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The title compound, C15H16N2O4·0.5H2O, is the first structurally characterized example of an ester amide of a squaric acid amino acid derivative. There are two conformationally inequivalent organic mol­ecules and a water mol­ecule in the asymmetric unit. Molecules are linked via N—H...O and O—H...O hydrogen bonds to build the non-centrosymmetric crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006361/cf6327sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006361/cf6327Isup2.hkl
Contains datablock I

CCDC reference: 238808

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • H-atom completeness 63%
  • R factor = 0.042
  • wR factor = 0.134
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 6.17 Ratio PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 7.11 Ratio PLAT360_ALERT_2_A Short C(sp3)-C(sp3) Bond C29 - C30 ... 1.22 Ang.
Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C29
Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.095 Value of mu given = 0.093 CHEMW01_ALERT_1_C The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.99 <> 1.01 Calculated formula weight = 307.3890 Formula weight given = 297.3000 CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C14 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O8 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C21 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C15 H16 N2 O4
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C15 H27 N2 O4.5 Atom count from _chemical_formula_moiety:C15 H17 N2 O4.5 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C15 H27 N2 O4.5 Atom count from the _atom_site data: C15 H17 N2 O4.5 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C15 H27 N2 O4.5 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 60.00 60.00 0.00 H 108.00 68.00 40.00 N 8.00 8.00 0.00 O 18.00 18.00 0.00 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.98 From the CIF: _reflns_number_total 3261 Count of symmetry unique reflns 3261 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 9 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-[(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]-3-phenylpropaneamide top
Crystal data top
C15H16N2O4·0.5H2OF(000) = 628
Mr = 297.3Dx = 1.247 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 22 reflections
a = 9.244 (3) Åθ = 18.0–19.1°
b = 12.115 (3) ŵ = 0.09 mm1
c = 14.2116 (19) ÅT = 293 K
β = 95.78 (2)°Prism, colorless
V = 1583.4 (7) Å30.26 × 0.26 × 0.18 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.047
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.4°
Graphite monochromatorh = 011
non–profiled ω/2θ scansk = 1414
6597 measured reflectionsl = 1717
3261 independent reflections3 standard reflections every 120 min
1854 reflections with I > 2σ(I) intensity decay: 8%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 0.89 w = 1/[σ2(Fo2) + (0.0843P)2 + 0.0866P]
where P = (Fo2 + 2Fc2)/3
3261 reflections(Δ/σ)max < 0.001
396 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = 0.14 e Å3
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
C10.1569 (7)0.6879 (4)0.7569 (4)0.0857 (16)
H10.23560.72130.73240.103*
C20.0276 (10)0.6764 (6)0.7004 (6)0.122 (3)
H20.01950.70120.63820.146*
C30.0876 (9)0.6288 (8)0.7362 (9)0.138 (4)
H30.17500.62140.69820.166*
C40.0775 (8)0.5924 (8)0.8252 (9)0.135 (3)
H40.15740.55980.84880.162*
C50.0523 (7)0.6033 (6)0.8823 (5)0.0990 (18)
H50.05910.57820.94440.119*
C60.1712 (5)0.6510 (4)0.8478 (4)0.0711 (13)
C70.3138 (5)0.6560 (4)0.9080 (3)0.0695 (13)
H7A0.29630.66370.97380.083*
H7B0.36780.72030.89060.083*
C80.4043 (5)0.5517 (4)0.8959 (3)0.0562 (10)
H80.34620.48680.90870.067*
C90.5427 (5)0.5514 (4)0.9633 (3)0.0655 (12)
C100.3816 (4)0.4774 (4)0.7356 (3)0.0549 (10)
C110.3928 (5)0.4630 (4)0.6335 (3)0.0682 (12)
C120.2894 (5)0.3684 (4)0.6345 (3)0.0670 (12)
C130.2844 (5)0.3897 (4)0.7339 (3)0.0582 (11)
C140.1106 (7)0.2623 (5)0.7783 (4)0.098 (2)
H14A0.15670.19900.75210.117*
H14B0.03650.29020.73110.117*
C150.0440 (6)0.2297 (5)0.8646 (4)0.0883 (16)
H15A0.02720.17320.84910.106*
H15B0.00190.29260.88980.106*
H15C0.11810.20200.91080.106*
C160.4378 (8)0.1520 (6)0.7746 (4)0.1006 (19)
H160.49260.11490.81600.121*
C170.3854 (11)0.2557 (8)0.7977 (7)0.141 (3)
H170.40210.28650.85560.170*
C180.3102 (11)0.3134 (8)0.7381 (11)0.156 (4)
H180.27740.38430.75360.188*
C190.2826 (10)0.2658 (8)0.6535 (9)0.139 (3)
H190.23010.30500.61210.167*
C200.3316 (7)0.1604 (5)0.6292 (5)0.0973 (19)
H200.31200.12910.57220.117*
C210.4104 (5)0.1022 (4)0.6911 (4)0.0715 (13)
C220.4626 (5)0.0115 (4)0.6669 (3)0.0655 (12)
H22A0.51420.01060.60400.079*
H22B0.53120.03330.71090.079*
C230.3409 (4)0.0981 (4)0.6697 (3)0.0563 (11)
H230.27960.08440.61860.068*
C240.4098 (5)0.2129 (4)0.6585 (3)0.0605 (12)
C250.1134 (4)0.0731 (3)0.7721 (3)0.0507 (9)
C260.0053 (4)0.0740 (4)0.8551 (3)0.0573 (11)
C270.1076 (5)0.0412 (4)0.7924 (3)0.0655 (12)
C280.0071 (4)0.0408 (4)0.7158 (3)0.0631 (12)
C290.1163 (8)0.0086 (10)0.5855 (5)0.153 (4)
H29A0.12900.08790.59020.184*
H29B0.19670.02540.62410.184*
C300.1233 (13)0.0185 (17)0.5036 (9)0.313 (13)
H30A0.21540.00370.48410.469*
H30B0.04640.01650.46400.469*
H30C0.11360.09720.49800.469*
N10.5547 (4)0.4757 (4)1.0279 (3)0.0750 (11)
H1A0.63100.47301.06780.090*
H1B0.48620.42821.03100.090*
N20.4432 (4)0.5452 (3)0.7989 (2)0.0553 (9)
H2A0.51030.58840.78260.066*
N30.4076 (5)0.2624 (4)0.5774 (3)0.0772 (11)
H3A0.44520.32710.56900.093*
H3B0.36870.23050.53210.093*
N40.2530 (3)0.0967 (3)0.7604 (2)0.0550 (9)
H4A0.29520.11230.81000.066*
O10.6376 (4)0.6212 (4)0.9560 (3)0.1103 (14)
O20.4588 (5)0.5094 (3)0.5749 (2)0.0913 (11)
O30.2346 (4)0.3035 (4)0.5751 (2)0.0953 (12)
O40.2178 (4)0.3475 (3)0.8041 (2)0.0718 (9)
O50.4633 (4)0.2531 (3)0.7263 (2)0.0822 (10)
O60.0083 (3)0.0944 (3)0.9388 (2)0.0782 (9)
O70.2383 (3)0.0227 (4)0.8026 (2)0.0889 (11)
O80.0177 (3)0.0206 (4)0.6244 (2)0.0918 (13)
O90.3044 (5)0.3391 (4)1.0522 (2)0.0743 (9)
HW10.321 (6)0.265 (6)1.049 (4)0.10 (2)*
HW20.208 (8)0.343 (6)1.036 (5)0.12 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.094 (4)0.063 (3)0.095 (4)0.004 (3)0.014 (3)0.004 (3)
C20.128 (6)0.085 (5)0.141 (6)0.017 (5)0.042 (6)0.002 (4)
C30.088 (6)0.103 (6)0.209 (10)0.028 (5)0.053 (7)0.033 (7)
C40.069 (5)0.118 (7)0.220 (10)0.006 (4)0.027 (6)0.045 (7)
C50.083 (4)0.092 (4)0.126 (5)0.003 (3)0.029 (4)0.019 (4)
C60.067 (3)0.058 (3)0.089 (4)0.010 (2)0.010 (3)0.013 (3)
C70.075 (3)0.073 (3)0.061 (3)0.005 (3)0.011 (2)0.015 (2)
C80.056 (2)0.067 (3)0.046 (2)0.004 (2)0.0069 (18)0.003 (2)
C90.067 (3)0.076 (3)0.054 (2)0.013 (3)0.004 (2)0.005 (2)
C100.062 (2)0.056 (3)0.047 (2)0.008 (2)0.0092 (18)0.003 (2)
C110.086 (3)0.068 (3)0.053 (2)0.007 (3)0.017 (2)0.000 (2)
C120.087 (3)0.066 (3)0.049 (2)0.000 (3)0.011 (2)0.008 (2)
C130.067 (3)0.057 (3)0.052 (2)0.001 (2)0.011 (2)0.002 (2)
C140.129 (5)0.091 (4)0.075 (3)0.049 (4)0.019 (3)0.017 (3)
C150.086 (4)0.093 (4)0.089 (4)0.028 (3)0.024 (3)0.011 (3)
C160.116 (5)0.090 (5)0.094 (4)0.025 (4)0.001 (4)0.003 (3)
C170.160 (8)0.081 (6)0.173 (8)0.026 (6)0.036 (7)0.027 (6)
C180.134 (7)0.063 (5)0.256 (14)0.003 (5)0.059 (8)0.004 (7)
C190.118 (6)0.088 (6)0.205 (10)0.022 (5)0.013 (6)0.042 (6)
C200.102 (4)0.083 (4)0.103 (4)0.013 (4)0.010 (3)0.026 (3)
C210.065 (3)0.073 (3)0.073 (3)0.004 (3)0.011 (2)0.022 (3)
C220.054 (2)0.073 (3)0.067 (3)0.004 (2)0.003 (2)0.014 (2)
C230.050 (2)0.076 (3)0.043 (2)0.009 (2)0.0028 (17)0.011 (2)
C240.053 (3)0.077 (3)0.050 (2)0.006 (2)0.001 (2)0.011 (2)
C250.048 (2)0.051 (2)0.053 (2)0.0017 (19)0.0049 (18)0.0041 (18)
C260.061 (2)0.058 (3)0.052 (3)0.003 (2)0.001 (2)0.008 (2)
C270.053 (3)0.078 (3)0.065 (3)0.006 (2)0.004 (2)0.016 (2)
C280.055 (2)0.082 (3)0.053 (2)0.008 (2)0.0076 (19)0.008 (2)
C290.101 (4)0.284 (12)0.077 (4)0.087 (7)0.025 (3)0.008 (6)
C300.224 (12)0.54 (3)0.199 (11)0.200 (17)0.140 (10)0.187 (16)
N10.065 (2)0.092 (3)0.065 (2)0.008 (2)0.0063 (18)0.018 (2)
N20.059 (2)0.059 (2)0.0489 (18)0.0043 (18)0.0101 (16)0.0000 (17)
N30.097 (3)0.077 (3)0.058 (2)0.016 (3)0.012 (2)0.001 (2)
N40.0440 (18)0.072 (2)0.0490 (18)0.0048 (17)0.0031 (14)0.0058 (17)
O10.089 (3)0.112 (3)0.124 (3)0.041 (3)0.019 (2)0.037 (3)
O20.138 (3)0.084 (2)0.0568 (18)0.016 (2)0.035 (2)0.0009 (17)
O30.122 (3)0.101 (3)0.065 (2)0.026 (2)0.020 (2)0.027 (2)
O40.088 (2)0.072 (2)0.0563 (17)0.0249 (19)0.0145 (15)0.0086 (15)
O50.100 (3)0.084 (2)0.0668 (19)0.033 (2)0.0276 (18)0.0035 (18)
O60.080 (2)0.095 (3)0.0580 (19)0.0121 (19)0.0029 (15)0.0008 (18)
O70.0472 (18)0.129 (3)0.088 (2)0.019 (2)0.0014 (15)0.015 (2)
O80.0646 (19)0.153 (4)0.0586 (19)0.027 (2)0.0124 (15)0.003 (2)
O90.080 (3)0.083 (3)0.0614 (19)0.004 (2)0.0161 (17)0.0014 (18)
Geometric parameters (Å, º) top
C1—C61.361 (7)C17—H170.930
C1—C21.377 (9)C18—C191.380 (14)
C1—H10.930C18—H180.930
C2—C31.354 (12)C19—C201.386 (12)
C2—H20.930C19—H190.930
C3—C41.333 (12)C20—C211.390 (8)
C3—H30.930C20—H200.930
C4—C51.386 (11)C21—C221.488 (8)
C4—H40.930C22—C231.536 (6)
C5—C61.375 (8)C22—H22A0.970
C5—H50.930C22—H22B0.970
C6—C71.498 (7)C23—N41.453 (5)
C7—C81.535 (7)C23—C241.531 (7)
C7—H7A0.970C23—H230.980
C7—H7B0.970C24—O51.227 (5)
C8—N21.461 (5)C24—N31.302 (6)
C8—C91.519 (6)C25—N41.315 (5)
C8—H80.980C25—C281.384 (6)
C9—O11.229 (6)C25—C261.467 (6)
C9—N11.295 (6)C26—O61.218 (5)
C10—N21.306 (5)C26—C271.492 (6)
C10—C131.390 (6)C27—O71.223 (5)
C10—C111.475 (6)C27—C281.441 (6)
C11—O21.218 (5)C28—O81.317 (5)
C11—C121.493 (7)C29—C301.218 (10)
C12—O31.226 (5)C29—O81.450 (7)
C12—C131.440 (6)C29—H29A0.970
C13—O41.327 (5)C29—H29B0.970
C14—O41.452 (6)C30—H30A0.960
C14—C151.480 (7)C30—H30B0.960
C14—H14A0.970C30—H30C0.960
C14—H14B0.970N1—H1A0.860
C15—H15A0.960N1—H1B0.860
C15—H15B0.960N2—H2A0.860
C15—H15C0.960N3—H3A0.860
C16—C171.375 (11)N3—H3B0.860
C16—C211.377 (8)N4—H4A0.860
C16—H160.930O9—HW10.91 (7)
C17—C181.344 (14)O9—HW20.90 (7)
C6—C1—C2121.0 (7)C19—C18—H18120.5
C6—C1—H1119.5C18—C19—C20121.1 (9)
C2—C1—H1119.5C18—C19—H19119.4
C3—C2—C1119.6 (8)C20—C19—H19119.4
C3—C2—H2120.2C19—C20—C21119.3 (8)
C1—C2—H2120.2C19—C20—H20120.4
C4—C3—C2120.9 (8)C21—C20—H20120.4
C4—C3—H3119.5C16—C21—C20118.5 (6)
C2—C3—H3119.5C16—C21—C22121.4 (5)
C3—C4—C5119.9 (8)C20—C21—C22120.1 (5)
C3—C4—H4120.1C21—C22—C23114.0 (4)
C5—C4—H4120.1C21—C22—H22A108.8
C6—C5—C4120.5 (7)C23—C22—H22A108.8
C6—C5—H5119.8C21—C22—H22B108.8
C4—C5—H5119.8C23—C22—H22B108.8
C1—C6—C5118.1 (6)H22A—C22—H22B107.7
C1—C6—C7121.6 (5)N4—C23—C24107.0 (3)
C5—C6—C7120.1 (5)N4—C23—C22111.0 (4)
C6—C7—C8111.1 (4)C24—C23—C22108.8 (3)
C6—C7—H7A109.4N4—C23—H23110.0
C8—C7—H7A109.4C24—C23—H23110.0
C6—C7—H7B109.4C22—C23—H23110.0
C8—C7—H7B109.4O5—C24—N3123.8 (5)
H7A—C7—H7B108.0O5—C24—C23118.4 (4)
N2—C8—C9108.9 (3)N3—C24—C23117.9 (4)
N2—C8—C7109.8 (3)N4—C25—C28137.1 (4)
C9—C8—C7111.4 (4)N4—C25—C26132.8 (4)
N2—C8—H8108.9C28—C25—C2690.0 (3)
C9—C8—H8108.9O6—C26—C25134.9 (4)
C7—C8—H8108.9O6—C26—C27136.3 (4)
O1—C9—N1122.4 (4)C25—C26—C2788.8 (3)
O1—C9—C8120.6 (4)O6—C26—C28178.2 (4)
N1—C9—C8117.0 (4)O7—C27—C28137.0 (4)
N2—C10—C13136.8 (4)O7—C27—C26136.1 (4)
N2—C10—C11133.0 (4)C28—C27—C2686.9 (3)
C13—C10—C1190.1 (4)O8—C28—C25129.5 (4)
O2—C11—C10135.1 (5)O8—C28—C27136.2 (4)
O2—C11—C12136.5 (4)C25—C28—C2794.3 (3)
C10—C11—C1288.4 (4)O8—C28—C26176.2 (3)
O2—C11—C13178.2 (4)C30—C29—O8115.4 (7)
O3—C12—C13137.6 (5)C30—C29—H29A108.4
O3—C12—C11134.9 (4)O8—C29—H29A108.4
C13—C12—C1187.5 (4)C30—C29—H29B108.4
O4—C13—C10129.0 (4)O8—C29—H29B108.4
O4—C13—C12137.0 (4)H29A—C29—H29B107.5
C10—C13—C1294.0 (3)C29—C30—H30A109.5
O4—C13—C11175.7 (4)C29—C30—H30B109.5
O4—C14—C15108.2 (4)H30A—C30—H30B109.5
O4—C14—H14A110.1C29—C30—H30C109.5
C15—C14—H14A110.1H30A—C30—H30C109.5
O4—C14—H14B110.1H30B—C30—H30C109.5
C15—C14—H14B110.1C9—N1—H1A120.0
H14A—C14—H14B108.4C9—N1—H1B120.0
C14—C15—H15A109.5H1A—N1—H1B120.0
C14—C15—H15B109.5C10—N2—C8123.5 (3)
H15A—C15—H15B109.5C10—N2—H2A118.3
C14—C15—H15C109.5C8—N2—H2A118.3
H15A—C15—H15C109.5C24—N3—H3A120.0
H15B—C15—H15C109.5C24—N3—H3B120.0
C17—C16—C21121.0 (8)H3A—N3—H3B120.0
C17—C16—H16119.5C25—N4—C23124.7 (3)
C21—C16—H16119.5C25—N4—H4A117.7
C18—C17—C16121.1 (10)C23—N4—H4A117.7
C18—C17—H17119.4C13—O4—C14116.2 (3)
C16—C17—H17119.4C28—O8—C29116.1 (4)
C17—C18—C19119.0 (9)HW1—O9—HW2102 (6)
C17—C18—H18120.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O7i0.862.102.922 (5)160
N1—H1B···O90.862.052.894 (5)169
N2—H2A···O5ii0.862.102.821 (4)141
N3—H3A···O2iii0.862.173.026 (5)170
N3—H3B···O3iv0.862.102.930 (5)162
N4—H4A···O9v0.862.052.860 (4)155
O9—HW1···O1vi0.91 (8)1.78 (8)2.698 (6)177 (6)
O9—HW2···O6vii0.89 (6)2.06 (6)2.869 (6)149 (5)
Symmetry codes: (i) x+1, y+1/2, z+2; (ii) x+1, y+1, z; (iii) x1, y1, z; (iv) x, y1/2, z+1; (v) x, y1/2, z+2; (vi) x+1, y1/2, z+2; (vii) x, y+1/2, z+2.
 

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