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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 10| October 2010| Page o2524
doi:10.1107/S1600536810035725

N,N′-Di­benzyl-N′′-(2,6-di­fluoro­benzo­yl)-N,N′-di­methyl­phospho­ric tri­amide

Mehrdad Pourayoubi,a* Atekeh Tarahhomi,a Arnold L. Rheingoldb and James A. Golenb

aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 4 September 2010; accepted 6 September 2010; online 11 September 2010)

The phosphoryl and carbonyl groups in the title compound, C23H24F2N3O2P, are anti to each other. The P atom is in a tetra­hedral coordination environment and the environment of each N atom is essentially planar, the average bond angles at the two N atoms being 119.9 and 119.1°. The H atom of the C(=O)NHP(=O) group is involved in an inter­molecular –P=O⋯H–N– hydrogen bond, forming centrosymmetric dimers.

Related literature

For related structures, see: Pourayoubi & Sabbaghi (2009[Pourayoubi, M. & Sabbaghi, F. (2009). J. Chem. Crystallogr. 39, 874-880.]); Sabbaghi et al. (2010[Sabbaghi, F., Pourayoubi, M., Toghraee, M. & Divjakovic, V. (2010). Acta Cryst. E66, o344.]).

[Scheme 1]

Experimental

Crystal data

  • C23H24F2N3O2P

  • Mr = 443.42

  • Triclinic, [P \overline 1]

  • a = 9.9370 (11) Å

  • b = 11.1093 (15) Å

  • c = 11.5902 (14) Å

  • α = 89.101 (4)°

  • β = 67.826 (4)°

  • γ = 71.664 (4)°

  • V = 1116.9 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 200 K

  • 0.30 × 0.25 × 0.20 mm
Data collection

  • Bruker SMART X2S benchtop CCD area-detector diffractometer

  • Absorption correction: multi-scan SADABS (Bruker, 2005[Bruker (2005). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.968

  • 13602 measured reflections

  • 5173 independent reflections

  • 3851 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.126

  • S = 1.03

  • 5173 reflections

  • 286 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2i 0.83 (2) 1.92 (2) 2.752 (2) 173 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2005[Bruker (2005). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035725/ng5027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035725/ng5027Isup2.hkl

checkCIF report


Comment top

Following the previous works about carbacylamidophosphates with a C(═O)NHP(═O) skeleton such as P(O)[NHC(O)C6H4(4-NO2)][N(CH(CH3)2)(CH2C6H5)]2 (Pourayoubi & Sabbaghi, 2009) and P(O)[NHC(O)C6H4(4-NO2)][NHC6H11]2 (Sabbaghi et al., 2010), here, we report the synthesis and crystal structure of title compound, P(O)[NHC(O)C6H3(2,6-F2)][N(CH3)(CH2C6H5)]2. The phosphoryl and carbonyl groups are anti to each other and the phosphorus atom has a slightly distorted tetrahedral configuration (Fig. 1). The bond angles around the P atom are in the range of 107.11 (8)°-114.81 (8)°. The P1–N2 and P1–N3 bond lengths (1.6405 (14) Å and 1.6266 (16) Å) are shorter than the P1–N1 bond (1.6886 (15) Å). The environment of the nitrogen atoms is essentially planar; the angles C23–N3–P1, C16–N3–C23 and C16–N3–P1 are 117.53 (14)°, 116.19 (17)° and 126.13 (14)°, respectively (with average = 119.9°). A similar result was obtained for the bond angles around N2 atom (average = 119.1°). Furthermore, the angle C7–N1–P1 is 126.79 (13)°. The P═O bond length of 1.4796 (13) Å is standard for phosphoramidate compounds. The hydrogen atom of the C(═O)NHP(═O) group is involved in an intermolecular –P═O···H–N– hydrogen bond (see Table 1) to form a centrosymmetric dimeric aggregate.

Related literature top

For related structures, see: Pourayoubi & Sabbaghi (2009); Sabbaghi et al. (2010).

Experimental top

The reaction of phosphorus pentachloride (3.478 g, 16.7 mmol) and 2,6-difluorobenzamide (2.624 g, 16.7 mmol) in dry CCl4 at 358 K (3 h) and then the treatment of formic acid (0.769 g, 16.7 mmol) at ice bath temperature leads to 2,6-F2—C6H3C(O)NHP(O)Cl2. To a solution of 2,6-F2—C6H3C(O)NHP(O)Cl2 (0.411 g, 1.5 mmol) in dry CHCl3, a solution of N-methylbenzylamine (0.727 g, 6 mmol) in dry CHCl3 was added dropwise at 273 K. After 4 h stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals were obtained from a solution of the title compound in CH3OH and n-C7H14 (5:1) after slow evaporation at room temperature. IR (KBr, cm-1): 3446, 3042, 2867, 1690, 1607, 1465, 1369, 1210, 1150, 1019, 865, 823, 763, 725.

Refinement top

APEX2 software was used for preliminary determination of the unit cell. Determination of integral intensities and unit cell refinement were performed using SAINT and data were corrected for absorption using SADABS. Structure was solved by direct methods and all non-hydrogen atoms were refined as anisotropic by Fourier full matrix least squares. Hydrogen H1A was found from a Fourier difference map and was allowed to refine and all other hydrogen atoms were placed in calculated positions with appropriate riding factors.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. An ORTEP-style plot of title compound. Ellipsoids are given at the 50% probability level.
N,N'-Dibenzyl-N''-(2,6-difluorobenzoyl)- N,N'-dimethylphosphoric triamide top
Crystal data top
C23H24F2N3O2PZ = 2
Mr = 443.42F(000) = 464
Triclinic, P1Dx = 1.318 Mg m−3
a = 9.9370 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1093 (15) ÅCell parameters from 5531 reflections
c = 11.5902 (14) Åθ = 2.4–27.8°
α = 89.101 (4)°µ = 0.16 mm−1
β = 67.826 (4)°T = 200 K
γ = 71.664 (4)°BLOCK, colorless
V = 1116.9 (2) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART X2S benchtop CCD area-detector
diffractometer		5173 independent reflections
Radiation source: fine-focus sealed tube3851 reflections with I > 2σ(I)
Curved silicon crystal monochromatorRint = 0.036
phi and ω scansθmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan
SADABS (Bruker, 2005)		h = −13→13
Tmin = 0.952, Tmax = 0.968k = −14→14
13602 measured reflectionsl = −15→15
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.2218P]
where P = (Fo2 + 2Fc2)/3
5173 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C23H24F2N3O2Pγ = 71.664 (4)°
Mr = 443.42V = 1116.9 (2) Å3
Triclinic, P1Z = 2
a = 9.9370 (11) ÅMo Kα radiation
b = 11.1093 (15) ŵ = 0.16 mm−1
c = 11.5902 (14) ÅT = 200 K
α = 89.101 (4)°0.30 × 0.25 × 0.20 mm
β = 67.826 (4)°
Data collection top
Bruker SMART X2S benchtop CCD area-detector
diffractometer		5173 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2005)		3851 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.968Rint = 0.036
13602 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.37 e Å−3
5173 reflectionsΔρmin = −0.32 e Å−3
286 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.

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
P10.66485 (5)0.42270 (4)0.29906 (4)0.02461 (13)
F10.41237 (17)0.18210 (16)0.50507 (15)0.0723 (5)
F20.16095 (14)0.43844 (12)0.27352 (13)0.0532 (4)
O10.50833 (16)0.27969 (15)0.19272 (13)0.0445 (4)
O20.68882 (13)0.46617 (12)0.40757 (12)0.0323 (3)
N10.48905 (16)0.40601 (15)0.35526 (15)0.0277 (3)
N20.79630 (15)0.28474 (13)0.22927 (13)0.0246 (3)
N30.66719 (17)0.52094 (15)0.19333 (15)0.0358 (4)
C10.2810 (2)0.2390 (2)0.4858 (2)0.0449 (5)
C20.1464 (3)0.2189 (3)0.5632 (2)0.0583 (7)
H2A0.14430.16780.62990.070*
C30.0152 (3)0.2755 (3)0.5402 (2)0.0573 (7)
H3A−0.07850.26340.59240.069*
C40.0174 (2)0.3490 (2)0.4434 (2)0.0485 (6)
H4A−0.07330.38800.42820.058*
C50.1560 (2)0.3646 (2)0.36861 (19)0.0370 (5)
C60.2916 (2)0.31110 (18)0.38644 (17)0.0315 (4)
C70.4403 (2)0.32953 (18)0.30107 (17)0.0309 (4)
C80.86123 (19)0.24379 (17)0.09447 (16)0.0280 (4)
H8A0.82680.31730.05090.034*
H8B0.82120.17710.07920.034*
C91.03733 (19)0.19106 (16)0.03916 (16)0.0250 (4)
C101.1236 (2)0.22336 (17)0.09620 (17)0.0296 (4)
H10A1.07270.27970.17200.035*
C111.2842 (2)0.17395 (19)0.04339 (18)0.0341 (4)
H11A1.34190.19640.08360.041*
C121.3599 (2)0.09219 (18)−0.06744 (19)0.0358 (5)
H12A1.46930.0584−0.10330.043*
C131.2756 (2)0.06030 (19)−0.12524 (19)0.0393 (5)
H13A1.32700.0049−0.20170.047*
C141.1147 (2)0.10908 (18)−0.07202 (18)0.0336 (4)
H14A1.05750.0859−0.11230.040*
C150.8149 (2)0.18153 (18)0.30902 (18)0.0351 (4)
H15A0.92290.12610.27670.053*
H15B0.74970.13130.30840.053*
H15C0.78420.21840.39510.053*
C160.5493 (2)0.56887 (19)0.14191 (18)0.0382 (5)
H16A0.49170.50830.15350.046*
H16B0.60100.57050.05060.046*
C170.4345 (2)0.70157 (17)0.20021 (17)0.0290 (4)
C180.3442 (2)0.76890 (19)0.13718 (19)0.0360 (5)
H18A0.35380.73080.06040.043*
C190.2409 (2)0.8908 (2)0.1858 (2)0.0402 (5)
H19A0.17960.93550.14260.048*
C200.2266 (2)0.9478 (2)0.2971 (2)0.0414 (5)
H20A0.15681.03190.32970.050*
C210.3144 (2)0.88166 (19)0.36020 (18)0.0399 (5)
H21A0.30470.92020.43680.048*
C220.4176 (2)0.75831 (18)0.31215 (18)0.0344 (4)
H22A0.47670.71300.35690.041*
C230.7939 (3)0.5743 (2)0.1510 (3)0.0603 (7)
H23A0.84980.55370.05990.091*
H23B0.86460.53760.19250.091*
H23C0.75160.66730.17240.091*
H1A0.429 (2)0.442 (2)0.427 (2)0.038 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0173 (2)0.0247 (2)0.0261 (2)−0.00350 (17)−0.00496 (17)−0.00334 (17)
F10.0611 (9)0.0976 (12)0.0788 (11)−0.0319 (9)−0.0460 (8)0.0389 (9)
F20.0449 (7)0.0539 (8)0.0632 (9)−0.0087 (6)−0.0301 (7)0.0035 (7)
O10.0354 (8)0.0614 (10)0.0329 (8)−0.0183 (7)−0.0068 (6)−0.0151 (7)
O20.0208 (6)0.0398 (7)0.0315 (7)−0.0084 (5)−0.0061 (5)−0.0112 (6)
N10.0182 (7)0.0342 (8)0.0262 (8)−0.0076 (6)−0.0044 (6)−0.0074 (7)
N20.0206 (7)0.0242 (7)0.0231 (7)−0.0022 (6)−0.0064 (6)0.0009 (6)
N30.0259 (8)0.0294 (8)0.0446 (10)−0.0035 (7)−0.0107 (7)0.0096 (7)
C10.0398 (12)0.0603 (14)0.0426 (12)−0.0222 (11)−0.0200 (10)0.0059 (11)
C20.0607 (16)0.0738 (18)0.0467 (14)−0.0402 (14)−0.0133 (12)0.0104 (13)
C30.0415 (13)0.0695 (17)0.0565 (15)−0.0329 (13)−0.0022 (11)−0.0100 (13)
C40.0249 (10)0.0540 (14)0.0626 (15)−0.0107 (10)−0.0140 (10)−0.0199 (12)
C50.0305 (10)0.0391 (11)0.0407 (11)−0.0086 (8)−0.0152 (9)−0.0073 (9)
C60.0242 (9)0.0382 (10)0.0320 (10)−0.0110 (8)−0.0100 (8)−0.0080 (8)
C70.0229 (9)0.0361 (10)0.0314 (10)−0.0061 (8)−0.0110 (8)−0.0053 (8)
C80.0242 (9)0.0297 (9)0.0241 (9)−0.0045 (7)−0.0065 (7)−0.0026 (7)
C90.0220 (8)0.0247 (9)0.0249 (9)−0.0068 (7)−0.0062 (7)0.0030 (7)
C100.0291 (9)0.0305 (9)0.0268 (9)−0.0079 (8)−0.0100 (8)0.0001 (7)
C110.0277 (10)0.0394 (11)0.0377 (11)−0.0139 (8)−0.0135 (8)0.0078 (9)
C120.0202 (9)0.0349 (10)0.0431 (11)−0.0073 (8)−0.0042 (8)0.0062 (9)
C130.0289 (10)0.0364 (11)0.0366 (11)−0.0061 (8)0.0008 (8)−0.0093 (9)
C140.0275 (9)0.0347 (10)0.0341 (10)−0.0113 (8)−0.0063 (8)−0.0046 (8)
C150.0328 (10)0.0314 (10)0.0344 (10)−0.0050 (8)−0.0106 (8)0.0058 (8)
C160.0437 (11)0.0322 (10)0.0317 (10)−0.0024 (9)−0.0158 (9)0.0019 (8)
C170.0267 (9)0.0288 (9)0.0299 (9)−0.0078 (7)−0.0107 (8)0.0061 (8)
C180.0359 (10)0.0403 (11)0.0377 (11)−0.0136 (9)−0.0202 (9)0.0070 (9)
C190.0299 (10)0.0413 (12)0.0511 (13)−0.0066 (9)−0.0222 (9)0.0147 (10)
C200.0324 (10)0.0326 (11)0.0463 (12)−0.0009 (8)−0.0100 (9)0.0057 (9)
C210.0426 (12)0.0362 (11)0.0322 (11)−0.0068 (9)−0.0103 (9)0.0014 (9)
C220.0364 (10)0.0304 (10)0.0323 (10)−0.0030 (8)−0.0158 (8)0.0060 (8)
C230.0362 (12)0.0495 (14)0.0853 (19)−0.0157 (11)−0.0129 (12)0.0317 (13)
Geometric parameters (Å, º) top
P1—O21.4796 (13)C10—H10A0.9500
P1—N31.6266 (16)C11—C121.385 (3)
P1—N21.6405 (14)C11—H11A0.9500
P1—N11.6886 (15)C12—C131.377 (3)
F1—C11.360 (2)C12—H12A0.9500
F2—C51.359 (2)C13—C141.397 (3)
O1—C71.219 (2)C13—H13A0.9500
N1—C71.362 (2)C14—H14A0.9500
N1—H1A0.83 (2)C15—H15A0.9800
N2—C81.463 (2)C15—H15B0.9800
N2—C151.471 (2)C15—H15C0.9800
N3—C161.462 (2)C16—C171.524 (3)
N3—C231.474 (3)C16—H16A0.9900
C1—C61.383 (3)C16—H16B0.9900
C1—C21.386 (3)C17—C221.380 (3)
C2—C31.380 (4)C17—C181.397 (3)
C2—H2A0.9500C18—C191.385 (3)
C3—C41.375 (3)C18—H18A0.9500
C3—H3A0.9500C19—C201.384 (3)
C4—C51.386 (3)C19—H19A0.9500
C4—H4A0.9500C20—C211.378 (3)
C5—C61.383 (3)C20—H20A0.9500
C6—C71.512 (3)C21—C221.396 (3)
C8—C91.529 (2)C21—H21A0.9500
C8—H8A0.9900C22—H22A0.9500
C8—H8B0.9900C23—H23A0.9800
C9—C141.389 (2)C23—H23B0.9800
C9—C101.389 (2)C23—H23C0.9800
C10—C111.395 (2)
O2—P1—N3114.81 (8)C12—C11—C10120.19 (18)
O2—P1—N2110.54 (7)C12—C11—H11A119.9
N3—P1—N2107.66 (8)C10—C11—H11A119.9
O2—P1—N1107.11 (8)C13—C12—C11119.55 (17)
N3—P1—N1107.24 (8)C13—C12—H12A120.2
N2—P1—N1109.34 (8)C11—C12—H12A120.2
C7—N1—P1126.79 (13)C12—C13—C14120.31 (18)
C7—N1—H1A116.4 (14)C12—C13—H13A119.8
P1—N1—H1A116.5 (14)C14—C13—H13A119.8
C8—N2—C15115.44 (14)C9—C14—C13120.73 (18)
C8—N2—P1125.15 (12)C9—C14—H14A119.6
C15—N2—P1116.63 (11)C13—C14—H14A119.6
C16—N3—C23116.19 (17)N2—C15—H15A109.5
C16—N3—P1126.13 (14)N2—C15—H15B109.5
C23—N3—P1117.53 (14)H15A—C15—H15B109.5
F1—C1—C6117.31 (18)N2—C15—H15C109.5
F1—C1—C2119.0 (2)H15A—C15—H15C109.5
C6—C1—C2123.7 (2)H15B—C15—H15C109.5
C3—C2—C1117.9 (2)N3—C16—C17114.79 (16)
C3—C2—H2A121.1N3—C16—H16A108.6
C1—C2—H2A121.1C17—C16—H16A108.6
C4—C3—C2121.4 (2)N3—C16—H16B108.6
C4—C3—H3A119.3C17—C16—H16B108.6
C2—C3—H3A119.3H16A—C16—H16B107.5
C3—C4—C5118.0 (2)C22—C17—C18118.77 (17)
C3—C4—H4A121.0C22—C17—C16122.46 (16)
C5—C4—H4A121.0C18—C17—C16118.76 (17)
F2—C5—C6117.05 (18)C19—C18—C17120.47 (19)
F2—C5—C4119.21 (19)C19—C18—H18A119.8
C6—C5—C4123.7 (2)C17—C18—H18A119.8
C5—C6—C1115.30 (18)C20—C19—C18120.37 (18)
C5—C6—C7121.65 (18)C20—C19—H19A119.8
C1—C6—C7123.04 (17)C18—C19—H19A119.8
O1—C7—N1123.93 (17)C21—C20—C19119.48 (19)
O1—C7—C6121.61 (16)C21—C20—H20A120.3
N1—C7—C6114.46 (15)C19—C20—H20A120.3
N2—C8—C9112.58 (14)C20—C21—C22120.33 (19)
N2—C8—H8A109.1C20—C21—H21A119.8
C9—C8—H8A109.1C22—C21—H21A119.8
N2—C8—H8B109.1C17—C22—C21120.56 (18)
C9—C8—H8B109.1C17—C22—H22A119.7
H8A—C8—H8B107.8C21—C22—H22A119.7
C14—C9—C10118.49 (16)N3—C23—H23A109.5
C14—C9—C8119.50 (15)N3—C23—H23B109.5
C10—C9—C8122.01 (15)H23A—C23—H23B109.5
C9—C10—C11120.73 (17)N3—C23—H23C109.5
C9—C10—H10A119.6H23A—C23—H23C109.5
C11—C10—H10A119.6H23B—C23—H23C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.83 (2)1.92 (2)2.752 (2)173 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC23H24F2N3O2P
Mr443.42
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)9.9370 (11), 11.1093 (15), 11.5902 (14)
α, β, γ (°)89.101 (4), 67.826 (4), 71.664 (4)
V (Å3)1116.9 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART X2S benchtop CCD area-detector
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2005)
Tmin, Tmax0.952, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections		13602, 5173, 3851
Rint0.036
(sin θ/λ)max (Å−1)0.657
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.126, 1.03
No. of reflections5173
No. of parameters286
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.37, −0.32

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.83 (2)1.92 (2)2.752 (2)173 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.
 

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged. The authors wish to thank Bruker AXS, Inc. for the use of one of their SMART X2S benchtop instruments.

References

First citationBruker (2005). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationPourayoubi, M. & Sabbaghi, F. (2009). J. Chem. Crystallogr. 39, 874–880.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSabbaghi, F., Pourayoubi, M., Toghraee, M. & Divjakovic, V. (2010). Acta Cryst. E66, o344.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 10| October 2010| Page o2524
doi:10.1107/S1600536810035725
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