Ethyl 4-hydr-oxy-2,6-diphenyl-1-(2-thio-morpholinopropano-yl)-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title compound, C(27)H(32)N(2)O(4)S, the thio-morpholine ring adopts a chair conformation and the tetra-hydro-pyridine ring is in a distorted envelope conformation. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O inter-action and the crystal packing is stabilized by an inter-molecular C-H⋯O inter-action, generating an S(6) motif and a dimer of the type R(2) (2)(18), respectively.

Related literature

For the synthesis and biological activity of 2,6-diaryl­piperidin-4-one derivatives, see: Aridoss, Balasubramanian, Parthiban, Ramachandran & Kabilan (2007 ▶); Aridoss, Balasubramanian, Parthiban & Kabilan (2007 ▶); Aridoss, Parthiban et al. (2009 ▶). For a related structure, see: Aridoss, Gayathri et al. (2009 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C27H32N2O4S

M = 480.61

Triclinic,

a = 9.904 (3) Å

b = 11.400 (4) Å

c = 12.103 (4) Å

α = 93.908 (18)°

β = 104.941 (15)°

γ = 106.819 (16)°

V = 1248.7 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (; Bruker, 1999 ▶) T min = 0.952, T max = 0.968

26182 measured reflections

5707 independent reflections

4543 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.117

S = 1.01

5707 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049186/is2490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049186/is2490Isup2.hkl

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

C27H32N2O4S	Z = 2
Mr = 480.61	F(000) = 512
Triclinic, P1	Dx = 1.278 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.904 (3) Å	Cell parameters from 5338 reflections
b = 11.400 (4) Å	θ = 2.3–27.8°
c = 12.103 (4) Å	µ = 0.17 mm−1
α = 93.908 (18)°	T = 293 K
β = 104.941 (15)°	Block, colorless
γ = 106.819 (16)°	0.30 × 0.25 × 0.20 mm
V = 1248.7 (7) Å3

Bruker Kappa APEXII CCD diffractometer	5707 independent reflections
Radiation source: fine-focus sealed tube	4543 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scan	θmax = 27.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→12
Tmin = 0.952, Tmax = 0.968	k = −14→14
26182 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2715P] where P = (Fo2 + 2Fc2)/3
5707 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.36 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
C1	1.19148 (14)	0.27730 (12)	0.23357 (11)	0.0347 (3)
H1	1.2819	0.2883	0.2959	0.042*
C2	1.22176 (15)	0.24683 (13)	0.12043 (12)	0.0400 (3)
H2A	1.2817	0.3218	0.1013	0.048*
H2B	1.2769	0.1885	0.1293	0.048*
C3	1.08292 (15)	0.19255 (12)	0.02448 (11)	0.0371 (3)
C4	0.95026 (14)	0.14479 (11)	0.04268 (10)	0.0331 (3)
C5	0.93213 (13)	0.13505 (11)	0.16238 (10)	0.0310 (3)
H5	0.8828	0.0472	0.1626	0.037*
C6	1.10345 (14)	0.08311 (12)	0.31764 (10)	0.0337 (3)
C7	1.25989 (15)	0.11016 (13)	0.39709 (11)	0.0357 (3)
H7	1.3274	0.1358	0.3501	0.043*
C8	1.45086 (15)	0.27218 (15)	0.54032 (13)	0.0478 (4)
H8A	1.4994	0.2871	0.4801	0.057*
H8B	1.4889	0.2154	0.5853	0.057*
C9	1.4863 (2)	0.39292 (17)	0.61776 (16)	0.0611 (4)
H9A	1.4450	0.4485	0.5733	0.073*
H9B	1.5924	0.4315	0.6454	0.073*
C10	1.2279 (2)	0.29267 (17)	0.65584 (14)	0.0574 (4)
H10A	1.1697	0.2655	0.7082	0.069*
H10B	1.1886	0.3499	0.6126	0.069*
C11	1.21338 (17)	0.18191 (15)	0.57289 (12)	0.0457 (3)
H11A	1.2508	0.1239	0.6163	0.055*
H11B	1.1099	0.1405	0.5329	0.055*
C12	1.15095 (14)	0.39523 (12)	0.24545 (11)	0.0358 (3)
C13	1.12638 (16)	0.43177 (14)	0.34780 (13)	0.0448 (3)
H13	1.1291	0.3814	0.4051	0.054*
C14	1.0980 (2)	0.54136 (16)	0.36610 (16)	0.0577 (4)
H14	1.0809	0.5643	0.4352	0.069*
C15	1.0948 (2)	0.61727 (16)	0.28258 (18)	0.0640 (5)
H15	1.0773	0.6922	0.2955	0.077*
C16	1.1173 (2)	0.58217 (16)	0.18069 (17)	0.0608 (4)
H16	1.1135	0.6327	0.1235	0.073*
C17	1.14591 (18)	0.47184 (13)	0.16176 (13)	0.0471 (3)
H17	1.1618	0.4490	0.0921	0.057*
C18	0.83851 (13)	0.20571 (12)	0.19968 (11)	0.0332 (3)
C19	0.80193 (16)	0.18358 (14)	0.30119 (12)	0.0425 (3)
H19	0.8339	0.1262	0.3429	0.051*
C20	0.71920 (19)	0.24515 (16)	0.34109 (15)	0.0547 (4)
H20	0.6955	0.2294	0.4093	0.066*
C21	0.6719 (2)	0.32964 (16)	0.28039 (16)	0.0597 (4)
H21	0.6165	0.3720	0.3075	0.072*
C22	0.7062 (2)	0.35187 (16)	0.17939 (16)	0.0555 (4)
H22	0.6733	0.4090	0.1379	0.067*
C23	0.78906 (16)	0.29013 (13)	0.13889 (12)	0.0423 (3)
H23	0.8116	0.3057	0.0702	0.051*
C24	1.2782 (2)	−0.00907 (15)	0.43919 (14)	0.0524 (4)
H24A	1.3719	0.0096	0.4965	0.079*
H24B	1.2733	−0.0661	0.3751	0.079*
H24C	1.2008	−0.0457	0.4725	0.079*
C25	0.82265 (15)	0.08996 (12)	−0.05693 (11)	0.0369 (3)
C26	0.56361 (17)	−0.00482 (15)	−0.12584 (13)	0.0494 (4)
H26A	0.4891	−0.0668	−0.1038	0.059*
H26B	0.5820	−0.0430	−0.1922	0.059*
C27	0.5094 (2)	0.1005 (2)	−0.15733 (19)	0.0757 (6)
H27A	0.4967	0.1411	−0.0904	0.114*
H27B	0.4167	0.0701	−0.2167	0.114*
H27C	0.5797	0.1585	−0.1852	0.114*
N1	1.07728 (11)	0.16791 (10)	0.24818 (9)	0.0326 (2)
N2	1.29325 (11)	0.21563 (10)	0.48737 (9)	0.0336 (2)
O1	1.00568 (11)	−0.01107 (9)	0.31843 (9)	0.0454 (2)
O2	1.10662 (12)	0.19398 (11)	−0.07897 (9)	0.0520 (3)
H2	1.0283	0.1614	−0.1296	0.078*
O3	0.82742 (12)	0.08937 (11)	−0.15678 (8)	0.0539 (3)
O4	0.69839 (10)	0.03850 (9)	−0.03050 (8)	0.0406 (2)
S1	1.41530 (6)	0.37181 (4)	0.73873 (4)	0.06261 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0296 (6)	0.0326 (6)	0.0350 (6)	0.0045 (5)	0.0035 (5)	0.0060 (5)
C2	0.0337 (7)	0.0390 (7)	0.0460 (8)	0.0076 (5)	0.0137 (6)	0.0064 (6)
C3	0.0431 (7)	0.0354 (7)	0.0351 (7)	0.0139 (6)	0.0140 (6)	0.0047 (5)
C4	0.0358 (6)	0.0322 (6)	0.0299 (6)	0.0116 (5)	0.0070 (5)	0.0025 (5)
C5	0.0288 (6)	0.0298 (6)	0.0289 (6)	0.0052 (5)	0.0041 (5)	0.0032 (5)
C6	0.0370 (7)	0.0346 (7)	0.0286 (6)	0.0105 (5)	0.0090 (5)	0.0055 (5)
C7	0.0362 (7)	0.0409 (7)	0.0306 (6)	0.0146 (5)	0.0078 (5)	0.0069 (5)
C8	0.0320 (7)	0.0619 (10)	0.0434 (8)	0.0100 (7)	0.0079 (6)	0.0019 (7)
C9	0.0495 (9)	0.0547 (10)	0.0591 (10)	−0.0010 (8)	0.0049 (8)	−0.0027 (8)
C10	0.0655 (11)	0.0708 (11)	0.0464 (9)	0.0303 (9)	0.0250 (8)	0.0069 (8)
C11	0.0438 (8)	0.0530 (9)	0.0390 (7)	0.0094 (7)	0.0169 (6)	0.0063 (6)
C12	0.0307 (6)	0.0302 (6)	0.0368 (7)	0.0014 (5)	0.0032 (5)	0.0031 (5)
C13	0.0459 (8)	0.0404 (7)	0.0407 (7)	0.0057 (6)	0.0097 (6)	0.0036 (6)
C14	0.0615 (10)	0.0485 (9)	0.0599 (10)	0.0124 (8)	0.0215 (8)	−0.0046 (8)
C15	0.0691 (12)	0.0387 (9)	0.0863 (13)	0.0184 (8)	0.0259 (10)	0.0066 (8)
C16	0.0725 (11)	0.0420 (9)	0.0709 (11)	0.0196 (8)	0.0213 (9)	0.0216 (8)
C17	0.0546 (9)	0.0389 (8)	0.0446 (8)	0.0112 (7)	0.0125 (7)	0.0101 (6)
C18	0.0293 (6)	0.0327 (6)	0.0313 (6)	0.0049 (5)	0.0051 (5)	0.0003 (5)
C19	0.0429 (7)	0.0467 (8)	0.0379 (7)	0.0131 (6)	0.0130 (6)	0.0062 (6)
C20	0.0576 (10)	0.0613 (10)	0.0484 (9)	0.0173 (8)	0.0248 (8)	0.0013 (7)
C21	0.0619 (10)	0.0562 (10)	0.0693 (11)	0.0254 (8)	0.0285 (9)	−0.0019 (8)
C22	0.0611 (10)	0.0474 (9)	0.0641 (10)	0.0279 (8)	0.0167 (8)	0.0086 (8)
C23	0.0455 (8)	0.0413 (7)	0.0403 (7)	0.0150 (6)	0.0117 (6)	0.0060 (6)
C24	0.0642 (10)	0.0485 (9)	0.0429 (8)	0.0280 (8)	0.0018 (7)	0.0064 (7)
C25	0.0422 (7)	0.0358 (7)	0.0311 (6)	0.0146 (6)	0.0065 (5)	0.0017 (5)
C26	0.0395 (8)	0.0513 (9)	0.0411 (8)	0.0069 (6)	−0.0052 (6)	−0.0004 (6)
C27	0.0595 (11)	0.0746 (13)	0.0794 (13)	0.0234 (10)	−0.0081 (10)	0.0230 (11)
N1	0.0296 (5)	0.0308 (5)	0.0314 (5)	0.0059 (4)	0.0030 (4)	0.0054 (4)
N2	0.0291 (5)	0.0398 (6)	0.0302 (5)	0.0091 (4)	0.0077 (4)	0.0055 (4)
O1	0.0431 (5)	0.0415 (5)	0.0446 (5)	0.0043 (4)	0.0088 (4)	0.0161 (4)
O2	0.0516 (6)	0.0649 (7)	0.0388 (5)	0.0120 (5)	0.0204 (5)	0.0043 (5)
O3	0.0537 (6)	0.0723 (8)	0.0297 (5)	0.0162 (6)	0.0084 (4)	0.0000 (5)
O4	0.0352 (5)	0.0447 (5)	0.0327 (5)	0.0077 (4)	0.0010 (4)	0.0018 (4)
S1	0.0835 (3)	0.0571 (3)	0.0407 (2)	0.0286 (2)	0.0031 (2)	−0.00484 (18)

C1—N1	1.4773 (16)	C12—C13	1.382 (2)
C1—C2	1.5142 (19)	C13—C14	1.373 (2)
C1—C12	1.5182 (19)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.375 (3)
C2—C3	1.4861 (19)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.363 (3)
C2—H2B	0.9700	C15—H15	0.9300
C3—O2	1.3323 (16)	C16—C17	1.384 (2)
C3—C4	1.3501 (19)	C16—H16	0.9300
C4—C25	1.4477 (18)	C17—H17	0.9300
C4—C5	1.5126 (17)	C18—C23	1.375 (2)
C5—N1	1.4665 (16)	C18—C19	1.3867 (19)
C5—C18	1.5202 (18)	C19—C20	1.374 (2)
C5—H5	0.9800	C19—H19	0.9300
C6—O1	1.2227 (16)	C20—C21	1.367 (3)
C6—N1	1.3609 (17)	C20—H20	0.9300
C6—C7	1.5281 (18)	C21—C22	1.371 (2)
C7—N2	1.4675 (18)	C21—H21	0.9300
C7—C24	1.526 (2)	C22—C23	1.380 (2)
C7—H7	0.9800	C22—H22	0.9300
C8—N2	1.4520 (18)	C23—H23	0.9300
C8—C9	1.507 (2)	C24—H24A	0.9600
C8—H8A	0.9700	C24—H24B	0.9600
C8—H8B	0.9700	C24—H24C	0.9600
C9—S1	1.782 (2)	C25—O3	1.2212 (17)
C9—H9A	0.9700	C25—O4	1.3310 (17)
C9—H9B	0.9700	C26—O4	1.4505 (16)
C10—C11	1.507 (2)	C26—C27	1.485 (3)
C10—S1	1.792 (2)	C26—H26A	0.9700
C10—H10A	0.9700	C26—H26B	0.9700
C10—H10B	0.9700	C27—H27A	0.9600
C11—N2	1.4647 (17)	C27—H27B	0.9600
C11—H11A	0.9700	C27—H27C	0.9600
C11—H11B	0.9700	O2—H2	0.8200
C12—C17	1.382 (2)
N1—C1—C2	107.66 (11)	C12—C13—H13	119.5
N1—C1—C12	112.16 (11)	C13—C14—C15	120.20 (16)
C2—C1—C12	114.82 (11)	C13—C14—H14	119.9
N1—C1—H1	107.3	C15—C14—H14	119.9
C2—C1—H1	107.3	C16—C15—C14	119.63 (16)
C12—C1—H1	107.3	C16—C15—H15	120.2
C3—C2—C1	111.58 (11)	C14—C15—H15	120.2
C3—C2—H2A	109.3	C15—C16—C17	120.40 (16)
C1—C2—H2A	109.3	C15—C16—H16	119.8
C3—C2—H2B	109.3	C17—C16—H16	119.8
C1—C2—H2B	109.3	C12—C17—C16	120.56 (15)
H2A—C2—H2B	108.0	C12—C17—H17	119.7
O2—C3—C4	125.09 (13)	C16—C17—H17	119.7
O2—C3—C2	112.09 (12)	C23—C18—C19	118.54 (13)
C4—C3—C2	122.79 (12)	C23—C18—C5	123.75 (12)
C3—C4—C25	118.29 (12)	C19—C18—C5	117.71 (12)
C3—C4—C5	122.64 (11)	C20—C19—C18	120.98 (14)
C25—C4—C5	118.79 (11)	C20—C19—H19	119.5
N1—C5—C4	109.82 (10)	C18—C19—H19	119.5
N1—C5—C18	110.60 (10)	C21—C20—C19	119.88 (15)
C4—C5—C18	116.73 (10)	C21—C20—H20	120.1
N1—C5—H5	106.3	C19—C20—H20	120.1
C4—C5—H5	106.3	C20—C21—C22	119.83 (15)
C18—C5—H5	106.3	C20—C21—H21	120.1
O1—C6—N1	121.77 (12)	C22—C21—H21	120.1
O1—C6—C7	120.49 (12)	C21—C22—C23	120.49 (15)
N1—C6—C7	117.73 (11)	C21—C22—H22	119.8
N2—C7—C24	116.11 (11)	C23—C22—H22	119.8
N2—C7—C6	109.40 (10)	C18—C23—C22	120.26 (14)
C24—C7—C6	109.39 (12)	C18—C23—H23	119.9
N2—C7—H7	107.2	C22—C23—H23	119.9
C24—C7—H7	107.2	C7—C24—H24A	109.5
C6—C7—H7	107.2	C7—C24—H24B	109.5
N2—C8—C9	111.80 (13)	H24A—C24—H24B	109.5
N2—C8—H8A	109.3	C7—C24—H24C	109.5
C9—C8—H8A	109.3	H24A—C24—H24C	109.5
N2—C8—H8B	109.3	H24B—C24—H24C	109.5
C9—C8—H8B	109.3	O3—C25—O4	122.39 (12)
H8A—C8—H8B	107.9	O3—C25—C4	123.53 (13)
C8—C9—S1	112.18 (12)	O4—C25—C4	114.08 (11)
C8—C9—H9A	109.2	O4—C26—C27	110.13 (13)
S1—C9—H9A	109.2	O4—C26—H26A	109.6
C8—C9—H9B	109.2	C27—C26—H26A	109.6
S1—C9—H9B	109.2	O4—C26—H26B	109.6
H9A—C9—H9B	107.9	C27—C26—H26B	109.6
C11—C10—S1	112.47 (12)	H26A—C26—H26B	108.1
C11—C10—H10A	109.1	C26—C27—H27A	109.5
S1—C10—H10A	109.1	C26—C27—H27B	109.5
C11—C10—H10B	109.1	H27A—C27—H27B	109.5
S1—C10—H10B	109.1	C26—C27—H27C	109.5
H10A—C10—H10B	107.8	H27A—C27—H27C	109.5
N2—C11—C10	112.61 (13)	H27B—C27—H27C	109.5
N2—C11—H11A	109.1	C6—N1—C5	117.56 (10)
C10—C11—H11A	109.1	C6—N1—C1	125.05 (11)
N2—C11—H11B	109.1	C5—N1—C1	115.92 (10)
C10—C11—H11B	109.1	C8—N2—C11	112.46 (11)
H11A—C11—H11B	107.8	C8—N2—C7	111.81 (11)
C17—C12—C13	118.22 (14)	C11—N2—C7	111.79 (11)
C17—C12—C1	123.25 (13)	C3—O2—H2	109.5
C13—C12—C1	118.41 (12)	C25—O4—C26	116.77 (11)
C14—C13—C12	120.97 (15)	C9—S1—C10	95.98 (8)
C14—C13—H13	119.5
N1—C1—C2—C3	48.04 (14)	C18—C19—C20—C21	0.0 (2)
C12—C1—C2—C3	−77.64 (14)	C19—C20—C21—C22	0.5 (3)
C1—C2—C3—O2	164.35 (11)	C20—C21—C22—C23	−0.4 (3)
C1—C2—C3—C4	−17.41 (18)	C19—C18—C23—C22	0.6 (2)
O2—C3—C4—C25	0.3 (2)	C5—C18—C23—C22	−179.08 (13)
C2—C3—C4—C25	−177.71 (12)	C21—C22—C23—C18	−0.2 (2)
O2—C3—C4—C5	174.15 (12)	C3—C4—C25—O3	−3.3 (2)
C2—C3—C4—C5	−3.9 (2)	C5—C4—C25—O3	−177.40 (13)
C3—C4—C5—N1	−7.76 (17)	C3—C4—C25—O4	176.05 (12)
C25—C4—C5—N1	166.06 (11)	C5—C4—C25—O4	1.95 (17)
C3—C4—C5—C18	119.13 (14)	O1—C6—N1—C5	−8.07 (18)
C25—C4—C5—C18	−67.04 (15)	C7—C6—N1—C5	172.90 (10)
O1—C6—C7—N2	−110.36 (14)	O1—C6—N1—C1	−173.66 (12)
N1—C6—C7—N2	68.68 (14)	C7—C6—N1—C1	7.31 (18)
O1—C6—C7—C24	17.86 (18)	C4—C5—N1—C6	−123.91 (12)
N1—C6—C7—C24	−163.10 (12)	C18—C5—N1—C6	105.82 (13)
N2—C8—C9—S1	64.32 (17)	C4—C5—N1—C1	42.99 (14)
S1—C10—C11—N2	−61.25 (16)	C18—C5—N1—C1	−87.27 (13)
N1—C1—C12—C17	−125.18 (14)	C2—C1—N1—C6	101.21 (14)
C2—C1—C12—C17	−1.86 (18)	C12—C1—N1—C6	−131.53 (13)
N1—C1—C12—C13	58.79 (15)	C2—C1—N1—C5	−64.58 (14)
C2—C1—C12—C13	−177.89 (12)	C12—C1—N1—C5	62.67 (14)
C17—C12—C13—C14	−0.1 (2)	C9—C8—N2—C11	−63.15 (17)
C1—C12—C13—C14	176.10 (14)	C9—C8—N2—C7	170.12 (13)
C12—C13—C14—C15	−0.5 (3)	C10—C11—N2—C8	61.90 (17)
C13—C14—C15—C16	1.1 (3)	C10—C11—N2—C7	−171.36 (12)
C14—C15—C16—C17	−1.1 (3)	C24—C7—N2—C8	75.03 (16)
C13—C12—C17—C16	0.2 (2)	C6—C7—N2—C8	−160.59 (11)
C1—C12—C17—C16	−175.88 (14)	C24—C7—N2—C11	−52.06 (16)
C15—C16—C17—C12	0.5 (3)	C6—C7—N2—C11	72.31 (14)
N1—C5—C18—C23	116.73 (13)	O3—C25—O4—C26	−7.80 (19)
C4—C5—C18—C23	−9.78 (18)	C4—C25—O4—C26	172.84 (11)
N1—C5—C18—C19	−62.99 (15)	C27—C26—O4—C25	−81.20 (18)
C4—C5—C18—C19	170.50 (11)	C8—C9—S1—C10	−55.24 (14)
C23—C18—C19—C20	−0.6 (2)	C11—C10—S1—C9	53.83 (14)
C5—C18—C19—C20	179.18 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.85	2.560 (2)	144
C24—H24B···O3i	0.96	2.54	3.285 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.85	2.560 (2)	144
C24—H24B⋯O3i	0.96	2.54	3.285 (2)	135

Symmetry code: (i) .