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In the title compound, C23H17ClF3NO3, the dihedral angle between the dihydro­anthracene and cyclo­propane ring systems is 58.5 (4)°. The amino H atom forms an intra­molecular hydrogen bond to a carbonyl O atom of the dioxodihydro­anthracene moiety. The crystal packing is further stabilized by an inter­molecular C—H...F contact.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704408X/bt2502sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680704408X/bt2502Isup2.hkl
Contains datablock I

CCDC reference: 667267

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.120
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.07 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C4 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, an important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). The title compound may have some insecticide activity. The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound.

The dihedral angles between the dihydroanthracen moiety and the cycloprapane groug is 58.5 (4)°. The fluoro in CF3 and methyl hydrogen in another molecule are linked by an intermolecular C—H···F hydrogen bond. The carbonyl atom O2 forms an intramolecular hydrogen bond to atom N1.

Related literature top

For related literature, see: Liu et al. (2006); Punja (1981).

Experimental top

The title compound was prepared according to the method of Liu et al. (2006). 3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid 0.97 g (4.0 mmol) was dispersed in SOCl2(15 ml), and a drop of anhydrous DMF was added. The mixture was heated to reflux for 4 h. SOCl2 was removed by rotoevaporation. The crude the product could be directly disolved in anhydrous toluene, mixed with aminopyridine (0.90 g,4.1 mmol). Then, triethylamine was dropped into the solution. After 12 h stirring at room temperature, the reaction mixture was poured into hexane. The red precipitate was filtrated off and recrystallized from acetone and a small amount of water (50:1) over 3 d at ambient temperature.

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(C). The amino H atom of was located in a difference map and freely refined.

Structure description top

3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, an important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). The title compound may have some insecticide activity. The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound.

The dihedral angles between the dihydroanthracen moiety and the cycloprapane groug is 58.5 (4)°. The fluoro in CF3 and methyl hydrogen in another molecule are linked by an intermolecular C—H···F hydrogen bond. The carbonyl atom O2 forms an intramolecular hydrogen bond to atom N1.

For related literature, see: Liu et al. (2006); Punja (1981).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along a axis. The C—H···F contact is shown as a dashed line.
(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-N-(9,10-dioxo-9,10- dihydroanthracen-1-yl)-2,2-dimethylcyclopropanecarboxamide top
Crystal data top
C23H17ClF3NO3Z = 2
Mr = 447.83F(000) = 460
Triclinic, P1Dx = 1.515 Mg m3
a = 8.127 (1) ÅMo Kα radiation, λ = 0.71070 Å
b = 8.1518 (9) ÅCell parameters from 2347 reflections
c = 15.821 (2) Åθ = 2.6–27.9°
α = 79.518 (8)°µ = 0.25 mm1
β = 88.256 (9)°T = 113 K
γ = 72.328 (8)°Platelet, yellow
V = 981.7 (2) Å30.26 × 0.24 × 0.10 mm
Data collection top
Rigaku Saturn
diffractometer
4630 independent reflections
Radiation source: rotating anode3258 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.034
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.6°
ω scansh = 1010
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1010
Tmin = 0.924, Tmax = 0.975l = 2017
7669 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0616P)2]
where P = (Fo2 + 2Fc2)/3
4630 reflections(Δ/σ)max < 0.001
287 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C23H17ClF3NO3γ = 72.328 (8)°
Mr = 447.83V = 981.7 (2) Å3
Triclinic, P1Z = 2
a = 8.127 (1) ÅMo Kα radiation
b = 8.1518 (9) ŵ = 0.25 mm1
c = 15.821 (2) ÅT = 113 K
α = 79.518 (8)°0.26 × 0.24 × 0.10 mm
β = 88.256 (9)°
Data collection top
Rigaku Saturn
diffractometer
4630 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
3258 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.975Rint = 0.034
7669 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.34 e Å3
4630 reflectionsΔρmin = 0.34 e Å3
287 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
Cl10.15058 (7)0.51727 (7)0.13945 (4)0.03385 (16)
F10.10806 (19)0.87745 (17)0.10610 (8)0.0423 (4)
F20.12094 (18)0.81308 (18)0.03437 (10)0.0489 (4)
F30.1147 (2)0.79087 (17)0.01174 (8)0.0429 (4)
O10.4957 (2)0.4919 (2)0.20203 (8)0.0300 (4)
O20.67461 (17)0.07963 (17)0.47055 (8)0.0214 (3)
O30.8801 (2)0.52026 (19)0.62598 (9)0.0310 (4)
N10.5423 (2)0.3304 (2)0.33821 (10)0.0196 (3)
C10.4817 (2)0.3672 (3)0.25405 (11)0.0199 (4)
C20.3993 (2)0.2382 (2)0.23394 (11)0.0184 (4)
H20.38660.15020.28460.022*
C30.4193 (3)0.1739 (3)0.14854 (11)0.0210 (4)
C40.2483 (2)0.2995 (2)0.16698 (11)0.0180 (4)
H40.15360.24520.18160.022*
C50.5315 (3)0.2333 (3)0.07951 (12)0.0289 (5)
H5A0.65060.15580.08890.043*
H5B0.52880.35340.08180.043*
H5C0.48820.22930.02300.043*
C60.4225 (3)0.0144 (3)0.15474 (13)0.0291 (5)
H6A0.54020.09180.16940.044*
H6B0.38530.03100.09940.044*
H6C0.34410.04230.19950.044*
C70.1912 (2)0.4809 (2)0.12117 (11)0.0178 (4)
H70.27870.53210.10060.021*
C80.0293 (2)0.5801 (3)0.10575 (11)0.0187 (4)
C90.0175 (3)0.7647 (3)0.05808 (12)0.0211 (4)
C100.6061 (2)0.4383 (3)0.37939 (11)0.0186 (4)
C110.5739 (3)0.6158 (3)0.34485 (12)0.0229 (4)
H110.51380.66310.29110.027*
C120.6285 (3)0.7231 (3)0.38801 (13)0.0242 (4)
H120.60570.84350.36370.029*
C130.7166 (3)0.6567 (3)0.46663 (12)0.0232 (4)
H130.75310.73170.49610.028*
C140.7510 (2)0.4816 (2)0.50191 (12)0.0181 (4)
C150.8468 (2)0.4175 (3)0.58665 (12)0.0207 (4)
C160.9029 (2)0.2269 (3)0.61968 (11)0.0187 (4)
C171.0105 (3)0.1594 (3)0.69284 (12)0.0229 (4)
H171.04480.23620.72210.027*
C181.0673 (3)0.0194 (3)0.72283 (12)0.0248 (4)
H181.14170.06520.77230.030*
C191.0158 (3)0.1321 (3)0.68083 (11)0.0217 (4)
H191.05640.25490.70110.026*
C200.9051 (2)0.0654 (3)0.60921 (11)0.0192 (4)
H200.86730.14240.58170.023*
C210.8494 (2)0.1138 (2)0.57768 (11)0.0170 (4)
C220.7344 (2)0.1811 (2)0.49952 (11)0.0166 (4)
C230.6969 (2)0.3674 (2)0.45955 (11)0.0178 (4)
H10.543 (3)0.224 (3)0.3731 (14)0.033 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0159 (2)0.0332 (3)0.0444 (3)0.0065 (2)0.0019 (2)0.0122 (2)
F10.0587 (10)0.0220 (7)0.0316 (7)0.0105 (7)0.0018 (6)0.0075 (6)
F20.0305 (8)0.0247 (7)0.0816 (10)0.0090 (6)0.0053 (7)0.0159 (7)
F30.0691 (11)0.0251 (7)0.0297 (6)0.0104 (7)0.0262 (7)0.0051 (6)
O10.0368 (9)0.0360 (9)0.0218 (7)0.0221 (8)0.0028 (6)0.0030 (7)
O20.0242 (7)0.0145 (7)0.0259 (7)0.0061 (6)0.0047 (5)0.0034 (6)
O30.0389 (9)0.0224 (8)0.0351 (8)0.0101 (7)0.0090 (7)0.0108 (7)
N10.0218 (8)0.0160 (8)0.0198 (8)0.0049 (7)0.0036 (6)0.0014 (7)
C10.0154 (9)0.0233 (11)0.0198 (9)0.0047 (8)0.0012 (7)0.0026 (8)
C20.0183 (9)0.0181 (10)0.0164 (8)0.0042 (8)0.0022 (7)0.0010 (8)
C30.0205 (10)0.0178 (10)0.0197 (9)0.0019 (8)0.0038 (7)0.0032 (8)
C40.0151 (9)0.0149 (10)0.0210 (8)0.0016 (8)0.0033 (7)0.0003 (8)
C50.0228 (11)0.0300 (12)0.0256 (10)0.0041 (9)0.0036 (8)0.0050 (10)
C60.0365 (12)0.0161 (11)0.0287 (10)0.0012 (9)0.0059 (9)0.0039 (9)
C70.0166 (9)0.0180 (10)0.0192 (8)0.0054 (8)0.0017 (7)0.0043 (8)
C80.0184 (9)0.0207 (10)0.0168 (8)0.0067 (8)0.0007 (7)0.0017 (8)
C90.0221 (10)0.0178 (10)0.0218 (9)0.0026 (8)0.0012 (7)0.0051 (8)
C100.0174 (9)0.0171 (10)0.0220 (9)0.0057 (8)0.0027 (7)0.0045 (8)
C110.0232 (10)0.0187 (10)0.0238 (9)0.0034 (8)0.0006 (8)0.0012 (8)
C120.0284 (11)0.0129 (10)0.0288 (10)0.0049 (9)0.0031 (8)0.0003 (8)
C130.0264 (11)0.0184 (10)0.0275 (10)0.0091 (9)0.0018 (8)0.0072 (9)
C140.0182 (9)0.0156 (10)0.0213 (9)0.0054 (8)0.0024 (7)0.0051 (8)
C150.0201 (10)0.0194 (10)0.0245 (9)0.0070 (8)0.0014 (7)0.0075 (8)
C160.0179 (9)0.0192 (10)0.0193 (9)0.0050 (8)0.0010 (7)0.0055 (8)
C170.0241 (10)0.0247 (11)0.0209 (9)0.0075 (9)0.0025 (8)0.0062 (9)
C180.0246 (10)0.0275 (12)0.0183 (9)0.0041 (9)0.0039 (7)0.0004 (9)
C190.0220 (10)0.0190 (10)0.0204 (9)0.0027 (8)0.0023 (7)0.0004 (8)
C200.0199 (9)0.0174 (10)0.0198 (9)0.0050 (8)0.0026 (7)0.0032 (8)
C210.0150 (9)0.0172 (10)0.0179 (8)0.0036 (8)0.0028 (7)0.0036 (8)
C220.0172 (9)0.0152 (10)0.0183 (8)0.0050 (8)0.0022 (7)0.0052 (8)
C230.0161 (9)0.0165 (10)0.0205 (9)0.0042 (8)0.0019 (7)0.0043 (8)
Geometric parameters (Å, º) top
Cl1—C81.7295 (19)C7—H70.9500
F1—C91.331 (2)C8—C91.495 (3)
F2—C91.324 (2)C10—C111.398 (3)
F3—C91.325 (2)C10—C231.421 (2)
O1—C11.218 (2)C11—C121.378 (2)
O2—C221.2353 (19)C11—H110.9500
O3—C151.224 (2)C12—C131.388 (3)
N1—C11.382 (2)C12—H120.9500
N1—C101.405 (2)C13—C141.379 (3)
N1—H10.94 (3)C13—H130.9500
C1—C21.489 (2)C14—C231.416 (2)
C2—C31.523 (2)C14—C151.496 (3)
C2—C41.547 (2)C15—C161.478 (3)
C2—H21.0000C16—C171.394 (2)
C3—C51.508 (3)C16—C211.402 (2)
C3—C61.512 (3)C17—C181.384 (3)
C3—C41.512 (3)C17—H170.9500
C4—C71.463 (3)C18—C191.390 (3)
C4—H41.0000C18—H180.9500
C5—H5A0.9800C19—C201.389 (2)
C5—H5B0.9800C19—H190.9500
C5—H5C0.9800C20—C211.391 (3)
C6—H6A0.9800C20—H200.9500
C6—H6B0.9800C21—C221.489 (2)
C6—H6C0.9800C22—C231.476 (3)
C7—C81.321 (3)
C1—N1—C10126.38 (17)F2—C9—C8111.90 (16)
C1—N1—H1119.3 (12)F3—C9—C8112.83 (14)
C10—N1—H1114.3 (12)F1—C9—C8111.76 (16)
O1—C1—N1123.11 (16)C11—C10—N1120.95 (17)
O1—C1—C2123.92 (15)C11—C10—C23119.70 (16)
N1—C1—C2112.97 (17)N1—C10—C23119.27 (17)
C1—C2—C3123.23 (16)C12—C11—C10120.66 (17)
C1—C2—C4119.42 (16)C12—C11—H11119.7
C3—C2—C458.98 (11)C10—C11—H11119.7
C1—C2—H2114.6C11—C12—C13120.57 (18)
C3—C2—H2114.6C11—C12—H12119.7
C4—C2—H2114.6C13—C12—H12119.7
C5—C3—C6114.14 (17)C14—C13—C12119.96 (16)
C5—C3—C4119.85 (17)C14—C13—H13120.0
C6—C3—C4115.70 (17)C12—C13—H13120.0
C5—C3—C2121.19 (16)C13—C14—C23121.12 (16)
C6—C3—C2114.75 (16)C13—C14—C15117.53 (15)
C4—C3—C261.29 (12)C23—C14—C15121.34 (17)
C7—C4—C3121.31 (16)O3—C15—C16121.59 (17)
C7—C4—C2120.40 (14)O3—C15—C14120.61 (18)
C3—C4—C259.72 (12)C16—C15—C14117.78 (14)
C7—C4—H4114.8C17—C16—C21119.91 (18)
C3—C4—H4114.8C17—C16—C15119.68 (16)
C2—C4—H4114.8C21—C16—C15120.41 (16)
C3—C5—H5A109.5C18—C17—C16120.01 (16)
C3—C5—H5B109.5C18—C17—H17120.0
H5A—C5—H5B109.5C16—C17—H17120.0
C3—C5—H5C109.5C17—C18—C19120.22 (17)
H5A—C5—H5C109.5C17—C18—H18119.9
H5B—C5—H5C109.5C19—C18—H18119.9
C3—C6—H6A109.5C20—C19—C18120.09 (19)
C3—C6—H6B109.5C20—C19—H19120.0
H6A—C6—H6B109.5C18—C19—H19120.0
C3—C6—H6C109.5C19—C20—C21120.19 (16)
H6A—C6—H6C109.5C19—C20—H20119.9
H6B—C6—H6C109.5C21—C20—H20119.9
C8—C7—C4126.07 (17)C20—C21—C16119.56 (16)
C8—C7—H7117.0C20—C21—C22119.03 (15)
C4—C7—H7117.0C16—C21—C22121.41 (17)
C7—C8—C9122.53 (17)O2—C22—C23122.63 (16)
C7—C8—Cl1125.14 (16)O2—C22—C21119.02 (16)
C9—C8—Cl1112.31 (14)C23—C22—C21118.35 (14)
F2—C9—F3107.74 (17)C14—C23—C10117.99 (17)
F2—C9—F1106.43 (15)C14—C23—C22119.72 (16)
F3—C9—F1105.76 (16)C10—C23—C22122.29 (15)
C10—N1—C1—O18.9 (3)C12—C13—C14—C15179.79 (18)
C10—N1—C1—C2171.50 (18)C13—C14—C15—O35.9 (3)
O1—C1—C2—C337.9 (3)C23—C14—C15—O3173.82 (19)
N1—C1—C2—C3141.67 (18)C13—C14—C15—C16172.65 (18)
O1—C1—C2—C432.4 (3)C23—C14—C15—C167.6 (3)
N1—C1—C2—C4148.07 (17)O3—C15—C16—C176.4 (3)
C1—C2—C3—C52.4 (3)C14—C15—C16—C17172.18 (17)
C4—C2—C3—C5109.4 (2)O3—C15—C16—C21173.94 (19)
C1—C2—C3—C6146.10 (19)C14—C15—C16—C217.5 (3)
C4—C2—C3—C6106.97 (19)C21—C16—C17—C181.4 (3)
C1—C2—C3—C4106.9 (2)C15—C16—C17—C18178.27 (18)
C5—C3—C4—C72.2 (2)C16—C17—C18—C190.8 (3)
C6—C3—C4—C7145.25 (16)C17—C18—C19—C200.9 (3)
C2—C3—C4—C7109.31 (17)C18—C19—C20—C211.9 (3)
C5—C3—C4—C2111.49 (18)C19—C20—C21—C161.3 (3)
C6—C3—C4—C2105.44 (18)C19—C20—C21—C22178.45 (17)
C1—C2—C4—C72.5 (3)C17—C16—C21—C200.4 (3)
C3—C2—C4—C7110.8 (2)C15—C16—C21—C20179.28 (17)
C1—C2—C4—C3113.3 (2)C17—C16—C21—C22179.90 (17)
C3—C4—C7—C8152.17 (17)C15—C16—C21—C220.4 (3)
C2—C4—C7—C8136.94 (19)C20—C21—C22—O28.5 (3)
C4—C7—C8—C9179.86 (16)C16—C21—C22—O2171.75 (18)
C4—C7—C8—Cl11.9 (3)C20—C21—C22—C23171.26 (17)
C7—C8—C9—F20.0 (2)C16—C21—C22—C238.5 (3)
Cl1—C8—C9—F2178.45 (13)C13—C14—C23—C100.1 (3)
C7—C8—C9—F3121.71 (19)C15—C14—C23—C10179.84 (16)
Cl1—C8—C9—F359.84 (19)C13—C14—C23—C22179.41 (17)
C7—C8—C9—F1119.26 (19)C15—C14—C23—C220.3 (3)
Cl1—C8—C9—F159.20 (17)C11—C10—C23—C140.3 (3)
C1—N1—C10—C1116.6 (3)N1—C10—C23—C14176.43 (17)
C1—N1—C10—C23166.71 (18)C11—C10—C23—C22179.80 (18)
N1—C10—C11—C12176.31 (18)N1—C10—C23—C223.1 (3)
C23—C10—C11—C120.4 (3)O2—C22—C23—C14171.94 (18)
C10—C11—C12—C130.0 (3)C21—C22—C23—C148.3 (3)
C11—C12—C13—C140.4 (3)O2—C22—C23—C107.5 (3)
C12—C13—C14—C230.5 (3)C21—C22—C23—C10172.25 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.94 (3)1.89 (2)2.639 (2)134.7 (18)
C5—H5A···F1i0.982.493.412 (3)158
Symmetry code: (i) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC23H17ClF3NO3
Mr447.83
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)8.127 (1), 8.1518 (9), 15.821 (2)
α, β, γ (°)79.518 (8), 88.256 (9), 72.328 (8)
V3)981.7 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.26 × 0.24 × 0.10
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.924, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
7669, 4630, 3258
Rint0.034
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.120, 1.01
No. of reflections4630
No. of parameters287
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.34

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL Bruker (1997), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.94 (3)1.89 (2)2.639 (2)134.7 (18)
C5—H5A···F1i0.982.493.412 (3)158
Symmetry code: (i) x+1, y1, z.
 

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