2a,8a-Di­chloro-2a,8a-di­hydro-1-phenyl­di­chloro­cyclo­buta­[b]­naphthalene-3,8-dione

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.

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

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Computing details

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

Crystal data

C18H10Cl2O2	Z = 2
Mr = 329.16	F(000) = 336
Triclinic, P1	Dx = 1.508 Mg m^−3
a = 7.1114 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3052 (8) Å	Cell parameters from 2166 reflections
c = 13.8250 (13) Å	θ = 2.7–28.3°
α = 77.338 (2)°	µ = 0.45 mm^−1
β = 81.395 (2)°	T = 293 K
γ = 65.793 (2)°	Block, colourless
V = 724.98 (12) Å^3	0.42 × 0.40 × 0.06 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2482 independent reflections
Radiation source: fine-focus sealed tube	2009 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.7°
ω scans	h = −8→8
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.833, Tmax = 0.974	l = −16→13
3542 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	All H-atom parameters refined
S = 1.15	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.345P] where P = (Fo^2 + 2Fc^2)/3
2482 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.32682 (15)	0.85046 (11)	0.27295 (6)	0.0573 (3)
Cl2	0.56105 (14)	1.10013 (13)	0.17250 (7)	0.0629 (3)
O1	0.2362 (3)	0.8796 (3)	0.48039 (16)	0.0460 (5)
O2	0.5347 (4)	1.3570 (4)	0.29171 (18)	0.0621 (7)
C1	0.2478 (4)	1.1596 (4)	0.4792 (2)	0.0346 (6)
C2	0.1764 (5)	1.1637 (5)	0.5779 (2)	0.0442 (7)
C3	0.1704 (5)	1.2970 (5)	0.6243 (3)	0.0534 (8)
C4	0.2368 (5)	1.4299 (5)	0.5715 (3)	0.0514 (8)
C5	0.3105 (5)	1.4264 (4)	0.4749 (3)	0.0443 (7)
C6	0.3201 (4)	1.2916 (4)	0.4267 (2)	0.0348 (6)
C7	0.4176 (4)	1.2829 (4)	0.3253 (2)	0.0396 (7)
C8	0.3560 (4)	1.1879 (4)	0.2610 (2)	0.0376 (6)
C9	0.1428 (4)	1.3048 (4)	0.2212 (2)	0.0380 (7)
C10	0.0564 (5)	1.1965 (4)	0.2751 (2)	0.0395 (7)
C11	0.2482 (4)	1.0549 (4)	0.3185 (2)	0.0367 (6)
C12	0.2473 (4)	1.0154 (4)	0.4322 (2)	0.0345 (6)
C13	0.0726 (5)	1.4746 (4)	0.1534 (2)	0.0412 (7)
C14	−0.1308 (6)	1.5554 (4)	0.1294 (2)	0.0516 (8)
C15	−0.1983 (8)	1.7140 (5)	0.0618 (3)	0.0681 (11)
C16	−0.0657 (9)	1.7923 (5)	0.0191 (3)	0.0750 (13)
C17	0.1396 (10)	1.7154 (6)	0.0421 (3)	0.0784 (13)
C18	0.2105 (7)	1.5564 (5)	0.1095 (3)	0.0582 (9)
H2	0.136 (4)	1.074 (4)	0.611 (2)	0.036 (8)*
H3	0.097 (5)	1.301 (4)	0.697 (2)	0.051 (9)*
H4	0.243 (5)	1.523 (5)	0.602 (3)	0.058 (10)*
H5	0.351 (5)	1.509 (5)	0.438 (2)	0.047 (9)*
H10	−0.080 (5)	1.204 (4)	0.284 (2)	0.049 (9)*
H14	−0.237 (6)	1.492 (5)	0.159 (3)	0.071 (11)*
H15	−0.345 (7)	1.766 (6)	0.044 (3)	0.088 (14)*
H16	−0.122 (6)	1.898 (5)	−0.028 (3)	0.066 (11)*
H17	0.233 (6)	1.762 (5)	0.011 (3)	0.067 (11)*
H18	0.351 (6)	1.497 (5)	0.124 (3)	0.068 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0764 (6)	0.0433 (5)	0.0581 (5)	−0.0251 (4)	−0.0016 (4)	−0.0192 (4)
Cl2	0.0542 (5)	0.0671 (6)	0.0563 (6)	−0.0190 (4)	0.0235 (4)	−0.0167 (4)
O1	0.0523 (13)	0.0382 (11)	0.0504 (13)	−0.0255 (10)	−0.0032 (10)	0.0020 (10)
O2	0.0626 (15)	0.0850 (18)	0.0581 (15)	−0.0548 (15)	0.0023 (12)	−0.0038 (13)
C1	0.0315 (14)	0.0347 (15)	0.0368 (15)	−0.0129 (12)	−0.0034 (12)	−0.0037 (12)
C2	0.0422 (17)	0.0495 (19)	0.0426 (18)	−0.0217 (15)	0.0002 (14)	−0.0065 (15)
C3	0.0484 (19)	0.065 (2)	0.048 (2)	−0.0191 (17)	−0.0005 (15)	−0.0212 (17)
C4	0.0443 (18)	0.052 (2)	0.063 (2)	−0.0140 (16)	−0.0080 (16)	−0.0265 (17)
C5	0.0401 (17)	0.0387 (17)	0.061 (2)	−0.0199 (14)	−0.0113 (15)	−0.0076 (15)
C6	0.0262 (14)	0.0356 (15)	0.0436 (16)	−0.0135 (12)	−0.0062 (12)	−0.0036 (12)
C7	0.0310 (15)	0.0422 (16)	0.0475 (18)	−0.0203 (13)	−0.0046 (13)	0.0018 (13)
C8	0.0332 (15)	0.0428 (16)	0.0358 (15)	−0.0177 (13)	0.0059 (12)	−0.0051 (12)
C9	0.0417 (16)	0.0409 (16)	0.0336 (15)	−0.0176 (13)	−0.0009 (12)	−0.0088 (12)
C10	0.0330 (16)	0.0466 (17)	0.0426 (17)	−0.0206 (14)	−0.0038 (13)	−0.0040 (13)
C11	0.0398 (16)	0.0330 (14)	0.0413 (16)	−0.0184 (12)	−0.0007 (12)	−0.0072 (12)
C12	0.0267 (14)	0.0337 (15)	0.0416 (16)	−0.0119 (12)	−0.0021 (11)	−0.0037 (12)
C13	0.0567 (19)	0.0377 (16)	0.0304 (15)	−0.0197 (14)	−0.0001 (13)	−0.0081 (12)
C14	0.066 (2)	0.0421 (18)	0.0418 (18)	−0.0136 (17)	−0.0106 (16)	−0.0088 (14)
C15	0.096 (3)	0.043 (2)	0.054 (2)	−0.010 (2)	−0.022 (2)	−0.0076 (17)
C16	0.126 (4)	0.037 (2)	0.051 (2)	−0.020 (2)	−0.021 (2)	0.0012 (17)
C17	0.129 (4)	0.054 (2)	0.062 (3)	−0.056 (3)	0.005 (3)	0.001 (2)
C18	0.075 (3)	0.054 (2)	0.053 (2)	−0.036 (2)	−0.0023 (19)	−0.0035 (17)

Geometric parameters (Å, º)

Cl1—C11	1.782 (3)	C8—C11	1.602 (4)
Cl2—C8	1.772 (3)	C9—C10	1.328 (4)
O1—C12	1.205 (3)	C9—C13	1.450 (4)
O2—C7	1.211 (3)	C10—C11	1.491 (4)
C1—C2	1.387 (4)	C10—H10	0.94 (3)
C1—C6	1.413 (4)	C11—C12	1.533 (4)
C1—C12	1.483 (4)	C13—C14	1.380 (5)
C2—C3	1.379 (5)	C13—C18	1.406 (5)
C2—H2	0.92 (3)	C14—C15	1.383 (5)
C3—C4	1.394 (5)	C14—H14	1.07 (4)
C3—H3	1.07 (3)	C15—C16	1.353 (6)
C4—C5	1.362 (5)	C15—H15	1.00 (5)
C4—H4	0.98 (4)	C16—C17	1.388 (7)
C5—C6	1.397 (4)	C16—H16	0.94 (4)
C5—H5	0.88 (3)	C17—C18	1.386 (6)
C6—C7	1.470 (4)	C17—H17	0.91 (4)
C7—C8	1.521 (4)	C18—H18	0.95 (4)
C8—C9	1.534 (4)
C2—C1—C6	119.1 (3)	C9—C10—C11	97.1 (2)
C2—C1—C12	118.8 (3)	C9—C10—H10	132.5 (19)
C6—C1—C12	122.1 (2)	C11—C10—H10	130 (2)
C3—C2—C1	120.9 (3)	C10—C11—C12	116.3 (2)
C3—C2—H2	121.9 (18)	C10—C11—C8	84.6 (2)
C1—C2—H2	117.2 (18)	C12—C11—C8	116.7 (2)
C2—C3—C4	119.8 (3)	C10—C11—Cl1	112.6 (2)
C2—C3—H3	116.7 (17)	C12—C11—Cl1	109.58 (19)
C4—C3—H3	123.0 (17)	C8—C11—Cl1	115.34 (19)
C5—C4—C3	120.1 (3)	O1—C12—C1	122.2 (3)
C5—C4—H4	117 (2)	O1—C12—C11	121.9 (2)
C3—C4—H4	123 (2)	C1—C12—C11	115.8 (2)
C4—C5—C6	121.1 (3)	C14—C13—C18	119.3 (3)
C4—C5—H5	123 (2)	C14—C13—C9	119.8 (3)
C6—C5—H5	116 (2)	C18—C13—C9	120.9 (3)
C5—C6—C1	119.0 (3)	C13—C14—C15	120.5 (4)
C5—C6—C7	119.5 (3)	C13—C14—H14	121 (2)
C1—C6—C7	121.4 (2)	C15—C14—H14	119 (2)
O2—C7—C6	121.5 (3)	C16—C15—C14	120.3 (4)
O2—C7—C8	120.6 (3)	C16—C15—H15	121 (2)
C6—C7—C8	117.8 (2)	C14—C15—H15	118 (3)
C7—C8—C9	111.3 (2)	C15—C16—C17	120.8 (4)
C7—C8—C11	116.2 (2)	C15—C16—H16	115 (2)
C9—C8—C11	84.9 (2)	C17—C16—H16	124 (2)
C7—C8—Cl2	110.05 (19)	C18—C17—C16	119.9 (4)
C9—C8—Cl2	116.8 (2)	C18—C17—H17	118 (3)
C11—C8—Cl2	115.7 (2)	C16—C17—H17	122 (2)
C10—C9—C13	136.0 (3)	C17—C18—C13	119.3 (4)
C10—C9—C8	93.2 (2)	C17—C18—H18	122 (2)
C13—C9—C8	130.7 (3)	C13—C18—H18	119 (2)
C6—C1—C2—C3	1.7 (4)	C7—C8—C11—C10	107.9 (3)
C12—C1—C2—C3	−178.8 (3)	C9—C8—C11—C10	−3.35 (19)
C1—C2—C3—C4	0.0 (5)	Cl2—C8—C11—C10	−120.7 (2)
C2—C3—C4—C5	−1.1 (5)	C7—C8—C11—C12	−8.8 (3)
C3—C4—C5—C6	0.4 (5)	C9—C8—C11—C12	−120.1 (2)
C4—C5—C6—C1	1.3 (4)	Cl2—C8—C11—C12	122.6 (2)
C4—C5—C6—C7	−174.6 (3)	C7—C8—C11—Cl1	−139.6 (2)
C2—C1—C6—C5	−2.3 (4)	C9—C8—C11—Cl1	109.1 (2)
C12—C1—C6—C5	178.2 (2)	Cl2—C8—C11—Cl1	−8.2 (3)
C2—C1—C6—C7	173.5 (3)	C2—C1—C12—O1	−18.5 (4)
C12—C1—C6—C7	−6.0 (4)	C6—C1—C12—O1	161.1 (3)
C5—C6—C7—O2	19.2 (4)	C2—C1—C12—C11	157.8 (3)
C1—C6—C7—O2	−156.6 (3)	C6—C1—C12—C11	−22.6 (4)
C5—C6—C7—C8	−156.9 (3)	C10—C11—C12—O1	107.6 (3)
C1—C6—C7—C8	27.3 (4)	C8—C11—C12—O1	−154.9 (3)
O2—C7—C8—C9	−99.8 (3)	Cl1—C11—C12—O1	−21.5 (3)
C6—C7—C8—C9	76.3 (3)	C10—C11—C12—C1	−68.7 (3)
O2—C7—C8—C11	165.3 (3)	C8—C11—C12—C1	28.8 (3)
C6—C7—C8—C11	−18.6 (4)	Cl1—C11—C12—C1	162.20 (19)
O2—C7—C8—Cl2	31.3 (3)	C10—C9—C13—C14	−3.2 (5)
C6—C7—C8—Cl2	−152.6 (2)	C8—C9—C13—C14	−179.3 (3)
C7—C8—C9—C10	−112.4 (3)	C10—C9—C13—C18	178.4 (3)
C11—C8—C9—C10	3.8 (2)	C8—C9—C13—C18	2.4 (5)
Cl2—C8—C9—C10	120.1 (2)	C18—C13—C14—C15	0.9 (5)
C7—C8—C9—C13	64.9 (4)	C9—C13—C14—C15	−177.5 (3)
C11—C8—C9—C13	−179.0 (3)	C13—C14—C15—C16	−0.5 (5)
Cl2—C8—C9—C13	−62.7 (4)	C14—C15—C16—C17	0.1 (6)
C13—C9—C10—C11	178.9 (3)	C15—C16—C17—C18	0.0 (6)
C8—C9—C10—C11	−4.1 (2)	C16—C17—C18—C13	0.3 (6)
C9—C10—C11—C12	121.0 (3)	C14—C13—C18—C17	−0.8 (5)
C9—C10—C11—C8	3.9 (2)	C9—C13—C18—C17	177.6 (3)
C9—C10—C11—Cl1	−111.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.91 (3)	2.51 (3)	2.822 (4)	100 (2)
C5—H5···O2	0.88 (4)	2.52 (3)	2.822 (5)	101 (3)
C10—H10···O2^i	0.94 (4)	2.50 (4)	3.379 (5)	156 (3)

Symmetry code: (i) x−1, y, z.