3-Chloro­benzoxazolo­[3,2-b]­isoquinolin-6-one

The title mol­ecule, C₁₅H₈ClNO₂, is essentially planar. The molecular packing in the crystal is stabilized by weak intermolecular C—H...π interactions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.150
• Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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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 and PLATON (Spek, 2003).

3-Chlorobenzoxazolo[3,2-b]isoquinolin-6-one

Crystal data

C15H8ClNO2	F(000) = 552
Mr = 269.67	Dx = 1.550 Mg m^−3
Monoclinic, P21/c	Melting point: 484(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.831 (2) Å	Cell parameters from 2228 reflections
b = 5.9716 (6) Å	θ = 2.6–28.3°
c = 8.1549 (8) Å	µ = 0.33 mm^−1
β = 95.195 (2)°	T = 293 K
V = 1155.7 (2) Å^3	Block, colorless
Z = 4	0.40 × 0.24 × 0.24 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2823 independent reflections
Radiation source: fine-focus sealed tube	1976 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.6°
ω scans	h = −31→23
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→7
Tmin = 0.881, Tmax = 0.926	l = −10→10
7010 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) = 0.150	All H-atom parameters refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.7591P] where P = (Fo^2 + 2Fc^2)/3
2823 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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	0.04180 (3)	0.31642 (15)	0.83327 (11)	0.0615 (3)
O1	0.23110 (8)	−0.2951 (3)	0.9522 (2)	0.0408 (5)
O2	0.25420 (7)	0.3438 (3)	0.6735 (2)	0.0406 (5)
C1	0.19150 (10)	0.0271 (4)	0.8487 (3)	0.0320 (5)
C2	0.14925 (11)	0.1827 (5)	0.8142 (3)	0.0366 (6)
C3	0.09737 (11)	0.1282 (5)	0.8700 (3)	0.0412 (6)
C4	0.08815 (12)	−0.0682 (5)	0.9534 (4)	0.0472 (7)
C5	0.13134 (12)	−0.2221 (5)	0.9880 (4)	0.0447 (7)
C6	0.18240 (11)	−0.1688 (4)	0.9335 (3)	0.0363 (6)
C7	0.27110 (11)	−0.1800 (4)	0.8766 (3)	0.0330 (5)
C8	0.32409 (11)	−0.2438 (4)	0.8622 (3)	0.0350 (6)
C9	0.35816 (10)	−0.0951 (4)	0.7770 (3)	0.0326 (5)
C10	0.41469 (12)	−0.1453 (5)	0.7530 (4)	0.0426 (7)
C11	0.44672 (12)	−0.0027 (5)	0.6705 (4)	0.0463 (7)
C12	0.42478 (12)	0.1997 (5)	0.6086 (4)	0.0455 (7)
C13	0.37016 (11)	0.2558 (5)	0.6302 (3)	0.0371 (6)
C14	0.33606 (10)	0.1102 (4)	0.7127 (3)	0.0300 (5)
C15	0.27758 (10)	0.1748 (4)	0.7274 (3)	0.0297 (5)
N1	0.24785 (8)	0.0177 (3)	0.8132 (2)	0.0303 (5)
H2	0.1551 (10)	0.318 (5)	0.764 (3)	0.030 (7)*
H4	0.0507 (13)	−0.097 (5)	0.984 (3)	0.051 (8)*
H5	0.1234 (14)	−0.356 (5)	1.042 (4)	0.058 (9)*
H8	0.3374 (10)	−0.380 (5)	0.903 (3)	0.032 (7)*
H10	0.4292 (12)	−0.276 (5)	0.790 (4)	0.046 (8)*
H11	0.4832 (11)	−0.044 (5)	0.657 (3)	0.037 (7)*
H12	0.4460 (11)	0.298 (5)	0.557 (3)	0.033 (7)*
H13	0.3540 (11)	0.396 (5)	0.593 (3)	0.038 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0344 (4)	0.0637 (5)	0.0872 (6)	0.0059 (3)	0.0090 (4)	0.0104 (4)
O1	0.0433 (10)	0.0349 (10)	0.0447 (11)	−0.0026 (8)	0.0068 (8)	0.0112 (8)
O2	0.0414 (10)	0.0353 (10)	0.0453 (11)	0.0035 (8)	0.0040 (8)	0.0115 (8)
C1	0.0339 (12)	0.0344 (13)	0.0277 (12)	−0.0060 (10)	0.0020 (9)	−0.0008 (10)
C2	0.0369 (13)	0.0350 (14)	0.0377 (14)	−0.0049 (11)	0.0024 (11)	0.0030 (12)
C3	0.0300 (12)	0.0457 (16)	0.0475 (16)	−0.0018 (11)	0.0014 (11)	−0.0035 (12)
C4	0.0367 (15)	0.0566 (19)	0.0492 (17)	−0.0116 (14)	0.0081 (12)	0.0036 (14)
C5	0.0453 (16)	0.0444 (17)	0.0448 (16)	−0.0128 (13)	0.0063 (12)	0.0089 (13)
C6	0.0407 (14)	0.0338 (13)	0.0341 (13)	−0.0036 (11)	0.0016 (10)	0.0025 (11)
C7	0.0430 (14)	0.0268 (12)	0.0291 (12)	−0.0039 (11)	0.0019 (10)	0.0017 (10)
C8	0.0428 (14)	0.0271 (13)	0.0351 (14)	0.0030 (11)	0.0025 (11)	0.0036 (11)
C9	0.0379 (13)	0.0326 (13)	0.0270 (12)	0.0007 (11)	0.0009 (10)	−0.0037 (10)
C10	0.0438 (15)	0.0399 (16)	0.0440 (16)	0.0054 (13)	0.0036 (12)	0.0008 (13)
C11	0.0347 (14)	0.0569 (19)	0.0484 (17)	0.0024 (13)	0.0101 (12)	−0.0018 (14)
C12	0.0426 (15)	0.0516 (18)	0.0437 (16)	−0.0105 (14)	0.0113 (12)	0.0055 (14)
C13	0.0430 (15)	0.0356 (14)	0.0330 (14)	−0.0029 (12)	0.0055 (11)	0.0009 (11)
C14	0.0371 (12)	0.0305 (12)	0.0222 (11)	−0.0014 (10)	0.0017 (9)	−0.0010 (9)
C15	0.0374 (12)	0.0275 (12)	0.0241 (11)	−0.0036 (10)	0.0022 (9)	0.0005 (10)
N1	0.0318 (10)	0.0289 (11)	0.0301 (11)	0.0002 (8)	0.0024 (8)	0.0025 (8)

Geometric parameters (Å, º)

Cl1—C3	1.742 (3)	C7—N1	1.384 (3)
O1—C7	1.367 (3)	C8—C9	1.425 (4)
O1—C6	1.381 (3)	C8—H8	0.92 (3)
O2—C15	1.216 (3)	C9—C10	1.411 (4)
C1—C2	1.380 (4)	C9—C14	1.416 (3)
C1—C6	1.386 (3)	C10—C11	1.362 (4)
C1—N1	1.400 (3)	C10—H10	0.89 (3)
C2—C3	1.394 (4)	C11—C12	1.393 (4)
C2—H2	0.92 (3)	C11—H11	0.92 (3)
C3—C4	1.383 (4)	C12—C13	1.371 (4)
C4—C5	1.389 (4)	C12—H12	0.90 (3)
C4—H4	0.96 (3)	C13—C14	1.403 (3)
C5—C6	1.370 (4)	C13—H13	0.96 (3)
C5—H5	0.94 (3)	C14—C15	1.461 (3)
C7—C8	1.334 (4)	C15—N1	1.401 (3)
C7—O1—C6	106.78 (19)	C10—C9—C14	117.4 (2)
C2—C1—C6	121.7 (2)	C10—C9—C8	121.9 (2)
C2—C1—N1	132.9 (2)	C14—C9—C8	120.7 (2)
C6—C1—N1	105.4 (2)	C11—C10—C9	121.4 (3)
C1—C2—C3	115.4 (2)	C11—C10—H10	119.6 (19)
C1—C2—H2	122.9 (15)	C9—C10—H10	119.0 (19)
C3—C2—H2	121.6 (15)	C10—C11—C12	120.9 (3)
C4—C3—C2	122.9 (3)	C10—C11—H11	118.0 (17)
C4—C3—Cl1	118.7 (2)	C12—C11—H11	121.2 (17)
C2—C3—Cl1	118.4 (2)	C13—C12—C11	119.7 (3)
C3—C4—C5	120.9 (3)	C13—C12—H12	118.5 (17)
C3—C4—H4	118.3 (18)	C11—C12—H12	121.8 (17)
C5—C4—H4	120.9 (19)	C12—C13—C14	120.6 (3)
C6—C5—C4	116.4 (3)	C12—C13—H13	122.2 (16)
C6—C5—H5	125 (2)	C14—C13—H13	117.2 (16)
C4—C5—H5	119 (2)	C13—C14—C9	120.1 (2)
C5—C6—O1	126.8 (2)	C13—C14—C15	118.3 (2)
C5—C6—C1	122.8 (3)	C9—C14—C15	121.6 (2)
O1—C6—C1	110.4 (2)	O2—C15—N1	120.1 (2)
C8—C7—O1	126.9 (2)	O2—C15—C14	126.8 (2)
C8—C7—N1	124.1 (2)	N1—C15—C14	113.2 (2)
O1—C7—N1	109.0 (2)	C7—N1—C1	108.41 (19)
C7—C8—C9	116.8 (2)	C7—N1—C15	123.7 (2)
C7—C8—H8	121.0 (16)	C1—N1—C15	127.9 (2)
C9—C8—H8	122.1 (16)
C6—C1—C2—C3	−0.2 (4)	C10—C11—C12—C13	−0.4 (5)
N1—C1—C2—C3	179.1 (2)	C11—C12—C13—C14	−0.6 (4)
C1—C2—C3—C4	−0.4 (4)	C12—C13—C14—C9	1.1 (4)
C1—C2—C3—Cl1	179.47 (19)	C12—C13—C14—C15	−178.0 (2)
C2—C3—C4—C5	0.9 (5)	C10—C9—C14—C13	−0.6 (3)
Cl1—C3—C4—C5	−179.0 (2)	C8—C9—C14—C13	179.5 (2)
C3—C4—C5—C6	−0.7 (4)	C10—C9—C14—C15	178.4 (2)
C4—C5—C6—O1	−179.6 (3)	C8—C9—C14—C15	−1.5 (3)
C4—C5—C6—C1	0.2 (4)	C13—C14—C15—O2	0.8 (4)
C7—O1—C6—C5	178.9 (3)	C9—C14—C15—O2	−178.2 (2)
C7—O1—C6—C1	−0.9 (3)	C13—C14—C15—N1	−179.5 (2)
C2—C1—C6—C5	0.3 (4)	C9—C14—C15—N1	1.5 (3)
N1—C1—C6—C5	−179.1 (2)	C8—C7—N1—C1	178.9 (2)
C2—C1—C6—O1	−179.9 (2)	O1—C7—N1—C1	−0.4 (3)
N1—C1—C6—O1	0.6 (3)	C8—C7—N1—C15	−0.5 (4)
C6—O1—C7—C8	−178.5 (2)	O1—C7—N1—C15	−179.8 (2)
C6—O1—C7—N1	0.8 (3)	C2—C1—N1—C7	−179.5 (3)
O1—C7—C8—C9	179.8 (2)	C6—C1—N1—C7	−0.1 (3)
N1—C7—C8—C9	0.6 (4)	C2—C1—N1—C15	−0.2 (4)
C7—C8—C9—C10	−179.5 (2)	C6—C1—N1—C15	179.2 (2)
C7—C8—C9—C14	0.4 (4)	O2—C15—N1—C7	179.1 (2)
C14—C9—C10—C11	−0.3 (4)	C14—C15—N1—C7	−0.6 (3)
C8—C9—C10—C11	179.5 (3)	O2—C15—N1—C1	−0.1 (4)
C9—C10—C11—C12	0.8 (5)	C14—C15—N1—C1	−179.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg(B)^i	0.92 (3)	2.79 (3)	3.532 (4)	139 (2)
C13—H13···Cg(A)^ii	0.96 (3)	2.75 (3)	3.476 (4)	133 (2)

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