[(2E)-2-Benzyl­idene­hydrazino]­tri­cyclo­hexyl­phospho­nium chloride

In the title compound, C₂₅H₄₀N₂P⁺·Cl⁻, the cation structure (at 150 K) is intermediate between those of the imino­phospho­rane and the yl­ide, consistent with delocalization of the positive charge between the P and the adjacent N atoms. The cation and anion are linked by a strong N—H...Cl hydrogen bond.

S1. Comment

The character of the P≐N bond in iminophosphoranes is usually described by the resonance of two canonical forms, the ylide R₃P⁺—N^-X and the iminophosphorane proper R₃P═NX. The relative contributions of the two, i.e. the multiplicity of the bond, are easily affected by the nature of the substituents, the overall molecular charge, hydrogen bonds and weak intermolecular interactions. Thus, diffraction studies of iminotriphenylphosphorane, (I), revealed two different, but similar, polymorphs with significantly different P≐N bond lengths of 1.524 (3) Å (Grün et al., 1996) and 1.582 (2) Å (Davidson et al., 1998). The exact nature of the π component of the bond and the role in it of the d orbitals of the phosphorus atom remain a subject of controversy (Johnson, 1993). Herein we report the structure of the title salt, (II), obtained as an incidental by-product in a synthesis of a ruthenium carbene complex, which can add useful data to the discussion. \sch

The asymmetric unit of (II) comprises one cation and one chloride anion (Fig. 1), linked by a strong hydrogen bond (Table 2). It is noteworthy that there are no hydrogen bonds involving the NH group in the crystal structure of either polymorph of (I).

The P—N1—N2—C7—C1 moiety is approximately planar, and the displacements of these atoms from their mean plane do not exceed 0.1 Å. The non-weighted mean plane makes a dihedral angle of 25.1 (1)° with the plane of the adjacent phenyl ring. The N2═C7 bond distance [1.285 (2) Å] is close to the standard value for the double bond, 1.279 (8) Å (Allen et al., 1987). The N1—N2 distance [1.399 (1) Å] is similar to that of the single bond in N-protonated benzalazine (Noltemeyer et al., 1983) 1.402 (8) Å, which also has a transoid conformation. Thus, the resonance is restricted mainly to the two canonical forms with the positive charge localized on either the P or the N1 atoms, viz. Cy₃P⁺—NH—N═CHPh or Cy₃P═ NH⁺—N═CHPh. The P≐N distance of 1.651 (1) Å in (II) indicates a considerable shift towards the ylide structure compared to (I), although it is still a long way shorter than the purely single P—N bond of 1.769 Å (Bart et al., 1982). Protonation of an iminophosphorane molecule is known to produce such a shift: compare P═N 1.603 Å in Ph₃PNPh (Böhm et al., 1988) to 1.624–1.628 Å in Ph₃PN⁺HPh (Böhm et al., 1988; Llamas-Saiz et al., 1992). The only previously studied cation with a PN(H)N chain, Ph₃P⁺—NH—NMe₂ (Stoldt & Kreher, 1978), displays the bond distances P—N 1.640 (3) and N—N 1.425 (4) Å.

Related literature

For related literature, see: Allen et al. (1987); Böhm et al. (1988); Bart et al. (1982); Davidson et al. (1998); Grün et al. (1996); Johnson (1993); Llamas-Saiz, Foces-Foces, Elguero, Molina, Alajarin & Vidal (1992); Noltemeyer et al. (1983); Stoldt & Kreher (1978).

S2. Experimental

A solution of phenyldiazomethane (2 equivalents) in dichloromethane was added to a mixture of [η⁶-(p-cymene)RuCl]₂ (1 equivalent) and tricyclohexyl phosphine (2 equivalents), also in dichloromethane, at 195 K under nitrogen. The mixture was then allowed to warm up slowly to room temperature, the solvent was removed under vacuum and the remaining solid (the target ruthenium complex) was washed with ether. The ether wash, being kept at ca 248 K (in a freezer) for several weeks, yielded the crystals of (II).

S3. Refinement

All H atoms were refined in an isotropic approximation; bond distances Csp²—H from 0.91 (2) to 0.99 (2) Å, Csp³—H from 0.96 (2) to 1.01 (2) Å.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. Molecular structure of (II) showing 50% probability displacement ellipsoids.

(2E)-1,2-Diaza-3-phenylprop-2-enyl-tri(cyclohexyl)phosphonium chloride

Crystal data

C25H40N2P^+·Cl^−	F(000) = 944
Mr = 435.01	Dx = 1.160 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.106 (3) Å	Cell parameters from 512 reflections
b = 13.187 (3) Å	θ = 12.0–27.5°
c = 15.819 (4) Å	µ = 0.23 mm^−1
β = 99.62 (2)°	T = 150 K
V = 2490 (1) Å^3	Ellipsoid, yellow
Z = 4	0.40 × 0.30 × 0.30 mm

Data collection

SMART 1K CCD area detector diffractometer	5420 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 29.0°, θmin = 2.0°
Detector resolution: 8 pixels mm^-1	h = −16→15
ω scans	k = −17→17
18481 measured reflections	l = −16→21
6546 independent reflections

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F^2) = 0.087	All H-atom parameters refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0288P)^2 + 1.0707P] where P = (Fo^2 + 2Fc^2)/3
6546 reflections	(Δ/σ)max < 0.001
422 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. The data collection nominally covered over a hemisphere of reciprocal space, by a combination of four sets of ω scans; each set at different ϕ and/or 2θ angles and each scan covering 0.3° in ω. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing duplicate reflections. Crystal to detector distance 4.5 cm.

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.

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

	x	y	z	Uiso*/Ueq
P	0.23511 (3)	0.05867 (2)	0.142887 (19)	0.01749 (7)
N1	0.20492 (9)	−0.05437 (8)	0.10044 (7)	0.0218 (2)
H1	0.1629 (14)	−0.0943 (14)	0.1260 (11)	0.037 (5)*
N2	0.27409 (9)	−0.09840 (8)	0.04803 (7)	0.0202 (2)
C1	0.31818 (10)	−0.25085 (9)	−0.02239 (8)	0.0205 (2)
C2	0.31377 (12)	−0.35683 (11)	−0.02206 (9)	0.0297 (3)
H2	0.2712 (14)	−0.3903 (13)	0.0184 (11)	0.035 (4)*
C3	0.36522 (14)	−0.41292 (12)	−0.07923 (11)	0.0373 (4)
H3	0.3622 (16)	−0.4817 (16)	−0.0793 (13)	0.051 (5)*
C4	0.41886 (12)	−0.36399 (12)	−0.13801 (10)	0.0328 (3)
H4	0.4546 (15)	−0.4019 (15)	−0.1771 (12)	0.047 (5)*
C5	0.42363 (12)	−0.25872 (11)	−0.13919 (9)	0.0289 (3)
H5	0.4608 (15)	−0.2259 (13)	−0.1784 (11)	0.039 (5)*
C6	0.37454 (11)	−0.20230 (10)	−0.08137 (9)	0.0244 (3)
H6	0.3774 (13)	−0.1304 (13)	−0.0820 (10)	0.033 (4)*
C7	0.25955 (10)	−0.19424 (9)	0.03674 (8)	0.0206 (2)
H7	0.2072 (12)	−0.2322 (12)	0.0651 (10)	0.024 (4)*
C11	0.10919 (10)	0.08594 (9)	0.18786 (8)	0.0194 (2)
H11	0.1054 (12)	0.0251 (12)	0.2202 (10)	0.023 (4)*
C12	0.11617 (11)	0.17844 (10)	0.24849 (9)	0.0248 (3)
H121	0.1871 (14)	0.1798 (13)	0.2886 (11)	0.035 (4)*
H122	0.1146 (14)	0.2413 (13)	0.2131 (11)	0.033 (4)*
C13	0.01575 (12)	0.17678 (12)	0.29641 (9)	0.0304 (3)
H131	0.0229 (14)	0.1147 (13)	0.3340 (11)	0.036 (4)*
H132	0.0209 (13)	0.2354 (13)	0.3339 (11)	0.032 (4)*
C14	−0.09548 (12)	0.17530 (12)	0.23390 (10)	0.0301 (3)
H141	−0.1601 (14)	0.1708 (13)	0.2639 (11)	0.038 (5)*
H142	−0.1048 (13)	0.2410 (13)	0.2029 (10)	0.032 (4)*
C15	−0.09994 (11)	0.08839 (11)	0.16934 (9)	0.0263 (3)
H151	−0.1700 (14)	0.0928 (13)	0.1297 (11)	0.034 (4)*
H152	−0.1006 (13)	0.0242 (13)	0.1992 (10)	0.032 (4)*
C16	0.00032 (11)	0.09009 (11)	0.12163 (8)	0.0235 (3)
H161	−0.0012 (13)	0.1529 (13)	0.0889 (10)	0.031 (4)*
H162	−0.0041 (13)	0.0328 (13)	0.0831 (10)	0.029 (4)*
C21	0.26782 (10)	0.14527 (9)	0.06066 (8)	0.0203 (2)
H21	0.3466 (12)	0.1298 (11)	0.0573 (9)	0.023 (4)*
C22	0.26112 (12)	0.25714 (10)	0.08825 (8)	0.0253 (3)
H221	0.1825 (14)	0.2739 (12)	0.0923 (10)	0.031 (4)*
H222	0.3078 (14)	0.2697 (13)	0.1448 (11)	0.034 (4)*
C23	0.29727 (14)	0.32725 (11)	0.02065 (9)	0.0303 (3)
H231	0.2899 (14)	0.3980 (14)	0.0383 (11)	0.041 (5)*
H232	0.3759 (14)	0.3136 (12)	0.0184 (10)	0.032 (4)*
C24	0.22830 (13)	0.30853 (11)	−0.06790 (9)	0.0299 (3)
H241	0.1442 (16)	0.3240 (14)	−0.0663 (12)	0.043 (5)*
H242	0.2536 (14)	0.3528 (13)	−0.1108 (11)	0.038 (5)*
C25	0.23582 (13)	0.19802 (11)	−0.09443 (9)	0.0301 (3)
H251	0.3128 (13)	0.1805 (12)	−0.0995 (10)	0.024 (4)*
H252	0.1908 (14)	0.1853 (13)	−0.1506 (11)	0.037 (5)*
C26	0.19719 (12)	0.12706 (11)	−0.02828 (8)	0.0266 (3)
H261	0.1159 (14)	0.1412 (13)	−0.0260 (10)	0.035 (4)*
H262	0.2044 (14)	0.0571 (14)	−0.0443 (11)	0.036 (4)*
C31	0.35429 (10)	0.05542 (9)	0.22992 (8)	0.0203 (2)
H31	0.3702 (13)	0.1258 (13)	0.2446 (10)	0.031 (4)*
C32	0.32735 (12)	−0.00127 (11)	0.30945 (9)	0.0268 (3)
H321	0.2597 (14)	0.0267 (13)	0.3285 (11)	0.034 (4)*
H322	0.3093 (13)	−0.0730 (13)	0.2940 (11)	0.033 (4)*
C33	0.42827 (13)	0.00425 (12)	0.38240 (9)	0.0324 (3)
H331	0.4405 (14)	0.0759 (14)	0.3992 (11)	0.035 (4)*
H332	0.4099 (14)	−0.0333 (13)	0.4317 (11)	0.038 (5)*
C34	0.53360 (13)	−0.03895 (12)	0.35528 (10)	0.0357 (3)
H341	0.5970 (16)	−0.0315 (14)	0.4016 (12)	0.048 (5)*
H342	0.5231 (15)	−0.1130 (15)	0.3469 (12)	0.045 (5)*
C35	0.55877 (12)	0.01197 (13)	0.27400 (10)	0.0348 (3)
H351	0.6254 (16)	−0.0186 (14)	0.2545 (12)	0.045 (5)*
H352	0.5774 (15)	0.0836 (14)	0.2862 (11)	0.041 (5)*
C36	0.45792 (11)	0.00660 (11)	0.20123 (9)	0.0276 (3)
H361	0.4412 (13)	−0.0664 (13)	0.1859 (10)	0.034 (4)*
H362	0.4742 (13)	0.0384 (12)	0.1489 (11)	0.031 (4)*
Cl	0.06267 (3)	−0.19971 (3)	0.18592 (2)	0.03053 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.02065 (15)	0.01530 (14)	0.01687 (14)	−0.00094 (11)	0.00414 (11)	−0.00036 (11)
N1	0.0268 (5)	0.0175 (5)	0.0240 (5)	−0.0040 (4)	0.0123 (4)	−0.0035 (4)
N2	0.0220 (5)	0.0203 (5)	0.0193 (5)	−0.0002 (4)	0.0060 (4)	−0.0029 (4)
C1	0.0215 (6)	0.0207 (6)	0.0190 (6)	−0.0007 (4)	0.0024 (4)	−0.0026 (4)
C2	0.0385 (8)	0.0221 (7)	0.0314 (7)	−0.0051 (5)	0.0141 (6)	−0.0039 (5)
C3	0.0480 (9)	0.0221 (7)	0.0460 (9)	−0.0057 (6)	0.0196 (7)	−0.0116 (6)
C4	0.0334 (7)	0.0320 (7)	0.0356 (8)	−0.0012 (6)	0.0130 (6)	−0.0130 (6)
C5	0.0276 (7)	0.0325 (7)	0.0296 (7)	−0.0009 (5)	0.0132 (5)	−0.0017 (6)
C6	0.0248 (6)	0.0222 (6)	0.0274 (6)	0.0006 (5)	0.0082 (5)	−0.0004 (5)
C7	0.0234 (6)	0.0204 (6)	0.0187 (6)	−0.0015 (5)	0.0057 (5)	−0.0002 (4)
C11	0.0214 (6)	0.0184 (6)	0.0189 (6)	−0.0001 (4)	0.0049 (4)	−0.0010 (4)
C12	0.0264 (6)	0.0238 (6)	0.0247 (6)	−0.0007 (5)	0.0058 (5)	−0.0064 (5)
C13	0.0338 (7)	0.0336 (8)	0.0256 (7)	−0.0013 (6)	0.0102 (6)	−0.0082 (6)
C14	0.0286 (7)	0.0329 (7)	0.0314 (7)	0.0014 (6)	0.0126 (6)	−0.0033 (6)
C15	0.0232 (6)	0.0298 (7)	0.0258 (6)	0.0007 (5)	0.0039 (5)	0.0006 (5)
C16	0.0234 (6)	0.0272 (6)	0.0197 (6)	0.0007 (5)	0.0027 (5)	−0.0012 (5)
C21	0.0241 (6)	0.0187 (6)	0.0183 (5)	−0.0017 (4)	0.0044 (4)	0.0012 (4)
C22	0.0370 (7)	0.0181 (6)	0.0207 (6)	−0.0034 (5)	0.0049 (5)	0.0012 (5)
C23	0.0408 (8)	0.0225 (7)	0.0277 (7)	−0.0068 (6)	0.0056 (6)	0.0043 (5)
C24	0.0360 (8)	0.0289 (7)	0.0248 (7)	−0.0015 (6)	0.0054 (6)	0.0096 (5)
C25	0.0390 (8)	0.0320 (7)	0.0192 (6)	−0.0028 (6)	0.0047 (6)	0.0032 (5)
C26	0.0360 (7)	0.0242 (7)	0.0186 (6)	−0.0060 (5)	0.0017 (5)	0.0003 (5)
C31	0.0227 (6)	0.0178 (6)	0.0198 (6)	−0.0005 (4)	0.0021 (4)	0.0010 (4)
C32	0.0296 (7)	0.0282 (7)	0.0222 (6)	−0.0004 (5)	0.0027 (5)	0.0066 (5)
C33	0.0361 (8)	0.0349 (8)	0.0239 (7)	−0.0005 (6)	−0.0017 (6)	0.0047 (6)
C34	0.0335 (8)	0.0339 (8)	0.0350 (8)	0.0049 (6)	−0.0077 (6)	0.0035 (6)
C35	0.0242 (7)	0.0417 (9)	0.0366 (8)	0.0027 (6)	−0.0008 (6)	−0.0023 (7)
C36	0.0233 (6)	0.0321 (7)	0.0271 (7)	0.0025 (5)	0.0030 (5)	−0.0012 (6)
Cl	0.03254 (17)	0.02713 (17)	0.03531 (18)	−0.00013 (13)	0.01558 (14)	0.00991 (13)

Geometric parameters (Å, º)

P—N1	1.6506 (11)	C16—H162	0.966 (16)
P—C31	1.8207 (13)	C21—C26	1.5382 (18)
P—C11	1.8225 (13)	C21—C22	1.5444 (18)
P—C21	1.8235 (13)	C21—H21	0.985 (15)
N1—N2	1.3992 (14)	C22—C23	1.5318 (18)
N1—H1	0.876 (18)	C22—H221	0.990 (16)
N2—C7	1.2845 (16)	C22—H222	0.989 (17)
C1—C2	1.3987 (18)	C23—C24	1.526 (2)
C1—C6	1.3994 (18)	C23—H231	0.982 (19)
C1—C7	1.4689 (17)	C23—H232	0.976 (17)
C2—C3	1.393 (2)	C24—C25	1.523 (2)
C2—H2	0.990 (17)	C24—H241	1.043 (18)
C3—C4	1.380 (2)	C24—H242	0.981 (18)
C3—H3	0.91 (2)	C25—C26	1.5340 (19)
C4—C5	1.390 (2)	C25—H251	0.977 (15)
C4—H4	0.954 (19)	C25—H252	0.976 (17)
C5—C6	1.3875 (18)	C26—H261	1.008 (17)
C5—H5	0.931 (18)	C26—H262	0.965 (18)
C6—H6	0.948 (17)	C31—C36	1.5442 (18)
C7—H7	0.974 (15)	C31—C32	1.5443 (18)
C11—C16	1.5415 (18)	C31—H31	0.968 (17)
C11—C12	1.5454 (17)	C32—C33	1.536 (2)
C11—H11	0.956 (15)	C32—H321	0.990 (17)
C12—C13	1.5365 (19)	C32—H322	0.992 (17)
C12—H121	0.978 (17)	C33—C34	1.522 (2)
C12—H122	0.999 (17)	C33—H331	0.985 (18)
C13—C14	1.532 (2)	C33—H332	0.980 (18)
C13—H131	1.007 (18)	C34—C35	1.526 (2)
C13—H132	0.970 (17)	C34—H341	0.973 (19)
C14—C15	1.530 (2)	C34—H342	0.991 (19)
C14—H141	0.982 (17)	C35—C36	1.533 (2)
C14—H142	0.993 (17)	C35—H351	0.996 (19)
C15—C16	1.5328 (18)	C35—H352	0.983 (19)
C15—H151	0.969 (17)	C36—H361	1.005 (17)
C15—H152	0.971 (17)	C36—H362	0.977 (17)
C16—H161	0.976 (17)
N1—P—C31	112.33 (6)	C26—C21—H21	108.3 (9)
N1—P—C11	101.20 (6)	C22—C21—H21	108.1 (9)
C31—P—C11	108.56 (6)	P—C21—H21	103.6 (9)
N1—P—C21	109.58 (6)	C23—C22—C21	110.16 (11)
C31—P—C21	108.36 (6)	C23—C22—H221	107.4 (9)
C11—P—C21	116.77 (6)	C21—C22—H221	109.2 (10)
N2—N1—P	120.13 (8)	C23—C22—H222	110.1 (10)
N2—N1—H1	118.4 (12)	C21—C22—H222	111.5 (10)
P—N1—H1	117.5 (12)	H221—C22—H222	108.4 (13)
C7—N2—N1	114.14 (10)	C24—C23—C22	111.51 (12)
C2—C1—C6	118.87 (12)	C24—C23—H231	110.6 (10)
C2—C1—C7	118.85 (11)	C22—C23—H231	109.0 (10)
C6—C1—C7	122.23 (11)	C24—C23—H232	108.9 (10)
C3—C2—C1	120.43 (13)	C22—C23—H232	107.9 (10)
C3—C2—H2	121.4 (10)	H231—C23—H232	108.8 (14)
C1—C2—H2	118.2 (10)	C25—C24—C23	111.03 (12)
C4—C3—C2	120.06 (14)	C25—C24—H241	107.3 (10)
C4—C3—H3	119.3 (13)	C23—C24—H241	109.5 (10)
C2—C3—H3	120.6 (13)	C25—C24—H242	109.8 (10)
C3—C4—C5	120.10 (13)	C23—C24—H242	110.6 (10)
C3—C4—H4	120.5 (12)	H241—C24—H242	108.6 (14)
C5—C4—H4	119.3 (12)	C24—C25—C26	110.89 (12)
C6—C5—C4	120.23 (13)	C24—C25—H251	110.5 (9)
C6—C5—H5	119.8 (11)	C26—C25—H251	108.4 (9)
C4—C5—H5	120.0 (11)	C24—C25—H252	111.4 (10)
C5—C6—C1	120.30 (13)	C26—C25—H252	109.2 (10)
C5—C6—H6	120.6 (10)	H251—C25—H252	106.3 (13)
C1—C6—H6	119.1 (10)	C25—C26—C21	110.03 (11)
N2—C7—C1	121.27 (11)	C25—C26—H261	108.8 (10)
N2—C7—H7	121.8 (9)	C21—C26—H261	109.6 (9)
C1—C7—H7	116.9 (9)	C25—C26—H262	110.6 (10)
C16—C11—C12	110.22 (10)	C21—C26—H262	109.2 (10)
C16—C11—P	114.69 (9)	H261—C26—H262	108.6 (14)
C12—C11—P	115.82 (9)	C36—C31—C32	109.28 (11)
C16—C11—H11	106.3 (9)	C36—C31—P	111.57 (9)
C12—C11—H11	109.4 (9)	C32—C31—P	112.26 (9)
P—C11—H11	99.3 (9)	C36—C31—H31	109.4 (9)
C13—C12—C11	109.22 (11)	C32—C31—H31	109.2 (10)
C13—C12—H121	111.2 (10)	P—C31—H31	105.0 (9)
C11—C12—H121	111.6 (10)	C33—C32—C31	109.84 (11)
C13—C12—H122	110.3 (9)	C33—C32—H321	110.4 (10)
C11—C12—H122	108.2 (10)	C31—C32—H321	111.4 (10)
H121—C12—H122	106.3 (13)	C33—C32—H322	110.2 (9)
C14—C13—C12	111.37 (12)	C31—C32—H322	109.2 (10)
C14—C13—H131	110.5 (10)	H321—C32—H322	105.8 (13)
C12—C13—H131	107.8 (10)	C34—C33—C32	111.66 (13)
C14—C13—H132	111.4 (10)	C34—C33—H331	109.8 (10)
C12—C13—H132	108.3 (10)	C32—C33—H331	108.2 (10)
H131—C13—H132	107.3 (13)	C34—C33—H332	110.3 (10)
C15—C14—C13	111.69 (12)	C32—C33—H332	108.4 (10)
C15—C14—H141	109.6 (10)	H331—C33—H332	108.3 (14)
C13—C14—H141	111.9 (10)	C33—C34—C35	111.56 (12)
C15—C14—H142	109.6 (10)	C33—C34—H341	110.0 (11)
C13—C14—H142	108.9 (10)	C35—C34—H341	110.3 (11)
H141—C14—H142	104.9 (13)	C33—C34—H342	108.2 (11)
C14—C15—C16	112.04 (11)	C35—C34—H342	111.1 (11)
C14—C15—H151	108.5 (10)	H341—C34—H342	105.5 (15)
C16—C15—H151	111.1 (10)	C34—C35—C36	111.48 (13)
C14—C15—H152	109.3 (10)	C34—C35—H351	111.6 (11)
C16—C15—H152	108.9 (10)	C36—C35—H351	109.5 (10)
H151—C15—H152	106.9 (13)	C34—C35—H352	109.2 (11)
C15—C16—C11	108.80 (11)	C36—C35—H352	108.6 (10)
C15—C16—H161	109.1 (9)	H351—C35—H352	106.2 (15)
C11—C16—H161	109.2 (9)	C35—C36—C31	110.13 (12)
C15—C16—H162	109.5 (10)	C35—C36—H361	109.2 (9)
C11—C16—H162	110.6 (9)	C31—C36—H361	109.2 (9)
H161—C16—H162	109.6 (13)	C35—C36—H362	111.6 (9)
C26—C21—C22	111.11 (11)	C31—C36—H362	111.0 (10)
C26—C21—P	113.63 (9)	H361—C36—H362	105.5 (13)
C22—C21—P	111.64 (8)
C21—P—N1—N2	47.17 (11)	N1—N2—C7—C1	174.65 (10)
P—N1—N2—C7	163.26 (9)	N2—C7—C1—C6	−12.84 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl	0.876 (18)	2.165 (18)	3.0406 (12)	177.0 (16)