6-Benzyl-2-[(triphenyl-λ-phosphanyl-idene)amino]-4,5,6,7-tetra-hydro-thieno[2,3-c]pyridine-3-carbonitrile.

In the title compound, C(33)H(28)N(3)PS, the P atom has a distorted tetra-hedral PNC(3) environment, formed by the N atom and three aryl rings. No inter-molecular hydrogen-bonding inter-actions or π-π stacking inter-actions are present in the crystal structure.

Related literature

For general background to the potential use of imino­phospho­ranes in the synthesis of N-heterocyclic compounds by means of an aza-Wittig reaction, see: Bräse et al. (2005 ▶); Ding et al. (2005 ▶); Huang et al. (2009a ▶,b ▶); Liu et al. (2008 ▶); Palacios et al. (2007 ▶). For a related structure, see: Muller (2011 ▶).

Experimental

Crystal data

pan class="Chemical">C33H28N3PS

M = 529.61

Monoclinic,

a = 8.926 (4) Å

b = 27.537 (12) Å

c = 11.719 (5) Å

β = 101.970 (4)°

V = 2818 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.23 × 0.15 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.973

25582 measured reflections

6415 independent reflections

5506 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.145

S = 1.09

6415 reflections

343 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.40 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035082/aa2019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035082/aa2019Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035082/aa2019Isup3.cml

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

C33H28N3PS	F(000) = 1112
Mr = 529.61	Dx = 1.248 Mg m−3
Monoclinic, P21/c	Melting point: 463 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.926 (4) Å	Cell parameters from 6648 reflections
b = 27.537 (12) Å	θ = 2.7–27.5°
c = 11.719 (5) Å	µ = 0.20 mm−1
β = 101.970 (4)°	T = 296 K
V = 2818 (2) Å3	Block, yellow
Z = 4	0.23 × 0.15 × 0.14 mm

Bruker SMART CCD diffractometer	6415 independent reflections
Radiation source: fine-focus sealed tube	5506 reflections with I > 2σ(I)
graphite	Rint = 0.078
CCD Profile fitting scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.965, Tmax = 0.973	k = −35→35
25582 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.6222P] where P = (Fo2 + 2Fc2)/3
6415 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.35 e Å−3
14 restraints	Δρmin = −0.40 e Å−3

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
S1	0.39018 (6)	0.490734 (17)	0.21538 (4)	0.04728 (14)
P11	0.32811 (5)	0.375360 (16)	0.10480 (4)	0.03695 (13)
C2	0.29442 (19)	0.44156 (6)	0.26335 (15)	0.0385 (4)
N10	0.26996 (18)	0.39751 (5)	0.21202 (13)	0.0430 (3)
C24	0.2666 (2)	0.31289 (7)	0.10029 (15)	0.0423 (4)
C3	0.2455 (2)	0.45503 (7)	0.36345 (15)	0.0409 (4)
C18	0.2416 (2)	0.40262 (7)	−0.03330 (16)	0.0433 (4)
C9	0.2855 (2)	0.50376 (7)	0.40134 (15)	0.0431 (4)
C4	0.2442 (3)	0.52902 (8)	0.50410 (17)	0.0533 (5)
H4A	0.2822	0.5103	0.5742	0.064*
H4B	0.1336	0.5310	0.4932	0.064*
C12	0.5327 (2)	0.37745 (7)	0.11612 (16)	0.0431 (4)
C8	0.3613 (2)	0.52716 (7)	0.32988 (17)	0.0467 (4)
C30	0.1641 (2)	0.42171 (7)	0.42103 (16)	0.0482 (4)
C19	0.1165 (2)	0.43269 (8)	−0.03768 (18)	0.0526 (5)
H19	0.0819	0.4395	0.0302	0.063*
N6	0.3003 (2)	0.60358 (7)	0.40430 (17)	0.0624 (5)
C7	0.4035 (3)	0.57978 (8)	0.3403 (2)	0.0613 (6)
H7A	0.5089	0.5835	0.3818	0.074*
H7B	0.3932	0.5941	0.2635	0.074*
C29	0.1868 (3)	0.29638 (8)	0.18196 (19)	0.0559 (5)
H29	0.1703	0.3171	0.2409	0.067*
N31	0.0979 (3)	0.39483 (8)	0.46615 (18)	0.0729 (6)
C13	0.6239 (2)	0.34442 (9)	0.18892 (19)	0.0573 (5)
H13	0.5789	0.3190	0.2221	0.069*
C5	0.3120 (3)	0.58015 (9)	0.5189 (2)	0.0666 (6)
H5A	0.2575	0.5994	0.5665	0.080*
H5B	0.4187	0.5784	0.5586	0.080*
C33	0.3007 (3)	0.67981 (8)	0.2956 (2)	0.0681 (6)
C27	0.1534 (3)	0.21872 (9)	0.0894 (3)	0.0765 (8)
H27	0.1140	0.1874	0.0849	0.092*
C23	0.2916 (3)	0.39258 (10)	−0.13584 (18)	0.0643 (6)
H23	0.3761	0.3726	−0.1341	0.077*
C25	0.2919 (3)	0.28159 (8)	0.0134 (2)	0.0628 (6)
H25	0.3471	0.2920	−0.0413	0.075*
C26	0.2338 (4)	0.23443 (9)	0.0087 (2)	0.0775 (8)
H26	0.2499	0.2134	−0.0498	0.093*
C17	0.6018 (3)	0.41492 (9)	0.0675 (2)	0.0630 (6)
H17	0.5420	0.4372	0.0184	0.076*
C16	0.7602 (3)	0.41936 (11)	0.0916 (3)	0.0805 (8)
H16	0.8063	0.4446	0.0587	0.097*
C36	0.2460 (5)	0.72224 (11)	0.0748 (3)	0.0943 (9)
H36	0.2282	0.7364	0.0012	0.113*
C15	0.8486 (3)	0.38665 (12)	0.1639 (3)	0.0797 (8)
H15	0.9546	0.3898	0.1803	0.096*
C14	0.7818 (3)	0.34928 (11)	0.2122 (2)	0.0748 (7)
H14	0.8427	0.3271	0.2607	0.090*
C28	0.1311 (3)	0.24919 (9)	0.1766 (3)	0.0753 (7)
H28	0.0786	0.2383	0.2324	0.090*
C22	0.2153 (3)	0.41234 (12)	−0.2402 (2)	0.0827 (9)
H22	0.2480	0.4053	−0.3087	0.099*
C20	0.0417 (3)	0.45287 (10)	−0.1435 (2)	0.0723 (7)
H20	−0.0416	0.4734	−0.1462	0.087*
C21	0.0922 (3)	0.44216 (12)	−0.2433 (2)	0.0802 (8)
H21	0.0420	0.4553	−0.3140	0.096*
C35	0.3784 (4)	0.72998 (12)	0.1508 (4)	0.0936 (10)
H35	0.4520	0.7499	0.1292	0.112*
C32	0.3298 (4)	0.65581 (9)	0.4136 (3)	0.0824 (8)
H32A	0.4353	0.6613	0.4526	0.099*
H32B	0.2643	0.6704	0.4607	0.099*
C38	0.1630 (3)	0.67270 (10)	0.2154 (3)	0.0808 (8)
H38	0.0867	0.6536	0.2358	0.097*
C34	0.4080 (3)	0.70931 (11)	0.2599 (3)	0.0888 (9)
H34	0.5013	0.7152	0.3103	0.107*
C37	0.1393 (4)	0.69361 (12)	0.1064 (3)	0.0931 (10)
H37	0.0478	0.6879	0.0537	0.112*

	U11	U22	U33	U12	U13	U23
S1	0.0532 (3)	0.0445 (3)	0.0489 (3)	−0.00073 (19)	0.0216 (2)	−0.00419 (18)
P11	0.0375 (2)	0.0411 (2)	0.0327 (2)	0.00167 (17)	0.00837 (17)	−0.00069 (16)
C2	0.0377 (8)	0.0432 (9)	0.0346 (8)	0.0036 (7)	0.0076 (7)	0.0006 (6)
N10	0.0485 (8)	0.0442 (8)	0.0386 (8)	−0.0012 (6)	0.0143 (7)	−0.0042 (6)
C24	0.0422 (9)	0.0443 (9)	0.0374 (9)	0.0003 (7)	0.0014 (7)	−0.0019 (7)
C3	0.0432 (9)	0.0476 (9)	0.0314 (8)	0.0064 (7)	0.0065 (7)	0.0001 (7)
C18	0.0415 (9)	0.0501 (10)	0.0376 (9)	−0.0001 (7)	0.0070 (7)	0.0037 (7)
C9	0.0423 (9)	0.0505 (10)	0.0348 (9)	0.0091 (8)	0.0040 (7)	−0.0045 (7)
C4	0.0608 (12)	0.0609 (12)	0.0356 (9)	0.0127 (9)	0.0040 (9)	−0.0081 (8)
C12	0.0400 (9)	0.0491 (10)	0.0406 (9)	0.0035 (7)	0.0094 (7)	−0.0051 (7)
C8	0.0450 (9)	0.0462 (9)	0.0492 (10)	0.0052 (8)	0.0104 (8)	−0.0090 (8)
C30	0.0582 (11)	0.0536 (10)	0.0339 (9)	0.0080 (9)	0.0119 (8)	0.0017 (7)
C19	0.0443 (10)	0.0608 (12)	0.0512 (11)	0.0049 (9)	0.0064 (9)	0.0052 (9)
N6	0.0780 (13)	0.0471 (9)	0.0629 (11)	0.0041 (9)	0.0170 (10)	−0.0168 (8)
C7	0.0602 (12)	0.0494 (11)	0.0773 (15)	−0.0018 (10)	0.0213 (11)	−0.0146 (10)
C29	0.0691 (13)	0.0484 (11)	0.0515 (11)	−0.0074 (9)	0.0158 (10)	0.0022 (8)
N31	0.0974 (16)	0.0704 (13)	0.0583 (12)	−0.0061 (11)	0.0330 (12)	0.0098 (9)
C13	0.0485 (11)	0.0683 (13)	0.0529 (12)	0.0064 (10)	0.0056 (9)	0.0076 (10)
C5	0.0779 (15)	0.0678 (14)	0.0499 (12)	0.0049 (12)	0.0036 (11)	−0.0212 (10)
C33	0.0764 (15)	0.0455 (11)	0.0805 (16)	0.0092 (10)	0.0119 (13)	−0.0187 (10)
C27	0.0892 (18)	0.0464 (12)	0.0819 (18)	−0.0119 (12)	−0.0100 (15)	0.0005 (11)
C23	0.0621 (13)	0.0937 (17)	0.0391 (11)	0.0135 (12)	0.0152 (10)	0.0084 (10)
C25	0.0818 (15)	0.0564 (12)	0.0504 (12)	0.0022 (11)	0.0143 (11)	−0.0109 (9)
C26	0.103 (2)	0.0541 (13)	0.0662 (16)	0.0051 (13)	−0.0043 (14)	−0.0223 (11)
C17	0.0470 (11)	0.0652 (13)	0.0806 (16)	0.0025 (10)	0.0220 (11)	0.0123 (11)
C16	0.0498 (13)	0.0850 (18)	0.112 (2)	−0.0080 (12)	0.0288 (14)	0.0093 (16)
C36	0.119 (3)	0.0695 (18)	0.095 (2)	0.0008 (18)	0.025 (2)	−0.0063 (15)
C15	0.0403 (11)	0.114 (2)	0.0847 (19)	−0.0037 (13)	0.0122 (12)	−0.0092 (16)
C14	0.0482 (12)	0.105 (2)	0.0668 (16)	0.0173 (13)	0.0017 (11)	0.0068 (14)
C28	0.0913 (18)	0.0535 (13)	0.0814 (17)	−0.0172 (12)	0.0187 (14)	0.0079 (12)
C22	0.0768 (17)	0.132 (3)	0.0392 (12)	−0.0004 (17)	0.0118 (12)	0.0154 (13)
C20	0.0526 (12)	0.0819 (16)	0.0743 (17)	0.0134 (12)	−0.0057 (12)	0.0194 (13)
C21	0.0652 (15)	0.113 (2)	0.0549 (15)	−0.0024 (15)	−0.0054 (12)	0.0301 (14)
C35	0.105 (2)	0.0723 (18)	0.115 (3)	−0.0176 (17)	0.048 (2)	−0.0176 (17)
C32	0.1019 (19)	0.0533 (13)	0.0851 (17)	0.0030 (13)	0.0036 (15)	−0.0268 (11)
C38	0.0603 (14)	0.0636 (15)	0.116 (2)	−0.0038 (12)	0.0126 (15)	0.0062 (15)
C34	0.0697 (16)	0.0736 (17)	0.117 (3)	−0.0124 (14)	0.0048 (17)	−0.0369 (17)
C37	0.086 (2)	0.0790 (19)	0.101 (2)	0.0032 (16)	−0.0105 (18)	0.0071 (17)

S1—C8	1.737 (2)	C33—C34	1.385 (4)
S1—C2	1.7550 (19)	C33—C38	1.397 (4)
P11—N10	1.5782 (16)	C33—C32	1.506 (4)
P11—C24	1.803 (2)	C27—C28	1.368 (4)
P11—C12	1.804 (2)	C27—C26	1.371 (4)
P11—C18	1.8057 (19)	C27—H27	0.9300
C2—N10	1.351 (2)	C23—C22	1.382 (3)
C2—C3	1.385 (2)	C23—H23	0.9300
C24—C29	1.383 (3)	C25—C26	1.395 (3)
C24—C25	1.388 (3)	C25—H25	0.9300
C3—C30	1.424 (3)	C26—H26	0.9300
C3—C9	1.435 (3)	C17—C16	1.389 (3)
C18—C19	1.383 (3)	C17—H17	0.9300
C18—C23	1.394 (3)	C16—C15	1.369 (4)
C9—C8	1.345 (3)	C16—H16	0.9300
C9—C4	1.501 (2)	C36—C35	1.341 (5)
C4—C5	1.528 (3)	C36—C37	1.347 (5)
C4—H4A	0.9700	C36—H36	0.9300
C4—H4B	0.9700	C15—C14	1.369 (4)
C12—C17	1.384 (3)	C15—H15	0.9300
C12—C13	1.389 (3)	C14—H14	0.9300
C8—C7	1.496 (3)	C28—H28	0.9300
C30—N31	1.143 (3)	C22—C21	1.367 (4)
C19—C20	1.396 (3)	C22—H22	0.9300
C19—H19	0.9300	C20—C21	1.370 (4)
N6—C7	1.458 (3)	C20—H20	0.9300
N6—C32	1.462 (3)	C21—H21	0.9300
N6—C5	1.474 (3)	C35—C34	1.373 (5)
C7—H7A	0.9700	C35—H35	0.9300
C7—H7B	0.9700	C32—H32A	0.9700
C29—C28	1.388 (3)	C32—H32B	0.9700
C29—H29	0.9300	C38—C37	1.376 (4)
C13—C14	1.386 (3)	C38—H38	0.9300
C13—H13	0.9300	C34—H34	0.9300
C5—H5A	0.9700	C37—H37	0.9300
C5—H5B	0.9700
C8—S1—C2	92.17 (9)	C34—C33—C38	116.4 (3)
N10—P11—C24	104.09 (8)	C34—C33—C32	122.4 (3)
N10—P11—C12	115.09 (8)	C38—C33—C32	121.1 (3)
C24—P11—C12	109.28 (8)	C28—C27—C26	120.0 (2)
N10—P11—C18	113.76 (9)	C28—C27—H27	120.0
C24—P11—C18	107.42 (9)	C26—C27—H27	120.0
C12—P11—C18	106.90 (9)	C22—C23—C18	119.8 (2)
N10—C2—C3	124.56 (16)	C22—C23—H23	120.1
N10—C2—S1	126.48 (13)	C18—C23—H23	120.1
C3—C2—S1	108.96 (13)	C24—C25—C26	119.4 (2)
C2—N10—P11	130.67 (13)	C24—C25—H25	120.3
C29—C24—C25	119.31 (19)	C26—C25—H25	120.3
C29—C24—P11	119.39 (15)	C27—C26—C25	120.7 (2)
C25—C24—P11	121.24 (16)	C27—C26—H26	119.7
C2—C3—C30	120.69 (17)	C25—C26—H26	119.7
C2—C3—C9	114.23 (16)	C12—C17—C16	120.2 (2)
C30—C3—C9	125.07 (16)	C12—C17—H17	119.9
C19—C18—C23	119.18 (18)	C16—C17—H17	119.9
C19—C18—P11	118.30 (15)	C15—C16—C17	120.0 (3)
C23—C18—P11	122.44 (16)	C15—C16—H16	120.0
C8—C9—C3	112.36 (16)	C17—C16—H16	120.0
C8—C9—C4	121.09 (18)	C35—C36—C37	119.1 (3)
C3—C9—C4	126.47 (17)	C35—C36—H36	120.5
C9—C4—C5	111.13 (18)	C37—C36—H36	120.5
C9—C4—H4A	109.4	C16—C15—C14	120.4 (2)
C5—C4—H4A	109.4	C16—C15—H15	119.8
C9—C4—H4B	109.4	C14—C15—H15	119.8
C5—C4—H4B	109.4	C15—C14—C13	120.2 (2)
H4A—C4—H4B	108.0	C15—C14—H14	119.9
C17—C12—C13	119.13 (19)	C13—C14—H14	119.9
C17—C12—P11	121.62 (15)	C27—C28—C29	120.1 (3)
C13—C12—P11	118.64 (15)	C27—C28—H28	120.0
C9—C8—C7	124.33 (18)	C29—C28—H28	120.0
C9—C8—S1	112.26 (15)	C21—C22—C23	120.4 (2)
C7—C8—S1	123.18 (16)	C21—C22—H22	119.8
N31—C30—C3	179.3 (2)	C23—C22—H22	119.8
C18—C19—C20	120.3 (2)	C21—C20—C19	119.4 (2)
C18—C19—H19	119.8	C21—C20—H20	120.3
C20—C19—H19	119.8	C19—C20—H20	120.3
C7—N6—C32	110.9 (2)	C22—C21—C20	120.8 (2)
C7—N6—C5	109.80 (19)	C22—C21—H21	119.6
C32—N6—C5	112.64 (19)	C20—C21—H21	119.6
N6—C7—C8	107.58 (18)	C36—C35—C34	121.7 (3)
N6—C7—H7A	110.2	C36—C35—H35	119.1
C8—C7—H7A	110.2	C34—C35—H35	119.1
N6—C7—H7B	110.2	N6—C32—C33	111.7 (2)
C8—C7—H7B	110.2	N6—C32—H32A	109.3
H7A—C7—H7B	108.5	C33—C32—H32A	109.3
C24—C29—C28	120.5 (2)	N6—C32—H32B	109.3
C24—C29—H29	119.8	C33—C32—H32B	109.3
C28—C29—H29	119.8	H32A—C32—H32B	107.9
C14—C13—C12	120.0 (2)	C37—C38—C33	120.7 (3)
C14—C13—H13	120.0	C37—C38—H38	119.7
C12—C13—H13	120.0	C33—C38—H38	119.7
N6—C5—C4	110.37 (17)	C35—C34—C33	120.8 (3)
N6—C5—H5A	109.6	C35—C34—H34	119.6
C4—C5—H5A	109.6	C33—C34—H34	119.6
N6—C5—H5B	109.6	C36—C37—C38	121.2 (3)
C4—C5—H5B	109.6	C36—C37—H37	119.4
H5A—C5—H5B	108.1	C38—C37—H37	119.4
C8—S1—C2—N10	179.48 (17)	P11—C18—C19—C20	−177.18 (18)
C8—S1—C2—C3	−0.05 (14)	C32—N6—C7—C8	−177.4 (2)
C3—C2—N10—P11	−174.79 (14)	C5—N6—C7—C8	57.4 (2)
S1—C2—N10—P11	5.7 (3)	C9—C8—C7—N6	−22.4 (3)
C24—P11—N10—C2	173.39 (17)	S1—C8—C7—N6	151.68 (16)
C12—P11—N10—C2	53.8 (2)	C25—C24—C29—C28	−0.6 (3)
C18—P11—N10—C2	−70.01 (19)	P11—C24—C29—C28	176.58 (19)
N10—P11—C24—C29	0.25 (18)	C17—C12—C13—C14	0.1 (3)
C12—P11—C24—C29	123.69 (16)	P11—C12—C13—C14	−171.05 (19)
C18—P11—C24—C29	−120.68 (16)	C7—N6—C5—C4	−69.2 (2)
N10—P11—C24—C25	177.42 (17)	C32—N6—C5—C4	166.6 (2)
C12—P11—C24—C25	−59.14 (19)	C9—C4—C5—N6	39.9 (3)
C18—P11—C24—C25	56.49 (19)	C19—C18—C23—C22	−0.5 (4)
N10—C2—C3—C30	0.5 (3)	P11—C18—C23—C22	176.3 (2)
S1—C2—C3—C30	−179.95 (14)	C29—C24—C25—C26	1.3 (3)
N10—C2—C3—C9	179.89 (16)	P11—C24—C25—C26	−175.92 (18)
S1—C2—C3—C9	−0.57 (19)	C28—C27—C26—C25	−0.9 (4)
N10—P11—C18—C19	−11.62 (19)	C24—C25—C26—C27	−0.5 (4)
C24—P11—C18—C19	103.01 (17)	C13—C12—C17—C16	−0.2 (4)
C12—P11—C18—C19	−139.79 (16)	P11—C12—C17—C16	170.7 (2)
N10—P11—C18—C23	171.61 (18)	C12—C17—C16—C15	−0.1 (4)
C24—P11—C18—C23	−73.8 (2)	C17—C16—C15—C14	0.4 (5)
C12—P11—C18—C23	43.4 (2)	C16—C15—C14—C13	−0.5 (5)
C2—C3—C9—C8	1.1 (2)	C12—C13—C14—C15	0.2 (4)
C30—C3—C9—C8	−179.54 (17)	C26—C27—C28—C29	1.5 (4)
C2—C3—C9—C4	177.94 (17)	C24—C29—C28—C27	−0.8 (4)
C30—C3—C9—C4	−2.7 (3)	C18—C23—C22—C21	0.8 (4)
C8—C9—C4—C5	−5.3 (3)	C18—C19—C20—C21	0.8 (4)
C3—C9—C4—C5	178.09 (18)	C23—C22—C21—C20	−0.2 (5)
N10—P11—C12—C17	−94.91 (19)	C19—C20—C21—C22	−0.6 (4)
C24—P11—C12—C17	148.44 (18)	C37—C36—C35—C34	0.3 (5)
C18—P11—C12—C17	32.5 (2)	C7—N6—C32—C33	62.6 (3)
N10—P11—C12—C13	76.04 (18)	C5—N6—C32—C33	−173.9 (2)
C24—P11—C12—C13	−40.61 (18)	C34—C33—C32—N6	−127.8 (3)
C18—P11—C12—C13	−156.57 (16)	C38—C33—C32—N6	51.2 (3)
C3—C9—C8—C7	173.52 (19)	C34—C33—C38—C37	1.1 (4)
C4—C9—C8—C7	−3.5 (3)	C32—C33—C38—C37	−178.0 (3)
C3—C9—C8—S1	−1.1 (2)	C36—C35—C34—C33	−0.5 (5)
C4—C9—C8—S1	−178.14 (14)	C38—C33—C34—C35	−0.2 (4)
C2—S1—C8—C9	0.68 (15)	C32—C33—C34—C35	179.0 (3)
C2—S1—C8—C7	−174.02 (18)	C35—C36—C37—C38	0.7 (5)
C23—C18—C19—C20	−0.3 (3)	C33—C38—C37—C36	−1.4 (5)