catena-Poly[[[di­aqua­bis­(seleno­cyanato-κN)iron(II)]-μ-1,2-bis­(pyridin-4-yl)ethane-κ²N:N′] 1,2-bis­(pyridin-4-yl)ethane disolvate dihydrate]

The title compound, {[Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]·2C₁₂H₁₂N₂·2H₂O}_n, was obtained by the reaction of iron(II) sulfate hepta­hydrate and potassium seleno­cyanate with 1,2-bis­(pyridin-4-yl)ethane (bpa) in water. The Fe^II cation is coordinated by two N-bonded seleno­cyanate anions, two water mol­ecules and two 1,2-bis­(pyridin-4-yl)ethane (bpa) ligands in a slightly distorted octa­hedral geometry. In addition, two non-coordinating bpa mol­ecules and two water mol­ecules are present. The Fe^II cation is located on a center of inversion while the coordinating bpa ligand is located on a twofold rotation axis. The Fe^II cations are linked by the bpa ligands into chains along the b-axis direction, which are further connected into layers perpedicular to the c axis by O—H...N and O—H...O hydrogen bonds to the non-coordin­ating bpa and the water mol­ecules. The crystal studied was twinned by pseudo-merohedry (180° rotation along c*; contribution of the minor twin component 3.7%).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.119
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT927_ALERT_1_A Reported and Calculated  wR2 Differ by .........    -0.2055

Author Response: The crystal is twinned by pseudo-merohedry (rotation around (1 0 0) and twinning was included in the refinement (Twin law -1 0 0, 0 -1 0, 1 0 1)

Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1O1   ..  H2O2    ..       1.98 Ang.
PLAT926_ALERT_1_B Reported and Calculated   R1 Differ by .........    -0.0346
PLAT928_ALERT_1_B Reported and Calculated    S value   Differ by .     -1.879

Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         44
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4
PLAT920_ALERT_1_C Theta(Max)  in CIF and FCF Differ by ...........       0.12 Deg.
PLAT924_ALERT_1_C The Reported and Calculated Rho(min) Differ by .       1.44 eA-3
PLAT925_ALERT_1_C The Reported and Calculated Rho(max) Differ by .       1.14 eA-3
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.72 eA-3
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.65 eA-3
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.63 eA-3
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.56 eA-3
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.55 eA-3
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.51 eA-3
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.84 eA-3
PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density      -1.57 eA-3
PLAT976_ALERT_2_C Negative Residual Density at 0.89A from O2     .      -1.01 eA-3

Alert level G
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........          4
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         91

   1 ALERT level A = Most likely a serious problem - resolve or explain
   3 ALERT level B = A potentially serious problem, consider carefully
  15 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

S1. Comment

In our recent work we have reported on the synthesis and characterization of cobalt(II) and iron(II) selenocyanate coordination polymers that show coexistence of metamagnetism and a slow relaxation of the magnetization (Boeckmann & Näther, 2011; Wöhlert et al., 2012 and Boeckmann et al., 2012). These compounds can be prepared by thermal decomposition of suitable precursor compounds that contain volatile ligands like e.g. water in hydrates and therefore, such compounds are of extreme importance for our project. In the course of these investigations we obtained such a precursor based on 1,2-bis(pyridin-4-yl)ethane (bpa), which was characterized by single-crystal X-ray diffraction.

In the crystal structure of the title compound Fe(NCSe)₂(C₁₂H₁₂N₂)(H₂O)₂]_n^.2C₁₂H₁₂N₂^.2H₂O solvate each Fe^II cation is coordinated by two N-bonded selenocyanate anions, two water molecules and two bpa ligands (Fig. 1). The FeN₄O₂ octahedra are slightly distorted with distances in the range of 2.071 (4) Å to 2.344 (4) Å. The angles arround the Fe^II cations are in the range of 86.91 (16) ° to 93.09 (16) ° and of 180 ° (Tab. 1). Each Fe^II cation is located on a center of inversion while the coordinating bpa ligand is located on a twofold rotation axis. The iron(II) cations are connected by the bpa ligands into one dimensional polymeric chains, which elongate in the direction of the crystallographic b-axis (Fig. 2). These chains are linked by intermolecular O—H···N and O—H···O hydrogen bonding into layers by non-coordinating bpa ligands and water molecules perpedicular to c (Fig. 2, Tab. 2).

Related literature

For background to this work see: Boeckmann & Näther (2011); Wöhlert et al. (2012); Boeckmann et al. (2012).

S2. Experimental

FeSO₄×7H₂O, KNCSe and 1,2-bis(pyridin-4-yl)ethane were obtained from Alfa Aesar. All chemicals were used without further purification. 0.15 mmol (43 mg) FeSO₄×7H₂O and 0.2 mmol (28 mg) KNCSe were reacted with 0.6 mmol (109 mg) 1,2-bis(pyridin-4-yl)ethane in 1 ml water. Red single-crystals of the title compound were obtained after three days.

S3. Refinement

All H atoms were positions with idealized geometry and were refined isotropically with U_iso(H) = 1.2 U_eq(C) using a riding model with C—H = 0.93 Å and C—H₂ = 0.97 Å. The O—H hydrogen atom were located in a difference map, their bond lengths were set to an ideal value of 0.82 Å, and finally they were refined using a riding model with U_iso(H) = 1.5 U_eq(O). Twinning by pseudo-merohedry of the crystal by a 180° rotation along c* was taken into account, using a twin matrix (-1 0 0 0 -1 0 1 0 1; BASF parameter: 0.03696) which lowered the R value from 6.16 to 4.5%.

Computing details

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures

	Fig. 1. : Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = -x + 2, -y, -z + 1; ii = -x + 2, -y + 1, -z + 1; iii = x, y - 1, z.
	Fig. 2. : Crystal structure of the title compound with O–H–N and O–H–O hydrogen bonding shown as dashed lines (black = iron, blue = nitrogen, orange = selenium, red = oxygen, grey = carbon, white = hydrogen).

catena-Poly[[[diaquabis(selenocyanato-κN)iron(II)]-µ-1,2-bis(pyridin-4-yl)ethane-κ²N:N'] 1,2-bis(pyridin-4-yl)ethane disolvate dihydrate]

Crystal data

[Fe(NCSe)2(C12H12N2)(H2O)2]·2C12H12N2·2H2O	F(000) = 908
Mr = 890.58	Dx = 1.498 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20183 reflections
a = 8.0790 (6) Å	θ = 2.4–27.5°
b = 14.1870 (7) Å	µ = 2.28 mm^−1
c = 17.6553 (12) Å	T = 293 K
β = 102.645 (8)°	Block, red
V = 1974.5 (2) Å^3	0.23 × 0.16 × 0.09 mm
Z = 2

Data collection

Stoe IPDS-2 diffractometer	4540 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
ω scan	θmax = 27.5°, θmin = 2.4°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −10→10
Tmin = 0.645, Tmax = 0.818	k = −18→18
20183 measured reflections	l = −22→22

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) = 0.119	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 4.2316P] where P = (Fo^2 + 2Fc^2)/3
4540 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.88 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Fe1	1.0000	0.0000	0.5000	0.01501 (15)
N1	1.0298 (4)	−0.0036 (2)	0.62294 (18)	0.0224 (6)
C1	0.9954 (4)	−0.0081 (2)	0.6834 (2)	0.0174 (7)
Se1	0.94592 (5)	−0.01632 (3)	0.77704 (2)	0.02554 (12)
N10	0.9925 (4)	0.16528 (19)	0.50356 (18)	0.0189 (6)
C10	1.0341 (5)	0.2181 (2)	0.4477 (2)	0.0229 (8)
H10	1.0757	0.1878	0.4090	0.028*
C11	1.0186 (5)	0.3159 (2)	0.4442 (2)	0.0246 (8)
H11	1.0494	0.3489	0.4040	0.030*
C12	0.9576 (5)	0.3639 (2)	0.5007 (2)	0.0223 (8)
C13	0.9174 (6)	0.3093 (2)	0.5604 (2)	0.0251 (8)
H13	0.8780	0.3379	0.6004	0.030*
C14	0.9370 (5)	0.2119 (2)	0.5591 (2)	0.0229 (8)
H14	0.9099	0.1770	0.5994	0.027*
C15	0.9243 (6)	0.4693 (2)	0.4954 (3)	0.0353 (11)
H15A	0.8506	0.4826	0.4454	0.042*
H15B	0.8631	0.4864	0.5349	0.042*
N20	0.5764 (5)	0.1671 (2)	0.6762 (2)	0.0319 (8)
C20	0.6829 (6)	0.2156 (3)	0.7307 (3)	0.0319 (9)
H20	0.7699	0.1830	0.7635	0.038*
C21	0.6708 (6)	0.3120 (3)	0.7410 (3)	0.0296 (9)
H21	0.7474	0.3429	0.7801	0.036*
C22	0.5421 (5)	0.3616 (2)	0.6920 (2)	0.0254 (8)
C23	0.4316 (6)	0.3110 (3)	0.6357 (3)	0.0320 (9)
H23	0.3433	0.3414	0.6020	0.038*
C24	0.4532 (6)	0.2150 (3)	0.6300 (3)	0.0342 (10)
H24	0.3775	0.1821	0.5918	0.041*
C25	0.5290 (6)	0.4669 (3)	0.6976 (2)	0.0291 (9)
H25A	0.6028	0.4888	0.7453	0.035*
H25B	0.4135	0.4844	0.6987	0.035*
C26	0.5799 (6)	0.5132 (3)	0.6283 (2)	0.0277 (8)
H26A	0.6899	0.4891	0.6241	0.033*
H26B	0.4986	0.4955	0.5815	0.033*
C27	0.5889 (5)	0.6193 (2)	0.6332 (2)	0.0229 (8)
C28	0.6949 (5)	0.6639 (3)	0.6955 (2)	0.0253 (8)
H28	0.7595	0.6288	0.7359	0.030*
C29	0.7026 (5)	0.7616 (3)	0.6964 (2)	0.0283 (8)
H29	0.7759	0.7909	0.7376	0.034*
C30	0.5083 (7)	0.7723 (3)	0.5820 (3)	0.0365 (10)
H30	0.4436	0.8091	0.5429	0.044*
C31	0.4938 (6)	0.6753 (3)	0.5756 (3)	0.0329 (9)
H31	0.4209	0.6480	0.5332	0.039*
N21	0.6101 (5)	0.8156 (2)	0.6412 (2)	0.0309 (8)
O1	1.2588 (3)	0.00213 (19)	0.50632 (15)	0.0241 (5)
H1O1	1.2976	−0.0004	0.4672	0.036*
H2O1	1.3430	−0.0061	0.5412	0.036*
O2	1.4393 (4)	0.00140 (17)	0.39471 (15)	0.0227 (5)
H1O2	1.3985	−0.0371	0.3612	0.034*
H2O2	1.3942	0.0526	0.3828	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0173 (3)	0.0124 (3)	0.0164 (3)	0.0008 (2)	0.0059 (3)	0.0003 (2)
N1	0.0271 (16)	0.0203 (14)	0.0197 (15)	0.0008 (12)	0.0049 (13)	0.0006 (11)
C1	0.0183 (16)	0.0117 (14)	0.0204 (17)	0.0007 (12)	0.0007 (13)	−0.0002 (11)
Se1	0.0285 (2)	0.03071 (19)	0.01874 (19)	−0.00250 (16)	0.00811 (15)	−0.00011 (14)
N10	0.0242 (15)	0.0135 (13)	0.0199 (14)	0.0008 (11)	0.0067 (12)	0.0008 (10)
C10	0.032 (2)	0.0146 (15)	0.0268 (19)	−0.0005 (14)	0.0168 (17)	−0.0018 (13)
C11	0.034 (2)	0.0159 (15)	0.029 (2)	−0.0030 (14)	0.0198 (18)	0.0026 (13)
C12	0.0263 (19)	0.0118 (15)	0.032 (2)	−0.0015 (13)	0.0132 (17)	−0.0007 (13)
C13	0.037 (2)	0.0166 (16)	0.0266 (19)	0.0007 (15)	0.0166 (17)	−0.0031 (14)
C14	0.034 (2)	0.0151 (15)	0.0214 (17)	0.0023 (14)	0.0110 (16)	0.0017 (13)
C15	0.045 (3)	0.0125 (16)	0.059 (3)	0.0014 (16)	0.034 (2)	−0.0004 (16)
N20	0.044 (2)	0.0205 (15)	0.0312 (18)	0.0000 (14)	0.0075 (17)	−0.0019 (13)
C20	0.034 (2)	0.0256 (19)	0.036 (2)	0.0033 (16)	0.0073 (19)	0.0017 (16)
C21	0.033 (2)	0.0226 (18)	0.034 (2)	−0.0059 (15)	0.0077 (18)	−0.0015 (15)
C22	0.031 (2)	0.0181 (16)	0.032 (2)	−0.0014 (14)	0.0172 (18)	−0.0003 (14)
C23	0.038 (2)	0.0248 (19)	0.032 (2)	0.0006 (16)	0.0034 (19)	0.0013 (15)
C24	0.048 (3)	0.0226 (18)	0.029 (2)	−0.0054 (17)	0.003 (2)	−0.0039 (15)
C25	0.034 (2)	0.0204 (17)	0.037 (2)	−0.0012 (15)	0.0168 (19)	−0.0042 (15)
C26	0.037 (2)	0.0181 (16)	0.030 (2)	0.0010 (15)	0.0115 (18)	−0.0013 (14)
C27	0.0235 (19)	0.0179 (16)	0.029 (2)	0.0002 (13)	0.0098 (16)	−0.0015 (13)
C28	0.025 (2)	0.0213 (17)	0.032 (2)	0.0019 (14)	0.0101 (17)	0.0002 (14)
C29	0.031 (2)	0.0211 (17)	0.034 (2)	−0.0025 (15)	0.0099 (18)	−0.0030 (15)
C30	0.047 (3)	0.0242 (19)	0.037 (2)	0.0062 (18)	0.007 (2)	0.0079 (16)
C31	0.040 (2)	0.0262 (19)	0.030 (2)	−0.0027 (17)	0.0022 (19)	0.0004 (15)
N21	0.040 (2)	0.0194 (15)	0.036 (2)	0.0017 (14)	0.0137 (17)	0.0011 (13)
O1	0.0186 (13)	0.0350 (14)	0.0195 (12)	0.0013 (10)	0.0059 (11)	0.0015 (10)
O2	0.0271 (14)	0.0174 (11)	0.0231 (13)	0.0031 (10)	0.0043 (11)	−0.0012 (9)

Geometric parameters (Å, º)

Fe1—O1	2.069 (3)	C21—H21	0.9300
Fe1—O1^i	2.069 (3)	C22—C23	1.383 (6)
Fe1—N1^i	2.132 (3)	C22—C25	1.503 (5)
Fe1—N1	2.132 (3)	C23—C24	1.379 (6)
Fe1—N10^i	2.347 (3)	C23—H23	0.9300
Fe1—N10	2.347 (3)	C24—H24	0.9300
N1—C1	1.162 (5)	C25—C26	1.522 (6)
C1—Se1	1.788 (4)	C25—H25A	0.9700
N10—C10	1.339 (5)	C25—H25B	0.9700
N10—C14	1.339 (5)	C26—C27	1.508 (5)
C10—C11	1.393 (5)	C26—H26A	0.9700
C10—H10	0.9300	C26—H26B	0.9700
C11—C12	1.384 (5)	C27—C31	1.383 (6)
C11—H11	0.9300	C27—C28	1.390 (5)
C12—C13	1.402 (5)	C28—C29	1.388 (5)
C12—C15	1.519 (5)	C28—H28	0.9300
C13—C14	1.392 (5)	C29—N21	1.333 (5)
C13—H13	0.9300	C29—H29	0.9300
C14—H14	0.9300	C30—N21	1.330 (6)
C15—C15^ii	1.481 (9)	C30—C31	1.384 (6)
C15—H15A	0.9700	C30—H30	0.9300
C15—H15B	0.9700	C31—H31	0.9300
N20—C24	1.327 (6)	O1—H1O1	0.8201
N20—C20	1.333 (6)	O1—H2O1	0.8201
C20—C21	1.386 (5)	O2—H1O2	0.8199
C20—H20	0.9300	O2—H2O2	0.8200
C21—C22	1.390 (6)
O1—Fe1—O1^i	180.000 (1)	C20—C21—C22	118.9 (4)
O1—Fe1—N1^i	86.68 (12)	C20—C21—H21	120.5
O1^i—Fe1—N1^i	93.32 (12)	C22—C21—H21	120.5
O1—Fe1—N1	93.32 (12)	C23—C22—C21	117.5 (3)
O1^i—Fe1—N1	86.68 (12)	C23—C22—C25	121.3 (4)
N1^i—Fe1—N1	180.000 (1)	C21—C22—C25	121.1 (4)
O1—Fe1—N10^i	89.09 (11)	C24—C23—C22	119.6 (4)
O1^i—Fe1—N10^i	90.91 (11)	C24—C23—H23	120.2
N1^i—Fe1—N10^i	89.69 (11)	C22—C23—H23	120.2
N1—Fe1—N10^i	90.31 (11)	N20—C24—C23	123.4 (4)
O1—Fe1—N10	90.91 (11)	N20—C24—H24	118.3
O1^i—Fe1—N10	89.09 (11)	C23—C24—H24	118.3
N1^i—Fe1—N10	90.31 (11)	C22—C25—C26	109.9 (3)
N1—Fe1—N10	89.69 (11)	C22—C25—H25A	109.7
N10^i—Fe1—N10	180.000 (1)	C26—C25—H25A	109.7
C1—N1—Fe1	160.1 (3)	C22—C25—H25B	109.7
N1—C1—Se1	178.9 (3)	C26—C25—H25B	109.7
C10—N10—C14	116.2 (3)	H25A—C25—H25B	108.2
C10—N10—Fe1	121.8 (2)	C27—C26—C25	113.8 (3)
C14—N10—Fe1	121.8 (2)	C27—C26—H26A	108.8
N10—C10—C11	123.7 (3)	C25—C26—H26A	108.8
N10—C10—H10	118.1	C27—C26—H26B	108.8
C11—C10—H10	118.1	C25—C26—H26B	108.8
C12—C11—C10	120.1 (3)	H26A—C26—H26B	107.7
C12—C11—H11	120.0	C31—C27—C28	117.9 (3)
C10—C11—H11	120.0	C31—C27—C26	121.3 (4)
C11—C12—C13	116.5 (3)	C28—C27—C26	120.8 (3)
C11—C12—C15	121.8 (3)	C29—C28—C27	118.8 (4)
C13—C12—C15	121.6 (3)	C29—C28—H28	120.6
C14—C13—C12	119.4 (3)	C27—C28—H28	120.6
C14—C13—H13	120.3	N21—C29—C28	123.3 (4)
C12—C13—H13	120.3	N21—C29—H29	118.3
N10—C14—C13	124.0 (3)	C28—C29—H29	118.3
N10—C14—H14	118.0	N21—C30—C31	123.3 (4)
C13—C14—H14	118.0	N21—C30—H30	118.3
C15^ii—C15—C12	116.2 (5)	C31—C30—H30	118.3
C15^ii—C15—H15A	108.2	C27—C31—C30	119.2 (4)
C12—C15—H15A	108.2	C27—C31—H31	120.4
C15^ii—C15—H15B	108.2	C30—C31—H31	120.4
C12—C15—H15B	108.2	C30—N21—C29	117.4 (3)
H15A—C15—H15B	107.4	Fe1—O1—H1O1	121.5
C24—N20—C20	117.3 (3)	Fe1—O1—H2O1	134.5
N20—C20—C21	123.4 (4)	H1O1—O1—H2O1	102.6
N20—C20—H20	118.3	H1O2—O2—H2O2	108.6
C21—C20—H20	118.3

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.82	1.89	2.696 (4)	166
O1—H2O1···O2^iii	0.82	1.87	2.672 (4)	165
O2—H1O2···N20^i	0.82	1.98	2.688 (4)	144
O2—H2O2···N21^ii	0.82	1.92	2.682 (4)	155

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+3, −y, −z+1.