4,8,9,10-Tetra­phenyl-1,3-di­aza­adamantan-6-one

In the mol­ecule of the title compound, C₃₂H₂₈N₂O, two of the four phenyl substituents occupy axial and the other two occupy equatorial positions relative to their respective C₅N rings of the adamantane framework. The crystal packing is characterized by weak C—H...O interactions. The packing features are distinctly different from those of the crystals of the methoxy- and chloro-substituted analogues.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.118
• Data-to-parameter ratio = 10.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5554


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

4,8,9,10-Tetraphenyl-1,3-diazaadamantan-6-one

Crystal data

C32H28N2O	F(000) = 968
Mr = 456.56	Dx = 1.256 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 1016 reflections
a = 11.7347 (14) Å	θ = 16–32°
b = 11.6976 (13) Å	µ = 0.59 mm^−1
c = 17.6391 (14) Å	T = 293 K
β = 94.32 (1)°	Needle, colourless
V = 2414.4 (5) Å^3	0.30 × 0.26 × 0.13 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	3425 independent reflections
Radiation source: fine-focus sealed tube	2919 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
Detector resolution: 8 pixels mm^-1	θmax = 58.9°, θmin = 3.8°
ω scans	h = −7→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→11
Tmin = 0.92, Tmax = 0.93	l = −19→16
9728 measured reflections

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) = 0.118	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.7546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3425 reflections	Δρmax = 0.22 e Å^−3
317 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (5)

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
O1	0.04494 (11)	0.23243 (13)	0.81304 (7)	0.0568 (4)
N1	0.34669 (12)	0.08425 (13)	0.83056 (8)	0.0416 (4)
C2	0.39311 (15)	0.09042 (16)	0.75479 (10)	0.0430 (4)
H2A	0.4662	0.1295	0.7600	0.052*
H2B	0.4068	0.0133	0.7374	0.052*
N3	0.31790 (12)	0.14985 (13)	0.69630 (8)	0.0411 (4)
C4	0.30333 (15)	0.26893 (15)	0.72345 (9)	0.0412 (4)
H4	0.3809	0.2974	0.7365	0.049*
C41	0.25181 (15)	0.34968 (15)	0.66254 (10)	0.0430 (4)
C42	0.14654 (18)	0.40241 (18)	0.66471 (11)	0.0557 (5)
H42	0.1022	0.3880	0.7052	0.067*
C43	0.1061 (2)	0.4765 (2)	0.60732 (12)	0.0653 (6)
H43	0.0349	0.5108	0.6096	0.078*
C44	0.1706 (2)	0.49950 (18)	0.54698 (12)	0.0624 (6)
H44	0.1430	0.5485	0.5083	0.075*
C45	0.27641 (19)	0.44908 (18)	0.54448 (11)	0.0577 (6)
H45	0.3210	0.4651	0.5044	0.069*
C46	0.31644 (17)	0.37493 (17)	0.60126 (11)	0.0509 (5)
H46	0.3878	0.3411	0.5987	0.061*
C5	0.24444 (15)	0.26666 (16)	0.79953 (9)	0.0419 (4)
H5	0.2299	0.3444	0.8172	0.050*
C6	0.13571 (15)	0.19731 (17)	0.79254 (9)	0.0428 (5)
C7	0.15330 (15)	0.07787 (16)	0.76379 (9)	0.0418 (4)
H7	0.0807	0.0362	0.7582	0.050*
C8	0.23818 (14)	0.01906 (16)	0.82403 (10)	0.0416 (4)
H8	0.2048	0.0257	0.8731	0.050*
C81	0.26028 (15)	−0.10773 (16)	0.81148 (10)	0.0450 (5)
C82	0.34901 (17)	−0.16051 (18)	0.85505 (12)	0.0570 (5)
H82	0.3933	−0.1176	0.8905	0.068*
C83	0.37275 (19)	−0.27513 (19)	0.84674 (14)	0.0663 (6)
H83	0.4322	−0.3088	0.8766	0.080*
C84	0.30800 (19)	−0.34003 (19)	0.79392 (14)	0.0641 (6)
H84	0.3248	−0.4169	0.7873	0.077*
C85	0.21865 (18)	−0.28987 (18)	0.75136 (12)	0.0588 (6)
H85	0.1742	−0.3334	0.7163	0.071*
C86	0.19431 (17)	−0.17494 (17)	0.76025 (11)	0.0521 (5)
H86	0.1330	−0.1424	0.7315	0.063*
C9	0.32541 (15)	0.20001 (16)	0.85941 (10)	0.0430 (4)
H9	0.2830	0.1904	0.9048	0.052*
C91	0.43676 (16)	0.26184 (16)	0.88513 (10)	0.0446 (5)
C92	0.44226 (18)	0.37947 (17)	0.89234 (12)	0.0572 (5)
H92	0.3774	0.4231	0.8795	0.069*
C93	0.54295 (19)	0.43349 (19)	0.91836 (13)	0.0651 (6)
H93	0.5451	0.5128	0.9222	0.078*
C94	0.63916 (19)	0.3710 (2)	0.93847 (13)	0.0630 (6)
H94	0.7066	0.4072	0.9560	0.076*
C95	0.63462 (19)	0.2548 (2)	0.93249 (15)	0.0725 (7)
H95	0.6995	0.2117	0.9464	0.087*
C96	0.53496 (18)	0.20016 (19)	0.90603 (13)	0.0638 (6)
H96	0.5338	0.1209	0.9022	0.077*
C10	0.20908 (14)	0.08395 (16)	0.68665 (9)	0.0404 (4)
H10	0.2312	0.0054	0.6753	0.048*
C101	0.12842 (15)	0.12158 (15)	0.61951 (10)	0.0424 (4)
C102	0.01304 (16)	0.1409 (2)	0.62516 (11)	0.0575 (6)
H102	−0.0170	0.1350	0.6723	0.069*
C103	−0.05862 (19)	0.1690 (2)	0.56173 (12)	0.0672 (6)
H103	−0.1358	0.1824	0.5668	0.081*
C104	−0.0160 (2)	0.1770 (2)	0.49134 (13)	0.0683 (6)
H104	−0.0640	0.1952	0.4487	0.082*
C105	0.09871 (19)	0.1576 (2)	0.48493 (11)	0.0611 (6)
H105	0.1281	0.1627	0.4375	0.073*
C106	0.17031 (17)	0.13074 (17)	0.54786 (10)	0.0491 (5)
H106	0.2476	0.1186	0.5425	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0472 (8)	0.0753 (10)	0.0478 (8)	0.0098 (7)	0.0038 (6)	−0.0103 (7)
N1	0.0425 (8)	0.0428 (8)	0.0390 (8)	−0.0005 (7)	−0.0001 (6)	0.0022 (7)
C2	0.0416 (10)	0.0462 (11)	0.0411 (10)	0.0038 (8)	0.0022 (8)	0.0037 (8)
N3	0.0411 (8)	0.0444 (9)	0.0376 (8)	0.0025 (7)	0.0026 (6)	0.0022 (7)
C4	0.0442 (10)	0.0425 (10)	0.0367 (9)	0.0011 (8)	0.0005 (7)	0.0011 (8)
C41	0.0518 (11)	0.0380 (10)	0.0383 (10)	−0.0012 (8)	−0.0026 (8)	0.0005 (8)
C42	0.0616 (12)	0.0575 (13)	0.0477 (11)	0.0119 (10)	0.0034 (9)	0.0029 (10)
C43	0.0731 (14)	0.0652 (14)	0.0555 (13)	0.0193 (12)	−0.0095 (11)	0.0031 (11)
C44	0.0900 (16)	0.0476 (12)	0.0464 (12)	0.0031 (12)	−0.0160 (11)	0.0061 (9)
C45	0.0764 (14)	0.0520 (12)	0.0441 (11)	−0.0101 (11)	0.0012 (10)	0.0067 (10)
C46	0.0556 (11)	0.0481 (12)	0.0485 (11)	−0.0038 (9)	0.0005 (9)	0.0068 (9)
C5	0.0470 (10)	0.0432 (10)	0.0348 (9)	0.0054 (8)	−0.0012 (8)	−0.0016 (8)
C6	0.0424 (10)	0.0582 (12)	0.0273 (9)	0.0071 (9)	−0.0014 (7)	0.0030 (8)
C7	0.0401 (9)	0.0494 (11)	0.0357 (9)	0.0002 (8)	0.0013 (7)	0.0018 (8)
C8	0.0425 (9)	0.0484 (11)	0.0338 (9)	−0.0012 (8)	0.0014 (7)	0.0027 (8)
C81	0.0448 (10)	0.0470 (11)	0.0434 (10)	−0.0025 (9)	0.0040 (8)	0.0061 (9)
C82	0.0568 (12)	0.0523 (13)	0.0600 (13)	−0.0016 (10)	−0.0085 (10)	0.0043 (10)
C83	0.0623 (13)	0.0558 (14)	0.0792 (15)	0.0076 (11)	−0.0052 (11)	0.0104 (12)
C84	0.0639 (13)	0.0443 (12)	0.0849 (16)	−0.0003 (10)	0.0112 (12)	0.0011 (11)
C85	0.0614 (13)	0.0508 (13)	0.0638 (13)	−0.0100 (10)	0.0025 (10)	−0.0024 (10)
C86	0.0489 (11)	0.0526 (12)	0.0539 (12)	−0.0067 (9)	−0.0022 (9)	0.0049 (10)
C9	0.0493 (10)	0.0447 (11)	0.0346 (9)	0.0020 (8)	0.0002 (8)	0.0027 (8)
C91	0.0524 (11)	0.0457 (11)	0.0349 (9)	−0.0002 (9)	−0.0025 (8)	0.0025 (8)
C92	0.0609 (12)	0.0469 (12)	0.0617 (13)	0.0039 (10)	−0.0100 (10)	0.0036 (10)
C93	0.0759 (15)	0.0473 (13)	0.0695 (14)	−0.0086 (11)	−0.0110 (12)	0.0031 (11)
C94	0.0603 (13)	0.0615 (14)	0.0646 (14)	−0.0131 (11)	−0.0116 (10)	0.0020 (11)
C95	0.0571 (13)	0.0605 (15)	0.0955 (18)	0.0020 (11)	−0.0227 (12)	−0.0052 (13)
C96	0.0611 (13)	0.0460 (12)	0.0807 (15)	0.0028 (10)	−0.0185 (11)	−0.0007 (11)
C10	0.0434 (10)	0.0433 (10)	0.0344 (9)	0.0015 (8)	0.0028 (7)	−0.0009 (8)
C101	0.0502 (11)	0.0406 (10)	0.0355 (9)	−0.0001 (8)	−0.0016 (8)	−0.0022 (8)
C102	0.0505 (11)	0.0811 (15)	0.0401 (11)	0.0047 (10)	−0.0011 (9)	−0.0035 (10)
C103	0.0522 (12)	0.0933 (18)	0.0542 (13)	0.0068 (12)	−0.0096 (10)	0.0014 (12)
C104	0.0707 (15)	0.0833 (17)	0.0475 (13)	−0.0047 (12)	−0.0176 (11)	0.0106 (11)
C105	0.0739 (15)	0.0717 (15)	0.0370 (11)	−0.0051 (12)	0.0003 (10)	0.0076 (10)
C106	0.0540 (11)	0.0539 (12)	0.0395 (10)	0.0001 (9)	0.0029 (9)	0.0032 (9)

Geometric parameters (Å, º)

O1—C6	1.222 (2)	C82—H82	0.9300
N1—C9	1.474 (2)	C83—C84	1.384 (3)
N1—C8	1.481 (2)	C83—H83	0.9300
N1—C2	1.483 (2)	C84—C85	1.374 (3)
C2—N3	1.480 (2)	C84—H84	0.9300
C2—H2A	0.9700	C85—C86	1.386 (3)
C2—H2B	0.9700	C85—H85	0.9300
N3—C4	1.487 (2)	C86—H86	0.9300
N3—C10	1.490 (2)	C9—C91	1.532 (3)
C4—C41	1.521 (2)	C9—H9	0.9800
C4—C5	1.555 (2)	C91—C92	1.383 (3)
C4—H4	0.9800	C91—C96	1.386 (3)
C41—C42	1.384 (3)	C92—C93	1.387 (3)
C41—C46	1.398 (3)	C92—H92	0.9300
C42—C43	1.389 (3)	C93—C94	1.369 (3)
C42—H42	0.9300	C93—H93	0.9300
C43—C44	1.378 (3)	C94—C95	1.364 (3)
C43—H43	0.9300	C94—H94	0.9300
C44—C45	1.379 (3)	C95—C96	1.383 (3)
C44—H44	0.9300	C95—H95	0.9300
C45—C46	1.380 (3)	C96—H96	0.9300
C45—H45	0.9300	C10—C101	1.524 (2)
C46—H46	0.9300	C10—H10	0.9800
C5—C6	1.509 (3)	C101—C102	1.384 (3)
C5—C9	1.573 (2)	C101—C106	1.394 (3)
C5—H5	0.9800	C102—C103	1.387 (3)
C6—C7	1.506 (3)	C102—H102	0.9300
C7—C10	1.555 (2)	C103—C104	1.376 (3)
C7—C8	1.560 (2)	C103—H103	0.9300
C7—H7	0.9800	C104—C105	1.378 (3)
C8—C81	1.525 (3)	C104—H104	0.9300
C8—H8	0.9800	C105—C106	1.377 (3)
C81—C86	1.389 (3)	C105—H105	0.9300
C81—C82	1.391 (3)	C106—H106	0.9300
C82—C83	1.379 (3)
C9—N1—C8	109.43 (14)	C81—C82—H82	119.3
C9—N1—C2	110.47 (14)	C82—C83—C84	120.0 (2)
C8—N1—C2	109.09 (13)	C82—C83—H83	120.0
N3—C2—N1	114.27 (13)	C84—C83—H83	120.0
N3—C2—H2A	108.7	C85—C84—C83	119.4 (2)
N1—C2—H2A	108.7	C85—C84—H84	120.3
N3—C2—H2B	108.7	C83—C84—H84	120.3
N1—C2—H2B	108.7	C84—C85—C86	120.5 (2)
H2A—C2—H2B	107.6	C84—C85—H85	119.7
C2—N3—C4	107.01 (13)	C86—C85—H85	119.7
C2—N3—C10	107.32 (13)	C85—C86—C81	120.88 (19)
C4—N3—C10	113.76 (13)	C85—C86—H86	119.6
N3—C4—C41	113.80 (14)	C81—C86—H86	119.6
N3—C4—C5	109.34 (14)	N1—C9—C91	111.90 (14)
C41—C4—C5	116.19 (14)	N1—C9—C5	109.44 (14)
N3—C4—H4	105.5	C91—C9—C5	115.04 (15)
C41—C4—H4	105.5	N1—C9—H9	106.6
C5—C4—H4	105.5	C91—C9—H9	106.6
C42—C41—C46	117.69 (17)	C5—C9—H9	106.6
C42—C41—C4	124.42 (17)	C92—C91—C96	117.48 (18)
C46—C41—C4	117.86 (16)	C92—C91—C9	121.99 (17)
C41—C42—C43	121.0 (2)	C96—C91—C9	120.44 (17)
C41—C42—H42	119.5	C91—C92—C93	121.09 (19)
C43—C42—H42	119.5	C91—C92—H92	119.5
C44—C43—C42	120.5 (2)	C93—C92—H92	119.5
C44—C43—H43	119.8	C94—C93—C92	120.5 (2)
C42—C43—H43	119.8	C94—C93—H93	119.8
C43—C44—C45	119.30 (19)	C92—C93—H93	119.8
C43—C44—H44	120.3	C95—C94—C93	119.0 (2)
C45—C44—H44	120.3	C95—C94—H94	120.5
C44—C45—C46	120.3 (2)	C93—C94—H94	120.5
C44—C45—H45	119.9	C94—C95—C96	120.9 (2)
C46—C45—H45	119.9	C94—C95—H95	119.5
C45—C46—C41	121.27 (19)	C96—C95—H95	119.5
C45—C46—H46	119.4	C95—C96—C91	121.0 (2)
C41—C46—H46	119.4	C95—C96—H96	119.5
C6—C5—C4	111.50 (14)	C91—C96—H96	119.5
C6—C5—C9	104.63 (14)	N3—C10—C101	114.58 (14)
C4—C5—C9	107.62 (14)	N3—C10—C7	109.70 (13)
C6—C5—H5	111.0	C101—C10—C7	114.54 (14)
C4—C5—H5	111.0	N3—C10—H10	105.7
C9—C5—H5	111.0	C101—C10—H10	105.7
O1—C6—C7	123.81 (17)	C7—C10—H10	105.7
O1—C6—C5	123.08 (18)	C102—C101—C106	117.81 (17)
C7—C6—C5	112.94 (15)	C102—C101—C10	123.02 (16)
C6—C7—C10	109.24 (15)	C106—C101—C10	119.07 (16)
C6—C7—C8	106.05 (14)	C101—C102—C103	121.16 (19)
C10—C7—C8	109.07 (14)	C101—C102—H102	119.4
C6—C7—H7	110.8	C103—C102—H102	119.4
C10—C7—H7	110.8	C104—C103—C102	120.3 (2)
C8—C7—H7	110.8	C104—C103—H103	119.9
N1—C8—C81	110.95 (14)	C102—C103—H103	119.9
N1—C8—C7	109.08 (14)	C103—C104—C105	119.1 (2)
C81—C8—C7	115.90 (15)	C103—C104—H104	120.4
N1—C8—H8	106.8	C105—C104—H104	120.4
C81—C8—H8	106.8	C106—C105—C104	120.8 (2)
C7—C8—H8	106.8	C106—C105—H105	119.6
C86—C81—C82	117.74 (18)	C104—C105—H105	119.6
C86—C81—C8	123.55 (16)	C105—C106—C101	120.85 (18)
C82—C81—C8	118.68 (17)	C105—C106—H106	119.6
C83—C82—C81	121.4 (2)	C101—C106—H106	119.6
C83—C82—H82	119.3
C9—N1—C2—N3	−58.82 (19)	C81—C82—C83—C84	0.3 (3)
C8—N1—C2—N3	61.51 (19)	C82—C83—C84—C85	−1.5 (3)
N1—C2—N3—C4	60.90 (18)	C83—C84—C85—C86	0.9 (3)
N1—C2—N3—C10	−61.56 (19)	C84—C85—C86—C81	0.8 (3)
C2—N3—C4—C41	166.43 (14)	C82—C81—C86—C85	−2.0 (3)
C10—N3—C4—C41	−75.22 (18)	C8—C81—C86—C85	−179.99 (18)
C2—N3—C4—C5	−61.82 (16)	C8—N1—C9—C91	166.56 (13)
C10—N3—C4—C5	56.53 (17)	C2—N1—C9—C91	−73.31 (17)
N3—C4—C41—C42	115.3 (2)	C8—N1—C9—C5	−64.71 (17)
C5—C4—C41—C42	−13.0 (3)	C2—N1—C9—C5	55.42 (18)
N3—C4—C41—C46	−66.5 (2)	C6—C5—C9—N1	61.04 (17)
C5—C4—C41—C46	165.12 (16)	C4—C5—C9—N1	−57.67 (18)
C46—C41—C42—C43	0.9 (3)	C6—C5—C9—C91	−171.99 (15)
C4—C41—C42—C43	179.06 (19)	C4—C5—C9—C91	69.31 (19)
C41—C42—C43—C44	−0.4 (3)	N1—C9—C91—C92	160.10 (17)
C42—C43—C44—C45	−0.6 (3)	C5—C9—C91—C92	34.4 (2)
C43—C44—C45—C46	1.0 (3)	N1—C9—C91—C96	−23.4 (2)
C44—C45—C46—C41	−0.4 (3)	C5—C9—C91—C96	−149.10 (18)
C42—C41—C46—C45	−0.5 (3)	C96—C91—C92—C93	1.0 (3)
C4—C41—C46—C45	−178.79 (17)	C9—C91—C92—C93	177.64 (18)
N3—C4—C5—C6	−52.52 (18)	C91—C92—C93—C94	−0.8 (3)
C41—C4—C5—C6	77.95 (19)	C92—C93—C94—C95	0.1 (4)
N3—C4—C5—C9	61.68 (17)	C93—C94—C95—C96	0.5 (4)
C41—C4—C5—C9	−167.85 (15)	C94—C95—C96—C91	−0.3 (4)
C4—C5—C6—O1	−130.25 (17)	C92—C91—C96—C95	−0.5 (3)
C9—C5—C6—O1	113.71 (18)	C9—C91—C96—C95	−177.2 (2)
C4—C5—C6—C7	54.42 (19)	C2—N3—C10—C101	−170.58 (14)
C9—C5—C6—C7	−61.63 (17)	C4—N3—C10—C101	71.24 (18)
O1—C6—C7—C10	129.04 (17)	C2—N3—C10—C7	58.95 (17)
C5—C6—C7—C10	−55.67 (18)	C4—N3—C10—C7	−59.23 (18)
O1—C6—C7—C8	−113.54 (18)	C6—C7—C10—N3	56.44 (18)
C5—C6—C7—C8	61.75 (18)	C8—C7—C10—N3	−59.06 (19)
C9—N1—C8—C81	−167.43 (14)	C6—C7—C10—C101	−74.05 (19)
C2—N1—C8—C81	71.60 (17)	C8—C7—C10—C101	170.45 (15)
C9—N1—C8—C7	63.72 (17)	N3—C10—C101—C102	−132.51 (19)
C2—N1—C8—C7	−57.25 (18)	C7—C10—C101—C102	−4.4 (3)
C6—C7—C8—N1	−59.91 (18)	N3—C10—C101—C106	51.4 (2)
C10—C7—C8—N1	57.62 (18)	C7—C10—C101—C106	179.46 (16)
C6—C7—C8—C81	174.05 (14)	C106—C101—C102—C103	−0.3 (3)
C10—C7—C8—C81	−68.42 (19)	C10—C101—C102—C103	−176.4 (2)
N1—C8—C81—C86	−137.98 (17)	C101—C102—C103—C104	0.6 (4)
C7—C8—C81—C86	−12.9 (2)	C102—C103—C104—C105	−0.5 (4)
N1—C8—C81—C82	44.0 (2)	C103—C104—C105—C106	−0.1 (4)
C7—C8—C81—C82	169.11 (16)	C104—C105—C106—C101	0.5 (3)
C86—C81—C82—C83	1.4 (3)	C102—C101—C106—C105	−0.3 (3)
C8—C81—C82—C83	179.53 (19)	C10—C101—C106—C105	175.97 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C86—H86···O1^i	0.93	2.62	3.191 (2)	120
C105—H105···O1^ii	0.93	2.64	3.310 (2)	130

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