Diethyl 2-[(5-meth-oxy-2-methyl-1-phenyl-sulfonyl-1H-indol-3-yl)methyl-ene]malonate.

In the title compound, C(24)H(25)NO(7)S, the sulfonyl-bound phenyl ring is approximately perpendicular to the indole ring system [dihedral angle = 87.72 (5)°]. The methyl group of one of the ester units is disordered over two positions with occupancies of 0.527 (13) and 0.473 (13). An intra-molecular C-H⋯O hydrogen bond is observed. In the crystal structure, mol-ecules are linked into a ribbon structure running along the c axis by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions involving the pyrrole ring.

Related literature

For general background on indoles, see: El-Sayed et al. (1986 ▶); Farhanullah et al. (2004 ▶); Okabe & Adachi (1998 ▶); Schollmeyer et al. (1995 ▶). For the Thorpe–Ingold effect, see: Bassindale (1984 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For a related structure, see: Chakkaravarthi et al. (2008 ▶).

Experimental

Crystal data

C24H25NO7S

M = 471.51

Triclinic,

a = 8.7597 (2) Å

b = 10.9029 (2) Å

c = 12.5186 (3) Å

α = 88.402 (1)°

β = 79.723 (1)°

γ = 83.635 (2)°

V = 1169.13 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.964, T max = 0.971

27454 measured reflections

6218 independent reflections

4628 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.176

S = 1.07

6218 reflections

309 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019369/ci2774sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019369/ci2774Isup2.hkl

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

C24H25NO7S	Z = 2
Mr = 471.51	F(000) = 496
Triclinic, P1	Dx = 1.339 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7597 (2) Å	Cell parameters from 6218 reflections
b = 10.9029 (2) Å	θ = 1.6–29.1°
c = 12.5186 (3) Å	µ = 0.18 mm−1
α = 88.402 (1)°	T = 293 K
β = 79.723 (1)°	Block, yellow
γ = 83.635 (2)°	0.22 × 0.18 × 0.15 mm
V = 1169.13 (4) Å3

Bruker Kappa-APEXII area-detector diffractometer	6218 independent reflections
Radiation source: fine-focus sealed tube	4628 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 29.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.964, Tmax = 0.971	k = −14→14
27454 measured reflections	l = −17→17

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.09P)2 + 0.3748P] where P = (Fo2 + 2Fc2)/3
6218 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 0.66 e Å−3
16 restraints	Δρmin = −0.45 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	Occ. (<1)
C2	0.1929 (2)	0.26604 (18)	0.44185 (16)	0.0459 (4)
C3	0.2837 (2)	0.35252 (17)	0.39343 (15)	0.0423 (4)
C4	0.2631 (2)	0.45572 (17)	0.46608 (14)	0.0390 (4)
C5	0.1556 (2)	0.43026 (17)	0.55745 (15)	0.0399 (4)
C6	0.1105 (2)	0.51428 (18)	0.64167 (15)	0.0462 (4)
H6	0.0372	0.4979	0.7023	0.055*
C7	0.1787 (2)	0.62274 (19)	0.63165 (16)	0.0482 (4)
H7	0.1523	0.6797	0.6876	0.058*
C8	0.2861 (2)	0.64990 (18)	0.54028 (16)	0.0442 (4)
C9	0.3283 (2)	0.56763 (18)	0.45571 (15)	0.0427 (4)
H9	0.3979	0.5861	0.3937	0.051*
C10	0.1592 (2)	0.15262 (18)	0.70459 (16)	0.0461 (4)
C11	0.2091 (3)	0.0301 (2)	0.68271 (18)	0.0550 (5)
H11	0.1655	−0.0122	0.6342	0.066*
C12	0.3239 (3)	−0.0290 (2)	0.7332 (2)	0.0682 (6)
H12	0.3584	−0.1117	0.7190	0.082*
C13	0.3875 (3)	0.0341 (3)	0.8045 (2)	0.0745 (7)
H13	0.4654	−0.0061	0.8384	0.089*
C14	0.3377 (4)	0.1551 (3)	0.8262 (2)	0.0756 (7)
H14	0.3818	0.1968	0.8749	0.091*
C15	0.2218 (3)	0.2167 (2)	0.77638 (19)	0.0611 (6)
H15	0.1873	0.2993	0.7911	0.073*
C16	0.1853 (4)	0.1390 (2)	0.4038 (2)	0.0672 (6)
H16A	0.0883	0.1354	0.3790	0.101*
H16B	0.1924	0.0813	0.4625	0.101*
H16C	0.2704	0.1183	0.3452	0.101*
C17	0.3945 (2)	0.34685 (18)	0.29260 (16)	0.0465 (4)
H17	0.4866	0.3808	0.2952	0.056*
C18	0.3860 (2)	0.30077 (18)	0.19641 (16)	0.0470 (4)
C19	0.2432 (2)	0.2538 (2)	0.17047 (16)	0.0506 (5)
C20	0.1390 (3)	0.0829 (3)	0.1115 (3)	0.0788 (8)
H20A	0.1112	0.1196	0.0452	0.095*
H20B	0.0494	0.0975	0.1693	0.095*
C21	0.1827 (5)	−0.0488 (3)	0.0973 (3)	0.1081 (12)
H21A	0.0969	−0.0865	0.0789	0.162*
H21B	0.2087	−0.0846	0.1636	0.162*
H21C	0.2714	−0.0625	0.0400	0.162*
C22	0.5148 (3)	0.3041 (2)	0.10308 (19)	0.0587 (5)
C23	0.7754 (4)	0.3516 (4)	0.0435 (3)	0.1053 (13)
H23A	0.7917	0.2818	−0.0051	0.126*
H23B	0.8686	0.3537	0.0748	0.126*
C24	0.7462 (13)	0.4658 (8)	−0.0169 (9)	0.136 (4)	0.527 (13)
H24A	0.8345	0.4753	−0.0730	0.204*	0.527 (13)
H24B	0.7299	0.5346	0.0315	0.204*	0.527 (13)
H24C	0.6551	0.4626	−0.0491	0.204*	0.527 (13)
C24'	0.8132 (13)	0.4810 (6)	0.0454 (10)	0.125 (4)	0.473 (13)
H24D	0.9014	0.4925	−0.0102	0.187*	0.473 (13)
H24E	0.8375	0.4977	0.1150	0.187*	0.473 (13)
H24F	0.7251	0.5364	0.0326	0.187*	0.473 (13)
C25	0.4367 (3)	0.8015 (2)	0.4473 (2)	0.0655 (6)
H25A	0.4678	0.8809	0.4593	0.098*
H25B	0.3789	0.8073	0.3887	0.098*
H25C	0.5277	0.7433	0.4291	0.098*
N1	0.10926 (19)	0.31258 (15)	0.54194 (13)	0.0450 (4)
O1	−0.07993 (18)	0.31630 (15)	0.71397 (14)	0.0640 (4)
O2	−0.05720 (19)	0.14123 (16)	0.59054 (15)	0.0668 (5)
O3	0.11914 (19)	0.31388 (18)	0.17716 (15)	0.0703 (5)
O4	0.27014 (18)	0.13750 (15)	0.13834 (14)	0.0620 (4)
O5	0.5020 (3)	0.2806 (3)	0.01285 (16)	0.1019 (8)
O6	0.6431 (2)	0.3383 (2)	0.12855 (16)	0.0883 (7)
O7	0.34224 (19)	0.76187 (14)	0.54229 (13)	0.0588 (4)
S1	0.01286 (6)	0.23002 (5)	0.64069 (4)	0.04951 (16)

	U11	U22	U33	U12	U13	U23
C2	0.0544 (10)	0.0432 (10)	0.0434 (9)	−0.0068 (8)	−0.0163 (8)	0.0002 (8)
C3	0.0455 (9)	0.0434 (9)	0.0398 (9)	−0.0034 (7)	−0.0130 (7)	−0.0031 (7)
C4	0.0372 (8)	0.0437 (9)	0.0376 (8)	−0.0026 (7)	−0.0115 (7)	−0.0017 (7)
C5	0.0388 (8)	0.0407 (9)	0.0412 (9)	−0.0036 (7)	−0.0111 (7)	0.0038 (7)
C6	0.0467 (10)	0.0499 (10)	0.0397 (9)	−0.0027 (8)	−0.0031 (7)	0.0012 (8)
C7	0.0522 (10)	0.0478 (10)	0.0436 (10)	−0.0023 (8)	−0.0064 (8)	−0.0076 (8)
C8	0.0439 (9)	0.0434 (10)	0.0473 (10)	−0.0062 (7)	−0.0128 (8)	−0.0022 (8)
C9	0.0397 (8)	0.0478 (10)	0.0414 (9)	−0.0075 (7)	−0.0079 (7)	−0.0001 (7)
C10	0.0471 (9)	0.0492 (10)	0.0428 (9)	−0.0094 (8)	−0.0088 (8)	0.0095 (8)
C11	0.0635 (12)	0.0507 (11)	0.0528 (11)	−0.0101 (9)	−0.0147 (10)	0.0068 (9)
C12	0.0740 (15)	0.0624 (14)	0.0659 (15)	0.0076 (12)	−0.0171 (12)	0.0075 (12)
C13	0.0711 (15)	0.0868 (14)	0.0675 (15)	0.0054 (13)	−0.0279 (13)	0.0119 (13)
C14	0.0849 (18)	0.0880 (15)	0.0622 (14)	−0.0091 (14)	−0.0347 (14)	−0.0049 (13)
C15	0.0748 (15)	0.0584 (13)	0.0537 (12)	−0.0061 (11)	−0.0216 (11)	−0.0009 (10)
C16	0.1018 (19)	0.0461 (11)	0.0566 (13)	−0.0175 (12)	−0.0155 (13)	−0.0015 (10)
C17	0.0470 (10)	0.0458 (10)	0.0471 (10)	−0.0044 (8)	−0.0089 (8)	−0.0051 (8)
C18	0.0461 (10)	0.0489 (10)	0.0460 (10)	−0.0036 (8)	−0.0078 (8)	−0.0071 (8)
C19	0.0474 (10)	0.0630 (12)	0.0409 (9)	−0.0042 (9)	−0.0062 (8)	−0.0079 (9)
C20	0.0690 (16)	0.093 (2)	0.0817 (18)	−0.0299 (14)	−0.0183 (13)	−0.0193 (15)
C21	0.112 (3)	0.092 (2)	0.126 (3)	−0.050 (2)	−0.008 (2)	−0.026 (2)
C22	0.0522 (11)	0.0685 (14)	0.0543 (12)	−0.0114 (10)	−0.0009 (9)	−0.0172 (10)
C23	0.0772 (19)	0.128 (3)	0.105 (2)	−0.044 (2)	0.0246 (15)	−0.035 (2)
C24	0.135 (4)	0.136 (4)	0.136 (4)	−0.0144 (11)	−0.0234 (12)	0.0001 (10)
C24'	0.125 (4)	0.125 (4)	0.125 (4)	−0.0152 (11)	−0.0213 (12)	0.0003 (10)
C25	0.0642 (14)	0.0622 (14)	0.0728 (15)	−0.0255 (11)	−0.0089 (11)	0.0043 (11)
N1	0.0512 (9)	0.0430 (8)	0.0429 (8)	−0.0096 (7)	−0.0122 (7)	0.0052 (6)
O1	0.0498 (8)	0.0646 (10)	0.0700 (10)	−0.0029 (7)	0.0056 (7)	0.0129 (8)
O2	0.0590 (9)	0.0645 (10)	0.0867 (12)	−0.0265 (8)	−0.0296 (8)	0.0149 (9)
O3	0.0480 (8)	0.0871 (12)	0.0744 (11)	0.0051 (8)	−0.0117 (8)	−0.0208 (9)
O4	0.0545 (8)	0.0616 (9)	0.0736 (10)	−0.0097 (7)	−0.0169 (7)	−0.0169 (8)
O5	0.0799 (13)	0.169 (2)	0.0583 (11)	−0.0429 (14)	0.0093 (9)	−0.0447 (13)
O6	0.0620 (11)	0.1307 (18)	0.0742 (12)	−0.0402 (11)	0.0049 (8)	−0.0285 (12)
O7	0.0675 (9)	0.0513 (8)	0.0599 (9)	−0.0203 (7)	−0.0080 (7)	−0.0071 (7)
S1	0.0422 (3)	0.0513 (3)	0.0567 (3)	−0.0116 (2)	−0.0114 (2)	0.0123 (2)

C2—C3	1.360 (3)	C17—H17	0.93
C2—N1	1.411 (3)	C18—C22	1.475 (3)
C2—C16	1.490 (3)	C18—C19	1.493 (3)
C3—C4	1.442 (2)	C19—O3	1.196 (3)
C3—C17	1.447 (3)	C19—O4	1.324 (3)
C4—C5	1.388 (3)	C20—O4	1.445 (3)
C4—C9	1.396 (3)	C20—C21	1.452 (5)
C5—C6	1.390 (3)	C20—H20A	0.97
C5—N1	1.416 (2)	C20—H20B	0.97
C6—C7	1.376 (3)	C21—H21A	0.96
C6—H6	0.93	C21—H21B	0.96
C7—C8	1.393 (3)	C21—H21C	0.96
C7—H7	0.93	C22—O5	1.193 (3)
C8—O7	1.368 (2)	C22—O6	1.316 (3)
C8—C9	1.379 (3)	C23—O6	1.445 (3)
C9—H9	0.93	C23—C24	1.461 (5)
C10—C15	1.376 (3)	C23—C24'	1.486 (5)
C10—C11	1.378 (3)	C23—H23A	0.97
C10—S1	1.756 (2)	C23—H23B	0.97
C11—C12	1.373 (3)	C24—H24A	0.96
C11—H11	0.93	C24—H24B	0.96
C12—C13	1.370 (4)	C24—H24C	0.96
C12—H12	0.93	C24'—H24D	0.96
C13—C14	1.362 (4)	C24'—H24E	0.96
C13—H13	0.93	C24'—H24F	0.96
C14—C15	1.386 (3)	C25—O7	1.409 (3)
C14—H14	0.93	C25—H25A	0.96
C15—H15	0.93	C25—H25B	0.96
C16—H16A	0.96	C25—H25C	0.96
C16—H16B	0.96	N1—S1	1.6690 (16)
C16—H16C	0.96	O1—S1	1.4141 (17)
C17—C18	1.335 (3)	O2—S1	1.4181 (17)
C3—C2—N1	108.67 (16)	O4—C19—C18	111.98 (17)
C3—C2—C16	128.0 (2)	O4—C20—C21	108.4 (3)
N1—C2—C16	123.20 (19)	O4—C20—H20A	110.0
C2—C3—C4	107.82 (17)	C21—C20—H20A	110.0
C2—C3—C17	129.75 (18)	O4—C20—H20B	110.0
C4—C3—C17	122.24 (17)	C21—C20—H20B	110.0
C5—C4—C9	120.75 (17)	H20A—C20—H20B	108.4
C5—C4—C3	108.18 (16)	C20—C21—H21A	109.5
C9—C4—C3	131.05 (17)	C20—C21—H21B	109.5
C4—C5—C6	121.34 (17)	H21A—C21—H21B	109.5
C4—C5—N1	106.95 (16)	C20—C21—H21C	109.5
C6—C5—N1	131.70 (17)	H21A—C21—H21C	109.5
C7—C6—C5	117.28 (18)	H21B—C21—H21C	109.5
C7—C6—H6	121.4	O5—C22—O6	123.5 (2)
C5—C6—H6	121.4	O5—C22—C18	122.8 (2)
C6—C7—C8	122.06 (18)	O6—C22—C18	113.66 (19)
C6—C7—H7	119.0	O6—C23—C24	109.3 (5)
C8—C7—H7	119.0	O6—C23—C24'	107.6 (5)
O7—C8—C9	124.44 (18)	O6—C23—H23A	109.8
O7—C8—C7	114.95 (17)	C24—C23—H23A	109.8
C9—C8—C7	120.60 (18)	C24'—C23—H23A	140.2
C8—C9—C4	117.94 (17)	O6—C23—H23B	109.8
C8—C9—H9	121.0	C24—C23—H23B	109.8
C4—C9—H9	121.0	C24'—C23—H23B	70.5
C15—C10—C11	121.2 (2)	H23A—C23—H23B	108.3
C15—C10—S1	118.66 (17)	C23—C24—H24A	109.5
C11—C10—S1	120.13 (16)	C23—C24—H24B	109.5
C12—C11—C10	119.4 (2)	H24A—C24—H24B	109.5
C12—C11—H11	120.3	C23—C24—H24C	109.5
C10—C11—H11	120.3	H24A—C24—H24C	109.5
C13—C12—C11	119.9 (2)	H24B—C24—H24C	109.5
C13—C12—H12	120.1	C23—C24'—H24D	109.5
C11—C12—H12	120.1	C23—C24'—H24E	109.5
C14—C13—C12	120.7 (2)	H24D—C24'—H24E	109.5
C14—C13—H13	119.7	C23—C24'—H24F	109.5
C12—C13—H13	119.7	H24D—C24'—H24F	109.5
C13—C14—C15	120.5 (2)	H24E—C24'—H24F	109.5
C13—C14—H14	119.7	O7—C25—H25A	109.5
C15—C14—H14	119.7	O7—C25—H25B	109.5
C10—C15—C14	118.3 (2)	H25A—C25—H25B	109.5
C10—C15—H15	120.8	O7—C25—H25C	109.5
C14—C15—H15	120.8	H25A—C25—H25C	109.5
C2—C16—H16A	109.5	H25B—C25—H25C	109.5
C2—C16—H16B	109.5	C2—N1—C5	108.32 (15)
H16A—C16—H16B	109.5	C2—N1—S1	125.65 (13)
C2—C16—H16C	109.5	C5—N1—S1	123.91 (13)
H16A—C16—H16C	109.5	C19—O4—C20	116.42 (19)
H16B—C16—H16C	109.5	C22—O6—C23	119.1 (2)
C18—C17—C3	130.42 (19)	C8—O7—C25	117.79 (17)
C18—C17—H17	114.8	O1—S1—O2	120.42 (11)
C3—C17—H17	114.8	O1—S1—N1	106.20 (9)
C17—C18—C22	121.49 (19)	O2—S1—N1	107.38 (10)
C17—C18—C19	123.87 (18)	O1—S1—C10	108.77 (10)
C22—C18—C19	114.37 (17)	O2—S1—C10	108.50 (10)
O3—C19—O4	123.8 (2)	N1—S1—C10	104.43 (9)
O3—C19—C18	124.2 (2)
N1—C2—C3—C4	2.4 (2)	C17—C18—C19—O4	−122.7 (2)
C16—C2—C3—C4	−173.8 (2)	C22—C18—C19—O4	63.2 (2)
N1—C2—C3—C17	177.27 (18)	C17—C18—C22—O5	−168.7 (3)
C16—C2—C3—C17	1.0 (3)	C19—C18—C22—O5	5.6 (4)
C2—C3—C4—C5	−1.4 (2)	C17—C18—C22—O6	9.7 (3)
C17—C3—C4—C5	−176.76 (16)	C19—C18—C22—O6	−176.0 (2)
C2—C3—C4—C9	−179.75 (18)	C3—C2—N1—C5	−2.5 (2)
C17—C3—C4—C9	4.9 (3)	C16—C2—N1—C5	173.94 (19)
C9—C4—C5—C6	−0.6 (3)	C3—C2—N1—S1	−166.42 (13)
C3—C4—C5—C6	−179.14 (16)	C16—C2—N1—S1	10.0 (3)
C9—C4—C5—N1	178.41 (15)	C4—C5—N1—C2	1.58 (19)
C3—C4—C5—N1	−0.13 (19)	C6—C5—N1—C2	−179.56 (19)
C4—C5—C6—C7	−1.1 (3)	C4—C5—N1—S1	165.83 (13)
N1—C5—C6—C7	−179.83 (18)	C6—C5—N1—S1	−15.3 (3)
C5—C6—C7—C8	1.4 (3)	O3—C19—O4—C20	−0.6 (3)
C6—C7—C8—O7	179.45 (18)	C18—C19—O4—C20	179.8 (2)
C6—C7—C8—C9	0.0 (3)	C21—C20—O4—C19	−169.9 (3)
O7—C8—C9—C4	178.90 (17)	O5—C22—O6—C23	1.6 (5)
C7—C8—C9—C4	−1.7 (3)	C18—C22—O6—C23	−176.8 (3)
C5—C4—C9—C8	2.0 (3)	C24—C23—O6—C22	75.7 (6)
C3—C4—C9—C8	−179.87 (18)	C24'—C23—O6—C22	121.2 (6)
C15—C10—C11—C12	−0.2 (3)	C9—C8—O7—C25	6.9 (3)
S1—C10—C11—C12	179.85 (18)	C7—C8—O7—C25	−172.56 (19)
C10—C11—C12—C13	0.0 (4)	C2—N1—S1—O1	−167.59 (16)
C11—C12—C13—C14	0.2 (4)	C5—N1—S1—O1	30.90 (18)
C12—C13—C14—C15	−0.1 (5)	C2—N1—S1—O2	−37.54 (18)
C11—C10—C15—C14	0.3 (4)	C5—N1—S1—O2	160.94 (15)
S1—C10—C15—C14	−179.8 (2)	C2—N1—S1—C10	77.54 (17)
C13—C14—C15—C10	−0.1 (4)	C5—N1—S1—C10	−83.98 (16)
C2—C3—C17—C18	41.7 (3)	C15—C10—S1—O1	−34.6 (2)
C4—C3—C17—C18	−144.1 (2)	C11—C10—S1—O1	145.35 (17)
C3—C17—C18—C22	−179.7 (2)	C15—C10—S1—O2	−167.21 (18)
C3—C17—C18—C19	6.6 (4)	C11—C10—S1—O2	12.7 (2)
C17—C18—C19—O3	57.7 (3)	C15—C10—S1—N1	78.50 (19)
C22—C18—C19—O3	−116.4 (2)	C11—C10—S1—N1	−101.59 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.32	2.901 (3)	120
C14—H14···O5i	0.93	2.42	3.349 (3)	173
C25—H25C···Cg1ii	0.96	2.92	3.515 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.32	2.901 (3)	120
C14—H14⋯O5i	0.93	2.42	3.349 (3)	173
C25—H25C⋯Cg1ii	0.96	2.92	3.515 (3)	140

Symmetry codes: (i) ; (ii) .