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The title mol­ecule, C15H8ClNO2, is essentially planar. In the solid state, the mol­ecules form sheet-like structures parallel to (011), which are stabilized by weak C—H...O hydrogen bonds and π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019274/cv6078sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019274/cv6078Isup2.hkl
Contains datablock I

CCDC reference: 177222

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.069
  • wR factor = 0.173
  • Data-to-parameter ratio = 11.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

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, 1990).

2-Chlorobenzoxazolo[3,2-b]isoquinolin-6-one top
Crystal data top
C15H8ClNO2Z = 2
Mr = 269.67F(000) = 276
Triclinic, P1Dx = 1.546 Mg m3
a = 7.6104 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8699 (7) ÅCell parameters from 2122 reflections
c = 9.8571 (9) Åθ = 2.1–29.6°
α = 81.891 (2)°µ = 0.33 mm1
β = 83.268 (2)°T = 293 K
γ = 85.499 (2)°Slab, yellow
V = 579.29 (9) Å30.28 × 0.20 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1976 independent reflections
Radiation source: fine-focus sealed tube1244 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.1°
ω scansh = 96
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 99
Tmin = 0.915, Tmax = 0.968l = 1011
3273 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0746P)2]
where P = (Fo2 + 2Fc2)/3
1976 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.37 e Å3
Special details top

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 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 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 (Å2) top
xyzUiso*/Ueq
Cl10.05080 (16)0.73131 (14)0.02619 (12)0.0661 (5)
O10.1434 (3)0.3367 (3)0.4778 (2)0.0378 (7)
O20.7372 (3)0.3159 (3)0.3842 (3)0.0494 (7)
N10.4401 (3)0.3178 (3)0.4435 (3)0.0292 (7)
C10.3802 (4)0.4267 (4)0.3308 (3)0.0294 (8)
C20.4660 (5)0.5129 (4)0.2139 (4)0.0358 (9)
H20.58900.50850.19760.043*
C30.3590 (5)0.6069 (4)0.1212 (4)0.0378 (9)
H30.41120.66860.04110.045*
C40.1762 (5)0.6103 (4)0.1462 (4)0.0385 (9)
C50.0889 (5)0.5231 (4)0.2632 (4)0.0394 (9)
H50.03410.52470.27920.047*
C60.1977 (5)0.4338 (4)0.3539 (4)0.0321 (8)
C70.2942 (4)0.2648 (4)0.5328 (4)0.0309 (8)
C80.3030 (5)0.1589 (4)0.6504 (4)0.0370 (9)
H80.20170.12830.70830.044*
C90.4778 (5)0.0944 (4)0.6829 (4)0.0319 (8)
C100.5022 (5)0.0216 (4)0.8019 (4)0.0424 (10)
H100.40420.05670.86190.051*
C110.6701 (6)0.0843 (5)0.8308 (4)0.0476 (11)
H110.68410.15960.91100.057*
C120.8177 (5)0.0366 (5)0.7423 (4)0.0458 (10)
H120.93000.08150.76200.055*
C130.7984 (5)0.0771 (4)0.6252 (4)0.0403 (9)
H130.89800.11070.56650.048*
C140.6287 (4)0.1432 (4)0.5934 (4)0.0321 (8)
C150.6157 (5)0.2623 (4)0.4669 (4)0.0343 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0657 (8)0.0723 (8)0.0567 (8)0.0052 (6)0.0270 (6)0.0157 (6)
O10.0239 (14)0.0445 (14)0.0405 (15)0.0031 (11)0.0006 (11)0.0083 (11)
O20.0278 (16)0.0661 (17)0.0495 (17)0.0096 (13)0.0009 (13)0.0101 (13)
N10.0240 (16)0.0299 (15)0.0322 (17)0.0045 (12)0.0029 (12)0.0021 (12)
C10.030 (2)0.0265 (16)0.032 (2)0.0021 (14)0.0060 (15)0.0020 (14)
C20.034 (2)0.0344 (18)0.037 (2)0.0057 (16)0.0018 (16)0.0024 (16)
C30.044 (2)0.0341 (19)0.033 (2)0.0054 (16)0.0022 (17)0.0035 (15)
C40.043 (2)0.0341 (19)0.038 (2)0.0047 (17)0.0127 (18)0.0010 (16)
C50.034 (2)0.0372 (19)0.046 (2)0.0005 (16)0.0068 (18)0.0004 (17)
C60.030 (2)0.0304 (18)0.033 (2)0.0038 (15)0.0006 (15)0.0005 (15)
C70.0225 (19)0.0317 (18)0.037 (2)0.0028 (14)0.0017 (15)0.0020 (15)
C80.033 (2)0.040 (2)0.037 (2)0.0090 (16)0.0009 (16)0.0011 (17)
C90.035 (2)0.0275 (17)0.034 (2)0.0041 (14)0.0056 (16)0.0054 (14)
C100.047 (3)0.038 (2)0.040 (2)0.0108 (18)0.0028 (18)0.0036 (16)
C110.060 (3)0.036 (2)0.048 (3)0.0067 (19)0.022 (2)0.0064 (18)
C120.042 (2)0.041 (2)0.056 (3)0.0023 (18)0.020 (2)0.0024 (19)
C130.034 (2)0.038 (2)0.049 (2)0.0034 (16)0.0080 (18)0.0036 (17)
C140.030 (2)0.0277 (17)0.040 (2)0.0030 (14)0.0083 (16)0.0049 (15)
C150.028 (2)0.0364 (19)0.039 (2)0.0073 (16)0.0047 (16)0.0041 (16)
Geometric parameters (Å, º) top
Cl1—C41.738 (3)C5—H50.93
O1—C71.374 (4)C7—C81.333 (5)
O1—C61.384 (4)C8—C91.442 (5)
O2—C151.219 (4)C8—H80.93
N1—C71.386 (4)C9—C101.402 (5)
N1—C11.402 (4)C9—C141.407 (5)
N1—C151.408 (4)C10—C111.380 (5)
C1—C21.374 (5)C10—H100.93
C1—C61.379 (5)C11—C121.382 (6)
C2—C31.391 (5)C11—H110.93
C2—H20.93C12—C131.372 (5)
C3—C41.383 (5)C12—H120.93
C3—H30.93C13—C141.407 (5)
C4—C51.382 (5)C13—H130.93
C5—C61.373 (5)C14—C151.459 (5)
C7—O1—C6106.9 (2)C7—C8—C9116.4 (3)
C7—N1—C1108.6 (3)C7—C8—H8121.8
C7—N1—C15123.0 (3)C9—C8—H8121.8
C1—N1—C15128.4 (3)C10—C9—C14118.2 (3)
C2—C1—C6121.3 (3)C10—C9—C8121.2 (3)
C2—C1—N1133.0 (3)C14—C9—C8120.5 (3)
C6—C1—N1105.6 (3)C11—C10—C9120.6 (4)
C1—C2—C3116.4 (3)C11—C10—H10119.7
C1—C2—H2121.8C9—C10—H10119.7
C3—C2—H2121.8C10—C11—C12120.9 (3)
C4—C3—C2121.1 (3)C10—C11—H11119.6
C4—C3—H3119.5C12—C11—H11119.6
C2—C3—H3119.5C13—C12—C11119.9 (4)
C5—C4—C3122.8 (3)C13—C12—H12120.1
C5—C4—Cl1118.6 (3)C11—C12—H12120.1
C3—C4—Cl1118.6 (3)C12—C13—C14120.4 (4)
C6—C5—C4114.8 (4)C12—C13—H13119.8
C6—C5—H5122.6C14—C13—H13119.8
C4—C5—H5122.6C9—C14—C13120.0 (3)
C5—C6—C1123.5 (3)C9—C14—C15122.0 (3)
C5—C6—O1126.1 (3)C13—C14—C15118.1 (3)
C1—C6—O1110.4 (3)O2—C15—N1119.2 (3)
C8—C7—O1127.0 (3)O2—C15—C14127.3 (3)
C8—C7—N1124.6 (3)N1—C15—C14113.5 (3)
O1—C7—N1108.5 (3)
C7—N1—C1—C2179.5 (4)C15—N1—C7—O1177.8 (3)
C15—N1—C1—C21.2 (6)O1—C7—C8—C9177.3 (3)
C7—N1—C1—C61.2 (4)N1—C7—C8—C91.3 (5)
C15—N1—C1—C6177.1 (3)C7—C8—C9—C10178.1 (3)
C6—C1—C2—C30.1 (5)C7—C8—C9—C140.1 (5)
N1—C1—C2—C3178.1 (3)C14—C9—C10—C110.8 (5)
C1—C2—C3—C40.8 (5)C8—C9—C10—C11179.1 (3)
C2—C3—C4—C50.4 (6)C9—C10—C11—C121.1 (6)
C2—C3—C4—Cl1179.8 (3)C10—C11—C12—C131.3 (6)
C3—C4—C5—C60.7 (5)C11—C12—C13—C141.1 (6)
Cl1—C4—C5—C6178.7 (3)C10—C9—C14—C130.6 (5)
C4—C5—C6—C11.5 (5)C8—C9—C14—C13178.9 (3)
C4—C5—C6—O1180.0 (3)C10—C9—C14—C15179.6 (3)
C2—C1—C6—C51.1 (5)C8—C9—C14—C151.3 (5)
N1—C1—C6—C5177.4 (3)C12—C13—C14—C90.8 (5)
C2—C1—C6—O1179.9 (3)C12—C13—C14—C15179.4 (3)
N1—C1—C6—O11.3 (4)C7—N1—C15—O2179.4 (3)
C7—O1—C6—C5177.7 (3)C1—N1—C15—O22.6 (5)
C7—O1—C6—C11.0 (4)C7—N1—C15—C140.4 (4)
C6—O1—C7—C8178.6 (3)C1—N1—C15—C14177.7 (3)
C6—O1—C7—N10.2 (3)C9—C14—C15—O2178.2 (3)
C1—N1—C7—C8179.4 (3)C13—C14—C15—O21.6 (6)
C15—N1—C7—C81.1 (5)C9—C14—C15—N11.5 (5)
C1—N1—C7—O10.6 (4)C13—C14—C15—N1178.7 (3)
 

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