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The structure of the centrosymmetric title compound, C8H6Cl2N2O2·2C3H7NO, shows that the hydro­ximo­yl chloride substituent has an essentially planar arrangement and the dihedral angle between this plane and the benzene plane is 18.3 (4)°. The hydro­ximo­yl chloride group has a cis configuration. The packing can be described as a polymeric arrangement of mol­ecules linked through O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018738/is6081sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018738/is6081Isup2.hkl
Contains datablock I

CCDC reference: 277701

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.104
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06
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 1 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,4-Bis[chloro(hydroximino)methyl]benzene N,N'-dimethylformamide disolvate top
Crystal data top
C8H6Cl2N2O2·2C3H7NOZ = 1
Mr = 379.24F(000) = 198
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2021 (18) ÅCell parameters from 1128 reflections
b = 7.600 (2) Åθ = 3.2–25.6°
c = 10.849 (3) ŵ = 0.38 mm1
α = 100.589 (4)°T = 294 K
β = 92.777 (5)°Block, colorless
γ = 113.518 (4)°0.40 × 0.26 × 0.22 mm
V = 456.7 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1856 independent reflections
Radiation source: fine-focus sealed tube1373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 76
Tmin = 0.843, Tmax = 0.920k = 89
2599 measured reflectionsl = 1311
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0422P)2 + 0.1801P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.27 e Å3
1856 reflectionsΔρmin = 0.23 e Å3
115 parameters
Special details top

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
Cl10.39559 (10)0.03690 (8)0.84070 (6)0.0592 (2)
N10.7926 (3)0.0116 (3)0.82425 (19)0.0508 (5)
O10.6277 (3)0.1960 (2)0.76023 (18)0.0660 (5)
H10.720 (5)0.251 (4)0.737 (3)0.083 (10)*
C10.7003 (4)0.1053 (3)0.86551 (19)0.0421 (5)
C20.8517 (3)0.3077 (3)0.93650 (18)0.0393 (5)
C31.0813 (4)0.3545 (3)0.9877 (2)0.0471 (5)
H31.13690.25660.98010.057*
C40.7707 (4)0.4561 (3)0.9501 (2)0.0467 (5)
H40.61610.42720.91710.056*
N20.9843 (3)0.3554 (3)0.62271 (18)0.0488 (5)
O20.8126 (4)0.5657 (3)0.66138 (18)0.0727 (5)
C50.9821 (5)0.5248 (3)0.6752 (2)0.0558 (6)
H51.11880.61960.72630.067*
C60.7753 (5)0.2000 (4)0.5443 (3)0.0712 (8)
H6A0.65380.24670.53560.107*
H6B0.71860.08890.58320.107*
H6C0.81500.16130.46230.107*
C71.1923 (5)0.3165 (5)0.6396 (3)0.0796 (8)
H7A1.31510.42740.69650.119*
H7B1.24690.29450.55940.119*
H7C1.15310.20180.67430.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0438 (3)0.0490 (3)0.0785 (4)0.0216 (2)0.0015 (3)0.0035 (3)
N10.0494 (10)0.0368 (9)0.0637 (12)0.0208 (8)0.0060 (9)0.0012 (8)
O10.0553 (10)0.0402 (9)0.0924 (14)0.0226 (8)0.0012 (9)0.0133 (8)
C10.0421 (11)0.0419 (11)0.0444 (12)0.0206 (9)0.0057 (9)0.0076 (9)
C20.0421 (11)0.0378 (10)0.0404 (11)0.0206 (9)0.0056 (9)0.0050 (8)
C30.0480 (12)0.0418 (11)0.0576 (14)0.0287 (10)0.0027 (10)0.0033 (10)
C40.0390 (11)0.0456 (12)0.0563 (13)0.0230 (9)0.0008 (9)0.0023 (10)
N20.0450 (10)0.0409 (10)0.0579 (12)0.0185 (8)0.0040 (8)0.0036 (8)
O20.0827 (13)0.0690 (12)0.0801 (13)0.0511 (11)0.0131 (10)0.0025 (9)
C50.0612 (14)0.0462 (13)0.0551 (14)0.0204 (11)0.0066 (11)0.0040 (11)
C60.0705 (17)0.0504 (14)0.0748 (18)0.0162 (13)0.0039 (14)0.0043 (13)
C70.0663 (18)0.083 (2)0.104 (2)0.0459 (16)0.0075 (16)0.0223 (17)
Geometric parameters (Å, º) top
Cl1—C11.740 (2)N2—C51.314 (3)
N1—C11.266 (3)N2—C71.445 (3)
N1—O11.387 (2)N2—C61.450 (3)
O1—H10.86 (3)O2—C51.220 (3)
C1—C21.477 (3)C5—H50.9300
C2—C31.382 (3)C6—H6A0.9600
C2—C41.395 (3)C6—H6B0.9600
C3—C4i1.377 (3)C6—H6C0.9600
C3—H30.9300C7—H7A0.9600
C4—C3i1.377 (3)C7—H7B0.9600
C4—H40.9300C7—H7C0.9600
C1—N1—O1113.36 (18)C7—N2—C6117.4 (2)
N1—O1—H1100 (2)O2—C5—N2124.3 (2)
N1—C1—C2120.19 (19)O2—C5—H5117.9
N1—C1—Cl1122.12 (17)N2—C5—H5117.9
C2—C1—Cl1117.69 (15)N2—C6—H6A109.5
C3—C2—C4118.61 (19)N2—C6—H6B109.5
C3—C2—C1119.97 (18)H6A—C6—H6B109.5
C4—C2—C1121.40 (19)N2—C6—H6C109.5
C4i—C3—C2121.13 (19)H6A—C6—H6C109.5
C4i—C3—H3119.4H6B—C6—H6C109.5
C2—C3—H3119.4N2—C7—H7A109.5
C3i—C4—C2120.26 (19)N2—C7—H7B109.5
C3i—C4—H4119.9H7A—C7—H7B109.5
C2—C4—H4119.9N2—C7—H7C109.5
C5—N2—C7122.0 (2)H7A—C7—H7C109.5
C5—N2—C6120.6 (2)H7B—C7—H7C109.5
O1—N1—C1—C2179.71 (18)C4—C2—C3—C4i0.7 (4)
O1—N1—C1—Cl10.8 (3)C1—C2—C3—C4i177.3 (2)
N1—C1—C2—C317.5 (3)C3—C2—C4—C3i0.7 (4)
Cl1—C1—C2—C3162.93 (17)C1—C2—C4—C3i177.3 (2)
N1—C1—C2—C4160.5 (2)C7—N2—C5—O2178.3 (3)
Cl1—C1—C2—C419.1 (3)C6—N2—C5—O21.4 (4)
Symmetry code: (i) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2ii0.86 (3)1.79 (3)2.609 (2)159 (3)
Symmetry code: (ii) x, y1, z.
 

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