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In the title compound, C18H10Cl2O2, the tetra­hydro­benzene ring adopts a boat conformation, and the cyclo­butene ring is almost coplanar with the attached phenyl ring. There are two intramolecular C—H...O interactions, each forming a five-membered ring. The crystal structure is stabilized by intermolecular C—H...O and π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024012/wn6192sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024012/wn6192Isup2.hkl
Contains datablock I

CCDC reference: 227025

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.128
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.97
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H10 Cl2 O2
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

2a,8a-Dichloro-2a,8a-dihydro-1-phenyldichlorocyclobuta[b]naphthalene-3,8-dione top
Crystal data top
C18H10Cl2O2Z = 2
Mr = 329.16F(000) = 336
Triclinic, P1Dx = 1.508 Mg m3
a = 7.1114 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3052 (8) ÅCell parameters from 2166 reflections
c = 13.8250 (13) Åθ = 2.7–28.3°
α = 77.338 (2)°µ = 0.45 mm1
β = 81.395 (2)°T = 293 K
γ = 65.793 (2)°Block, colourless
V = 724.98 (12) Å30.42 × 0.40 × 0.06 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2482 independent reflections
Radiation source: fine-focus sealed tube2009 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.7°
ω scansh = 88
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 99
Tmin = 0.833, Tmax = 0.974l = 1613
3542 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) = 0.128All H-atom parameters refined
S = 1.15 w = 1/[σ2(Fo2) + (0.055P)2 + 0.345P]
where P = (Fo2 + 2Fc2)/3
2482 reflections(Δ/σ)max < 0.001
239 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.24 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*/Ueq
Cl10.32682 (15)0.85046 (11)0.27295 (6)0.0573 (3)
Cl20.56105 (14)1.10013 (13)0.17250 (7)0.0629 (3)
O10.2362 (3)0.8796 (3)0.48039 (16)0.0460 (5)
O20.5347 (4)1.3570 (4)0.29171 (18)0.0621 (7)
C10.2478 (4)1.1596 (4)0.4792 (2)0.0346 (6)
C20.1764 (5)1.1637 (5)0.5779 (2)0.0442 (7)
C30.1704 (5)1.2970 (5)0.6243 (3)0.0534 (8)
C40.2368 (5)1.4299 (5)0.5715 (3)0.0514 (8)
C50.3105 (5)1.4264 (4)0.4749 (3)0.0443 (7)
C60.3201 (4)1.2916 (4)0.4267 (2)0.0348 (6)
C70.4176 (4)1.2829 (4)0.3253 (2)0.0396 (7)
C80.3560 (4)1.1879 (4)0.2610 (2)0.0376 (6)
C90.1428 (4)1.3048 (4)0.2212 (2)0.0380 (7)
C100.0564 (5)1.1965 (4)0.2751 (2)0.0395 (7)
C110.2482 (4)1.0549 (4)0.3185 (2)0.0367 (6)
C120.2473 (4)1.0154 (4)0.4322 (2)0.0345 (6)
C130.0726 (5)1.4746 (4)0.1534 (2)0.0412 (7)
C140.1308 (6)1.5554 (4)0.1294 (2)0.0516 (8)
C150.1983 (8)1.7140 (5)0.0618 (3)0.0681 (11)
C160.0657 (9)1.7923 (5)0.0191 (3)0.0750 (13)
C170.1396 (10)1.7154 (6)0.0421 (3)0.0784 (13)
C180.2105 (7)1.5564 (5)0.1095 (3)0.0582 (9)
H20.136 (4)1.074 (4)0.611 (2)0.036 (8)*
H30.097 (5)1.301 (4)0.697 (2)0.051 (9)*
H40.243 (5)1.523 (5)0.602 (3)0.058 (10)*
H50.351 (5)1.509 (5)0.438 (2)0.047 (9)*
H100.080 (5)1.204 (4)0.284 (2)0.049 (9)*
H140.237 (6)1.492 (5)0.159 (3)0.071 (11)*
H150.345 (7)1.766 (6)0.044 (3)0.088 (14)*
H160.122 (6)1.898 (5)0.028 (3)0.066 (11)*
H170.233 (6)1.762 (5)0.011 (3)0.067 (11)*
H180.351 (6)1.497 (5)0.124 (3)0.068 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0764 (6)0.0433 (5)0.0581 (5)0.0251 (4)0.0016 (4)0.0192 (4)
Cl20.0542 (5)0.0671 (6)0.0563 (6)0.0190 (4)0.0235 (4)0.0167 (4)
O10.0523 (13)0.0382 (11)0.0504 (13)0.0255 (10)0.0032 (10)0.0020 (10)
O20.0626 (15)0.0850 (18)0.0581 (15)0.0548 (15)0.0023 (12)0.0038 (13)
C10.0315 (14)0.0347 (15)0.0368 (15)0.0129 (12)0.0034 (12)0.0037 (12)
C20.0422 (17)0.0495 (19)0.0426 (18)0.0217 (15)0.0002 (14)0.0065 (15)
C30.0484 (19)0.065 (2)0.048 (2)0.0191 (17)0.0005 (15)0.0212 (17)
C40.0443 (18)0.052 (2)0.063 (2)0.0140 (16)0.0080 (16)0.0265 (17)
C50.0401 (17)0.0387 (17)0.061 (2)0.0199 (14)0.0113 (15)0.0076 (15)
C60.0262 (14)0.0356 (15)0.0436 (16)0.0135 (12)0.0062 (12)0.0036 (12)
C70.0310 (15)0.0422 (16)0.0475 (18)0.0203 (13)0.0046 (13)0.0018 (13)
C80.0332 (15)0.0428 (16)0.0358 (15)0.0177 (13)0.0059 (12)0.0051 (12)
C90.0417 (16)0.0409 (16)0.0336 (15)0.0176 (13)0.0009 (12)0.0088 (12)
C100.0330 (16)0.0466 (17)0.0426 (17)0.0206 (14)0.0038 (13)0.0040 (13)
C110.0398 (16)0.0330 (14)0.0413 (16)0.0184 (12)0.0007 (12)0.0072 (12)
C120.0267 (14)0.0337 (15)0.0416 (16)0.0119 (12)0.0021 (11)0.0037 (12)
C130.0567 (19)0.0377 (16)0.0304 (15)0.0197 (14)0.0001 (13)0.0081 (12)
C140.066 (2)0.0421 (18)0.0418 (18)0.0136 (17)0.0106 (16)0.0088 (14)
C150.096 (3)0.043 (2)0.054 (2)0.010 (2)0.022 (2)0.0076 (17)
C160.126 (4)0.037 (2)0.051 (2)0.020 (2)0.021 (2)0.0012 (17)
C170.129 (4)0.054 (2)0.062 (3)0.056 (3)0.005 (3)0.001 (2)
C180.075 (3)0.054 (2)0.053 (2)0.036 (2)0.0023 (19)0.0035 (17)
Geometric parameters (Å, º) top
Cl1—C111.782 (3)C8—C111.602 (4)
Cl2—C81.772 (3)C9—C101.328 (4)
O1—C121.205 (3)C9—C131.450 (4)
O2—C71.211 (3)C10—C111.491 (4)
C1—C21.387 (4)C10—H100.94 (3)
C1—C61.413 (4)C11—C121.533 (4)
C1—C121.483 (4)C13—C141.380 (5)
C2—C31.379 (5)C13—C181.406 (5)
C2—H20.92 (3)C14—C151.383 (5)
C3—C41.394 (5)C14—H141.07 (4)
C3—H31.07 (3)C15—C161.353 (6)
C4—C51.362 (5)C15—H151.00 (5)
C4—H40.98 (4)C16—C171.388 (7)
C5—C61.397 (4)C16—H160.94 (4)
C5—H50.88 (3)C17—C181.386 (6)
C6—C71.470 (4)C17—H170.91 (4)
C7—C81.521 (4)C18—H180.95 (4)
C8—C91.534 (4)
C2—C1—C6119.1 (3)C9—C10—C1197.1 (2)
C2—C1—C12118.8 (3)C9—C10—H10132.5 (19)
C6—C1—C12122.1 (2)C11—C10—H10130 (2)
C3—C2—C1120.9 (3)C10—C11—C12116.3 (2)
C3—C2—H2121.9 (18)C10—C11—C884.6 (2)
C1—C2—H2117.2 (18)C12—C11—C8116.7 (2)
C2—C3—C4119.8 (3)C10—C11—Cl1112.6 (2)
C2—C3—H3116.7 (17)C12—C11—Cl1109.58 (19)
C4—C3—H3123.0 (17)C8—C11—Cl1115.34 (19)
C5—C4—C3120.1 (3)O1—C12—C1122.2 (3)
C5—C4—H4117 (2)O1—C12—C11121.9 (2)
C3—C4—H4123 (2)C1—C12—C11115.8 (2)
C4—C5—C6121.1 (3)C14—C13—C18119.3 (3)
C4—C5—H5123 (2)C14—C13—C9119.8 (3)
C6—C5—H5116 (2)C18—C13—C9120.9 (3)
C5—C6—C1119.0 (3)C13—C14—C15120.5 (4)
C5—C6—C7119.5 (3)C13—C14—H14121 (2)
C1—C6—C7121.4 (2)C15—C14—H14119 (2)
O2—C7—C6121.5 (3)C16—C15—C14120.3 (4)
O2—C7—C8120.6 (3)C16—C15—H15121 (2)
C6—C7—C8117.8 (2)C14—C15—H15118 (3)
C7—C8—C9111.3 (2)C15—C16—C17120.8 (4)
C7—C8—C11116.2 (2)C15—C16—H16115 (2)
C9—C8—C1184.9 (2)C17—C16—H16124 (2)
C7—C8—Cl2110.05 (19)C18—C17—C16119.9 (4)
C9—C8—Cl2116.8 (2)C18—C17—H17118 (3)
C11—C8—Cl2115.7 (2)C16—C17—H17122 (2)
C10—C9—C13136.0 (3)C17—C18—C13119.3 (4)
C10—C9—C893.2 (2)C17—C18—H18122 (2)
C13—C9—C8130.7 (3)C13—C18—H18119 (2)
C6—C1—C2—C31.7 (4)C7—C8—C11—C10107.9 (3)
C12—C1—C2—C3178.8 (3)C9—C8—C11—C103.35 (19)
C1—C2—C3—C40.0 (5)Cl2—C8—C11—C10120.7 (2)
C2—C3—C4—C51.1 (5)C7—C8—C11—C128.8 (3)
C3—C4—C5—C60.4 (5)C9—C8—C11—C12120.1 (2)
C4—C5—C6—C11.3 (4)Cl2—C8—C11—C12122.6 (2)
C4—C5—C6—C7174.6 (3)C7—C8—C11—Cl1139.6 (2)
C2—C1—C6—C52.3 (4)C9—C8—C11—Cl1109.1 (2)
C12—C1—C6—C5178.2 (2)Cl2—C8—C11—Cl18.2 (3)
C2—C1—C6—C7173.5 (3)C2—C1—C12—O118.5 (4)
C12—C1—C6—C76.0 (4)C6—C1—C12—O1161.1 (3)
C5—C6—C7—O219.2 (4)C2—C1—C12—C11157.8 (3)
C1—C6—C7—O2156.6 (3)C6—C1—C12—C1122.6 (4)
C5—C6—C7—C8156.9 (3)C10—C11—C12—O1107.6 (3)
C1—C6—C7—C827.3 (4)C8—C11—C12—O1154.9 (3)
O2—C7—C8—C999.8 (3)Cl1—C11—C12—O121.5 (3)
C6—C7—C8—C976.3 (3)C10—C11—C12—C168.7 (3)
O2—C7—C8—C11165.3 (3)C8—C11—C12—C128.8 (3)
C6—C7—C8—C1118.6 (4)Cl1—C11—C12—C1162.20 (19)
O2—C7—C8—Cl231.3 (3)C10—C9—C13—C143.2 (5)
C6—C7—C8—Cl2152.6 (2)C8—C9—C13—C14179.3 (3)
C7—C8—C9—C10112.4 (3)C10—C9—C13—C18178.4 (3)
C11—C8—C9—C103.8 (2)C8—C9—C13—C182.4 (5)
Cl2—C8—C9—C10120.1 (2)C18—C13—C14—C150.9 (5)
C7—C8—C9—C1364.9 (4)C9—C13—C14—C15177.5 (3)
C11—C8—C9—C13179.0 (3)C13—C14—C15—C160.5 (5)
Cl2—C8—C9—C1362.7 (4)C14—C15—C16—C170.1 (6)
C13—C9—C10—C11178.9 (3)C15—C16—C17—C180.0 (6)
C8—C9—C10—C114.1 (2)C16—C17—C18—C130.3 (6)
C9—C10—C11—C12121.0 (3)C14—C13—C18—C170.8 (5)
C9—C10—C11—C83.9 (2)C9—C13—C18—C17177.6 (3)
C9—C10—C11—Cl1111.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.91 (3)2.51 (3)2.822 (4)100 (2)
C5—H5···O20.88 (4)2.52 (3)2.822 (5)101 (3)
C10—H10···O2i0.94 (4)2.50 (4)3.379 (5)156 (3)
Symmetry code: (i) x1, y, z.
 

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