Methyl (2Z)-2-({N-[2-(hy-droxy-meth-yl)phen-yl]-4-methyl-benzene-sulfonamido}-meth-yl)-3-phenyl-prop-2-enoate.

In the title compound, C(25)H(25)NO(5)S, the O atom of the hy-droxy group is disordered over two positions, with occupancies of 0.820 (2) and 0.180 (2). The sulfonyl-bound benzene ring forms dihedral angles of 31.8 (1) and 60.7 (1)°, respectively, with the hy-droxy-methyl-benzene and phenyl rings. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, generating an S(8) ring motif. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds and 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 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H25NO5S

M = 451.52

Triclinic,

a = 7.9528 (3) Å

b = 9.5396 (3) Å

c = 15.3299 (5) Å

α = 88.253 (2)°

β = 83.571 (1)°

γ = 76.215 (2)°

V = 1122.42 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.18 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 = 0.959, T max = 0.971

25861 measured reflections

7132 independent reflections

5255 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.05

7132 reflections

297 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.31 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/S1600536812000864/bt5779sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000864/bt5779Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000864/bt5779Isup3.cml

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

C25H25NO5S	Z = 2
Mr = 451.52	F(000) = 476
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9528 (3) Å	Cell parameters from 7307 reflections
b = 9.5396 (3) Å	θ = 1.3–31.3°
c = 15.3299 (5) Å	µ = 0.18 mm−1
α = 88.253 (2)°	T = 293 K
β = 83.571 (1)°	Block, colourless
γ = 76.215 (2)°	0.23 × 0.21 × 0.16 mm
V = 1122.42 (7) Å3

Bruker APEXII CCD diffractometer	7132 independent reflections
Radiation source: fine-focus sealed tube	5255 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 31.3°, θmin = 1.3°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.959, Tmax = 0.971	l = −21→22
25861 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.1756P] where P = (Fo2 + 2Fc2)/3
7132 reflections	(Δ/σ)max < 0.001
297 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.31 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	Occ. (<1)
C1	0.20025 (16)	0.58467 (13)	0.36181 (8)	0.0327 (2)
C2	0.03176 (18)	0.65951 (14)	0.39145 (9)	0.0401 (3)
H2	−0.0629	0.6363	0.3699	0.048*
C3	0.0045 (2)	0.76791 (16)	0.45268 (10)	0.0511 (4)
H3	−0.1082	0.8175	0.4725	0.061*
C4	0.1448 (3)	0.80219 (17)	0.48427 (11)	0.0575 (4)
H4	0.1271	0.8762	0.5248	0.069*
C5	0.3121 (2)	0.72685 (16)	0.45592 (10)	0.0515 (4)
H5	0.4056	0.7507	0.4783	0.062*
C6	0.34408 (18)	0.61594 (14)	0.39460 (9)	0.0393 (3)
C8	0.04825 (17)	0.61769 (13)	0.16515 (8)	0.0343 (3)
C9	−0.05349 (19)	0.55105 (14)	0.12048 (9)	0.0410 (3)
H9	−0.0160	0.4536	0.1064	0.049*
C10	−0.2116 (2)	0.63118 (16)	0.09707 (10)	0.0469 (3)
H10	−0.2801	0.5867	0.0672	0.056*
C11	−0.26927 (19)	0.77612 (15)	0.11741 (10)	0.0443 (3)
C12	−0.1653 (2)	0.84054 (14)	0.16182 (10)	0.0460 (3)
H12	−0.2029	0.9380	0.1758	0.055*
C13	−0.0071 (2)	0.76351 (14)	0.18575 (9)	0.0423 (3)
H13	0.0615	0.8085	0.2152	0.051*
C14	−0.4407 (2)	0.8624 (2)	0.09128 (14)	0.0681 (5)
H14A	−0.4480	0.8451	0.0306	0.102*
H14B	−0.4493	0.9632	0.0997	0.102*
H14C	−0.5343	0.8338	0.1268	0.102*
C15	0.11357 (16)	0.36554 (12)	0.31857 (8)	0.0339 (2)
H15A	0.0152	0.3908	0.2843	0.041*
H15B	0.0683	0.3736	0.3801	0.041*
C16	0.20914 (16)	0.21190 (13)	0.29938 (8)	0.0350 (3)
C17	0.16244 (17)	0.12583 (14)	0.24467 (9)	0.0393 (3)
H17	0.2324	0.0328	0.2378	0.047*
C18	0.01129 (17)	0.16300 (13)	0.19390 (9)	0.0364 (3)
C19	0.0349 (2)	0.14001 (16)	0.10405 (10)	0.0459 (3)
H19	0.1452	0.0979	0.0768	0.055*
C20	−0.1044 (2)	0.17926 (17)	0.05454 (10)	0.0530 (4)
H20	−0.0870	0.1655	−0.0059	0.064*
C21	−0.2684 (2)	0.23862 (17)	0.09474 (11)	0.0528 (4)
H21	−0.3616	0.2661	0.0613	0.063*
C22	−0.29490 (19)	0.25740 (16)	0.18413 (11)	0.0482 (3)
H22	−0.4065	0.2948	0.2114	0.058*
C23	−0.15595 (18)	0.22084 (15)	0.23353 (9)	0.0403 (3)
H23	−0.1744	0.2350	0.2939	0.048*
C24	0.36113 (17)	0.15603 (14)	0.34979 (9)	0.0385 (3)
C25	0.6052 (2)	−0.03467 (18)	0.36773 (12)	0.0552 (4)
H25A	0.6903	0.0223	0.3604	0.083*
H25B	0.6568	−0.1303	0.3459	0.083*
H25C	0.5648	−0.0397	0.4289	0.083*
N1	0.22546 (13)	0.47007 (10)	0.29838 (7)	0.0317 (2)
O2	0.36596 (14)	0.61308 (12)	0.18924 (7)	0.0517 (3)
O3	0.29601 (13)	0.38840 (11)	0.14434 (6)	0.0463 (2)
O4	0.39010 (15)	0.21719 (12)	0.41165 (8)	0.0565 (3)
O5	0.46033 (14)	0.03080 (11)	0.31967 (7)	0.0522 (3)
S1	0.24992 (4)	0.51837 (3)	0.19400 (2)	0.03568 (9)
C7	0.52803 (19)	0.53288 (18)	0.36886 (11)	0.0509 (4)
H7A	0.5850	0.5067	0.4217	0.061*	0.820 (2)
H7B	0.5248	0.4441	0.3405	0.061*	0.820 (2)
H7C	0.5370	0.4333	0.3870	0.061*	0.180 (2)
H7D	0.5488	0.5337	0.3053	0.061*	0.180 (2)
O1A	0.62756 (19)	0.60607 (18)	0.31313 (10)	0.0630 (4)	0.820 (2)
H1A	0.5817	0.6274	0.2677	0.095*	0.820 (2)
O1B	0.6587 (8)	0.5806 (8)	0.4002 (4)	0.0630 (4)	0.180 (2)
H1B	0.6916	0.5313	0.4426	0.095*	0.180 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0352 (6)	0.0318 (5)	0.0329 (6)	−0.0103 (5)	−0.0073 (5)	0.0012 (4)
C2	0.0375 (7)	0.0411 (7)	0.0410 (7)	−0.0077 (5)	−0.0050 (5)	−0.0004 (5)
C3	0.0522 (9)	0.0453 (7)	0.0490 (8)	0.0005 (7)	−0.0006 (7)	−0.0060 (6)
C4	0.0780 (12)	0.0469 (8)	0.0479 (9)	−0.0131 (8)	−0.0075 (8)	−0.0130 (7)
C5	0.0619 (10)	0.0499 (8)	0.0506 (8)	−0.0235 (7)	−0.0166 (7)	−0.0052 (6)
C6	0.0404 (7)	0.0410 (6)	0.0412 (7)	−0.0157 (6)	−0.0117 (5)	0.0007 (5)
C8	0.0372 (6)	0.0345 (6)	0.0325 (6)	−0.0101 (5)	−0.0069 (5)	0.0034 (5)
C9	0.0461 (7)	0.0339 (6)	0.0444 (7)	−0.0090 (5)	−0.0124 (6)	−0.0010 (5)
C10	0.0471 (8)	0.0449 (7)	0.0533 (8)	−0.0144 (6)	−0.0185 (6)	0.0033 (6)
C11	0.0422 (7)	0.0425 (7)	0.0469 (8)	−0.0079 (6)	−0.0077 (6)	0.0134 (6)
C12	0.0571 (9)	0.0318 (6)	0.0468 (8)	−0.0062 (6)	−0.0066 (6)	0.0045 (5)
C13	0.0543 (8)	0.0351 (6)	0.0408 (7)	−0.0139 (6)	−0.0114 (6)	0.0013 (5)
C14	0.0516 (10)	0.0588 (10)	0.0901 (14)	−0.0034 (8)	−0.0194 (9)	0.0235 (9)
C15	0.0310 (6)	0.0329 (6)	0.0398 (6)	−0.0107 (5)	−0.0060 (5)	0.0000 (5)
C16	0.0316 (6)	0.0341 (6)	0.0408 (6)	−0.0093 (5)	−0.0079 (5)	0.0025 (5)
C17	0.0337 (6)	0.0343 (6)	0.0502 (8)	−0.0065 (5)	−0.0083 (5)	−0.0041 (5)
C18	0.0352 (6)	0.0316 (6)	0.0449 (7)	−0.0099 (5)	−0.0096 (5)	−0.0053 (5)
C19	0.0446 (8)	0.0464 (7)	0.0468 (8)	−0.0111 (6)	−0.0021 (6)	−0.0097 (6)
C20	0.0671 (10)	0.0552 (8)	0.0417 (8)	−0.0198 (8)	−0.0144 (7)	−0.0038 (6)
C21	0.0543 (9)	0.0470 (8)	0.0627 (10)	−0.0127 (7)	−0.0288 (8)	0.0006 (7)
C22	0.0341 (7)	0.0471 (7)	0.0645 (9)	−0.0079 (6)	−0.0120 (6)	−0.0089 (7)
C23	0.0368 (7)	0.0434 (7)	0.0430 (7)	−0.0122 (5)	−0.0061 (5)	−0.0076 (5)
C24	0.0355 (6)	0.0372 (6)	0.0448 (7)	−0.0107 (5)	−0.0099 (5)	0.0052 (5)
C25	0.0428 (8)	0.0558 (9)	0.0626 (10)	0.0017 (7)	−0.0180 (7)	0.0089 (7)
N1	0.0315 (5)	0.0334 (5)	0.0332 (5)	−0.0115 (4)	−0.0074 (4)	−0.0002 (4)
O2	0.0446 (6)	0.0671 (7)	0.0514 (6)	−0.0299 (5)	−0.0065 (5)	0.0116 (5)
O3	0.0406 (5)	0.0528 (6)	0.0407 (5)	−0.0009 (4)	−0.0032 (4)	−0.0082 (4)
O4	0.0584 (7)	0.0547 (6)	0.0587 (7)	−0.0063 (5)	−0.0291 (5)	−0.0066 (5)
O5	0.0452 (6)	0.0466 (5)	0.0611 (7)	0.0038 (5)	−0.0211 (5)	−0.0034 (5)
S1	0.03119 (16)	0.04236 (17)	0.03454 (16)	−0.01077 (12)	−0.00391 (11)	0.00105 (12)
C7	0.0365 (7)	0.0594 (9)	0.0609 (9)	−0.0160 (7)	−0.0129 (6)	−0.0015 (7)
O1A	0.0481 (8)	0.0859 (10)	0.0618 (9)	−0.0297 (7)	−0.0067 (6)	0.0066 (8)
O1B	0.0481 (8)	0.0859 (10)	0.0618 (9)	−0.0297 (7)	−0.0067 (6)	0.0066 (8)

C1—C2	1.3926 (18)	C16—C24	1.4897 (17)
C1—C6	1.3966 (17)	C17—C18	1.4717 (18)
C1—N1	1.4484 (15)	C17—H17	0.9300
C2—C3	1.380 (2)	C18—C19	1.3863 (19)
C2—H2	0.9300	C18—C23	1.3900 (19)
C3—C4	1.375 (2)	C19—C20	1.385 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.381 (2)	C20—C21	1.375 (2)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.395 (2)	C21—C22	1.374 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.504 (2)	C22—C23	1.3799 (19)
C8—C9	1.3869 (18)	C22—H22	0.9300
C8—C13	1.3901 (18)	C23—H23	0.9300
C8—S1	1.7535 (13)	C24—O4	1.1998 (17)
C9—C10	1.3859 (19)	C24—O5	1.3288 (16)
C9—H9	0.9300	C25—O5	1.4419 (17)
C10—C11	1.383 (2)	C25—H25A	0.9600
C10—H10	0.9300	C25—H25B	0.9600
C11—C12	1.385 (2)	C25—H25C	0.9600
C11—C14	1.505 (2)	N1—S1	1.6548 (10)
C12—C13	1.379 (2)	O2—S1	1.4323 (10)
C12—H12	0.9300	O3—S1	1.4247 (10)
C13—H13	0.9300	C7—O1B	1.367 (4)
C14—H14A	0.9600	C7—O1A	1.385 (2)
C14—H14B	0.9600	C7—H7A	0.9700
C14—H14C	0.9600	C7—H7B	0.9700
C15—N1	1.4915 (15)	C7—H7C	0.9700
C15—C16	1.5025 (17)	C7—H7D	0.9700
C15—H15A	0.9700	O1A—H7D	1.0542
C15—H15B	0.9700	O1A—H1A	0.8200
C16—C17	1.3315 (18)	O1B—H1B	0.8200
C2—C1—C6	120.74 (12)	C20—C19—H19	119.8
C2—C1—N1	119.33 (11)	C18—C19—H19	119.8
C6—C1—N1	119.89 (11)	C21—C20—C19	120.00 (14)
C3—C2—C1	120.35 (13)	C21—C20—H20	120.0
C3—C2—H2	119.8	C19—C20—H20	120.0
C1—C2—H2	119.8	C22—C21—C20	120.15 (14)
C4—C3—C2	119.66 (14)	C22—C21—H21	119.9
C4—C3—H3	120.2	C20—C21—H21	119.9
C2—C3—H3	120.2	C21—C22—C23	120.04 (14)
C3—C4—C5	120.15 (14)	C21—C22—H22	120.0
C3—C4—H4	119.9	C23—C22—H22	120.0
C5—C4—H4	119.9	C22—C23—C18	120.64 (13)
C4—C5—C6	121.63 (15)	C22—C23—H23	119.7
C4—C5—H5	119.2	C18—C23—H23	119.7
C6—C5—H5	119.2	O4—C24—O5	123.50 (12)
C5—C6—C1	117.44 (13)	O4—C24—C16	123.47 (12)
C5—C6—C7	119.57 (13)	O5—C24—C16	113.03 (11)
C1—C6—C7	122.96 (12)	O5—C25—H25A	109.5
C9—C8—C13	120.41 (12)	O5—C25—H25B	109.5
C9—C8—S1	119.85 (10)	H25A—C25—H25B	109.5
C13—C8—S1	119.73 (10)	O5—C25—H25C	109.5
C10—C9—C8	119.29 (12)	H25A—C25—H25C	109.5
C10—C9—H9	120.4	H25B—C25—H25C	109.5
C8—C9—H9	120.4	C1—N1—C15	115.15 (10)
C11—C10—C9	121.12 (13)	C1—N1—S1	115.85 (8)
C11—C10—H10	119.4	C15—N1—S1	115.24 (8)
C9—C10—H10	119.4	C24—O5—C25	116.57 (12)
C10—C11—C12	118.59 (13)	O3—S1—O2	119.99 (7)
C10—C11—C14	120.71 (14)	O3—S1—N1	106.47 (6)
C12—C11—C14	120.69 (14)	O2—S1—N1	105.76 (6)
C13—C12—C11	121.53 (13)	O3—S1—C8	107.61 (6)
C13—C12—H12	119.2	O2—S1—C8	107.99 (6)
C11—C12—H12	119.2	N1—S1—C8	108.60 (6)
C12—C13—C8	119.05 (13)	O1B—C7—O1A	60.6 (3)
C12—C13—H13	120.5	O1B—C7—C6	117.5 (3)
C8—C13—H13	120.5	O1A—C7—C6	114.78 (14)
C11—C14—H14A	109.5	O1B—C7—H7A	49.6
C11—C14—H14B	109.5	O1A—C7—H7A	108.6
H14A—C14—H14B	109.5	C6—C7—H7A	108.6
C11—C14—H14C	109.5	O1B—C7—H7B	132.9
H14A—C14—H14C	109.5	O1A—C7—H7B	108.6
H14B—C14—H14C	109.5	C6—C7—H7B	108.6
N1—C15—C16	112.99 (10)	H7A—C7—H7B	107.5
N1—C15—H15A	109.0	O1B—C7—H7C	108.7
C16—C15—H15A	109.0	O1A—C7—H7C	135.8
N1—C15—H15B	109.0	C6—C7—H7C	108.0
C16—C15—H15B	109.0	H7A—C7—H7C	65.9
H15A—C15—H15B	107.8	H7B—C7—H7C	44.2
C17—C16—C24	120.28 (12)	O1B—C7—H7D	107.1
C17—C16—C15	124.55 (11)	O1A—C7—H7D	49.4
C24—C16—C15	115.12 (11)	C6—C7—H7D	107.9
C16—C17—C18	126.57 (12)	H7A—C7—H7D	143.1
C16—C17—H17	116.7	H7B—C7—H7D	64.9
C18—C17—H17	116.7	H7C—C7—H7D	107.2
C19—C18—C23	118.62 (12)	C7—O1A—H7D	44.3
C19—C18—C17	119.55 (12)	C7—O1A—H1A	109.5
C23—C18—C17	121.83 (12)	H7D—O1A—H1A	71.9
C20—C19—C18	120.50 (14)	C7—O1B—H1B	109.5
C6—C1—C2—C3	1.2 (2)	C21—C22—C23—C18	−0.9 (2)
N1—C1—C2—C3	179.20 (12)	C19—C18—C23—C22	−1.3 (2)
C1—C2—C3—C4	0.2 (2)	C17—C18—C23—C22	178.71 (13)
C2—C3—C4—C5	−1.1 (3)	C17—C16—C24—O4	−165.13 (15)
C3—C4—C5—C6	0.6 (3)	C15—C16—C24—O4	12.34 (19)
C4—C5—C6—C1	0.8 (2)	C17—C16—C24—O5	14.26 (19)
C4—C5—C6—C7	−177.31 (15)	C15—C16—C24—O5	−168.28 (11)
C2—C1—C6—C5	−1.67 (19)	C2—C1—N1—C15	−46.81 (15)
N1—C1—C6—C5	−179.64 (12)	C6—C1—N1—C15	131.19 (12)
C2—C1—C6—C7	176.36 (13)	C2—C1—N1—S1	91.87 (12)
N1—C1—C6—C7	−1.61 (19)	C6—C1—N1—S1	−90.13 (12)
C13—C8—C9—C10	−0.4 (2)	C16—C15—N1—C1	−139.33 (11)
S1—C8—C9—C10	−179.19 (11)	C16—C15—N1—S1	81.74 (11)
C8—C9—C10—C11	0.1 (2)	O4—C24—O5—C25	2.6 (2)
C9—C10—C11—C12	0.1 (2)	C16—C24—O5—C25	−176.78 (12)
C9—C10—C11—C14	179.67 (15)	C1—N1—S1—O3	172.29 (8)
C10—C11—C12—C13	0.0 (2)	C15—N1—S1—O3	−49.07 (10)
C14—C11—C12—C13	−179.51 (15)	C1—N1—S1—O2	43.60 (10)
C11—C12—C13—C8	−0.4 (2)	C15—N1—S1—O2	−177.76 (8)
C9—C8—C13—C12	0.6 (2)	C1—N1—S1—C8	−72.09 (10)
S1—C8—C13—C12	179.34 (11)	C15—N1—S1—C8	66.55 (9)
N1—C15—C16—C17	−122.13 (14)	C9—C8—S1—O3	15.29 (13)
N1—C15—C16—C24	60.53 (14)	C13—C8—S1—O3	−163.49 (11)
C24—C16—C17—C18	176.84 (13)	C9—C8—S1—O2	146.17 (11)
C15—C16—C17—C18	−0.4 (2)	C13—C8—S1—O2	−32.61 (13)
C16—C17—C18—C19	127.54 (16)	C9—C8—S1—N1	−99.59 (12)
C16—C17—C18—C23	−52.5 (2)	C13—C8—S1—N1	81.63 (12)
C23—C18—C19—C20	2.5 (2)	C5—C6—C7—O1B	−6.8 (4)
C17—C18—C19—C20	−177.55 (13)	C1—C6—C7—O1B	175.2 (4)
C18—C19—C20—C21	−1.4 (2)	C5—C6—C7—O1A	−75.15 (19)
C19—C20—C21—C22	−0.8 (2)	C1—C6—C7—O1A	106.87 (16)
C20—C21—C22—C23	2.0 (2)

Cg1 and Cg2 are the centroids of the C18–C23 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2	0.82	2.23	2.958 (2)	147.
C9—H9···Cg1	0.93	2.80	3.545 (2)	138.
C5—H5···O4i	0.93	2.54	3.429 (2)	160.
C14—H14C···O2ii	0.96	2.55	3.359 (2)	143.
C12—H12···Cg1iii	0.93	2.72	3.506 (2)	143.
C20—H20···Cg2iv	0.93	2.92	3.593 (2)	130.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C23 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2	0.82	2.23	2.958 (2)	147
C9—H9⋯Cg1	0.93	2.80	3.545 (2)	138
C5—H5⋯O4i	0.93	2.54	3.429 (2)	160
C14—H14C⋯O2ii	0.96	2.55	3.359 (2)	143
C12—H12⋯Cg1iii	0.93	2.72	3.506 (2)	143
C20—H20⋯Cg2iv	0.93	2.92	3.593 (2)	130

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