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The title compound, C13H20Cl3N2O4P, was prepared by the reaction of N-isopropyl­benzyl­amine and CCl3C(O)N(H)P(O)Cl2, followed by crystallization from CH3OH and CH3CN. Centrosymmetric dimers of anions are hydrogen-bonded to neighbouring cations (via –P—O...H—N– and –C=O...H—N– hydrogen bonds) in a one-dimensional polymeric chain. Furthermore, a Cl...Cl inter­action (3.242 Å) and a C—H...π short contact are present in the crystal structure, the former between two adjacent anions and the latter between two neighbouring cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050428/lx2024sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050428/lx2024Isup2.hkl
Contains datablock I

CCDC reference: 648424

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.076
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 70 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Phosphate derivatives (XYP(O)O-, where X, Y = O-, OH, OR, OAr, NRR', halide ion,···) have attracted significant attention due to their utility in supramolecular chemistry and crystal engineering and their ability as the metal complexing agents (Wisser & Janiak, 2007; Ślepokura & Lis, 2006). There is a little reports on N-acylated phosphate derivatives, RC(O)N(H)P(O)R1O- (Gholivand et al., 2005) but the investigation about this area are of special interest in this context: 1) having an ionic structure and possibility the exchange of cation to obtain desirable solubility and hydrophobicity which is required to bio-study 2) bearing a close structural resemblance to the β-diketone frame, 3) usually acting as effective chelating groups (Amirkhanov et al., 1997). In previous works, we report on the structure of phosphate compounds containing PO2Cl2- (Gholivand & Pourayoubi, 2004) and CF3C(O)N(H)P(O)(O)[NH(tert,-C4H9]- anions (Gholivand et al., 2005).

Here, we report the crystal structure of the title compound, N-Benzyl-2-propanaminium O-methyl trichloroacetamidophosphate (Fig. 1). Phosphorus atom in the anion of title compound has a distorted tetrahedral geometry. Centrosymmetric dimmers of anions which is produced via two equal N1—H1N···O2ii hydrogen bonds (Table 1 and Fig. 2) are hydrogen bonded to neighboring cations in a one-dimensional polymeric chain. Furthermore, the crystal packing is stabilized by Cl···Cl (distance 3.242 Å) electrostatic interaction and C—H···π short contact between a hydrogen of the C4 and the phenyl group (Table 1 and Fig. 2, the centroid of the C5–C10 phenyl ring and the symmetry codes are as in Fig. 2).

Related literature top

For related literature, see: Amirkhanov et al. (1997); Gholivand & Pourayoubi (2004); Gholivand et al. (2005); Kirsanov & Makitra (1956); Sheldrick (1997); Wisser & Janiak (2007); Ślepokura & Lis (2006).

Experimental top

N-isopropylbenzylamine (1.133 g, 7.594 mmol) was added to a solution of CCl3C(O)N(H)P(O)Cl2 (0.530 g, 1.899 mmol) (Kirsanov & Makitra, 1956) in CCl4 (20 ml) and stirred at 273 K. After 12 h, the solvent removed and the residue that formed was stirred with H2O. After drying, the solid was recrystallized from CH3OH and CH3CN.

Refinement top

The hydrogen atoms of NH and NH2 groups were located in difference Fourier maps and the all parameters were freely refined. All H atoms of C were geometrically located in ideal positions and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms, 0.98 Å for methyl H atoms, and 0.99 Å for methylene H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms and 1.5Ueq(C) for methyl H atoms.

Structure description top

Phosphate derivatives (XYP(O)O-, where X, Y = O-, OH, OR, OAr, NRR', halide ion,···) have attracted significant attention due to their utility in supramolecular chemistry and crystal engineering and their ability as the metal complexing agents (Wisser & Janiak, 2007; Ślepokura & Lis, 2006). There is a little reports on N-acylated phosphate derivatives, RC(O)N(H)P(O)R1O- (Gholivand et al., 2005) but the investigation about this area are of special interest in this context: 1) having an ionic structure and possibility the exchange of cation to obtain desirable solubility and hydrophobicity which is required to bio-study 2) bearing a close structural resemblance to the β-diketone frame, 3) usually acting as effective chelating groups (Amirkhanov et al., 1997). In previous works, we report on the structure of phosphate compounds containing PO2Cl2- (Gholivand & Pourayoubi, 2004) and CF3C(O)N(H)P(O)(O)[NH(tert,-C4H9]- anions (Gholivand et al., 2005).

Here, we report the crystal structure of the title compound, N-Benzyl-2-propanaminium O-methyl trichloroacetamidophosphate (Fig. 1). Phosphorus atom in the anion of title compound has a distorted tetrahedral geometry. Centrosymmetric dimmers of anions which is produced via two equal N1—H1N···O2ii hydrogen bonds (Table 1 and Fig. 2) are hydrogen bonded to neighboring cations in a one-dimensional polymeric chain. Furthermore, the crystal packing is stabilized by Cl···Cl (distance 3.242 Å) electrostatic interaction and C—H···π short contact between a hydrogen of the C4 and the phenyl group (Table 1 and Fig. 2, the centroid of the C5–C10 phenyl ring and the symmetry codes are as in Fig. 2).

For related literature, see: Amirkhanov et al. (1997); Gholivand & Pourayoubi (2004); Gholivand et al. (2005); Kirsanov & Makitra (1956); Sheldrick (1997); Wisser & Janiak (2007); Ślepokura & Lis (2006).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2005).

Figures top
[Figure 1] Fig. 1. Structure of title compound showing the atom-labeling scheme with thermal ellipsoid at 50% probability.
[Figure 2] Fig. 2. The N—H···O hydrogen bonds, Cl···Cl and C—H···π interations (dotted lines) in the title compound. [Symmetry code: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 2, -y + 2, -z + 1; (iii) -x + 2, -y + 2, -z; (iv) -x + 2, -y + 1, -z.]
N-Benzyl-2-propanaminium O-methyl trichloroacetamidophosphate top
Crystal data top
C13H20Cl3N2O4PZ = 2
Mr = 405.63F(000) = 420
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5690 (7) ÅCell parameters from 511 reflections
b = 9.7554 (7) Åθ = 3–27°
c = 10.5083 (7) ŵ = 0.60 mm1
α = 78.757 (1)°T = 120 K
β = 73.902 (1)°Prism, colourless
γ = 83.115 (2)°0.35 × 0.20 × 0.20 mm
V = 922.14 (11) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4012 independent reflections
Radiation source: fine-focus sealed tube3317 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.1°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)
k = 1212
Tmin = 0.817, Tmax = 0.889l = 1313
7569 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0303P)2 + 0.4098P]
where P = (Fo2 + 2Fc2)/3
4012 reflections(Δ/σ)max < 0.001
223 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C13H20Cl3N2O4Pγ = 83.115 (2)°
Mr = 405.63V = 922.14 (11) Å3
Triclinic, P1Z = 2
a = 9.5690 (7) ÅMo Kα radiation
b = 9.7554 (7) ŵ = 0.60 mm1
c = 10.5083 (7) ÅT = 120 K
α = 78.757 (1)°0.35 × 0.20 × 0.20 mm
β = 73.902 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4012 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)
3317 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.889Rint = 0.023
7569 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.40 e Å3
4012 reflectionsΔρmin = 0.37 e Å3
223 parameters
Special details top

Experimental. Spectroscopic analysis: IR (KBr, cm-1) 3417, 3039, 2983, 2940, 2841, 2705, 2434, 1712, 1601, 1469, 1394, 1257, 1233, 1185, 1094, 1057, 865, 810, 749, 676; 31P & 1H-NMR {(D6)DMSO}: 2.74 (1P). 1H-NMR ((D6)DMSO) 1.27 (6H, CH3), 3.86 (1H, CH), 4.09 (2H, CH2), 4.31 (3H, OCH3), 7.10–7.53 (7H, 5 Ar—H & 2 NH), 8.82 (1H, NH); Anal. Calc.: C 38.49, H 4.97, N 6.91. found: C 38.40, H 4.91, N 6.87.

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
P1.08073 (5)0.93186 (5)0.29290 (4)0.01267 (11)
Cl10.80897 (6)0.61153 (6)0.65929 (5)0.02861 (13)
Cl20.62282 (5)0.84713 (5)0.56791 (5)0.02585 (12)
Cl30.64223 (5)0.58645 (5)0.47578 (5)0.02247 (12)
O11.04164 (14)0.95140 (13)0.16261 (12)0.0156 (3)
O21.10748 (15)1.05510 (14)0.34305 (12)0.0203 (3)
O31.21581 (14)0.81854 (14)0.28100 (13)0.0216 (3)
O40.90319 (14)0.68874 (13)0.30462 (12)0.0179 (3)
N10.94452 (17)0.85137 (16)0.41709 (15)0.0156 (3)
H1N0.923 (2)0.882 (2)0.492 (2)0.028 (6)*
N20.87102 (16)0.83093 (15)0.04059 (15)0.0120 (3)
H2NB0.923 (2)0.844 (2)0.100 (2)0.019 (5)*
H2NA0.896 (2)0.899 (2)0.030 (2)0.024 (6)*
C10.87439 (19)0.74740 (18)0.40134 (16)0.0133 (4)
C20.7413 (2)0.70091 (19)0.52235 (17)0.0165 (4)
C31.2809 (3)0.7801 (3)0.3920 (3)0.0404 (6)
H3A1.37070.72080.36580.061*
H3B1.21260.72840.46880.061*
H3C1.30380.86480.41700.061*
C40.9180 (2)0.69270 (18)0.00419 (18)0.0166 (4)
H4A0.87340.68640.07720.020*
H4B0.88220.61690.07180.020*
C51.0810 (2)0.67174 (18)0.05357 (17)0.0147 (4)
C61.1466 (2)0.68353 (19)0.19101 (18)0.0181 (4)
H6A1.08870.70800.25340.022*
C71.2966 (2)0.6595 (2)0.23676 (19)0.0222 (4)
H7A1.34090.66680.33050.027*
C81.3821 (2)0.6250 (2)0.14661 (19)0.0217 (4)
H8A1.48470.60820.17830.026*
C91.3171 (2)0.6150 (2)0.00961 (19)0.0205 (4)
H9A1.37540.59180.05250.025*
C101.1677 (2)0.63857 (18)0.03649 (18)0.0164 (4)
H10A1.12380.63210.13020.020*
C110.71066 (19)0.84825 (19)0.10844 (18)0.0164 (4)
H11A0.68710.77260.18880.020*
C120.6802 (2)0.9887 (2)0.1561 (2)0.0227 (4)
H12A0.74010.99210.21730.034*
H12B0.57681.00060.20330.034*
H12C0.70391.06410.07850.034*
C130.6198 (2)0.8340 (2)0.0142 (2)0.0236 (4)
H13A0.63630.73880.00660.035*
H13B0.64830.90160.06900.035*
H13C0.51630.85250.05760.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0146 (2)0.0143 (2)0.0096 (2)0.00439 (18)0.00358 (17)0.00053 (17)
Cl10.0312 (3)0.0351 (3)0.0186 (2)0.0134 (2)0.0111 (2)0.0109 (2)
Cl20.0193 (3)0.0232 (3)0.0332 (3)0.00429 (19)0.0020 (2)0.0118 (2)
Cl30.0223 (3)0.0209 (2)0.0264 (2)0.01088 (19)0.00513 (19)0.00544 (19)
O10.0198 (7)0.0157 (6)0.0122 (6)0.0049 (5)0.0055 (5)0.0007 (5)
O20.0270 (8)0.0215 (7)0.0140 (6)0.0128 (6)0.0035 (5)0.0027 (5)
O30.0174 (7)0.0226 (7)0.0234 (7)0.0012 (6)0.0071 (6)0.0003 (6)
O40.0233 (7)0.0167 (7)0.0145 (6)0.0043 (5)0.0043 (5)0.0039 (5)
N10.0201 (8)0.0174 (8)0.0102 (7)0.0073 (6)0.0026 (6)0.0027 (6)
N20.0141 (8)0.0103 (7)0.0118 (7)0.0013 (6)0.0044 (6)0.0008 (6)
C10.0147 (9)0.0129 (8)0.0126 (8)0.0019 (7)0.0060 (7)0.0013 (7)
C20.0187 (10)0.0160 (9)0.0155 (8)0.0053 (7)0.0045 (7)0.0018 (7)
C30.0419 (15)0.0336 (13)0.0541 (15)0.0008 (11)0.0358 (13)0.0048 (11)
C40.0175 (9)0.0127 (9)0.0211 (9)0.0002 (7)0.0059 (7)0.0059 (7)
C50.0157 (9)0.0095 (8)0.0192 (9)0.0006 (7)0.0033 (7)0.0055 (7)
C60.0218 (10)0.0168 (9)0.0173 (9)0.0001 (8)0.0066 (8)0.0051 (7)
C70.0250 (11)0.0225 (10)0.0167 (9)0.0021 (8)0.0005 (8)0.0057 (8)
C80.0165 (10)0.0189 (10)0.0265 (10)0.0023 (8)0.0019 (8)0.0036 (8)
C90.0196 (10)0.0188 (10)0.0237 (10)0.0020 (8)0.0097 (8)0.0016 (8)
C100.0197 (10)0.0136 (9)0.0147 (8)0.0007 (7)0.0027 (7)0.0026 (7)
C110.0130 (9)0.0166 (9)0.0183 (9)0.0008 (7)0.0029 (7)0.0025 (7)
C120.0182 (10)0.0223 (10)0.0286 (10)0.0054 (8)0.0055 (8)0.0117 (8)
C130.0172 (10)0.0255 (11)0.0318 (11)0.0014 (8)0.0108 (8)0.0088 (9)
Geometric parameters (Å, º) top
P—O21.478 (1)C4—H4B0.9900
P—O11.489 (1)C5—C101.393 (2)
P—O31.591 (1)C5—C61.394 (2)
P—N11.709 (2)C6—C71.388 (3)
Cl1—C21.772 (2)C6—H6A0.9500
Cl2—C21.768 (2)C7—C81.386 (3)
Cl3—C21.764 (2)C7—H7A0.9500
O3—C31.437 (2)C8—C91.390 (3)
O4—C11.212 (2)C8—H8A0.9500
N1—C11.340 (2)C9—C101.383 (3)
N1—H1N0.86 (2)C9—H9A0.9500
N2—C41.492 (2)C10—H10A0.9500
N2—C111.507 (2)C11—C121.518 (3)
N2—H2NB0.93 (2)C11—C131.522 (2)
N2—H2NA0.89 (2)C11—H11A1.0000
C1—C21.568 (2)C12—H12A0.9800
C3—H3A0.9800C12—H12B0.9800
C3—H3B0.9800C12—H12C0.9800
C3—H3C0.9800C13—H13A0.9800
C4—C51.503 (3)C13—H13B0.9800
C4—H4A0.9900C13—H13C0.9800
O2—P—O1119.68 (7)C10—C5—C6119.34 (17)
O2—P—O3111.84 (8)C10—C5—C4120.82 (16)
O1—P—O3105.46 (7)C6—C5—C4119.83 (16)
O2—P—N1105.49 (8)C7—C6—C5120.01 (17)
O1—P—N1108.94 (7)C7—C6—H6A120.0
O3—P—N1104.44 (8)C5—C6—H6A120.0
C3—O3—P118.41 (14)C8—C7—C6120.40 (18)
C1—N1—P123.40 (13)C8—C7—H7A119.8
C1—N1—H1N121.3 (15)C6—C7—H7A119.8
P—N1—H1N115.3 (15)C7—C8—C9119.67 (18)
C4—N2—C11113.87 (13)C7—C8—H8A120.2
C4—N2—H2NB110.0 (13)C9—C8—H8A120.2
C11—N2—H2NB108.1 (13)C10—C9—C8120.13 (17)
C4—N2—H2NA109.0 (14)C10—C9—H9A119.9
C11—N2—H2NA110.7 (14)C8—C9—H9A119.9
H2NB—N2—H2NA104.8 (18)C9—C10—C5120.43 (17)
O4—C1—N1126.73 (16)C9—C10—H10A119.8
O4—C1—C2118.51 (15)C5—C10—H10A119.8
N1—C1—C2114.75 (15)N2—C11—C12108.21 (14)
C1—C2—Cl3109.39 (12)N2—C11—C13110.70 (15)
C1—C2—Cl2110.96 (12)C12—C11—C13112.64 (16)
Cl3—C2—Cl2108.20 (10)N2—C11—H11A108.4
C1—C2—Cl1108.37 (12)C12—C11—H11A108.4
Cl3—C2—Cl1109.21 (10)C13—C11—H11A108.4
Cl2—C2—Cl1110.69 (10)C11—C12—H12A109.5
O3—C3—H3A109.5C11—C12—H12B109.5
O3—C3—H3B109.5H12A—C12—H12B109.5
H3A—C3—H3B109.5C11—C12—H12C109.5
O3—C3—H3C109.5H12A—C12—H12C109.5
H3A—C3—H3C109.5H12B—C12—H12C109.5
H3B—C3—H3C109.5C11—C13—H13A109.5
N2—C4—C5112.12 (14)C11—C13—H13B109.5
N2—C4—H4A109.2H13A—C13—H13B109.5
C5—C4—H4A109.2C11—C13—H13C109.5
N2—C4—H4B109.2H13A—C13—H13C109.5
C5—C4—H4B109.2H13B—C13—H13C109.5
H4A—C4—H4B107.9
O2—P—O3—C346.85 (16)C11—N2—C4—C5172.01 (14)
O1—P—O3—C3178.48 (14)N2—C4—C5—C1076.1 (2)
N1—P—O3—C366.75 (16)N2—C4—C5—C6104.87 (18)
O2—P—N1—C1169.64 (15)C10—C5—C6—C71.3 (3)
O1—P—N1—C139.97 (17)C4—C5—C6—C7177.78 (17)
O3—P—N1—C172.32 (16)C5—C6—C7—C80.6 (3)
P—N1—C1—O46.3 (3)C6—C7—C8—C90.3 (3)
P—N1—C1—C2173.17 (12)C7—C8—C9—C100.4 (3)
O4—C1—C2—Cl39.6 (2)C8—C9—C10—C50.4 (3)
N1—C1—C2—Cl3169.95 (13)C6—C5—C10—C91.2 (3)
O4—C1—C2—Cl2128.87 (15)C4—C5—C10—C9177.87 (16)
N1—C1—C2—Cl250.65 (18)C4—N2—C11—C12176.53 (14)
O4—C1—C2—Cl1109.40 (16)C4—N2—C11—C1359.6 (2)
N1—C1—C2—Cl171.08 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···Cgi0.992.86 (2)3.635 (2)135
N1—H1N···O2ii0.86 (2)1.88 (2)2.743 (2)175 (2)
N2—H2NB···O10.93 (2)1.95 (2)2.811 (2)153 (2)
N2—H2NA···O1iii0.89 (2)1.84 (2)2.727 (2)173 (2)
N2—H2NB···O40.93 (2)2.35 (2)2.930 (2)120 (2)
Symmetry codes: (i) x2, y1, z; (ii) x+2, y+2, z+1; (iii) x+2, y+2, z.

Experimental details

Crystal data
Chemical formulaC13H20Cl3N2O4P
Mr405.63
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)9.5690 (7), 9.7554 (7), 10.5083 (7)
α, β, γ (°)78.757 (1), 73.902 (1), 83.115 (2)
V3)922.14 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.60
Crystal size (mm)0.35 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1999)
Tmin, Tmax0.817, 0.889
No. of measured, independent and
observed [I > 2σ(I)] reflections
7569, 4012, 3317
Rint0.023
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.076, 1.03
No. of reflections4012
No. of parameters223
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.37

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···Cgi0.992.86 (2)3.635 (2)135
N1—H1N···O2ii0.86 (2)1.88 (2)2.743 (2)175 (2)
N2—H2NB···O10.93 (2)1.95 (2)2.811 (2)153 (2)
N2—H2NA···O1iii0.89 (2)1.84 (2)2.727 (2)173 (2)
N2—H2NB···O40.93 (2)2.35 (2)2.930 (2)120 (2)
Symmetry codes: (i) x2, y1, z; (ii) x+2, y+2, z+1; (iii) x+2, y+2, z.
 

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