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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
CCDC reference: 272057
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (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
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-2
H- chromen-2-one
top
Crystal data top
C9H4ClNO4 | F(000) = 456.0 |
Mr = 225.59 | Dx = 1.646 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.5110 (4) Å | θ = 30.0–35.0° |
b = 13.526 (1) Å | µ = 3.71 mm−1 |
c = 8.6612 (5) Å | T = 297 K |
β = 114.119 (5)° | Rod, yellow |
V = 910.0 (1) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.032 |
Radiation source: sealed X-ray tube | θmax = 74.9° |
ω/2θ scans | h = −10→0 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→16 |
Tmin = 0.433, Tmax = 0.478 | l = −9→10 |
2084 measured reflections | 3 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) = 0.198 | Δρmax = 0.34 e Å−3 |
S = 1.21 | Δρmin = −0.43 e Å−3 |
1876 reflections | Extinction correction: type 2 Gaussian isotropic (Zachariasen, 1967) |
137 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl4 | 0.48318 (6) | 0.53267 (4) | 0.70590 (7) | 0.0588 (2) | |
O1 | 0.0943 (2) | 0.2946 (1) | 0.4628 (2) | 0.0512 (4) | |
O2 | 0.2479 (2) | 0.1891 (1) | 0.6613 (2) | 0.0644 (5) | |
O31 | 0.4867 (4) | 0.3193 (3) | 0.9598 (3) | 0.126 (1) | |
O32 | 0.6406 (3) | 0.3048 (2) | 0.8216 (3) | 0.0882 (7) | |
N3 | 0.5066 (2) | 0.3235 (1) | 0.8317 (2) | 0.0560 (5) | |
C2 | 0.2346 (3) | 0.2710 (1) | 0.6051 (2) | 0.0449 (5) | |
C3 | 0.3588 (2) | 0.3501 (1) | 0.6775 (2) | 0.0418 (4) | |
C4 | 0.3365 (2) | 0.4414 (1) | 0.6111 (2) | 0.0404 (4) | |
C41 | 0.1877 (2) | 0.4628 (1) | 0.4585 (2) | 0.0408 (5) | |
C5 | 0.1554 (3) | 0.5538 (2) | 0.3737 (3) | 0.0568 (6) | |
C6 | 0.0120 (4) | 0.5651 (2) | 0.2250 (3) | 0.0693 (7) | |
C7 | −0.1028 (4) | 0.4875 (2) | 0.1593 (3) | 0.0704 (7) | |
C8 | −0.0756 (3) | 0.3978 (2) | 0.2400 (3) | 0.0599 (6) | |
C11 | 0.0705 (2) | 0.3865 (1) | 0.3882 (2) | 0.0437 (5) | |
H5 | 0.2325 | 0.6073 | 0.4184 | 0.0684* | |
H6 | −0.0099 | 0.6265 | 0.1674 | 0.0832* | |
H7 | −0.2015 | 0.4966 | 0.0561 | 0.0843* | |
H8 | −0.1553 | 0.3452 | 0.1957 | 0.0720* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.0559 (5) | 0.0475 (5) | 0.0649 (5) | −0.0141 (2) | 0.0163 (3) | −0.0122 (2) |
O1 | 0.0460 (8) | 0.0391 (7) | 0.0570 (8) | −0.0034 (5) | 0.0093 (6) | −0.0047 (5) |
O2 | 0.065 (1) | 0.0415 (8) | 0.084 (1) | −0.0004 (6) | 0.0272 (9) | 0.0135 (7) |
O31 | 0.097 (2) | 0.227 (3) | 0.0478 (10) | 0.024 (2) | 0.022 (1) | 0.037 (1) |
O32 | 0.0502 (10) | 0.122 (2) | 0.076 (1) | 0.022 (1) | 0.0095 (8) | 0.009 (1) |
N3 | 0.0504 (10) | 0.062 (1) | 0.0451 (8) | 0.0000 (8) | 0.0085 (7) | 0.0060 (7) |
C2 | 0.0443 (9) | 0.0388 (9) | 0.0506 (9) | 0.0011 (7) | 0.0184 (7) | 0.0017 (7) |
C3 | 0.0395 (9) | 0.0448 (9) | 0.0384 (8) | 0.0013 (6) | 0.0132 (7) | 0.0010 (6) |
C4 | 0.0437 (9) | 0.0387 (9) | 0.0394 (8) | −0.0047 (7) | 0.0177 (7) | −0.0057 (6) |
C41 | 0.0440 (10) | 0.0398 (10) | 0.0398 (9) | 0.0053 (6) | 0.0182 (8) | 0.0013 (6) |
C5 | 0.063 (1) | 0.048 (1) | 0.063 (1) | 0.0087 (9) | 0.028 (1) | 0.0136 (9) |
C6 | 0.081 (2) | 0.069 (2) | 0.060 (1) | 0.026 (1) | 0.030 (1) | 0.025 (1) |
C7 | 0.065 (1) | 0.090 (2) | 0.043 (1) | 0.031 (1) | 0.009 (1) | 0.009 (1) |
C8 | 0.047 (1) | 0.069 (1) | 0.050 (1) | 0.0070 (9) | 0.0056 (8) | −0.0098 (9) |
C11 | 0.0438 (9) | 0.0436 (9) | 0.0393 (9) | 0.0060 (7) | 0.0124 (7) | −0.0023 (6) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.709 (2) | C41—C5 | 1.402 (3) |
O1—C2 | 1.358 (2) | C41—C11 | 1.390 (3) |
O1—C11 | 1.377 (2) | C5—C6 | 1.374 (4) |
O2—C2 | 1.197 (2) | C6—C7 | 1.388 (4) |
O31—N3 | 1.190 (3) | C7—C8 | 1.372 (4) |
O32—N3 | 1.207 (3) | C8—C11 | 1.383 (3) |
N3—C3 | 1.457 (2) | C5—H5 | 0.946 |
C2—C3 | 1.454 (3) | C7—H7 | 0.952 |
C3—C4 | 1.342 (3) | C6—H6 | 0.947 |
C4—C41 | 1.438 (3) | C8—H8 | 0.948 |
| | | |
Cl4···O2i | 2.981 (2) | O2···C6iv | 3.585 (3) |
Cl4···O31ii | 3.443 (3) | O31···C2v | 3.144 (3) |
O1···O2iii | 3.371 (2) | O31···O32v | 3.316 (3) |
O1···C6iv | 3.448 (3) | O31···C3v | 3.415 (3) |
O2···C11v | 3.100 (2) | O32···C5vi | 3.454 (3) |
O2···O31iii | 3.176 (3) | C4···C7vii | 3.474 (3) |
O2···C8v | 3.310 (3) | C5···C11vii | 3.441 (3) |
O2···C41v | 3.490 (2) | | |
| | | |
C2—O1—C11 | 122.9 (1) | C41—C5—C6 | 119.8 (2) |
O31—N3—O32 | 123.8 (2) | C5—C6—C7 | 120.5 (2) |
O31—N3—C3 | 117.9 (2) | C6—C7—C8 | 121.1 (2) |
O32—N3—C3 | 118.2 (2) | C7—C8—C11 | 118.1 (2) |
O1—C2—O2 | 119.2 (2) | O1—C11—C41 | 121.5 (2) |
O1—C2—C3 | 115.7 (1) | O1—C11—C8 | 116.0 (2) |
O2—C2—C3 | 125.1 (2) | C41—C11—C8 | 122.4 (2) |
N3—C3—C2 | 114.6 (2) | C41—C5—H5 | 120.15 |
N3—C3—C4 | 122.6 (2) | C6—C7—H7 | 119.36 |
C2—C3—C4 | 122.8 (2) | C6—C5—H5 | 120.03 |
Cl4—C4—C3 | 120.7 (1) | C8—C7—H7 | 119.58 |
Cl4—C4—C41 | 119.5 (1) | C5—C6—H6 | 119.94 |
C3—C4—C41 | 119.8 (2) | C7—C8—H8 | 120.85 |
C4—C41—C5 | 124.7 (2) | C7—C6—H6 | 119.56 |
C4—C41—C11 | 117.2 (2) | C11—C8—H8 | 121.03 |
C5—C41—C11 | 118.1 (2) | | |
| | | |
Cl4—C4—C3—N3 | 0.1 (2) | N3—C3—C4—C41 | 180.0 (2) |
Cl4—C4—C3—C2 | 177.7 (1) | C2—O1—C11—C41 | −2.2 (3) |
Cl4—C4—C41—C5 | 3.1 (3) | C2—O1—C11—C8 | 177.5 (2) |
Cl4—C4—C41—C11 | −178.8 (1) | C2—C3—C4—C41 | −2.4 (3) |
O1—C2—C3—N3 | 179.0 (2) | C3—C2—O1—C11 | 1.1 (3) |
O1—C2—C3—C4 | 1.2 (3) | C3—C4—C41—C5 | −176.8 (2) |
O1—C11—C41—C4 | 0.9 (3) | C3—C4—C41—C11 | 1.3 (2) |
O1—C11—C41—C5 | 179.2 (2) | C4—C41—C5—C6 | 177.6 (2) |
O1—C11—C8—C7 | −178.7 (2) | C4—C41—C11—C8 | −178.8 (2) |
O2—C2—O1—C11 | −178.8 (2) | C41—C5—C6—C7 | 1.0 (4) |
O2—C2—C3—N3 | −1.1 (3) | C41—C11—C8—C7 | 1.0 (3) |
O2—C2—C3—C4 | −178.8 (2) | C5—C41—C11—C8 | −0.5 (3) |
O31—N3—C3—C2 | −76.8 (3) | C5—C6—C7—C8 | −0.5 (4) |
O31—N3—C3—C4 | 101.0 (3) | C6—C5—C41—C11 | −0.5 (3) |
O32—N3—C3—C2 | 101.5 (2) | C6—C7—C8—C11 | −0.5 (4) |
O32—N3—C3—C4 | −80.7 (3) | C6—C7—C8—C11 | −0.5 (4) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+1/2, z−1/2; (iv) −x, y−1/2, −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···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cl4 | 0.95 | 2.73 | 3.096 (3) | 104 |
C6—H6···O1viii | 0.95 | 2.51 | 3.449 (3) | 172 |
Symmetry code: (viii) −x, y+1/2, −z+1/2. |
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