Two (Z)-N-aryl-3-benzylideneisoindolin-1-ones

Two isoindolin-1-one derivatives, (Z)-3-benzyl­idene-N-phenyl­isoindolin-1-one, C₂₁H₁₅NO, (II), and (Z)-3-benzyl­idene-N-(4-methoxy­phenyl)­isoindolin-1-one, C₂₂H₁₇NO₂, (III), were synthesized by the palladium-catalysed heteroannulation. The mol­ecules of both compounds have a Z configuration. The interplanar angles between the five- and six-membered rings of the isoindolinone moiety in (II) and (III) are 1.66 (11) and 2.26 (7)°, respectively. The phenyl rings at the N-position in (II) and (III) are twisted out of the C₄N ring plane by 62.77 (11) and 67.10 (7)°, respectively. The substitutions at the N and C-3 positions of the isoindolinone system have little influence on the molecular dimensions of the resulting compounds.

S1. Comment

The isoindolinone (phthalimidine) system (I) is present in a number of natural products. Many isoindolinone derivatives display biological activity as potential anti-inflammatory agents, antipsychotics (Zhuang et al., 1998; Linden et al., 1997) and inhibitors of human CCRF-CEM lymphoblastic leukaemic cells (Taylor et al., 1997). The majority of structurally determined isoindolinone systems are either N-substituted or have a hydroxy substituent at the 3-position (Brady et al., 1998; McNab et al., 1997; Barrett et al., 1996; Feeder & Jones 1996). As part of an ongoing program on the synthesis and characterization of new heterocyclic systems containing an isoindolinone moiety, we have recently reported the crystal structures of several N– and C₃-substituted derivatives (Khan et al., 1998; Kundu et al., 1999; Guha et al., 1999). The molecular configurations, E or Z, of these compounds are influenced by the type of substituents. To study the effect of substitution on the conformation of the resulting compounds and to build up a hierarchy for such systems, X-ray analyses of (Z)-3-benzylidene-N-phenylisoindolin-1-one, (II), and (Z)-3-benzylidene-N-(p-methoxyphenyl)isoindolin-1-one, (III), were undertaken.

The Z configuration of the molecules of (II) and (III), which contain essentially planar isoindolinone and phenyl moieties, are established by the torsion angle N—C14—C15—C16 of 5.4 (5) and 3.3 (4)° in (II) and (III), respectively. The bond lengths and angles observed for the heterocyclic ring in (II) and (III) are similar to those reported for substituted isoindolinone structures (Kundu et al., 1999; Khan et al., 1998; McNab et al., 1997; Feeder & Jones, 1996). The angles between the five- and six-membered rings of the isoindolinone system in (II) and (III) are 1.66 (11) and 2.26 (7)°, respectively; the maximum deviation from planarity for an atom in either ring plane is 0.009 (3) Å for C7 in (II), with the carbonyl-O atom 0.030 (3) Å [in (2)] and 0.004 (2) Å [in (III)] away from the C₄N planes. The phenyl rings (C1—C6) and (C16—C21) in (II) are twisted out of the C₄N ring plane with dihedral angles 62.77 (11) and 55.72 (10)°, respectively; the corresponding values are 67.10 (7) and 55.05 (7)° in (III). In the fused six-membered ring (C8—C13) of (II) and (III), the angles at C9 and C12 are less than 118°, an effect previously noted by McNab et al. (1997). The cis orientation of O2—C22 with respect to C3—C4 about the O2—C3 bond in (III) results in repulsion between the C4 and C22 atoms and because of this the bond angle C4—C3—O2 is increased by about 9° (Table 3) compared to C2—C3—O2. The torsion angle C4—C3—O2—C22 is 7.3 (3)°. In both the structures, the carbonyl atoms (O, O1) are involved in weak C—H···O intermolecular hydrogen bonds (Tables 2 and 4).

A comparison of geometrical parameters of various isoindolinone derivatives (Table 5) reveals that substitutions at N– and/or C₃(14)- positions have apparently little influence on the molecular dimensions. The dihedral angles between the isoindolinone moiety and the planar parts of the R1/R2 groups in different compounds (Table 5) indicate an approximate molecular coplanarity for the N-unsubstituted derivative (Kundu et al., 1999) while the alkyl/aryl substitutions at both the N– and C₃– positions introduce considerable puckering in the resulting molecules.

S2. Experimental

2-(2'-Phenylethynyl)-N-phenyl benzamide (PEPB) was synthesized by stirring a mixture of 2-iodo-N-phenyl benzamide (1 mmol) with phenylacetylene (1.2 mmol) in dimethylformamide (DMF) (5 ml) at 353 K for 16 h in the presence of bis(triphenylphosphine)palladium(II) chloride (3.5 mol%), cuprous iodide (8 mol%) and triethylamine (4 mmol). After usual workup and purification by chromatography (silica gel 60–80 mesh), the product (PEPB) was cyclized to 3-benzylidene-N-phenylisoindolin-1-one, (II), m.p. 470 (1) K, by refluxing with sodium ethoxide in ethanol for 4 h. Single crystals suitable for X-ray analysis were obtained from ethanol. Elemental analysis: calculated for C₂₁H₁₅NO: C 84.82, H 5.08, N 4.71%; found: C 84.49, H 5.13, N 4.60%. Starting with 2-iodo-N-p-anisyl benzamide, the procedure as described above yielded 2-(2'-phenylethynyl)-N-p-methoxyphenylbenzamide (PEMB), which on cyclization afforded 3-benzylidene-N-(4-methoxyphenyl)isoindolin-1-one, (III), m.p. 441 (1) K. Single crystals suitable for X-ray analysis were obtained from ethanol. Elemental analysis: calculated for C₂₂H₁₇NO₂, C 80.91, H 5.23, N 4.27%; found: C 80.90, H 5.36, N 4.13%.

S3. Refinement

All H-atoms were generated using HFIX in SHELX93 (Sheldrick, 1993). U_iso for H atoms were assigned as 1.2 times U_eq of the parent non-H atoms before anisotropic refinement.

Computing details

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: MULTAN88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL93 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (II) showing the 50% probability displacement ellipsoids.
	Fig. 2. The molecular structure of (III) showing the 50% probability displacement ellipsoids.

(II) (Z)-3-benzylidene-N-phenylisoindolin-1-one

Crystal data

C21H15NO	Dx = 1.293 Mg m^−3
Mr = 297.34	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 9.366 (3) Å	θ = 25.1–29.8°
b = 19.875 (1) Å	µ = 0.62 mm^−1
c = 8.204 (9) Å	T = 293 K
V = 1527.2 (17) Å^3	Prism, colourless
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 624

Data collection

Rigaku AFC5R diffractometer	1403 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.000
Graphite monochromator	θmax = 79.7°, θmin = 4.5°
ω–2θ scans	h = 0→11
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = 0→23
Tmin = 0.815, Tmax = 0.856	l = 0→10
1589 measured reflections	3 standard reflections every 100 reflections
1589 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.106	Calculated w = 1/[σ^2(Fo^2) + (0.0652P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = −0.005
1589 reflections	Δρmax = 0.16 e Å^−3
208 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Absolute structure: could not ascertained
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.6 (7)

Special details

Refinement. Both the structures were solved by direct methods and refined by full-matrix least squares techniques.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N	0.3855 (3)	0.70495 (11)	0.6379 (3)	0.0473 (5)
O	0.4031 (3)	0.61300 (11)	0.8094 (2)	0.0750 (7)
C1	0.4946 (3)	0.76486 (15)	0.8630 (3)	0.0572 (7)
H1	0.5749	0.7376	0.8539	0.064*
C2	0.4907 (4)	0.8157 (2)	0.9775 (4)	0.0662 (9)
H2	0.5688	0.8226	1.0456	0.079*
C3	0.3725 (4)	0.8564 (2)	0.9917 (3)	0.0658 (9)
H3	0.3714	0.8913	1.0673	0.079*
C4	0.2552 (4)	0.8451 (2)	0.8930 (4)	0.0639 (8)
H4	0.1746	0.8721	0.9029	0.068*
C5	0.2577 (3)	0.79367 (14)	0.7795 (4)	0.0528 (7)
H5	0.1780	0.7853	0.7150	0.052*
C6	0.3789 (3)	0.75477 (13)	0.7623 (3)	0.0464 (6)
C7	0.3933 (3)	0.63635 (14)	0.6729 (3)	0.0516 (7)
C8	0.3869 (3)	0.60185 (14)	0.5141 (3)	0.0477 (6)
C9	0.3956 (4)	0.53350 (15)	0.4786 (4)	0.0587 (8)
H9	0.4061	0.5016	0.5607	0.064*
C10	0.3879 (4)	0.51475 (15)	0.3160 (4)	0.0620 (8)
H10	0.3930	0.4695	0.2879	0.077*
C11	0.3730 (3)	0.5624 (2)	0.1960 (4)	0.0594 (7)
H11	0.3684	0.5486	0.0879	0.067*
C12	0.3648 (3)	0.63022 (15)	0.2311 (3)	0.0518 (7)
H12	0.3545	0.6620	0.1487	0.067*
C13	0.3723 (3)	0.64933 (13)	0.3936 (3)	0.0449 (6)
C14	0.3718 (3)	0.71650 (13)	0.4677 (3)	0.0409 (5)
C15	0.3627 (3)	0.77449 (14)	0.3868 (3)	0.0474 (6)
H15	0.3458	0.7701	0.2756	0.052*
C16	0.3751 (3)	0.84448 (13)	0.4446 (3)	0.0439 (6)
C17	0.2704 (3)	0.8911 (2)	0.4065 (4)	0.0560 (7)
H17	0.1931	0.8783	0.3424	0.061*
C18	0.2797 (4)	0.9563 (2)	0.4624 (4)	0.0661 (9)
H18	0.2088	0.9872	0.4361	0.076*
C19	0.3933 (4)	0.97573 (15)	0.5571 (4)	0.0635 (8)
H19	0.3974	1.0192	0.5987	0.071*
C20	0.5008 (3)	0.9309 (2)	0.5902 (4)	0.0593 (7)
H20	0.5799	0.9445	0.6502	0.085*
C21	0.4915 (3)	0.86590 (14)	0.5347 (3)	0.0494 (6)
H21	0.5646	0.8357	0.5579	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0598 (13)	0.0417 (12)	0.0405 (10)	0.0026 (11)	−0.0007 (11)	0.0033 (9)
O	0.115 (2)	0.0582 (13)	0.0516 (11)	0.0077 (14)	−0.0024 (14)	0.0156 (10)
C1	0.063 (2)	0.064 (2)	0.0449 (13)	0.009 (2)	−0.0047 (14)	0.0035 (14)
C2	0.083 (2)	0.070 (2)	0.0458 (14)	0.000 (2)	−0.012 (2)	0.0021 (15)
C3	0.096 (3)	0.058 (2)	0.0434 (14)	0.001 (2)	0.010 (2)	−0.0015 (13)
C4	0.073 (2)	0.060 (2)	0.058 (2)	0.012 (2)	0.017 (2)	−0.001 (2)
C5	0.0487 (14)	0.056 (2)	0.0539 (14)	−0.0013 (14)	0.0052 (13)	0.0016 (14)
C6	0.0578 (15)	0.0455 (14)	0.0358 (11)	−0.0005 (14)	0.0057 (13)	0.0056 (11)
C7	0.057 (2)	0.046 (2)	0.0515 (14)	0.0044 (14)	0.0011 (15)	0.0083 (13)
C8	0.0466 (14)	0.0451 (15)	0.0513 (14)	0.0007 (13)	0.0014 (13)	0.0041 (12)
C9	0.062 (2)	0.045 (2)	0.069 (2)	0.0050 (14)	−0.001 (2)	0.0065 (15)
C10	0.065 (2)	0.048 (2)	0.074 (2)	0.0005 (15)	0.003 (2)	−0.0125 (15)
C11	0.059 (2)	0.062 (2)	0.057 (2)	0.000 (2)	0.006 (2)	−0.0146 (14)
C12	0.055 (2)	0.056 (2)	0.0452 (12)	−0.0010 (15)	0.0032 (13)	−0.0027 (12)
C13	0.0401 (13)	0.048 (2)	0.0467 (13)	0.0018 (13)	0.0032 (13)	0.0019 (11)
C14	0.0384 (12)	0.0472 (14)	0.0370 (11)	−0.0001 (12)	0.0014 (11)	0.0005 (10)
C15	0.0515 (15)	0.0494 (15)	0.0413 (12)	−0.0031 (13)	−0.0015 (13)	0.0042 (11)
C16	0.0453 (14)	0.0457 (14)	0.0406 (12)	−0.0028 (12)	0.0042 (12)	0.0066 (11)
C17	0.050 (2)	0.057 (2)	0.061 (2)	0.0008 (14)	−0.0100 (14)	0.003 (2)
C18	0.066 (2)	0.052 (2)	0.080 (2)	0.010 (2)	−0.002 (2)	−0.002 (2)
C19	0.076 (2)	0.049 (2)	0.066 (2)	−0.011 (2)	0.009 (2)	−0.004 (2)
C20	0.059 (2)	0.064 (2)	0.0545 (15)	−0.019 (2)	−0.004 (2)	0.005 (2)
C21	0.0437 (14)	0.054 (2)	0.0503 (14)	−0.0024 (13)	0.0004 (13)	0.0109 (13)

Geometric parameters (Å, º)

N—C7	1.395 (3)	C10—H10	0.930
N—C14	1.421 (3)	C11—C12	1.380 (4)
N—C6	1.423 (3)	C11—H11	0.930
O—C7	1.216 (3)	C12—C13	1.388 (4)
C1—C6	1.377 (4)	C12—H12	0.930
C1—C2	1.381 (4)	C13—C14	1.467 (4)
C1—H1	0.930	C14—C15	1.333 (4)
C2—C3	1.376 (5)	C15—C16	1.474 (4)
C2—H2	0.930	C15—H15	0.930
C3—C4	1.383 (5)	C16—C21	1.384 (4)
C3—H3	0.930	C16—C17	1.385 (4)
C4—C5	1.383 (4)	C17—C18	1.377 (4)
C4—H4	0.930	C17—H17	0.930
C5—C6	1.381 (4)	C18—C19	1.373 (5)
C5—H5	0.930	C18—H18	0.930
C7—C8	1.473 (4)	C19—C20	1.371 (4)
C8—C13	1.374 (4)	C19—H19	0.930
C8—C9	1.392 (4)	C20—C21	1.373 (4)
C9—C10	1.387 (5)	C20—H20	0.930
C9—H9	0.930	C21—H21	0.930
C10—C11	1.373 (4)
C7—N—C14	111.4 (2)	C10—C11—C12	122.0 (3)
C7—N—C6	122.3 (2)	C10—C11—H11	119.0
C14—N—C6	126.0 (2)	C12—C11—H11	119.0
C6—C1—C2	119.6 (3)	C11—C12—C13	117.7 (3)
C6—C1—H1	120.2	C11—C12—H12	121.2
C2—C1—H1	120.2	C13—C12—H12	121.2
C3—C2—C1	120.6 (3)	C8—C13—C12	120.6 (3)
C3—C2—H2	119.7	C8—C13—C14	109.1 (2)
C1—C2—H2	119.7	C12—C13—C14	130.3 (2)
C2—C3—C4	119.6 (3)	C15—C14—N	129.4 (2)
C2—C3—H3	120.2	C15—C14—C13	125.5 (2)
C4—C3—H3	120.2	N—C14—C13	105.1 (2)
C3—C4—C5	120.0 (3)	C14—C15—C16	130.6 (2)
C3—C4—H4	120.0	C14—C15—H15	114.7
C5—C4—H4	120.0	C16—C15—H15	114.7
C6—C5—C4	119.8 (3)	C21—C16—C17	118.2 (3)
C6—C5—H5	120.1	C21—C16—C15	121.6 (2)
C4—C5—H5	120.1	C17—C16—C15	120.2 (3)
C1—C6—C5	120.3 (3)	C18—C17—C16	120.6 (3)
C1—C6—N	119.8 (3)	C18—C17—H17	119.7
C5—C6—N	119.9 (3)	C16—C17—H17	119.7
O—C7—N	124.5 (3)	C19—C18—C17	120.2 (3)
O—C7—C8	129.8 (3)	C19—C18—H18	119.9
N—C7—C8	105.7 (2)	C17—C18—H18	119.9
C13—C8—C9	121.7 (3)	C18—C19—C20	119.9 (3)
C13—C8—C7	108.7 (2)	C18—C19—H19	120.1
C9—C8—C7	129.6 (3)	C20—C19—H19	120.1
C10—C9—C8	117.5 (3)	C19—C20—C21	119.9 (3)
C10—C9—H9	121.3	C19—C20—H20	120.0
C8—C9—H9	121.3	C21—C20—H20	120.0
C11—C10—C9	120.6 (3)	C20—C21—C16	121.1 (3)
C11—C10—H10	119.7	C20—C21—H21	119.5
C9—C10—H10	119.7	C16—C21—H21	119.5
C6—C1—C2—C3	−0.1 (5)	C7—C8—C13—C12	179.5 (3)
C1—C2—C3—C4	1.6 (5)	C9—C8—C13—C14	−177.8 (3)
C2—C3—C4—C5	−0.7 (5)	C7—C8—C13—C14	1.2 (3)
C3—C4—C5—C6	−1.6 (4)	C11—C12—C13—C8	−0.3 (5)
C2—C1—C6—C5	−2.3 (4)	C11—C12—C13—C14	177.6 (3)
C2—C1—C6—N	176.4 (3)	C7—N—C14—C15	−179.3 (3)
C4—C5—C6—C1	3.1 (4)	C6—N—C14—C15	6.4 (5)
C4—C5—C6—N	−175.6 (3)	C7—N—C14—C13	−0.4 (3)
C7—N—C6—C1	66.8 (4)	C6—N—C14—C13	−174.8 (3)
C14—N—C6—C1	−119.4 (3)	C8—C13—C14—C15	178.4 (3)
C7—N—C6—C5	−114.5 (3)	C12—C13—C14—C15	0.3 (5)
C14—N—C6—C5	59.4 (4)	C8—C13—C14—N	−0.6 (3)
C14—N—C7—O	−178.8 (3)	C12—C13—C14—N	−178.6 (3)
C6—N—C7—O	−4.2 (5)	N—C14—C15—C16	5.4 (5)
C14—N—C7—C8	1.1 (3)	C13—C14—C15—C16	−173.2 (3)
C6—N—C7—C8	175.7 (3)	C14—C15—C16—C21	52.8 (4)
O—C7—C8—C13	178.5 (4)	C14—C15—C16—C17	−128.5 (3)
N—C7—C8—C13	−1.4 (3)	C21—C16—C17—C18	−2.5 (4)
O—C7—C8—C9	−2.6 (6)	C15—C16—C17—C18	178.8 (3)
N—C7—C8—C9	177.5 (3)	C16—C17—C18—C19	0.0 (5)
C13—C8—C9—C10	−0.4 (5)	C17—C18—C19—C20	2.8 (5)
C7—C8—C9—C10	−179.3 (3)	C18—C19—C20—C21	−2.9 (5)
C8—C9—C10—C11	0.3 (5)	C19—C20—C21—C16	0.2 (4)
C9—C10—C11—C12	−0.1 (5)	C17—C16—C21—C20	2.4 (4)
C10—C11—C12—C13	0.1 (5)	C15—C16—C21—C20	−178.9 (3)
C9—C8—C13—C12	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D···A	D—H···A
C11—H11···O^i	3.339 (5)	132.6 (2)
C12—H12···O^i	3.495 (5)	116.1 (2)
C19—H19···O^ii	3.504 (4)	139.4 (2)

Symmetry codes: (i) x, y, z−1; (ii) −x+1, y+1/2, −z+3/2.

(III) (Z)—N-(p-anisyl)-3-benzylidene isoindolin-1-one

Crystal data

C22H17NO2	F(000) = 688
Mr = 327.37	Dx = 1.330 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
a = 8.577 (6) Å	Cell parameters from 25 reflections
b = 10.542 (4) Å	θ = 28.8–39.9°
c = 18.272 (4) Å	µ = 0.68 mm^−1
β = 98.34 (4)°	T = 293 K
V = 1634.7 (13) Å^3	Prism, colourless
Z = 4	0.35 × 0.25 × 0.10 mm

Data collection

Rigaku AFC5R diffractometer	2220 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.000
Graphite monochromator	θmax = 78.9°, θmin = 4.9°
ω–2θ scans	h = 0→10
Absorption correction: empirical (using intensity measurements) North et al., 1968	k = 0→13
Tmin = 0.878, Tmax = 0.934	l = −22→22
2810 measured reflections	3 standard reflections every 100 reflections
2810 independent reflections	intensity decay: <2%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.03	Calculated w = 1/[σ^2(Fo^2) + (0.0252P)^2 + 0.5728P] where P = (Fo^2 + 2Fc^2)/3
2810 reflections	(Δ/σ)max = −0.004
226 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N	0.9504 (2)	0.2242 (2)	0.54014 (9)	0.0454 (4)
O1	0.7774 (2)	0.3255 (2)	0.44993 (9)	0.0671 (5)
O2	0.5438 (2)	−0.0217 (2)	0.70398 (9)	0.0649 (5)
C1	0.8210 (2)	0.2044 (2)	0.65002 (12)	0.0472 (5)
H1	0.8797	0.2728	0.6711	0.058*
C2	0.7220 (3)	0.1408 (2)	0.69022 (12)	0.0493 (5)
H2	0.7145	0.1657	0.7384	0.060*
C3	0.6331 (2)	0.0391 (2)	0.65864 (12)	0.0470 (5)
C4	0.6393 (2)	0.0057 (2)	0.58609 (12)	0.0525 (6)
H4	0.5763	−0.0596	0.5640	0.066*
C5	0.7407 (2)	0.0703 (2)	0.54633 (11)	0.0494 (5)
H5	0.7455	0.0479	0.4975	0.052*
C6	0.8341 (2)	0.1675 (2)	0.57860 (11)	0.0423 (5)
C7	0.9109 (3)	0.3039 (2)	0.47895 (12)	0.0488 (5)
C8	1.0624 (3)	0.3493 (2)	0.45941 (12)	0.0471 (5)
C9	1.0921 (3)	0.4276 (2)	0.40179 (12)	0.0578 (6)
H9	1.0102	0.4630	0.3693	0.072*
C10	1.2477 (3)	0.4510 (2)	0.39463 (14)	0.0631 (7)
H10	1.2711	0.5028	0.3565	0.078*
C11	1.3690 (3)	0.3987 (2)	0.44318 (14)	0.0629 (7)
H11	1.4726	0.4154	0.4368	0.067*
C12	1.3396 (3)	0.3217 (2)	0.50124 (13)	0.0564 (6)
H12	1.4218	0.2875	0.5341	0.060*
C13	1.1837 (2)	0.2972 (2)	0.50879 (11)	0.0458 (5)
C14	1.1156 (2)	0.2166 (2)	0.56185 (11)	0.0428 (5)
C15	1.1975 (2)	0.1509 (2)	0.61738 (12)	0.0481 (5)
H15	1.3058	0.1637	0.6230	0.059*
C16	1.1453 (2)	0.0618 (2)	0.67117 (11)	0.0432 (5)
C17	1.1953 (2)	0.0786 (2)	0.74638 (12)	0.0494 (5)
H17	1.2626	0.1455	0.7620	0.062*
C18	1.1469 (3)	−0.0019 (2)	0.79830 (12)	0.0553 (6)
H18	1.1802	0.0117	0.8484	0.060*
C19	1.0487 (3)	−0.1028 (2)	0.77537 (13)	0.0568 (6)
H19	1.0140	−0.1564	0.8101	0.089*
C20	1.0025 (3)	−0.1236 (2)	0.70116 (13)	0.0535 (6)
H20	0.9377	−0.1922	0.6858	0.072*
C21	1.0514 (2)	−0.0433 (2)	0.64907 (12)	0.0473 (5)
H21	1.0215	−0.0595	0.5990	0.047*
C22	0.4659 (3)	−0.1354 (3)	0.6773 (2)	0.0691 (7)
H22A	0.4083	−0.1689	0.7143	0.074*
H22B	0.5424	−0.1965	0.6667	0.087*
H22C	0.3943	−0.1174	0.6331	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0418 (9)	0.0509 (11)	0.0433 (10)	−0.0021 (8)	0.0053 (8)	0.0059 (8)
O1	0.0543 (10)	0.0802 (13)	0.0633 (10)	0.0036 (9)	−0.0027 (8)	0.0196 (9)
O2	0.0594 (10)	0.0767 (12)	0.0624 (10)	−0.0124 (9)	0.0219 (8)	0.0044 (9)
C1	0.0506 (12)	0.0421 (12)	0.0481 (12)	0.0007 (10)	0.0046 (10)	−0.0044 (10)
C2	0.0544 (13)	0.0517 (13)	0.0447 (12)	0.0040 (10)	0.0168 (10)	−0.0060 (10)
C3	0.0388 (11)	0.0537 (13)	0.0497 (12)	0.0025 (10)	0.0103 (9)	0.0063 (11)
C4	0.0453 (12)	0.0615 (15)	0.0491 (13)	−0.0098 (11)	0.0016 (10)	−0.0025 (11)
C5	0.0474 (12)	0.0634 (14)	0.0366 (11)	−0.0039 (11)	0.0037 (9)	−0.0042 (10)
C6	0.0396 (10)	0.0467 (12)	0.0406 (11)	0.0012 (9)	0.0054 (9)	0.0029 (9)
C7	0.0529 (13)	0.0501 (13)	0.0429 (12)	0.0002 (11)	0.0053 (10)	0.0022 (10)
C8	0.0567 (13)	0.0436 (12)	0.0419 (12)	−0.0052 (10)	0.0103 (10)	−0.0040 (10)
C9	0.077 (2)	0.0502 (13)	0.0469 (13)	−0.0034 (12)	0.0103 (12)	0.0039 (11)
C10	0.083 (2)	0.0553 (15)	0.0550 (14)	−0.0162 (14)	0.0244 (13)	0.0000 (12)
C11	0.065 (2)	0.063 (2)	0.065 (2)	−0.0178 (13)	0.0245 (13)	−0.0071 (13)
C12	0.0534 (13)	0.0583 (15)	0.0582 (14)	−0.0069 (11)	0.0103 (11)	−0.0021 (12)
C13	0.0500 (12)	0.0450 (12)	0.0433 (11)	−0.0056 (10)	0.0097 (9)	−0.0045 (10)
C14	0.0430 (11)	0.0426 (11)	0.0430 (11)	−0.0044 (9)	0.0070 (9)	−0.0040 (9)
C15	0.0427 (11)	0.0496 (13)	0.0514 (13)	−0.0025 (10)	0.0052 (10)	0.0013 (10)
C16	0.0390 (10)	0.0424 (11)	0.0478 (12)	0.0036 (9)	0.0050 (9)	0.0001 (10)
C17	0.0481 (12)	0.0468 (12)	0.0511 (13)	0.0001 (10)	−0.0003 (10)	−0.0039 (11)
C18	0.0592 (14)	0.064 (2)	0.0418 (12)	0.0042 (12)	0.0047 (10)	−0.0012 (11)
C19	0.0627 (14)	0.0514 (14)	0.0574 (14)	0.0027 (12)	0.0125 (12)	0.0096 (12)
C20	0.0543 (13)	0.0421 (12)	0.064 (2)	−0.0028 (10)	0.0097 (11)	−0.0006 (11)
C21	0.0484 (12)	0.0453 (12)	0.0470 (12)	0.0035 (10)	0.0030 (10)	−0.0044 (10)
C22	0.0600 (15)	0.064 (2)	0.085 (2)	−0.0077 (13)	0.0175 (14)	0.0159 (15)

Geometric parameters (Å, º)

N—C7	1.400 (3)	C11—C12	1.387 (3)
N—C14	1.417 (3)	C11—H11	0.930
N—C6	1.432 (3)	C12—C13	1.388 (3)
O1—C7	1.211 (3)	C12—H12	0.930
O2—C3	1.366 (2)	C13—C14	1.473 (3)
O2—C22	1.424 (3)	C14—C15	1.340 (3)
C1—C2	1.376 (3)	C15—C16	1.475 (3)
C1—C6	1.382 (3)	C15—H15	0.930
C1—H1	0.930	C16—C17	1.390 (3)
C2—C3	1.391 (3)	C16—C21	1.394 (3)
C2—H2	0.930	C17—C18	1.380 (3)
C3—C4	1.380 (3)	C17—H17	0.930
C4—C5	1.390 (3)	C18—C19	1.384 (3)
C4—H4	0.930	C18—H18	0.930
C5—C6	1.379 (3)	C19—C20	1.374 (3)
C5—H5	0.930	C19—H19	0.930
C7—C8	1.476 (3)	C20—C21	1.384 (3)
C8—C13	1.388 (3)	C20—H20	0.930
C8—C9	1.390 (3)	C21—H21	0.930
C9—C10	1.382 (3)	C22—H22A	0.960
C9—H9	0.930	C22—H22B	0.960
C10—C11	1.381 (4)	C22—H22C	0.960
C10—H10	0.930
C7—N—C14	111.9 (2)	C13—C12—C11	118.0 (2)
C7—N—C6	122.5 (2)	C13—C12—H12	121.0
C14—N—C6	125.3 (2)	C11—C12—H12	121.0
C3—O2—C22	117.7 (2)	C12—C13—C8	120.3 (2)
C2—C1—C6	120.5 (2)	C12—C13—C14	130.7 (2)
C2—C1—H1	119.7	C8—C13—C14	108.9 (2)
C6—C1—H1	119.7	C15—C14—N	129.4 (2)
C1—C2—C3	119.9 (2)	C15—C14—C13	125.6 (2)
C1—C2—H2	120.1	N—C14—C13	105.0 (2)
C3—C2—H2	120.1	C14—C15—C16	131.1 (2)
O2—C3—C4	124.5 (2)	C14—C15—H15	114.5
O2—C3—C2	115.5 (2)	C16—C15—H15	114.5
C4—C3—C2	120.0 (2)	C17—C16—C21	118.0 (2)
C3—C4—C5	119.4 (2)	C17—C16—C15	119.8 (2)
C3—C4—H4	120.3	C21—C16—C15	122.1 (2)
C5—C4—H4	120.3	C18—C17—C16	121.4 (2)
C6—C5—C4	120.6 (2)	C18—C17—H17	119.3
C6—C5—H5	119.7	C16—C17—H17	119.3
C4—C5—H5	119.7	C17—C18—C19	119.6 (2)
C5—C6—C1	119.4 (2)	C17—C18—H18	120.2
C5—C6—N	120.2 (2)	C19—C18—H18	120.2
C1—C6—N	120.2 (2)	C20—C19—C18	119.8 (2)
O1—C7—N	124.5 (2)	C20—C19—H19	120.1
O1—C7—C8	130.0 (2)	C18—C19—H19	120.1
N—C7—C8	105.5 (2)	C19—C20—C21	120.6 (2)
C13—C8—C9	121.7 (2)	C19—C20—H20	119.7
C13—C8—C7	108.5 (2)	C21—C20—H20	119.7
C9—C8—C7	129.8 (2)	C20—C21—C16	120.5 (2)
C10—C9—C8	117.6 (2)	C20—C21—H21	119.8
C10—C9—H9	121.2	C16—C21—H21	119.8
C8—C9—H9	121.2	O2—C22—H22A	109.5
C11—C10—C9	121.1 (2)	O2—C22—H22B	109.5
C11—C10—H10	119.5	H22A—C22—H22B	109.5
C9—C10—H10	119.5	O2—C22—H22C	109.5
C10—C11—C12	121.4 (2)	H22A—C22—H22C	109.5
C10—C11—H11	119.3	H22B—C22—H22C	109.5
C12—C11—H11	119.3
C6—C1—C2—C3	−0.6 (3)	C10—C11—C12—C13	0.7 (4)
C22—O2—C3—C4	7.3 (3)	C11—C12—C13—C8	−0.2 (3)
C22—O2—C3—C2	−172.5 (2)	C11—C12—C13—C14	177.2 (2)
C1—C2—C3—O2	177.1 (2)	C9—C8—C13—C12	−0.6 (3)
C1—C2—C3—C4	−2.7 (3)	C7—C8—C13—C12	178.0 (2)
O2—C3—C4—C5	−176.7 (2)	C9—C8—C13—C14	−178.5 (2)
C2—C3—C4—C5	3.1 (3)	C7—C8—C13—C14	0.0 (2)
C3—C4—C5—C6	−0.2 (3)	C7—N—C14—C15	179.8 (2)
C4—C5—C6—C1	−3.0 (3)	C6—N—C14—C15	4.9 (3)
C4—C5—C6—N	173.1 (2)	C7—N—C14—C13	−0.8 (2)
C2—C1—C6—C5	3.4 (3)	C6—N—C14—C13	−175.7 (2)
C2—C1—C6—N	−172.7 (2)	C12—C13—C14—C15	2.2 (4)
C7—N—C6—C5	72.0 (3)	C8—C13—C14—C15	179.8 (2)
C14—N—C6—C5	−113.6 (2)	C12—C13—C14—N	−177.2 (2)
C7—N—C6—C1	−111.8 (2)	C8—C13—C14—N	0.5 (2)
C14—N—C6—C1	62.6 (3)	N—C14—C15—C16	3.3 (4)
C14—N—C7—O1	179.7 (2)	C13—C14—C15—C16	−176.0 (2)
C6—N—C7—O1	−5.2 (3)	C14—C15—C16—C17	−128.6 (3)
C14—N—C7—C8	0.8 (2)	C14—C15—C16—C21	54.0 (3)
C6—N—C7—C8	175.9 (2)	C21—C16—C17—C18	−3.4 (3)
O1—C7—C8—C13	−179.3 (2)	C15—C16—C17—C18	179.0 (2)
N—C7—C8—C13	−0.5 (2)	C16—C17—C18—C19	1.0 (3)
O1—C7—C8—C9	−0.9 (4)	C17—C18—C19—C20	1.2 (4)
N—C7—C8—C9	177.9 (2)	C18—C19—C20—C21	−1.0 (4)
C13—C8—C9—C10	0.8 (3)	C19—C20—C21—C16	−1.6 (3)
C7—C8—C9—C10	−177.4 (2)	C17—C16—C21—C20	3.7 (3)
C8—C9—C10—C11	−0.2 (4)	C15—C16—C21—C20	−178.8 (2)
C9—C10—C11—C12	−0.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D···A	D—H···A
C18—H18···O1^i	3.389 (3)	146.4 (1)
C22—H22C···O1^ii	3.517 (3)	119.9 (2)
C11—H11···O1^iii	3.572 (4)	146.7 (2)

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y, −z+1; (iii) x+1, y, z.