4-Amino-8-cyclo-pent-yloxy-7-meth-oxy-2H-chromen-2-one monohydrate.

The asymmetric unit of the title compound, C(15)H(17)NO(4)·H(2)O, contains two organic mol-ecules with marginal differences between them and two water molecules. The chromine rings in both mol-ecules are essentially planar, with maximum deviations of 0.012 (2) and 0.060 (2) Å. The five-membered cyclo-pentane rings adopt envelope conformations in both mol-ecules. In the crystal, the components are linked by N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, resulting in a three-dimensional network.

Related literature

For applications of the title compound in the treatment or prevention of disease, see: Scherlach et al. (2011 ▶); Luan et al. (2011 ▶); Yang et al. (2011 ▶). For a related structure, see: Doriguetto et al. (2006 ▶).

Experimental

Crystal data

C15H17NO4·H2O

M = 293.31

Monoclinic,

a = 20.3651 (4) Å

b = 7.43162 (16) Å

c = 19.4049 (4) Å

β = 91.0792 (18)°

V = 2936.32 (11) Å3

Z = 8

Cu Kα radiation

μ = 0.83 mm−1

T = 153 K

0.36 × 0.31 × 0.20 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2006 ▶) T min = 0.754, T max = 0.851

13804 measured reflections

5167 independent reflections

4701 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.193

S = 1.08

5167 reflections

394 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S160053681201450X/pv2524sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201450X/pv2524Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201450X/pv2524Isup3.cml

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

C15H17NO4·H2O	F(000) = 1248
Mr = 293.31	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 13804 reflections
a = 20.3651 (4) Å	θ = 4.6–67.0°
b = 7.43162 (16) Å	µ = 0.83 mm−1
c = 19.4049 (4) Å	T = 153 K
β = 91.0792 (18)°	Block, yellow
V = 2936.32 (11) Å3	0.36 × 0.31 × 0.20 mm
Z = 8

Agilent Xcalibur Atlas Gemini ultra diffractometer	5167 independent reflections
Radiation source: fine-focus sealed tube	4701 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 67.0°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2006)	h = −21→24
Tmin = 0.754, Tmax = 0.851	k = −8→8
13804 measured reflections	l = −21→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.193	w = 1/[σ2(Fo2) + (0.103P)2 + 4.5099P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
5167 reflections	Δρmax = 0.38 e Å−3
394 parameters	Δρmin = −0.30 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (5)

Experimental. Absorption correction: empirical absorption correction using spherical harmonics implemented in SCALE3 ABSPACK scaling algorithm (Agilent, 2006)

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
O1	0.31349 (9)	0.6751 (3)	0.05051 (9)	0.0277 (5)
O2	0.40956 (8)	0.6823 (3)	0.10419 (9)	0.0196 (4)
O3	0.53980 (8)	0.6560 (2)	0.08977 (8)	0.0189 (4)
O4	0.62167 (8)	0.6828 (3)	0.19846 (9)	0.0251 (5)
N1	0.32021 (10)	0.7551 (3)	0.29237 (11)	0.0239 (5)
H1A	0.2771	0.7601	0.2944	0.029*
H1B	0.3443	0.7650	0.3303	0.029*
C1	0.34144 (12)	0.6908 (4)	0.10708 (13)	0.0214 (6)
C2	0.31268 (12)	0.7164 (4)	0.17122 (14)	0.0227 (6)
H2	0.2662	0.7230	0.1732	0.027*
C3	0.34885 (12)	0.7326 (4)	0.23200 (13)	0.0194 (5)
C4	0.42038 (12)	0.7240 (3)	0.22795 (13)	0.0183 (5)
C5	0.44727 (12)	0.6996 (3)	0.16325 (13)	0.0174 (5)
C6	0.51502 (12)	0.6893 (3)	0.15391 (12)	0.0180 (5)
C7	0.46357 (12)	0.7384 (4)	0.28460 (13)	0.0203 (6)
H7	0.4464	0.7561	0.3293	0.024*
C8	0.53058 (13)	0.7274 (4)	0.27689 (13)	0.0212 (6)
H8	0.5590	0.7377	0.3160	0.025*
C9	0.55674 (12)	0.7012 (3)	0.21161 (13)	0.0195 (5)
C10	0.66766 (13)	0.7058 (4)	0.25445 (14)	0.0281 (6)
H10A	0.7124	0.6893	0.2378	0.042*
H10B	0.6589	0.6166	0.2903	0.042*
H10C	0.6632	0.8271	0.2736	0.042*
C11	0.54069 (13)	0.8129 (4)	0.04407 (13)	0.0215 (6)
H11	0.4969	0.8737	0.0423	0.026*
C12	0.55964 (14)	0.7436 (4)	−0.02734 (13)	0.0262 (6)
H12A	0.5295	0.7927	−0.0633	0.031*
H12B	0.5575	0.6106	−0.0289	0.031*
C13	0.63040 (16)	0.8087 (5)	−0.03896 (17)	0.0371 (8)
H13A	0.6577	0.7101	−0.0573	0.044*
H13B	0.6308	0.9105	−0.0718	0.044*
C14	0.65589 (14)	0.8678 (4)	0.03183 (16)	0.0317 (7)
H14A	0.6904	0.9609	0.0278	0.038*
H14B	0.6738	0.7645	0.0583	0.038*
C15	0.59466 (12)	0.9438 (4)	0.06545 (14)	0.0246 (6)
H15A	0.6002	0.9477	0.1162	0.030*
H15B	0.5849	1.0665	0.0483	0.030*
O5	−0.18130 (8)	0.1918 (3)	0.70123 (9)	0.0248 (5)
O6	−0.08754 (8)	0.2503 (3)	0.65200 (9)	0.0200 (4)
O7	0.04038 (8)	0.3412 (2)	0.67260 (9)	0.0199 (4)
O8	0.12364 (8)	0.3338 (3)	0.56941 (9)	0.0251 (5)
N2	−0.17177 (11)	0.1820 (3)	0.45783 (11)	0.0255 (5)
H2A	−0.2141	0.1598	0.4532	0.031*
H2B	−0.1475	0.1940	0.4211	0.031*
C16	−0.15351 (12)	0.2038 (4)	0.64569 (13)	0.0201 (6)
C17	−0.18055 (12)	0.1794 (4)	0.57953 (13)	0.0217 (6)
H17	−0.2258	0.1492	0.5751	0.026*
C18	−0.14447 (12)	0.1972 (4)	0.52039 (13)	0.0200 (6)
C19	−0.07400 (12)	0.2311 (4)	0.52828 (13)	0.0193 (5)
C20	−0.04892 (12)	0.2580 (4)	0.59489 (13)	0.0183 (5)
C21	0.01742 (12)	0.2956 (4)	0.60801 (13)	0.0189 (5)
C22	−0.03026 (13)	0.2365 (4)	0.47378 (13)	0.0219 (6)
H22	−0.0462	0.2182	0.4280	0.026*
C23	0.03603 (13)	0.2680 (4)	0.48542 (13)	0.0224 (6)
H23	0.0653	0.2691	0.4478	0.027*
C24	0.05997 (12)	0.2983 (4)	0.55240 (14)	0.0207 (6)
C25	0.17107 (13)	0.3265 (4)	0.51606 (15)	0.0283 (6)
H25A	0.2149	0.3496	0.5358	0.043*
H25B	0.1606	0.4178	0.4811	0.043*
H25C	0.1702	0.2069	0.4947	0.043*
C26	0.04488 (13)	0.1944 (4)	0.72309 (13)	0.0241 (6)
H26	0.0012	0.1355	0.7292	0.029*
C27	0.06993 (14)	0.2795 (5)	0.79080 (14)	0.0333 (7)
H27A	0.0707	0.4123	0.7868	0.040*
H27B	0.0411	0.2460	0.8293	0.040*
C28	0.13955 (14)	0.2063 (4)	0.80336 (16)	0.0319 (7)
H28A	0.1695	0.3028	0.8198	0.038*
H28B	0.1395	0.1083	0.8379	0.038*
C29	0.16034 (14)	0.1360 (4)	0.73356 (16)	0.0325 (7)
H29A	0.1945	0.0420	0.7385	0.039*
H29B	0.1770	0.2344	0.7043	0.039*
C30	0.09641 (14)	0.0582 (4)	0.70385 (14)	0.0291 (6)
H30A	0.0987	0.0450	0.6532	0.035*
H30B	0.0869	−0.0607	0.7244	0.035*
O1W	0.13246 (12)	0.6480 (3)	0.66569 (10)	0.0392 (6)
H1AA	0.1427	0.6601	0.7076	0.059*
H1AB	0.1154	0.5456	0.6612	0.059*
O2W	0.63303 (11)	0.3753 (3)	0.07811 (10)	0.0325 (5)
H2AA	0.6077	0.4646	0.0784	0.049*
H2AB	0.6437	0.3589	0.0370	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0165 (9)	0.0481 (13)	0.0185 (9)	0.0032 (8)	−0.0009 (7)	−0.0048 (8)
O2	0.0114 (8)	0.0306 (10)	0.0168 (9)	0.0015 (7)	0.0012 (6)	−0.0020 (7)
O3	0.0168 (8)	0.0235 (10)	0.0165 (9)	0.0023 (7)	0.0044 (6)	0.0003 (7)
O4	0.0110 (8)	0.0421 (12)	0.0222 (10)	0.0022 (8)	0.0008 (7)	−0.0008 (8)
N1	0.0139 (10)	0.0391 (14)	0.0188 (11)	−0.0010 (9)	0.0034 (8)	−0.0013 (10)
C1	0.0152 (12)	0.0268 (14)	0.0222 (13)	0.0013 (10)	0.0007 (10)	−0.0015 (10)
C2	0.0139 (12)	0.0306 (15)	0.0237 (13)	0.0003 (10)	0.0034 (10)	−0.0012 (11)
C3	0.0176 (12)	0.0194 (13)	0.0214 (13)	0.0000 (10)	0.0037 (10)	−0.0003 (10)
C4	0.0169 (12)	0.0179 (13)	0.0201 (13)	0.0005 (9)	0.0028 (10)	0.0004 (10)
C5	0.0180 (12)	0.0168 (12)	0.0173 (12)	0.0001 (9)	−0.0003 (9)	0.0003 (9)
C6	0.0167 (12)	0.0207 (13)	0.0168 (12)	0.0016 (10)	0.0034 (9)	0.0000 (10)
C7	0.0202 (13)	0.0224 (14)	0.0184 (12)	0.0010 (10)	0.0031 (10)	−0.0001 (10)
C8	0.0190 (12)	0.0273 (14)	0.0173 (13)	0.0003 (10)	−0.0005 (10)	0.0005 (10)
C9	0.0136 (12)	0.0213 (13)	0.0238 (13)	0.0014 (10)	0.0021 (10)	0.0009 (10)
C10	0.0152 (13)	0.0407 (17)	0.0281 (15)	0.0001 (11)	−0.0034 (11)	−0.0030 (12)
C11	0.0188 (13)	0.0265 (14)	0.0193 (13)	0.0039 (10)	0.0034 (10)	0.0032 (10)
C12	0.0288 (14)	0.0318 (15)	0.0181 (13)	0.0018 (12)	0.0038 (11)	0.0003 (11)
C13	0.0357 (17)	0.0392 (18)	0.0371 (17)	−0.0026 (14)	0.0202 (13)	−0.0049 (14)
C14	0.0206 (14)	0.0311 (16)	0.0436 (17)	−0.0031 (12)	0.0088 (12)	0.0001 (13)
C15	0.0232 (13)	0.0258 (14)	0.0250 (13)	0.0000 (11)	0.0049 (10)	−0.0001 (11)
O5	0.0157 (9)	0.0397 (12)	0.0191 (9)	0.0004 (8)	0.0029 (7)	0.0009 (8)
O6	0.0131 (8)	0.0313 (10)	0.0158 (9)	−0.0018 (7)	0.0012 (6)	−0.0015 (7)
O7	0.0166 (8)	0.0252 (10)	0.0177 (9)	−0.0024 (7)	−0.0007 (7)	−0.0008 (7)
O8	0.0128 (9)	0.0396 (12)	0.0231 (10)	−0.0041 (8)	0.0028 (7)	−0.0010 (8)
N2	0.0145 (10)	0.0433 (15)	0.0186 (11)	−0.0029 (10)	−0.0007 (8)	−0.0006 (10)
C16	0.0140 (12)	0.0244 (14)	0.0220 (13)	0.0031 (10)	0.0026 (10)	0.0007 (10)
C17	0.0123 (12)	0.0291 (15)	0.0238 (13)	−0.0007 (10)	−0.0006 (10)	−0.0001 (11)
C18	0.0179 (13)	0.0223 (13)	0.0199 (13)	0.0016 (10)	−0.0009 (10)	0.0006 (10)
C19	0.0173 (13)	0.0201 (13)	0.0203 (13)	−0.0005 (10)	0.0001 (10)	0.0005 (10)
C20	0.0174 (12)	0.0204 (13)	0.0173 (12)	0.0028 (10)	0.0029 (9)	0.0010 (10)
C21	0.0172 (12)	0.0219 (13)	0.0174 (12)	0.0012 (10)	−0.0012 (9)	0.0001 (10)
C22	0.0197 (13)	0.0295 (15)	0.0163 (12)	−0.0008 (11)	0.0000 (10)	−0.0010 (10)
C23	0.0194 (13)	0.0294 (15)	0.0184 (13)	−0.0003 (11)	0.0055 (10)	0.0013 (10)
C24	0.0160 (12)	0.0215 (13)	0.0247 (13)	−0.0017 (10)	0.0010 (10)	0.0013 (10)
C25	0.0157 (12)	0.0407 (17)	0.0289 (15)	−0.0029 (12)	0.0073 (10)	0.0013 (12)
C26	0.0179 (13)	0.0349 (16)	0.0196 (13)	−0.0031 (11)	−0.0010 (10)	0.0068 (11)
C27	0.0278 (15)	0.054 (2)	0.0178 (13)	0.0073 (14)	−0.0013 (11)	−0.0015 (13)
C28	0.0281 (15)	0.0321 (16)	0.0352 (16)	0.0000 (12)	−0.0121 (12)	−0.0022 (12)
C29	0.0224 (14)	0.0341 (17)	0.0409 (17)	0.0075 (12)	−0.0003 (12)	0.0044 (13)
C30	0.0345 (15)	0.0259 (15)	0.0266 (14)	0.0012 (12)	−0.0040 (11)	0.0003 (11)
O1W	0.0633 (15)	0.0337 (12)	0.0203 (10)	−0.0172 (11)	−0.0063 (10)	0.0017 (9)
O2W	0.0448 (12)	0.0328 (12)	0.0201 (10)	0.0148 (10)	0.0079 (8)	0.0028 (8)

O1—C1	1.233 (3)	O6—C16	1.390 (3)
O2—C5	1.374 (3)	O7—C21	1.372 (3)
O2—C1	1.391 (3)	O7—C26	1.468 (3)
O3—C6	1.374 (3)	O8—C24	1.358 (3)
O3—C11	1.465 (3)	O8—C25	1.430 (3)
O4—C9	1.358 (3)	N2—C18	1.331 (3)
O4—C10	1.431 (3)	N2—H2A	0.8800
N1—C3	1.329 (3)	N2—H2B	0.8800
N1—H1A	0.8800	C16—C17	1.399 (4)
N1—H1B	0.8800	C17—C18	1.381 (4)
C1—C2	1.398 (4)	C17—H17	0.9500
C2—C3	1.384 (4)	C18—C19	1.462 (3)
C2—H2	0.9500	C19—C20	1.395 (4)
C3—C4	1.462 (3)	C19—C22	1.396 (4)
C4—C5	1.391 (3)	C20—C21	1.398 (4)
C4—C7	1.399 (4)	C21—C24	1.397 (4)
C5—C6	1.397 (3)	C22—C23	1.385 (4)
C6—C9	1.395 (4)	C22—H22	0.9500
C7—C8	1.378 (4)	C23—C24	1.398 (4)
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.397 (4)	C25—H25A	0.9800
C8—H8	0.9500	C25—H25B	0.9800
C10—H10A	0.9800	C25—H25C	0.9800
C10—H10B	0.9800	C26—C30	1.510 (4)
C10—H10C	0.9800	C26—C27	1.537 (4)
C11—C15	1.520 (4)	C26—H26	1.0000
C11—C12	1.534 (4)	C27—C28	1.534 (4)
C11—H11	1.0000	C27—H27A	0.9900
C12—C13	1.541 (4)	C27—H27B	0.9900
C12—H12A	0.9900	C28—C29	1.519 (4)
C12—H12B	0.9900	C28—H28A	0.9900
C13—C14	1.524 (4)	C28—H28B	0.9900
C13—H13A	0.9900	C29—C30	1.528 (4)
C13—H13B	0.9900	C29—H29A	0.9900
C14—C15	1.526 (4)	C29—H29B	0.9900
C14—H14A	0.9900	C30—H30A	0.9900
C14—H14B	0.9900	C30—H30B	0.9900
C15—H15A	0.9900	O1W—H1AA	0.8400
C15—H15B	0.9900	O1W—H1AB	0.8400
O5—C16	1.230 (3)	O2W—H2AA	0.8400
O6—C20	1.372 (3)	O2W—H2AB	0.8400
C5—O2—C1	120.30 (19)	C21—O7—C26	116.2 (2)
C6—O3—C11	114.45 (19)	C24—O8—C25	118.1 (2)
C9—O4—C10	118.1 (2)	C18—N2—H2A	120.0
C3—N1—H1A	120.0	C18—N2—H2B	120.0
C3—N1—H1B	120.0	H2A—N2—H2B	120.0
H1A—N1—H1B	120.0	O5—C16—O6	113.6 (2)
O1—C1—O2	113.8 (2)	O5—C16—C17	127.9 (2)
O1—C1—C2	127.7 (2)	O6—C16—C17	118.4 (2)
O2—C1—C2	118.5 (2)	C18—C17—C16	122.9 (2)
C3—C2—C1	123.0 (2)	C18—C17—H17	118.5
C3—C2—H2	118.5	C16—C17—H17	118.5
C1—C2—H2	118.5	N2—C18—C17	122.0 (2)
N1—C3—C2	121.8 (2)	N2—C18—C19	120.2 (2)
N1—C3—C4	120.5 (2)	C17—C18—C19	117.8 (2)
C2—C3—C4	117.7 (2)	C20—C19—C22	118.0 (2)
C5—C4—C7	117.8 (2)	C20—C19—C18	117.6 (2)
C5—C4—C3	117.6 (2)	C22—C19—C18	124.4 (2)
C7—C4—C3	124.5 (2)	O6—C20—C19	122.5 (2)
O2—C5—C4	122.8 (2)	O6—C20—C21	115.3 (2)
O2—C5—C6	115.1 (2)	C19—C20—C21	122.2 (2)
C4—C5—C6	122.1 (2)	O7—C21—C24	119.8 (2)
O3—C6—C9	120.6 (2)	O7—C21—C20	121.8 (2)
O3—C6—C5	120.5 (2)	C24—C21—C20	118.3 (2)
C9—C6—C5	118.7 (2)	C23—C22—C19	121.0 (2)
C8—C7—C4	121.3 (2)	C23—C22—H22	119.5
C8—C7—H7	119.4	C19—C22—H22	119.5
C4—C7—H7	119.4	C22—C23—C24	120.1 (2)
C7—C8—C9	120.1 (2)	C22—C23—H23	120.0
C7—C8—H8	119.9	C24—C23—H23	120.0
C9—C8—H8	119.9	O8—C24—C21	114.7 (2)
O4—C9—C6	115.0 (2)	O8—C24—C23	124.9 (2)
O4—C9—C8	125.0 (2)	C21—C24—C23	120.4 (2)
C6—C9—C8	120.0 (2)	O8—C25—H25A	109.5
O4—C10—H10A	109.5	O8—C25—H25B	109.5
O4—C10—H10B	109.5	H25A—C25—H25B	109.5
H10A—C10—H10B	109.5	O8—C25—H25C	109.5
O4—C10—H10C	109.5	H25A—C25—H25C	109.5
H10A—C10—H10C	109.5	H25B—C25—H25C	109.5
H10B—C10—H10C	109.5	O7—C26—C30	111.6 (2)
O3—C11—C15	111.2 (2)	O7—C26—C27	106.3 (2)
O3—C11—C12	106.6 (2)	C30—C26—C27	105.4 (2)
C15—C11—C12	105.6 (2)	O7—C26—H26	111.1
O3—C11—H11	111.1	C30—C26—H26	111.1
C15—C11—H11	111.1	C27—C26—H26	111.1
C12—C11—H11	111.1	C28—C27—C26	106.3 (2)
C11—C12—C13	106.2 (2)	C28—C27—H27A	110.5
C11—C12—H12A	110.5	C26—C27—H27A	110.5
C13—C12—H12A	110.5	C28—C27—H27B	110.5
C11—C12—H12B	110.5	C26—C27—H27B	110.5
C13—C12—H12B	110.5	H27A—C27—H27B	108.7
H12A—C12—H12B	108.7	C29—C28—C27	104.6 (2)
C14—C13—C12	105.2 (2)	C29—C28—H28A	110.8
C14—C13—H13A	110.7	C27—C28—H28A	110.8
C12—C13—H13A	110.7	C29—C28—H28B	110.8
C14—C13—H13B	110.7	C27—C28—H28B	110.8
C12—C13—H13B	110.7	H28A—C28—H28B	108.9
H13A—C13—H13B	108.8	C28—C29—C30	102.5 (2)
C13—C14—C15	103.0 (2)	C28—C29—H29A	111.3
C13—C14—H14A	111.2	C30—C29—H29A	111.3
C15—C14—H14A	111.2	C28—C29—H29B	111.3
C13—C14—H14B	111.2	C30—C29—H29B	111.3
C15—C14—H14B	111.2	H29A—C29—H29B	109.2
H14A—C14—H14B	109.1	C26—C30—C29	104.1 (2)
C11—C15—C14	103.8 (2)	C26—C30—H30A	110.9
C11—C15—H15A	111.0	C29—C30—H30A	110.9
C14—C15—H15A	111.0	C26—C30—H30B	110.9
C11—C15—H15B	111.0	C29—C30—H30B	110.9
C14—C15—H15B	111.0	H30A—C30—H30B	108.9
H15A—C15—H15B	109.0	H1AA—O1W—H1AB	106.9
C20—O6—C16	120.44 (19)	H2AA—O2W—H2AB	106.9
C5—O2—C1—O1	179.3 (2)	C20—O6—C16—O5	175.9 (2)
C5—O2—C1—C2	−0.3 (4)	C20—O6—C16—C17	−5.0 (4)
O1—C1—C2—C3	−179.9 (3)	O5—C16—C17—C18	179.7 (3)
O2—C1—C2—C3	−0.4 (4)	O6—C16—C17—C18	0.8 (4)
C1—C2—C3—N1	−179.3 (3)	C16—C17—C18—N2	−176.7 (3)
C1—C2—C3—C4	0.6 (4)	C16—C17—C18—C19	4.2 (4)
N1—C3—C4—C5	179.8 (2)	N2—C18—C19—C20	175.8 (3)
C2—C3—C4—C5	−0.2 (4)	C17—C18—C19—C20	−5.2 (4)
N1—C3—C4—C7	−0.1 (4)	N2—C18—C19—C22	−4.9 (4)
C2—C3—C4—C7	179.9 (3)	C17—C18—C19—C22	174.1 (3)
C1—O2—C5—C4	0.7 (4)	C16—O6—C20—C19	4.0 (4)
C1—O2—C5—C6	−179.8 (2)	C16—O6—C20—C21	−176.3 (2)
C7—C4—C5—O2	179.5 (2)	C22—C19—C20—O6	−178.2 (2)
C3—C4—C5—O2	−0.5 (4)	C18—C19—C20—O6	1.2 (4)
C7—C4—C5—C6	0.0 (4)	C22—C19—C20—C21	2.2 (4)
C3—C4—C5—C6	−179.9 (2)	C18—C19—C20—C21	−178.4 (2)
C11—O3—C6—C9	−105.6 (3)	C26—O7—C21—C24	−110.7 (3)
C11—O3—C6—C5	78.9 (3)	C26—O7—C21—C20	73.9 (3)
O2—C5—C6—O3	−2.8 (3)	O6—C20—C21—O7	−6.9 (4)
C4—C5—C6—O3	176.7 (2)	C19—C20—C21—O7	172.7 (2)
O2—C5—C6—C9	−178.4 (2)	O6—C20—C21—C24	177.5 (2)
C4—C5—C6—C9	1.1 (4)	C19—C20—C21—C24	−2.8 (4)
C5—C4—C7—C8	−0.5 (4)	C20—C19—C22—C23	−0.2 (4)
C3—C4—C7—C8	179.4 (3)	C18—C19—C22—C23	−179.5 (3)
C4—C7—C8—C9	−0.1 (4)	C19—C22—C23—C24	−1.1 (4)
C10—O4—C9—C6	175.8 (2)	C25—O8—C24—C21	175.7 (2)
C10—O4—C9—C8	−5.2 (4)	C25—O8—C24—C23	−5.1 (4)
O3—C6—C9—O4	1.8 (4)	O7—C21—C24—O8	5.1 (4)
C5—C6—C9—O4	177.5 (2)	C20—C21—C24—O8	−179.3 (2)
O3—C6—C9—C8	−177.3 (2)	O7—C21—C24—C23	−174.2 (2)
C5—C6—C9—C8	−1.6 (4)	C20—C21—C24—C23	1.4 (4)
C7—C8—C9—O4	−177.8 (3)	C22—C23—C24—O8	−178.7 (3)
C7—C8—C9—C6	1.2 (4)	C22—C23—C24—C21	0.5 (4)
C6—O3—C11—C15	73.9 (3)	C21—O7—C26—C30	66.9 (3)
C6—O3—C11—C12	−171.6 (2)	C21—O7—C26—C27	−178.7 (2)
O3—C11—C12—C13	−107.8 (2)	O7—C26—C27—C28	−111.5 (3)
C15—C11—C12—C13	10.6 (3)	C30—C26—C27—C28	7.1 (3)
C11—C12—C13—C14	14.6 (3)	C26—C27—C28—C29	18.4 (3)
C12—C13—C14—C15	−34.0 (3)	C27—C28—C29—C30	−36.6 (3)
O3—C11—C15—C14	83.5 (2)	O7—C26—C30—C29	85.1 (3)
C12—C11—C15—C14	−31.7 (3)	C27—C26—C30—C29	−29.9 (3)
C13—C14—C15—C11	40.8 (3)	C28—C29—C30—C26	41.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.88	1.99	2.861 (3)	172
N1—H1B···O2Wii	0.88	2.00	2.816 (3)	153
N2—H2A···O1iii	0.88	2.03	2.888 (3)	166
N2—H2B···O1Wi	0.88	2.08	2.838 (3)	144
O1W—H1AA···O5iv	0.84	1.94	2.769 (3)	170
O2W—H2AB···O1v	0.84	1.94	2.767 (3)	168
O1W—H1AB···O7	0.84	2.17	2.956 (3)	156
O1W—H1AB···O8	0.84	2.39	2.994 (3)	130
O2W—H2AA···O3	0.84	2.00	2.833 (3)	171
C7—H7···O2Wii	0.95	2.60	3.493 (3)	158
C15—H15B···O2Wvi	0.99	2.56	3.309 (4)	133
C11—H11···O2	1.00	2.59	3.091 (3)	111
C15—H15A···O4	0.99	2.57	3.267 (3)	128
C26—H26···O6	1.00	2.48	3.035 (3)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.88	1.99	2.861 (3)	172
N1—H1B⋯O2Wii	0.88	2.00	2.816 (3)	153
N2—H2A⋯O1iii	0.88	2.03	2.888 (3)	166
N2—H2B⋯O1Wi	0.88	2.08	2.838 (3)	144
O1W—H1AA⋯O5iv	0.84	1.94	2.769 (3)	170
O2W—H2AB⋯O1v	0.84	1.94	2.767 (3)	168
O1W—H1AB⋯O7	0.84	2.17	2.956 (3)	156
O1W—H1AB⋯O8	0.84	2.39	2.994 (3)	130
O2W—H2AA⋯O3	0.84	2.00	2.833 (3)	171
C7—H7⋯O2Wii	0.95	2.60	3.493 (3)	158
C15—H15B⋯O2Wvi	0.99	2.56	3.309 (4)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .