Literature DB >> 22259540

1-Benzyl-4-chloro-indoline-2,3-dione.

De Cai Wang, Bo Rong Leng, Gui Bin Wang, Ping Wei, Ping Kai Ou-Yang.   

Abstract

There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(10)ClNO(2), which differ in the dihedral angles between the mean planes of the phenyl ring and the 4-chloro-indoline-2,3-dione ring system [59.48 (9) and 79.0 (1)°]. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds, forming polymeric chains in [100].

Entities:  

Year:  2011        PMID: 22259540      PMCID: PMC3254398          DOI: 10.1107/S1600536811051816

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


Related literature

For the preparation, see: Bouhfid et al. (2005 ▶). For a related structure and background to isatin derivatives, see: Liu et al. (2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H10ClNO2 M = 271.69 Orthorhombic, a = 22.864 (5) Å b = 16.600 (3) Å c = 13.335 (3) Å V = 5061.2 (18) Å3 Z = 16 Mo Kα radiation μ = 0.30 mm−1 T = 293 K 0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.916, T max = 0.971 4623 measured reflections 4623 independent reflections 1929 reflections with I > 2σ(I) 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.064 wR(F 2) = 0.117 S = 1.00 4623 reflections 343 parameters H-atom parameters constrained Δρmax = 0.18 e Å−3 Δρmin = −0.20 e Å−3 Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051816/hb6540sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051816/hb6540Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811051816/hb6540Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H10ClNO2F(000) = 2240
Mr = 271.69Dx = 1.426 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 22.864 (5) Åθ = 9–13°
b = 16.600 (3) ŵ = 0.30 mm1
c = 13.335 (3) ÅT = 293 K
V = 5061.2 (18) Å3Block, yellow
Z = 160.30 × 0.20 × 0.10 mm
Enraf–Nonius CAD-4 diffractometer1929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
graphiteθmax = 25.4°, θmin = 1.8°
ω/2θ scansh = 0→27
Absorption correction: ψ scan (North et al., 1968)k = 0→20
Tmin = 0.916, Tmax = 0.971l = 0→16
4623 measured reflections3 standard reflections every 200 reflections
4623 independent reflections intensity decay: 1%
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.032P)2] where P = (Fo2 + 2Fc2)/3
4623 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.20 e Å3
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.
xyzUiso*/Ueq
Cl10.61720 (4)0.52555 (7)0.54905 (10)0.0902 (4)
C10.73389 (14)0.5069 (2)0.5352 (3)0.0438 (9)
N10.83104 (11)0.47219 (17)0.5229 (2)0.0506 (8)
O10.82562 (10)0.33371 (14)0.5350 (2)0.0681 (8)
O20.70097 (10)0.36781 (14)0.5538 (2)0.0628 (8)
C20.68738 (15)0.5601 (2)0.5384 (3)0.0522 (10)
C30.69793 (18)0.6420 (2)0.5343 (3)0.0644 (12)
H3A0.66710.67850.53580.077*
C40.7549 (2)0.6687 (2)0.5278 (3)0.0649 (12)
H4A0.76170.72390.52690.078*
C50.80188 (17)0.6178 (2)0.5228 (3)0.0540 (11)
H5A0.83980.63750.51730.065*
C60.79077 (15)0.5362 (2)0.5261 (3)0.0452 (9)
C70.80405 (15)0.3997 (2)0.5335 (3)0.0490 (10)
C80.73753 (16)0.4189 (2)0.5423 (3)0.0489 (10)
C90.89331 (15)0.4816 (2)0.5095 (3)0.0576 (11)
H9A0.90020.52070.45670.069*
H9B0.90960.43060.48760.069*
C100.92469 (15)0.5083 (2)0.6021 (3)0.0525 (10)
C110.96343 (16)0.5718 (2)0.5974 (3)0.0721 (13)
H11A0.96930.59900.53730.086*
C120.9933 (2)0.5946 (3)0.6822 (5)0.0975 (17)
H12A1.01960.63730.67900.117*
C130.9849 (2)0.5558 (4)0.7704 (5)0.1020 (19)
H13A1.00540.57170.82730.122*
C140.9457 (2)0.4926 (3)0.7757 (4)0.0911 (15)
H14A0.93980.46570.83600.109*
C150.91552 (17)0.4698 (2)0.6912 (3)0.0674 (12)
H15A0.88860.42790.69470.081*
O30.78599 (12)0.39116 (16)0.7763 (2)0.0807 (9)
O40.66106 (12)0.42670 (16)0.7850 (2)0.0824 (9)
N20.65413 (13)0.28816 (19)0.7866 (2)0.0596 (9)
Cl20.86828 (5)0.23348 (8)0.78394 (10)0.1009 (5)
C160.69392 (17)0.2242 (2)0.7838 (3)0.0512 (10)
C170.6827 (2)0.1434 (2)0.7823 (3)0.0699 (12)
H17A0.64440.12450.78110.084*
C180.7288 (2)0.0906 (2)0.7827 (3)0.0789 (14)
H18A0.72140.03550.78170.095*
C190.7861 (2)0.1170 (3)0.7845 (3)0.0767 (14)
H19A0.81670.08020.78590.092*
C200.79739 (17)0.1997 (3)0.7842 (3)0.0633 (11)
C210.75154 (15)0.2526 (2)0.7840 (3)0.0506 (10)
C220.74875 (18)0.3404 (2)0.7816 (3)0.0551 (11)
C230.68310 (19)0.3602 (3)0.7847 (3)0.0618 (11)
C240.59128 (16)0.2818 (3)0.7776 (3)0.0758 (13)
H24A0.58270.24320.72520.091*
H24B0.57640.33360.75560.091*
C250.55801 (16)0.2574 (2)0.8702 (3)0.0587 (11)
C260.58256 (16)0.2129 (2)0.9452 (3)0.0647 (12)
H26A0.62230.20090.94370.078*
C270.5485 (2)0.1861 (3)1.0228 (3)0.0774 (13)
H27A0.56530.15451.07270.093*
C280.4906 (2)0.2049 (3)1.0284 (4)0.0900 (16)
H28A0.46770.18641.08130.108*
C290.46671 (18)0.2517 (3)0.9539 (5)0.0910 (16)
H29A0.42750.26620.95730.109*
C300.49984 (18)0.2771 (2)0.8754 (3)0.0736 (13)
H30A0.48300.30790.82490.088*
U11U22U33U12U13U23
Cl10.0555 (7)0.0927 (9)0.1224 (10)0.0131 (6)0.0004 (7)0.0070 (8)
C10.046 (2)0.043 (2)0.042 (2)0.0025 (19)0.001 (2)−0.0029 (19)
N10.0396 (17)0.0442 (18)0.068 (2)−0.0015 (15)0.0006 (17)−0.0029 (18)
O10.0652 (17)0.0403 (16)0.099 (2)0.0090 (14)−0.0063 (16)−0.0039 (16)
O20.0551 (16)0.0472 (16)0.086 (2)−0.0117 (14)−0.0087 (16)−0.0008 (15)
C20.059 (2)0.048 (2)0.050 (3)0.007 (2)0.001 (2)−0.002 (2)
C30.077 (3)0.052 (3)0.064 (3)0.018 (2)0.000 (3)0.001 (2)
C40.096 (3)0.048 (3)0.051 (3)0.002 (3)0.001 (3)−0.002 (2)
C50.066 (3)0.040 (2)0.056 (3)−0.008 (2)0.007 (2)0.002 (2)
C60.050 (2)0.043 (2)0.043 (2)0.0059 (19)−0.0061 (19)−0.001 (2)
C70.049 (2)0.043 (2)0.056 (3)−0.001 (2)−0.009 (2)−0.002 (2)
C80.050 (2)0.046 (3)0.050 (3)−0.007 (2)−0.010 (2)−0.005 (2)
C90.055 (2)0.054 (3)0.063 (3)−0.002 (2)0.010 (2)0.000 (2)
C100.045 (2)0.055 (3)0.058 (3)0.0001 (19)0.007 (2)0.001 (2)
C110.056 (3)0.071 (3)0.089 (4)−0.019 (2)0.008 (3)−0.004 (3)
C120.066 (3)0.097 (4)0.129 (5)−0.017 (3)−0.007 (4)−0.031 (4)
C130.081 (4)0.126 (5)0.099 (5)0.016 (4)−0.041 (4)−0.041 (4)
C140.100 (4)0.100 (4)0.073 (4)0.022 (3)−0.012 (3)0.006 (3)
C150.070 (3)0.056 (3)0.076 (3)0.004 (2)−0.006 (3)0.002 (3)
O30.090 (2)0.0580 (18)0.095 (2)−0.0212 (17)0.0114 (19)0.0033 (18)
O40.107 (2)0.0579 (18)0.082 (2)0.0191 (17)0.0051 (19)0.0061 (18)
N20.057 (2)0.059 (2)0.063 (2)−0.0011 (18)0.003 (2)0.003 (2)
Cl20.0643 (7)0.1260 (11)0.1124 (11)0.0158 (8)0.0084 (8)0.0130 (9)
C160.068 (3)0.042 (2)0.044 (2)−0.002 (2)0.000 (2)−0.001 (2)
C170.097 (3)0.053 (3)0.060 (3)−0.018 (3)0.010 (3)−0.008 (3)
C180.137 (5)0.039 (3)0.060 (3)0.003 (3)0.008 (3)0.000 (2)
C190.105 (4)0.070 (3)0.055 (3)0.031 (3)0.007 (3)−0.002 (3)
C200.072 (3)0.066 (3)0.052 (3)0.011 (2)0.009 (2)0.001 (2)
C210.061 (2)0.044 (2)0.047 (2)−0.004 (2)0.003 (2)−0.0032 (19)
C220.073 (3)0.048 (3)0.044 (2)−0.007 (2)0.006 (2)0.000 (2)
C230.084 (3)0.052 (3)0.049 (3)0.008 (3)0.007 (2)0.000 (3)
C240.064 (3)0.099 (3)0.065 (3)−0.002 (2)−0.018 (3)0.006 (3)
C250.047 (2)0.069 (3)0.060 (3)0.002 (2)−0.010 (2)−0.005 (2)
C260.055 (3)0.088 (3)0.051 (3)0.007 (2)−0.002 (2)−0.003 (3)
C270.087 (3)0.082 (3)0.063 (3)0.012 (3)0.012 (3)−0.001 (3)
C280.090 (4)0.092 (4)0.088 (4)−0.016 (3)0.035 (3)−0.023 (3)
C290.055 (3)0.091 (4)0.128 (5)−0.001 (3)0.011 (4)−0.024 (4)
C300.057 (3)0.074 (3)0.090 (4)0.002 (2)−0.021 (3)0.002 (3)
Cl1—C21.710 (4)O3—C221.200 (4)
C1—C21.383 (4)O4—C231.213 (4)
C1—C61.394 (4)N2—C231.368 (4)
C1—C81.465 (4)N2—C161.399 (4)
N1—C71.359 (4)N2—C241.446 (4)
N1—C61.407 (4)Cl2—C201.715 (4)
N1—C91.444 (4)C16—C171.366 (4)
O1—C71.202 (4)C16—C211.399 (4)
O2—C81.201 (4)C17—C181.372 (5)
C2—C31.382 (4)C17—H17A0.9300
C3—C41.378 (5)C18—C191.381 (5)
C3—H3A0.9300C18—H18A0.9300
C4—C51.369 (5)C19—C201.397 (5)
C4—H4A0.9300C19—H19A0.9300
C5—C61.379 (4)C20—C211.368 (5)
C5—H5A0.9300C21—C221.459 (5)
C7—C81.558 (4)C22—C231.537 (5)
C9—C101.496 (5)C24—C251.506 (5)
C9—H9A0.9700C24—H24A0.9700
C9—H9B0.9700C24—H24B0.9700
C10—C151.365 (5)C25—C261.364 (5)
C10—C111.378 (4)C25—C301.371 (5)
C11—C121.374 (6)C26—C271.369 (5)
C11—H11A0.9300C26—H26A0.9300
C12—C131.354 (6)C27—C281.363 (5)
C12—H12A0.9300C27—H27A0.9300
C13—C141.381 (6)C28—C291.374 (6)
C13—H13A0.9300C28—H28A0.9300
C14—C151.375 (5)C29—C301.359 (5)
C14—H14A0.9300C29—H29A0.9300
C15—H15A0.9300C30—H30A0.9300
C2—C1—C6119.8 (3)C23—N2—C16110.4 (3)
C2—C1—C8132.7 (3)C23—N2—C24122.9 (4)
C6—C1—C8107.5 (3)C16—N2—C24126.1 (3)
C7—N1—C6111.6 (3)C17—C16—N2128.6 (4)
C7—N1—C9123.8 (3)C17—C16—C21120.6 (4)
C6—N1—C9124.6 (3)N2—C16—C21110.9 (3)
C3—C2—C1119.5 (3)C16—C17—C18118.8 (4)
C3—C2—Cl1119.8 (3)C16—C17—H17A120.6
C1—C2—Cl1120.7 (3)C18—C17—H17A120.6
C4—C3—C2118.9 (4)C17—C18—C19121.8 (4)
C4—C3—H3A120.5C17—C18—H18A119.1
C2—C3—H3A120.5C19—C18—H18A119.1
C5—C4—C3123.1 (4)C18—C19—C20119.2 (4)
C5—C4—H4A118.4C18—C19—H19A120.4
C3—C4—H4A118.4C20—C19—H19A120.4
C4—C5—C6117.4 (4)C21—C20—C19119.3 (4)
C4—C5—H5A121.3C21—C20—Cl2121.0 (3)
C6—C5—H5A121.3C19—C20—Cl2119.7 (4)
C5—C6—C1121.2 (3)C20—C21—C16120.3 (4)
C5—C6—N1128.4 (3)C20—C21—C22132.4 (4)
C1—C6—N1110.4 (3)C16—C21—C22107.2 (3)
O1—C7—N1128.5 (3)O3—C22—C21132.2 (4)
O1—C7—C8125.9 (3)O3—C22—C23123.0 (4)
N1—C7—C8105.6 (3)C21—C22—C23104.8 (3)
O2—C8—C1132.3 (4)O4—C23—N2126.5 (4)
O2—C8—C7123.0 (3)O4—C23—C22126.9 (4)
C1—C8—C7104.8 (3)N2—C23—C22106.6 (3)
N1—C9—C10113.7 (3)N2—C24—C25117.0 (3)
N1—C9—H9A108.8N2—C24—H24A108.1
C10—C9—H9A108.8C25—C24—H24A108.1
N1—C9—H9B108.8N2—C24—H24B108.1
C10—C9—H9B108.8C25—C24—H24B108.1
H9A—C9—H9B107.7H24A—C24—H24B107.3
C15—C10—C11119.7 (4)C26—C25—C30119.4 (4)
C15—C10—C9120.4 (4)C26—C25—C24122.7 (4)
C11—C10—C9119.8 (4)C30—C25—C24117.9 (4)
C12—C11—C10119.5 (4)C25—C26—C27119.8 (4)
C12—C11—H11A120.2C25—C26—H26A120.1
C10—C11—H11A120.2C27—C26—H26A120.1
C13—C12—C11120.8 (5)C28—C27—C26121.3 (5)
C13—C12—H12A119.6C28—C27—H27A119.4
C11—C12—H12A119.6C26—C27—H27A119.4
C12—C13—C14119.8 (5)C27—C28—C29118.4 (5)
C12—C13—H13A120.1C27—C28—H28A120.8
C14—C13—H13A120.1C29—C28—H28A120.8
C15—C14—C13119.5 (5)C30—C29—C28120.7 (4)
C15—C14—H14A120.2C30—C29—H29A119.6
C13—C14—H14A120.2C28—C29—H29A119.6
C10—C15—C14120.5 (4)C29—C30—C25120.4 (4)
C10—C15—H15A119.8C29—C30—H30A119.8
C14—C15—H15A119.8C25—C30—H30A119.8
C6—C1—C2—C3−1.2 (6)C23—N2—C16—C17−178.5 (4)
C8—C1—C2—C3177.0 (4)C24—N2—C16—C17−7.2 (6)
C6—C1—C2—Cl1179.7 (3)C23—N2—C16—C212.4 (5)
C8—C1—C2—Cl1−2.1 (6)C24—N2—C16—C21173.7 (4)
C1—C2—C3—C4−0.5 (6)N2—C16—C17—C18−178.0 (4)
Cl1—C2—C3—C4178.6 (3)C21—C16—C17—C181.1 (6)
C2—C3—C4—C51.7 (6)C16—C17—C18—C190.0 (7)
C3—C4—C5—C6−1.1 (6)C17—C18—C19—C20−1.1 (7)
C4—C5—C6—C1−0.7 (6)C18—C19—C20—C211.2 (7)
C4—C5—C6—N1−179.5 (3)C18—C19—C20—Cl2−178.7 (4)
C2—C1—C6—C51.8 (6)C19—C20—C21—C16−0.1 (6)
C8—C1—C6—C5−176.8 (3)Cl2—C20—C21—C16179.7 (3)
C2—C1—C6—N1−179.2 (3)C19—C20—C21—C22−178.6 (4)
C8—C1—C6—N12.2 (4)Cl2—C20—C21—C221.3 (7)
C7—N1—C6—C5176.6 (4)C17—C16—C21—C20−1.0 (6)
C9—N1—C6—C5−3.8 (6)N2—C16—C21—C20178.2 (4)
C7—N1—C6—C1−2.4 (4)C17—C16—C21—C22177.8 (3)
C9—N1—C6—C1177.2 (3)N2—C16—C21—C22−3.0 (5)
C6—N1—C7—O1−179.3 (4)C20—C21—C22—O32.6 (8)
C9—N1—C7—O11.1 (6)C16—C21—C22—O3−176.0 (4)
C6—N1—C7—C81.4 (4)C20—C21—C22—C23−179.0 (4)
C9—N1—C7—C8−178.2 (3)C16—C21—C22—C232.4 (4)
C2—C1—C8—O2−0.8 (8)C16—N2—C23—O4179.0 (4)
C6—C1—C8—O2177.5 (4)C24—N2—C23—O47.4 (7)
C2—C1—C8—C7−179.6 (4)C16—N2—C23—C22−0.8 (4)
C6—C1—C8—C7−1.3 (4)C24—N2—C23—C22−172.4 (3)
O1—C7—C8—O21.7 (6)O3—C22—C23—O4−2.2 (7)
N1—C7—C8—O2−179.0 (3)C21—C22—C23—O4179.2 (4)
O1—C7—C8—C1−179.3 (4)O3—C22—C23—N2177.6 (4)
N1—C7—C8—C1−0.1 (4)C21—C22—C23—N2−1.0 (4)
C7—N1—C9—C10−102.9 (4)C23—N2—C24—C25−109.5 (4)
C6—N1—C9—C1077.5 (4)C16—N2—C24—C2580.3 (5)
N1—C9—C10—C1549.4 (5)N2—C24—C25—C26−25.9 (6)
N1—C9—C10—C11−131.1 (3)N2—C24—C25—C30158.0 (4)
C15—C10—C11—C121.2 (6)C30—C25—C26—C272.3 (6)
C9—C10—C11—C12−178.3 (4)C24—C25—C26—C27−173.8 (4)
C10—C11—C12—C13−0.3 (7)C25—C26—C27—C28−1.9 (6)
C11—C12—C13—C14−0.2 (8)C26—C27—C28—C290.0 (7)
C12—C13—C14—C15−0.1 (7)C27—C28—C29—C301.5 (7)
C11—C10—C15—C14−1.6 (6)C28—C29—C30—C25−1.1 (7)
C9—C10—C15—C14177.9 (4)C26—C25—C30—C29−0.8 (6)
C13—C14—C15—C101.1 (7)C24—C25—C30—C29175.5 (4)
D—H···AD—HH···AD···AD—H···A
C3—H3A···O1i0.932.583.228 (4)127
C4—H4A···O2i0.932.563.473 (4)167
C18—H18A···O3ii0.932.403.329 (4)173
C19—H19A···O4ii0.932.603.382 (6)142
C26—H26A···O2iii0.932.593.350 (4)140
C29—H29A···O1iv0.932.593.505 (5)169
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C3—H3A⋯O1i0.932.583.228 (4)127
C4—H4A⋯O2i0.932.563.473 (4)167
C18—H18A⋯O3ii0.932.403.329 (4)173
C19—H19A⋯O4ii0.932.603.382 (6)142
C26—H26A⋯O2iii0.932.593.350 (4)140
C29—H29A⋯O1iv0.932.593.505 (5)169

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

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  1-Benzyl-6-chloro-indoline-2,3-dione.

Authors:  Hua-Quan Liu; Dong-Mei Fan; De-Cai Wang; Ping-Kai Ou-Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-25

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total

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