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The title compound, C14H12N4O2, is the first example of a heterocyclic substituted hydroxamic derivative. The asymmetric unit consists of two molecules. The molecules are linked into centrosymmetric R44(20) tetramers by four strong hydrogen bonds of the N-H...O and N-H...N types. These tetramers are connected through C-H...O interactions into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108018003/sf3081sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108018003/sf3081Isup2.hkl
Contains datablock I

CCDC reference: 700025

Comment top

Recently, much attention has been focused on studies of the physicochemical, structural and catalytic properties of 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione (Jadrijević-Mladar Takač et al., 2006; Hirai et al., 2003, 2004; Caira et al., 2006). Active organooxyisocyanate derivatives have been employed as precursors in the synthesis of 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione. Intensive investigation of the properties of organooxyisocyanates revealed that, because of their low stability, only some compounds could serve as donors of the organooxyisocyanate group (Staab & Benz, 1961; Major & Hedrick, 1965; Berndt, 1970). Butula & Jadrijević-Mladar Takač (2000) reported that benzotriazole-1-carboxylic acid benzyloxy-amide, (I), can be used as a solid benzyloxyisocyanate donor.

Annealing of (I) to a sufficiently high temperature induces decomposition to benzotriazole [one of the most effective inhibitors of copper corrosion in neutral and alkaline conditions (Cotton & Scholes, 1967)] and benzyloxyisocyanate, a precursor for building 1,3,5-tribenzyloxy-1,3,5-triazinane-2,4,6-trione. 1,3,5-Tribenzyloxy-1,3,5-triazinane-2,4,6-trione can be easily converted to 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione by reduction with hydrogen. The benzyloxyaminocarbonyl group can be easily reduced to the hydroxylamine group, thus providing an alternative path for synthesis of hydroxamic acids and hydroxyureas. With this goal in mind and in an attempt to understand further the structure of hydroxamic acid and its derivatives (Matković-Čalogović et al., 2003; Đilović et al., 2006, 2007), the structure of (I) was determined using the single-crystal X-ray diffraction method.

The title compound is an example of a valuable precursor in hydroxamic acid chemistry. The asymmetric unit of (I) consists of two crystallographically independent molecules. A view of (I), including the atom-labeling scheme, is shown in Fig. 1, and selected geometric parameters are shown in Table 1. A trans configuration of the carbonyl O atoms with respect to the amide H atom is observed, and the N2 atom of the 1,2,3-triazole unit is in a cis configuration with respect to the amide N atom. Compound (I) contains two terminal aromatic (and also planar) substituents (the benzotriazole and phenyl rings), which are connected to the N-methoxy formamide segment. If we exclude the benzyl group, the rest of molecule is almost planar. The planes of the two symmetrically independent molecules are almost orthogonal [82.53 (1)°]. The molecules are linked into centrosymmetric tetramers to give a very rare structural motif [R44(20); Etter et al., 1990]. This four-membered circuit is formed by molecules found at symmetry sites (x, y, z) and (-x + 1, -y + 1, -z + 1), which are linked together by four hydrogen bonds of the N—H···O and N—H···N types (Table 2 and Fig. 2). In addition, the tetramers in the crystal structure are connected through C—H···O van der Waals interactions to form a three-dimensional network (Table 1 and Fig. 3).

Related literature top

For related literature, see: Berndt (1970); Butula & Jadrijević-Mladar Takač (2000); Caira et al. (2006); Cotton & Scholes (1967); Etter et al. (1990); Hirai et al. (2003, 2004); Major & Hedrick (1965); Matković-Čalogović, Bešić, Biruš & Gabričević (2003); Sheldrick (2008); Staab & Benz (1961); Đilović et al. (2006, 2007).

Experimental top

Benzotriazole-1-carboxylic acid benzyloxyamide was synthesized by a previously published procedure (Butula et al., 2000). The structure and purity were confirmed by means of thin-layer chromatography, FT–IR and NMR analyses. The compound was crystallized by slow evaporation from a saturated diethyl ether solution at room temperature (the beaker containing the solution was covered with aluminium foil to slow down evaporation). Colorless crystals of good quality were obtained after three weeks, and these were stable for several months when exposed to the atmosphere.

Refinement top

H atoms were constrained to ideal geometry using an appropriate riding model, with C—H = 0.93–0.97Å and N—H = 0.86Å, and with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of (I), with the atom-labeling scheme. Displacement ellipsoids are shown at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of (I), showing the tetramers connected by hydrogen bonding. Only one tetramer is shown.
[Figure 3] Fig. 3. The three-dimensional network in (I), indicating the hydrogen bonding and C—H···π interactions. Only one layer of molecules is shown.
N-benzyloxy-1H-benzotriazole-1-carboxamide top
Crystal data top
C14H12N4O2Z = 8
Mr = 268.28F(000) = 1120
Monoclinic, P21/cDx = 1.327 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.4267 (9) ŵ = 0.09 mm1
b = 20.6647 (7) ÅT = 293 K
c = 11.0684 (5) ÅPrism, colorless
β = 119.020 (4)°0.80 × 0.50 × 0.40 mm
V = 2685.5 (3) Å3
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
5236 independent reflections
Radiation source: fine-focus sealed tube3136 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 26.0°, θmin = 3.9°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 1616
Tmin = 0.929, Tmax = 0.964k = 2524
17530 measured reflectionsl = 1313
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0729P)2 + 0.0868P]
where P = (Fo2 + 2Fc2)/3
5236 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C14H12N4O2V = 2685.5 (3) Å3
Mr = 268.28Z = 8
Monoclinic, P21/cMo Kα radiation
a = 13.4267 (9) ŵ = 0.09 mm1
b = 20.6647 (7) ÅT = 293 K
c = 11.0684 (5) Å0.80 × 0.50 × 0.40 mm
β = 119.020 (4)°
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
5236 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
3136 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.964Rint = 0.020
17530 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.05Δρmax = 0.15 e Å3
5236 reflectionsΔρmin = 0.17 e Å3
361 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

The non-hydrogen atomic positions were determined by direct methods with SHELXS (Sheldrick, 1990) and refined to convergence by the full-matrix least-squares method with anisotropic thermal parameters using SHELXL97 (Sheldrick, 1997). At this stage the positions of all hydrogen atoms were obtained from the difference Fourier map. However, the number of observed reflections did not justify the refinement of hydrogen atoms with isotropic thermal parameters so they were determined on stereochemical grounds, each riding on their carrier atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.05750 (15)0.54847 (9)0.15734 (18)0.0619 (5)
C120.0921 (2)0.60431 (11)0.1177 (2)0.0994 (8)
H12A0.16410.59350.19800.119*
H12B0.04520.56570.08750.119*
C130.03353 (19)0.65620 (9)0.1519 (2)0.0737 (5)
C140.0899 (2)0.69158 (11)0.2692 (2)0.0924 (7)
H140.16650.68320.32860.111*
C150.0364 (4)0.73939 (14)0.3021 (3)0.1243 (11)
H150.07690.76260.38370.149*
C160.0713 (5)0.75271 (17)0.2195 (5)0.1420 (14)
H160.10620.78590.24200.170*
C170.1324 (3)0.71840 (19)0.1013 (5)0.1383 (12)
H170.20920.72740.04390.166*
C180.0791 (2)0.66963 (13)0.0668 (3)0.1064 (8)
H180.12010.64620.01430.128*
C190.11694 (14)0.42756 (9)0.34449 (19)0.0632 (5)
C1100.08703 (18)0.38276 (9)0.4499 (2)0.0758 (5)
H1100.14160.35910.45960.091*
C1110.02665 (19)0.37525 (10)0.5389 (2)0.0811 (6)
H1110.05010.34570.61100.097*
C1120.10800 (17)0.41061 (10)0.5243 (2)0.0763 (6)
H1120.18450.40380.58720.092*
C1130.08058 (14)0.45503 (9)0.42133 (19)0.0657 (5)
H1130.13570.47880.41280.079*
C1140.03495 (14)0.46238 (8)0.33038 (17)0.0575 (4)
N110.14141 (13)0.57951 (8)0.05157 (16)0.0802 (5)
H110.21160.56940.02190.096*
N120.09740 (11)0.50097 (7)0.21676 (14)0.0614 (4)
N130.21174 (11)0.49021 (8)0.16611 (16)0.0729 (4)
N140.22329 (12)0.44640 (8)0.24205 (17)0.0732 (4)
O110.04309 (10)0.55717 (6)0.20421 (14)0.0811 (4)
O120.11077 (11)0.62878 (6)0.00859 (13)0.0750 (4)
C210.53559 (14)0.45700 (8)0.20891 (16)0.0558 (4)
C220.51440 (18)0.40227 (9)0.03991 (18)0.0744 (5)
H22A0.44840.42360.03580.089*
H22B0.57630.43330.07250.089*
C230.54794 (17)0.34586 (8)0.13544 (19)0.0632 (5)
C240.65719 (18)0.32140 (10)0.1935 (2)0.0766 (6)
H240.70920.33950.17040.092*
C250.6900 (2)0.27063 (11)0.2849 (2)0.0934 (7)
H250.76420.25510.32380.112*
C260.6165 (3)0.24325 (12)0.3188 (3)0.1029 (8)
H260.64010.20890.38070.123*
C270.5077 (3)0.26523 (12)0.2634 (3)0.1017 (8)
H270.45690.24600.28700.122*
C280.4728 (2)0.31721 (11)0.1703 (2)0.0853 (6)
H280.39840.33240.13180.102*
C290.46956 (14)0.58683 (8)0.44864 (17)0.0586 (4)
C2100.49630 (17)0.63497 (9)0.5149 (2)0.0730 (5)
H2100.44020.66100.58180.088*
C2110.60840 (18)0.64265 (10)0.4779 (2)0.0830 (6)
H2110.62920.67450.52080.100*
C2120.69266 (17)0.60355 (10)0.3766 (2)0.0833 (6)
H2120.76830.61030.35370.100*
C2130.66768 (14)0.55586 (9)0.3100 (2)0.0690 (5)
H2130.72420.53010.24270.083*
C2140.55337 (13)0.54781 (8)0.34827 (16)0.0557 (4)
N210.45613 (13)0.43003 (7)0.18702 (15)0.0686 (4)
H210.38710.44390.22850.082*
N220.49401 (10)0.50768 (7)0.30783 (13)0.0564 (4)
N230.37900 (11)0.52190 (8)0.38059 (16)0.0682 (4)
N240.36489 (12)0.56878 (8)0.46365 (16)0.0706 (4)
O210.63545 (10)0.44262 (6)0.15447 (13)0.0728 (4)
O220.48790 (10)0.37882 (6)0.09524 (11)0.0659 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0510 (10)0.0733 (13)0.0594 (11)0.0063 (8)0.0252 (9)0.0040 (9)
C120.146 (2)0.0805 (16)0.0901 (16)0.0269 (14)0.0718 (16)0.0189 (13)
C130.0923 (15)0.0643 (13)0.0715 (14)0.0054 (10)0.0452 (12)0.0104 (10)
C140.1135 (18)0.0827 (16)0.0788 (16)0.0013 (13)0.0450 (14)0.0066 (13)
C150.208 (4)0.082 (2)0.100 (2)0.013 (2)0.088 (3)0.0037 (15)
C160.212 (4)0.105 (3)0.166 (4)0.063 (3)0.137 (4)0.042 (3)
C170.108 (2)0.148 (3)0.165 (3)0.042 (2)0.071 (2)0.045 (3)
C180.1058 (19)0.0939 (18)0.1041 (19)0.0010 (15)0.0389 (16)0.0033 (14)
C190.0548 (10)0.0685 (12)0.0677 (12)0.0002 (8)0.0309 (9)0.0057 (9)
C1100.0817 (14)0.0694 (13)0.0889 (14)0.0035 (10)0.0513 (12)0.0003 (11)
C1110.0879 (15)0.0768 (14)0.0812 (14)0.0158 (11)0.0430 (13)0.0140 (11)
C1120.0662 (12)0.0808 (14)0.0762 (14)0.0101 (10)0.0301 (10)0.0029 (11)
C1130.0523 (10)0.0743 (12)0.0672 (12)0.0027 (8)0.0264 (9)0.0022 (10)
C1140.0533 (9)0.0625 (11)0.0592 (11)0.0009 (8)0.0294 (8)0.0057 (8)
N110.0575 (9)0.0964 (12)0.0730 (11)0.0117 (8)0.0208 (8)0.0192 (9)
N120.0419 (7)0.0782 (10)0.0610 (9)0.0033 (6)0.0225 (7)0.0002 (8)
N130.0450 (8)0.0929 (12)0.0759 (10)0.0046 (7)0.0256 (7)0.0034 (9)
N140.0560 (9)0.0846 (12)0.0819 (11)0.0068 (8)0.0359 (9)0.0012 (9)
O110.0461 (7)0.1024 (10)0.0862 (9)0.0092 (6)0.0253 (7)0.0087 (8)
O120.0822 (9)0.0732 (9)0.0691 (8)0.0093 (7)0.0364 (7)0.0007 (7)
C210.0519 (10)0.0614 (11)0.0472 (9)0.0060 (8)0.0187 (8)0.0066 (8)
C220.0961 (14)0.0641 (12)0.0613 (12)0.0019 (10)0.0368 (11)0.0068 (10)
C230.0777 (12)0.0565 (11)0.0567 (11)0.0099 (9)0.0336 (10)0.0110 (9)
C240.0832 (14)0.0752 (14)0.0663 (12)0.0098 (11)0.0323 (11)0.0025 (11)
C250.1028 (17)0.0816 (16)0.0763 (15)0.0022 (13)0.0280 (14)0.0022 (12)
C260.155 (3)0.0763 (16)0.0764 (16)0.0097 (17)0.0551 (18)0.0002 (12)
C270.159 (3)0.0762 (17)0.1069 (19)0.0390 (16)0.094 (2)0.0189 (14)
C280.0957 (15)0.0805 (15)0.0925 (16)0.0175 (12)0.0557 (13)0.0230 (13)
C290.0509 (9)0.0641 (11)0.0519 (10)0.0030 (8)0.0178 (8)0.0040 (8)
C2100.0736 (13)0.0723 (12)0.0650 (12)0.0100 (9)0.0272 (10)0.0085 (10)
C2110.0788 (14)0.0771 (14)0.0937 (16)0.0007 (10)0.0424 (12)0.0114 (12)
C2120.0641 (12)0.0832 (14)0.1028 (16)0.0001 (10)0.0406 (12)0.0061 (13)
C2130.0521 (10)0.0719 (13)0.0740 (12)0.0067 (8)0.0235 (9)0.0026 (10)
C2140.0506 (9)0.0596 (11)0.0514 (10)0.0034 (7)0.0205 (8)0.0069 (8)
N210.0602 (9)0.0770 (10)0.0681 (10)0.0164 (7)0.0307 (8)0.0181 (8)
N220.0437 (7)0.0653 (9)0.0520 (8)0.0079 (6)0.0167 (6)0.0025 (7)
N230.0466 (8)0.0811 (11)0.0673 (10)0.0080 (7)0.0201 (7)0.0062 (8)
N240.0535 (9)0.0793 (11)0.0660 (10)0.0109 (7)0.0186 (7)0.0106 (8)
O210.0494 (7)0.0884 (9)0.0677 (8)0.0141 (6)0.0183 (6)0.0087 (7)
O220.0792 (8)0.0597 (8)0.0580 (7)0.0090 (6)0.0328 (6)0.0011 (6)
Geometric parameters (Å, º) top
C11—O111.2024 (19)C21—O211.2104 (19)
C11—N111.331 (2)C21—N211.326 (2)
C11—N121.423 (2)C21—N221.419 (2)
C12—O121.439 (2)C22—O221.443 (2)
C12—C131.483 (3)C22—C231.489 (2)
C12—H12A0.9700C22—H22A0.9700
C12—H12B0.9700C22—H22B0.9700
C13—C141.356 (3)C23—C281.376 (3)
C13—C181.367 (3)C23—C241.380 (3)
C14—C151.370 (4)C24—C251.374 (3)
C14—H140.9300C24—H240.9300
C15—C161.312 (5)C25—C261.339 (4)
C15—H150.9300C25—H250.9300
C16—C171.359 (5)C26—C271.359 (4)
C16—H160.9300C26—H260.9300
C17—C181.393 (4)C27—C281.403 (3)
C17—H170.9300C27—H270.9300
C18—H180.9300C28—H280.9300
C19—N141.380 (2)C29—C2101.383 (2)
C19—C1141.386 (2)C29—N241.384 (2)
C19—C1101.388 (3)C29—C2141.392 (2)
C110—C1111.366 (3)C210—C2111.364 (3)
C110—H1100.9300C210—H2100.9300
C111—C1121.387 (3)C211—C2121.400 (3)
C111—H1110.9300C211—H2110.9300
C112—C1131.367 (3)C212—C2131.366 (3)
C112—H1120.9300C212—H2120.9300
C113—C1141.388 (2)C213—C2141.390 (2)
C113—H1130.9300C213—H2130.9300
C114—N121.378 (2)C214—N221.367 (2)
N11—O121.3839 (19)N21—O221.3831 (17)
N11—H110.8600N21—H210.8600
N12—N131.3732 (18)N22—N231.3830 (18)
N13—N141.295 (2)N23—N241.2847 (19)
O11—C11—N11126.99 (18)O21—C21—N21126.94 (17)
O11—C11—N12119.98 (16)O21—C21—N22119.43 (16)
N11—C11—N12113.03 (15)N21—C21—N22113.63 (14)
O12—C12—C13106.87 (16)O22—C22—C23108.10 (14)
O12—C12—H12A110.3O22—C22—H22A110.1
C13—C12—H12A110.3C23—C22—H22A110.1
O12—C12—H12B110.3O22—C22—H22B110.1
C13—C12—H12B110.3C23—C22—H22B110.1
H12A—C12—H12B108.6H22A—C22—H22B108.4
C14—C13—C18117.9 (2)C28—C23—C24118.0 (2)
C14—C13—C12121.0 (2)C28—C23—C22121.7 (2)
C18—C13—C12121.1 (2)C24—C23—C22120.27 (18)
C13—C14—C15121.5 (3)C25—C24—C23120.7 (2)
C13—C14—H14119.2C25—C24—H24119.6
C15—C14—H14119.2C23—C24—H24119.6
C16—C15—C14120.5 (3)C26—C25—C24120.8 (3)
C16—C15—H15119.7C26—C25—H25119.6
C14—C15—H15119.7C24—C25—H25119.6
C15—C16—C17120.6 (3)C25—C26—C27120.6 (2)
C15—C16—H16119.7C25—C26—H26119.7
C17—C16—H16119.7C27—C26—H26119.7
C16—C17—C18119.4 (3)C26—C27—C28119.3 (2)
C16—C17—H17120.3C26—C27—H27120.3
C18—C17—H17120.3C28—C27—H27120.3
C13—C18—C17120.1 (3)C23—C28—C27120.4 (2)
C13—C18—H18119.9C23—C28—H28119.8
C17—C18—H18119.9C27—C28—H28119.8
N14—C19—C114108.83 (16)C210—C29—N24129.80 (16)
N14—C19—C110129.87 (18)C210—C29—C214121.51 (16)
C114—C19—C110121.30 (17)N24—C29—C214108.68 (15)
C111—C110—C19116.63 (19)C211—C210—C29117.20 (18)
C111—C110—H110121.7C211—C210—H210121.4
C19—C110—H110121.7C29—C210—H210121.4
C110—C111—C112121.6 (2)C210—C211—C212121.2 (2)
C110—C111—H111119.2C210—C211—H211119.4
C112—C111—H111119.2C212—C211—H211119.4
C113—C112—C111122.81 (19)C213—C212—C211122.28 (19)
C113—C112—H112118.6C213—C212—H212118.9
C111—C112—H112118.6C211—C212—H212118.9
C112—C113—C114115.60 (17)C212—C213—C214116.48 (17)
C112—C113—H113122.2C212—C213—H213121.8
C114—C113—H113122.2C214—C213—H213121.8
N12—C114—C19103.79 (14)N22—C214—C213134.90 (16)
N12—C114—C113134.14 (16)N22—C214—C29103.81 (14)
C19—C114—C113122.05 (17)C213—C214—C29121.29 (17)
C11—N11—O12117.09 (15)C21—N21—O22117.84 (14)
C11—N11—H11121.5C21—N21—H21121.1
O12—N11—H11121.5O22—N21—H21121.1
N13—N12—C114110.11 (14)C214—N22—N23110.12 (13)
N13—N12—C11121.33 (14)C214—N22—C21128.79 (13)
C114—N12—C11128.49 (14)N23—N22—C21121.08 (14)
N14—N13—N12108.08 (14)N24—N23—N22108.20 (14)
N13—N14—C19109.18 (14)N23—N24—C29109.19 (13)
N11—O12—C12111.04 (14)N21—O22—C22109.73 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O21i0.862.052.785 (2)143
N21—H21···N140.862.132.900 (3)149
C15—H15···O12ii0.932.563.380 (5)148
C212—H212···O11iii0.932.513.252 (6)137
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC14H12N4O2
Mr268.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.4267 (9), 20.6647 (7), 11.0684 (5)
β (°) 119.020 (4)
V3)2685.5 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.80 × 0.50 × 0.40
Data collection
DiffractometerOxford Diffraction Xcalibur CCD
diffractometer
Absorption correctionAnalytical
(CrysAlis RED; Oxford Diffraction, 2003)
Tmin, Tmax0.929, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
17530, 5236, 3136
Rint0.020
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.138, 1.05
No. of reflections5236
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O21i0.862.052.785 (2)143
N21—H21···N140.862.132.900 (3)149
C15—H15···O12ii0.932.563.380 (5)148
C212—H212···O11iii0.932.513.252 (6)137
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2; (iii) x1, y, z.
 

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