1,3-Bis(2,6-diisopropyl-phen-yl)imidazolidin-2-yl-idene.

The title compound, C(27)H(38)N(2), is the first reported free imidazolidin-2-yl-idene carbene with 2,6-diisopropyl-phenyl groups in the 1,3-positions. The five-membered ring adopts a twisted conformation and the dihedral angle between the aromatic rings is 48.81 (6)°. Both isopropyl groups attached to one of the benzene rings are disordered over two sets of sites in 0.74 (2):0.26 (2) and 0.599 (8):0.401 (8) ratios.

Related literature

There are few examples in the literature of crystallograph­ic­ally characterized free ylidenes with ortho-alkyl substituted phenyl groups in the 1,3-positions: for related structures see: Arduengo et al. (1991 ▶, 1992 ▶, 1995 ▶, 1999 ▶). For background to free carbenes, see: Igau et al. (1989 ▶) and for Arduengo-type carbenes, see: Pauling (1980 ▶).

Experimental

Crystal data

C27H38N2

M = 390.59

Monoclinic,

a = 20.835 (7) Å

b = 5.922 (2) Å

c = 19.694 (7) Å

β = 93.090 (4)°

V = 2426.2 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.06 mm−1

T = 150 K

0.50 × 0.34 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.716, T max = 0.746

22607 measured reflections

4259 independent reflections

3326 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.01

4259 reflections

319 parameters

168 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029922/hb5563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029922/hb5563Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H38N2	F(000) = 856
Mr = 390.59	Dx = 1.069 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9396 reflections
a = 20.835 (7) Å	θ = 2.2–28.4°
b = 5.922 (2) Å	µ = 0.06 mm−1
c = 19.694 (7) Å	T = 150 K
β = 93.090 (4)°	Block, colourless
V = 2426.2 (14) Å3	0.50 × 0.34 × 0.12 mm
Z = 4

Bruker APEXII CCD diffractometer	4259 independent reflections
Radiation source: fine-focus sealed tube	3326 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −24→24
Tmin = 0.716, Tmax = 0.746	k = −7→7
22607 measured reflections	l = −23→23

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.6416P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
4259 reflections	Δρmax = 0.18 e Å−3
319 parameters	Δρmin = −0.14 e Å−3
168 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (6)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.21083 (5)	0.66151 (18)	0.15446 (5)	0.0270 (3)
N2	0.30506 (5)	0.79278 (17)	0.17711 (5)	0.0263 (3)
C1	0.24262 (6)	0.8528 (2)	0.17156 (6)	0.0252 (3)
C2	0.25298 (6)	0.4697 (2)	0.13858 (8)	0.0379 (4)
H2A	0.2557	0.4496	0.0889	0.046*
H2B	0.2382	0.3272	0.1589	0.046*
C3	0.31647 (6)	0.5471 (2)	0.17175 (8)	0.0369 (4)
H3A	0.3248	0.4771	0.2170	0.044*
H3B	0.3528	0.5136	0.1429	0.044*
C4	0.35630 (6)	0.9431 (2)	0.19756 (6)	0.0251 (3)
C5	0.36374 (6)	1.0164 (2)	0.26515 (7)	0.0286 (3)
C6	0.41414 (6)	1.1635 (2)	0.28223 (7)	0.0327 (3)
H6A	0.4197	1.2172	0.3276	0.039*
C7	0.45624 (6)	1.2329 (2)	0.23476 (7)	0.0330 (3)
H7A	0.4904	1.3331	0.2475	0.040*
C8	0.44864 (6)	1.1564 (2)	0.16868 (7)	0.0301 (3)
H8A	0.4779	1.2043	0.1363	0.036*
C9	0.39891 (6)	1.0107 (2)	0.14862 (6)	0.0268 (3)
C10	0.39200 (6)	0.9307 (2)	0.07521 (7)	0.0324 (3)
H10A	0.3536	0.8297	0.0707	0.039*
C11	0.45050 (7)	0.7930 (3)	0.05695 (8)	0.0427 (4)
H11A	0.4566	0.6670	0.0889	0.064*
H11B	0.4888	0.8896	0.0596	0.064*
H11C	0.4437	0.7340	0.0106	0.064*
C12	0.38055 (8)	1.1287 (3)	0.02624 (7)	0.0461 (4)
H12A	0.3424	1.2128	0.0387	0.069*
H12B	0.3739	1.0714	−0.0203	0.069*
H12C	0.4180	1.2290	0.0290	0.069*
C13	0.31902 (7)	0.9415 (3)	0.31916 (7)	0.0366 (3)
H13A	0.2890	0.8257	0.2984	0.044*
C14	0.27892 (8)	1.1385 (3)	0.34266 (9)	0.0580 (5)
H14A	0.2547	1.2044	0.3035	0.087*
H14B	0.3073	1.2533	0.3639	0.087*
H14C	0.2489	1.0847	0.3757	0.087*
C15	0.35625 (8)	0.8326 (3)	0.37951 (8)	0.0608 (5)
H15A	0.3810	0.7042	0.3636	0.091*
H15B	0.3260	0.7799	0.4125	0.091*
H15C	0.3856	0.9438	0.4011	0.091*
C16	0.14366 (6)	0.6519 (2)	0.13366 (6)	0.0268 (3)
C17	0.10301 (6)	0.5242 (2)	0.17292 (7)	0.0320 (3)
C18	0.03883 (6)	0.5047 (3)	0.15029 (8)	0.0390 (4)
H18A	0.0104	0.4177	0.1759	0.047*
C19	0.01594 (7)	0.6089 (3)	0.09170 (8)	0.0431 (4)
H19A	−0.0280	0.5931	0.0770	0.052*
C20	0.05626 (7)	0.7360 (3)	0.05408 (7)	0.0408 (4)
H20A	0.0396	0.8082	0.0138	0.049*
C21	0.12121 (6)	0.7610 (2)	0.07385 (7)	0.0317 (3)
C22B	0.1629 (5)	0.9020 (16)	0.0300 (6)	0.0390 (10)	0.74 (2)
H22A	0.2022	0.9410	0.0591	0.047*	0.74 (2)
C23B	0.1861 (4)	0.7654 (14)	−0.0289 (4)	0.0624 (15)	0.74 (2)
H23A	0.2075	0.6282	−0.0116	0.094*	0.74 (2)
H23B	0.2164	0.8558	−0.0539	0.094*	0.74 (2)
H23C	0.1493	0.7240	−0.0595	0.094*	0.74 (2)
C24B	0.1334 (4)	1.1277 (10)	0.0058 (4)	0.0546 (15)	0.74 (2)
H24A	0.1183	1.2108	0.0449	0.082*	0.74 (2)
H24B	0.0972	1.0989	−0.0269	0.082*	0.74 (2)
H24C	0.1660	1.2175	−0.0161	0.082*	0.74 (2)
C22A	0.1707 (15)	0.880 (4)	0.0293 (14)	0.037 (2)	0.26 (2)
H22B	0.2152	0.8825	0.0512	0.045*	0.26 (2)
C23A	0.1669 (12)	0.755 (4)	−0.0425 (9)	0.056 (3)	0.26 (2)
H23D	0.1970	0.8264	−0.0726	0.083*	0.26 (2)
H23E	0.1231	0.7667	−0.0630	0.083*	0.26 (2)
H23F	0.1783	0.5958	−0.0361	0.083*	0.26 (2)
C24A	0.1448 (11)	1.106 (3)	0.0164 (12)	0.044 (3)	0.26 (2)
H24D	0.1483	1.1944	0.0585	0.066*	0.26 (2)
H24E	0.0995	1.0942	0.0006	0.066*	0.26 (2)
H24F	0.1690	1.1802	−0.0185	0.066*	0.26 (2)
C25B	0.1227 (4)	0.4253 (16)	0.2422 (5)	0.0339 (9)	0.599 (8)
H25A	0.1698	0.4534	0.2505	0.041*	0.599 (8)
C26B	0.1126 (4)	0.1722 (14)	0.2434 (5)	0.0444 (11)	0.599 (8)
H26A	0.1338	0.1030	0.2053	0.067*	0.599 (8)
H26B	0.0665	0.1392	0.2392	0.067*	0.599 (8)
H26C	0.1310	0.1106	0.2864	0.067*	0.599 (8)
C27B	0.0885 (3)	0.5341 (5)	0.30107 (14)	0.0470 (10)	0.599 (8)
H27A	0.0932	0.6986	0.2989	0.070*	0.599 (8)
H27B	0.1077	0.4787	0.3445	0.070*	0.599 (8)
H27C	0.0428	0.4945	0.2974	0.070*	0.599 (8)
C25A	0.1323 (7)	0.398 (2)	0.2352 (7)	0.0383 (16)	0.401 (8)
H25B	0.1779	0.3604	0.2266	0.046*	0.401 (8)
C26A	0.0966 (7)	0.178 (2)	0.2496 (10)	0.065 (3)	0.401 (8)
H26D	0.1186	0.0995	0.2882	0.097*	0.401 (8)
H26E	0.0961	0.0802	0.2094	0.097*	0.401 (8)
H26F	0.0523	0.2121	0.2606	0.097*	0.401 (8)
C27A	0.1321 (4)	0.5605 (9)	0.2935 (2)	0.0548 (18)	0.401 (8)
H27D	0.1528	0.4903	0.3340	0.082*	0.401 (8)
H27E	0.0876	0.6000	0.3024	0.082*	0.401 (8)
H27F	0.1556	0.6974	0.2821	0.082*	0.401 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0214 (5)	0.0227 (6)	0.0366 (6)	0.0006 (5)	−0.0017 (4)	0.0014 (5)
N2	0.0228 (5)	0.0192 (6)	0.0366 (6)	0.0009 (4)	−0.0017 (4)	0.0016 (5)
C1	0.0237 (6)	0.0264 (7)	0.0252 (6)	0.0000 (5)	0.0002 (5)	0.0032 (5)
C2	0.0277 (7)	0.0221 (7)	0.0631 (10)	0.0019 (6)	−0.0051 (7)	−0.0008 (7)
C3	0.0273 (7)	0.0222 (7)	0.0604 (10)	0.0013 (6)	−0.0051 (6)	0.0017 (7)
C4	0.0214 (6)	0.0200 (6)	0.0333 (7)	0.0017 (5)	−0.0039 (5)	0.0019 (5)
C5	0.0268 (7)	0.0271 (7)	0.0314 (7)	0.0055 (6)	−0.0025 (5)	0.0023 (6)
C6	0.0329 (7)	0.0307 (8)	0.0335 (7)	0.0045 (6)	−0.0076 (6)	−0.0036 (6)
C7	0.0271 (7)	0.0255 (7)	0.0454 (8)	−0.0016 (6)	−0.0087 (6)	−0.0008 (6)
C8	0.0236 (7)	0.0277 (7)	0.0390 (8)	−0.0006 (6)	0.0004 (5)	0.0050 (6)
C9	0.0234 (6)	0.0242 (7)	0.0323 (7)	0.0035 (5)	−0.0020 (5)	0.0023 (6)
C10	0.0300 (7)	0.0345 (8)	0.0328 (7)	−0.0010 (6)	0.0016 (6)	−0.0018 (6)
C11	0.0435 (9)	0.0424 (9)	0.0427 (9)	0.0055 (7)	0.0069 (7)	−0.0045 (7)
C12	0.0572 (10)	0.0485 (10)	0.0323 (8)	0.0104 (8)	−0.0014 (7)	0.0008 (7)
C13	0.0358 (8)	0.0432 (9)	0.0308 (7)	0.0016 (7)	0.0011 (6)	0.0052 (6)
C14	0.0544 (10)	0.0698 (12)	0.0518 (10)	0.0190 (9)	0.0202 (8)	0.0124 (9)
C15	0.0571 (11)	0.0747 (13)	0.0510 (10)	0.0123 (10)	0.0059 (8)	0.0300 (10)
C16	0.0222 (6)	0.0249 (7)	0.0329 (7)	0.0004 (5)	−0.0017 (5)	−0.0027 (6)
C17	0.0276 (7)	0.0295 (7)	0.0389 (7)	−0.0019 (6)	0.0014 (6)	−0.0008 (6)
C18	0.0272 (7)	0.0397 (9)	0.0505 (9)	−0.0065 (6)	0.0053 (6)	−0.0013 (7)
C19	0.0238 (7)	0.0504 (10)	0.0542 (10)	−0.0020 (7)	−0.0073 (7)	−0.0055 (8)
C20	0.0354 (8)	0.0459 (9)	0.0397 (8)	0.0025 (7)	−0.0100 (7)	0.0000 (7)
C21	0.0302 (7)	0.0328 (7)	0.0317 (7)	0.0006 (6)	−0.0023 (5)	−0.0022 (6)
C22B	0.029 (2)	0.048 (2)	0.0391 (18)	0.0014 (14)	−0.0040 (14)	0.0110 (14)
C23B	0.071 (3)	0.055 (2)	0.064 (3)	0.016 (2)	0.032 (3)	0.016 (2)
C24B	0.075 (4)	0.0357 (17)	0.054 (3)	0.0053 (15)	0.009 (2)	0.0093 (14)
C22A	0.047 (6)	0.037 (5)	0.027 (4)	−0.004 (4)	−0.005 (5)	0.011 (3)
C23A	0.088 (8)	0.045 (5)	0.035 (4)	0.006 (6)	0.014 (5)	0.001 (4)
C24A	0.053 (6)	0.034 (4)	0.044 (6)	−0.003 (4)	−0.003 (5)	0.002 (3)
C25B	0.024 (2)	0.0335 (19)	0.0445 (17)	0.0001 (19)	0.0031 (16)	0.0070 (17)
C26B	0.044 (3)	0.0332 (15)	0.057 (3)	0.0022 (19)	0.009 (2)	0.0067 (13)
C27B	0.063 (3)	0.0396 (15)	0.0390 (12)	0.0043 (16)	0.0089 (15)	0.0040 (11)
C25A	0.040 (5)	0.035 (4)	0.041 (3)	0.003 (3)	0.012 (2)	0.0096 (16)
C26A	0.073 (7)	0.044 (3)	0.079 (5)	−0.010 (4)	0.018 (5)	0.020 (3)
C27A	0.075 (5)	0.052 (2)	0.0371 (18)	0.009 (3)	−0.001 (2)	0.005 (2)

N1—C1	1.3458 (16)	C18—C19	1.371 (2)
N1—C16	1.4380 (16)	C18—H18A	0.9500
N1—C2	1.4793 (17)	C19—C20	1.374 (2)
N2—C1	1.3474 (16)	C19—H19A	0.9500
N2—C4	1.4309 (16)	C20—C21	1.3959 (19)
N2—C3	1.4790 (17)	C20—H20A	0.9500
C2—C3	1.5144 (19)	C21—C22B	1.509 (9)
C2—H2A	0.9900	C21—C22A	1.56 (3)
C2—H2B	0.9900	C22B—C23B	1.515 (9)
C3—H3A	0.9900	C22B—C24B	1.537 (6)
C3—H3B	0.9900	C22B—H22A	1.0000
C4—C5	1.4007 (18)	C23B—H23A	0.9800
C4—C9	1.4034 (18)	C23B—H23B	0.9800
C5—C6	1.3915 (19)	C23B—H23C	0.9800
C5—C13	1.5176 (19)	C24B—H24A	0.9800
C6—C7	1.379 (2)	C24B—H24B	0.9800
C6—H6A	0.9500	C24B—H24C	0.9800
C7—C8	1.3791 (19)	C22A—C24A	1.458 (17)
C7—H7A	0.9500	C22A—C23A	1.59 (3)
C8—C9	1.3894 (18)	C22A—H22B	1.0000
C8—H8A	0.9500	C23A—H23D	0.9800
C9—C10	1.5205 (19)	C23A—H23E	0.9800
C10—C11	1.526 (2)	C23A—H23F	0.9800
C10—C12	1.529 (2)	C24A—H24D	0.9800
C10—H10A	1.0000	C24A—H24E	0.9800
C11—H11A	0.9800	C24A—H24F	0.9800
C11—H11B	0.9800	C25B—C26B	1.514 (11)
C11—H11C	0.9800	C25B—C27B	1.535 (6)
C12—H12A	0.9800	C25B—H25A	1.0000
C12—H12B	0.9800	C26B—H26A	0.9800
C12—H12C	0.9800	C26B—H26B	0.9800
C13—C14	1.521 (2)	C26B—H26C	0.9800
C13—C15	1.527 (2)	C27B—H27A	0.9800
C13—H13A	1.0000	C27B—H27B	0.9800
C14—H14A	0.9800	C27B—H27C	0.9800
C14—H14B	0.9800	C25A—C27A	1.497 (10)
C14—H14C	0.9800	C25A—C26A	1.537 (18)
C15—H15A	0.9800	C25A—H25B	1.0000
C15—H15B	0.9800	C26A—H26D	0.9800
C15—H15C	0.9800	C26A—H26E	0.9800
C16—C17	1.3992 (19)	C26A—H26F	0.9800
C16—C21	1.4015 (18)	C27A—H27D	0.9800
C17—C18	1.3913 (19)	C27A—H27E	0.9800
C17—C25B	1.521 (11)	C27A—H27F	0.9800
C17—C25A	1.534 (18)
C1—N1—C16	124.27 (10)	C18—C19—C20	120.34 (13)
C1—N1—C2	114.15 (10)	C18—C19—H19A	119.8
C16—N1—C2	119.28 (10)	C20—C19—H19A	119.8
C1—N2—C4	124.14 (11)	C19—C20—C21	121.30 (14)
C1—N2—C3	114.32 (10)	C19—C20—H20A	119.3
C4—N2—C3	120.77 (10)	C21—C20—H20A	119.3
N1—C1—N2	104.98 (11)	C20—C21—C16	117.39 (13)
N1—C2—C3	101.04 (11)	C20—C21—C22B	118.6 (4)
N1—C2—H2A	111.6	C16—C21—C22B	124.0 (4)
C3—C2—H2A	111.6	C20—C21—C22A	123.5 (12)
N1—C2—H2B	111.6	C16—C21—C22A	118.7 (11)
C3—C2—H2B	111.6	C21—C22B—C23B	111.1 (7)
H2A—C2—H2B	109.4	C21—C22B—C24B	115.2 (6)
N2—C3—C2	100.85 (10)	C23B—C22B—C24B	111.4 (8)
N2—C3—H3A	111.6	C21—C22B—H22A	106.2
C2—C3—H3A	111.6	C23B—C22B—H22A	106.2
N2—C3—H3B	111.6	C24B—C22B—H22A	106.2
C2—C3—H3B	111.6	C22B—C23B—H23A	109.5
H3A—C3—H3B	109.4	C22B—C23B—H23B	109.5
C5—C4—C9	121.50 (12)	H23A—C23B—H23B	109.5
C5—C4—N2	120.20 (11)	C22B—C23B—H23C	109.5
C9—C4—N2	118.29 (11)	H23A—C23B—H23C	109.5
C6—C5—C4	117.85 (12)	H23B—C23B—H23C	109.5
C6—C5—C13	119.82 (12)	C22B—C24B—H24A	109.5
C4—C5—C13	122.33 (12)	C22B—C24B—H24B	109.5
C7—C6—C5	121.48 (13)	H24A—C24B—H24B	109.5
C7—C6—H6A	119.3	C22B—C24B—H24C	109.5
C5—C6—H6A	119.3	H24A—C24B—H24C	109.5
C6—C7—C8	119.80 (12)	H24B—C24B—H24C	109.5
C6—C7—H7A	120.1	C24A—C22A—C21	105.2 (18)
C8—C7—H7A	120.1	C24A—C22A—C23A	106 (2)
C7—C8—C9	121.22 (13)	C21—C22A—C23A	107 (2)
C7—C8—H8A	119.4	C24A—C22A—H22B	112.9
C9—C8—H8A	119.4	C21—C22A—H22B	112.9
C8—C9—C4	118.13 (12)	C23A—C22A—H22B	112.9
C8—C9—C10	119.64 (12)	C22A—C23A—H23D	109.5
C4—C9—C10	122.22 (11)	C22A—C23A—H23E	109.5
C9—C10—C11	110.78 (11)	H23D—C23A—H23E	109.5
C9—C10—C12	111.37 (12)	C22A—C23A—H23F	109.5
C11—C10—C12	111.15 (12)	H23D—C23A—H23F	109.5
C9—C10—H10A	107.8	H23E—C23A—H23F	109.5
C11—C10—H10A	107.8	C22A—C24A—H24D	109.5
C12—C10—H10A	107.8	C22A—C24A—H24E	109.5
C10—C11—H11A	109.5	H24D—C24A—H24E	109.5
C10—C11—H11B	109.5	C22A—C24A—H24F	109.5
H11A—C11—H11B	109.5	H24D—C24A—H24F	109.5
C10—C11—H11C	109.5	H24E—C24A—H24F	109.5
H11A—C11—H11C	109.5	C26B—C25B—C17	111.3 (7)
H11B—C11—H11C	109.5	C26B—C25B—C27B	109.5 (7)
C10—C12—H12A	109.5	C17—C25B—C27B	113.7 (6)
C10—C12—H12B	109.5	C26B—C25B—H25A	107.4
H12A—C12—H12B	109.5	C17—C25B—H25A	107.4
C10—C12—H12C	109.5	C27B—C25B—H25A	107.4
H12A—C12—H12C	109.5	C25B—C26B—H26A	109.5
H12B—C12—H12C	109.5	C25B—C26B—H26B	109.5
C5—C13—C14	110.94 (12)	H26A—C26B—H26B	109.5
C5—C13—C15	111.32 (12)	C25B—C26B—H26C	109.5
C14—C13—C15	110.57 (13)	H26A—C26B—H26C	109.5
C5—C13—H13A	108.0	H26B—C26B—H26C	109.5
C14—C13—H13A	108.0	C25B—C27B—H27A	109.5
C15—C13—H13A	108.0	C25B—C27B—H27B	109.5
C13—C14—H14A	109.5	H27A—C27B—H27B	109.5
C13—C14—H14B	109.5	C25B—C27B—H27C	109.5
H14A—C14—H14B	109.5	H27A—C27B—H27C	109.5
C13—C14—H14C	109.5	H27B—C27B—H27C	109.5
H14A—C14—H14C	109.5	C27A—C25A—C17	106.4 (9)
H14B—C14—H14C	109.5	C27A—C25A—C26A	112.5 (11)
C13—C15—H15A	109.5	C17—C25A—C26A	112.7 (12)
C13—C15—H15B	109.5	C27A—C25A—H25B	108.4
H15A—C15—H15B	109.5	C17—C25A—H25B	108.4
C13—C15—H15C	109.5	C26A—C25A—H25B	108.4
H15A—C15—H15C	109.5	C25A—C26A—H26D	109.5
H15B—C15—H15C	109.5	C25A—C26A—H26E	109.5
C17—C16—C21	121.95 (12)	H26D—C26A—H26E	109.5
C17—C16—N1	118.22 (11)	C25A—C26A—H26F	109.5
C21—C16—N1	119.78 (11)	H26D—C26A—H26F	109.5
C18—C17—C16	117.89 (13)	H26E—C26A—H26F	109.5
C18—C17—C25B	117.6 (4)	C25A—C27A—H27D	109.5
C16—C17—C25B	124.2 (4)	C25A—C27A—H27E	109.5
C18—C17—C25A	123.3 (6)	H27D—C27A—H27E	109.5
C16—C17—C25A	118.6 (6)	C25A—C27A—H27F	109.5
C19—C18—C17	121.12 (13)	H27D—C27A—H27F	109.5
C19—C18—H18A	119.4	H27E—C27A—H27F	109.5
C17—C18—H18A	119.4