Crystal and geometry-optimized structure, and Hirshfeld surface analysis of 1-(2-bromo­eth­yl)indoline-2,3-dione

In the title compound, the isatin (1H-indole-2,3-dione) moiety is almost planar (r.m.s. deviation = 0.026 Å). In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming layers parallel to the ab plane, and enclosing (24) loops.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.055
• wR factor = 0.084
• Data-to-parameter ratio = 24.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.007 Ang.
PLAT369_ALERT_2_C Long    C(sp2)-C(sp2) Bond  C7     -   C8     ..       1.54 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      6.354 Check
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         84 %

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        198 Note
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           2 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           2 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: QMOL (Gans & Shalloway, 2001) and Mercury (Macrae et al., 2008).; software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

1-(2-Bromoethyl)indoline-2,3-dione

Crystal data

C10H8BrNO2	Dx = 1.726 Mg m^−3
Mr = 254.08	Melting point: 406 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 4.6834 (2) Å	Cell parameters from 2844 reflections
b = 12.9567 (7) Å	θ = 2.5–26.7°
c = 16.1130 (8) Å	µ = 4.18 mm^−1
V = 977.76 (8) Å^3	T = 293 K
Z = 4	Block, brown
F(000) = 504	0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1663 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
ω and φ scan	θmax = 32.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→6
Tmin = 0.419, Tmax = 0.498	k = −19→17
8226 measured reflections	l = −22→18
3150 independent reflections

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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0167P)^2 + 0.3638P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3150 reflections	Δρmax = 0.70 e Å^−3
127 parameters	Δρmin = −0.59 e Å^−3
0 restraints	Absolute structure: Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.83217 (12)	0.83821 (4)	0.06227 (4)	0.0609 (2)
O1	0.4527 (9)	0.7005 (3)	0.2349 (3)	0.0719 (13)
O2	0.8447 (9)	0.6409 (2)	0.3684 (2)	0.0688 (10)
N1	0.6516 (8)	0.8607 (2)	0.2584 (2)	0.0378 (8)
C1	0.8490 (10)	0.9005 (3)	0.3156 (3)	0.0326 (9)
C2	0.9288 (9)	1.0020 (3)	0.3268 (3)	0.0429 (12)
H2	0.8520	1.0548	0.2947	0.051*
C3	1.1289 (12)	1.0218 (4)	0.3883 (3)	0.0538 (14)
H3	1.1896	1.0894	0.3966	0.065*
C4	1.2414 (10)	0.9446 (4)	0.4377 (4)	0.0572 (14)
H4	1.3755	0.9606	0.4783	0.069*
C5	1.1551 (10)	0.8445 (4)	0.4267 (3)	0.0503 (11)
H5	1.2276	0.7920	0.4599	0.060*
C6	0.9592 (9)	0.8233 (4)	0.3656 (3)	0.0362 (11)
C7	0.8222 (12)	0.7276 (3)	0.3414 (3)	0.0447 (12)
C8	0.6167 (11)	0.7569 (4)	0.2703 (3)	0.0458 (13)
C9	0.4985 (10)	0.9198 (4)	0.1964 (3)	0.0464 (12)
H9A	0.4179	0.9805	0.2227	0.056*
H9B	0.3412	0.8784	0.1757	0.056*
C10	0.6765 (12)	0.9533 (3)	0.1248 (3)	0.0499 (12)
H10A	0.8325	0.9956	0.1451	0.060*
H10B	0.5612	0.9955	0.0881	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0714 (3)	0.0570 (3)	0.0543 (3)	−0.0008 (3)	0.0059 (3)	−0.0069 (3)
O1	0.090 (3)	0.055 (2)	0.071 (3)	−0.036 (2)	−0.003 (2)	−0.012 (2)
O2	0.102 (3)	0.0323 (18)	0.072 (3)	0.005 (2)	0.013 (3)	0.0138 (17)
N1	0.042 (2)	0.035 (2)	0.036 (2)	−0.0055 (19)	−0.001 (2)	0.0022 (16)
C1	0.038 (2)	0.032 (2)	0.028 (2)	−0.001 (2)	0.007 (2)	−0.0028 (18)
C2	0.057 (3)	0.029 (2)	0.043 (3)	−0.001 (2)	0.006 (2)	0.000 (2)
C3	0.069 (4)	0.045 (3)	0.047 (3)	−0.016 (3)	0.011 (3)	−0.015 (3)
C4	0.060 (3)	0.078 (4)	0.034 (3)	−0.011 (2)	0.003 (3)	−0.007 (3)
C5	0.053 (2)	0.063 (3)	0.036 (3)	0.006 (3)	0.004 (3)	0.008 (3)
C6	0.045 (2)	0.038 (3)	0.026 (3)	0.002 (2)	0.006 (2)	−0.001 (2)
C7	0.060 (3)	0.032 (2)	0.043 (3)	0.003 (3)	0.017 (3)	0.002 (2)
C8	0.058 (3)	0.038 (3)	0.041 (3)	−0.011 (3)	0.010 (3)	−0.005 (2)
C9	0.041 (3)	0.053 (3)	0.045 (3)	0.004 (2)	−0.004 (3)	0.000 (3)
C10	0.061 (3)	0.040 (2)	0.048 (3)	0.005 (3)	−0.005 (3)	0.005 (2)

Geometric parameters (Å, º)

Br1—C10	1.942 (5)	C4—C5	1.370 (7)
O1—C8	1.204 (6)	C4—H4	0.9300
O2—C7	1.210 (5)	C5—C6	1.373 (6)
N1—C8	1.367 (5)	C5—H5	0.9300
N1—C1	1.404 (6)	C6—C7	1.449 (6)
N1—C9	1.449 (6)	C7—C8	1.544 (7)
C1—C2	1.380 (6)	C9—C10	1.488 (7)
C1—C6	1.384 (6)	C9—H9A	0.9700
C2—C3	1.388 (7)	C9—H9B	0.9700
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.382 (7)	C10—H10B	0.9700
C3—H3	0.9300
C8—N1—C1	110.4 (4)	C1—C6—C7	107.2 (4)
C8—N1—C9	123.9 (4)	O2—C7—C6	131.3 (5)
C1—N1—C9	125.7 (4)	O2—C7—C8	123.3 (5)
C2—C1—C6	120.7 (4)	C6—C7—C8	105.4 (4)
C2—C1—N1	128.0 (4)	O1—C8—N1	127.4 (5)
C6—C1—N1	111.2 (4)	O1—C8—C7	126.9 (5)
C1—C2—C3	116.9 (4)	N1—C8—C7	105.7 (4)
C1—C2—H2	121.5	N1—C9—C10	114.3 (4)
C3—C2—H2	121.5	N1—C9—H9A	108.7
C4—C3—C2	122.3 (5)	C10—C9—H9A	108.7
C4—C3—H3	118.8	N1—C9—H9B	108.7
C2—C3—H3	118.8	C10—C9—H9B	108.7
C5—C4—C3	119.9 (5)	H9A—C9—H9B	107.6
C5—C4—H4	120.1	C9—C10—Br1	112.9 (3)
C3—C4—H4	120.1	C9—C10—H10A	109.0
C4—C5—C6	118.6 (5)	Br1—C10—H10A	109.0
C4—C5—H5	120.7	C9—C10—H10B	109.0
C6—C5—H5	120.7	Br1—C10—H10B	109.0
C5—C6—C1	121.5 (4)	H10A—C10—H10B	107.8
C5—C6—C7	131.3 (5)
C8—N1—C1—C2	−175.9 (5)	C5—C6—C7—O2	−0.3 (9)
C9—N1—C1—C2	2.7 (7)	C1—C6—C7—O2	−178.2 (6)
C8—N1—C1—C6	2.1 (5)	C5—C6—C7—C8	178.1 (5)
C9—N1—C1—C6	−179.4 (4)	C1—C6—C7—C8	0.2 (5)
C6—C1—C2—C3	1.9 (7)	C1—N1—C8—O1	175.8 (5)
N1—C1—C2—C3	179.7 (4)	C9—N1—C8—O1	−2.8 (8)
C1—C2—C3—C4	−1.2 (7)	C1—N1—C8—C7	−1.8 (5)
C2—C3—C4—C5	−0.1 (8)	C9—N1—C8—C7	179.6 (4)
C3—C4—C5—C6	0.7 (8)	O2—C7—C8—O1	2.0 (8)
C4—C5—C6—C1	0.0 (7)	C6—C7—C8—O1	−176.6 (5)
C4—C5—C6—C7	−177.6 (5)	O2—C7—C8—N1	179.6 (5)
C2—C1—C6—C5	−1.4 (7)	C6—C7—C8—N1	1.0 (5)
N1—C1—C6—C5	−179.5 (4)	C8—N1—C9—C10	−107.9 (5)
C2—C1—C6—C7	176.8 (4)	C1—N1—C9—C10	73.7 (6)
N1—C1—C6—C7	−1.3 (5)	N1—C9—C10—Br1	62.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.93	2.41	3.286 (6)	156
C10—H10A···O2^ii	0.97	2.42	3.309 (6)	151

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2.