Ethyl 2-(4-hy-droxy-3-meth-oxy-phen-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate monohydrate.

In the title compound, C(24)H(27)N(3)O(5)·H(2)O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intra-molecular C-H⋯π inter-action is observed. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π-π stacking [centroid-centroid distance = 3.6632 (9) Å] and C-H⋯O inter-actions.

Related literature

For the biological activity of benzimidazole derivatives, see: Rao et al. (2002 ▶); Thakurdesai et al. (2007 ▶); Dubey & Sanyal (2010 ▶). For related structures, see: Yoon et al. (2011 ▶). For the ring conformation, see: Cremer & Pople (1975) ▶.

Experimental

Crystal data

C24H27N3O5·H2O

M = 455.50

Triclinic,

a = 9.7460 (8) Å

b = 10.0436 (8) Å

c = 12.6072 (10) Å

α = 85.737 (1)°

β = 89.684 (2)°

γ = 70.238 (1)°

V = 1157.91 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.43 × 0.32 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.985

18195 measured reflections

6686 independent reflections

4485 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.185

S = 1.07

6686 reflections

312 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052391/is5022sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052391/is5022Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052391/is5022Isup3.cml

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

C24H27N3O5·H2O	Z = 2
Mr = 455.50	F(000) = 484
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7460 (8) Å	Cell parameters from 4470 reflections
b = 10.0436 (8) Å	θ = 2.5–29.5°
c = 12.6072 (10) Å	µ = 0.10 mm−1
α = 85.737 (1)°	T = 296 K
β = 89.684 (2)°	Block, brown
γ = 70.238 (1)°	0.43 × 0.32 × 0.16 mm
V = 1157.91 (16) Å3

Bruker APEXII DUO CCD area-detector diffractometer	6686 independent reflections
Radiation source: fine-focus sealed tube	4485 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.960, Tmax = 0.985	k = −14→14
18195 measured reflections	l = −17→17

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0974P)2 + 0.1068P] where P = (Fo2 + 2Fc2)/3
6686 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.26 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
O1	−0.17090 (17)	0.13373 (19)	0.18216 (12)	0.0762 (4)
O2	−0.35072 (14)	0.11827 (17)	0.28604 (13)	0.0702 (4)
O3	0.1298 (3)	0.2186 (2)	1.00505 (19)	0.1183 (8)
O4	0.64165 (13)	0.40228 (14)	0.73582 (10)	0.0538 (3)
O5	0.64019 (13)	0.14280 (12)	0.76404 (10)	0.0552 (3)
N1	0.17611 (13)	0.25473 (14)	0.43596 (10)	0.0416 (3)
N2	0.09463 (13)	0.23337 (13)	0.60105 (10)	0.0401 (3)
N3	0.12756 (16)	0.41105 (17)	0.89776 (11)	0.0529 (4)
C1	0.04959 (15)	0.21973 (15)	0.43129 (12)	0.0379 (3)
C2	−0.02368 (16)	0.19669 (16)	0.34357 (13)	0.0412 (3)
H2A	0.0100	0.2035	0.2749	0.049*
C3	−0.14954 (15)	0.16306 (15)	0.36302 (13)	0.0421 (3)
C4	−0.20115 (16)	0.15385 (17)	0.46613 (14)	0.0456 (4)
H4A	−0.2863	0.1325	0.4759	0.055*
C5	−0.12959 (16)	0.17542 (17)	0.55325 (13)	0.0443 (3)
H5A	−0.1636	0.1686	0.6218	0.053*
C6	−0.00288 (15)	0.20810 (15)	0.53349 (12)	0.0378 (3)
C7	0.19826 (15)	0.26220 (15)	0.53799 (12)	0.0386 (3)
C8	0.31855 (15)	0.29914 (16)	0.58469 (12)	0.0391 (3)
C9	0.42362 (16)	0.19835 (15)	0.65042 (12)	0.0419 (3)
H9A	0.4206	0.1068	0.6616	0.050*
C10	0.53227 (15)	0.23334 (15)	0.69912 (12)	0.0397 (3)
C11	0.53539 (16)	0.37285 (16)	0.68324 (12)	0.0399 (3)
C12	0.43197 (17)	0.47134 (16)	0.61670 (13)	0.0436 (3)
H12A	0.4346	0.5630	0.6051	0.052*
C13	0.32404 (17)	0.43507 (16)	0.56685 (13)	0.0437 (3)
H13A	0.2557	0.5019	0.5216	0.052*
C14	−0.23434 (18)	0.13642 (17)	0.27471 (15)	0.0492 (4)
C15	−0.2499 (4)	0.1148 (4)	0.0897 (2)	0.1125 (11)
H15A	−0.2417	0.0159	0.0893	0.135*
H15B	−0.3524	0.1707	0.0942	0.135*
C16	−0.1953 (5)	0.1561 (5)	−0.0036 (3)	0.1330 (14)
H16A	−0.2453	0.1380	−0.0633	0.199*
H16B	−0.0930	0.1034	−0.0068	0.199*
H16C	−0.2095	0.2556	−0.0055	0.199*
C17	0.07375 (17)	0.25520 (17)	0.71444 (12)	0.0440 (3)
H17A	0.1679	0.2234	0.7510	0.053*
H17B	0.0174	0.1990	0.7447	0.053*
C18	−0.00473 (18)	0.41025 (18)	0.73095 (13)	0.0489 (4)
H18A	−0.1024	0.4388	0.7003	0.059*
H18B	0.0462	0.4669	0.6936	0.059*
C19	−0.01470 (19)	0.4404 (2)	0.84774 (15)	0.0574 (4)
H19A	−0.0725	0.5393	0.8537	0.069*
H19B	−0.0644	0.3828	0.8853	0.069*
C20	0.2172 (3)	0.4956 (3)	0.86944 (19)	0.0786 (7)
H20A	0.1655	0.5951	0.8783	0.094*
H20B	0.2485	0.4851	0.7964	0.094*
C21	0.3479 (3)	0.4349 (4)	0.9482 (2)	0.0957 (9)
H21A	0.4390	0.4191	0.9113	0.115*
H21B	0.3420	0.4996	1.0028	0.115*
C22	0.3385 (3)	0.2990 (3)	0.9957 (2)	0.0910 (8)
H22A	0.3541	0.2909	1.0721	0.109*
H22B	0.4112	0.2194	0.9659	0.109*
C23	0.1884 (3)	0.3012 (2)	0.96930 (17)	0.0675 (5)
C24	0.6452 (2)	−0.0001 (2)	0.7783 (2)	0.0696 (6)
H24A	0.7301	−0.0550	0.8204	0.104*
H24B	0.6497	−0.0381	0.7102	0.104*
H24C	0.5593	−0.0041	0.8141	0.104*
O1W	0.63716 (17)	0.67068 (15)	0.71300 (12)	0.0565 (3)
H2W1	0.556 (3)	0.736 (3)	0.7004 (18)	0.073 (7)*
H1W1	0.703 (3)	0.695 (2)	0.6663 (19)	0.076 (7)*
H1O4	0.630 (3)	0.493 (3)	0.7238 (18)	0.075 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0729 (9)	0.1176 (13)	0.0612 (9)	−0.0609 (9)	−0.0102 (7)	−0.0141 (8)
O2	0.0485 (7)	0.0835 (10)	0.0904 (10)	−0.0369 (7)	−0.0121 (7)	−0.0103 (8)
O3	0.1466 (19)	0.0967 (14)	0.1279 (17)	−0.0717 (14)	−0.0518 (14)	0.0407 (12)
O4	0.0477 (6)	0.0476 (7)	0.0739 (8)	−0.0271 (5)	−0.0160 (6)	−0.0001 (6)
O5	0.0519 (6)	0.0420 (6)	0.0730 (8)	−0.0197 (5)	−0.0242 (6)	0.0066 (5)
N1	0.0363 (6)	0.0502 (7)	0.0435 (7)	−0.0221 (5)	−0.0036 (5)	−0.0006 (5)
N2	0.0382 (6)	0.0431 (7)	0.0430 (7)	−0.0192 (5)	−0.0022 (5)	−0.0026 (5)
N3	0.0548 (8)	0.0617 (9)	0.0458 (8)	−0.0234 (7)	−0.0013 (6)	−0.0086 (6)
C1	0.0316 (6)	0.0379 (7)	0.0462 (8)	−0.0151 (6)	−0.0041 (5)	0.0001 (6)
C2	0.0367 (7)	0.0432 (8)	0.0460 (8)	−0.0171 (6)	−0.0052 (6)	−0.0011 (6)
C3	0.0338 (7)	0.0362 (7)	0.0577 (9)	−0.0139 (6)	−0.0086 (6)	−0.0017 (6)
C4	0.0337 (7)	0.0423 (8)	0.0641 (10)	−0.0177 (6)	−0.0005 (7)	−0.0005 (7)
C5	0.0383 (7)	0.0458 (8)	0.0514 (9)	−0.0186 (6)	0.0033 (6)	−0.0004 (6)
C6	0.0337 (6)	0.0348 (7)	0.0457 (8)	−0.0131 (5)	−0.0038 (5)	0.0002 (5)
C7	0.0346 (7)	0.0388 (7)	0.0443 (8)	−0.0155 (6)	−0.0037 (6)	−0.0003 (6)
C8	0.0364 (7)	0.0419 (7)	0.0423 (8)	−0.0180 (6)	−0.0025 (6)	−0.0020 (6)
C9	0.0419 (7)	0.0351 (7)	0.0528 (9)	−0.0189 (6)	−0.0077 (6)	−0.0008 (6)
C10	0.0365 (7)	0.0366 (7)	0.0473 (8)	−0.0145 (6)	−0.0073 (6)	0.0006 (6)
C11	0.0360 (7)	0.0406 (7)	0.0478 (8)	−0.0191 (6)	0.0000 (6)	−0.0047 (6)
C12	0.0432 (8)	0.0378 (7)	0.0545 (9)	−0.0208 (6)	−0.0018 (6)	0.0015 (6)
C13	0.0417 (7)	0.0418 (8)	0.0491 (8)	−0.0176 (6)	−0.0066 (6)	0.0039 (6)
C14	0.0426 (8)	0.0444 (8)	0.0645 (11)	−0.0203 (7)	−0.0120 (7)	−0.0002 (7)
C15	0.124 (2)	0.192 (3)	0.0685 (16)	−0.112 (3)	−0.0155 (15)	−0.0232 (18)
C16	0.184 (4)	0.162 (3)	0.088 (2)	−0.108 (3)	−0.050 (2)	0.003 (2)
C17	0.0454 (8)	0.0480 (8)	0.0404 (8)	−0.0189 (7)	−0.0021 (6)	−0.0004 (6)
C18	0.0408 (8)	0.0543 (9)	0.0485 (9)	−0.0118 (7)	−0.0045 (6)	−0.0056 (7)
C19	0.0480 (9)	0.0665 (11)	0.0564 (10)	−0.0157 (8)	0.0059 (8)	−0.0154 (8)
C20	0.0812 (14)	0.1101 (19)	0.0640 (12)	−0.0598 (14)	−0.0060 (11)	0.0033 (12)
C21	0.0717 (15)	0.157 (3)	0.0758 (15)	−0.0603 (18)	−0.0095 (12)	−0.0113 (16)
C22	0.0764 (15)	0.103 (2)	0.0856 (17)	−0.0190 (15)	−0.0253 (13)	−0.0107 (14)
C23	0.0776 (13)	0.0626 (12)	0.0628 (12)	−0.0239 (11)	−0.0135 (10)	−0.0052 (9)
C24	0.0683 (12)	0.0404 (9)	0.0982 (16)	−0.0193 (9)	−0.0323 (11)	0.0140 (9)
O1W	0.0552 (7)	0.0477 (7)	0.0723 (9)	−0.0254 (6)	0.0088 (6)	−0.0028 (6)

O1—C14	1.315 (2)	C11—C12	1.382 (2)
O1—C15	1.460 (2)	C12—C13	1.391 (2)
O2—C14	1.214 (2)	C12—H12A	0.9300
O3—C23	1.216 (3)	C13—H13A	0.9300
O4—C11	1.3575 (17)	C15—C16	1.382 (5)
O4—H1O4	0.88 (3)	C15—H15A	0.9700
O5—C10	1.3621 (18)	C15—H15B	0.9700
O5—C24	1.418 (2)	C16—H16A	0.9600
N1—C7	1.317 (2)	C16—H16B	0.9600
N1—C1	1.3944 (17)	C16—H16C	0.9600
N2—C7	1.3750 (19)	C17—C18	1.515 (2)
N2—C6	1.3774 (18)	C17—H17A	0.9700
N2—C17	1.465 (2)	C17—H17B	0.9700
N3—C23	1.341 (3)	C18—C19	1.521 (2)
N3—C20	1.437 (3)	C18—H18A	0.9700
N3—C19	1.453 (2)	C18—H18B	0.9700
C1—C2	1.395 (2)	C19—H19A	0.9700
C1—C6	1.395 (2)	C19—H19B	0.9700
C2—C3	1.394 (2)	C20—C21	1.542 (3)
C2—H2A	0.9300	C20—H20A	0.9700
C3—C4	1.399 (2)	C20—H20B	0.9700
C3—C14	1.483 (2)	C21—C22	1.481 (4)
C4—C5	1.373 (2)	C21—H21A	0.9700
C4—H4A	0.9300	C21—H21B	0.9700
C5—C6	1.398 (2)	C22—C23	1.494 (3)
C5—H5A	0.9300	C22—H22A	0.9700
C7—C8	1.4808 (19)	C22—H22B	0.9700
C8—C13	1.386 (2)	C24—H24A	0.9600
C8—C9	1.394 (2)	C24—H24B	0.9600
C9—C10	1.3830 (19)	C24—H24C	0.9600
C9—H9A	0.9300	O1W—H2W1	0.85 (3)
C10—C11	1.411 (2)	O1W—H1W1	0.95 (3)
C14—O1—C15	117.16 (17)	C16—C15—H15B	109.4
C11—O4—H1O4	109.2 (16)	O1—C15—H15B	109.4
C10—O5—C24	117.13 (13)	H15A—C15—H15B	108.0
C7—N1—C1	104.76 (12)	C15—C16—H16A	109.5
C7—N2—C6	106.56 (12)	C15—C16—H16B	109.5
C7—N2—C17	126.45 (12)	H16A—C16—H16B	109.5
C6—N2—C17	125.80 (13)	C15—C16—H16C	109.5
C23—N3—C20	114.78 (18)	H16A—C16—H16C	109.5
C23—N3—C19	123.57 (18)	H16B—C16—H16C	109.5
C20—N3—C19	121.59 (17)	N2—C17—C18	110.95 (13)
N1—C1—C2	129.84 (14)	N2—C17—H17A	109.4
N1—C1—C6	109.94 (12)	C18—C17—H17A	109.4
C2—C1—C6	120.21 (13)	N2—C17—H17B	109.4
C3—C2—C1	117.26 (15)	C18—C17—H17B	109.4
C3—C2—H2A	121.4	H17A—C17—H17B	108.0
C1—C2—H2A	121.4	C17—C18—C19	112.78 (15)
C2—C3—C4	121.49 (14)	C17—C18—H18A	109.0
C2—C3—C14	121.05 (15)	C19—C18—H18A	109.0
C4—C3—C14	117.46 (14)	C17—C18—H18B	109.0
C5—C4—C3	121.84 (14)	C19—C18—H18B	109.0
C5—C4—H4A	119.1	H18A—C18—H18B	107.8
C3—C4—H4A	119.1	N3—C19—C18	112.58 (14)
C4—C5—C6	116.48 (15)	N3—C19—H19A	109.1
C4—C5—H5A	121.8	C18—C19—H19A	109.1
C6—C5—H5A	121.8	N3—C19—H19B	109.1
N2—C6—C1	105.75 (12)	C18—C19—H19B	109.1
N2—C6—C5	131.54 (14)	H19A—C19—H19B	107.8
C1—C6—C5	122.71 (13)	N3—C20—C21	103.2 (2)
N1—C7—N2	112.96 (12)	N3—C20—H20A	111.1
N1—C7—C8	125.86 (13)	C21—C20—H20A	111.1
N2—C7—C8	121.17 (13)	N3—C20—H20B	111.1
C13—C8—C9	119.76 (13)	C21—C20—H20B	111.1
C13—C8—C7	120.35 (13)	H20A—C20—H20B	109.1
C9—C8—C7	119.84 (13)	C22—C21—C20	105.7 (2)
C10—C9—C8	120.56 (13)	C22—C21—H21A	110.6
C10—C9—H9A	119.7	C20—C21—H21A	110.6
C8—C9—H9A	119.7	C22—C21—H21B	110.6
O5—C10—C9	125.15 (13)	C20—C21—H21B	110.6
O5—C10—C11	115.23 (12)	H21A—C21—H21B	108.7
C9—C10—C11	119.62 (13)	C21—C22—C23	106.0 (2)
O4—C11—C12	123.67 (13)	C21—C22—H22A	110.5
O4—C11—C10	117.02 (13)	C23—C22—H22A	110.5
C12—C11—C10	119.31 (13)	C21—C22—H22B	110.5
C11—C12—C13	120.81 (13)	C23—C22—H22B	110.5
C11—C12—H12A	119.6	H22A—C22—H22B	108.7
C13—C12—H12A	119.6	O3—C23—N3	125.0 (2)
C8—C13—C12	119.90 (14)	O3—C23—C22	126.9 (2)
C8—C13—H13A	120.1	N3—C23—C22	108.1 (2)
C12—C13—H13A	120.1	O5—C24—H24A	109.5
O2—C14—O1	122.90 (16)	O5—C24—H24B	109.5
O2—C14—C3	123.72 (18)	H24A—C24—H24B	109.5
O1—C14—C3	113.38 (14)	O5—C24—H24C	109.5
C16—C15—O1	111.0 (2)	H24A—C24—H24C	109.5
C16—C15—H15A	109.4	H24B—C24—H24C	109.5
O1—C15—H15A	109.4	H2W1—O1W—H1W1	105 (2)
C7—N1—C1—C2	−179.26 (15)	C8—C9—C10—C11	0.9 (2)
C7—N1—C1—C6	0.55 (16)	O5—C10—C11—O4	−1.7 (2)
N1—C1—C2—C3	−179.84 (15)	C9—C10—C11—O4	177.88 (14)
C6—C1—C2—C3	0.4 (2)	O5—C10—C11—C12	178.61 (14)
C1—C2—C3—C4	0.5 (2)	C9—C10—C11—C12	−1.8 (2)
C1—C2—C3—C14	−179.84 (13)	O4—C11—C12—C13	−178.67 (15)
C2—C3—C4—C5	−0.9 (2)	C10—C11—C12—C13	1.0 (2)
C14—C3—C4—C5	179.39 (14)	C9—C8—C13—C12	−1.7 (2)
C3—C4—C5—C6	0.4 (2)	C7—C8—C13—C12	175.77 (14)
C7—N2—C6—C1	1.43 (15)	C11—C12—C13—C8	0.7 (2)
C17—N2—C6—C1	169.57 (13)	C15—O1—C14—O2	3.1 (3)
C7—N2—C6—C5	−179.21 (16)	C15—O1—C14—C3	−177.2 (2)
C17—N2—C6—C5	−11.1 (3)	C2—C3—C14—O2	−173.74 (17)
N1—C1—C6—N2	−1.25 (16)	C4—C3—C14—O2	5.9 (2)
C2—C1—C6—N2	178.58 (13)	C2—C3—C14—O1	6.5 (2)
N1—C1—C6—C5	179.31 (14)	C4—C3—C14—O1	−173.82 (15)
C2—C1—C6—C5	−0.9 (2)	C14—O1—C15—C16	161.8 (3)
C4—C5—C6—N2	−178.83 (15)	C7—N2—C17—C18	77.86 (19)
C4—C5—C6—C1	0.4 (2)	C6—N2—C17—C18	−87.97 (18)
C1—N1—C7—N2	0.40 (17)	N2—C17—C18—C19	−173.95 (13)
C1—N1—C7—C8	−178.76 (14)	C23—N3—C19—C18	−108.7 (2)
C6—N2—C7—N1	−1.19 (17)	C20—N3—C19—C18	68.2 (2)
C17—N2—C7—N1	−169.23 (14)	C17—C18—C19—N3	63.3 (2)
C6—N2—C7—C8	178.01 (13)	C23—N3—C20—C21	−7.6 (3)
C17—N2—C7—C8	10.0 (2)	C19—N3—C20—C21	175.20 (18)
N1—C7—C8—C13	67.7 (2)	N3—C20—C21—C22	13.8 (3)
N2—C7—C8—C13	−111.44 (17)	C20—C21—C22—C23	−15.0 (3)
N1—C7—C8—C9	−114.92 (18)	C20—N3—C23—O3	178.6 (3)
N2—C7—C8—C9	65.99 (19)	C19—N3—C23—O3	−4.3 (3)
C13—C8—C9—C10	0.8 (2)	C20—N3—C23—C22	−1.7 (3)
C7—C8—C9—C10	−176.60 (14)	C19—N3—C23—C22	175.38 (18)
C24—O5—C10—C9	3.3 (3)	C21—C22—C23—O3	−169.5 (3)
C24—O5—C10—C11	−177.18 (17)	C21—C22—C23—N3	10.8 (3)
C8—C9—C10—O5	−179.58 (15)

Cg4 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O2i	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W—H1W1···N1ii	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4—H1O4···O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16—H16A···O5iii	0.96	2.44	3.380 (3)	166.
C20—H20B···Cg4	0.97	2.86	3.750 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O2i	0.85 (3)	2.06 (3)	2.879 (2)	164 (2)
O1W—H1W1⋯N1ii	0.95 (3)	1.90 (3)	2.8416 (19)	176 (2)
O4—H1O4⋯O1W	0.88 (3)	1.80 (3)	2.675 (2)	169 (3)
C16—H16A⋯O5iii	0.96	2.44	3.380 (3)	166
C20—H20B⋯Cg4	0.97	2.86	3.750 (3)	153

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