3-Benzyl­idene-1-(2,6-di­chloro­phenyl)­indolin-2-one

The phenyl and di­chloro­phenyl rings of the title mol­ecule, C₂₁H₁₃Cl₂NO, are oriented at angles of 39.3 (1) and 77.8 (1)°, respectively, with respect to the central indoline ring. The crystal structure is stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.107
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: SHELXL97.

3-Benzylidene-[N-(2,6-dichlorophenyl)-indolin-2-one]

Crystal data

C21H13Cl2NO	F(000) = 752
Mr = 366.22	Dx = 1.378 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.242 (5) Å	θ = 10–15°
b = 19.232 (12) Å	µ = 0.38 mm^−1
c = 10.319 (5) Å	T = 293 K
β = 105.80 (4)°	Plate, white
V = 1764.8 (17) Å^3	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	2276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→22
Tmin = 0.896, Tmax = 0.929	l = −12→11
3290 measured reflections	2 standard reflections every 100 reflections
3090 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0294P)^2 + 1.0794P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3090 reflections	Δρmax = 0.27 e Å^−3
227 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (8)

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	0.47556 (11)	0.27210 (4)	0.10827 (10)	0.0924 (3)
Cl2	0.15949 (9)	0.50626 (4)	−0.05194 (9)	0.0811 (3)
O1	0.3571 (2)	0.44759 (10)	0.28208 (19)	0.0645 (5)
N1	0.2359 (2)	0.37615 (11)	0.1072 (2)	0.0513 (5)
C1	0.2566 (3)	0.40735 (13)	0.2324 (3)	0.0482 (6)
C2	0.1302 (3)	0.38254 (12)	0.2858 (2)	0.0460 (6)
C3	−0.0696 (3)	0.28542 (14)	0.1842 (3)	0.0616 (7)
H3	−0.1141	0.2841	0.2549	0.074*
C4	−0.1196 (3)	0.24138 (16)	0.0755 (3)	0.0728 (9)
H4	−0.1977	0.2105	0.0734	0.087*
C5	−0.0549 (3)	0.24278 (17)	−0.0299 (3)	0.0770 (9)
H5	−0.0916	0.2136	−0.1033	0.092*
C6	0.0642 (3)	0.28698 (15)	−0.0285 (3)	0.0669 (8)
H6	0.1090	0.2875	−0.0990	0.080*
C7	0.1129 (3)	0.32973 (13)	0.0807 (3)	0.0500 (6)
C8	0.0471 (2)	0.33167 (12)	0.1880 (2)	0.0461 (6)
C9	0.3255 (3)	0.39048 (13)	0.0189 (2)	0.0497 (6)
C10	0.3016 (3)	0.44970 (14)	−0.0610 (3)	0.0544 (6)
C11	0.3901 (3)	0.46469 (16)	−0.1456 (3)	0.0670 (8)
H11	0.3730	0.5048	−0.1980	0.080*
C12	0.5031 (3)	0.42005 (16)	−0.1515 (3)	0.0697 (8)
H12	0.5627	0.4300	−0.2087	0.084*
C13	0.5301 (3)	0.36092 (16)	−0.0750 (3)	0.0695 (8)
H13	0.6069	0.3308	−0.0806	0.083*
C14	0.4421 (3)	0.34636 (14)	0.0108 (3)	0.0580 (7)
C15	0.1149 (3)	0.41034 (13)	0.4003 (3)	0.0519 (6)
H15	0.1948	0.4379	0.4472	0.062*
C16	−0.0092 (3)	0.40376 (12)	0.4625 (2)	0.0516 (6)
C17	−0.1573 (3)	0.39822 (15)	0.3861 (3)	0.0640 (7)
H17	−0.1786	0.3966	0.2927	0.077*
C18	−0.2739 (4)	0.39499 (17)	0.4457 (4)	0.0800 (9)
H18	−0.3728	0.3917	0.3929	0.096*
C19	−0.2426 (5)	0.39672 (18)	0.5828 (4)	0.0918 (11)
H19	−0.3206	0.3933	0.6234	0.110*
C20	−0.0982 (5)	0.40346 (17)	0.6609 (4)	0.0868 (11)
H20	−0.0786	0.4049	0.7541	0.104*
C21	0.0189 (4)	0.40815 (14)	0.6018 (3)	0.0671 (8)
H21	0.1168	0.4143	0.6553	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0994 (6)	0.0695 (5)	0.1249 (8)	0.0220 (4)	0.0586 (6)	0.0289 (5)
Cl2	0.0662 (5)	0.0833 (6)	0.1008 (6)	0.0203 (4)	0.0346 (4)	0.0217 (5)
O1	0.0558 (11)	0.0755 (13)	0.0667 (12)	−0.0196 (10)	0.0243 (9)	−0.0112 (10)
N1	0.0488 (12)	0.0565 (12)	0.0556 (12)	−0.0109 (10)	0.0262 (10)	−0.0035 (10)
C1	0.0446 (13)	0.0486 (14)	0.0541 (15)	−0.0005 (11)	0.0180 (11)	0.0029 (12)
C2	0.0438 (13)	0.0455 (13)	0.0511 (14)	0.0021 (10)	0.0169 (11)	0.0072 (11)
C3	0.0540 (15)	0.0620 (17)	0.0772 (19)	−0.0073 (13)	0.0322 (14)	0.0019 (15)
C4	0.0600 (17)	0.0661 (19)	0.100 (2)	−0.0217 (14)	0.0338 (17)	−0.0153 (17)
C5	0.0712 (19)	0.078 (2)	0.086 (2)	−0.0246 (16)	0.0282 (17)	−0.0265 (17)
C6	0.0649 (17)	0.0745 (19)	0.0692 (18)	−0.0154 (15)	0.0320 (15)	−0.0154 (15)
C7	0.0460 (13)	0.0494 (14)	0.0577 (15)	−0.0047 (11)	0.0194 (12)	−0.0003 (12)
C8	0.0414 (12)	0.0462 (13)	0.0534 (14)	0.0008 (10)	0.0176 (11)	0.0057 (11)
C9	0.0471 (13)	0.0556 (15)	0.0524 (14)	−0.0085 (11)	0.0236 (12)	−0.0034 (12)
C10	0.0474 (14)	0.0603 (16)	0.0587 (16)	−0.0020 (12)	0.0200 (12)	0.0031 (13)
C11	0.0696 (18)	0.0719 (19)	0.0660 (18)	−0.0057 (15)	0.0295 (15)	0.0120 (15)
C12	0.076 (2)	0.080 (2)	0.0682 (19)	−0.0128 (16)	0.0455 (16)	−0.0057 (16)
C13	0.0663 (18)	0.0706 (19)	0.086 (2)	0.0012 (15)	0.0451 (17)	−0.0090 (17)
C14	0.0603 (16)	0.0527 (15)	0.0672 (17)	−0.0026 (12)	0.0280 (14)	−0.0027 (13)
C15	0.0545 (14)	0.0520 (14)	0.0518 (15)	−0.0025 (12)	0.0189 (12)	0.0041 (12)
C16	0.0641 (16)	0.0434 (13)	0.0547 (15)	−0.0004 (12)	0.0284 (13)	0.0016 (11)
C17	0.0626 (18)	0.0715 (18)	0.0644 (17)	0.0077 (14)	0.0284 (14)	0.0026 (14)
C18	0.0687 (19)	0.088 (2)	0.097 (3)	0.0025 (17)	0.0460 (18)	−0.0050 (19)
C19	0.106 (3)	0.090 (2)	0.107 (3)	−0.010 (2)	0.076 (3)	−0.015 (2)
C20	0.131 (3)	0.079 (2)	0.070 (2)	−0.008 (2)	0.062 (2)	−0.0138 (18)
C21	0.087 (2)	0.0616 (17)	0.0591 (17)	−0.0056 (15)	0.0307 (16)	−0.0098 (14)

Geometric parameters (Å, º)

Cl1—C14	1.725 (3)	C10—C11	1.379 (4)
Cl2—C10	1.728 (3)	C11—C12	1.366 (4)
O1—C1	1.210 (3)	C11—H11	0.93
N1—C1	1.389 (3)	C12—C13	1.368 (4)
N1—C7	1.412 (3)	C12—H12	0.93
N1—C9	1.416 (3)	C13—C14	1.385 (4)
C1—C2	1.498 (3)	C13—H13	0.93
C2—C15	1.339 (3)	C15—C16	1.465 (3)
C2—C8	1.464 (3)	C15—H15	0.93
C3—C4	1.381 (4)	C16—C17	1.385 (4)
C3—C8	1.391 (3)	C16—C21	1.392 (4)
C3—H3	0.93	C17—C18	1.380 (4)
C4—C5	1.376 (4)	C17—H17	0.93
C4—H4	0.93	C18—C19	1.365 (5)
C5—C6	1.388 (4)	C18—H18	0.93
C5—H5	0.93	C19—C20	1.364 (5)
C6—C7	1.369 (4)	C19—H19	0.93
C6—H6	0.93	C20—C21	1.382 (4)
C7—C8	1.401 (3)	C20—H20	0.93
C9—C10	1.388 (4)	C21—H21	0.93
C9—C14	1.392 (3)
C1—N1—C7	110.68 (19)	C12—C11—C10	119.3 (3)
C1—N1—C9	123.9 (2)	C12—C11—H11	120.4
C7—N1—C9	125.4 (2)	C10—C11—H11	120.4
O1—C1—N1	124.5 (2)	C11—C12—C13	121.2 (3)
O1—C1—C2	129.3 (2)	C11—C12—H12	119.4
N1—C1—C2	106.3 (2)	C13—C12—H12	119.4
C15—C2—C8	135.5 (2)	C12—C13—C14	119.4 (3)
C15—C2—C1	118.5 (2)	C12—C13—H13	120.3
C8—C2—C1	105.9 (2)	C14—C13—H13	120.3
C4—C3—C8	120.0 (3)	C13—C14—C9	120.9 (3)
C4—C3—H3	120.0	C13—C14—Cl1	119.8 (2)
C8—C3—H3	120.0	C9—C14—Cl1	119.3 (2)
C5—C4—C3	120.6 (3)	C2—C15—C16	129.5 (2)
C5—C4—H4	119.7	C2—C15—H15	115.3
C3—C4—H4	119.7	C16—C15—H15	115.3
C4—C5—C6	121.2 (3)	C17—C16—C21	118.1 (2)
C4—C5—H5	119.4	C17—C16—C15	121.8 (2)
C6—C5—H5	119.4	C21—C16—C15	120.0 (3)
C7—C6—C5	117.3 (3)	C18—C17—C16	121.4 (3)
C7—C6—H6	121.4	C18—C17—H17	119.3
C5—C6—H6	121.4	C16—C17—H17	119.3
C6—C7—C8	123.4 (2)	C19—C18—C17	119.3 (3)
C6—C7—N1	127.3 (2)	C19—C18—H18	120.3
C8—C7—N1	109.3 (2)	C17—C18—H18	120.3
C3—C8—C7	117.5 (2)	C20—C19—C18	120.8 (3)
C3—C8—C2	134.8 (2)	C20—C19—H19	119.6
C7—C8—C2	107.7 (2)	C18—C19—H19	119.6
C10—C9—C14	117.7 (2)	C19—C20—C21	120.2 (3)
C10—C9—N1	121.1 (2)	C19—C20—H20	119.9
C14—C9—N1	121.2 (2)	C21—C20—H20	119.9
C11—C10—C9	121.4 (2)	C20—C21—C16	120.2 (3)
C11—C10—Cl2	119.6 (2)	C20—C21—H21	119.9
C9—C10—Cl2	118.98 (19)	C16—C21—H21	119.9
C7—N1—C1—O1	177.4 (2)	C1—N1—C9—C14	99.5 (3)
C9—N1—C1—O1	−3.5 (4)	C7—N1—C9—C14	−81.6 (3)
C7—N1—C1—C2	−4.2 (3)	C14—C9—C10—C11	−0.1 (4)
C9—N1—C1—C2	174.9 (2)	N1—C9—C10—C11	178.9 (2)
O1—C1—C2—C15	4.8 (4)	C14—C9—C10—Cl2	−179.1 (2)
N1—C1—C2—C15	−173.5 (2)	N1—C9—C10—Cl2	−0.2 (3)
O1—C1—C2—C8	−177.1 (3)	C9—C10—C11—C12	0.4 (4)
N1—C1—C2—C8	4.7 (2)	Cl2—C10—C11—C12	179.5 (2)
C8—C3—C4—C5	−0.1 (5)	C10—C11—C12—C13	−0.1 (5)
C3—C4—C5—C6	1.6 (5)	C11—C12—C13—C14	−0.5 (5)
C4—C5—C6—C7	−0.9 (5)	C12—C13—C14—C9	0.9 (4)
C5—C6—C7—C8	−1.2 (4)	C12—C13—C14—Cl1	−179.8 (2)
C5—C6—C7—N1	176.6 (3)	C10—C9—C14—C13	−0.6 (4)
C1—N1—C7—C6	−176.1 (3)	N1—C9—C14—C13	−179.5 (2)
C9—N1—C7—C6	4.9 (4)	C10—C9—C14—Cl1	−179.9 (2)
C1—N1—C7—C8	2.0 (3)	N1—C9—C14—Cl1	1.1 (3)
C9—N1—C7—C8	−177.0 (2)	C8—C2—C15—C16	−7.9 (5)
C4—C3—C8—C7	−2.0 (4)	C1—C2—C15—C16	169.6 (2)
C4—C3—C8—C2	−177.4 (3)	C2—C15—C16—C17	−34.1 (4)
C6—C7—C8—C3	2.7 (4)	C2—C15—C16—C21	150.7 (3)
N1—C7—C8—C3	−175.5 (2)	C21—C16—C17—C18	−1.9 (4)
C6—C7—C8—C2	179.3 (2)	C15—C16—C17—C18	−177.2 (3)
N1—C7—C8—C2	1.1 (3)	C16—C17—C18—C19	−0.5 (5)
C15—C2—C8—C3	−10.1 (5)	C17—C18—C19—C20	1.8 (5)
C1—C2—C8—C3	172.2 (3)	C18—C19—C20—C21	−0.5 (6)
C15—C2—C8—C7	174.2 (3)	C19—C20—C21—C16	−2.1 (5)
C1—C2—C8—C7	−3.5 (3)	C17—C16—C21—C20	3.2 (4)
C1—N1—C9—C10	−79.5 (3)	C15—C16—C21—C20	178.6 (3)
C7—N1—C9—C10	99.5 (3)