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The structure of the centrosymmetric title compound, C
8H
6Cl
2N
2O
2·2C
3H
7NO, 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
CCDC reference: 277701
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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
C8H6Cl2N2O2·2C3H7NO | Z = 1 |
Mr = 379.24 | F(000) = 198 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2021 (18) Å | Cell parameters from 1128 reflections |
b = 7.600 (2) Å | θ = 3.2–25.6° |
c = 10.849 (3) Å | µ = 0.38 mm−1 |
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 tube | 1373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→6 |
Tmin = 0.843, Tmax = 0.920 | k = −8→9 |
2599 measured reflections | l = −13→11 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.04 | Δρmax = 0.27 e Å−3 |
1856 reflections | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.39559 (10) | 0.03690 (8) | 0.84070 (6) | 0.0592 (2) | |
N1 | 0.7926 (3) | −0.0116 (3) | 0.82425 (19) | 0.0508 (5) | |
O1 | 0.6277 (3) | −0.1960 (2) | 0.76023 (18) | 0.0660 (5) | |
H1 | 0.720 (5) | −0.251 (4) | 0.737 (3) | 0.083 (10)* | |
C1 | 0.7003 (4) | 0.1053 (3) | 0.86551 (19) | 0.0421 (5) | |
C2 | 0.8517 (3) | 0.3077 (3) | 0.93650 (18) | 0.0393 (5) | |
C3 | 1.0813 (4) | 0.3545 (3) | 0.9877 (2) | 0.0471 (5) | |
H3 | 1.1369 | 0.2566 | 0.9801 | 0.057* | |
C4 | 0.7707 (4) | 0.4561 (3) | 0.9501 (2) | 0.0467 (5) | |
H4 | 0.6161 | 0.4272 | 0.9171 | 0.056* | |
N2 | 0.9843 (3) | 0.3554 (3) | 0.62271 (18) | 0.0488 (5) | |
O2 | 0.8126 (4) | 0.5657 (3) | 0.66138 (18) | 0.0727 (5) | |
C5 | 0.9821 (5) | 0.5248 (3) | 0.6752 (2) | 0.0558 (6) | |
H5 | 1.1188 | 0.6196 | 0.7263 | 0.067* | |
C6 | 0.7753 (5) | 0.2000 (4) | 0.5443 (3) | 0.0712 (8) | |
H6A | 0.6538 | 0.2467 | 0.5356 | 0.107* | |
H6B | 0.7186 | 0.0889 | 0.5832 | 0.107* | |
H6C | 0.8150 | 0.1613 | 0.4623 | 0.107* | |
C7 | 1.1923 (5) | 0.3165 (5) | 0.6396 (3) | 0.0796 (8) | |
H7A | 1.3151 | 0.4274 | 0.6965 | 0.119* | |
H7B | 1.2469 | 0.2945 | 0.5594 | 0.119* | |
H7C | 1.1531 | 0.2018 | 0.6743 | 0.119* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0438 (3) | 0.0490 (3) | 0.0785 (4) | 0.0216 (2) | −0.0015 (3) | −0.0035 (3) |
N1 | 0.0494 (10) | 0.0368 (9) | 0.0637 (12) | 0.0208 (8) | 0.0060 (9) | −0.0012 (8) |
O1 | 0.0553 (10) | 0.0402 (9) | 0.0924 (14) | 0.0226 (8) | 0.0012 (9) | −0.0133 (8) |
C1 | 0.0421 (11) | 0.0419 (11) | 0.0444 (12) | 0.0206 (9) | 0.0057 (9) | 0.0076 (9) |
C2 | 0.0421 (11) | 0.0378 (10) | 0.0404 (11) | 0.0206 (9) | 0.0056 (9) | 0.0050 (8) |
C3 | 0.0480 (12) | 0.0418 (11) | 0.0576 (14) | 0.0287 (10) | 0.0027 (10) | 0.0033 (10) |
C4 | 0.0390 (11) | 0.0456 (12) | 0.0563 (13) | 0.0230 (9) | −0.0008 (9) | 0.0023 (10) |
N2 | 0.0450 (10) | 0.0409 (10) | 0.0579 (12) | 0.0185 (8) | 0.0040 (8) | 0.0036 (8) |
O2 | 0.0827 (13) | 0.0690 (12) | 0.0801 (13) | 0.0511 (11) | 0.0131 (10) | 0.0025 (9) |
C5 | 0.0612 (14) | 0.0462 (13) | 0.0551 (14) | 0.0204 (11) | 0.0066 (11) | 0.0040 (11) |
C6 | 0.0705 (17) | 0.0504 (14) | 0.0748 (18) | 0.0162 (13) | −0.0039 (14) | −0.0043 (13) |
C7 | 0.0663 (18) | 0.083 (2) | 0.104 (2) | 0.0459 (16) | 0.0075 (16) | 0.0223 (17) |
Geometric parameters (Å, º) top
Cl1—C1 | 1.740 (2) | N2—C5 | 1.314 (3) |
N1—C1 | 1.266 (3) | N2—C7 | 1.445 (3) |
N1—O1 | 1.387 (2) | N2—C6 | 1.450 (3) |
O1—H1 | 0.86 (3) | O2—C5 | 1.220 (3) |
C1—C2 | 1.477 (3) | C5—H5 | 0.9300 |
C2—C3 | 1.382 (3) | C6—H6A | 0.9600 |
C2—C4 | 1.395 (3) | C6—H6B | 0.9600 |
C3—C4i | 1.377 (3) | C6—H6C | 0.9600 |
C3—H3 | 0.9300 | C7—H7A | 0.9600 |
C4—C3i | 1.377 (3) | C7—H7B | 0.9600 |
C4—H4 | 0.9300 | C7—H7C | 0.9600 |
| | | |
C1—N1—O1 | 113.36 (18) | C7—N2—C6 | 117.4 (2) |
N1—O1—H1 | 100 (2) | O2—C5—N2 | 124.3 (2) |
N1—C1—C2 | 120.19 (19) | O2—C5—H5 | 117.9 |
N1—C1—Cl1 | 122.12 (17) | N2—C5—H5 | 117.9 |
C2—C1—Cl1 | 117.69 (15) | N2—C6—H6A | 109.5 |
C3—C2—C4 | 118.61 (19) | N2—C6—H6B | 109.5 |
C3—C2—C1 | 119.97 (18) | H6A—C6—H6B | 109.5 |
C4—C2—C1 | 121.40 (19) | N2—C6—H6C | 109.5 |
C4i—C3—C2 | 121.13 (19) | H6A—C6—H6C | 109.5 |
C4i—C3—H3 | 119.4 | H6B—C6—H6C | 109.5 |
C2—C3—H3 | 119.4 | N2—C7—H7A | 109.5 |
C3i—C4—C2 | 120.26 (19) | N2—C7—H7B | 109.5 |
C3i—C4—H4 | 119.9 | H7A—C7—H7B | 109.5 |
C2—C4—H4 | 119.9 | N2—C7—H7C | 109.5 |
C5—N2—C7 | 122.0 (2) | H7A—C7—H7C | 109.5 |
C5—N2—C6 | 120.6 (2) | H7B—C7—H7C | 109.5 |
| | | |
O1—N1—C1—C2 | 179.71 (18) | C4—C2—C3—C4i | −0.7 (4) |
O1—N1—C1—Cl1 | −0.8 (3) | C1—C2—C3—C4i | 177.3 (2) |
N1—C1—C2—C3 | −17.5 (3) | C3—C2—C4—C3i | 0.7 (4) |
Cl1—C1—C2—C3 | 162.93 (17) | C1—C2—C4—C3i | −177.3 (2) |
N1—C1—C2—C4 | 160.5 (2) | C7—N2—C5—O2 | 178.3 (3) |
Cl1—C1—C2—C4 | −19.1 (3) | C6—N2—C5—O2 | −1.4 (4) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2ii | 0.86 (3) | 1.79 (3) | 2.609 (2) | 159 (3) |
Symmetry code: (ii) x, y−1, z. |
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