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In the title compound, 4-chloro-3-nitro-2H-chromen-2-one, C9H4ClNO4, the coumarin core has a planar conformation. The Cl atom accepts one of the bifurcated lone pairs of the keto O atom with sp2 hybridization state. The other lone pair is donated to the pyran ring of a neighboring mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011943/ob6503sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011943/ob6503Isup2.hkl
Contains datablock I

CCDC reference: 272057

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.198
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl4 .. O2 .. 2.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: CAD-4 Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SIR88 (Burla et al., 1989); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.

4-chloro-3-nitro-2H- chromen-2-one top
Crystal data top
C9H4ClNO4F(000) = 456.0
Mr = 225.59Dx = 1.646 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.5110 (4) Åθ = 30.0–35.0°
b = 13.526 (1) ŵ = 3.71 mm1
c = 8.6612 (5) ÅT = 297 K
β = 114.119 (5)°Rod, yellow
V = 910.0 (1) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.032
Radiation source: sealed X-ray tubeθmax = 74.9°
ω/2θ scansh = 100
Absorption correction: ψ scan
(North et al., 1968)
k = 016
Tmin = 0.433, Tmax = 0.478l = 910
2084 measured reflections3 standard reflections every 300 reflections
1876 independent reflections intensity decay: none
1727 reflections with F2 > 2.0σ(F2)
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.157(Max(Fo2,0) + 2Fc2)/3)2]
R[F2 > 2σ(F2)] = 0.047(Δ/σ)max = 0.0003
wR(F2) = 0.198Δρmax = 0.34 e Å3
S = 1.21Δρmin = 0.43 e Å3
1876 reflectionsExtinction correction: type 2 Gaussian isotropic (Zachariasen, 1967)
137 parametersExtinction coefficient: 0.39 (6)
H-atom parameters not refined
Special details top

Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl40.48318 (6)0.53267 (4)0.70590 (7)0.0588 (2)
O10.0943 (2)0.2946 (1)0.4628 (2)0.0512 (4)
O20.2479 (2)0.1891 (1)0.6613 (2)0.0644 (5)
O310.4867 (4)0.3193 (3)0.9598 (3)0.126 (1)
O320.6406 (3)0.3048 (2)0.8216 (3)0.0882 (7)
N30.5066 (2)0.3235 (1)0.8317 (2)0.0560 (5)
C20.2346 (3)0.2710 (1)0.6051 (2)0.0449 (5)
C30.3588 (2)0.3501 (1)0.6775 (2)0.0418 (4)
C40.3365 (2)0.4414 (1)0.6111 (2)0.0404 (4)
C410.1877 (2)0.4628 (1)0.4585 (2)0.0408 (5)
C50.1554 (3)0.5538 (2)0.3737 (3)0.0568 (6)
C60.0120 (4)0.5651 (2)0.2250 (3)0.0693 (7)
C70.1028 (4)0.4875 (2)0.1593 (3)0.0704 (7)
C80.0756 (3)0.3978 (2)0.2400 (3)0.0599 (6)
C110.0705 (2)0.3865 (1)0.3882 (2)0.0437 (5)
H50.23250.60730.41840.0684*
H60.00990.62650.16740.0832*
H70.20150.49660.05610.0843*
H80.15530.34520.19570.0720*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl40.0559 (5)0.0475 (5)0.0649 (5)0.0141 (2)0.0163 (3)0.0122 (2)
O10.0460 (8)0.0391 (7)0.0570 (8)0.0034 (5)0.0093 (6)0.0047 (5)
O20.065 (1)0.0415 (8)0.084 (1)0.0004 (6)0.0272 (9)0.0135 (7)
O310.097 (2)0.227 (3)0.0478 (10)0.024 (2)0.022 (1)0.037 (1)
O320.0502 (10)0.122 (2)0.076 (1)0.022 (1)0.0095 (8)0.009 (1)
N30.0504 (10)0.062 (1)0.0451 (8)0.0000 (8)0.0085 (7)0.0060 (7)
C20.0443 (9)0.0388 (9)0.0506 (9)0.0011 (7)0.0184 (7)0.0017 (7)
C30.0395 (9)0.0448 (9)0.0384 (8)0.0013 (6)0.0132 (7)0.0010 (6)
C40.0437 (9)0.0387 (9)0.0394 (8)0.0047 (7)0.0177 (7)0.0057 (6)
C410.0440 (10)0.0398 (10)0.0398 (9)0.0053 (6)0.0182 (8)0.0013 (6)
C50.063 (1)0.048 (1)0.063 (1)0.0087 (9)0.028 (1)0.0136 (9)
C60.081 (2)0.069 (2)0.060 (1)0.026 (1)0.030 (1)0.025 (1)
C70.065 (1)0.090 (2)0.043 (1)0.031 (1)0.009 (1)0.009 (1)
C80.047 (1)0.069 (1)0.050 (1)0.0070 (9)0.0056 (8)0.0098 (9)
C110.0438 (9)0.0436 (9)0.0393 (9)0.0060 (7)0.0124 (7)0.0023 (6)
Geometric parameters (Å, º) top
Cl4—C41.709 (2)C41—C51.402 (3)
O1—C21.358 (2)C41—C111.390 (3)
O1—C111.377 (2)C5—C61.374 (4)
O2—C21.197 (2)C6—C71.388 (4)
O31—N31.190 (3)C7—C81.372 (4)
O32—N31.207 (3)C8—C111.383 (3)
N3—C31.457 (2)C5—H50.946
C2—C31.454 (3)C7—H70.952
C3—C41.342 (3)C6—H60.947
C4—C411.438 (3)C8—H80.948
Cl4···O2i2.981 (2)O2···C6iv3.585 (3)
Cl4···O31ii3.443 (3)O31···C2v3.144 (3)
O1···O2iii3.371 (2)O31···O32v3.316 (3)
O1···C6iv3.448 (3)O31···C3v3.415 (3)
O2···C11v3.100 (2)O32···C5vi3.454 (3)
O2···O31iii3.176 (3)C4···C7vii3.474 (3)
O2···C8v3.310 (3)C5···C11vii3.441 (3)
O2···C41v3.490 (2)
C2—O1—C11122.9 (1)C41—C5—C6119.8 (2)
O31—N3—O32123.8 (2)C5—C6—C7120.5 (2)
O31—N3—C3117.9 (2)C6—C7—C8121.1 (2)
O32—N3—C3118.2 (2)C7—C8—C11118.1 (2)
O1—C2—O2119.2 (2)O1—C11—C41121.5 (2)
O1—C2—C3115.7 (1)O1—C11—C8116.0 (2)
O2—C2—C3125.1 (2)C41—C11—C8122.4 (2)
N3—C3—C2114.6 (2)C41—C5—H5120.15
N3—C3—C4122.6 (2)C6—C7—H7119.36
C2—C3—C4122.8 (2)C6—C5—H5120.03
Cl4—C4—C3120.7 (1)C8—C7—H7119.58
Cl4—C4—C41119.5 (1)C5—C6—H6119.94
C3—C4—C41119.8 (2)C7—C8—H8120.85
C4—C41—C5124.7 (2)C7—C6—H6119.56
C4—C41—C11117.2 (2)C11—C8—H8121.03
C5—C41—C11118.1 (2)
Cl4—C4—C3—N30.1 (2)N3—C3—C4—C41180.0 (2)
Cl4—C4—C3—C2177.7 (1)C2—O1—C11—C412.2 (3)
Cl4—C4—C41—C53.1 (3)C2—O1—C11—C8177.5 (2)
Cl4—C4—C41—C11178.8 (1)C2—C3—C4—C412.4 (3)
O1—C2—C3—N3179.0 (2)C3—C2—O1—C111.1 (3)
O1—C2—C3—C41.2 (3)C3—C4—C41—C5176.8 (2)
O1—C11—C41—C40.9 (3)C3—C4—C41—C111.3 (2)
O1—C11—C41—C5179.2 (2)C4—C41—C5—C6177.6 (2)
O1—C11—C8—C7178.7 (2)C4—C41—C11—C8178.8 (2)
O2—C2—O1—C11178.8 (2)C41—C5—C6—C71.0 (4)
O2—C2—C3—N31.1 (3)C41—C11—C8—C71.0 (3)
O2—C2—C3—C4178.8 (2)C5—C41—C11—C80.5 (3)
O31—N3—C3—C276.8 (3)C5—C6—C7—C80.5 (4)
O31—N3—C3—C4101.0 (3)C6—C5—C41—C110.5 (3)
O32—N3—C3—C2101.5 (2)C6—C7—C8—C110.5 (4)
O32—N3—C3—C480.7 (3)C6—C7—C8—C110.5 (4)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y+1, z+2; (iii) x, y+1/2, z1/2; (iv) x, y1/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x+1, y+1, z+1; (vii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cl40.952.733.096 (3)104
C6—H6···O1viii0.952.513.449 (3)172
Symmetry code: (viii) x, y+1/2, z+1/2.
 

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