[N,N-Bis(2,6-diisopropyl-phen-yl)pent-2-ene-2,4-diiminato(1-)]bis-(1,2,4-diaza-phosphol-1-yl)aluminium(III).

In the title compound, [Al(C(29)H(41)N(2))(C(2)H(2)N(2)P)(2)], the Al(III) atom is coordinated by four N atoms from β-diketiminate and 1,2,4-diaza-phospho-lide ligands in a slightly distorted tetra-hedral fashion.

Related literature

For similar related 1,2,4-diaza­phospho­lide complexes, see: Schmidpeter & Willhalm (1984 ▶); Cui et al. (2000 ▶); Ding et al. (2001 ▶); Kumar et al. (2004 ▶, 2005 ▶); Zheng et al. (2006 ▶); Wan et al. (2008 ▶); Pi et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

[Al(C29H41N2)(C2H2N2P)2]

M = 614.67

Triclinic,

a = 10.578 (4) Å

b = 12.578 (5) Å

c = 13.498 (5) Å

α = 92.059 (5)°

β = 98.766 (5)°

γ = 96.516 (5)°

V = 1760.8 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.35 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.940, T max = 0.965

7337 measured reflections

6082 independent reflections

4238 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.224

S = 1.02

6082 reflections

389 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et n class="Chemical">al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049007/bq2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049007/bq2246Isup2.hkl

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

[Al(C29H41N2)(C2H2N2P)2]	Z = 2
Mr = 614.67	F(000) = 656
Triclinic, P1	Dx = 1.159 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.578 (4) Å	Cell parameters from 872 reflections
b = 12.578 (5) Å	θ = 3.4–25.6°
c = 13.498 (5) Å	µ = 0.18 mm−1
α = 92.059 (5)°	T = 293 K
β = 98.766 (5)°	Sheet, yellow
γ = 96.516 (5)°	0.35 × 0.20 × 0.20 mm
V = 1760.8 (11) Å3

Bruker SMART APEXII CCD area-detector diffractometer	6082 independent reflections
Radiation source: fine-focus sealed tube	4238 reflections with I > 2σ(I)
graphite	Rint = 0.037
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
Tmin = 0.940, Tmax = 0.965	k = −11→14
7337 measured reflections	l = −16→12

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.075	w = 1/[σ2(Fo2) + (0.1531P)2 + ] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.224	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.47 e Å−3
6082 reflections	Δρmin = −0.56 e Å−3
389 parameters

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
Al1	0.22665 (7)	0.79946 (6)	0.78731 (6)	0.0419 (3)
P1	−0.16571 (10)	0.71060 (10)	0.62146 (10)	0.0880 (4)
P2	0.18913 (13)	1.08771 (11)	0.97295 (11)	0.1047 (5)
N1	0.0608 (2)	0.7524 (2)	0.7248 (2)	0.0574 (6)
N2	−0.0133 (3)	0.7202 (4)	0.7910 (3)	0.1033 (13)
N3	0.2190 (2)	0.9204 (2)	0.86843 (18)	0.0537 (6)
N4	0.3412 (2)	0.9627 (2)	0.9076 (2)	0.0652 (7)
N5	0.3149 (2)	0.70050 (18)	0.86114 (16)	0.0479 (6)
N6	0.3367 (2)	0.83042 (17)	0.69477 (16)	0.0435 (5)
C1	−0.1375 (5)	0.6917 (5)	0.7425 (4)	0.125 (2)
H1	−0.2025	0.6632	0.7766	0.149*
C2	−0.0057 (4)	0.7533 (3)	0.6309 (3)	0.0762 (10)
H2	0.0327	0.7753	0.5763	0.091*
C3	0.1292 (3)	0.9771 (3)	0.8954 (3)	0.0717 (9)
H3	0.0415	0.9581	0.8738	0.086*
C4	0.3387 (4)	1.0485 (3)	0.9637 (3)	0.0806 (11)
H4	0.4141	1.0871	0.9975	0.097*
C5	0.5225 (3)	0.6473 (3)	0.9408 (3)	0.0738 (10)
H5A	0.5084	0.6655	1.0076	0.111*
H5B	0.6123	0.6638	0.9364	0.111*
H5C	0.4967	0.5722	0.9253	0.111*
C6	0.4445 (3)	0.7107 (2)	0.8674 (2)	0.0504 (7)
C7	0.5112 (3)	0.7783 (2)	0.8092 (2)	0.0525 (7)
H7	0.6000	0.7900	0.8291	0.063*
C8	0.4642 (3)	0.8307 (2)	0.7260 (2)	0.0493 (7)
C9	0.5580 (3)	0.8893 (3)	0.6683 (3)	0.0737 (10)
H9A	0.5349	0.8682	0.5983	0.111*
H9B	0.6432	0.8721	0.6920	0.111*
H9C	0.5562	0.9651	0.6778	0.111*
C10	0.2540 (3)	0.6173 (3)	0.9171 (2)	0.0582 (8)
C11	0.2390 (3)	0.6407 (3)	1.0157 (3)	0.0725 (10)
C12	0.1862 (4)	0.5554 (5)	1.0671 (4)	0.0997 (16)
H12	0.1770	0.5676	1.1339	0.120*
C13	0.1485 (5)	0.4568 (5)	1.0230 (5)	0.1080 (17)
H13	0.1132	0.4027	1.0593	0.130*
C14	0.1618 (4)	0.4355 (4)	0.9258 (4)	0.0977 (14)
H14	0.1370	0.3667	0.8966	0.117*
C15	0.2122 (3)	0.5161 (3)	0.8695 (3)	0.0715 (10)
C16	0.2732 (4)	0.7513 (4)	1.0672 (3)	0.0849 (12)
H16	0.3084	0.7988	1.0194	0.102*
C17	0.3773 (6)	0.7541 (6)	1.1615 (3)	0.138 (2)
H17A	0.3416	0.7163	1.2133	0.207*
H17B	0.4057	0.8272	1.1849	0.207*
H17C	0.4491	0.7207	1.1450	0.207*
C18	0.1544 (5)	0.7959 (5)	1.0947 (4)	0.1133 (16)
H18A	0.0886	0.7905	1.0366	0.170*
H18B	0.1766	0.8697	1.1178	0.170*
H18C	0.1231	0.7555	1.1468	0.170*
C19	0.2203 (4)	0.4905 (3)	0.7606 (3)	0.0836 (11)
H19	0.2347	0.5587	0.7289	0.100*
C20	0.0958 (6)	0.4301 (5)	0.7050 (5)	0.142 (2)
H20A	0.0760	0.3648	0.7371	0.213*
H20B	0.1056	0.4137	0.6368	0.213*
H20C	0.0271	0.4737	0.7059	0.213*
C21	0.3319 (6)	0.4291 (5)	0.7488 (5)	0.149 (2)
H21A	0.4112	0.4722	0.7761	0.224*
H21B	0.3313	0.4118	0.6789	0.224*
H21C	0.3242	0.3642	0.7839	0.224*
C22	0.2938 (3)	0.8573 (2)	0.5916 (2)	0.0476 (6)
C23	0.2616 (3)	0.9594 (2)	0.5707 (2)	0.0548 (7)
C24	0.2151 (4)	0.9782 (3)	0.4717 (3)	0.0702 (9)
H24	0.1928	1.0458	0.4561	0.084*
C25	0.2012 (4)	0.8998 (4)	0.3964 (3)	0.0782 (10)
H25	0.1699	0.9140	0.3306	0.094*
C26	0.2336 (4)	0.8011 (3)	0.4187 (3)	0.0776 (10)
H26	0.2243	0.7484	0.3672	0.093*
C27	0.2802 (3)	0.7761 (3)	0.5160 (2)	0.0613 (8)
C28	0.2762 (4)	1.0491 (3)	0.6497 (3)	0.0691 (9)
H28	0.3124	1.0225	0.7140	0.083*
C29	0.3710 (4)	1.1436 (3)	0.6248 (3)	0.0898 (12)
H29A	0.4510	1.1183	0.6161	0.135*
H29B	0.3860	1.1975	0.6789	0.135*
H29C	0.3348	1.1737	0.5641	0.135*
C30	0.1480 (5)	1.0861 (4)	0.6605 (3)	0.0971 (14)
H30A	0.1175	1.1232	0.6023	0.146*
H30B	0.1579	1.1336	0.7193	0.146*
H30C	0.0869	1.0252	0.6669	0.146*
C31	0.3132 (4)	0.6642 (3)	0.5355 (3)	0.0788 (10)
H31	0.3299	0.6582	0.6084	0.095*
C32	0.2037 (7)	0.5800 (4)	0.4934 (5)	0.143 (2)
H32A	0.1274	0.5943	0.5193	0.214*
H32B	0.2253	0.5107	0.5125	0.214*
H32C	0.1885	0.5813	0.4215	0.214*
C33	0.4358 (7)	0.6444 (5)	0.4945 (6)	0.163 (3)
H33A	0.4168	0.6331	0.4228	0.244*
H33B	0.4681	0.5822	0.5232	0.244*
H33C	0.4996	0.7056	0.5117	0.244*

	U11	U22	U33	U12	U13	U23
Al1	0.0409 (4)	0.0430 (5)	0.0436 (4)	0.0117 (3)	0.0059 (3)	0.0077 (3)
P1	0.0608 (6)	0.0820 (7)	0.1125 (9)	0.0055 (5)	−0.0134 (5)	0.0134 (6)
P2	0.0950 (8)	0.0948 (9)	0.1276 (10)	0.0281 (7)	0.0282 (7)	−0.0450 (8)
N1	0.0461 (13)	0.0545 (15)	0.0702 (16)	0.0116 (11)	0.0003 (11)	0.0041 (12)
N2	0.069 (2)	0.160 (4)	0.084 (2)	0.013 (2)	0.0102 (17)	0.052 (2)
N3	0.0525 (13)	0.0565 (15)	0.0545 (13)	0.0158 (12)	0.0100 (11)	−0.0011 (11)
N4	0.0556 (15)	0.0683 (18)	0.0710 (17)	0.0125 (13)	0.0084 (12)	−0.0148 (14)
N5	0.0490 (13)	0.0486 (13)	0.0482 (12)	0.0112 (11)	0.0077 (10)	0.0143 (10)
N6	0.0479 (12)	0.0416 (12)	0.0439 (12)	0.0139 (10)	0.0088 (9)	0.0069 (9)
C1	0.087 (3)	0.152 (5)	0.157 (5)	0.031 (3)	0.061 (3)	0.084 (4)
C2	0.071 (2)	0.086 (3)	0.069 (2)	0.005 (2)	0.0050 (17)	0.0152 (19)
C3	0.0625 (19)	0.077 (2)	0.082 (2)	0.0228 (18)	0.0210 (16)	−0.0035 (18)
C4	0.073 (2)	0.079 (3)	0.085 (2)	0.0090 (19)	0.0056 (18)	−0.029 (2)
C5	0.062 (2)	0.081 (2)	0.083 (2)	0.0280 (18)	0.0020 (17)	0.0361 (19)
C6	0.0485 (15)	0.0505 (16)	0.0531 (15)	0.0147 (13)	0.0034 (12)	0.0080 (13)
C7	0.0419 (14)	0.0551 (17)	0.0626 (17)	0.0149 (13)	0.0074 (12)	0.0071 (14)
C8	0.0491 (15)	0.0446 (15)	0.0570 (16)	0.0123 (13)	0.0119 (12)	0.0037 (12)
C9	0.0579 (19)	0.086 (3)	0.084 (2)	0.0121 (18)	0.0261 (17)	0.026 (2)
C10	0.0487 (16)	0.066 (2)	0.0618 (18)	0.0156 (15)	0.0032 (13)	0.0298 (15)
C11	0.0610 (19)	0.100 (3)	0.0609 (19)	0.0191 (19)	0.0094 (15)	0.0404 (19)
C12	0.080 (3)	0.142 (5)	0.087 (3)	0.028 (3)	0.023 (2)	0.069 (3)
C13	0.086 (3)	0.109 (4)	0.132 (4)	0.008 (3)	0.016 (3)	0.073 (4)
C14	0.081 (3)	0.078 (3)	0.136 (4)	0.012 (2)	0.009 (3)	0.057 (3)
C15	0.0608 (19)	0.060 (2)	0.094 (3)	0.0116 (17)	0.0055 (18)	0.0335 (19)
C16	0.083 (2)	0.124 (4)	0.0481 (18)	0.015 (2)	0.0081 (17)	0.019 (2)
C17	0.114 (4)	0.229 (7)	0.066 (3)	0.032 (4)	−0.004 (3)	0.000 (4)
C18	0.112 (4)	0.148 (5)	0.089 (3)	0.034 (3)	0.029 (3)	0.012 (3)
C19	0.098 (3)	0.0468 (19)	0.105 (3)	0.0131 (19)	0.010 (2)	0.0077 (19)
C20	0.137 (5)	0.130 (5)	0.139 (5)	−0.030 (4)	−0.008 (4)	0.003 (4)
C21	0.143 (5)	0.138 (5)	0.175 (6)	0.058 (4)	0.028 (4)	−0.031 (4)
C22	0.0482 (14)	0.0521 (16)	0.0449 (14)	0.0108 (13)	0.0095 (11)	0.0087 (12)
C23	0.0603 (17)	0.0542 (17)	0.0519 (16)	0.0130 (14)	0.0088 (13)	0.0122 (13)
C24	0.078 (2)	0.072 (2)	0.064 (2)	0.0208 (19)	0.0079 (16)	0.0246 (17)
C25	0.086 (2)	0.099 (3)	0.0493 (18)	0.018 (2)	0.0036 (16)	0.0194 (19)
C26	0.092 (3)	0.091 (3)	0.0501 (18)	0.016 (2)	0.0098 (17)	−0.0016 (18)
C27	0.072 (2)	0.0618 (19)	0.0533 (17)	0.0107 (16)	0.0168 (14)	0.0032 (14)
C28	0.094 (2)	0.0515 (18)	0.0631 (19)	0.0244 (18)	0.0038 (17)	0.0110 (15)
C29	0.108 (3)	0.060 (2)	0.095 (3)	0.006 (2)	−0.002 (2)	0.013 (2)
C30	0.122 (4)	0.087 (3)	0.097 (3)	0.052 (3)	0.033 (3)	0.012 (2)
C31	0.111 (3)	0.059 (2)	0.069 (2)	0.017 (2)	0.017 (2)	−0.0058 (16)
C32	0.202 (6)	0.065 (3)	0.139 (5)	−0.008 (4)	−0.023 (4)	−0.014 (3)
C33	0.169 (6)	0.097 (4)	0.255 (8)	0.072 (4)	0.089 (6)	0.026 (5)

Al1—N1	1.848 (3)	C16—H16	0.9800
Al1—N6	1.855 (2)	C17—H17A	0.9600
Al1—N3	1.858 (3)	C17—H17B	0.9600
Al1—N5	1.867 (2)	C17—H17C	0.9600
P1—C1	1.646 (6)	C18—H18A	0.9600
P1—C2	1.700 (4)	C18—H18B	0.9600
P2—C3	1.711 (4)	C18—H18C	0.9600
P2—C4	1.731 (4)	C19—C21	1.506 (7)
N1—N2	1.320 (4)	C19—C20	1.518 (7)
N1—C2	1.354 (4)	C19—H19	0.9800
N2—C1	1.378 (6)	C20—H20A	0.9600
N3—C3	1.336 (4)	C20—H20B	0.9600
N3—N4	1.360 (4)	C20—H20C	0.9600
N4—C4	1.301 (4)	C21—H21A	0.9600
N5—C6	1.352 (4)	C21—H21B	0.9600
N5—C10	1.460 (4)	C21—H21C	0.9600
N6—C8	1.350 (4)	C22—C23	1.393 (4)
N6—C22	1.461 (3)	C22—C27	1.397 (4)
C1—H1	0.9300	C23—C24	1.390 (4)
C2—H2	0.9300	C23—C28	1.503 (4)
C3—H3	0.9300	C24—C25	1.370 (5)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.502 (4)	C25—C26	1.356 (5)
C5—H5A	0.9600	C25—H25	0.9300
C5—H5B	0.9600	C26—C27	1.391 (5)
C5—H5C	0.9600	C26—H26	0.9300
C6—C7	1.384 (4)	C27—C31	1.511 (5)
C7—C8	1.379 (4)	C28—C30	1.509 (6)
C7—H7	0.9300	C28—C29	1.546 (6)
C8—C9	1.498 (4)	C28—H28	0.9800
C9—H9A	0.9600	C29—H29A	0.9600
C9—H9B	0.9600	C29—H29B	0.9600
C9—H9C	0.9600	C29—H29C	0.9600
C10—C11	1.389 (5)	C30—H30A	0.9600
C10—C15	1.398 (5)	C30—H30B	0.9600
C11—C12	1.407 (6)	C30—H30C	0.9600
C11—C16	1.513 (6)	C31—C32	1.504 (7)
C12—C13	1.347 (7)	C31—C33	1.527 (7)
C12—H12	0.9300	C31—H31	0.9800
C13—C14	1.361 (7)	C32—H32A	0.9600
C13—H13	0.9300	C32—H32B	0.9600
C14—C15	1.395 (5)	C32—H32C	0.9600
C14—H14	0.9300	C33—H33A	0.9600
C15—C19	1.511 (6)	C33—H33B	0.9600
C16—C18	1.523 (6)	C33—H33C	0.9600
C16—C17	1.548 (6)
N1—Al1—N6	111.60 (12)	C16—C17—H17C	109.5
N1—Al1—N3	107.50 (11)	H17A—C17—H17C	109.5
N6—Al1—N3	110.79 (11)	H17B—C17—H17C	109.5
N1—Al1—N5	116.84 (12)	C16—C18—H18A	109.5
N6—Al1—N5	99.77 (10)	C16—C18—H18B	109.5
N3—Al1—N5	110.22 (11)	H18A—C18—H18B	109.5
C1—P1—C2	86.8 (2)	C16—C18—H18C	109.5
C3—P2—C4	85.27 (17)	H18A—C18—H18C	109.5
N2—N1—C2	112.7 (3)	H18B—C18—H18C	109.5
N2—N1—Al1	110.9 (2)	C21—C19—C15	112.2 (4)
C2—N1—Al1	135.9 (3)	C21—C19—C20	110.1 (4)
N1—N2—C1	109.3 (3)	C15—C19—C20	112.1 (4)
C3—N3—N4	113.3 (3)	C21—C19—H19	107.4
C3—N3—Al1	138.0 (2)	C15—C19—H19	107.4
N4—N3—Al1	108.65 (18)	C20—C19—H19	107.4
C4—N4—N3	109.9 (3)	C19—C20—H20A	109.5
C6—N5—C10	118.2 (2)	C19—C20—H20B	109.5
C6—N5—Al1	117.43 (19)	H20A—C20—H20B	109.5
C10—N5—Al1	124.27 (18)	C19—C20—H20C	109.5
C8—N6—C22	118.4 (2)	H20A—C20—H20C	109.5
C8—N6—Al1	117.63 (18)	H20B—C20—H20C	109.5
C22—N6—Al1	123.90 (17)	C19—C21—H21A	109.5
N2—C1—P1	116.9 (3)	C19—C21—H21B	109.5
N2—C1—H1	121.6	H21A—C21—H21B	109.5
P1—C1—H1	121.6	C19—C21—H21C	109.5
N1—C2—P1	114.1 (3)	H21A—C21—H21C	109.5
N1—C2—H2	122.9	H21B—C21—H21C	109.5
P1—C2—H2	122.9	C23—C22—C27	121.4 (3)
N3—C3—P2	114.3 (3)	C23—C22—N6	120.7 (2)
N3—C3—H3	122.8	C27—C22—N6	117.8 (3)
P2—C3—H3	122.8	C24—C23—C22	117.8 (3)
N4—C4—P2	117.2 (3)	C24—C23—C28	119.2 (3)
N4—C4—H4	121.4	C22—C23—C28	123.0 (3)
P2—C4—H4	121.4	C25—C24—C23	121.7 (3)
C6—C5—H5A	109.5	C25—C24—H24	119.2
C6—C5—H5B	109.5	C23—C24—H24	119.2
H5A—C5—H5B	109.5	C26—C25—C24	119.4 (3)
C6—C5—H5C	109.5	C26—C25—H25	120.3
H5A—C5—H5C	109.5	C24—C25—H25	120.3
H5B—C5—H5C	109.5	C25—C26—C27	122.3 (3)
N5—C6—C7	123.2 (3)	C25—C26—H26	118.9
N5—C6—C5	119.6 (3)	C27—C26—H26	118.9
C7—C6—C5	117.2 (3)	C26—C27—C22	117.5 (3)
C8—C7—C6	129.0 (3)	C26—C27—C31	119.4 (3)
C8—C7—H7	115.5	C22—C27—C31	123.2 (3)
C6—C7—H7	115.5	C23—C28—C30	111.5 (3)
N6—C8—C7	122.1 (3)	C23—C28—C29	110.2 (3)
N6—C8—C9	119.2 (3)	C30—C28—C29	110.5 (3)
C7—C8—C9	118.8 (3)	C23—C28—H28	108.2
C8—C9—H9A	109.5	C30—C28—H28	108.2
C8—C9—H9B	109.5	C29—C28—H28	108.2
H9A—C9—H9B	109.5	C28—C29—H29A	109.5
C8—C9—H9C	109.5	C28—C29—H29B	109.5
H9A—C9—H9C	109.5	H29A—C29—H29B	109.5
H9B—C9—H9C	109.5	C28—C29—H29C	109.5
C11—C10—C15	121.9 (3)	H29A—C29—H29C	109.5
C11—C10—N5	119.3 (3)	H29B—C29—H29C	109.5
C15—C10—N5	118.8 (3)	C28—C30—H30A	109.5
C10—C11—C12	116.5 (4)	C28—C30—H30B	109.5
C10—C11—C16	123.5 (3)	H30A—C30—H30B	109.5
C12—C11—C16	120.1 (4)	C28—C30—H30C	109.5
C13—C12—C11	122.2 (5)	H30A—C30—H30C	109.5
C13—C12—H12	118.9	H30B—C30—H30C	109.5
C11—C12—H12	118.9	C32—C31—C27	112.0 (4)
C12—C13—C14	120.7 (4)	C32—C31—C33	110.7 (5)
C12—C13—H13	119.7	C27—C31—C33	111.0 (4)
C14—C13—H13	119.7	C32—C31—H31	107.6
C13—C14—C15	120.5 (5)	C27—C31—H31	107.6
C13—C14—H14	119.8	C33—C31—H31	107.6
C15—C14—H14	119.8	C31—C32—H32A	109.5
C14—C15—C10	118.2 (4)	C31—C32—H32B	109.5
C14—C15—C19	118.9 (4)	H32A—C32—H32B	109.5
C10—C15—C19	122.9 (3)	C31—C32—H32C	109.5
C11—C16—C18	111.3 (4)	H32A—C32—H32C	109.5
C11—C16—C17	112.8 (4)	H32B—C32—H32C	109.5
C18—C16—C17	109.8 (4)	C31—C33—H33A	109.5
C11—C16—H16	107.6	C31—C33—H33B	109.5
C18—C16—H16	107.6	H33A—C33—H33B	109.5
C17—C16—H16	107.6	C31—C33—H33C	109.5
C16—C17—H17A	109.5	H33A—C33—H33C	109.5
C16—C17—H17B	109.5	H33B—C33—H33C	109.5
H17A—C17—H17B	109.5