2-(4-Fluoro-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

In the title compound, C25H15FN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.1534 (16) Å for the C atom connected to the 4-fluoro-2-nitro-phenyl ring. It is almost orthogonal to the phenyl-sulfonyl and nitro-phenyl rings, making dihedral angles of 88.45 (8) and 79.26 (7)°, respectively. The mol-ecular structure is stabilized by O-H⋯O and C-H⋯O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol-ecules are linked by two C-H⋯O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, so forming a two-dimensional network lying parallel to (001). There are also supra-molecular R 4 (3)(28) graph-set ring motifs enclosed within these networks.

Related literature

For the biological activity and uses of carbazole derivatives, see: Itoigawa et al. (2000 ▶); Ramsewak et al. (1999 ▶). For their electronic properties and applications, see: Friend et al. (1999 ▶); Zhang et al. (2004 ▶). For a related structure, see: Gopinath et al. (2013 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the the Thrope–Ingold effect, see: Bassindale (1984 ▶).

Experimental

Crystal data

C25H15FN2O6S

M = 490.45

Monoclinic,

a = 8.124 (5) Å

b = 14.191 (5) Å

c = 18.607 (5) Å

β = 93.820 (5)°

V = 2140.4 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Brukker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.930, T max = 0.949

31082 measured reflections

7207 independent reflections

4725 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.143

S = 1.01

7207 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814002633/su2695sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002633/su2695Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002633/su2695Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H15FN2O6S	F(000) = 1008
Mr = 490.45	Dx = 1.522 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7207 reflections
a = 8.124 (5) Å	θ = 2.2–31.7°
b = 14.191 (5) Å	µ = 0.21 mm−1
c = 18.607 (5) Å	T = 296 K
β = 93.820 (5)°	Block, yellow
V = 2140.4 (16) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Brukker Kappa APEXII CCD diffractometer	7207 independent reflections
Radiation source: fine-focus sealed tube	4725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω & φ scans	θmax = 31.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.930, Tmax = 0.949	k = −20→20
31082 measured reflections	l = −26→27

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.4156P] where P = (Fo2 + 2Fc2)/3
7207 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.44 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	0.22774 (18)	0.88060 (12)	−0.01369 (8)	0.0374 (3)
C2	0.1387 (2)	0.83895 (14)	−0.07118 (9)	0.0495 (4)
H2	0.1307	0.7738	−0.0757	0.059*
C3	0.0621 (2)	0.89880 (16)	−0.12166 (10)	0.0566 (5)
H3	−0.0006	0.8729	−0.1604	0.068*
C4	0.0754 (2)	0.99483 (15)	−0.11661 (10)	0.0552 (5)
H4	0.0208	1.0325	−0.1514	0.066*
C5	0.1683 (2)	1.03627 (14)	−0.06079 (9)	0.0482 (4)
H5	0.1798	1.1014	−0.0582	0.058*
C6	0.24489 (19)	0.97816 (12)	−0.00809 (8)	0.0378 (3)
C7	0.33800 (19)	0.99774 (11)	0.05859 (8)	0.0361 (3)
C8	0.37439 (17)	0.91229 (10)	0.09332 (8)	0.0338 (3)
C9	0.45053 (19)	0.90720 (11)	0.16234 (8)	0.0368 (3)
H9	0.4734	0.8494	0.1843	0.044*
C10	0.49084 (19)	0.99004 (11)	0.19702 (8)	0.0366 (3)
C11	0.4656 (2)	1.07785 (11)	0.16215 (9)	0.0412 (4)
C12	0.3891 (2)	1.08113 (11)	0.09237 (9)	0.0408 (4)
C13	0.5105 (3)	1.16400 (13)	0.19907 (11)	0.0577 (5)
H13	0.5595	1.1591	0.2455	0.069*
C14	0.10618 (19)	0.73000 (10)	0.11778 (9)	0.0380 (3)
C15	0.1077 (2)	0.76246 (12)	0.18780 (10)	0.0470 (4)
H15	0.2061	0.7803	0.2125	0.056*
C16	−0.0402 (3)	0.76793 (15)	0.22048 (13)	0.0623 (5)
H16	−0.0425	0.7906	0.2673	0.075*
C17	−0.1846 (3)	0.73945 (18)	0.18295 (16)	0.0730 (7)
H17	−0.2839	0.7433	0.2049	0.088*
C18	−0.1833 (3)	0.70603 (18)	0.11453 (15)	0.0729 (7)
H18	−0.2812	0.6863	0.0905	0.087*
C19	−0.0383 (2)	0.70121 (14)	0.08066 (12)	0.0558 (5)
H19	−0.0374	0.6790	0.0337	0.067*
C20	0.55668 (19)	0.98415 (11)	0.27357 (8)	0.0367 (3)
C21	0.7260 (2)	0.98788 (14)	0.29145 (10)	0.0503 (4)
H21	0.7975	0.9992	0.2554	0.060*
C22	0.7897 (2)	0.97524 (15)	0.36099 (11)	0.0550 (5)
H22	0.9028	0.9789	0.3721	0.066*
C23	0.6842 (2)	0.95715 (13)	0.41362 (10)	0.0500 (4)
C24	0.5168 (2)	0.95119 (12)	0.39949 (10)	0.0460 (4)
H24	0.4468	0.9375	0.4356	0.055*
C25	0.45671 (19)	0.96635 (11)	0.32961 (8)	0.0367 (3)
N1	0.31385 (16)	0.83887 (9)	0.04768 (7)	0.0369 (3)
N2	0.27697 (18)	0.96048 (12)	0.31633 (8)	0.0497 (4)
O1	0.35888 (18)	1.16282 (9)	0.05773 (7)	0.0589 (4)
H1	0.3946	1.2066	0.0830	0.088*
O2	0.4894 (3)	1.24286 (10)	0.17434 (9)	0.0816 (5)
O3	0.26853 (16)	0.67320 (8)	0.01041 (7)	0.0514 (3)
O4	0.42270 (13)	0.70889 (8)	0.12536 (6)	0.0419 (3)
O5	0.20964 (17)	1.00982 (13)	0.27085 (9)	0.0735 (5)
O6	0.2029 (2)	0.90511 (16)	0.35160 (11)	0.1023 (7)
F1	0.74611 (17)	0.94386 (10)	0.48170 (7)	0.0770 (4)
S1	0.28971 (5)	0.72821 (3)	0.07403 (2)	0.03511 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0366 (7)	0.0465 (8)	0.0296 (7)	−0.0002 (6)	0.0053 (6)	0.0006 (6)
C2	0.0556 (10)	0.0548 (10)	0.0374 (9)	−0.0056 (8)	−0.0022 (7)	−0.0026 (7)
C3	0.0590 (11)	0.0758 (14)	0.0339 (9)	−0.0018 (10)	−0.0047 (8)	0.0001 (9)
C4	0.0575 (11)	0.0727 (13)	0.0352 (9)	0.0114 (9)	0.0013 (8)	0.0106 (8)
C5	0.0543 (10)	0.0519 (10)	0.0392 (9)	0.0066 (8)	0.0093 (8)	0.0095 (7)
C6	0.0378 (8)	0.0447 (8)	0.0319 (8)	0.0003 (6)	0.0092 (6)	0.0038 (6)
C7	0.0382 (8)	0.0376 (7)	0.0333 (8)	−0.0016 (6)	0.0089 (6)	0.0028 (6)
C8	0.0331 (7)	0.0355 (7)	0.0333 (7)	−0.0034 (5)	0.0059 (6)	−0.0021 (6)
C9	0.0406 (8)	0.0347 (7)	0.0349 (8)	−0.0031 (6)	0.0017 (6)	0.0009 (6)
C10	0.0386 (8)	0.0391 (8)	0.0325 (8)	−0.0048 (6)	0.0066 (6)	−0.0027 (6)
C11	0.0521 (9)	0.0346 (7)	0.0382 (8)	−0.0067 (6)	0.0114 (7)	−0.0024 (6)
C12	0.0482 (9)	0.0353 (8)	0.0401 (9)	−0.0015 (6)	0.0125 (7)	0.0036 (6)
C13	0.0858 (14)	0.0397 (9)	0.0481 (11)	−0.0105 (9)	0.0095 (10)	−0.0066 (8)
C14	0.0328 (7)	0.0342 (7)	0.0472 (9)	0.0001 (6)	0.0033 (6)	0.0046 (6)
C15	0.0430 (9)	0.0484 (9)	0.0504 (10)	0.0018 (7)	0.0084 (7)	0.0019 (8)
C16	0.0641 (13)	0.0635 (12)	0.0624 (13)	0.0120 (10)	0.0268 (10)	0.0099 (10)
C17	0.0427 (11)	0.0805 (15)	0.099 (2)	0.0087 (10)	0.0262 (12)	0.0261 (14)
C18	0.0370 (10)	0.0903 (17)	0.0909 (19)	−0.0082 (10)	0.0017 (10)	0.0159 (14)
C19	0.0393 (9)	0.0626 (11)	0.0643 (13)	−0.0084 (8)	−0.0046 (8)	0.0023 (10)
C20	0.0407 (8)	0.0355 (7)	0.0342 (8)	−0.0041 (6)	0.0039 (6)	−0.0051 (6)
C21	0.0396 (9)	0.0625 (11)	0.0495 (10)	−0.0061 (8)	0.0085 (7)	−0.0077 (8)
C22	0.0401 (9)	0.0656 (12)	0.0581 (12)	0.0034 (8)	−0.0046 (8)	−0.0095 (9)
C23	0.0586 (11)	0.0491 (10)	0.0407 (9)	0.0097 (8)	−0.0084 (8)	−0.0021 (7)
C24	0.0520 (10)	0.0486 (9)	0.0377 (9)	0.0037 (7)	0.0063 (7)	0.0011 (7)
C25	0.0368 (8)	0.0380 (7)	0.0352 (8)	−0.0002 (6)	0.0031 (6)	−0.0031 (6)
N1	0.0413 (7)	0.0368 (6)	0.0322 (7)	−0.0038 (5)	−0.0001 (5)	−0.0018 (5)
N2	0.0401 (8)	0.0659 (10)	0.0436 (8)	−0.0019 (7)	0.0071 (6)	0.0000 (7)
O1	0.0898 (10)	0.0357 (6)	0.0513 (8)	−0.0036 (6)	0.0053 (7)	0.0092 (5)
O2	0.1389 (17)	0.0368 (7)	0.0692 (11)	−0.0122 (8)	0.0074 (10)	−0.0030 (7)
O3	0.0634 (8)	0.0438 (6)	0.0469 (7)	0.0007 (6)	0.0015 (6)	−0.0146 (5)
O4	0.0353 (6)	0.0406 (6)	0.0492 (7)	0.0047 (4)	−0.0024 (5)	−0.0001 (5)
O5	0.0471 (8)	0.1079 (13)	0.0652 (10)	0.0121 (8)	0.0009 (7)	0.0162 (9)
O6	0.0562 (10)	0.1501 (19)	0.1014 (14)	−0.0264 (11)	0.0103 (9)	0.0524 (14)
F1	0.0809 (9)	0.0987 (10)	0.0484 (7)	0.0167 (7)	−0.0194 (6)	0.0070 (7)
S1	0.03481 (19)	0.03234 (18)	0.0381 (2)	0.00070 (14)	0.00198 (14)	−0.00437 (14)

C1—C2	1.384 (2)	C14—S1	1.7459 (18)
C1—C6	1.395 (2)	C15—C16	1.384 (3)
C1—N1	1.427 (2)	C15—H15	0.9300
C2—C3	1.383 (3)	C16—C17	1.385 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.370 (3)	C17—C18	1.359 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.375 (3)	C18—C19	1.374 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.395 (2)	C19—H19	0.9300
C5—H5	0.9300	C20—C25	1.387 (2)
C6—C7	1.437 (2)	C20—C21	1.394 (2)
C7—C12	1.390 (2)	C21—C22	1.373 (3)
C7—C8	1.396 (2)	C21—H21	0.9300
C8—C9	1.390 (2)	C22—C23	1.368 (3)
C8—N1	1.4117 (19)	C22—H22	0.9300
C9—C10	1.370 (2)	C23—F1	1.345 (2)
C9—H9	0.9300	C23—C24	1.370 (3)
C10—C11	1.414 (2)	C24—C25	1.375 (2)
C10—C20	1.490 (2)	C24—H24	0.9300
C11—C12	1.402 (2)	C25—N2	1.467 (2)
C11—C13	1.437 (2)	N1—S1	1.6608 (14)
C12—O1	1.3411 (19)	N2—O5	1.202 (2)
C13—O2	1.218 (2)	N2—O6	1.209 (2)
C13—H13	0.9300	O1—H1	0.8200
C14—C15	1.381 (3)	O3—S1	1.4189 (12)
C14—C19	1.384 (2)	O4—S1	1.4202 (13)
C2—C1—C6	121.76 (15)	C16—C15—H15	120.7
C2—C1—N1	130.13 (16)	C15—C16—C17	119.5 (2)
C6—C1—N1	108.11 (13)	C15—C16—H16	120.2
C3—C2—C1	116.81 (18)	C17—C16—H16	120.2
C3—C2—H2	121.6	C18—C17—C16	121.0 (2)
C1—C2—H2	121.6	C18—C17—H17	119.5
C4—C3—C2	122.32 (18)	C16—C17—H17	119.5
C4—C3—H3	118.8	C17—C18—C19	120.5 (2)
C2—C3—H3	118.8	C17—C18—H18	119.8
C3—C4—C5	120.94 (17)	C19—C18—H18	119.8
C3—C4—H4	119.5	C18—C19—C14	118.7 (2)
C5—C4—H4	119.5	C18—C19—H19	120.6
C4—C5—C6	118.34 (18)	C14—C19—H19	120.6
C4—C5—H5	120.8	C25—C20—C21	116.44 (16)
C6—C5—H5	120.8	C25—C20—C10	122.55 (15)
C1—C6—C5	119.77 (16)	C21—C20—C10	120.77 (15)
C1—C6—C7	107.50 (14)	C22—C21—C20	121.61 (17)
C5—C6—C7	132.61 (16)	C22—C21—H21	119.2
C12—C7—C8	118.84 (15)	C20—C21—H21	119.2
C12—C7—C6	132.79 (15)	C23—C22—C21	118.93 (17)
C8—C7—C6	108.34 (14)	C23—C22—H22	120.5
C9—C8—C7	122.70 (14)	C21—C22—H22	120.5
C9—C8—N1	129.30 (14)	F1—C23—C22	119.16 (18)
C7—C8—N1	107.94 (13)	F1—C23—C24	118.45 (18)
C10—C9—C8	117.92 (14)	C22—C23—C24	122.38 (18)
C10—C9—H9	121.0	C23—C24—C25	117.19 (17)
C8—C9—H9	121.0	C23—C24—H24	121.4
C9—C10—C11	121.16 (15)	C25—C24—H24	121.4
C9—C10—C20	117.47 (14)	C24—C25—C20	123.41 (16)
C11—C10—C20	121.34 (14)	C24—C25—N2	115.91 (15)
C12—C11—C10	119.74 (14)	C20—C25—N2	120.66 (15)
C12—C11—C13	119.79 (16)	C8—N1—C1	107.92 (12)
C10—C11—C13	120.40 (16)	C8—N1—S1	124.30 (11)
O1—C12—C7	118.61 (15)	C1—N1—S1	124.56 (11)
O1—C12—C11	121.96 (15)	O5—N2—O6	122.76 (17)
C7—C12—C11	119.40 (14)	O5—N2—C25	119.13 (15)
O2—C13—C11	125.2 (2)	O6—N2—C25	118.10 (16)
O2—C13—H13	117.4	C12—O1—H1	109.5
C11—C13—H13	117.4	O3—S1—O4	119.96 (7)
C15—C14—C19	121.56 (17)	O3—S1—N1	106.50 (7)
C15—C14—S1	119.38 (13)	O4—S1—N1	106.35 (7)
C19—C14—S1	119.04 (15)	O3—S1—C14	109.70 (8)
C14—C15—C16	118.67 (18)	O4—S1—C14	108.93 (8)
C14—C15—H15	120.7	N1—S1—C14	104.19 (7)
C6—C1—C2—C3	−2.3 (3)	C15—C14—C19—C18	0.5 (3)
N1—C1—C2—C3	177.26 (16)	S1—C14—C19—C18	−177.66 (16)
C1—C2—C3—C4	1.4 (3)	C9—C10—C20—C25	−75.8 (2)
C2—C3—C4—C5	0.8 (3)	C11—C10—C20—C25	102.15 (19)
C3—C4—C5—C6	−1.9 (3)	C9—C10—C20—C21	98.30 (19)
C2—C1—C6—C5	1.2 (2)	C11—C10—C20—C21	−83.8 (2)
N1—C1—C6—C5	−178.45 (14)	C25—C20—C21—C22	−0.4 (3)
C2—C1—C6—C7	177.77 (15)	C10—C20—C21—C22	−174.86 (17)
N1—C1—C6—C7	−1.89 (17)	C20—C21—C22—C23	1.0 (3)
C4—C5—C6—C1	0.9 (2)	C21—C22—C23—F1	179.39 (18)
C4—C5—C6—C7	−174.60 (17)	C21—C22—C23—C24	0.0 (3)
C1—C6—C7—C12	−178.73 (17)	F1—C23—C24—C25	179.14 (16)
C5—C6—C7—C12	−2.8 (3)	C22—C23—C24—C25	−1.4 (3)
C1—C6—C7—C8	−0.87 (17)	C23—C24—C25—C20	2.0 (3)
C5—C6—C7—C8	175.08 (16)	C23—C24—C25—N2	−179.38 (16)
C12—C7—C8—C9	4.2 (2)	C21—C20—C25—C24	−1.1 (2)
C6—C7—C8—C9	−174.01 (14)	C10—C20—C25—C24	173.19 (16)
C12—C7—C8—N1	−178.49 (13)	C21—C20—C25—N2	−179.64 (15)
C6—C7—C8—N1	3.30 (16)	C10—C20—C25—N2	−5.3 (2)
C7—C8—C9—C10	0.0 (2)	C9—C8—N1—C1	172.62 (15)
N1—C8—C9—C10	−176.72 (14)	C7—C8—N1—C1	−4.45 (16)
C8—C9—C10—C11	−4.0 (2)	C9—C8—N1—S1	12.2 (2)
C8—C9—C10—C20	173.94 (14)	C7—C8—N1—S1	−164.88 (11)
C9—C10—C11—C12	3.8 (2)	C2—C1—N1—C8	−175.68 (16)
C20—C10—C11—C12	−174.03 (15)	C6—C1—N1—C8	3.93 (16)
C9—C10—C11—C13	−179.24 (16)	C2—C1—N1—S1	−15.3 (2)
C20—C10—C11—C13	2.9 (2)	C6—C1—N1—S1	164.29 (11)
C8—C7—C12—O1	177.74 (14)	C24—C25—N2—O5	147.23 (18)
C6—C7—C12—O1	−4.6 (3)	C20—C25—N2—O5	−34.1 (2)
C8—C7—C12—C11	−4.3 (2)	C24—C25—N2—O6	−33.4 (3)
C6—C7—C12—C11	173.39 (16)	C20—C25—N2—O6	145.2 (2)
C10—C11—C12—O1	178.36 (15)	C8—N1—S1—O3	−165.23 (12)
C13—C11—C12—O1	1.4 (3)	C1—N1—S1—O3	37.55 (14)
C10—C11—C12—C7	0.5 (2)	C8—N1—S1—O4	−36.20 (14)
C13—C11—C12—C7	−176.50 (16)	C1—N1—S1—O4	166.58 (12)
C12—C11—C13—O2	−0.9 (3)	C8—N1—S1—C14	78.81 (14)
C10—C11—C13—O2	−177.9 (2)	C1—N1—S1—C14	−78.41 (14)
C19—C14—C15—C16	−1.4 (3)	C15—C14—S1—O3	166.60 (13)
S1—C14—C15—C16	176.77 (14)	C19—C14—S1—O3	−15.16 (16)
C14—C15—C16—C17	1.1 (3)	C15—C14—S1—O4	33.48 (15)
C15—C16—C17—C18	0.1 (3)	C19—C14—S1—O4	−148.28 (14)
C16—C17—C18—C19	−1.0 (4)	C15—C14—S1—N1	−79.71 (14)
C17—C18—C19—C14	0.7 (3)	C19—C14—S1—N1	98.53 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.89	2.611 (3)	146
C2—H2···O3	0.93	2.37	2.956 (3)	121
C9—H9···O4	0.93	2.30	2.902 (3)	122
C18—H18···O4i	0.93	2.55	3.221 (3)	129
C13—H13···O4ii	0.93	2.50	3.337 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.89	2.611 (3)	146
C2—H2⋯O3	0.93	2.37	2.956 (3)	121
C9—H9⋯O4	0.93	2.30	2.902 (3)	122
C18—H18⋯O4i	0.93	2.55	3.221 (3)	129
C13—H13⋯O4ii	0.93	2.50	3.337 (3)	150

Symmetry codes: (i) ; (ii) .