Methyl (2Z)-2-{[N-(2-formyl-phen-yl)-4-methyl-benzene-sulfonamido]-meth-yl}-3-(naphthalen-1-yl)prop-2-enoate.

In the title compound, C(29)H(25)NO(5)S, the sulfonyl-bound benzene ring forms dihedral angles of 42.1 (1) and 48.5 (1)°, respectively, with the formyl-substituted benzene ring and the naphthalene residue. In the crystal, pairs of C-H⋯O inter-actions lead to the formation of R(2) (2)(10) inversion dimers, which are linked by further C-H⋯O inter-actions into supra-molecular tapes running along [100]. The crystal packing is further stabilized by C-H⋯π inter-actions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For resonance effects of acrylate, see: Merlino (1971 ▶); Varghese et al. (1986 ▶). For related structures, see: Madhanraj et al. (2011 ▶); Aziz-ur-Rehman et al. (2010 ▶).

Experimental

Crystal data

C29H25NO5S

M = 499.56

Triclinic,

a = 8.0162 (3) Å

b = 12.0887 (5) Å

c = 13.8703 (6) Å

α = 107.788 (2)°

β = 90.068 (1)°

γ = 93.446 (2)°

V = 1277.27 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.23 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.974

22485 measured reflections

4932 independent reflections

3520 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.01

4932 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S160053681200058X/bt5780sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200058X/bt5780Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200058X/bt5780Isup3.cml

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

C29H25NO5S	Z = 2
Mr = 499.56	F(000) = 524
Triclinic, P1	Dx = 1.299 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0162 (3) Å	Cell parameters from 4958 reflections
b = 12.0887 (5) Å	θ = 1.5–25.9°
c = 13.8703 (6) Å	µ = 0.17 mm−1
α = 107.788 (2)°	T = 293 K
β = 90.068 (1)°	Block, colourless
γ = 93.446 (2)°	0.23 × 0.21 × 0.16 mm
V = 1277.27 (9) Å3

Bruker APEXII CCD diffractometer	4932 independent reflections
Radiation source: fine-focus sealed tube	3520 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 25.9°, θmin = 2.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.963, Tmax = 0.974	l = −17→16
22485 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.1916P] where P = (Fo2 + 2Fc2)/3
4932 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.16584 (5)	0.44112 (4)	0.73002 (4)	0.05990 (17)
N1	0.15470 (16)	0.34007 (12)	0.78747 (11)	0.0497 (3)
O5	0.34851 (16)	0.31525 (12)	1.04708 (11)	0.0702 (4)
C8	−0.0019 (2)	0.41133 (15)	0.64232 (14)	0.0507 (4)
C1	0.1799 (2)	0.22349 (15)	0.72522 (12)	0.0487 (4)
O2	0.31605 (15)	0.42505 (14)	0.67383 (13)	0.0834 (5)
O3	0.14348 (18)	0.54886 (11)	0.80521 (12)	0.0800 (4)
O4	0.27092 (17)	0.47877 (12)	1.02354 (12)	0.0765 (4)
C23	−0.0828 (2)	0.01039 (16)	0.87084 (13)	0.0548 (4)
C18	−0.0968 (2)	0.13048 (16)	0.92080 (13)	0.0553 (4)
C16	0.1067 (2)	0.30378 (15)	0.94720 (12)	0.0507 (4)
C2	0.0452 (2)	0.14657 (17)	0.68456 (14)	0.0610 (5)
H2	−0.0632	0.1698	0.6979	0.073*
C17	0.0536 (2)	0.20561 (16)	0.96421 (13)	0.0553 (4)
H17	0.1187	0.1813	1.0086	0.066*
C9	−0.1560 (2)	0.44809 (17)	0.67467 (15)	0.0602 (5)
H9	−0.1710	0.4899	0.7422	0.072*
C15	0.0337 (2)	0.35257 (15)	0.87105 (14)	0.0551 (4)
H15A	−0.0719	0.3108	0.8447	0.066*
H15B	0.0138	0.4340	0.9023	0.066*
C6	0.3421 (2)	0.18822 (17)	0.70641 (15)	0.0617 (5)
C24	0.2488 (2)	0.37625 (16)	1.00878 (13)	0.0544 (4)
C11	−0.2700 (3)	0.36137 (19)	0.50739 (17)	0.0692 (5)
C26	0.0718 (3)	−0.04169 (18)	0.85611 (15)	0.0659 (5)
H26	0.1698	0.0040	0.8795	0.079*
C22	−0.2299 (3)	−0.06165 (18)	0.83382 (15)	0.0681 (5)
C21	−0.3850 (3)	−0.0120 (2)	0.8509 (2)	0.0887 (7)
H21	−0.4820	−0.0587	0.8274	0.106*
O1	0.63132 (19)	0.24067 (17)	0.72916 (18)	0.1204 (7)
C13	0.0203 (3)	0.3499 (2)	0.54323 (16)	0.0786 (6)
H13	0.1250	0.3251	0.5209	0.094*
C7	0.4908 (2)	0.2635 (2)	0.7536 (2)	0.0795 (6)
H7	0.4748	0.3321	0.8050	0.095*
C10	−0.2882 (2)	0.42301 (19)	0.60714 (16)	0.0687 (5)
H10	−0.3926	0.4484	0.6296	0.082*
C19	−0.2510 (3)	0.1742 (2)	0.93437 (17)	0.0738 (6)
H19	−0.2600	0.2532	0.9665	0.089*
C3	0.0714 (3)	0.0355 (2)	0.62431 (17)	0.0826 (7)
H3	−0.0193	−0.0168	0.5979	0.099*
C29	−0.2140 (4)	−0.1803 (2)	0.78207 (17)	0.0890 (8)
H29	−0.3091	−0.2276	0.7551	0.107*
C5	0.3645 (3)	0.0768 (2)	0.6432 (2)	0.0884 (7)
H5	0.4722	0.0532	0.6281	0.106*
C14	−0.4162 (3)	0.3322 (3)	0.4336 (2)	0.1124 (10)
H14A	−0.4909	0.3942	0.4516	0.169*
H14B	−0.4744	0.2613	0.4357	0.169*
H14C	−0.3765	0.3227	0.3664	0.169*
C27	0.0799 (3)	−0.1572 (2)	0.80839 (17)	0.0830 (7)
H27	0.1828	−0.1903	0.8008	0.100*
C25	0.4827 (2)	0.3807 (2)	1.11357 (17)	0.0789 (6)
H25A	0.5534	0.4210	1.0777	0.118*
H25B	0.5469	0.3286	1.1362	0.118*
H25C	0.4369	0.4361	1.1710	0.118*
C20	−0.3964 (3)	0.1018 (2)	0.9005 (2)	0.0898 (7)
H20	−0.5008	0.1324	0.9124	0.108*
C28	−0.0645 (4)	−0.2266 (2)	0.77079 (19)	0.0961 (8)
H28	−0.0576	−0.3056	0.7376	0.115*
C12	−0.1141 (3)	0.3253 (2)	0.47704 (17)	0.0897 (7)
H12	−0.0991	0.2830	0.4097	0.108*
C4	0.2318 (4)	0.0018 (2)	0.60314 (19)	0.0966 (8)
H4	0.2491	−0.0728	0.5612	0.116*

	U11	U22	U33	U12	U13	U23
S1	0.0404 (2)	0.0595 (3)	0.0869 (4)	−0.00416 (19)	−0.0106 (2)	0.0344 (3)
N1	0.0424 (7)	0.0498 (8)	0.0576 (9)	0.0038 (6)	−0.0025 (6)	0.0174 (7)
O5	0.0600 (8)	0.0685 (8)	0.0787 (9)	−0.0140 (6)	−0.0221 (7)	0.0211 (7)
C8	0.0427 (9)	0.0513 (10)	0.0631 (11)	0.0025 (7)	0.0010 (8)	0.0252 (9)
C1	0.0480 (9)	0.0540 (10)	0.0472 (9)	0.0049 (8)	−0.0019 (7)	0.0196 (8)
O2	0.0380 (7)	0.1093 (11)	0.1291 (13)	0.0009 (7)	0.0055 (7)	0.0759 (10)
O3	0.0795 (9)	0.0463 (7)	0.1094 (12)	−0.0062 (6)	−0.0360 (8)	0.0186 (8)
O4	0.0716 (9)	0.0545 (8)	0.0906 (10)	−0.0055 (7)	−0.0083 (8)	0.0049 (7)
C23	0.0625 (11)	0.0603 (11)	0.0440 (9)	−0.0096 (9)	−0.0043 (8)	0.0222 (9)
C18	0.0530 (10)	0.0621 (11)	0.0513 (10)	−0.0062 (8)	−0.0016 (8)	0.0202 (9)
C16	0.0454 (9)	0.0539 (10)	0.0464 (9)	0.0010 (8)	0.0030 (7)	0.0061 (8)
C2	0.0609 (11)	0.0650 (12)	0.0562 (11)	−0.0023 (9)	−0.0071 (9)	0.0183 (10)
C17	0.0529 (10)	0.0618 (11)	0.0470 (10)	−0.0031 (8)	−0.0031 (8)	0.0119 (9)
C9	0.0449 (10)	0.0726 (12)	0.0624 (11)	0.0091 (9)	0.0000 (8)	0.0186 (10)
C15	0.0441 (9)	0.0538 (10)	0.0635 (11)	0.0063 (8)	0.0013 (8)	0.0116 (9)
C6	0.0578 (11)	0.0662 (12)	0.0699 (12)	0.0160 (9)	0.0065 (9)	0.0315 (10)
C24	0.0489 (10)	0.0552 (11)	0.0511 (10)	−0.0014 (8)	0.0051 (8)	0.0053 (9)
C11	0.0646 (13)	0.0755 (13)	0.0728 (14)	−0.0040 (10)	−0.0153 (10)	0.0321 (11)
C26	0.0715 (13)	0.0700 (13)	0.0585 (11)	−0.0008 (10)	0.0024 (10)	0.0237 (10)
C22	0.0767 (14)	0.0709 (13)	0.0592 (12)	−0.0224 (11)	−0.0120 (10)	0.0288 (10)
C21	0.0653 (15)	0.1012 (19)	0.1063 (19)	−0.0308 (13)	−0.0220 (13)	0.0485 (16)
O1	0.0474 (9)	0.1394 (16)	0.206 (2)	0.0216 (9)	0.0138 (11)	0.0966 (15)
C13	0.0608 (13)	0.1092 (18)	0.0691 (14)	0.0235 (12)	0.0120 (11)	0.0287 (13)
C7	0.0494 (12)	0.0868 (15)	0.1220 (19)	0.0099 (10)	−0.0032 (12)	0.0603 (14)
C10	0.0453 (10)	0.0889 (15)	0.0774 (14)	0.0068 (9)	−0.0011 (10)	0.0330 (12)
C19	0.0590 (12)	0.0762 (14)	0.0869 (15)	0.0012 (10)	0.0072 (11)	0.0265 (12)
C3	0.1072 (19)	0.0684 (14)	0.0654 (13)	−0.0105 (13)	−0.0183 (13)	0.0134 (11)
C29	0.120 (2)	0.0722 (16)	0.0704 (15)	−0.0366 (15)	−0.0162 (14)	0.0236 (13)
C5	0.0900 (18)	0.0843 (17)	0.0969 (18)	0.0357 (14)	0.0201 (14)	0.0312 (14)
C14	0.106 (2)	0.128 (2)	0.107 (2)	−0.0087 (17)	−0.0507 (17)	0.0438 (18)
C27	0.1054 (19)	0.0709 (15)	0.0753 (15)	0.0135 (13)	0.0159 (13)	0.0248 (12)
C25	0.0586 (12)	0.0940 (16)	0.0771 (14)	−0.0224 (11)	−0.0221 (10)	0.0208 (12)
C20	0.0501 (12)	0.1022 (19)	0.126 (2)	−0.0058 (12)	−0.0021 (13)	0.0500 (17)
C28	0.145 (3)	0.0615 (14)	0.0779 (16)	−0.0086 (17)	0.0134 (17)	0.0187 (12)
C12	0.0936 (18)	0.115 (2)	0.0557 (13)	0.0193 (14)	−0.0014 (12)	0.0162 (13)
C4	0.133 (2)	0.0681 (15)	0.0801 (17)	0.0262 (16)	0.0096 (16)	0.0062 (13)

S1—O3	1.4194 (15)	C11—C14	1.508 (3)
S1—O2	1.4258 (14)	C26—C27	1.356 (3)
S1—N1	1.6483 (14)	C26—H26	0.9300
S1—C8	1.7572 (18)	C22—C21	1.402 (3)
N1—C1	1.436 (2)	C22—C29	1.408 (3)
N1—C15	1.490 (2)	C21—C20	1.345 (3)
O5—C24	1.332 (2)	C21—H21	0.9300
O5—C25	1.443 (2)	O1—C7	1.200 (2)
C8—C13	1.366 (3)	C13—C12	1.373 (3)
C8—C9	1.367 (2)	C13—H13	0.9300
C1—C2	1.381 (2)	C7—H7	0.9300
C1—C6	1.393 (2)	C10—H10	0.9300
O4—C24	1.195 (2)	C19—C20	1.404 (3)
C23—C26	1.411 (3)	C19—H19	0.9300
C23—C18	1.416 (2)	C3—C4	1.377 (3)
C23—C22	1.419 (3)	C3—H3	0.9300
C18—C19	1.364 (3)	C29—C28	1.342 (4)
C18—C17	1.474 (2)	C29—H29	0.9300
C16—C17	1.325 (2)	C5—C4	1.356 (4)
C16—C24	1.488 (2)	C5—H5	0.9300
C16—C15	1.492 (2)	C14—H14A	0.9600
C2—C3	1.376 (3)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C17—H17	0.9300	C27—C28	1.389 (3)
C9—C10	1.371 (3)	C27—H27	0.9300
C9—H9	0.9300	C25—H25A	0.9600
C15—H15A	0.9700	C25—H25B	0.9600
C15—H15B	0.9700	C25—H25C	0.9600
C6—C5	1.387 (3)	C20—H20	0.9300
C6—C7	1.477 (3)	C28—H28	0.9300
C11—C10	1.369 (3)	C12—H12	0.9300
C11—C12	1.372 (3)	C4—H4	0.9300
O3—S1—O2	119.86 (10)	C21—C22—C23	118.7 (2)
O3—S1—N1	106.84 (9)	C29—C22—C23	118.6 (2)
O2—S1—N1	106.02 (8)	C20—C21—C22	121.4 (2)
O3—S1—C8	108.59 (8)	C20—C21—H21	119.3
O2—S1—C8	107.37 (9)	C22—C21—H21	119.3
N1—S1—C8	107.59 (8)	C8—C13—C12	119.1 (2)
C1—N1—C15	116.53 (13)	C8—C13—H13	120.5
C1—N1—S1	116.14 (11)	C12—C13—H13	120.5
C15—N1—S1	117.98 (11)	O1—C7—C6	123.5 (2)
C24—O5—C25	116.36 (15)	O1—C7—H7	118.3
C13—C8—C9	120.22 (18)	C6—C7—H7	118.3
C13—C8—S1	120.42 (14)	C11—C10—C9	121.44 (19)
C9—C8—S1	119.35 (15)	C11—C10—H10	119.3
C2—C1—C6	120.04 (17)	C9—C10—H10	119.3
C2—C1—N1	120.62 (15)	C18—C19—C20	121.0 (2)
C6—C1—N1	119.33 (15)	C18—C19—H19	119.5
C26—C23—C18	122.86 (17)	C20—C19—H19	119.5
C26—C23—C22	118.01 (19)	C2—C3—C4	120.0 (2)
C18—C23—C22	119.13 (18)	C2—C3—H3	120.0
C19—C18—C23	119.57 (17)	C4—C3—H3	120.0
C19—C18—C17	120.37 (18)	C28—C29—C22	121.4 (2)
C23—C18—C17	119.91 (16)	C28—C29—H29	119.3
C17—C16—C24	119.54 (17)	C22—C29—H29	119.3
C17—C16—C15	125.68 (16)	C4—C5—C6	121.0 (2)
C24—C16—C15	114.77 (16)	C4—C5—H5	119.5
C3—C2—C1	119.9 (2)	C6—C5—H5	119.5
C3—C2—H2	120.0	C11—C14—H14A	109.5
C1—C2—H2	120.0	C11—C14—H14B	109.5
C16—C17—C18	127.39 (17)	H14A—C14—H14B	109.5
C16—C17—H17	116.3	C11—C14—H14C	109.5
C18—C17—H17	116.3	H14A—C14—H14C	109.5
C8—C9—C10	119.69 (19)	H14B—C14—H14C	109.5
C8—C9—H9	120.2	C26—C27—C28	120.4 (2)
C10—C9—H9	120.2	C26—C27—H27	119.8
N1—C15—C16	108.06 (13)	C28—C27—H27	119.8
N1—C15—H15A	110.1	O5—C25—H25A	109.5
C16—C15—H15A	110.1	O5—C25—H25B	109.5
N1—C15—H15B	110.1	H25A—C25—H25B	109.5
C16—C15—H15B	110.1	O5—C25—H25C	109.5
H15A—C15—H15B	108.4	H25A—C25—H25C	109.5
C5—C6—C1	118.6 (2)	H25B—C25—H25C	109.5
C5—C6—C7	118.7 (2)	C21—C20—C19	120.1 (2)
C1—C6—C7	122.60 (18)	C21—C20—H20	120.0
O4—C24—O5	123.14 (17)	C19—C20—H20	120.0
O4—C24—C16	123.83 (18)	C29—C28—C27	120.4 (2)
O5—C24—C16	113.03 (16)	C29—C28—H28	119.8
C10—C11—C12	117.65 (19)	C27—C28—H28	119.8
C10—C11—C14	121.4 (2)	C11—C12—C13	121.9 (2)
C12—C11—C14	121.0 (2)	C11—C12—H12	119.0
C27—C26—C23	121.1 (2)	C13—C12—H12	119.0
C27—C26—H26	119.4	C5—C4—C3	120.3 (2)
C23—C26—H26	119.4	C5—C4—H4	119.9
C21—C22—C29	122.7 (2)	C3—C4—H4	119.9
O3—S1—N1—C1	−177.99 (11)	C25—O5—C24—C16	−175.82 (15)
O2—S1—N1—C1	−49.07 (14)	C17—C16—C24—O4	−154.66 (19)
C8—S1—N1—C1	65.57 (13)	C15—C16—C24—O4	24.1 (2)
O3—S1—N1—C15	36.52 (13)	C17—C16—C24—O5	24.6 (2)
O2—S1—N1—C15	165.44 (12)	C15—C16—C24—O5	−156.62 (15)
C8—S1—N1—C15	−79.92 (13)	C18—C23—C26—C27	179.60 (18)
O3—S1—C8—C13	149.02 (17)	C22—C23—C26—C27	−0.3 (3)
O2—S1—C8—C13	18.05 (19)	C26—C23—C22—C21	177.87 (18)
N1—S1—C8—C13	−95.69 (17)	C18—C23—C22—C21	−2.0 (3)
O3—S1—C8—C9	−32.37 (17)	C26—C23—C22—C29	−1.7 (3)
O2—S1—C8—C9	−163.34 (14)	C18—C23—C22—C29	178.44 (17)
N1—S1—C8—C9	82.92 (15)	C29—C22—C21—C20	−179.9 (2)
C15—N1—C1—C2	49.3 (2)	C23—C22—C21—C20	0.5 (3)
S1—N1—C1—C2	−96.70 (17)	C9—C8—C13—C12	−0.3 (3)
C15—N1—C1—C6	−130.40 (16)	S1—C8—C13—C12	178.28 (18)
S1—N1—C1—C6	83.60 (17)	C5—C6—C7—O1	11.4 (3)
C26—C23—C18—C19	−178.47 (18)	C1—C6—C7—O1	−170.5 (2)
C22—C23—C18—C19	1.4 (3)	C12—C11—C10—C9	0.0 (3)
C26—C23—C18—C17	−2.9 (3)	C14—C11—C10—C9	179.0 (2)
C22—C23—C18—C17	177.00 (16)	C8—C9—C10—C11	0.2 (3)
C6—C1—C2—C3	−0.9 (3)	C23—C18—C19—C20	0.7 (3)
N1—C1—C2—C3	179.41 (17)	C17—C18—C19—C20	−174.9 (2)
C24—C16—C17—C18	171.62 (16)	C1—C2—C3—C4	−1.1 (3)
C15—C16—C17—C18	−7.0 (3)	C21—C22—C29—C28	−177.0 (2)
C19—C18—C17—C16	−58.0 (3)	C23—C22—C29—C28	2.6 (3)
C23—C18—C17—C16	126.4 (2)	C1—C6—C5—C4	−2.3 (3)
C13—C8—C9—C10	0.0 (3)	C7—C6—C5—C4	175.8 (2)
S1—C8—C9—C10	−178.60 (15)	C23—C26—C27—C28	1.5 (3)
C1—N1—C15—C16	67.76 (17)	C22—C21—C20—C19	1.5 (4)
S1—N1—C15—C16	−146.88 (12)	C18—C19—C20—C21	−2.2 (4)
C17—C16—C15—N1	−108.93 (19)	C22—C29—C28—C27	−1.4 (4)
C24—C16—C15—N1	72.38 (17)	C26—C27—C28—C29	−0.6 (4)
C2—C1—C6—C5	2.6 (3)	C10—C11—C12—C13	−0.3 (4)
N1—C1—C6—C5	−177.71 (17)	C14—C11—C12—C13	−179.4 (2)
C2—C1—C6—C7	−175.45 (18)	C8—C13—C12—C11	0.5 (4)
N1—C1—C6—C7	4.3 (3)	C6—C5—C4—C3	0.3 (4)
C25—O5—C24—O4	3.5 (3)	C2—C3—C4—C5	1.4 (4)

Cg is the centroid of the C22/C23/C26–C29 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25A···O4i	0.96	2.50	3.462 (3)	177.
C10—H10···O2ii	0.93	2.44	3.305 (2)	155.
C17—H17···Cgiii	0.93	2.78	3.528 (2)	138.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C22/C23/C26–C29 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25A⋯O4i	0.96	2.50	3.462 (3)	177
C10—H10⋯O2ii	0.93	2.44	3.305 (2)	155
C17—H17⋯Cgiii	0.93	2.78	3.528 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) .