9-(3-Methoxy-phen-yl)-6,6-dimethyl-4-phenyl-2,3,5,6,7,9-hexa-hydro-thieno[3,2-b]quinolin-8(4H)-one 1,1-dioxide.

The title compound, C(26)H(27)NO(4)S, with a thiophene ring fused to a quinoline ring, was synthesized via the condensation of dihydro-thio-phen-3(2H)-one 1,1-dioxide, 5,5-dimethyl-3-(phenyl-amino)cyclo-hex-2-enone and 3-methoxy-benzaldehyde in refluxing ethanol. In the crystal structure, the thiophene dioxide ring and the pyridine ring adopt envelope conformations. The connection of the pyridine ring to the phenyl and benzene rings can be described by the C-C-C-C and C-N-C-C torsion angles of 45.5 (2) and 88.7 (2)°, respectively. The cyclo-hex-2-enone ring is in a half-chair conformation. The crystal packing is stabilized by non-classical inter-molecular C-H⋯O hydrogen bonds with the carbonyl O and sulfone O atoms acting as acceptors.

Related literature

For the use of thienoquinoline compounds as ATP-sensitive potassium channel openers, see: Altenbach et al. (2006 ▶); Carroll et al. (1999 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H27NO4S

M = 449.55

Monoclinic,

a = 11.2488 (14) Å

b = 14.8013 (18) Å

c = 13.3866 (16) Å

β = 92.747 (7)°

V = 2226.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 113 K

0.20 × 0.14 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.965, T max = 0.979

14414 measured reflections

4843 independent reflections

3756 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.125

S = 1.04

4843 reflections

293 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.50 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003600/hg2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003600/hg2633Isup2.hkl

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

C26H27NO4S	F(000) = 952
Mr = 449.55	Dx = 1.341 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 6501 reflections
a = 11.2488 (14) Å	θ = 2.1–27.9°
b = 14.8013 (18) Å	µ = 0.18 mm−1
c = 13.3866 (16) Å	T = 113 K
β = 92.747 (7)°	Prism, colourless
V = 2226.3 (5) Å3	0.20 × 0.14 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	4843 independent reflections
Radiation source: rotating anode	3756 reflections with I > 2σ(I)
confocal	Rint = 0.042
Detector resolution: 7.31 pixels mm-1	θmax = 27.0°, θmin = 2.1°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→18
Tmin = 0.965, Tmax = 0.979	l = −17→17
14414 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0695P)2] where P = (Fo2 + 2Fc2)/3
4843 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.50 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
S1	0.50415 (4)	0.22372 (3)	−0.24228 (3)	0.02432 (15)
O1	0.67631 (11)	0.38885 (9)	0.10478 (10)	0.0322 (3)
O2	0.60626 (12)	0.26632 (10)	−0.28274 (10)	0.0340 (4)
O3	0.51009 (13)	0.12739 (9)	−0.22990 (10)	0.0362 (4)
O4	0.82561 (12)	0.04112 (9)	0.02547 (11)	0.0367 (4)
N1	0.29857 (13)	0.34280 (10)	−0.05766 (10)	0.0227 (3)
C1	0.37176 (16)	0.37342 (12)	0.02191 (12)	0.0204 (4)
C2	0.49043 (15)	0.35533 (11)	0.02666 (12)	0.0207 (4)
C3	0.54944 (16)	0.28912 (12)	−0.04180 (12)	0.0203 (4)
H3	0.6250	0.3166	−0.0640	0.024*
C4	0.46602 (16)	0.27653 (11)	−0.13172 (12)	0.0203 (4)
C5	0.35101 (16)	0.29912 (12)	−0.13692 (12)	0.0211 (4)
C6	0.31187 (16)	0.42871 (13)	0.09903 (12)	0.0261 (4)
H6A	0.2341	0.4009	0.1120	0.031*
H6B	0.2965	0.4901	0.0719	0.031*
C7	0.38522 (16)	0.43672 (13)	0.19812 (12)	0.0253 (4)
C8	0.51206 (17)	0.46420 (13)	0.17341 (13)	0.0267 (4)
H8A	0.5100	0.5256	0.1441	0.032*
H8B	0.5622	0.4666	0.2362	0.032*
C9	0.56777 (17)	0.40077 (12)	0.10200 (13)	0.0234 (4)
C10	0.32863 (19)	0.50833 (15)	0.26286 (14)	0.0377 (5)
H10A	0.3274	0.5664	0.2277	0.057*
H10B	0.3751	0.5142	0.3263	0.057*
H10C	0.2470	0.4903	0.2761	0.057*
C11	0.38867 (18)	0.34685 (14)	0.25481 (14)	0.0322 (5)
H11A	0.4339	0.3544	0.3187	0.048*
H11B	0.4270	0.3009	0.2147	0.048*
H11C	0.3073	0.3278	0.2673	0.048*
C12	0.57895 (15)	0.19902 (12)	0.00974 (12)	0.0212 (4)
C13	0.68665 (15)	0.15746 (12)	−0.00304 (13)	0.0223 (4)
H13	0.7437	0.1860	−0.0425	0.027*
C14	0.71314 (17)	0.07423 (12)	0.04109 (13)	0.0260 (4)
C15	0.63009 (18)	0.03180 (13)	0.09773 (14)	0.0301 (5)
H15	0.6474	−0.0251	0.1278	0.036*
C16	0.52138 (18)	0.07310 (13)	0.11024 (14)	0.0306 (5)
H16	0.4640	0.0441	0.1490	0.037*
C17	0.49544 (17)	0.15579 (13)	0.06716 (14)	0.0272 (4)
H17	0.4206	0.1835	0.0765	0.033*
C18	0.8431 (2)	−0.05287 (14)	0.04084 (17)	0.0420 (6)
H18A	0.8341	−0.0673	0.1115	0.063*
H18B	0.9233	−0.0696	0.0220	0.063*
H18C	0.7841	−0.0867	−0.0004	0.063*
C19	0.27918 (16)	0.27641 (13)	−0.23133 (13)	0.0259 (4)
H19A	0.2288	0.3283	−0.2531	0.031*
H19B	0.2272	0.2237	−0.2206	0.031*
C20	0.36954 (17)	0.25471 (14)	−0.30969 (13)	0.0272 (4)
H20A	0.3827	0.3082	−0.3522	0.033*
H20B	0.3406	0.2043	−0.3530	0.033*
C21	0.17165 (15)	0.35858 (12)	−0.06443 (12)	0.0191 (4)
C22	0.12586 (16)	0.43661 (12)	−0.10791 (13)	0.0249 (4)
H22	0.1775	0.4823	−0.1304	0.030*
C23	0.00324 (17)	0.44714 (14)	−0.11823 (14)	0.0313 (5)
H23	−0.0294	0.5006	−0.1477	0.038*
C24	−0.07112 (17)	0.38065 (14)	−0.08602 (14)	0.0310 (5)
H24	−0.1549	0.3878	−0.0945	0.037*
C25	−0.02438 (18)	0.30363 (14)	−0.04146 (14)	0.0302 (5)
H25	−0.0761	0.2582	−0.0186	0.036*
C26	0.09729 (17)	0.29238 (12)	−0.02991 (13)	0.0243 (4)
H26	0.1296	0.2397	0.0014	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0256 (3)	0.0268 (3)	0.0206 (2)	0.0037 (2)	0.00181 (18)	−0.00228 (17)
O1	0.0230 (8)	0.0349 (8)	0.0380 (8)	−0.0037 (6)	−0.0065 (6)	−0.0019 (6)
O2	0.0275 (8)	0.0469 (9)	0.0284 (7)	−0.0030 (7)	0.0088 (6)	−0.0039 (6)
O3	0.0512 (10)	0.0241 (8)	0.0331 (7)	0.0076 (7)	−0.0011 (6)	−0.0037 (6)
O4	0.0319 (8)	0.0281 (8)	0.0498 (9)	0.0111 (6)	0.0000 (7)	0.0000 (6)
N1	0.0185 (8)	0.0308 (9)	0.0186 (7)	0.0034 (7)	−0.0010 (6)	−0.0043 (6)
C1	0.0239 (10)	0.0198 (9)	0.0175 (8)	−0.0001 (8)	−0.0004 (7)	0.0021 (7)
C2	0.0239 (10)	0.0200 (9)	0.0180 (8)	−0.0002 (8)	−0.0013 (7)	0.0024 (7)
C3	0.0175 (9)	0.0229 (9)	0.0205 (8)	−0.0008 (8)	0.0004 (7)	0.0013 (7)
C4	0.0229 (10)	0.0201 (9)	0.0179 (8)	0.0007 (8)	0.0009 (7)	0.0011 (7)
C5	0.0233 (10)	0.0233 (10)	0.0166 (8)	0.0001 (8)	−0.0002 (7)	0.0000 (7)
C6	0.0270 (10)	0.0309 (11)	0.0200 (9)	0.0056 (9)	−0.0019 (7)	−0.0029 (7)
C7	0.0289 (10)	0.0285 (10)	0.0184 (8)	−0.0006 (9)	−0.0011 (7)	−0.0010 (7)
C8	0.0335 (11)	0.0257 (10)	0.0205 (8)	−0.0053 (9)	−0.0039 (7)	0.0005 (7)
C9	0.0265 (11)	0.0217 (10)	0.0219 (8)	−0.0033 (8)	−0.0017 (7)	0.0071 (7)
C10	0.0452 (13)	0.0437 (13)	0.0241 (10)	0.0038 (10)	−0.0005 (9)	−0.0104 (9)
C11	0.0328 (11)	0.0409 (12)	0.0229 (9)	−0.0069 (10)	0.0015 (8)	0.0045 (8)
C12	0.0200 (9)	0.0230 (9)	0.0203 (8)	−0.0004 (8)	−0.0030 (7)	−0.0004 (7)
C13	0.0207 (10)	0.0237 (10)	0.0222 (8)	−0.0030 (8)	−0.0016 (7)	0.0000 (7)
C14	0.0281 (10)	0.0224 (10)	0.0266 (9)	0.0040 (9)	−0.0062 (7)	−0.0036 (7)
C15	0.0410 (12)	0.0212 (10)	0.0272 (9)	−0.0015 (9)	−0.0067 (8)	0.0030 (7)
C16	0.0371 (12)	0.0283 (11)	0.0266 (9)	−0.0071 (10)	0.0019 (8)	0.0043 (8)
C17	0.0240 (10)	0.0294 (11)	0.0281 (9)	−0.0008 (9)	0.0007 (8)	0.0015 (8)
C18	0.0487 (14)	0.0300 (12)	0.0463 (13)	0.0140 (11)	−0.0088 (10)	0.0000 (10)
C19	0.0223 (10)	0.0343 (11)	0.0208 (9)	0.0036 (8)	−0.0027 (7)	−0.0048 (7)
C20	0.0294 (11)	0.0332 (11)	0.0190 (8)	0.0032 (9)	−0.0002 (7)	−0.0027 (8)
C21	0.0173 (9)	0.0237 (10)	0.0161 (8)	0.0025 (8)	−0.0004 (6)	−0.0023 (7)
C22	0.0273 (10)	0.0244 (10)	0.0232 (9)	−0.0014 (9)	0.0024 (7)	0.0024 (7)
C23	0.0300 (11)	0.0340 (12)	0.0296 (10)	0.0097 (10)	−0.0028 (8)	0.0008 (8)
C24	0.0183 (10)	0.0429 (12)	0.0319 (10)	0.0014 (9)	0.0007 (8)	−0.0072 (9)
C25	0.0287 (11)	0.0360 (12)	0.0265 (10)	−0.0094 (10)	0.0073 (8)	−0.0042 (8)
C26	0.0284 (11)	0.0238 (10)	0.0209 (8)	0.0010 (8)	0.0018 (7)	0.0000 (7)

S1—O3	1.4367 (14)	C11—H11B	0.9800
S1—O2	1.4388 (14)	C11—H11C	0.9800
S1—C4	1.7453 (17)	C12—C13	1.377 (2)
S1—C20	1.7851 (19)	C12—C17	1.397 (2)
O1—C9	1.232 (2)	C13—C14	1.392 (2)
O4—C14	1.382 (2)	C13—H13	0.9500
O4—C18	1.419 (2)	C14—C15	1.382 (3)
N1—C1	1.391 (2)	C15—C16	1.384 (3)
N1—C5	1.397 (2)	C15—H15	0.9500
N1—C21	1.445 (2)	C16—C17	1.378 (3)
C1—C2	1.360 (2)	C16—H16	0.9500
C1—C6	1.502 (2)	C17—H17	0.9500
C2—C9	1.464 (2)	C18—H18A	0.9800
C2—C3	1.516 (2)	C18—H18B	0.9800
C3—C4	1.502 (2)	C18—H18C	0.9800
C3—C12	1.531 (2)	C19—C20	1.529 (2)
C3—H3	1.0000	C19—H19A	0.9900
C4—C5	1.335 (2)	C19—H19B	0.9900
C5—C19	1.505 (2)	C20—H20A	0.9900
C6—C7	1.533 (2)	C20—H20B	0.9900
C6—H6A	0.9900	C21—C22	1.382 (2)
C6—H6B	0.9900	C21—C26	1.382 (3)
C7—C10	1.527 (3)	C22—C23	1.388 (2)
C7—C11	1.531 (3)	C22—H22	0.9500
C7—C8	1.535 (3)	C23—C24	1.374 (3)
C8—C9	1.499 (2)	C23—H23	0.9500
C8—H8A	0.9900	C24—C25	1.379 (3)
C8—H8B	0.9900	C24—H24	0.9500
C10—H10A	0.9800	C25—C26	1.380 (3)
C10—H10B	0.9800	C25—H25	0.9500
C10—H10C	0.9800	C26—H26	0.9500
C11—H11A	0.9800
O3—S1—O2	116.41 (8)	C7—C11—H11C	109.5
O3—S1—C4	111.02 (8)	H11A—C11—H11C	109.5
O2—S1—C4	110.86 (8)	H11B—C11—H11C	109.5
O3—S1—C20	110.30 (9)	C13—C12—C17	118.86 (17)
O2—S1—C20	111.73 (9)	C13—C12—C3	120.42 (15)
C4—S1—C20	94.40 (8)	C17—C12—C3	120.66 (16)
C14—O4—C18	116.59 (15)	C12—C13—C14	120.95 (16)
C1—N1—C5	118.46 (14)	C12—C13—H13	119.5
C1—N1—C21	122.83 (14)	C14—C13—H13	119.5
C5—N1—C21	118.62 (14)	O4—C14—C15	124.72 (17)
C2—C1—N1	121.02 (15)	O4—C14—C13	115.37 (16)
C2—C1—C6	123.14 (15)	C15—C14—C13	119.89 (17)
N1—C1—C6	115.82 (15)	C14—C15—C16	119.33 (18)
C1—C2—C9	119.43 (16)	C14—C15—H15	120.3
C1—C2—C3	123.79 (15)	C16—C15—H15	120.3
C9—C2—C3	116.78 (15)	C17—C16—C15	120.80 (18)
C4—C3—C2	106.85 (14)	C17—C16—H16	119.6
C4—C3—C12	111.52 (14)	C15—C16—H16	119.6
C2—C3—C12	112.49 (14)	C16—C17—C12	120.16 (18)
C4—C3—H3	108.6	C16—C17—H17	119.9
C2—C3—H3	108.6	C12—C17—H17	119.9
C12—C3—H3	108.6	O4—C18—H18A	109.5
C5—C4—C3	125.27 (15)	O4—C18—H18B	109.5
C5—C4—S1	110.17 (13)	H18A—C18—H18B	109.5
C3—C4—S1	124.45 (13)	O4—C18—H18C	109.5
C4—C5—N1	121.31 (16)	H18A—C18—H18C	109.5
C4—C5—C19	117.90 (15)	H18B—C18—H18C	109.5
N1—C5—C19	120.79 (15)	C5—C19—C20	105.97 (15)
C1—C6—C7	113.35 (15)	C5—C19—H19A	110.5
C1—C6—H6A	108.9	C20—C19—H19A	110.5
C7—C6—H6A	108.9	C5—C19—H19B	110.5
C1—C6—H6B	108.9	C20—C19—H19B	110.5
C7—C6—H6B	108.9	H19A—C19—H19B	108.7
H6A—C6—H6B	107.7	C19—C20—S1	106.42 (12)
C10—C7—C11	108.85 (15)	C19—C20—H20A	110.4
C10—C7—C6	108.84 (15)	S1—C20—H20A	110.4
C11—C7—C6	111.20 (15)	C19—C20—H20B	110.4
C10—C7—C8	110.82 (16)	S1—C20—H20B	110.4
C11—C7—C8	109.59 (15)	H20A—C20—H20B	108.6
C6—C7—C8	107.54 (14)	C22—C21—C26	120.93 (17)
C9—C8—C7	113.13 (15)	C22—C21—N1	120.58 (16)
C9—C8—H8A	109.0	C26—C21—N1	118.45 (16)
C7—C8—H8A	109.0	C21—C22—C23	118.96 (17)
C9—C8—H8B	109.0	C21—C22—H22	120.5
C7—C8—H8B	109.0	C23—C22—H22	120.5
H8A—C8—H8B	107.8	C24—C23—C22	120.34 (18)
O1—C9—C2	120.68 (16)	C24—C23—H23	119.8
O1—C9—C8	120.96 (16)	C22—C23—H23	119.8
C2—C9—C8	118.34 (16)	C23—C24—C25	120.17 (18)
C7—C10—H10A	109.5	C23—C24—H24	119.9
C7—C10—H10B	109.5	C25—C24—H24	119.9
H10A—C10—H10B	109.5	C24—C25—C26	120.24 (18)
C7—C10—H10C	109.5	C24—C25—H25	119.9
H10A—C10—H10C	109.5	C26—C25—H25	119.9
H10B—C10—H10C	109.5	C25—C26—C21	119.34 (17)
C7—C11—H11A	109.5	C25—C26—H26	120.3
C7—C11—H11B	109.5	C21—C26—H26	120.3
H11A—C11—H11B	109.5
C5—N1—C1—C2	−5.1 (2)	C3—C2—C9—O1	4.0 (2)
C21—N1—C1—C2	178.44 (16)	C1—C2—C9—C8	1.6 (2)
C5—N1—C1—C6	173.45 (15)	C3—C2—C9—C8	−177.86 (14)
C21—N1—C1—C6	−3.0 (2)	C7—C8—C9—O1	−150.05 (16)
N1—C1—C2—C9	169.93 (15)	C7—C8—C9—C2	31.8 (2)
C6—C1—C2—C9	−8.5 (3)	C4—C3—C12—C13	102.89 (19)
N1—C1—C2—C3	−10.6 (3)	C2—C3—C12—C13	−137.09 (17)
C6—C1—C2—C3	170.97 (16)	C4—C3—C12—C17	−74.5 (2)
C1—C2—C3—C4	19.8 (2)	C2—C3—C12—C17	45.5 (2)
C9—C2—C3—C4	−160.73 (14)	C17—C12—C13—C14	−0.7 (3)
C1—C2—C3—C12	−102.88 (19)	C3—C12—C13—C14	−178.12 (16)
C9—C2—C3—C12	76.58 (19)	C18—O4—C14—C15	20.7 (3)
C2—C3—C4—C5	−16.6 (2)	C18—O4—C14—C13	−160.75 (17)
C12—C3—C4—C5	106.73 (19)	C12—C13—C14—O4	−177.86 (16)
C2—C3—C4—S1	167.50 (12)	C12—C13—C14—C15	0.7 (3)
C12—C3—C4—S1	−69.21 (19)	O4—C14—C15—C16	178.14 (17)
O3—S1—C4—C5	−101.22 (14)	C13—C14—C15—C16	−0.3 (3)
O2—S1—C4—C5	127.76 (13)	C14—C15—C16—C17	−0.1 (3)
C20—S1—C4—C5	12.50 (14)	C15—C16—C17—C12	0.2 (3)
O3—S1—C4—C3	75.25 (16)	C13—C12—C17—C16	0.2 (3)
O2—S1—C4—C3	−55.77 (17)	C3—C12—C17—C16	177.65 (17)
C20—S1—C4—C3	−171.03 (15)	C4—C5—C19—C20	−15.2 (2)
C3—C4—C5—N1	3.8 (3)	N1—C5—C19—C20	164.53 (16)
S1—C4—C5—N1	−179.73 (14)	C5—C19—C20—S1	22.30 (18)
C3—C4—C5—C19	−176.43 (16)	O3—S1—C20—C19	93.82 (14)
S1—C4—C5—C19	0.0 (2)	O2—S1—C20—C19	−135.03 (13)
C1—N1—C5—C4	8.5 (2)	C4—S1—C20—C19	−20.51 (14)
C21—N1—C5—C4	−174.82 (16)	C1—N1—C21—C22	87.6 (2)
C1—N1—C5—C19	−171.20 (16)	C5—N1—C21—C22	−88.9 (2)
C21—N1—C5—C19	5.4 (2)	C1—N1—C21—C26	−94.8 (2)
C2—C1—C6—C7	−18.6 (2)	C5—N1—C21—C26	88.66 (19)
N1—C1—C6—C7	162.88 (15)	C26—C21—C22—C23	−1.1 (3)
C1—C6—C7—C10	169.02 (16)	N1—C21—C22—C23	176.38 (15)
C1—C6—C7—C11	−71.1 (2)	C21—C22—C23—C24	−0.3 (3)
C1—C6—C7—C8	48.9 (2)	C22—C23—C24—C25	1.2 (3)
C10—C7—C8—C9	−174.50 (15)	C23—C24—C25—C26	−0.7 (3)
C11—C7—C8—C9	65.35 (19)	C24—C25—C26—C21	−0.7 (3)
C6—C7—C8—C9	−55.65 (19)	C22—C21—C26—C25	1.6 (3)
C1—C2—C9—O1	−176.51 (16)	N1—C21—C26—C25	−175.93 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1i	0.95	2.53	3.409 (2)	154
C23—H23···O3ii	0.95	2.51	3.353 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯O1i	0.95	2.53	3.409 (2)	154
C23—H23⋯O3ii	0.95	2.51	3.353 (2)	148

Symmetry codes: (i) ; (ii) .