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In the main mol­ecule of the title compound, C22H12Cl2O4·0.25C6H12, the rings are planar. The asymmetric unit contains only one-half of a half-occupancy cyclo­hexane ring (site symmetry 111) and has a distorted chair conformation. Intra­molecular C—H...Cl and C—H...O hydrogen bonds may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602410X/hk2067sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602410X/hk2067Isup2.hkl
Contains datablock I

CCDC reference: 613731

Key indicators

  • Single-crystal X-ray study
  • T = 315 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.086
  • wR factor = 0.229
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.66 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C17 -C22 1.36 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C22 H12 Cl2 O4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); 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.

3,7-Dichloro-3,7-diphenylbenzo[1,2 - c;4,5 - c']difuran-1,5(3H,7H)-dione cyclohexane 0.25-solvate top
Crystal data top
C22H12Cl4O8·0.25C6H12F(000) = 1776
Mr = 432.26Dx = 1.321 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 10.817 (2) Åθ = 9–12°
b = 13.679 (3) ŵ = 0.33 mm1
c = 29.370 (6) ÅT = 315 K
V = 4345.8 (15) Å3Block, colourless
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.4°
ω/2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 016
Tmin = 0.909, Tmax = 0.938l = 036
4254 measured reflections3 standard reflections every 120 min
4254 independent reflections intensity decay: none
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.07P)2 + 6P]
where P = (Fo2 + 2Fc2)/3
4254 reflections(Δ/σ)max = 0.007
280 parametersΔρmax = 0.78 e Å3
21 restraintsΔρmin = 0.29 e Å3
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)
Cl10.22613 (15)0.23586 (15)0.10989 (6)0.0747 (6)
Cl20.25046 (17)0.16080 (14)0.27214 (5)0.0679 (5)
O10.1629 (4)0.0509 (3)0.10193 (14)0.0560 (12)
O20.1269 (4)0.0714 (3)0.15031 (16)0.0617 (12)
O30.3138 (5)0.3540 (3)0.15162 (17)0.0746 (14)
O40.3551 (4)0.2289 (3)0.19925 (14)0.0570 (11)
C10.1507 (8)0.1805 (7)0.0351 (3)0.099 (3)
H1A0.21250.19800.05550.119*
C20.0360 (8)0.1570 (6)0.0506 (3)0.081 (2)
H2A0.01790.16160.08150.097*
C30.0510 (7)0.1272 (6)0.0210 (3)0.083 (3)
H3A0.12800.10750.03170.100*
C40.0270 (6)0.1258 (5)0.0241 (2)0.069 (2)
H4A0.08880.10610.04410.082*
C50.0879 (5)0.1531 (5)0.04154 (19)0.0534 (17)
C60.1749 (7)0.1785 (6)0.0104 (2)0.080 (2)
H6A0.25370.19500.02050.096*
C70.1137 (5)0.1452 (5)0.0918 (2)0.0528 (16)
C80.0985 (5)0.0083 (5)0.1362 (2)0.0489 (15)
C90.0049 (5)0.0718 (4)0.1493 (2)0.0430 (14)
C100.0964 (5)0.0574 (4)0.18183 (19)0.0440 (15)
H10A0.09940.00220.20030.053*
C110.1831 (5)0.1321 (4)0.18459 (19)0.0396 (13)
C120.1759 (5)0.2144 (4)0.15759 (19)0.0418 (14)
C130.0836 (5)0.2310 (4)0.1260 (2)0.0480 (15)
H13A0.07950.28770.10860.058*
C140.0028 (5)0.1557 (4)0.12231 (18)0.0425 (14)
C150.2840 (6)0.2767 (5)0.1676 (2)0.0533 (17)
C160.2980 (5)0.1394 (5)0.2140 (2)0.0492 (16)
C170.3871 (5)0.0558 (5)0.2105 (2)0.0502 (16)
C180.4784 (6)0.0568 (6)0.1783 (2)0.068 (2)
H18A0.48740.11140.15970.081*
C190.5570 (7)0.0212 (7)0.1728 (3)0.088 (3)
H19A0.61810.01970.15060.106*
C200.5445 (7)0.1000 (7)0.2001 (3)0.084 (3)
H20A0.59840.15250.19680.101*
C210.4546 (7)0.1038 (6)0.2321 (3)0.079 (2)
H21A0.44620.15850.25060.094*
C220.3759 (6)0.0255 (5)0.2367 (2)0.0602 (18)
H22A0.31340.02820.25840.072*
C230.0550 (16)0.4977 (14)0.0451 (6)0.109 (6)0.50
H23A0.10930.45300.06110.131*0.50
H23B0.03220.54880.06640.131*0.50
C240.0572 (15)0.4443 (12)0.0330 (5)0.102 (6)0.50
H24A0.03720.37520.03460.123*0.50
H24B0.11710.45690.05690.123*0.50
C250.1212 (12)0.4603 (11)0.0107 (5)0.074 (4)0.50
H25A0.19300.50090.00490.089*0.50
H25B0.15120.39750.02140.089*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0563 (10)0.1074 (15)0.0604 (10)0.0330 (10)0.0005 (9)0.0031 (10)
Cl20.0683 (11)0.0879 (13)0.0474 (9)0.0067 (10)0.0007 (9)0.0095 (9)
O10.039 (2)0.071 (3)0.058 (3)0.013 (2)0.010 (2)0.004 (2)
O20.048 (3)0.060 (3)0.078 (3)0.016 (2)0.002 (2)0.004 (3)
O30.084 (4)0.062 (3)0.078 (3)0.026 (3)0.006 (3)0.001 (3)
O40.048 (3)0.065 (3)0.058 (3)0.014 (2)0.008 (2)0.001 (2)
C10.092 (7)0.157 (9)0.048 (5)0.026 (6)0.018 (5)0.003 (5)
C20.080 (6)0.101 (6)0.061 (5)0.008 (5)0.015 (4)0.007 (5)
C30.056 (5)0.132 (8)0.061 (5)0.007 (5)0.003 (4)0.007 (5)
C40.051 (4)0.111 (6)0.043 (4)0.016 (4)0.008 (3)0.006 (4)
C50.033 (3)0.086 (5)0.041 (3)0.004 (3)0.006 (3)0.001 (3)
C60.053 (4)0.135 (7)0.053 (4)0.015 (5)0.005 (4)0.002 (5)
C70.035 (3)0.079 (5)0.045 (4)0.008 (3)0.006 (3)0.001 (3)
C80.032 (3)0.059 (4)0.056 (4)0.002 (3)0.004 (3)0.004 (3)
C90.028 (3)0.052 (4)0.049 (4)0.004 (3)0.001 (3)0.010 (3)
C100.035 (3)0.048 (4)0.048 (4)0.004 (3)0.002 (3)0.000 (3)
C110.032 (3)0.042 (3)0.044 (3)0.003 (3)0.001 (3)0.002 (3)
C120.039 (3)0.042 (3)0.044 (3)0.003 (3)0.003 (3)0.006 (3)
C130.047 (3)0.048 (4)0.049 (4)0.002 (3)0.002 (3)0.001 (3)
C140.032 (3)0.052 (4)0.044 (3)0.003 (3)0.003 (2)0.005 (3)
C150.057 (4)0.055 (4)0.047 (4)0.013 (4)0.005 (3)0.011 (3)
C160.040 (3)0.061 (4)0.047 (4)0.011 (3)0.001 (3)0.001 (3)
C170.028 (3)0.062 (4)0.061 (4)0.002 (3)0.007 (3)0.008 (3)
C180.040 (4)0.091 (6)0.072 (5)0.002 (4)0.003 (4)0.009 (4)
C190.041 (5)0.120 (8)0.104 (7)0.007 (5)0.009 (4)0.031 (6)
C200.053 (5)0.089 (7)0.109 (8)0.018 (5)0.026 (5)0.041 (6)
C210.072 (6)0.061 (5)0.103 (7)0.005 (4)0.026 (5)0.011 (4)
C220.046 (4)0.070 (5)0.065 (5)0.004 (4)0.007 (3)0.009 (4)
C230.108 (10)0.136 (10)0.083 (9)0.009 (8)0.005 (8)0.003 (8)
C240.127 (10)0.098 (9)0.082 (8)0.040 (8)0.041 (7)0.035 (7)
C250.056 (7)0.063 (7)0.104 (9)0.018 (6)0.002 (7)0.005 (7)
Geometric parameters (Å, º) top
Cl1—C71.817 (6)C11—C161.517 (7)
Cl2—C161.808 (6)C12—C131.382 (7)
O1—C81.357 (7)C12—C151.476 (8)
O1—C71.426 (7)C13—C141.394 (8)
O2—C81.207 (7)C13—H13A0.9300
O3—C151.201 (7)C16—C171.500 (8)
O4—C151.372 (7)C17—C221.358 (8)
O4—C161.438 (7)C17—C181.367 (9)
C1—C21.361 (10)C18—C191.373 (10)
C1—C61.361 (10)C18—H18A0.9300
C1—H1A0.9300C19—C201.350 (11)
C2—C31.345 (10)C19—H19A0.9300
C2—H2A0.9300C20—C211.353 (11)
C3—C41.351 (9)C20—H20A0.9300
C3—H3A0.9300C21—C221.376 (9)
C4—C51.395 (7)C21—H21A0.9300
C4—H4A0.9300C22—H22A0.9300
C5—C61.358 (8)C23—C25i1.365 (19)
C5—C71.505 (8)C23—C241.460 (9)
C6—H6A0.9300C23—H23A0.9700
C7—C141.505 (7)C23—H23B0.9700
C8—C91.467 (8)C24—C251.475 (9)
C9—C101.389 (7)C24—H24A0.9700
C9—C141.399 (8)C24—H24B0.9700
C10—C111.389 (7)C25—C23i1.365 (19)
C10—H10A0.9300C25—H25A0.9700
C11—C121.379 (7)C25—H25B0.9700
C8—O1—C7110.6 (4)C9—C14—C7107.9 (5)
C15—O4—C16111.6 (4)O3—C15—O4122.2 (6)
C2—C1—C6120.1 (8)O3—C15—C12130.0 (6)
C2—C1—H1A120.0O4—C15—C12107.7 (5)
C6—C1—H1A120.0O4—C16—C17110.7 (5)
C3—C2—C1119.5 (8)O4—C16—C11103.7 (5)
C3—C2—H2A120.3C17—C16—C11115.9 (5)
C1—C2—H2A120.3O4—C16—Cl2105.6 (4)
C2—C3—C4120.3 (7)C17—C16—Cl2111.8 (5)
C2—C3—H3A119.9C11—C16—Cl2108.4 (4)
C4—C3—H3A119.9C22—C17—C18117.7 (7)
C3—C4—C5121.8 (6)C22—C17—C16121.9 (6)
C3—C4—H4A119.1C18—C17—C16120.3 (7)
C5—C4—H4A119.1C17—C18—C19121.4 (8)
C6—C5—C4116.1 (6)C17—C18—H18A119.3
C6—C5—C7123.4 (6)C19—C18—H18A119.3
C4—C5—C7120.4 (5)C20—C19—C18119.3 (8)
C5—C6—C1122.2 (7)C20—C19—H19A120.4
C5—C6—H6A118.9C18—C19—H19A120.4
C1—C6—H6A118.9C21—C20—C19121.0 (8)
O1—C7—C14105.1 (5)C21—C20—H20A119.5
O1—C7—C5109.8 (5)C19—C20—H20A119.5
C14—C7—C5115.4 (5)C20—C21—C22118.9 (8)
O1—C7—Cl1107.8 (4)C20—C21—H21A120.5
C14—C7—Cl1107.1 (4)C22—C21—H21A120.5
C5—C7—Cl1111.2 (4)C17—C22—C21121.7 (7)
O2—C8—O1120.8 (6)C17—C22—H22A119.1
O2—C8—C9129.7 (6)C21—C22—H22A119.1
O1—C8—C9109.4 (5)C25i—C23—C24117.8 (14)
C10—C9—C14123.3 (5)C25i—C23—H23A107.8
C10—C9—C8129.8 (6)C24—C23—H23A107.8
C14—C9—C8106.9 (5)C25i—C23—H23B107.9
C11—C10—C9114.6 (5)C24—C23—H23B107.8
C11—C10—H10A122.7H23A—C23—H23B107.2
C9—C10—H10A122.7C23—C24—C25121.8 (12)
C12—C11—C10121.9 (5)C23—C24—H24A106.9
C12—C11—C16108.6 (5)C25—C24—H24A106.9
C10—C11—C16129.4 (5)C23—C24—H24B106.9
C11—C12—C13124.1 (5)C25—C24—H24B106.9
C11—C12—C15108.2 (5)H24A—C24—H24B106.7
C13—C12—C15127.7 (6)C23i—C25—C24117.4 (11)
C12—C13—C14114.5 (5)C23i—C25—H25A107.9
C12—C13—H13A122.7C24—C25—H25A107.9
C14—C13—H13A122.7C23i—C25—H25B107.9
C13—C14—C9121.5 (5)C24—C25—H25B107.9
C13—C14—C7130.7 (6)H25A—C25—H25B107.2
C6—C1—C2—C33.3 (14)C8—C9—C14—C70.3 (6)
C1—C2—C3—C43.7 (14)O1—C7—C14—C13177.3 (6)
C2—C3—C4—C51.2 (13)C5—C7—C14—C1356.2 (9)
C3—C4—C5—C61.7 (12)Cl1—C7—C14—C1368.2 (7)
C3—C4—C5—C7176.5 (7)O1—C7—C14—C92.2 (6)
C4—C5—C6—C12.2 (13)C5—C7—C14—C9123.3 (6)
C7—C5—C6—C1176.8 (8)Cl1—C7—C14—C9112.3 (5)
C2—C1—C6—C50.3 (15)C16—O4—C15—O3178.4 (6)
C8—O1—C7—C143.4 (6)C16—O4—C15—C123.8 (6)
C8—O1—C7—C5128.1 (5)C11—C12—C15—O3179.4 (7)
C8—O1—C7—Cl1110.5 (4)C13—C12—C15—O31.4 (11)
C6—C5—C7—O184.6 (8)C11—C12—C15—O41.8 (6)
C4—C5—C7—O189.7 (7)C13—C12—C15—O4176.2 (5)
C6—C5—C7—C14156.9 (7)C15—O4—C16—C17129.0 (5)
C4—C5—C7—C1428.8 (10)C15—O4—C16—C114.0 (6)
C6—C5—C7—Cl134.6 (9)C15—O4—C16—Cl2109.9 (4)
C4—C5—C7—Cl1151.0 (6)C12—C11—C16—O42.8 (6)
C7—O1—C8—O2178.9 (6)C10—C11—C16—O4175.4 (5)
C7—O1—C8—C93.3 (6)C12—C11—C16—C17124.3 (6)
O2—C8—C9—C101.0 (11)C10—C11—C16—C1753.9 (8)
O1—C8—C9—C10178.5 (6)C12—C11—C16—Cl2109.1 (5)
O2—C8—C9—C14179.3 (6)C10—C11—C16—Cl272.7 (7)
O1—C8—C9—C141.8 (6)O4—C16—C17—C22154.9 (6)
C14—C9—C10—C112.0 (8)C11—C16—C17—C2287.4 (7)
C8—C9—C10—C11178.3 (6)Cl2—C16—C17—C2237.5 (7)
C9—C10—C11—C121.3 (8)O4—C16—C17—C1829.3 (8)
C9—C10—C11—C16176.7 (5)C11—C16—C17—C1888.4 (7)
C10—C11—C12—C130.4 (9)Cl2—C16—C17—C18146.7 (5)
C16—C11—C12—C13178.8 (5)C22—C17—C18—C190.5 (10)
C10—C11—C12—C15177.7 (5)C16—C17—C18—C19176.5 (6)
C16—C11—C12—C150.7 (6)C17—C18—C19—C200.6 (12)
C11—C12—C13—C141.5 (8)C18—C19—C20—C211.1 (12)
C15—C12—C13—C14176.3 (5)C19—C20—C21—C220.4 (12)
C12—C13—C14—C90.8 (8)C18—C17—C22—C211.3 (10)
C12—C13—C14—C7178.7 (5)C16—C17—C22—C21177.2 (6)
C10—C9—C14—C131.0 (9)C20—C21—C22—C170.8 (10)
C8—C9—C14—C13179.3 (5)C25i—C23—C24—C2520 (3)
C10—C9—C14—C7179.4 (5)C23—C24—C25—C23i20 (3)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···Cl10.932.703.076 (6)105
C18—H18A···O40.932.452.775 (9)101
C22—H22A···Cl20.932.703.069 (7)104
 

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