Methyl 3-(1H-indole-3-carboxamido)propionate hemihydrate.

The title compound, C(13)H(14)N(2)O(3)·0.5H(2)O, was synthesized by the condensation of methyl 3-amino-propionate with 3-trichloro-acetyl-indole. The two organic mol-ecules in the asymmetric unit are both close to planar, with r.m.s. deviations from the best fit plane through all of the non-H atoms of 0.004 (2) Å for mol-ecule A and 0.006 (1) Å for mol-ecule B. Also, the five- and six-membered rings of the indole systems are inclined at 1.67 (8) and 1.50 (8)° in mol-ecules A and B, respectively. In the crystal structure, the organic molecules are connected by inter-molecular N-H⋯O hydrogen bonds, forming chains. O-H⋯O and N-H⋯O hydrogen-bond inter-actions involving the water molecules inter-link these chains, forming double chains approximately parallel to the a axis.

Related literature

For the bioactivity of indole derivatives, see: Fabio et al. (2007 ▶); Sharma et al. (2004 ▶). For related structures, see: Huang et al. (2009 ▶); Siddiquee et al. (2009 ▶). For reference structural data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C13H14N2O3·0.5H2O

M = 255.27

Monoclinic,

a = 10.8220 (13) Å

b = 9.7668 (12) Å

c = 23.623 (3) Å

β = 92.422 (2)°

V = 2494.6 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.46 × 0.43 × 0.39 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.962

13021 measured reflections

5484 independent reflections

4349 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.07

5484 reflections

336 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018015/sj2794sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018015/sj2794Isup2.hkl

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

C13H14N2O3·0.5H2O	F(000) = 1080
Mr = 255.27	Dx = 1.359 Mg m−3
Monoclinic, P21/n	Melting point: 409 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.8220 (13) Å	Cell parameters from 7482 reflections
b = 9.7668 (12) Å	θ = 2.3–27.1°
c = 23.623 (3) Å	µ = 0.10 mm−1
β = 92.422 (2)°	T = 173 K
V = 2494.6 (5) Å3	Block, yellow
Z = 8	0.46 × 0.43 × 0.39 mm

Bruker SMART 1K CCD area-detector diffractometer	5484 independent reflections
Radiation source: fine-focus sealed tube	4349 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.955, Tmax = 0.962	k = −8→12
13021 measured reflections	l = −30→30

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) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.3718P] where P = (Fo2 + 2Fc2)/3
5484 reflections	(Δ/σ)max = 0.001
336 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 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 > 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	0.80813 (13)	−0.08599 (15)	0.03833 (6)	0.0318 (3)
H1	0.8269	−0.0666	0.0002	0.038*
C2	0.71838 (12)	−0.02181 (14)	0.06810 (6)	0.0272 (3)
C3	0.72133 (12)	−0.08192 (14)	0.12390 (6)	0.0275 (3)
C4	0.65431 (14)	−0.06387 (16)	0.17297 (6)	0.0341 (3)
H4	0.5917	0.0041	0.1743	0.041*
C5	0.68093 (15)	−0.14651 (17)	0.21922 (6)	0.0398 (4)
H5	0.6352	−0.1356	0.2524	0.048*
C6	0.77349 (16)	−0.24579 (17)	0.21840 (7)	0.0421 (4)
H6	0.7892	−0.3012	0.2510	0.051*
C7	0.84253 (14)	−0.26528 (16)	0.17145 (7)	0.0373 (3)
H7	0.9061	−0.3323	0.1710	0.045*
C8	0.81497 (12)	−0.18210 (14)	0.12439 (6)	0.0297 (3)
C9	0.62911 (13)	0.08453 (15)	0.04984 (6)	0.0305 (3)
C10	0.53881 (13)	0.24140 (15)	−0.01892 (6)	0.0311 (3)
H10A	0.5536	0.3226	0.0055	0.037*
H10B	0.4544	0.2074	−0.0125	0.037*
C11	0.54663 (13)	0.28339 (15)	−0.08026 (6)	0.0321 (3)
H11A	0.6316	0.3150	−0.0872	0.039*
H11B	0.5286	0.2034	−0.1050	0.039*
C12	0.45597 (13)	0.39641 (15)	−0.09478 (6)	0.0308 (3)
C13	0.39062 (16)	0.55673 (18)	−0.16381 (7)	0.0433 (4)
H13A	0.3959	0.6307	−0.1358	0.065*
H13B	0.3056	0.5222	−0.1670	0.065*
H13C	0.4145	0.5917	−0.2007	0.065*
C14	0.29377 (13)	0.36840 (16)	0.06182 (6)	0.0341 (3)
H14	0.3102	0.3692	0.0226	0.041*
C15	0.21024 (12)	0.45232 (14)	0.08725 (6)	0.0290 (3)
C16	0.21441 (12)	0.41712 (14)	0.14649 (6)	0.0284 (3)
C17	0.15418 (14)	0.46235 (16)	0.19450 (6)	0.0354 (3)
H17	0.0928	0.5317	0.1913	0.042*
C18	0.18574 (16)	0.40417 (17)	0.24654 (7)	0.0432 (4)
H18	0.1446	0.4335	0.2791	0.052*
C19	0.27677 (16)	0.30334 (18)	0.25209 (7)	0.0441 (4)
H19	0.2977	0.2669	0.2885	0.053*
C20	0.33663 (15)	0.25580 (17)	0.20592 (7)	0.0399 (4)
H20	0.3981	0.1866	0.2097	0.048*
C21	0.30395 (13)	0.31267 (15)	0.15322 (6)	0.0319 (3)
C22	0.13786 (12)	0.56060 (14)	0.05926 (6)	0.0290 (3)
C23	0.08226 (13)	0.69102 (15)	−0.02576 (6)	0.0301 (3)
H23A	0.1048	0.7807	−0.0088	0.036*
H23B	−0.0072	0.6763	−0.0211	0.036*
C24	0.10799 (13)	0.69297 (15)	−0.08814 (6)	0.0328 (3)
H24A	0.1972	0.7095	−0.0929	0.039*
H24B	0.0866	0.6029	−0.1051	0.039*
C25	0.03353 (13)	0.80346 (15)	−0.11816 (6)	0.0310 (3)
C26	−0.01206 (18)	0.91058 (19)	−0.20573 (7)	0.0497 (4)
H26A	−0.1005	0.8992	−0.1997	0.075*
H26B	0.0033	0.8978	−0.2460	0.075*
H26C	0.0139	1.0028	−0.1940	0.075*
N1	0.86589 (11)	−0.18166 (13)	0.07191 (5)	0.0333 (3)
H1A	0.9265	−0.2351	0.0617	0.040*
N2	0.62849 (11)	0.13484 (13)	−0.00271 (5)	0.0317 (3)
H2	0.6811	0.1044	−0.0272	0.038*
N3	0.34897 (12)	0.28454 (14)	0.10095 (5)	0.0375 (3)
H3	0.4048	0.2220	0.0940	0.045*
N4	0.15203 (11)	0.58337 (12)	0.00368 (5)	0.0320 (3)
H4A	0.2039	0.5327	−0.0150	0.038*
O1	0.55464 (11)	0.12826 (13)	0.08443 (5)	0.0466 (3)
O2	0.37724 (10)	0.43840 (12)	−0.06434 (4)	0.0405 (3)
O3	0.47321 (10)	0.44687 (12)	−0.14607 (4)	0.0393 (3)
O4	0.06489 (10)	0.63299 (11)	0.08581 (4)	0.0396 (3)
O5	−0.03955 (10)	0.87601 (12)	−0.09532 (4)	0.0402 (3)
O6	0.05767 (10)	0.80986 (12)	−0.17246 (4)	0.0413 (3)
O1W	0.20002 (11)	0.89955 (13)	0.09463 (5)	0.0507 (3)
H1B	0.1537	0.8301	0.0994	0.076*
H1C	0.1592	0.9704	0.1031	0.076*

	U11	U22	U33	U12	U13	U23
C1	0.0314 (7)	0.0312 (7)	0.0330 (7)	0.0062 (6)	0.0043 (5)	0.0008 (6)
C2	0.0245 (6)	0.0256 (6)	0.0314 (7)	0.0024 (5)	0.0014 (5)	−0.0018 (5)
C3	0.0257 (6)	0.0249 (6)	0.0317 (7)	0.0006 (5)	−0.0005 (5)	−0.0032 (5)
C4	0.0347 (7)	0.0341 (8)	0.0338 (7)	0.0017 (6)	0.0035 (6)	−0.0060 (6)
C5	0.0477 (9)	0.0418 (9)	0.0303 (7)	−0.0043 (7)	0.0050 (6)	−0.0012 (6)
C6	0.0537 (10)	0.0372 (8)	0.0349 (8)	−0.0022 (7)	−0.0066 (7)	0.0058 (7)
C7	0.0395 (8)	0.0307 (7)	0.0411 (8)	0.0050 (6)	−0.0056 (6)	0.0029 (6)
C8	0.0279 (7)	0.0270 (7)	0.0341 (7)	0.0006 (5)	−0.0005 (5)	−0.0024 (6)
C9	0.0288 (7)	0.0297 (7)	0.0331 (7)	0.0048 (6)	−0.0001 (5)	−0.0024 (6)
C10	0.0319 (7)	0.0298 (7)	0.0315 (7)	0.0067 (6)	−0.0002 (5)	−0.0002 (6)
C11	0.0298 (7)	0.0335 (7)	0.0329 (7)	0.0029 (6)	0.0000 (6)	−0.0017 (6)
C12	0.0311 (7)	0.0322 (7)	0.0289 (7)	−0.0009 (6)	−0.0006 (5)	−0.0002 (6)
C13	0.0491 (9)	0.0457 (9)	0.0353 (8)	0.0135 (8)	0.0020 (7)	0.0086 (7)
C14	0.0337 (7)	0.0351 (8)	0.0337 (7)	0.0100 (6)	0.0053 (6)	0.0028 (6)
C15	0.0259 (6)	0.0268 (7)	0.0345 (7)	0.0041 (5)	0.0027 (5)	0.0002 (6)
C16	0.0268 (6)	0.0243 (6)	0.0341 (7)	0.0008 (5)	0.0004 (5)	0.0001 (5)
C17	0.0389 (8)	0.0294 (7)	0.0381 (8)	0.0072 (6)	0.0045 (6)	−0.0022 (6)
C18	0.0561 (10)	0.0393 (9)	0.0347 (8)	0.0068 (7)	0.0078 (7)	−0.0024 (7)
C19	0.0588 (10)	0.0387 (9)	0.0344 (8)	0.0063 (8)	−0.0015 (7)	0.0052 (7)
C20	0.0431 (8)	0.0356 (8)	0.0409 (8)	0.0106 (7)	−0.0001 (7)	0.0071 (7)
C21	0.0304 (7)	0.0303 (7)	0.0352 (7)	0.0044 (6)	0.0033 (6)	0.0009 (6)
C22	0.0263 (6)	0.0261 (7)	0.0348 (7)	0.0031 (5)	0.0018 (5)	0.0007 (6)
C23	0.0299 (7)	0.0281 (7)	0.0324 (7)	0.0049 (6)	0.0010 (5)	0.0012 (6)
C24	0.0331 (7)	0.0315 (7)	0.0341 (7)	0.0051 (6)	0.0048 (6)	−0.0007 (6)
C25	0.0335 (7)	0.0303 (7)	0.0293 (7)	−0.0022 (6)	0.0032 (5)	−0.0012 (6)
C26	0.0705 (12)	0.0463 (10)	0.0321 (8)	0.0024 (9)	−0.0013 (8)	0.0089 (7)
N1	0.0307 (6)	0.0316 (6)	0.0378 (7)	0.0109 (5)	0.0052 (5)	0.0001 (5)
N2	0.0305 (6)	0.0324 (6)	0.0323 (6)	0.0086 (5)	0.0027 (5)	0.0000 (5)
N3	0.0371 (7)	0.0375 (7)	0.0381 (7)	0.0170 (6)	0.0061 (5)	0.0035 (5)
N4	0.0322 (6)	0.0307 (6)	0.0333 (6)	0.0102 (5)	0.0046 (5)	0.0017 (5)
O1	0.0473 (6)	0.0551 (7)	0.0382 (6)	0.0289 (6)	0.0098 (5)	0.0055 (5)
O2	0.0419 (6)	0.0452 (6)	0.0348 (5)	0.0147 (5)	0.0070 (4)	0.0054 (5)
O3	0.0441 (6)	0.0426 (6)	0.0314 (5)	0.0128 (5)	0.0050 (4)	0.0057 (5)
O4	0.0419 (6)	0.0392 (6)	0.0381 (6)	0.0197 (5)	0.0084 (4)	0.0045 (5)
O5	0.0467 (6)	0.0393 (6)	0.0350 (5)	0.0148 (5)	0.0056 (5)	0.0025 (5)
O6	0.0523 (7)	0.0422 (6)	0.0298 (5)	0.0042 (5)	0.0061 (5)	0.0037 (5)
O1W	0.0556 (7)	0.0471 (7)	0.0506 (7)	0.0176 (6)	0.0152 (6)	0.0011 (6)

C1—N1	1.3606 (18)	C15—C16	1.4399 (19)
C1—C2	1.3744 (19)	C15—C22	1.4579 (19)
C1—H1	0.9500	C16—C17	1.403 (2)
C2—C3	1.4421 (19)	C16—C21	1.4114 (19)
C2—C9	1.4706 (19)	C17—C18	1.384 (2)
C3—C4	1.404 (2)	C17—H17	0.9500
C3—C8	1.4083 (19)	C18—C19	1.395 (2)
C4—C5	1.379 (2)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.373 (2)
C5—C6	1.395 (2)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.395 (2)
C6—C7	1.376 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—N3	1.3743 (19)
C7—C8	1.399 (2)	C22—O4	1.2485 (17)
C7—H7	0.9500	C22—N4	1.3467 (18)
C8—N1	1.3779 (19)	C23—N4	1.4543 (17)
C9—O1	1.2470 (17)	C23—C24	1.511 (2)
C9—N2	1.3348 (18)	C23—H23A	0.9900
C10—N2	1.4630 (17)	C23—H23B	0.9900
C10—C11	1.512 (2)	C24—C25	1.506 (2)
C10—H10A	0.9900	C24—H24A	0.9900
C10—H10B	0.9900	C24—H24B	0.9900
C11—C12	1.507 (2)	C25—O5	1.2062 (18)
C11—H11A	0.9900	C25—O6	1.3212 (17)
C11—H11B	0.9900	C26—O6	1.451 (2)
C12—O2	1.2095 (17)	C26—H26A	0.9800
C12—O3	1.3285 (17)	C26—H26B	0.9800
C13—O3	1.4470 (19)	C26—H26C	0.9800
C13—H13A	0.9800	N1—H1A	0.8800
C13—H13B	0.9800	N2—H2	0.8800
C13—H13C	0.9800	N3—H3	0.8800
C14—N3	1.3548 (19)	N4—H4A	0.8800
C14—C15	1.377 (2)	O1W—H1B	0.8533
C14—H14	0.9500	O1W—H1C	0.8497
N1—C1—C2	109.39 (12)	C21—C16—C15	105.98 (12)
N1—C1—H1	125.3	C18—C17—C16	118.89 (14)
C2—C1—H1	125.3	C18—C17—H17	120.6
C1—C2—C3	107.05 (12)	C16—C17—H17	120.6
C1—C2—C9	129.92 (13)	C17—C18—C19	121.33 (15)
C3—C2—C9	122.99 (12)	C17—C18—H18	119.3
C4—C3—C8	118.49 (13)	C19—C18—H18	119.3
C4—C3—C2	135.33 (13)	C20—C19—C18	121.28 (15)
C8—C3—C2	106.17 (12)	C20—C19—H19	119.4
C5—C4—C3	118.86 (14)	C18—C19—H19	119.4
C5—C4—H4	120.6	C19—C20—C21	117.64 (14)
C3—C4—H4	120.6	C19—C20—H20	121.2
C4—C5—C6	121.47 (15)	C21—C20—H20	121.2
C4—C5—H5	119.3	N3—C21—C20	129.50 (13)
C6—C5—H5	119.3	N3—C21—C16	108.12 (12)
C7—C6—C5	121.46 (15)	C20—C21—C16	122.37 (14)
C7—C6—H6	119.3	O4—C22—N4	119.79 (12)
C5—C6—H6	119.3	O4—C22—C15	121.47 (13)
C6—C7—C8	117.08 (14)	N4—C22—C15	118.73 (12)
C6—C7—H7	121.5	N4—C23—C24	111.22 (11)
C8—C7—H7	121.5	N4—C23—H23A	109.4
N1—C8—C7	129.56 (13)	C24—C23—H23A	109.4
N1—C8—C3	107.79 (12)	N4—C23—H23B	109.4
C7—C8—C3	122.63 (14)	C24—C23—H23B	109.4
O1—C9—N2	120.34 (13)	H23A—C23—H23B	108.0
O1—C9—C2	118.97 (13)	C25—C24—C23	110.56 (11)
N2—C9—C2	120.68 (12)	C25—C24—H24A	109.5
N2—C10—C11	112.37 (11)	C23—C24—H24A	109.5
N2—C10—H10A	109.1	C25—C24—H24B	109.5
C11—C10—H10A	109.1	C23—C24—H24B	109.5
N2—C10—H10B	109.1	H24A—C24—H24B	108.1
C11—C10—H10B	109.1	O5—C25—O6	124.53 (13)
H10A—C10—H10B	107.9	O5—C25—C24	123.92 (13)
C12—C11—C10	110.78 (12)	O6—C25—C24	111.54 (12)
C12—C11—H11A	109.5	O6—C26—H26A	109.5
C10—C11—H11A	109.5	O6—C26—H26B	109.5
C12—C11—H11B	109.5	H26A—C26—H26B	109.5
C10—C11—H11B	109.5	O6—C26—H26C	109.5
H11A—C11—H11B	108.1	H26A—C26—H26C	109.5
O2—C12—O3	123.10 (13)	H26B—C26—H26C	109.5
O2—C12—C11	125.54 (13)	C1—N1—C8	109.60 (11)
O3—C12—C11	111.36 (12)	C1—N1—H1A	125.2
O3—C13—H13A	109.5	C8—N1—H1A	125.2
O3—C13—H13B	109.5	C9—N2—C10	118.86 (11)
H13A—C13—H13B	109.5	C9—N2—H2	120.6
O3—C13—H13C	109.5	C10—N2—H2	120.6
H13A—C13—H13C	109.5	C14—N3—C21	109.23 (12)
H13B—C13—H13C	109.5	C14—N3—H3	125.4
N3—C14—C15	109.93 (13)	C21—N3—H3	125.4
N3—C14—H14	125.0	C22—N4—C23	120.49 (11)
C15—C14—H14	125.0	C22—N4—H4A	119.8
C14—C15—C16	106.73 (12)	C23—N4—H4A	119.8
C14—C15—C22	125.74 (13)	C12—O3—C13	115.49 (12)
C16—C15—C22	127.45 (12)	C25—O6—C26	116.00 (12)
C17—C16—C21	118.46 (13)	H1B—O1W—H1C	107.6
C17—C16—C15	135.56 (13)
N1—C1—C2—C3	0.15 (16)	C16—C17—C18—C19	0.8 (3)
N1—C1—C2—C9	−177.67 (14)	C17—C18—C19—C20	−1.5 (3)
C1—C2—C3—C4	−179.04 (15)	C18—C19—C20—C21	0.5 (3)
C9—C2—C3—C4	−1.0 (2)	C19—C20—C21—N3	179.75 (16)
C1—C2—C3—C8	−0.29 (15)	C19—C20—C21—C16	1.1 (2)
C9—C2—C3—C8	177.72 (12)	C17—C16—C21—N3	179.37 (13)
C8—C3—C4—C5	−1.3 (2)	C15—C16—C21—N3	−1.26 (16)
C2—C3—C4—C5	177.35 (15)	C17—C16—C21—C20	−1.7 (2)
C3—C4—C5—C6	0.8 (2)	C15—C16—C21—C20	177.67 (14)
C4—C5—C6—C7	0.2 (2)	C14—C15—C22—O4	−179.26 (14)
C5—C6—C7—C8	−0.6 (2)	C16—C15—C22—O4	−3.1 (2)
C6—C7—C8—N1	−177.99 (14)	C14—C15—C22—N4	−0.2 (2)
C6—C7—C8—C3	0.1 (2)	C16—C15—C22—N4	175.97 (13)
C4—C3—C8—N1	179.32 (12)	N4—C23—C24—C25	179.09 (12)
C2—C3—C8—N1	0.31 (15)	C23—C24—C25—O5	−2.6 (2)
C4—C3—C8—C7	0.9 (2)	C23—C24—C25—O6	177.96 (12)
C2—C3—C8—C7	−178.12 (13)	C2—C1—N1—C8	0.05 (16)
C1—C2—C9—O1	179.73 (15)	C7—C8—N1—C1	178.05 (15)
C3—C2—C9—O1	2.2 (2)	C3—C8—N1—C1	−0.23 (16)
C1—C2—C9—N2	−1.0 (2)	O1—C9—N2—C10	−0.2 (2)
C3—C2—C9—N2	−178.56 (12)	C2—C9—N2—C10	−179.46 (12)
N2—C10—C11—C12	−178.09 (12)	C11—C10—N2—C9	−177.74 (12)
C10—C11—C12—O2	−8.0 (2)	C15—C14—N3—C21	−0.72 (18)
C10—C11—C12—O3	171.58 (12)	C20—C21—N3—C14	−177.58 (16)
N3—C14—C15—C16	−0.08 (17)	C16—C21—N3—C14	1.25 (17)
N3—C14—C15—C22	176.72 (13)	O4—C22—N4—C23	−0.5 (2)
C14—C15—C16—C17	−179.97 (16)	C15—C22—N4—C23	−179.56 (13)
C22—C15—C16—C17	3.3 (3)	C24—C23—N4—C22	−177.04 (12)
C14—C15—C16—C21	0.82 (16)	O2—C12—O3—C13	−0.2 (2)
C22—C15—C16—C21	−175.91 (14)	C11—C12—O3—C13	−179.74 (13)
C21—C16—C17—C18	0.7 (2)	O5—C25—O6—C26	−1.2 (2)
C15—C16—C17—C18	−178.40 (16)	C24—C25—O6—C26	178.26 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.88	2.04	2.8219 (15)	148
N2—H2···O1Wii	0.88	2.09	2.9348 (17)	161
N3—H3···O1	0.88	1.88	2.7404 (16)	164
N4—H4A···O2	0.88	2.43	3.2952 (15)	167
O1W—H1B···O4	0.85	2.17	2.9890 (18)	161
O1W—H1C···O5iii	0.85	1.98	2.7970 (16)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.88	2.04	2.8219 (15)	148
N2—H2⋯O1Wii	0.88	2.09	2.9348 (17)	161
N3—H3⋯O1	0.88	1.88	2.7404 (16)	164
N4—H4A⋯O2	0.88	2.43	3.2952 (15)	167
O1W—H1B⋯O4	0.85	2.17	2.9890 (18)	161
O1W—H1C⋯O5iii	0.85	1.98	2.7970 (16)	160

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