(3R,4S)-3-Phenyl-1-[(R)-1-phenyl­ethyl]-4-[(R)-1-phenylethyliminomethyl]azetidin-2-one

The configuration of the chiral ring atoms of the title compound, C₂₆H₂₆N₂O, obtained in an enantioselective synthesis, has been established relative to the known R configuration of the α-methyl­benzyl moieties. The crystal packing involves a two-dimensional network of C—H...π interactions between the aromatic rings.

S1. Comment

Azetidin-2-ones are of interest as potential building blocks for the synthesis of antibiotic agents (Morin & Gorman, 1982). They can be prepared via zinc-mediated condensations of ester enolates with imines. During a study on 3-amino-substituted azetidin-2-ones it was established that the zinc-mediated condensation resulted in an exclusive trans arrangement of substituents on the newly formed four-membered ring. The enantioselective synthesis favoured the formation of the (3R,4S) configuration on the new chiral centres (van der Steen et al., 1992). During a study on the enantioselective synthesis of 3-hydrocarbon-substituted azetidin-2-ones, the title compound, (I), was one of the compounds prepared (Kleijn et al., 1992). \scheme

Compound (I) was obtained in a trans configuration with an enantiomeric excess of 64%. A crystal structure determination of the predominant diastereoisomer was undertaken to establish the absolute configurations of the atoms in the ring fragment with respect to the known configuration of the (R)-α-methylbenzyl moieties. The absolute configurations of the newly formed chiral centres in the four-membered ring are R on C3 and S on C4. This shows that the enantioselective syntheses of the 3-amino- and the 3-hydrocarbon-substituted azetidin-2-ones favour the same absolute configurations in the newly formed four-membered ring.

The bond lengths and angles in (I) are well within the range reported in similar structures (Cambridge Structural Database, October 1999 version; Allen et al., 1993). The central four-membered ring is slightly bent, as is illustrated by the puckering parameter q(2) which amounts to 0.080 (2) Å (Cremer & Pople, 1975). The improper torsion angle N1—C2—C4—C3, another measure for the puckering of the four-membered ring, takes the value 171.2 (2)°, which is well within the range found in the CSD (160–180°).

Due to the lack of classic hydrogen bond donors, the packing is determined by weaker interactions. No C—H···O or C—H···N interactions are present, not even for those C—H groups neighbouring electronegative moieties. The only directional interactions in the structure appear to be C—H···π hydrogen bonds. In ring A (atoms C7–C12), the atoms C8 and C11, positioned para with respect to each other, donate a C—H···π bond to the B-rings (atoms C14–C19) of the molecules at (1/2 + x, 1/2 - y, 1 - z) and (1/2 + x, 3/2 - y, 1 - z) (geometric details are given in in Table 2), thus creating an infinite string of edge-face π-systems (Hunter, 1994) running in the [010] direction. This string of aromatic rings intersects with a similar string of C—H···π bonded ring systems, consisting of ring C (atoms C24–C29) and ring A, where the latter now acts as the acceptor. This string, which runs in the [100] direction, contains alternating intra- and intermolecular C—H···π interactions. The two intersecting strings create a two-dimensional network with base vectors [100] and [010]. The two symmetry-related two-dimensional C—H···π networks that are located at approximately z = 0.85 and z = 0.65 are joined by a C—H···π interaction between C17 of ring B and ring C, creating a `bilayer' of C—H···π bonded aromatic rings (Fig. 2). Rings A and B accept C—H···π donations from other phenyl rings on both sides of their π-systems. In contrast, ring C receives a C—H···π interaction from another phenyl ring on only one side of its π-system. The other side of ring C receives a C—H···π bond from the methyl group, C6 (geometric details are included in Table 2; this interaction is not drawn in Fig. 2).

S2. Experimental

Details of the synthesis of (I) are given elsewhere (Kleijn et al., 1992). Light yellow crystals were obtained from a solution in diethyl ether (m.p. 360 K).

S3. Refinement

H atoms were introduced at calculated positions, and included in the refinement riding on their carrier atoms. Methyl moieties were refined as rigid groups, allowing for rotation around the C—C bonds, while maintaining tetrahedral geometry at the methyl C atoms. The isotropic displacement parameters of the H atoms were set to a fixed value, related to the equivalent isotropic displacement parameter of the carrier atom by a factor of 1.5 for the methyl H atoms and a factor of 1.2 for all other H atoms. For 2104 Friedel pairs the intensities of both members were measured, i.e. 76% of the total number of Friedel pairs with θ < θ_max. Due to the lack of anomalous scatterers, the absolute configuration could not be established reliably, as is illustrated by the value of -0.3 (19) obtained for the Flack x parameter (Flack, 1983) derived during a structure factor calculation using all data (meaning that only the symmetry-related intensities were averaged and not the Friedel pairs). The absolute structure was therefore set in accordance with the known configuration of the (R)-α-methylbenzyl moieties. Since there is no significant dispersion, the final refinement cycles were carried out using a data set in which the Friedel-related reflections were also averaged.

Computing details

Data collection: locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97-2 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: PLATON.

Figures

Fig. 1. Displacement ellipsoid plot of (I) drawn at the 30% probability level (PLATON; Spek, 1999). H atoms have an arbitrary radius. Ring labels A, B and C refer to π-systems accepting C—H···π bonds.

Fig. 2. Packing diagram for (I), showing the bilayer of C—H···π bonded aromatic rings. Only the aromatic C atoms and those H atoms involved in the interactions are shown. Atoms belonging to the rings in the back layer are drawn as black spheres, atoms belonging to rings in the front layer are drawn as white spheres. Ring labels A, B and C refer to the ring classification defined in Fig. 1. The Me···π interaction has been omitted for clarity.

(3R,4S)-3-Phenyl-1-[(R)-1-phenylethyl]-4-[(R)-1-phenylethyliminomethyl]azet idin-2-one

Crystal data

C26H26N2O	Dx = 1.186 Mg m^−3
Mr = 382.49	Melting point: 360 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.4958 (10) Å	θ = 11.5–14.0°
b = 10.1947 (8) Å	µ = 0.07 mm^−1
c = 22.124 (2) Å	T = 293 K
V = 2141.7 (3) Å^3	Block, light yellow
Z = 4	0.4 × 0.4 × 0.2 mm
F(000) = 816

Data collection

Enraf-Nonius CAD-4T diffractometer	Rint = 0.027
Radiation source: rotating anode	θmax = 27.5°, θmin = 1.8°
Graphite monochromator	h = 0→12
ω/2θ scans	k = 0→13
5566 measured reflections	l = −28→28
2783 independent reflections	3 standard reflections every 60 min
2033 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.1317P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.040	(Δ/σ)max = 0.001
wR(F^2) = 0.106	Δρmax = 0.17 e Å^−3
S = 1.02	Δρmin = −0.16 e Å^−3
2783 reflections	Extinction correction: SHELXL97-2 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
265 parameters	Extinction coefficient: 0.0114 (16)
0 restraints	Absolute structure: see text

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
O13	0.30671 (19)	0.31146 (19)	0.43217 (8)	0.0640 (6)
N1	0.22007 (18)	0.4889 (2)	0.48973 (8)	0.0444 (6)
N21	−0.0867 (2)	0.5727 (2)	0.57702 (8)	0.0493 (6)
C2	0.2170 (3)	0.3740 (2)	0.45833 (10)	0.0467 (7)
C3	0.0588 (2)	0.3552 (2)	0.47042 (9)	0.0441 (7)
C4	0.0663 (2)	0.4948 (2)	0.49916 (9)	0.0421 (6)
C5	0.3212 (2)	0.5952 (3)	0.49775 (10)	0.0489 (7)
C6	0.4662 (3)	0.5575 (3)	0.47531 (12)	0.0773 (13)
C7	0.3262 (2)	0.6395 (2)	0.56324 (9)	0.0411 (6)
C8	0.3503 (3)	0.5511 (2)	0.60949 (11)	0.0509 (8)
C9	0.3594 (3)	0.5941 (3)	0.66879 (11)	0.0597 (9)
C10	0.3453 (3)	0.7240 (3)	0.68185 (13)	0.0634 (9)
C11	0.3222 (3)	0.8134 (3)	0.63675 (13)	0.0604 (9)
C12	0.3117 (2)	0.7708 (2)	0.57735 (11)	0.0492 (8)
C14	−0.0452 (2)	0.3352 (2)	0.42006 (9)	0.0421 (6)
C15	−0.0041 (3)	0.3020 (3)	0.36178 (10)	0.0535 (8)
C16	−0.1051 (3)	0.2837 (3)	0.31704 (12)	0.0636 (10)
C17	−0.2440 (3)	0.2964 (3)	0.32973 (12)	0.0619 (9)
C18	−0.2873 (3)	0.3289 (3)	0.38722 (12)	0.0581 (9)
C19	−0.1873 (2)	0.3484 (2)	0.43204 (11)	0.0509 (8)
C20	0.0184 (2)	0.5052 (2)	0.56318 (9)	0.0443 (7)
C22	−0.1294 (3)	0.5709 (3)	0.64164 (11)	0.0557 (8)
C23	−0.2580 (4)	0.4864 (4)	0.64857 (18)	0.0993 (16)
C24	−0.1464 (3)	0.7120 (3)	0.66165 (9)	0.0497 (7)
C25	−0.0329 (3)	0.7761 (3)	0.68612 (13)	0.0695 (10)
C26	−0.0441 (5)	0.9078 (4)	0.70292 (14)	0.0919 (15)
C27	−0.1694 (5)	0.9723 (4)	0.69464 (15)	0.0943 (16)
C28	−0.2815 (4)	0.9089 (3)	0.67113 (15)	0.0804 (11)
C29	−0.2707 (3)	0.7796 (3)	0.65455 (12)	0.0609 (9)
H31	0.04460	0.28900	0.50200	0.0530*
H41	0.02180	0.56110	0.47340	0.0510*
H51	0.28880	0.66970	0.47350	0.0590*
H61	0.52900	0.63060	0.48000	0.1160*
H62	0.46090	0.53380	0.43340	0.1160*
H63	0.50060	0.48430	0.49830	0.1160*
H81	0.36050	0.46240	0.60080	0.0610*
H91	0.37510	0.53410	0.69970	0.0720*
H101	0.35140	0.75230	0.72170	0.0760*
H111	0.31360	0.90200	0.64590	0.0730*
H121	0.29470	0.83130	0.54670	0.0590*
H151	0.09090	0.29210	0.35270	0.0640*
H161	−0.07700	0.26260	0.27800	0.0760*
H171	−0.31050	0.28300	0.29950	0.0740*
H181	−0.38270	0.33780	0.39590	0.0700*
H191	−0.21640	0.37080	0.47080	0.0610*
H201	0.06760	0.46090	0.59330	0.0530*
H221	−0.05290	0.53150	0.66520	0.0670*
H231	−0.28830	0.48770	0.69000	0.1490*
H232	−0.23590	0.39810	0.63700	0.1490*
H233	−0.33200	0.51950	0.62320	0.1490*
H251	0.05180	0.73180	0.69150	0.0830*
H261	0.03270	0.95130	0.71960	0.1100*
H271	−0.17720	1.06020	0.70530	0.1130*
H281	−0.36640	0.95300	0.66620	0.0970*
H291	−0.34850	0.73710	0.63830	0.0730*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O13	0.0583 (10)	0.0700 (12)	0.0638 (11)	0.0150 (9)	0.0054 (9)	−0.0146 (10)
N1	0.0422 (10)	0.0505 (11)	0.0406 (9)	−0.0002 (9)	0.0022 (8)	−0.0063 (9)
N21	0.0472 (11)	0.0601 (12)	0.0407 (10)	0.0047 (9)	0.0032 (9)	−0.0052 (9)
C2	0.0496 (12)	0.0510 (13)	0.0395 (11)	0.0061 (12)	−0.0016 (10)	−0.0003 (11)
C3	0.0512 (12)	0.0436 (12)	0.0374 (10)	0.0012 (11)	−0.0010 (9)	−0.0017 (10)
C4	0.0429 (11)	0.0472 (12)	0.0363 (10)	0.0023 (10)	−0.0026 (9)	−0.0040 (10)
C5	0.0488 (12)	0.0579 (13)	0.0400 (11)	−0.0087 (11)	−0.0026 (10)	0.0031 (11)
C6	0.0551 (16)	0.112 (3)	0.0647 (16)	−0.0182 (17)	0.0174 (14)	−0.0226 (17)
C7	0.0344 (10)	0.0477 (12)	0.0413 (11)	−0.0052 (10)	−0.0010 (9)	0.0016 (10)
C8	0.0554 (14)	0.0500 (13)	0.0474 (12)	0.0050 (12)	−0.0047 (12)	0.0003 (11)
C9	0.0565 (15)	0.0789 (18)	0.0438 (13)	0.0052 (15)	−0.0064 (12)	0.0078 (13)
C10	0.0469 (14)	0.093 (2)	0.0502 (13)	−0.0008 (15)	−0.0018 (12)	−0.0188 (15)
C11	0.0525 (15)	0.0588 (16)	0.0700 (16)	−0.0005 (13)	−0.0015 (13)	−0.0171 (14)
C12	0.0411 (12)	0.0495 (14)	0.0569 (13)	−0.0031 (11)	−0.0028 (11)	0.0024 (11)
C14	0.0501 (12)	0.0376 (11)	0.0386 (10)	−0.0037 (10)	−0.0019 (10)	−0.0016 (9)
C15	0.0531 (14)	0.0610 (15)	0.0463 (12)	−0.0030 (13)	0.0045 (11)	−0.0090 (12)
C16	0.0740 (19)	0.0783 (18)	0.0386 (12)	−0.0099 (16)	−0.0011 (12)	−0.0130 (13)
C17	0.0679 (17)	0.0693 (17)	0.0486 (14)	−0.0122 (15)	−0.0162 (12)	−0.0042 (13)
C18	0.0492 (14)	0.0657 (17)	0.0593 (14)	−0.0074 (13)	−0.0033 (12)	−0.0012 (13)
C19	0.0552 (14)	0.0547 (14)	0.0427 (12)	−0.0052 (12)	0.0023 (11)	−0.0029 (11)
C20	0.0421 (12)	0.0534 (13)	0.0373 (10)	−0.0005 (11)	−0.0007 (9)	−0.0040 (10)
C22	0.0582 (15)	0.0627 (16)	0.0462 (12)	0.0067 (13)	0.0146 (12)	−0.0020 (12)
C23	0.104 (3)	0.078 (2)	0.116 (3)	−0.024 (2)	0.053 (2)	−0.021 (2)
C24	0.0488 (13)	0.0658 (15)	0.0345 (10)	−0.0027 (13)	0.0117 (10)	−0.0028 (11)
C25	0.0542 (16)	0.095 (2)	0.0592 (15)	−0.0116 (16)	0.0068 (13)	−0.0018 (16)
C26	0.110 (3)	0.100 (3)	0.0658 (18)	−0.042 (3)	0.012 (2)	−0.0222 (19)
C27	0.147 (4)	0.064 (2)	0.072 (2)	−0.009 (2)	0.042 (2)	−0.0152 (17)
C28	0.097 (2)	0.0652 (19)	0.079 (2)	0.015 (2)	0.029 (2)	0.0031 (17)
C29	0.0610 (16)	0.0691 (18)	0.0525 (14)	0.0044 (15)	0.0096 (12)	0.0016 (13)

Geometric parameters (Å, º)

O13—C2	1.211 (3)	C26—C27	1.372 (6)
N1—C2	1.362 (3)	C27—C28	1.350 (6)
N1—C4	1.476 (3)	C28—C29	1.372 (4)
N1—C5	1.459 (3)	C3—H31	0.9807
N21—C20	1.250 (3)	C4—H41	0.9799
N21—C22	1.486 (3)	C5—H51	0.9795
C2—C3	1.538 (3)	C6—H61	0.9601
C3—C4	1.560 (3)	C6—H62	0.9595
C3—C14	1.503 (3)	C6—H63	0.9604
C4—C20	1.491 (3)	C8—H81	0.9295
C5—C6	1.513 (3)	C9—H91	0.9295
C5—C7	1.518 (3)	C10—H101	0.9294
C7—C8	1.383 (3)	C11—H111	0.9293
C7—C12	1.381 (3)	C12—H121	0.9307
C8—C9	1.386 (3)	C15—H151	0.9297
C9—C10	1.362 (4)	C16—H161	0.9292
C10—C11	1.369 (4)	C17—H171	0.9299
C11—C12	1.388 (4)	C18—H181	0.9305
C14—C15	1.389 (3)	C19—H191	0.9294
C14—C19	1.382 (3)	C20—H201	0.9307
C15—C16	1.391 (4)	C22—H221	0.9802
C16—C17	1.355 (4)	C23—H231	0.9608
C17—C18	1.377 (4)	C23—H232	0.9591
C18—C19	1.387 (4)	C23—H233	0.9606
C22—C23	1.502 (5)	C25—H251	0.9301
C22—C24	1.514 (4)	C26—H261	0.9299
C24—C25	1.372 (4)	C27—H271	0.9296
C24—C29	1.376 (4)	C28—H281	0.9295
C25—C26	1.397 (5)	C29—H291	0.9288
O13···C6	3.082 (4)	H31···O13^ii	2.8763
O13···C15	3.338 (3)	H41···C19	3.0793
O13···C19^i	3.418 (3)	H41···C12^vi	2.8597
O13···H62	2.6986	H41···H121^vi	2.4600
O13···H151	2.7073	H51···H121	2.3108
O13···H31^i	2.8763	H51···C29^v	2.9346
O13···H191^i	2.8476	H62···O13	2.6986
O13···H232^i	2.6589	H62···C2	2.8848
N1···H81	2.8088	H62···C26^v	3.0745
C2···C19^i	3.442 (3)	H62···C27^v	3.0918
C6···O13	3.082 (4)	H63···C2	3.0494
C7···C20	3.228 (3)	H63···C8	2.9244
C8···C20	3.347 (3)	H81···N1	2.8088
C11···C25	3.565 (4)	H81···C15^i	3.0990
C15···O13	3.338 (3)	H101···H161^iv	2.4827
C19···C2^ii	3.442 (3)	H111···C18^v	2.9969
C19···O13^ii	3.418 (3)	H111···C19^v	3.0738
C20···C8	3.347 (3)	H121···H51	2.3108
C20···C7	3.228 (3)	H121···H41^v	2.4600
C25···C11	3.565 (4)	H151···O13	2.7073
C2···H151	2.7554	H151···C2	2.7554
C2···H63	3.0494	H151···H232^i	2.5528
C2···H62	2.8848	H161···C10^viii	3.0634
C2···H191^i	3.0144	H161···H101^viii	2.4827
C4···H191	3.0328	H171···C24^ix	3.0775
C8···H201	2.8601	H171···C25^ix	2.9776
C8···H233^iii	3.0491	H191···C4	3.0328
C8···H63	2.9244	H191···O13^ii	2.8476
C10···H291^iii	3.0660	H191···C2^ii	3.0144
C10···H161^iv	3.0634	H201···C8	2.8601
C10···H251	2.7963	H201···H221	2.0875
C11···H251	2.9584	H221···H201	2.0875
C12···H41^v	2.8597	H221···H251	2.3445
C15···H81^ii	3.0990	H231···C29	3.0820
C15···H281^v	2.8864	H232···O13^ii	2.6589
C18···H111^vi	2.9969	H232···H151^ii	2.5528
C19···H41	3.0793	H233···C8^x	3.0491
C19···H111^vi	3.0738	H233···C29	2.8020
C23···H291	2.7060	H233···H291	2.2488
C24···H171^vii	3.0775	H251···C10	2.7963
C25···H171^vii	2.9776	H251···C11	2.9584
C26···H62^vi	3.0745	H251···H221	2.3445
C27···H62^vi	3.0918	H281···C15^vi	2.8864
C29···H231	3.0820	H291···C10^x	3.0660
C29···H233	2.8020	H291···C23	2.7060
C29···H51^vi	2.9346	H291···H233	2.2488
C2—N1—C4	94.93 (18)	N1—C5—H51	107.62
C2—N1—C5	135.6 (2)	C6—C5—H51	107.64
C4—N1—C5	127.13 (19)	C7—C5—H51	107.57
C20—N21—C22	116.5 (2)	C5—C6—H61	109.42
O13—C2—N1	132.9 (2)	C5—C6—H62	109.47
O13—C2—C3	134.8 (2)	C5—C6—H63	109.46
N1—C2—C3	92.26 (18)	H61—C6—H62	109.42
C2—C3—C4	84.99 (14)	H61—C6—H63	109.55
C2—C3—C14	122.00 (17)	H62—C6—H63	109.51
C4—C3—C14	117.12 (16)	C7—C8—H81	119.89
N1—C4—C3	87.16 (15)	C9—C8—H81	119.80
N1—C4—C20	116.03 (16)	C8—C9—H91	119.89
C3—C4—C20	115.97 (17)	C10—C9—H91	119.97
N1—C5—C6	111.7 (2)	C9—C10—H101	119.80
N1—C5—C7	110.95 (18)	C11—C10—H101	119.65
C6—C5—C7	111.11 (18)	C10—C11—H111	120.16
C5—C7—C8	121.2 (2)	C12—C11—H111	120.28
C5—C7—C12	120.0 (2)	C7—C12—H121	119.66
C8—C7—C12	118.7 (2)	C11—C12—H121	119.67
C7—C8—C9	120.3 (2)	C14—C15—H151	119.98
C8—C9—C10	120.1 (2)	C16—C15—H151	120.05
C9—C10—C11	120.6 (3)	C15—C16—H161	119.64
C10—C11—C12	119.6 (3)	C17—C16—H161	119.63
C7—C12—C11	120.7 (2)	C16—C17—H171	119.87
C3—C14—C15	122.46 (19)	C18—C17—H171	119.79
C3—C14—C19	119.10 (18)	C17—C18—H181	120.31
C15—C14—C19	118.4 (2)	C19—C18—H181	120.33
C14—C15—C16	120.0 (2)	C14—C19—H191	119.42
C15—C16—C17	120.7 (3)	C18—C19—H191	119.42
C16—C17—C18	120.3 (3)	N21—C20—H201	119.50
C17—C18—C19	119.4 (3)	C4—C20—H201	119.50
C14—C19—C18	121.2 (2)	N21—C22—H221	108.33
N21—C20—C4	121.01 (18)	C23—C22—H221	108.25
N21—C22—C23	109.1 (2)	C24—C22—H221	108.24
N21—C22—C24	107.4 (2)	C22—C23—H231	109.44
C23—C22—C24	115.4 (3)	C22—C23—H232	109.46
C22—C24—C25	119.0 (3)	C22—C23—H233	109.49
C22—C24—C29	122.3 (3)	H231—C23—H232	109.46
C25—C24—C29	118.7 (3)	H231—C23—H233	109.48
C24—C25—C26	120.2 (3)	H232—C23—H233	109.50
C25—C26—C27	119.4 (4)	C24—C25—H251	119.91
C26—C27—C28	120.4 (4)	C26—C25—H251	119.89
C27—C28—C29	120.3 (3)	C25—C26—H261	120.28
C24—C29—C28	121.0 (3)	C27—C26—H261	120.31
C2—C3—H31	110.12	C26—C27—H271	119.82
C4—C3—H31	110.10	C28—C27—H271	119.78
C14—C3—H31	110.15	C27—C28—H281	119.85
N1—C4—H41	111.87	C29—C28—H281	119.88
C3—C4—H41	111.87	C24—C29—H291	119.53
C20—C4—H41	111.83	C28—C29—H291	119.48
C4—N1—C2—O13	174.6 (3)	C6—C5—C7—C8	−71.0 (3)
C4—N1—C2—C3	−6.51 (16)	C6—C5—C7—C12	106.6 (3)
C5—N1—C2—O13	11.9 (4)	C8—C7—C12—C11	0.5 (3)
C5—N1—C2—C3	−169.2 (2)	C5—C7—C12—C11	−177.2 (2)
C2—N1—C4—C3	6.42 (16)	C5—C7—C8—C9	177.7 (2)
C2—N1—C4—C20	124.05 (19)	C12—C7—C8—C9	0.1 (4)
C5—N1—C4—C3	171.3 (2)	C7—C8—C9—C10	−0.3 (4)
C5—N1—C4—C20	−71.1 (3)	C8—C9—C10—C11	−0.1 (4)
C2—N1—C5—C6	−13.7 (4)	C9—C10—C11—C12	0.7 (4)
C2—N1—C5—C7	−138.3 (2)	C10—C11—C12—C7	−0.9 (4)
C4—N1—C5—C6	−171.9 (2)	C3—C14—C15—C16	179.5 (2)
C4—N1—C5—C7	63.5 (3)	C15—C14—C19—C18	0.1 (4)
C22—N21—C20—C4	177.1 (2)	C19—C14—C15—C16	0.4 (4)
C20—N21—C22—C23	−104.5 (3)	C3—C14—C19—C18	−179.0 (2)
C20—N21—C22—C24	129.8 (2)	C14—C15—C16—C17	−0.8 (5)
O13—C2—C3—C14	−56.0 (4)	C15—C16—C17—C18	0.6 (5)
N1—C2—C3—C4	6.16 (16)	C16—C17—C18—C19	−0.1 (4)
O13—C2—C3—C4	−175.0 (3)	C17—C18—C19—C14	−0.3 (4)
N1—C2—C3—C14	125.2 (2)	C23—C22—C24—C29	−34.8 (4)
C14—C3—C4—N1	−129.24 (17)	C23—C22—C24—C25	147.1 (3)
C14—C3—C4—C20	113.1 (2)	N21—C22—C24—C25	−91.0 (3)
C2—C3—C4—N1	−5.69 (14)	N21—C22—C24—C29	87.1 (3)
C2—C3—C4—C20	−123.36 (18)	C22—C24—C25—C26	177.6 (3)
C4—C3—C14—C15	117.2 (2)	C25—C24—C29—C28	0.4 (4)
C2—C3—C14—C15	15.4 (3)	C29—C24—C25—C26	−0.5 (4)
C2—C3—C14—C19	−165.52 (19)	C22—C24—C29—C28	−177.6 (3)
C4—C3—C14—C19	−63.7 (2)	C24—C25—C26—C27	−0.1 (5)
C3—C4—C20—N21	−116.2 (2)	C25—C26—C27—C28	0.8 (5)
N1—C4—C20—N21	143.7 (2)	C26—C27—C28—C29	−0.8 (5)
N1—C5—C7—C8	53.9 (3)	C27—C28—C29—C24	0.2 (5)
N1—C5—C7—C12	−128.4 (2)

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1, y, z; (iv) −x+1/2, −y+1, z+1/2; (v) x+1/2, −y+3/2, −z+1; (vi) x−1/2, −y+3/2, −z+1; (vii) −x−1/2, −y+1, z+1/2; (viii) −x+1/2, −y+1, z−1/2; (ix) −x−1/2, −y+1, z−1/2; (x) x−1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H62···Cg3^v	0.96	3.00	3.741 (3)	135
C8—H81···Cg2^i	0.93	2.89	3.757 (3)	156
C11—H111···Cg2^v	0.93	2.94	3.801 (3)	155
C17—H171···Cg3^ix	0.93	2.98	3.753 (3)	141
C25—H251···Cg1	0.93	3.14	3.890 (3)	139
C29—H291···Cg1^x	0.93	3.07	3.929 (3)	155

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