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In the title compound, C15H11Cl4NO4, the isoindole unit is planar. The dihedral angle between the isoindole unit and the furan ring is 84.91 (4)°. The mol­ecules are linked via inter­molecular O—H...O hydrogen bonds, forming a three-dimensional network. π–π Inter­actions are also observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013736/sj2264sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013736/sj2264Isup2.hkl
Contains datablock I

CCDC reference: 643662

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.033
  • wR factor = 0.089
  • Data-to-parameter ratio = 42.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O3 .. 3.15 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact Cl2 .. C1 .. 3.24 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4,5,6,7-Tetrachloro-3-furan-3-yl-3-hydroxy-2-(3-hydroxypropyl)-2,3- dihydroisoindol-1-one top
Crystal data top
C15H11Cl4NO4F(000) = 832
Mr = 411.05Dx = 1.686 Mg m3
Monoclinic, P21/cMelting point: 467-468 K K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.6531 (3) ÅCell parameters from 10023 reflections
b = 9.8856 (2) Åθ = 2.8–40.0°
c = 15.1278 (4) ŵ = 0.75 mm1
β = 111.716 (1)°T = 100 K
V = 1619.01 (7) Å3Block, colorless
Z = 40.55 × 0.45 × 0.32 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
10023 independent reflections
Radiation source: fine-focus sealed tube8567 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.33 pixels mm-1θmax = 40.0°, θmin = 2.8°
ω scansh = 2021
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1717
Tmin = 0.682, Tmax = 0.794l = 2726
48681 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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.4085P]
where P = (Fo2 + 2Fc2)/3
10023 reflections(Δ/σ)max = 0.001
234 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl10.096731 (18)0.218790 (19)0.094557 (14)0.01675 (4)
Cl20.114774 (19)0.09396 (2)0.123938 (14)0.01836 (4)
Cl30.26082 (2)0.269248 (19)0.030224 (17)0.02212 (4)
Cl40.396491 (19)0.13045 (2)0.089862 (16)0.02005 (4)
O10.25753 (6)0.42350 (6)0.01794 (4)0.01666 (10)
O20.39701 (7)0.15943 (8)0.16767 (5)0.02229 (12)
O30.04376 (6)0.28663 (7)0.19934 (4)0.01703 (10)
O40.55616 (6)0.67193 (7)0.17043 (4)0.01892 (11)
N10.30181 (6)0.31855 (7)0.10793 (5)0.01447 (10)
C10.07069 (8)0.33998 (10)0.24951 (6)0.02071 (14)
H1A0.12450.30770.30790.030 (4)*
C20.09430 (9)0.44558 (10)0.20249 (7)0.02391 (16)
H2A0.16570.49790.22170.036 (4)*
C30.01260 (8)0.46122 (9)0.11675 (7)0.02088 (14)
H3A0.02470.52590.06950.042 (5)*
C40.09203 (7)0.36278 (7)0.11870 (5)0.01356 (11)
C50.22043 (7)0.32570 (7)0.05283 (5)0.01242 (10)
C60.22784 (6)0.17990 (7)0.01803 (5)0.01143 (10)
C70.17521 (7)0.12217 (7)0.04121 (5)0.01227 (10)
C80.18609 (7)0.01823 (7)0.05610 (5)0.01346 (10)
C90.25299 (7)0.09732 (7)0.01475 (6)0.01486 (11)
C100.31060 (7)0.03617 (7)0.04148 (5)0.01418 (11)
C110.29546 (7)0.10191 (7)0.05778 (5)0.01288 (10)
C120.33961 (7)0.19204 (8)0.11750 (5)0.01484 (11)
C130.31028 (7)0.42923 (9)0.16890 (6)0.01756 (13)
H13A0.24560.49440.17470.024 (3)*
H13B0.29590.39380.23190.021 (3)*
C140.43430 (7)0.50137 (8)0.13223 (6)0.01650 (12)
H14A0.44170.55430.07640.025 (4)*
H14B0.50050.43530.11410.026 (4)*
C150.44533 (8)0.59336 (9)0.20888 (6)0.01737 (13)
H15A0.44740.53950.26190.030 (4)*
H15B0.37430.65290.23210.019 (3)*
H1O40.5752 (16)0.6887 (18)0.2175 (13)0.036 (4)*
H1O10.3157 (16)0.3945 (18)0.0638 (13)0.036 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01933 (8)0.01664 (7)0.01758 (8)0.00247 (6)0.01067 (6)0.00040 (6)
Cl20.01989 (8)0.01754 (7)0.01688 (8)0.00558 (6)0.00591 (6)0.00336 (6)
Cl30.02223 (9)0.00975 (6)0.03139 (10)0.00113 (6)0.00644 (7)0.00230 (6)
Cl40.01737 (8)0.01742 (8)0.02523 (9)0.00434 (6)0.00773 (7)0.00497 (6)
O10.0198 (2)0.01131 (19)0.0167 (2)0.00126 (19)0.00433 (19)0.00175 (17)
O20.0232 (3)0.0276 (3)0.0218 (3)0.0029 (2)0.0150 (2)0.0008 (2)
O30.0149 (2)0.0203 (2)0.0143 (2)0.0015 (2)0.00349 (18)0.00011 (19)
O40.0188 (2)0.0228 (3)0.0155 (2)0.0072 (2)0.00672 (19)0.0009 (2)
N10.0140 (2)0.0143 (2)0.0168 (2)0.0002 (2)0.0078 (2)0.0037 (2)
C10.0154 (3)0.0271 (4)0.0168 (3)0.0015 (3)0.0026 (2)0.0048 (3)
C20.0188 (3)0.0256 (4)0.0249 (4)0.0084 (3)0.0053 (3)0.0065 (3)
C30.0208 (3)0.0179 (3)0.0227 (3)0.0073 (3)0.0065 (3)0.0017 (3)
C40.0137 (3)0.0128 (2)0.0142 (3)0.0011 (2)0.0052 (2)0.0018 (2)
C50.0130 (2)0.0106 (2)0.0138 (2)0.0002 (2)0.0052 (2)0.00128 (19)
C60.0115 (2)0.0100 (2)0.0128 (2)0.00038 (19)0.00456 (19)0.00078 (19)
C70.0127 (2)0.0114 (2)0.0129 (2)0.0001 (2)0.0050 (2)0.00076 (19)
C80.0134 (2)0.0114 (2)0.0144 (3)0.0013 (2)0.0036 (2)0.0016 (2)
C90.0142 (3)0.0097 (2)0.0180 (3)0.0003 (2)0.0029 (2)0.0005 (2)
C100.0125 (2)0.0120 (2)0.0169 (3)0.0018 (2)0.0041 (2)0.0015 (2)
C110.0122 (2)0.0123 (2)0.0144 (3)0.0008 (2)0.0052 (2)0.0002 (2)
C120.0134 (3)0.0173 (3)0.0147 (3)0.0000 (2)0.0061 (2)0.0007 (2)
C130.0154 (3)0.0195 (3)0.0172 (3)0.0019 (2)0.0054 (2)0.0066 (2)
C140.0162 (3)0.0176 (3)0.0155 (3)0.0029 (2)0.0057 (2)0.0028 (2)
C150.0175 (3)0.0208 (3)0.0136 (3)0.0059 (3)0.0056 (2)0.0009 (2)
Geometric parameters (Å, º) top
Cl1—C71.7164 (7)C3—H3A0.9300
Cl2—C81.7132 (7)C4—C51.5043 (10)
Cl3—C91.7135 (7)C5—C61.5259 (9)
Cl4—C101.7170 (7)C6—C71.3828 (9)
O1—C51.3876 (9)C6—C111.3883 (10)
O1—H1O10.822 (18)C7—C81.4043 (10)
O2—C121.2261 (9)C8—C91.4041 (11)
O3—C41.3651 (10)C9—C101.4008 (11)
O3—C11.3725 (10)C10—C111.3867 (10)
O4—C151.4332 (10)C11—C121.4895 (10)
O4—H1O40.837 (18)C13—C141.5204 (11)
N1—C121.3514 (10)C13—H13A0.9700
N1—C131.4578 (10)C13—H13B0.9700
N1—C51.4778 (9)C14—C151.5161 (11)
C1—C21.3476 (14)C14—H14A0.9700
C1—H1A0.9300C14—H14B0.9700
C2—C31.4361 (13)C15—H15A0.9700
C2—H2A0.9300C15—H15B0.9700
C3—C41.3509 (11)
C5—O1—H1O1109.4 (13)C7—C8—Cl2119.53 (6)
C4—O3—C1106.08 (7)C10—C9—C8120.01 (6)
C15—O4—H1O4104.2 (12)C10—C9—Cl3119.85 (6)
C12—N1—C13121.72 (6)C8—C9—Cl3120.11 (6)
C12—N1—C5114.03 (6)C11—C10—C9118.34 (7)
C13—N1—C5121.93 (6)C11—C10—Cl4120.96 (6)
C2—C1—O3110.62 (8)C9—C10—Cl4120.70 (6)
C2—C1—H1A124.7C10—C11—C6121.66 (7)
O3—C1—H1A124.7C10—C11—C12130.30 (7)
C1—C2—C3106.37 (8)C6—C11—C12108.01 (6)
C1—C2—H2A126.8O2—C12—N1125.72 (7)
C3—C2—H2A126.8O2—C12—C11127.46 (7)
C4—C3—C2105.97 (8)N1—C12—C11106.81 (6)
C4—C3—H3A127.0N1—C13—C14113.51 (7)
C2—C3—H3A127.0N1—C13—H13A108.9
C3—C4—O3110.95 (7)C14—C13—H13A108.9
C3—C4—C5133.06 (7)N1—C13—H13B108.9
O3—C4—C5115.95 (6)C14—C13—H13B108.9
O1—C5—N1112.75 (6)H13A—C13—H13B107.7
O1—C5—C4106.91 (6)C15—C14—C13109.90 (6)
N1—C5—C4109.06 (6)C15—C14—H14A109.7
O1—C5—C6115.49 (6)C13—C14—H14A109.7
N1—C5—C6100.56 (5)C15—C14—H14B109.7
C4—C5—C6111.98 (6)C13—C14—H14B109.7
C7—C6—C11120.70 (6)H14A—C14—H14B108.2
C7—C6—C5129.16 (6)O4—C15—C14109.47 (6)
C11—C6—C5110.11 (6)O4—C15—H15A109.8
C6—C7—C8118.46 (6)C14—C15—H15A109.8
C6—C7—Cl1121.09 (5)O4—C15—H15B109.8
C8—C7—Cl1120.45 (5)C14—C15—H15B109.8
C9—C8—C7120.73 (6)H15A—C15—H15B108.2
C9—C8—Cl2119.73 (5)
C4—O3—C1—C20.16 (10)C6—C7—C8—Cl2176.49 (6)
O3—C1—C2—C30.35 (11)Cl1—C7—C8—Cl22.79 (9)
C1—C2—C3—C40.41 (11)C7—C8—C9—C100.50 (11)
C2—C3—C4—O30.33 (10)Cl2—C8—C9—C10179.44 (6)
C2—C3—C4—C5177.99 (8)C7—C8—C9—Cl3177.71 (6)
C1—O3—C4—C30.12 (9)Cl2—C8—C9—Cl31.23 (9)
C1—O3—C4—C5178.22 (6)C8—C9—C10—C112.51 (11)
C12—N1—C5—O1130.69 (7)Cl3—C9—C10—C11175.71 (6)
C13—N1—C5—O166.34 (9)C8—C9—C10—Cl4178.13 (6)
C12—N1—C5—C4110.72 (7)Cl3—C9—C10—Cl43.66 (9)
C13—N1—C5—C452.25 (9)C9—C10—C11—C61.61 (11)
C12—N1—C5—C67.13 (8)Cl4—C10—C11—C6179.03 (6)
C13—N1—C5—C6170.10 (7)C9—C10—C11—C12176.64 (7)
C3—C4—C5—O14.40 (11)Cl4—C10—C11—C122.72 (12)
O3—C4—C5—O1173.17 (6)C7—C6—C11—C101.38 (11)
C3—C4—C5—N1126.59 (9)C5—C6—C11—C10176.62 (7)
O3—C4—C5—N150.99 (8)C7—C6—C11—C12179.98 (7)
C3—C4—C5—C6123.02 (9)C5—C6—C11—C121.98 (8)
O3—C4—C5—C659.41 (8)C13—N1—C12—O29.35 (13)
O1—C5—C6—C755.36 (10)C5—N1—C12—O2172.35 (8)
N1—C5—C6—C7177.00 (7)C13—N1—C12—C11169.31 (7)
C4—C5—C6—C767.31 (9)C5—N1—C12—C116.30 (9)
O1—C5—C6—C11126.85 (7)C10—C11—C12—O22.32 (14)
N1—C5—C6—C115.21 (8)C6—C11—C12—O2176.12 (8)
C4—C5—C6—C11110.47 (7)C10—C11—C12—N1179.06 (8)
C11—C6—C7—C83.38 (11)C6—C11—C12—N12.50 (9)
C5—C6—C7—C8174.20 (7)C12—N1—C13—C1487.06 (10)
C11—C6—C7—Cl1177.34 (6)C5—N1—C13—C14111.28 (8)
C5—C6—C7—Cl15.07 (11)N1—C13—C14—C15167.92 (7)
C6—C7—C8—C92.45 (11)C13—C14—C15—O4173.65 (7)
Cl1—C7—C8—C9178.27 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O4i0.822 (19)1.866 (19)2.6868 (9)178 (2)
O4—H1O4···O2ii0.837 (19)1.903 (19)2.7020 (10)159.1 (18)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1/2, z1/2.
 

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