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The title compound, C29H45Cl3NO·0.5C5H12O, is a rare example of a crystalline tri­chloro­acetimidate and has a structure similar to that reported for analogous species.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100825X/tk6022sup1.cif
Contains datablocks sim1, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100825X/tk6022Isup2.hkl
Contains datablock I

CCDC reference: 170307

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.010 Å
  • Disorder in solvent or counterion
  • R factor = 0.078
  • wR factor = 0.221
  • Data-to-parameter ratio = 8.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 45.00 Perc. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2926 Count of symmetry unique reflns 2961 Completeness (_total/calc) 98.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4B (Harms, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C29H45Cl3NO·0.5C5H12OF(000) = 1240
Mr = 574.08Dx = 1.213 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 29.037 (13) ÅCell parameters from 25 reflections
b = 9.072 (6) Åθ = 9–16°
c = 12.628 (6) ŵ = 0.32 mm1
β = 109.14 (7)°T = 173 K
V = 3143 (3) Å3Plate, colorless
Z = 40.50 × 0.50 × 0.30 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2640 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
ω scansh = 330
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 010
Tmin = 0.857, Tmax = 0.911l = 1214
3008 measured reflections3 standard reflections every 100 reflections
2926 independent reflections intensity decay: <2%
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)] = 0.078H-atom parameters constrained
wR(F2) = 0.221 w = 1/[σ2(Fo2) + (0.1249P)2 + 13.5363P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.048
2926 reflectionsΔρmax = 0.97 e Å3
358 parametersΔρmin = 0.72 e Å3
8 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (18)
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)
Cl110.01083 (10)0.0125 (3)0.3192 (2)0.0697 (8)
Cl120.00509 (11)0.2983 (3)0.3199 (3)0.0861 (10)
Cl130.07229 (9)0.1487 (5)0.50617 (18)0.0843 (9)
O10.07050 (19)0.1069 (6)0.2047 (4)0.0447 (13)
N10.1259 (3)0.2227 (10)0.3493 (7)0.062 (2)
C280.0834 (3)0.1651 (10)0.3022 (6)0.050 (2)
C10.1044 (2)0.1309 (9)0.0568 (6)0.0371 (15)
H1C0.11710.23300.04630.045*
H1D0.08420.11980.13650.045*
C20.0719 (2)0.1086 (9)0.0158 (6)0.0415 (17)
H2A0.05650.01010.00140.050*
H2B0.04590.18410.00260.050*
C30.1029 (3)0.1215 (8)0.1368 (6)0.0398 (17)
H3A0.11860.22110.14990.048*
C40.1418 (3)0.0057 (9)0.1692 (6)0.0402 (16)
H4A0.16190.01830.24890.048*
H4B0.12660.09310.16030.048*
C50.1741 (3)0.0175 (7)0.0962 (5)0.0328 (14)
C60.2215 (2)0.0192 (7)0.1417 (5)0.0326 (14)
H6A0.23480.01570.22120.039*
C70.2566 (2)0.0265 (8)0.0764 (5)0.0331 (15)
H7A0.27270.12420.08860.040*
H7B0.28220.04910.10590.040*
C80.2323 (2)0.0022 (7)0.0501 (5)0.0275 (13)
H8A0.22680.10580.06470.033*
C90.1830 (2)0.0811 (8)0.0907 (5)0.0289 (13)
H9A0.18970.18670.06820.035*
C100.1474 (2)0.0242 (8)0.0314 (5)0.0308 (14)
C110.1608 (2)0.0798 (9)0.2208 (5)0.0355 (15)
H11A0.13150.14340.24350.043*
H11B0.15020.02180.24590.043*
C120.1963 (2)0.1336 (9)0.2812 (5)0.0340 (14)
H12A0.20410.23890.26360.041*
H12B0.18060.12420.36330.041*
C130.2431 (2)0.0428 (7)0.2438 (5)0.0268 (13)
C140.2645 (2)0.0593 (7)0.1145 (5)0.0271 (13)
H14A0.26870.16740.09880.033*
C150.3155 (2)0.0053 (8)0.0864 (5)0.0327 (14)
H15A0.33750.03440.01460.039*
H15B0.31480.11410.08160.039*
C160.3318 (2)0.0453 (8)0.1867 (5)0.0347 (15)
H16A0.35670.12410.16250.042*
H16B0.34610.03850.21540.042*
C170.2854 (2)0.1040 (7)0.2800 (5)0.0295 (14)
H17A0.28510.21380.27300.035*
C180.2331 (3)0.1197 (8)0.2805 (6)0.0365 (16)
H18A0.21950.12480.36240.055*
H18B0.26360.17560.25470.055*
H18C0.20980.16180.24760.055*
C190.1284 (3)0.1321 (9)0.0713 (6)0.0413 (17)
H19A0.10610.16420.03190.062*
H19B0.11100.13050.15220.062*
H19C0.15590.20060.05500.062*
C200.2863 (2)0.0675 (8)0.3993 (5)0.0353 (15)
H20A0.28870.04200.40480.042*
C210.2408 (3)0.1169 (11)0.4917 (6)0.047 (2)
H21A0.24360.09150.56470.070*
H21B0.21220.06730.48300.070*
H21C0.23700.22380.48710.070*
C220.3316 (2)0.1351 (10)0.4167 (5)0.0391 (15)
H22A0.32830.24370.41840.047*
H22B0.36050.10920.35180.047*
C230.3403 (3)0.0844 (9)0.5244 (6)0.0433 (17)
H23A0.34120.02470.52600.052*
H23B0.31290.11780.59010.052*
C240.3878 (2)0.1448 (11)0.5329 (5)0.0437 (17)
H24A0.41530.09470.47620.052*
H24B0.38990.25090.51370.052*
C250.3946 (3)0.1277 (10)0.6466 (8)0.063 (2)
H25A0.37000.19470.69840.075*
C260.3853 (3)0.0228 (11)0.7004 (8)0.068 (3)
H26A0.35300.05770.70250.103*
H26B0.38640.01670.77690.103*
H26C0.41020.09180.65660.103*
C270.4449 (3)0.1883 (11)0.6420 (8)0.060 (2)
H27A0.44910.17540.71530.091*
H27B0.44680.29340.62290.091*
H27C0.47060.13470.58490.091*
C290.0451 (2)0.1490 (9)0.3604 (5)0.0371 (15)
C1000.00000.3864 (11)0.00000.065 (4)
C2000.0400 (14)0.467 (6)0.034 (4)0.067 (14)0.50
H20B0.02570.51520.10440.101*0.50
H20C0.05550.53850.02270.101*0.50
H20D0.06380.39660.03960.101*0.50
O20.0252 (7)0.2675 (17)0.0709 (13)0.081 (6)0.50
C5000.0429 (10)0.323 (3)0.1845 (16)0.071 (7)0.50
H50A0.05930.24560.23500.106*0.50
H50B0.06520.40270.18920.106*0.50
H50C0.01570.35730.20470.106*0.50
C3000.0192 (10)0.299 (3)0.1115 (16)0.081 (12)0.50
H30A0.00630.24990.13030.121*0.50
H30B0.04290.22830.10620.121*0.50
H30C0.03460.37010.16860.121*0.50
C4000.0397 (15)0.493 (5)0.011 (4)0.055 (11)0.50
H40A0.05330.54210.05950.082*0.50
H40B0.06460.43560.02670.082*0.50
H40C0.02700.56420.06940.082*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.0944 (18)0.0650 (15)0.0753 (15)0.0431 (14)0.0625 (14)0.0222 (12)
Cl120.0665 (16)0.0654 (17)0.129 (3)0.0240 (13)0.0362 (16)0.0253 (17)
Cl130.0711 (14)0.133 (3)0.0412 (10)0.0221 (18)0.0076 (9)0.0039 (15)
O10.054 (3)0.044 (3)0.054 (3)0.019 (2)0.041 (2)0.024 (2)
N10.056 (4)0.071 (5)0.061 (4)0.013 (4)0.023 (3)0.013 (4)
C280.061 (4)0.056 (5)0.044 (4)0.029 (4)0.033 (3)0.024 (4)
C10.034 (3)0.038 (4)0.047 (4)0.004 (3)0.023 (3)0.005 (3)
C20.036 (3)0.043 (4)0.050 (4)0.007 (3)0.021 (3)0.008 (3)
C30.044 (4)0.031 (4)0.057 (4)0.009 (3)0.035 (3)0.014 (3)
C40.052 (4)0.040 (4)0.038 (4)0.009 (4)0.026 (3)0.006 (3)
C50.047 (4)0.026 (3)0.029 (3)0.001 (3)0.017 (3)0.006 (3)
C60.046 (4)0.026 (3)0.027 (3)0.000 (3)0.014 (3)0.001 (3)
C70.042 (4)0.033 (4)0.028 (3)0.004 (3)0.017 (3)0.002 (3)
C80.037 (3)0.024 (3)0.024 (3)0.001 (3)0.014 (2)0.001 (3)
C90.038 (3)0.028 (3)0.026 (3)0.001 (3)0.017 (3)0.003 (3)
C100.041 (3)0.031 (3)0.026 (3)0.002 (3)0.019 (3)0.008 (3)
C110.033 (3)0.045 (4)0.030 (3)0.003 (3)0.012 (3)0.003 (3)
C120.034 (3)0.043 (4)0.028 (3)0.007 (3)0.014 (2)0.004 (3)
C130.033 (3)0.028 (3)0.025 (3)0.006 (3)0.016 (2)0.002 (2)
C140.032 (3)0.025 (3)0.025 (3)0.001 (3)0.011 (2)0.003 (3)
C150.037 (3)0.038 (4)0.029 (3)0.007 (3)0.018 (3)0.008 (3)
C160.036 (3)0.036 (4)0.035 (3)0.010 (3)0.015 (3)0.008 (3)
C170.036 (3)0.026 (3)0.028 (3)0.001 (3)0.012 (3)0.003 (3)
C180.046 (4)0.035 (4)0.036 (4)0.008 (3)0.023 (3)0.005 (3)
C190.045 (4)0.036 (4)0.046 (4)0.009 (3)0.019 (3)0.010 (3)
C200.040 (4)0.035 (4)0.035 (3)0.006 (3)0.019 (3)0.005 (3)
C210.045 (4)0.065 (6)0.035 (3)0.003 (4)0.019 (3)0.003 (4)
C220.041 (3)0.046 (4)0.037 (3)0.007 (4)0.022 (3)0.008 (3)
C230.055 (4)0.037 (4)0.049 (4)0.001 (3)0.033 (4)0.008 (3)
C240.037 (3)0.065 (5)0.034 (3)0.008 (4)0.019 (3)0.004 (4)
C250.073 (5)0.061 (6)0.074 (6)0.011 (5)0.052 (5)0.006 (5)
C260.060 (5)0.100 (8)0.060 (5)0.016 (6)0.040 (4)0.021 (6)
C270.066 (5)0.070 (6)0.069 (5)0.008 (5)0.053 (5)0.006 (5)
C290.041 (3)0.035 (4)0.040 (3)0.006 (3)0.019 (3)0.003 (3)
C1000.046 (6)0.028 (6)0.109 (11)0.0000.007 (7)0.000
C2000.047 (16)0.039 (13)0.09 (3)0.001 (10)0.015 (15)0.017 (16)
O20.087 (13)0.035 (10)0.150 (16)0.018 (7)0.080 (12)0.004 (10)
C5000.090 (17)0.068 (15)0.088 (15)0.002 (13)0.074 (14)0.005 (13)
C3000.062 (15)0.026 (12)0.18 (4)0.020 (11)0.08 (2)0.01 (2)
C4000.054 (17)0.06 (3)0.058 (15)0.015 (14)0.023 (13)0.004 (17)
Geometric parameters (Å, º) top
Cl11—C291.752 (8)C14—C151.523 (9)
Cl12—C291.749 (8)C15—C161.559 (8)
Cl13—C291.749 (7)C16—C171.566 (9)
O1—C281.277 (9)C17—C201.551 (9)
O1—C31.474 (7)C20—C211.516 (10)
N1—C281.291 (10)C20—C221.531 (9)
C28—C291.527 (9)C22—C231.534 (10)
C1—C101.530 (10)C23—C241.521 (9)
C1—C21.528 (9)C24—C251.519 (10)
C2—C31.502 (10)C25—C261.510 (9)
C3—C41.498 (11)C25—C271.544 (8)
C4—C51.519 (9)C100—O21.439 (10)
C5—C61.306 (10)C100—O2i1.439 (10)
C5—C101.544 (9)C100—C400i1.543 (10)
C6—C71.506 (9)C100—C4001.543 (10)
C7—C81.536 (8)C100—C2001.544 (10)
C8—C141.518 (8)C100—C200i1.544 (10)
C8—C91.529 (9)C100—C300i1.550 (10)
C9—C101.549 (8)C100—C3001.550 (10)
C9—C111.557 (8)C200—C400i0.37 (10)
C10—C191.544 (10)O2—C300i0.66 (2)
C11—C121.548 (9)O2—C5001.446 (10)
C12—C131.527 (9)C500—C300i0.98 (3)
C13—C171.546 (8)C300—O2i0.66 (2)
C13—C181.544 (10)C300—C500i0.98 (3)
C13—C141.552 (8)C400—C200i0.37 (10)
C28—O1—C3118.8 (5)C25—C24—C23115.5 (6)
O1—C28—N1123.1 (7)C26—C25—C24117.3 (7)
O1—C28—C29113.2 (6)C26—C25—C27111.5 (7)
N1—C28—C29123.6 (6)C24—C25—C27110.0 (7)
C10—C1—C2114.4 (6)C28—C29—Cl12107.7 (6)
C3—C2—C1108.6 (5)C28—C29—Cl13111.0 (5)
O1—C3—C4110.3 (6)Cl12—C29—Cl13109.6 (4)
O1—C3—C2107.5 (5)C28—C29—Cl11111.7 (5)
C4—C3—C2111.7 (6)Cl12—C29—Cl11107.6 (4)
C3—C4—C5110.2 (6)Cl13—C29—Cl11109.1 (4)
C6—C5—C4120.3 (6)O2—C100—O2i82.9 (17)
C6—C5—C10123.7 (6)O2—C100—C400i130.8 (19)
C4—C5—C10116.0 (6)O2i—C100—C400i106 (2)
C5—C6—C7124.3 (6)O2—C100—C400106 (2)
C6—C7—C8113.6 (5)O2i—C100—C400130.8 (19)
C14—C8—C9109.5 (5)C400i—C100—C400103 (4)
C14—C8—C7110.8 (5)O2—C100—C200117 (2)
C9—C8—C7110.0 (5)O2i—C100—C200104 (2)
C8—C9—C10112.4 (5)C400i—C100—C20014 (4)
C8—C9—C11111.7 (5)C400—C100—C200112.5 (14)
C10—C9—C11113.3 (5)O2—C100—C200i104 (2)
C1—C10—C5109.9 (5)O2i—C100—C200i117 (2)
C1—C10—C19109.4 (6)C400i—C100—C200i112.5 (14)
C5—C10—C19107.9 (6)C400—C100—C200i14 (4)
C1—C10—C9108.5 (5)C200—C100—C200i124 (4)
C5—C10—C9109.3 (5)O2—C100—C300i25.1 (9)
C19—C10—C9111.9 (5)O2i—C100—C300i98.1 (15)
C12—C11—C9113.9 (5)C400i—C100—C300i107 (2)
C13—C12—C11110.3 (6)C400—C100—C300i110 (2)
C12—C13—C17115.3 (5)C200—C100—C300i94 (2)
C12—C13—C18111.2 (6)C200i—C100—C300i114 (2)
C17—C13—C18110.1 (5)O2—C100—C30098.1 (15)
C12—C13—C14106.3 (5)O2i—C100—C30025.1 (9)
C17—C13—C14101.2 (5)C400i—C100—C300110 (2)
C18—C13—C14112.3 (5)C400—C100—C300107 (2)
C15—C14—C8117.8 (5)C200—C100—C300114 (2)
C15—C14—C13103.3 (5)C200i—C100—C30094 (2)
C8—C14—C13115.3 (5)C300i—C100—C300119 (2)
C14—C15—C16103.2 (5)C400i—C200—C10083 (3)
C15—C16—C17107.2 (5)C300i—O2—C10086.9 (14)
C13—C17—C20118.6 (5)C300i—O2—C50034 (3)
C13—C17—C16103.1 (5)C100—O2—C500107.5 (17)
C20—C17—C16111.9 (5)C300i—C500—O222.4 (17)
C21—C20—C22110.1 (6)O2i—C300—C500i123 (5)
C21—C20—C17113.4 (5)O2i—C300—C10068.0 (12)
C22—C20—C17110.1 (6)C500i—C300—C100133 (3)
C20—C22—C23114.0 (6)C200i—C400—C10083 (3)
C22—C23—C24111.9 (6)
Symmetry code: (i) x, y, z.
 

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