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The structure of the title compound, C20H20N4O14·H2O·CH3CN, dimerizes in the solid state to form an open-ended box which holds two H2O and two CH3CN mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028564/ac6196sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028564/ac6196Isup2.hkl
Contains datablock I

CCDC reference: 287429

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.119
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O2 .. C15 .. 2.91 Ang. PLAT731_ALERT_1_B Bond Calc 0.84(7), Rep 0.839(10) ...... 7.00 su-Rat O1W -H1W 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.84(7), Rep 0.839(10) ...... 7.00 su-Rat O1W -H1W 1.555 1.555 PLAT736_ALERT_1_B H...A Calc 2.31(7), Rep 2.314(17) ...... 4.12 su-Rat H1W -O13 1.555 2.566
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT430_ALERT_2_C Short Inter D...A Contact O9 .. O12 .. 2.88 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O9 .. C16 .. 2.98 Ang. PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Rat O1W -H2W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Rat O1W -H2W 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.10(4), Rep 2.105(16) ...... 2.50 su-Rat H2W -N5 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C20 H20 N4 O14 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H3 N PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The complexation ability of crown ethers has been well studied with regard to alkali metal ions and ammonium derivatized guests (Gokel et al., 2004). Functionalized dibenzocrown ethers offer a versatile means for incorporation into supramolecular constructs, allowing potential applications in artificial photosynthesis and molecular devices to be developed (Langford et al., 2002). We report here the X-ray structure of the tetranitrodibenzocrown ether, (I), an important precursor to a family of antipodally arranged bichromophoric systems.

The synthesis of (I) was achieved using a previously described method (Duggan et al., 2001). Slow evaporation from a mixture of CH3CN and H2O (1:1 (v/v) produced crystals suitable for X-ray analysis. The crystal structure reveals a single crown ether in the asymmetric unit (Figure 1), cocrystallized with one molecule of CH3CN and one of H2O. Both solvent molecules participate in hydrogen bonding; the H2O molecule bridges (I) and CH3CN, with DA distances of 2.314*(17)*Å and 2.105*(16)*Å, respectively (see Table 1).

Molecules of (I) dimerize in the solid state to form open-ended boxes in which two molecules of H2O and two molecules CH3CN are housed, as shown in Figure 2. Edge-on stacking of (I) forms channels (ca 8 Å wide and 15 Å long) which are filled by the included solvent molecules. The stacking is stabilized by π-π interacts between crown ethers with a mean plane distance of 3.61 Å.

Experimental top

The title compound was synthesized by a literature procedure (Duggan et al., 2001). Yellow crystals suitable for X-ray analysis were grown by slow evaporation of a CH3CN and H2O (1:1 (v/v) solution of the compound.

Refinement top

All H atoms were placed in idealized positions except for the water H atoms. DFIX restraints were placed on O1W—H1W and O1W—H2W fixing their distances to 0.83 Å.

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL-SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL-DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

Figures top
[Figure 1] Fig. 1. : ORTEP representation of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms omitted for clarity.
[Figure 2] Fig. 2. : Solid-state dimer formed by (I), with included solvent, showing the extent of hydrogen bonding (dashed lines). H atoms on the crown ether have been omitted for clarity.
2,3,11,12-[4',4'',5',5''-Tetranitro]dibenzo- 1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene top
Crystal data top
C20H20N4O14·C2H3N·H2OF(000) = 624
Mr = 599.47Dx = 1.509 Mg m3
Triclinic, P1Melting point: 500.0 K
a = 10.766 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.648 (2) ÅCell parameters from 25863 reflections
c = 11.813 (2) Åθ = 4–25°
α = 69.89 (3)°µ = 0.13 mm1
β = 74.07 (3)°T = 173 K
γ = 75.84 (3)°Square Prism, yellow
V = 1319.0 (5) Å30.2 × 0.17 × 0.13 mm
Z = 2
Data collection top
Nonius Kappa CCD
diffractometer
Rint = 0.089
non–profiled ω/phi/2θ scansθmax = 27.9°, θmin = 3.6°
25863 measured reflectionsh = 1214
6200 independent reflectionsk = 1515
3503 reflections with I > 2σ(I)l = 1515
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0527P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.33 e Å3
6200 reflectionsΔρmin = 0.32 e Å3
388 parameters
Crystal data top
C20H20N4O14·C2H3N·H2Oγ = 75.84 (3)°
Mr = 599.47V = 1319.0 (5) Å3
Triclinic, P1Z = 2
a = 10.766 (2) ÅMo Kα radiation
b = 11.648 (2) ŵ = 0.13 mm1
c = 11.813 (2) ÅT = 173 K
α = 69.89 (3)°0.2 × 0.17 × 0.13 mm
β = 74.07 (3)°
Data collection top
Nonius Kappa CCD
diffractometer
3503 reflections with I > 2σ(I)
25863 measured reflectionsRint = 0.089
6200 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0502 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.33 e Å3
6200 reflectionsΔρmin = 0.32 e Å3
388 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.02049 (14)0.04783 (15)0.71817 (13)0.0286 (4)
N10.08497 (15)0.03473 (17)0.69138 (16)0.0212 (4)
C10.09711 (18)0.11985 (19)0.56734 (18)0.0160 (5)
O20.13729 (14)0.05053 (16)0.76382 (14)0.0341 (4)
N20.33208 (15)0.12392 (18)0.54922 (16)0.0217 (4)
C20.20964 (17)0.17069 (19)0.50378 (18)0.0156 (5)
O30.36188 (14)0.01181 (15)0.59397 (15)0.0321 (4)
N30.67320 (15)1.04738 (17)0.22889 (16)0.0183 (4)
C30.21171 (18)0.25927 (19)0.39075 (19)0.0166 (5)
H30.28910.29360.34770.02*
O40.39854 (13)0.20068 (15)0.53746 (14)0.0305 (4)
N40.43397 (16)1.16356 (17)0.11986 (17)0.0225 (4)
C40.10158 (18)0.29863 (19)0.33950 (18)0.0151 (4)
O50.11593 (11)0.28987 (13)0.34810 (12)0.0179 (3)
N50.1810 (2)0.4509 (2)0.5664 (2)0.0457 (6)
C50.01232 (17)0.24593 (19)0.40408 (18)0.0150 (4)
O60.37364 (12)0.41809 (13)0.31948 (14)0.0238 (4)
C60.01333 (18)0.15724 (19)0.51712 (18)0.0158 (5)
H60.08990.12180.56050.019*
O70.40666 (12)0.66497 (13)0.16790 (13)0.0226 (4)
C70.23412 (17)0.23930 (19)0.41428 (19)0.0181 (5)
H7A0.26940.26310.49120.022*
H7B0.21530.14770.43630.022*
O80.73205 (14)0.99783 (14)0.33310 (14)0.0305 (4)
C80.33139 (19)0.28942 (19)0.3333 (2)0.0202 (5)
H8A0.2910.27650.25160.024*
H8B0.40740.24520.37020.024*
O90.71560 (13)1.14530 (14)0.15939 (14)0.0249 (4)
C90.47470 (19)0.4686 (2)0.2514 (2)0.0228 (5)
H9A0.55030.42450.29320.027*
H9B0.44250.45870.16780.027*
O100.50879 (13)1.20624 (14)0.20022 (14)0.0282 (4)
C100.51535 (18)0.6021 (2)0.2429 (2)0.0238 (5)
H10A0.5930.63710.20490.029*
H10B0.53840.61280.32620.029*
O110.35600 (15)1.22058 (15)0.03517 (16)0.0375 (4)
C110.42184 (18)0.78621 (19)0.15826 (18)0.0175 (5)
O120.19711 (11)0.76582 (13)0.06956 (12)0.0183 (3)
C120.53883 (17)0.8564 (2)0.19896 (18)0.0170 (5)
H120.61540.81950.23620.02*
O130.06939 (12)0.63579 (13)0.07761 (12)0.0198 (3)
C130.54420 (17)0.97959 (19)0.18549 (18)0.0158 (5)
O140.09253 (12)0.38498 (13)0.23002 (12)0.0181 (3)
C140.43502 (18)1.03608 (19)0.12722 (18)0.0153 (4)
C150.31705 (18)0.96735 (19)0.08419 (18)0.0165 (5)
H150.24251.00660.04270.02*
C160.30806 (17)0.8426 (2)0.10151 (18)0.0162 (5)
C170.08053 (17)0.8215 (2)0.00916 (19)0.0184 (5)
H17A0.05550.85290.06630.022*
H17B0.09730.89210.0640.022*
C180.02814 (18)0.72468 (19)0.02932 (18)0.0179 (5)
H18A0.0030.68270.07380.021*
H18B0.10280.76440.08560.021*
C190.16790 (18)0.53838 (19)0.04634 (19)0.0188 (5)
H19A0.24620.57280.00870.023*
H19B0.13480.49760.00220.023*
C200.20376 (18)0.44587 (19)0.16121 (19)0.0189 (5)
H20A0.28060.38430.14020.023*
H20B0.22630.4880.2110.023*
C210.1733 (2)0.5116 (2)0.4661 (2)0.0276 (5)
C220.1643 (2)0.5876 (2)0.3397 (2)0.0290 (6)
H22A0.22850.57110.30480.043*
H22B0.0760.56810.29220.043*
H22C0.18240.67530.33620.043*
O1W0.15280 (18)0.2267 (2)0.7753 (2)0.0473 (5)
H1W0.131 (6)0.254 (6)0.823 (5)0.23 (3)*
H2W0.149 (5)0.291 (3)0.714 (4)0.19 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0326 (9)0.0262 (10)0.0224 (9)0.0106 (7)0.0046 (7)0.0015 (7)
N10.0194 (9)0.0259 (12)0.0165 (10)0.0011 (8)0.0053 (8)0.0047 (9)
C10.0203 (11)0.0152 (12)0.0122 (11)0.0019 (8)0.0031 (8)0.0045 (9)
O20.0353 (9)0.0503 (12)0.0210 (9)0.0100 (8)0.0131 (7)0.0082 (8)
N20.0176 (9)0.0263 (12)0.0195 (10)0.0015 (8)0.0049 (7)0.0056 (9)
C20.0150 (10)0.0164 (12)0.0175 (12)0.0004 (8)0.0053 (8)0.0082 (10)
O30.0290 (8)0.0231 (10)0.0380 (10)0.0035 (7)0.0150 (7)0.0004 (8)
N30.0169 (9)0.0181 (11)0.0224 (11)0.0030 (8)0.0038 (8)0.0094 (9)
C30.0152 (10)0.0167 (12)0.0192 (12)0.0049 (8)0.0010 (8)0.0075 (10)
O40.0212 (8)0.0370 (11)0.0385 (10)0.0103 (7)0.0116 (7)0.0094 (8)
N40.0173 (9)0.0212 (11)0.0285 (11)0.0002 (8)0.0057 (8)0.0083 (9)
C40.0173 (10)0.0117 (11)0.0142 (11)0.0008 (8)0.0015 (8)0.0037 (9)
O50.0129 (7)0.0199 (9)0.0187 (8)0.0047 (6)0.0044 (6)0.0006 (7)
N50.0694 (16)0.0335 (14)0.0317 (14)0.0045 (11)0.0094 (11)0.0103 (12)
C50.0142 (10)0.0163 (12)0.0158 (11)0.0010 (8)0.0042 (8)0.0065 (9)
O60.0204 (8)0.0153 (9)0.0382 (10)0.0000 (6)0.0138 (7)0.0071 (7)
C60.0151 (10)0.0156 (12)0.0169 (11)0.0046 (8)0.0006 (8)0.0057 (10)
O70.0142 (7)0.0152 (9)0.0350 (9)0.0027 (6)0.0008 (6)0.0064 (7)
C70.0147 (10)0.0168 (12)0.0208 (12)0.0063 (8)0.0015 (8)0.0023 (10)
O80.0268 (8)0.0261 (10)0.0303 (10)0.0068 (7)0.0092 (7)0.0083 (8)
C80.0160 (10)0.0175 (13)0.0250 (13)0.0031 (8)0.0032 (9)0.0044 (10)
O90.0243 (8)0.0231 (10)0.0271 (9)0.0065 (7)0.0126 (7)0.0086 (8)
C90.0165 (10)0.0182 (13)0.0344 (14)0.0036 (9)0.0093 (9)0.0050 (11)
O100.0253 (8)0.0273 (10)0.0366 (10)0.0013 (7)0.0049 (7)0.0202 (8)
C100.0122 (10)0.0193 (13)0.0363 (14)0.0046 (9)0.0030 (9)0.0040 (11)
O110.0354 (9)0.0234 (10)0.0465 (11)0.0142 (8)0.0094 (8)0.0091 (8)
C110.0195 (10)0.0150 (12)0.0171 (11)0.0036 (9)0.0055 (8)0.0018 (10)
O120.0119 (7)0.0160 (8)0.0227 (8)0.0012 (6)0.0010 (6)0.0033 (7)
C120.0126 (10)0.0183 (12)0.0178 (12)0.0034 (8)0.0020 (8)0.0027 (9)
O130.0178 (7)0.0196 (9)0.0153 (8)0.0032 (6)0.0021 (6)0.0023 (7)
C130.0142 (10)0.0190 (13)0.0140 (11)0.0014 (8)0.0056 (8)0.0055 (10)
O140.0139 (7)0.0175 (8)0.0183 (8)0.0043 (6)0.0029 (6)0.0012 (7)
C140.0173 (10)0.0153 (12)0.0153 (11)0.0017 (8)0.0070 (8)0.0049 (9)
C150.0157 (10)0.0174 (12)0.0158 (11)0.0028 (8)0.0057 (8)0.0023 (9)
C160.0139 (10)0.0201 (13)0.0140 (11)0.0002 (8)0.0050 (8)0.0049 (9)
C170.0107 (10)0.0210 (13)0.0198 (12)0.0042 (8)0.0004 (8)0.0029 (10)
C180.0187 (10)0.0172 (12)0.0137 (11)0.0019 (8)0.0042 (8)0.0005 (9)
C190.0159 (10)0.0171 (12)0.0181 (12)0.0021 (8)0.0008 (8)0.0025 (10)
C200.0125 (10)0.0144 (12)0.0240 (12)0.0035 (8)0.0000 (8)0.0007 (10)
C210.0307 (12)0.0228 (14)0.0308 (16)0.0027 (10)0.0036 (10)0.0134 (12)
C220.0309 (12)0.0253 (14)0.0271 (14)0.0036 (10)0.0018 (10)0.0073 (11)
O1W0.0468 (11)0.0504 (14)0.0398 (12)0.0001 (9)0.0073 (9)0.0144 (11)
Geometric parameters (Å, º) top
O1—N11.226 (2)C9—H9A0.99
N1—O21.228 (2)C9—H9B0.99
N1—C11.451 (3)C10—H10A0.99
C1—C61.382 (3)C10—H10B0.99
C1—C21.389 (3)C11—C121.386 (3)
N2—O31.225 (2)C11—C161.422 (3)
N2—O41.226 (2)O12—C161.353 (2)
N2—C21.469 (2)O12—C171.447 (2)
C2—C31.377 (3)C12—C131.376 (3)
N3—O91.221 (2)C12—H120.95
N3—O81.230 (2)O13—C191.426 (2)
N3—C131.472 (3)O13—C181.431 (2)
C3—C41.385 (3)C13—C141.383 (3)
C3—H30.95O14—C201.443 (2)
N4—O111.225 (2)C14—C151.393 (3)
N4—O101.227 (2)C15—C161.378 (3)
N4—C141.460 (3)C15—H150.95
C4—O141.349 (2)C17—C181.504 (3)
C4—C51.413 (3)C17—H17A0.99
O5—C51.355 (2)C17—H17B0.99
O5—C71.443 (2)C18—H18A0.99
N5—C211.143 (3)C18—H18B0.99
C5—C61.378 (3)C19—C201.493 (3)
O6—C91.421 (2)C19—H19A0.99
O6—C81.421 (2)C19—H19B0.99
C6—H60.95C20—H20A0.99
O7—C111.349 (2)C20—H20B0.99
O7—C101.447 (2)C21—C221.441 (3)
C7—C81.490 (3)C22—H22A0.98
C7—H7A0.99C22—H22B0.98
C7—H7B0.99C22—H22C0.98
C8—H8A0.99O1W—H1W0.839 (10)
C8—H8B0.99O1W—H2W0.841 (10)
C9—C101.484 (3)
O1—N1—O2123.82 (18)C9—C10—H10B110.1
O1—N1—C1117.59 (16)H10A—C10—H10B108.5
O2—N1—C1118.57 (17)O7—C11—C12124.44 (17)
C6—C1—C2120.21 (19)O7—C11—C16116.03 (17)
C6—C1—N1116.85 (17)C12—C11—C16119.53 (19)
C2—C1—N1122.74 (17)C16—O12—C17116.53 (16)
O3—N2—O4124.61 (17)C13—C12—C11120.08 (18)
O3—N2—C2118.28 (17)C13—C12—H12120
O4—N2—C2117.10 (18)C11—C12—H12120
C3—C2—C1120.24 (17)C19—O13—C18111.52 (15)
C3—C2—N2118.30 (17)C12—C13—C14120.75 (18)
C1—C2—N2121.23 (18)C12—C13—N3116.22 (16)
O9—N3—O8124.85 (17)C14—C13—N3122.91 (18)
O9—N3—C13118.77 (17)C4—O14—C20118.39 (14)
O8—N3—C13116.35 (18)C13—C14—C15119.93 (19)
C2—C3—C4120.34 (17)C13—C14—N4122.27 (17)
C2—C3—H3119.8C15—C14—N4117.48 (17)
C4—C3—H3119.8C16—C15—C14120.24 (18)
O11—N4—O10123.91 (19)C16—C15—H15119.9
O11—N4—C14117.85 (17)C14—C15—H15119.9
O10—N4—C14118.22 (17)O12—C16—C15125.20 (17)
O14—C4—C3125.32 (17)O12—C16—C11115.43 (18)
O14—C4—C5115.48 (16)C15—C16—C11119.37 (17)
C3—C4—C5119.20 (18)O12—C17—C18108.51 (16)
C5—O5—C7116.27 (15)O12—C17—H17A110
O5—C5—C6124.44 (16)C18—C17—H17A110
O5—C5—C4115.56 (17)O12—C17—H17B110
C6—C5—C4120.00 (17)C18—C17—H17B110
C9—O6—C8111.66 (15)H17A—C17—H17B108.4
C5—C6—C1120.01 (17)O13—C18—C17109.43 (16)
C5—C6—H6120O13—C18—H18A109.8
C1—C6—H6120C17—C18—H18A109.8
C11—O7—C10116.24 (15)O13—C18—H18B109.8
O5—C7—C8108.16 (16)C17—C18—H18B109.8
O5—C7—H7A110.1H18A—C18—H18B108.2
C8—C7—H7A110.1O13—C19—C20109.41 (16)
O5—C7—H7B110.1O13—C19—H19A109.8
C8—C7—H7B110.1C20—C19—H19A109.8
H7A—C7—H7B108.4O13—C19—H19B109.8
O6—C8—C7109.27 (17)C20—C19—H19B109.8
O6—C8—H8A109.8H19A—C19—H19B108.2
C7—C8—H8A109.8O14—C20—C19107.88 (15)
O6—C8—H8B109.8O14—C20—H20A110.1
C7—C8—H8B109.8C19—C20—H20A110.1
H8A—C8—H8B108.3O14—C20—H20B110.1
O6—C9—C10108.58 (17)C19—C20—H20B110.1
O6—C9—H9A110H20A—C20—H20B108.4
C10—C9—H9A110N5—C21—C22179.5 (3)
O6—C9—H9B110C21—C22—H22A109.5
C10—C9—H9B110C21—C22—H22B109.5
H9A—C9—H9B108.4H22A—C22—H22B109.5
O7—C10—C9107.83 (16)C21—C22—H22C109.5
O7—C10—H10A110.1H22A—C22—H22C109.5
C9—C10—H10A110.1H22B—C22—H22C109.5
O7—C10—H10B110.1H1W—O1W—H2W97 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O13i0.84 (1)2.31 (2)3.141 (3)169 (7)
O1W—H2W···N50.84 (1)2.11 (2)2.932 (3)168 (5)
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC20H20N4O14·C2H3N·H2O
Mr599.47
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)10.766 (2), 11.648 (2), 11.813 (2)
α, β, γ (°)69.89 (3), 74.07 (3), 75.84 (3)
V3)1319.0 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.2 × 0.17 × 0.13
Data collection
DiffractometerNonius Kappa CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25863, 6200, 3503
Rint0.089
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.119, 1.00
No. of reflections6200
No. of parameters388
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.32

Computer programs: COLLECT (Nonius, 1997-2000), HKL-SCALEPACK (Otwinowski & Minor, 1997), HKL-DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O13i0.839 (10)2.314 (17)3.141 (3)169 (7)
O1W—H2W···N50.841 (10)2.105 (16)2.932 (3)168 (5)
Symmetry code: (i) x, y+1, z+1.
 

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