N-(Tri­phenyl­methyl­sulfanyl)­phthal­imide

The title compound, C₂₇H₁₉NO₂S, contains chains of fused (19) rings formed by intermolecular C—H...O=C hydrogen bonds and running along the [011] and [01] directions. These chains are linked through short intermol­ecular C—H...π contacts, giving rise to sheets. The conformation of the title compound is dominated primarily by the nearly orthogonal lone-pair orbitals on the N and S atoms.

S1. Comment

This paper forms part of our continuing study of the synthesis and structural characterization of sulfur divalent compounds. We are particularly interested in the utility of the title compound, (I) (Fig. 1 and Table 1), as a convenient reagent for sulfenamide synthesis (Harpp et al., 1971). A search of the Cambridge Structural Database (CSD; Version 5.25; Allen, 2002) for the thiophthalimide fragment with an S-alkyl or S-aryl substituent yielded only two examples, N-(2-nitrophenylthio)phthalimide (CSD refcode DETGOY; Iwasaki et al., 1986) and N-(trichloromethylthio)phthalimide (GUHDUI; Carle et al., 2000).

The thiophthalimide fragment in (I) is almost planar, with a dihedral angle of 2.1 (2)° between the N1/C20/C21/C26/C27 and C21–C26 planes. This value is similar ?to that of 1.4 ° in?? N-(2-nitrophenylthio)phthalimide (Iwasaki et al., 1986). The six-membered ring of the phthalimide group is planar, with deviations within 0.020 (2) Å. The five-membered ring is distorted, with significant out-of-plane deviations for atoms C20 [0.014 (1) Å] and C21 [0.015 (2) Å]. The S—N distance is shorter than the normal S—N single bond length (1.74 Å) but is usual for this type of structure, many of which have S—N single bonds in the range 1.63–1.68 Å as a result of the contribution of π character to the S—N bond. The C13—Cn bonds [n = 1, 7 and 14; mean 1.537 (4) Å] are all well above the upper quartile value of 1.521 Å for C for Csp³—C_aryl bonds (Allen et al., 1987). The mean of the 18 phenyl C—C distances is 1.381 (5) Å. The C—S distance is comparable with the value of 1.894 (2) Å found in N,N-dibenzyltriphenylmethanesulfenamide (Brito et al., 2004). The dihedral angles between phenyl rings C1–C6 and C7–C12, C1–C6 and C14–C19, and C7–C12 and C14–C19 are 81.9 (1), 57.5 (1) and 78.0 (1)°.

The crystal structure of (I) is built from weak intermolecular C—H···O=C and C—H···π interactions (Table 2). The molecules act as double donors in C—H···O hydrogen bonds, linking molecules related by the n-glide planes (Fig. 2 A and Table 2), so generating chains of fused R²₂(19) rings (Bernstein et al., 1995) along the [011] direction. Chains related by translation along [010] are linked through a C—H··· π interaction, where the C4/H4 group at (x, y, z) acts as a donor to the centroid (Cg in Fig. 2a and Table 2) of the C7–C12 aryl ring at (x, 1 + y, z), giving rise to sheets. An equivalent sheet, related to the previous one by the twofold screw axes along c, is generated in a similar way by means of chains running along the [0–11] direction (Fig. 2 b). The crystal is built up of these types of sheets, connected only by van der Waals interactions (Fig. 3).

S2. Experimental

A heptane solution of trichloromethanesulfenyl chloride was added dropwise to a stirred dimethylformamide solution of phthalimide and triethylamine, producing (I) (Wunderly, 1972). Crystals suitable for X-ray analysis were grown by slow evaporation from dichloromethane–diethyl ether (1:1) at room temperature. IR (KBr, cm⁻¹): 2360 (m), 1774(m), 1718 (versus), 1440–1491 (w), 1340 (w), 1276 (versus), 1169 (m), 1089 (w), 1039 (m), 865 (m), 715–789 (m), 669 (m), 626 (w), 525–578 (w), 488 (w); UV/vis (CH₂Cl₂, nm): λ 285 (sh), 292, 302; MS(EI): m/z: 244, 243, 242, 241, 240, 239, 228, 166, 165, 147, 77, 76; m.p. 469 K.

S3. Refinement

H atoms were positioned geometrically (C—H = 0.93 Å), riding on their carrier atoms, with U_iso(H) set to 1.2 times U_eq of the parent atom. The orientation of the structure with respect to the polar axis (Jones, 1986) was determined on the basis of 2010 Friedel pairs. The number of unique reflections in the merged set is 2457.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H-atom radii are arbitrary.
	Fig. 2. (a) A view of the packing of (I) along the a axis, showing the C—H···π interactions between the [011] chains. [Symmetry codes: (i) 3/2 − x,1/2 + y,1/2 + z; (ii) 3/2 − x,-1/2 + y, −1/2 + z; (iii) x,1 + y,z.] (b) A view of the packing of (I) along the a axis, showing the [0–11] chains. [Symmetry codes: (iv) 1 − x, −y,1/2 + z; (v) −1/2 + x, 1/2 − y,z; (vi) 1 − x, 1 − y,-1/2 + z.]
	Fig. 3. A view of the packing of (I) along the b axis, showing the [011] and [0–11] chains. [Symmetry codes: (i) 3/2 − x,1/2 + y,1/2 + z; (ii) 3/2 − x,-1/2 + y,-1/2 + z.]

N-(Triphenylmethylsulfanyl)phthalimide

Crystal data

C27H19NO2S	Dx = 1.345 Mg m^−3
Mr = 421.49	Melting point: 469 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2257 reflections
a = 14.790 (15) Å	θ = 2.6–27.5°
b = 9.373 (8) Å	µ = 0.18 mm^−1
c = 15.01 (3) Å	T = 298 K
V = 2081 (5) Å^3	Prism, colourless
Z = 4	0.40 × 0.25 × 0.19 mm
F(000) = 880

Data collection

Nonius KappaCCD area-detector diffractometer	4484 independent reflections
Radiation source: fine-focus sealed tube	3966 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −19→18
Tmin = 0.943, Tmax = 0.960	k = −12→11
17690 measured reflections	l = −18→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 0.1932P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max = 0.004
S = 1.19	Δρmax = 0.24 e Å^−3
4484 reflections	Δρmin = −0.32 e Å^−3
280 parameters	Absolute structure: Flack (1983)
1 restraint	Absolute structure parameter: 0.01 (7)
Primary atom site location: structure-invariant direct methods

Special details

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.

Mean plane data SHELXL97 for (I) #################################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

13.1928 (0.0251) x − 2.0213 (0.0111) y + 5.9638 (0.0194) z = 9.3695 (0.0173) * 0.0079 (0.0013) N1 * −0.0138 (0.0013) C20 * 0.0150 (0.0015) C21 * −0.0105 (0.0015) C26 * 0.0013 (0.0013) C27 Rms deviation of fitted atoms = 0.0109 13.2637 (0.0253) x − 1.6938 (0.0117) y + 6.0625 (0.0198) z = 9.4228 (0.0174) A ngle to previous plane (with approximate e.s.d.) = 2.06 (0.17) * −0.0035 (0.0018) C21 * −0.0028 (0.0022) C22 * 0.0046 (0.0023) C23 * −0.0002 (0.0022) C24 * −0.0060 (0.0019) C25 * 0.0078 (0.0018) C26 Rms deviation of fitted atoms = 0.0048 13.2450 (0.0249) x − 2.0225 (0.0089) y + 5.8423 (0.0149) z = 9.3535 (0.0171) A ngle to previous plane (with approximate e.s.d.) = 2.18 (0.16) * 0.0016 (0.0019) C20 * 0.0192 (0.0016) C21 * −0.0156 (0.0016) C26 * 0.0011 (0.0019) C27 * 0.0201 (0.0015) N1 * −0.0079 (0.0014) O1 * −0.0186 (0.0014) O2 0.0975 (0.0028) S1 Rms deviation of fitted atoms = 0.0143 4.6341 (0.0168) x + 7.7052 (0.0150) y − 7.1371 (0.0193) z = 3.5106 (0.0151) A ngle to previous plane (with approximate e.s.d.) = 85.31 (0.13) * −0.0020 (0.0016) C7 * −0.0082 (0.0016) C8 * 0.0123 (0.0017) C9

* −0.0062 (0.0018) C10 * −0.0041 (0.0020) C11 * 0.0082 (0.0018) C12 Rms deviation of fitted atoms = 0.0076 10.3354 (0.0225) x − 0.2295 (0.0101) y + 10.7319 (0.0231) z = 10.7496 (0.0216) A ngle to previous plane (with approximate e.s.d.) = 81.89 (0.13) * 0.0069 (0.0017) C1 * −0.0082 (0.0019) C2 * 0.0034 (0.0021) C3 * 0.0027 (0.0021) C4 * −0.0039 (0.0019) C5 * −0.0009 (0.0017) C6 Rms deviation of fitted atoms = 0.0050 14.1449 (0.0261) x − 2.0756 (0.0101) y − 2.8602 (0.0157) z = 9.7535 (0.0201) A ngle to previous plane (with approximate e.s.d.) = 57.48 (0.13)

* −0.0161 (0.0015) C14 * 0.0138 (0.0015) C15 * 0.0001 (0.0017) C16 * −0.0120 (0.0018) C17 * 0.0095 (0.0019) C18

* 0.0047 (0.0018) C19 Rms deviation of fitted atoms = 0.0108 4.6341 (0.0168) x + 7.7052 (0.0150) y − 7.1371 (0.0193) z = 3.5106 (0.0151) A ngle to previous plane (with approximate e.s.d.) = 77.98 (0.13) * −0.0020 (0.0016) C7 * −0.0082 (0.0016) C8 * 0.0123 (0.0017) C9 * −0.0062 (0.0018) C10 * −0.0041 (0.0020) C11 * 0.0082 (0.0018) C12 Rms deviation of fitted atoms = 0.0076

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

	x	y	z	Uiso*/Ueq
S1	0.64887 (3)	0.23718 (6)	0.22875 (5)	0.04120 (17)
N1	0.59754 (11)	0.10601 (18)	0.28646 (14)	0.0355 (4)
O1	0.55996 (15)	0.2368 (2)	0.41214 (16)	0.0678 (6)
O2	0.61016 (13)	−0.0809 (2)	0.18653 (13)	0.0598 (5)
C1	0.79519 (14)	0.3912 (2)	0.24485 (16)	0.0333 (5)
C2	0.74670 (18)	0.4938 (2)	0.29233 (19)	0.0457 (6)
H2	0.7025	0.4649	0.3326	0.055*
C3	0.76334 (19)	0.6381 (2)	0.2805 (2)	0.0539 (7)
H3	0.7312	0.705	0.3136	0.065*
C4	0.82632 (18)	0.6824 (2)	0.2207 (2)	0.0529 (6)
H4	0.8371	0.7793	0.2127	0.063*
C5	0.87380 (18)	0.5842 (3)	0.1723 (2)	0.0487 (6)
H5	0.9166	0.6149	0.1311	0.058*
C6	0.85895 (15)	0.4392 (2)	0.18374 (16)	0.0377 (5)
H6	0.8918	0.3736	0.1504	0.045*
C7	0.82789 (14)	0.1370 (2)	0.19384 (14)	0.0312 (5)
C8	0.91675 (14)	0.1036 (2)	0.21639 (17)	0.0378 (5)
H8	0.9403	0.1367	0.27	0.045*
C9	0.97075 (17)	0.0223 (2)	0.16081 (19)	0.0449 (6)
H9	1.0305	0.0042	0.1763	0.054*
C10	0.9367 (2)	−0.0312 (3)	0.08350 (19)	0.0525 (7)
H10	0.9724	−0.0883	0.047	0.063*
C11	0.85002 (19)	−0.0006 (3)	0.0600 (2)	0.0592 (8)
H11	0.8267	−0.0365	0.007	0.071*
C12	0.79599 (17)	0.0838 (3)	0.11432 (18)	0.0482 (6)
H12	0.7372	0.1048	0.0967	0.058*
C13	0.77347 (14)	0.2315 (2)	0.25777 (15)	0.0305 (5)
C14	0.78589 (13)	0.1774 (2)	0.35333 (15)	0.0305 (5)
C15	0.77030 (14)	0.0331 (2)	0.37048 (17)	0.0365 (5)
H15	0.7541	−0.0272	0.3239	0.044*
C16	0.77854 (17)	−0.0213 (3)	0.45552 (19)	0.0470 (6)
H16	0.7665	−0.1172	0.4661	0.056*
C17	0.80438 (17)	0.0655 (3)	0.52455 (18)	0.0514 (7)
H17	0.809	0.029	0.582	0.062*
C18	0.8233 (2)	0.2063 (3)	0.50842 (19)	0.0537 (7)
H18	0.8425	0.2647	0.5548	0.064*
C19	0.81399 (18)	0.2619 (2)	0.42373 (19)	0.0434 (6)
H19	0.8268	0.3577	0.4138	0.052*
C20	0.58719 (15)	−0.0364 (2)	0.25749 (16)	0.0379 (5)
C21	0.54394 (15)	−0.1118 (3)	0.33244 (17)	0.0408 (6)
C22	0.5220 (2)	−0.2549 (3)	0.3407 (3)	0.0609 (8)
H22	0.5342	−0.3192	0.2951	0.073*
C23	0.4816 (2)	−0.2984 (4)	0.4180 (3)	0.0737 (10)
H23	0.4666	−0.3941	0.4254	0.088*
C24	0.4630 (2)	−0.2037 (5)	0.4844 (3)	0.0746 (10)
H24	0.4352	−0.2367	0.536	0.09*
C25	0.48408 (19)	−0.0592 (4)	0.4777 (2)	0.0628 (8)
H25	0.4705	0.0047	0.5231	0.075*
C26	0.52625 (16)	−0.0158 (3)	0.39983 (17)	0.0426 (6)
C27	0.56107 (15)	0.1263 (3)	0.37293 (17)	0.0414 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0316 (3)	0.0426 (3)	0.0494 (4)	−0.0002 (2)	−0.0061 (3)	0.0107 (3)
N1	0.0312 (10)	0.0399 (10)	0.0354 (11)	−0.0056 (7)	0.0002 (8)	−0.0049 (8)
O1	0.0658 (14)	0.0668 (13)	0.0708 (16)	−0.0025 (9)	0.0135 (12)	−0.0369 (11)
O2	0.0674 (13)	0.0632 (12)	0.0488 (12)	−0.0187 (9)	0.0160 (10)	−0.0229 (9)
C1	0.0348 (10)	0.0273 (10)	0.0377 (13)	−0.0018 (7)	−0.0022 (10)	−0.0016 (8)
C2	0.0513 (14)	0.0350 (12)	0.0508 (16)	−0.0007 (10)	0.0099 (13)	0.0026 (11)
C3	0.0615 (17)	0.0316 (12)	0.0687 (19)	0.0041 (11)	0.0070 (15)	−0.0048 (12)
C4	0.0578 (15)	0.0331 (12)	0.0678 (18)	−0.0083 (10)	−0.0039 (15)	0.0048 (13)
C5	0.0440 (13)	0.0444 (14)	0.0575 (17)	−0.0114 (11)	0.0026 (13)	0.0071 (12)
C6	0.0384 (12)	0.0358 (12)	0.0389 (13)	−0.0019 (8)	0.0008 (10)	0.0029 (9)
C7	0.0360 (11)	0.0282 (10)	0.0293 (12)	−0.0054 (8)	0.0033 (9)	−0.0005 (8)
C8	0.0404 (12)	0.0362 (12)	0.0366 (14)	−0.0011 (8)	0.0005 (11)	−0.0045 (10)
C9	0.0419 (13)	0.0360 (12)	0.0567 (17)	0.0013 (9)	0.0120 (12)	−0.0006 (11)
C10	0.0598 (18)	0.0435 (14)	0.0543 (17)	−0.0130 (12)	0.0253 (14)	−0.0137 (12)
C11	0.064 (2)	0.0714 (19)	0.0422 (16)	−0.0202 (14)	0.0103 (14)	−0.0285 (14)
C12	0.0456 (15)	0.0621 (16)	0.0371 (14)	−0.0125 (11)	−0.0010 (12)	−0.0098 (11)
C13	0.0273 (10)	0.0335 (11)	0.0308 (12)	−0.0020 (8)	−0.0007 (9)	0.0012 (8)
C14	0.0266 (10)	0.0337 (12)	0.0312 (12)	0.0029 (8)	0.0000 (9)	−0.0019 (9)
C15	0.0342 (11)	0.0336 (12)	0.0416 (14)	0.0022 (9)	−0.0023 (10)	0.0001 (9)
C16	0.0412 (13)	0.0475 (14)	0.0522 (17)	0.0073 (10)	0.0033 (12)	0.0164 (12)
C17	0.0481 (15)	0.0750 (19)	0.0311 (14)	0.0110 (12)	0.0032 (12)	0.0102 (12)
C18	0.0564 (16)	0.0677 (18)	0.0369 (15)	0.0054 (13)	−0.0034 (13)	−0.0108 (13)
C19	0.0452 (14)	0.0434 (14)	0.0417 (15)	0.0004 (10)	−0.0022 (12)	−0.0054 (10)
C20	0.0316 (11)	0.0437 (13)	0.0382 (14)	−0.0074 (9)	−0.0003 (10)	−0.0089 (10)
C21	0.0321 (12)	0.0493 (15)	0.0409 (14)	−0.0121 (9)	−0.0014 (10)	0.0002 (11)
C22	0.0527 (17)	0.0553 (18)	0.075 (2)	−0.0147 (12)	−0.0021 (16)	0.0037 (15)
C23	0.063 (2)	0.077 (2)	0.081 (3)	−0.0234 (16)	−0.0068 (18)	0.033 (2)
C24	0.0531 (18)	0.111 (3)	0.059 (2)	−0.0179 (18)	0.0017 (16)	0.042 (2)
C25	0.0484 (16)	0.104 (2)	0.0364 (17)	−0.0029 (15)	−0.0020 (13)	0.0053 (16)
C26	0.0308 (12)	0.0651 (17)	0.0319 (14)	−0.0037 (11)	−0.0022 (10)	0.0038 (11)
C27	0.0304 (12)	0.0566 (15)	0.0372 (14)	0.0007 (10)	−0.0001 (11)	−0.0117 (11)

Geometric parameters (Å, º)

S1—N1	1.685 (2)	C11—C12	1.390 (4)
S1—C13	1.894 (3)	C11—H11	0.93
N1—C20	1.412 (3)	C12—H12	0.93
N1—C27	1.419 (4)	C13—C14	1.533 (4)
O1—C27	1.191 (3)	C14—C19	1.384 (4)
O2—C20	1.193 (3)	C14—C15	1.396 (3)
C1—C6	1.390 (3)	C15—C16	1.380 (4)
C1—C2	1.395 (3)	C15—H15	0.93
C1—C13	1.543 (3)	C16—C17	1.372 (4)
C2—C3	1.386 (4)	C16—H16	0.93
C2—H2	0.93	C17—C18	1.370 (4)
C3—C4	1.358 (4)	C17—H17	0.93
C3—H3	0.93	C18—C19	1.381 (5)
C4—C5	1.367 (4)	C18—H18	0.93
C4—H4	0.93	C19—H19	0.93
C5—C6	1.388 (4)	C20—C21	1.475 (4)
C5—H5	0.93	C21—C26	1.379 (4)
C6—H6	0.93	C21—C22	1.386 (4)
C7—C12	1.377 (4)	C22—C23	1.368 (6)
C7—C8	1.393 (3)	C22—H22	0.93
C7—C13	1.534 (3)	C23—C24	1.362 (6)
C8—C9	1.384 (3)	C23—H23	0.93
C8—H8	0.93	C24—C25	1.394 (5)
C9—C10	1.361 (4)	C24—H24	0.93
C9—H9	0.93	C25—C26	1.386 (4)
C10—C11	1.361 (4)	C25—H25	0.93
C10—H10	0.93	C26—C27	1.484 (4)
N1—S1—C13	107.44 (10)	C7—C13—S1	112.49 (16)
C20—N1—C27	111.56 (19)	C1—C13—S1	98.42 (13)
C20—N1—S1	125.47 (18)	C19—C14—C15	117.6 (2)
C27—N1—S1	122.95 (17)	C19—C14—C13	124.2 (2)
C6—C1—C2	117.6 (2)	C15—C14—C13	118.25 (19)
C6—C1—C13	122.52 (19)	C16—C15—C14	120.9 (2)
C2—C1—C13	119.8 (2)	C16—C15—H15	119.5
C3—C2—C1	121.0 (2)	C14—C15—H15	119.5
C3—C2—H2	119.5	C17—C16—C15	120.3 (2)
C1—C2—H2	119.5	C17—C16—H16	119.9
C4—C3—C2	120.3 (2)	C15—C16—H16	119.8
C4—C3—H3	119.9	C18—C17—C16	119.6 (3)
C2—C3—H3	119.9	C18—C17—H17	120.2
C3—C4—C5	119.9 (2)	C16—C17—H17	120.2
C3—C4—H4	120.1	C17—C18—C19	120.4 (3)
C5—C4—H4	120.1	C17—C18—H18	119.8
C4—C5—C6	120.8 (2)	C19—C18—H18	119.8
C4—C5—H5	119.6	C18—C19—C14	121.1 (2)
C6—C5—H5	119.6	C18—C19—H19	119.4
C5—C6—C1	120.4 (2)	C14—C19—H19	119.4
C5—C6—H6	119.8	O2—C20—N1	125.1 (2)
C1—C6—H6	119.8	O2—C20—C21	129.6 (2)
C12—C7—C8	116.9 (2)	N1—C20—C21	105.4 (2)
C12—C7—C13	124.9 (2)	C26—C21—C22	121.5 (3)
C8—C7—C13	118.2 (2)	C26—C21—C20	109.2 (2)
C9—C8—C7	121.5 (2)	C22—C21—C20	129.3 (3)
C9—C8—H8	119.3	C23—C22—C21	117.8 (3)
C7—C8—H8	119.3	C23—C22—H22	121.1
C10—C9—C8	120.3 (3)	C21—C22—H22	121.1
C10—C9—H9	119.9	C24—C23—C22	121.0 (3)
C8—C9—H9	119.9	C24—C23—H23	119.5
C11—C10—C9	119.5 (2)	C22—C23—H23	119.5
C11—C10—H10	120.3	C23—C24—C25	122.3 (3)
C9—C10—H10	120.3	C23—C24—H24	118.8
C10—C11—C12	120.6 (3)	C25—C24—H24	118.8
C10—C11—H11	119.7	C26—C25—C24	116.6 (3)
C12—C11—H11	119.7	C26—C25—H25	121.7
C7—C12—C11	121.2 (3)	C24—C25—H25	121.7
C7—C12—H12	119.4	C21—C26—C25	120.8 (3)
C11—C12—H12	119.4	C21—C26—C27	108.7 (2)
C14—C13—C7	109.36 (18)	C25—C26—C27	130.5 (3)
C14—C13—C1	114.43 (18)	O1—C27—N1	125.0 (2)
C7—C13—C1	111.87 (18)	O1—C27—C26	129.9 (3)
C14—C13—S1	109.94 (14)	N1—C27—C26	105.1 (2)
C13—S1—N1—C20	−88.2 (2)	C1—C13—C14—C15	−178.14 (18)
C13—S1—N1—C27	90.02 (19)	S1—C13—C14—C15	72.2 (2)
C6—C1—C2—C3	−1.6 (4)	C19—C14—C15—C16	3.0 (3)
C13—C1—C2—C3	−178.5 (2)	C13—C14—C15—C16	−178.6 (2)
C1—C2—C3—C4	1.3 (4)	C14—C15—C16—C17	−1.5 (3)
C2—C3—C4—C5	−0.3 (5)	C15—C16—C17—C18	−1.0 (4)
C3—C4—C5—C6	−0.4 (4)	C16—C17—C18—C19	1.8 (4)
C4—C5—C6—C1	0.1 (4)	C17—C18—C19—C14	−0.3 (4)
C2—C1—C6—C5	0.9 (3)	C15—C14—C19—C18	−2.1 (3)
C13—C1—C6—C5	177.7 (2)	C13—C14—C19—C18	179.6 (2)
C12—C7—C8—C9	0.8 (3)	C27—N1—C20—O2	178.2 (2)
C13—C7—C8—C9	−178.1 (2)	S1—N1—C20—O2	−3.4 (3)
C7—C8—C9—C10	−2.2 (3)	C27—N1—C20—C21	−2.0 (2)
C8—C9—C10—C11	2.0 (4)	S1—N1—C20—C21	176.39 (15)
C9—C10—C11—C12	−0.4 (4)	O2—C20—C21—C26	−177.5 (3)
C8—C7—C12—C11	0.8 (3)	N1—C20—C21—C26	2.7 (3)
C13—C7—C12—C11	179.6 (2)	O2—C20—C21—C22	2.6 (4)
C10—C11—C12—C7	−1.0 (4)	N1—C20—C21—C22	−177.1 (3)
C12—C7—C13—C14	134.6 (2)	C26—C21—C22—C23	0.2 (4)
C8—C7—C13—C14	−46.6 (2)	C20—C21—C22—C23	−179.9 (3)
C12—C7—C13—C1	−97.6 (3)	C21—C22—C23—C24	0.6 (5)
C8—C7—C13—C1	81.3 (3)	C22—C23—C24—C25	−0.3 (5)
C12—C7—C13—S1	12.1 (3)	C23—C24—C25—C26	−0.7 (4)
C8—C7—C13—S1	−169.03 (16)	C22—C21—C26—C25	−1.3 (4)
C6—C1—C13—C14	123.3 (2)	C20—C21—C26—C25	178.9 (2)
C2—C1—C13—C14	−60.1 (3)	C22—C21—C26—C27	177.5 (2)
C6—C1—C13—C7	−1.8 (3)	C20—C21—C26—C27	−2.4 (3)
C2—C1—C13—C7	174.9 (2)	C24—C25—C26—C21	1.4 (4)
C6—C1—C13—S1	−120.3 (2)	C24—C25—C26—C27	−177.0 (3)
C2—C1—C13—S1	56.4 (3)	C20—N1—C27—O1	−178.9 (2)
N1—S1—C13—C14	−30.72 (16)	S1—N1—C27—O1	2.6 (3)
N1—S1—C13—C7	91.42 (19)	C20—N1—C27—C26	0.6 (2)
N1—S1—C13—C1	−150.62 (14)	S1—N1—C27—C26	−177.82 (15)
C7—C13—C14—C19	126.5 (2)	C21—C26—C27—O1	−179.4 (3)
C1—C13—C14—C19	0.1 (3)	C25—C26—C27—O1	−0.8 (5)
S1—C13—C14—C19	−109.5 (2)	C21—C26—C27—N1	1.1 (2)
C7—C13—C14—C15	−51.7 (2)	C25—C26—C27—N1	179.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2^i	0.93	2.55	3.478 (5)	177
C10—H10···O1^ii	0.93	2.65	3.369 (5)	135
C4—H4···Cg^iii	0.93	2.87	3.778 (8)	164

Symmetry codes: (i) −x+3/2, y+1/2, z+1/2; (ii) −x+3/2, y−1/2, z−1/2; (iii) x, y+1, z.