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The asymmetric unit of the title compound comprises the monohydrated form of the natural product arcyriaflavin A [systematic name: 12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione monohydrate], C20H11N3O2·H2O. Individual mol­ecular units are engaged in hydrogen-bonding inter­actions, forming two-dimensional zigzag supra­molecular layers parallel to the (\overline{1}02) plane. The close packing of the layers is mediated by strong co-operative π–π stacking inter­actions, in tandem with inter­layer hydrogen bonds invol­ving the solvent water mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110052741/gt3028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110052741/gt3028Isup2.hkl
Contains datablock I

CCDC reference: 817042

Comment top

Arcyriaflavin A is a natural product belonging to the family of indolocarbazole alkaloids. This family has potential therapeutic application in the treatment of cancer (Sánchez et al., 2006) because of its ability to inhibit protein kinases. The most widely known indolocarbazole alkaloid is staurosporine, a potent inhibitor of phospholipid/Ca2+-dependent protein kinase (protein kinase C) from rat brain (Tamaoki et al., 1986). Several of its derivatives have already entered clinical trials as anticancer agents (Sánchez et al., 2006), and it was also the model drug for the study of Meggers and co-workers on the design of metal complexes as protein kinase inhibitors (Bregman et al., 2006). The title compound, (I), is an attractive aglycone staurosporine derivative, first isolated from the myxomycete Arcyria denudata (Steglich, 1989). It has a wide span of cytotoxic and antiproliferative action, ranging from moderate antibiotic activity against fungi and bacteria (Keller & Everhart, 2010) to in vitro antiviral properties towards the human cytomegalovirus (Slater et al., 1999) and cytotoxicity towards the K562 human chronic myelogenous leukemia cell line (Liu et al., 2007). In addition, it also works via kinase inhibition, namely of the cyclin-dependent kinase 4 (CDK4) (Zhu et al., 2003).

The asymmetric unit of (I) comprises an arcyriaflavin A molecule and a solvent water molecule (Fig. 1). The organic molecules arrange themselves in a zig-zag fashion, forming layers parallel to the (1 0 2) plane (Fig. 2a). Within these layers, the molecules are interconnected by strong directional hydrogen bonds [D···A distances in the range 2.811 (2)–3.066 (2) Å, D—H···A angles greater than ca 156°; see Table 1 for specific details (dashed lines in Fig. 2)]. On the other hand, the dominant supramolecular contacts between adjacent layers are ππ stacking forces (Fig. 2b), with a distance between aromatic rings of ca 3.38 Å.

Within each layer, the arcyriaflavin A molecules are arranged into dimers via two N···O hydrogen bonds related by a centre of inversion, forming a hydrogen-bonding pattern that can be described by an R22(8) graph-set motif (Grell et al., 1999). It is noteworthy that the two molecular units are not coplanar, with the mean planes being ca 0.65 Å from each other. The β-diamine group (atoms N1 and N2) acts as a two-proton donor to the neighbouring solvent water molecule, forming a ring of graph set R12(7). The water molecule bridges adjacent arcyriaflavin A molecules from two distinct supramolecular layers via O—H···O hydrogen-bonding interactions with the carbonyl groups (atoms O1 and O2). One of these interactions (O1W···O1), together with the aforementioned R12(7) and R22(8) rings, promotes the formation of the two-dimensional supramolecular layers. The remaining interaction of the water molecule [O1W···O2iii; symmetry code: (iii) -x + 1, -y + 1, -z + 1] connects different layers, as shown in Fig. 2(b).

Related literature top

For related literature, see: Bregman et al. (2006); Grell et al. (1999); Keller & Everhart (2010); Liu et al. (2007); Sánchez et al. (2006); Slater et al. (1999); Steglich (1989); Tamaoki et al. (1986); Zhu et al. (2003).

Experimental top

Arcyriaflavin A was purchased from Tocris Bioscience (>98% purity) and used as received without further purification. Orange needle crystals [Block given in CIF tables - please clarify] suitable for the crystallographic studies reported here were isolated over a period of one week by slow evaporation from an ethanolic solution.

Refinement top

H atoms bound to aromatic C atoms were placed in their idealized positions and included in the final structural model in a riding-motion approximation, with C—H = 0.95 Å, and with Uiso(H) = 1.2Ueq(C). H atoms associated with the solvent water molecule and the N—H groups were located directly from a difference Fourier map. The positions of these atoms were refined and Uiso(H) = 1.5Ueq(N,O).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. (a) Schematic representation of the two-dimensional supramolecular layer formed by the hydrogen-bonding interactions between arcyriaflavin A and water molecules. (b) Simplified crystal packing, showing the hydrogen-bonding connections between adjacent layers via the solvent water molecule. Hydrogen bonds are represented as dashed lines. See Table 1 for geometric details of these interactions.
12,13-Dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole- 5,7(6H)-dione monohydrate top
Crystal data top
C20H11N3O2·H2OF(000) = 712
Mr = 343.33Dx = 1.465 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1965 reflections
a = 4.7347 (1) Åθ = 3.2–26.8°
b = 18.1877 (7) ŵ = 0.10 mm1
c = 18.1068 (6) ÅT = 150 K
β = 93.594 (2)°Needle, orange
V = 1556.17 (9) Å30.11 × 0.04 × 0.03 mm
Z = 4
Data collection top
Bruker X8 APEXII KappaCCD
diffractometer
4172 independent reflections
Radiation source: fine-focus sealed tube2477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ω and ϕ scansθmax = 29.1°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 66
Tmin = 0.989, Tmax = 0.997k = 2424
13901 measured reflectionsl = 2324
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0682P)2]
where P = (Fo2 + 2Fc2)/3
4172 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C20H11N3O2·H2OV = 1556.17 (9) Å3
Mr = 343.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.7347 (1) ŵ = 0.10 mm1
b = 18.1877 (7) ÅT = 150 K
c = 18.1068 (6) Å0.11 × 0.04 × 0.03 mm
β = 93.594 (2)°
Data collection top
Bruker X8 APEXII KappaCCD
diffractometer
4172 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
2477 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.997Rint = 0.057
13901 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.26 e Å3
4172 reflectionsΔρmin = 0.24 e Å3
250 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.5189 (3)0.69064 (10)0.14881 (9)0.0239 (4)
H10.564 (4)0.7334 (13)0.1205 (11)0.036*
N21.0080 (3)0.77362 (9)0.24051 (9)0.0252 (4)
H20.971 (4)0.7998 (13)0.1964 (12)0.038*
N30.7397 (4)0.51761 (10)0.42005 (9)0.0305 (4)
H30.757 (4)0.4792 (13)0.4543 (12)0.046*
O10.3928 (3)0.46754 (8)0.34051 (7)0.0331 (4)
O21.0902 (3)0.59252 (8)0.47367 (7)0.0353 (4)
C10.3171 (4)0.63734 (11)0.13025 (10)0.0236 (4)
C20.1380 (4)0.63151 (12)0.06676 (11)0.0273 (5)
H2A0.14320.66650.02790.033*
C30.0471 (4)0.57315 (12)0.06214 (11)0.0290 (5)
H3A0.17240.56820.01940.035*
C40.0559 (4)0.52084 (11)0.11878 (10)0.0270 (5)
H40.18680.48130.11390.032*
C50.1242 (4)0.52627 (11)0.18163 (10)0.0240 (4)
H50.11850.49070.21990.029*
C60.3147 (3)0.58492 (11)0.18796 (10)0.0212 (4)
C70.5280 (3)0.60824 (11)0.24366 (10)0.0208 (4)
C80.6491 (4)0.67331 (11)0.21664 (10)0.0210 (4)
C90.8653 (4)0.71063 (11)0.25726 (10)0.0224 (4)
C100.9719 (4)0.68393 (11)0.32719 (10)0.0214 (4)
C111.1894 (4)0.73449 (11)0.35359 (10)0.0226 (4)
C121.2044 (4)0.78945 (11)0.29831 (10)0.0245 (4)
C131.3936 (4)0.84801 (11)0.30593 (12)0.0302 (5)
H131.40110.88480.26880.036*
C141.5698 (4)0.85051 (12)0.36959 (12)0.0329 (5)
H141.70130.88980.37630.039*
C151.5596 (4)0.79679 (12)0.42438 (11)0.0302 (5)
H151.68470.80020.46730.036*
C161.3711 (4)0.73869 (11)0.41747 (11)0.0265 (4)
H161.36520.70250.45520.032*
C170.5662 (4)0.51610 (11)0.35512 (11)0.0261 (4)
C180.6368 (4)0.58159 (10)0.31263 (10)0.0216 (4)
C190.8534 (4)0.61916 (11)0.35307 (10)0.0215 (4)
C200.9177 (4)0.57823 (11)0.42180 (11)0.0266 (4)
O1W0.2162 (4)0.33447 (9)0.40166 (9)0.0430 (4)
H1X0.110 (5)0.3474 (15)0.4389 (16)0.064*
H1Y0.297 (5)0.3775 (16)0.3810 (14)0.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0245 (8)0.0244 (9)0.0227 (9)0.0021 (7)0.0014 (6)0.0034 (7)
N20.0265 (8)0.0234 (9)0.0261 (9)0.0001 (7)0.0045 (7)0.0026 (7)
N30.0389 (10)0.0268 (10)0.0246 (10)0.0077 (8)0.0064 (7)0.0065 (8)
O10.0385 (8)0.0266 (8)0.0332 (8)0.0101 (7)0.0058 (6)0.0030 (7)
O20.0439 (8)0.0332 (9)0.0270 (8)0.0081 (7)0.0115 (7)0.0025 (7)
C10.0206 (9)0.0246 (11)0.0258 (10)0.0052 (8)0.0047 (8)0.0003 (8)
C20.0252 (10)0.0334 (12)0.0231 (10)0.0067 (9)0.0001 (8)0.0025 (9)
C30.0262 (10)0.0353 (13)0.0248 (10)0.0063 (9)0.0037 (8)0.0035 (9)
C40.0238 (9)0.0281 (12)0.0290 (11)0.0011 (8)0.0007 (8)0.0058 (9)
C50.0238 (9)0.0236 (11)0.0249 (10)0.0034 (8)0.0035 (7)0.0006 (8)
C60.0203 (9)0.0226 (10)0.0209 (9)0.0062 (7)0.0034 (7)0.0017 (8)
C70.0185 (8)0.0212 (10)0.0228 (10)0.0037 (7)0.0022 (7)0.0023 (8)
C80.0211 (9)0.0231 (10)0.0188 (9)0.0044 (7)0.0023 (7)0.0002 (8)
C90.0234 (9)0.0189 (10)0.0256 (10)0.0027 (8)0.0066 (7)0.0018 (8)
C100.0225 (9)0.0202 (10)0.0219 (10)0.0034 (8)0.0039 (7)0.0027 (8)
C110.0204 (9)0.0199 (10)0.0280 (10)0.0020 (7)0.0056 (7)0.0057 (8)
C120.0233 (9)0.0229 (11)0.0279 (10)0.0022 (8)0.0073 (8)0.0030 (9)
C130.0311 (10)0.0242 (11)0.0365 (12)0.0016 (9)0.0108 (9)0.0002 (9)
C140.0262 (10)0.0283 (12)0.0448 (13)0.0064 (9)0.0079 (9)0.0078 (10)
C150.0257 (10)0.0297 (12)0.0350 (12)0.0027 (9)0.0017 (8)0.0101 (10)
C160.0248 (9)0.0272 (11)0.0275 (11)0.0004 (8)0.0022 (8)0.0035 (9)
C170.0285 (10)0.0251 (11)0.0246 (10)0.0010 (8)0.0013 (8)0.0024 (9)
C180.0234 (9)0.0195 (10)0.0217 (9)0.0011 (7)0.0015 (7)0.0011 (8)
C190.0242 (9)0.0212 (10)0.0190 (9)0.0012 (8)0.0005 (7)0.0009 (8)
C200.0292 (10)0.0247 (11)0.0257 (10)0.0025 (8)0.0011 (8)0.0003 (9)
O1W0.0635 (11)0.0303 (10)0.0357 (9)0.0068 (8)0.0077 (8)0.0019 (8)
Geometric parameters (Å, º) top
N1—C81.376 (2)C7—C181.407 (3)
N1—C11.388 (2)C7—C81.415 (3)
N1—H10.96 (2)C8—C91.398 (3)
N2—C91.374 (2)C9—C101.419 (3)
N2—C121.386 (2)C10—C191.398 (3)
N2—H20.94 (2)C10—C111.440 (3)
N3—C201.387 (2)C11—C161.400 (3)
N3—C171.392 (2)C11—C121.419 (3)
N3—H30.93 (2)C12—C131.393 (3)
O1—C171.223 (2)C13—C141.381 (3)
O2—C201.233 (2)C13—H130.9500
C1—C21.389 (3)C14—C151.395 (3)
C1—C61.415 (3)C14—H140.9500
C2—C31.376 (3)C15—C161.384 (3)
C2—H2A0.9500C15—H150.9500
C3—C41.402 (3)C16—H160.9500
C3—H3A0.9500C17—C181.468 (3)
C4—C51.382 (3)C18—C191.400 (2)
C4—H40.9500C19—C201.466 (3)
C5—C61.397 (3)O1W—H1X0.90 (3)
C5—H50.9500O1W—H1Y0.96 (3)
C6—C71.446 (2)
C8—N1—C1108.61 (16)C8—C9—C10120.72 (18)
C8—N1—H1123.9 (12)C19—C10—C9117.37 (17)
C1—N1—H1127.4 (12)C19—C10—C11136.10 (17)
C9—N2—C12108.82 (16)C9—C10—C11106.54 (17)
C9—N2—H2122.9 (13)C16—C11—C12119.28 (17)
C12—N2—H2128.3 (13)C16—C11—C10134.35 (18)
C20—N3—C17111.15 (16)C12—C11—C10106.37 (16)
C20—N3—H3123.5 (14)N2—C12—C13129.09 (19)
C17—N3—H3124.6 (14)N2—C12—C11108.99 (17)
N1—C1—C2128.97 (18)C13—C12—C11121.92 (18)
N1—C1—C6109.22 (16)C14—C13—C12117.32 (19)
C2—C1—C6121.81 (18)C14—C13—H13121.3
C3—C2—C1117.55 (18)C12—C13—H13121.3
C3—C2—H2A121.2C13—C14—C15121.63 (19)
C1—C2—H2A121.2C13—C14—H14119.2
C2—C3—C4121.83 (18)C15—C14—H14119.2
C2—C3—H3A119.1C16—C15—C14121.43 (19)
C4—C3—H3A119.1C16—C15—H15119.3
C5—C4—C3120.60 (19)C14—C15—H15119.3
C5—C4—H4119.7C15—C16—C11118.42 (19)
C3—C4—H4119.7C15—C16—H16120.8
C4—C5—C6118.94 (18)C11—C16—H16120.8
C4—C5—H5120.5O1—C17—N3123.34 (19)
C6—C5—H5120.5O1—C17—C18130.11 (18)
C5—C6—C1119.26 (17)N3—C17—C18106.55 (16)
C5—C6—C7134.47 (18)C19—C18—C7120.77 (18)
C1—C6—C7106.26 (16)C19—C18—C17107.77 (16)
C18—C7—C8117.47 (16)C7—C18—C17131.46 (17)
C18—C7—C6135.99 (18)C10—C19—C18122.13 (17)
C8—C7—C6106.53 (16)C10—C19—C20130.25 (17)
N1—C8—C9129.09 (18)C18—C19—C20107.62 (17)
N1—C8—C7109.37 (16)O2—C20—N3123.89 (18)
C9—C8—C7121.53 (16)O2—C20—C19129.20 (19)
N2—C9—C8130.00 (18)N3—C20—C19106.90 (16)
N2—C9—C10109.28 (16)H1X—O1W—H1Y110 (2)
C8—N1—C1—C2178.92 (18)C9—N2—C12—C13179.37 (18)
C8—N1—C1—C60.8 (2)C9—N2—C12—C110.6 (2)
N1—C1—C2—C3179.33 (18)C16—C11—C12—N2179.52 (16)
C6—C1—C2—C31.0 (3)C10—C11—C12—N20.3 (2)
C1—C2—C3—C40.4 (3)C16—C11—C12—C130.5 (3)
C2—C3—C4—C50.3 (3)C10—C11—C12—C13179.64 (16)
C3—C4—C5—C60.2 (3)N2—C12—C13—C14179.52 (18)
C4—C5—C6—C10.4 (2)C11—C12—C13—C140.5 (3)
C4—C5—C6—C7179.78 (19)C12—C13—C14—C150.1 (3)
N1—C1—C6—C5179.23 (16)C13—C14—C15—C160.3 (3)
C2—C1—C6—C51.0 (3)C14—C15—C16—C110.3 (3)
N1—C1—C6—C70.31 (19)C12—C11—C16—C150.1 (3)
C2—C1—C6—C7179.41 (17)C10—C11—C16—C15179.89 (19)
C5—C6—C7—C181.9 (4)C20—N3—C17—O1179.32 (18)
C1—C6—C7—C18178.7 (2)C20—N3—C17—C180.8 (2)
C5—C6—C7—C8179.69 (19)C8—C7—C18—C191.0 (3)
C1—C6—C7—C80.25 (19)C6—C7—C18—C19179.36 (19)
C1—N1—C8—C9179.70 (18)C8—C7—C18—C17178.38 (18)
C1—N1—C8—C70.9 (2)C6—C7—C18—C170.1 (4)
C18—C7—C8—N1179.50 (15)O1—C17—C18—C19179.1 (2)
C6—C7—C8—N10.73 (19)N3—C17—C18—C191.0 (2)
C18—C7—C8—C91.1 (3)O1—C17—C18—C70.4 (4)
C6—C7—C8—C9179.85 (16)N3—C17—C18—C7179.48 (19)
C12—N2—C9—C8179.86 (18)C9—C10—C19—C180.4 (3)
C12—N2—C9—C100.6 (2)C11—C10—C19—C18179.86 (19)
N1—C8—C9—N20.9 (3)C9—C10—C19—C20179.69 (18)
C7—C8—C9—N2179.85 (17)C11—C10—C19—C200.2 (4)
N1—C8—C9—C10179.67 (17)C7—C18—C19—C100.3 (3)
C7—C8—C9—C100.4 (3)C17—C18—C19—C10179.22 (16)
N2—C9—C10—C19179.20 (16)C7—C18—C19—C20179.60 (16)
C8—C9—C10—C190.4 (3)C17—C18—C19—C200.8 (2)
N2—C9—C10—C110.41 (19)C17—N3—C20—O2179.34 (19)
C8—C9—C10—C11179.98 (16)C17—N3—C20—C190.3 (2)
C19—C10—C11—C160.4 (4)C10—C19—C20—O21.3 (4)
C9—C10—C11—C16179.9 (2)C18—C19—C20—O2178.6 (2)
C19—C10—C11—C12179.5 (2)C10—C19—C20—N3179.72 (18)
C9—C10—C11—C120.05 (19)C18—C19—C20—N30.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1Wi0.96 (2)2.16 (2)3.065 (2)155.6 (17)
N2—H2···O1Wi0.94 (2)2.03 (2)2.939 (2)161.8 (19)
N3—H3···O2ii0.93 (2)1.95 (2)2.858 (2)163.1 (19)
O1W—H1X···O2iii0.90 (3)2.19 (3)3.062 (2)164 (2)
O1W—H1Y···O10.96 (3)1.86 (3)2.810 (2)171 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC20H11N3O2·H2O
Mr343.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)4.7347 (1), 18.1877 (7), 18.1068 (6)
β (°) 93.594 (2)
V3)1556.17 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.11 × 0.04 × 0.03
Data collection
DiffractometerBruker X8 APEXII KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1998)
Tmin, Tmax0.989, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
13901, 4172, 2477
Rint0.057
(sin θ/λ)max1)0.684
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.141, 1.00
No. of reflections4172
No. of parameters250
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.24

Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1Wi0.96 (2)2.16 (2)3.065 (2)155.6 (17)
N2—H2···O1Wi0.94 (2)2.03 (2)2.939 (2)161.8 (19)
N3—H3···O2ii0.93 (2)1.95 (2)2.858 (2)163.1 (19)
O1W—H1X···O2iii0.90 (3)2.19 (3)3.062 (2)164 (2)
O1W—H1Y···O10.96 (3)1.86 (3)2.810 (2)171 (2)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1.
 

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