4-Acet­amido-2-methoxy-5-[3-(phenyl­sulfanyl)indole-2-carbonyl]­benzoic acid

In the title compound, C₂₅H₂₀N₂O₅S, the indole ring system is planar. The dihedral angles between the indole moiety and the two substituent aromatic rings are 73.6 (1) and 44.4 (1)°. The structure is influenced by intramolecular O—H...O, N—H...O and C—H...O hydrogen bonds and the crystal structure is stabilized by intermolecular N—H...O hydrogen bonds and C—H...π and C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.118
• Data-to-parameter ratio = 17.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

An X-ray study of the title compound, (I), was of interest because indole derivatives exhibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). The indole ring system is present in a number of natural products, many of which are found to possess antidepressant (Grinev et al., 1984), antimicrobial (Gadaginamath & Patil, 1999) and anti-inflammatory (Rodriguez et al., 1985) activities. Indoles have been proved to display high aldose reductose inhibitory activity (Rajeswaran et al., 1999).

The structure of (I), with the atom-numbering scheme, is shown in Fig. 1. The C—N and C—S bond distances are in good agreement with previously reported values in related strucutres (Sivaraman et al., 1994a, 1994b, 1994c). The C—O, C=O and C_phenyl—C_phenyl distances are comparable with the corresponding mean values reported by Allen et al. (1987). The geometry of the indole ring system is comparable to our recent findings (Sankaranarayanan et al., 2001, 2003a,b). The sum of the angles around N25 [359.8 (1)°] is indicative of sp² hybridization. The exocyclic angles around C20 show considerable asymmetry with O4—C20—C21 [121.8 (2)°] being wider than O4—C20—C19 [116.4 (1)°]. This may be due to the steric repulsion between H21 and H24C separated by 2.22 Å. The conformation of the attachment of the two phenyl rings to the indole moiety is described by the torsion angles C10—S1—C3—C2 [110.0 (2)°] and C17—C16—C2—N1 [−160.8 (2)°]. The torsion angles C24—O4—C20—C21 [−10.2 (2)°] and C24—O4—C20—C19 [170.1 (2)°] indicate that the methoxy group is nearly coplanar with the attached ring. The dihedral angles between the indole moiety and the two phenyl rings A (C10—C15) and B (C17—C22) are 73.6 (1) and 44.4 (1)°, respectively. The dihedral angle between the two phenyl rings is 78.2 (1)°.

In the molecular structure, the conformations of the substituents in the phenyl ring B are influenced by intramolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 2). The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds, C—H···O and C—H···π interactions (Table 2 and Fig. 2). In Table 2, CgA denotes the centroid of the phenyl ring A.

S2. Experimental

The title compound was prepared by the oxidation of the corresponding 2-benzoylindole derivative by Sarrett reagent, CrO₃-Pyridine (Arumugam & Srinivasan, 2003). Single crystals were obtained from methanol by slow evaporation.

S3. Refinement

All C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms and refined isotropically. Atoms H1, H25 and H3 attached to atoms N1, N25 and O3, respectively were located from a difference Fourier map and refined isotropically. The range of N—H distances is 0.87 (2)–0.95 (2) Å and the O—H distance is 0.87 (2) Å.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing of the molecules, viewed down the b axis.

2-Methoxy-4-acetamido-5-(3'-phenylthio indol-2-oyl)benzoic acid

Crystal data

C25H20N2O5S	F(000) = 960
Mr = 460.49	Dx = 1.410 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8224 reflections
a = 10.8499 (2) Å	θ = 2.1–28.4°
b = 10.5171 (2) Å	µ = 0.19 mm^−1
c = 19.0168 (3) Å	T = 293 K
β = 92.104 (1)°	Block, yellow
V = 2168.53 (7) Å^3	0.46 × 0.22 × 0.20 mm
Z = 4

Data collection

Siemens SMART CCD area detector diffractometer	3386 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 28.4°, θmin = 2.1°
ω scans	h = −14→10
17151 measured reflections	k = −14→14
5372 independent reflections	l = −25→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0564P)^2] where P = Fo^2 + 2Fc^2)/3
5372 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.00188 (4)	0.78661 (4)	0.17746 (2)	0.04203 (14)
O1	0.16827 (13)	0.38507 (11)	0.23275 (6)	0.0491 (3)
O2	0.29567 (16)	0.87967 (13)	0.07523 (7)	0.0719 (5)
O3	0.27234 (15)	0.84512 (14)	−0.03733 (7)	0.0581 (4)
O4	0.19947 (13)	0.62226 (11)	−0.07632 (6)	0.0455 (3)
O5	0.05664 (16)	0.21624 (13)	−0.00484 (7)	0.0671 (5)
N1	0.14497 (15)	0.57026 (15)	0.32859 (7)	0.0383 (4)
C2	0.12107 (16)	0.59509 (15)	0.25820 (8)	0.0333 (4)
C3	0.06235 (16)	0.71201 (16)	0.25248 (8)	0.0337 (4)
C4	0.05257 (16)	0.76003 (16)	0.32246 (8)	0.0353 (4)
C5	0.10376 (16)	0.66803 (16)	0.36862 (8)	0.0360 (4)
C6	0.10721 (18)	0.68437 (18)	0.44147 (9)	0.0444 (5)
H6	0.1400	0.6226	0.4717	0.053*
C7	0.0601 (2)	0.7955 (2)	0.46627 (10)	0.0524 (5)
H7	0.0606	0.8091	0.5146	0.063*
C8	0.0112 (2)	0.8890 (2)	0.42141 (10)	0.0533 (5)
H8	−0.0186	0.9639	0.4405	0.064*
C9	0.00602 (18)	0.87292 (18)	0.34971 (10)	0.0460 (5)
H9	−0.0275	0.9354	0.3201	0.055*
C10	−0.16206 (17)	0.77897 (17)	0.19148 (9)	0.0413 (4)
C11	−0.2153 (2)	0.6999 (2)	0.24001 (10)	0.0534 (5)
H11	−0.1660	0.6510	0.2706	0.064*
C12	−0.3420 (2)	0.6944 (3)	0.24259 (14)	0.0799 (8)
H12	−0.3781	0.6404	0.2746	0.096*
C13	−0.4155 (3)	0.7675 (4)	0.19847 (17)	0.0997 (11)
H13	−0.5009	0.7631	0.2007	0.120*
C14	−0.3629 (3)	0.8469 (3)	0.15132 (16)	0.0904 (9)
H14	−0.4128	0.8968	0.1216	0.108*
C15	−0.2371 (2)	0.8534 (2)	0.14742 (11)	0.0623 (6)
H15	−0.2020	0.9078	0.1152	0.075*
C16	0.15537 (15)	0.49363 (16)	0.20886 (8)	0.0344 (4)
C17	0.17132 (15)	0.52181 (15)	0.13376 (8)	0.0326 (4)
C18	0.21314 (15)	0.64110 (16)	0.11339 (8)	0.0339 (4)
H18	0.2335	0.7004	0.1482	0.041*
C19	0.22569 (15)	0.67516 (15)	0.04365 (8)	0.0332 (4)
C20	0.19318 (16)	0.58430 (16)	−0.00770 (8)	0.0332 (4)
C21	0.15624 (16)	0.46349 (16)	0.00996 (8)	0.0357 (4)
H21	0.1372	0.4044	−0.0251	0.043*
C22	0.14743 (15)	0.43000 (15)	0.08052 (8)	0.0323 (4)
C23	0.26754 (18)	0.80649 (17)	0.02932 (10)	0.0431 (4)
C24	0.1867 (2)	0.52885 (18)	−0.13080 (9)	0.0512 (5)
H24A	0.2475	0.4635	−0.1231	0.077*
H24B	0.1984	0.5683	−0.1756	0.077*
H24C	0.1058	0.4921	−0.1303	0.077*
N25	0.11273 (15)	0.30799 (13)	0.10023 (8)	0.0389 (4)
C26	0.07243 (17)	0.20881 (16)	0.05801 (10)	0.0412 (4)
C27	0.0470 (2)	0.08889 (17)	0.09730 (11)	0.0559 (6)
H27A	−0.0400	0.0721	0.0951	0.084*
H27B	0.0747	0.0982	0.1455	0.084*
H27C	0.0899	0.0194	0.0764	0.084*
H1	0.1746 (17)	0.4987 (18)	0.3447 (9)	0.044 (5)*
H25	0.1252 (18)	0.2945 (18)	0.1495 (10)	0.054 (6)*
H3	0.258 (2)	0.779 (2)	−0.0634 (12)	0.084 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0440 (3)	0.0440 (3)	0.0381 (2)	0.0066 (2)	0.00179 (19)	0.0112 (2)
O1	0.0735 (10)	0.0341 (7)	0.0398 (7)	0.0091 (7)	0.0046 (6)	0.0013 (6)
O2	0.1186 (15)	0.0405 (8)	0.0570 (9)	−0.0304 (9)	0.0108 (9)	−0.0145 (7)
O3	0.0889 (12)	0.0368 (8)	0.0491 (8)	−0.0121 (8)	0.0092 (8)	0.0029 (7)
O4	0.0693 (9)	0.0370 (7)	0.0307 (6)	−0.0076 (6)	0.0066 (6)	−0.0031 (5)
O5	0.1092 (14)	0.0454 (8)	0.0459 (8)	−0.0242 (8)	−0.0105 (8)	−0.0039 (7)
N1	0.0519 (10)	0.0330 (8)	0.0297 (7)	0.0095 (7)	−0.0020 (7)	0.0016 (6)
C2	0.0387 (9)	0.0341 (9)	0.0271 (8)	0.0017 (7)	0.0002 (7)	0.0011 (7)
C3	0.0370 (9)	0.0324 (9)	0.0319 (8)	0.0014 (8)	0.0029 (7)	0.0025 (7)
C4	0.0385 (9)	0.0341 (9)	0.0334 (9)	0.0012 (7)	0.0017 (7)	−0.0012 (7)
C5	0.0393 (10)	0.0352 (9)	0.0336 (9)	0.0015 (8)	0.0021 (7)	−0.0043 (7)
C6	0.0510 (12)	0.0492 (11)	0.0325 (9)	0.0019 (9)	−0.0021 (8)	−0.0016 (8)
C7	0.0588 (13)	0.0612 (13)	0.0372 (10)	−0.0006 (11)	0.0023 (9)	−0.0161 (10)
C8	0.0613 (14)	0.0472 (12)	0.0514 (12)	0.0091 (10)	0.0033 (10)	−0.0178 (10)
C9	0.0521 (12)	0.0374 (10)	0.0485 (11)	0.0062 (9)	0.0011 (9)	−0.0047 (8)
C10	0.0431 (10)	0.0416 (10)	0.0388 (9)	0.0063 (9)	−0.0029 (8)	−0.0124 (8)
C11	0.0511 (13)	0.0603 (13)	0.0492 (11)	−0.0053 (10)	0.0087 (9)	−0.0147 (10)
C12	0.0603 (16)	0.107 (2)	0.0743 (17)	−0.0194 (16)	0.0245 (14)	−0.0361 (15)
C13	0.0424 (15)	0.160 (3)	0.097 (2)	0.0097 (18)	0.0014 (15)	−0.058 (2)
C14	0.0609 (18)	0.116 (2)	0.093 (2)	0.0358 (17)	−0.0193 (15)	−0.0338 (18)
C15	0.0571 (14)	0.0658 (15)	0.0629 (14)	0.0171 (12)	−0.0127 (11)	−0.0094 (11)
C16	0.0363 (10)	0.0321 (9)	0.0348 (9)	0.0029 (7)	0.0004 (7)	−0.0015 (7)
C17	0.0344 (9)	0.0298 (9)	0.0337 (8)	0.0023 (7)	0.0035 (7)	−0.0039 (7)
C18	0.0358 (9)	0.0317 (9)	0.0345 (9)	−0.0001 (7)	0.0040 (7)	−0.0078 (7)
C19	0.0349 (9)	0.0285 (9)	0.0367 (9)	−0.0015 (7)	0.0052 (7)	−0.0043 (7)
C20	0.0357 (9)	0.0337 (9)	0.0303 (8)	0.0003 (7)	0.0036 (7)	−0.0031 (7)
C21	0.0422 (10)	0.0302 (9)	0.0349 (9)	−0.0019 (8)	0.0015 (7)	−0.0073 (7)
C22	0.0335 (9)	0.0274 (8)	0.0363 (9)	0.0012 (7)	0.0042 (7)	−0.0025 (7)
C23	0.0505 (11)	0.0337 (10)	0.0456 (10)	−0.0032 (9)	0.0103 (9)	−0.0046 (8)
C24	0.0725 (15)	0.0508 (12)	0.0306 (9)	−0.0091 (11)	0.0047 (9)	−0.0075 (8)
N25	0.0515 (10)	0.0286 (8)	0.0367 (8)	−0.0021 (7)	0.0050 (7)	−0.0016 (6)
C26	0.0469 (11)	0.0298 (9)	0.0469 (11)	−0.0021 (8)	0.0022 (8)	−0.0033 (8)
C27	0.0717 (15)	0.0325 (10)	0.0637 (13)	−0.0070 (10)	0.0052 (11)	0.0005 (9)

Geometric parameters (Å, º)

S1—C3	1.750 (2)	C11—H11	0.93
S1—C10	1.770 (2)	C12—C13	1.372 (4)
O1—C16	1.235 (2)	C12—H12	0.93
O2—C23	1.195 (2)	C13—C14	1.365 (4)
O3—C23	1.334 (2)	C13—H13	0.93
O3—H3	0.87 (2)	C14—C15	1.372 (3)
O4—C20	1.369 (2)	C14—H14	0.93
O4—C24	1.431 (2)	C15—H15	0.93
O5—C26	1.204 (2)	C16—C17	1.475 (2)
N1—C5	1.364 (2)	C17—C18	1.394 (2)
N1—C2	1.379 (2)	C17—C22	1.416 (2)
N1—H1	0.87 (2)	C18—C19	1.385 (2)
C2—C3	1.387 (2)	C18—H18	0.93
C2—C16	1.478 (2)	C19—C20	1.402 (2)
C3—C4	1.431 (2)	C19—C23	1.482 (2)
C4—C9	1.397 (2)	C20—C21	1.378 (2)
C4—C5	1.407 (2)	C21—C22	1.394 (2)
C5—C6	1.395 (2)	C21—H21	0.93
C6—C7	1.366 (3)	C22—N25	1.393 (2)
C6—H6	0.93	C24—H24A	0.96
C7—C8	1.394 (3)	C24—H24B	0.96
C7—H7	0.93	C24—H24C	0.96
C8—C9	1.373 (3)	N25—C26	1.378 (2)
C8—H8	0.93	N25—H25	0.95 (2)
C9—H9	0.93	C26—C27	1.497 (2)
C10—C11	1.384 (3)	C27—H27A	0.96
C10—C15	1.388 (3)	C27—H27B	0.96
C11—C12	1.379 (3)	C27—H27C	0.96
C3—S1—C10	102.75 (8)	C14—C15—C10	120.1 (2)
C23—O3—H3	106.7 (15)	C14—C15—H15	119.9
C20—O4—C24	118.89 (13)	C10—C15—H15	119.9
C5—N1—C2	110.18 (14)	O1—C16—C17	121.76 (14)
C5—N1—H1	125.4 (12)	O1—C16—C2	117.50 (14)
C2—N1—H1	124.1 (12)	C17—C16—C2	120.74 (14)
N1—C2—C3	108.26 (13)	C18—C17—C22	117.90 (14)
N1—C2—C16	115.91 (14)	C18—C17—C16	120.06 (14)
C3—C2—C16	135.72 (14)	C22—C17—C16	122.04 (14)
C2—C3—C4	106.82 (14)	C19—C18—C17	122.91 (15)
C2—C3—S1	128.99 (12)	C19—C18—H18	118.5
C4—C3—S1	123.98 (13)	C17—C18—H18	118.5
C9—C4—C5	119.53 (15)	C18—C19—C20	117.36 (15)
C9—C4—C3	133.22 (17)	C18—C19—C23	117.30 (15)
C5—C4—C3	107.25 (14)	C20—C19—C23	125.30 (15)
N1—C5—C6	130.50 (16)	O4—C20—C21	121.8 (2)
N1—C5—C4	107.47 (14)	O4—C20—C19	116.4 (1)
C6—C5—C4	122.0 (2)	C21—C20—C19	121.79 (15)
C7—C6—C5	116.8 (2)	C20—C21—C22	119.91 (15)
C7—C6—H6	121.6	C20—C21—H21	120.0
C5—C6—H6	121.6	C22—C21—H21	120.0
C6—C7—C8	122.1 (2)	N25—C22—C21	121.38 (15)
C6—C7—H7	119.0	N25—C22—C17	118.69 (14)
C8—C7—H7	119.0	C21—C22—C17	119.92 (15)
C9—C8—C7	121.46 (17)	O2—C23—O3	118.69 (17)
C9—C8—H8	119.3	O2—C23—C19	122.51 (17)
C7—C8—H8	119.3	O3—C23—C19	118.79 (16)
C8—C9—C4	118.1 (2)	O4—C24—H24A	109.5
C8—C9—H9	121.0	O4—C24—H24B	109.5
C4—C9—H9	121.0	H24A—C24—H24B	109.5
C11—C10—C15	119.4 (2)	O4—C24—H24C	109.5
C11—C10—S1	124.30 (16)	H24A—C24—H24C	109.5
C15—C10—S1	116.15 (16)	H24B—C24—H24C	109.5
C12—C11—C10	119.3 (2)	C26—N25—C22	128.6 (2)
C12—C11—H11	120.3	C26—N25—H25	119.4 (12)
C10—C11—H11	120.3	C22—N25—H25	111.8 (12)
C13—C12—C11	120.8 (3)	O5—C26—N25	124.1 (2)
C13—C12—H12	119.6	O5—C26—C27	121.88 (17)
C11—C12—H12	119.6	N25—C26—C27	114.1 (2)
C14—C13—C12	119.8 (3)	C26—C27—H27A	109.5
C14—C13—H13	120.1	C26—C27—H27B	109.5
C12—C13—H13	120.1	H27A—C27—H27B	109.5
C13—C14—C15	120.5 (3)	C26—C27—H27C	109.5
C13—C14—H14	119.8	H27A—C27—H27C	109.5
C15—C14—H14	119.8	H27B—C27—H27C	109.5
C5—N1—C2—C3	−0.2 (2)	N1—C2—C16—O1	20.2 (2)
C5—N1—C2—C16	−177.02 (15)	C3—C2—C16—O1	−155.4 (2)
N1—C2—C3—C4	0.96 (19)	N1—C2—C16—C17	−160.8 (2)
C16—C2—C3—C4	176.84 (19)	C3—C2—C16—C17	23.6 (3)
N1—C2—C3—S1	−173.90 (13)	O1—C16—C17—C18	−149.97 (17)
C16—C2—C3—S1	2.0 (3)	C2—C16—C17—C18	31.1 (2)
C10—S1—C3—C2	110.0 (2)	O1—C16—C17—C22	28.9 (3)
C10—S1—C3—C4	−64.03 (16)	C2—C16—C17—C22	−150.09 (16)
C2—C3—C4—C9	178.0 (2)	C22—C17—C18—C19	3.6 (3)
S1—C3—C4—C9	−6.8 (3)	C16—C17—C18—C19	−177.53 (15)
C2—C3—C4—C5	−1.34 (19)	C17—C18—C19—C20	0.6 (2)
S1—C3—C4—C5	173.84 (13)	C17—C18—C19—C23	178.17 (16)
C2—N1—C5—C6	179.63 (18)	C24—O4—C20—C21	−10.2 (2)
C2—N1—C5—C4	−0.6 (2)	C24—O4—C20—C19	170.1 (2)
C9—C4—C5—N1	−178.24 (17)	C18—C19—C20—O4	176.36 (15)
C3—C4—C5—N1	1.2 (2)	C23—C19—C20—O4	−1.0 (3)
C9—C4—C5—C6	1.5 (3)	C18—C19—C20—C21	−3.3 (3)
C3—C4—C5—C6	−179.03 (16)	C23—C19—C20—C21	179.35 (17)
N1—C5—C6—C7	178.7 (2)	O4—C20—C21—C22	−177.99 (15)
C4—C5—C6—C7	−1.0 (3)	C19—C20—C21—C22	1.7 (3)
C5—C6—C7—C8	−0.3 (3)	C20—C21—C22—N25	−178.72 (16)
C6—C7—C8—C9	1.2 (3)	C20—C21—C22—C17	2.7 (2)
C7—C8—C9—C4	−0.6 (3)	C18—C17—C22—N25	176.19 (15)
C5—C4—C9—C8	−0.6 (3)	C16—C17—C22—N25	−2.7 (2)
C3—C4—C9—C8	−179.94 (19)	C18—C17—C22—C21	−5.2 (2)
C3—S1—C10—C11	−16.15 (17)	C16—C17—C22—C21	175.91 (15)
C3—S1—C10—C15	167.43 (15)	C18—C19—C23—O2	3.6 (3)
C15—C10—C11—C12	1.5 (3)	C20—C19—C23—O2	−179.02 (19)
S1—C10—C11—C12	−174.85 (15)	C18—C19—C23—O3	−175.40 (17)
C10—C11—C12—C13	−1.0 (3)	C20—C19—C23—O3	2.0 (3)
C11—C12—C13—C14	0.1 (4)	C21—C22—N25—C26	−6.4 (3)
C12—C13—C14—C15	0.4 (4)	C17—C22—N25—C26	172.23 (17)
C13—C14—C15—C10	0.1 (4)	C22—N25—C26—O5	−3.0 (3)
C11—C10—C15—C14	−1.0 (3)	C22—N25—C26—C27	178.05 (17)
S1—C10—C15—C14	175.56 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.87 (2)	1.78 (3)	2.574 (2)	151 (2)
N25—H25···O1	0.95 (2)	1.89 (2)	2.695 (2)	140 (2)
C18—H18···O2	0.93	2.45	2.770 (2)	100
C21—H21···O5	0.93	2.20	2.826 (2)	124
N1—H1···O2^i	0.87 (2)	1.99 (2)	2.773 (2)	150 (2)
C13—H13···O1^ii	0.93	2.59	3.320 (3)	136
C24—H24A···CgA^iii	0.96	2.89	3.598 (2)	132

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x−1/2, y+1/2, −z+1/2; (iii) −x, −y+1, −z.