (10)
C9	0.0466 (12)	0.0604 (13)	0.0609 (13)	0.0148 (10)	0.0042 (10)	0.0227 (11)
C10	0.0355 (10)	0.0590 (13)	0.0612 (13)	0.0075 (9)	−0.0015 (9)	0.0265 (10)
C11	0.0369 (11)	0.0558 (13)	0.0629 (13)	0.0024 (9)	−0.0050 (9)	0.0263 (11)
C12	0.0390 (11)	0.0576 (13)	0.0551 (12)	0.0010 (9)	−0.0013 (9)	0.0264 (10)
C13	0.0374 (11)	0.0680 (14)	0.0565 (12)	0.0018 (10)	0.0007 (9)	0.0356 (11)
C14	0.0478 (13)	0.0762 (16)	0.0789 (16)	0.0125 (11)	−0.0031 (12)	0.0383 (13)
C15	0.0526 (14)	0.105 (2)	0.098 (2)	0.0235 (14)	−0.0020 (14)	0.0545 (18)
C16	0.0439 (14)	0.125 (3)	0.100 (2)	0.0134 (15)	−0.0094 (14)	0.061 (2)
C17	0.0486 (14)	0.107 (2)	0.0709 (16)	−0.0033 (14)	−0.0101 (12)	0.0456 (15)
C18	0.0449 (12)	0.0793 (16)	0.0620 (14)	−0.0005 (11)	−0.0013 (10)	0.0387 (12)
C19	0.0595 (15)	0.0812 (17)	0.0556 (14)	−0.0027 (13)	−0.0064 (12)	0.0191 (12)
C20	0.0644 (15)	0.0715 (16)	0.0592 (14)	0.0120 (12)	0.0015 (12)	0.0157 (12)
C21	0.0420 (11)	0.0615 (13)	0.0555 (12)	0.0058 (9)	0.0036 (10)	0.0261 (10)

Geometric parameters (Å, º) top

O1—C2	1.375 (3)	C8—C21	1.515 (3)
O1—C1	1.410 (4)	C8—C10	1.518 (3)
O2—C11	1.361 (2)	C8—H8A	0.9800
O2—C12	1.393 (3)	C9—C10	1.414 (3)
N1—C9	1.153 (3)	C10—C11	1.348 (3)
N2—C11	1.344 (3)	C12—C21	1.354 (3)
N2—H2	0.96 (3)	C12—C13	1.429 (3)
N2—H1	0.90 (3)	C13—C14	1.405 (3)
C1—H1A	0.9600	C13—C18	1.417 (3)
C1—H1B	0.9600	C14—C15	1.377 (3)
C1—H1C	0.9600	C14—H14A	0.9300
C2—C3	1.376 (3)	C15—C16	1.398 (4)
C2—C7	1.377 (3)	C15—H15A	0.9300
C3—C4	1.378 (3)	C16—C17	1.352 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.385 (3)	C17—C18	1.417 (3)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.374 (3)	C18—C19	1.407 (4)
C5—C8	1.532 (3)	C19—C20	1.365 (3)
C6—C7	1.387 (3)	C19—H19A	0.9300
C6—H6A	0.9300	C20—C21	1.417 (3)
C7—H7A	0.9300	C20—H20A	0.9300

C2—O1—C1	118.5 (2)	C11—C10—C9	119.4 (2)
C11—O2—C12	119.09 (16)	C11—C10—C8	123.13 (18)
C11—N2—H2	116.3 (17)	C9—C10—C8	117.47 (18)
C11—N2—H1	121.3 (16)	N2—C11—C10	127.1 (2)
H2—N2—H1	120 (2)	N2—C11—O2	110.26 (18)
O1—C1—H1A	109.5	C10—C11—O2	122.6 (2)
O1—C1—H1B	109.5	C21—C12—O2	122.50 (18)
H1A—C1—H1B	109.5	C21—C12—C13	123.3 (2)
O1—C1—H1C	109.5	O2—C12—C13	114.15 (18)
H1A—C1—H1C	109.5	C14—C13—C18	119.1 (2)
H1B—C1—H1C	109.5	C14—C13—C12	123.1 (2)
O1—C2—C3	116.3 (2)	C18—C13—C12	117.8 (2)
O1—C2—C7	124.4 (2)	C15—C14—C13	119.9 (2)
C3—C2—C7	119.3 (2)	C15—C14—H14A	120.0
C2—C3—C4	120.4 (2)	C13—C14—H14A	120.0
C2—C3—H3A	119.8	C14—C15—C16	120.9 (3)
C4—C3—H3A	119.8	C14—C15—H15A	119.5
C3—C4—C5	121.4 (2)	C16—C15—H15A	119.5
C3—C4—H4A	119.3	C17—C16—C15	120.4 (2)
C5—C4—H4A	119.3	C17—C16—H16A	119.8
C6—C5—C4	117.3 (2)	C15—C16—H16A	119.8
C6—C5—C8	121.15 (18)	C16—C17—C18	120.6 (3)
C4—C5—C8	121.51 (19)	C16—C17—H17A	119.7
C5—C6—C7	122.0 (2)	C18—C17—H17A	119.7
C5—C6—H6A	119.0	C19—C18—C13	118.7 (2)
C7—C6—H6A	119.0	C19—C18—C17	122.2 (2)
C2—C7—C6	119.6 (2)	C13—C18—C17	119.0 (2)
C2—C7—H7A	120.2	C20—C19—C18	120.9 (2)
C6—C7—H7A	120.2	C20—C19—H19A	119.6
C21—C8—C10	109.44 (17)	C18—C19—H19A	119.6
C21—C8—C5	111.38 (16)	C19—C20—C21	121.9 (2)
C10—C8—C5	111.96 (17)	C19—C20—H20A	119.1
C21—C8—H8A	108.0	C21—C20—H20A	119.1
C10—C8—H8A	108.0	C12—C21—C20	117.2 (2)
C5—C8—H8A	108.0	C12—C21—C8	122.2 (2)
N1—C9—C10	177.3 (2)	C20—C21—C8	120.52 (19)

C1—O1—C2—C3	−179.5 (2)	C11—O2—C12—C13	−177.54 (17)
C1—O1—C2—C7	0.5 (4)	C21—C12—C13—C14	176.3 (2)
O1—C2—C3—C4	179.2 (2)	O2—C12—C13—C14	−2.0 (3)
C7—C2—C3—C4	−0.8 (4)	C21—C12—C13—C18	−3.0 (3)
C2—C3—C4—C5	0.3 (4)	O2—C12—C13—C18	178.74 (17)
C3—C4—C5—C6	0.2 (3)	C18—C13—C14—C15	1.9 (3)
C3—C4—C5—C8	179.3 (2)	C12—C13—C14—C15	−177.4 (2)
C4—C5—C6—C7	−0.2 (3)	C13—C14—C15—C16	−0.8 (4)
C8—C5—C6—C7	−179.3 (2)	C14—C15—C16—C17	−0.6 (4)
O1—C2—C7—C6	−179.2 (2)	C15—C16—C17—C18	0.9 (4)
C3—C2—C7—C6	0.8 (4)	C14—C13—C18—C19	179.4 (2)
C5—C6—C7—C2	−0.3 (4)	C12—C13—C18—C19	−1.2 (3)
C6—C5—C8—C21	−49.6 (3)	C14—C13—C18—C17	−1.6 (3)
C4—C5—C8—C21	131.3 (2)	C12—C13—C18—C17	177.71 (19)
C6—C5—C8—C10	73.3 (2)	C16—C17—C18—C19	179.2 (2)
C4—C5—C8—C10	−105.8 (2)	C16—C17—C18—C13	0.2 (4)
N1—C9—C10—C11	−176 (100)	C13—C18—C19—C20	3.4 (4)
N1—C9—C10—C8	2 (5)	C17—C18—C19—C20	−175.5 (2)
C21—C8—C10—C11	9.8 (3)	C18—C19—C20—C21	−1.7 (4)
C5—C8—C10—C11	−114.2 (2)	O2—C12—C21—C20	−177.11 (19)
C21—C8—C10—C9	−168.21 (18)	C13—C12—C21—C20	4.7 (3)
C5—C8—C10—C9	67.8 (2)	O2—C12—C21—C8	4.3 (3)
C9—C10—C11—N2	−3.5 (4)	C13—C12—C21—C8	−173.90 (18)
C8—C10—C11—N2	178.5 (2)	C19—C20—C21—C12	−2.4 (3)
C9—C10—C11—O2	175.18 (19)	C19—C20—C21—C8	176.3 (2)
C8—C10—C11—O2	−2.8 (3)	C10—C8—C21—C12	−10.4 (3)
C12—O2—C11—N2	174.00 (18)	C5—C8—C21—C12	113.9 (2)
C12—O2—C11—C10	−4.9 (3)	C10—C8—C21—C20	170.99 (19)
C11—O2—C12—C21	4.2 (3)	C5—C8—C21—C20	−64.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cg1	0.93	2.77	3.1243	104

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O₂
M_r	328.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.4140 (13), 10.643 (2), 13.308 (3)
α, β, γ (°)	108.59 (3), 96.11 (3), 96.95 (3)
V (Å³)	844.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.4 × 0.4 × 0.2

Data collection
Diffractometer	Nonius CAD4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3594, 3287, 2023
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.202, 1.02
No. of reflections	3287
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C2	1.375 (3)	N1—C9	1.153 (3)
O1—C1	1.410 (4)	N2—C11	1.344 (3)
O2—C11	1.361 (2)	C5—C8	1.532 (3)
O2—C12	1.393 (3)	C9—C10	1.414 (3)

C2—O1—C1	118.5 (2)	C9—C10—C8	117.47 (18)
C11—O2—C12	119.09 (16)	N2—C11—C10	127.1 (2)
O1—C2—C3	116.3 (2)	N2—C11—O2	110.26 (18)
O1—C2—C7	124.4 (2)	C10—C11—O2	122.6 (2)
C6—C5—C8	121.15 (18)	C21—C12—O2	122.50 (18)
C4—C5—C8	121.51 (19)	O2—C12—C13	114.15 (18)
C21—C8—C5	111.38 (16)	C14—C13—C12	123.1 (2)
C10—C8—C5	111.96 (17)	C19—C18—C17	122.2 (2)
N1—C9—C10	177.3 (2)	C20—C21—C8	120.52 (19)
C11—C10—C9	119.4 (2)