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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-3-(2-Chloro-3,3,3-tri­fluoro­prop-1-en­yl)-2,2-di­methyl-N,N-di­phenyl­cyclo­propane­carboxamide

aSchool of Materials and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
*Correspondence e-mail: yfytju@yahoo.com

(Received 8 November 2007; accepted 20 November 2007; online 6 December 2007)

The title compound, C21H19ClF3NO, was synthesized from 3-[(E)-2-chloro-3,3,3-trifluoro­prop-1-en­yl]-2,2-dimethyl­cyclo­propane­carboxylic acid and diphenyl­amine. The propenyl and carboxamide substituents lie on the same side of the cyclo­propane ring plane, with the two methyl substituents on either side of the plane. The phenyl rings of the carboxamide are inclined at an angle of 84.6 (3)° to one another. The F atoms are disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

For the preparation of the title compound, see: Liu et al. (2006[Liu, D.-Q., Feng, Y.-Q., Liu, D.-W. & Zhang, S.-S. (2006). Acta Cryst. E62, o1747-o1748.]). For the insecticidal properties of related compounds, see: Punja (1981[Punja, N. (1981). European Patent EP 0 031 199.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19ClF3NO

  • Mr = 393.82

  • Monoclinic, P 21 /n

  • a = 9.247 (6) Å

  • b = 21.443 (14) Å

  • c = 10.025 (7) Å

  • β = 99.068 (11)°

  • V = 1963 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 294 (2) K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.960

  • 11179 measured reflections

  • 4030 independent reflections

  • 2379 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.00

  • 4030 reflections

  • 274 parameters

  • 60 restraints

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL

Supporting information


Comment top

3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate in the preparation of tefluthrinan a useful insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). Diphenylamine is also a structure which has bioactivity. We reasoned that a structure containing both of these bioactive components may show enhanced insecticidal activity and prepared the title compound (I), whose structure is repoerted here Fig. 1.

The the propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The benzene rings of the carboxamide are inclined at 95.4 (3)° to one another. The crystal packing of (I) is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Liu et al. (2006). For the insecticidal properties of related compounds, see: Punja (1981).

Experimental top

The title compound was prepared according to the method of Liu et al. (2006). The product was recrystallized from methanol and ethyl acetate (5:1, v/v) over 3 days at ambient temperature, giving colourless single crystals of (I).

Refinement top

H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined using riding model with Uiso(H) = 1.2Ueq(carrier). The fluorine atoms of the trifluoromethyl group were disordered over two conformations. The occupancy factor for the major component refined to 0.56 (3).

Structure description top

3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate in the preparation of tefluthrinan a useful insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). Diphenylamine is also a structure which has bioactivity. We reasoned that a structure containing both of these bioactive components may show enhanced insecticidal activity and prepared the title compound (I), whose structure is repoerted here Fig. 1.

The the propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The benzene rings of the carboxamide are inclined at 95.4 (3)° to one another. The crystal packing of (I) is shown in Fig. 2.

For the preparation of the title compound, see: Liu et al. (2006). For the insecticidal properties of related compounds, see: Punja (1981).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal structure of (I), viewed along the a axis.
(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N,N- diphenylcyclopropanecarboxamide top
Crystal data top
C21H19ClF3NOF(000) = 816
Mr = 393.82Dx = 1.333 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2995 reflections
a = 9.247 (6) Åθ = 2.2–24.7°
b = 21.443 (14) ŵ = 0.23 mm1
c = 10.025 (7) ÅT = 294 K
β = 99.068 (11)°Prism, colourles
V = 1963 (2) Å30.22 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4030 independent reflections
Radiation source: fine-focus sealed tube2379 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1110
Tmin = 0.951, Tmax = 0.960k = 2026
11179 measured reflectionsl = 1211
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.4369P]
where P = (Fo2 + 2Fc2)/3
4030 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 0.30 e Å3
60 restraintsΔρmin = 0.32 e Å3
Crystal data top
C21H19ClF3NOV = 1963 (2) Å3
Mr = 393.82Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.247 (6) ŵ = 0.23 mm1
b = 21.443 (14) ÅT = 294 K
c = 10.025 (7) Å0.22 × 0.20 × 0.18 mm
β = 99.068 (11)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4030 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2379 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.960Rint = 0.034
11179 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04260 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.00Δρmax = 0.30 e Å3
4030 reflectionsΔρmin = 0.32 e Å3
274 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)
Cl10.52632 (8)0.07861 (4)0.13621 (8)0.0975 (3)
F10.732 (2)0.0017 (7)0.0236 (16)0.111 (4)0.44 (3)
F20.9287 (12)0.0254 (10)0.1498 (12)0.096 (3)0.44 (3)
F30.823 (2)0.0915 (7)0.0041 (15)0.122 (3)0.44 (3)
F1'0.7705 (16)0.0077 (4)0.0400 (14)0.103 (3)0.56 (3)
F2'0.9394 (7)0.0532 (8)0.1380 (10)0.094 (2)0.56 (3)
F3'0.7669 (19)0.0895 (6)0.0073 (10)0.123 (3)0.56 (3)
O11.00435 (15)0.11409 (7)0.53022 (16)0.0659 (4)
N10.96418 (16)0.19188 (7)0.67253 (17)0.0483 (4)
C10.7965 (3)0.04904 (14)0.0946 (3)0.0799 (8)
C20.7085 (2)0.06733 (10)0.1994 (2)0.0600 (6)
C30.7634 (2)0.07596 (10)0.3275 (2)0.0560 (5)
H30.86300.06830.35280.067*
C40.6825 (2)0.09642 (9)0.4335 (2)0.0542 (5)
H40.58220.11030.40030.065*
C50.7013 (2)0.06512 (9)0.5698 (2)0.0535 (5)
C60.7573 (2)0.13142 (9)0.5584 (2)0.0544 (5)
H60.69690.16370.59140.065*
C70.8048 (3)0.01108 (11)0.5998 (3)0.0745 (7)
H7A0.75800.02640.56240.112*
H7B0.83110.00650.69580.112*
H7C0.89130.01860.56050.112*
C80.5658 (3)0.06042 (12)0.6365 (3)0.0760 (7)
H8A0.50110.09450.60710.114*
H8B0.59350.06210.73280.114*
H8C0.51680.02170.61170.114*
C90.9165 (2)0.14478 (10)0.5816 (2)0.0522 (5)
C101.1194 (2)0.19815 (9)0.7161 (2)0.0473 (5)
C111.2001 (2)0.14777 (11)0.7713 (2)0.0565 (5)
H111.15450.10980.78110.068*
C121.3491 (3)0.15412 (13)0.8119 (2)0.0683 (7)
H121.40400.12020.84890.082*
C131.4170 (3)0.21036 (14)0.7978 (3)0.0739 (7)
H131.51770.21420.82360.089*
C141.3366 (3)0.26020 (13)0.7462 (3)0.0740 (7)
H141.38220.29840.73870.089*
C151.1871 (2)0.25455 (10)0.7048 (2)0.0621 (6)
H151.13260.28880.66930.074*
C160.8725 (2)0.24001 (9)0.7137 (2)0.0444 (5)
C170.7857 (2)0.27642 (9)0.6197 (2)0.0521 (5)
H170.78300.26890.52800.063*
C180.7031 (2)0.32397 (10)0.6614 (3)0.0636 (6)
H180.64400.34800.59740.076*
C190.7068 (2)0.33616 (11)0.7943 (3)0.0666 (7)
H190.65070.36840.82120.080*
C200.7929 (3)0.30110 (12)0.8887 (3)0.0686 (7)
H200.79600.30980.98000.082*
C210.8759 (2)0.25253 (11)0.8494 (2)0.0588 (6)
H210.93370.22840.91420.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0740 (4)0.1102 (6)0.0929 (5)0.0004 (4)0.0339 (4)0.0028 (4)
F10.105 (6)0.125 (6)0.095 (4)0.004 (4)0.010 (4)0.058 (5)
F20.079 (3)0.134 (7)0.074 (3)0.000 (4)0.005 (3)0.020 (5)
F30.135 (7)0.135 (5)0.104 (5)0.029 (5)0.041 (5)0.025 (4)
F1'0.103 (5)0.094 (3)0.112 (5)0.001 (3)0.013 (4)0.025 (3)
F2'0.081 (2)0.128 (6)0.076 (3)0.022 (3)0.0197 (18)0.023 (4)
F3'0.140 (7)0.161 (5)0.070 (3)0.007 (4)0.021 (4)0.033 (3)
O10.0450 (8)0.0741 (10)0.0785 (11)0.0020 (7)0.0097 (7)0.0341 (9)
N10.0402 (8)0.0436 (9)0.0607 (10)0.0005 (7)0.0063 (7)0.0123 (8)
C10.090 (2)0.089 (2)0.0554 (16)0.0193 (17)0.0049 (15)0.0049 (16)
C20.0611 (13)0.0561 (13)0.0569 (14)0.0085 (11)0.0086 (11)0.0024 (11)
C30.0467 (11)0.0594 (13)0.0579 (14)0.0005 (10)0.0041 (10)0.0032 (11)
C40.0409 (10)0.0512 (12)0.0669 (14)0.0016 (9)0.0023 (10)0.0055 (11)
C50.0501 (12)0.0486 (12)0.0617 (14)0.0026 (10)0.0081 (10)0.0088 (11)
C60.0424 (11)0.0460 (12)0.0740 (15)0.0006 (9)0.0068 (10)0.0165 (10)
C70.0812 (17)0.0595 (15)0.0812 (17)0.0102 (13)0.0081 (13)0.0081 (13)
C80.0708 (16)0.0765 (17)0.0849 (18)0.0165 (13)0.0252 (13)0.0172 (14)
C90.0468 (11)0.0495 (12)0.0599 (13)0.0007 (10)0.0071 (10)0.0109 (11)
C100.0410 (10)0.0492 (12)0.0520 (12)0.0002 (9)0.0080 (9)0.0095 (10)
C110.0550 (12)0.0571 (13)0.0557 (13)0.0045 (11)0.0039 (10)0.0044 (11)
C120.0585 (14)0.0866 (18)0.0575 (14)0.0222 (13)0.0017 (11)0.0091 (13)
C130.0442 (12)0.102 (2)0.0748 (17)0.0020 (14)0.0063 (12)0.0263 (15)
C140.0519 (14)0.0751 (17)0.0971 (19)0.0140 (13)0.0184 (13)0.0202 (15)
C150.0514 (12)0.0518 (13)0.0837 (16)0.0025 (10)0.0128 (11)0.0073 (12)
C160.0417 (10)0.0407 (11)0.0521 (12)0.0068 (9)0.0111 (9)0.0072 (9)
C170.0576 (12)0.0478 (12)0.0521 (12)0.0015 (10)0.0120 (10)0.0005 (10)
C180.0583 (13)0.0469 (13)0.0854 (18)0.0058 (11)0.0109 (12)0.0011 (12)
C190.0548 (13)0.0531 (14)0.097 (2)0.0060 (11)0.0264 (13)0.0219 (14)
C200.0665 (15)0.0822 (17)0.0622 (15)0.0136 (14)0.0256 (12)0.0277 (13)
C210.0568 (13)0.0690 (15)0.0508 (13)0.0025 (11)0.0087 (10)0.0044 (11)
Geometric parameters (Å, º) top
Cl1—C21.721 (2)C8—H8A0.9600
F1—C11.324 (8)C8—H8B0.9600
F2—C11.357 (7)C8—H8C0.9600
F3—C11.334 (8)C10—C151.375 (3)
F1'—C11.340 (7)C10—C111.378 (3)
F2'—C11.328 (6)C11—C121.381 (3)
F3'—C11.336 (7)C11—H110.9300
O1—C91.221 (2)C12—C131.377 (4)
N1—C91.385 (3)C12—H120.9300
N1—C161.437 (2)C13—C141.357 (4)
N1—C101.439 (2)C13—H130.9300
C1—C21.480 (4)C14—C151.385 (3)
C2—C31.317 (3)C14—H140.9300
C3—C41.460 (3)C15—H150.9300
C3—H30.9300C16—C171.380 (3)
C4—C51.508 (3)C16—C211.382 (3)
C4—C61.529 (3)C17—C181.378 (3)
C4—H40.9800C17—H170.9300
C5—C71.502 (3)C18—C191.353 (3)
C5—C81.514 (3)C18—H180.9300
C5—C61.523 (3)C19—C201.363 (3)
C6—C91.481 (3)C19—H190.9300
C6—H60.9800C20—C211.387 (3)
C7—H7A0.9600C20—H200.9300
C7—H7B0.9600C21—H210.9300
C7—H7C0.9600
C9—N1—C16124.86 (16)C5—C8—H8A109.5
C9—N1—C10117.84 (16)C5—C8—H8B109.5
C16—N1—C10116.81 (15)H8A—C8—H8B109.5
F1—C1—F3105.7 (11)C5—C8—H8C109.5
F2'—C1—F3'106.3 (6)H8A—C8—H8C109.5
F2'—C1—F1'107.5 (6)H8B—C8—H8C109.5
F3'—C1—F1'106.0 (8)O1—C9—N1120.42 (18)
F1—C1—F2103.4 (8)O1—C9—C6122.70 (19)
F3—C1—F2106.5 (7)N1—C9—C6116.76 (18)
F1—C1—C2109.6 (8)C15—C10—C11119.9 (2)
F2'—C1—C2112.3 (5)C15—C10—N1120.15 (18)
F3—C1—C2118.7 (8)C11—C10—N1119.98 (18)
F3'—C1—C2107.6 (7)C10—C11—C12119.6 (2)
F1'—C1—C2116.6 (6)C10—C11—H11120.2
F2—C1—C2111.7 (6)C12—C11—H11120.2
C3—C2—C1124.0 (2)C13—C12—C11120.4 (2)
C3—C2—Cl1122.9 (2)C13—C12—H12119.8
C1—C2—Cl1113.06 (17)C11—C12—H12119.8
C2—C3—C4126.0 (2)C14—C13—C12119.8 (2)
C2—C3—H3117.0C14—C13—H13120.1
C4—C3—H3117.0C12—C13—H13120.1
C3—C4—C5121.75 (18)C13—C14—C15120.5 (2)
C3—C4—C6121.70 (18)C13—C14—H14119.8
C5—C4—C660.22 (14)C15—C14—H14119.8
C3—C4—H4114.2C10—C15—C14119.9 (2)
C5—C4—H4114.2C10—C15—H15120.1
C6—C4—H4114.2C14—C15—H15120.1
C7—C5—C4120.27 (19)C17—C16—C21118.89 (19)
C7—C5—C8113.9 (2)C17—C16—N1121.07 (18)
C4—C5—C8116.37 (19)C21—C16—N1119.96 (18)
C7—C5—C6121.44 (19)C18—C17—C16120.2 (2)
C4—C5—C660.57 (14)C18—C17—H17119.9
C8—C5—C6114.21 (18)C16—C17—H17119.9
C9—C6—C5120.64 (17)C19—C18—C17120.8 (2)
C9—C6—C4122.29 (18)C19—C18—H18119.6
C5—C6—C459.21 (14)C17—C18—H18119.6
C9—C6—H6114.5C18—C19—C20119.9 (2)
C5—C6—H6114.5C18—C19—H19120.0
C4—C6—H6114.5C20—C19—H19120.0
C5—C7—H7A109.5C19—C20—C21120.4 (2)
C5—C7—H7B109.5C19—C20—H20119.8
H7A—C7—H7B109.5C21—C20—H20119.8
C5—C7—H7C109.5C16—C21—C20119.8 (2)
H7A—C7—H7C109.5C16—C21—H21120.1
H7B—C7—H7C109.5C20—C21—H21120.1
F1—C1—C2—C3131.3 (10)C16—N1—C9—C619.7 (3)
F2'—C1—C2—C311.5 (9)C10—N1—C9—C6168.66 (18)
F3—C1—C2—C3107.2 (10)C5—C6—C9—O147.4 (3)
F3'—C1—C2—C3128.0 (8)C4—C6—C9—O123.3 (3)
F1'—C1—C2—C3113.2 (8)C5—C6—C9—N1128.5 (2)
F2—C1—C2—C317.3 (11)C4—C6—C9—N1160.74 (19)
F1—C1—C2—Cl150.5 (10)C9—N1—C10—C15126.5 (2)
F2'—C1—C2—Cl1166.7 (8)C16—N1—C10—C1545.8 (3)
F3—C1—C2—Cl170.9 (10)C9—N1—C10—C1154.5 (3)
F3'—C1—C2—Cl150.2 (8)C16—N1—C10—C11133.2 (2)
F1'—C1—C2—Cl168.6 (8)C15—C10—C11—C121.5 (3)
F2—C1—C2—Cl1164.5 (11)N1—C10—C11—C12179.52 (19)
C1—C2—C3—C4177.4 (2)C10—C11—C12—C130.2 (3)
Cl1—C2—C3—C40.7 (3)C11—C12—C13—C141.3 (4)
C2—C3—C4—C5134.6 (2)C12—C13—C14—C151.4 (4)
C2—C3—C4—C6153.1 (2)C11—C10—C15—C141.3 (3)
C3—C4—C5—C70.4 (3)N1—C10—C15—C14179.7 (2)
C6—C4—C5—C7111.4 (2)C13—C14—C15—C100.2 (4)
C3—C4—C5—C8144.8 (2)C9—N1—C16—C1753.0 (3)
C6—C4—C5—C8104.2 (2)C10—N1—C16—C17118.7 (2)
C3—C4—C5—C6111.0 (2)C9—N1—C16—C21130.3 (2)
C7—C5—C6—C92.2 (3)C10—N1—C16—C2158.1 (2)
C4—C5—C6—C9111.7 (2)C21—C16—C17—C180.6 (3)
C8—C5—C6—C9140.5 (2)N1—C16—C17—C18177.38 (17)
C7—C5—C6—C4109.5 (2)C16—C17—C18—C190.7 (3)
C8—C5—C6—C4107.8 (2)C17—C18—C19—C200.1 (3)
C3—C4—C6—C92.1 (3)C18—C19—C20—C210.6 (3)
C5—C4—C6—C9109.0 (2)C17—C16—C21—C200.1 (3)
C3—C4—C6—C5111.1 (2)N1—C16—C21—C20176.72 (18)
C16—N1—C9—O1164.25 (19)C19—C20—C21—C160.7 (3)
C10—N1—C9—O17.4 (3)

Experimental details

Crystal data
Chemical formulaC21H19ClF3NO
Mr393.82
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)9.247 (6), 21.443 (14), 10.025 (7)
β (°) 99.068 (11)
V3)1963 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.951, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
11179, 4030, 2379
Rint0.034
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.119, 1.00
No. of reflections4030
No. of parameters274
No. of restraints60
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.32

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

 

Acknowledgements

This work was supported by the National Natural Science Foundation (No. 20376059)

References

First citationBruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLiu, D.-Q., Feng, Y.-Q., Liu, D.-W. & Zhang, S.-S. (2006). Acta Cryst. E62, o1747–o1748.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationPunja, N. (1981). European Patent EP 0 031 199.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar

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