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

In the title compound, C25H15ClN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.152 (3) Å for the C atom to which the 4-chloro-2-nitro-phenyl ring is attached. Its mean plane is almost orthogonal to the phenyl-sulfonyl and nitro-phenyl rings, making dihedral angles of 82.64 (14) and 79.89 (13)°, respectively. The N atom of the nitro group deviates by 0.032 (3) Å from the benzene ring to which it is attached. The mol-ecular structure features intra-molecular O-H⋯O and C-H⋯O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, forming a two-dimensional network lying parallel to (001). There are also R 4 (3)(28) supra-molecular 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 related structures, see: Chakkaravarthi et al. (2008 ▶). For bond-length distortions, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ▶).

Experimental

Crystal data

C25H15ClN2O6S

M = 506.91

Monoclinic,

a = 8.1947 (15) Å

b = 14.384 (3) Å

c = 18.795 (3) Å

β = 90.963 (9)°

V = 2215.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.910, T max = 0.939

16586 measured reflections

3893 independent reflections

2809 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.172

S = 1.05

3893 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAIn class="Chemical">NT (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/S1600536813022253/su2632sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022253/su2632Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022253/su2632Isup3.cml

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

C25H15ClN2O6S	F(000) = 1040
Mr = 506.91	Dx = 1.520 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3893 reflections
a = 8.1947 (15) Å	θ = 1.8–25.0°
b = 14.384 (3) Å	µ = 0.31 mm−1
c = 18.795 (3) Å	T = 296 K
β = 90.963 (9)°	Block, yellow
V = 2215.2 (7) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3893 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω & φ scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.910, Tmax = 0.939	k = −17→15
16586 measured reflections	l = −22→22

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) = 0.172	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0933P)2 + 0.9326P] where P = (Fo2 + 2Fc2)/3
3893 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.40 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	0.2551 (3)	0.6180 (2)	0.50926 (15)	0.0528 (8)
C2	0.3370 (4)	0.6615 (3)	0.56478 (17)	0.0671 (9)
H2	0.3374	0.7259	0.5694	0.081*
C3	0.4184 (4)	0.6050 (4)	0.61323 (19)	0.0788 (12)
H3	0.4772	0.6323	0.6505	0.095*
C4	0.4150 (5)	0.5097 (4)	0.60796 (19)	0.0780 (11)
H4	0.4717	0.4740	0.6414	0.094*
C5	0.3290 (4)	0.4662 (3)	0.55391 (19)	0.0685 (9)
H5	0.3241	0.4017	0.5512	0.082*
C6	0.2497 (3)	0.5214 (2)	0.50362 (16)	0.0536 (8)
C7	0.1606 (3)	0.4993 (2)	0.43898 (16)	0.0505 (7)
C8	0.1173 (3)	0.5826 (2)	0.40603 (16)	0.0469 (7)
C9	0.0421 (3)	0.5859 (2)	0.33864 (16)	0.0494 (7)
H9	0.0132	0.6421	0.3175	0.059*
C10	0.0132 (3)	0.5029 (2)	0.30519 (16)	0.0501 (7)
C11	0.0462 (4)	0.4168 (2)	0.33792 (18)	0.0561 (8)
C12	0.1204 (4)	0.4155 (2)	0.40598 (18)	0.0569 (8)
C13	0.0128 (5)	0.3305 (3)	0.3022 (2)	0.0770 (11)
H13	−0.0318	0.3342	0.2565	0.092*
C14	0.3698 (3)	0.7616 (2)	0.37430 (17)	0.0493 (7)
C15	0.3674 (4)	0.7328 (2)	0.3047 (2)	0.0622 (9)
H15	0.2690	0.7201	0.2813	0.075*
C16	0.5117 (5)	0.7232 (3)	0.2703 (2)	0.0809 (11)
H16	0.5125	0.7035	0.2232	0.097*
C17	0.6562 (5)	0.7428 (3)	0.3057 (3)	0.0918 (14)
H17	0.7546	0.7355	0.2824	0.110*
C18	0.6566 (5)	0.7726 (3)	0.3743 (3)	0.0935 (14)
H18	0.7549	0.7870	0.3971	0.112*
C19	0.5137 (4)	0.7815 (3)	0.4098 (2)	0.0722 (10)
H19	0.5135	0.8007	0.4571	0.087*
C20	−0.0564 (3)	0.5080 (2)	0.23145 (16)	0.0503 (7)
C21	−0.2215 (4)	0.5008 (3)	0.21838 (19)	0.0681 (9)
H21	−0.2892	0.4855	0.2558	0.082*
C22	−0.2902 (4)	0.5152 (3)	0.1522 (2)	0.0718 (10)
H22	−0.4023	0.5092	0.1451	0.086*
C23	−0.1919 (4)	0.5385 (3)	0.09668 (19)	0.0658 (9)
C24	−0.0268 (4)	0.5468 (2)	0.10637 (17)	0.0592 (8)
H24	0.0399	0.5635	0.0689	0.071*
C25	0.0376 (3)	0.5298 (2)	0.17300 (16)	0.0519 (7)
Cl1	−0.27788 (15)	0.55884 (9)	0.01388 (6)	0.1018 (4)
N1	0.1664 (3)	0.65682 (17)	0.45026 (13)	0.0503 (6)
N2	0.2158 (3)	0.5375 (2)	0.18092 (15)	0.0664 (8)
O1	0.1583 (3)	0.33589 (17)	0.43974 (14)	0.0784 (7)
H1	0.1286	0.2916	0.4153	0.118*
O2	0.0370 (5)	0.25321 (19)	0.32590 (17)	0.1032 (10)
O3	0.2092 (3)	0.82164 (17)	0.48325 (13)	0.0717 (7)
O4	0.0573 (2)	0.78288 (15)	0.37344 (12)	0.0569 (6)
O5	0.2857 (3)	0.4869 (2)	0.22158 (17)	0.0960 (9)
O6	0.2834 (3)	0.5962 (3)	0.14560 (17)	0.1149 (12)
S1	0.18862 (9)	0.76577 (5)	0.42149 (4)	0.0504 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0501 (15)	0.063 (2)	0.0456 (16)	−0.0008 (13)	0.0061 (13)	0.0019 (15)
C2	0.071 (2)	0.081 (3)	0.0489 (19)	−0.0099 (18)	0.0001 (16)	−0.0027 (17)
C3	0.071 (2)	0.116 (4)	0.049 (2)	−0.006 (2)	−0.0034 (17)	0.004 (2)
C4	0.076 (2)	0.108 (4)	0.051 (2)	0.013 (2)	0.0055 (18)	0.022 (2)
C5	0.073 (2)	0.077 (2)	0.057 (2)	0.0105 (18)	0.0189 (17)	0.0186 (19)
C6	0.0520 (16)	0.065 (2)	0.0445 (16)	−0.0013 (14)	0.0122 (13)	0.0055 (15)
C7	0.0482 (15)	0.0523 (19)	0.0514 (17)	−0.0029 (13)	0.0147 (13)	0.0056 (15)
C8	0.0425 (13)	0.0495 (18)	0.0490 (16)	−0.0033 (12)	0.0080 (12)	−0.0036 (14)
C9	0.0498 (15)	0.0492 (18)	0.0492 (17)	−0.0020 (13)	0.0025 (13)	−0.0023 (14)
C10	0.0496 (15)	0.0516 (19)	0.0494 (17)	−0.0076 (13)	0.0112 (13)	−0.0078 (15)
C11	0.0650 (18)	0.0476 (19)	0.0564 (19)	−0.0101 (14)	0.0183 (15)	−0.0057 (15)
C12	0.0645 (18)	0.048 (2)	0.0587 (19)	−0.0016 (14)	0.0212 (15)	0.0053 (16)
C13	0.106 (3)	0.059 (2)	0.068 (2)	−0.011 (2)	0.024 (2)	−0.0087 (19)
C14	0.0473 (15)	0.0424 (17)	0.0580 (18)	−0.0019 (12)	−0.0019 (13)	0.0068 (14)
C15	0.0558 (17)	0.062 (2)	0.069 (2)	0.0010 (15)	0.0040 (16)	0.0054 (17)
C16	0.080 (3)	0.083 (3)	0.080 (3)	0.008 (2)	0.025 (2)	0.015 (2)
C17	0.059 (2)	0.099 (3)	0.118 (4)	0.007 (2)	0.030 (2)	0.031 (3)
C18	0.051 (2)	0.109 (4)	0.121 (4)	−0.011 (2)	−0.002 (2)	0.025 (3)
C19	0.0564 (18)	0.077 (3)	0.083 (3)	−0.0145 (16)	−0.0066 (17)	0.010 (2)
C20	0.0544 (15)	0.0457 (18)	0.0511 (17)	−0.0051 (13)	0.0080 (13)	−0.0111 (14)
C21	0.0545 (17)	0.083 (3)	0.068 (2)	−0.0100 (16)	0.0110 (16)	−0.0126 (19)
C22	0.0532 (18)	0.084 (3)	0.078 (3)	0.0019 (16)	−0.0033 (18)	−0.017 (2)
C23	0.070 (2)	0.060 (2)	0.067 (2)	0.0141 (16)	−0.0138 (18)	−0.0133 (18)
C24	0.0674 (19)	0.058 (2)	0.0519 (19)	0.0037 (15)	0.0072 (15)	−0.0045 (15)
C25	0.0532 (16)	0.0508 (19)	0.0519 (18)	−0.0011 (13)	0.0042 (14)	−0.0087 (14)
Cl1	0.1052 (8)	0.1192 (10)	0.0800 (7)	0.0313 (7)	−0.0284 (6)	−0.0017 (6)
N1	0.0544 (13)	0.0517 (16)	0.0449 (13)	−0.0047 (11)	0.0020 (11)	−0.0015 (12)
N2	0.0553 (15)	0.093 (2)	0.0514 (16)	−0.0074 (15)	0.0070 (13)	−0.0066 (16)
O1	0.1124 (19)	0.0498 (15)	0.0736 (16)	0.0026 (13)	0.0212 (14)	0.0123 (12)
O2	0.174 (3)	0.0460 (17)	0.091 (2)	−0.0101 (17)	0.026 (2)	−0.0035 (15)
O3	0.0860 (15)	0.0605 (15)	0.0685 (15)	−0.0006 (12)	−0.0026 (12)	−0.0224 (12)
O4	0.0465 (10)	0.0543 (14)	0.0696 (14)	0.0067 (9)	−0.0036 (10)	−0.0058 (11)
O5	0.0603 (14)	0.134 (3)	0.093 (2)	0.0160 (15)	0.0053 (14)	0.0219 (19)
O6	0.0769 (17)	0.171 (3)	0.097 (2)	−0.045 (2)	0.0073 (16)	0.041 (2)
S1	0.0506 (4)	0.0452 (5)	0.0552 (5)	0.0003 (3)	−0.0015 (3)	−0.0074 (3)

C1—C2	1.381 (4)	C14—S1	1.743 (3)
C1—C6	1.394 (5)	C15—C16	1.364 (5)
C1—N1	1.429 (4)	C15—H15	0.9300
C2—C3	1.384 (5)	C16—C17	1.378 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.375 (6)	C17—C18	1.359 (7)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.377 (5)	C18—C19	1.364 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.388 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.374 (4)
C6—C7	1.442 (4)	C20—C25	1.388 (4)
C7—C12	1.392 (5)	C21—C22	1.373 (5)
C7—C8	1.392 (4)	C21—H21	0.9300
C8—C9	1.400 (4)	C22—C23	1.370 (5)
C8—N1	1.408 (4)	C22—H22	0.9300
C9—C10	1.369 (4)	C23—C24	1.367 (5)
C9—H9	0.9300	C23—Cl1	1.723 (4)
C10—C11	1.406 (4)	C24—C25	1.373 (4)
C10—C20	1.492 (4)	C24—H24	0.9300
C11—C12	1.407 (5)	C25—N2	1.469 (4)
C11—C13	1.435 (5)	N1—S1	1.669 (3)
C12—O1	1.343 (4)	N2—O5	1.196 (4)
C13—O2	1.213 (5)	N2—O6	1.213 (4)
C13—H13	0.9300	O1—H1	0.8200
C14—C15	1.372 (5)	O3—S1	1.420 (2)
C14—C19	1.375 (4)	O4—S1	1.415 (2)
C2—C1—C6	121.6 (3)	C14—C15—H15	120.5
C2—C1—N1	130.1 (3)	C15—C16—C17	119.7 (4)
C6—C1—N1	108.4 (3)	C15—C16—H16	120.2
C1—C2—C3	117.0 (4)	C17—C16—H16	120.2
C1—C2—H2	121.5	C18—C17—C16	120.7 (4)
C3—C2—H2	121.5	C18—C17—H17	119.6
C4—C3—C2	122.0 (4)	C16—C17—H17	119.6
C4—C3—H3	119.0	C17—C18—C19	120.4 (4)
C2—C3—H3	119.0	C17—C18—H18	119.8
C3—C4—C5	121.0 (4)	C19—C18—H18	119.8
C3—C4—H4	119.5	C18—C19—C14	118.6 (4)
C5—C4—H4	119.5	C18—C19—H19	120.7
C4—C5—C6	118.0 (4)	C14—C19—H19	120.7
C4—C5—H5	121.0	C21—C20—C25	115.7 (3)
C6—C5—H5	121.0	C21—C20—C10	121.5 (3)
C5—C6—C1	120.3 (3)	C25—C20—C10	122.5 (3)
C5—C6—C7	132.2 (3)	C22—C21—C20	122.6 (3)
C1—C6—C7	107.4 (3)	C22—C21—H21	118.7
C12—C7—C8	119.3 (3)	C20—C21—H21	118.7
C12—C7—C6	132.8 (3)	C23—C22—C21	119.3 (3)
C8—C7—C6	107.8 (3)	C23—C22—H22	120.4
C7—C8—C9	122.5 (3)	C21—C22—H22	120.4
C7—C8—N1	108.8 (3)	C24—C23—C22	120.9 (3)
C9—C8—N1	128.7 (3)	C24—C23—Cl1	119.6 (3)
C10—C9—C8	117.1 (3)	C22—C23—Cl1	119.5 (3)
C10—C9—H9	121.4	C23—C24—C25	118.1 (3)
C8—C9—H9	121.4	C23—C24—H24	121.0
C9—C10—C11	122.4 (3)	C25—C24—H24	121.0
C9—C10—C20	116.4 (3)	C24—C25—C20	123.5 (3)
C11—C10—C20	121.2 (3)	C24—C25—N2	116.5 (3)
C10—C11—C12	119.1 (3)	C20—C25—N2	120.1 (3)
C10—C11—C13	121.5 (3)	C8—N1—C1	107.4 (2)
C12—C11—C13	119.3 (3)	C8—N1—S1	123.5 (2)
O1—C12—C7	118.5 (3)	C1—N1—S1	124.1 (2)
O1—C12—C11	122.2 (3)	O5—N2—O6	123.7 (3)
C7—C12—C11	119.3 (3)	O5—N2—C25	118.9 (3)
O2—C13—C11	126.4 (4)	O6—N2—C25	117.4 (3)
O2—C13—H13	116.8	C12—O1—H1	109.5
C11—C13—H13	116.8	O4—S1—O3	120.14 (14)
C15—C14—C19	121.6 (3)	O4—S1—N1	106.50 (13)
C15—C14—S1	119.8 (2)	O3—S1—N1	106.18 (14)
C19—C14—S1	118.5 (3)	O4—S1—C14	109.06 (14)
C16—C15—C14	119.0 (3)	O3—S1—C14	110.19 (15)
C16—C15—H15	120.5	N1—S1—C14	103.37 (13)
C6—C1—C2—C3	2.3 (5)	C15—C14—C19—C18	0.3 (5)
N1—C1—C2—C3	−177.4 (3)	S1—C14—C19—C18	175.9 (3)
C1—C2—C3—C4	−1.8 (5)	C9—C10—C20—C21	−95.9 (4)
C2—C3—C4—C5	−0.3 (6)	C11—C10—C20—C21	83.9 (4)
C3—C4—C5—C6	1.9 (5)	C9—C10—C20—C25	77.3 (4)
C4—C5—C6—C1	−1.4 (5)	C11—C10—C20—C25	−102.9 (4)
C4—C5—C6—C7	175.0 (3)	C25—C20—C21—C22	−0.8 (5)
C2—C1—C6—C5	−0.7 (4)	C10—C20—C21—C22	172.9 (3)
N1—C1—C6—C5	179.0 (3)	C20—C21—C22—C23	−0.6 (6)
C2—C1—C6—C7	−177.9 (3)	C21—C22—C23—C24	0.5 (6)
N1—C1—C6—C7	1.8 (3)	C21—C22—C23—Cl1	−178.7 (3)
C5—C6—C7—C12	1.8 (5)	C22—C23—C24—C25	0.9 (5)
C1—C6—C7—C12	178.6 (3)	Cl1—C23—C24—C25	−179.8 (3)
C5—C6—C7—C8	−175.4 (3)	C23—C24—C25—C20	−2.5 (5)
C1—C6—C7—C8	1.4 (3)	C23—C24—C25—N2	178.8 (3)
C12—C7—C8—C9	−3.6 (4)	C21—C20—C25—C24	2.4 (5)
C6—C7—C8—C9	174.1 (2)	C10—C20—C25—C24	−171.2 (3)
C12—C7—C8—N1	178.3 (2)	C21—C20—C25—N2	−178.9 (3)
C6—C7—C8—N1	−4.0 (3)	C10—C20—C25—N2	7.5 (5)
C7—C8—C9—C10	−0.5 (4)	C7—C8—N1—C1	5.1 (3)
N1—C8—C9—C10	177.2 (2)	C9—C8—N1—C1	−172.9 (3)
C8—C9—C10—C11	4.2 (4)	C7—C8—N1—S1	161.01 (19)
C8—C9—C10—C20	−175.9 (2)	C9—C8—N1—S1	−16.9 (4)
C9—C10—C11—C12	−3.7 (4)	C2—C1—N1—C8	175.5 (3)
C20—C10—C11—C12	176.4 (3)	C6—C1—N1—C8	−4.2 (3)
C9—C10—C11—C13	179.1 (3)	C2—C1—N1—S1	19.7 (4)
C20—C10—C11—C13	−0.7 (4)	C6—C1—N1—S1	−160.0 (2)
C8—C7—C12—O1	−177.8 (3)	C24—C25—N2—O5	−145.9 (3)
C6—C7—C12—O1	5.2 (5)	C20—C25—N2—O5	35.2 (5)
C8—C7—C12—C11	4.0 (4)	C24—C25—N2—O6	34.5 (5)
C6—C7—C12—C11	−173.0 (3)	C20—C25—N2—O6	−144.3 (3)
C10—C11—C12—O1	−178.7 (3)	C8—N1—S1—O4	40.4 (2)
C13—C11—C12—O1	−1.5 (5)	C1—N1—S1—O4	−167.7 (2)
C10—C11—C12—C7	−0.5 (4)	C8—N1—S1—O3	169.5 (2)
C13—C11—C12—C7	176.7 (3)	C1—N1—S1—O3	−38.5 (3)
C10—C11—C13—O2	179.9 (4)	C8—N1—S1—C14	−74.5 (2)
C12—C11—C13—O2	2.8 (6)	C1—N1—S1—C14	77.5 (2)
C19—C14—C15—C16	0.5 (5)	C15—C14—S1—O4	−29.1 (3)
S1—C14—C15—C16	−175.0 (3)	C19—C14—S1—O4	155.3 (3)
C14—C15—C16—C17	−0.3 (6)	C15—C14—S1—O3	−162.9 (3)
C15—C16—C17—C18	−0.7 (6)	C19—C14—S1—O3	21.4 (3)
C16—C17—C18—C19	1.6 (7)	C15—C14—S1—N1	84.0 (3)
C17—C18—C19—C14	−1.3 (6)	C19—C14—S1—N1	−91.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.91	2.629 (4)	146
C2—H2···O3	0.93	2.36	2.949 (5)	121
C9—H9···O4	0.93	2.31	2.910 (4)	122
C13—H13···O4i	0.93	2.56	3.411 (4)	153
C18—H18···O4ii	0.93	2.53	3.287 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.91	2.629 (4)	146
C2—H2⋯O3	0.93	2.36	2.949 (5)	121
C9—H9⋯O4	0.93	2.31	2.910 (4)	122
C13—H13⋯O4i	0.93	2.56	3.411 (4)	153
C18—H18⋯O4ii	0.93	2.53	3.287 (4)	139

Symmetry codes: (i) ; (ii) .