(2,6-Diisopropyl-phen-yl)(2-thienylmethyl-ene)amine.

The title compound, C(17)H(21)NS, was prepared by the condensation of thio-phene-2-carbaldehyde with 2,6-diiso-propyl-aniline. It crystallizes with two mol-ecules in the asymmetric unit. The mol-ecules are inter-connected via a C-H⋯N hydrogen bond. The dihedral angles between the thio-phene and phenyl rings are 81.7 (7) and 85.5 (7)°.

Related literature

For the synthetic procedure, see: Drisko & McKennis (1952 ▶); Wang et al. (2007 ▶). For related structures, see: Kazak et al. (2000 ▶); Małeki et al. (2007 ▶). For the organometallic chemistry of related ligands, see: Imhof (1997a ▶,b ▶).

Experimental

Crystal data

C17H21NS

M = 271.42

Monoclinic,

a = 10.0877 (9) Å

b = 14.275 (3) Å

c = 11.4503 (9) Å

β = 109.651 (8)°

V = 1552.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.51 × 0.43 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.884, T max = 0.939

2222 measured reflections

2096 independent reflections

2055 reflections with I > 2σ(I)

R int = 0.023

θmax = 23.0°

3 standard reflections frequency: 120 min intensity decay: 0.02%

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.08

2096 reflections

353 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: SET4 (de Boer et al., 1984 ▶); data reduction: MolEN (Enraf–Nonius, 1990 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1990 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006291/bt2882sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006291/bt2882Isup2.hkl

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

C17H21NS	F(000) = 584
Mr = 271.42	Dx = 1.161 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 10.0877 (9) Å	θ = 36.5–42.8°
b = 14.275 (3) Å	µ = 0.20 mm−1
c = 11.4503 (9) Å	T = 173 K
β = 109.651 (8)°	Cube, yellow
V = 1552.8 (4) Å3	0.51 × 0.43 × 0.33 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 23.0°, θmin = 1.9°
ω/2θ scans	h = −11→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.884, Tmax = 0.939	l = 0→12
2222 measured reflections	3 standard reflections every 120 min
2096 independent reflections	intensity decay: 0.02%

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.2045P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2096 reflections	Δρmax = 0.20 e Å−3
353 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0222 (27)

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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	0.92670 (8)	0.27773 (6)	0.17143 (7)	0.0403 (2)
C1	0.8043 (4)	0.3644 (2)	0.1137 (3)	0.0455 (8)
H1	0.8191	0.4169	0.0716	0.055*
C2	0.6842 (4)	0.3472 (2)	0.1367 (3)	0.0441 (8)
H2	0.6065	0.3868	0.1122	0.053*
C3	0.6886 (3)	0.2627 (2)	0.2017 (3)	0.0373 (7)
H3	0.6143	0.2407	0.2250	0.045*
C4	0.8135 (3)	0.2166 (2)	0.2268 (2)	0.0304 (7)
C5	0.8510 (3)	0.1257 (2)	0.2850 (2)	0.0290 (6)
H5	0.7887	0.0959	0.3170	0.035*
N1	0.9657 (2)	0.08570 (16)	0.2936 (2)	0.0307 (6)
C6	0.9982 (3)	−0.0052 (2)	0.3474 (3)	0.0303 (6)
C7	1.0936 (3)	−0.0118 (2)	0.4707 (3)	0.0332 (7)
C8	1.1362 (3)	−0.1004 (2)	0.5183 (3)	0.0402 (7)
H8	1.1975	−0.1061	0.5994	0.048*
C9	1.0900 (4)	−0.1802 (2)	0.4487 (3)	0.0459 (8)
H9	1.1204	−0.2389	0.4822	0.055*
C10	0.9987 (4)	−0.1719 (2)	0.3292 (3)	0.0481 (9)
H10	0.9695	−0.2259	0.2820	0.058*
C11	0.9485 (3)	−0.0855 (2)	0.2764 (3)	0.0371 (7)
C12	1.1462 (3)	0.0744 (2)	0.5499 (3)	0.0425 (8)
H12	1.1123	0.1299	0.4980	0.051*
C13	1.3055 (5)	0.0779 (4)	0.6001 (6)	0.0936 (16)
H13A	1.3415	0.0749	0.5326	0.112*
H13B	1.3405	0.0258	0.6547	0.112*
H13C	1.3353	0.1354	0.6449	0.112*
C14	1.0880 (6)	0.0770 (3)	0.6541 (5)	0.0860 (15)
H14A	1.1285	0.1288	0.7079	0.103*
H14B	1.1105	0.0196	0.7002	0.103*
H14C	0.9876	0.0844	0.6211	0.103*
C15	0.8490 (4)	−0.0815 (2)	0.1424 (3)	0.0483 (9)
H15	0.8103	−0.0180	0.1261	0.058*
C16	0.7261 (4)	−0.1501 (3)	0.1206 (4)	0.0586 (10)
H16A	0.6602	−0.1416	0.0384	0.070*
H16B	0.6800	−0.1386	0.1802	0.070*
H16C	0.7611	−0.2132	0.1296	0.070*
C17	0.9284 (4)	−0.1013 (3)	0.0537 (3)	0.0595 (10)
H17A	0.8637	−0.1017	−0.0299	0.071*
H17B	0.9739	−0.1611	0.0728	0.071*
H17C	0.9979	−0.0534	0.0621	0.071*
S2	1.45567 (7)	0.01922 (5)	0.12971 (7)	0.0362 (2)
C18	1.3736 (3)	0.1201 (2)	0.0597 (3)	0.0364 (7)
H18	1.4044	0.1563	0.0064	0.044*
C19	1.2598 (3)	0.1407 (2)	0.0909 (3)	0.0376 (7)
H19	1.2027	0.1927	0.0613	0.045*
C20	1.2366 (3)	0.0744 (2)	0.1739 (3)	0.0338 (7)
H20	1.1629	0.0785	0.2052	0.041*
C21	1.3337 (3)	0.0036 (2)	0.2034 (2)	0.0299 (6)
C22	1.3372 (3)	−0.0769 (2)	0.2809 (3)	0.0306 (7)
H22	1.2697	−0.0816	0.3194	0.037*
N2	1.4285 (3)	−0.14133 (17)	0.2987 (2)	0.0330 (6)
C23	1.4182 (3)	−0.2197 (2)	0.3739 (2)	0.0284 (6)
C24	1.3357 (3)	−0.2969 (2)	0.3184 (3)	0.0298 (6)
C25	1.3289 (3)	−0.3717 (2)	0.3932 (3)	0.0336 (7)
H25	1.2725	−0.4229	0.3582	0.040*
C26	1.4047 (3)	−0.3717 (2)	0.5197 (3)	0.0346 (7)
H26	1.3980	−0.4222	0.5688	0.041*
C27	1.4899 (3)	−0.2964 (2)	0.5719 (3)	0.0351 (7)
H27	1.5428	−0.2977	0.6559	0.042*
C28	1.4983 (3)	−0.2185 (2)	0.5012 (3)	0.0318 (6)
C29	1.2653 (3)	−0.3020 (2)	0.1779 (3)	0.0349 (7)
H29	1.2322	−0.2389	0.1487	0.042*
C30	1.3730 (4)	−0.3295 (3)	0.1190 (3)	0.0516 (9)
H30A	1.4096	−0.3905	0.1478	0.062*
H30B	1.4484	−0.2847	0.1413	0.062*
H30C	1.3294	−0.3306	0.0304	0.062*
C31	1.1389 (3)	−0.3669 (3)	0.1358 (3)	0.0480 (8)
H31A	1.0931	−0.3608	0.0479	0.058*
H31B	1.0741	−0.3506	0.1777	0.058*
H31C	1.1694	−0.4305	0.1553	0.058*
C32	1.5953 (3)	−0.1370 (2)	0.5574 (3)	0.0417 (8)
H32	1.5458	−0.0794	0.5207	0.050*
C33	1.6322 (5)	−0.1290 (3)	0.6970 (3)	0.0681 (12)
H33A	1.6913	−0.0753	0.7265	0.082*
H33B	1.6812	−0.1844	0.7360	0.082*
H33C	1.5475	−0.1222	0.7168	0.082*
C34	1.7288 (4)	−0.1426 (3)	0.5227 (4)	0.0704 (12)
H34A	1.7039	−0.1416	0.4340	0.084*
H34B	1.7781	−0.1997	0.5546	0.084*
H34C	1.7884	−0.0901	0.5576	0.084*

	U11	U22	U33	U12	U13	U23
S1	0.0442 (4)	0.0359 (4)	0.0387 (4)	0.0012 (4)	0.0110 (3)	0.0054 (4)
C1	0.065 (2)	0.0341 (18)	0.0314 (17)	0.0049 (17)	0.0084 (16)	0.0048 (15)
C2	0.0512 (19)	0.0363 (18)	0.0319 (17)	0.0130 (15)	−0.0027 (15)	0.0002 (15)
C3	0.0383 (15)	0.0336 (18)	0.0328 (16)	0.0051 (14)	0.0023 (13)	−0.0005 (14)
C4	0.0334 (14)	0.0325 (16)	0.0187 (14)	0.0017 (12)	0.0000 (12)	−0.0056 (13)
C5	0.0338 (14)	0.0297 (15)	0.0189 (14)	−0.0001 (13)	0.0028 (11)	−0.0028 (13)
N1	0.0334 (13)	0.0268 (13)	0.0280 (13)	0.0034 (11)	0.0051 (10)	0.0002 (11)
C6	0.0343 (14)	0.0281 (16)	0.0286 (16)	0.0019 (12)	0.0109 (12)	0.0022 (13)
C7	0.0403 (16)	0.0293 (16)	0.0282 (16)	0.0003 (13)	0.0090 (13)	0.0033 (13)
C8	0.0479 (17)	0.0363 (17)	0.0280 (16)	0.0050 (15)	0.0018 (14)	0.0030 (15)
C9	0.064 (2)	0.0281 (17)	0.0399 (19)	0.0096 (16)	0.0093 (16)	0.0048 (15)
C10	0.064 (2)	0.0284 (17)	0.044 (2)	0.0051 (16)	0.0069 (17)	−0.0067 (15)
C11	0.0416 (16)	0.0295 (16)	0.0340 (17)	0.0049 (13)	0.0045 (14)	−0.0049 (14)
C12	0.0499 (18)	0.0313 (17)	0.0337 (16)	−0.0038 (15)	−0.0023 (14)	0.0059 (15)
C13	0.065 (3)	0.080 (4)	0.124 (4)	−0.029 (3)	0.016 (3)	−0.031 (3)
C14	0.140 (4)	0.055 (3)	0.081 (3)	−0.010 (3)	0.062 (3)	−0.028 (3)
C15	0.058 (2)	0.0320 (17)	0.0383 (19)	0.0107 (16)	−0.0054 (16)	−0.0065 (15)
C16	0.0452 (19)	0.062 (2)	0.056 (2)	0.0053 (17)	0.0012 (18)	−0.016 (2)
C17	0.069 (2)	0.064 (2)	0.0341 (18)	−0.008 (2)	0.0018 (16)	0.0017 (19)
S2	0.0377 (4)	0.0345 (4)	0.0361 (4)	0.0016 (3)	0.0120 (3)	0.0049 (3)
C18	0.0454 (17)	0.0320 (16)	0.0280 (15)	−0.0045 (14)	0.0073 (13)	0.0094 (14)
C19	0.0380 (16)	0.0284 (16)	0.0393 (17)	0.0013 (14)	0.0034 (14)	0.0053 (15)
C20	0.0354 (15)	0.0311 (16)	0.0320 (15)	0.0005 (13)	0.0074 (12)	0.0013 (13)
C21	0.0335 (14)	0.0277 (15)	0.0216 (14)	−0.0030 (12)	0.0003 (11)	0.0013 (13)
C22	0.0325 (15)	0.0292 (15)	0.0257 (15)	−0.0037 (13)	0.0038 (12)	0.0001 (13)
N2	0.0393 (13)	0.0289 (13)	0.0270 (13)	0.0025 (11)	0.0060 (11)	0.0055 (11)
C23	0.0325 (13)	0.0270 (14)	0.0243 (14)	0.0045 (13)	0.0076 (12)	0.0066 (13)
C24	0.0343 (14)	0.0282 (15)	0.0248 (15)	0.0058 (12)	0.0070 (12)	0.0067 (13)
C25	0.0398 (15)	0.0281 (15)	0.0296 (16)	0.0006 (14)	0.0072 (13)	−0.0006 (14)
C26	0.0493 (16)	0.0261 (15)	0.0289 (16)	0.0040 (14)	0.0138 (13)	0.0061 (13)
C27	0.0437 (16)	0.0370 (17)	0.0205 (15)	0.0036 (14)	0.0053 (12)	0.0029 (14)
C28	0.0379 (13)	0.0261 (14)	0.0290 (14)	0.0035 (14)	0.0080 (11)	0.0041 (14)
C29	0.0394 (16)	0.0342 (16)	0.0240 (16)	0.0010 (13)	0.0013 (13)	0.0053 (13)
C30	0.0513 (19)	0.076 (3)	0.0222 (16)	0.0061 (18)	0.0056 (14)	0.0009 (17)
C31	0.0544 (18)	0.051 (2)	0.0296 (16)	−0.0086 (18)	0.0019 (14)	0.0020 (17)
C32	0.0548 (19)	0.0315 (17)	0.0286 (17)	−0.0016 (15)	0.0007 (15)	0.0032 (14)
C33	0.108 (3)	0.047 (2)	0.0354 (19)	−0.028 (2)	0.005 (2)	−0.0012 (18)
C34	0.057 (2)	0.069 (3)	0.073 (3)	−0.021 (2)	0.006 (2)	−0.011 (2)

S1—C1	1.715 (3)	S2—C18	1.719 (3)
S1—C4	1.719 (3)	S2—C21	1.724 (3)
C1—C2	1.345 (5)	C18—C19	1.345 (4)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.411 (5)	C19—C20	1.415 (4)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.364 (4)	C20—C21	1.368 (4)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.449 (4)	C21—C22	1.445 (4)
C5—N1	1.264 (3)	C22—N2	1.269 (4)
C5—H5	0.9300	C22—H22	0.9300
N1—C6	1.427 (4)	N2—C23	1.437 (4)
C6—C11	1.398 (4)	C23—C24	1.398 (4)
C6—C7	1.419 (4)	C23—C28	1.409 (4)
C7—C8	1.387 (5)	C24—C25	1.385 (4)
C7—C12	1.515 (4)	C24—C29	1.526 (4)
C8—C9	1.379 (5)	C25—C26	1.393 (4)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.374 (5)	C26—C27	1.381 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.392 (5)	C27—C28	1.395 (5)
C10—H10	0.9300	C27—H27	0.9300
C11—C15	1.527 (4)	C28—C32	1.517 (4)
C12—C14	1.498 (6)	C29—C30	1.511 (5)
C12—C13	1.514 (5)	C29—C31	1.518 (5)
C12—H12	0.9800	C29—H29	0.9800
C13—H13A	0.9600	C30—H30A	0.9600
C13—H13B	0.9600	C30—H30B	0.9600
C13—H13C	0.9600	C30—H30C	0.9600
C14—H14A	0.9600	C31—H31A	0.9600
C14—H14B	0.9600	C31—H31B	0.9600
C14—H14C	0.9600	C31—H31C	0.9600
C15—C17	1.517 (5)	C32—C33	1.519 (5)
C15—C16	1.533 (5)	C32—C34	1.530 (5)
C15—H15	0.9800	C32—H32	0.9800
C16—H16A	0.9600	C33—H33A	0.9600
C16—H16B	0.9600	C33—H33B	0.9600
C16—H16C	0.9600	C33—H33C	0.9600
C17—H17A	0.9600	C34—H34A	0.9600
C17—H17B	0.9600	C34—H34B	0.9600
C17—H17C	0.9600	C34—H34C	0.9600
C1—S1—C4	91.53 (16)	C18—S2—C21	91.46 (14)
C2—C1—S1	111.8 (3)	C19—C18—S2	112.3 (2)
C2—C1—H1	124.1	C19—C18—H18	123.8
S1—C1—H1	124.1	S2—C18—H18	123.8
C1—C2—C3	112.9 (3)	C18—C19—C20	112.3 (3)
C1—C2—H2	123.6	C18—C19—H19	123.8
C3—C2—H2	123.6	C20—C19—H19	123.8
C4—C3—C2	112.8 (3)	C21—C20—C19	113.2 (3)
C4—C3—H3	123.6	C21—C20—H20	123.4
C2—C3—H3	123.6	C19—C20—H20	123.4
C3—C4—C5	127.5 (3)	C20—C21—C22	127.3 (3)
C3—C4—S1	111.0 (2)	C20—C21—S2	110.7 (2)
C5—C4—S1	121.4 (2)	C22—C21—S2	121.9 (2)
N1—C5—C4	122.0 (3)	N2—C22—C21	122.8 (3)
N1—C5—H5	119.0	N2—C22—H22	118.6
C4—C5—H5	119.0	C21—C22—H22	118.6
C5—N1—C6	121.0 (3)	C22—N2—C23	117.8 (2)
C11—C6—C7	121.0 (3)	C24—C23—C28	121.8 (3)
C11—C6—N1	120.6 (2)	C24—C23—N2	119.5 (2)
C7—C6—N1	118.1 (2)	C28—C23—N2	118.6 (3)
C8—C7—C6	117.9 (3)	C25—C24—C23	118.1 (3)
C8—C7—C12	120.4 (2)	C25—C24—C29	120.8 (3)
C6—C7—C12	121.7 (3)	C23—C24—C29	120.8 (3)
C9—C8—C7	121.8 (3)	C24—C25—C26	121.3 (3)
C9—C8—H8	119.1	C24—C25—H25	119.3
C7—C8—H8	119.1	C26—C25—H25	119.3
C10—C9—C8	119.2 (3)	C27—C26—C25	119.6 (3)
C10—C9—H9	120.4	C27—C26—H26	120.2
C8—C9—H9	120.4	C25—C26—H26	120.2
C9—C10—C11	122.2 (3)	C26—C27—C28	121.3 (3)
C9—C10—H10	118.9	C26—C27—H27	119.3
C11—C10—H10	118.9	C28—C27—H27	119.3
C10—C11—C6	117.9 (3)	C27—C28—C23	117.7 (3)
C10—C11—C15	119.4 (3)	C27—C28—C32	121.5 (3)
C6—C11—C15	122.7 (3)	C23—C28—C32	120.8 (3)
C14—C12—C7	110.2 (3)	C30—C29—C31	110.7 (3)
C14—C12—C13	110.3 (4)	C30—C29—C24	109.5 (2)
C7—C12—C13	111.6 (3)	C31—C29—C24	114.1 (3)
C14—C12—H12	108.2	C30—C29—H29	107.4
C7—C12—H12	108.2	C31—C29—H29	107.4
C13—C12—H12	108.2	C24—C29—H29	107.4
C12—C13—H13A	109.5	C29—C30—H30A	109.5
C12—C13—H13B	109.5	C29—C30—H30B	109.5
H13A—C13—H13B	109.5	H30A—C30—H30B	109.5
C12—C13—H13C	109.5	C29—C30—H30C	109.5
H13A—C13—H13C	109.5	H30A—C30—H30C	109.5
H13B—C13—H13C	109.5	H30B—C30—H30C	109.5
C12—C14—H14A	109.5	C29—C31—H31A	109.5
C12—C14—H14B	109.5	C29—C31—H31B	109.5
H14A—C14—H14B	109.5	H31A—C31—H31B	109.5
C12—C14—H14C	109.5	C29—C31—H31C	109.5
H14A—C14—H14C	109.5	H31A—C31—H31C	109.5
H14B—C14—H14C	109.5	H31B—C31—H31C	109.5
C17—C15—C11	110.4 (3)	C28—C32—C33	113.5 (3)
C17—C15—C16	110.7 (3)	C28—C32—C34	110.4 (3)
C11—C15—C16	111.2 (3)	C33—C32—C34	110.6 (3)
C17—C15—H15	108.1	C28—C32—H32	107.4
C11—C15—H15	108.1	C33—C32—H32	107.4
C16—C15—H15	108.1	C34—C32—H32	107.4
C15—C16—H16A	109.5	C32—C33—H33A	109.5
C15—C16—H16B	109.5	C32—C33—H33B	109.5
H16A—C16—H16B	109.5	H33A—C33—H33B	109.5
C15—C16—H16C	109.5	C32—C33—H33C	109.5
H16A—C16—H16C	109.5	H33A—C33—H33C	109.5
H16B—C16—H16C	109.5	H33B—C33—H33C	109.5
C15—C17—H17A	109.5	C32—C34—H34A	109.5
C15—C17—H17B	109.5	C32—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
C15—C17—H17C	109.5	C32—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5
C4—S1—C1—C2	0.4 (3)	C21—S2—C18—C19	0.1 (2)
S1—C1—C2—C3	−0.2 (4)	S2—C18—C19—C20	0.3 (3)
C1—C2—C3—C4	−0.2 (4)	C18—C19—C20—C21	−0.5 (4)
C2—C3—C4—C5	−176.0 (3)	C19—C20—C21—C22	−177.2 (3)
C2—C3—C4—S1	0.5 (3)	C19—C20—C21—S2	0.6 (3)
C1—S1—C4—C3	−0.5 (2)	C18—S2—C21—C20	−0.4 (2)
C1—S1—C4—C5	176.2 (2)	C18—S2—C21—C22	177.6 (2)
C3—C4—C5—N1	173.4 (3)	C20—C21—C22—N2	176.8 (3)
S1—C4—C5—N1	−2.8 (4)	S2—C21—C22—N2	−0.8 (4)
C4—C5—N1—C6	−177.8 (2)	C21—C22—N2—C23	−177.7 (2)
C5—N1—C6—C11	84.0 (3)	C22—N2—C23—C24	88.5 (3)
C5—N1—C6—C7	−102.3 (3)	C22—N2—C23—C28	−94.9 (3)
C11—C6—C7—C8	0.1 (4)	C28—C23—C24—C25	3.0 (4)
N1—C6—C7—C8	−173.5 (3)	N2—C23—C24—C25	179.5 (2)
C11—C6—C7—C12	−178.7 (3)	C28—C23—C24—C29	−172.0 (3)
N1—C6—C7—C12	7.6 (4)	N2—C23—C24—C29	4.5 (4)
C6—C7—C8—C9	1.0 (5)	C23—C24—C25—C26	−1.7 (4)
C12—C7—C8—C9	179.9 (3)	C29—C24—C25—C26	173.2 (3)
C7—C8—C9—C10	−0.5 (5)	C24—C25—C26—C27	−0.8 (4)
C8—C9—C10—C11	−1.4 (6)	C25—C26—C27—C28	2.2 (4)
C9—C10—C11—C6	2.5 (5)	C26—C27—C28—C23	−0.9 (4)
C9—C10—C11—C15	179.1 (3)	C26—C27—C28—C32	−178.1 (3)
C7—C6—C11—C10	−1.8 (4)	C24—C23—C28—C27	−1.7 (4)
N1—C6—C11—C10	171.7 (3)	N2—C23—C28—C27	−178.2 (3)
C7—C6—C11—C15	−178.3 (3)	C24—C23—C28—C32	175.5 (3)
N1—C6—C11—C15	−4.8 (5)	N2—C23—C28—C32	−1.0 (4)
C8—C7—C12—C14	−67.3 (4)	C25—C24—C29—C30	−97.0 (3)
C6—C7—C12—C14	111.6 (4)	C23—C24—C29—C30	77.8 (4)
C8—C7—C12—C13	55.6 (5)	C25—C24—C29—C31	27.7 (4)
C6—C7—C12—C13	−125.6 (4)	C23—C24—C29—C31	−157.5 (3)
C10—C11—C15—C17	−72.7 (4)	C27—C28—C32—C33	−23.4 (5)
C6—C11—C15—C17	103.7 (4)	C23—C28—C32—C33	159.5 (3)
C10—C11—C15—C16	50.5 (4)	C27—C28—C32—C34	101.4 (4)
C6—C11—C15—C16	−133.1 (3)	C23—C28—C32—C34	−75.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N1	0.93	2.52	3.449 (8)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N1	0.93	2.52	3.449 (8)	178