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

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COMMUNICATIONS
ISSN: 2056-9890

(1H-1,2,3-Benzotriazol-1-yl)methyl 2,2-di­methyl­propano­ate

aDepartment of Applied Chemistry, School of Material Science and Engineering, Nanjing University of Aeronautics and Astronautics, Nanjing, Jiangsu Province 210016, People's Republic of China
*Correspondence e-mail: xusennuaa@163.com

(Received 14 February 2012; accepted 8 March 2012; online 14 March 2012)

In the title compound, C12H15N3O2, the dihedral angle between the mean planes of the benzene and triazole rings is 0.331 (53) °. The side chain of the pivalate unit forms a dihedral angle of 69.04 (12)° with the benzotriazole unit. The ester group and two methyl groups of the pivalate unit are disordered with an occupancy ratio of 0.731 (3):0.269 (3). In the crystal, weak ππ stacking inter­actions are observed between inversion-related benzene rings [centroid–centroid distance = 3.9040 (1) Å].

Related literature

For a related structure, see: Li & Chen (2011[Li, X.-X. & Chen, Z. (2011). Acta Cryst. E67, o140.]). For applications of benzotriazole derivatives, see: Wan & Lv (2010[Wan, J. & Lv, P.-C. (2010). J. Chem. Inf. Comput. Sci. 122, 597-606.]). For related coordination compounds, see: Hang & Ye (2008[Hang, T. & Ye, Q. (2008). Acta Cryst. E64, m758.]); Xu & Shen (2012[Xu, S. & Shen, Y. (2012). Acta Cryst. E68, m369.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15N3O2

  • Mr = 233.27

  • Monoclinic, P 21 /c

  • a = 8.1507 (3) Å

  • b = 16.7258 (8) Å

  • c = 9.2967 (4) Å

  • β = 98.354 (3)°

  • V = 1253.94 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.30 × 0.25 × 0.22 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.981

  • 9487 measured reflections

  • 2206 independent reflections

  • 1738 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.128

  • S = 1.03

  • 2206 reflections

  • 214 parameters

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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.10 e Å−3

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and SMART. 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Nobenzotriazole derivatives have been extensively studied, not only for their potential application in antibacterial activities (Wan & Lv, 2010), but also for synthesizing benzotriazole coordination complexs (Hang & Ye, 2008). In continuing our work with new benzotriazole coordination complexs (Xu & Shen, 2012), we have synthesized a new N-donor benzotriazole derivative ligand, C12H15N3O2, Fig. 1 Bond lengths and angles are similar to those in related benzotriazol-1-yl intermediate derivatives (Li & Chen, 2011, Wan & Lv, 2010). The ester group and two methyl groups in the pivalate unit are disordered, In the crystal, weak ππ stacking interactions are abserved between the inversion related phenyl rings (centroid-centroid distances = 3.9040 (1)°).

Related literature top

For a related structure, see: Li & Chen (2011). For applications of benzotriazole derivatives, see: Wan & Lv (2010). For related coordination compounds, see: Hang & Ye (2008); Xu & Shen (2012).

Experimental top

To a 250 ml round flask was added (1H-benzo[d][1,2,3]triazol-1-yl)methanol(3.73 g, 0.025 mol), methylene chloride(20 mL) and triethylamine(7.0 mL) with magnetic stirring atroom tempertature for 1 h. Pivaloyl chloride(3.32 g, 0.028 mol) was then added to the solution in the ice bath. The mixture was then refluxed for 6 h at 303 K under a nitrogen atmosphere. When the reaction was completed, the solvent was evaporated in vacuo, and the residue was washed with distilled water and purified by recrystallization from diethyl ether (Yield: 83.2%). Colorless crystals suitable for X-ray analysis were obtained by slow evaporation from diethyl ether at room temperature.

Refinement top

The H atoms on the CH2 group were located by difference maps and freely refined without constraints. H atoms bonded to the remaining C atoms were included in calculated positions and treated as riding with C–H = 0.93–0.97Å and Uiso(H)=1.2Ueq(aromatic C) or Uiso(H) = 1.5Ueq(CH3). The ester(–O—CO–) and two methyl groups (C10, C11) in the pivalate unit are disordered over two side positions with site occupation factors 0.731 (3)/0.269 (3). The C—C, C—O distances and angles of the disordered groups were refined without restraints.

Structure description top

Nobenzotriazole derivatives have been extensively studied, not only for their potential application in antibacterial activities (Wan & Lv, 2010), but also for synthesizing benzotriazole coordination complexs (Hang & Ye, 2008). In continuing our work with new benzotriazole coordination complexs (Xu & Shen, 2012), we have synthesized a new N-donor benzotriazole derivative ligand, C12H15N3O2, Fig. 1 Bond lengths and angles are similar to those in related benzotriazol-1-yl intermediate derivatives (Li & Chen, 2011, Wan & Lv, 2010). The ester group and two methyl groups in the pivalate unit are disordered, In the crystal, weak ππ stacking interactions are abserved between the inversion related phenyl rings (centroid-centroid distances = 3.9040 (1)°).

For a related structure, see: Li & Chen (2011). For applications of benzotriazole derivatives, see: Wan & Lv (2010). For related coordination compounds, see: Hang & Ye (2008); Xu & Shen (2012).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. Dashed lines indicate disordered ester and methyl groups.
(1H-1,2,3-Benzotriazol-1-yl)methyl 2,2-dimethylpropanoate top
Crystal data top
C12H15N3O2F(000) = 496
Mr = 233.27Dx = 1.236 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3348 reflections
a = 8.1507 (3) Åθ = 2.5–26.7°
b = 16.7258 (8) ŵ = 0.09 mm1
c = 9.2967 (4) ÅT = 296 K
β = 98.354 (3)°Block, colourless
V = 1253.94 (9) Å30.30 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2206 independent reflections
Radiation source: fine-focus sealed tube1738 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 2.4°
phi and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
k = 1919
Tmin = 0.975, Tmax = 0.981l = 1110
9487 measured reflections
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)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.060P)2 + 0.1761P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2206 reflectionsΔρmax = 0.18 e Å3
214 parametersΔρmin = 0.10 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.240 (12)
Crystal data top
C12H15N3O2V = 1253.94 (9) Å3
Mr = 233.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1507 (3) ŵ = 0.09 mm1
b = 16.7258 (8) ÅT = 296 K
c = 9.2967 (4) Å0.30 × 0.25 × 0.22 mm
β = 98.354 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2206 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1738 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.981Rint = 0.037
9487 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.18 e Å3
2206 reflectionsΔρmin = 0.10 e Å3
214 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*/UeqOcc. (<1)
O10.2265 (3)0.74088 (14)0.5551 (2)0.0766 (6)0.731 (3)
O20.1680 (2)0.82951 (11)0.3775 (2)0.0968 (7)0.731 (3)
O1A0.1824 (8)0.7730 (4)0.4914 (9)0.0822 (19)0.269 (3)
O2A0.3972 (6)0.6944 (3)0.5729 (7)0.111 (2)0.269 (3)
N10.04557 (15)0.65313 (9)0.40894 (14)0.0722 (4)
N20.05972 (18)0.66728 (11)0.28420 (19)0.0925 (5)
N30.0594 (2)0.60557 (12)0.19956 (17)0.0958 (5)
C10.11500 (17)0.57919 (10)0.40336 (15)0.0648 (4)
C20.2279 (2)0.53528 (13)0.49892 (19)0.0840 (6)
H20.27390.55510.58930.101*
C30.2672 (2)0.46083 (15)0.4516 (3)0.1008 (7)
H30.34280.42970.51180.121*
C40.1986 (3)0.43031 (14)0.3178 (3)0.1009 (7)
H40.22830.37930.29150.121*
C50.0898 (3)0.47290 (13)0.2249 (2)0.0927 (6)
H50.04460.45240.13490.111*
C60.04751 (19)0.54945 (11)0.26945 (18)0.0744 (5)
C70.0640 (2)0.71089 (15)0.5249 (3)0.0871 (6)
H1M0.025 (3)0.7513 (14)0.502 (2)0.120 (8)*
H2M0.055 (3)0.6865 (14)0.618 (3)0.127 (8)*
C80.2642 (4)0.80275 (16)0.4734 (3)0.0621 (6)0.731 (3)
C90.44199 (18)0.83291 (9)0.52164 (16)0.0637 (4)
C100.5617 (4)0.7648 (2)0.5330 (4)0.1025 (11)0.731 (3)
H10A0.53240.72650.60170.154*0.731 (3)
H10B0.67170.78440.56500.154*0.731 (3)
H10C0.55810.73990.43960.154*0.731 (3)
C110.4801 (6)0.8957 (3)0.4141 (4)0.1158 (13)0.731 (3)
H11A0.47030.87250.31870.174*0.731 (3)
H11B0.59100.91510.44190.174*0.731 (3)
H11C0.40310.93920.41350.174*0.731 (3)
C120.4501 (3)0.87363 (13)0.6689 (2)0.0948 (6)
H12A0.36710.91470.66330.142*
H12B0.55780.89700.69560.142*
H12C0.43040.83490.74070.142*
C8A0.3453 (9)0.7596 (5)0.5306 (7)0.0724 (18)0.269 (3)
C10A0.6271 (11)0.8008 (6)0.4959 (10)0.093 (3)0.269 (3)
H10D0.67350.76840.57700.139*0.269 (3)
H10E0.69830.84580.48730.139*0.269 (3)
H10F0.61720.76960.40850.139*0.269 (3)
C11A0.3845 (15)0.8843 (7)0.3900 (12)0.111 (3)0.269 (3)
H11D0.35970.85090.30570.166*0.269 (3)
H11E0.47050.92140.37560.166*0.269 (3)
H11F0.28680.91320.40520.166*0.269 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0696 (14)0.0778 (14)0.0794 (12)0.0172 (11)0.0009 (9)0.0118 (10)
O20.0858 (12)0.0929 (13)0.1025 (14)0.0056 (10)0.0178 (10)0.0215 (11)
O1A0.062 (4)0.068 (4)0.118 (5)0.009 (3)0.017 (3)0.009 (3)
O2A0.076 (3)0.093 (4)0.156 (5)0.011 (3)0.008 (3)0.044 (4)
N10.0554 (7)0.0852 (10)0.0737 (8)0.0143 (7)0.0016 (6)0.0047 (7)
N20.0710 (9)0.1006 (12)0.0981 (12)0.0067 (8)0.0137 (8)0.0126 (10)
N30.0864 (10)0.1078 (13)0.0844 (10)0.0175 (9)0.0168 (8)0.0037 (10)
C10.0488 (7)0.0823 (11)0.0636 (9)0.0170 (7)0.0091 (6)0.0083 (8)
C20.0680 (10)0.1065 (15)0.0754 (10)0.0131 (10)0.0034 (8)0.0167 (10)
C30.0809 (12)0.1038 (16)0.1190 (17)0.0079 (11)0.0189 (12)0.0314 (14)
C40.0994 (15)0.0939 (15)0.1166 (17)0.0059 (12)0.0396 (13)0.0078 (14)
C50.0960 (13)0.1002 (15)0.0861 (12)0.0315 (12)0.0270 (11)0.0105 (12)
C60.0626 (9)0.0894 (12)0.0709 (10)0.0198 (8)0.0083 (7)0.0050 (9)
C70.0694 (11)0.0980 (14)0.0957 (14)0.0240 (11)0.0185 (9)0.0136 (12)
C80.0670 (15)0.0573 (14)0.0606 (13)0.0068 (15)0.0046 (13)0.0034 (12)
C90.0650 (9)0.0635 (9)0.0618 (9)0.0068 (7)0.0064 (6)0.0023 (7)
C100.0652 (17)0.106 (3)0.134 (3)0.0108 (16)0.0070 (16)0.040 (2)
C110.133 (3)0.126 (3)0.091 (2)0.052 (3)0.025 (2)0.0067 (19)
C120.1017 (14)0.1004 (14)0.0820 (12)0.0055 (11)0.0122 (10)0.0232 (11)
C8A0.060 (4)0.082 (5)0.074 (4)0.001 (4)0.003 (3)0.017 (4)
C10A0.079 (5)0.093 (6)0.109 (6)0.010 (4)0.024 (4)0.003 (5)
C11A0.107 (7)0.100 (7)0.114 (7)0.021 (6)0.022 (6)0.040 (5)
Geometric parameters (Å, º) top
O1—C81.345 (4)C8—C91.539 (4)
O1—C71.406 (3)C9—C8A1.466 (8)
O2—C81.186 (3)C9—C101.493 (3)
O1A—C8A1.344 (10)C9—C111.512 (4)
O1A—C71.481 (8)C9—C11A1.513 (9)
O2A—C8A1.215 (10)C9—C121.522 (2)
N1—N21.3594 (19)C9—C10A1.651 (9)
N1—C11.364 (2)C10—H10A0.9600
N1—C71.439 (2)C10—H10B0.9600
N2—N31.298 (2)C10—H10C0.9600
N3—C61.378 (2)C11—H11A0.9600
C1—C61.379 (2)C11—H11B0.9600
C1—C21.392 (2)C11—H11C0.9600
C2—C31.374 (3)C12—H12A0.9600
C2—H20.9300C12—H12B0.9600
C3—C41.385 (3)C12—H12C0.9600
C3—H30.9300C10A—H10D0.9600
C4—C51.348 (3)C10A—H10E0.9600
C4—H40.9300C10A—H10F0.9600
C5—C61.404 (3)C11A—H11D0.9600
C5—H50.9300C11A—H11E0.9600
C7—H1M0.99 (2)C11A—H11F0.9600
C7—H2M0.97 (2)
C8—O1—C7116.6 (3)C11—C9—C11A30.7 (3)
C8A—O1A—C7118.3 (8)C8A—C9—C12106.0 (3)
N2—N1—C1109.84 (14)C10—C9—C12109.57 (19)
N2—N1—C7120.41 (17)C11—C9—C12107.3 (2)
C1—N1—C7129.67 (16)C11A—C9—C12116.2 (5)
N3—N2—N1108.78 (15)C8A—C9—C841.5 (3)
N2—N3—C6108.23 (14)C10—C9—C8110.42 (19)
N1—C1—C6104.36 (14)C11—C9—C8108.1 (2)
N1—C1—C2133.91 (16)C11A—C9—C877.4 (4)
C6—C1—C2121.73 (18)C12—C9—C8108.94 (14)
C3—C2—C1115.92 (18)C8A—C9—C10A104.2 (4)
C3—C2—H2122.0C10—C9—C10A33.0 (3)
C1—C2—H2122.0C11—C9—C10A81.4 (4)
C2—C3—C4122.6 (2)C11A—C9—C10A104.5 (6)
C2—C3—H3118.7C12—C9—C10A110.8 (4)
C4—C3—H3118.7C8—C9—C10A133.9 (4)
C5—C4—C3121.5 (2)C9—C10—H10A109.5
C5—C4—H4119.2C9—C10—H10B109.5
C3—C4—H4119.2C9—C10—H10C109.5
C4—C5—C6117.38 (19)C9—C11—H11A109.5
C4—C5—H5121.3C9—C11—H11B109.5
C6—C5—H5121.3C9—C11—H11C109.5
N3—C6—C1108.78 (17)C9—C12—H12A109.5
N3—C6—C5130.39 (18)C9—C12—H12B109.5
C1—C6—C5120.82 (18)H12A—C12—H12B109.5
O1—C7—N1112.46 (17)C9—C12—H12C109.5
O1—C7—O1A33.7 (2)H12A—C12—H12C109.5
N1—C7—O1A108.3 (3)H12B—C12—H12C109.5
O1—C7—H1M115.9 (14)O2A—C8A—O1A121.4 (8)
N1—C7—H1M107.8 (13)O2A—C8A—C9127.2 (6)
O1A—C7—H1M87.4 (14)O1A—C8A—C9111.3 (7)
O1—C7—H2M99.3 (14)C9—C10A—H10D109.5
N1—C7—H2M111.8 (14)C9—C10A—H10E109.5
O1A—C7—H2M128.2 (14)H10D—C10A—H10E109.5
H1M—C7—H2M109.4 (18)C9—C10A—H10F109.5
O2—C8—O1122.3 (4)H10D—C10A—H10F109.5
O2—C8—C9125.9 (3)H10E—C10A—H10F109.5
O1—C8—C9111.7 (2)C9—C11A—H11D109.5
C8A—C9—C1073.1 (3)C9—C11A—H11E109.5
C8A—C9—C11141.4 (3)H11D—C11A—H11E109.5
C10—C9—C11112.4 (3)C9—C11A—H11F109.5
C8A—C9—C11A114.5 (5)H11D—C11A—H11F109.5
C10—C9—C11A127.8 (6)H11E—C11A—H11F109.5
C1—N1—N2—N30.27 (18)C7—O1—C8—O22.4 (4)
C7—N1—N2—N3177.51 (15)C7—O1—C8—C9177.12 (17)
N1—N2—N3—C60.17 (19)O2—C8—C9—C8A157.5 (5)
N2—N1—C1—C60.25 (16)O1—C8—C9—C8A23.0 (4)
C7—N1—C1—C6177.16 (14)O2—C8—C9—C10130.2 (3)
N2—N1—C1—C2179.74 (16)O1—C8—C9—C1050.3 (3)
C7—N1—C1—C22.8 (3)O2—C8—C9—C116.9 (3)
N1—C1—C2—C3179.88 (16)O1—C8—C9—C11173.7 (3)
C6—C1—C2—C30.1 (2)O2—C8—C9—C11A4.3 (6)
C1—C2—C3—C40.5 (3)O1—C8—C9—C11A176.3 (6)
C2—C3—C4—C50.8 (3)O2—C8—C9—C12109.4 (2)
C3—C4—C5—C60.5 (3)O1—C8—C9—C1270.0 (2)
N2—N3—C6—C10.02 (19)O2—C8—C9—C10A102.3 (5)
N2—N3—C6—C5179.30 (17)O1—C8—C9—C10A78.2 (5)
N1—C1—C6—N30.14 (16)C7—O1A—C8A—O2A10.7 (10)
C2—C1—C6—N3179.85 (14)C7—O1A—C8A—C9166.6 (4)
N1—C1—C6—C5179.54 (13)C10—C9—C8A—O2A17.8 (7)
C2—C1—C6—C50.5 (2)C11—C9—C8A—O2A122.8 (7)
C4—C5—C6—N3179.41 (17)C11A—C9—C8A—O2A142.3 (9)
C4—C5—C6—C10.2 (2)C12—C9—C8A—O2A88.2 (7)
C8—O1—C7—N185.2 (3)C8—C9—C8A—O2A171.1 (10)
C8—O1—C7—O1A4.4 (4)C10A—C9—C8A—O2A28.7 (9)
N2—N1—C7—O1118.0 (2)C10—C9—C8A—O1A165.1 (6)
C1—N1—C7—O165.3 (3)C11—C9—C8A—O1A60.2 (8)
N2—N1—C7—O1A82.3 (3)C11A—C9—C8A—O1A40.7 (9)
C1—N1—C7—O1A101.1 (4)C12—C9—C8A—O1A88.8 (6)
C8A—O1A—C7—O117.8 (4)C8—C9—C8A—O1A11.8 (4)
C8A—O1A—C7—N185.5 (6)C10A—C9—C8A—O1A154.2 (6)

Experimental details

Crystal data
Chemical formulaC12H15N3O2
Mr233.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.1507 (3), 16.7258 (8), 9.2967 (4)
β (°) 98.354 (3)
V3)1253.94 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.25 × 0.22
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.975, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
9487, 2206, 1738
Rint0.037
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.128, 1.03
No. of reflections2206
No. of parameters214
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.10

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the Natural Science Foundation of Jiangsu Province of China (BK2008401) and the Natural Science Foundation of China (21172107)

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHang, T. & Ye, Q. (2008). Acta Cryst. E64, m758.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, X.-X. & Chen, Z. (2011). Acta Cryst. E67, o140.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWan, J. & Lv, P.-C. (2010). J. Chem. Inf. Comput. Sci. 122, 597–606.  CAS Google Scholar
First citationXu, S. & Shen, Y. (2012). Acta Cryst. E68, m369.  CSD CrossRef IUCr Journals Google Scholar

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