2a,5a-Di­chloro-4-methyl-1-methyl­ene-2-phenyl-2a,5a-di­hydro­cyclo­buta­[c]­pyrrole-3,5-dione

In the title compound, C₁₄H₁₁Cl₂NO₂, the pyrrolidine ring is planar within 0.050 (3) Å and the cyclo­butane ring is planar within 0.059 (3) Å. The dihedral angle between these two planes is 67.4 (2)°. The packing of the mol­ecules in the crystal is stabilized by C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.138
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99

   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: 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,5a-Dichloro-4-methyl-1-methylene-2-phenyl-2a,5a-dihydrocyclobuta[c]pyrrole- 3,5-dione

Crystal data

C14H11Cl2NO2	F(000) = 1216
Mr = 296.14	Dx = 1.471 Mg m^−3
Monoclinic, C2/c	Melting point: 407-408 K K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.8302 (11) Å	Cell parameters from 3429 reflections
b = 7.3973 (5) Å	θ = 2.9–28.1°
c = 25.3885 (18) Å	µ = 0.48 mm^−1
β = 106.167 (1)°	T = 293 K
V = 2675.1 (3) Å^3	Plate, colourless
Z = 8	0.48 × 0.20 × 0.16 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	2656 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.9°
ω scans	h = −18→19
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→9
Tmin = 0.802, Tmax = 0.927	l = −33→33
8171 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 3.9853P] where P = (Fo^2 + 2Fc^2)/3
3302 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.27 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	−0.01248 (4)	0.95649 (9)	0.07205 (3)	0.0386 (2)
Cl2	0.10127 (6)	0.92538 (11)	0.20482 (3)	0.0495 (2)
O1	0.09626 (15)	0.6853 (3)	0.01726 (8)	0.0524 (6)
O2	0.27917 (15)	0.7240 (3)	0.19346 (9)	0.0571 (6)
N1	0.20372 (15)	0.6917 (3)	0.10169 (10)	0.0355 (5)
C1	0.11558 (18)	0.7078 (4)	0.06601 (11)	0.0333 (6)
C2	0.04696 (17)	0.7578 (3)	0.09887 (10)	0.0277 (5)
C3	0.10893 (18)	0.7510 (4)	0.15935 (10)	0.0314 (6)
C4	0.20898 (19)	0.7243 (4)	0.15627 (12)	0.0368 (6)
C5	0.2864 (2)	0.6441 (4)	0.08401 (15)	0.0481 (8)
H5A	0.2889	0.7187	0.0535	0.072*
H5B	0.2827	0.5194	0.0732	0.072*
H5C	0.3420	0.6631	0.1137	0.072*
C6	0.06019 (18)	0.5739 (4)	0.16548 (11)	0.0338 (6)
C7	−0.01225 (19)	0.5920 (4)	0.10977 (11)	0.0314 (6)
C8	−0.11163 (18)	0.6327 (3)	0.11099 (11)	0.0303 (5)
C9	−0.1848 (2)	0.6099 (4)	0.06379 (12)	0.0390 (7)
C10	−0.2768 (2)	0.6453 (5)	0.06369 (14)	0.0457 (8)
C11	−0.2962 (2)	0.7040 (4)	0.11067 (14)	0.0452 (7)
C12	−0.2244 (2)	0.7273 (5)	0.15780 (14)	0.0456 (7)
C13	−0.1328 (2)	0.6916 (4)	0.15785 (12)	0.0405 (7)
C14	0.0794 (3)	0.4499 (5)	0.20380 (15)	0.0510 (8)
H14B	0.040 (3)	0.344 (5)	0.1978 (14)	0.059 (10)*
H13	−0.085 (2)	0.708 (4)	0.1898 (12)	0.038 (8)*
H7	−0.0099 (18)	0.497 (4)	0.0871 (11)	0.027 (7)*
H9	−0.172 (2)	0.568 (5)	0.0330 (14)	0.051 (9)*
H10	−0.320 (2)	0.625 (5)	0.0327 (15)	0.062 (11)*
H11	−0.358 (2)	0.736 (4)	0.1114 (12)	0.045 (9)*
H12	−0.237 (2)	0.768 (5)	0.1862 (14)	0.053 (10)*
H14A	0.132 (2)	0.466 (5)	0.2363 (15)	0.055 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0284 (3)	0.0391 (4)	0.0477 (4)	0.0070 (3)	0.0093 (3)	0.0131 (3)
Cl2	0.0708 (5)	0.0432 (4)	0.0358 (4)	0.0038 (4)	0.0172 (3)	−0.0105 (3)
O1	0.0493 (12)	0.0805 (17)	0.0320 (11)	0.0001 (12)	0.0193 (9)	−0.0085 (11)
O2	0.0337 (11)	0.0698 (16)	0.0558 (14)	−0.0002 (11)	−0.0074 (10)	−0.0026 (12)
N1	0.0267 (11)	0.0378 (13)	0.0436 (13)	0.0043 (9)	0.0123 (9)	−0.0009 (10)
C1	0.0311 (13)	0.0367 (15)	0.0356 (15)	0.0013 (11)	0.0153 (11)	−0.0015 (12)
C2	0.0260 (12)	0.0312 (13)	0.0259 (12)	0.0064 (10)	0.0076 (9)	0.0004 (10)
C3	0.0342 (13)	0.0334 (14)	0.0253 (12)	0.0054 (11)	0.0063 (10)	−0.0037 (11)
C4	0.0318 (14)	0.0325 (14)	0.0436 (16)	0.0012 (11)	0.0061 (12)	0.0008 (12)
C5	0.0324 (14)	0.0426 (17)	0.077 (2)	0.0069 (13)	0.0285 (15)	0.0027 (16)
C6	0.0339 (13)	0.0368 (15)	0.0326 (14)	0.0085 (11)	0.0123 (11)	0.0032 (11)
C7	0.0368 (14)	0.0272 (13)	0.0333 (14)	0.0016 (11)	0.0147 (11)	−0.0036 (11)
C8	0.0328 (13)	0.0261 (13)	0.0333 (14)	−0.0042 (10)	0.0117 (11)	0.0008 (10)
C9	0.0443 (16)	0.0396 (16)	0.0329 (15)	−0.0038 (13)	0.0105 (12)	−0.0050 (12)
C10	0.0315 (15)	0.0517 (19)	0.0467 (18)	−0.0085 (13)	−0.0012 (13)	−0.0013 (15)
C11	0.0333 (15)	0.0456 (18)	0.059 (2)	−0.0035 (13)	0.0169 (14)	0.0005 (15)
C12	0.0416 (16)	0.055 (2)	0.0451 (18)	0.0004 (14)	0.0204 (14)	−0.0040 (15)
C13	0.0329 (14)	0.0560 (19)	0.0328 (15)	−0.0022 (13)	0.0096 (12)	−0.0051 (13)
C14	0.058 (2)	0.046 (2)	0.0484 (19)	0.0125 (17)	0.0140 (16)	0.0129 (16)

Geometric parameters (Å, º)

Cl1—C2	1.751 (3)	C6—C7	1.525 (4)
Cl2—C3	1.756 (3)	C7—C8	1.513 (4)
O1—C1	1.202 (3)	C7—H7	0.92 (3)
O2—C4	1.195 (3)	C8—C13	1.383 (4)
N1—C1	1.373 (3)	C8—C9	1.385 (4)
N1—C4	1.387 (4)	C9—C10	1.388 (4)
N1—C5	1.462 (3)	C9—H9	0.91 (4)
C1—C2	1.530 (4)	C10—C11	1.373 (5)
C2—C3	1.555 (3)	C10—H10	0.88 (3)
C2—C7	1.577 (4)	C11—C12	1.373 (4)
C3—C4	1.520 (4)	C11—H11	0.94 (3)
C3—C6	1.525 (4)	C12—C13	1.383 (4)
C5—H5A	0.96	C12—H12	0.85 (4)
C5—H5B	0.96	C13—H13	0.93 (3)
C5—H5C	0.96	C14—H14B	0.96 (4)
C6—C14	1.309 (4)	C14—H14A	0.97 (4)
C1—N1—C4	115.0 (2)	C3—C6—C7	93.5 (2)
C1—N1—C5	123.0 (2)	C8—C7—C6	115.9 (2)
C4—N1—C5	122.0 (2)	C8—C7—C2	116.2 (2)
O1—C1—N1	125.3 (2)	C6—C7—C2	87.03 (19)
O1—C1—C2	126.2 (2)	C8—C7—H7	111.9 (16)
N1—C1—C2	108.5 (2)	C6—C7—H7	112.0 (17)
C1—C2—C3	103.34 (19)	C2—C7—H7	111.5 (17)
C1—C2—C7	113.3 (2)	C13—C8—C9	118.2 (3)
C3—C2—C7	90.37 (19)	C13—C8—C7	122.4 (2)
C1—C2—Cl1	109.28 (18)	C9—C8—C7	119.4 (2)
C3—C2—Cl1	120.40 (18)	C8—C9—C10	120.7 (3)
C7—C2—Cl1	118.44 (17)	C8—C9—H9	119 (2)
C4—C3—C6	113.0 (2)	C10—C9—H9	120 (2)
C4—C3—C2	105.7 (2)	C11—C10—C9	120.1 (3)
C6—C3—C2	87.82 (19)	C11—C10—H10	124 (2)
C4—C3—Cl2	111.84 (19)	C9—C10—H10	116 (2)
C6—C3—Cl2	116.41 (19)	C12—C11—C10	119.8 (3)
C2—C3—Cl2	119.79 (18)	C12—C11—H11	118.0 (19)
O2—C4—N1	125.7 (3)	C10—C11—H11	122.1 (19)
O2—C4—C3	127.4 (3)	C11—C12—C13	120.0 (3)
N1—C4—C3	106.8 (2)	C11—C12—H12	119 (2)
N1—C5—H5A	109.5	C13—C12—H12	121 (2)
N1—C5—H5B	109.5	C8—C13—C12	121.2 (3)
H5A—C5—H5B	109.5	C8—C13—H13	119.3 (19)
N1—C5—H5C	109.5	C12—C13—H13	119.6 (19)
H5A—C5—H5C	109.5	C6—C14—H14B	117 (2)
H5B—C5—H5C	109.5	C6—C14—H14A	120 (2)
C14—C6—C3	131.8 (3)	H14B—C14—H14A	123 (3)
C14—C6—C7	134.6 (3)
C4—N1—C1—O1	179.9 (3)	C4—C3—C6—C14	61.6 (4)
C5—N1—C1—O1	0.0 (5)	C2—C3—C6—C14	167.7 (3)
C4—N1—C1—C2	−0.4 (3)	Cl2—C3—C6—C14	−69.9 (4)
C5—N1—C1—C2	179.7 (2)	C4—C3—C6—C7	−114.8 (2)
O1—C1—C2—C3	175.0 (3)	C2—C3—C6—C7	−8.67 (19)
N1—C1—C2—C3	−4.7 (3)	Cl2—C3—C6—C7	113.7 (2)
O1—C1—C2—C7	78.7 (4)	C14—C6—C7—C8	74.5 (4)
N1—C1—C2—C7	−101.0 (2)	C3—C6—C7—C8	−109.3 (2)
O1—C1—C2—Cl1	−55.7 (4)	C14—C6—C7—C2	−167.7 (3)
N1—C1—C2—Cl1	124.6 (2)	C3—C6—C7—C2	8.56 (19)
C1—C2—C3—C4	7.6 (3)	C1—C2—C7—C8	−146.1 (2)
C7—C2—C3—C4	121.7 (2)	C3—C2—C7—C8	109.2 (2)
Cl1—C2—C3—C4	−114.6 (2)	Cl1—C2—C7—C8	−16.2 (3)
C1—C2—C3—C6	−105.7 (2)	C1—C2—C7—C6	96.3 (2)
C7—C2—C3—C6	8.37 (18)	C3—C2—C7—C6	−8.38 (18)
Cl1—C2—C3—C6	132.15 (19)	Cl1—C2—C7—C6	−133.75 (19)
C1—C2—C3—Cl2	134.9 (2)	C6—C7—C8—C13	14.7 (4)
C7—C2—C3—Cl2	−111.0 (2)	C2—C7—C8—C13	−85.4 (3)
Cl1—C2—C3—Cl2	12.7 (3)	C6—C7—C8—C9	−165.1 (3)
C1—N1—C4—O2	−177.1 (3)	C2—C7—C8—C9	94.8 (3)
C5—N1—C4—O2	2.8 (5)	C13—C8—C9—C10	−0.1 (4)
C1—N1—C4—C3	5.5 (3)	C7—C8—C9—C10	179.7 (3)
C5—N1—C4—C3	−174.6 (2)	C8—C9—C10—C11	0.1 (5)
C6—C3—C4—O2	−91.1 (4)	C9—C10—C11—C12	−0.1 (5)
C2—C3—C4—O2	174.6 (3)	C10—C11—C12—C13	0.0 (5)
Cl2—C3—C4—O2	42.6 (4)	C9—C8—C13—C12	−0.1 (5)
C6—C3—C4—N1	86.3 (3)	C7—C8—C13—C12	−179.8 (3)
C2—C3—C4—N1	−8.1 (3)	C11—C12—C13—C8	0.1 (5)
Cl2—C3—C4—N1	−140.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5C···O2	0.96	2.49	2.872 (4)	103
C5—H5B···CgP^i	0.96	2.75	3.579 (3)	145

Symmetry code: (i) x+1/2, y−1/2, z.