Diethyl 1-(p-fluoro­phenyl)-5-oxo-3-(2-thienyl)­pyrrolidine-2,2-di­carboxyl­ate

In the title compound, C₂₀H₂₀FNO₅S, the pyrrolidine ring adopts an envelope conformation. The fluoro­phenyl and thio­phene rings are individually planar. The molecular and crystal structures are stabilized by intra- and intermolecular C-H...O interactions.

S1. Comment

N-Phenyl-γ-lactams have been observed to exhibit Gram-positive and Gram-negative antibacterial activities (Ray et al., 1995). Though the bioactivity of the γ-lactam derivatives is controlled by the substitutents attached to the γ-lactam ring which correspond to the ability of several proteins to inhibit the crosslinking of the bacterial wall (Baldwin et al., 1984), the introduction of a thiophene ring was obtained to enhance the bioactivities of the γ-lactam systems to be comparable with those of ampicilines (Kar et al., 1998). The title compound, (I), one of the thieno-γ-lactam derivatives having fluoro and gem-diethyl ester substituents, was synthesized in order to obtain a novel γ-lactam analogue with potential as a biological surrogate. The crystal structure of (I) was undertaken in order to elucidate its molecular conformation.

The bond lengths and angles in (I) show normal values and agree with those of related structures studied previously (Kandasamy et al., 1995; Sivakumar et al., 1995; Ray et al., 1997). The pyrrolidine ring adopts an envelope conformation, with atom C9 deviating by -0.196 (3) Å from the C10/N1/C7/C8 plane and with puckering parameters (Cremer & Pople, 1975) Q₂ = 0.319 (3) Å and ϕ₂ = 114.9 (5)°. The fluorophenyl and thiophene rings are planar to within ±0.007 (4) and ±0.001 (4) Å, respectively, with a dihedral angle of 67.1 (2)° between them. These fluorophenyl and thiophene rings form dihedral angles of 81.7 (2) and 46.8 (2)° with respect to the pyrrolidine ring, corresponding to an equatorial and a bisectional configuration, respectively.

One of the two ethyl carboxylate groups shows disorder in the C15 and C16 atoms, and both the major and minor configurations are in a crisscross pattern and deviate from the C10/C14/O4/O5 plane by 0.46 (2) and 0.73 (3) Å for C15A and C16A, and by -0.05 (2) and 1.31 (2) Å for C15B and C16B. In the other ethyl carboxylate group, atom O3 deviates by -0.118 (4) Å from the C10/C11/O2/C12/C13 plane, which makes an angle of 50.3 (3) with the pyrrolidine-ring plane.

The molecular structure of (I) is maintained by an intramolecular interaction between C9 and O2 [2.718 (3) Å]. In the crystal, the molecules form four C—H···O interactions (Table 2) which, together with van der Waals interactions, stabilize the crystal structure.

Related literature

For related literature, see: Baldwin et al. (1984); Cremer & Pople (1975); Kandasamy et al. (1995); Kar et al. (1998); Ray et al. (1995, 1997); Sivakumar et al. (1995).

S2. Experimental

The title compound was synthesized from p-fluoroaniline (Aldrich) through the formation of arylaminomalonate (bromoethylmalonate) and condensation with 3-(2-thienyl)acrloyl chloride in the present of triethylamine in an overall yield of 80%.

S3. Refinement

After checking their presence in the difference map, all H atoms were fixed geometrically and allowed to ride on their attached parent atoms (C—H = 0.93–0.98 Å). Due to the large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

	Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing diagram of the title compound viewed down the b axis. Disordered components are not shown as they are not involved in any hydrogen bonding or weak interactions.

Diethyl 1-(p-fluorophenyl)-5-oxo-3-(2-thienyl)pyrrolidine-2,2-dicarboxylate

Crystal data

C20H20FNO5S	Z = 2
Mr = 405.43	F(000) = 424
Triclinic, P1	Dx = 1.369 Mg m^−3
a = 9.6560 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1195 (1) Å	Cell parameters from 3864 reflections
c = 12.3126 (2) Å	θ = 1.8–28.6°
α = 110.704 (1)°	µ = 0.21 mm^−1
β = 92.659 (1)°	T = 293 K
γ = 115.856 (1)°	Slab, colourless
V = 983.58 (3) Å^3	0.42 × 0.32 × 0.16 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3391 independent reflections
Radiation source: fine-focus sealed tube	2358 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
ω scans	h = −9→11
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −11→12
Tmin = 0.919, Tmax = 0.968	l = −11→14
5604 measured 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.096P)^2] where P = (Fo^2 + 2Fc^2)/3
3391 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.09020 (9)	0.42654 (8)	0.36062 (7)	0.0538 (3)
F1	−0.8995 (3)	−0.6360 (3)	0.0284 (2)	0.1039 (8)
O1	−0.4219 (2)	−0.1151 (2)	0.49515 (18)	0.0609 (6)
O2	−0.2608 (2)	0.1873 (2)	0.20841 (17)	0.0499 (5)
O3	−0.3428 (3)	−0.0689 (2)	0.08644 (18)	0.0656 (6)
O4	−0.0970 (3)	−0.1343 (3)	0.2981 (2)	0.0696 (7)
O5	−0.0139 (2)	0.0271 (2)	0.2020 (2)	0.0623 (6)
N1	−0.3565 (2)	−0.0818 (2)	0.32687 (18)	0.0385 (5)
C1	−0.4900 (3)	−0.3678 (3)	0.1864 (3)	0.0541 (7)
H1A	−0.3951	−0.3700	0.1965	0.065*
C2	−0.6275 (4)	−0.5069 (4)	0.1116 (3)	0.0648 (9)
H2A	−0.6257	−0.6025	0.0698	0.078*
C3	−0.7642 (4)	−0.5000 (4)	0.1010 (3)	0.0640 (9)
C4	−0.7720 (4)	−0.3616 (4)	0.1586 (3)	0.0644 (9)
H4A	−0.8676	−0.3607	0.1488	0.077*
C5	−0.6352 (3)	−0.2232 (4)	0.2317 (3)	0.0518 (7)
H5A	−0.6376	−0.1275	0.2718	0.062*
C6	−0.4948 (3)	−0.2274 (3)	0.2450 (2)	0.0394 (6)
C7	−0.3332 (3)	−0.0375 (3)	0.4479 (2)	0.0440 (6)
C8	−0.1802 (3)	0.1185 (3)	0.5078 (2)	0.0470 (7)
H8A	−0.0966	0.1000	0.5338	0.056*
H8B	−0.1924	0.1938	0.5765	0.056*
C9	−0.1432 (3)	0.1832 (3)	0.4114 (2)	0.0357 (6)
H9A	−0.2019	0.2419	0.4128	0.043*
C10	−0.2229 (3)	0.0244 (3)	0.2924 (2)	0.0335 (5)
C11	−0.2825 (3)	0.0410 (3)	0.1830 (2)	0.0389 (6)
C12	−0.3036 (4)	0.2198 (4)	0.1086 (3)	0.0647 (9)
H12A	−0.2372	0.2093	0.0529	0.078*
H12B	−0.4133	0.1433	0.0664	0.078*
C13	−0.2807 (5)	0.3832 (5)	0.1572 (4)	0.0902 (13)
H13A	−0.3108	0.4063	0.0936	0.135*
H13B	−0.1712	0.4582	0.1967	0.135*
H13C	−0.3449	0.3932	0.2136	0.135*
C14	−0.1066 (3)	−0.0411 (3)	0.2632 (2)	0.0427 (6)
C15A	0.1305 (14)	0.0007 (14)	0.2144 (19)	0.054 (3)	0.44 (3)
H15A	0.1762	0.0315	0.2970	0.065*	0.44 (3)
H15B	0.1047	−0.1100	0.1665	0.065*	0.44 (3)
C16A	0.236 (2)	0.114 (2)	0.166 (3)	0.098 (6)	0.44 (3)
H16A	0.3345	0.1124	0.1679	0.147*	0.44 (3)
H16B	0.2551	0.2214	0.2136	0.147*	0.44 (3)
H16C	0.1853	0.0811	0.0849	0.147*	0.44 (3)
C15B	0.1098 (13)	−0.0059 (12)	0.1538 (18)	0.067 (3)	0.56 (3)
H15C	0.1019	−0.0147	0.0725	0.081*	0.56 (3)
H15D	0.0958	−0.1073	0.1528	0.081*	0.56 (3)
C16B	0.2680 (12)	0.1277 (14)	0.2299 (15)	0.074 (3)	0.56 (3)
H16D	0.3492	0.1086	0.1970	0.112*	0.56 (3)
H16E	0.2771	0.1326	0.3094	0.112*	0.56 (3)
H16F	0.2800	0.2281	0.2325	0.112*	0.56 (3)
C17	0.0285 (3)	0.2981 (3)	0.4312 (2)	0.0372 (6)
C18	0.1550 (3)	0.3283 (4)	0.5096 (3)	0.0515 (7)
H18A	0.1472	0.2719	0.5566	0.062*
C19	0.2994 (4)	0.4552 (4)	0.5111 (3)	0.0677 (9)
H19A	0.3964	0.4906	0.5594	0.081*
C20	0.2827 (4)	0.5190 (4)	0.4363 (3)	0.0632 (9)
H20B	0.3656	0.6032	0.4269	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0530 (5)	0.0419 (4)	0.0652 (6)	0.0149 (4)	0.0177 (4)	0.0308 (4)
F1	0.0750 (15)	0.0696 (13)	0.0794 (16)	−0.0152 (11)	−0.0156 (11)	0.0075 (11)
O1	0.0632 (14)	0.0548 (12)	0.0485 (13)	0.0072 (10)	0.0128 (10)	0.0318 (10)
O2	0.0661 (13)	0.0474 (11)	0.0400 (11)	0.0287 (10)	0.0007 (9)	0.0220 (9)
O3	0.0940 (17)	0.0498 (12)	0.0332 (12)	0.0239 (12)	−0.0073 (11)	0.0131 (10)
O4	0.0700 (15)	0.0665 (14)	0.0853 (18)	0.0407 (13)	0.0032 (12)	0.0374 (13)
O5	0.0516 (13)	0.0469 (12)	0.0833 (17)	0.0234 (10)	0.0317 (11)	0.0202 (11)
N1	0.0390 (12)	0.0329 (11)	0.0310 (12)	0.0063 (9)	0.0032 (9)	0.0149 (9)
C1	0.0515 (18)	0.0394 (16)	0.060 (2)	0.0155 (14)	0.0101 (14)	0.0180 (14)
C2	0.073 (2)	0.0368 (16)	0.056 (2)	0.0106 (16)	0.0109 (16)	0.0094 (14)
C3	0.054 (2)	0.0513 (19)	0.0424 (18)	−0.0051 (16)	0.0002 (14)	0.0136 (15)
C4	0.0419 (18)	0.065 (2)	0.064 (2)	0.0104 (16)	0.0066 (15)	0.0246 (18)
C5	0.0432 (17)	0.0485 (16)	0.0543 (19)	0.0143 (14)	0.0097 (13)	0.0220 (14)
C6	0.0395 (15)	0.0342 (13)	0.0356 (14)	0.0087 (11)	0.0056 (11)	0.0172 (11)
C7	0.0443 (15)	0.0389 (14)	0.0407 (16)	0.0100 (12)	0.0062 (12)	0.0214 (12)
C8	0.0483 (16)	0.0467 (15)	0.0309 (15)	0.0094 (13)	0.0014 (12)	0.0187 (12)
C9	0.0370 (14)	0.0343 (13)	0.0322 (14)	0.0128 (11)	0.0054 (10)	0.0161 (11)
C10	0.0333 (13)	0.0312 (12)	0.0302 (13)	0.0103 (10)	0.0024 (10)	0.0143 (10)
C11	0.0384 (14)	0.0383 (14)	0.0349 (15)	0.0131 (12)	0.0050 (11)	0.0176 (12)
C12	0.090 (3)	0.071 (2)	0.0464 (19)	0.045 (2)	0.0019 (17)	0.0341 (17)
C13	0.148 (4)	0.089 (3)	0.074 (3)	0.076 (3)	0.027 (2)	0.050 (2)
C14	0.0399 (15)	0.0361 (14)	0.0423 (16)	0.0143 (12)	−0.0012 (11)	0.0125 (12)
C15A	0.049 (5)	0.053 (5)	0.059 (8)	0.029 (4)	0.020 (6)	0.016 (6)
C16A	0.069 (11)	0.115 (10)	0.128 (15)	0.045 (9)	0.059 (11)	0.064 (12)
C15B	0.054 (5)	0.068 (4)	0.073 (8)	0.034 (4)	0.025 (6)	0.015 (5)
C16B	0.050 (5)	0.075 (5)	0.093 (8)	0.031 (4)	0.011 (5)	0.029 (6)
C17	0.0404 (14)	0.0312 (12)	0.0326 (14)	0.0129 (11)	0.0065 (11)	0.0114 (11)
C18	0.0414 (16)	0.0612 (18)	0.0419 (17)	0.0170 (14)	0.0056 (12)	0.0216 (14)
C19	0.0378 (17)	0.084 (2)	0.050 (2)	0.0118 (16)	0.0034 (13)	0.0179 (17)
C20	0.0488 (19)	0.0494 (17)	0.061 (2)	0.0047 (14)	0.0198 (15)	0.0151 (15)

Geometric parameters (Å, º)

S1—C20	1.704 (3)	C9—C10	1.573 (3)
S1—C17	1.724 (2)	C9—H9A	0.9800
F1—C3	1.361 (3)	C10—C11	1.531 (3)
O1—C7	1.213 (3)	C10—C14	1.532 (4)
O2—C11	1.315 (3)	C12—C13	1.453 (5)
O2—C12	1.465 (3)	C12—H12A	0.9700
O3—C11	1.194 (3)	C12—H12B	0.9700
O4—C14	1.201 (3)	C13—H13A	0.9600
O5—C14	1.318 (3)	C13—H13B	0.9600
O5—C15B	1.471 (10)	C13—H13C	0.9600
O5—C15A	1.540 (12)	C15A—C16A	1.49 (3)
N1—C7	1.372 (3)	C15A—H15A	0.9700
N1—C6	1.442 (3)	C15A—H15B	0.9700
N1—C10	1.471 (3)	C16A—H16A	0.9600
C1—C6	1.370 (4)	C16A—H16B	0.9600
C1—C2	1.390 (4)	C16A—H16C	0.9600
C1—H1A	0.9300	C15B—C16B	1.49 (2)
C2—C3	1.354 (5)	C15B—H15C	0.9700
C2—H2A	0.9300	C15B—H15D	0.9700
C3—C4	1.366 (5)	C16B—H16D	0.9600
C4—C5	1.379 (4)	C16B—H16E	0.9600
C4—H4A	0.9300	C16B—H16F	0.9600
C5—C6	1.379 (4)	C17—C18	1.369 (4)
C5—H5A	0.9300	C18—C19	1.419 (4)
C7—C8	1.503 (4)	C18—H18A	0.9300
C8—C9	1.533 (3)	C19—C20	1.337 (5)
C8—H8A	0.9700	C19—H19A	0.9300
C8—H8B	0.9700	C20—H20B	0.9300
C9—C17	1.497 (3)
C20—S1—C17	92.45 (14)	C13—C12—H12A	110.1
C11—O2—C12	117.1 (2)	O2—C12—H12A	110.1
C14—O5—C15B	127.4 (7)	C13—C12—H12B	110.1
C14—O5—C15A	106.2 (7)	O2—C12—H12B	110.1
C7—N1—C6	121.00 (19)	H12A—C12—H12B	108.4
C7—N1—C10	113.42 (19)	C12—C13—H13A	109.5
C6—N1—C10	125.37 (19)	C12—C13—H13B	109.5
C6—C1—C2	119.7 (3)	H13A—C13—H13B	109.5
C6—C1—H1A	120.1	C12—C13—H13C	109.5
C2—C1—H1A	120.1	H13A—C13—H13C	109.5
C3—C2—C1	118.5 (3)	H13B—C13—H13C	109.5
C3—C2—H2A	120.7	O4—C14—O5	125.6 (3)
C1—C2—H2A	120.7	O4—C14—C10	123.8 (3)
C2—C3—F1	118.8 (3)	O5—C14—C10	110.4 (2)
C2—C3—C4	122.8 (3)	C16A—C15A—O5	98.9 (15)
F1—C3—C4	118.4 (3)	C16A—C15A—H15A	112.0
C3—C4—C5	118.7 (3)	O5—C15A—H15A	112.0
C3—C4—H4A	120.7	C16A—C15A—H15B	112.0
C5—C4—H4A	120.7	O5—C15A—H15B	112.0
C6—C5—C4	119.7 (3)	H15A—C15A—H15B	109.7
C6—C5—H5A	120.2	C15A—C16A—H16A	109.5
C4—C5—H5A	120.2	C15A—C16A—H16B	109.5
C1—C6—C5	120.6 (3)	H16A—C16A—H16B	109.5
C1—C6—N1	121.7 (2)	C15A—C16A—H16C	109.5
C5—C6—N1	117.6 (2)	H16A—C16A—H16C	109.5
O1—C7—N1	124.4 (2)	H16B—C16A—H16C	109.5
O1—C7—C8	127.5 (3)	O5—C15B—C16B	109.2 (11)
N1—C7—C8	108.0 (2)	O5—C15B—H15C	109.8
C7—C8—C9	104.5 (2)	C16B—C15B—H15C	109.8
C7—C8—H8A	110.8	O5—C15B—H15D	109.8
C9—C8—H8A	110.8	C16B—C15B—H15D	109.8
C7—C8—H8B	110.8	H15C—C15B—H15D	108.3
C9—C8—H8B	110.8	C15B—C16B—H16D	109.5
H8A—C8—H8B	108.9	C15B—C16B—H16E	109.5
C17—C9—C8	113.9 (2)	H16D—C16B—H16E	109.5
C17—C9—C10	117.5 (2)	C15B—C16B—H16F	109.5
C8—C9—C10	102.68 (18)	H16D—C16B—H16F	109.5
C17—C9—H9A	107.4	H16E—C16B—H16F	109.5
C8—C9—H9A	107.4	C18—C17—C9	128.1 (2)
C10—C9—H9A	107.4	C18—C17—S1	110.2 (2)
N1—C10—C11	110.58 (19)	C9—C17—S1	121.57 (18)
N1—C10—C14	111.24 (19)	C17—C18—C19	112.4 (3)
C11—C10—C14	108.8 (2)	C17—C18—H18A	123.8
N1—C10—C9	101.06 (18)	C19—C18—H18A	123.8
C11—C10—C9	115.42 (19)	C20—C19—C18	113.6 (3)
C14—C10—C9	109.59 (19)	C20—C19—H19A	123.2
O3—C11—O2	124.9 (2)	C18—C19—H19A	123.2
O3—C11—C10	122.6 (2)	C19—C20—S1	111.4 (2)
O2—C11—C10	112.5 (2)	C19—C20—H20B	124.3
C13—C12—O2	108.0 (3)	S1—C20—H20B	124.3
C6—C1—C2—C3	−1.4 (5)	C12—O2—C11—O3	−4.7 (4)
C1—C2—C3—F1	−179.7 (3)	C12—O2—C11—C10	175.9 (2)
C1—C2—C3—C4	1.4 (5)	N1—C10—C11—O3	−67.4 (3)
C2—C3—C4—C5	−0.6 (5)	C14—C10—C11—O3	55.0 (3)
F1—C3—C4—C5	−179.6 (3)	C9—C10—C11—O3	178.6 (3)
C3—C4—C5—C6	−0.1 (5)	N1—C10—C11—O2	111.9 (2)
C2—C1—C6—C5	0.8 (4)	C14—C10—C11—O2	−125.6 (2)
C2—C1—C6—N1	177.7 (3)	C9—C10—C11—O2	−2.0 (3)
C4—C5—C6—C1	0.0 (4)	C11—O2—C12—C13	176.2 (3)
C4—C5—C6—N1	−177.0 (2)	C15B—O5—C14—O4	6.1 (9)
C7—N1—C6—C1	−98.2 (3)	C15A—O5—C14—O4	−14.8 (7)
C10—N1—C6—C1	76.1 (3)	C15B—O5—C14—C10	−178.0 (8)
C7—N1—C6—C5	78.8 (3)	C15A—O5—C14—C10	161.1 (7)
C10—N1—C6—C5	−106.9 (3)	N1—C10—C14—O4	−21.4 (3)
C6—N1—C7—O1	1.2 (4)	C11—C10—C14—O4	−143.4 (3)
C10—N1—C7—O1	−173.8 (2)	C9—C10—C14—O4	89.5 (3)
C6—N1—C7—C8	−179.8 (2)	N1—C10—C14—O5	162.6 (2)
C10—N1—C7—C8	5.2 (3)	C11—C10—C14—O5	40.6 (3)
O1—C7—C8—C9	−165.2 (3)	C9—C10—C14—O5	−86.5 (2)
N1—C7—C8—C9	15.9 (3)	C14—O5—C15A—C16A	−167.8 (16)
C7—C8—C9—C17	−156.9 (2)	C15B—O5—C15A—C16A	49.2 (19)
C7—C8—C9—C10	−28.8 (3)	C14—O5—C15B—C16B	−104.2 (13)
C7—N1—C10—C11	−145.9 (2)	C15A—O5—C15B—C16B	−57.5 (19)
C6—N1—C10—C11	39.4 (3)	C8—C9—C17—C18	12.7 (4)
C7—N1—C10—C14	93.1 (2)	C10—C9—C17—C18	−107.4 (3)
C6—N1—C10—C14	−81.6 (3)	C8—C9—C17—S1	−161.93 (19)
C7—N1—C10—C9	−23.1 (2)	C10—C9—C17—S1	78.0 (2)
C6—N1—C10—C9	162.1 (2)	C20—S1—C17—C18	−0.2 (2)
C17—C9—C10—N1	156.56 (19)	C20—S1—C17—C9	175.3 (2)
C8—C9—C10—N1	30.8 (2)	C9—C17—C18—C19	−175.0 (3)
C17—C9—C10—C11	−84.1 (3)	S1—C17—C18—C19	0.2 (3)
C8—C9—C10—C11	150.1 (2)	C17—C18—C19—C20	0.0 (4)
C17—C9—C10—C14	39.1 (3)	C18—C19—C20—S1	−0.2 (4)
C8—C9—C10—C14	−86.7 (2)	C17—S1—C20—C19	0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O4^i	0.97	2.54	3.415 (4)	150
C9—H9A···O2	0.98	2.36	2.718 (3)	100
C12—H12B···O3^ii	0.97	2.59	3.443 (5)	147
C18—H18A···O4^i	0.93	2.57	3.496 (5)	171
C20—H20B···O1^iii	0.93	2.47	3.327 (4)	154

Symmetry codes: (i) −x, −y, −z+1; (ii) −x−1, −y, −z; (iii) x+1, y+1, z.