Literature DB >> 24860355

6-Chloro-8-nitro-4-oxo-4H-chromene-3-carbaldehyde.

Yoshinobu Ishikawa1.   

Abstract

In the title compound, C10H4ClNO5, the non-H atoms of the 6-chloro-chromone unit are coplanar (r.m.s. deviation = 0.017 Å) with the largest deviation from the mean plane [0.031 (2) Å] being found for the C=O C atom. The nitro group (NO2) is inclined to the chromone unit mean plane by 13.3 (2) °. The formyl group is also twisted with respect to the attached ring [C-C-C-O torsion angles = 10.8 (4) and -171.8 (2)°]. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds forming slab-like networks lying parallel to (-301). The slabs are linked by π-π inter-actions involving the benzene rings of the chromone units [centroid-centroid distance = 3.770 (3) Å].

Entities:  

Year:  2014        PMID： 24860355      PMCID： PMC4011269          DOI： 10.1107/S1600536814007788

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Ishikawa & Motohashi (2013 ▶); Ishikawa (2014 ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶); Sirimulla et al. (2013 ▶).

Experimental

Crystal data

C10H4ClNO5 M = 253.60 Monoclinic, a = 18.585 (9) Å b = 10.4918 (17) Å c = 11.094 (3) Å β = 119.23 (3)° V = 1887.7 (12) Å3 Z = 8 Mo Kα radiation μ = 0.41 mm−1 T = 100 K 0.38 × 0.22 × 0.18 mm

Data collection

Rigaku AFC-7R diffractometer 2588 measured reflections 2173 independent reflections 1903 reflections with F 2 > 2σ(F 2) R int = 0.019 3 standard reflections every 150 reflections intensity decay: −0.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.098 S = 1.05 2173 reflections 154 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.38 e Å−3 Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 1989 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814007788/tk5305sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007788/tk5305Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814007788/tk5305Isup3.cml CCDC reference: 996005 Additional supporting information: crystallographic information; 3D view; checkCIF report
C10H4ClNO5F(000) = 1024.00
Mr = 253.60Dx = 1.785 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 18.585 (9) Åθ = 15.4–17.5°
b = 10.4918 (17) ŵ = 0.41 mm−1
c = 11.094 (3) ÅT = 100 K
β = 119.23 (3)°Plate, yellow
V = 1887.7 (12) Å30.38 × 0.22 × 0.18 mm
Z = 8
Rigaku AFC-7R diffractometerθmax = 27.5°
ω–2θ scansh = −13→24
2588 measured reflectionsk = 0→13
2173 independent reflectionsl = −14→12
1903 reflections with F2 > 2σ(F2)3 standard reflections every 150 reflections
Rint = 0.019 intensity decay: −0.7%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0464P)2 + 3.8081P] where P = (Fo2 + 2Fc2)/3
2173 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods
Refinement. Refinement was performed using all reflections. 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).
xyzUiso*/Ueq
Cl10.44735 (3)0.12307 (4)0.37638 (4)0.02112 (14)
O10.32475 (8)0.53278 (12)−0.03825 (12)0.0162 (3)
O20.44970 (8)0.63260 (12)0.36926 (13)0.0197 (3)
O30.30625 (11)0.16061 (14)−0.15276 (15)0.0321 (4)
O40.25980 (8)0.35147 (13)−0.21525 (13)0.0220 (3)
O50.34664 (10)0.91339 (13)0.07444 (15)0.0259 (4)
N10.30008 (9)0.27227 (15)−0.12702 (15)0.0172 (3)
C10.33433 (11)0.65518 (17)0.00207 (18)0.0164 (4)
C20.37408 (11)0.69511 (16)0.13480 (18)0.0151 (4)
C30.41012 (11)0.60278 (16)0.24645 (17)0.0146 (4)
C40.42517 (10)0.37048 (16)0.29954 (17)0.0143 (4)
C50.41278 (10)0.24532 (16)0.25645 (17)0.0152 (4)
C60.37215 (10)0.21418 (17)0.11583 (18)0.0157 (4)
C70.34310 (10)0.31087 (17)0.01960 (17)0.0144 (4)
C80.39566 (10)0.46805 (16)0.20106 (17)0.0132 (4)
C90.35390 (10)0.43954 (16)0.06022 (17)0.0136 (4)
C100.38301 (12)0.83413 (18)0.16297 (19)0.0191 (4)
H10.31140.7185−0.06790.0197*
H20.45350.39030.39530.0172*
H30.36470.12760.08720.0188*
H40.41890.86220.25460.0229*
U11U22U33U12U13U23
Cl10.0291 (3)0.0136 (3)0.0160 (3)0.00127 (17)0.00746 (18)0.00454 (15)
O10.0234 (7)0.0120 (6)0.0106 (6)0.0016 (5)0.0061 (5)0.0011 (5)
O20.0231 (7)0.0158 (7)0.0127 (6)−0.0004 (5)0.0029 (6)−0.0029 (5)
O30.0562 (11)0.0153 (7)0.0186 (7)−0.0017 (7)0.0133 (7)−0.0070 (6)
O40.0250 (7)0.0227 (7)0.0114 (6)0.0001 (6)0.0035 (6)−0.0006 (5)
O50.0394 (9)0.0143 (7)0.0239 (7)0.0011 (6)0.0154 (7)0.0019 (6)
N10.0220 (8)0.0170 (8)0.0125 (7)−0.0043 (6)0.0083 (6)−0.0037 (6)
C10.0212 (9)0.0119 (8)0.0159 (9)0.0026 (7)0.0089 (7)0.0024 (7)
C20.0179 (8)0.0120 (8)0.0148 (8)0.0005 (7)0.0075 (7)−0.0002 (7)
C30.0158 (8)0.0137 (8)0.0128 (8)−0.0005 (7)0.0059 (7)−0.0011 (7)
C40.0156 (8)0.0140 (9)0.0114 (8)0.0000 (7)0.0050 (7)0.0004 (7)
C50.0173 (8)0.0134 (8)0.0133 (8)0.0016 (7)0.0063 (7)0.0028 (7)
C60.0190 (8)0.0127 (8)0.0162 (8)−0.0022 (7)0.0092 (7)−0.0024 (7)
C70.0167 (8)0.0158 (8)0.0100 (8)−0.0027 (7)0.0059 (7)−0.0035 (7)
C80.0146 (8)0.0125 (8)0.0118 (8)−0.0003 (6)0.0059 (7)−0.0005 (6)
C90.0158 (8)0.0128 (8)0.0116 (8)0.0010 (6)0.0062 (7)0.0013 (6)
C100.0250 (10)0.0136 (9)0.0187 (9)−0.0025 (7)0.0107 (8)−0.0013 (7)
Cl1—C51.7301 (18)C3—C81.480 (3)
O1—C11.343 (3)C4—C51.378 (3)
O1—C91.366 (2)C4—C81.399 (3)
O2—C31.231 (2)C5—C61.400 (3)
O3—N11.224 (3)C6—C71.377 (3)
O4—N11.2220 (19)C7—C91.406 (3)
O5—C101.210 (3)C8—C91.396 (3)
N1—C71.476 (3)C1—H10.950
C1—C21.352 (3)C4—H20.950
C2—C31.453 (3)C6—H30.950
C2—C101.484 (3)C10—H40.950
O1···O42.5723 (18)C6···N1iii3.266 (4)
O1···N12.865 (2)C6···C5v3.544 (4)
O1···C32.853 (3)C6···C7iii3.530 (3)
O2···C13.566 (3)C7···O2vi3.207 (3)
O2···C42.833 (3)C7···N1iii3.516 (4)
O2···C102.911 (3)C7···C6iii3.530 (3)
O3···C62.670 (3)C7···C7iii3.511 (4)
O3···C93.590 (3)C8···C4v3.487 (4)
O4···C63.526 (3)C8···C8v3.479 (4)
O4···C92.834 (3)C9···O2vi3.452 (3)
O5···C12.803 (3)C10···O3iv3.011 (4)
C1···C82.751 (3)C10···N1iv3.544 (4)
C2···C92.777 (3)C10···C1viii3.529 (4)
C4···C72.781 (3)Cl1···H22.8102
C5···C92.786 (3)Cl1···H32.8003
C6···C82.789 (3)O2···H22.5550
Cl1···Cl1i3.5748 (10)O2···H42.6525
Cl1···O2ii3.5947 (15)O3···H32.3584
Cl1···O4iii3.371 (3)O5···H12.4692
Cl1···O5iv3.535 (3)N1···H32.5702
Cl1···C6v3.448 (3)C1···H43.2764
O1···O2vi3.433 (3)C3···H13.2794
O1···O3vii3.365 (2)C3···H22.6539
O1···O5viii3.062 (3)C3···H42.7252
O1···C4vi3.321 (3)C4···H33.2742
O2···Cl1ii3.5947 (15)C6···H23.2764
O2···O1iv3.433 (3)C9···H13.1800
O2···O3iv3.352 (3)C9···H23.2847
O2···O4iv3.183 (3)C9···H33.2837
O2···N1iv2.974 (3)C10···H12.5450
O2···C1v3.551 (3)H1···H43.4766
O2···C2v3.362 (4)Cl1···H1iv3.3241
O2···C3v3.435 (4)Cl1···H3v3.3146
O2···C4ii3.250 (3)Cl1···H4x2.9832
O2···C7iv3.207 (3)O1···H2vi2.9400
O2···C9iv3.452 (3)O2···H2ii2.3513
O3···O1ix3.365 (2)O3···H1ix2.8519
O3···O2vi3.352 (3)O3···H4vi2.7560
O3···O4ix3.524 (2)O4···H1ix2.5249
O3···O5x3.435 (3)O4···H3iii3.2607
O3···O5vi3.542 (3)O5···H1viii3.2161
O3···C1ix3.458 (3)O5···H3xi2.2666
O3···C2vi3.512 (4)N1···H1ix3.0357
O3···C10vi3.011 (4)N1···H3iii3.4641
O4···Cl1iii3.371 (3)N1···H4vi3.3795
O4···O2vi3.183 (3)C1···H1viii3.4007
O4···O3vii3.524 (2)C1···H2vi3.0167
O4···O5ix3.538 (3)C2···H1viii3.2806
O4···C1ix3.463 (3)C3···H2ii3.5197
O4···C2vi3.312 (4)C4···H1iv3.2457
O4···C3vi3.062 (4)C5···H1iv3.3272
O4···C5iii3.177 (3)C7···H2v3.5199
O4···C6iii3.217 (3)C7···H3iii3.5024
O5···Cl1vi3.535 (3)C8···H2v3.5485
O5···O1viii3.062 (3)C9···H2v3.4053
O5···O3xi3.435 (3)C10···H1viii3.2794
O5···O3iv3.542 (3)C10···H3xi3.1660
O5···O4vii3.538 (3)C10···H4v3.3452
O5···C1viii3.124 (4)H1···Cl1vi3.3241
O5···C6xi3.191 (3)H1···O3vii2.8519
N1···O2vi2.974 (3)H1···O4vii2.5249
N1···C2vi3.541 (4)H1···O5viii3.2161
N1···C3vi3.267 (4)H1···N1vii3.0357
N1···C5iii3.492 (3)H1···C1viii3.4007
N1···C6iii3.266 (4)H1···C2viii3.2806
N1···C7iii3.516 (4)H1···C4vi3.2457
N1···C10vi3.544 (4)H1···C5vi3.3272
C1···O2v3.551 (3)H1···C10viii3.2794
C1···O3vii3.458 (3)H1···H1viii3.3600
C1···O4vii3.463 (3)H1···H2vi3.0810
C1···O5viii3.124 (4)H2···O1iv2.9400
C1···C4vi3.417 (4)H2···O2ii2.3513
C1···C10viii3.529 (4)H2···C1iv3.0167
C2···O2v3.362 (4)H2···C3ii3.5197
C2···O3iv3.512 (4)H2···C7v3.5199
C2···O4iv3.312 (4)H2···C8v3.5485
C2···N1iv3.541 (4)H2···C9v3.4053
C3···O2v3.435 (4)H2···H1iv3.0810
C3···O4iv3.062 (4)H2···H2ii3.1238
C3···N1iv3.267 (4)H3···Cl1v3.3146
C3···C3v3.303 (4)H3···O4iii3.2607
C4···O1iv3.321 (3)H3···O5x2.2666
C4···O2ii3.250 (3)H3···N1iii3.4641
C4···C1iv3.417 (4)H3···C7iii3.5024
C4···C4v3.454 (4)H3···C10x3.1660
C4···C8v3.487 (4)H3···H4x3.2237
C5···O4iii3.177 (3)H4···Cl1xi2.9832
C5···N1iii3.492 (3)H4···O3iv2.7560
C5···C5v3.314 (4)H4···N1iv3.3795
C5···C6v3.544 (4)H4···C10v3.3452
C6···Cl1v3.448 (3)H4···H3xi3.2237
C6···O4iii3.217 (3)H4···H4v3.0665
C6···O5x3.191 (3)
C1—O1—C9118.83 (14)N1—C7—C9122.16 (15)
O3—N1—O4123.66 (15)C6—C7—C9121.20 (16)
O3—N1—C7117.23 (14)C3—C8—C4119.75 (15)
O4—N1—C7119.10 (16)C3—C8—C9119.65 (15)
O1—C1—C2124.91 (16)C4—C8—C9120.59 (16)
C1—C2—C3120.08 (16)O1—C9—C7119.50 (15)
C1—C2—C10118.65 (16)O1—C9—C8121.89 (15)
C3—C2—C10121.21 (15)C7—C9—C8118.60 (15)
O2—C3—C2123.47 (16)O5—C10—C2122.94 (16)
O2—C3—C8122.01 (15)O1—C1—H1117.543
C2—C3—C8114.53 (14)C2—C1—H1117.546
C5—C4—C8119.41 (16)C5—C4—H2120.299
Cl1—C5—C4120.22 (13)C8—C4—H2120.290
Cl1—C5—C6118.66 (14)C5—C6—H3120.469
C4—C5—C6121.12 (16)C7—C6—H3120.471
C5—C6—C7119.06 (17)O5—C10—H4118.529
N1—C7—C6116.64 (16)C2—C10—H4118.529
C1—O1—C9—C7178.93 (17)C5—C4—C8—C3−178.83 (17)
C1—O1—C9—C8−2.2 (3)C5—C4—C8—C90.1 (3)
C9—O1—C1—C22.8 (3)C8—C4—C5—Cl1−179.02 (16)
C9—O1—C1—H1−177.2C8—C4—C5—C60.9 (3)
O3—N1—C7—C6−12.8 (3)H2—C4—C5—Cl11.0
O3—N1—C7—C9167.45 (19)H2—C4—C5—C6−179.1
O4—N1—C7—C6166.20 (17)H2—C4—C8—C31.2
O4—N1—C7—C9−13.5 (3)H2—C4—C8—C9−179.9
O1—C1—C2—C3−0.2 (4)Cl1—C5—C6—C7178.84 (13)
O1—C1—C2—C10177.18 (18)Cl1—C5—C6—H3−1.1
H1—C1—C2—C3179.8C4—C5—C6—C7−1.0 (3)
H1—C1—C2—C10−2.8C4—C5—C6—H3179.0
C1—C2—C3—O2177.3 (2)C5—C6—C7—N1−179.42 (17)
C1—C2—C3—C8−2.7 (3)C5—C6—C7—C90.3 (3)
C1—C2—C10—O510.8 (4)H3—C6—C7—N10.6
C1—C2—C10—H4−169.2H3—C6—C7—C9−179.7
C3—C2—C10—O5−171.8 (2)N1—C7—C9—O1−0.8 (3)
C3—C2—C10—H48.2N1—C7—C9—C8−179.69 (17)
C10—C2—C3—O2−0.1 (4)C6—C7—C9—O1179.53 (18)
C10—C2—C3—C8−179.99 (19)C6—C7—C9—C80.6 (3)
O2—C3—C8—C42.1 (4)C3—C8—C9—O1−0.8 (3)
O2—C3—C8—C9−176.81 (19)C3—C8—C9—C7178.10 (17)
C2—C3—C8—C4−177.99 (18)C4—C8—C9—O1−179.68 (18)
C2—C3—C8—C93.1 (3)C4—C8—C9—C7−0.8 (3)
D—H···AD—HH···AD···AD—H···A
C1—H1···O4vii0.952.533.463 (3)169
C4—H2···O2ii0.952.353.250 (3)158
C6—H3···O5x0.952.273.191 (3)164
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1⋯O4i 0.952.533.463 (3)169
C4—H2⋯O2ii 0.952.353.250 (3)158
C6—H3⋯O5iii 0.952.273.191 (3)164

Symmetry codes: (i) ; (ii) ; (iii) .

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