3a,8c-Dichloro-8b-phenyl-3a,3b,8b,8c-tetra­hydro-2-methyl-1H-[1]benzothieno[2′,3′:3,4]cyclo­buta[1,2-c]pyrrole-1,3(2H)-dione

In the title compound, C₁₉H₁₃Cl₂NO₂S, the cyclo­butane ring is slightly folded. The crystal structure is stabilized by intra- and inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 288 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.160
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3a,8c-Dichloro-8 b-phenyl-3a,3 b,8 b,8c-tetrahydro-2-methyl-1H- [1]benzothieno[2',3':3,4]cyclobuta[1,2-c]pyrrole-1,3(2H)-dione

Crystal data

C19H13Cl2NO2S	Z = 2
Mr = 390.26	F(000) = 400
Triclinic, P1	Dx = 1.463 Mg m^−3
Hall symbol: -P 1	Melting point: 470.2 K
a = 8.3390 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6810 (17) Å	Cell parameters from 25 reflections
c = 13.268 (3) Å	θ = 1.7–25.0°
α = 71.08 (3)°	µ = 0.50 mm^−1
β = 77.21 (3)°	T = 288 K
γ = 85.31 (3)°	Block, colorless
V = 886.0 (4) Å^3	0.30 × 0.28 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = −10→10
Tmin = 0.846, Tmax = 0.870	l = −15→15
3361 measured reflections	3 standard reflections every 200 reflections
3122 independent reflections	intensity decay: none

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0695P)^2 + 1.998P] where P = (Fo^2 + 2Fc^2)/3
3122 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.43 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	0.10447 (14)	0.01736 (15)	0.59784 (9)	0.0567 (3)
Cl2	0.03422 (13)	−0.04026 (12)	0.85702 (8)	0.0487 (3)
S	0.42757 (13)	0.24483 (16)	0.54497 (8)	0.0536 (3)
O1	−0.1498 (4)	0.2748 (5)	0.8798 (3)	0.0708 (10)
O2	−0.1009 (4)	0.3334 (5)	0.5228 (3)	0.0663 (9)
N	−0.1450 (4)	0.3364 (5)	0.6983 (3)	0.0502 (9)
C1	−0.2878 (6)	0.4463 (7)	0.6954 (5)	0.0791 (17)
H1A	−0.3073	0.4862	0.6226	0.119*
H1B	−0.2672	0.5363	0.7177	0.119*
H1C	−0.3826	0.3885	0.7439	0.119*
C2	−0.0888 (5)	0.2604 (5)	0.7932 (3)	0.0445 (10)
C3	0.0629 (4)	0.1582 (4)	0.7660 (3)	0.0333 (8)
C4	0.2355 (4)	0.2405 (4)	0.7439 (3)	0.0320 (8)
C5	0.2415 (4)	0.3690 (4)	0.7964 (3)	0.0341 (8)
C6	0.1974 (5)	0.3322 (5)	0.9090 (3)	0.0436 (9)
H6	0.1580	0.2292	0.9515	0.052*
C7	0.2113 (6)	0.4452 (6)	0.9582 (4)	0.0525 (11)
H7	0.1811	0.4182	1.0336	0.063*
C8	0.2687 (6)	0.5967 (6)	0.8981 (4)	0.0586 (12)
H8	0.2787	0.6723	0.9324	0.070*
C9	0.3115 (6)	0.6376 (5)	0.7877 (4)	0.0576 (12)
H9	0.3505	0.7414	0.7467	0.069*
C10	0.2972 (5)	0.5247 (5)	0.7359 (3)	0.0441 (9)
H10	0.3252	0.5539	0.6604	0.053*
C11	0.3756 (4)	0.1187 (4)	0.7603 (3)	0.0320 (8)
C12	0.4127 (5)	0.0219 (5)	0.8586 (3)	0.0406 (9)
H12	0.3438	0.0236	0.9237	0.049*
C13	0.5510 (5)	−0.0769 (5)	0.8602 (4)	0.0522 (11)
H13	0.5753	−0.1401	0.9266	0.063*
C14	0.6530 (5)	−0.0830 (6)	0.7653 (4)	0.0559 (12)
H14	0.7443	−0.1521	0.7679	0.067*
C15	0.6218 (5)	0.0119 (6)	0.6662 (4)	0.0538 (11)
H15	0.6930	0.0100	0.6019	0.065*
C16	0.4812 (4)	0.1112 (5)	0.6639 (3)	0.0397 (9)
C17	0.2355 (4)	0.2950 (5)	0.6195 (3)	0.0376 (8)
H17	0.2090	0.4112	0.5917	0.045*
C18	0.0808 (4)	0.1862 (5)	0.6431 (3)	0.0381 (8)
C19	−0.0651 (5)	0.2908 (5)	0.6106 (3)	0.0458 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0566 (7)	0.0724 (8)	0.0492 (6)	−0.0066 (5)	−0.0059 (5)	−0.0321 (5)
Cl2	0.0476 (6)	0.0487 (6)	0.0412 (5)	−0.0168 (4)	−0.0118 (4)	0.0031 (4)
S	0.0376 (6)	0.0824 (8)	0.0305 (5)	−0.0054 (5)	0.0028 (4)	−0.0091 (5)
O1	0.0427 (18)	0.122 (3)	0.056 (2)	0.0160 (19)	−0.0053 (15)	−0.046 (2)
O2	0.0569 (19)	0.092 (3)	0.0480 (18)	−0.0029 (18)	−0.0318 (15)	−0.0051 (17)
N	0.0337 (18)	0.059 (2)	0.056 (2)	0.0082 (16)	−0.0168 (16)	−0.0135 (18)
C1	0.046 (3)	0.093 (4)	0.111 (5)	0.031 (3)	−0.039 (3)	−0.042 (4)
C2	0.030 (2)	0.061 (3)	0.044 (2)	−0.0019 (18)	−0.0069 (17)	−0.020 (2)
C3	0.0286 (18)	0.044 (2)	0.0236 (17)	−0.0030 (15)	−0.0058 (13)	−0.0051 (15)
C4	0.0284 (18)	0.0351 (18)	0.0268 (17)	0.0001 (14)	−0.0051 (14)	−0.0027 (14)
C5	0.0270 (18)	0.0337 (19)	0.0378 (19)	0.0000 (14)	−0.0084 (15)	−0.0051 (15)
C6	0.053 (2)	0.041 (2)	0.035 (2)	−0.0060 (18)	−0.0068 (17)	−0.0092 (17)
C7	0.061 (3)	0.058 (3)	0.049 (2)	0.004 (2)	−0.016 (2)	−0.028 (2)
C8	0.064 (3)	0.048 (3)	0.072 (3)	0.003 (2)	−0.014 (2)	−0.031 (2)
C9	0.058 (3)	0.034 (2)	0.080 (3)	−0.0060 (19)	−0.013 (2)	−0.016 (2)
C10	0.038 (2)	0.040 (2)	0.045 (2)	−0.0002 (17)	−0.0049 (17)	−0.0026 (17)
C11	0.0283 (17)	0.0364 (19)	0.0335 (18)	−0.0035 (14)	−0.0075 (14)	−0.0124 (15)
C12	0.038 (2)	0.043 (2)	0.043 (2)	0.0020 (17)	−0.0154 (17)	−0.0131 (17)
C13	0.050 (3)	0.051 (2)	0.064 (3)	0.009 (2)	−0.032 (2)	−0.017 (2)
C14	0.037 (2)	0.057 (3)	0.084 (3)	0.012 (2)	−0.024 (2)	−0.031 (3)
C15	0.032 (2)	0.067 (3)	0.066 (3)	−0.001 (2)	−0.001 (2)	−0.031 (2)
C16	0.0306 (19)	0.049 (2)	0.041 (2)	−0.0024 (16)	−0.0066 (16)	−0.0158 (17)
C17	0.0318 (19)	0.049 (2)	0.0261 (18)	−0.0055 (16)	−0.0045 (14)	−0.0030 (16)
C18	0.0332 (19)	0.051 (2)	0.0283 (18)	−0.0019 (17)	−0.0069 (15)	−0.0090 (16)
C19	0.039 (2)	0.057 (3)	0.040 (2)	−0.0028 (18)	−0.0154 (18)	−0.0066 (19)

Geometric parameters (Å, º)

Cl1—C18	1.738 (4)	C6—H6	0.9300
Cl2—C3	1.753 (4)	C7—C8	1.360 (7)
S—C16	1.754 (4)	C7—H7	0.9300
S—C17	1.788 (4)	C8—C9	1.360 (7)
O1—C2	1.191 (5)	C8—H8	0.9300
O2—C19	1.199 (5)	C9—C10	1.393 (6)
N—C19	1.367 (6)	C9—H9	0.9300
N—C2	1.383 (5)	C10—H10	0.9300
N—C1	1.463 (5)	C11—C12	1.388 (5)
C1—H1A	0.9600	C11—C16	1.400 (5)
C1—H1B	0.9600	C12—C13	1.380 (6)
C1—H1C	0.9600	C12—H12	0.9300
C2—C3	1.530 (5)	C13—C14	1.368 (7)
C3—C18	1.543 (5)	C13—H13	0.9300
C3—C4	1.586 (5)	C14—C15	1.374 (7)
C4—C5	1.503 (5)	C14—H14	0.9300
C4—C11	1.514 (5)	C15—C16	1.397 (6)
C4—C17	1.562 (5)	C15—H15	0.9300
C5—C10	1.386 (5)	C17—C18	1.576 (5)
C5—C6	1.392 (5)	C17—H17	0.9800
C6—C7	1.366 (6)	C18—C19	1.512 (5)
C16—S—C17	91.91 (17)	C8—C9—H9	119.9
C19—N—C2	114.7 (3)	C10—C9—H9	119.9
C19—N—C1	123.0 (4)	C5—C10—C9	120.3 (4)
C2—N—C1	122.1 (4)	C5—C10—H10	119.8
N—C1—H1A	109.5	C9—C10—H10	119.8
N—C1—H1B	109.5	C12—C11—C16	118.1 (3)
H1A—C1—H1B	109.5	C12—C11—C4	127.2 (3)
N—C1—H1C	109.5	C16—C11—C4	114.6 (3)
H1A—C1—H1C	109.5	C13—C12—C11	120.4 (4)
H1B—C1—H1C	109.5	C13—C12—H12	119.8
O1—C2—N	124.8 (4)	C11—C12—H12	119.8
O1—C2—C3	127.3 (4)	C14—C13—C12	120.8 (4)
C2—C3—C18	103.4 (3)	C14—C13—H13	119.6
N—C2—C3	107.9 (3)	C12—C13—H13	119.6
C2—C3—C4	116.0 (3)	C13—C14—C15	120.7 (4)
C18—C3—C4	90.6 (3)	C13—C14—H14	119.6
C2—C3—Cl2	108.2 (3)	C15—C14—H14	119.6
C18—C3—Cl2	119.2 (3)	C14—C15—C16	118.8 (4)
C4—C3—Cl2	117.9 (2)	C14—C15—H15	120.6
C5—C4—C11	111.8 (3)	C16—C15—H15	120.6
C5—C4—C17	118.7 (3)	C15—C16—C11	121.1 (4)
C11—C4—C17	105.7 (3)	C15—C16—S	124.6 (3)
C5—C4—C3	116.8 (3)	C11—C16—S	114.2 (3)
C11—C4—C3	113.3 (3)	C4—C17—C18	90.3 (3)
C17—C4—C3	88.2 (3)	C4—C17—S	110.6 (2)
C10—C5—C6	117.7 (4)	C18—C17—S	119.6 (3)
C10—C5—C4	121.8 (3)	C4—C17—H17	111.5
C6—C5—C4	120.5 (3)	C18—C17—H17	111.5
C7—C6—C5	121.0 (4)	S—C17—H17	111.5
C7—C6—H6	119.5	C19—C18—C3	105.9 (3)
C5—C6—H6	119.5	C19—C18—C17	110.6 (3)
C8—C7—C6	120.7 (4)	C3—C18—C17	89.3 (3)
C8—C7—H7	119.7	C19—C18—Cl1	111.9 (3)
C6—C7—H7	119.7	C3—C18—Cl1	118.4 (3)
C7—C8—C9	120.0 (4)	C17—C18—Cl1	118.4 (3)
C7—C8—H8	120.0	O2—C19—N	125.6 (4)
C9—C8—H8	120.0	O2—C19—C18	126.9 (4)
C8—C9—C10	120.2 (4)	N—C19—C18	107.4 (3)
C19—N—C2—O1	−174.4 (4)	C13—C14—C15—C16	−1.9 (7)
C1—N—C2—O1	0.7 (7)	C14—C15—C16—C11	1.9 (6)
C19—N—C2—C3	6.0 (5)	C14—C15—C16—S	177.6 (3)
C1—N—C2—C3	−178.9 (4)	C12—C11—C16—C15	−1.3 (6)
O1—C2—C3—C18	179.5 (4)	C4—C11—C16—C15	176.0 (4)
N—C2—C3—C18	−0.9 (4)	C12—C11—C16—S	−177.4 (3)
O1—C2—C3—C4	−83.1 (5)	C4—C11—C16—S	−0.1 (4)
N—C2—C3—C4	96.5 (4)	C17—S—C16—C15	174.7 (4)
O1—C2—C3—Cl2	52.1 (5)	C17—S—C16—C11	−9.3 (3)
N—C2—C3—Cl2	−128.3 (3)	C5—C4—C17—C18	−129.1 (3)
C2—C3—C4—C5	25.7 (4)	C11—C4—C17—C18	104.4 (3)
C18—C3—C4—C5	131.1 (3)	C3—C4—C17—C18	−9.3 (3)
Cl2—C3—C4—C5	−105.1 (3)	C5—C4—C17—S	108.9 (3)
C2—C3—C4—C11	157.8 (3)	C11—C4—C17—S	−17.5 (3)
C18—C3—C4—C11	−96.8 (3)	C3—C4—C17—S	−131.3 (3)
Cl2—C3—C4—C11	27.0 (4)	C16—S—C17—C4	15.7 (3)
C2—C3—C4—C17	−95.8 (3)	C16—S—C17—C18	−87.1 (3)
C18—C3—C4—C17	9.5 (3)	C2—C3—C18—C19	−3.7 (4)
Cl2—C3—C4—C17	133.4 (3)	C4—C3—C18—C19	−120.7 (3)
C11—C4—C5—C10	103.1 (4)	Cl2—C3—C18—C19	116.4 (3)
C17—C4—C5—C10	−20.4 (5)	C2—C3—C18—C17	107.6 (3)
C3—C4—C5—C10	−124.1 (4)	C4—C3—C18—C17	−9.5 (3)
C11—C4—C5—C6	−74.0 (4)	Cl2—C3—C18—C17	−132.3 (3)
C17—C4—C5—C6	162.5 (3)	C2—C3—C18—Cl1	−130.2 (3)
C3—C4—C5—C6	58.8 (4)	C4—C3—C18—Cl1	112.8 (3)
C10—C5—C6—C7	−1.0 (6)	Cl2—C3—C18—Cl1	−10.1 (4)
C4—C5—C6—C7	176.2 (4)	C4—C17—C18—C19	116.4 (3)
C5—C6—C7—C8	−0.1 (7)	S—C17—C18—C19	−129.6 (3)
C6—C7—C8—C9	0.7 (7)	C4—C17—C18—C3	9.6 (3)
C7—C8—C9—C10	−0.2 (7)	S—C17—C18—C3	123.7 (3)
C6—C5—C10—C9	1.5 (6)	C4—C17—C18—Cl1	−112.6 (3)
C4—C5—C10—C9	−175.7 (4)	S—C17—C18—Cl1	1.5 (4)
C8—C9—C10—C5	−0.9 (7)	C2—N—C19—O2	174.8 (4)
C5—C4—C11—C12	57.7 (5)	C1—N—C19—O2	−0.1 (7)
C17—C4—C11—C12	−171.7 (3)	C2—N—C19—C18	−8.5 (5)
C3—C4—C11—C12	−76.8 (4)	C1—N—C19—C18	176.5 (4)
C5—C4—C11—C16	−119.3 (3)	C3—C18—C19—O2	−176.2 (4)
C17—C4—C11—C16	11.3 (4)	C17—C18—C19—O2	88.5 (5)
C3—C4—C11—C16	106.2 (3)	Cl1—C18—C19—O2	−45.8 (5)
C16—C11—C12—C13	0.8 (6)	C3—C18—C19—N	7.2 (4)
C4—C11—C12—C13	−176.1 (4)	C17—C18—C19—N	−88.2 (4)
C11—C12—C13—C14	−0.9 (6)	Cl1—C18—C19—N	137.5 (3)
C12—C13—C14—C15	1.5 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2	0.96	2.50	2.874 (7)	103
C17—H17···O2^i	0.98	2.48	3.410 (6)	159

Symmetry code: (i) −x, −y+1, −z+1.