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In the title compound, C17H14N4O7S, the dihedral angle between the two benzene rings is 9.04 (15)°. The centroid–centroid distance of 3.9825 (19) Å between nearly parallel benzene rings of adjacent mol­ecules suggests the existence of π-π stacking. Inter­molecular and intra-mol­ecular N—H...O hydrogen bonding is present in the structure. The eth­oxy group is disordered over two sets of sites with an occupancy ratio of 0.580 (15):0.420 (15). The crystal studied was an inversion twin.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811012918/xu5177sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536811012918/xu5177Isup2.hkl
Contains datablock I

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.037
  • wR factor = 0.095
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.390 From the CIF: _refine_ls_abs_structure_Flack_su 0.080 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) .. 4.29 Ratio PLAT234_ALERT_4_C Large Hirshfeld Difference C16 -- C17 .. 0.25 Ang. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 6 PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 81 Perc.
Alert level G 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 25.03 From the CIF: _reflns_number_total 3011 Count of symmetry unique reflns 1671 Completeness (_total/calc) 180.19% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1340 Fraction of Friedel pairs measured 0.802 Are heavy atom types Z>Si present yes PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 6 PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites .... 6 PLAT033_ALERT_4_G Flack x Parameter Value Deviates from Zero ..... 0.39 PLAT242_ALERT_2_G Check Low Ueq as Compared to Neighbors for C16' PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 10 Perc. PLAT432_ALERT_2_G Short Inter X...Y Contact O3 .. C15 .. 2.91 Ang. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 42 PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 73 Perc.
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 8 ALERT level C = Check. Ensure it is not caused by an omission or oversight 9 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The background to this study has been set in our previous work on the structural chemistry of N,N'-disubstituted thiourea (Saeed et al., 2010). Herein, as a continuation of these studies, the structure of the title compound, (I), C17H14N4O7S, is described.

The compound is slightly twisted. The nitro groups are 3.9 (5)° and 17 (1)° from the phenyl ring plane of C10—C15. The thiourea plane is making a dihedral angle of 5.3 (2)° with the amido group and makes a dihedral angle of 31.35 (17)° with the phenyl ring plane of C2—C7.

There are inter-molecular N—H···O H-bond interactions which link the molecules to form 1-D chain in the crystal lattice. There are also weak π···π between neighbouring rings in the crystal lattice.

Related literature top

For background to this study and a related structure, see: Saeed et al. (2010).

Experimental top

A solution of 3,5-dinitrobenzoyl chloride (0.01 mol) in anhydrous acetone (75 ml) and 3% tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst (PTC) in anhydrous acetone was added dropwise to a suspension of dry potassium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 50 min. After cooling to room temperature, a solution of ethyl-orthoamino benzoate (0.01 mol) in anhydrous acetone (25 ml) was added dropwise and the resulting mixture refluxed for 3 h. Hydrochloric acid (0.1 N, 300 ml) was added, and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethyl acetate.

Refinement top

N-bound H-atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed at geometrical positions with C—H = 0.93–0.97 Å and refined using riding model with Uiso(H) =1.2Ueq(C). The ethoxy group is disordered over two sites, the occupancy ratio was refined to 0.580 (15):0.420 (15). Distance and displacement restraints were used for the disordered components.

Structure description top

The background to this study has been set in our previous work on the structural chemistry of N,N'-disubstituted thiourea (Saeed et al., 2010). Herein, as a continuation of these studies, the structure of the title compound, (I), C17H14N4O7S, is described.

The compound is slightly twisted. The nitro groups are 3.9 (5)° and 17 (1)° from the phenyl ring plane of C10—C15. The thiourea plane is making a dihedral angle of 5.3 (2)° with the amido group and makes a dihedral angle of 31.35 (17)° with the phenyl ring plane of C2—C7.

There are inter-molecular N—H···O H-bond interactions which link the molecules to form 1-D chain in the crystal lattice. There are also weak π···π between neighbouring rings in the crystal lattice.

For background to this study and a related structure, see: Saeed et al. (2010).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEP plot of the compound was shown at 50% probability thermal ellipsoids with the atom numbering scheme (only the major component was shown).
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the a axis.
Ethyl 2-[3-(3,5-Dinitrobenzoyl)thioureido]benzoate top
Crystal data top
C17H14N4O7SF(000) = 864
Mr = 418.38Dx = 1.461 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 6458 reflections
a = 11.7264 (19) Åθ = 2.1–25.0°
b = 16.617 (3) ŵ = 0.22 mm1
c = 9.9630 (16) ÅT = 299 K
β = 101.522 (2)°Block, yellow
V = 1902.3 (5) Å30.27 × 0.16 × 0.08 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer
3011 independent reflections
Radiation source: fine-focus sealed tube2727 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω and φ scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1313
Tmin = 0.943, Tmax = 0.983k = 1915
4944 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.3273P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3011 reflectionsΔρmax = 0.22 e Å3
301 parametersΔρmin = 0.24 e Å3
42 restraintsAbsolute structure: Flack (1983), 1340 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.39 (8)
Crystal data top
C17H14N4O7SV = 1902.3 (5) Å3
Mr = 418.38Z = 4
Monoclinic, CcMo Kα radiation
a = 11.7264 (19) ŵ = 0.22 mm1
b = 16.617 (3) ÅT = 299 K
c = 9.9630 (16) Å0.27 × 0.16 × 0.08 mm
β = 101.522 (2)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
3011 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2727 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.983Rint = 0.014
4944 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095Δρmax = 0.22 e Å3
S = 1.10Δρmin = 0.24 e Å3
3011 reflectionsAbsolute structure: Flack (1983), 1340 Friedel pairs
301 parametersAbsolute structure parameter: 0.39 (8)
42 restraints
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*/UeqOcc. (<1)
S10.94150 (8)0.19793 (4)0.68183 (8)0.0759 (3)
O20.8103 (2)0.05570 (13)1.0967 (3)0.0866 (7)
O30.99391 (19)0.01499 (10)0.97679 (18)0.0663 (5)
O41.0187 (3)0.31100 (14)0.9255 (4)0.1022 (8)
O51.1263 (3)0.35915 (14)0.7937 (3)0.1095 (10)
O61.2496 (4)0.1832 (2)0.4646 (3)0.1355 (14)
O71.2710 (4)0.0571 (3)0.5114 (4)0.1459 (15)
N10.9176 (2)0.13747 (12)0.9269 (2)0.0543 (5)
H10.911 (2)0.0912 (17)0.974 (3)0.064 (8)*
H20.997 (2)0.0472 (15)0.704 (3)0.045 (7)*
N20.9902 (2)0.05353 (12)0.7789 (2)0.0555 (5)
N31.0798 (3)0.30348 (14)0.8423 (3)0.0773 (8)
N41.2402 (3)0.1244 (3)0.5338 (3)0.0976 (10)
C10.7736 (3)0.11786 (17)1.1281 (3)0.0647 (7)
C20.8103 (2)0.19844 (15)1.0865 (3)0.0563 (6)
C30.7770 (3)0.26756 (18)1.1485 (3)0.0713 (8)
H30.72960.26261.21250.086*
C40.8124 (4)0.3418 (2)1.1176 (4)0.0842 (10)
H40.78850.38701.15960.101*
C50.8830 (3)0.35007 (17)1.0248 (3)0.0782 (9)
H50.90800.40101.00510.094*
C60.9179 (3)0.28322 (16)0.9596 (3)0.0657 (7)
H60.96620.28960.89680.079*
C70.8809 (2)0.20717 (14)0.9882 (2)0.0531 (6)
C80.9476 (2)0.13033 (14)0.8043 (3)0.0525 (6)
C91.0156 (2)0.01157 (13)0.8622 (2)0.0518 (6)
C101.0713 (2)0.08065 (14)0.8043 (3)0.0539 (6)
C111.0528 (2)0.15737 (14)0.8509 (3)0.0555 (6)
H111.01030.16500.91930.067*
C121.0991 (2)0.22190 (15)0.7933 (3)0.0595 (7)
C131.1609 (3)0.21360 (18)0.6905 (3)0.0695 (8)
H131.18900.25820.65080.083*
C141.1797 (3)0.1366 (2)0.6489 (3)0.0677 (8)
C151.1379 (3)0.07002 (16)0.7053 (3)0.0618 (7)
H151.15420.01860.67750.074*
O10.7136 (10)0.1247 (5)1.2262 (9)0.083 (2)0.580 (15)
C160.6730 (10)0.0532 (7)1.2838 (13)0.113 (4)0.580 (15)
H16A0.69310.05481.38300.135*0.580 (15)
H16B0.70770.00561.25230.135*0.580 (15)
C170.5404 (10)0.0522 (6)1.2345 (19)0.161 (6)0.580 (15)
H17A0.50700.01251.28510.193*0.580 (15)
H17B0.52190.03921.13870.193*0.580 (15)
H17C0.50930.10421.24890.193*0.580 (15)
O1'0.6758 (12)0.1178 (7)1.1805 (14)0.085 (3)0.420 (15)
C16'0.6436 (15)0.0411 (7)1.2287 (14)0.084 (4)0.420 (15)
H16C0.71190.00731.25490.101*0.420 (15)
H16D0.58890.01391.15710.101*0.420 (15)
C17'0.5883 (19)0.0568 (8)1.3511 (18)0.134 (6)0.420 (15)
H17D0.57380.00651.39200.161*0.420 (15)
H17E0.51620.08501.32190.161*0.420 (15)
H17F0.63990.08881.41690.161*0.420 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1117 (6)0.0590 (4)0.0655 (4)0.0263 (4)0.0381 (4)0.0158 (3)
O20.1105 (17)0.0589 (12)0.1056 (17)0.0112 (11)0.0580 (14)0.0120 (11)
O30.1054 (16)0.0478 (10)0.0498 (10)0.0112 (9)0.0252 (10)0.0004 (7)
O40.131 (2)0.0570 (13)0.122 (2)0.0046 (13)0.031 (2)0.0083 (13)
O50.118 (2)0.0524 (12)0.153 (3)0.0257 (13)0.0147 (19)0.0192 (14)
O60.172 (3)0.163 (3)0.0823 (18)0.073 (3)0.052 (2)0.0065 (18)
O70.179 (4)0.131 (3)0.163 (3)0.028 (3)0.119 (3)0.026 (2)
N10.0734 (15)0.0413 (10)0.0509 (12)0.0056 (9)0.0185 (10)0.0003 (8)
N20.0776 (15)0.0480 (11)0.0434 (12)0.0094 (10)0.0178 (11)0.0029 (9)
N30.0820 (18)0.0479 (13)0.092 (2)0.0105 (12)0.0056 (16)0.0079 (13)
N40.099 (2)0.123 (3)0.0795 (19)0.049 (2)0.0396 (17)0.0068 (19)
C10.076 (2)0.0658 (17)0.0559 (15)0.0108 (14)0.0209 (14)0.0059 (12)
C20.0635 (17)0.0569 (14)0.0459 (13)0.0114 (11)0.0046 (12)0.0053 (10)
C30.081 (2)0.0679 (18)0.0663 (18)0.0144 (14)0.0178 (16)0.0096 (14)
C40.103 (3)0.0639 (19)0.086 (2)0.0187 (17)0.0186 (19)0.0250 (16)
C50.103 (2)0.0453 (14)0.084 (2)0.0031 (14)0.0121 (18)0.0134 (13)
C60.080 (2)0.0526 (14)0.0644 (17)0.0012 (12)0.0144 (15)0.0065 (12)
C70.0631 (16)0.0459 (12)0.0478 (13)0.0070 (10)0.0049 (12)0.0029 (10)
C80.0577 (15)0.0476 (13)0.0520 (13)0.0034 (10)0.0100 (11)0.0010 (10)
C90.0643 (17)0.0453 (13)0.0462 (14)0.0029 (10)0.0119 (12)0.0023 (10)
C100.0649 (17)0.0507 (13)0.0445 (12)0.0062 (11)0.0069 (12)0.0030 (10)
C110.0637 (17)0.0486 (13)0.0516 (13)0.0047 (11)0.0056 (12)0.0062 (10)
C120.0622 (17)0.0462 (13)0.0641 (17)0.0098 (11)0.0015 (14)0.0033 (11)
C130.0718 (19)0.0740 (18)0.0574 (16)0.0290 (14)0.0001 (14)0.0162 (14)
C140.0655 (18)0.082 (2)0.0568 (16)0.0240 (14)0.0151 (14)0.0023 (14)
C150.0686 (18)0.0592 (14)0.0581 (15)0.0113 (13)0.0138 (13)0.0029 (12)
O10.103 (6)0.083 (3)0.075 (4)0.006 (3)0.043 (4)0.008 (3)
C160.130 (8)0.116 (7)0.104 (7)0.012 (5)0.053 (6)0.018 (5)
C170.191 (12)0.086 (5)0.212 (14)0.002 (6)0.056 (10)0.002 (7)
O1'0.087 (6)0.081 (4)0.093 (7)0.005 (4)0.035 (5)0.008 (4)
C16'0.090 (7)0.070 (5)0.108 (8)0.013 (4)0.055 (6)0.007 (5)
C17'0.209 (14)0.092 (7)0.135 (10)0.039 (8)0.116 (10)0.024 (7)
Geometric parameters (Å, º) top
S1—C81.649 (2)C6—C71.385 (4)
O2—C11.185 (3)C6—H60.9300
O3—C91.219 (3)C9—C101.493 (3)
O4—N31.205 (4)C10—C151.386 (4)
O5—N31.222 (4)C10—C111.388 (3)
O6—N41.213 (4)C11—C121.377 (4)
O7—N41.210 (5)C11—H110.9300
N1—C81.342 (3)C12—C131.375 (4)
N1—C71.416 (3)C13—C141.376 (5)
N1—H10.91 (3)C13—H130.9300
N2—C91.360 (3)C14—C151.375 (4)
N2—C81.412 (3)C15—H150.9300
N2—H20.77 (3)O1—C161.442 (8)
N3—C121.474 (4)C16—C171.535 (9)
N4—C141.478 (4)C16—H16A0.9700
C1—O11.318 (10)C16—H16B0.9700
C1—O1'1.351 (14)C17—H17A0.9600
C1—C21.490 (4)C17—H17B0.9600
C2—C31.396 (4)C17—H17C0.9600
C2—C71.410 (4)O1'—C16'1.440 (9)
C3—C41.356 (5)C16'—C17'1.514 (9)
C3—H30.9300C16'—H16C0.9700
C4—C51.365 (5)C16'—H16D0.9700
C4—H40.9300C17'—H17D0.9600
C5—C61.389 (4)C17'—H17E0.9600
C5—H50.9300C17'—H17F0.9600
C8—N1—C7128.5 (2)N2—C9—C10115.8 (2)
C8—N1—H1117.1 (18)C15—C10—C11120.2 (2)
C7—N1—H1114.0 (18)C15—C10—C9122.0 (2)
C9—N2—C8130.7 (2)C11—C10—C9117.9 (2)
C9—N2—H2115.4 (18)C12—C11—C10118.4 (3)
C8—N2—H2113.8 (19)C12—C11—H11120.8
O4—N3—O5124.6 (3)C10—C11—H11120.8
O4—N3—C12118.4 (2)C13—C12—C11122.8 (3)
O5—N3—C12117.1 (3)C13—C12—N3118.5 (2)
O7—N4—O6125.1 (4)C11—C12—N3118.6 (3)
O7—N4—C14118.6 (3)C12—C13—C14117.2 (2)
O6—N4—C14116.2 (4)C12—C13—H13121.4
O2—C1—O1123.2 (5)C14—C13—H13121.4
O2—C1—O1'118.9 (6)C15—C14—C13122.3 (3)
O2—C1—C2124.7 (3)C15—C14—N4118.1 (3)
O1—C1—C2110.8 (4)C13—C14—N4119.5 (3)
O1'—C1—C2115.0 (5)C14—C15—C10119.0 (3)
C3—C2—C7118.5 (2)C14—C15—H15120.5
C3—C2—C1119.6 (3)C10—C15—H15120.5
C7—C2—C1121.9 (2)C1—O1—C16119.4 (9)
C4—C3—C2121.5 (3)O1—C16—C17106.0 (9)
C4—C3—H3119.2O1—C16—H16A110.5
C2—C3—H3119.2C17—C16—H16A110.5
C3—C4—C5120.0 (3)O1—C16—H16B110.5
C3—C4—H4120.0C17—C16—H16B110.5
C5—C4—H4120.0H16A—C16—H16B108.7
C4—C5—C6120.7 (3)C1—O1'—C16'115.3 (10)
C4—C5—H5119.6O1'—C16'—C17'107.4 (10)
C6—C5—H5119.6O1'—C16'—H16C110.2
C7—C6—C5120.0 (3)C17'—C16'—H16C110.2
C7—C6—H6120.0O1'—C16'—H16D110.2
C5—C6—H6120.0C17'—C16'—H16D110.2
C6—C7—C2119.3 (2)H16C—C16'—H16D108.5
C6—C7—N1121.5 (2)C16'—C17'—H17D109.5
C2—C7—N1119.1 (2)C16'—C17'—H17E109.5
N1—C8—N2114.2 (2)H17D—C17'—H17E109.5
N1—C8—S1129.22 (19)C16'—C17'—H17F109.5
N2—C8—S1116.62 (19)H17D—C17'—H17F109.5
O3—C9—N2123.2 (2)H17E—C17'—H17F109.5
O3—C9—C10121.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.91 (3)1.95 (3)2.672 (3)134 (2)
N1—H1···O30.91 (3)2.01 (3)2.700 (3)131 (2)
N2—H2···O3i0.77 (3)2.32 (3)3.086 (3)172 (2)
Symmetry code: (i) x, y, z1/2.

Experimental details

Crystal data
Chemical formulaC17H14N4O7S
Mr418.38
Crystal system, space groupMonoclinic, Cc
Temperature (K)299
a, b, c (Å)11.7264 (19), 16.617 (3), 9.9630 (16)
β (°) 101.522 (2)
V3)1902.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.27 × 0.16 × 0.08
Data collection
DiffractometerBruker SMART 1000 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.943, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
4944, 3011, 2727
Rint0.014
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.095, 1.10
No. of reflections3011
No. of parameters301
No. of restraints42
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.24
Absolute structureFlack (1983), 1340 Friedel pairs
Absolute structure parameter0.39 (8)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.91 (3)1.95 (3)2.672 (3)134 (2)
N1—H1···O30.91 (3)2.01 (3)2.700 (3)131 (2)
N2—H2···O3i0.77 (3)2.32 (3)3.086 (3)172 (2)
Symmetry code: (i) x, y, z1/2.
 

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