1-Benzyl-3,5-bis-(2-thienylmethyl-ene)-4-piperidone.

In the title compound, C(22)H(19)NOS(2), the thio-phene rings form angles of 69.74 (18) and 65.56 (16)° with the benzene ring. The piperidone ring adopts a half-chair conformation due to the presence of the conjugated ketone systems. Both thio-phene rings are disordered over two orientations [occupancies of 0.758 (2)/0.242 (2) and 0.588 (2)/0.412 (2)] at 180° from one another. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds, C-H⋯π and aromatic π-π stacking inter-actions [shortest centroid-centroid separation = 3.865 (3) Å] help to stabilize the packing.

Related literature

For general background to 3,5-bis(arylidene)-4-piperidone derivatives, see: Baluja et al. (1964 ▶). Benvenuto et al. (1993 ▶); Dimmock et al. (1983 ▶); Dimmock et al. (2003 ▶); El-Subbagh et al. (2000 ▶). For details of the synthesis, see: Pati et al. (2009 ▶).

Experimental

Crystal data

C22H19NOS2

M = 377.50

Triclinic,

a = 5.7110 (11) Å

b = 9.4072 (19) Å

c = 17.338 (4) Å

α = 87.82 (3)°

β = 87.55 (3)°

γ = 81.99 (3)°

V = 921.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 113 K

0.19 × 0.16 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.945, T max = 0.971

9377 measured reflections

4321 independent reflections

3660 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.05

4321 reflections

268 parameters

58 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033923/bg2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033923/bg2287Isup2.hkl

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

C22H19NOS2	Z = 2
Mr = 377.50	F(000) = 396
Triclinic, P1	Dx = 1.361 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7110 (11) Å	Cell parameters from 2974 reflections
b = 9.4072 (19) Å	θ = 2.3–27.4°
c = 17.338 (4) Å	µ = 0.30 mm−1
α = 87.82 (3)°	T = 113 K
β = 87.55 (3)°	Block, colorless
γ = 81.99 (3)°	0.19 × 0.16 × 0.10 mm
V = 921.1 (3) Å3

Rigaku Saturn CCD area-detector diffractometer	4321 independent reflections
Radiation source: rotating anode	3660 reflections with I > 2σ(I)
confocal	Rint = 0.031
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.2°
ω and φ scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→12
Tmin = 0.945, Tmax = 0.971	l = −22→22
9377 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.2715P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
4321 reflections	Δρmax = 0.33 e Å−3
268 parameters	Δρmin = −0.23 e Å−3
58 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: 0.062 (7)

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)
O1	0.10269 (17)	1.04217 (11)	0.40042 (6)	0.0258 (2)
N1	0.6906 (2)	0.83369 (11)	0.29936 (6)	0.0179 (2)
S1	0.62468 (11)	1.24588 (7)	0.15845 (4)	0.02485 (18)	0.757 (2)
C1	0.5420 (7)	1.3962 (7)	0.1016 (3)	0.0266 (8)	0.757 (2)
H1	0.6425	1.4337	0.0632	0.032*	0.757 (2)
C2	0.3140 (7)	1.4554 (5)	0.1182 (4)	0.0254 (7)	0.757 (2)
H2	0.2357	1.5379	0.0920	0.031*	0.757 (2)
C3	0.2069 (10)	1.3777 (7)	0.1801 (4)	0.0271 (8)	0.757 (2)
H3	0.0490	1.4040	0.1993	0.033*	0.757 (2)
C4	0.3533 (11)	1.2632 (9)	0.2086 (6)	0.0188 (9)	0.757 (2)
S1'	0.1590 (8)	1.4029 (5)	0.1772 (3)	0.0271 (8)	0.243 (2)
C1'	0.351 (2)	1.4701 (19)	0.1149 (13)	0.0254 (7)	0.243 (2)
H1'	0.3151	1.5556	0.0842	0.031*	0.243 (2)
C2'	0.563 (3)	1.388 (2)	0.1139 (13)	0.0266 (8)	0.243 (2)
H2'	0.6929	1.4068	0.0808	0.032*	0.243 (2)
C3'	0.5729 (16)	1.2660 (11)	0.1688 (6)	0.02485 (18)	0.243 (2)
H3'	0.7127	1.2021	0.1794	0.030*	0.243 (2)
C4'	0.357 (3)	1.255 (3)	0.2029 (19)	0.0188 (9)	0.243 (2)
C5	0.2893 (2)	1.17132 (14)	0.27215 (8)	0.0193 (3)
H5	0.1337	1.1968	0.2935	0.023*
C6	0.4133 (2)	1.05527 (14)	0.30644 (7)	0.0178 (3)
C7	0.3030 (2)	0.99300 (14)	0.37716 (8)	0.0187 (3)
C8	0.4454 (2)	0.87146 (14)	0.41855 (7)	0.0182 (3)
C9	0.6814 (2)	0.81022 (14)	0.38344 (7)	0.0190 (3)
H9A	0.8074	0.8558	0.4061	0.023*
H9B	0.7113	0.7059	0.3960	0.023*
C10	0.6555 (2)	0.98827 (14)	0.27952 (8)	0.0198 (3)
H10A	0.6743	1.0031	0.2229	0.024*
H10B	0.7767	1.0351	0.3041	0.024*
C11	0.3543 (2)	0.82590 (14)	0.48683 (7)	0.0197 (3)
H11	0.2046	0.8765	0.5019	0.024*
S2	0.7205 (3)	0.61663 (12)	0.53477 (8)	0.0240 (2)	0.5857 (19)
C12	0.445 (3)	0.716 (4)	0.5395 (19)	0.0203 (8)	0.5857 (19)
C13	0.3181 (9)	0.6735 (6)	0.6021 (3)	0.0232 (3)	0.5857 (19)
H13	0.1606	0.7155	0.6145	0.028*	0.5857 (19)
C14	0.4430 (6)	0.5605 (3)	0.64780 (19)	0.0247 (7)	0.5857 (19)
H14	0.3802	0.5200	0.6939	0.030*	0.5857 (19)
C15	0.6667 (8)	0.5177 (7)	0.6164 (4)	0.0290 (11)	0.5857 (19)
H15	0.7766	0.4427	0.6375	0.035*	0.5857 (19)
S2'	0.3013 (3)	0.64625 (16)	0.61623 (9)	0.0232 (3)	0.4143 (19)
C12'	0.469 (4)	0.710 (6)	0.540 (3)	0.0203 (8)	0.4143 (19)
C13'	0.6958 (16)	0.6399 (9)	0.5400 (5)	0.0240 (2)	0.4143 (19)
H13'	0.8182	0.6600	0.5041	0.029*	0.4143 (19)
C14'	0.7256 (14)	0.5307 (11)	0.6014 (6)	0.0290 (11)	0.4143 (19)
H14'	0.8709	0.4704	0.6095	0.035*	0.4143 (19)
C15'	0.5303 (10)	0.5224 (5)	0.6456 (3)	0.0247 (7)	0.4143 (19)
H15'	0.5202	0.4562	0.6880	0.030*	0.4143 (19)
C16	0.9204 (2)	0.76582 (15)	0.26799 (8)	0.0215 (3)
H16A	0.9432	0.6628	0.2840	0.026*
H16B	1.0479	0.8110	0.2900	0.026*
C17	0.9401 (2)	0.77921 (14)	0.18092 (8)	0.0196 (3)
C18	1.1212 (3)	0.84215 (15)	0.14380 (9)	0.0267 (3)
H18	1.2351	0.8780	0.1734	0.032*
C19	1.1376 (3)	0.85323 (17)	0.06335 (9)	0.0342 (4)
H19	1.2626	0.8962	0.0383	0.041*
C20	0.9723 (3)	0.80178 (18)	0.02021 (9)	0.0355 (4)
H20	0.9831	0.8093	−0.0346	0.043*
C21	0.7906 (3)	0.73904 (18)	0.05690 (9)	0.0329 (4)
H21	0.6764	0.7038	0.0272	0.039*
C22	0.7747 (3)	0.72757 (16)	0.13676 (8)	0.0251 (3)
H22	0.6499	0.6841	0.1616	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0185 (5)	0.0275 (5)	0.0292 (5)	0.0011 (4)	0.0057 (4)	0.0033 (4)
N1	0.0179 (6)	0.0160 (5)	0.0182 (5)	0.0023 (4)	0.0023 (4)	0.0001 (4)
S1	0.0206 (4)	0.0249 (3)	0.0266 (3)	0.0014 (2)	0.0062 (2)	0.0067 (2)
C1	0.0339 (12)	0.0242 (11)	0.021 (2)	−0.0028 (9)	0.0019 (13)	0.0046 (10)
C2	0.0331 (16)	0.0182 (13)	0.0241 (10)	−0.0003 (12)	−0.0031 (13)	0.0014 (8)
C3	0.0295 (19)	0.0229 (17)	0.0278 (7)	0.0002 (12)	−0.0064 (11)	0.0057 (9)
C4	0.0208 (7)	0.0175 (12)	0.0176 (17)	−0.0004 (6)	−0.0005 (6)	−0.0038 (13)
S1'	0.0295 (19)	0.0229 (17)	0.0278 (7)	0.0002 (12)	−0.0064 (11)	0.0057 (9)
C1'	0.0331 (16)	0.0182 (13)	0.0241 (10)	−0.0003 (12)	−0.0031 (13)	0.0014 (8)
C2'	0.0339 (12)	0.0242 (11)	0.021 (2)	−0.0028 (9)	0.0019 (13)	0.0046 (10)
C3'	0.0206 (4)	0.0249 (3)	0.0266 (3)	0.0014 (2)	0.0062 (2)	0.0067 (2)
C4'	0.0208 (7)	0.0175 (12)	0.0176 (17)	−0.0004 (6)	−0.0005 (6)	−0.0038 (13)
C5	0.0174 (6)	0.0186 (6)	0.0218 (6)	−0.0022 (5)	0.0005 (5)	−0.0015 (5)
C6	0.0170 (6)	0.0171 (6)	0.0194 (6)	−0.0029 (5)	0.0005 (5)	−0.0030 (5)
C7	0.0178 (6)	0.0168 (6)	0.0214 (6)	−0.0023 (5)	0.0001 (5)	−0.0029 (5)
C8	0.0185 (7)	0.0174 (6)	0.0193 (6)	−0.0036 (5)	−0.0007 (5)	−0.0032 (5)
C9	0.0182 (6)	0.0192 (6)	0.0187 (6)	−0.0002 (5)	−0.0001 (5)	0.0006 (5)
C10	0.0192 (7)	0.0173 (6)	0.0216 (6)	0.0005 (5)	0.0025 (5)	0.0014 (5)
C11	0.0202 (7)	0.0189 (6)	0.0202 (6)	−0.0031 (5)	0.0001 (5)	−0.0030 (5)
S2	0.0215 (5)	0.0240 (5)	0.0242 (4)	0.0047 (3)	−0.0041 (3)	0.0019 (3)
C12	0.025 (3)	0.019 (2)	0.0171 (7)	−0.004 (3)	−0.002 (3)	−0.0014 (8)
C13	0.0233 (5)	0.0290 (7)	0.0169 (7)	−0.0053 (4)	0.0021 (4)	0.0048 (4)
C14	0.035 (2)	0.0210 (17)	0.0186 (8)	−0.0037 (13)	−0.0021 (14)	0.0007 (11)
C15	0.041 (3)	0.0247 (15)	0.021 (3)	0.000 (2)	−0.010 (2)	0.0045 (12)
S2'	0.0233 (5)	0.0290 (7)	0.0169 (7)	−0.0053 (4)	0.0021 (4)	0.0048 (4)
C12'	0.025 (3)	0.019 (2)	0.0171 (7)	−0.004 (3)	−0.002 (3)	−0.0014 (8)
C13'	0.0215 (5)	0.0240 (5)	0.0242 (4)	0.0047 (3)	−0.0041 (3)	0.0019 (3)
C14'	0.041 (3)	0.0247 (15)	0.021 (3)	0.000 (2)	−0.010 (2)	0.0045 (12)
C15'	0.035 (2)	0.0210 (17)	0.0186 (8)	−0.0037 (13)	−0.0021 (14)	0.0007 (11)
C16	0.0192 (7)	0.0220 (6)	0.0215 (7)	0.0042 (5)	−0.0006 (5)	−0.0021 (5)
C17	0.0187 (7)	0.0162 (6)	0.0218 (6)	0.0047 (5)	0.0023 (5)	−0.0008 (5)
C18	0.0243 (7)	0.0219 (7)	0.0327 (8)	−0.0012 (6)	0.0043 (6)	−0.0001 (6)
C19	0.0343 (9)	0.0281 (8)	0.0359 (9)	0.0034 (7)	0.0152 (7)	0.0090 (6)
C20	0.0445 (10)	0.0348 (8)	0.0204 (7)	0.0153 (7)	0.0056 (7)	0.0043 (6)
C21	0.0342 (9)	0.0361 (8)	0.0257 (7)	0.0073 (7)	−0.0061 (6)	−0.0059 (6)
C22	0.0225 (7)	0.0264 (7)	0.0252 (7)	0.0002 (6)	0.0018 (5)	−0.0024 (6)

O1—C7	1.2301 (17)	C11—C12	1.413 (4)
N1—C9	1.4659 (16)	C11—C12'	1.497 (5)
N1—C16	1.4688 (17)	C11—H11	0.9500
N1—C10	1.4696 (16)	S2—C15	1.704 (4)
S1—C1	1.715 (3)	S2—C12	1.716 (6)
S1—C4	1.735 (3)	C12—C13	1.355 (6)
C1—C2	1.366 (4)	C13—C14	1.428 (5)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.439 (6)	C14—C15	1.381 (5)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.359 (5)	C15—H15	0.9500
C3—H3	0.9500	S2'—C15'	1.707 (5)
C4—C5	1.441 (3)	S2'—C12'	1.735 (7)
S1'—C1'	1.677 (9)	C12'—C13'	1.372 (8)
S1'—C4'	1.720 (9)	C13'—C14'	1.450 (7)
C1'—C2'	1.342 (9)	C13'—H13'	0.9500
C1'—H1'	0.9500	C14'—C15'	1.336 (6)
C2'—C3'	1.458 (8)	C14'—H14'	0.9500
C2'—H2'	0.9500	C15'—H15'	0.9500
C3'—C4'	1.361 (9)	C16—C17	1.5108 (18)
C3'—H3'	0.9500	C16—H16A	0.9900
C4'—C5	1.479 (9)	C16—H16B	0.9900
C5—C6	1.3484 (19)	C17—C18	1.385 (2)
C5—H5	0.9500	C17—C22	1.390 (2)
C6—C7	1.4917 (18)	C18—C19	1.395 (2)
C6—C10	1.5007 (18)	C18—H18	0.9500
C7—C8	1.4870 (18)	C19—C20	1.378 (3)
C8—C11	1.3515 (19)	C19—H19	0.9500
C8—C9	1.5031 (18)	C20—C21	1.384 (3)
C9—H9A	0.9900	C20—H20	0.9500
C9—H9B	0.9900	C21—C22	1.385 (2)
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900	C22—H22	0.9500
C9—N1—C16	109.11 (10)	C8—C11—C12	130.8 (5)
C9—N1—C10	110.22 (10)	C8—C11—C12'	126.7 (6)
C16—N1—C10	110.54 (11)	C8—C11—H11	114.6
C1—S1—C4	92.37 (16)	C12—C11—H11	114.6
C2—C1—S1	111.8 (2)	C12'—C11—H11	118.6
C2—C1—H1	124.1	C15—S2—C12	92.9 (2)
S1—C1—H1	124.1	C13—C12—C11	123.1 (5)
C1—C2—C3	111.8 (3)	C13—C12—S2	110.5 (3)
C1—C2—H2	124.1	C11—C12—S2	126.4 (4)
C3—C2—H2	124.1	C12—C13—C14	114.0 (4)
C4—C3—C2	113.5 (4)	C12—C13—H13	123.0
C4—C3—H3	123.3	C14—C13—H13	123.0
C2—C3—H3	123.3	C15—C14—C13	111.2 (3)
C3—C4—C5	123.9 (4)	C15—C14—H14	124.4
C3—C4—S1	110.5 (3)	C13—C14—H14	124.4
C5—C4—S1	125.6 (2)	C14—C15—S2	111.3 (3)
C1'—S1'—C4'	93.9 (4)	C14—C15—H15	124.3
C2'—C1'—S1'	111.4 (5)	S2—C15—H15	124.3
C2'—C1'—H1'	124.3	C15'—S2'—C12'	93.0 (3)
S1'—C1'—H1'	124.3	C13'—C12'—C11	130.6 (6)
C1'—C2'—C3'	112.9 (6)	C13'—C12'—S2'	110.3 (4)
C1'—C2'—H2'	123.5	C11—C12'—S2'	119.1 (5)
C3'—C2'—H2'	123.5	C12'—C13'—C14'	111.5 (5)
C4'—C3'—C2'	111.5 (6)	C12'—C13'—H13'	124.2
C4'—C3'—H3'	124.3	C14'—C13'—H13'	124.2
C2'—C3'—H3'	124.3	C15'—C14'—C13'	114.0 (5)
C3'—C4'—C5	130.6 (14)	C15'—C14'—H14'	123.0
C3'—C4'—S1'	109.9 (6)	C13'—C14'—H14'	123.0
C5—C4'—S1'	116.2 (8)	C14'—C15'—S2'	111.3 (4)
C6—C5—C4	130.75 (18)	C14'—C15'—H15'	124.4
C6—C5—C4'	128.6 (4)	S2'—C15'—H15'	124.4
C6—C5—H5	114.6	N1—C16—C17	112.48 (11)
C4—C5—H5	114.6	N1—C16—H16A	109.1
C4'—C5—H5	116.6	C17—C16—H16A	109.1
C5—C6—C7	117.13 (12)	N1—C16—H16B	109.1
C5—C6—C10	124.42 (12)	C17—C16—H16B	109.1
C7—C6—C10	118.43 (11)	H16A—C16—H16B	107.8
O1—C7—C8	121.69 (12)	C18—C17—C22	118.98 (13)
O1—C7—C6	120.77 (12)	C18—C17—C16	121.17 (13)
C8—C7—C6	117.54 (11)	C22—C17—C16	119.85 (13)
C11—C8—C7	117.02 (12)	C17—C18—C19	120.50 (15)
C11—C8—C9	124.41 (12)	C17—C18—H18	119.8
C7—C8—C9	118.55 (11)	C19—C18—H18	119.8
N1—C9—C8	111.58 (11)	C20—C19—C18	119.98 (15)
N1—C9—H9A	109.3	C20—C19—H19	120.0
C8—C9—H9A	109.3	C18—C19—H19	120.0
N1—C9—H9B	109.3	C19—C20—C21	119.85 (14)
C8—C9—H9B	109.3	C19—C20—H20	120.1
H9A—C9—H9B	108.0	C21—C20—H20	120.1
N1—C10—C6	110.42 (11)	C20—C21—C22	120.19 (16)
N1—C10—H10A	109.6	C20—C21—H21	119.9
C6—C10—H10A	109.6	C22—C21—H21	119.9
N1—C10—H10B	109.6	C21—C22—C17	120.50 (15)
C6—C10—H10B	109.6	C21—C22—H22	119.7
H10A—C10—H10B	108.1	C17—C22—H22	119.7
C4—S1—C1—C2	−1.8 (8)	C9—N1—C10—C6	−63.56 (14)
S1—C1—C2—C3	1.4 (9)	C16—N1—C10—C6	175.74 (11)
C1—C2—C3—C4	−0.1 (12)	C5—C6—C10—N1	−150.83 (13)
C2—C3—C4—C5	178.1 (10)	C7—C6—C10—N1	31.04 (16)
C2—C3—C4—S1	−1.2 (13)	C7—C8—C11—C12	−180 (3)
C1—S1—C4—C3	1.7 (10)	C9—C8—C11—C12	−1(3)
C1—S1—C4—C5	−177.6 (10)	C7—C8—C11—C12'	−177 (4)
C4'—S1'—C1'—C2'	−2(3)	C9—C8—C11—C12'	1(4)
S1'—C1'—C2'—C3'	−2(3)	C8—C11—C12—C13	−173 (2)
C1'—C2'—C3'—C4'	6(4)	C8—C11—C12—S2	7(6)
C2'—C3'—C4'—C5	−166 (3)	C15—S2—C12—C13	0(3)
C2'—C3'—C4'—S1'	−7(4)	C15—S2—C12—C11	−179 (4)
C1'—S1'—C4'—C3'	5(3)	C11—C12—C13—C14	−180 (3)
C1'—S1'—C4'—C5	167 (3)	S2—C12—C13—C14	0(4)
C3—C4—C5—C6	−180.0 (8)	C12—C13—C14—C15	−1(3)
S1—C4—C5—C6	−0.7 (15)	C13—C14—C15—S2	1.3 (7)
C3—C4—C5—C4'	117 (16)	C12—S2—C15—C14	−0.9 (19)
S1—C4—C5—C4'	−64 (14)	C8—C11—C12'—C13'	11 (9)
C3'—C4'—C5—C6	−20 (6)	C8—C11—C12'—S2'	−169 (2)
S1'—C4'—C5—C6	−177.4 (12)	C15'—S2'—C12'—C13'	−2(5)
C3'—C4'—C5—C4	100 (18)	C15'—S2'—C12'—C11	178 (5)
S1'—C4'—C5—C4	−57 (12)	C11—C12'—C13'—C14'	−178 (6)
C4—C5—C6—C7	173.6 (8)	S2'—C12'—C13'—C14'	2(5)
C4'—C5—C6—C7	179 (2)	C12'—C13'—C14'—C15'	−1(4)
C4—C5—C6—C10	−4.6 (8)	C13'—C14'—C15'—S2'	−0.4 (13)
C4'—C5—C6—C10	1(2)	C12'—S2'—C15'—C14'	1(3)
C5—C6—C7—O1	3.41 (19)	C9—N1—C16—C17	177.35 (11)
C10—C6—C7—O1	−178.32 (12)	C10—N1—C16—C17	−61.29 (15)
C5—C6—C7—C8	−175.80 (12)	N1—C16—C17—C18	123.42 (14)
C10—C6—C7—C8	2.48 (18)	N1—C16—C17—C22	−56.69 (16)
O1—C7—C8—C11	−6.0 (2)	C22—C17—C18—C19	−0.1 (2)
C6—C7—C8—C11	173.18 (12)	C16—C17—C18—C19	179.75 (12)
O1—C7—C8—C9	175.57 (12)	C17—C18—C19—C20	0.2 (2)
C6—C7—C8—C9	−5.24 (18)	C18—C19—C20—C21	−0.1 (2)
C16—N1—C9—C8	−177.33 (11)	C19—C20—C21—C22	−0.1 (2)
C10—N1—C9—C8	61.11 (15)	C20—C21—C22—C17	0.2 (2)
C11—C8—C9—N1	155.81 (13)	C18—C17—C22—C21	−0.1 (2)
C7—C8—C9—N1	−25.90 (16)	C16—C17—C22—C21	−179.98 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.99	2.59	3.4946 (18)	151
C10—H10B···O1i	0.99	2.56	3.4747 (18)	153
C11—H11···O1ii	0.95	2.45	3.319 (2)	153
C13—H13···O1ii	0.95	2.56	3.338 (6)	140
C2—H2···Cg6iii	0.95	2.68	3.520 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.99	2.59	3.4946 (18)	151
C10—H10B⋯O1i	0.99	2.56	3.4747 (18)	153
C11—H11⋯O1ii	0.95	2.45	3.319 (2)	153
C13—H13⋯O1ii	0.95	2.56	3.338 (6)	140
C2—H2⋯Cg6iii	0.95	2.68	3.520 (5)	148

Symmetry codes: (i) ; (ii) ; (iii) .