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In the mol­ecule of the title compound, C23H20ClFN2O4, the cyclo­hexene ring is not planar and has a flattened boat conformation. Inter­molecular C—H...O hydrogen bonds, linking the independent mol­ecules into dimers, may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040116/hk2141sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040116/hk2141Isup2.hkl
Contains datablock I

CCDC reference: 627797

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.150
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C3 - C4 ... 1.41 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

2-[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenoxy]-N-methyl-N-phenyl-acetamide top
Crystal data top
C23H20ClFN2O4F(000) = 920
Mr = 442.86Dx = 1.411 Mg m3
Monoclinic, P21/cMelting point: 434 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.008 (2) ÅCell parameters from 25 reflections
b = 15.213 (3) Åθ = 10–13°
c = 14.231 (3) ŵ = 0.23 mm1
β = 105.88 (3)°T = 294 K
V = 2084.0 (8) Å3Block, colourless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD4
diffractometer
2527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ω/2θ scansh = 1211
Absorption correction: ψ scan
(North et al., 1968)
k = 018
Tmin = 0.888, Tmax = 0.956l = 017
4087 measured reflections3 standard reflections every 120 min
4087 independent reflections intensity decay: none
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.07P)2 + 0.4P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4087 reflectionsΔρmax = 0.30 e Å3
280 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.039 (3)
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
Cl0.50104 (11)0.22414 (6)0.11029 (7)0.0790 (3)
F0.8907 (2)0.01113 (13)0.24853 (13)0.0744 (6)
O10.8933 (2)0.05173 (14)0.07800 (15)0.0597 (6)
O20.8099 (2)0.16244 (14)0.19923 (15)0.0584 (6)
O30.5027 (2)0.14139 (12)0.06958 (13)0.0497 (5)
O40.7093 (2)0.19489 (14)0.14616 (16)0.0640 (6)
N10.8472 (2)0.08038 (15)0.07070 (16)0.0457 (6)
N20.6676 (2)0.08793 (16)0.25982 (17)0.0505 (6)
C10.9128 (3)0.2266 (2)0.0807 (2)0.0531 (8)
C20.9336 (4)0.3189 (2)0.1123 (3)0.0703 (10)
H2A0.84450.34540.10980.084*
H2B0.99090.32140.17930.084*
C31.0016 (6)0.3689 (3)0.0485 (3)0.1155 (17)
H3A1.10080.36830.07940.139*
H3B0.97130.42960.04760.139*
C40.9810 (6)0.3423 (3)0.0491 (3)0.1072 (16)
H4A0.89010.36310.08610.129*
H4B1.04900.37250.07450.129*
C50.9892 (4)0.2467 (2)0.0703 (3)0.0708 (10)
H5A1.08470.23090.06560.085*
H5B0.93370.23440.13630.085*
C60.9381 (3)0.1939 (2)0.0007 (2)0.0505 (7)
C70.8941 (3)0.1011 (2)0.0113 (2)0.0462 (7)
C80.8514 (3)0.15688 (19)0.1278 (2)0.0476 (7)
C90.7732 (3)0.00308 (18)0.0806 (2)0.0439 (7)
C100.6763 (3)0.03096 (18)0.0006 (2)0.0439 (7)
H10A0.66440.00440.06120.053*
C110.5977 (3)0.10320 (18)0.0073 (2)0.0428 (6)
C120.6113 (3)0.13993 (18)0.0993 (2)0.0485 (7)
C130.7085 (3)0.1079 (2)0.1799 (2)0.0551 (8)
H13A0.71840.13310.24100.066*
C140.7911 (3)0.0383 (2)0.1694 (2)0.0514 (7)
C160.5017 (3)0.11152 (19)0.16479 (19)0.0462 (7)
H16A0.42380.13770.21270.055*
H16B0.48990.04820.16820.055*
C170.6355 (3)0.13566 (19)0.1887 (2)0.0457 (7)
C180.7949 (4)0.1085 (3)0.2856 (3)0.0846 (12)
H18A0.84100.15680.24640.127*
H18B0.77300.12440.35340.127*
H18C0.85480.05810.27400.127*
C190.5840 (3)0.01744 (19)0.3112 (2)0.0469 (7)
C200.6347 (4)0.0672 (2)0.2989 (2)0.0645 (9)
H20A0.72140.07850.25600.077*
C210.5565 (5)0.1349 (2)0.3503 (3)0.0772 (11)
H21A0.59160.19180.34260.093*
C220.4276 (5)0.1195 (2)0.4128 (3)0.0746 (11)
H22A0.37500.16580.44650.090*
C230.3770 (4)0.0354 (2)0.4250 (3)0.0689 (10)
H23A0.28940.02470.46690.083*
C240.4549 (4)0.0336 (2)0.3754 (2)0.0579 (8)
H24A0.42090.09070.38520.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.1187 (8)0.0601 (5)0.0634 (5)0.0319 (5)0.0336 (5)0.0101 (4)
F0.0868 (14)0.0774 (13)0.0484 (11)0.0169 (11)0.0008 (10)0.0045 (9)
O10.0774 (15)0.0577 (13)0.0517 (12)0.0042 (11)0.0309 (11)0.0103 (10)
O20.0684 (14)0.0627 (14)0.0511 (12)0.0157 (11)0.0283 (11)0.0130 (10)
O30.0640 (13)0.0451 (11)0.0422 (11)0.0140 (10)0.0181 (10)0.0019 (9)
O40.0734 (15)0.0506 (13)0.0682 (15)0.0161 (12)0.0200 (12)0.0137 (11)
N10.0584 (15)0.0415 (13)0.0419 (13)0.0103 (11)0.0216 (11)0.0052 (10)
N20.0567 (15)0.0493 (14)0.0500 (14)0.0060 (12)0.0223 (12)0.0064 (12)
C10.0613 (18)0.0492 (17)0.0543 (18)0.0111 (15)0.0253 (15)0.0053 (14)
C20.092 (2)0.054 (2)0.074 (2)0.0185 (19)0.038 (2)0.0094 (17)
C30.205 (5)0.067 (3)0.098 (3)0.036 (3)0.080 (3)0.003 (2)
C40.180 (5)0.069 (2)0.096 (3)0.032 (3)0.077 (3)0.001 (2)
C50.096 (3)0.065 (2)0.063 (2)0.0146 (19)0.0408 (19)0.0020 (17)
C60.0585 (18)0.0490 (17)0.0472 (16)0.0074 (14)0.0199 (14)0.0003 (13)
C70.0504 (17)0.0510 (18)0.0406 (15)0.0013 (14)0.0179 (13)0.0000 (14)
C80.0516 (17)0.0494 (17)0.0427 (16)0.0090 (14)0.0148 (14)0.0058 (14)
C90.0558 (17)0.0371 (15)0.0410 (15)0.0007 (13)0.0168 (13)0.0013 (12)
C100.0581 (18)0.0368 (15)0.0409 (15)0.0009 (13)0.0203 (14)0.0035 (12)
C110.0519 (16)0.0358 (15)0.0439 (15)0.0000 (13)0.0183 (13)0.0025 (12)
C120.073 (2)0.0357 (15)0.0431 (16)0.0001 (14)0.0255 (15)0.0061 (13)
C130.079 (2)0.0471 (18)0.0400 (16)0.0004 (16)0.0177 (16)0.0084 (14)
C140.0614 (19)0.0490 (18)0.0395 (16)0.0001 (15)0.0066 (15)0.0003 (14)
C160.0549 (17)0.0451 (16)0.0393 (15)0.0048 (14)0.0145 (13)0.0028 (13)
C170.0561 (18)0.0381 (16)0.0427 (16)0.0023 (14)0.0131 (14)0.0029 (13)
C180.073 (2)0.101 (3)0.093 (3)0.023 (2)0.046 (2)0.025 (2)
C190.0617 (19)0.0422 (16)0.0440 (16)0.0025 (15)0.0264 (15)0.0029 (13)
C200.081 (2)0.055 (2)0.063 (2)0.0085 (18)0.0289 (18)0.0042 (17)
C210.112 (3)0.044 (2)0.086 (3)0.005 (2)0.047 (3)0.0069 (19)
C220.108 (3)0.053 (2)0.076 (3)0.029 (2)0.047 (2)0.0212 (19)
C230.076 (2)0.070 (2)0.060 (2)0.0148 (19)0.0191 (18)0.0112 (18)
C240.071 (2)0.0427 (17)0.0601 (19)0.0050 (16)0.0179 (17)0.0033 (15)
Geometric parameters (Å, º) top
Cl—C121.726 (3)C16—C171.514 (4)
F—C141.348 (3)C19—C201.377 (4)
O1—C71.209 (4)C19—C241.385 (5)
O2—C81.202 (4)C20—C211.377 (5)
O3—C111.367 (3)C21—C221.372 (7)
O3—C161.427 (3)C22—C231.369 (5)
O4—C171.216 (4)C23—C241.381 (5)
N1—C71.408 (4)C2—H2A0.9704
N1—C81.413 (4)C2—H2B0.9696
N1—C91.417 (4)C3—H3A0.9696
N2—C171.354 (4)C3—H3B0.9709
N2—C181.453 (5)C4—H4A0.9710
N2—C191.432 (4)C4—H4B0.9693
C1—C21.472 (4)C5—H5A0.9699
C1—C61.347 (4)C5—H5B0.9696
C1—C81.476 (4)C10—H10A0.9300
C2—C31.485 (6)C13—H13A0.9304
C3—C41.407 (6)C16—H16A0.9697
C4—C51.492 (6)C16—H16B0.9701
C5—C61.471 (5)C18—H18A0.9608
C6—C71.474 (4)C18—H18B0.9601
C9—C101.389 (4)C18—H18C0.9593
C9—C141.379 (4)C20—H20A0.9302
C10—C111.374 (4)C21—H21A0.9293
C11—C121.395 (4)C22—H22A0.9301
C12—C131.374 (4)C23—H23A0.9298
C13—C141.376 (4)C24—H24A0.9294
C11—O3—C16116.6 (2)C22—C23—C24120.5 (4)
C7—N1—C8109.1 (2)C19—C24—C23119.8 (3)
C7—N1—C9124.8 (2)C1—C2—H2A109.48
C8—N1—C9124.1 (2)C1—C2—H2B109.51
C17—N2—C18118.5 (3)C3—C2—H2A109.58
C17—N2—C19124.0 (2)C3—C2—H2B109.54
C18—N2—C19117.6 (3)H2A—C2—H2B108.06
C2—C1—C6124.8 (3)C2—C3—H3A107.55
C2—C1—C8126.1 (3)C2—C3—H3B107.55
C6—C1—C8109.0 (3)C4—C3—H3A107.48
C1—C2—C3110.6 (3)C4—C3—H3B107.44
C2—C3—C4119.2 (4)H3A—C3—H3B106.99
C3—C4—C5118.6 (4)C3—C4—H4A107.71
C4—C5—C6110.3 (3)C3—C4—H4B107.68
C1—C6—C5124.0 (3)C5—C4—H4A107.65
C1—C6—C7108.7 (3)C5—C4—H4B107.67
C5—C6—C7127.1 (3)H4A—C4—H4B107.01
O1—C7—N1125.4 (3)C4—C5—H5A109.59
O1—C7—C6127.8 (3)C4—C5—H5B109.59
N1—C7—C6106.7 (2)C6—C5—H5A109.62
O2—C8—N1125.6 (3)C6—C5—H5B109.52
O2—C8—C1128.1 (3)H5A—C5—H5B108.15
N1—C8—C1106.3 (2)C9—C10—H10A119.50
N1—C9—C10119.4 (2)C11—C10—H10A119.50
N1—C9—C14122.0 (3)C12—C13—H13A120.26
C10—C9—C14118.6 (3)C14—C13—H13A120.32
C9—C10—C11121.0 (3)O3—C16—H16A109.41
O3—C11—C10124.2 (2)O3—C16—H16B109.45
O3—C11—C12116.7 (2)C17—C16—H16A109.43
C10—C11—C12119.1 (3)C17—C16—H16B109.43
Cl—C12—C11118.8 (2)H16A—C16—H16B108.01
Cl—C12—C13120.8 (2)N2—C18—H18A109.45
C11—C12—C13120.4 (3)N2—C18—H18B109.46
C12—C13—C14119.4 (3)N2—C18—H18C109.52
F—C14—C9120.4 (3)H18A—C18—H18B109.40
F—C14—C13118.3 (2)H18A—C18—H18C109.46
C9—C14—C13121.3 (3)H18B—C18—H18C109.53
O3—C16—C17111.1 (2)C19—C20—H20A120.08
O4—C17—N2122.2 (3)C21—C20—H20A120.20
O4—C17—C16121.4 (3)C20—C21—H21A119.51
N2—C17—C16116.3 (2)C22—C21—H21A119.57
N2—C19—C20119.5 (3)C21—C22—H22A120.27
N2—C19—C24120.9 (3)C23—C22—H22A120.31
C20—C19—C24119.6 (3)C22—C23—H23A119.73
C19—C20—C21119.7 (3)C24—C23—H23A119.74
C20—C21—C22120.9 (3)C19—C24—H24A120.13
C21—C22—C23119.4 (3)C23—C24—H24A120.10
C6—C1—C2—C36.5 (6)C16—O3—C11—C12172.0 (2)
C8—C1—C2—C3178.5 (4)C9—C10—C11—O3178.5 (2)
C1—C2—C3—C428.4 (7)C9—C10—C11—C123.2 (4)
C2—C3—C4—C544.1 (8)O3—C11—C12—C13177.2 (3)
C3—C4—C5—C633.0 (6)C10—C11—C12—C134.3 (4)
C2—C1—C6—C50.6 (5)O3—C11—C12—Cl4.4 (4)
C8—C1—C6—C5175.1 (3)C10—C11—C12—Cl174.1 (2)
C2—C1—C6—C7175.5 (3)C11—C12—C13—C141.0 (5)
C8—C1—C6—C70.2 (4)Cl—C12—C13—C14177.3 (2)
C4—C5—C6—C111.5 (5)C12—C13—C14—F176.5 (3)
C4—C5—C6—C7162.5 (4)C12—C13—C14—C93.6 (5)
C8—N1—C7—O1174.1 (3)C10—C9—C14—F175.4 (3)
C9—N1—C7—O19.8 (5)N1—C9—C14—F6.7 (4)
C8—N1—C7—C63.8 (3)C10—C9—C14—C134.7 (4)
C9—N1—C7—C6168.1 (3)N1—C9—C14—C13173.3 (3)
C1—C6—C7—O1175.4 (3)C11—O3—C16—C1765.8 (3)
C5—C6—C7—O10.7 (5)C19—N2—C17—O4179.6 (3)
C1—C6—C7—N12.4 (3)C18—N2—C17—O40.1 (4)
C5—C6—C7—N1177.1 (3)C19—N2—C17—C160.6 (4)
C7—N1—C8—O2175.0 (3)C18—N2—C17—C16179.9 (3)
C9—N1—C8—O210.5 (5)O3—C16—C17—O421.3 (4)
C7—N1—C8—C13.6 (3)O3—C16—C17—N2158.9 (2)
C9—N1—C8—C1168.1 (3)C17—N2—C19—C20113.3 (3)
C6—C1—C8—O2176.5 (3)C18—N2—C19—C2066.2 (4)
C2—C1—C8—O20.9 (5)C17—N2—C19—C2468.8 (4)
C6—C1—C8—N12.1 (3)C18—N2—C19—C24111.7 (4)
C2—C1—C8—N1177.7 (3)C24—C19—C20—C210.2 (5)
C7—N1—C9—C14145.0 (3)N2—C19—C20—C21178.1 (3)
C8—N1—C9—C1452.9 (4)C19—C20—C21—C221.0 (5)
C7—N1—C9—C1037.1 (4)C20—C21—C22—C230.9 (6)
C8—N1—C9—C10125.0 (3)C21—C22—C23—C240.4 (5)
C14—C9—C10—C111.3 (4)C22—C23—C24—C191.5 (5)
N1—C9—C10—C11176.7 (2)C20—C19—C24—C231.4 (5)
C16—O3—C11—C109.7 (4)N2—C19—C24—C23179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16A···O2i0.972.433.119 (4)128
Symmetry code: (i) x+1, y, z.
 

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